NO310069B1 - Nye-4-(oksyalkoksyfenyl)-3-oksy-piperidiner for behandling av hjerte- og nyreinsuffisiens - Google Patents

Nye-4-(oksyalkoksyfenyl)-3-oksy-piperidiner for behandling av hjerte- og nyreinsuffisiens Download PDF

Info

Publication number: NO310069B1
Authority: NO; Norway
Prior art keywords: alkyl; alkoxy; phenyl; ylmethoxy; naphthalen
Prior art date: 1995-09-07

Application number

NO980954A

Other languages

English (en)

Norwegian (no)

Other versions

NO980954L (no

NO980954D0 (no

Inventor

Alfred Binggeli

Volker Breu

Daniel Bur

Walter Fischli

Rolf Gueller

Hans-Peter Maerki

Georges Hirth

Marcel Mueller

Christian Oefner

Heinz Stadler

Eric Vieira

Maurice Wilhelm

Wolfgang Wostl

Original Assignee

Hoffmann La Roche

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1995-09-07

Filing date

1998-03-05

Publication date

2001-05-14

1998-03-05 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1998-03-05 Publication of NO980954D0 publication Critical patent/NO980954D0/no

1998-04-28 Publication of NO980954L publication Critical patent/NO980954L/no

2001-05-14 Publication of NO310069B1 publication Critical patent/NO310069B1/no

Links

206010019280 Heart failures Diseases 0.000 title claims description 5
208000001647 Renal Insufficiency Diseases 0.000 title claims description 4
201000006370 kidney failure Diseases 0.000 title description 2
230000000747 cardiac effect Effects 0.000 title 1
-1 cyano, carboxy Chemical group 0.000 claims description 248
150000001875 compounds Chemical class 0.000 claims description 187
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 101
238000000034 method Methods 0.000 claims description 95
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 84
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 51
229960000583 acetic acid Drugs 0.000 claims description 38
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
125000000217 alkyl group Chemical group 0.000 claims description 26
239000001257 hydrogen Substances 0.000 claims description 24
229910052739 hydrogen Inorganic materials 0.000 claims description 24
229910052736 halogen Inorganic materials 0.000 claims description 23
150000002367 halogens Chemical class 0.000 claims description 22
125000006239 protecting group Chemical group 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 21
125000001424 substituent group Chemical group 0.000 claims description 21
125000004432 carbon atom Chemical group C* 0.000 claims description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
125000001624 naphthyl group Chemical group 0.000 claims description 18
238000010992 reflux Methods 0.000 claims description 18
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
125000004076 pyridyl group Chemical group 0.000 claims description 17
150000002431 hydrogen Chemical class 0.000 claims description 15
125000003545 alkoxy group Chemical group 0.000 claims description 13
125000004093 cyano group Chemical group *C#N 0.000 claims description 13
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
239000012362 glacial acetic acid Substances 0.000 claims description 10
239000003960 organic solvent Substances 0.000 claims description 10
125000004043 oxo group Chemical group O=* 0.000 claims description 10
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 9
229920006395 saturated elastomer Polymers 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims description 8
206010020772 Hypertension Diseases 0.000 claims description 7
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 7
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
125000005842 heteroatom Chemical group 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
125000001425 triazolyl group Chemical group 0.000 claims description 6
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
239000011701 zinc Substances 0.000 claims description 6
229910052725 zinc Inorganic materials 0.000 claims description 6
125000005605 benzo group Chemical group 0.000 claims description 5
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
238000005903 acid hydrolysis reaction Methods 0.000 claims description 4
125000005530 alkylenedioxy group Chemical group 0.000 claims description 4
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
125000002883 imidazolyl group Chemical group 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000000951 phenoxy group Chemical class [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
125000003373 pyrazinyl group Chemical group 0.000 claims description 4
239000002461 renin inhibitor Substances 0.000 claims description 4
229940086526 renin-inhibitors Drugs 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
229940102001 zinc bromide Drugs 0.000 claims description 4
WUKPAJHFMBKCMX-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-ylmethoxy)-4-(4-fluorophenyl)piperidine Chemical compound C1=CC(F)=CC=C1C1C(OCC=2C=C3OCOC3=CC=2)CNCC1 WUKPAJHFMBKCMX-UHFFFAOYSA-N 0.000 claims description 3
239000005977 Ethylene Substances 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
125000003831 tetrazolyl group Chemical group 0.000 claims description 3
FZAFAUXIODKSBH-KZXHCJOXSA-N (2r)-3-[7-[[(3r,4r)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxymethyl]naphthalen-2-yl]oxypropane-1,2-diol Chemical compound C1=CC([C@H]2CCNC[C@@H]2OCC=2C=CC3=CC=C(C=C3C=2)OC[C@H](O)CO)=CC=C1OCCCOCC1=CC=CC=C1 FZAFAUXIODKSBH-KZXHCJOXSA-N 0.000 claims description 2
FZAFAUXIODKSBH-MYZAEBQFSA-N (2s)-3-[7-[[(3r,4r)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxymethyl]naphthalen-2-yl]oxypropane-1,2-diol Chemical compound C1=CC([C@H]2CCNC[C@@H]2OCC=2C=CC3=CC=C(C=C3C=2)OC[C@@H](O)CO)=CC=C1OCCCOCC1=CC=CC=C1 FZAFAUXIODKSBH-MYZAEBQFSA-N 0.000 claims description 2
OIOVXGGCZBNFSE-SYBRLPANSA-N (3r,4r)-3-[(1,4-dimethoxynaphthalen-2-yl)methoxy]-4-[4-[3-(2-methoxyphenoxy)propoxy]phenyl]piperidine Chemical compound COC1=CC=CC=C1OCCCOC1=CC=C([C@@H]2[C@H](CNCC2)OCC=2C(=C3C=CC=CC3=C(OC)C=2)OC)C=C1 OIOVXGGCZBNFSE-SYBRLPANSA-N 0.000 claims description 2
GQZNHBAQKXQYIV-SJHOIFEDSA-N (3r,4r)-3-[(1,4-dimethoxynaphthalen-2-yl)methoxy]-4-[4-[3-[(2-methoxyphenyl)methoxy]propoxy]phenyl]piperidine Chemical compound COC1=CC=CC=C1COCCCOC1=CC=C([C@@H]2[C@H](CNCC2)OCC=2C(=C3C=CC=CC3=C(OC)C=2)OC)C=C1 GQZNHBAQKXQYIV-SJHOIFEDSA-N 0.000 claims description 2
NOZRXDYWCRPRSB-MPZFMJHNSA-N (3r,4r,5s)-3-[(1,4-dimethoxynaphthalen-2-yl)methoxy]-4-[4-[3-[(2-methoxyphenyl)methoxy]propoxy]phenyl]-5-(2h-tetrazol-5-ylmethyl)piperidine Chemical compound COC1=CC=CC=C1COCCCOC1=CC=C([C@@H]2[C@H](CNC[C@H]2CC=2NN=NN=2)OCC=2C(=C3C=CC=CC3=C(OC)C=2)OC)C=C1 NOZRXDYWCRPRSB-MPZFMJHNSA-N 0.000 claims description 2
WUAIVTZASDYIOE-XLDNGHKCSA-N (3s,4r,5r)-3-(methoxymethyl)-5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidine Chemical compound C1=CC([C@@H]2[C@@H](OCC=3C=C4C=CC=CC4=CC=3)CNC[C@H]2COC)=CC=C1OCCCOCC1=CC=CC=C1 WUAIVTZASDYIOE-XLDNGHKCSA-N 0.000 claims description 2
UNIHNYUCROCRPH-ULNSLHSMSA-N (3s,4s,5r)-5-[(4-methoxyphenyl)methoxy]-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-ol Chemical compound C1=CC(OC)=CC=C1CO[C@@H]1[C@@H](C=2C=CC(OCCCOCC=3C=CC=CC=3)=CC=2)[C@H](O)CNC1 UNIHNYUCROCRPH-ULNSLHSMSA-N 0.000 claims description 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
OBPFLVNGKXWSPT-SYRLMZQMSA-N 1-[[(3s,4r,5r)-5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]methyl]imidazolidin-2-one Chemical compound O=C1NCCN1C[C@H]1[C@H](C=2C=CC(OCCCOCC=3C=CC=CC=3)=CC=2)[C@@H](OCC=2C=C3C=CC=CC3=CC=2)CNC1 OBPFLVNGKXWSPT-SYRLMZQMSA-N 0.000 claims description 2
TWSDLMCSIFRJDC-VIZCGCQYSA-N 2-(4-cyclohexylbutoxy)-5-[(3r,4r)-3-[(1,4-dimethoxynaphthalen-2-yl)methoxy]piperidin-4-yl]pyrimidine Chemical compound N1=CC([C@H]2CCNC[C@@H]2OCC=2C=C(C3=CC=CC=C3C=2OC)OC)=CN=C1OCCCCC1CCCCC1 TWSDLMCSIFRJDC-VIZCGCQYSA-N 0.000 claims description 2
PJZUGRXNVXFQNC-PLJDCMBSSA-N 3-[(3s,4s,5r)-5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxypropan-1-ol Chemical compound C1=CC([C@@H]2[C@@H](OCC=3C=C4C=CC=CC4=CC=3)CNC[C@H]2OCCCO)=CC=C1OCCCOCC1=CC=CC=C1 PJZUGRXNVXFQNC-PLJDCMBSSA-N 0.000 claims description 2
SHAMCHNYKIYNST-AMAPPZPBSA-N 4-[2-[7-[[(3r,4r)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxymethyl]naphthalen-2-yl]oxyethyl]morpholine Chemical compound C=1C=C([C@@H]2[C@H](CNCC2)OCC=2C=C3C=C(OCCN4CCOCC4)C=CC3=CC=2)C=CC=1OCCCOCC1=CC=CC=C1 SHAMCHNYKIYNST-AMAPPZPBSA-N 0.000 claims description 2
BGAWAKUWOBKLJF-MINDXDAISA-N 4-[2-[[(3s,4r,5r)-5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]methoxy]ethyl]morpholine Chemical compound C=1C=C([C@@H]2[C@H](CNC[C@H]2COCCN2CCOCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCCOCC1=CC=CC=C1 BGAWAKUWOBKLJF-MINDXDAISA-N 0.000 claims description 2
UXRWZYYMQOXLII-PPTMTGTBSA-N 7-[[(3r,4r)-4-[4-[3-[(2-methoxyphenyl)methoxy]propoxy]phenyl]piperidin-3-yl]oxymethyl]-1,2,3,4-tetrahydroquinoline Chemical compound COC1=CC=CC=C1COCCCOC1=CC=C([C@@H]2[C@H](CNCC2)OCC=2C=C3NCCCC3=CC=2)C=C1 UXRWZYYMQOXLII-PPTMTGTBSA-N 0.000 claims description 2
OTVOEZNYPLBKLK-PPTMTGTBSA-N 7-[[(3r,4r)-4-[4-[3-[(2-methoxyphenyl)methoxy]propoxy]phenyl]piperidin-3-yl]oxymethyl]quinoline Chemical compound COC1=CC=CC=C1COCCCOC1=CC=C([C@@H]2[C@H](CNCC2)OCC=2C=C3N=CC=CC3=CC=2)C=C1 OTVOEZNYPLBKLK-PPTMTGTBSA-N 0.000 claims description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
RQVPNCSWOUIVAQ-RGRQWMLTSA-N [(3s,4r,5r)-5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]methanol Chemical compound C1=CC([C@@H]2[C@@H](OCC=3C=C4C=CC=CC4=CC=3)CNC[C@H]2CO)=CC=C1OCCCOCC1=CC=CC=C1 RQVPNCSWOUIVAQ-RGRQWMLTSA-N 0.000 claims description 2
239000013543 active substance Substances 0.000 claims description 2
125000002947 alkylene group Chemical group 0.000 claims description 2
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
125000002757 morpholinyl group Chemical group 0.000 claims description 2
ABNIRSHNIAQENF-RHNUXINZSA-N n-ethyl-n-[[(3s,4r,5r)-5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]methyl]ethanamine Chemical compound C1=CC([C@@H]2[C@@H](OCC=3C=C4C=CC=CC4=CC=3)CNC[C@H]2CN(CC)CC)=CC=C1OCCCOCC1=CC=CC=C1 ABNIRSHNIAQENF-RHNUXINZSA-N 0.000 claims description 2
125000002971 oxazolyl group Chemical group 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000003226 pyrazolyl group Chemical group 0.000 claims description 2
125000000168 pyrrolyl group Chemical group 0.000 claims description 2
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 2
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 2
125000004306 triazinyl group Chemical group 0.000 claims description 2
239000004146 Propane-1,2-diol Substances 0.000 claims 2
239000000571 coke Substances 0.000 claims 2
229960004063 propylene glycol Drugs 0.000 claims 2
NEPVAKOZRPVHEM-RTBURBONSA-N (3r,4r)-3-(3-chlorophenoxy)-4-(3,4-dimethylphenoxy)piperidine Chemical compound C1=C(C)C(C)=CC=C1O[C@H]1[C@H](OC=2C=C(Cl)C=CC=2)CNCC1 NEPVAKOZRPVHEM-RTBURBONSA-N 0.000 claims 1
CKFYLSMACGXFQB-XHFCRVKJSA-N 4-[[(3s,4r,5r)-5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]methylsulfanyl]pyridine Chemical compound C=1C=C([C@@H]2[C@H](CNC[C@H]2CSC=2C=CN=CC=2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCCOCC1=CC=CC=C1 CKFYLSMACGXFQB-XHFCRVKJSA-N 0.000 claims 1
YNZOWKPPAKUTGP-ZUKKLESISA-N 5-[(3r,4r)-3-[(1,4-dimethoxynaphthalen-2-yl)methoxy]piperidin-4-yl]-2-[3-[(2-methoxyphenyl)methoxy]propoxy]pyridine Chemical compound COC1=CC=CC=C1COCCCOC1=CC=C([C@@H]2[C@H](CNCC2)OCC=2C(=C3C=CC=CC3=C(OC)C=2)OC)C=N1 YNZOWKPPAKUTGP-ZUKKLESISA-N 0.000 claims 1
102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 claims 1
125000005037 alkyl phenyl group Chemical group 0.000 claims 1
229910052731 fluorine Inorganic materials 0.000 claims 1
239000011737 fluorine Substances 0.000 claims 1
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 474
239000007787 solid Substances 0.000 description 261
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 250
239000000243 solution Substances 0.000 description 249
239000000203 mixture Substances 0.000 description 228
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 188
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 169
239000012230 colorless oil Substances 0.000 description 126
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 121
239000003921 oil Substances 0.000 description 110
235000019198 oils Nutrition 0.000 description 110
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 108
230000002829 reductive effect Effects 0.000 description 108
238000006243 chemical reaction Methods 0.000 description 99
238000005804 alkylation reaction Methods 0.000 description 95
230000029936 alkylation Effects 0.000 description 94
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 91
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 87
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 85
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 84
239000000741 silica gel Substances 0.000 description 82
229910002027 silica gel Inorganic materials 0.000 description 82
239000012074 organic phase Substances 0.000 description 78
239000003480 eluent Substances 0.000 description 74
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 70
238000003776 cleavage reaction Methods 0.000 description 66
230000007017 scission Effects 0.000 description 66
239000002904 solvent Substances 0.000 description 62
235000019439 ethyl acetate Nutrition 0.000 description 56
239000011541 reaction mixture Substances 0.000 description 56
229910052943 magnesium sulfate Inorganic materials 0.000 description 54
235000019341 magnesium sulphate Nutrition 0.000 description 54
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 51
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 51
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 44
239000012043 crude product Substances 0.000 description 44
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 42
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 41
RUHJZSZTSCSTCC-UHFFFAOYSA-N 2-(bromomethyl)naphthalene Chemical compound C1=CC=CC2=CC(CBr)=CC=C21 RUHJZSZTSCSTCC-UHFFFAOYSA-N 0.000 description 37
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 32
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 31
239000006260 foam Substances 0.000 description 31
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
238000004587 chromatography analysis Methods 0.000 description 28
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 28
229910000041 hydrogen chloride Inorganic materials 0.000 description 28
239000007858 starting material Substances 0.000 description 28
238000000746 purification Methods 0.000 description 26
239000011347 resin Substances 0.000 description 26
229920005989 resin Polymers 0.000 description 26
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 25
229910004298 SiO 2 Inorganic materials 0.000 description 24
229910021529 ammonia Inorganic materials 0.000 description 24
LHHCSNFAOIFYRV-DOVBMPENSA-N boceprevir Chemical compound O=C([C@@H]1[C@@H]2[C@@H](C2(C)C)CN1C(=O)[C@@H](NC(=O)NC(C)(C)C)C(C)(C)C)NC(C(=O)C(N)=O)CC1CCC1 LHHCSNFAOIFYRV-DOVBMPENSA-N 0.000 description 24
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
238000010626 work up procedure Methods 0.000 description 24
230000010933 acylation Effects 0.000 description 23
238000005917 acylation reaction Methods 0.000 description 23
239000000843 powder Substances 0.000 description 23
230000009467 reduction Effects 0.000 description 23
229910052938 sodium sulfate Inorganic materials 0.000 description 23
235000011152 sodium sulphate Nutrition 0.000 description 23
239000002253 acid Substances 0.000 description 22
ORWYRWWVDCYOMK-HBZPZAIKSA-N angiotensin I Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C1=CC=C(O)C=C1 ORWYRWWVDCYOMK-HBZPZAIKSA-N 0.000 description 22
238000009833 condensation Methods 0.000 description 21
230000005494 condensation Effects 0.000 description 21
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
239000013078 crystal Substances 0.000 description 20
238000006197 hydroboration reaction Methods 0.000 description 20
JBCONEBMULKDJJ-UHFFFAOYSA-N tert-butyl 4-[4-(2-hydroxyethyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(CCO)C=C1 JBCONEBMULKDJJ-UHFFFAOYSA-N 0.000 description 20
125000004356 hydroxy functional group Chemical group O* 0.000 description 19
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 18
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 17
239000000725 suspension Substances 0.000 description 17
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 17
GNXDGBIGABRJNZ-UHFFFAOYSA-N 4-(4-chlorophenyl)-1-methylpiperidin-3-ol Chemical compound OC1CN(C)CCC1C1=CC=C(Cl)C=C1 GNXDGBIGABRJNZ-UHFFFAOYSA-N 0.000 description 16
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 15
239000002585 base Substances 0.000 description 15
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 15
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 15
SJZKULRDWHPHGG-UHFFFAOYSA-N 1-benzylpiperidin-4-one Chemical compound C1CC(=O)CCN1CC1=CC=CC=C1 SJZKULRDWHPHGG-UHFFFAOYSA-N 0.000 description 14
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 14
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
239000003054 catalyst Substances 0.000 description 14
238000003379 elimination reaction Methods 0.000 description 14
150000002148 esters Chemical group 0.000 description 14
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
239000000126 substance Substances 0.000 description 14
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 14
RSWGJHLUYNHPMX-ONCXSQPRSA-N abietic acid Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(O)=O RSWGJHLUYNHPMX-ONCXSQPRSA-N 0.000 description 13
238000012512 characterization method Methods 0.000 description 13
239000003795 chemical substances by application Substances 0.000 description 13
238000000354 decomposition reaction Methods 0.000 description 13
230000008030 elimination Effects 0.000 description 13
229910000027 potassium carbonate Inorganic materials 0.000 description 13
UQDVRZMOHUIMMQ-UHFFFAOYSA-N tert-butyl 4-[4-(2-hydroxyethoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(OCCO)C=C1 UQDVRZMOHUIMMQ-UHFFFAOYSA-N 0.000 description 13
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 12
FXCYIHBYSVDOEV-UHFFFAOYSA-N tert-butyl 4-(4-fluorophenyl)-3-hydroxypiperidine-1-carboxylate Chemical compound OC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(F)C=C1 FXCYIHBYSVDOEV-UHFFFAOYSA-N 0.000 description 12
LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 description 11
ZYYUBKBRPATXQK-UHFFFAOYSA-N 4-[4-(hydroxymethyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C1=CC(CO)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(C(O)=O)CC1 ZYYUBKBRPATXQK-UHFFFAOYSA-N 0.000 description 11
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
230000015572 biosynthetic process Effects 0.000 description 11
239000000047 product Substances 0.000 description 11
239000012312 sodium hydride Substances 0.000 description 11
229910000104 sodium hydride Inorganic materials 0.000 description 11
101800000734 Angiotensin-1 Proteins 0.000 description 10
102400000344 Angiotensin-1 Human genes 0.000 description 10
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 10
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 10
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 10
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 10
235000017557 sodium bicarbonate Nutrition 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
235000011121 sodium hydroxide Nutrition 0.000 description 10
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 10
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 9
239000012442 inert solvent Substances 0.000 description 9
238000004519 manufacturing process Methods 0.000 description 9
230000003647 oxidation Effects 0.000 description 9
238000007254 oxidation reaction Methods 0.000 description 9
229910052763 palladium Inorganic materials 0.000 description 9
239000011734 sodium Substances 0.000 description 9
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
229910052786 argon Inorganic materials 0.000 description 8
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
238000009903 catalytic hydrogenation reaction Methods 0.000 description 8
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 8
150000003333 secondary alcohols Chemical class 0.000 description 8
238000003786 synthesis reaction Methods 0.000 description 8
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
150000001412 amines Chemical class 0.000 description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
239000003153 chemical reaction reagent Substances 0.000 description 7
238000005660 chlorination reaction Methods 0.000 description 7
125000004494 ethyl ester group Chemical group 0.000 description 7
239000004744 fabric Substances 0.000 description 7
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
NBOAJKKARIFZFK-UHFFFAOYSA-N 1-benzyl-4-(4-fluorophenyl)piperidin-3-ol Chemical compound C1CC(C=2C=CC(F)=CC=2)C(O)CN1CC1=CC=CC=C1 NBOAJKKARIFZFK-UHFFFAOYSA-N 0.000 description 6
KQFJBAQBSLFZEN-UHFFFAOYSA-N 4-[4-(2-hydroxyethoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C1=CC(OCCO)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(C(O)=O)CC1 KQFJBAQBSLFZEN-UHFFFAOYSA-N 0.000 description 6
108090000783 Renin Proteins 0.000 description 6
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 6
230000002152 alkylating effect Effects 0.000 description 6
235000019270 ammonium chloride Nutrition 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 6
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
238000001816 cooling Methods 0.000 description 6
238000002425 crystallisation Methods 0.000 description 6
230000008025 crystallization Effects 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
239000003112 inhibitor Substances 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 6
125000003386 piperidinyl group Chemical group 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
239000012279 sodium borohydride Substances 0.000 description 6
229910000033 sodium borohydride Inorganic materials 0.000 description 6
BSUOHACWZPMFEW-UHFFFAOYSA-N tert-butyl 4-[4-(hydroxymethyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(CO)C=C1 BSUOHACWZPMFEW-UHFFFAOYSA-N 0.000 description 6
238000012360 testing method Methods 0.000 description 6
HBZNNDPZKSNEBF-UHFFFAOYSA-N 2-[4-[1-[(2-methylpropan-2-yl)oxycarbonyl]-3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]acetic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(CC(O)=O)C=C1 HBZNNDPZKSNEBF-UHFFFAOYSA-N 0.000 description 5
HOYKLMVYCVTQGV-UHFFFAOYSA-N 3-(chloromethyl)-1-phenylmethoxynaphthalene Chemical compound C=12C=CC=CC2=CC(CCl)=CC=1OCC1=CC=CC=C1 HOYKLMVYCVTQGV-UHFFFAOYSA-N 0.000 description 5
102000005862 Angiotensin II Human genes 0.000 description 5
101800000733 Angiotensin-2 Proteins 0.000 description 5
CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 5
239000012448 Lithium borohydride Substances 0.000 description 5
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 5
102100028255 Renin Human genes 0.000 description 5
125000004036 acetal group Chemical group 0.000 description 5
150000001298 alcohols Chemical class 0.000 description 5
150000001299 aldehydes Chemical class 0.000 description 5
229950006323 angiotensin ii Drugs 0.000 description 5
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 5
244000309464 bull Species 0.000 description 5
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 5
239000006185 dispersion Substances 0.000 description 5
150000002118 epoxides Chemical class 0.000 description 5
TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 5
DTSSCQVCVYZGSI-UHFFFAOYSA-N methyl 3-amino-2,5-dichlorobenzoate Chemical compound COC(=O)C1=CC(Cl)=CC(N)=C1Cl DTSSCQVCVYZGSI-UHFFFAOYSA-N 0.000 description 5
UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 5
150000002924 oxiranes Chemical class 0.000 description 5
235000012976 tarts Nutrition 0.000 description 5
ZARPYLRJFXAKRQ-UHFFFAOYSA-N tert-butyl 4-(4-bromophenyl)-3-hydroxypiperidine-1-carboxylate Chemical compound OC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(Br)C=C1 ZARPYLRJFXAKRQ-UHFFFAOYSA-N 0.000 description 5
LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 4
GIGRWGTZFONRKA-UHFFFAOYSA-N 1-(bromomethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CBr)C=C1 GIGRWGTZFONRKA-UHFFFAOYSA-N 0.000 description 4
MOHYOXXOKFQHDC-UHFFFAOYSA-N 1-(chloromethyl)-4-methoxybenzene Chemical compound COC1=CC=C(CCl)C=C1 MOHYOXXOKFQHDC-UHFFFAOYSA-N 0.000 description 4
IIXQVVWSHGXXIR-UHFFFAOYSA-N 1-benzyl-4-(4-hydroxyphenyl)piperidin-3-ol Chemical compound C1CC(C=2C=CC(O)=CC=2)C(O)CN1CC1=CC=CC=C1 IIXQVVWSHGXXIR-UHFFFAOYSA-N 0.000 description 4
ORLCYMQZIPSODD-UHFFFAOYSA-N 1-chloro-2-[chloro(2,2,2-trichloroethoxy)phosphoryl]oxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(=O)OCC(Cl)(Cl)Cl ORLCYMQZIPSODD-UHFFFAOYSA-N 0.000 description 4
MQKSSFLWVWGBIZ-UHFFFAOYSA-N 2-(bromomethyl)-1-methoxynaphthalene Chemical compound C1=CC=C2C(OC)=C(CBr)C=CC2=C1 MQKSSFLWVWGBIZ-UHFFFAOYSA-N 0.000 description 4
ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 4
HQOJGQRBAWDDRQ-UHFFFAOYSA-N 4-[4-(2-hydroxyethyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C1=CC(CCO)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(C(O)=O)CC1 HQOJGQRBAWDDRQ-UHFFFAOYSA-N 0.000 description 4
MCTCGRVEOIQYAI-UHFFFAOYSA-N 4-[4-(3-hydroxypropoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C1=CC(OCCCO)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(C(O)=O)CC1 MCTCGRVEOIQYAI-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 4
239000002168 alkylating agent Substances 0.000 description 4
229940100198 alkylating agent Drugs 0.000 description 4
239000000010 aprotic solvent Substances 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
229910002091 carbon monoxide Inorganic materials 0.000 description 4
238000006555 catalytic reaction Methods 0.000 description 4
CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 4
230000032050 esterification Effects 0.000 description 4
238000005886 esterification reaction Methods 0.000 description 4
239000007903 gelatin capsule Substances 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
230000007062 hydrolysis Effects 0.000 description 4
238000006460 hydrolysis reaction Methods 0.000 description 4
239000005457 ice water Substances 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
239000007788 liquid Substances 0.000 description 4
230000000269 nucleophilic effect Effects 0.000 description 4
XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical class O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 4
229920005862 polyol Polymers 0.000 description 4
150000003077 polyols Chemical class 0.000 description 4
238000012545 processing Methods 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
AJASTZDEVUUDKP-UHFFFAOYSA-N tert-butyl 3-hydroxy-4-(4-hydroxyphenyl)piperidine-1-carboxylate Chemical compound OC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(O)C=C1 AJASTZDEVUUDKP-UHFFFAOYSA-N 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
FHDKYDIBZIKLHN-UHFFFAOYSA-N 1-benzyl-4-(3-fluorophenyl)piperidin-3-ol Chemical compound C1CC(C=2C=C(F)C=CC=2)C(O)CN1CC1=CC=CC=C1 FHDKYDIBZIKLHN-UHFFFAOYSA-N 0.000 description 3
FGUXWHJEVONFPV-UHFFFAOYSA-N 1-benzyl-4-(3-hydroxyphenyl)piperidin-3-ol Chemical compound C1CC(C=2C=C(O)C=CC=2)C(O)CN1CC1=CC=CC=C1 FGUXWHJEVONFPV-UHFFFAOYSA-N 0.000 description 3
BDEYRIMMANLYDV-UHFFFAOYSA-N 1-benzyl-4-(4-bromophenyl)piperidin-3-ol Chemical compound C1CC(C=2C=CC(Br)=CC=2)C(O)CN1CC1=CC=CC=C1 BDEYRIMMANLYDV-UHFFFAOYSA-N 0.000 description 3
BROWSDUVKNBAHK-UHFFFAOYSA-N 1-benzyl-4-(4-methoxyphenyl)piperidin-3-ol Chemical compound C1=CC(OC)=CC=C1C1C(O)CN(CC=2C=CC=CC=2)CC1 BROWSDUVKNBAHK-UHFFFAOYSA-N 0.000 description 3
IKXLBTKYQYYYNN-UHFFFAOYSA-N 2,2,2-trichloroethyl 4-[3-(2-hydroxyethoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound OCCOC1=CC=CC(C2C(CN(CC2)C(=O)OCC(Cl)(Cl)Cl)OCC=2C=C3C=CC=CC3=CC=2)=C1 IKXLBTKYQYYYNN-UHFFFAOYSA-N 0.000 description 3
QPLJYAKLSCXZSF-UHFFFAOYSA-N 2,2,2-trichloroethyl carbamate Chemical compound NC(=O)OCC(Cl)(Cl)Cl QPLJYAKLSCXZSF-UHFFFAOYSA-N 0.000 description 3
FXKASOSOVAVXTA-UHFFFAOYSA-N 2-(2-iodoethoxy)oxane Chemical compound ICCOC1CCCCO1 FXKASOSOVAVXTA-UHFFFAOYSA-N 0.000 description 3
HJNHUFQGDJLQRS-UHFFFAOYSA-N 2-(3-bromopropoxy)oxane Chemical compound BrCCCOC1CCCCO1 HJNHUFQGDJLQRS-UHFFFAOYSA-N 0.000 description 3
KYAPAOHLPIORMS-UHFFFAOYSA-N 2-(bromomethyl)-4-methoxyquinazoline Chemical compound C1=CC=C2C(OC)=NC(CBr)=NC2=C1 KYAPAOHLPIORMS-UHFFFAOYSA-N 0.000 description 3
BPXKZEMBEZGUAH-UHFFFAOYSA-N 2-(chloromethoxy)ethyl-trimethylsilane Chemical compound C[Si](C)(C)CCOCCl BPXKZEMBEZGUAH-UHFFFAOYSA-N 0.000 description 3
XXOUDRUICBBFBV-UHFFFAOYSA-N 2-[[3-(chloromethyl)naphthalen-1-yl]oxymethoxy]ethyl-trimethylsilane Chemical compound C1=CC=C2C(OCOCC[Si](C)(C)C)=CC(CCl)=CC2=C1 XXOUDRUICBBFBV-UHFFFAOYSA-N 0.000 description 3
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
JPGLCEGGYMERBU-UHFFFAOYSA-N 3-hydroxy-4-(4-hydroxyphenyl)piperidine-1-carboxylic acid Chemical compound OC1CN(C(O)=O)CCC1C1=CC=C(O)C=C1 JPGLCEGGYMERBU-UHFFFAOYSA-N 0.000 description 3
VKRVGCOHWPOPGQ-UHFFFAOYSA-N 4-(2-trimethylsilylethoxymethoxy)benzoic acid Chemical compound C[Si](C)(C)CCOCOC1=CC=C(C(O)=O)C=C1 VKRVGCOHWPOPGQ-UHFFFAOYSA-N 0.000 description 3
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
PVROXHOVNNTQFD-UHFFFAOYSA-N 4-(4-bromophenyl)piperidin-3-ol Chemical compound OC1CNCCC1C1=CC=C(Br)C=C1 PVROXHOVNNTQFD-UHFFFAOYSA-N 0.000 description 3
SEDFKIHVEDFLGY-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[(1-methoxynaphthalen-2-yl)methoxy]piperidine-1-carboxylic acid Chemical compound C1=CC2=CC=CC=C2C(OC)=C1COC1CN(C(O)=O)CCC1C1=CC=C(F)C=C1 SEDFKIHVEDFLGY-UHFFFAOYSA-N 0.000 description 3
GBIDZLQNISORRN-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[(3-methoxynaphthalen-2-yl)methoxy]piperidine-1-carboxylic acid Chemical compound COC1=CC2=CC=CC=C2C=C1COC1CN(C(O)=O)CCC1C1=CC=C(F)C=C1 GBIDZLQNISORRN-UHFFFAOYSA-N 0.000 description 3
UNLSYPQBBUKZMY-UHFFFAOYSA-N 4-(4-fluorophenyl)piperidin-3-ol Chemical compound OC1CNCCC1C1=CC=C(F)C=C1 UNLSYPQBBUKZMY-UHFFFAOYSA-N 0.000 description 3
WXQFUNDPPZSNJQ-UHFFFAOYSA-N 4-[4-(aminomethyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C1=CC(CN)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(C(O)=O)CC1 WXQFUNDPPZSNJQ-UHFFFAOYSA-N 0.000 description 3
IDDIPDKBTSGVOC-UHFFFAOYSA-N 4-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenoxy]-1-phenylbutan-1-one Chemical compound C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCCC(=O)C1=CC=CC=C1 IDDIPDKBTSGVOC-UHFFFAOYSA-N 0.000 description 3
JRDOVDQMUHMTLN-UHFFFAOYSA-N 5-(bromomethyl)-1-benzofuran Chemical compound BrCC1=CC=C2OC=CC2=C1 JRDOVDQMUHMTLN-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
239000002841 Lewis acid Substances 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
RBYGDVHOECIAFC-UHFFFAOYSA-L acetonitrile;palladium(2+);dichloride Chemical compound [Cl-].[Cl-].[Pd+2].CC#N.CC#N RBYGDVHOECIAFC-UHFFFAOYSA-L 0.000 description 3
150000001409 amidines Chemical class 0.000 description 3
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 3
229910000085 borane Inorganic materials 0.000 description 3
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
230000031709 bromination Effects 0.000 description 3
238000005893 bromination reaction Methods 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
239000000872 buffer Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000007859 condensation product Substances 0.000 description 3
238000005859 coupling reaction Methods 0.000 description 3
238000001212 derivatisation Methods 0.000 description 3
239000008298 dragée Substances 0.000 description 3
125000001033 ether group Chemical group 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
150000004678 hydrides Chemical class 0.000 description 3
238000011534 incubation Methods 0.000 description 3
150000007517 lewis acids Chemical class 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
150000002642 lithium compounds Chemical class 0.000 description 3
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
LZMQNYZCJHABJF-UHFFFAOYSA-N methyl 4-(1-benzyl-3-hydroxypiperidin-4-yl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1C(O)CN(CC=2C=CC=CC=2)CC1 LZMQNYZCJHABJF-UHFFFAOYSA-N 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
239000007800 oxidant agent Substances 0.000 description 3
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
150000003053 piperidines Chemical class 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000002994 raw material Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
238000000926 separation method Methods 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 3
238000003756 stirring Methods 0.000 description 3
YFPFPXYJJJHRDQ-UHFFFAOYSA-N tert-butyl 3-(naphthalen-2-ylmethoxy)-4-[4-(2-phenylsulfanylethyl)phenyl]piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1CCSC1=CC=CC=C1 YFPFPXYJJJHRDQ-UHFFFAOYSA-N 0.000 description 3
UPLXCFYPRDOCSF-UHFFFAOYSA-N tert-butyl 3-(naphthalen-2-ylmethoxy)-4-phenylpiperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=CC=C1 UPLXCFYPRDOCSF-UHFFFAOYSA-N 0.000 description 3
ARQSLQQTHBEPMF-UHFFFAOYSA-N tert-butyl 3-hydroxy-4-[4-(2-trityloxyethyl)phenyl]piperidine-1-carboxylate Chemical compound OC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1CCOC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ARQSLQQTHBEPMF-UHFFFAOYSA-N 0.000 description 3
HWNKSGVMOCONJS-UHFFFAOYSA-N tert-butyl 3-hydroxy-4-phenylpiperidine-1-carboxylate Chemical compound OC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=CC=C1 HWNKSGVMOCONJS-UHFFFAOYSA-N 0.000 description 3
RUAZHWDGALQEQE-UHFFFAOYSA-N tert-butyl 4-(4-chlorophenyl)-3,4-dihydroxypiperidine-1-carboxylate Chemical compound OC1CN(C(=O)OC(C)(C)C)CCC1(O)C1=CC=C(Cl)C=C1 RUAZHWDGALQEQE-UHFFFAOYSA-N 0.000 description 3
QNLPASOPSIEBOQ-UHFFFAOYSA-N tert-butyl 4-(4-cyanophenyl)-3-hydroxypiperidine-1-carboxylate Chemical compound OC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(C#N)C=C1 QNLPASOPSIEBOQ-UHFFFAOYSA-N 0.000 description 3
VLDVCWDUHRSKFX-UHFFFAOYSA-N tert-butyl 4-[4-(2-hydroxyethoxy)phenyl]-3-[[4-(2-trimethylsilylethoxymethoxy)naphthalen-2-yl]methoxy]piperidine-1-carboxylate Chemical compound C=1C(OCOCC[Si](C)(C)C)=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(OCCO)C=C1 VLDVCWDUHRSKFX-UHFFFAOYSA-N 0.000 description 3
YNVOMSDITJMNET-UHFFFAOYSA-N thiophene-3-carboxylic acid Chemical compound OC(=O)C=1C=CSC=1 YNVOMSDITJMNET-UHFFFAOYSA-N 0.000 description 3
UZGZPQGJNHDHKO-UHFFFAOYSA-N (1-methoxynaphthalen-2-yl)methanol Chemical compound C1=CC=C2C(OC)=C(CO)C=CC2=C1 UZGZPQGJNHDHKO-UHFFFAOYSA-N 0.000 description 2
RUEMLKUMKKDJTF-UHFFFAOYSA-N (2z)-n-diazoniopyridine-2-carboximidate Chemical compound [N-]=[N+]=NC(=O)C1=CC=CC=N1 RUEMLKUMKKDJTF-UHFFFAOYSA-N 0.000 description 2
QUFXVYRFRKHGBW-UHFFFAOYSA-N (3-methoxynaphthalen-2-yl)methanol Chemical compound C1=CC=C2C=C(CO)C(OC)=CC2=C1 QUFXVYRFRKHGBW-UHFFFAOYSA-N 0.000 description 2
ZGYSKNTXDRCQBO-PXJZQJOASA-N (3r,4r)-4-(4-fluorophenyl)-3-[(4-phenylmethoxynaphthalen-2-yl)methoxy]piperidine Chemical compound C1=CC(F)=CC=C1[C@@H]1[C@@H](OCC=2C=C3C=CC=CC3=C(OCC=3C=CC=CC=3)C=2)CNCC1 ZGYSKNTXDRCQBO-PXJZQJOASA-N 0.000 description 2
ZGYSKNTXDRCQBO-LMSSTIIKSA-N (3s,4s)-4-(4-fluorophenyl)-3-[(4-phenylmethoxynaphthalen-2-yl)methoxy]piperidine Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](OCC=2C=C3C=CC=CC3=C(OCC=3C=CC=CC=3)C=2)CNCC1 ZGYSKNTXDRCQBO-LMSSTIIKSA-N 0.000 description 2
QZWQACWDEVFKFZ-UHFFFAOYSA-N (4-phenylmethoxynaphthalen-2-yl)methanol Chemical compound C=12C=CC=CC2=CC(CO)=CC=1OCC1=CC=CC=C1 QZWQACWDEVFKFZ-UHFFFAOYSA-N 0.000 description 2
UAWVMPOAIVZWFQ-UHFFFAOYSA-N 1-(chloromethyl)-2-methoxybenzene Chemical compound COC1=CC=CC=C1CCl UAWVMPOAIVZWFQ-UHFFFAOYSA-N 0.000 description 2
VGISFWWEOGVMED-UHFFFAOYSA-N 1-(chloromethyl)-3-methoxybenzene Chemical compound COC1=CC=CC(CCl)=C1 VGISFWWEOGVMED-UHFFFAOYSA-N 0.000 description 2
RNESHYJZFJASOC-UHFFFAOYSA-N 1-benzyl-3-(naphthalen-2-ylmethoxy)-4-(3-phenylmethoxyphenyl)piperidine Chemical compound C=1C=C2C=CC=CC2=CC=1COC(C(CC1)C=2C=C(OCC=3C=CC=CC=3)C=CC=2)CN1CC1=CC=CC=C1 RNESHYJZFJASOC-UHFFFAOYSA-N 0.000 description 2
SARJXPOVMVTXQS-UHFFFAOYSA-N 1-benzyl-4-(2-fluorophenyl)piperidin-3-ol Chemical compound C1CC(C=2C(=CC=CC=2)F)C(O)CN1CC1=CC=CC=C1 SARJXPOVMVTXQS-UHFFFAOYSA-N 0.000 description 2
CRIXZDFDDHJKEU-UHFFFAOYSA-N 1-benzyl-4-(3-bromophenyl)-3,6-dihydro-2h-pyridine Chemical compound BrC1=CC=CC(C=2CCN(CC=3C=CC=CC=3)CC=2)=C1 CRIXZDFDDHJKEU-UHFFFAOYSA-N 0.000 description 2
LOXDBSYFCGJVLF-UHFFFAOYSA-N 1-benzyl-4-(3-bromophenyl)piperidin-3-ol Chemical compound C1CC(C=2C=C(Br)C=CC=2)C(O)CN1CC1=CC=CC=C1 LOXDBSYFCGJVLF-UHFFFAOYSA-N 0.000 description 2
PUIYDQLGQMSTDE-UHFFFAOYSA-N 1-benzyl-4-(3-methoxyphenyl)piperidin-3-ol Chemical compound COC1=CC=CC(C2C(CN(CC=3C=CC=CC=3)CC2)O)=C1 PUIYDQLGQMSTDE-UHFFFAOYSA-N 0.000 description 2
GJVMVDZUAGQRTM-UHFFFAOYSA-N 1-benzyl-4-(3-phenylmethoxyphenyl)piperidin-3-ol Chemical compound C1CC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)C(O)CN1CC1=CC=CC=C1 GJVMVDZUAGQRTM-UHFFFAOYSA-N 0.000 description 2
IXIPFXSBPXIFIC-UHFFFAOYSA-N 1-benzyl-4-(4-bromophenyl)-3,6-dihydro-2h-pyridine Chemical compound C1=CC(Br)=CC=C1C(CC1)=CCN1CC1=CC=CC=C1 IXIPFXSBPXIFIC-UHFFFAOYSA-N 0.000 description 2
MZPGLOYTGMFUGC-UHFFFAOYSA-N 1-benzyl-4-(4-bromophenyl)piperidin-4-ol Chemical compound C1CC(O)(C=2C=CC(Br)=CC=2)CCN1CC1=CC=CC=C1 MZPGLOYTGMFUGC-UHFFFAOYSA-N 0.000 description 2
DGODCJUPOVOBKP-UHFFFAOYSA-N 1-benzyl-4-(4-methoxyphenyl)-3,6-dihydro-2h-pyridine Chemical compound C1=CC(OC)=CC=C1C(CC1)=CCN1CC1=CC=CC=C1 DGODCJUPOVOBKP-UHFFFAOYSA-N 0.000 description 2
AZKLLUOQRGMUAL-UHFFFAOYSA-N 1-benzyl-4-(4-methylphenyl)piperidin-3-ol Chemical compound C1=CC(C)=CC=C1C1C(O)CN(CC=2C=CC=CC=2)CC1 AZKLLUOQRGMUAL-UHFFFAOYSA-N 0.000 description 2
XSZMKTWZEOSWMR-UHFFFAOYSA-N 1-benzyl-4-[4-(2-hydroxyethyl)phenyl]piperidin-3-ol Chemical compound C1=CC(CCO)=CC=C1C1C(O)CN(CC=2C=CC=CC=2)CC1 XSZMKTWZEOSWMR-UHFFFAOYSA-N 0.000 description 2
YQNWVIPVOVXCHM-UHFFFAOYSA-N 1-benzyl-4-[4-(2-hydroxyethyl)phenyl]piperidin-4-ol Chemical compound C1=CC(CCO)=CC=C1C1(O)CCN(CC=2C=CC=CC=2)CC1 YQNWVIPVOVXCHM-UHFFFAOYSA-N 0.000 description 2
OYFGBYMODNFJND-UHFFFAOYSA-N 1-benzyl-4-[4-(hydroxymethyl)phenyl]piperidin-3-ol Chemical compound C1=CC(CO)=CC=C1C1C(O)CN(CC=2C=CC=CC=2)CC1 OYFGBYMODNFJND-UHFFFAOYSA-N 0.000 description 2
YWMACOLPZHNSRQ-UHFFFAOYSA-N 1-benzyl-4-[4-[2-(oxan-2-yloxy)ethyl]phenyl]piperidin-4-ol Chemical compound C1CC(O)(C=2C=CC(CCOC3OCCCC3)=CC=2)CCN1CC1=CC=CC=C1 YWMACOLPZHNSRQ-UHFFFAOYSA-N 0.000 description 2
CSGYCLHHNZPUOE-UHFFFAOYSA-N 2,2,2-trichloroethyl 3-(naphthalen-2-ylmethoxy)-4-[3-(2,2,2-trichloroethoxycarbonyloxy)phenyl]piperidine-1-carboxylate Chemical compound ClC(Cl)(Cl)COC(=O)OC1=CC=CC(C2C(CN(CC2)C(=O)OCC(Cl)(Cl)Cl)OCC=2C=C3C=CC=CC3=CC=2)=C1 CSGYCLHHNZPUOE-UHFFFAOYSA-N 0.000 description 2
MFSQJBYFVIRSNQ-UHFFFAOYSA-N 2,2,2-trichloroethyl 3-(naphthalen-2-ylmethoxy)-4-[3-[3-(pyridin-2-ylcarbamoyloxy)propoxy]phenyl]piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OCC(Cl)(Cl)Cl)CCC1C(C=1)=CC=CC=1OCCCOC(=O)NC1=CC=CC=N1 MFSQJBYFVIRSNQ-UHFFFAOYSA-N 0.000 description 2
WLTKKLRMBQAIID-UHFFFAOYSA-N 2,2,2-trichloroethyl 3-(naphthalen-2-ylmethoxy)-4-[4-[3-(pyridin-2-ylcarbamoyloxy)propoxy]phenyl]piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OCC(Cl)(Cl)Cl)CCC1C(C=C1)=CC=C1OCCCOC(=O)NC1=CC=CC=N1 WLTKKLRMBQAIID-UHFFFAOYSA-N 0.000 description 2
VLNFHXYAKDIVNJ-UHFFFAOYSA-N 2,2,2-trichloroethyl 4-(4-methoxyphenyl)-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(C(=O)OCC(Cl)(Cl)Cl)CC1 VLNFHXYAKDIVNJ-UHFFFAOYSA-N 0.000 description 2
PBJJNBDLSHSGMY-UHFFFAOYSA-N 2,2,2-trichloroethyl 4-[3-(2-carbamoyloxyethoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound NC(=O)OCCOC1=CC=CC(C2C(CN(CC2)C(=O)OCC(Cl)(Cl)Cl)OCC=2C=C3C=CC=CC3=CC=2)=C1 PBJJNBDLSHSGMY-UHFFFAOYSA-N 0.000 description 2
FDWIYDABJNPWBT-UHFFFAOYSA-N 2,2,2-trichloroethyl 4-[4-(2-carbamoyloxyethoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C1=CC(OCCOC(=O)N)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(C(=O)OCC(Cl)(Cl)Cl)CC1 FDWIYDABJNPWBT-UHFFFAOYSA-N 0.000 description 2
GGKLOTVVGQZECC-UHFFFAOYSA-N 2,2,2-trichloroethyl 4-[4-(2-hydroxyethoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C1=CC(OCCO)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(C(=O)OCC(Cl)(Cl)Cl)CC1 GGKLOTVVGQZECC-UHFFFAOYSA-N 0.000 description 2
JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 2
ZIIKCLODGCOQLO-UHFFFAOYSA-N 2-(bromomethyl)-3-methoxynaphthalene Chemical compound C1=CC=C2C=C(CBr)C(OC)=CC2=C1 ZIIKCLODGCOQLO-UHFFFAOYSA-N 0.000 description 2
QGXNHCXKWFNKCG-UHFFFAOYSA-N 2-(bromomethyl)benzonitrile Chemical compound BrCC1=CC=CC=C1C#N QGXNHCXKWFNKCG-UHFFFAOYSA-N 0.000 description 2
125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 description 2
KHQVQQIRFOORKH-UHFFFAOYSA-N 2-[4-(1-benzyl-3,6-dihydro-2h-pyridin-4-yl)phenyl]ethanol Chemical compound C1=CC(CCO)=CC=C1C(CC1)=CCN1CC1=CC=CC=C1 KHQVQQIRFOORKH-UHFFFAOYSA-N 0.000 description 2
HQUAGDCTSVPACV-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)-1-(2,2,2-trichloroethoxycarbonyl)piperidin-4-yl]phenoxy]ethyl morpholine-4-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OCC(Cl)(Cl)Cl)CCC1C(C=C1)=CC=C1OCCOC(=O)N1CCOCC1 HQUAGDCTSVPACV-UHFFFAOYSA-N 0.000 description 2
SOCOWNSJZAIPCR-UHFFFAOYSA-N 2-[[2-[[3-[[4-(4-fluorophenyl)piperidin-3-yl]oxymethyl]naphthalen-1-yl]oxymethyl]phenoxy]methoxy]ethyl-trimethylsilane Chemical compound C[Si](C)(C)CCOCOC1=CC=CC=C1COC1=CC(COC2C(CCNC2)C=2C=CC(F)=CC=2)=CC2=CC=CC=C12 SOCOWNSJZAIPCR-UHFFFAOYSA-N 0.000 description 2
JHWOWIMCORWISE-UHFFFAOYSA-N 2-[[3-[[1-benzyl-4-(4-fluorophenyl)piperidin-3-yl]oxymethyl]naphthalen-1-yl]oxymethoxy]ethyl-trimethylsilane Chemical compound C=1C2=CC=CC=C2C(OCOCC[Si](C)(C)C)=CC=1COC(C(CC1)C=2C=CC(F)=CC=2)CN1CC1=CC=CC=C1 JHWOWIMCORWISE-UHFFFAOYSA-N 0.000 description 2
SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
HXHFEKAWTYKRBS-UHFFFAOYSA-N 3-(1-benzofuran-5-ylmethoxy)-4-(4-fluorophenyl)piperidine-1-carboxylic acid Chemical compound C=1C=C2OC=CC2=CC=1COC1CN(C(=O)O)CCC1C1=CC=C(F)C=C1 HXHFEKAWTYKRBS-UHFFFAOYSA-N 0.000 description 2
DWZMFDSIMGSOPK-UHFFFAOYSA-N 3-(2,3-dihydro-1,4-benzodioxin-6-ylmethoxy)-4-(4-fluorophenyl)piperidine-1-carboxylic acid Chemical compound C=1C=C2OCCOC2=CC=1COC1CN(C(=O)O)CCC1C1=CC=C(F)C=C1 DWZMFDSIMGSOPK-UHFFFAOYSA-N 0.000 description 2
QULTWYFCLCBDNW-UHFFFAOYSA-N 3-(2,3-dihydro-1,4-benzodioxin-6-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidine Chemical compound C=1C=C(C2C(CNCC2)OCC=2C=C3OCCOC3=CC=2)C=CC=1OCCCOCC1=CC=CC=C1 QULTWYFCLCBDNW-UHFFFAOYSA-N 0.000 description 2
CNQCWYFDIQSALX-UHFFFAOYSA-N 3-(chloromethyl)pyridine Chemical compound ClCC1=CC=CN=C1 CNQCWYFDIQSALX-UHFFFAOYSA-N 0.000 description 2
WUAIVTZASDYIOE-UHFFFAOYSA-N 3-(methoxymethyl)-5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidine Chemical compound COCC1CNCC(OCC=2C=C3C=CC=CC3=CC=2)C1C(C=C1)=CC=C1OCCCOCC1=CC=CC=C1 WUAIVTZASDYIOE-UHFFFAOYSA-N 0.000 description 2
BOPLTGQXUHIQHA-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-(2-phenylsulfanylethoxy)phenyl]piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1OCCSC1=CC=CC=C1 BOPLTGQXUHIQHA-UHFFFAOYSA-N 0.000 description 2
JQPDZUHJNHLRKQ-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylsulfanylpropyl)phenyl]piperidine Chemical compound C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1CCCSC1=CC=CC=C1 JQPDZUHJNHLRKQ-UHFFFAOYSA-N 0.000 description 2
KDRHFQALQKJMER-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-(pyridin-2-ylcarbamoyloxymethyl)phenyl]piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1COC(=O)NC1=CC=CC=N1 KDRHFQALQKJMER-UHFFFAOYSA-N 0.000 description 2
IYCYMGADGMJRIG-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-[2-(1,2,4-triazol-1-yl)ethoxy]phenyl]piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1OCCN1C=NC=N1 IYCYMGADGMJRIG-UHFFFAOYSA-N 0.000 description 2
KLLSXZNJVRRXBH-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-[2-(thiophene-2-carbonyloxy)ethoxy]phenyl]piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1OCCOC(=O)C1=CC=CS1 KLLSXZNJVRRXBH-UHFFFAOYSA-N 0.000 description 2
OXTNCQMOKLOUAM-UHFFFAOYSA-N 3-Oxoglutaric acid Chemical class OC(=O)CC(=O)CC(O)=O OXTNCQMOKLOUAM-UHFFFAOYSA-N 0.000 description 2
OIOVXGGCZBNFSE-UHFFFAOYSA-N 3-[(1,4-dimethoxynaphthalen-2-yl)methoxy]-4-[4-[3-(2-methoxyphenoxy)propoxy]phenyl]piperidine Chemical compound COC1=CC=CC=C1OCCCOC1=CC=C(C2C(CNCC2)OCC=2C(=C3C=CC=CC3=C(OC)C=2)OC)C=C1 OIOVXGGCZBNFSE-UHFFFAOYSA-N 0.000 description 2
FZAFAUXIODKSBH-UHFFFAOYSA-N 3-[7-[[4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxymethyl]naphthalen-2-yl]oxypropane-1,2-diol Chemical compound C=1C2=CC(OCC(O)CO)=CC=C2C=CC=1COC1CNCCC1C(C=C1)=CC=C1OCCCOCC1=CC=CC=C1 FZAFAUXIODKSBH-UHFFFAOYSA-N 0.000 description 2
FMQGDGHNMKJAEZ-UHFFFAOYSA-N 3-[[4-(4-fluorophenyl)piperidin-3-yl]oxymethyl]naphthalen-2-ol Chemical compound OC1=CC2=CC=CC=C2C=C1COC1CNCCC1C1=CC=C(F)C=C1 FMQGDGHNMKJAEZ-UHFFFAOYSA-N 0.000 description 2
OYMGUVYYTDDNNE-UHFFFAOYSA-N 3-[[6-[[4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxymethyl]naphthalen-2-yl]methoxy]propane-1,2-diol Chemical compound C1=CC2=CC(COCC(O)CO)=CC=C2C=C1COC1CNCCC1C(C=C1)=CC=C1OCCCOCC1=CC=CC=C1 OYMGUVYYTDDNNE-UHFFFAOYSA-N 0.000 description 2
GMIBQBWHDQDVMJ-UHFFFAOYSA-N 3-[[7-[[4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxymethyl]naphthalen-2-yl]methoxy]propane-1,2-diol Chemical compound C=1C2=CC(COCC(O)CO)=CC=C2C=CC=1COC1CNCCC1C(C=C1)=CC=C1OCCCOCC1=CC=CC=C1 GMIBQBWHDQDVMJ-UHFFFAOYSA-N 0.000 description 2
HGZXQCCQZLSOPP-UHFFFAOYSA-N 3-amino-1-phenylpropan-1-one Chemical compound NCCC(=O)C1=CC=CC=C1 HGZXQCCQZLSOPP-UHFFFAOYSA-N 0.000 description 2
IHCCAYCGZOLTEU-UHFFFAOYSA-N 3-furoic acid Chemical compound OC(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-N 0.000 description 2
JCTJTECFHAJHIG-UHFFFAOYSA-N 3-hydroxy-4-[4-(trityloxymethyl)phenyl]piperidine-1-carboxylic acid Chemical compound OC1CN(C(O)=O)CCC1C(C=C1)=CC=C1COC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 JCTJTECFHAJHIG-UHFFFAOYSA-N 0.000 description 2
ZGWZBGFZKUOGCK-UHFFFAOYSA-N 3-hydroxy-4-phenylpiperidine-1-carboxylic acid Chemical compound OC1CN(C(O)=O)CCC1C1=CC=CC=C1 ZGWZBGFZKUOGCK-UHFFFAOYSA-N 0.000 description 2
RUQIUASLAXJZIE-UHFFFAOYSA-N 3-methoxybenzoyl chloride Chemical compound COC1=CC=CC(C(Cl)=O)=C1 RUQIUASLAXJZIE-UHFFFAOYSA-N 0.000 description 2
WOLQNVQBMXBCEI-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-1-benzylpiperidin-4-ol Chemical compound C1CC(O)(C=2C=C3OCOC3=CC=2)CCN1CC1=CC=CC=C1 WOLQNVQBMXBCEI-UHFFFAOYSA-N 0.000 description 2
TUOKSVYJOBACRD-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C1=C2OCOC2=CC(C2CCN(CC2OCC=2C=C3C=CC=CC3=CC=2)C(=O)O)=C1 TUOKSVYJOBACRD-UHFFFAOYSA-N 0.000 description 2
BUVSYWMKYNUAED-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-3-[(2-cyanophenyl)methoxy]piperidine-1-carboxylic acid Chemical compound C1N(C(=O)O)CCC(C=2C=C3OCOC3=CC=2)C1OCC1=CC=CC=C1C#N BUVSYWMKYNUAED-UHFFFAOYSA-N 0.000 description 2
VSBGYXLMXWFFBC-UHFFFAOYSA-N 4-(3-methoxycarbonylphenyl)-3-[(4-phenylmethoxynaphthalen-2-yl)methoxy]piperidine-1-carboxylic acid Chemical compound COC(=O)C1=CC=CC(C2C(CN(CC2)C(O)=O)OCC=2C=C3C=CC=CC3=C(OCC=3C=CC=CC=3)C=2)=C1 VSBGYXLMXWFFBC-UHFFFAOYSA-N 0.000 description 2
RXCHTAQKLLGDPX-UHFFFAOYSA-N 4-(4-chlorophenyl)-1-methyl-3-(naphthalen-2-ylmethoxy)piperidine Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C)CCC1C1=CC=C(Cl)C=C1 RXCHTAQKLLGDPX-UHFFFAOYSA-N 0.000 description 2
XYEJGPJYARWICG-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[(3-phenylmethoxyphenyl)methoxy]piperidine-1-carboxylic acid Chemical compound C1N(C(=O)O)CCC(C=2C=CC(F)=CC=2)C1OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 XYEJGPJYARWICG-UHFFFAOYSA-N 0.000 description 2
DONYTWVVCAEPKO-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[(4-hydroxynaphthalen-2-yl)methoxy]piperidine-1-carboxylic acid Chemical compound C=1C(O)=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C1=CC=C(F)C=C1 DONYTWVVCAEPKO-UHFFFAOYSA-N 0.000 description 2
GOSLNEVIPPEFKZ-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[(4-phenylmethoxynaphthalen-2-yl)methoxy]-5-propylpiperidine Chemical compound C=1C=C(F)C=CC=1C1C(CCC)CNCC1OCC(C=C1C=CC=CC1=1)=CC=1OCC1=CC=CC=C1 GOSLNEVIPPEFKZ-UHFFFAOYSA-N 0.000 description 2
OBJYRCISTWXUSY-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[(5-hydroxynaphthalen-2-yl)methoxy]piperidine-1-carboxylic acid Chemical compound C=1C=C2C(O)=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C1=CC=C(F)C=C1 OBJYRCISTWXUSY-UHFFFAOYSA-N 0.000 description 2
GYPRZUMOPISFLB-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[[4-(3-methoxypropoxy)naphthalen-2-yl]methoxy]piperidine-1-carboxylic acid Chemical compound C=1C2=CC=CC=C2C(OCCCOC)=CC=1COC1CN(C(O)=O)CCC1C1=CC=C(F)C=C1 GYPRZUMOPISFLB-UHFFFAOYSA-N 0.000 description 2
ADUHNAIOJWPQOB-UHFFFAOYSA-N 4-(4-methylphenyl)piperidin-3-ol Chemical compound C1=CC(C)=CC=C1C1C(O)CNCC1 ADUHNAIOJWPQOB-UHFFFAOYSA-N 0.000 description 2
QSDBXYQFVVQUSB-UHFFFAOYSA-N 4-[3-(fluoromethyl)phenyl]-3-[(4-phenylmethoxynaphthalen-2-yl)methoxy]piperidine-1-carboxylic acid Chemical compound C1N(C(=O)O)CCC(C=2C=C(CF)C=CC=2)C1OCC(C=C1C=CC=CC1=1)=CC=1OCC1=CC=CC=C1 QSDBXYQFVVQUSB-UHFFFAOYSA-N 0.000 description 2
CBEOPFXNZADZHQ-UHFFFAOYSA-N 4-[4-(2-benzoyloxyethoxy)phenyl]-3-[[4-[(2-methoxyphenyl)methoxy]naphthalen-2-yl]methoxy]piperidine-1-carboxylic acid Chemical compound COC1=CC=CC=C1COC1=CC(COC2C(CCN(C2)C(O)=O)C=2C=CC(OCCOC(=O)C=3C=CC=CC=3)=CC=2)=CC2=CC=CC=C12 CBEOPFXNZADZHQ-UHFFFAOYSA-N 0.000 description 2
PXWBXAGKXKICLD-UHFFFAOYSA-N 4-[4-(2-cyanoethyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C1=CC=C(CCC#N)C=C1 PXWBXAGKXKICLD-UHFFFAOYSA-N 0.000 description 2
FKAVKCAFNNFADS-UHFFFAOYSA-N 4-[4-(2-hydrazinyl-2-oxoethyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C1=CC(CC(=O)NN)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(C(O)=O)CC1 FKAVKCAFNNFADS-UHFFFAOYSA-N 0.000 description 2
IIUAKLZUKPBNAL-UHFFFAOYSA-N 4-[4-(2-hydroxyethoxy)phenyl]-3-[(4-hydroxynaphthalen-2-yl)methoxy]piperidine-1-carboxylic acid Chemical compound C1=CC(OCCO)=CC=C1C1C(OCC=2C=C3C=CC=CC3=C(O)C=2)CN(C(O)=O)CC1 IIUAKLZUKPBNAL-UHFFFAOYSA-N 0.000 description 2
YZCGDUOGHJBKKA-UHFFFAOYSA-N 4-[4-(2-hydroxyethoxy)phenyl]-3-[[4-[(2-methoxyphenyl)methoxy]naphthalen-2-yl]methoxy]piperidine-1-carboxylic acid Chemical compound COC1=CC=CC=C1COC1=CC(COC2C(CCN(C2)C(O)=O)C=2C=CC(OCCO)=CC=2)=CC2=CC=CC=C12 YZCGDUOGHJBKKA-UHFFFAOYSA-N 0.000 description 2
VRAJSGXEQJORRM-UHFFFAOYSA-N 4-[4-(2-methoxy-2-oxoethyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C1=CC(CC(=O)OC)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(C(O)=O)CC1 VRAJSGXEQJORRM-UHFFFAOYSA-N 0.000 description 2
JKUOWLKOGSOKCF-UHFFFAOYSA-N 4-[4-(3-ethoxy-3-oxoprop-1-enyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C1=CC(C=CC(=O)OCC)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(C(O)=O)CC1 JKUOWLKOGSOKCF-UHFFFAOYSA-N 0.000 description 2
YKHMZASVWOPUAW-UHFFFAOYSA-N 4-[4-(3-ethoxy-3-oxopropyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C1=CC(CCC(=O)OCC)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(C(O)=O)CC1 YKHMZASVWOPUAW-UHFFFAOYSA-N 0.000 description 2
AIDNZGIOVINOTG-UHFFFAOYSA-N 4-[4-(3-hydroxyprop-1-enyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C1=CC(C=CCO)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(C(O)=O)CC1 AIDNZGIOVINOTG-UHFFFAOYSA-N 0.000 description 2
LSAYDEITTIFZAF-UHFFFAOYSA-N 4-[4-(4-methoxy-4-phenylbutoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C=1C=C(C2C(CN(CC2)C(O)=O)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCCC(OC)C1=CC=CC=C1 LSAYDEITTIFZAF-UHFFFAOYSA-N 0.000 description 2
BSZIEIBCKWATPF-UHFFFAOYSA-N 4-[4-(hydroxymethyl)phenyl]piperidin-3-ol Chemical compound C1=CC(CO)=CC=C1C1C(O)CNCC1 BSZIEIBCKWATPF-UHFFFAOYSA-N 0.000 description 2
LNMVSETTYLGJAO-UHFFFAOYSA-N 4-[4-[2-(2-methylsulfanylbenzoyl)oxyethoxy]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound CSC1=CC=CC=C1C(=O)OCCOC1=CC=C(C2C(CN(CC2)C(O)=O)OCC=2C=C3C=CC=CC3=CC=2)C=C1 LNMVSETTYLGJAO-UHFFFAOYSA-N 0.000 description 2
XHLINERPARVVBX-UHFFFAOYSA-N 4-[4-[3-(1-benzothiophen-5-ylmethoxy)piperidin-4-yl]phenoxy]-1-phenylbutan-1-one Chemical compound C=1C=C(C2C(CNCC2)OCC=2C=C3C=CSC3=CC=2)C=CC=1OCCCC(=O)C1=CC=CC=C1 XHLINERPARVVBX-UHFFFAOYSA-N 0.000 description 2
UJNVXFOUYGZUOX-UHFFFAOYSA-N 4-[4-[3-(2,3-dihydro-1h-inden-5-ylmethoxy)piperidin-4-yl]phenoxy]-1-phenylbutan-1-one Chemical compound C=1C=C(C2C(CNCC2)OCC=2C=C3CCCC3=CC=2)C=CC=1OCCCC(=O)C1=CC=CC=C1 UJNVXFOUYGZUOX-UHFFFAOYSA-N 0.000 description 2
USHADBBRWTVXSK-UHFFFAOYSA-N 4-[4-[3-(methylamino)propoxy]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C1=CC(OCCCNC)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(C(O)=O)CC1 USHADBBRWTVXSK-UHFFFAOYSA-N 0.000 description 2
FGVHWMUZVQOVKU-UHFFFAOYSA-N 4-[4-[3-[(4-hydroxynaphthalen-2-yl)methoxy]piperidin-4-yl]phenoxy]-1-phenylbutan-1-one Chemical compound C=1C2=CC=CC=C2C(O)=CC=1COC1CNCCC1C(C=C1)=CC=C1OCCCC(=O)C1=CC=CC=C1 FGVHWMUZVQOVKU-UHFFFAOYSA-N 0.000 description 2
OVADVZVMJGPKAT-UHFFFAOYSA-N 4-cyclohexyl-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C1CCCCC1 OVADVZVMJGPKAT-UHFFFAOYSA-N 0.000 description 2
FOQVMHRXEHFCNW-UHFFFAOYSA-N 5-(bromomethyl)-1-benzothiophene Chemical compound BrCC1=CC=C2SC=CC2=C1 FOQVMHRXEHFCNW-UHFFFAOYSA-N 0.000 description 2
UNIHNYUCROCRPH-UHFFFAOYSA-N 5-[(4-methoxyphenyl)methoxy]-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-ol Chemical compound C1=CC(OC)=CC=C1COC1C(C=2C=CC(OCCCOCC=3C=CC=CC=3)=CC=2)C(O)CNC1 UNIHNYUCROCRPH-UHFFFAOYSA-N 0.000 description 2
UVADKWYZZBPGTB-UHFFFAOYSA-N 6-(bromomethyl)isoquinoline;hydrobromide Chemical compound Br.C1=NC=CC2=CC(CBr)=CC=C21 UVADKWYZZBPGTB-UHFFFAOYSA-N 0.000 description 2
OSRARURJYPOUOV-UHFFFAOYSA-N 6-methylquinoxaline Chemical compound N1=CC=NC2=CC(C)=CC=C21 OSRARURJYPOUOV-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
125000006847 BOC protecting group Chemical group 0.000 description 2
239000005711 Benzoic acid Substances 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 2
DIWVBIXQCNRCFE-UHFFFAOYSA-N DL-alpha-Methoxyphenylacetic acid Chemical compound COC(C(O)=O)C1=CC=CC=C1 DIWVBIXQCNRCFE-UHFFFAOYSA-N 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
RPTUSVTUFVMDQK-UHFFFAOYSA-N Hidralazin Chemical compound C1=CC=C2C(NN)=NN=CC2=C1 RPTUSVTUFVMDQK-UHFFFAOYSA-N 0.000 description 2
101000579218 Homo sapiens Renin Proteins 0.000 description 2
WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical compound O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 description 2
239000005864 Sulphur Substances 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
JCMCCXIQKZLWMV-UHFFFAOYSA-N [6-(2-trimethylsilylethoxymethoxy)naphthalen-2-yl]methanol Chemical compound C1=C(CO)C=CC2=CC(OCOCC[Si](C)(C)C)=CC=C21 JCMCCXIQKZLWMV-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
125000004450 alkenylene group Chemical group 0.000 description 2
150000001346 alkyl aryl ethers Chemical class 0.000 description 2
125000004419 alkynylene group Chemical group 0.000 description 2
150000004808 allyl alcohols Chemical class 0.000 description 2
BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
150000004645 aluminates Chemical class 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
235000010233 benzoic acid Nutrition 0.000 description 2
RROBIDXNTUAHFW-UHFFFAOYSA-N benzotriazol-1-yloxy-tris(dimethylamino)phosphanium Chemical compound C1=CC=C2N(O[P+](N(C)C)(N(C)C)N(C)C)N=NC2=C1 RROBIDXNTUAHFW-UHFFFAOYSA-N 0.000 description 2
239000004327 boric acid Substances 0.000 description 2
MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 2
238000005661 deetherification reaction Methods 0.000 description 2
AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 description 2
238000005906 dihydroxylation reaction Methods 0.000 description 2
150000002009 diols Chemical class 0.000 description 2
LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000002255 enzymatic effect Effects 0.000 description 2
GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 2
NJCAEIMHWVLHBX-UHFFFAOYSA-N ethyl 4-(2-trimethylsilylethoxymethoxy)naphthalene-2-carboxylate Chemical compound C1=CC=CC2=CC(C(=O)OCC)=CC(OCOCC[Si](C)(C)C)=C21 NJCAEIMHWVLHBX-UHFFFAOYSA-N 0.000 description 2
QMCMRBCASLXWFT-UHFFFAOYSA-N ethyl 4-hydroxynaphthalene-2-carboxylate Chemical compound C1=CC=CC2=CC(C(=O)OCC)=CC(O)=C21 QMCMRBCASLXWFT-UHFFFAOYSA-N 0.000 description 2
HFBCYSDXUCTZDV-UHFFFAOYSA-N ethyl 4-phenylmethoxynaphthalene-2-carboxylate Chemical compound C=12C=CC=CC2=CC(C(=O)OCC)=CC=1OCC1=CC=CC=C1 HFBCYSDXUCTZDV-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000003925 fat Substances 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
238000007031 hydroxymethylation reaction Methods 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
229910052500 inorganic mineral Inorganic materials 0.000 description 2
XIRLIZNMBKEUDD-UHFFFAOYSA-N isoquinolin-6-ylmethanol Chemical compound C1=NC=CC2=CC(CO)=CC=C21 XIRLIZNMBKEUDD-UHFFFAOYSA-N 0.000 description 2
210000003734 kidney Anatomy 0.000 description 2
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 2
229910052808 lithium carbonate Inorganic materials 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
MHCFAGZWMAWTNR-UHFFFAOYSA-M lithium perchlorate Chemical compound [Li+].[O-]Cl(=O)(=O)=O MHCFAGZWMAWTNR-UHFFFAOYSA-M 0.000 description 2
229910001486 lithium perchlorate Inorganic materials 0.000 description 2
229940118019 malondialdehyde Drugs 0.000 description 2
IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
SDXVIIWTDAOZNC-UHFFFAOYSA-N methyl 2-(2-trimethylsilylethoxymethoxy)benzoate Chemical compound COC(=O)C1=CC=CC=C1OCOCC[Si](C)(C)C SDXVIIWTDAOZNC-UHFFFAOYSA-N 0.000 description 2
RNZWRMPZWONDRK-UHFFFAOYSA-N methyl 7-(2-trimethylsilylethoxymethoxy)naphthalene-2-carboxylate Chemical compound C1=CC(OCOCC[Si](C)(C)C)=CC2=CC(C(=O)OC)=CC=C21 RNZWRMPZWONDRK-UHFFFAOYSA-N 0.000 description 2
QEXDKAQVYPQVSE-UHFFFAOYSA-N methyl 8-(2-trimethylsilylethoxymethoxy)naphthalene-2-carboxylate Chemical compound C1=CC=C(OCOCC[Si](C)(C)C)C2=CC(C(=O)OC)=CC=C21 QEXDKAQVYPQVSE-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
239000011707 mineral Substances 0.000 description 2
238000006011 modification reaction Methods 0.000 description 2
XMWFMEYDRNJSOO-UHFFFAOYSA-N morpholine-4-carbonyl chloride Chemical compound ClC(=O)N1CCOCC1 XMWFMEYDRNJSOO-UHFFFAOYSA-N 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical class CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 2
229960003512 nicotinic acid Drugs 0.000 description 2
235000001968 nicotinic acid Nutrition 0.000 description 2
239000011664 nicotinic acid Substances 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
150000002902 organometallic compounds Chemical class 0.000 description 2
239000012285 osmium tetroxide Substances 0.000 description 2
229910000489 osmium tetroxide Inorganic materials 0.000 description 2
230000001590 oxidative effect Effects 0.000 description 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
230000036961 partial effect Effects 0.000 description 2
150000004707 phenolate Chemical class 0.000 description 2
229910000073 phosphorus hydride Inorganic materials 0.000 description 2
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 2
VDVJGIYXDVPQLP-UHFFFAOYSA-N piperonylic acid Chemical compound OC(=O)C1=CC=C2OCOC2=C1 VDVJGIYXDVPQLP-UHFFFAOYSA-N 0.000 description 2
239000011591 potassium Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
150000003138 primary alcohols Chemical class 0.000 description 2
AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 2
239000003586 protic polar solvent Substances 0.000 description 2
NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 description 2
238000003127 radioimmunoassay Methods 0.000 description 2
239000012217 radiopharmaceutical Substances 0.000 description 2
229940121896 radiopharmaceutical Drugs 0.000 description 2
230000002799 radiopharmaceutical effect Effects 0.000 description 2
229910052703 rhodium Inorganic materials 0.000 description 2
239000010948 rhodium Substances 0.000 description 2
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
238000007127 saponification reaction Methods 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 2
239000011877 solvent mixture Substances 0.000 description 2
239000000758 substrate Substances 0.000 description 2
150000003457 sulfones Chemical class 0.000 description 2
239000000829 suppository Substances 0.000 description 2
ZGZZDPKVGNGSAJ-UHFFFAOYSA-N tert-butyl 3-(1-benzothiophen-5-ylmethoxy)-4-(4-fluorophenyl)piperidine-1-carboxylate Chemical compound C=1C=C2SC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(F)C=C1 ZGZZDPKVGNGSAJ-UHFFFAOYSA-N 0.000 description 2
ALNFNNNTLXPSLW-UHFFFAOYSA-N tert-butyl 3-(naphthalen-2-ylmethoxy)-4-[4-(2-phenoxyethyl)phenyl]piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1CCOC1=CC=CC=C1 ALNFNNNTLXPSLW-UHFFFAOYSA-N 0.000 description 2
UWZTYXRIEUWRBJ-UHFFFAOYSA-N tert-butyl 3-(naphthalen-2-ylmethoxy)-4-[4-(3-oxo-3-phenylpropyl)phenyl]piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1CCC(=O)C1=CC=CC=C1 UWZTYXRIEUWRBJ-UHFFFAOYSA-N 0.000 description 2
PXDIDQNZHUXVFA-UHFFFAOYSA-N tert-butyl 3-(naphthalen-2-ylmethoxy)-4-[4-(naphthalen-2-ylmethoxymethyl)phenyl]piperidine-1-carboxylate Chemical compound C1=CC=CC2=CC(COCC3=CC=C(C=C3)C3CCN(CC3OCC=3C=C4C=CC=CC4=CC=3)C(=O)OC(C)(C)C)=CC=C21 PXDIDQNZHUXVFA-UHFFFAOYSA-N 0.000 description 2
LZQNCVTYSUJYMH-UHFFFAOYSA-N tert-butyl 3-(naphthalen-2-ylmethoxy)-4-[4-[3-(2-phenyl-1,3-dioxolan-2-yl)propoxy]phenyl]piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1OCCCC1(C=2C=CC=CC=2)OCCO1 LZQNCVTYSUJYMH-UHFFFAOYSA-N 0.000 description 2
PYJPIRJFBVPUBP-UHFFFAOYSA-N tert-butyl 3-[(1-methoxynaphthalen-2-yl)methoxy]-4-[4-(2-phenoxyethyl)phenyl]piperidine-1-carboxylate Chemical compound C1=CC2=CC=CC=C2C(OC)=C1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1CCOC1=CC=CC=C1 PYJPIRJFBVPUBP-UHFFFAOYSA-N 0.000 description 2
AEUYNLGARTWIIF-UHFFFAOYSA-N tert-butyl 3-[(4-methoxyphenyl)methoxy]-4-(4-methylphenyl)piperidine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1COC1C(C=2C=CC(C)=CC=2)CCN(C(=O)OC(C)(C)C)C1 AEUYNLGARTWIIF-UHFFFAOYSA-N 0.000 description 2
OXEDCRUNMDAUPS-UHFFFAOYSA-N tert-butyl 3-[(4-methoxyphenyl)methoxy]-4-[3-(trifluoromethyl)phenyl]piperidine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1COC1C(C=2C=C(C=CC=2)C(F)(F)F)CCN(C(=O)OC(C)(C)C)C1 OXEDCRUNMDAUPS-UHFFFAOYSA-N 0.000 description 2
PFQANSJALXAQFT-UHFFFAOYSA-N tert-butyl 3-[[2-(aminomethyl)phenyl]methoxy]-4-phenylpiperidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C=CC=CC=2)C1OCC1=CC=CC=C1CN PFQANSJALXAQFT-UHFFFAOYSA-N 0.000 description 2
HVKZLUGLKTVPDJ-UHFFFAOYSA-N tert-butyl 3-hydroxy-4-(3-methoxycarbonylphenyl)piperidine-1-carboxylate Chemical compound COC(=O)C1=CC=CC(C2C(CN(CC2)C(=O)OC(C)(C)C)O)=C1 HVKZLUGLKTVPDJ-UHFFFAOYSA-N 0.000 description 2
JDKNNWOXJUGUBM-UHFFFAOYSA-N tert-butyl 3-hydroxy-4-(4-methoxycarbonylphenyl)piperidine-1-carboxylate Chemical compound C1=CC(C(=O)OC)=CC=C1C1C(O)CN(C(=O)OC(C)(C)C)CC1 JDKNNWOXJUGUBM-UHFFFAOYSA-N 0.000 description 2
FYTOCUHAQHZOGJ-UHFFFAOYSA-N tert-butyl 3-hydroxy-4-(4-phenylmethoxyphenyl)piperidine-1-carboxylate Chemical compound OC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1OCC1=CC=CC=C1 FYTOCUHAQHZOGJ-UHFFFAOYSA-N 0.000 description 2
ARBOKZRMOAKEBR-UHFFFAOYSA-N tert-butyl 3-hydroxy-4-[4-(hydroxymethyl)phenyl]piperidine-1-carboxylate Chemical compound OC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(CO)C=C1 ARBOKZRMOAKEBR-UHFFFAOYSA-N 0.000 description 2
ZVKOCRMICMFQAT-UHFFFAOYSA-N tert-butyl 4-(3-bromophenyl)-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=CC(Br)=C1 ZVKOCRMICMFQAT-UHFFFAOYSA-N 0.000 description 2
YAJXSLUCCNXMES-UHFFFAOYSA-N tert-butyl 4-(3-bromophenyl)-3-hydroxypiperidine-1-carboxylate Chemical compound OC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=CC(Br)=C1 YAJXSLUCCNXMES-UHFFFAOYSA-N 0.000 description 2
KIHPIQPZCQTRHF-UHFFFAOYSA-N tert-butyl 4-(3-methoxycarbonylphenyl)-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound COC(=O)C1=CC=CC(C2C(CN(CC2)C(=O)OC(C)(C)C)OCC=2C=C3C=CC=CC3=CC=2)=C1 KIHPIQPZCQTRHF-UHFFFAOYSA-N 0.000 description 2
WGVNXGZMMOTHEG-UHFFFAOYSA-N tert-butyl 4-(4-chlorophenyl)-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C=CC(Cl)=CC=2)=C1 WGVNXGZMMOTHEG-UHFFFAOYSA-N 0.000 description 2
HCXQLAOLEFZTMI-UHFFFAOYSA-N tert-butyl 4-(4-cyanophenyl)-3-[[4-(2-trimethylsilylethoxymethoxy)naphthalen-2-yl]methoxy]piperidine-1-carboxylate Chemical compound C=1C(OCOCC[Si](C)(C)C)=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(C#N)C=C1 HCXQLAOLEFZTMI-UHFFFAOYSA-N 0.000 description 2
OZENVXDMYWXOIX-UHFFFAOYSA-N tert-butyl 4-(4-fluorophenyl)-3-[(4-methoxyphenyl)methoxy]piperidine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1COC1C(C=2C=CC(F)=CC=2)CCN(C(=O)OC(C)(C)C)C1 OZENVXDMYWXOIX-UHFFFAOYSA-N 0.000 description 2
YLGHBIGZUPHLNC-UHFFFAOYSA-N tert-butyl 4-(4-fluorophenyl)-3-[[3-(2-trimethylsilylethoxymethoxy)naphthalen-2-yl]methoxy]piperidine-1-carboxylate Chemical compound C=1C2=CC=CC=C2C=C(OCOCC[Si](C)(C)C)C=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(F)C=C1 YLGHBIGZUPHLNC-UHFFFAOYSA-N 0.000 description 2
QIKXYLSJWIVRGV-UHFFFAOYSA-N tert-butyl 4-[3-(hydroxymethyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=CC(CO)=C1 QIKXYLSJWIVRGV-UHFFFAOYSA-N 0.000 description 2
QRTUNSDVVDQRND-UHFFFAOYSA-N tert-butyl 4-[4-(2-methylsulfonyloxyethoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(OCCOS(C)(=O)=O)C=C1 QRTUNSDVVDQRND-UHFFFAOYSA-N 0.000 description 2
PUNCNWYRXSXNIB-UHFFFAOYSA-N tert-butyl 4-[4-(2-phenylmethoxyethoxy)phenyl]-3-[(4-phenylmethoxynaphthalen-2-yl)methoxy]piperidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C=CC(OCCOCC=3C=CC=CC=3)=CC=2)C1OCC(C=C1C=CC=CC1=1)=CC=1OCC1=CC=CC=C1 PUNCNWYRXSXNIB-UHFFFAOYSA-N 0.000 description 2
JJSQHYHSTKMBAA-UHFFFAOYSA-N tert-butyl 4-[4-(3-ethoxy-3-oxoprop-1-enyl)phenyl]-3-hydroxypiperidine-1-carboxylate Chemical compound C1=CC(C=CC(=O)OCC)=CC=C1C1C(O)CN(C(=O)OC(C)(C)C)CC1 JJSQHYHSTKMBAA-UHFFFAOYSA-N 0.000 description 2
CLCDHBTWXKRQHA-UHFFFAOYSA-N tert-butyl 4-[4-(3-methylsulfonyloxypropoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(OCCCOS(C)(=O)=O)C=C1 CLCDHBTWXKRQHA-UHFFFAOYSA-N 0.000 description 2
HCQMMDKRIBSQDS-UHFFFAOYSA-N tert-butyl 4-[4-[2-(4-chlorobenzoyl)oxyethoxy]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1OCCOC(=O)C1=CC=C(Cl)C=C1 HCQMMDKRIBSQDS-UHFFFAOYSA-N 0.000 description 2
HECJFCWRAPPSOX-UHFFFAOYSA-N tert-butyl 4-[4-[2-(benzenesulfonyl)ethoxy]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1OCCS(=O)(=O)C1=CC=CC=C1 HECJFCWRAPPSOX-UHFFFAOYSA-N 0.000 description 2
KDSDBBPVYBVAKS-UHFFFAOYSA-N tert-butyl 4-[4-[2-(benzenesulfonyl)ethyl]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1CCS(=O)(=O)C1=CC=CC=C1 KDSDBBPVYBVAKS-UHFFFAOYSA-N 0.000 description 2
AHFWVSWAJVIUGE-UHFFFAOYSA-N tert-butyl 4-[4-[2-(cyclopropanecarbonyloxy)ethyl]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1CCOC(=O)C1CC1 AHFWVSWAJVIUGE-UHFFFAOYSA-N 0.000 description 2
PYZDXROLWBLZBN-UHFFFAOYSA-N tert-butyl 4-[4-[2-(furan-2-carbonyloxy)ethoxy]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1OCCOC(=O)C1=CC=CO1 PYZDXROLWBLZBN-UHFFFAOYSA-N 0.000 description 2
QVXYGWGMCJFZNZ-UHFFFAOYSA-N tert-butyl 4-cyclohexyl-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1CCCCC1 QVXYGWGMCJFZNZ-UHFFFAOYSA-N 0.000 description 2
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 2
125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
150000003568 thioethers Chemical class 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
150000003606 tin compounds Chemical class 0.000 description 2
230000009466 transformation Effects 0.000 description 2
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 2
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 2
238000005866 tritylation reaction Methods 0.000 description 2
239000002966 varnish Substances 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
239000000052 vinegar Substances 0.000 description 2
235000021419 vinegar Nutrition 0.000 description 2
239000001993 wax Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
PAXWODJTHKJQDZ-VHSXEESVSA-N (1r,4s)-1,7,7-trimethyl-2-oxo-3-oxabicyclo[2.2.1]heptane-4-carbonyl chloride Chemical compound C1C[C@]2(C(Cl)=O)OC(=O)[C@@]1(C)C2(C)C PAXWODJTHKJQDZ-VHSXEESVSA-N 0.000 description 1
UDEQFYWNFHWPRH-UHFFFAOYSA-N (2-carbonochloridoylphenyl)methyl benzoate Chemical compound ClC(=O)C1=CC=CC=C1COC(=O)C1=CC=CC=C1 UDEQFYWNFHWPRH-UHFFFAOYSA-N 0.000 description 1
SGFGPRQNDOOJQC-WCUKECLNSA-N (2r)-3-[2-[7-[[(3r,4r)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxymethyl]naphthalen-2-yl]oxyethoxy]propane-1,2-diol Chemical compound C1=CC([C@H]2CCNC[C@@H]2OCC=2C=CC3=CC=C(C=C3C=2)OCCOC[C@H](O)CO)=CC=C1OCCCOCC1=CC=CC=C1 SGFGPRQNDOOJQC-WCUKECLNSA-N 0.000 description 1
OYMGUVYYTDDNNE-VWXDNAKMSA-N (2r)-3-[[6-[[(3r,4r)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxymethyl]naphthalen-2-yl]methoxy]propane-1,2-diol Chemical compound C1=CC([C@H]2CCNC[C@@H]2OCC2=CC3=CC=C(C=C3C=C2)COC[C@H](O)CO)=CC=C1OCCCOCC1=CC=CC=C1 OYMGUVYYTDDNNE-VWXDNAKMSA-N 0.000 description 1
GMIBQBWHDQDVMJ-VWXDNAKMSA-N (2r)-3-[[7-[[(3r,4r)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxymethyl]naphthalen-2-yl]methoxy]propane-1,2-diol Chemical compound C1=CC([C@H]2CCNC[C@@H]2OCC=2C=CC3=CC=C(C=C3C=2)COC[C@H](O)CO)=CC=C1OCCCOCC1=CC=CC=C1 GMIBQBWHDQDVMJ-VWXDNAKMSA-N 0.000 description 1
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
YKFCISHFRZHKHY-NGQGLHOPSA-N (2s)-2-amino-3-(3,4-dihydroxyphenyl)-2-methylpropanoic acid;trihydrate Chemical compound O.O.O.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1.OC(=O)[C@](N)(C)CC1=CC=C(O)C(O)=C1 YKFCISHFRZHKHY-NGQGLHOPSA-N 0.000 description 1
SGFGPRQNDOOJQC-DLTAMOENSA-N (2s)-3-[2-[7-[[(3r,4r)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxymethyl]naphthalen-2-yl]oxyethoxy]propane-1,2-diol Chemical compound C1=CC([C@H]2CCNC[C@@H]2OCC=2C=CC3=CC=C(C=C3C=2)OCCOC[C@@H](O)CO)=CC=C1OCCCOCC1=CC=CC=C1 SGFGPRQNDOOJQC-DLTAMOENSA-N 0.000 description 1
OYMGUVYYTDDNNE-GSGZQRTFSA-N (2s)-3-[[6-[[(3r,4r)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxymethyl]naphthalen-2-yl]methoxy]propane-1,2-diol Chemical compound C1=CC([C@H]2CCNC[C@@H]2OCC2=CC3=CC=C(C=C3C=C2)COC[C@@H](O)CO)=CC=C1OCCCOCC1=CC=CC=C1 OYMGUVYYTDDNNE-GSGZQRTFSA-N 0.000 description 1
GMIBQBWHDQDVMJ-GSGZQRTFSA-N (2s)-3-[[7-[[(3r,4r)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxymethyl]naphthalen-2-yl]methoxy]propane-1,2-diol Chemical compound C1=CC([C@H]2CCNC[C@@H]2OCC=2C=CC3=CC=C(C=C3C=2)COC[C@@H](O)CO)=CC=C1OCCCOCC1=CC=CC=C1 GMIBQBWHDQDVMJ-GSGZQRTFSA-N 0.000 description 1
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
GKCHUTZTJAFTHQ-JXFVGPSASA-N (3s,4s,5r)-5-[(1,4-dimethoxynaphthalen-2-yl)methoxy]-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-ol Chemical compound C1=CC([C@H]2[C@H](O)CNC[C@@H]2OCC=2C=C(C3=CC=CC=C3C=2OC)OC)=CC=C1OCCCOCC1=CC=CC=C1 GKCHUTZTJAFTHQ-JXFVGPSASA-N 0.000 description 1
YAYWBPOXJMPJGF-RDKKHIPBSA-N (3s,4s,5r)-5-[(1,4-dimethoxynaphthalen-2-yl)methoxy]-4-[4-[3-[(2-methoxyphenyl)methoxy]propoxy]phenyl]piperidin-3-ol Chemical compound COC1=CC=CC=C1COCCCOC1=CC=C([C@@H]2[C@H](CNC[C@H]2O)OCC=2C(=C3C=CC=CC3=C(OC)C=2)OC)C=C1 YAYWBPOXJMPJGF-RDKKHIPBSA-N 0.000 description 1
METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 description 1
IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 description 1
TWBNMYSKRDRHAT-RCWTXCDDSA-N (S)-timolol hemihydrate Chemical compound O.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1.CC(C)(C)NC[C@H](O)COC1=NSN=C1N1CCOCC1 TWBNMYSKRDRHAT-RCWTXCDDSA-N 0.000 description 1
SYSZENVIJHPFNL-UHFFFAOYSA-N (alpha-D-mannosyl)7-beta-D-mannosyl-diacetylchitobiosyl-L-asparagine, isoform B (protein) Chemical compound COC1=CC=C(I)C=C1 SYSZENVIJHPFNL-UHFFFAOYSA-N 0.000 description 1
GRZHHTYDZVRPIC-UHFFFAOYSA-N (benzyloxy)acetic acid Chemical compound OC(=O)COCC1=CC=CC=C1 GRZHHTYDZVRPIC-UHFFFAOYSA-N 0.000 description 1
KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
150000008083 1,2,3,6-tetrahydropyridines Chemical class 0.000 description 1
FMGGHNGKHRCJLL-UHFFFAOYSA-N 1,2-bis(chloromethyl)benzene Chemical compound ClCC1=CC=CC=C1CCl FMGGHNGKHRCJLL-UHFFFAOYSA-N 0.000 description 1
JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 1
SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
XKFWNKQOVRNGIJ-UHFFFAOYSA-N 1-(2-trimethylsilylethoxymethoxy)naphthalene-2-carboxylic acid Chemical compound C[Si](C)(C)CCOCOC1=C(C=CC2=CC=CC=C21)C(=O)O XKFWNKQOVRNGIJ-UHFFFAOYSA-N 0.000 description 1
QZNQSIHCDAGZIA-UHFFFAOYSA-N 1-(bromomethyl)-4-tert-butylbenzene Chemical compound CC(C)(C)C1=CC=C(CBr)C=C1 QZNQSIHCDAGZIA-UHFFFAOYSA-N 0.000 description 1
RZJGKPNCYQZFGR-UHFFFAOYSA-N 1-(bromomethyl)naphthalene Chemical compound C1=CC=C2C(CBr)=CC=CC2=C1 RZJGKPNCYQZFGR-UHFFFAOYSA-N 0.000 description 1
MKXVKELDRLNWGV-UHFFFAOYSA-N 1-(chloromethyl)-3-phenylmethoxybenzene Chemical compound ClCC1=CC=CC(OCC=2C=CC=CC=2)=C1 MKXVKELDRLNWGV-UHFFFAOYSA-N 0.000 description 1
IATNZRYVIRYKDJ-UHFFFAOYSA-N 1-(chloromethyl)-4-phenoxybenzene Chemical compound C1=CC(CCl)=CC=C1OC1=CC=CC=C1 IATNZRYVIRYKDJ-UHFFFAOYSA-N 0.000 description 1
HLQZCRVEEQKNMS-UHFFFAOYSA-N 1-(chloromethyl)-4-phenylbenzene Chemical group C1=CC(CCl)=CC=C1C1=CC=CC=C1 HLQZCRVEEQKNMS-UHFFFAOYSA-N 0.000 description 1
OBPFLVNGKXWSPT-UHFFFAOYSA-N 1-[[5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]methyl]imidazolidin-2-one Chemical group O=C1NCCN1CC1C(C=2C=CC(OCCCOCC=3C=CC=CC=3)=CC=2)C(OCC=2C=C3C=CC=CC3=CC=2)CNC1 OBPFLVNGKXWSPT-UHFFFAOYSA-N 0.000 description 1
GFMKWVHCFWDCGU-UHFFFAOYSA-N 1-benzyl-3-(naphthalen-2-ylmethoxy)-4-[3-[3-(oxan-2-yloxy)propoxy]phenyl]piperidine Chemical compound C=1C=CC(C2C(CN(CC=3C=CC=CC=3)CC2)OCC=2C=C3C=CC=CC3=CC=2)=CC=1OCCCOC1CCCCO1 GFMKWVHCFWDCGU-UHFFFAOYSA-N 0.000 description 1
QXZBWXNTDCLOQP-UHFFFAOYSA-N 1-benzyl-4-(1,2-dihydroacenaphthylen-5-yl)-3,6-dihydro-2h-pyridine Chemical compound C1CC(C=2C=3C=CC=C4CCC(C=34)=CC=2)=CCN1CC1=CC=CC=C1 QXZBWXNTDCLOQP-UHFFFAOYSA-N 0.000 description 1
BQGPKXGTRDXORC-UHFFFAOYSA-N 1-benzyl-4-(1,2-dihydroacenaphthylen-5-yl)piperidin-4-ol Chemical compound C1CC(O)(C=2C=3C=CC=C4CCC(C=34)=CC=2)CCN1CC1=CC=CC=C1 BQGPKXGTRDXORC-UHFFFAOYSA-N 0.000 description 1
ZNVAJJDHKBCQES-UHFFFAOYSA-N 1-benzyl-4-(2-fluorophenyl)-3,6-dihydro-2h-pyridine Chemical compound FC1=CC=CC=C1C(CC1)=CCN1CC1=CC=CC=C1 ZNVAJJDHKBCQES-UHFFFAOYSA-N 0.000 description 1
DYIFQINSHWHQSY-UHFFFAOYSA-N 1-benzyl-4-(2-fluorophenyl)piperidin-4-ol Chemical compound C1CC(O)(C=2C(=CC=CC=2)F)CCN1CC1=CC=CC=C1 DYIFQINSHWHQSY-UHFFFAOYSA-N 0.000 description 1
ZTGJVEWQUBETBR-UHFFFAOYSA-N 1-benzyl-4-(3,4-dimethoxyphenyl)-3,6-dihydro-2h-pyridine Chemical compound C1=C(OC)C(OC)=CC=C1C(CC1)=CCN1CC1=CC=CC=C1 ZTGJVEWQUBETBR-UHFFFAOYSA-N 0.000 description 1
CYGSPEZWUWAFQL-UHFFFAOYSA-N 1-benzyl-4-(3-bromophenyl)piperidin-4-ol Chemical compound C1CC(O)(C=2C=C(Br)C=CC=2)CCN1CC1=CC=CC=C1 CYGSPEZWUWAFQL-UHFFFAOYSA-N 0.000 description 1
QQHKQZSDGCYPOJ-UHFFFAOYSA-N 1-benzyl-4-(3-fluorophenyl)-3,6-dihydro-2h-pyridine Chemical compound FC1=CC=CC(C=2CCN(CC=3C=CC=CC=3)CC=2)=C1 QQHKQZSDGCYPOJ-UHFFFAOYSA-N 0.000 description 1
IHQGFLMQQFOKNI-UHFFFAOYSA-N 1-benzyl-4-(3-methoxyphenyl)-3,6-dihydro-2h-pyridine Chemical compound COC1=CC=CC(C=2CCN(CC=3C=CC=CC=3)CC=2)=C1 IHQGFLMQQFOKNI-UHFFFAOYSA-N 0.000 description 1
UYMKVWIIAQEYEC-UHFFFAOYSA-N 1-benzyl-4-(3-methoxyphenyl)piperidin-4-ol Chemical compound COC1=CC=CC(C2(O)CCN(CC=3C=CC=CC=3)CC2)=C1 UYMKVWIIAQEYEC-UHFFFAOYSA-N 0.000 description 1
JCTYLKGNCVUPLT-UHFFFAOYSA-N 1-benzyl-4-(3-phenylmethoxyphenyl)-3,6-dihydro-2h-pyridine Chemical compound C=1C=CC=CC=1COC(C=1)=CC=CC=1C(CC1)=CCN1CC1=CC=CC=C1 JCTYLKGNCVUPLT-UHFFFAOYSA-N 0.000 description 1
XMRKNROGTZWRAV-UHFFFAOYSA-N 1-benzyl-4-(3-phenylmethoxyphenyl)piperidin-4-ol Chemical compound C1CC(O)(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)CCN1CC1=CC=CC=C1 XMRKNROGTZWRAV-UHFFFAOYSA-N 0.000 description 1
XIWOFLXZXBGWKN-UHFFFAOYSA-N 1-benzyl-4-(4-methoxyphenyl)-3-(naphthalen-2-ylmethoxy)piperidine Chemical compound C1=CC(OC)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(CC=2C=CC=CC=2)CC1 XIWOFLXZXBGWKN-UHFFFAOYSA-N 0.000 description 1
XRTONVAVTOLDRB-UHFFFAOYSA-N 1-benzyl-4-(4-methoxyphenyl)piperidin-4-ol Chemical compound C1=CC(OC)=CC=C1C1(O)CCN(CC=2C=CC=CC=2)CC1 XRTONVAVTOLDRB-UHFFFAOYSA-N 0.000 description 1
QFBFAIOZZKORIP-UHFFFAOYSA-N 1-benzyl-4-(4-methylphenyl)-3,6-dihydro-2h-pyridine Chemical compound C1=CC(C)=CC=C1C(CC1)=CCN1CC1=CC=CC=C1 QFBFAIOZZKORIP-UHFFFAOYSA-N 0.000 description 1
AZGNTLLAVWZVIQ-UHFFFAOYSA-N 1-benzyl-4-(4-methylphenyl)piperidin-4-ol Chemical compound C1=CC(C)=CC=C1C1(O)CCN(CC=2C=CC=CC=2)CC1 AZGNTLLAVWZVIQ-UHFFFAOYSA-N 0.000 description 1
IUUFZGDBMMRDKB-UHFFFAOYSA-N 1-benzyl-4-[3-[3-(oxan-2-yloxy)propoxy]phenyl]piperidin-3-ol Chemical compound C1CC(C=2C=C(OCCCOC3OCCCC3)C=CC=2)C(O)CN1CC1=CC=CC=C1 IUUFZGDBMMRDKB-UHFFFAOYSA-N 0.000 description 1
ZQXBOUZSXOIRGK-UHFFFAOYSA-N 1-benzyl-4-naphthalen-1-yl-3,6-dihydro-2h-pyridine Chemical compound C1CC(C=2C3=CC=CC=C3C=CC=2)=CCN1CC1=CC=CC=C1 ZQXBOUZSXOIRGK-UHFFFAOYSA-N 0.000 description 1
NYYHQXPTKJISQZ-UHFFFAOYSA-N 1-benzyl-4-naphthalen-1-ylpiperidin-3-ol Chemical compound C1CC(C=2C3=CC=CC=C3C=CC=2)C(O)CN1CC1=CC=CC=C1 NYYHQXPTKJISQZ-UHFFFAOYSA-N 0.000 description 1
CTVMDXPXVZMYEM-UHFFFAOYSA-N 1-benzyl-4-naphthalen-2-yl-3,6-dihydro-2h-pyridine Chemical compound C1CC(C=2C=C3C=CC=CC3=CC=2)=CCN1CC1=CC=CC=C1 CTVMDXPXVZMYEM-UHFFFAOYSA-N 0.000 description 1
CZLILGYORALRBX-UHFFFAOYSA-N 1-benzyl-4-naphthalen-2-ylpiperidin-3-ol Chemical compound C1CC(C=2C=C3C=CC=CC3=CC=2)C(O)CN1CC1=CC=CC=C1 CZLILGYORALRBX-UHFFFAOYSA-N 0.000 description 1
MBGNVMXEELOHBQ-UHFFFAOYSA-N 1-benzyl-4-naphthalen-2-ylpiperidin-4-ol Chemical compound C1CC(O)(C=2C=C3C=CC=CC3=CC=2)CCN1CC1=CC=CC=C1 MBGNVMXEELOHBQ-UHFFFAOYSA-N 0.000 description 1
IPWBFGUBXWMIPR-UHFFFAOYSA-N 1-bromo-2-fluorobenzene Chemical compound FC1=CC=CC=C1Br IPWBFGUBXWMIPR-UHFFFAOYSA-N 0.000 description 1
YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 description 1
QDFKKJYEIFBEFC-UHFFFAOYSA-N 1-bromo-3-fluorobenzene Chemical compound FC1=CC=CC(Br)=C1 QDFKKJYEIFBEFC-UHFFFAOYSA-N 0.000 description 1
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
WFPDYYHUULCORF-UHFFFAOYSA-N 1-bromoethoxybenzene Chemical compound CC(Br)OC1=CC=CC=C1 WFPDYYHUULCORF-UHFFFAOYSA-N 0.000 description 1
BASMANVIUSSIIM-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)benzene Chemical compound ClCC1=CC=CC=C1Cl BASMANVIUSSIIM-UHFFFAOYSA-N 0.000 description 1
BQLHMMQUVJCTAN-UHFFFAOYSA-N 1-chloro-3-methoxypropane Chemical compound COCCCCl BQLHMMQUVJCTAN-UHFFFAOYSA-N 0.000 description 1
JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
RSHBAGGASAJQCH-UHFFFAOYSA-N 1-iodo-3-methoxybenzene Chemical compound COC1=CC=CC(I)=C1 RSHBAGGASAJQCH-UHFFFAOYSA-N 0.000 description 1
QMKHOPJXDQAHBG-UHFFFAOYSA-N 1-iodo-3-phenylmethoxybenzene Chemical compound IC1=CC=CC(OCC=2C=CC=CC=2)=C1 QMKHOPJXDQAHBG-UHFFFAOYSA-N 0.000 description 1
QKFKOISIBFBPFF-VFBMNZBOSA-N 1-methyl-4-[2-[(3s,4r,5r)-5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxyethyl]piperazine Chemical compound C1CN(C)CCN1CCO[C@H]1[C@H](C=2C=CC(OCCCOCC=3C=CC=CC=3)=CC=2)[C@@H](OCC=2C=C3C=CC=CC3=CC=2)CNC1 QKFKOISIBFBPFF-VFBMNZBOSA-N 0.000 description 1
QKFKOISIBFBPFF-UHFFFAOYSA-N 1-methyl-4-[2-[5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxyethyl]piperazine Chemical group C1CN(C)CCN1CCOC1C(C=2C=CC(OCCCOCC=3C=CC=CC=3)=CC=2)C(OCC=2C=C3C=CC=CC3=CC=2)CNC1 QKFKOISIBFBPFF-UHFFFAOYSA-N 0.000 description 1
ANUDIJSMAVVPTC-RGULYWFUSA-N 1-methyl-4-[2-[7-[[(3r,4r)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxymethyl]naphthalen-2-yl]oxyethyl]piperazine Chemical compound C1CN(C)CCN1CCOC1=CC=C(C=CC(CO[C@@H]2[C@H](CCNC2)C=2C=CC(OCCCOCC=3C=CC=CC=3)=CC=2)=C2)C2=C1 ANUDIJSMAVVPTC-RGULYWFUSA-N 0.000 description 1
FZHZVVBNXWNQLS-UHFFFAOYSA-N 1-methyl-4-[2-[7-[[4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxymethyl]naphthalen-2-yl]oxyethyl]piperazine;hydrochloride Chemical group Cl.C1CN(C)CCN1CCOC1=CC=C(C=CC(COC2C(CCNC2)C=2C=CC(OCCCOCC=3C=CC=CC=3)=CC=2)=C2)C2=C1 FZHZVVBNXWNQLS-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
CJXASCLMZSMFTL-UHFFFAOYSA-N 1-phenyl-5-[(1-phenyltetrazol-5-yl)disulfanyl]tetrazole Chemical compound N=1N=NN(C=2C=CC=CC=2)C=1SSC1=NN=NN1C1=CC=CC=C1 CJXASCLMZSMFTL-UHFFFAOYSA-N 0.000 description 1
KYWMCFOWDYFYLV-UHFFFAOYSA-N 1h-imidazole-2-carboxylic acid Chemical compound OC(=O)C1=NC=CN1 KYWMCFOWDYFYLV-UHFFFAOYSA-N 0.000 description 1
GGYCYRLHWXXXPA-UHFFFAOYSA-N 2,2,2-trichloroethyl 3-(naphthalen-2-ylmethoxy)-4-[3-[3-(oxan-2-yloxy)propoxy]phenyl]piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OCC(Cl)(Cl)Cl)CCC1C(C=1)=CC=CC=1OCCCOC1CCCCO1 GGYCYRLHWXXXPA-UHFFFAOYSA-N 0.000 description 1
DGAMDFQEBYFDIB-UHFFFAOYSA-N 2,2,2-trichloroethyl 4-(3-fluorophenyl)-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound FC1=CC=CC(C2C(CN(CC2)C(=O)OCC(Cl)(Cl)Cl)OCC=2C=C3C=CC=CC3=CC=2)=C1 DGAMDFQEBYFDIB-UHFFFAOYSA-N 0.000 description 1
XRZMJGLYQGNIDO-UHFFFAOYSA-N 2,2,2-trichloroethyl 4-(4-bromophenyl)-3-(2,2,2-trichloroethoxycarbonyloxy)piperidine-1-carboxylate Chemical compound ClC(Cl)(Cl)COC(=O)OC1CN(C(=O)OCC(Cl)(Cl)Cl)CCC1C1=CC=C(Br)C=C1 XRZMJGLYQGNIDO-UHFFFAOYSA-N 0.000 description 1
ZKOAMBWHBHICDS-UHFFFAOYSA-N 2,2,2-trichloroethyl 4-(4-chlorophenyl)-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C1=CC(Cl)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(C(=O)OCC(Cl)(Cl)Cl)CC1 ZKOAMBWHBHICDS-UHFFFAOYSA-N 0.000 description 1
SJCXNUXDDQUWCQ-UHFFFAOYSA-N 2,2,2-trichloroethyl 4-[3-(2-benzoyloxyethoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OCC(Cl)(Cl)Cl)CCC1C(C=1)=CC=CC=1OCCOC(=O)C1=CC=CC=C1 SJCXNUXDDQUWCQ-UHFFFAOYSA-N 0.000 description 1
QJXSSAIQAMXANW-UHFFFAOYSA-N 2,2,2-trichloroethyl 4-[3-(3-hydroxypropoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound OCCCOC1=CC=CC(C2C(CN(CC2)C(=O)OCC(Cl)(Cl)Cl)OCC=2C=C3C=CC=CC3=CC=2)=C1 QJXSSAIQAMXANW-UHFFFAOYSA-N 0.000 description 1
KVVJBSVVSABSOX-UHFFFAOYSA-N 2,2,2-trichloroethyl 4-[3-(4-benzoyloxybutoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OCC(Cl)(Cl)Cl)CCC1C(C=1)=CC=CC=1OCCCCOC(=O)C1=CC=CC=C1 KVVJBSVVSABSOX-UHFFFAOYSA-N 0.000 description 1
GOPMRQYKDLONOG-UHFFFAOYSA-N 2,2,2-trichloroethyl 4-[3-(4-hydroxybutoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound OCCCCOC1=CC=CC(C2C(CN(CC2)C(=O)OCC(Cl)(Cl)Cl)OCC=2C=C3C=CC=CC3=CC=2)=C1 GOPMRQYKDLONOG-UHFFFAOYSA-N 0.000 description 1
KFNVOWCABYFCRU-UHFFFAOYSA-N 2,2,2-trichloroethyl 4-[4-(3-carbamoyloxypropoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C1=CC(OCCCOC(=O)N)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(C(=O)OCC(Cl)(Cl)Cl)CC1 KFNVOWCABYFCRU-UHFFFAOYSA-N 0.000 description 1
SZAMATDNLLRWLV-UHFFFAOYSA-N 2,2,2-trichloroethyl 4-[4-(3-hydroxypropoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C1=CC(OCCCO)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(C(=O)OCC(Cl)(Cl)Cl)CC1 SZAMATDNLLRWLV-UHFFFAOYSA-N 0.000 description 1
IRSVDHPYXFLLDS-UHFFFAOYSA-N 2,4-dichloro-1-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1Cl IRSVDHPYXFLLDS-UHFFFAOYSA-N 0.000 description 1
JBLIDPPHFGWTKU-UHFFFAOYSA-N 2,6-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=C(Cl)C=CC=C1Cl JBLIDPPHFGWTKU-UHFFFAOYSA-N 0.000 description 1
NDXRPDJVAUCBOH-UHFFFAOYSA-N 2,6-dimethoxybenzoyl chloride Chemical compound COC1=CC=CC(OC)=C1C(Cl)=O NDXRPDJVAUCBOH-UHFFFAOYSA-N 0.000 description 1
SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 1
MNGUYQVJFSKJOJ-UHFFFAOYSA-N 2-(3-chloropropyl)-2-phenyl-1,3-dioxolane Chemical compound C=1C=CC=CC=1C1(CCCCl)OCCO1 MNGUYQVJFSKJOJ-UHFFFAOYSA-N 0.000 description 1
CUJJQXBLYHZXEJ-VIZCGCQYSA-N 2-(3-cyclohexylpropoxy)-5-[(3r,4r)-3-[(1,4-dimethoxynaphthalen-2-yl)methoxy]piperidin-4-yl]pyridine Chemical compound N1=CC([C@H]2CCNC[C@@H]2OCC=2C=C(C3=CC=CC=C3C=2OC)OC)=CC=C1OCCCC1CCCCC1 CUJJQXBLYHZXEJ-VIZCGCQYSA-N 0.000 description 1
DFXFQWZHKKEJDM-UHFFFAOYSA-N 2-(4-bromobutoxy)oxane Chemical compound BrCCCCOC1CCCCO1 DFXFQWZHKKEJDM-UHFFFAOYSA-N 0.000 description 1
CXJOONIFSVSFAD-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetyl chloride Chemical compound COC1=CC=C(CC(Cl)=O)C=C1 CXJOONIFSVSFAD-UHFFFAOYSA-N 0.000 description 1
VQGXSJJMMTUKKV-UHFFFAOYSA-N 2-(bromomethyl)-5-phenyl-1,3,4-oxadiazole Chemical compound O1C(CBr)=NN=C1C1=CC=CC=C1 VQGXSJJMMTUKKV-UHFFFAOYSA-N 0.000 description 1
LSGCBNJHZGJEEJ-UHFFFAOYSA-N 2-(chloromethyl)-1-benzofuran Chemical compound C1=CC=C2OC(CCl)=CC2=C1 LSGCBNJHZGJEEJ-UHFFFAOYSA-N 0.000 description 1
JHDSVVPTMIYVGV-UHFFFAOYSA-N 2-(chloromethyl)-1-benzothiophene Chemical compound C1=CC=C2SC(CCl)=CC2=C1 JHDSVVPTMIYVGV-UHFFFAOYSA-N 0.000 description 1
TXZFBHYDQGYOIT-UHFFFAOYSA-N 2-(chloromethyl)benzoyl chloride Chemical compound ClCC1=CC=CC=C1C(Cl)=O TXZFBHYDQGYOIT-UHFFFAOYSA-N 0.000 description 1
NJWIMFZLESWFIM-UHFFFAOYSA-N 2-(chloromethyl)pyridine Chemical compound ClCC1=CC=CC=N1 NJWIMFZLESWFIM-UHFFFAOYSA-N 0.000 description 1
DDEAEWMDOSXKBX-UHFFFAOYSA-N 2-(chloromethyl)quinoline Chemical compound C1=CC=CC2=NC(CCl)=CC=C21 DDEAEWMDOSXKBX-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
PRKWVSHZYDOZLP-UHFFFAOYSA-N 2-[(6,7-dichloro-2-methyl-1-oxo-2-phenyl-3h-inden-5-yl)oxy]acetic acid Chemical compound C1C2=CC(OCC(O)=O)=C(Cl)C(Cl)=C2C(=O)C1(C)C1=CC=CC=C1 PRKWVSHZYDOZLP-UHFFFAOYSA-N 0.000 description 1
HGKHQEVNPHCQCH-UHFFFAOYSA-N 2-[2-(4-bromophenyl)ethoxy]oxane Chemical compound C1=CC(Br)=CC=C1CCOC1OCCCC1 HGKHQEVNPHCQCH-UHFFFAOYSA-N 0.000 description 1
KVXZOWNZJYJZMO-UHFFFAOYSA-N 2-[2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]ethylsulfanyl]-1,3-benzothiazole Chemical compound C1=CC=C2SC(SCCC=3C=CC(=CC=3)C3C(CNCC3)OCC=3C=C4C=CC=CC4=CC=3)=NC2=C1 KVXZOWNZJYJZMO-UHFFFAOYSA-N 0.000 description 1
REXGEZZYAJFECU-UHFFFAOYSA-N 2-[3-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenoxy]ethanol Chemical compound OCCOC1=CC=CC(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)=C1 REXGEZZYAJFECU-UHFFFAOYSA-N 0.000 description 1
YKHQXLOZZUPUSK-UHFFFAOYSA-N 2-[3-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenoxy]ethyl n-pyridin-2-ylcarbamate Chemical compound C=1C=CC(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)=CC=1OCCOC(=O)NC1=CC=CC=N1 YKHQXLOZZUPUSK-UHFFFAOYSA-N 0.000 description 1
RBJQRSLXJMEBNQ-UHFFFAOYSA-N 2-[3-[[4-(4-fluorophenyl)piperidin-3-yl]oxymethyl]naphthalen-1-yl]oxyethanol Chemical compound C=1C2=CC=CC=C2C(OCCO)=CC=1COC1CNCCC1C1=CC=C(F)C=C1 RBJQRSLXJMEBNQ-UHFFFAOYSA-N 0.000 description 1
JKTZVAHEVZVCGZ-UHFFFAOYSA-N 2-[3-[[4-(4-fluorophenyl)piperidin-3-yl]oxymethyl]naphthalen-1-yl]oxyethyl n-pyridin-2-ylcarbamate Chemical compound C1=CC(F)=CC=C1C1C(OCC=2C=C3C=CC=CC3=C(OCCOC(=O)NC=3N=CC=CC=3)C=2)CNCC1 JKTZVAHEVZVCGZ-UHFFFAOYSA-N 0.000 description 1
UBEZUKQSXXGPJP-UHFFFAOYSA-N 2-[4-[1-[(2-methylpropan-2-yl)oxycarbonyl]-3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenoxy]ethyl pyridine-3-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1OCCOC(=O)C1=CC=CN=C1 UBEZUKQSXXGPJP-UHFFFAOYSA-N 0.000 description 1
HMSFXGSFECUBCE-UHFFFAOYSA-N 2-[4-[1-[(2-methylpropan-2-yl)oxycarbonyl]-3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]ethyl pyridine-3-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1CCOC(=O)C1=CC=CN=C1 HMSFXGSFECUBCE-UHFFFAOYSA-N 0.000 description 1
IHCCLXNEEPMSIO-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 IHCCLXNEEPMSIO-UHFFFAOYSA-N 0.000 description 1
QKGOCPKYHOEAKB-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenoxy]ethanol Chemical compound C1=CC(OCCO)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CNCC1 QKGOCPKYHOEAKB-UHFFFAOYSA-N 0.000 description 1
DKGSUDNTQUCRHW-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenoxy]ethyl 1,3-benzodioxole-5-carboxylate;hydrochloride Chemical compound Cl.C1=C2OCOC2=CC(C(OCCOC=2C=CC(=CC=2)C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)=O)=C1 DKGSUDNTQUCRHW-UHFFFAOYSA-N 0.000 description 1
ZOTGNCYJSHSUFY-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenoxy]ethyl 2-methylsulfanylbenzoate hydrochloride Chemical compound Cl.CSC1=CC=CC=C1C(=O)OCCOC1=CC=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=C1 ZOTGNCYJSHSUFY-UHFFFAOYSA-N 0.000 description 1
IOWOVPBHLNRYJP-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenoxy]ethyl furan-2-carboxylate;hydrochloride Chemical compound Cl.C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCOC(=O)C1=CC=CO1 IOWOVPBHLNRYJP-UHFFFAOYSA-N 0.000 description 1
LITZEXYHPRWUTF-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenoxy]ethyl furan-3-carboxylate;hydrochloride Chemical compound Cl.C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCOC(=O)C=1C=COC=1 LITZEXYHPRWUTF-UHFFFAOYSA-N 0.000 description 1
PWLDAYHUFVXDEJ-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenoxy]ethyl pyridine-3-carboxylate;hydrochloride Chemical compound Cl.C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCOC(=O)C1=CC=CN=C1 PWLDAYHUFVXDEJ-UHFFFAOYSA-N 0.000 description 1
HAXWNJCQXHPTBG-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenoxy]ethyl thiophene-2-carboxylate;hydrochloride Chemical compound Cl.C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCOC(=O)C1=CC=CS1 HAXWNJCQXHPTBG-UHFFFAOYSA-N 0.000 description 1
ZISLZIUPLJEELP-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenoxy]ethyl thiophene-3-carboxylate;hydrochloride Chemical compound Cl.C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCOC(=O)C=1C=CSC=1 ZISLZIUPLJEELP-UHFFFAOYSA-N 0.000 description 1
LDTBDNCMYXMDLE-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]-N-phenacylacetamide Chemical compound C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1CC(=O)NCC(=O)C1=CC=CC=C1 LDTBDNCMYXMDLE-UHFFFAOYSA-N 0.000 description 1
NDXAQMKVBKAQAK-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]-n-(3-oxo-3-phenylpropyl)acetamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1CC(=O)NCCC(=O)C1=CC=CC=C1 NDXAQMKVBKAQAK-UHFFFAOYSA-N 0.000 description 1
PFVLZAOHARKYEX-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]-n-phenacylacetamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1CC(=O)NCC(=O)C1=CC=CC=C1 PFVLZAOHARKYEX-UHFFFAOYSA-N 0.000 description 1
ZRBWDNFQMVPTLQ-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]ethanol;hydrochloride Chemical compound Cl.C1=CC(CCO)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CNCC1 ZRBWDNFQMVPTLQ-UHFFFAOYSA-N 0.000 description 1
IIBSNAWPYLKQEX-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]ethyl 1h-imidazole-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1CCOC(=O)C1=NC=CN1 IIBSNAWPYLKQEX-UHFFFAOYSA-N 0.000 description 1
CDGYBXZKMWPZDU-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]ethyl 2,6-dichlorobenzoate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.ClC1=CC=CC(Cl)=C1C(=O)OCCC1=CC=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=C1 CDGYBXZKMWPZDU-UHFFFAOYSA-N 0.000 description 1
YKXWWIFCFLIZPY-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]ethyl 2,6-dimethoxybenzoate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.COC1=CC=CC(OC)=C1C(=O)OCCC1=CC=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=C1 YKXWWIFCFLIZPY-UHFFFAOYSA-N 0.000 description 1
ZLIKPIQHJVEPMQ-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]ethyl 2-acetyloxybenzoate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC(=O)OC1=CC=CC=C1C(=O)OCCC1=CC=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=C1 ZLIKPIQHJVEPMQ-UHFFFAOYSA-N 0.000 description 1
HQBOGMQDSGLZFC-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]ethyl 2-chlorobenzoate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.ClC1=CC=CC=C1C(=O)OCCC1=CC=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=C1 HQBOGMQDSGLZFC-UHFFFAOYSA-N 0.000 description 1
KCQGNKZTUXZCTQ-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]ethyl 2-methoxybenzoate;hydrochloride Chemical compound Cl.COC1=CC=CC=C1C(=O)OCCC1=CC=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=C1 KCQGNKZTUXZCTQ-UHFFFAOYSA-N 0.000 description 1
LNMGVCRSIIBHKB-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]ethyl 2-thiophen-2-ylacetate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1CCOC(=O)CC1=CC=CS1 LNMGVCRSIIBHKB-UHFFFAOYSA-N 0.000 description 1
KVJJNTSUVUGJQM-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]ethyl 3-methoxybenzoate;hydrochloride Chemical compound Cl.COC1=CC=CC(C(=O)OCCC=2C=CC(=CC=2)C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)=C1 KVJJNTSUVUGJQM-UHFFFAOYSA-N 0.000 description 1
OHVZKJFCXMGLIF-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]ethyl cyclohexanecarboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1CCOC(=O)C1CCCCC1 OHVZKJFCXMGLIF-UHFFFAOYSA-N 0.000 description 1
JPUPBDHIYLRQOJ-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]ethyl cyclopropanecarboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1CCOC(=O)C1CC1 JPUPBDHIYLRQOJ-UHFFFAOYSA-N 0.000 description 1
NMEZCMJDGIWMBC-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]ethyl n-pyridin-2-ylcarbamate;hydrochloride Chemical compound Cl.C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1CCOC(=O)NC1=CC=CC=N1 NMEZCMJDGIWMBC-UHFFFAOYSA-N 0.000 description 1
OCVHGANOTGEYLE-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]ethyl pyridine-2-carboxylate Chemical compound C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1CCOC(=O)C1=CC=CC=N1 OCVHGANOTGEYLE-UHFFFAOYSA-N 0.000 description 1
RWIMDQVYRQBDMU-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]ethyl pyridine-3-carboxylate;hydrochloride Chemical compound Cl.C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1CCOC(=O)C1=CC=CN=C1 RWIMDQVYRQBDMU-UHFFFAOYSA-N 0.000 description 1
WBXPBYNDHPRPFR-UHFFFAOYSA-N 2-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]ethyl thiophene-3-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1CCOC(=O)C=1C=CSC=1 WBXPBYNDHPRPFR-UHFFFAOYSA-N 0.000 description 1
GNZDJFLTIXWLKK-UHFFFAOYSA-N 2-[4-[3-[(4-phenylmethoxynaphthalen-2-yl)methoxy]piperidin-4-yl]phenyl]ethyl benzoate;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(=O)OCCC(C=C1)=CC=C1C1CCNCC1OCC(C=C1C=CC=CC1=1)=CC=1OCC1=CC=CC=C1 GNZDJFLTIXWLKK-UHFFFAOYSA-N 0.000 description 1
DSPWLOQFYHGKMW-UHFFFAOYSA-N 2-[4-[3-[[4-[(2-methoxyphenyl)methoxy]naphthalen-2-yl]methoxy]piperidin-4-yl]phenoxy]ethyl benzoate;hydrochloride Chemical compound Cl.COC1=CC=CC=C1COC1=CC(COC2C(CCNC2)C=2C=CC(OCCOC(=O)C=3C=CC=CC=3)=CC=2)=CC2=CC=CC=C12 DSPWLOQFYHGKMW-UHFFFAOYSA-N 0.000 description 1
XKIJFRWKTNBSOC-UHFFFAOYSA-N 2-[[2-(chloromethyl)phenoxy]methoxy]ethyl-trimethylsilane Chemical compound C[Si](C)(C)CCOCOC1=CC=CC=C1CCl XKIJFRWKTNBSOC-UHFFFAOYSA-N 0.000 description 1
UESOQGYQDWPBLI-UHFFFAOYSA-N 2-[[3-(bromomethyl)naphthalen-2-yl]oxymethoxy]ethyl-trimethylsilane Chemical compound C1=CC=C2C=C(CBr)C(OCOCC[Si](C)(C)C)=CC2=C1 UESOQGYQDWPBLI-UHFFFAOYSA-N 0.000 description 1
KSEKVMWIHZQPDK-UHFFFAOYSA-N 2-[[3-[[4-(4-fluorophenyl)piperidin-3-yl]oxymethyl]naphthalen-1-yl]oxymethyl]phenol Chemical compound OC1=CC=CC=C1COC1=CC(COC2C(CCNC2)C=2C=CC(F)=CC=2)=CC2=CC=CC=C12 KSEKVMWIHZQPDK-UHFFFAOYSA-N 0.000 description 1
QBODSZLECQGOCW-UHFFFAOYSA-N 2-[[3-[[4-(4-fluorophenyl)piperidin-3-yl]oxymethyl]naphthalen-1-yl]oxymethyl]pyridine Chemical compound C1=CC(F)=CC=C1C1C(OCC=2C=C3C=CC=CC3=C(OCC=3N=CC=CC=3)C=2)CNCC1 QBODSZLECQGOCW-UHFFFAOYSA-N 0.000 description 1
IWIAOCBWXSXXKA-UHFFFAOYSA-N 2-[[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]methyl]-5-phenyl-1,3,4-oxadiazole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C2C=CC=CC2=CC=1COC1CNCCC1C(C=C1)=CC=C1CC(O1)=NN=C1C1=CC=CC=C1 IWIAOCBWXSXXKA-UHFFFAOYSA-N 0.000 description 1
OUUTYBIJDZMIMC-UHFFFAOYSA-N 2-[[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]methylsulfanyl]-6-nitro-1,3-benzothiazole;hydrochloride Chemical compound Cl.C1=CC=CC2=CC(COC3CNCCC3C3=CC=C(C=C3)CSC3=NC4=CC=C(C=C4S3)[N+](=O)[O-])=CC=C21 OUUTYBIJDZMIMC-UHFFFAOYSA-N 0.000 description 1
XUSPJFCEHPMGLV-UHFFFAOYSA-N 2-[[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]methylsulfanyl]pyrimidine Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CNCCC1C(C=C1)=CC=C1CSC1=NC=CC=N1 XUSPJFCEHPMGLV-UHFFFAOYSA-N 0.000 description 1
UWRLWIDEXIDWIL-UHFFFAOYSA-N 2-[[7-(chloromethyl)naphthalen-1-yl]oxymethoxy]ethyl-trimethylsilane Chemical compound C1=C(CCl)C=C2C(OCOCC[Si](C)(C)C)=CC=CC2=C1 UWRLWIDEXIDWIL-UHFFFAOYSA-N 0.000 description 1
VAOHIFYJWBATMP-GPOMZPHUSA-N 2-[[7-[[(3r,4r)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxymethyl]naphthalen-2-yl]methoxy]ethanol Chemical compound C1=CC([C@H]2CCNC[C@@H]2OCC=2C=CC3=CC=C(C=C3C=2)COCCO)=CC=C1OCCCOCC1=CC=CC=C1 VAOHIFYJWBATMP-GPOMZPHUSA-N 0.000 description 1
VAOHIFYJWBATMP-UHFFFAOYSA-N 2-[[7-[[4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxymethyl]naphthalen-2-yl]methoxy]ethanol Chemical compound C=1C2=CC(COCCO)=CC=C2C=CC=1COC1CNCCC1C(C=C1)=CC=C1OCCCOCC1=CC=CC=C1 VAOHIFYJWBATMP-UHFFFAOYSA-N 0.000 description 1
HEQOJEGTZCTHCF-UHFFFAOYSA-N 2-amino-1-phenylethanone Chemical compound NCC(=O)C1=CC=CC=C1 HEQOJEGTZCTHCF-UHFFFAOYSA-N 0.000 description 1
APSMUYYLXZULMS-UHFFFAOYSA-N 2-bromonaphthalene Chemical compound C1=CC=CC2=CC(Br)=CC=C21 APSMUYYLXZULMS-UHFFFAOYSA-N 0.000 description 1
PBIUDEUWYGBHDW-UHFFFAOYSA-N 2-chloro-1-pyridin-3-ylethanone;hydrochloride Chemical compound Cl.ClCC(=O)C1=CC=CN=C1 PBIUDEUWYGBHDW-UHFFFAOYSA-N 0.000 description 1
JIVPVXMEBJLZRO-CQSZACIVSA-N 2-chloro-5-[(1r)-1-hydroxy-3-oxo-2h-isoindol-1-yl]benzenesulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC([C@@]2(O)C3=CC=CC=C3C(=O)N2)=C1 JIVPVXMEBJLZRO-CQSZACIVSA-N 0.000 description 1
FHEOPAAMRFEMFM-UHFFFAOYSA-N 2-chloroethylcyclopropane Chemical compound ClCCC1CC1 FHEOPAAMRFEMFM-UHFFFAOYSA-N 0.000 description 1
ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical compound OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 description 1
LWJQGKJCZOGGPJ-UHFFFAOYSA-N 2-methylsulfanylbenzoic acid Chemical compound CSC1=CC=CC=C1C(O)=O LWJQGKJCZOGGPJ-UHFFFAOYSA-N 0.000 description 1
PCLKVJBRTCQNDU-UHFFFAOYSA-N 2-methylsulfonylpyridine Chemical compound CS(=O)(=O)C1=CC=CC=N1 PCLKVJBRTCQNDU-UHFFFAOYSA-N 0.000 description 1
VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
QISAUDWTBBNJIR-UHFFFAOYSA-N 2-phenylmethoxyacetyl chloride Chemical compound ClC(=O)COCC1=CC=CC=C1 QISAUDWTBBNJIR-UHFFFAOYSA-N 0.000 description 1
RCNOGGGBSSVMAS-UHFFFAOYSA-N 2-thiophen-3-ylacetic acid Chemical compound OC(=O)CC=1C=CSC=1 RCNOGGGBSSVMAS-UHFFFAOYSA-N 0.000 description 1
IGEKNGAZSXAUDU-UHFFFAOYSA-N 2-trimethylsilylethyl 4-(3-bromophenyl)-3-(2-trimethylsilylethoxycarbonyloxy)piperidine-1-carboxylate Chemical compound C[Si](C)(C)CCOC(=O)OC1CN(C(=O)OCC[Si](C)(C)C)CCC1C1=CC=CC(Br)=C1 IGEKNGAZSXAUDU-UHFFFAOYSA-N 0.000 description 1
WGLBDDSHTXOXDA-UHFFFAOYSA-N 2-trimethylsilylethyl 4-(4-fluorophenyl)-3-[[6-(2-trimethylsilylethoxymethoxy)naphthalen-2-yl]methoxy]piperidine-1-carboxylate Chemical compound C1=CC2=CC(OCOCC[Si](C)(C)C)=CC=C2C=C1COC1CN(C(=O)OCC[Si](C)(C)C)CCC1C1=CC=C(F)C=C1 WGLBDDSHTXOXDA-UHFFFAOYSA-N 0.000 description 1
FCMXYBHKXLRETA-UHFFFAOYSA-N 2-trimethylsilylethyl 4-(4-fluorophenyl)-3-[[7-(2-trimethylsilylethoxymethoxy)naphthalen-2-yl]methoxy]piperidine-1-carboxylate Chemical compound C=1C2=CC(OCOCC[Si](C)(C)C)=CC=C2C=CC=1COC1CN(C(=O)OCC[Si](C)(C)C)CCC1C1=CC=C(F)C=C1 FCMXYBHKXLRETA-UHFFFAOYSA-N 0.000 description 1
NMKSAYKQLCHXDK-UHFFFAOYSA-N 3,3-diphenyl-N-(1-phenylethyl)-1-propanamine Chemical compound C=1C=CC=CC=1C(C)NCCC(C=1C=CC=CC=1)C1=CC=CC=C1 NMKSAYKQLCHXDK-UHFFFAOYSA-N 0.000 description 1
FTHPLWDYWAKYCY-UHFFFAOYSA-N 3,5-dimethoxybenzoyl chloride Chemical compound COC1=CC(OC)=CC(C(Cl)=O)=C1 FTHPLWDYWAKYCY-UHFFFAOYSA-N 0.000 description 1
LIENSDCLUZNZOH-UHFFFAOYSA-N 3-(1-benzofuran-2-ylmethoxy)-4-(4-chlorophenyl)piperidine Chemical compound C1=CC(Cl)=CC=C1C1C(OCC=2OC3=CC=CC=C3C=2)CNCC1 LIENSDCLUZNZOH-UHFFFAOYSA-N 0.000 description 1
LSOPAJYDXIOCSL-UHFFFAOYSA-N 3-(1-benzothiophen-2-ylmethoxy)-4-(4-chlorophenyl)piperidine Chemical compound C1=CC(Cl)=CC=C1C1C(OCC=2SC3=CC=CC=C3C=2)CNCC1 LSOPAJYDXIOCSL-UHFFFAOYSA-N 0.000 description 1
BDZHYPOERSUMDS-UHFFFAOYSA-N 3-(1-benzothiophen-5-ylmethoxy)-4-(4-fluorophenyl)piperidine Chemical compound C1=CC(F)=CC=C1C1C(OCC=2C=C3C=CSC3=CC=2)CNCC1 BDZHYPOERSUMDS-UHFFFAOYSA-N 0.000 description 1
FSCQSJZHGNSGMR-UHFFFAOYSA-N 3-(2,3-dihydro-1,4-benzodioxin-6-ylmethoxy)-4-(4-fluorophenyl)piperidine Chemical compound C1=CC(F)=CC=C1C1C(OCC=2C=C3OCCOC3=CC=2)CNCC1 FSCQSJZHGNSGMR-UHFFFAOYSA-N 0.000 description 1
MPHKKUXSKHBKBV-UHFFFAOYSA-N 3-(2,3-dihydro-1h-inden-5-ylmethoxy)-4-(4-fluorophenyl)piperidine Chemical compound C1=CC(F)=CC=C1C1C(OCC=2C=C3CCCC3=CC=2)CNCC1 MPHKKUXSKHBKBV-UHFFFAOYSA-N 0.000 description 1
XZSGEEVVPTWADE-UHFFFAOYSA-N 3-(2,3-dihydro-1h-inden-5-ylmethoxy)-4-(4-fluorophenyl)piperidine-1-carboxylic acid Chemical compound C=1C=C2CCCC2=CC=1COC1CN(C(=O)O)CCC1C1=CC=C(F)C=C1 XZSGEEVVPTWADE-UHFFFAOYSA-N 0.000 description 1
IHWCWYONVXLNHA-XUPAESTNSA-N 3-(4-methylpiperazin-1-yl)propyl-[[(3S,4R,5R)-5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]methyl]carbamic acid Chemical compound C1CN(C)CCN1CCCN(C(O)=O)C[C@H]1[C@H](C=2C=CC(OCCCOCC=3C=CC=CC=3)=CC=2)[C@@H](OCC=2C=C3C=CC=CC3=CC=2)CNC1 IHWCWYONVXLNHA-XUPAESTNSA-N 0.000 description 1
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
JSDMASFTJDMHGE-UHFFFAOYSA-N 3-(methoxymethyl)-5-(naphthalen-2-ylmethoxy)-4-[4-(phenylmethoxymethyl)phenyl]piperidine Chemical group COCC1CNCC(OCC=2C=C3C=CC=CC3=CC=2)C1C(C=C1)=CC=C1COCC1=CC=CC=C1 JSDMASFTJDMHGE-UHFFFAOYSA-N 0.000 description 1
UCMSQIAMVNZMRY-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-(5,6,7,8-tetrahydronaphthalen-2-yl)piperidine Chemical compound C1=CC=CC2=CC(COC3C(CCNC3)C=3C=C4CCCCC4=CC=3)=CC=C21 UCMSQIAMVNZMRY-UHFFFAOYSA-N 0.000 description 1
QMVJFHAJSNEPJF-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[3-(trifluoromethyl)phenyl]piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C1=CC=CC(C(F)(F)F)=C1 QMVJFHAJSNEPJF-UHFFFAOYSA-N 0.000 description 1
NFZGQPMCJCPNPI-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-(2-oxo-2-phenacyloxyethyl)phenyl]piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1CC(=O)OCC(=O)C1=CC=CC=C1 NFZGQPMCJCPNPI-UHFFFAOYSA-N 0.000 description 1
ZXHFPCBEJRKEAX-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-(2-phenoxyethoxy)phenyl]piperidine Chemical compound C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCOC1=CC=CC=C1 ZXHFPCBEJRKEAX-UHFFFAOYSA-N 0.000 description 1
PMKAXYIYDINRAX-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-(2-phenoxyethoxy)phenyl]piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1OCCOC1=CC=CC=C1 PMKAXYIYDINRAX-UHFFFAOYSA-N 0.000 description 1
BLXZPSKTPGYZCO-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-(2-phenoxyethyl)phenyl]piperidine Chemical compound C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1CCOC1=CC=CC=C1 BLXZPSKTPGYZCO-UHFFFAOYSA-N 0.000 description 1
GJILJTBTLYHBPL-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-(2-phenylmethoxyethoxy)phenyl]piperidine Chemical compound C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCOCC1=CC=CC=C1 GJILJTBTLYHBPL-UHFFFAOYSA-N 0.000 description 1
JKLHISUMBVQTRX-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-(2-phenylmethoxyethoxy)phenyl]piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1OCCOCC1=CC=CC=C1 JKLHISUMBVQTRX-UHFFFAOYSA-N 0.000 description 1
KBPJUNCHSFFTPR-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-(2-phenylsulfanylethoxy)phenyl]piperidine;hydrochloride Chemical compound Cl.C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCSC1=CC=CC=C1 KBPJUNCHSFFTPR-UHFFFAOYSA-N 0.000 description 1
CTWNFSAGTXUJEQ-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-(2-phenylsulfanylethyl)phenyl]piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1CCSC1=CC=CC=C1 CTWNFSAGTXUJEQ-UHFFFAOYSA-N 0.000 description 1
VWDUGGHZIJJTOK-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-(2-trityloxyethyl)phenyl]piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1CCOC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 VWDUGGHZIJJTOK-UHFFFAOYSA-N 0.000 description 1
SBQHXMHGXWOGFR-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidine Chemical group C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCCOCC1=CC=CC=C1 SBQHXMHGXWOGFR-UHFFFAOYSA-N 0.000 description 1
NWFIIEXVPSFODF-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-(naphthalen-2-ylmethoxymethyl)phenyl]piperidine;hydrochloride Chemical compound Cl.C1=CC=CC2=CC(COC3CNCCC3C3=CC=C(C=C3)COCC=3C=C4C=CC=CC4=CC=3)=CC=C21 NWFIIEXVPSFODF-UHFFFAOYSA-N 0.000 description 1
QCJORSIOLSVXCR-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-(pyrimidin-2-ylsulfanylmethyl)phenyl]piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1CSC1=NC=CC=N1 QCJORSIOLSVXCR-UHFFFAOYSA-N 0.000 description 1
VPXZGVBSKHLEJA-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-[(1-phenyltetrazol-5-yl)sulfanylmethyl]phenyl]piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1CSC1=NN=NN1C1=CC=CC=C1 VPXZGVBSKHLEJA-UHFFFAOYSA-N 0.000 description 1
NONUQVXBYABZLB-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-[(1-phenyltetrazol-5-yl)sulfanylmethyl]phenyl]piperidine;hydrochloride Chemical compound Cl.C=1C=C2C=CC=CC2=CC=1COC1CNCCC1C(C=C1)=CC=C1CSC1=NN=NN1C1=CC=CC=C1 NONUQVXBYABZLB-UHFFFAOYSA-N 0.000 description 1
RHNUEUXRDNSNIJ-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-[(3-oxo-3-phenylpropyl)carbamoyl]phenyl]piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1C(=O)NCCC(=O)C1=CC=CC=C1 RHNUEUXRDNSNIJ-UHFFFAOYSA-N 0.000 description 1
FBTLGPZLKBGRGZ-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-[(3-phenyl-1,2,4-oxadiazol-5-yl)methyl]phenyl]piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1CC(ON=1)=NC=1C1=CC=CC=C1 FBTLGPZLKBGRGZ-UHFFFAOYSA-N 0.000 description 1
IANWXFPKWOKIBW-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-[(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]phenyl]piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1CC(O1)=NN=C1C1=CC=CC=C1 IANWXFPKWOKIBW-UHFFFAOYSA-N 0.000 description 1
SDYXPQUKOSBSBK-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-[(6-nitro-1,3-benzothiazol-2-yl)sulfanylmethyl]phenyl]piperidine-1-carboxylic acid Chemical compound C1=C([N+]([O-])=O)C=C2SC(SCC3=CC=C(C=C3)C3CCN(CC3OCC=3C=C4C=CC=CC4=CC=3)C(=O)O)=NC2=C1 SDYXPQUKOSBSBK-UHFFFAOYSA-N 0.000 description 1
BDLPWCHQOMHBEA-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-[2-(1,2,4-triazol-1-yl)ethoxy]phenyl]piperidine;hydrochloride Chemical compound Cl.C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCN1C=NC=N1 BDLPWCHQOMHBEA-UHFFFAOYSA-N 0.000 description 1
YXDIDTDFVHJPTL-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-[2-(2-thiophen-3-ylacetyl)oxyethyl]phenyl]piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1CCOC(=O)CC=1C=CSC=1 YXDIDTDFVHJPTL-UHFFFAOYSA-N 0.000 description 1
INRAPKZZNLOEFY-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-[2-[4-(2-trimethylsilylethoxymethoxy)benzoyl]oxyethoxy]phenyl]piperidine-1-carboxylic acid Chemical compound C1=CC(OCOCC[Si](C)(C)C)=CC=C1C(=O)OCCOC1=CC=C(C2C(CN(CC2)C(O)=O)OCC=2C=C3C=CC=CC3=CC=2)C=C1 INRAPKZZNLOEFY-UHFFFAOYSA-N 0.000 description 1
GATBVZWDPSFYPK-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-[3-(2-phenyl-1,3-dioxolan-2-yl)propoxy]phenyl]piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1OCCCC1(C=2C=CC=CC=2)OCCO1 GATBVZWDPSFYPK-UHFFFAOYSA-N 0.000 description 1
MFGRBKXYVZYKCC-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-[4-[[4-(2-trimethylsilylethoxymethoxy)benzoyl]oxymethyl]phenyl]piperidine-1-carboxylic acid Chemical compound C1=CC(OCOCC[Si](C)(C)C)=CC=C1C(=O)OCC1=CC=C(C2C(CN(CC2)C(O)=O)OCC=2C=C3C=CC=CC3=CC=2)C=C1 MFGRBKXYVZYKCC-UHFFFAOYSA-N 0.000 description 1
CLTKEDPZPCYCIO-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)-4-phenylpiperidine Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CNCCC1C1=CC=CC=C1 CLTKEDPZPCYCIO-UHFFFAOYSA-N 0.000 description 1
ZBAZATDSUZUCSR-UHFFFAOYSA-N 3-(naphthalen-2-ylmethoxy)piperidine Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CCCNC1 ZBAZATDSUZUCSR-UHFFFAOYSA-N 0.000 description 1
GQZNHBAQKXQYIV-UHFFFAOYSA-N 3-[(1,4-dimethoxynaphthalen-2-yl)methoxy]-4-[4-[3-[(2-methoxyphenyl)methoxy]propoxy]phenyl]piperidine Chemical group COC1=CC=CC=C1COCCCOC1=CC=C(C2C(CNCC2)OCC=2C(=C3C=CC=CC3=C(OC)C=2)OC)C=C1 GQZNHBAQKXQYIV-UHFFFAOYSA-N 0.000 description 1
ALTOXSGQLPIMPC-UHFFFAOYSA-N 3-[(1-methoxynaphthalen-2-yl)methoxy]-4-[4-(2-phenoxyethyl)phenyl]piperidine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC2=CC=CC=C2C(OC)=C1COC1CNCCC1C(C=C1)=CC=C1CCOC1=CC=CC=C1 ALTOXSGQLPIMPC-UHFFFAOYSA-N 0.000 description 1
CWAIVSJTIPVJOV-UHFFFAOYSA-N 3-[(2-methoxyphenyl)methoxy]-4-[4-(naphthalen-2-ylmethoxy)phenyl]piperidine-1-carboxylic acid Chemical compound COC1=CC=CC=C1COC1C(C=2C=CC(OCC=3C=C4C=CC=CC4=CC=3)=CC=2)CCN(C(O)=O)C1 CWAIVSJTIPVJOV-UHFFFAOYSA-N 0.000 description 1
REFNVRSTFHMFOP-UHFFFAOYSA-N 3-[(2-methoxyphenyl)methoxy]-4-[4-(naphthalen-2-ylmethoxy)phenyl]piperidine;hydrochloride Chemical compound Cl.COC1=CC=CC=C1COC1C(C=2C=CC(OCC=3C=C4C=CC=CC4=CC=3)=CC=2)CCNC1 REFNVRSTFHMFOP-UHFFFAOYSA-N 0.000 description 1
XRKGXMWNRJQBGA-UHFFFAOYSA-N 3-[(4-butoxynaphthalen-2-yl)methoxy]-4-(4-fluorophenyl)piperidine Chemical compound C=1C2=CC=CC=C2C(OCCCC)=CC=1COC1CNCCC1C1=CC=C(F)C=C1 XRKGXMWNRJQBGA-UHFFFAOYSA-N 0.000 description 1
VELNHVMQQHCIGS-UHFFFAOYSA-N 3-[(4-hydroxynaphthalen-2-yl)methoxy]-4-[4-(2-phenylmethoxyethoxy)phenyl]piperidine-1-carboxylic acid Chemical compound C=1C(O)=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1OCCOCC1=CC=CC=C1 VELNHVMQQHCIGS-UHFFFAOYSA-N 0.000 description 1
DIYXHZCXHYXFPZ-UHFFFAOYSA-N 3-[(4-methoxyphenyl)methoxy]-4-[3-(trifluoromethyl)phenyl]piperidine Chemical compound C1=CC(OC)=CC=C1COC1C(C=2C=C(C=CC=2)C(F)(F)F)CCNC1 DIYXHZCXHYXFPZ-UHFFFAOYSA-N 0.000 description 1
BIVDZIVOGLKRAO-UHFFFAOYSA-N 3-[(4-methoxyphenyl)methoxy]-4-phenylpiperidine Chemical compound C1=CC(OC)=CC=C1COC1C(C=2C=CC=CC=2)CCNC1 BIVDZIVOGLKRAO-UHFFFAOYSA-N 0.000 description 1
ZYORYPAYQUZBQL-UHFFFAOYSA-N 3-[(4-methoxyphenyl)methoxy]-4-phenylpiperidine-1-carboxylic acid Chemical compound C1=CC(OC)=CC=C1COC1C(C=2C=CC=CC=2)CCN(C(O)=O)C1 ZYORYPAYQUZBQL-UHFFFAOYSA-N 0.000 description 1
YMSJLGUNSQEQQK-UHFFFAOYSA-N 3-[(4-phenylmethoxynaphthalen-2-yl)methoxy]-4-[4-(2-trityloxyethyl)phenyl]piperidine-1-carboxylic acid Chemical compound C1N(C(=O)O)CCC(C=2C=CC(CCOC(C=3C=CC=CC=3)(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C1OCC(C=C1C=CC=CC1=1)=CC=1OCC1=CC=CC=C1 YMSJLGUNSQEQQK-UHFFFAOYSA-N 0.000 description 1
RNNQCNRKQICPJV-UHFFFAOYSA-N 3-[1-benzyl-3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenol Chemical compound OC1=CC=CC(C2C(CN(CC=3C=CC=CC=3)CC2)OCC=2C=C3C=CC=CC3=CC=2)=C1 RNNQCNRKQICPJV-UHFFFAOYSA-N 0.000 description 1
WKYSWVUYVVLYQA-UHFFFAOYSA-N 3-[2-[7-[[4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxymethyl]naphthalen-2-yl]oxyethoxy]propane-1,2-diol;hydrochloride Chemical compound Cl.C=1C2=CC(OCCOCC(O)CO)=CC=C2C=CC=1COC1CNCCC1C(C=C1)=CC=C1OCCCOCC1=CC=CC=C1 WKYSWVUYVVLYQA-UHFFFAOYSA-N 0.000 description 1
XYSNWLOMHIGJEE-UHFFFAOYSA-N 3-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenol Chemical compound OC1=CC=CC(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)=C1 XYSNWLOMHIGJEE-UHFFFAOYSA-N 0.000 description 1
OBVALKVRECDPNK-UHFFFAOYSA-N 3-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenoxy]propyl 2,2-dimethylpropanoate Chemical compound C1=CC(OCCCOC(=O)C(C)(C)C)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CNCC1 OBVALKVRECDPNK-UHFFFAOYSA-N 0.000 description 1
DVTPNFOMGMFJGR-UHFFFAOYSA-N 3-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]prop-2-enyl benzoate Chemical compound C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1C=CCOC(=O)C1=CC=CC=C1 DVTPNFOMGMFJGR-UHFFFAOYSA-N 0.000 description 1
JSOWXNNCMWIPAF-UHFFFAOYSA-N 3-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]propanenitrile;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC(CCC#N)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CNCC1 JSOWXNNCMWIPAF-UHFFFAOYSA-N 0.000 description 1
PJZUGRXNVXFQNC-UHFFFAOYSA-N 3-[5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxypropan-1-ol Chemical group OCCCOC1CNCC(OCC=2C=C3C=CC=CC3=CC=2)C1C(C=C1)=CC=C1OCCCOCC1=CC=CC=C1 PJZUGRXNVXFQNC-UHFFFAOYSA-N 0.000 description 1
TXTPYLJGPKDWNS-UHFFFAOYSA-N 3-[[1-[2-(1,3-dioxolan-2-yl)ethoxy]naphthalen-2-yl]methoxy]-4-(4-fluorophenyl)piperidine Chemical compound C1=CC(F)=CC=C1C1C(OCC=2C(=C3C=CC=CC3=CC=2)OCCC2OCCO2)CNCC1 TXTPYLJGPKDWNS-UHFFFAOYSA-N 0.000 description 1
BVWHBUIPAKVIPU-UHFFFAOYSA-N 3-[[3-[[4-(4-fluorophenyl)piperidin-3-yl]oxymethyl]naphthalen-1-yl]oxymethyl]pyridine Chemical compound C1=CC(F)=CC=C1C1C(OCC=2C=C3C=CC=CC3=C(OCC=3C=NC=CC=3)C=2)CNCC1 BVWHBUIPAKVIPU-UHFFFAOYSA-N 0.000 description 1
HRPRXMSYMSQQOY-UHFFFAOYSA-N 3-[[4-(1,3-benzodioxol-5-ylmethoxy)naphthalen-2-yl]methoxy]-4-(4-fluorophenyl)piperidine Chemical compound C1=CC(F)=CC=C1C1C(OCC=2C=C3C=CC=CC3=C(OCC=3C=C4OCOC4=CC=3)C=2)CNCC1 HRPRXMSYMSQQOY-UHFFFAOYSA-N 0.000 description 1
LJRQKECYNPVEFF-UHFFFAOYSA-N 3-[[4-(1,3-benzodioxol-5-ylmethoxy)naphthalen-2-yl]methoxy]-4-(4-fluorophenyl)piperidine-1-carboxylic acid Chemical compound C=1C(OCC=2C=C3OCOC3=CC=2)=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C1=CC=C(F)C=C1 LJRQKECYNPVEFF-UHFFFAOYSA-N 0.000 description 1
RZUGFTTWWYRYEG-UHFFFAOYSA-N 3-[[4-(2-cyclopropylethoxy)naphthalen-2-yl]methoxy]-4-(4-fluorophenyl)piperidine Chemical compound C1=CC(F)=CC=C1C1C(OCC=2C=C3C=CC=CC3=C(OCCC3CC3)C=2)CNCC1 RZUGFTTWWYRYEG-UHFFFAOYSA-N 0.000 description 1
HWYHCHSEKBUOSE-UHFFFAOYSA-N 3-[[4-(2-cyclopropylethoxy)naphthalen-2-yl]methoxy]-4-(4-fluorophenyl)piperidine-1-carboxylic acid Chemical compound C1N(C(=O)O)CCC(C=2C=CC(F)=CC=2)C1OCC(C=C1C=CC=CC1=1)=CC=1OCCC1CC1 HWYHCHSEKBUOSE-UHFFFAOYSA-N 0.000 description 1
SCLSLRSKQOMCHP-UHFFFAOYSA-N 3-[[4-(4-chlorophenyl)piperidin-3-yl]oxymethyl]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(OCC=2C=NC=CC=2)CNCC1 SCLSLRSKQOMCHP-UHFFFAOYSA-N 0.000 description 1
TVMPNEVFHRYCSK-UHFFFAOYSA-N 3-[[4-(4-fluorophenyl)piperidin-3-yl]oxymethyl]naphthalen-1-ol Chemical compound C=1C2=CC=CC=C2C(O)=CC=1COC1CNCCC1C1=CC=C(F)C=C1 TVMPNEVFHRYCSK-UHFFFAOYSA-N 0.000 description 1
SBMQWTABJUNHGA-UHFFFAOYSA-N 3-[[4-[2-(1,3-dioxolan-2-yl)ethoxy]naphthalen-2-yl]methoxy]-4-(4-fluorophenyl)piperidine Chemical compound C1=CC(F)=CC=C1C1C(OCC=2C=C3C=CC=CC3=C(OCCC3OCCO3)C=2)CNCC1 SBMQWTABJUNHGA-UHFFFAOYSA-N 0.000 description 1
WJRVBHKIMYODNG-UHFFFAOYSA-N 3-[[4-[4-(2-phenoxyethoxy)phenyl]piperidin-3-yl]oxymethyl]naphthalen-1-ol Chemical compound C=1C2=CC=CC=C2C(O)=CC=1COC1CNCCC1C(C=C1)=CC=C1OCCOC1=CC=CC=C1 WJRVBHKIMYODNG-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
OIIUMDSRAWZKOS-UHFFFAOYSA-N 3-hydroxy-4-(3-methoxycarbonylphenyl)piperidine-1-carboxylic acid Chemical compound COC(=O)C1=CC=CC(C2C(CN(CC2)C(O)=O)O)=C1 OIIUMDSRAWZKOS-UHFFFAOYSA-N 0.000 description 1
KNEITDLNMXUJCB-UHFFFAOYSA-N 3-hydroxy-4-(4-methoxycarbonylphenyl)piperidine-1-carboxylic acid Chemical compound C1=CC(C(=O)OC)=CC=C1C1C(O)CN(C(O)=O)CC1 KNEITDLNMXUJCB-UHFFFAOYSA-N 0.000 description 1
YQBXPHWIICUGLP-UHFFFAOYSA-N 3-hydroxy-4-(4-methylphenyl)piperidine-1-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1C(O)CN(C(O)=O)CC1 YQBXPHWIICUGLP-UHFFFAOYSA-N 0.000 description 1
QHLQGVZJGYKXKO-UHFFFAOYSA-N 3-hydroxy-4-(5,6,7,8-tetrahydronaphthalen-2-yl)piperidine-1-carboxylic acid Chemical compound OC1CN(C(O)=O)CCC1C1=CC=C(CCCC2)C2=C1 QHLQGVZJGYKXKO-UHFFFAOYSA-N 0.000 description 1
OUCVTQVRHWSLSD-UHFFFAOYSA-N 3-hydroxy-4-[3-(trifluoromethyl)phenyl]piperidine-1-carboxylic acid Chemical compound OC1CN(C(O)=O)CCC1C1=CC=CC(C(F)(F)F)=C1 OUCVTQVRHWSLSD-UHFFFAOYSA-N 0.000 description 1
HAHHQNQKEVBUNT-UHFFFAOYSA-N 3-hydroxy-4-[4-(2-phenoxyethoxy)phenyl]piperidine-1-carboxylic acid Chemical compound OC1CN(C(O)=O)CCC1C(C=C1)=CC=C1OCCOC1=CC=CC=C1 HAHHQNQKEVBUNT-UHFFFAOYSA-N 0.000 description 1
BUJWSPPFVDBZCP-UHFFFAOYSA-N 3-hydroxy-4-[4-(2-trityloxyethyl)phenyl]piperidine-1-carboxylic acid Chemical compound OC1CN(C(O)=O)CCC1C(C=C1)=CC=C1CCOC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BUJWSPPFVDBZCP-UHFFFAOYSA-N 0.000 description 1
LGGNIOGKJNAZGA-UHFFFAOYSA-N 3-hydroxy-4-[4-(hydroxymethyl)phenyl]piperidine-1-carboxylic acid Chemical compound C1=CC(CO)=CC=C1C1C(O)CN(C(O)=O)CC1 LGGNIOGKJNAZGA-UHFFFAOYSA-N 0.000 description 1
ZCBMACSJJSACPO-UHFFFAOYSA-N 3-hydroxy-4-[4-(naphthalen-2-ylmethoxy)phenyl]piperidine-1-carboxylic acid Chemical compound OC1CN(C(O)=O)CCC1C(C=C1)=CC=C1OCC1=CC=C(C=CC=C2)C2=C1 ZCBMACSJJSACPO-UHFFFAOYSA-N 0.000 description 1
NORVRFCMAYDBFK-UHFFFAOYSA-N 3-hydroxy-4-[4-[(5-phenyl-1,3,4-oxadiazol-2-yl)methoxy]phenyl]piperidine-1-carboxylic acid Chemical compound OC1CN(C(O)=O)CCC1C(C=C1)=CC=C1OCC1=NN=C(C=2C=CC=CC=2)O1 NORVRFCMAYDBFK-UHFFFAOYSA-N 0.000 description 1
CZVLVNDHSCNEOG-UHFFFAOYSA-N 3-hydroxy-4-[4-[3-(2-phenyl-1,3-dioxolan-2-yl)propoxy]phenyl]piperidine-1-carboxylic acid Chemical compound OC1CN(C(O)=O)CCC1C(C=C1)=CC=C1OCCCC1(C=2C=CC=CC=2)OCCO1 CZVLVNDHSCNEOG-UHFFFAOYSA-N 0.000 description 1
ZVOUUIQNXDQZMV-UHFFFAOYSA-N 3-naphthalen-2-yloxy-4-(4-phenylmethoxyphenyl)piperidine Chemical compound C=1C=C(C2C(CNCC2)OC=2C=C3C=CC=CC3=CC=2)C=CC=1OCC1=CC=CC=C1 ZVOUUIQNXDQZMV-UHFFFAOYSA-N 0.000 description 1
UIAGMCDKSXEBJQ-IBGZPJMESA-N 3-o-(2-methoxyethyl) 5-o-propan-2-yl (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)[C@H]1C1=CC=CC([N+]([O-])=O)=C1 UIAGMCDKSXEBJQ-IBGZPJMESA-N 0.000 description 1
GTJSMMDVCLTCIP-UHFFFAOYSA-N 4-(1,2-dihydroacenaphthylen-5-yl)-3-(naphthalen-2-ylmethoxy)piperidine Chemical compound C1=CC=CC2=CC(COC3C(CCNC3)C=3C=4C=CC=C5CCC(C=45)=CC=3)=CC=C21 GTJSMMDVCLTCIP-UHFFFAOYSA-N 0.000 description 1
VUWFEGZUOYYXNE-UHFFFAOYSA-N 4-(1,2-dihydroacenaphthylen-5-yl)piperidin-3-ol Chemical compound OC1CNCCC1C1=CC=C2C3=C1C=CC=C3CC2 VUWFEGZUOYYXNE-UHFFFAOYSA-N 0.000 description 1
MZUPZHLMMGZWCE-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-1,2,3,6-tetrahydropyridine Chemical compound C1=C2OCOC2=CC=C1C1=CCNCC1 MZUPZHLMMGZWCE-UHFFFAOYSA-N 0.000 description 1
IOGFOEFWUBITBR-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid Chemical compound O1COC2=C1C=CC(=C2)C=1CCN(CC=1)C(=O)O IOGFOEFWUBITBR-UHFFFAOYSA-N 0.000 description 1
MZCBLCCLXLPAEJ-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-3-(naphthalen-2-ylmethoxy)piperidine;hydrochloride Chemical compound Cl.C1=CC=CC2=CC(COC3C(CCNC3)C=3C=C4OCOC4=CC=3)=CC=C21 MZCBLCCLXLPAEJ-UHFFFAOYSA-N 0.000 description 1
DOINURWRUCEEOD-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-3-[(2-carbamoylphenyl)methoxy]piperidine-1-carboxylic acid Chemical compound NC(=O)C1=CC=CC=C1COC1C(C=2C=C3OCOC3=CC=2)CCN(C(O)=O)C1 DOINURWRUCEEOD-UHFFFAOYSA-N 0.000 description 1
UUFFABAJKABYOF-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-3-hydroxypiperidine-1-carboxylic acid Chemical compound OC1CN(C(O)=O)CCC1C1=CC=C(OCO2)C2=C1 UUFFABAJKABYOF-UHFFFAOYSA-N 0.000 description 1
UUHFPVGBVZXWGM-UHFFFAOYSA-N 4-(2-fluorophenyl)-3-(naphthalen-2-ylmethoxy)piperidine Chemical compound FC1=CC=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CNCC1 UUHFPVGBVZXWGM-UHFFFAOYSA-N 0.000 description 1
YEHORHVGKALBGI-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-3-(naphthalen-2-ylmethoxy)piperidine Chemical compound C1=C(OC)C(OC)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CNCC1 YEHORHVGKALBGI-UHFFFAOYSA-N 0.000 description 1
MEWUFLKNVNEUNK-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)-3-hydroxypiperidine-1-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC=C1C1C(O)CN(C(O)=O)CC1 MEWUFLKNVNEUNK-UHFFFAOYSA-N 0.000 description 1
GKFPBMJXFZKWCY-UHFFFAOYSA-N 4-(3,4-dimethoxyphenyl)piperidin-3-ol Chemical compound C1=C(OC)C(OC)=CC=C1C1C(O)CNCC1 GKFPBMJXFZKWCY-UHFFFAOYSA-N 0.000 description 1
RVNAXLPPTKPJKL-UHFFFAOYSA-N 4-(3-bromophenyl)-3-(naphthalen-2-ylmethoxy)piperidine Chemical compound BrC1=CC=CC(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)=C1 RVNAXLPPTKPJKL-UHFFFAOYSA-N 0.000 description 1
DLBBJGIOFXTZKW-UHFFFAOYSA-N 4-(3-bromophenyl)piperidin-3-ol Chemical compound OC1CNCCC1C1=CC=CC(Br)=C1 DLBBJGIOFXTZKW-UHFFFAOYSA-N 0.000 description 1
SAYLAYXYGATQEB-UHFFFAOYSA-N 4-(3-bromophenyl)piperidin-4-ol Chemical compound C=1C=CC(Br)=CC=1C1(O)CCNCC1 SAYLAYXYGATQEB-UHFFFAOYSA-N 0.000 description 1
VGRXIZPJJCEGBA-UHFFFAOYSA-N 4-(3-chlorophenyl)-1-methylpiperidin-3-ol Chemical compound OC1CN(C)CCC1C1=CC=CC(Cl)=C1 VGRXIZPJJCEGBA-UHFFFAOYSA-N 0.000 description 1
BYISFPMFJLIVKW-UHFFFAOYSA-N 4-(3-chlorophenyl)-3-[(4-methoxyphenyl)methoxy]piperidine Chemical compound C1=CC(OC)=CC=C1COC1C(C=2C=C(Cl)C=CC=2)CCNC1 BYISFPMFJLIVKW-UHFFFAOYSA-N 0.000 description 1
RAYCTZOMJOFKCD-UHFFFAOYSA-N 4-(3-fluorophenyl)-3-[(4-phenylmethoxynaphthalen-2-yl)methoxy]piperidine Chemical compound FC1=CC=CC(C2C(CNCC2)OCC=2C=C3C=CC=CC3=C(OCC=3C=CC=CC=3)C=2)=C1 RAYCTZOMJOFKCD-UHFFFAOYSA-N 0.000 description 1
JDADGZGZZYPPNF-UHFFFAOYSA-N 4-(3-fluorophenyl)piperidin-3-ol Chemical compound OC1CNCCC1C1=CC=CC(F)=C1 JDADGZGZZYPPNF-UHFFFAOYSA-N 0.000 description 1
UHWXWBPDHHMNSG-UHFFFAOYSA-N 4-(4-bromophenyl)-3-(naphthalen-2-ylmethoxy)piperidine Chemical compound C1=CC(Br)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CNCC1 UHWXWBPDHHMNSG-UHFFFAOYSA-N 0.000 description 1
CDVUJMMCOFHLGY-UHFFFAOYSA-N 4-(4-bromophenyl)-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C1=CC=C(Br)C=C1 CDVUJMMCOFHLGY-UHFFFAOYSA-N 0.000 description 1
CPBWKFQYSMTPEZ-UHFFFAOYSA-N 4-(4-bromophenyl)-3-hydroxypiperidine-1-carboxylic acid Chemical compound OC1CN(C(O)=O)CCC1C1=CC=C(Br)C=C1 CPBWKFQYSMTPEZ-UHFFFAOYSA-N 0.000 description 1
QNLXJYQUWCNYBH-UHFFFAOYSA-N 4-(4-bromophenyl)piperidin-4-ol Chemical compound C=1C=C(Br)C=CC=1C1(O)CCNCC1 QNLXJYQUWCNYBH-UHFFFAOYSA-N 0.000 description 1
SXOMHACGFSJBIO-UHFFFAOYSA-N 4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridine Chemical compound C1=CC(Cl)=CC=C1C1=CCNCC1 SXOMHACGFSJBIO-UHFFFAOYSA-N 0.000 description 1
NEPOYLVMRQRLAT-UHFFFAOYSA-N 4-(4-chlorophenyl)-1-methyl-3,6-dihydro-2h-pyridine Chemical compound C1N(C)CCC(C=2C=CC(Cl)=CC=2)=C1 NEPOYLVMRQRLAT-UHFFFAOYSA-N 0.000 description 1
QQEYGMISCSVZRU-UHFFFAOYSA-N 4-(4-chlorophenyl)-3-(naphthalen-1-ylmethoxy)piperidine Chemical compound C1=CC(Cl)=CC=C1C1C(OCC=2C3=CC=CC=C3C=CC=2)CNCC1 QQEYGMISCSVZRU-UHFFFAOYSA-N 0.000 description 1
BSWSCNZANCLPFL-UHFFFAOYSA-N 4-(4-chlorophenyl)-3-(naphthalen-2-ylmethoxy)piperidin-4-ol Chemical compound C1CNCC(OCC=2C=C3C=CC=CC3=CC=2)C1(O)C1=CC=C(Cl)C=C1 BSWSCNZANCLPFL-UHFFFAOYSA-N 0.000 description 1
WCNBLNYOLUDNKY-UHFFFAOYSA-N 4-(4-chlorophenyl)-3-(naphthalen-2-ylmethoxy)piperidine Chemical compound C1=CC(Cl)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CNCC1 WCNBLNYOLUDNKY-UHFFFAOYSA-N 0.000 description 1
PTYGLRODYXSJPV-UHFFFAOYSA-N 4-(4-chlorophenyl)-3-[(3,4-dichlorophenyl)methoxy]piperidine Chemical compound C1=CC(Cl)=CC=C1C1C(OCC=2C=C(Cl)C(Cl)=CC=2)CNCC1 PTYGLRODYXSJPV-UHFFFAOYSA-N 0.000 description 1
CHWQIDYTIZRMJH-UHFFFAOYSA-N 4-(4-chlorophenyl)-3-[(4-methoxyphenyl)methoxy]piperidin-4-ol Chemical compound C1=CC(OC)=CC=C1COC1C(C=2C=CC(Cl)=CC=2)(O)CCNC1 CHWQIDYTIZRMJH-UHFFFAOYSA-N 0.000 description 1
QOSHLYKXQRXKGC-UHFFFAOYSA-N 4-(4-chlorophenyl)-3-[(4-phenylphenyl)methoxy]piperidine Chemical compound C1=CC(Cl)=CC=C1C1C(OCC=2C=CC(=CC=2)C=2C=CC=CC=2)CNCC1 QOSHLYKXQRXKGC-UHFFFAOYSA-N 0.000 description 1
HJDQHTBLOMCTCR-UHFFFAOYSA-N 4-(4-chlorophenyl)-3-[(5,5,8,8-tetramethyl-6,7-dihydronaphthalen-2-yl)methoxy]piperidine Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1COC1CNCCC1C1=CC=C(Cl)C=C1 HJDQHTBLOMCTCR-UHFFFAOYSA-N 0.000 description 1
FGUWRGWTTRIZIS-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-hydroxy-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1(O)C1=CC=C(Cl)C=C1 FGUWRGWTTRIZIS-UHFFFAOYSA-N 0.000 description 1
LAARAUFNPCHZTI-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-hydroxy-3-[(4-methoxyphenyl)methoxy]piperidine-1-carboxylic acid Chemical compound C1=CC(OC)=CC=C1COC1C(C=2C=CC(Cl)=CC=2)(O)CCN(C(O)=O)C1 LAARAUFNPCHZTI-UHFFFAOYSA-N 0.000 description 1
LZAYOZUFUAMFLD-UHFFFAOYSA-N 4-(4-chlorophenyl)-4-hydroxypiperidine Chemical compound C=1C=C(Cl)C=CC=1C1(O)CCNCC1 LZAYOZUFUAMFLD-UHFFFAOYSA-N 0.000 description 1
KMULVGFXFSSMKH-UHFFFAOYSA-N 4-(4-chlorophenyl)piperidin-3-ol Chemical compound OC1CNCCC1C1=CC=C(Cl)C=C1 KMULVGFXFSSMKH-UHFFFAOYSA-N 0.000 description 1
WCIRSIWGSNDCRX-UHFFFAOYSA-N 4-(4-cyanophenyl)-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C1=CC=C(C#N)C=C1 WCIRSIWGSNDCRX-UHFFFAOYSA-N 0.000 description 1
CTTBTYWBXXWBMU-UHFFFAOYSA-N 4-(4-fluorophenyl)-1,2,3,6-tetrahydropyridine;hydrochloride Chemical compound Cl.C1=CC(F)=CC=C1C1=CCNCC1 CTTBTYWBXXWBMU-UHFFFAOYSA-N 0.000 description 1
YYYDIUFEULMVFV-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-(5,6,7,8-tetrahydronaphthalen-2-ylmethoxy)piperidine Chemical compound C1=CC(F)=CC=C1C1C(OCC=2C=C3CCCCC3=CC=2)CNCC1 YYYDIUFEULMVFV-UHFFFAOYSA-N 0.000 description 1
ARINFRPPOWCGSG-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-(5,6,7,8-tetrahydronaphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C=1C=C2CCCCC2=CC=1COC1CN(C(=O)O)CCC1C1=CC=C(F)C=C1 ARINFRPPOWCGSG-UHFFFAOYSA-N 0.000 description 1
ZWAFVCGXLVUNKD-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[(1-hydroxynaphthalen-2-yl)methoxy]piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=C(O)C=1COC1CN(C(=O)O)CCC1C1=CC=C(F)C=C1 ZWAFVCGXLVUNKD-UHFFFAOYSA-N 0.000 description 1
ZWMKBMVRPNSTFC-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[(1-methoxynaphthalen-2-yl)methoxy]piperidine Chemical compound C1=CC2=CC=CC=C2C(OC)=C1COC1CNCCC1C1=CC=C(F)C=C1 ZWMKBMVRPNSTFC-UHFFFAOYSA-N 0.000 description 1
FUKKMDSTLGPRHZ-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[(1-phenylmethoxynaphthalen-2-yl)methoxy]piperidine Chemical compound C1=CC(F)=CC=C1C1C(OCC=2C(=C3C=CC=CC3=CC=2)OCC=2C=CC=CC=2)CNCC1 FUKKMDSTLGPRHZ-UHFFFAOYSA-N 0.000 description 1
AMVPGCKIXWCTPU-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[(3-methoxynaphthalen-2-yl)methoxy]piperidine Chemical compound COC1=CC2=CC=CC=C2C=C1COC1CNCCC1C1=CC=C(F)C=C1 AMVPGCKIXWCTPU-UHFFFAOYSA-N 0.000 description 1
KBYSCARPLAIWBI-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[(3-phenylmethoxyphenyl)methoxy]piperidine Chemical compound C1=CC(F)=CC=C1C1C(OCC=2C=C(OCC=3C=CC=CC=3)C=CC=2)CNCC1 KBYSCARPLAIWBI-UHFFFAOYSA-N 0.000 description 1
JFPWOEDIRXKKLW-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[(4-methoxynaphthalen-2-yl)methoxy]piperidine Chemical compound C=1C2=CC=CC=C2C(OC)=CC=1COC1CNCCC1C1=CC=C(F)C=C1 JFPWOEDIRXKKLW-UHFFFAOYSA-N 0.000 description 1
MBVMAWXTAISZQS-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[(4-methoxyphenyl)methoxy]piperidine Chemical compound C1=CC(OC)=CC=C1COC1C(C=2C=CC(F)=CC=2)CCNC1 MBVMAWXTAISZQS-UHFFFAOYSA-N 0.000 description 1
ZGYSKNTXDRCQBO-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[(4-phenylmethoxynaphthalen-2-yl)methoxy]piperidine Chemical compound C1=CC(F)=CC=C1C1C(OCC=2C=C3C=CC=CC3=C(OCC=3C=CC=CC=3)C=2)CNCC1 ZGYSKNTXDRCQBO-UHFFFAOYSA-N 0.000 description 1
DLEHGRPFYYISIU-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[(4-phenylmethoxynaphthalen-2-yl)methoxy]piperidine-1-carboxylic acid Chemical compound C1N(C(=O)O)CCC(C=2C=CC(F)=CC=2)C1OCC(C=C1C=CC=CC1=1)=CC=1OCC1=CC=CC=C1 DLEHGRPFYYISIU-UHFFFAOYSA-N 0.000 description 1
HLKSCAJHXVELAQ-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[(5-methoxynaphthalen-2-yl)methoxy]piperidine Chemical compound C=1C=C2C(OC)=CC=CC2=CC=1COC1CNCCC1C1=CC=C(F)C=C1 HLKSCAJHXVELAQ-UHFFFAOYSA-N 0.000 description 1
PQBMBXOMUCORDR-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[(5-phenylmethoxynaphthalen-2-yl)methoxy]piperidine Chemical compound C1=CC(F)=CC=C1C1C(OCC=2C=C3C=CC=C(OCC=4C=CC=CC=4)C3=CC=2)CNCC1 PQBMBXOMUCORDR-UHFFFAOYSA-N 0.000 description 1
BFXODBQXOHZOOM-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[(6-methoxynaphthalen-2-yl)methoxy]piperidine Chemical compound C1=CC2=CC(OC)=CC=C2C=C1COC1CNCCC1C1=CC=C(F)C=C1 BFXODBQXOHZOOM-UHFFFAOYSA-N 0.000 description 1
QVMHPYDYAANPBP-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[(7-methoxynaphthalen-2-yl)methoxy]piperidine Chemical compound C=1C2=CC(OC)=CC=C2C=CC=1COC1CNCCC1C1=CC=C(F)C=C1 QVMHPYDYAANPBP-UHFFFAOYSA-N 0.000 description 1
QWYRKPKEEGODHS-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[(7-phenylmethoxynaphthalen-2-yl)methoxy]piperidine Chemical compound C1=CC(F)=CC=C1C1C(OCC=2C=C3C=C(OCC=4C=CC=CC=4)C=CC3=CC=2)CNCC1 QWYRKPKEEGODHS-UHFFFAOYSA-N 0.000 description 1
NAOPGXNLLLOYSR-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[(8-methoxynaphthalen-2-yl)methoxy]piperidine Chemical compound C1=C2C(OC)=CC=CC2=CC=C1COC1CNCCC1C1=CC=C(F)C=C1 NAOPGXNLLLOYSR-UHFFFAOYSA-N 0.000 description 1
RVQCKBSEZUIWFE-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[(8-phenylmethoxynaphthalen-2-yl)methoxy]piperidine Chemical compound C1=CC(F)=CC=C1C1C(OCC=2C=C3C(OCC=4C=CC=CC=4)=CC=CC3=CC=2)CNCC1 RVQCKBSEZUIWFE-UHFFFAOYSA-N 0.000 description 1
SPZRRYWQTMXFAX-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[(8-phenylmethoxynaphthalen-2-yl)methoxy]piperidine-1-carboxylic acid Chemical compound C1N(C(=O)O)CCC(C=2C=CC(F)=CC=2)C1OCC(C=C12)=CC=C1C=CC=C2OCC1=CC=CC=C1 SPZRRYWQTMXFAX-UHFFFAOYSA-N 0.000 description 1
CJMQZKBIAOXELJ-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[[1-(2-trimethylsilylethoxymethoxy)naphthalen-2-yl]methoxy]piperidine-1-carboxylic acid Chemical compound C1=CC2=CC=CC=C2C(OCOCC[Si](C)(C)C)=C1COC1CN(C(O)=O)CCC1C1=CC=C(F)C=C1 CJMQZKBIAOXELJ-UHFFFAOYSA-N 0.000 description 1
PGNGFWSBLZCFKE-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[[3-(2-trimethylsilylethoxymethoxy)naphthalen-2-yl]methoxy]piperidine-1-carboxylic acid Chemical compound C[Si](C)(C)CCOCOC1=CC2=CC=CC=C2C=C1COC1CN(C(O)=O)CCC1C1=CC=C(F)C=C1 PGNGFWSBLZCFKE-UHFFFAOYSA-N 0.000 description 1
MHQAPVVDHIZHSO-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[[4-(2-hydroxyethoxy)naphthalen-2-yl]methoxy]piperidine-1-carboxylic acid Chemical compound C=1C2=CC=CC=C2C(OCCO)=CC=1COC1CN(C(O)=O)CCC1C1=CC=C(F)C=C1 MHQAPVVDHIZHSO-UHFFFAOYSA-N 0.000 description 1
BSJJAROSMDZLRM-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[[4-(2-methoxyethoxy)naphthalen-2-yl]methoxy]piperidine Chemical compound C=1C2=CC=CC=C2C(OCCOC)=CC=1COC1CNCCC1C1=CC=C(F)C=C1 BSJJAROSMDZLRM-UHFFFAOYSA-N 0.000 description 1
VKIIXRSCGILLGM-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[[4-(2-methylpropoxy)naphthalen-2-yl]methoxy]piperidine Chemical compound C=1C2=CC=CC=C2C(OCC(C)C)=CC=1COC1CNCCC1C1=CC=C(F)C=C1 VKIIXRSCGILLGM-UHFFFAOYSA-N 0.000 description 1
CHKJTFABPNJMHF-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[[4-(2-trimethylsilylethoxymethoxy)naphthalen-2-yl]methoxy]piperidine-1-carboxylic acid Chemical compound C=1C2=CC=CC=C2C(OCOCC[Si](C)(C)C)=CC=1COC1CN(C(O)=O)CCC1C1=CC=C(F)C=C1 CHKJTFABPNJMHF-UHFFFAOYSA-N 0.000 description 1
WHMSTTZNASFWJY-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[[4-(3-methoxypropoxy)naphthalen-2-yl]methoxy]piperidine Chemical compound C=1C2=CC=CC=C2C(OCCCOC)=CC=1COC1CNCCC1C1=CC=C(F)C=C1 WHMSTTZNASFWJY-UHFFFAOYSA-N 0.000 description 1
RMUTYRBLLYNEBJ-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[[4-[(2-methoxyphenyl)methoxy]naphthalen-2-yl]methoxy]piperidine Chemical compound COC1=CC=CC=C1COC1=CC(COC2C(CCNC2)C=2C=CC(F)=CC=2)=CC2=CC=CC=C12 RMUTYRBLLYNEBJ-UHFFFAOYSA-N 0.000 description 1
QMDLHDWWMCTLGZ-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[[4-[(3-methoxyphenyl)methoxy]naphthalen-2-yl]methoxy]piperidine Chemical compound COC1=CC=CC(COC=2C3=CC=CC=C3C=C(COC3C(CCNC3)C=3C=CC(F)=CC=3)C=2)=C1 QMDLHDWWMCTLGZ-UHFFFAOYSA-N 0.000 description 1
AMUJASZQFZBODU-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[[4-[(4-methoxyphenyl)methoxy]naphthalen-2-yl]methoxy]piperidine Chemical compound C1=CC(OC)=CC=C1COC1=CC(COC2C(CCNC2)C=2C=CC(F)=CC=2)=CC2=CC=CC=C12 AMUJASZQFZBODU-UHFFFAOYSA-N 0.000 description 1
QTLZIZULLGARAJ-UHFFFAOYSA-N 4-(4-fluorophenyl)-3-[naphthalen-2-yl(1-phenylethoxy)methoxy]piperidine-1-carboxylic acid Chemical compound CC(C1=CC=CC=C1)OC(C2=CC3=CC=CC=C3C=C2)OC4CN(CCC4C5=CC=C(C=C5)F)C(=O)O QTLZIZULLGARAJ-UHFFFAOYSA-N 0.000 description 1
CWQAJUGYGJZUFG-UHFFFAOYSA-N 4-(4-hydroxyphenyl)piperidin-3-ol Chemical compound OC1CNCCC1C1=CC=C(O)C=C1 CWQAJUGYGJZUFG-UHFFFAOYSA-N 0.000 description 1
JCTPJCPNMPELHI-UHFFFAOYSA-N 4-(4-methoxycarbonylphenyl)-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C1=CC(C(=O)OC)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(C(O)=O)CC1 JCTPJCPNMPELHI-UHFFFAOYSA-N 0.000 description 1
YZMDTJZJPBEFNU-UHFFFAOYSA-N 4-(5,6,7,8-tetrahydronaphthalen-2-yl)piperidin-3-ol Chemical compound OC1CNCCC1C1=CC=C(CCCC2)C2=C1 YZMDTJZJPBEFNU-UHFFFAOYSA-N 0.000 description 1
AFMZZMPJGPDNBC-SBPNQFBHSA-N 4-[(3s,4s,5r)-5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxybutan-1-ol Chemical compound C1=CC([C@@H]2[C@@H](OCC=3C=C4C=CC=CC4=CC=3)CNC[C@H]2OCCCCO)=CC=C1OCCCOCC1=CC=CC=C1 AFMZZMPJGPDNBC-SBPNQFBHSA-N 0.000 description 1
LHDYMPLPHNVWSO-UHFFFAOYSA-N 4-[1-[(2-methylpropan-2-yl)oxycarbonyl]-3-(naphthalen-2-ylmethoxy)piperidin-4-yl]benzoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(C(O)=O)C=C1 LHDYMPLPHNVWSO-UHFFFAOYSA-N 0.000 description 1
QPDCVHOOSRJVPI-UHFFFAOYSA-N 4-[2-[5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxyethyl]morpholine Chemical group C=1C=C(C2C(CNCC2OCCN2CCOCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCCOCC1=CC=CC=C1 QPDCVHOOSRJVPI-UHFFFAOYSA-N 0.000 description 1
BGAWAKUWOBKLJF-UHFFFAOYSA-N 4-[2-[[5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]methoxy]ethyl]morpholine Chemical group C=1C=C(C2C(CNCC2COCCN2CCOCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCCOCC1=CC=CC=C1 BGAWAKUWOBKLJF-UHFFFAOYSA-N 0.000 description 1
OYVZVJZSECAHHE-UHFFFAOYSA-N 4-[3-(benzylcarbamoyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1 OYVZVJZSECAHHE-UHFFFAOYSA-N 0.000 description 1
ZBGFHKYQKWIUIQ-UHFFFAOYSA-N 4-[3-(hydroxymethyl)phenyl]-3-[(4-phenylmethoxynaphthalen-2-yl)methoxy]piperidine-1-carboxylic acid Chemical compound OCC1=CC=CC(C2C(CN(CC2)C(O)=O)OCC=2C=C3C=CC=CC3=C(OCC=3C=CC=CC=3)C=2)=C1 ZBGFHKYQKWIUIQ-UHFFFAOYSA-N 0.000 description 1
YWGBECYECPFSCF-UHFFFAOYSA-N 4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]-n-(3-oxo-3-phenylpropyl)benzamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1C(=O)NCCC(=O)C1=CC=CC=C1 YWGBECYECPFSCF-UHFFFAOYSA-N 0.000 description 1
PTJRKLASCXDYNX-UHFFFAOYSA-N 4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]-n-phenacylbenzamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1C(=O)NCC(=O)C1=CC=CC=C1 PTJRKLASCXDYNX-UHFFFAOYSA-N 0.000 description 1
IFYKRMQORZOMNY-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenyl]-1,2,3,6-tetrahydropyridine Chemical compound FC(F)(F)C1=CC=CC(C=2CCNCC=2)=C1 IFYKRMQORZOMNY-UHFFFAOYSA-N 0.000 description 1
GRVSNFYUBFPYMK-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenyl]piperidin-3-ol Chemical compound OC1CNCCC1C1=CC=CC(C(F)(F)F)=C1 GRVSNFYUBFPYMK-UHFFFAOYSA-N 0.000 description 1
ILKPZCKFWLTEBQ-UHFFFAOYSA-N 4-[3-(trifluoromethyl)phenyl]piperidin-4-ol Chemical compound C=1C=CC(C(F)(F)F)=CC=1C1(O)CCNCC1 ILKPZCKFWLTEBQ-UHFFFAOYSA-N 0.000 description 1
VURSJBCXCKTPCT-UHFFFAOYSA-N 4-[3-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenoxy]propyl]morpholine Chemical compound C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCCN1CCOCC1 VURSJBCXCKTPCT-UHFFFAOYSA-N 0.000 description 1
URYMLRVRAKFDNW-UHFFFAOYSA-N 4-[4-(1,3-benzothiazol-2-ylsulfanylmethyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C1=CC=C2SC(SCC3=CC=C(C=C3)C3CCN(CC3OCC=3C=C4C=CC=CC4=CC=3)C(=O)O)=NC2=C1 URYMLRVRAKFDNW-UHFFFAOYSA-N 0.000 description 1
YCSMIYXOPDLAGX-UHFFFAOYSA-N 4-[4-(2,2-dimethylpropanoyloxymethyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C1=CC(COC(=O)C(C)(C)C)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(C(O)=O)CC1 YCSMIYXOPDLAGX-UHFFFAOYSA-N 0.000 description 1
SDPZAFAQVAAFSH-UHFFFAOYSA-N 4-[4-(2-aminoethoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C1=CC(OCCN)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(C(O)=O)CC1 SDPZAFAQVAAFSH-UHFFFAOYSA-N 0.000 description 1
UDAGKMXCJUPXPY-UHFFFAOYSA-N 4-[4-(2-azidoethoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C1=CC=C(OCCN=[N+]=[N-])C=C1 UDAGKMXCJUPXPY-UHFFFAOYSA-N 0.000 description 1
IDLUMDITQKJBLY-UHFFFAOYSA-N 4-[4-(2-benzoyloxyethoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1OCCOC(=O)C1=CC=CC=C1 IDLUMDITQKJBLY-UHFFFAOYSA-N 0.000 description 1
DABSOZYXIGBQKZ-UHFFFAOYSA-N 4-[4-(2-hydroxyethyl)phenyl]-3-[(1-methoxynaphthalen-2-yl)methoxy]piperidine-1-carboxylic acid Chemical compound C1=CC2=CC=CC=C2C(OC)=C1COC1CN(C(O)=O)CCC1C1=CC=C(CCO)C=C1 DABSOZYXIGBQKZ-UHFFFAOYSA-N 0.000 description 1
ZRBSCPPJMXCLJP-UHFFFAOYSA-N 4-[4-(2-hydroxyethyl)phenyl]-3-[(4-phenylmethoxynaphthalen-2-yl)methoxy]piperidine-1-carboxylic acid Chemical compound C1=CC(CCO)=CC=C1C1C(OCC=2C=C3C=CC=CC3=C(OCC=3C=CC=CC=3)C=2)CN(C(O)=O)CC1 ZRBSCPPJMXCLJP-UHFFFAOYSA-N 0.000 description 1
KTUGVRUBVZWOPO-UHFFFAOYSA-N 4-[4-(2-hydroxyethyl)phenyl]piperidin-3-ol Chemical compound C1=CC(CCO)=CC=C1C1C(O)CNCC1 KTUGVRUBVZWOPO-UHFFFAOYSA-N 0.000 description 1
TZXJAJORSJDXOQ-UHFFFAOYSA-N 4-[4-(2-methoxyethyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine Chemical compound COCCC1=CC=C(C=C1)C1C(CNCC1)OCC1=CC2=CC=CC=C2C=C1 TZXJAJORSJDXOQ-UHFFFAOYSA-N 0.000 description 1
YAEAKMNTQDGEFS-UHFFFAOYSA-N 4-[4-(2-phenylmethoxyethoxy)phenyl]-3-[(4-phenylmethoxynaphthalen-2-yl)methoxy]piperidine Chemical compound C=1C=CC=CC=1COCCOC(C=C1)=CC=C1C1CCNCC1OCC(C=C1C=CC=CC1=1)=CC=1OCC1=CC=CC=C1 YAEAKMNTQDGEFS-UHFFFAOYSA-N 0.000 description 1
XKSHFWJKYQIDCW-UHFFFAOYSA-N 4-[4-(3-benzoyloxyprop-1-enyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1C=CCOC(=O)C1=CC=CC=C1 XKSHFWJKYQIDCW-UHFFFAOYSA-N 0.000 description 1
CFHSQKZQNNMRCY-UHFFFAOYSA-N 4-[4-(3-ethoxy-3-oxoprop-1-enyl)phenyl]-3-hydroxypiperidine-1-carboxylic acid Chemical compound C1=CC(C=CC(=O)OCC)=CC=C1C1C(O)CN(C(O)=O)CC1 CFHSQKZQNNMRCY-UHFFFAOYSA-N 0.000 description 1
AGIZCSRKVDPIGD-UHFFFAOYSA-N 4-[4-(3-ethoxy-3-oxopropyl)phenyl]-3-hydroxypiperidine-1-carboxylic acid Chemical compound C1=CC(CCC(=O)OCC)=CC=C1C1C(O)CN(C(O)=O)CC1 AGIZCSRKVDPIGD-UHFFFAOYSA-N 0.000 description 1
QVEMGCAHGWZBMR-UHFFFAOYSA-N 4-[4-(3-methoxyprop-1-enyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine Chemical compound C1=CC(C=CCOC)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CNCC1 QVEMGCAHGWZBMR-UHFFFAOYSA-N 0.000 description 1
HDWUJRABUYGVTE-UHFFFAOYSA-N 4-[4-(4-hydroxy-4-phenylbutoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C=1C=C(C2C(CN(CC2)C(O)=O)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCCC(O)C1=CC=CC=C1 HDWUJRABUYGVTE-UHFFFAOYSA-N 0.000 description 1
CUJUTONCOWBLOC-UHFFFAOYSA-N 4-[4-(4-methoxy-4-phenylbutoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine Chemical compound C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCCC(OC)C1=CC=CC=C1 CUJUTONCOWBLOC-UHFFFAOYSA-N 0.000 description 1
XPNOXODAMBQPIP-UHFFFAOYSA-N 4-[4-(aminomethyl)phenyl]-3-[[4-(2-trimethylsilylethoxymethoxy)naphthalen-2-yl]methoxy]piperidine-1-carboxylic acid Chemical compound C=1C2=CC=CC=C2C(OCOCC[Si](C)(C)C)=CC=1COC1CN(C(O)=O)CCC1C1=CC=C(CN)C=C1 XPNOXODAMBQPIP-UHFFFAOYSA-N 0.000 description 1
ZAAPZDMGNOWJRC-UHFFFAOYSA-N 4-[4-(benzamidomethyl)phenyl]-3-[[4-(2-trimethylsilylethoxymethoxy)naphthalen-2-yl]methoxy]piperidine-1-carboxylic acid Chemical compound C=1C2=CC=CC=C2C(OCOCC[Si](C)(C)C)=CC=1COC1CN(C(O)=O)CCC1C(C=C1)=CC=C1CNC(=O)C1=CC=CC=C1 ZAAPZDMGNOWJRC-UHFFFAOYSA-N 0.000 description 1
SPNQCTBNIWJBAW-UHFFFAOYSA-N 4-[4-(benzenesulfonamidomethyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1CNS(=O)(=O)C1=CC=CC=C1 SPNQCTBNIWJBAW-UHFFFAOYSA-N 0.000 description 1
HJLRIQJTPQAPSK-UHFFFAOYSA-N 4-[4-(benzoyloxymethyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1COC(=O)C1=CC=CC=C1 HJLRIQJTPQAPSK-UHFFFAOYSA-N 0.000 description 1
WCLAFFPRVFWOTG-UHFFFAOYSA-N 4-[4-(hydroxymethyl)phenyl]-3-[(1-methoxynaphthalen-2-yl)methoxy]piperidine-1-carboxylic acid Chemical compound C1=CC2=CC=CC=C2C(OC)=C1COC1CN(C(O)=O)CCC1C1=CC=C(CO)C=C1 WCLAFFPRVFWOTG-UHFFFAOYSA-N 0.000 description 1
UEVRDQXVHOYQBD-UHFFFAOYSA-N 4-[4-[(4-methoxyphenoxy)methyl]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine Chemical compound C1=CC(OC)=CC=C1OCC1=CC=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=C1 UEVRDQXVHOYQBD-UHFFFAOYSA-N 0.000 description 1
BOACAWGAPNXDKP-UHFFFAOYSA-N 4-[4-[2-(1,3-benzodioxole-5-carbonyloxy)ethoxy]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C1=C2OCOC2=CC(C(=O)OCCOC2=CC=C(C=C2)C2CCN(CC2OCC=2C=C3C=CC=CC3=CC=2)C(=O)O)=C1 BOACAWGAPNXDKP-UHFFFAOYSA-N 0.000 description 1
RELYQEMMFCRSSN-UHFFFAOYSA-N 4-[4-[2-(2,6-dichlorobenzoyl)oxyethyl]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1CCOC(=O)C1=C(Cl)C=CC=C1Cl RELYQEMMFCRSSN-UHFFFAOYSA-N 0.000 description 1
XNBMIRGUASDCND-UHFFFAOYSA-N 4-[4-[2-(2,6-dimethoxybenzoyl)oxyethyl]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound COC1=CC=CC(OC)=C1C(=O)OCCC1=CC=C(C2C(CN(CC2)C(O)=O)OCC=2C=C3C=CC=CC3=CC=2)C=C1 XNBMIRGUASDCND-UHFFFAOYSA-N 0.000 description 1
XNTZUULIIJBVEW-UHFFFAOYSA-N 4-[4-[2-(2-chlorobenzoyl)oxyethoxy]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1OCCOC(=O)C1=CC=CC=C1Cl XNTZUULIIJBVEW-UHFFFAOYSA-N 0.000 description 1
PCNXHCCXCSUDIG-UHFFFAOYSA-N 4-[4-[2-(2-methoxybenzoyl)oxyethyl]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound COC1=CC=CC=C1C(=O)OCCC1=CC=C(C2C(CN(CC2)C(O)=O)OCC=2C=C3C=CC=CC3=CC=2)C=C1 PCNXHCCXCSUDIG-UHFFFAOYSA-N 0.000 description 1
FUKYARBYNBXKRD-UHFFFAOYSA-N 4-[4-[2-(3-methoxybenzoyl)oxyethyl]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound COC1=CC=CC(C(=O)OCCC=2C=CC(=CC=2)C2C(CN(CC2)C(O)=O)OCC=2C=C3C=CC=CC3=CC=2)=C1 FUKYARBYNBXKRD-UHFFFAOYSA-N 0.000 description 1
IDAFOUVOZIUUAJ-UHFFFAOYSA-N 4-[4-[2-(4-bromophenoxy)ethoxy]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine Chemical compound C1=CC(Br)=CC=C1OCCOC1=CC=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=C1 IDAFOUVOZIUUAJ-UHFFFAOYSA-N 0.000 description 1
PRZBTAUHOLUCBZ-UHFFFAOYSA-N 4-[4-[2-(benzenesulfonyl)ethoxy]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine Chemical compound C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCS(=O)(=O)C1=CC=CC=C1 PRZBTAUHOLUCBZ-UHFFFAOYSA-N 0.000 description 1
XIQPGIYRVGNPQF-UHFFFAOYSA-N 4-[4-[2-(benzenesulfonyl)ethyl]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine;hydrochloride Chemical compound Cl.C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1CCS(=O)(=O)C1=CC=CC=C1 XIQPGIYRVGNPQF-UHFFFAOYSA-N 0.000 description 1
JFRGZJARKYIPGB-UHFFFAOYSA-N 4-[4-[2-(furan-3-carbonyloxy)ethoxy]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1OCCOC(=O)C=1C=COC=1 JFRGZJARKYIPGB-UHFFFAOYSA-N 0.000 description 1
IAHKCPPSCBTIRY-UHFFFAOYSA-N 4-[4-[2-[2-(benzoyloxymethyl)benzoyl]oxyethoxy]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1OCCOC(=O)C1=CC=CC=C1COC(=O)C1=CC=CC=C1 IAHKCPPSCBTIRY-UHFFFAOYSA-N 0.000 description 1
QCSBCZOAWQCNPP-UHFFFAOYSA-N 4-[4-[3-(1-benzothiophen-5-ylmethoxy)piperidin-4-yl]phenoxy]-1-phenylbutan-1-ol Chemical compound C=1C=C(C2C(CNCC2)OCC=2C=C3C=CSC3=CC=2)C=CC=1OCCCC(O)C1=CC=CC=C1 QCSBCZOAWQCNPP-UHFFFAOYSA-N 0.000 description 1
SBGDCMVHYNVGCF-UHFFFAOYSA-N 4-[4-[3-(2,2-dimethylpropanoyloxy)propoxy]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C1=CC(OCCCOC(=O)C(C)(C)C)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(C(O)=O)CC1 SBGDCMVHYNVGCF-UHFFFAOYSA-N 0.000 description 1
RLEPNMCLGHYLCM-UHFFFAOYSA-N 4-[4-[3-(2-chlorobenzoyl)oxypropyl]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylic acid Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)O)CCC1C(C=C1)=CC=C1CCCOC(=O)C1=CC=CC=C1Cl RLEPNMCLGHYLCM-UHFFFAOYSA-N 0.000 description 1
VONWBDVWUBHMPR-UHFFFAOYSA-N 4-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenoxy]-1-phenylbutan-1-ol Chemical compound C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCCC(O)C1=CC=CC=C1 VONWBDVWUBHMPR-UHFFFAOYSA-N 0.000 description 1
AFMZZMPJGPDNBC-UHFFFAOYSA-N 4-[5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]oxybutan-1-ol Chemical group OCCCCOC1CNCC(OCC=2C=C3C=CC=CC3=CC=2)C1C(C=C1)=CC=C1OCCCOCC1=CC=CC=C1 AFMZZMPJGPDNBC-UHFFFAOYSA-N 0.000 description 1
SFMKMVCSYTWISP-UHFFFAOYSA-N 4-[[3-[[4-(4-fluorophenyl)piperidin-3-yl]oxymethyl]naphthalen-1-yl]oxymethyl]pyridine Chemical compound C1=CC(F)=CC=C1C1C(OCC=2C=C3C=CC=CC3=C(OCC=3C=CN=CC=3)C=2)CNCC1 SFMKMVCSYTWISP-UHFFFAOYSA-N 0.000 description 1
CKFYLSMACGXFQB-UHFFFAOYSA-N 4-[[5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]methylsulfanyl]pyridine Chemical group C=1C=C(C2C(CNCC2CSC=2C=CN=CC=2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCCOCC1=CC=CC=C1 CKFYLSMACGXFQB-UHFFFAOYSA-N 0.000 description 1
RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
XILWHXOHGQCBIY-UHFFFAOYSA-N 4-cyclohexyl-3-(naphthalen-2-ylmethoxy)piperidine Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CNCCC1C1CCCCC1 XILWHXOHGQCBIY-UHFFFAOYSA-N 0.000 description 1
125000005274 4-hydroxybenzoic acid group Chemical group 0.000 description 1
YXQXYXXISMKTOX-UHFFFAOYSA-N 4-methoxy-2-methylquinazoline Chemical compound C1=CC=C2C(OC)=NC(C)=NC2=C1 YXQXYXXISMKTOX-UHFFFAOYSA-N 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
ANCPKAVEVIEXIZ-UHFFFAOYSA-N 4-naphthalen-1-yl-3-(naphthalen-2-ylmethoxy)piperidine Chemical compound C1=CC=CC2=CC(COC3C(CCNC3)C=3C4=CC=CC=C4C=CC=3)=CC=C21 ANCPKAVEVIEXIZ-UHFFFAOYSA-N 0.000 description 1
XXGGUXHEAAWLJD-UHFFFAOYSA-N 4-naphthalen-1-ylpiperidin-3-ol Chemical compound OC1CNCCC1C1=CC=CC2=CC=CC=C12 XXGGUXHEAAWLJD-UHFFFAOYSA-N 0.000 description 1
FARRLQPEWDADQF-UHFFFAOYSA-N 4-naphthalen-2-yl-1,2,3,6-tetrahydropyridine Chemical compound C1NCCC(C=2C=C3C=CC=CC3=CC=2)=C1 FARRLQPEWDADQF-UHFFFAOYSA-N 0.000 description 1
MLAFFBJWFRHJQB-UHFFFAOYSA-N 4-naphthalen-2-yl-3,6-dihydro-2H-pyridine-1-carboxylic acid Chemical compound C1=C(C=CC2=CC=CC=C12)C=1CCN(CC=1)C(=O)O MLAFFBJWFRHJQB-UHFFFAOYSA-N 0.000 description 1
IIFZHMJPRQRHLV-UHFFFAOYSA-N 4-naphthalen-2-yl-3-(naphthalen-2-ylmethoxy)piperidine Chemical compound C1=CC=CC2=CC(COC3C(CCNC3)C=3C=C4C=CC=CC4=CC=3)=CC=C21 IIFZHMJPRQRHLV-UHFFFAOYSA-N 0.000 description 1
OMPXTQYWYRWWPH-UHFFFAOYSA-N 4-phenyl-1,2,3,6-tetrahydropyridine Chemical compound C1NCCC(C=2C=CC=CC=2)=C1 OMPXTQYWYRWWPH-UHFFFAOYSA-N 0.000 description 1
NTPYAXLOZIFOSG-UHFFFAOYSA-N 4-phenyl-3-[[2-[(pyridine-3-carbonylamino)methyl]phenyl]methoxy]piperidine-1-carboxylic acid Chemical compound C1N(C(=O)O)CCC(C=2C=CC=CC=2)C1OCC1=CC=CC=C1CNC(=O)C1=CC=CN=C1 NTPYAXLOZIFOSG-UHFFFAOYSA-N 0.000 description 1
KPIUNMRQJGMTGZ-UHFFFAOYSA-N 4-phenylpiperidin-3-ol Chemical compound OC1CNCCC1C1=CC=CC=C1 KPIUNMRQJGMTGZ-UHFFFAOYSA-N 0.000 description 1
KQKFQBTWXOGINC-UHFFFAOYSA-N 4-phenylpiperidin-4-ol Chemical compound C=1C=CC=CC=1C1(O)CCNCC1 KQKFQBTWXOGINC-UHFFFAOYSA-N 0.000 description 1
DWSUJONSJJTODA-UHFFFAOYSA-N 5-(chloromethyl)-1,3-benzodioxole Chemical compound ClCC1=CC=C2OCOC2=C1 DWSUJONSJJTODA-UHFFFAOYSA-N 0.000 description 1
CVUZRMUCKVDRRQ-UHFFFAOYSA-N 5-(chloromethyl)-2,3-dihydro-1h-indene Chemical compound ClCC1=CC=C2CCCC2=C1 CVUZRMUCKVDRRQ-UHFFFAOYSA-N 0.000 description 1
GKCHUTZTJAFTHQ-UHFFFAOYSA-N 5-[(1,4-dimethoxynaphthalen-2-yl)methoxy]-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-ol Chemical compound COC=1C2=CC=CC=C2C(OC)=CC=1COC1CNCC(O)C1C(C=C1)=CC=C1OCCCOCC1=CC=CC=C1 GKCHUTZTJAFTHQ-UHFFFAOYSA-N 0.000 description 1
YAYWBPOXJMPJGF-UHFFFAOYSA-N 5-[(1,4-dimethoxynaphthalen-2-yl)methoxy]-4-[4-[3-[(2-methoxyphenyl)methoxy]propoxy]phenyl]piperidin-3-ol Chemical compound COC1=CC=CC=C1COCCCOC1=CC=C(C2C(CNCC2O)OCC=2C(=C3C=CC=CC3=C(OC)C=2)OC)C=C1 YAYWBPOXJMPJGF-UHFFFAOYSA-N 0.000 description 1
NESJFFCSMULUCX-UHFFFAOYSA-N 5-[[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenoxy]methyl]-3-phenyl-1,2,4-oxadiazole;2,2,2-trifluoroacetic acid Chemical group OC(=O)C(F)(F)F.C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCC(ON=1)=NC=1C1=CC=CC=C1 NESJFFCSMULUCX-UHFFFAOYSA-N 0.000 description 1
BCVHZDNNBHHZJU-UHFFFAOYSA-N 5-[[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenoxy]methyl]-3-phenyl-1,2-oxazole;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1OCC(ON=1)=CC=1C1=CC=CC=C1 BCVHZDNNBHHZJU-UHFFFAOYSA-N 0.000 description 1
QALKJGMGKYKMKE-UHFFFAOYSA-N 5-bromo-1,2-dihydroacenaphthylene Chemical compound C1CC2=CC=CC3=C2C1=CC=C3Br QALKJGMGKYKMKE-UHFFFAOYSA-N 0.000 description 1
FBOYMIDCHINJKC-UHFFFAOYSA-N 5-bromo-1,3-benzodioxole Chemical compound BrC1=CC=C2OCOC2=C1 FBOYMIDCHINJKC-UHFFFAOYSA-N 0.000 description 1
SMAMQSIENGBTRV-UHFFFAOYSA-N 5-hydroxynaphthalene-2-carboxylic acid Chemical compound OC1=CC=CC2=CC(C(=O)O)=CC=C21 SMAMQSIENGBTRV-UHFFFAOYSA-N 0.000 description 1
KCZQNAOFWQGLCN-UHFFFAOYSA-N 5-methyl-1-benzofuran Chemical compound CC1=CC=C2OC=CC2=C1 KCZQNAOFWQGLCN-UHFFFAOYSA-N 0.000 description 1
DOHZWDWNQFZIKH-UHFFFAOYSA-N 5-methyl-1-benzothiophene Chemical compound CC1=CC=C2SC=CC2=C1 DOHZWDWNQFZIKH-UHFFFAOYSA-N 0.000 description 1
239000001640 5-methylquinoxaline Substances 0.000 description 1
DMLZDWGHHYSKGY-UHFFFAOYSA-N 6-(bromomethyl)quinoxaline Chemical compound N1=CC=NC2=CC(CBr)=CC=C21 DMLZDWGHHYSKGY-UHFFFAOYSA-N 0.000 description 1
SSAGWEFEPFPFJC-UHFFFAOYSA-N 6-(chloromethyl)-1,1,4,4-tetramethyl-2,3-dihydronaphthalene Chemical compound ClCC1=CC=C2C(C)(C)CCC(C)(C)C2=C1 SSAGWEFEPFPFJC-UHFFFAOYSA-N 0.000 description 1
FDDVGEFFNYETAN-UHFFFAOYSA-N 6-(chloromethyl)-1,2,3,4-tetrahydronaphthalene Chemical compound C1CCCC2=CC(CCl)=CC=C21 FDDVGEFFNYETAN-UHFFFAOYSA-N 0.000 description 1
HARUWJZORCBAAL-UHFFFAOYSA-N 6-(chloromethyl)-2,3-dihydro-1,4-benzodioxine Chemical compound O1CCOC2=CC(CCl)=CC=C21 HARUWJZORCBAAL-UHFFFAOYSA-N 0.000 description 1
KAUQJMHLAFIZDU-UHFFFAOYSA-N 6-Hydroxy-2-naphthoic acid Chemical compound C1=C(O)C=CC2=CC(C(=O)O)=CC=C21 KAUQJMHLAFIZDU-UHFFFAOYSA-N 0.000 description 1
GTZPXQGFMUMVBC-UHFFFAOYSA-N 6-[[4-(4-fluorophenyl)piperidin-3-yl]oxymethyl]isoquinoline Chemical compound C1=CC(F)=CC=C1C1C(OCC=2C=C3C=CN=CC3=CC=2)CNCC1 GTZPXQGFMUMVBC-UHFFFAOYSA-N 0.000 description 1
IQGDEYNBPQSPGV-UHFFFAOYSA-N 6-[[4-(4-fluorophenyl)piperidin-3-yl]oxymethyl]naphthalen-2-ol Chemical compound C1=CC2=CC(O)=CC=C2C=C1COC1CNCCC1C1=CC=C(F)C=C1 IQGDEYNBPQSPGV-UHFFFAOYSA-N 0.000 description 1
QPOZGXKWWKLJDK-UHFFFAOYSA-N 6-nitro-3h-1,3-benzothiazole-2-thione Chemical compound [O-][N+](=O)C1=CC=C2NC(=S)SC2=C1 QPOZGXKWWKLJDK-UHFFFAOYSA-N 0.000 description 1
FGRRSMOVWCCRRC-MVSFAKPFSA-N 7-[[(3r,4r)-4-[4-[3-[(2-methoxyphenyl)methoxy]propoxy]phenyl]piperidin-3-yl]oxymethyl]-1h-quinolin-2-one Chemical compound COC1=CC=CC=C1COCCCOC1=CC=C([C@@H]2[C@H](CNCC2)OCC=2C=C3NC(=O)C=CC3=CC=2)C=C1 FGRRSMOVWCCRRC-MVSFAKPFSA-N 0.000 description 1
IKRJQZCDVDLJLS-BHYZAODMSA-N 7-[[(3r,4r)-4-[4-[3-[(2-methoxyphenyl)methoxy]propoxy]phenyl]piperidin-3-yl]oxymethyl]isoquinoline Chemical compound COC1=CC=CC=C1COCCCOC1=CC=C([C@@H]2[C@H](CNCC2)OCC=2C=C3C=NC=CC3=CC=2)C=C1 IKRJQZCDVDLJLS-BHYZAODMSA-N 0.000 description 1
GWRXXEBAJFCHJS-UHFFFAOYSA-N 7-[[4-(4-fluorophenyl)piperidin-3-yl]oxymethyl]naphthalen-1-ol Chemical compound C1=C2C(O)=CC=CC2=CC=C1COC1CNCCC1C1=CC=C(F)C=C1 GWRXXEBAJFCHJS-UHFFFAOYSA-N 0.000 description 1
UXRWZYYMQOXLII-UHFFFAOYSA-N 7-[[4-[4-[3-[(2-methoxyphenyl)methoxy]propoxy]phenyl]piperidin-3-yl]oxymethyl]-1,2,3,4-tetrahydroquinoline Chemical group COC1=CC=CC=C1COCCCOC1=CC=C(C2C(CNCC2)OCC=2C=C3NCCCC3=CC=2)C=C1 UXRWZYYMQOXLII-UHFFFAOYSA-N 0.000 description 1
FSXKKRVQMPPAMQ-UHFFFAOYSA-N 7-hydroxynaphthalene-2-carboxylic acid Chemical compound C1=CC(O)=CC2=CC(C(=O)O)=CC=C21 FSXKKRVQMPPAMQ-UHFFFAOYSA-N 0.000 description 1
ZPCQQOXOXNMOIJ-UHFFFAOYSA-N 8-hydroxynaphthalene-2-carboxylic acid Chemical compound C1=CC=C(O)C2=CC(C(=O)O)=CC=C21 ZPCQQOXOXNMOIJ-UHFFFAOYSA-N 0.000 description 1
239000005541 ACE inhibitor Substances 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
208000009304 Acute Kidney Injury Diseases 0.000 description 1
PQSUYGKTWSAVDQ-ZVIOFETBSA-N Aldosterone Chemical compound C([C@@]1([C@@H](C(=O)CO)CC[C@H]1[C@@H]1CC2)C=O)[C@H](O)[C@@H]1[C@]1(C)C2=CC(=O)CC1 PQSUYGKTWSAVDQ-ZVIOFETBSA-N 0.000 description 1
PQSUYGKTWSAVDQ-UHFFFAOYSA-N Aldosterone Natural products C1CC2C3CCC(C(=O)CO)C3(C=O)CC(O)C2C2(C)C1=CC(=O)CC2 PQSUYGKTWSAVDQ-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
229940123413 Angiotensin II antagonist Drugs 0.000 description 1
QMMRCKSBBNJCMR-KMZPNFOHSA-N Angiotensin III Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](NC(=O)[C@@H](N)CCCN=C(N)N)C(C)C)C1=CC=C(O)C=C1 QMMRCKSBBNJCMR-KMZPNFOHSA-N 0.000 description 1
101800000738 Angiotensin-3 Proteins 0.000 description 1
102400000348 Angiotensin-3 Human genes 0.000 description 1
108090001067 Angiotensinogen Proteins 0.000 description 1
102000004881 Angiotensinogen Human genes 0.000 description 1
108010064733 Angiotensins Proteins 0.000 description 1
102000015427 Angiotensins Human genes 0.000 description 1
ZETHHMPKDUSZQQ-UHFFFAOYSA-N Betulafolienepentol Natural products C1C=C(C)CCC(C(C)CCC=C(C)C)C2C(OC)OC(OC)C2=C1 ZETHHMPKDUSZQQ-UHFFFAOYSA-N 0.000 description 1
HVBOBJOYYLLHNQ-UHFFFAOYSA-N C(#N)C1=CC=C(C=C1)C1C(CNCC1)OCC1=CC2=CC=CC=C2C=C1.C(C)(C)(C)OC(=O)N1CC(C(CC1)C1=CC=C(C=C1)C#N)OCC1=CC2=CC=CC=C2C=C1 Chemical compound C(#N)C1=CC=C(C=C1)C1C(CNCC1)OCC1=CC2=CC=CC=C2C=C1.C(C)(C)(C)OC(=O)N1CC(C(CC1)C1=CC=C(C=C1)C#N)OCC1=CC2=CC=CC=C2C=C1 HVBOBJOYYLLHNQ-UHFFFAOYSA-N 0.000 description 1
JUJUBIIKAIALTI-UHFFFAOYSA-N C(C)(=O)[ClH]C(C=1C(O)=CC=CC=1)=O Chemical compound C(C)(=O)[ClH]C(C=1C(O)=CC=CC=1)=O JUJUBIIKAIALTI-UHFFFAOYSA-N 0.000 description 1
SBRGMZAHVFCJQB-UHFFFAOYSA-N C(C)(C)(C)OC(=O)N1CC(C(CC1)C1=CC=C(C=C1)C(N)C(CC1=CC=CC=C1)=O)OCC1=CC2=CC=CC=C2C=C1 Chemical compound C(C)(C)(C)OC(=O)N1CC(C(CC1)C1=CC=C(C=C1)C(N)C(CC1=CC=CC=C1)=O)OCC1=CC2=CC=CC=C2C=C1 SBRGMZAHVFCJQB-UHFFFAOYSA-N 0.000 description 1
NLPKGBIGZUXEHZ-UHFFFAOYSA-N C(C)(C)(C)OC(=O)N1CC(C(CC1)C1=CC=C(C=C1)CCOC)OCC1=CC2=CC=CC=C2C=C1 Chemical compound C(C)(C)(C)OC(=O)N1CC(C(CC1)C1=CC=C(C=C1)CCOC)OCC1=CC2=CC=CC=C2C=C1 NLPKGBIGZUXEHZ-UHFFFAOYSA-N 0.000 description 1
BXCZAPLHNCEXAZ-UHFFFAOYSA-N C(C1=CC=CC=C1)N1CC(C(CC1)C1=C(C=CC=C1)F)OCC1=CC2=CC=CC=C2C=C1.BrCC1=CC2=CC=CC=C2C=C1 Chemical compound C(C1=CC=CC=C1)N1CC(C(CC1)C1=C(C=CC=C1)F)OCC1=CC2=CC=CC=C2C=C1.BrCC1=CC2=CC=CC=C2C=C1 BXCZAPLHNCEXAZ-UHFFFAOYSA-N 0.000 description 1
HSKFLSCIJZSOSW-UHFFFAOYSA-N C(C1=CC=CC=C1)N1CC(C(CC1)C1=CC(=CC=C1)F)OCC1=CC2=CC=CC=C2C=C1.BrCC1=CC2=CC=CC=C2C=C1 Chemical compound C(C1=CC=CC=C1)N1CC(C(CC1)C1=CC(=CC=C1)F)OCC1=CC2=CC=CC=C2C=C1.BrCC1=CC2=CC=CC=C2C=C1 HSKFLSCIJZSOSW-UHFFFAOYSA-N 0.000 description 1
WMJPFXNQWIJSFS-UHFFFAOYSA-N CC(C1=CC=CC=C1)OC(C1=CC2=CC=CC=C2C=C1)OC(CNCC1)C1C(C=C1)=CC=C1F Chemical compound CC(C1=CC=CC=C1)OC(C1=CC2=CC=CC=C2C=C1)OC(CNCC1)C1C(C=C1)=CC=C1F WMJPFXNQWIJSFS-UHFFFAOYSA-N 0.000 description 1
229940127291 Calcium channel antagonist Drugs 0.000 description 1
WSPKQXZPSLKQNQ-UHFFFAOYSA-N Cl.C1=CC(OC)=CC=C1C(=O)OCCOC1=CC=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=C1 Chemical compound Cl.C1=CC(OC)=CC=C1C(=O)OCCOC1=CC=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=C1 WSPKQXZPSLKQNQ-UHFFFAOYSA-N 0.000 description 1
OYSJIGBBZDFWFN-UHFFFAOYSA-N Cl.C=1C=CC=C(C(=O)OCCOC=2C=CC(=CC=2)C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=1COC(=O)C1=CC=CC=C1 Chemical compound Cl.C=1C=CC=C(C(=O)OCCOC=2C=CC(=CC=2)C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=1COC(=O)C1=CC=CC=C1 OYSJIGBBZDFWFN-UHFFFAOYSA-N 0.000 description 1
YWQSZCBHYVSLIY-UHFFFAOYSA-N Cl.C=1C=CN=CC=1C(=O)NCC1=CC=CC=C1COC1CNCCC1C1=CC=CC=C1 Chemical compound Cl.C=1C=CN=CC=1C(=O)NCC1=CC=CC=C1COC1CNCCC1C1=CC=CC=C1 YWQSZCBHYVSLIY-UHFFFAOYSA-N 0.000 description 1
MDJIWVVOOJFZBF-UHFFFAOYSA-N ClC1=CC=C(C=C1)C1C(CN(CC1)C(=O)O)OCC1=CC2=CC=CC=C2C=C1 Chemical compound ClC1=CC=C(C=C1)C1C(CN(CC1)C(=O)O)OCC1=CC2=CC=CC=C2C=C1 MDJIWVVOOJFZBF-UHFFFAOYSA-N 0.000 description 1
GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
108010061435 Enalapril Proteins 0.000 description 1
JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
XJACLBAQMOBCTC-UHFFFAOYSA-N FC1=CC=C(C=C1)C1C(CNCC1)OCC1=CC2=CC=CC=C2C=C1.C(C)(C)(C)OC(=O)N1CC(C(CC1)C1=CC=C(C=C1)F)OCC1=CC2=CC=CC=C2C=C1 Chemical compound FC1=CC=C(C=C1)C1C(CNCC1)OCC1=CC2=CC=CC=C2C=C1.C(C)(C)(C)OC(=O)N1CC(C(CC1)C1=CC=C(C=C1)F)OCC1=CC2=CC=CC=C2C=C1 XJACLBAQMOBCTC-UHFFFAOYSA-N 0.000 description 1
XQLWNAFCTODIRK-UHFFFAOYSA-N Gallopamil Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC(OC)=C(OC)C(OC)=C1 XQLWNAFCTODIRK-UHFFFAOYSA-N 0.000 description 1
208000010412 Glaucoma Diseases 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
WDZVGELJXXEGPV-YIXHJXPBSA-N Guanabenz Chemical compound NC(N)=N\N=C\C1=C(Cl)C=CC=C1Cl WDZVGELJXXEGPV-YIXHJXPBSA-N 0.000 description 1
241000282412 Homo Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
HETCEOQFVDFGSY-UHFFFAOYSA-N Isopropenyl acetate Chemical compound CC(=C)OC(C)=O HETCEOQFVDFGSY-UHFFFAOYSA-N 0.000 description 1
229930194542 Keto Natural products 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
108010007859 Lisinopril Proteins 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
ZFMITUMMTDLWHR-UHFFFAOYSA-N Minoxidil Chemical compound NC1=[N+]([O-])C(N)=CC(N2CCCCC2)=N1 ZFMITUMMTDLWHR-UHFFFAOYSA-N 0.000 description 1
238000007126 N-alkylation reaction Methods 0.000 description 1
ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
YYVFXSYQSOZCOQ-UHFFFAOYSA-N Oxyquinoline sulfate Chemical compound [O-]S([O-])(=O)=O.C1=C[NH+]=C2C(O)=CC=CC2=C1.C1=C[NH+]=C2C(O)=CC=CC2=C1 YYVFXSYQSOZCOQ-UHFFFAOYSA-N 0.000 description 1
QZVCTJOXCFMACW-UHFFFAOYSA-N Phenoxybenzamine Chemical compound C=1C=CC=CC=1CN(CCCl)C(C)COC1=CC=CC=C1 QZVCTJOXCFMACW-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
208000033626 Renal failure acute Diseases 0.000 description 1
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 1
102000007562 Serum Albumin Human genes 0.000 description 1
108010071390 Serum Albumin Proteins 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229910000831 Steel Inorganic materials 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
239000000219 Sympatholytic Substances 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
241000473945 Theria <moth genus> Species 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
FNYLWPVRPXGIIP-UHFFFAOYSA-N Triamterene Chemical compound NC1=NC2=NC(N)=NC(N)=C2N=C1C1=CC=CC=C1 FNYLWPVRPXGIIP-UHFFFAOYSA-N 0.000 description 1
229910052770 Uranium Inorganic materials 0.000 description 1
QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
238000000441 X-ray spectroscopy Methods 0.000 description 1
XRBROVWUFNVUFQ-UHFFFAOYSA-N [1-(2-trimethylsilylethoxymethoxy)naphthalen-2-yl]methanol Chemical compound C1=CC=C2C(OCOCC[Si](C)(C)C)=C(CO)C=CC2=C1 XRBROVWUFNVUFQ-UHFFFAOYSA-N 0.000 description 1
KSUWNMOLJIBDKK-UHFFFAOYSA-N [2-(2-trimethylsilylethoxymethoxy)phenyl]methanol Chemical compound C[Si](C)(C)CCOCOC1=CC=CC=C1CO KSUWNMOLJIBDKK-UHFFFAOYSA-N 0.000 description 1
ISOKIVWNNWSUEA-UHFFFAOYSA-N [3-(2-trimethylsilylethoxymethoxy)naphthalen-2-yl]methanol Chemical compound C1=CC=C2C=C(CO)C(OCOCC[Si](C)(C)C)=CC2=C1 ISOKIVWNNWSUEA-UHFFFAOYSA-N 0.000 description 1
WHQCOCVDJSZWLV-UHFFFAOYSA-N [3-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]methyl benzoate;hydrochloride Chemical compound Cl.C=1C=CC(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)=CC=1COC(=O)C1=CC=CC=C1 WHQCOCVDJSZWLV-UHFFFAOYSA-N 0.000 description 1
PUIMIUATDOQGRI-UHFFFAOYSA-N [3-[3-[(4-phenylmethoxynaphthalen-2-yl)methoxy]piperidin-4-yl]phenyl]methanol Chemical compound OCC1=CC=CC(C2C(CNCC2)OCC=2C=C3C=CC=CC3=C(OCC=3C=CC=CC=3)C=2)=C1 PUIMIUATDOQGRI-UHFFFAOYSA-N 0.000 description 1
YDLFVGNNIKGALS-UHFFFAOYSA-N [4-(2-trimethylsilylethoxymethoxy)naphthalen-2-yl]methanol Chemical compound C1=CC=C2C(OCOCC[Si](C)(C)C)=CC(CO)=CC2=C1 YDLFVGNNIKGALS-UHFFFAOYSA-N 0.000 description 1
ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
GTLPRIUFZZKWIW-UHFFFAOYSA-N [4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]methanol Chemical compound C1=CC(CO)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CNCC1 GTLPRIUFZZKWIW-UHFFFAOYSA-N 0.000 description 1
PZJRTJIDYQAMRX-UHFFFAOYSA-N [4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]methyl 2,2-dimethylpropanoate;hydrochloride Chemical compound Cl.C1=CC(COC(=O)C(C)(C)C)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CNCC1 PZJRTJIDYQAMRX-UHFFFAOYSA-N 0.000 description 1
UTPFLFREMWPQNS-UHFFFAOYSA-N [4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]methyl 2-chlorobenzoate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.ClC1=CC=CC=C1C(=O)OCC1=CC=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=C1 UTPFLFREMWPQNS-UHFFFAOYSA-N 0.000 description 1
ADLZGZDDEQNPDH-UHFFFAOYSA-N [4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]methyl 3,5-dimethoxybenzoate;hydrochloride Chemical compound Cl.COC1=CC(OC)=CC(C(=O)OCC=2C=CC(=CC=2)C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)=C1 ADLZGZDDEQNPDH-UHFFFAOYSA-N 0.000 description 1
XELMQPRYEIDHLR-UHFFFAOYSA-N [4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]methyl cyclohexanecarboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1COC(=O)C1CCCCC1 XELMQPRYEIDHLR-UHFFFAOYSA-N 0.000 description 1
KKLNSPQFQAQNGK-UHFFFAOYSA-N [4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]methyl n-pyridin-2-ylcarbamate;hydrochloride Chemical compound Cl.C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1COC(=O)NC1=CC=CC=N1 KKLNSPQFQAQNGK-UHFFFAOYSA-N 0.000 description 1
LELDUMMNHBRHJO-UHFFFAOYSA-N [4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]methyl pyrazine-2-carboxylate;hydrochloride Chemical compound Cl.C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1COC(=O)C1=CN=CC=N1 LELDUMMNHBRHJO-UHFFFAOYSA-N 0.000 description 1
GRBRKKODDKWADK-UHFFFAOYSA-N [4-[3-[(1-methoxynaphthalen-2-yl)methoxy]piperidin-4-yl]phenyl]methyl 2-chlorobenzoate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC2=CC=CC=C2C(OC)=C1COC1CNCCC1C(C=C1)=CC=C1COC(=O)C1=CC=CC=C1Cl GRBRKKODDKWADK-UHFFFAOYSA-N 0.000 description 1
ZUOZMLJQPMSQEN-UHFFFAOYSA-N [4-[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenoxy]-1-phenylbutyl] benzoate Chemical compound C=1C=CC=CC=1C(=O)OC(CCCOC=1C=CC(=CC=1)C1C(CNCC1)OCC=1C=C2C=CC=CC2=CC=1)C1=CC=CC=C1 ZUOZMLJQPMSQEN-UHFFFAOYSA-N 0.000 description 1
ZXUQOCAOVDGPIX-UHFFFAOYSA-N [5-(2-trimethylsilylethoxymethoxy)naphthalen-2-yl]methanol Chemical compound OCC1=CC=C2C(OCOCC[Si](C)(C)C)=CC=CC2=C1 ZXUQOCAOVDGPIX-UHFFFAOYSA-N 0.000 description 1
WJVISQXZCRLPEN-UHFFFAOYSA-N [5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]methanol;hydrochloride Chemical compound Cl.OCC1CNCC(OCC=2C=C3C=CC=CC3=CC=2)C1C(C=C1)=CC=C1OCCCOCC1=CC=CC=C1 WJVISQXZCRLPEN-UHFFFAOYSA-N 0.000 description 1
OSLABEXNKYWVEY-UHFFFAOYSA-N [7-(2-trimethylsilylethoxymethoxy)naphthalen-2-yl]methanol Chemical compound C1=CC(CO)=CC2=CC(OCOCC[Si](C)(C)C)=CC=C21 OSLABEXNKYWVEY-UHFFFAOYSA-N 0.000 description 1
SPTHTORGPOCUBB-UHFFFAOYSA-N [8-(2-trimethylsilylethoxymethoxy)naphthalen-2-yl]methanol Chemical compound C1=C(CO)C=C2C(OCOCC[Si](C)(C)C)=CC=CC2=C1 SPTHTORGPOCUBB-UHFFFAOYSA-N 0.000 description 1
DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical compound [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
BZKPWHYZMXOIDC-UHFFFAOYSA-N acetazolamide Chemical compound CC(=O)NC1=NN=C(S(N)(=O)=O)S1 BZKPWHYZMXOIDC-UHFFFAOYSA-N 0.000 description 1
229960000571 acetazolamide Drugs 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
125000005396 acrylic acid ester group Chemical group 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
239000012190 activator Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
201000011040 acute kidney failure Diseases 0.000 description 1
208000012998 acute renal failure Diseases 0.000 description 1
210000004100 adrenal gland Anatomy 0.000 description 1
229960002478 aldosterone Drugs 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
239000002160 alpha blocker Substances 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
229940124308 alpha-adrenoreceptor antagonist Drugs 0.000 description 1
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 description 1
229960002576 amiloride Drugs 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
238000005915 ammonolysis reaction Methods 0.000 description 1
RNLQIBCLLYYYFJ-UHFFFAOYSA-N amrinone Chemical compound N1C(=O)C(N)=CC(C=2C=CN=CC=2)=C1 RNLQIBCLLYYYFJ-UHFFFAOYSA-N 0.000 description 1
229960002105 amrinone Drugs 0.000 description 1
239000002333 angiotensin II receptor antagonist Substances 0.000 description 1
229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
230000001705 anti-serotonergic effect Effects 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000001543 aryl boronic acids Chemical class 0.000 description 1
238000003556 assay Methods 0.000 description 1
229960002274 atenolol Drugs 0.000 description 1
IUKQLMGVFMDQDP-UHFFFAOYSA-N azane;piperidine Chemical compound N.C1CCNCC1 IUKQLMGVFMDQDP-UHFFFAOYSA-N 0.000 description 1
YEESUBCSWGVPCE-UHFFFAOYSA-N azanylidyneoxidanium iron(2+) pentacyanide Chemical compound [Fe++].[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.N#[O+] YEESUBCSWGVPCE-UHFFFAOYSA-N 0.000 description 1
MXOQNVMDKHLYCZ-UHFFFAOYSA-N benzamidoxime Chemical compound ON=C(N)C1=CC=CC=C1 MXOQNVMDKHLYCZ-UHFFFAOYSA-N 0.000 description 1
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
NDTSRXAMMQDVSW-UHFFFAOYSA-N benzthiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(S(N2)(=O)=O)=C1N=C2CSCC1=CC=CC=C1 NDTSRXAMMQDVSW-UHFFFAOYSA-N 0.000 description 1
229960001541 benzthiazide Drugs 0.000 description 1
CLCOXQROCAMRQO-UHFFFAOYSA-M benzyl-dimethyl-phenylazanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[N+](C)(C)CC1=CC=CC=C1 CLCOXQROCAMRQO-UHFFFAOYSA-M 0.000 description 1
239000003613 bile acid Substances 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
230000004531 blood pressure lowering effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
239000000337 buffer salt Substances 0.000 description 1
MAEIEVLCKWDQJH-UHFFFAOYSA-N bumetanide Chemical compound CCCCNC1=CC(C(O)=O)=CC(S(N)(=O)=O)=C1OC1=CC=CC=C1 MAEIEVLCKWDQJH-UHFFFAOYSA-N 0.000 description 1
229960004064 bumetanide Drugs 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
244000309466 calf Species 0.000 description 1
FAKRSMQSSFJEIM-RQJHMYQMSA-N captopril Chemical compound SC[C@@H](C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-RQJHMYQMSA-N 0.000 description 1
229960000830 captopril Drugs 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
230000021235 carbamoylation Effects 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
230000006315 carbonylation Effects 0.000 description 1
238000005810 carbonylation reaction Methods 0.000 description 1
LWAFSWPYPHEXKX-UHFFFAOYSA-N carteolol Chemical compound N1C(=O)CCC2=C1C=CC=C2OCC(O)CNC(C)(C)C LWAFSWPYPHEXKX-UHFFFAOYSA-N 0.000 description 1
229960001222 carteolol Drugs 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
229940083181 centrally acting adntiadrenergic agent methyldopa Drugs 0.000 description 1
SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
229960002155 chlorothiazide Drugs 0.000 description 1
229960001523 chlortalidone Drugs 0.000 description 1
208000020832 chronic kidney disease Diseases 0.000 description 1
208000022831 chronic renal failure syndrome Diseases 0.000 description 1
HHHKFGXWKKUNCY-FHWLQOOXSA-N cilazapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H]1C(N2[C@@H](CCCN2CCC1)C(O)=O)=O)CC1=CC=CC=C1 HHHKFGXWKKUNCY-FHWLQOOXSA-N 0.000 description 1
229960005025 cilazapril Drugs 0.000 description 1
150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
229960002896 clonidine Drugs 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
229910052681 coesite Inorganic materials 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000010276 construction Methods 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
229910052906 cristobalite Inorganic materials 0.000 description 1
230000009260 cross reactivity Effects 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
229910021641 deionized water Inorganic materials 0.000 description 1
230000001335 demethylating effect Effects 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
HEOKFDGOFROELJ-UHFFFAOYSA-N diacetal Natural products COc1ccc(C=C/c2cc(O)cc(OC3OC(COC(=O)c4cc(O)c(O)c(O)c4)C(O)C(O)C3O)c2)cc1O HEOKFDGOFROELJ-UHFFFAOYSA-N 0.000 description 1
238000010586 diagram Methods 0.000 description 1
229960004042 diazoxide Drugs 0.000 description 1
HSUGRBWQSSZJOP-RTWAWAEBSA-N diltiazem Chemical compound C1=CC(OC)=CC=C1[C@H]1[C@@H](OC(C)=O)C(=O)N(CCN(C)C)C2=CC=CC=C2S1 HSUGRBWQSSZJOP-RTWAWAEBSA-N 0.000 description 1
229960004166 diltiazem Drugs 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
VTIIJXUACCWYHX-UHFFFAOYSA-L disodium;carboxylatooxy carbonate Chemical compound [Na+].[Na+].[O-]C(=O)OOC([O-])=O VTIIJXUACCWYHX-UHFFFAOYSA-L 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
GBXSMTUPTTWBMN-XIRDDKMYSA-N enalapril Chemical compound C([C@@H](C(=O)OCC)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(O)=O)CC1=CC=CC=C1 GBXSMTUPTTWBMN-XIRDDKMYSA-N 0.000 description 1
229960000873 enalapril Drugs 0.000 description 1
150000002081 enamines Chemical class 0.000 description 1
238000006735 epoxidation reaction Methods 0.000 description 1
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
UCZLBERYFYDXOM-UHFFFAOYSA-N ethenyltin Chemical compound [Sn]C=C UCZLBERYFYDXOM-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
BCGHYEPYMXEJKN-UHFFFAOYSA-N ethyl 6-(2-trimethylsilylethoxymethoxy)naphthalene-2-carboxylate Chemical compound C1=C(OCOCC[Si](C)(C)C)C=CC2=CC(C(=O)OCC)=CC=C21 BCGHYEPYMXEJKN-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
XZSXCFWWZHTJMU-UHFFFAOYSA-N ethyl isoquinoline-6-carboxylate Chemical compound C1=NC=CC2=CC(C(=O)OCC)=CC=C21 XZSXCFWWZHTJMU-UHFFFAOYSA-N 0.000 description 1
FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
210000003722 extracellular fluid Anatomy 0.000 description 1
239000000284 extract Substances 0.000 description 1
229960002602 fendiline Drugs 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
UYGONJYYUKVHDD-UHFFFAOYSA-N flosequinan Chemical compound C1=C(F)C=C2N(C)C=C(S(C)=O)C(=O)C2=C1 UYGONJYYUKVHDD-UHFFFAOYSA-N 0.000 description 1
229960001606 flosequinan Drugs 0.000 description 1
SMANXXCATUTDDT-QPJJXVBHSA-N flunarizine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)N1CCN(C\C=C\C=2C=CC=CC=2)CC1 SMANXXCATUTDDT-QPJJXVBHSA-N 0.000 description 1
229960000326 flunarizine Drugs 0.000 description 1
LZLGHWHSUZVUFZ-HZPDHXFCSA-N folerogenin Chemical compound C1([C@@H]2[C@H](O)C(=O)C3=C(O)C=C(C=C3O2)OC)=CC=C(O)C=C1 LZLGHWHSUZVUFZ-HZPDHXFCSA-N 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
229960003883 furosemide Drugs 0.000 description 1
229960000457 gallopamil Drugs 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
229960004553 guanabenz Drugs 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
150000002390 heteroarenes Chemical class 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
229940088597 hormone Drugs 0.000 description 1
239000005556 hormone Substances 0.000 description 1
229960002474 hydralazine Drugs 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
229960002003 hydrochlorothiazide Drugs 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
150000002443 hydroxylamines Chemical class 0.000 description 1
150000007928 imidazolide derivatives Chemical class 0.000 description 1
150000003949 imides Chemical class 0.000 description 1
229950009607 indacrinone Drugs 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000008011 inorganic excipient Substances 0.000 description 1
238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
150000002497 iodine compounds Chemical class 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
ADAHADRJWVCICR-UHFFFAOYSA-N isoquinoline-6-carboxylic acid Chemical compound C1=NC=CC2=CC(C(=O)O)=CC=C21 ADAHADRJWVCICR-UHFFFAOYSA-N 0.000 description 1
FPCCSQOGAWCVBH-UHFFFAOYSA-N ketanserin Chemical compound C1=CC(F)=CC=C1C(=O)C1CCN(CCN2C(C3=CC=CC=C3NC2=O)=O)CC1 FPCCSQOGAWCVBH-UHFFFAOYSA-N 0.000 description 1
229960005417 ketanserin Drugs 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
208000017169 kidney disease Diseases 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
238000012417 linear regression Methods 0.000 description 1
229960002394 lisinopril Drugs 0.000 description 1
CZRQXSDBMCMPNJ-ZUIPZQNBSA-N lisinopril dihydrate Chemical compound O.O.C([C@H](N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(O)=O)C(O)=O)CC1=CC=CC=C1 CZRQXSDBMCMPNJ-ZUIPZQNBSA-N 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
229910001496 lithium tetrafluoroborate Inorganic materials 0.000 description 1
PUDLQTGOPPTYJT-UHFFFAOYSA-N lithium;bromobenzene Chemical compound [Li+].BrC1=CC=C[C-]=C1 PUDLQTGOPPTYJT-UHFFFAOYSA-N 0.000 description 1
210000004072 lung Anatomy 0.000 description 1
150000002680 magnesium Chemical class 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
IWCVDCOJSPWGRW-UHFFFAOYSA-M magnesium;benzene;chloride Chemical compound [Mg+2].[Cl-].C1=CC=[C-]C=C1 IWCVDCOJSPWGRW-UHFFFAOYSA-M 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical class O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
IUMLBPZTLMEDPR-UHFFFAOYSA-N methyl 1-(2-trimethylsilylethoxymethoxy)naphthalene-2-carboxylate Chemical compound C1=CC=CC2=C(OCOCC[Si](C)(C)C)C(C(=O)OC)=CC=C21 IUMLBPZTLMEDPR-UHFFFAOYSA-N 0.000 description 1
HMIBDRSTVGFJPB-UHFFFAOYSA-N methyl 1-hydroxynaphthalene-2-carboxylate Chemical compound C1=CC=CC2=C(O)C(C(=O)OC)=CC=C21 HMIBDRSTVGFJPB-UHFFFAOYSA-N 0.000 description 1
IKYRLYKWULPUNA-UHFFFAOYSA-N methyl 1-methoxynaphthalene-2-carboxylate Chemical compound C1=CC=CC2=C(OC)C(C(=O)OC)=CC=C21 IKYRLYKWULPUNA-UHFFFAOYSA-N 0.000 description 1
AVNJMHZVVXXJMV-UHFFFAOYSA-N methyl 3-(1-benzyl-3-hydroxypiperidin-4-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C2C(CN(CC=3C=CC=CC=3)CC2)O)=C1 AVNJMHZVVXXJMV-UHFFFAOYSA-N 0.000 description 1
ZXPFAUWLWRMPDA-UHFFFAOYSA-N methyl 3-(2-trimethylsilylethoxymethoxy)naphthalene-2-carboxylate Chemical compound C1=CC=C2C=C(OCOCC[Si](C)(C)C)C(C(=O)OC)=CC2=C1 ZXPFAUWLWRMPDA-UHFFFAOYSA-N 0.000 description 1
ASQXSRGHKJXCNF-UHFFFAOYSA-N methyl 3-(3-hydroxypiperidin-4-yl)benzoate Chemical compound COC(=O)C1=CC=CC(C2C(CNCC2)O)=C1 ASQXSRGHKJXCNF-UHFFFAOYSA-N 0.000 description 1
WVSAKLHWYJOBKV-UHFFFAOYSA-N methyl 3-[3-[(4-phenylmethoxynaphthalen-2-yl)methoxy]piperidin-4-yl]benzoate Chemical compound COC(=O)c1cccc(c1)C1CCNCC1OCc1cc(OCc2ccccc2)c2ccccc2c1 WVSAKLHWYJOBKV-UHFFFAOYSA-N 0.000 description 1
YVVBECLPRBAATK-UHFFFAOYSA-N methyl 3-hydroxynaphthalene-2-carboxylate Chemical compound C1=CC=C2C=C(O)C(C(=O)OC)=CC2=C1 YVVBECLPRBAATK-UHFFFAOYSA-N 0.000 description 1
MPLSAOVNAXJHHI-UHFFFAOYSA-N methyl 3-methoxynaphthalene-2-carboxylate Chemical compound C1=CC=C2C=C(OC)C(C(=O)OC)=CC2=C1 MPLSAOVNAXJHHI-UHFFFAOYSA-N 0.000 description 1
IOZSZSIGWWNVQL-UHFFFAOYSA-N methyl 5-(2-trimethylsilylethoxymethoxy)naphthalene-2-carboxylate Chemical compound C[Si](C)(C)CCOCOC1=CC=CC2=CC(C(=O)OC)=CC=C21 IOZSZSIGWWNVQL-UHFFFAOYSA-N 0.000 description 1
LENWVHZYLOZACS-UHFFFAOYSA-N methyl 5-hydroxynaphthalene-2-carboxylate Chemical compound OC1=CC=CC2=CC(C(=O)OC)=CC=C21 LENWVHZYLOZACS-UHFFFAOYSA-N 0.000 description 1
NRAOMQRRELNKIQ-UHFFFAOYSA-N methyl 7-hydroxynaphthalene-2-carboxylate Chemical compound C1=CC(O)=CC2=CC(C(=O)OC)=CC=C21 NRAOMQRRELNKIQ-UHFFFAOYSA-N 0.000 description 1
VCLWTCIPOBHLQQ-UHFFFAOYSA-N methyl 8-hydroxynaphthalene-2-carboxylate Chemical compound C1=CC=C(O)C2=CC(C(=O)OC)=CC=C21 VCLWTCIPOBHLQQ-UHFFFAOYSA-N 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
AQCHWTWZEMGIFD-UHFFFAOYSA-N metolazone Chemical compound CC1NC2=CC(Cl)=C(S(N)(=O)=O)C=C2C(=O)N1C1=CC=CC=C1C AQCHWTWZEMGIFD-UHFFFAOYSA-N 0.000 description 1
229960002817 metolazone Drugs 0.000 description 1
IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 description 1
229960002237 metoprolol Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229960003632 minoxidil Drugs 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
TWSOFWBBTQANHQ-VRQIXWKPSA-N n,n,n'-trimethyl-n'-[[(3s,4r,5r)-5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]methyl]ethane-1,2-diamine Chemical compound C1=CC([C@@H]2[C@@H](OCC=3C=C4C=CC=CC4=CC=3)CNC[C@H]2CN(C)CCN(C)C)=CC=C1OCCCOCC1=CC=CC=C1 TWSOFWBBTQANHQ-VRQIXWKPSA-N 0.000 description 1
DZKCWWXXTYBBDK-UHFFFAOYSA-N n-[[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]methyl]-2-phenylacetamide Chemical compound C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1CNC(=O)CC1=CC=CC=C1 DZKCWWXXTYBBDK-UHFFFAOYSA-N 0.000 description 1
LISUBEHLPYMJLG-UHFFFAOYSA-N n-[[4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]phenyl]methyl]benzenesulfonamide Chemical compound C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1CNS(=O)(=O)C1=CC=CC=C1 LISUBEHLPYMJLG-UHFFFAOYSA-N 0.000 description 1
QFANJNHLPHLKOP-UHFFFAOYSA-N n-[[4-[3-[(4-hydroxynaphthalen-2-yl)methoxy]piperidin-4-yl]phenyl]methyl]benzamide Chemical compound C=1C2=CC=CC=C2C(O)=CC=1COC1CNCCC1C(C=C1)=CC=C1CNC(=O)C1=CC=CC=C1 QFANJNHLPHLKOP-UHFFFAOYSA-N 0.000 description 1
NVIJIWFFJSMOBX-UHFFFAOYSA-N n-benzyl-4-[3-(naphthalen-2-ylmethoxy)piperidin-4-yl]benzamide Chemical compound C=1C=C(C2C(CNCC2)OCC=2C=C3C=CC=CC3=CC=2)C=CC=1C(=O)NCC1=CC=CC=C1 NVIJIWFFJSMOBX-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
ABNIRSHNIAQENF-UHFFFAOYSA-N n-ethyl-n-[[5-(naphthalen-2-ylmethoxy)-4-[4-(3-phenylmethoxypropoxy)phenyl]piperidin-3-yl]methyl]ethanamine Chemical group CCN(CC)CC1CNCC(OCC=2C=C3C=CC=CC3=CC=2)C1C(C=C1)=CC=C1OCCCOCC1=CC=CC=C1 ABNIRSHNIAQENF-UHFFFAOYSA-N 0.000 description 1
GNZODVGIXZMKFX-UHFFFAOYSA-N n-methyl-n-[3-[4-(3-naphthalen-2-yloxypiperidin-4-yl)phenoxy]propyl]benzamide Chemical compound C=1C=C(C2C(CNCC2)OC=2C=C3C=CC=CC3=CC=2)C=CC=1OCCCN(C)C(=O)C1=CC=CC=C1 GNZODVGIXZMKFX-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229960004255 nadolol Drugs 0.000 description 1
239000007922 nasal spray Substances 0.000 description 1
229960001783 nicardipine Drugs 0.000 description 1
QEKXARSPUFVXIX-UHFFFAOYSA-L nickel(2+);triphenylphosphane;dibromide Chemical compound [Ni+2].[Br-].[Br-].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QEKXARSPUFVXIX-UHFFFAOYSA-L 0.000 description 1
HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
229960001597 nifedipine Drugs 0.000 description 1
229960000715 nimodipine Drugs 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
229910000069 nitrogen hydride Inorganic materials 0.000 description 1
229960002460 nitroprusside Drugs 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000008012 organic excipient Substances 0.000 description 1
150000002900 organolithium compounds Chemical class 0.000 description 1
150000002901 organomagnesium compounds Chemical class 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
229910003445 palladium oxide Inorganic materials 0.000 description 1
JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 1
239000003415 peat Substances 0.000 description 1
239000000813 peptide hormone Substances 0.000 description 1
CYXKNKQEMFBLER-UHFFFAOYSA-N perhexiline Chemical compound C1CCCNC1CC(C1CCCCC1)C1CCCCC1 CYXKNKQEMFBLER-UHFFFAOYSA-N 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
229960003418 phenoxybenzamine Drugs 0.000 description 1
MRBDMNSDAVCSSF-UHFFFAOYSA-N phentolamine Chemical compound C1=CC(C)=CC=C1N(C=1C=C(O)C=CC=1)CC1=NCCN1 MRBDMNSDAVCSSF-UHFFFAOYSA-N 0.000 description 1
229960001999 phentolamine Drugs 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 1
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical class [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
IENZQIKPVFGBNW-UHFFFAOYSA-N prazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1=CC=CO1 IENZQIKPVFGBNW-UHFFFAOYSA-N 0.000 description 1
229960001289 prazosin Drugs 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
125000006410 propenylene group Chemical group 0.000 description 1
150000005599 propionic acid derivatives Chemical class 0.000 description 1
229960003712 propranolol Drugs 0.000 description 1
150000003216 pyrazines Chemical class 0.000 description 1
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
229910052701 rubidium Inorganic materials 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
229960001922 sodium perborate Drugs 0.000 description 1
229940045872 sodium percarbonate Drugs 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000001433 sodium tartrate Substances 0.000 description 1
229960002167 sodium tartrate Drugs 0.000 description 1
235000011004 sodium tartrates Nutrition 0.000 description 1
MDUSUFIKBUMDTJ-UHFFFAOYSA-N sodium;1h-1,2,4-triazole Chemical compound [Na].C=1N=CNN=1 MDUSUFIKBUMDTJ-UHFFFAOYSA-N 0.000 description 1
YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 description 1
229960002256 spironolactone Drugs 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000010959 steel Substances 0.000 description 1
229910052682 stishovite Inorganic materials 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
125000001174 sulfone group Chemical group 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
230000000948 sympatholitic effect Effects 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
VCKUSRYTPJJLNI-UHFFFAOYSA-N terazosin Chemical compound N=1C(N)=C2C=C(OC)C(OC)=CC2=NC=1N(CC1)CCN1C(=O)C1CCCO1 VCKUSRYTPJJLNI-UHFFFAOYSA-N 0.000 description 1
229960001693 terazosin Drugs 0.000 description 1
SFUGIFDOAWCXLO-UHFFFAOYSA-N tert-butyl 2-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCCC1OCC1=CC=C(C=CC=C2)C2=C1 SFUGIFDOAWCXLO-UHFFFAOYSA-N 0.000 description 1
WZDUMISBAHEPLN-UHFFFAOYSA-N tert-butyl 2-methoxypiperidine-1-carboxylate Chemical compound COC1CCCCN1C(=O)OC(C)(C)C WZDUMISBAHEPLN-UHFFFAOYSA-N 0.000 description 1
RPJGIIFMEAVROB-UHFFFAOYSA-N tert-butyl 3-(2,3-dihydro-1h-inden-5-ylmethoxy)-4-(4-fluorophenyl)piperidine-1-carboxylate Chemical compound C=1C=C2CCCC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(F)C=C1 RPJGIIFMEAVROB-UHFFFAOYSA-N 0.000 description 1
QSIRIOBJPITKPX-UHFFFAOYSA-N tert-butyl 3-(naphthalen-2-ylmethoxy)-4-(5,6,7,8-tetrahydronaphthalen-2-yl)piperidine-1-carboxylate Chemical compound C1CCCC2=CC(C3CCN(CC3OCC=3C=C4C=CC=CC4=CC=3)C(=O)OC(C)(C)C)=CC=C21 QSIRIOBJPITKPX-UHFFFAOYSA-N 0.000 description 1
SNTGCDKARCNVDQ-UHFFFAOYSA-N tert-butyl 3-(naphthalen-2-ylmethoxy)-4-[4-(2-phenylmethoxyethoxy)phenyl]piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1OCCOCC1=CC=CC=C1 SNTGCDKARCNVDQ-UHFFFAOYSA-N 0.000 description 1
XKMCMKCQAACYLR-UHFFFAOYSA-N tert-butyl 3-(naphthalen-2-ylmethoxy)-4-[4-(2-phenylsulfanylethoxy)phenyl]piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1OCCSC1=CC=CC=C1 XKMCMKCQAACYLR-UHFFFAOYSA-N 0.000 description 1
FBTZIISVXSQVGN-UHFFFAOYSA-N tert-butyl 3-(naphthalen-2-ylmethoxy)-4-[4-(2-trityloxyethyl)phenyl]piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1CCOC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 FBTZIISVXSQVGN-UHFFFAOYSA-N 0.000 description 1
RXBWBCOTPZQEJV-UHFFFAOYSA-N tert-butyl 3-(naphthalen-2-ylmethoxy)-4-[4-(4-oxo-4-phenylbutoxy)phenyl]piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1OCCCC(=O)C1=CC=CC=C1 RXBWBCOTPZQEJV-UHFFFAOYSA-N 0.000 description 1
LBJXTBWCDXMJNQ-UHFFFAOYSA-N tert-butyl 3-(naphthalen-2-ylmethoxy)-4-[4-(phenacylcarbamoyl)phenyl]piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1C(=O)NCC(=O)C1=CC=CC=C1 LBJXTBWCDXMJNQ-UHFFFAOYSA-N 0.000 description 1
KVJBIHKOLBMTPH-UHFFFAOYSA-N tert-butyl 3-(naphthalen-2-ylmethoxy)-4-[4-(trityloxymethyl)phenyl]piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1COC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 KVJBIHKOLBMTPH-UHFFFAOYSA-N 0.000 description 1
MCIRZVNTWMBVTO-UHFFFAOYSA-N tert-butyl 3-(naphthalen-2-ylmethoxy)-4-[4-[(1-phenyltetrazol-5-yl)sulfanylmethyl]phenyl]piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1CSC1=NN=NN1C1=CC=CC=C1 MCIRZVNTWMBVTO-UHFFFAOYSA-N 0.000 description 1
WWNCFGBQGPHZHL-UHFFFAOYSA-N tert-butyl 3-(naphthalen-2-ylmethoxy)-4-[4-[(3-oxo-3-phenylpropyl)carbamoyl]phenyl]piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1C(=O)NCCC(=O)C1=CC=CC=C1 WWNCFGBQGPHZHL-UHFFFAOYSA-N 0.000 description 1
NRVPVFWOJUVEMD-UHFFFAOYSA-N tert-butyl 3-(naphthalen-2-ylmethoxy)-4-[4-[(3-phenyl-1,2,4-oxadiazol-5-yl)methyl]phenyl]piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1CC(ON=1)=NC=1C1=CC=CC=C1 NRVPVFWOJUVEMD-UHFFFAOYSA-N 0.000 description 1
SLFVAJXQAWRONU-UHFFFAOYSA-N tert-butyl 3-(naphthalen-2-ylmethoxy)-4-[4-[2-(2-thiophen-3-ylacetyl)oxyethyl]phenyl]piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1CCOC(=O)CC=1C=CSC=1 SLFVAJXQAWRONU-UHFFFAOYSA-N 0.000 description 1
JGSZIEXYHBYBJR-UHFFFAOYSA-N tert-butyl 3-(naphthalen-2-ylmethoxy)-4-[4-[2-(thiophene-3-carbonyloxy)ethyl]phenyl]piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1CCOC(=O)C=1C=CSC=1 JGSZIEXYHBYBJR-UHFFFAOYSA-N 0.000 description 1
XUTWPKJNXLSBRT-UHFFFAOYSA-N tert-butyl 3-(naphthalen-2-ylmethoxy)-4-[4-[2-oxo-2-(phenacylamino)ethyl]phenyl]piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1CC(=O)NCC(=O)C1=CC=CC=C1 XUTWPKJNXLSBRT-UHFFFAOYSA-N 0.000 description 1
AQMLEAKWXBXZKT-UHFFFAOYSA-N tert-butyl 3-(naphthalen-2-ylmethoxy)-4-[4-[2-oxo-2-[(3-oxo-3-phenylpropyl)amino]ethyl]phenyl]piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1CC(=O)NCCC(=O)C1=CC=CC=C1 AQMLEAKWXBXZKT-UHFFFAOYSA-N 0.000 description 1
SHZGBDMUXPSVDK-UHFFFAOYSA-N tert-butyl 3-(naphthalen-2-ylmethoxy)-4-[4-[[(2-phenylacetyl)amino]methyl]phenyl]piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1CNC(=O)CC1=CC=CC=C1 SHZGBDMUXPSVDK-UHFFFAOYSA-N 0.000 description 1
ZJPPFKXNOOXDOA-UHFFFAOYSA-N tert-butyl 3-[(1-methoxynaphthalen-2-yl)methoxy]-4-[4-(trityloxymethyl)phenyl]piperidine-1-carboxylate Chemical compound C1=CC2=CC=CC=C2C(OC)=C1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1COC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ZJPPFKXNOOXDOA-UHFFFAOYSA-N 0.000 description 1
OAANPZVKOLXAQP-UHFFFAOYSA-N tert-butyl 3-[(2-cyanophenyl)methoxy]-4-phenylpiperidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C=CC=CC=2)C1OCC1=CC=CC=C1C#N OAANPZVKOLXAQP-UHFFFAOYSA-N 0.000 description 1
YXEQVFUYHYUOCO-UHFFFAOYSA-N tert-butyl 3-[(2-methoxyphenyl)methoxy]-4-[4-(naphthalen-2-ylmethoxy)phenyl]piperidine-1-carboxylate Chemical compound COC1=CC=CC=C1COC1C(C=2C=CC(OCC=3C=C4C=CC=CC4=CC=3)=CC=2)CCN(C(=O)OC(C)(C)C)C1 YXEQVFUYHYUOCO-UHFFFAOYSA-N 0.000 description 1
DTWLKHQTEKXMRG-UHFFFAOYSA-N tert-butyl 3-[(4-hydroxynaphthalen-2-yl)methoxy]-4-[4-(2-phenylmethoxyethoxy)phenyl]piperidine-1-carboxylate Chemical compound C=1C(O)=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1OCCOCC1=CC=CC=C1 DTWLKHQTEKXMRG-UHFFFAOYSA-N 0.000 description 1
PKHLGYDARGPVAM-UHFFFAOYSA-N tert-butyl 3-[(4-phenylmethoxynaphthalen-2-yl)methoxy]-4-[4-(2-trityloxyethyl)phenyl]piperidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C=CC(CCOC(C=3C=CC=CC=3)(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=2)C1OCC(C=C1C=CC=CC1=1)=CC=1OCC1=CC=CC=C1 PKHLGYDARGPVAM-UHFFFAOYSA-N 0.000 description 1
XOHXMMJHXLEVNM-UHFFFAOYSA-N tert-butyl 3-hydroxy-4-(4-methylphenyl)piperidine-1-carboxylate Chemical compound C1=CC(C)=CC=C1C1C(O)CN(C(=O)OC(C)(C)C)CC1 XOHXMMJHXLEVNM-UHFFFAOYSA-N 0.000 description 1
QZAXFDQNIHYLCS-UHFFFAOYSA-N tert-butyl 3-hydroxy-4-[4-(2-hydroxyethyl)phenyl]piperidine-1-carboxylate Chemical compound OC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(CCO)C=C1 QZAXFDQNIHYLCS-UHFFFAOYSA-N 0.000 description 1
LGCLILCDGVWEIR-UHFFFAOYSA-N tert-butyl 3-hydroxy-4-[4-(2-phenoxyethoxy)phenyl]piperidine-1-carboxylate Chemical compound OC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1OCCOC1=CC=CC=C1 LGCLILCDGVWEIR-UHFFFAOYSA-N 0.000 description 1
ZSCHWMMDUIXLSJ-UHFFFAOYSA-N tert-butyl 3-hydroxy-4-[4-(naphthalen-2-ylmethoxy)phenyl]piperidine-1-carboxylate Chemical compound OC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1OCC1=CC=C(C=CC=C2)C2=C1 ZSCHWMMDUIXLSJ-UHFFFAOYSA-N 0.000 description 1
ONHBUAMHVYRCCX-UHFFFAOYSA-N tert-butyl 3-hydroxy-4-[4-[3-(2-phenyl-1,3-dioxolan-2-yl)propoxy]phenyl]piperidine-1-carboxylate Chemical compound OC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1OCCCC1(C=2C=CC=CC=2)OCCO1 ONHBUAMHVYRCCX-UHFFFAOYSA-N 0.000 description 1
ZFOIHKXJUVRGSU-UHFFFAOYSA-N tert-butyl 3-hydroxy-4-naphthalen-1-ylpiperidine-1-carboxylate Chemical compound OC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=CC2=CC=CC=C12 ZFOIHKXJUVRGSU-UHFFFAOYSA-N 0.000 description 1
MUZXNGRBMODVSP-UHFFFAOYSA-N tert-butyl 3-naphthalen-2-yloxy-4-(4-phenylmethoxyphenyl)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1OC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1OCC1=CC=CC=C1 MUZXNGRBMODVSP-UHFFFAOYSA-N 0.000 description 1
ZXJWUZRWPRIZPX-UHFFFAOYSA-N tert-butyl 4-(1,2-dihydroacenaphthylen-5-yl)-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C1CC2=CC=CC3=C2C1=CC=C3C1CCN(C(=O)OC(C)(C)C)CC1OCC1=CC=C(C=CC=C2)C2=C1 ZXJWUZRWPRIZPX-UHFFFAOYSA-N 0.000 description 1
ICNRCASVLLSZQO-UHFFFAOYSA-N tert-butyl 4-(1,3-benzodioxol-5-yl)-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C1=C2OCOC2=CC(C2CCN(CC2OCC=2C=C3C=CC=CC3=CC=2)C(=O)OC(C)(C)C)=C1 ICNRCASVLLSZQO-UHFFFAOYSA-N 0.000 description 1
HPYMWZBHRDYGPM-UHFFFAOYSA-N tert-butyl 4-(1,3-benzodioxol-5-yl)-3-hydroxypiperidine-1-carboxylate Chemical compound OC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(OCO2)C2=C1 HPYMWZBHRDYGPM-UHFFFAOYSA-N 0.000 description 1
CDQDKOCOUZQBSA-UHFFFAOYSA-N tert-butyl 4-(3-fluorophenyl)-3-hydroxypiperidine-1-carboxylate Chemical compound OC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=CC(F)=C1 CDQDKOCOUZQBSA-UHFFFAOYSA-N 0.000 description 1
YBXMLIZYJHSGAX-UHFFFAOYSA-N tert-butyl 4-(4-bromophenyl)-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(Br)C=C1 YBXMLIZYJHSGAX-UHFFFAOYSA-N 0.000 description 1
XXHIUIDWKVIAOG-UHFFFAOYSA-N tert-butyl 4-(4-bromophenyl)-3-[(4-methoxyphenyl)methoxy]piperidine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1COC1C(C=2C=CC(Br)=CC=2)CCN(C(=O)OC(C)(C)C)C1 XXHIUIDWKVIAOG-UHFFFAOYSA-N 0.000 description 1
BATBEUHCKSWZEV-UHFFFAOYSA-N tert-butyl 4-(4-chlorophenyl)-3-[(3-phenoxyphenyl)methoxy]piperidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C=CC(Cl)=CC=2)C1OCC(C=1)=CC=CC=1OC1=CC=CC=C1 BATBEUHCKSWZEV-UHFFFAOYSA-N 0.000 description 1
IBHQJGAYTCBZOR-UHFFFAOYSA-N tert-butyl 4-(4-chlorophenyl)-3-hydroxypiperidine-1-carboxylate Chemical compound OC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(Cl)C=C1 IBHQJGAYTCBZOR-UHFFFAOYSA-N 0.000 description 1
NEIJDHCZWQVPRH-UHFFFAOYSA-N tert-butyl 4-(4-chlorophenyl)-4-hydroxy-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1(O)C1=CC=C(Cl)C=C1 NEIJDHCZWQVPRH-UHFFFAOYSA-N 0.000 description 1
RYFWABDPPGHGQT-UHFFFAOYSA-N tert-butyl 4-(4-chlorophenyl)-4-hydroxy-3-[(4-methoxyphenyl)methoxy]piperidine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1COC1C(C=2C=CC(Cl)=CC=2)(O)CCN(C(=O)OC(C)(C)C)C1 RYFWABDPPGHGQT-UHFFFAOYSA-N 0.000 description 1
IIGLILRPFNRFGZ-UHFFFAOYSA-N tert-butyl 4-(4-cyanophenyl)-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(C#N)C=C1 IIGLILRPFNRFGZ-UHFFFAOYSA-N 0.000 description 1
YLEYKTSIHBLOOL-UHFFFAOYSA-N tert-butyl 4-(4-fluorophenyl)-3-(5,6,7,8-tetrahydronaphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2CCCCC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(F)C=C1 YLEYKTSIHBLOOL-UHFFFAOYSA-N 0.000 description 1
SFYXBVNNQJBRJW-UHFFFAOYSA-N tert-butyl 4-(4-fluorophenyl)-3-(isoquinolin-6-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=NC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(F)C=C1 SFYXBVNNQJBRJW-UHFFFAOYSA-N 0.000 description 1
DRRQAPKFNXFBBU-UHFFFAOYSA-N tert-butyl 4-(4-fluorophenyl)-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(F)C=C1 DRRQAPKFNXFBBU-UHFFFAOYSA-N 0.000 description 1
NLKIPOLSWAXVLW-UHFFFAOYSA-N tert-butyl 4-(4-fluorophenyl)-3-[(4-methoxyquinazolin-2-yl)methoxy]piperidine-1-carboxylate Chemical compound N=1C2=CC=CC=C2C(OC)=NC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(F)C=C1 NLKIPOLSWAXVLW-UHFFFAOYSA-N 0.000 description 1
KQEQUEBMVKGMTE-UHFFFAOYSA-N tert-butyl 4-(4-methoxycarbonylphenyl)-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C1=CC(C(=O)OC)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(C(=O)OC(C)(C)C)CC1 KQEQUEBMVKGMTE-UHFFFAOYSA-N 0.000 description 1
ZJZBVQYOGZHZRF-UHFFFAOYSA-N tert-butyl 4-(4-methylphenyl)-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C1=CC(C)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(C(=O)OC(C)(C)C)CC1 ZJZBVQYOGZHZRF-UHFFFAOYSA-N 0.000 description 1
XKSFBWGMVZKZJD-UHFFFAOYSA-N tert-butyl 4-[3-(benzylcarbamoyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1 XKSFBWGMVZKZJD-UHFFFAOYSA-N 0.000 description 1
YZWXASNUPAXKAT-UHFFFAOYSA-N tert-butyl 4-[3-(hydroxymethyl)phenyl]-3-[(4-phenylmethoxynaphthalen-2-yl)methoxy]piperidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C=C(CO)C=CC=2)C1OCC(C=C1C=CC=CC1=1)=CC=1OCC1=CC=CC=C1 YZWXASNUPAXKAT-UHFFFAOYSA-N 0.000 description 1
NWRZRTLAVOUAOI-UHFFFAOYSA-N tert-butyl 4-[4-(2,2-dimethylpropanoyloxymethyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(COC(=O)C(C)(C)C)C=C1 NWRZRTLAVOUAOI-UHFFFAOYSA-N 0.000 description 1
IQMXNVGRPUQAIV-UHFFFAOYSA-N tert-butyl 4-[4-(2-aminoethoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(OCCN)C=C1 IQMXNVGRPUQAIV-UHFFFAOYSA-N 0.000 description 1
PJPKPADLVWXUGL-UHFFFAOYSA-N tert-butyl 4-[4-(2-benzamidoethoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1OCCNC(=O)C1=CC=CC=C1 PJPKPADLVWXUGL-UHFFFAOYSA-N 0.000 description 1
ANONQFPFUCWTQV-UHFFFAOYSA-N tert-butyl 4-[4-(2-hydroxyethoxy)phenyl]-3-[(4-hydroxynaphthalen-2-yl)methoxy]piperidine-1-carboxylate Chemical compound C=1C(O)=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(OCCO)C=C1 ANONQFPFUCWTQV-UHFFFAOYSA-N 0.000 description 1
INACUPCPTBGKBD-UHFFFAOYSA-N tert-butyl 4-[4-(2-hydroxyethyl)phenyl]-3-[(4-phenylmethoxynaphthalen-2-yl)methoxy]piperidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C=CC(CCO)=CC=2)C1OCC(C=C1C=CC=CC1=1)=CC=1OCC1=CC=CC=C1 INACUPCPTBGKBD-UHFFFAOYSA-N 0.000 description 1
ZWRXYJWSFVHIMX-UHFFFAOYSA-N tert-butyl 4-[4-(2-phenoxyethoxy)phenyl]-3-[[4-(2-trimethylsilylethoxymethoxy)naphthalen-2-yl]methoxy]piperidine-1-carboxylate Chemical compound C=1C(OCOCC[Si](C)(C)C)=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1OCCOC1=CC=CC=C1 ZWRXYJWSFVHIMX-UHFFFAOYSA-N 0.000 description 1
XNLCYCDWJAZVCJ-UHFFFAOYSA-N tert-butyl 4-[4-(3-benzoyloxyprop-1-enyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1C=CCOC(=O)C1=CC=CC=C1 XNLCYCDWJAZVCJ-UHFFFAOYSA-N 0.000 description 1
IZQVMWLQTUHOMT-UHFFFAOYSA-N tert-butyl 4-[4-(3-ethoxy-3-oxopropyl)phenyl]-3-hydroxypiperidine-1-carboxylate Chemical compound C1=CC(CCC(=O)OCC)=CC=C1C1C(O)CN(C(=O)OC(C)(C)C)CC1 IZQVMWLQTUHOMT-UHFFFAOYSA-N 0.000 description 1
CGKOETQDHRBSRQ-UHFFFAOYSA-N tert-butyl 4-[4-(3-hydroxyprop-1-enyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(C=CCO)C=C1 CGKOETQDHRBSRQ-UHFFFAOYSA-N 0.000 description 1
ZIHLHQLYTXNXBI-UHFFFAOYSA-N tert-butyl 4-[4-(3-hydroxypropoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical group C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(OCCCO)C=C1 ZIHLHQLYTXNXBI-UHFFFAOYSA-N 0.000 description 1
AICJIAKKRWXFQM-UHFFFAOYSA-N tert-butyl 4-[4-(3-hydroxypropyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(CCCO)C=C1 AICJIAKKRWXFQM-UHFFFAOYSA-N 0.000 description 1
UCJAZQSEULZVHX-UHFFFAOYSA-N tert-butyl 4-[4-(3-morpholin-4-ylpropoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1OCCCN1CCOCC1 UCJAZQSEULZVHX-UHFFFAOYSA-N 0.000 description 1
IXBYWIRDJBLBHC-UHFFFAOYSA-N tert-butyl 4-[4-(4-hydroxy-4-phenylbutoxy)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1OCCCC(O)C1=CC=CC=C1 IXBYWIRDJBLBHC-UHFFFAOYSA-N 0.000 description 1
FHUYWNBWRPCNJV-UHFFFAOYSA-N tert-butyl 4-[4-(aminomethyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(CN)C=C1 FHUYWNBWRPCNJV-UHFFFAOYSA-N 0.000 description 1
XNQPZNVAUHLYBJ-UHFFFAOYSA-N tert-butyl 4-[4-(benzamidomethyl)phenyl]-3-[[4-(2-trimethylsilylethoxymethoxy)naphthalen-2-yl]methoxy]piperidine-1-carboxylate Chemical compound C=1C(OCOCC[Si](C)(C)C)=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1CNC(=O)C1=CC=CC=C1 XNQPZNVAUHLYBJ-UHFFFAOYSA-N 0.000 description 1
SYXODBKPCGJMOU-UHFFFAOYSA-N tert-butyl 4-[4-(benzenesulfonamidomethyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1CNS(=O)(=O)C1=CC=CC=C1 SYXODBKPCGJMOU-UHFFFAOYSA-N 0.000 description 1
GHZXYQABPCPGHS-UHFFFAOYSA-N tert-butyl 4-[4-(hydroxymethyl)phenyl]-3-[(1-methoxynaphthalen-2-yl)methoxy]piperidine-1-carboxylate Chemical compound C1=CC2=CC=CC=C2C(OC)=C1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(CO)C=C1 GHZXYQABPCPGHS-UHFFFAOYSA-N 0.000 description 1
JPMSSLKKOXNNDS-UHFFFAOYSA-N tert-butyl 4-[4-(methoxycarbonyloxymethyl)phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C1=CC(COC(=O)OC)=CC=C1C1C(OCC=2C=C3C=CC=CC3=CC=2)CN(C(=O)OC(C)(C)C)CC1 JPMSSLKKOXNNDS-UHFFFAOYSA-N 0.000 description 1
CFZSQDWBJXXQRK-UHFFFAOYSA-N tert-butyl 4-[4-[(3,5-dimethoxybenzoyl)oxymethyl]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound COC1=CC(OC)=CC(C(=O)OCC=2C=CC(=CC=2)C2C(CN(CC2)C(=O)OC(C)(C)C)OCC=2C=C3C=CC=CC3=CC=2)=C1 CFZSQDWBJXXQRK-UHFFFAOYSA-N 0.000 description 1
PFUSTVSYTZGRQK-UHFFFAOYSA-N tert-butyl 4-[4-[(4-hydroxybenzoyl)oxymethyl]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1COC(=O)C1=CC=C(O)C=C1 PFUSTVSYTZGRQK-UHFFFAOYSA-N 0.000 description 1
AZBOEJHMEBFYRH-UHFFFAOYSA-N tert-butyl 4-[4-[2-(1,3-benzodioxole-5-carbonyloxy)ethoxy]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C1=C2OCOC2=CC(C(=O)OCCOC2=CC=C(C=C2)C2CCN(CC2OCC=2C=C3C=CC=CC3=CC=2)C(=O)OC(C)(C)C)=C1 AZBOEJHMEBFYRH-UHFFFAOYSA-N 0.000 description 1
QMJMFIYNPAVSBN-UHFFFAOYSA-N tert-butyl 4-[4-[2-(1H-imidazole-2-carbonyloxy)ethyl]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(C(C1)OCC2=CC3=CC=CC=C3C=C2)C4=CC=C(C=C4)CCOC(=O)C5=NC=CN5 QMJMFIYNPAVSBN-UHFFFAOYSA-N 0.000 description 1
JWYQASCZUVQGCS-UHFFFAOYSA-N tert-butyl 4-[4-[2-(2-chlorobenzoyl)oxyethyl]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1CC(C(CC1)C1=CC=C(C=C1)CCOC(C1=C(C=CC=C1)Cl)=O)OCC1=CC2=CC=CC=C2C=C1 JWYQASCZUVQGCS-UHFFFAOYSA-N 0.000 description 1
ODYUJZRFJHZZBC-UHFFFAOYSA-N tert-butyl 4-[4-[2-(2-methylsulfanylbenzoyl)oxyethoxy]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound CSC1=CC=CC=C1C(=O)OCCOC1=CC=C(C2C(CN(CC2)C(=O)OC(C)(C)C)OCC=2C=C3C=CC=CC3=CC=2)C=C1 ODYUJZRFJHZZBC-UHFFFAOYSA-N 0.000 description 1
ZXCPVTUHINKBRK-UHFFFAOYSA-N tert-butyl 4-[4-[2-(4-methoxybenzoyl)oxyethoxy]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1C(=O)OCCOC1=CC=C(C2C(CN(CC2)C(=O)OC(C)(C)C)OCC=2C=C3C=CC=CC3=CC=2)C=C1 ZXCPVTUHINKBRK-UHFFFAOYSA-N 0.000 description 1
CKGUNLDAJSHVPJ-UHFFFAOYSA-N tert-butyl 4-[4-[2-(cyclohexanecarbonyloxy)ethyl]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1CCOC(=O)C1CCCCC1 CKGUNLDAJSHVPJ-UHFFFAOYSA-N 0.000 description 1
KSZPQEALSOKOGD-UHFFFAOYSA-N tert-butyl 4-[4-[2-(furan-3-carbonyloxy)ethoxy]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1OCCOC(=O)C=1C=COC=1 KSZPQEALSOKOGD-UHFFFAOYSA-N 0.000 description 1
WEUFIRFVCKFDGK-UHFFFAOYSA-N tert-butyl 4-[4-[2-[2-(4-methoxyphenyl)acetyl]oxyethyl]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C1=CC(OC)=CC=C1CC(=O)OCCC1=CC=C(C2C(CN(CC2)C(=O)OC(C)(C)C)OCC=2C=C3C=CC=CC3=CC=2)C=C1 WEUFIRFVCKFDGK-UHFFFAOYSA-N 0.000 description 1
YSXNLLQWJQXANP-UHFFFAOYSA-N tert-butyl 4-[4-[2-[2-(chloromethyl)benzoyl]oxyethoxy]phenyl]-3-[[4-(2-trimethylsilylethoxymethoxy)naphthalen-2-yl]methoxy]piperidine-1-carboxylate Chemical compound C=1C(OCOCC[Si](C)(C)C)=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C(C=C1)=CC=C1OCCOC(=O)C1=CC=CC=C1CCl YSXNLLQWJQXANP-UHFFFAOYSA-N 0.000 description 1
BCWZOKDXNLZFOH-UHFFFAOYSA-N tert-butyl 4-[4-[3-(2,2-dimethylpropanoyloxy)propoxy]phenyl]-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=CC=1COC1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(OCCCOC(=O)C(C)(C)C)C=C1 BCWZOKDXNLZFOH-UHFFFAOYSA-N 0.000 description 1
WIZMETYOONJXGW-UHFFFAOYSA-N tert-butyl 4-naphthalen-1-yl-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C1=CC=C2C(C3CCN(CC3OCC=3C=C4C=CC=CC4=CC=3)C(=O)OC(C)(C)C)=CC=CC2=C1 WIZMETYOONJXGW-UHFFFAOYSA-N 0.000 description 1
MKBHQDPABNMEAN-UHFFFAOYSA-N tert-butyl 4-naphthalen-2-yl-3-(naphthalen-2-ylmethoxy)piperidine-1-carboxylate Chemical compound C1=CC=CC2=CC(C3CCN(CC3OCC=3C=C4C=CC=CC4=CC=3)C(=O)OC(C)(C)C)=CC=C21 MKBHQDPABNMEAN-UHFFFAOYSA-N 0.000 description 1
GEQGPILOVIRUMW-UHFFFAOYSA-N tert-butyl 4-phenyl-3-[[2-[(pyridine-3-carbonylamino)methyl]phenyl]methoxy]piperidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C=CC=CC=2)C1OCC1=CC=CC=C1CNC(=O)C1=CC=CN=C1 GEQGPILOVIRUMW-UHFFFAOYSA-N 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
150000003556 thioamides Chemical class 0.000 description 1
150000007944 thiolates Chemical class 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
229960004605 timolol Drugs 0.000 description 1
KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
229940110851 tolazine Drugs 0.000 description 1
JIVZKJJQOZQXQB-UHFFFAOYSA-N tolazoline Chemical compound C=1C=CC=CC=1CC1=NCCN1 JIVZKJJQOZQXQB-UHFFFAOYSA-N 0.000 description 1
125000005490 tosylate group Chemical group 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
229960001288 triamterene Drugs 0.000 description 1
150000003852 triazoles Chemical group 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
229910052905 tridymite Inorganic materials 0.000 description 1
BQFPCTXLBRVFJL-UHFFFAOYSA-N triethoxymethylbenzene Chemical compound CCOC(OCC)(OCC)C1=CC=CC=C1 BQFPCTXLBRVFJL-UHFFFAOYSA-N 0.000 description 1
150000008648 triflates Chemical class 0.000 description 1
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
UYPYRKYUKCHHIB-UHFFFAOYSA-N trimethylamine N-oxide Chemical compound C[N+](C)(C)[O-] UYPYRKYUKCHHIB-UHFFFAOYSA-N 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
150000008303 tropinone derivatives Chemical class 0.000 description 1
208000019553 vascular disease Diseases 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
229960001722 verapamil Drugs 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
150000003751 zinc Chemical class 0.000 description 1
VCQWRGCXUWPSGY-UHFFFAOYSA-L zinc;2,2,2-trifluoroacetate Chemical compound [Zn+2].[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F VCQWRGCXUWPSGY-UHFFFAOYSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/42—Oxygen atoms attached in position 3 or 5
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Ophthalmology & Optometry (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)
Pyridine Compounds (AREA)

NO980954A 1995-09-07 1998-03-05 Nye-4-(oksyalkoksyfenyl)-3-oksy-piperidiner for behandling av hjerte- og nyreinsuffisiens NO310069B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH254895		1995-09-07
CH187696		1996-07-26
PCT/EP1996/003803 WO1997009311A1 (fr)	1995-09-07	1996-08-29	Nouvelles 4-(oxyalcoxyphenyl)-3-oxy-piperidines utiles pour traiter l'insuffisance cardiaque et renale

Publications (3)

Publication Number	Publication Date
NO980954D0 NO980954D0 (no)	1998-03-05
NO980954L NO980954L (no)	1998-04-28
NO310069B1 true NO310069B1 (no)	2001-05-14

Family

ID=25688898

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO980954A NO310069B1 (no)	1995-09-07	1998-03-05	Nye-4-(oksyalkoksyfenyl)-3-oksy-piperidiner for behandling av hjerte- og nyreinsuffisiens

Country Status (26)

Country	Link
US (2)	US6051712A (fr)
EP (1)	EP0863875B1 (fr)
JP (1)	JP3648251B2 (fr)
KR (1)	KR100384979B1 (fr)
CN (1)	CN1256326C (fr)
AT (1)	ATE242213T1 (fr)
BR (1)	BR9610385A (fr)
CA (1)	CA2230931C (fr)
CY (1)	CY2488B1 (fr)
CZ (1)	CZ292327B6 (fr)
DE (1)	DE59610509D1 (fr)
DK (1)	DK0863875T3 (fr)
ES (1)	ES2201192T3 (fr)
HU (1)	HUP9900926A3 (fr)
IL (1)	IL123293A (fr)
MA (1)	MA23967A1 (fr)
MY (1)	MY121967A (fr)
NO (1)	NO310069B1 (fr)
NZ (1)	NZ315677A (fr)
PL (1)	PL193686B1 (fr)
PT (1)	PT863875E (fr)
RU (1)	RU2167865C2 (fr)
SA (1)	SA96170317B1 (fr)
TR (1)	TR199800409T1 (fr)
TW (1)	TW474932B (fr)
WO (1)	WO1997009311A1 (fr)

Families Citing this family (95)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU221921B1 (hu) *	1996-07-08	2003-02-28	Richter Gedeon Vegyészeti Gyár Rt.	N-benzil-piperidin- és tetrahidropiridinszármazékok és eljárás azok előállítására
ATE248147T1 (de)	1997-05-14	2003-09-15	Neurosearch As	Piperidine derivate als inhibitoren der neurotransmitter-wiederaufbaunahme
JP2002514222A (ja)	1997-05-29	2002-05-14	スミスクライン・ビーチャム・コーポレイション	新規方法
WO1999012532A2 (fr) *	1997-09-08	1999-03-18	F.Hoffmann-La Roche Ag	Derives de piperidine contre la malaria
TR200002904T2 (tr)	1998-04-10	2001-02-21	Japan Tobacco Inc.	Amidin bileşikleri
US6268499B1 (en)	1998-08-10	2001-07-31	Hoffman-La Roche Inc.	Process and intermediates for preparation of substituted piperidine-epoxides
US6274735B1 (en)	1998-08-10	2001-08-14	Hoffmann-La Roche Inc.	Process and intermediates for preparation of substituted piperidines
AU3818900A (en) *	1999-04-14	2000-11-02	F. Hoffmann-La Roche Ag	Process for the preparation of substituted piperidines
US6197959B1 (en) *	1999-04-27	2001-03-06	Hoffmann-La Roche Inc.	Piperidine derivatives
US6376672B1 (en) *	1999-04-27	2002-04-23	Hoffmann-La Roche Inc.	Naphthalenylmethoxypiperidines as renin inhibitors
IT1313702B1 (it) *	1999-08-02	2002-09-09	Chemi Spa	Processo per la preparazione di derivati 3-sostituiti di 4-fenil-piperidine.
WO2001016121A1 (fr) *	1999-08-31	2001-03-08	Merck & Co., Inc.	Composes heterocycliques et procedes d'utilisation de ceux-ci
MXPA02003740A (es) *	1999-10-15	2002-09-30	Hoffmann La Roche	Derivados de benzodiazepina.
HUP0300649A3 (en) *	2000-06-13	2003-10-28	Basf Ag	Fungicidal 5-phenyl substituted 2-(cyanoamino)pyrimidines, preparation and use thereof
US20060079533A1 (en) *	2001-03-23	2006-04-13	Nieman James A	Methods of treating alzheimer's disease
JP2005514362A (ja)	2001-11-19	2005-05-19	イーランファーマスーティカルズ、インコーポレイテッド	３，４二置換、３，５二置換、及び３，４，５置換ピペリジン及びピペラジン
CA2483241C (fr)	2002-04-29	2011-05-31	Actelion Pharmaceuticals Ltd	Nouveaux derives de diazabicyclononene
US20060009497A1 (en) *	2002-06-27	2006-01-12	Actelion Pharmaceuticals, Ltd.	Novel tetrahydropyridine derivatives as renin inhibitors
JP2006519229A (ja)	2003-02-13	2006-08-24	アルバート・アインシュタイン・カレッジ・オヴ・メディシン・オヴ・イェシヴァ・ユニヴァーシティ	視床下部内の長鎖脂肪アシルＣｏＡレベルの変調による摂食量およびグルコース産生量の調節
US20040204455A1 (en) *	2003-04-10	2004-10-14	Cody Wayne Livingston	Piperidine derivative rennin inhibitors
US20040214832A1 (en) *	2003-04-10	2004-10-28	Cuiman Cai	Piperazine derivative renin inhibitors
US20060217371A1 (en) *	2003-04-28	2006-09-28	Olivier Bezencon	Diazabicyclononene and tetrahydropyriddine derivatives as renin inhibitors
CN1972912A (zh) *	2003-04-29	2007-05-30	埃科特莱茵药品有限公司	新型3,4－二取代的1,2,3,6－四氢吡啶衍生物
BRPI0409818A (pt) *	2003-04-30	2006-05-09	Actelion Pharmaceuticals Ltd	compostos, composições farmacêuticas, método para o tratamento ou profilaxia de doenças, e, usos de compostos e de um ou mais compostos em combinação com outros compostos farmacologicamente ativos
CN1780663A (zh) *	2003-04-30	2006-05-31	埃科特莱茵药品有限公司	作为肾素抑制剂的新型3－位具有杂原子的9－氮杂双环壬烯衍生物
US20060205768A1 (en) *	2003-04-30	2006-09-14	Olivier Bezencon	Tropane derivatives and their use as ace inhibitors
MXPA05011711A (es) *	2003-05-02	2006-01-23	Actelion Pharmaceuticals Ltd	Derivados de diazabiciclononeno.
EP2080757A1 (fr) *	2003-07-24	2009-07-22	Euro-Celtique S.A.	Composés de hétéroaryl-tétrahydropipéridyle utiles pour traiter ou prévenir la douleur
TW200513461A (en)	2003-10-01	2005-04-16	Speedel Experimenta Ag	Organische verbindungen
AR045950A1 (es) *	2003-10-09	2005-11-16	Speedel Experimenta Ag	Compuestos derivados de piperazina, composiciones farmaceuticas que los contienen y su uso en la fabricacion de medicamentos.
US20070135405A1 (en) *	2003-10-23	2007-06-14	Olivier Bezencon	Novel diazabicyclononene and tetrahydropyridine derivatives with a new polar side-chain
BRPI0416976A (pt)	2003-11-26	2007-02-21	Novartis Ag	derivados de 4-fenilpiperidina como inibidores de renina
NZ549535A (en)	2004-03-17	2010-11-26	Novartis Ag	Use of aliskiren for treating renal and other disorders
JP2007223901A (ja) *	2004-03-24	2007-09-06	Takeda Chem Ind Ltd	複素環化合物およびその用途
AR053406A1 (es) *	2004-07-09	2007-05-09	Speedel Experimenta Ag	Derivados de piperidina como inhibidores de renina. composiciones farmaceuticas
AU2005276624B2 (en)	2004-08-25	2011-09-29	Actelion Pharmaceuticals Ltd.	Bicyclononene derivatives as renin inhibitors
GB0428526D0 (en)	2004-12-30	2005-02-09	Novartis Ag	Organic compounds
GB0500784D0 (en) *	2005-01-14	2005-02-23	Novartis Ag	Organic compounds
CA2595986A1 (fr) *	2005-01-28	2006-08-03	Actelion Pharmaceuticals Ltd	Acide 7-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}-3,9-diazabicyclo[3.3.31]non-6-ene-6-carboxylique cyclopropyl-(2,3-dimethylbenzyl)amide utilises comme inhibiteurs de la renine pour le traitement de l'hypertension
JP2008535825A (ja) *	2005-03-31	2008-09-04	シュペーデル・エクスペリメンタ・アーゲー	レニン阻害剤としての３，４，５−置換ピペリジン
TW200722424A (en)	2005-03-31	2007-06-16	Speedel Experimenta Ag	Substituted piperidines
CN101151262B (zh) *	2005-03-31	2011-07-06	斯皮德尔实验股份公司	取代的哌啶
EP1897879A3 (fr)	2005-03-31	2008-06-11	Speedel Experimenta AG	Pipéridines 2,4,5-substituées comme inhibiteurs de la rénine
EP1707202A1 (fr) *	2005-03-31	2006-10-04	Speedel Experimenta AG	Composes organiques
AR055756A1 (es) *	2005-03-31	2007-09-05	Speedel Experimenta Ag	Piperidinas sustituidas; procesos de preparacion y su uso como medicamentos
GB0508992D0 (en) *	2005-05-03	2005-06-08	Novartis Ag	Organic compounds
GB0510810D0 (en) *	2005-05-26	2005-06-29	Novartis Ag	Organic compounds
US7799805B2 (en) *	2005-05-27	2010-09-21	Actelion Pharmaceuticals Ltd.	Piperidine carboxylic acid amide derivatives
WO2006131884A2 (fr) *	2005-06-07	2006-12-14	Actelion Pharmaceuticals Ltd	Nouveaux derives de thiazole
GB0514203D0 (en)	2005-07-11	2005-08-17	Novartis Ag	Organic compounds
PT1910333E (pt) *	2005-07-26	2013-08-01	Sanofi Sa	Derivados de isoquinolona substituída com piperidinilo como inibidores da rho-cinase
MX2008001292A (es)	2005-07-29	2008-03-25	Hoffmann La Roche	Nuevos derivados de indol-3-il-carbonil-piperidina y piperazina.
GB0525673D0 (en) *	2005-12-16	2006-01-25	Novartis Ag	Organic compounds
US20070142389A1 (en) *	2005-12-20	2007-06-21	Pfizer Inc.	Piperidine derivatives
NZ569135A (en)	2005-12-30	2011-08-26	Novartis Ag	3,5-Substituted piperidine compounds as renin inhibitors
RU2415840C2 (ru) *	2005-12-30	2011-04-10	Новартис Аг	3,5-замещенные пиперидины, как ингибиторы ренина
EP1816122A3 (fr) *	2006-01-19	2007-09-19	Speedel Experimenta AG	Pipéridines substituées 3,4,5 en tant que composants thérapeutiques
TW200804359A (en) *	2006-01-19	2008-01-16	Speedel Experimenta Ag	Substituted 4-phenylpiperidines
KR20080091273A (ko) *	2006-02-02	2008-10-09	액테리온 파마슈티칼 리미티드	레닌 저해제로서의 2차 아민
US8084485B2 (en)	2006-03-31	2011-12-27	Vitae Pharmaceuticals, Inc.	6-(aminoalkyl)indazoles
RS52062B (sr)	2006-05-19	2012-06-30	Abbott Laboratories	Cns aktivni azabiciklični alkanski derivati koji su supstituisani spojenim bicikloheterociklom
AR061265A1 (es) *	2006-06-08	2008-08-13	Speedel Experimenta Ag	Piperidinas 2,5- disustituidas
CL2007002689A1 (es)	2006-09-18	2008-04-18	Vitae Pharmaceuticals Inc	Compuestos derivados de piperidin-1-carboxamida, inhibidores de la renina; compuestos intermediarios; composicion farmaceutica; y uso en el tratamiento de enfermedades tales como hipertension, insuficiencia cardiaca, fibrosis cardiaca, entre otras.
AU2007321671A1 (en) *	2006-11-17	2008-05-22	Merck Frosst Canada Ltd.	Renin inhibitors
US7638541B2 (en)	2006-12-28	2009-12-29	Metabolex Inc.	5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine
EP1987834A3 (fr)	2007-02-13	2008-11-19	Speedel Experimenta AG	Pipéridines substituées en tant que composants thérapeutiques
JP2010524879A (ja) *	2007-04-19	2010-07-22	エフ．ホフマン−ラロシュアーゲー	ジヒドロ−ベンゾ［ｂ］［１，４］ジアゼピン−２−オンスルホンアミド誘導体
EP2604599A1 (fr)	2007-04-27	2013-06-19	Purdue Pharma LP	Antagonistes de TRPV1 et utilisations de ceux-ci
WO2009000811A1 (fr)	2007-06-25	2008-12-31	Novartis Ag	Composés organiques
JP5489997B2 (ja)	2007-07-19	2014-05-14	シマベイセラピューティクス，インコーポレーテッド	糖尿病および代謝疾患の治療のためのＲＵＰ３またはＧＰＲｌ１９受容体のアゴニストとしてのＮ−アザ環状置換ピロール、ピラゾール、イミダゾール、トリアゾールおよびテトラゾール誘導体
EP2018862A1 (fr)	2007-07-25	2009-01-28	Speedel Experimenta AG	Pipéridines substituées en tant que composants thérapeutiques
AR068887A1 (es)	2007-10-18	2009-12-16	Speedel Experimenta Ag	Piperidinas trisustituidas
TW200922596A (en) *	2007-10-25	2009-06-01	Speedel Experimenta Ag	4,4-disubstituted piperidines
AU2008320806A1 (en) *	2007-11-02	2009-05-07	Novartis Ag	4,4-disubstituted piperidines as renin inhibitors
TW200932241A (en)	2007-12-05	2009-08-01	Speedel Experimenta Ag	Organic compounds
WO2009106599A2 (fr) *	2008-02-29	2009-09-03	Novartis Ag	Pipéridines substituées en tant que composés thérapeutiques
TW201002705A (en) *	2008-03-31	2010-01-16	Metabolex Inc	Oxymethylene aryl compounds and uses thereof
NZ589019A (en)	2008-05-05	2012-10-26	Merck Frosst Canada Ltd	3, 4 - substituted piperidine derivatives as renin inhibitors
CN102203074A (zh) *	2008-06-20	2011-09-28	麦它波莱克斯股份有限公司	芳基gpr119激动剂及其用途
WO2010013849A1 (fr)	2008-08-01	2010-02-04	日本ケミファ株式会社	Agoniste de gpr119
EP2163245A1 (fr)	2008-09-10	2010-03-17	Novartis Ag	Inhibiteurs de la rénine pour le traitement du psoriasis
JP2010090110A (ja) *	2008-09-12	2010-04-22	Sumitomo Chemical Co Ltd	Ｎ−置換−トランス−４−アジドピペリジン−３−オールの製造方法
AU2009326797B2 (en) *	2008-12-10	2012-12-13	Merck Canada Inc.	3,4 - substituted piperidine derivatives as renin inhibitors
EP2421828A2 (fr)	2009-04-24	2012-02-29	Cadila Healthcare Limited	Derivatifs de piperidine comme inhibiteurs de rénine
WO2011030139A1 (fr)	2009-09-11	2011-03-17	Astrazeneca Ab	Derives de 4-(pyrimidin-2-yl)-piperazine et de 4-(pyrimidin-2-yl)-piperidine utilises en tant que modulateurs du gpr119
WO2011041154A1 (fr) *	2009-10-01	2011-04-07	Metabolex, Inc.	Sels de la tétrazol-1-yl-phénoxyméthyl-thiazol-2-yl-pipéridinyl-pyrimidine substituée
EP2585048B1 (fr)	2010-06-23	2018-04-11	CymaBay Therapeutics, Inc.	Compositions de 5-éthyl-2-{4-[4-(4-tétrazol-1-yl-phénoxyméthyl)-thiazol-2-yl]-pipéridin-1-yl}-pyrimidine
US20120184572A1 (en) *	2011-01-13	2012-07-19	Metabolex, Inc.	Aryl gpr119 agonists and uses thereof
US9273043B2 (en)	2011-06-22	2016-03-01	Purdue Pharma L.P.	TRPV1 antagonists including dihydroxy substituent and uses thereof
WO2013088452A2 (fr)	2011-11-11	2013-06-20	Sun Pharma Advanced Research Company Ltd.	Dérivés de quinoléine utilisés en tant qu'inhibiteurs de la rénine
WO2013084241A1 (fr)	2011-12-09	2013-06-13	Cadila Healthcare Limited	Composés inhibiteurs de rénine
CN104370813A (zh) *	2014-10-22	2015-02-25	上海大学	异喹啉-6-甲醛的制备方法
EP3493807A1 (fr)	2016-08-03	2019-06-12	CymaBay Therapeutics, Inc.	Composés d'aryle d'oxyméthylène pour le traitement de maladies gastro-intestinales inflammatoires ou de troubles gastro-intestinaux
CN110041212B (zh) *	2019-05-21	2020-10-02	吉林大学	一种含氟多胺单体及其制备方法、一种聚酰亚胺及其制备方法和一种聚酰亚胺膜
CN119059990B (zh) *	2024-11-01	2025-02-07	安徽昊帆生物有限公司	1-氨基甲酸叔丁酯哌嗪的制备方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1545792B2 (de) *	1965-02-27	1975-08-07	Bayer Ag, 5090 Leverkusen	Verfahren zur Herstellung von 4-Hydroxyplperidinen
GB1422263A (en) *	1973-01-30	1976-01-21	Ferrosan As	4-phenyl-piperidine compounds
IE45511B1 (en) *	1976-09-01	1982-09-08	Ciba Geigy Ag	New derivatives of perhydro-aza-heterocycles and processesfor the production thereof
US4868181A (en) *	1986-08-04	1989-09-19	E. I. Du Pont De Nemours And Company	1,4-dihydropyridine derivatives with calcium agonist and alpha1 -antagonist activity
DK715988D0 (da) *	1988-12-22	1988-12-22	Ferrosan As	Etherifikation og dealkylering af piperidin-derivater samt intermediater
US5272156A (en) *	1989-09-19	1993-12-21	Allergan, Inc.	Acetylenes disubstituted with a heteroaromatic group and a 2-substituted 1,2,3,4-tetrahydroquinolinyl group having retinoid-like activity
RU2097378C1 (ru) *	1991-03-26	1997-11-27	Ф.Хоффманн-Ля Рош Аг	ПРОИЗВОДНЫЕ N-АЦИЛ- α -АМИНОКИСЛОТЫ ИЛИ ИХ ФИЗИОЛОГИЧЕСКИ ПРИЕМЛЕМЫЕ СОЛИ, ПРОСТЫЕ ИЛИ СЛОЖНЫЕ ЭФИРЫ, АМИДЫ ИЛИ ГИДРАТЫ И КОМПОЗИЦИЯ ИНГИБИРУЮЩАЯ СВЯЗЫВАНИЕ АДГЕЗИВНЫХ ПРОТЕИНОВ С ТРОМБОЦИТАМИ И АГРЕГАЦИЮ ТРОМБОЦИТОВ
US5545658A (en) *	1991-03-26	1996-08-13	Hoffman-La Roche Inc.	Amino acid derivatives

1996
- 1996-08-29 PL PL96325425A patent/PL193686B1/pl not_active IP Right Cessation
- 1996-08-29 JP JP51083797A patent/JP3648251B2/ja not_active Expired - Fee Related
- 1996-08-29 HU HU9900926A patent/HUP9900926A3/hu unknown
- 1996-08-29 IL IL12329396A patent/IL123293A/xx not_active IP Right Cessation
- 1996-08-29 TR TR1998/00409T patent/TR199800409T1/xx unknown
- 1996-08-29 ES ES96927715T patent/ES2201192T3/es not_active Expired - Lifetime
- 1996-08-29 EP EP96927715A patent/EP0863875B1/fr not_active Expired - Lifetime
- 1996-08-29 PT PT96927715T patent/PT863875E/pt unknown
- 1996-08-29 CA CA002230931A patent/CA2230931C/fr not_active Expired - Fee Related
- 1996-08-29 NZ NZ315677A patent/NZ315677A/en not_active IP Right Cessation
- 1996-08-29 RU RU98106388/04A patent/RU2167865C2/ru not_active IP Right Cessation
- 1996-08-29 DK DK96927715T patent/DK0863875T3/da active
- 1996-08-29 CZ CZ1998684A patent/CZ292327B6/cs not_active IP Right Cessation
- 1996-08-29 DE DE59610509T patent/DE59610509D1/de not_active Expired - Lifetime
- 1996-08-29 BR BR9610385A patent/BR9610385A/pt not_active IP Right Cessation
- 1996-08-29 WO PCT/EP1996/003803 patent/WO1997009311A1/fr not_active Ceased
- 1996-08-29 CN CNB961976748A patent/CN1256326C/zh not_active Expired - Fee Related
- 1996-08-29 AT AT96927715T patent/ATE242213T1/de active
- 1996-08-29 KR KR10-1998-0701707A patent/KR100384979B1/ko not_active Expired - Fee Related
- 1996-09-02 TW TW085110684A patent/TW474932B/zh not_active IP Right Cessation
- 1996-09-05 MY MYPI96003683A patent/MY121967A/en unknown
- 1996-09-06 MA MA24347A patent/MA23967A1/fr unknown
- 1996-09-24 SA SA96170317A patent/SA96170317B1/ar unknown
1998
- 1998-03-05 NO NO980954A patent/NO310069B1/no not_active IP Right Cessation
1999
- 1999-02-22 US US09/255,185 patent/US6051712A/en not_active Expired - Lifetime
- 1999-12-07 US US09/456,283 patent/US6150526A/en not_active Expired - Lifetime
2004
- 2004-12-03 CY CY0400088A patent/CY2488B1/xx unknown

Also Published As

Publication number	Publication date
CA2230931C (fr)	2009-05-19
HUP9900926A2 (hu)	1999-09-28
MA23967A1 (fr)	1997-04-01
CN1202152A (zh)	1998-12-16
JPH11500447A (ja)	1999-01-12
TW474932B (en)	2002-02-01
WO1997009311A1 (fr)	1997-03-13
NZ315677A (en)	2000-02-28
NO980954L (no)	1998-04-28
CZ68498A3 (cs)	1998-10-14
CA2230931A1 (fr)	1997-03-13
US6150526A (en)	2000-11-21
JP3648251B2 (ja)	2005-05-18
KR19990044459A (ko)	1999-06-25
TR199800409T1 (xx)	1998-05-21
MY121967A (en)	2006-03-31
RU2167865C2 (ru)	2001-05-27
AU6743296A (en)	1997-03-27
SA96170317B1 (ar)	2006-05-13
CN1256326C (zh)	2006-05-17
NO980954D0 (no)	1998-03-05
HK1016177A1 (en)	1999-10-29
CY2488B1 (en)	2005-06-03
PT863875E (pt)	2003-10-31
HUP9900926A3 (en)	2002-12-28
AU708616B2 (en)	1999-08-05
IL123293A (en)	2003-06-24
PL325425A1 (en)	1998-07-20
ES2201192T3 (es)	2004-03-16
IL123293A0 (en)	1998-09-24
US6051712A (en)	2000-04-18
MX9801814A (es)	1998-08-30
DE59610509D1 (de)	2003-07-10
DK0863875T3 (da)	2003-12-01
EP0863875B1 (fr)	2003-06-04
PL193686B1 (pl)	2007-03-30
ATE242213T1 (de)	2003-06-15
KR100384979B1 (ko)	2003-10-17
BR9610385A (pt)	1999-07-06
CZ292327B6 (cs)	2003-09-17
EP0863875A1 (fr)	1998-09-16

Legal Events

Date	Code	Title	Description
2014-03-24	MM1K	Lapsed by not paying the annual fees

Publication	Publication Date	Title
ES2201192T3 (es)	2004-03-16	Nuevos 4-(oxialcoxifenil)-3-oxi-piperidinas para el tratamiento de la insuficiencia cardiaca y renal.
US11098032B2 (en)	2021-08-24	Pyran dervatives as CYP11A1 (cytochrome P450 monooxygenase 11A1) inhibitors
AU700837B2 (en)	1999-01-14	1,4-di-substituted piperidine derivatives
JP2713394B2 (ja)	1998-02-16	トリアゾール化合物合成用中間体
CA2454613A1 (fr)	2003-01-16	Piperidines aniliniques substituees, utilisees comme antagonistes selectifs de la mch
NO320803B1 (no)	2006-01-30	Renin-inhibitorer, fremstilling av disse, fremstilling av preparater, samt anvendelse for fremstilling av medikamenter.
US20160376256A1 (en)	2016-12-29	Sulfonyl piperidine derivatives and their use for treating prokineticin mediated diseases
US7217740B2 (en)	2007-05-15	Diarylsulfones as 5-HT2A antagonists
KR19980703644A (ko)	1998-12-05	트리아졸 항진균제
EP0680962A2 (fr)	1995-11-08	Composés hétérocycliques
EP2164825B1 (fr)	2014-04-30	Dérivés de di(hétéro)arylcyclohexane, leur préparation, leur utilisation et compositions pharmaceutiques les comprenant
JPH10158167A (ja)	1998-06-16	トリアゾール誘導体を含有する医薬
AU773296B2 (en)	2004-05-20	Phenylsulphonyl derivatives as 5-HT receptor ligands
JP2902345B2 (ja)	1999-06-07	トリアゾール抗真菌剤
MXPA98001814A (en)	1998-11-12	New 4- (oxyalcoxyphenyl) -3-oxy-piperidines for the treatment of heart and rejuvenation insufficiency
US9790217B2 (en)	2017-10-17	Pyridinyloxy- and phenyloxy-pyrazolyl compounds
HK1016177B (en)	2006-09-01	New 4-(oxyalkoxyphenyl)-3-oxy-piperidines for treating heart and kidney insufficiency
HK1233250B (zh)	2021-03-05	新的吡啶基氧基-和苯基氧基-吡唑基化合物
HK1233250A1 (en)	2018-01-26	New pyridinyloxy- and phenyloxy-pyrazolyl compounds