CA1291995C - Acylalkyl et arylalkylene aminoheterocycliques a n substituee en tant qu'agents antisecretoires et antihistaminiques cardiovasculaires - Google Patents

Acylalkyl et arylalkylene aminoheterocycliques a n substituee en tant qu'agents antisecretoires et antihistaminiques cardiovasculaires

Info

Publication number: CA1291995C
Authority: CA; Canada
Prior art keywords: pharmaceutically acceptable; acceptable salt; compound; composition; bis
Prior art date: 1986-01-17
Legal status (The legal status 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 status listed.): Expired - Fee Related

Application number

CA000526931A

Other languages

English (en)

Inventor

James R. Shanklin, Jr.

Anthony G. Proakis

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

AH Robins Co Inc

Original Assignee

AH Robins Co Inc

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.)

1986-01-17

Filing date

1987-01-08

Publication date

1991-11-12

1987-01-08 Application filed by AH Robins Co Inc filed Critical AH Robins Co Inc

1991-11-12 Application granted granted Critical

1991-11-12 Publication of CA1291995C publication Critical patent/CA1291995C/fr

2008-11-12 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

230000001387 anti-histamine Effects 0.000 title abstract description 4
230000002526 effect on cardiovascular system Effects 0.000 title abstract description 4
239000000739 antihistaminic agent Substances 0.000 title abstract description 3
239000002731 stomach secretion inhibitor Substances 0.000 title abstract description 3
150000003839 salts Chemical class 0.000 claims abstract description 328
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 88
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 56
239000001257 hydrogen Substances 0.000 claims abstract description 56
229910052799 carbon Inorganic materials 0.000 claims abstract description 41
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 37
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 28
229910052760 oxygen Inorganic materials 0.000 claims abstract description 16
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 claims abstract description 8
230000000694 effects Effects 0.000 claims abstract description 5
229960001340 histamine Drugs 0.000 claims abstract description 4
229910052717 sulfur Inorganic materials 0.000 claims abstract 11
230000002496 gastric effect Effects 0.000 claims abstract 3
230000028327 secretion Effects 0.000 claims abstract 3
239000000203 mixture Substances 0.000 claims description 431
150000001875 compounds Chemical class 0.000 claims description 386
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 146
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 98
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 97
-1 loweralkyl Chemical class 0.000 claims description 95
WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 78
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 62
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 49
239000002253 acid Substances 0.000 claims description 47
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 37
150000002431 hydrogen Chemical class 0.000 claims description 28
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 28
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 26
125000000623 heterocyclic group Chemical group 0.000 claims description 14
150000001412 amines Chemical group 0.000 claims description 13
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 13
125000004093 cyano group Chemical group *C#N 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
150000004677 hydrates Chemical group 0.000 claims description 11
229910021645 metal ion Inorganic materials 0.000 claims description 11
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 10
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 6
241001465754 Metazoa Species 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 4
230000017531 blood circulation Effects 0.000 claims description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
229920006395 saturated elastomer Polymers 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims 8
JBZKUUWJMRWXNH-UHFFFAOYSA-N 1-[4-[3-(4-benzhydrylidenepiperidin-1-yl)propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN(CC1)CCC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 JBZKUUWJMRWXNH-UHFFFAOYSA-N 0.000 claims 4
FIMXBJKPXSYVFH-UHFFFAOYSA-N 1-[4-[3-[4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN(CC1)CCC1=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 FIMXBJKPXSYVFH-UHFFFAOYSA-N 0.000 claims 4
UOVDXOWGCPVUBQ-UHFFFAOYSA-N 1-[4-[3-[4-[bis(4-fluorophenyl)methyl]piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 UOVDXOWGCPVUBQ-UHFFFAOYSA-N 0.000 claims 3
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 3
MIFQEILTCPKYPC-UHFFFAOYSA-N 1-[2-(benzenesulfonyl)ethyl]-4-[bis(4-fluorophenyl)methyl]piperidine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)C1CCN(CCS(=O)(=O)C=2C=CC=CC=2)CC1 MIFQEILTCPKYPC-UHFFFAOYSA-N 0.000 claims 2
KUKSOFSCEMPYBB-UHFFFAOYSA-N 1-[3-(benzenesulfinyl)propyl]-4-[bis(4-fluorophenyl)methyl]piperidine Chemical compound FC1=CC=C(C=C1)C(C1CCN(CC1)CCCS(=O)C1=CC=CC=C1)C1=CC=C(C=C1)F KUKSOFSCEMPYBB-UHFFFAOYSA-N 0.000 claims 2
YNBVFYLJEABHGQ-UHFFFAOYSA-N 1-[3-(benzenesulfonyl)propyl]-4-[bis(4-fluorophenyl)methyl]piperidine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)C1CCN(CCCS(=O)(=O)C=2C=CC=CC=2)CC1 YNBVFYLJEABHGQ-UHFFFAOYSA-N 0.000 claims 2
RLCGPMLGZBKQKV-UHFFFAOYSA-N 1-[3-methoxy-4-[3-[4-[phenyl-[3-(trifluoromethyl)phenyl]methylidene]piperidin-1-yl]propoxy]phenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN(CC1)CCC1=C(C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 RLCGPMLGZBKQKV-UHFFFAOYSA-N 0.000 claims 2
HJRAUNMHERBPJG-UHFFFAOYSA-N 1-[4-[2-[4-[bis(4-fluorophenyl)methyl]piperidin-1-yl]ethoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCN1CCC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 HJRAUNMHERBPJG-UHFFFAOYSA-N 0.000 claims 2
QQTPFWHWKHMTSV-UHFFFAOYSA-N 1-[4-[3-[4-(cyclohexyl-hydroxy-phenylmethyl)piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(C(O)(C2CCCCC2)C=2C=CC=CC=2)CC1 QQTPFWHWKHMTSV-UHFFFAOYSA-N 0.000 claims 2
RGPVIYPWZPOWLD-UHFFFAOYSA-N 1-[4-[3-[4-[(4-fluorophenyl)-phenylmethyl]piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(C(C=2C=CC=CC=2)C=2C=CC(F)=CC=2)CC1 RGPVIYPWZPOWLD-UHFFFAOYSA-N 0.000 claims 2
JNALAIQAJMAAIL-UHFFFAOYSA-N 1-[4-[3-[4-[2,2-bis(4-fluorophenyl)-2-hydroxyethyl]piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(CC(O)(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 JNALAIQAJMAAIL-UHFFFAOYSA-N 0.000 claims 2
FVPCYOBHFAOFOE-UHFFFAOYSA-N 1-[4-[3-[4-[2,2-bis(4-fluorophenyl)ethyl]piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(CC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 FVPCYOBHFAOFOE-UHFFFAOYSA-N 0.000 claims 2
HPUPORXOVFFDTA-UHFFFAOYSA-N 1-[4-[3-[4-[bis(2,4-difluorophenyl)methyl]piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(C(C=2C(=CC(F)=CC=2)F)C=2C(=CC(F)=CC=2)F)CC1 HPUPORXOVFFDTA-UHFFFAOYSA-N 0.000 claims 2
QYPRPKLDCPCRCT-UHFFFAOYSA-N 1-[4-[3-[4-[cyclohexyl(phenyl)methyl]-3,6-dihydro-2h-pyridin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CC=C(C(C2CCCCC2)C=2C=CC=CC=2)CC1 QYPRPKLDCPCRCT-UHFFFAOYSA-N 0.000 claims 2
UULHSEWXPVMAPP-UHFFFAOYSA-N 1-[4-[3-[4-[cyclohexyl(phenyl)methyl]piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(C(C2CCCCC2)C=2C=CC=CC=2)CC1 UULHSEWXPVMAPP-UHFFFAOYSA-N 0.000 claims 2
CZWAEBFNMWSEGS-UHFFFAOYSA-N 1-[4-[3-[4-[cyclohexyl(phenyl)methylidene]piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN(CC1)CCC1=C(C=1C=CC=CC=1)C1CCCCC1 CZWAEBFNMWSEGS-UHFFFAOYSA-N 0.000 claims 2
MLYZFKSNIDVQFS-UHFFFAOYSA-N 1-[4-[3-[4-[hydroxy-bis(4-methylphenyl)methyl]piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(C(O)(C=2C=CC(C)=CC=2)C=2C=CC(C)=CC=2)CC1 MLYZFKSNIDVQFS-UHFFFAOYSA-N 0.000 claims 2
PTEAYHWSRKORAG-UHFFFAOYSA-N 1-[4-[3-[4-[hydroxy-phenyl-[3-(trifluoromethyl)phenyl]methyl]piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=C(C=CC=2)C(F)(F)F)CC1 PTEAYHWSRKORAG-UHFFFAOYSA-N 0.000 claims 2
NGEMVDRQVLOEJW-UHFFFAOYSA-N 1-[4-[5-[4-[bis(4-fluorophenyl)methyl]piperidin-1-yl]pentoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCCCN1CCC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 NGEMVDRQVLOEJW-UHFFFAOYSA-N 0.000 claims 2
LVRSLGTWNFOYDP-UHFFFAOYSA-N 2-[3-[4-[bis(4-fluorophenyl)methyl]piperidin-1-yl]propoxy]quinoline Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)C1CCN(CCCOC=2N=C3C=CC=CC3=CC=2)CC1 LVRSLGTWNFOYDP-UHFFFAOYSA-N 0.000 claims 2
QBQAGZWTHCAYQV-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methyl]-1-(3-naphthalen-2-yloxypropyl)piperidine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)C1CCN(CCCOC=2C=C3C=CC=CC3=CC=2)CC1 QBQAGZWTHCAYQV-UHFFFAOYSA-N 0.000 claims 2
VEPLOEKUVLWDMU-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methyl]-1-(3-phenylsulfanylpropyl)piperidine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)C1CCN(CCCSC=2C=CC=CC=2)CC1 VEPLOEKUVLWDMU-UHFFFAOYSA-N 0.000 claims 2
IUYWPGGHDIJQIM-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methyl]-1-[2-(4-chlorophenyl)sulfonylethyl]piperidine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)C1CCN(CCS(=O)(=O)C=2C=CC(Cl)=CC=2)CC1 IUYWPGGHDIJQIM-UHFFFAOYSA-N 0.000 claims 2
VWCNBOZKKJJWBV-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methylidene]-1-(2-phenylsulfanylethyl)piperidine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)=C1CCN(CCSC=2C=CC=CC=2)CC1 VWCNBOZKKJJWBV-UHFFFAOYSA-N 0.000 claims 2
IMKOIVGLLQJTOJ-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methylidene]-1-[2-(4-chlorophenyl)sulfonylethyl]piperidine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)=C1CCN(CCS(=O)(=O)C=2C=CC(Cl)=CC=2)CC1 IMKOIVGLLQJTOJ-UHFFFAOYSA-N 0.000 claims 2
ROFLXGAENAYDRT-UHFFFAOYSA-N 7-[3-[4-[bis(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]propoxy]chromen-2-one Chemical compound C1CN(CCCOC=2C=C3OC(=O)C=CC3=CC=2)CCC1C(O)(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 ROFLXGAENAYDRT-UHFFFAOYSA-N 0.000 claims 2
206010002383 Angina Pectoris Diseases 0.000 claims 2
229940127291 Calcium channel antagonist Drugs 0.000 claims 2
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 2
239000005977 Ethylene Substances 0.000 claims 2
206010020772 Hypertension Diseases 0.000 claims 2
239000000480 calcium channel blocker Substances 0.000 claims 2
230000003247 decreasing effect Effects 0.000 claims 2
UAUIUWUYUSNURT-UHFFFAOYSA-N ethyl 7-[3-[4-[bis(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]propoxy]-4-oxochromene-2-carboxylate Chemical compound C1=C2OC(C(=O)OCC)=CC(=O)C2=CC=C1OCCCN(CC1)CCC1C(O)(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 UAUIUWUYUSNURT-UHFFFAOYSA-N 0.000 claims 2
ONGLXADHGUOCPC-UHFFFAOYSA-N methyl 4-[4-[4-[bis(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]butoxy]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1OCCCCN1CCC(C(O)(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 ONGLXADHGUOCPC-UHFFFAOYSA-N 0.000 claims 2
BMRARLJDLIUFPA-UHFFFAOYSA-N n-[3-[4-[bis(4-fluorophenyl)methyl]piperidin-1-yl]propyl]-n-methylaniline Chemical compound C=1C=CC=CC=1N(C)CCCN(CC1)CCC1C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 BMRARLJDLIUFPA-UHFFFAOYSA-N 0.000 claims 2
LWTZBYRZQIGASG-UHFFFAOYSA-N n-[3-[4-[bis(4-fluorophenyl)methyl]piperidin-1-yl]propyl]aniline Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)C1CCN(CCCNC=2C=CC=CC=2)CC1 LWTZBYRZQIGASG-UHFFFAOYSA-N 0.000 claims 2
YNWHRSSANNRIEM-UHFFFAOYSA-N 1-[4-[2-[4-[bis(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]ethoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCN1CCC(C(O)(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 YNWHRSSANNRIEM-UHFFFAOYSA-N 0.000 claims 1
FYIBDZJGBOZTNV-UHFFFAOYSA-N 1-[4-[3-(4-benzhydrylpiperidin-1-yl)propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 FYIBDZJGBOZTNV-UHFFFAOYSA-N 0.000 claims 1
LZGTZRZRYXUCGB-UHFFFAOYSA-N 1-[4-[3-[3-[bis(4-fluorophenyl)-hydroxymethyl]pyrrolidin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CC(C(O)(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 LZGTZRZRYXUCGB-UHFFFAOYSA-N 0.000 claims 1
NMHBRYQBDQAZRP-UHFFFAOYSA-N 1-[4-[3-[4-[(3,4-difluorophenyl)-(4-fluorophenyl)methyl]piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(C(C=2C=CC(F)=CC=2)C=2C=C(F)C(F)=CC=2)CC1 NMHBRYQBDQAZRP-UHFFFAOYSA-N 0.000 claims 1
SXNQUTWAVUUOFI-UHFFFAOYSA-N 1-[4-[3-[4-[(4-fluorophenyl)-hydroxy-phenylmethyl]piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC(F)=CC=2)CC1 SXNQUTWAVUUOFI-UHFFFAOYSA-N 0.000 claims 1
YDXARWPQNQHLAN-UHFFFAOYSA-N 1-[4-[3-[4-[bis(3,4-difluorophenyl)-hydroxymethyl]piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(C(O)(C=2C=C(F)C(F)=CC=2)C=2C=C(F)C(F)=CC=2)CC1 YDXARWPQNQHLAN-UHFFFAOYSA-N 0.000 claims 1
XDXADXHUOLHEOB-UHFFFAOYSA-N 1-[4-[3-[4-[bis(3,4-difluorophenyl)methyl]piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(C(C=2C=C(F)C(F)=CC=2)C=2C=C(F)C(F)=CC=2)CC1 XDXADXHUOLHEOB-UHFFFAOYSA-N 0.000 claims 1
BTQCYONFXSTTLB-UHFFFAOYSA-N 1-[4-[3-[4-[bis(4-chlorophenyl)-hydroxymethyl]piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(C(O)(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)CC1 BTQCYONFXSTTLB-UHFFFAOYSA-N 0.000 claims 1
XXWICQFXPAIXDZ-UHFFFAOYSA-N 1-[4-[3-[4-[bis(4-chlorophenyl)methyl]piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(C(C=2C=CC(Cl)=CC=2)C=2C=CC(Cl)=CC=2)CC1 XXWICQFXPAIXDZ-UHFFFAOYSA-N 0.000 claims 1
MURGUZCJZNPBBZ-UHFFFAOYSA-N 1-[4-[3-[4-[bis(4-chlorophenyl)methylidene]piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN(CC1)CCC1=C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 MURGUZCJZNPBBZ-UHFFFAOYSA-N 0.000 claims 1
ZEBXFCFWCGBFOZ-UHFFFAOYSA-N 1-[4-[3-[4-[bis(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]propoxy]-2-methoxyphenyl]ethanone Chemical compound C1=C(C(C)=O)C(OC)=CC(OCCCN2CCC(CC2)C(O)(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)=C1 ZEBXFCFWCGBFOZ-UHFFFAOYSA-N 0.000 claims 1
QFUKWQQHSSRPQM-UHFFFAOYSA-N 1-[4-[3-[4-[bis(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(C(O)(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 QFUKWQQHSSRPQM-UHFFFAOYSA-N 0.000 claims 1
JTNMDLZECBZHEC-UHFFFAOYSA-N 1-[4-[3-[4-[bis(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]propoxy]-3-methylphenyl]ethanone Chemical compound CC1=CC(C(=O)C)=CC=C1OCCCN1CCC(C(O)(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 JTNMDLZECBZHEC-UHFFFAOYSA-N 0.000 claims 1
GQCCOGCEQBQUAD-UHFFFAOYSA-N 1-[4-[3-[4-[bis(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]propoxy]phenyl]-3-methylurea Chemical compound C1=CC(NC(=O)NC)=CC=C1OCCCN1CCC(C(O)(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 GQCCOGCEQBQUAD-UHFFFAOYSA-N 0.000 claims 1
DIRRXRQEQQIFRS-UHFFFAOYSA-N 1-[4-[3-[4-[bis(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]propoxy]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OCCCN1CCC(C(O)(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 DIRRXRQEQQIFRS-UHFFFAOYSA-N 0.000 claims 1
LJQMQRJWYCVHDU-UHFFFAOYSA-N 1-[4-[3-[4-[bis(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]propoxy]phenyl]propan-1-one Chemical compound C1=CC(C(=O)CC)=CC=C1OCCCN1CCC(C(O)(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 LJQMQRJWYCVHDU-UHFFFAOYSA-N 0.000 claims 1
FKRCUXNEGDSKAA-UHFFFAOYSA-N 1-[4-[3-[4-[bis(4-fluorophenyl)methyl]piperidin-1-yl]propoxy]-2-methoxyphenyl]ethanone Chemical compound C1=C(C(C)=O)C(OC)=CC(OCCCN2CCC(CC2)C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)=C1 FKRCUXNEGDSKAA-UHFFFAOYSA-N 0.000 claims 1
WQUFWOXKBAQRQU-UHFFFAOYSA-N 1-[4-[3-[4-[bis(4-fluorophenyl)methyl]piperidin-1-yl]propoxy]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OCCCN1CCC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 WQUFWOXKBAQRQU-UHFFFAOYSA-N 0.000 claims 1
QNDTWMFSONOQLL-UHFFFAOYSA-N 1-[4-[3-[4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl]propoxy]phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OCCCN(CC1)CCC1=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 QNDTWMFSONOQLL-UHFFFAOYSA-N 0.000 claims 1
UADUJKAMTSHJQS-UHFFFAOYSA-N 1-[4-[3-[4-[bis(4-methoxyphenyl)methyl]piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC(OC)=CC=1)C1CCN(CCCOC=2C(=CC(=CC=2)C(C)=O)OC)CC1 UADUJKAMTSHJQS-UHFFFAOYSA-N 0.000 claims 1
DTYSYXOVYCUFES-UHFFFAOYSA-N 1-[4-[3-[4-[bis(4-methylphenyl)methyl]piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(C(C=2C=CC(C)=CC=2)C=2C=CC(C)=CC=2)CC1 DTYSYXOVYCUFES-UHFFFAOYSA-N 0.000 claims 1
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VRQQRENDQSWBNX-UHFFFAOYSA-N 1-[4-[3-[4-[cyclohexyl-(4-fluorophenyl)methyl]piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(C(C2CCCCC2)C=2C=CC(F)=CC=2)CC1 VRQQRENDQSWBNX-UHFFFAOYSA-N 0.000 claims 1
WGWRMJSTSKBWJG-UHFFFAOYSA-N 1-[4-[3-[4-[hydroxy(diphenyl)methyl]piperidin-1-yl]propoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 WGWRMJSTSKBWJG-UHFFFAOYSA-N 0.000 claims 1
ZIBHRYATKGTOLV-UHFFFAOYSA-N 1-[4-[4-[4-[bis(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]butoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCCN1CCC(C(O)(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 ZIBHRYATKGTOLV-UHFFFAOYSA-N 0.000 claims 1
CFVVTFLCALCNSI-UHFFFAOYSA-N 1-[4-[4-[4-[bis(4-fluorophenyl)methyl]piperidin-1-yl]butoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCCN1CCC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 CFVVTFLCALCNSI-UHFFFAOYSA-N 0.000 claims 1
WBCREXFMPRZZOH-UHFFFAOYSA-N 1-[4-[5-[4-[bis(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]pentoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCCCN1CCC(C(O)(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 WBCREXFMPRZZOH-UHFFFAOYSA-N 0.000 claims 1
CEHIPXREZPZNMP-UHFFFAOYSA-N 1-[4-[6-[4-[bis(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]hexoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCCCCN1CCC(C(O)(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 CEHIPXREZPZNMP-UHFFFAOYSA-N 0.000 claims 1
UWLFVXHGEVICLM-UHFFFAOYSA-N 1-[4-[6-[4-[bis(4-fluorophenyl)methyl]piperidin-1-yl]hexoxy]-3-methoxyphenyl]ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCCCCCCN1CCC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 UWLFVXHGEVICLM-UHFFFAOYSA-N 0.000 claims 1
OHZZBAPTCRYJOS-UHFFFAOYSA-N 2-[(4-fluorophenyl)-[1-(3-phenoxypropyl)piperidin-4-yl]methyl]pyridine Chemical compound C1=CC(F)=CC=C1C(C=1N=CC=CC=1)C1CCN(CCCOC=2C=CC=CC=2)CC1 OHZZBAPTCRYJOS-UHFFFAOYSA-N 0.000 claims 1
KFNHRNXMDDSFMR-UHFFFAOYSA-N 2-[3-[4-[bis(4-fluorophenyl)methyl]piperidin-1-yl]propoxy]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1OCCCN1CCC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 KFNHRNXMDDSFMR-UHFFFAOYSA-N 0.000 claims 1
ZQPRRFYZVZLUAK-UHFFFAOYSA-N 2-[3-[4-[bis(4-fluorophenyl)methyl]piperidin-1-yl]propoxy]benzonitrile Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)C1CCN(CCCOC=2C(=CC=CC=2)C#N)CC1 ZQPRRFYZVZLUAK-UHFFFAOYSA-N 0.000 claims 1
VZEFTDVIMMMIAL-UHFFFAOYSA-N 2-[3-[4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl]propoxy]phenol Chemical compound OC1=CC=CC=C1OCCCN(CC1)CCC1=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 VZEFTDVIMMMIAL-UHFFFAOYSA-N 0.000 claims 1
KMHUXGIFENAMSP-UHFFFAOYSA-N 2-[4-[3-[4-[bis(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]propoxy]-3-methoxyphenyl]acetic acid Chemical compound COC1=CC(CC(O)=O)=CC=C1OCCCN1CCC(C(O)(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 KMHUXGIFENAMSP-UHFFFAOYSA-N 0.000 claims 1
YYWDCXGZAWTLEH-UHFFFAOYSA-N 3-[3-[4-[bis(4-fluorophenyl)methyl]piperidin-1-yl]propoxy]benzonitrile Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)C1CCN(CCCOC=2C=C(C=CC=2)C#N)CC1 YYWDCXGZAWTLEH-UHFFFAOYSA-N 0.000 claims 1
ZMDWVDOBEGZQJC-UHFFFAOYSA-N 3-piperidin-1-ylpropanamide Chemical compound NC(=O)CCN1CCCCC1 ZMDWVDOBEGZQJC-UHFFFAOYSA-N 0.000 claims 1
GADJVFLIQOBWRU-UHFFFAOYSA-N 4-[(4-fluorophenyl)-phenylmethyl]-1-(3-phenoxypropyl)piperidine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC=CC=1)C1CCN(CCCOC=2C=CC=CC=2)CC1 GADJVFLIQOBWRU-UHFFFAOYSA-N 0.000 claims 1
DFTYRSZAAHOFNM-UHFFFAOYSA-N 4-[3-[4-[bis(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]propoxy]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1OCCCN1CCC(C(O)(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 DFTYRSZAAHOFNM-UHFFFAOYSA-N 0.000 claims 1
IFIZNEASFIVALC-UHFFFAOYSA-N 4-[3-[4-[bis(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]propoxy]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1OCCCN1CCC(C(O)(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 IFIZNEASFIVALC-UHFFFAOYSA-N 0.000 claims 1
VHNHDYOULIPPPD-UHFFFAOYSA-N 4-[3-[4-[bis(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]propoxy]benzonitrile Chemical compound C=1C=C(F)C=CC=1C(C=1C=CC(F)=CC=1)(O)C(CC1)CCN1CCCOC1=CC=C(C#N)C=C1 VHNHDYOULIPPPD-UHFFFAOYSA-N 0.000 claims 1
BAARGQXTUQRRII-UHFFFAOYSA-N 4-[3-[4-[bis(4-fluorophenyl)methyl]piperidin-1-yl]propoxy]-3-methoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC=C1OCCCN1CCC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 BAARGQXTUQRRII-UHFFFAOYSA-N 0.000 claims 1
FHGZVEPHABTFNB-UHFFFAOYSA-N 4-[3-[4-[bis(4-fluorophenyl)methyl]piperidin-1-yl]propoxy]-3-methoxybenzonitrile Chemical compound COC1=CC(C#N)=CC=C1OCCCN1CCC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 FHGZVEPHABTFNB-UHFFFAOYSA-N 0.000 claims 1
LFEIQSMJVGSIIG-UHFFFAOYSA-N 4-[3-[4-[bis(4-fluorophenyl)methyl]piperidin-1-yl]propoxy]aniline Chemical compound C1=CC(N)=CC=C1OCCCN1CCC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 LFEIQSMJVGSIIG-UHFFFAOYSA-N 0.000 claims 1
SATPTBATSJDWCT-UHFFFAOYSA-N 4-[3-[4-[bis(4-fluorophenyl)methyl]piperidin-1-yl]propoxy]benzonitrile Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)C1CCN(CCCOC=2C=CC(=CC=2)C#N)CC1 SATPTBATSJDWCT-UHFFFAOYSA-N 0.000 claims 1
BTKJGCVHYCJIGL-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methyl]-1-(2-naphthalen-1-yloxyethyl)piperidine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)C1CCN(CCOC=2C3=CC=CC=C3C=CC=2)CC1 BTKJGCVHYCJIGL-UHFFFAOYSA-N 0.000 claims 1
WSQNLPBESBYNDO-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methyl]-1-(2-naphthalen-2-yloxyethyl)piperidine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)C1CCN(CCOC=2C=C3C=CC=CC3=CC=2)CC1 WSQNLPBESBYNDO-UHFFFAOYSA-N 0.000 claims 1
NDMPOHQIRNUXKV-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methyl]-1-(2-phenoxyethyl)piperidine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)C1CCN(CCOC=2C=CC=CC=2)CC1 NDMPOHQIRNUXKV-UHFFFAOYSA-N 0.000 claims 1
FCOOXVCEKKFVKU-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methyl]-1-(3-naphthalen-1-yloxypropyl)piperidine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)C1CCN(CCCOC=2C3=CC=CC=C3C=CC=2)CC1 FCOOXVCEKKFVKU-UHFFFAOYSA-N 0.000 claims 1
NFBYPQJXZYCVMG-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methyl]-1-(3-phenoxypropyl)piperidine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)C1CCN(CCCOC=2C=CC=CC=2)CC1 NFBYPQJXZYCVMG-UHFFFAOYSA-N 0.000 claims 1
UEGYTOQQURASTC-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methyl]-1-(4-phenoxybutyl)piperidine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)C1CCN(CCCCOC=2C=CC=CC=2)CC1 UEGYTOQQURASTC-UHFFFAOYSA-N 0.000 claims 1
VCCVXNZTCNSYEV-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methyl]-1-[2-(2,6-dichlorophenoxy)ethyl]piperidine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)C1CCN(CCOC=2C(=CC=CC=2Cl)Cl)CC1 VCCVXNZTCNSYEV-UHFFFAOYSA-N 0.000 claims 1
XUSYMHJIXGUSDH-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methyl]-1-[3-(2,6-dimethoxyphenoxy)propyl]piperidine Chemical compound COC1=CC=CC(OC)=C1OCCCN1CCC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 XUSYMHJIXGUSDH-UHFFFAOYSA-N 0.000 claims 1
NRIGZJHYSXCBPU-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methyl]-1-[3-(2-fluorophenoxy)propyl]piperidine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)C1CCN(CCCOC=2C(=CC=CC=2)F)CC1 NRIGZJHYSXCBPU-UHFFFAOYSA-N 0.000 claims 1
AFYKDIKAZAWWLP-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methyl]-1-[3-(2-methoxyphenoxy)propyl]piperidine Chemical compound COC1=CC=CC=C1OCCCN1CCC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 AFYKDIKAZAWWLP-UHFFFAOYSA-N 0.000 claims 1
HHETXZOBRUPZGW-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methyl]-1-[3-(3,4-dimethoxyphenoxy)propyl]piperidine Chemical compound C1=C(OC)C(OC)=CC=C1OCCCN1CCC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 HHETXZOBRUPZGW-UHFFFAOYSA-N 0.000 claims 1
NCRRWJCDQDYRBO-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methyl]-1-[3-(3,5-dimethoxyphenoxy)propyl]piperidine Chemical compound COC1=CC(OC)=CC(OCCCN2CCC(CC2)C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)=C1 NCRRWJCDQDYRBO-UHFFFAOYSA-N 0.000 claims 1
QMSHEELQMCQSNB-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methyl]-1-[3-(3-fluorophenoxy)propyl]piperidine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)C1CCN(CCCOC=2C=C(F)C=CC=2)CC1 QMSHEELQMCQSNB-UHFFFAOYSA-N 0.000 claims 1
QFUZLTFFDBWIFR-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methyl]-1-[3-(3-methoxyphenoxy)propyl]piperidine Chemical compound COC1=CC=CC(OCCCN2CCC(CC2)C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)=C1 QFUZLTFFDBWIFR-UHFFFAOYSA-N 0.000 claims 1
AVVPKERRLYTNNY-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methyl]-1-[3-(4-chlorophenoxy)propyl]piperidine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)C1CCN(CCCOC=2C=CC(Cl)=CC=2)CC1 AVVPKERRLYTNNY-UHFFFAOYSA-N 0.000 claims 1
GXCBCTCDJXWCEB-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methyl]-1-[3-(4-ethyl-2-methoxyphenoxy)propyl]piperidine Chemical compound COC1=CC(CC)=CC=C1OCCCN1CCC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 GXCBCTCDJXWCEB-UHFFFAOYSA-N 0.000 claims 1
VMAGGRADYNFDSG-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methyl]-1-[3-(4-fluorophenoxy)propyl]piperidine Chemical compound C1=CC(F)=CC=C1OCCCN1CCC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 VMAGGRADYNFDSG-UHFFFAOYSA-N 0.000 claims 1
BPPKFKDLVHEQBC-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methyl]-1-[3-(4-methoxyphenoxy)propyl]piperidine Chemical compound C1=CC(OC)=CC=C1OCCCN1CCC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 BPPKFKDLVHEQBC-UHFFFAOYSA-N 0.000 claims 1
LYDAYNYSZYYTGE-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methyl]-1-[3-(4-methylsulfonylpentoxy)propyl]piperidine Chemical compound C1CN(CCCOCCCC(C)S(C)(=O)=O)CCC1C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 LYDAYNYSZYYTGE-UHFFFAOYSA-N 0.000 claims 1
ANPYHBQRFSDIPQ-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methyl]-1-[3-(4-tert-butylphenoxy)propyl]piperidine Chemical compound C1=CC(C(C)(C)C)=CC=C1OCCCN1CCC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 ANPYHBQRFSDIPQ-UHFFFAOYSA-N 0.000 claims 1
PUBXUSJSRVTHBN-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methyl]-1-[3-[3-(trifluoromethyl)phenoxy]propyl]piperidine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)C1CCN(CCCOC=2C=C(C=CC=2)C(F)(F)F)CC1 PUBXUSJSRVTHBN-UHFFFAOYSA-N 0.000 claims 1
AXJJJXLDLPPMJY-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methylidene]-1-(3-phenoxypropyl)piperidine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)=C1CCN(CCCOC=2C=CC=CC=2)CC1 AXJJJXLDLPPMJY-UHFFFAOYSA-N 0.000 claims 1
WYEYYOMMPUMWMQ-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methylidene]-1-[3-(2-methoxyphenoxy)propyl]piperidine Chemical compound COC1=CC=CC=C1OCCCN(CC1)CCC1=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 WYEYYOMMPUMWMQ-UHFFFAOYSA-N 0.000 claims 1
KECWTQXFZVXILO-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methylidene]-1-[3-(3,4-dimethoxyphenoxy)propyl]piperidine Chemical compound C1=C(OC)C(OC)=CC=C1OCCCN(CC1)CCC1=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 KECWTQXFZVXILO-UHFFFAOYSA-N 0.000 claims 1
XVAKGOFXYJUYFL-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)methylidene]-1-[3-(4-tert-butylphenoxy)propyl]piperidine Chemical compound C1=CC(C(C)(C)C)=CC=C1OCCCN(CC1)CCC1=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 XVAKGOFXYJUYFL-UHFFFAOYSA-N 0.000 claims 1
RADPZLMEUCVRKZ-UHFFFAOYSA-N 4-[bis(4-methoxyphenyl)methyl]-1-[3-(3,4-dimethoxyphenoxy)propyl]piperidine Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC(OC)=CC=1)C1CCN(CCCOC=2C=C(OC)C(OC)=CC=2)CC1 RADPZLMEUCVRKZ-UHFFFAOYSA-N 0.000 claims 1
YOUAOUQBFOLGMD-UHFFFAOYSA-N 4-[bis(4-methoxyphenyl)methyl]-1-[3-(4-methoxyphenoxy)propyl]piperidine Chemical compound C1=CC(OC)=CC=C1OCCCN1CCC(C(C=2C=CC(OC)=CC=2)C=2C=CC(OC)=CC=2)CC1 YOUAOUQBFOLGMD-UHFFFAOYSA-N 0.000 claims 1
NECUCOPLSRJZLJ-UHFFFAOYSA-N 4-[bis(4-methoxyphenyl)methyl]-1-[3-(4-tert-butylphenoxy)propyl]piperidine Chemical compound C1=CC(OC)=CC=C1C(C=1C=CC(OC)=CC=1)C1CCN(CCCOC=2C=CC(=CC=2)C(C)(C)C)CC1 NECUCOPLSRJZLJ-UHFFFAOYSA-N 0.000 claims 1
GRCOXKIBNWXXGC-UHFFFAOYSA-N 4-[bis(4-methylphenyl)methyl]-1-[3-(2,6-dimethoxyphenoxy)propyl]piperidine Chemical compound COC1=CC=CC(OC)=C1OCCCN1CCC(C(C=2C=CC(C)=CC=2)C=2C=CC(C)=CC=2)CC1 GRCOXKIBNWXXGC-UHFFFAOYSA-N 0.000 claims 1
WUFCYJXXKHSJMC-UHFFFAOYSA-N 4-benzhydryl-1-(2-phenoxyethyl)piperidine Chemical compound C=1C=CC=CC=1OCCN(CC1)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 WUFCYJXXKHSJMC-UHFFFAOYSA-N 0.000 claims 1
FLMGWIOWOLBMLX-UHFFFAOYSA-N 4-benzhydryl-1-(3-phenoxypropyl)piperidine Chemical compound C1CC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1CCCOC1=CC=CC=C1 FLMGWIOWOLBMLX-UHFFFAOYSA-N 0.000 claims 1
DJWTUSMPGXUYFA-UHFFFAOYSA-N 4-benzhydryl-1-(4-phenoxybutyl)piperidine Chemical compound C=1C=CC=CC=1OCCCCN(CC1)CCC1C(C=1C=CC=CC=1)C1=CC=CC=C1 DJWTUSMPGXUYFA-UHFFFAOYSA-N 0.000 claims 1
NUOOSDPJYDMFRC-UHFFFAOYSA-N 4-benzhydrylidene-1-(3-phenoxypropyl)piperidine Chemical compound C1CC(=C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1CCCOC1=CC=CC=C1 NUOOSDPJYDMFRC-UHFFFAOYSA-N 0.000 claims 1
XVRKDOCEKLIOFL-UHFFFAOYSA-N 7-[3-[4-[bis(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]propoxy]-2,3-dihydrochromen-4-one Chemical compound C1CN(CCCOC=2C=C3OCCC(=O)C3=CC=2)CCC1C(O)(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 XVRKDOCEKLIOFL-UHFFFAOYSA-N 0.000 claims 1
CWIYSHXCFKCCAD-UHFFFAOYSA-N 8-[3-[4-[bis(4-fluorophenyl)methyl]piperidin-1-yl]propoxy]quinoline Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)C1CCN(CCCOC=2C3=NC=CC=C3C=CC=2)CC1 CWIYSHXCFKCCAD-UHFFFAOYSA-N 0.000 claims 1
101100272852 Clostridium botulinum (strain Langeland / NCTC 10281 / Type F) F gene Proteins 0.000 claims 1
235000010290 biphenyl Nutrition 0.000 claims 1
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JQBLCRRCBHPNJN-UHFFFAOYSA-N ethyl 2-[3-[4-[bis(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]propoxy]benzoate Chemical compound CCOC(=O)C1=CC=CC=C1OCCCN1CCC(C(O)(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 JQBLCRRCBHPNJN-UHFFFAOYSA-N 0.000 claims 1
BVGOCQMOAUSJMN-UHFFFAOYSA-N ethyl 2-[3-[4-[bis(4-fluorophenyl)methyl]piperidin-1-yl]propoxy]benzoate Chemical compound CCOC(=O)C1=CC=CC=C1OCCCN1CCC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 BVGOCQMOAUSJMN-UHFFFAOYSA-N 0.000 claims 1
BLZCKCKQDXOKBR-UHFFFAOYSA-N ethyl 4-[3-[4-[bis(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]propoxy]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1OCCCN1CCC(C(O)(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 BLZCKCKQDXOKBR-UHFFFAOYSA-N 0.000 claims 1
PQBUMTMEBNXSFQ-UHFFFAOYSA-N ethyl 4-[3-[4-[bis(4-fluorophenyl)methyl]piperidin-1-yl]propoxy]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1OCCCN1CCC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 PQBUMTMEBNXSFQ-UHFFFAOYSA-N 0.000 claims 1
NZDQPSFTRQFVOZ-UHFFFAOYSA-N ethyl 4-[3-[4-[bis(4-fluorophenyl)methylidene]piperidin-1-yl]propoxy]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1OCCCN(CC1)CCC1=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 NZDQPSFTRQFVOZ-UHFFFAOYSA-N 0.000 claims 1
UDBLIISLIQNOTN-UHFFFAOYSA-N ethyl 4-[3-[4-[bis(4-methoxyphenyl)methyl]piperidin-1-yl]propoxy]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1OCCCN1CCC(C(C=2C=CC(OC)=CC=2)C=2C=CC(OC)=CC=2)CC1 UDBLIISLIQNOTN-UHFFFAOYSA-N 0.000 claims 1
MSGZXXOBWLWAAV-UHFFFAOYSA-N ethyl n-[4-[3-[4-[bis(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]propoxy]phenyl]carbamate Chemical compound C1=CC(NC(=O)OCC)=CC=C1OCCCN1CCC(C(O)(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 MSGZXXOBWLWAAV-UHFFFAOYSA-N 0.000 claims 1
VFVLJJUSNBAEDB-UHFFFAOYSA-N methyl 4-[3-[4-[bis(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]propoxy]-3-methoxybenzoate Chemical compound COC1=CC(C(=O)OC)=CC=C1OCCCN1CCC(C(O)(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 VFVLJJUSNBAEDB-UHFFFAOYSA-N 0.000 claims 1
DNJLISQLMWIPEU-UHFFFAOYSA-N methyl 4-[3-[4-[bis(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]propoxy]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1OCCCN1CCC(C(O)(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 DNJLISQLMWIPEU-UHFFFAOYSA-N 0.000 claims 1
BFCOJXSJGZXOOA-UHFFFAOYSA-N methyl 4-[3-[4-[bis(4-fluorophenyl)methyl]piperidin-1-yl]propoxy]-3-methoxybenzoate Chemical compound COC1=CC(C(=O)OC)=CC=C1OCCCN1CCC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 BFCOJXSJGZXOOA-UHFFFAOYSA-N 0.000 claims 1
KKDGTWCUQKRHJM-UHFFFAOYSA-N methyl 4-[3-[4-[hydroxy(diphenyl)methyl]piperidin-1-yl]propoxy]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1OCCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 KKDGTWCUQKRHJM-UHFFFAOYSA-N 0.000 claims 1
GILWJCDRMYAEPK-UHFFFAOYSA-N n-[4-[3-[4-[bis(4-fluorophenyl)-hydroxymethyl]piperidin-1-yl]propoxy]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1OCCCN1CCC(C(O)(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 GILWJCDRMYAEPK-UHFFFAOYSA-N 0.000 claims 1
QCBNSZSMQVKLAQ-UHFFFAOYSA-N n-[4-[3-[4-[bis(4-fluorophenyl)methyl]piperidin-1-yl]propoxy]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1OCCCN1CCC(C(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 QCBNSZSMQVKLAQ-UHFFFAOYSA-N 0.000 claims 1
VHJIEEXYQFOSHG-UHFFFAOYSA-N n-[4-[3-[4-[bis(4-methylphenyl)methyl]piperidin-1-yl]propoxy]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1OCCCN1CCC(C(C=2C=CC(C)=CC=2)C=2C=CC(C)=CC=2)CC1 VHJIEEXYQFOSHG-UHFFFAOYSA-N 0.000 claims 1
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238000000354 decomposition reaction Methods 0.000 description 8
SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 8
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HCAJEUSONLESMK-UHFFFAOYSA-M cyclohexylsulfamate Chemical compound [O-]S(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-M 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
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
125000004212 difluorophenyl group Chemical group 0.000 description 1
239000000539 dimer Substances 0.000 description 1
ZWWQRMFIZFPUAA-UHFFFAOYSA-N dimethyl 2-methylidenebutanedioate Chemical compound COC(=O)CC(=C)C(=O)OC ZWWQRMFIZFPUAA-UHFFFAOYSA-N 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
MRHLFZXYRABVOZ-UHFFFAOYSA-N diphenyl(pyridin-4-yl)methanol Chemical compound C=1C=CC=CC=1C(C=1C=CN=CC=1)(O)C1=CC=CC=C1 MRHLFZXYRABVOZ-UHFFFAOYSA-N 0.000 description 1
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
229940052303 ethers for general anesthesia Drugs 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
VUILWWLHMVLGCX-UHFFFAOYSA-N ethyl 1-(3-phenoxypropyl)piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1CCCOC1=CC=CC=C1 VUILWWLHMVLGCX-UHFFFAOYSA-N 0.000 description 1
FNMLRMATQJCQCB-UHFFFAOYSA-N ethyl 2-(3-chloropropoxy)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1OCCCCl FNMLRMATQJCQCB-UHFFFAOYSA-N 0.000 description 1
AWPMWZHWVKXADV-UHFFFAOYSA-N ethyl 2-(4-hydroxy-3-methoxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC=C(O)C(OC)=C1 AWPMWZHWVKXADV-UHFFFAOYSA-N 0.000 description 1
ISQXCDWJOAJLLA-UHFFFAOYSA-N ethyl 2-propoxybenzoate Chemical compound CCCOC1=CC=CC=C1C(=O)OCC ISQXCDWJOAJLLA-UHFFFAOYSA-N 0.000 description 1
RKIMFICEWCXBCE-UHFFFAOYSA-N ethyl 7-hydroxy-4-oxochromene-2-carboxylate Chemical compound C1=C(O)C=C2OC(C(=O)OCC)=CC(=O)C2=C1 RKIMFICEWCXBCE-UHFFFAOYSA-N 0.000 description 1
WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 1
NBEMQPLNBYYUAZ-UHFFFAOYSA-N ethyl acetate;propan-2-one Chemical compound CC(C)=O.CCOC(C)=O NBEMQPLNBYYUAZ-UHFFFAOYSA-N 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
MCRPKBUFXAKDKI-UHFFFAOYSA-N ethyl pyridine-4-carboxylate Chemical compound CCOC(=O)C1=CC=NC=C1 MCRPKBUFXAKDKI-UHFFFAOYSA-N 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
238000011010 flushing procedure 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
238000007429 general method Methods 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
230000000004 hemodynamic effect Effects 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
QKGYJVXSKCDGOK-UHFFFAOYSA-N hexane;propan-2-ol Chemical compound CC(C)O.CCCCCC QKGYJVXSKCDGOK-UHFFFAOYSA-N 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
101150075287 hydD gene Proteins 0.000 description 1
GVLGAFRNYJVHBC-UHFFFAOYSA-N hydrate;hydrobromide Chemical compound O.Br GVLGAFRNYJVHBC-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
210000004964 innate lymphoid cell Anatomy 0.000 description 1
229910003480 inorganic solid Inorganic materials 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
238000003328 mesylation reaction Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
HNQIVZYLYMDVSB-NJFSPNSNSA-N methanesulfonamide Chemical compound [14CH3]S(N)(=O)=O HNQIVZYLYMDVSB-NJFSPNSNSA-N 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
XJLSEXAGTJCILF-UHFFFAOYSA-N nipecotic acid Chemical compound OC(=O)C1CCCNC1 XJLSEXAGTJCILF-UHFFFAOYSA-N 0.000 description 1
239000012299 nitrogen atmosphere Substances 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
HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
KLAKIAVEMQMVBT-UHFFFAOYSA-N p-hydroxy-phenacyl alcohol Natural products OCC(=O)C1=CC=C(O)C=C1 KLAKIAVEMQMVBT-UHFFFAOYSA-N 0.000 description 1
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical group O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 1
SKFLCXNDKRUHTA-UHFFFAOYSA-N phenyl(pyridin-4-yl)methanone Chemical compound C=1C=NC=CC=1C(=O)C1=CC=CC=C1 SKFLCXNDKRUHTA-UHFFFAOYSA-N 0.000 description 1
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
238000005086 pumping Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
125000000719 pyrrolidinyl group Chemical class 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000005057 refrigeration Methods 0.000 description 1
IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
238000012216 screening Methods 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000011343 solid material Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000012360 testing method Methods 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
239000012485 toluene extract Substances 0.000 description 1
238000007070 tosylation reaction Methods 0.000 description 1
238000009966 trimming Methods 0.000 description 1
ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical compound C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)

CA000526931A 1986-01-17 1987-01-08 Acylalkyl et arylalkylene aminoheterocycliques a n substituee en tant qu'agents antisecretoires et antihistaminiques cardiovasculaires Expired - Fee Related CA1291995C (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US81970186A	1986-01-17	1986-01-17
US819,701		1986-01-17
US15439088A	1988-02-10	1988-02-10
US154,390		1988-02-10

Publications (1)

Publication Number	Publication Date
CA1291995C true CA1291995C (fr)	1991-11-12

Family

ID=26851409

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000526931A Expired - Fee Related CA1291995C (fr)	1986-01-17	1987-01-08	Acylalkyl et arylalkylene aminoheterocycliques a n substituee en tant qu'agents antisecretoires et antihistaminiques cardiovasculaires

Country Status (1)

Country	Link
CA (1)	CA1291995C (fr)

1987
- 1987-01-08 CA CA000526931A patent/CA1291995C/fr not_active Expired - Fee Related

Legal Events

Date	Code	Title	Description
1996-05-12	MKLA	Lapsed

Publication	Publication Date	Title
US4950674A (en)	1990-08-21	Arylalkylheterocyclic amines,N-substituted by aryloxyalkyl group in a method for allergy treatment
CA1280421C (fr)	1991-02-19	Derives piperidinyl disubstitutes en 1,4
EP0235463A2 (fr)	1987-09-09	Arylalkyl et arylalkylène piperidines substitués sur l'azote utilisés comme agents antihistaminiques cardiovasculaires et antisécrétion
CA1340192C (fr)	1998-12-15	Amine cyclique
US5070087A (en)	1991-12-03	Aryl(alkyland alkylene)-N-((phenoxy and phenylthio)alkyl) aminoheterocyclics as cardiovascular, anthihistaminic, antisecretory and antiallergy agents
US5116846A (en)	1992-05-26	N-aralkyl piperidine derivatives as psychotropic drugs
US6867220B2 (en)	2005-03-15	Phenoxypropanolamines, method for producing them and pharmaceutical compositions containing them
AU8327191A (en)	1992-03-02	N-hydrocarbyl-4-substituted piperidines, their preparation and use as calcium blocking agents
US4783471A (en)	1988-11-08	N-aralkyl piperidine methanol derivatives and the uses thereof
US5021428A (en)	1991-06-04	Novel chemical compounds for the prophylactic treatment of migraine
HU196370B (en)	1988-11-28	Process for producing piperidine derivatives and pharmaceutical compositions comprising such compounds
US5198449A (en)	1993-03-30	N-substituted alpha-arylazacycloalkylmethanamines and their use as cardiovascular agents
KR900005368B1 (ko)	1990-07-28	N-치환된-아릴알킬 및 아릴알킬렌 아미노헤테로사이클릭 화합물
AU673754B2 (en)	1996-11-21	Tetrazole derivatives having antihistaminic and antiallergic activity
US5169096A (en)	1992-12-08	N-aralkyl-piperidine-methanol derivatives
US4912117A (en)	1990-03-27	Novel chemical compounds
BR112013021496A2 (pt)	2019-08-06	composto, composição farmacêutica, processo para a preparação de um composto, método para o tratamento de uma desordem do sistema nervoso central
CA2072520A1 (fr)	1992-12-28	Derives de 2-(1-piperidyl) ethanol, leur obtention et leurs applications therapeutiques
AU629535B2 (en)	1992-10-08	N-substituted-arylalkyl and arylalkylene aminoheterocyclics as cardiovascular antihistaminic and antisecretory agents
CA1291995C (fr)	1991-11-12	Acylalkyl et arylalkylene aminoheterocycliques a n substituee en tant qu'agents antisecretoires et antihistaminiques cardiovasculaires
US3426036A (en)	1969-02-04	N - (p - phenoxybenzoyl - lower alkyl)-4-phenyl-tetrahydropyridyl derivatives; the corresponding alcohol,carbamate and lower alkylene derivatives
US5486527A (en)	1996-01-23	Anticholinergic agents
EP0873990A1 (fr)	1998-10-28	Composes d'acide benzoique et leur emploi medical
EP0511222B1 (fr)	1994-12-07	Piperidines et pyrrolidines disubstituees comme agents anticholinergiques
AU629534B2 (en)	1992-10-08	New methods and related compounds