TW509687B - Novel piperazine derivatives having combined 5HT1A, 5HT1B and 5HT1D recept or antagonist activity and their use for the treatment and prophylaxis of various CNS disorders - Google Patents

Novel piperazine derivatives having combined 5HT1A, 5HT1B and 5HT1D recept or antagonist activity and their use for the treatment and prophylaxis of various CNS disorders Download PDF

Info

Publication number: TW509687B
Authority: TW; Taiwan
Prior art keywords: indole; dihydro; small; methyl; phenylaminocarbonyl
Prior art date: 1997-04-18

Application number

TW087105843A

Other languages

English (en)

Chinese (zh)

Inventor

Laramie Mary Gaster

Harshad Kantilal Rami

Paul Adrian Wyman

Original Assignee

Smithkline Beecham Plc

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.)

1997-04-18

Filing date

1998-04-17

Publication date

2002-11-11

1997-04-18 Priority claimed from GBGB9707829.9A external-priority patent/GB9707829D0/en

1998-01-29 Priority claimed from GBGB9801882.3A external-priority patent/GB9801882D0/en

1998-04-17 Application filed by Smithkline Beecham Plc filed Critical Smithkline Beecham Plc

2002-11-11 Application granted granted Critical

2002-11-11 Publication of TW509687B publication Critical patent/TW509687B/zh

Links

208000015114 central nervous system disease Diseases 0.000 title claims description 5
230000000694 effects Effects 0.000 title claims description 4
238000011282 treatment Methods 0.000 title description 13
239000005557 antagonist Substances 0.000 title description 3
101000783611 Takifugu rubripes 5-hydroxytryptamine receptor 1D Proteins 0.000 title 1
150000004885 piperazines Chemical class 0.000 title 1
238000011321 prophylaxis Methods 0.000 title 1
229940066771 systemic antihistamines piperazine derivative Drugs 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 326
-1 isoquinolmyl Chemical group 0.000 claims abstract description 303
238000000034 method Methods 0.000 claims abstract description 166
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
239000001257 hydrogen Substances 0.000 claims abstract description 31
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 15
229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
239000001301 oxygen Substances 0.000 claims abstract description 15
150000002431 hydrogen Chemical class 0.000 claims abstract description 13
229910052736 halogen Inorganic materials 0.000 claims abstract description 12
150000002367 halogens Chemical class 0.000 claims abstract description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
125000001624 naphthyl group Chemical group 0.000 claims abstract description 11
125000004076 pyridyl group Chemical group 0.000 claims abstract description 8
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
125000002541 furyl group Chemical group 0.000 claims abstract description 3
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract 2
125000002883 imidazolyl group Chemical group 0.000 claims abstract 2
125000001544 thienyl group Chemical group 0.000 claims abstract 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 199
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 73
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 73
230000002079 cooperative effect Effects 0.000 claims description 71
238000011049 filling Methods 0.000 claims description 69
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 57
CMVIZARQTOGMMI-UHFFFAOYSA-N 2-methyl-1H-hexazine Chemical compound CN1NN=NN=N1 CMVIZARQTOGMMI-UHFFFAOYSA-N 0.000 claims description 56
UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 claims description 53
239000007789 gas Substances 0.000 claims description 38
150000003839 salts Chemical class 0.000 claims description 37
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 36
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 32
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 28
125000000217 alkyl group Chemical group 0.000 claims description 21
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 19
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 18
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
239000000463 material Substances 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 13
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 10
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 10
150000003254 radicals Chemical class 0.000 claims description 10
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 9
239000000126 substance Substances 0.000 claims description 9
150000001412 amines Chemical class 0.000 claims description 8
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
239000002464 receptor antagonist Substances 0.000 claims description 4
229940044551 receptor antagonist Drugs 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 3
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
229910052721 tungsten Inorganic materials 0.000 claims description 3
206010012735 Diarrhoea Diseases 0.000 claims description 2
206010028980 Neoplasm Diseases 0.000 claims description 2
230000015572 biosynthetic process Effects 0.000 claims description 2
201000011510 cancer Diseases 0.000 claims description 2
238000009313 farming Methods 0.000 claims description 2
238000000855 fermentation Methods 0.000 claims description 2
230000004151 fermentation Effects 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
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 claims description 2
125000006239 protecting group Chemical group 0.000 claims description 2
PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 3
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 2
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 claims 2
229910052702 rhenium Inorganic materials 0.000 claims 2
AUCGNAJVFOZTHS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=C=N[CH]1 AUCGNAJVFOZTHS-UHFFFAOYSA-N 0.000 claims 1
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims 1
125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 1
AOCUIRLSFONLMP-UHFFFAOYSA-N C1(=CC=CC=2C3=CC=CC=C3CC12)C1CCNCC1 Chemical compound C1(=CC=CC=2C3=CC=CC=C3CC12)C1CCNCC1 AOCUIRLSFONLMP-UHFFFAOYSA-N 0.000 claims 1
VZJSIDSSYLLTQH-UHFFFAOYSA-N CCN1NN=NN=N1 Chemical compound CCN1NN=NN=N1 VZJSIDSSYLLTQH-UHFFFAOYSA-N 0.000 claims 1
NAEKXNBPQGUGCK-UHFFFAOYSA-N CN1N=NC=NN=N1 Chemical compound CN1N=NC=NN=N1 NAEKXNBPQGUGCK-UHFFFAOYSA-N 0.000 claims 1
PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 claims 1
241001674048 Phthiraptera Species 0.000 claims 1
241000270295 Serpentes Species 0.000 claims 1
241001122767 Theaceae Species 0.000 claims 1
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 1
125000000747 amidyl group Chemical group [H][N-]* 0.000 claims 1
235000013405 beer Nutrition 0.000 claims 1
ITQTTZVARXURQS-UHFFFAOYSA-N beta-methylpyridine Natural products CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 claims 1
229920002770 condensed tannin Polymers 0.000 claims 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
RJTZUHVCZIGJMB-UHFFFAOYSA-N hydron;1h-indole;chloride Chemical compound Cl.C1=CC=C2NC=CC2=C1 RJTZUHVCZIGJMB-UHFFFAOYSA-N 0.000 claims 1
JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims 1
230000006698 induction Effects 0.000 claims 1
239000010985 leather Substances 0.000 claims 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims 1
235000018192 pine bark supplement Nutrition 0.000 claims 1
229940106796 pycnogenol Drugs 0.000 claims 1
WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical group [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims 1
125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 1
210000002700 urine Anatomy 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 20
239000003795 chemical substances by application Substances 0.000 abstract description 6
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 abstract description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 5
125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 abstract 2
125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 abstract 1
125000001715 oxadiazolyl group Chemical group 0.000 abstract 1
125000002971 oxazolyl group Chemical group 0.000 abstract 1
125000003386 piperidinyl group Chemical group 0.000 abstract 1
125000003373 pyrazinyl group Chemical group 0.000 abstract 1
125000003226 pyrazolyl group Chemical group 0.000 abstract 1
125000002098 pyridazinyl group Chemical group 0.000 abstract 1
125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
125000000335 thiazolyl group Chemical group 0.000 abstract 1
238000005481 NMR spectroscopy Methods 0.000 description 170
239000007787 solid Substances 0.000 description 167
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 157
101150041968 CDC13 gene Proteins 0.000 description 147
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 100
239000000203 mixture Substances 0.000 description 86
239000000243 solution Substances 0.000 description 85
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 66
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 60
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 53
239000000843 powder Substances 0.000 description 45
239000002253 acid Substances 0.000 description 40
239000002585 base Substances 0.000 description 38
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 38
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 37
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
229910052786 argon Inorganic materials 0.000 description 33
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 32
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 32
238000003756 stirring Methods 0.000 description 31
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
239000012948 isocyanate Substances 0.000 description 26
150000002513 isocyanates Chemical class 0.000 description 26
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 25
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 25
239000006260 foam Substances 0.000 description 25
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
238000010992 reflux Methods 0.000 description 24
239000003921 oil Substances 0.000 description 23
235000019198 oils Nutrition 0.000 description 23
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
229910052757 nitrogen Inorganic materials 0.000 description 21
239000000284 extract Substances 0.000 description 19
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
235000019439 ethyl acetate Nutrition 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
239000012074 organic phase Substances 0.000 description 17
239000004202 carbamide Substances 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
239000012458 free base Substances 0.000 description 14
RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 13
KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
229910000027 potassium carbonate Inorganic materials 0.000 description 13
229960000583 acetic acid Drugs 0.000 description 12
239000000725 suspension Substances 0.000 description 12
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 11
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 11
239000000047 product Substances 0.000 description 11
DDXAGRCTJKBGRK-UHFFFAOYSA-N 4-pyridin-4-ylnaphthalen-1-amine Chemical compound C12=CC=CC=C2C(N)=CC=C1C1=CC=NC=C1 DDXAGRCTJKBGRK-UHFFFAOYSA-N 0.000 description 10
125000000638 benzylaminocarbonyl group Chemical group C(C1=CC=CC=C1)NC(=O)* 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
239000005711 Benzoic acid Substances 0.000 description 9
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 9
235000010233 benzoic acid Nutrition 0.000 description 9
230000027455 binding Effects 0.000 description 9
239000012141 concentrate Substances 0.000 description 9
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
235000008504 concentrate Nutrition 0.000 description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
239000000499 gel Substances 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
229910000029 sodium carbonate Inorganic materials 0.000 description 8
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 8
FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 7
LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
150000007857 hydrazones Chemical class 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
WKYQOSNHIPTONH-UHFFFAOYSA-N 9H-fluorene 1H-indole Chemical compound C1=CC=CC=2C3=CC=CC=C3CC12.N1C=CC2=CC=CC=C12 WKYQOSNHIPTONH-UHFFFAOYSA-N 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
125000003118 aryl group Chemical group 0.000 description 6
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 6
238000009434 installation Methods 0.000 description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
229910052763 palladium Inorganic materials 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
238000012360 testing method Methods 0.000 description 6
238000005160 1H NMR spectroscopy Methods 0.000 description 5
HPYNZHMRTTWQTB-UHFFFAOYSA-N 2,3-dimethylpyridine Chemical compound CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 5
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 5
SIAVMDKGVRXFAX-UHFFFAOYSA-N 4-carboxyphenylboronic acid Chemical compound OB(O)C1=CC=C(C(O)=O)C=C1 SIAVMDKGVRXFAX-UHFFFAOYSA-N 0.000 description 5
125000003341 7 membered heterocyclic group Chemical group 0.000 description 5
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000003814 drug Substances 0.000 description 5
238000003818 flash chromatography Methods 0.000 description 5
125000000623 heterocyclic group Chemical group 0.000 description 5
VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
238000007639 printing Methods 0.000 description 5
QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 5
150000003222 pyridines Chemical class 0.000 description 5
BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
239000004575 stone Substances 0.000 description 5
229910052717 sulfur Chemical group 0.000 description 5
239000011593 sulfur Chemical group 0.000 description 5
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 4
UBIOMSFKBWCPDF-UHFFFAOYSA-N 3-chloro-4-pyridin-4-ylaniline Chemical compound ClC1=CC(N)=CC=C1C1=CC=NC=C1 UBIOMSFKBWCPDF-UHFFFAOYSA-N 0.000 description 4
NPUQZHQMYVCZKK-UHFFFAOYSA-N 3-methyl-4-(6-methylpyridin-2-yl)aniline Chemical compound CC1=CC=CC(C=2C(=CC(N)=CC=2)C)=N1 NPUQZHQMYVCZKK-UHFFFAOYSA-N 0.000 description 4
PTBYEJHCGWGUHD-UHFFFAOYSA-N 4-(5-isocyanatonaphthalen-1-yl)pyridine Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1C1=CC=NC=C1 PTBYEJHCGWGUHD-UHFFFAOYSA-N 0.000 description 4
XLQSMYZSVYWOSX-UHFFFAOYSA-N 4h-indole Chemical compound C1C=CC=C2N=CC=C12 XLQSMYZSVYWOSX-UHFFFAOYSA-N 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
235000019502 Orange oil Nutrition 0.000 description 4
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 4
239000007983 Tris buffer Substances 0.000 description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
208000035475 disorder Diseases 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
238000002955 isolation Methods 0.000 description 4
239000010502 orange oil Substances 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
238000012856 packing Methods 0.000 description 4
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 4
HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 4
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
102000005962 receptors Human genes 0.000 description 4
108020003175 receptors Proteins 0.000 description 4
210000003625 skull Anatomy 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017550 sodium carbonate Nutrition 0.000 description 4
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 3
AHFMSNDOYCFEPH-UHFFFAOYSA-N 1,2-difluoroethane Chemical compound FCCF AHFMSNDOYCFEPH-UHFFFAOYSA-N 0.000 description 3
BDQNKCYCTYYMAA-UHFFFAOYSA-N 1-isocyanatonaphthalene Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1 BDQNKCYCTYYMAA-UHFFFAOYSA-N 0.000 description 3
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 3
PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 3
CKKQZQNCMQYCCC-UHFFFAOYSA-N 2-(4-pyridin-4-ylnaphthalen-1-yl)acetic acid Chemical compound C12=CC=CC=C2C(CC(=O)O)=CC=C1C1=CC=NC=C1 CKKQZQNCMQYCCC-UHFFFAOYSA-N 0.000 description 3
YLNZLZNYTVVZCQ-UHFFFAOYSA-N 2-(5-isocyanatonaphthalen-1-yl)-6-methylpyridine Chemical compound CC1=CC=CC(C=2C3=CC=CC(=C3C=CC=2)N=C=O)=N1 YLNZLZNYTVVZCQ-UHFFFAOYSA-N 0.000 description 3
LICVWQFWIOOBRO-UHFFFAOYSA-N 2-(5-pyridin-4-ylnaphthalen-1-yl)acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1C1=CC=NC=C1 LICVWQFWIOOBRO-UHFFFAOYSA-N 0.000 description 3
RVDVHSPEPYZRSQ-UHFFFAOYSA-N 3-methyl-4-pyrimidin-2-ylaniline Chemical compound CC1=CC(N)=CC=C1C1=NC=CC=N1 RVDVHSPEPYZRSQ-UHFFFAOYSA-N 0.000 description 3
102100027499 5-hydroxytryptamine receptor 1B Human genes 0.000 description 3
101710138639 5-hydroxytryptamine receptor 1B Proteins 0.000 description 3
235000001258 Cinchona calisaya Nutrition 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 3
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
POUDESKFUDQTBK-UHFFFAOYSA-N [4-(1-methyl-2H-pyridin-4-yl)phenyl]methanamine Chemical compound C1=C(C=CC(=C1)CN)C1=CCN(C=C1)C POUDESKFUDQTBK-UHFFFAOYSA-N 0.000 description 3
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
125000002619 bicyclic group Chemical group 0.000 description 3
125000002618 bicyclic heterocycle group Chemical group 0.000 description 3
230000033228 biological regulation Effects 0.000 description 3
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 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
238000004440 column chromatography Methods 0.000 description 3
239000006071 cream Substances 0.000 description 3
125000005842 heteroatom Chemical group 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
125000004356 hydroxy functional group Chemical group O* 0.000 description 3
239000010410 layer Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000011068 loading method Methods 0.000 description 3
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 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
238000000746 purification Methods 0.000 description 3
229960000948 quinine Drugs 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
239000012453 solvate Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 3
239000003053 toxin Substances 0.000 description 3
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
229910052722 tritium Inorganic materials 0.000 description 3
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
ZLOXFEJDHGQNOG-UHFFFAOYSA-N 1-nitroindole Chemical class C1=CC=C2N([N+](=O)[O-])C=CC2=C1 ZLOXFEJDHGQNOG-UHFFFAOYSA-N 0.000 description 2
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 description 2
PGFIHORVILKHIA-UHFFFAOYSA-N 2-bromopyrimidine Chemical compound BrC1=NC=CC=N1 PGFIHORVILKHIA-UHFFFAOYSA-N 0.000 description 2
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 2
CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
BZXOAZNFWYHPRW-UHFFFAOYSA-N 3-methyl-4-pyrimidin-5-ylaniline Chemical compound CC1=CC(N)=CC=C1C1=CN=CN=C1 BZXOAZNFWYHPRW-UHFFFAOYSA-N 0.000 description 2
VLJXXKKOSFGPHI-UHFFFAOYSA-N 3-methylhexane Chemical compound CCCC(C)CC VLJXXKKOSFGPHI-UHFFFAOYSA-N 0.000 description 2
LGQYFEIXVXGFKY-UHFFFAOYSA-N 3-pyrimidin-2-yloxyaniline Chemical compound NC1=CC=CC(OC=2N=CC=CN=2)=C1 LGQYFEIXVXGFKY-UHFFFAOYSA-N 0.000 description 2
ZGOFHPZQYOXFCP-UHFFFAOYSA-N 4-(1,3-thiazol-2-yl)aniline Chemical compound C1=CC(N)=CC=C1C1=NC=CS1 ZGOFHPZQYOXFCP-UHFFFAOYSA-N 0.000 description 2
GSYDYVSCEKJORV-UHFFFAOYSA-N 4-(1-methylpiperidin-4-yl)naphthalen-1-amine Chemical compound C1CN(C)CCC1C1=CC=C(N)C2=CC=CC=C12 GSYDYVSCEKJORV-UHFFFAOYSA-N 0.000 description 2
CDHZKSDNBZBJCU-UHFFFAOYSA-N 4-(2,6-dimethylpyridin-4-yl)-3-methylaniline Chemical compound CC1=NC(C)=CC(C=2C(=CC(N)=CC=2)C)=C1 CDHZKSDNBZBJCU-UHFFFAOYSA-N 0.000 description 2
WEWJKAFIXXEJKA-UHFFFAOYSA-N 4-(5-isocyanatonaphthalen-1-yl)-2,6-dimethylpyridine Chemical compound CC1=NC(C)=CC(C=2C3=CC=CC(=C3C=CC=2)N=C=O)=C1 WEWJKAFIXXEJKA-UHFFFAOYSA-N 0.000 description 2
DANLZOIRUUHIIX-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F DANLZOIRUUHIIX-UHFFFAOYSA-N 0.000 description 2
CUARLQDWYSRQDF-UHFFFAOYSA-N 5-Nitroacenaphthene Chemical compound C1CC2=CC=CC3=C2C1=CC=C3[N+](=O)[O-] CUARLQDWYSRQDF-UHFFFAOYSA-N 0.000 description 2
SZFXXNVLSUTKJF-UHFFFAOYSA-N 5-bromonaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1Br SZFXXNVLSUTKJF-UHFFFAOYSA-N 0.000 description 2
102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 description 2
101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 description 2
BJBWKLPFLJDGGC-UHFFFAOYSA-N 5-pyridin-4-ylnaphthalen-1-amine Chemical compound C1=CC=C2C(N)=CC=CC2=C1C1=CC=NC=C1 BJBWKLPFLJDGGC-UHFFFAOYSA-N 0.000 description 2
DLFLQXUYRFIFOK-UHFFFAOYSA-N 6-phenylpyridine-3-carboxylic acid Chemical compound N1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 DLFLQXUYRFIFOK-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
240000000662 Anethum graveolens Species 0.000 description 2
208000019901 Anxiety disease Diseases 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
101000869592 Daucus carota Major allergen Dau c 1 Chemical group 0.000 description 2
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
101000650136 Homo sapiens WAS/WASL-interacting protein family member 3 Chemical group 0.000 description 2
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
208000026139 Memory disease Diseases 0.000 description 2
241000361919 Metaphire sieboldi Species 0.000 description 2
101100447665 Mus musculus Gas2 gene Proteins 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
239000007832 Na2SO4 Substances 0.000 description 2
208000008589 Obesity Diseases 0.000 description 2
244000131316 Panax pseudoginseng Species 0.000 description 2
235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 2
235000003140 Panax quinquefolius Nutrition 0.000 description 2
240000004808 Saccharomyces cerevisiae Species 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
235000021355 Stearic acid Nutrition 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 2
102100027539 WAS/WASL-interacting protein family member 3 Human genes 0.000 description 2
125000003158 alcohol group Chemical group 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 2
HECLRDQVFMWTQS-HORUIINNSA-N bis[cyclopentadiene] Chemical compound C1C2[C@H]3CC=C[C@H]3C1C=C2 HECLRDQVFMWTQS-HORUIINNSA-N 0.000 description 2
239000004327 boric acid Substances 0.000 description 2
230000005587 bubbling Effects 0.000 description 2
239000000872 buffer Substances 0.000 description 2
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
239000002775 capsule Substances 0.000 description 2
125000001589 carboacyl group Chemical group 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
210000004978 chinese hamster ovary cell Anatomy 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
238000010511 deprotection reaction Methods 0.000 description 2
201000010099 disease Diseases 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
SHZIWNPUGXLXDT-UHFFFAOYSA-N ethyl hexanoate Chemical compound CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 2
GEHLEADVHVVTET-UHFFFAOYSA-N ethyl(methyl)azanium;chloride Chemical compound [Cl-].CC[NH2+]C GEHLEADVHVVTET-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
235000008434 ginseng Nutrition 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
239000007937 lozenge Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
235000013336 milk Nutrition 0.000 description 2
239000008267 milk Substances 0.000 description 2
210000004080 milk Anatomy 0.000 description 2
238000002156 mixing Methods 0.000 description 2
125000006502 nitrobenzyl group Chemical group 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
235000020824 obesity Nutrition 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
238000005192 partition Methods 0.000 description 2
125000001151 peptidyl group Chemical group 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
235000011056 potassium acetate Nutrition 0.000 description 2
235000015320 potassium carbonate Nutrition 0.000 description 2
235000011181 potassium carbonates Nutrition 0.000 description 2
CUNPJFGIODEJLQ-UHFFFAOYSA-M potassium;2,2,2-trifluoroacetate Chemical compound [K+].[O-]C(=O)C(F)(F)F CUNPJFGIODEJLQ-UHFFFAOYSA-M 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
230000002265 prevention Effects 0.000 description 2
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 2
RONWGALEIBILOG-VMJVVOMYSA-N quinine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21.C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 RONWGALEIBILOG-VMJVVOMYSA-N 0.000 description 2
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
SYUHGPGVQRZVTB-UHFFFAOYSA-N radon atom Chemical compound [Rn] SYUHGPGVQRZVTB-UHFFFAOYSA-N 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007921 spray Substances 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
239000008117 stearic acid Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
239000003826 tablet Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
229940098465 tincture Drugs 0.000 description 2
238000005406 washing Methods 0.000 description 2
VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
FUADXEJBHCKVBN-UHFFFAOYSA-N (3-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 FUADXEJBHCKVBN-UHFFFAOYSA-N 0.000 description 1
YOSXJLIIIZSXCC-UHFFFAOYSA-N (4-amino-2-methylphenyl)boronic acid Chemical compound CC1=CC(N)=CC=C1B(O)O YOSXJLIIIZSXCC-UHFFFAOYSA-N 0.000 description 1
RBKHNGHPZZZJCI-UHFFFAOYSA-N (4-aminophenyl)-phenylmethanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC=C1 RBKHNGHPZZZJCI-UHFFFAOYSA-N 0.000 description 1
LPXRLRBXBWDOPK-UHFFFAOYSA-N (4-benzylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1CC1=CC=CC=C1 LPXRLRBXBWDOPK-UHFFFAOYSA-N 0.000 description 1
SRCHLCSUUTVUNG-UHFFFAOYSA-N (5-ethylthiophen-2-yl)boronic acid Chemical compound CCC1=CC=C(B(O)O)S1 SRCHLCSUUTVUNG-UHFFFAOYSA-N 0.000 description 1
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
HDZGBIRSORQVNB-DSXUQNDKSA-N (r)-[(2s,4s,5r)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol;hydrobromide Chemical compound Br.C([C@H]([C@H](C1)C=C)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 HDZGBIRSORQVNB-DSXUQNDKSA-N 0.000 description 1
FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
FYWJWWMKCARWQG-UHFFFAOYSA-N 1,2-dichloro-3-isocyanatobenzene Chemical compound ClC1=CC=CC(N=C=O)=C1Cl FYWJWWMKCARWQG-UHFFFAOYSA-N 0.000 description 1
QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
OVISMSJCKCDOPU-UHFFFAOYSA-N 1,6-dichlorohexane Chemical compound ClCCCCCCCl OVISMSJCKCDOPU-UHFFFAOYSA-N 0.000 description 1
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
DRTQHJPVMGBUCF-UCVXFZOQSA-N 1-[(2s,3s,4s,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O[C@H]1[C@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UCVXFZOQSA-N 0.000 description 1
WJIFKOVZNJTSGO-UHFFFAOYSA-N 1-bromo-3-methylbenzene Chemical compound CC1=CC=CC(Br)=C1 WJIFKOVZNJTSGO-UHFFFAOYSA-N 0.000 description 1
AYFMPMKATOGAGY-UHFFFAOYSA-N 1-bromo-4-isocyanato-2-methylbenzene Chemical compound CC1=CC(N=C=O)=CC=C1Br AYFMPMKATOGAGY-UHFFFAOYSA-N 0.000 description 1
YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 1
WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 description 1
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 1
PNBUGOFIKAHZRW-UHFFFAOYSA-N 1-isocyanato-4-phenoxybenzene Chemical compound C1=CC(N=C=O)=CC=C1OC1=CC=CC=C1 PNBUGOFIKAHZRW-UHFFFAOYSA-N 0.000 description 1
SOXBGESONWKYDX-UHFFFAOYSA-N 1-methyl-6-nitronaphthalene Chemical compound [O-][N+](=O)C1=CC=C2C(C)=CC=CC2=C1 SOXBGESONWKYDX-UHFFFAOYSA-N 0.000 description 1
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical compound C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
VTZWOBVWOGYHSV-UHFFFAOYSA-N 1H-indole stilbene Chemical compound C1=CC=C2NC=CC2=C1.C=1C=CC=CC=1C=CC1=CC=CC=C1 VTZWOBVWOGYHSV-UHFFFAOYSA-N 0.000 description 1
WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 description 1
VIMWRMDQHHYVOY-UHFFFAOYSA-N 2-(4-bromonaphthalen-1-yl)acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=C(Br)C2=C1 VIMWRMDQHHYVOY-UHFFFAOYSA-N 0.000 description 1
VGGNOZLRRMBBQL-UHFFFAOYSA-N 2-(4-isocyanatophenyl)pyrimidine Chemical compound C1=CC(N=C=O)=CC=C1C1=NC=CC=N1 VGGNOZLRRMBBQL-UHFFFAOYSA-N 0.000 description 1
DRSTWYCPWPMIAP-UHFFFAOYSA-N 2-(5-bromonaphthalen-1-yl)acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1Br DRSTWYCPWPMIAP-UHFFFAOYSA-N 0.000 description 1
ZXXNHAMFZOJQMW-UHFFFAOYSA-N 2-(9H-fluoren-1-yl)pyrimidine Chemical compound N1=C(N=CC=C1)C1=CC=CC=2C3=CC=CC=C3CC1=2 ZXXNHAMFZOJQMW-UHFFFAOYSA-N 0.000 description 1
NNWUEBIEOFQMSS-UHFFFAOYSA-N 2-Methylpiperidine Chemical compound CC1CCCCN1 NNWUEBIEOFQMSS-UHFFFAOYSA-N 0.000 description 1
YCHPNSOKVRTPES-UHFFFAOYSA-N 2-bromo-1,3-oxazole Chemical compound BrC1=NC=CO1 YCHPNSOKVRTPES-UHFFFAOYSA-N 0.000 description 1
RXNZFHIEDZEUQM-UHFFFAOYSA-N 2-bromo-1,3-thiazole Chemical compound BrC1=NC=CS1 RXNZFHIEDZEUQM-UHFFFAOYSA-N 0.000 description 1
FQVOKXARZCJTIT-UHFFFAOYSA-N 2-bromopyrene Chemical compound C1=CC=C2C=CC3=CC(Br)=CC4=CC=C1C2=C43 FQVOKXARZCJTIT-UHFFFAOYSA-N 0.000 description 1
PTSLUOSUHFGQHV-UHFFFAOYSA-N 2-chloroheptane Chemical compound CCCCCC(C)Cl PTSLUOSUHFGQHV-UHFFFAOYSA-N 0.000 description 1
OYFIDALWMSGYLQ-UHFFFAOYSA-N 2-ethyl-n-phenylbutanamide Chemical compound CCC(CC)C(=O)NC1=CC=CC=C1 OYFIDALWMSGYLQ-UHFFFAOYSA-N 0.000 description 1
SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
VLRSADZEDXVUPG-UHFFFAOYSA-N 2-naphthalen-1-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CC2=CC=CC=C12 VLRSADZEDXVUPG-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000004105 2-pyridyl group Chemical class N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 description 1
LNVWRBNPXCUYJI-UHFFFAOYSA-N 3,5-dimethyl-1h-pyrazol-4-amine Chemical compound CC1=NNC(C)=C1N LNVWRBNPXCUYJI-UHFFFAOYSA-N 0.000 description 1
HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
OXVKPWUMGBURNN-UHFFFAOYSA-N 3-(4-isocyanatophenyl)-2,6-dimethylpyridine Chemical compound CC1=NC(C)=CC=C1C1=CC=C(N=C=O)C=C1 OXVKPWUMGBURNN-UHFFFAOYSA-N 0.000 description 1
125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 description 1
OOELYXBZHZKDLM-UHFFFAOYSA-N 3-methyl-4-(1,3-thiazol-2-yl)aniline Chemical compound CC1=CC(N)=CC=C1C1=NC=CS1 OOELYXBZHZKDLM-UHFFFAOYSA-N 0.000 description 1
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 1
XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 1
RTZZCYNQPHTPPL-UHFFFAOYSA-N 3-nitrophenol Chemical compound OC1=CC=CC([N+]([O-])=O)=C1 RTZZCYNQPHTPPL-UHFFFAOYSA-N 0.000 description 1
UCSYVYFGMFODMY-UHFFFAOYSA-N 3-phenoxyaniline Chemical compound NC1=CC=CC(OC=2C=CC=CC=2)=C1 UCSYVYFGMFODMY-UHFFFAOYSA-N 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
IFILUKNHOHCWPX-UHFFFAOYSA-N 4-(2,6-dimethylpyridin-3-yl)-3-methylaniline Chemical compound CC1=NC(C)=CC=C1C1=CC=C(N)C=C1C IFILUKNHOHCWPX-UHFFFAOYSA-N 0.000 description 1
PMUWXWKOTRQNGL-UHFFFAOYSA-N 4-(5-methyl-1,3-oxazol-2-yl)aniline Chemical compound O1C(C)=CN=C1C1=CC=C(N)C=C1 PMUWXWKOTRQNGL-UHFFFAOYSA-N 0.000 description 1
QSKZDXHSTLCYPB-UHFFFAOYSA-N 4-(furan-2-yl)aniline Chemical compound C1=CC(N)=CC=C1C1=CC=CO1 QSKZDXHSTLCYPB-UHFFFAOYSA-N 0.000 description 1
QGHDLJAZIIFENW-UHFFFAOYSA-N 4-[1,1,1,3,3,3-hexafluoro-2-(4-hydroxy-3-prop-2-enylphenyl)propan-2-yl]-2-prop-2-enylphenol Chemical group C1=C(CC=C)C(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C(CC=C)=C1 QGHDLJAZIIFENW-UHFFFAOYSA-N 0.000 description 1
KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
VTRFAYHJKSKHGY-UHFFFAOYSA-N 4-bromo-2,6-dimethylpyridine Chemical compound CC1=CC(Br)=CC(C)=N1 VTRFAYHJKSKHGY-UHFFFAOYSA-N 0.000 description 1
WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
VLVCDUSVTXIWGW-UHFFFAOYSA-N 4-iodoaniline Chemical compound NC1=CC=C(I)C=C1 VLVCDUSVTXIWGW-UHFFFAOYSA-N 0.000 description 1
XUPXMIAWKPTZLZ-UHFFFAOYSA-N 4-methylhexan-2-one Chemical compound CCC(C)CC(C)=O XUPXMIAWKPTZLZ-UHFFFAOYSA-N 0.000 description 1
FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 1
HBUWLNOJQAZUQZ-UHFFFAOYSA-N 4-naphthalen-1-ylpyridine Chemical compound C=1C=CC2=CC=CC=C2C=1C1=CC=NC=C1 HBUWLNOJQAZUQZ-UHFFFAOYSA-N 0.000 description 1
GKVYVZSNXXTOMQ-UHFFFAOYSA-N 4-pyridin-4-ylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=NC=C1 GKVYVZSNXXTOMQ-UHFFFAOYSA-N 0.000 description 1
BBMFYNRHMSMWFM-UHFFFAOYSA-N 4h-pyrimidine Chemical compound C1C=C[N]C=N1 BBMFYNRHMSMWFM-UHFFFAOYSA-N 0.000 description 1
COMBRYCXLDMDCU-UHFFFAOYSA-N 5-aminonaphthalene-1-carbonitrile Chemical compound C1=CC=C2C(N)=CC=CC2=C1C#N COMBRYCXLDMDCU-UHFFFAOYSA-N 0.000 description 1
NBMJISAJLZTPOX-UHFFFAOYSA-N 5-borononaphthalene-1-carboxylic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1C(O)=O NBMJISAJLZTPOX-UHFFFAOYSA-N 0.000 description 1
GYCPLYCTMDTEPU-UHFFFAOYSA-N 5-bromopyrimidine Chemical compound BrC1=CN=CN=C1 GYCPLYCTMDTEPU-UHFFFAOYSA-N 0.000 description 1
YPKBCLZFIYBSHK-UHFFFAOYSA-N 5-methylindole Chemical compound CC1=CC=C2NC=CC2=C1 YPKBCLZFIYBSHK-UHFFFAOYSA-N 0.000 description 1
VFTOHJFKIJLYKN-UHFFFAOYSA-N 7-nitro-9h-fluoren-2-ol Chemical group [O-][N+](=O)C1=CC=C2C3=CC=C(O)C=C3CC2=C1 VFTOHJFKIJLYKN-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 description 1
241000254032 Acrididae Species 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
208000000044 Amnesia Diseases 0.000 description 1
208000031091 Amnestic disease Diseases 0.000 description 1
206010002650 Anorexia nervosa and bulimia Diseases 0.000 description 1
241000239290 Araneae Species 0.000 description 1
241000473391 Archosargus rhomboidalis Species 0.000 description 1
PXGGFGPWMIBEPC-UHFFFAOYSA-N BC1=CC=C(C(O)=O)C=C1 Chemical compound BC1=CC=C(C(O)=O)C=C1 PXGGFGPWMIBEPC-UHFFFAOYSA-N 0.000 description 1
241000255789 Bombyx mori Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
XEPAUGJUSNGARB-UHFFFAOYSA-N C(C1=CC=CC=C1)(=N)N.C1=CC=CC=C1 Chemical class C(C1=CC=CC=C1)(=N)N.C1=CC=CC=C1 XEPAUGJUSNGARB-UHFFFAOYSA-N 0.000 description 1
XTQBKGNVFMBLCQ-SPSNFJOYSA-H C(\C=C\C(=O)[O-])(=O)[O-].[Lu+3].C(\C=C\C(=O)[O-])(=O)[O-].C(\C=C\C(=O)[O-])(=O)[O-].[Lu+3] Chemical compound C(\C=C\C(=O)[O-])(=O)[O-].[Lu+3].C(\C=C\C(=O)[O-])(=O)[O-].C(\C=C\C(=O)[O-])(=O)[O-].[Lu+3] XTQBKGNVFMBLCQ-SPSNFJOYSA-H 0.000 description 1
LPWIGHMEEXEYJK-UHFFFAOYSA-N CC1(C=CN(C(C1(Cl)Cl)(Cl)Cl)Cl)Cl Chemical compound CC1(C=CN(C(C1(Cl)Cl)(Cl)Cl)Cl)Cl LPWIGHMEEXEYJK-UHFFFAOYSA-N 0.000 description 1
WRRQQXXLKGTOED-UHFFFAOYSA-N CC1(C=CN(C(C1(F)F)(F)F)F)F Chemical compound CC1(C=CN(C(C1(F)F)(F)F)F)F WRRQQXXLKGTOED-UHFFFAOYSA-N 0.000 description 1
102100022210 COX assembly mitochondrial protein 2 homolog Human genes 0.000 description 1
241000269333 Caudata Species 0.000 description 1
241000282994 Cervidae Species 0.000 description 1
235000007516 Chrysanthemum Nutrition 0.000 description 1
244000189548 Chrysanthemum x morifolium Species 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
241000270722 Crocodylidae Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
208000020401 Depressive disease Diseases 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
101150009796 Dll3 gene Proteins 0.000 description 1
239000005766 Dodine Substances 0.000 description 1
208000030814 Eating disease Diseases 0.000 description 1
239000010282 Emodin Substances 0.000 description 1
208000017701 Endocrine disease Diseases 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
241000400611 Eucalyptus deanei Species 0.000 description 1
244000166102 Eucalyptus leucoxylon Species 0.000 description 1
235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
208000019454 Feeding and Eating disease Diseases 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
208000012895 Gastric disease Diseases 0.000 description 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
241000545744 Hirudinea Species 0.000 description 1
101000900446 Homo sapiens COX assembly mitochondrial protein 2 homolog Proteins 0.000 description 1
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 1
235000000177 Indigofera tinctoria Nutrition 0.000 description 1
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
208000019022 Mood disease Diseases 0.000 description 1
208000016285 Movement disease Diseases 0.000 description 1
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
ZUEOFUWQJWWJFD-UHFFFAOYSA-N O1N=C[BrH][BrH]1 Chemical compound O1N=C[BrH][BrH]1 ZUEOFUWQJWWJFD-UHFFFAOYSA-N 0.000 description 1
208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
206010033799 Paralysis Diseases 0.000 description 1
208000018737 Parkinson disease Diseases 0.000 description 1
206010034010 Parkinsonism Diseases 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
229910052778 Plutonium Inorganic materials 0.000 description 1
229920002873 Polyethylenimine Polymers 0.000 description 1
LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 1
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
241001115903 Raphus cucullatus Species 0.000 description 1
101100169873 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) DCK1 gene Proteins 0.000 description 1
241000269821 Scombridae Species 0.000 description 1
201000001880 Sexual dysfunction Diseases 0.000 description 1
206010041250 Social phobia Diseases 0.000 description 1
PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
244000269722 Thea sinensis Species 0.000 description 1
229910052776 Thorium Inorganic materials 0.000 description 1
240000007591 Tilia tomentosa Species 0.000 description 1
241000244317 Tillandsia usneoides Species 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 1
206010047163 Vasospasm Diseases 0.000 description 1
206010047924 Wheezing Diseases 0.000 description 1
LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
DUIRKDAXQIVVNZ-UHFFFAOYSA-N [4-(4-chlorophenoxy)phenyl]methanamine Chemical compound C1=CC(CN)=CC=C1OC1=CC=C(Cl)C=C1 DUIRKDAXQIVVNZ-UHFFFAOYSA-N 0.000 description 1
SHIYKHFFMRDJJC-UHFFFAOYSA-L [Na+].[Na+].[O-]O[O-] Chemical compound [Na+].[Na+].[O-]O[O-] SHIYKHFFMRDJJC-UHFFFAOYSA-L 0.000 description 1
WJEIYVAPNMUNIU-UHFFFAOYSA-N [Na].OC(O)=O Chemical compound [Na].OC(O)=O WJEIYVAPNMUNIU-UHFFFAOYSA-N 0.000 description 1
JHZICVAIDBTSOQ-UHFFFAOYSA-N [O-2].[Na+].[Ar].[Na+] Chemical compound [O-2].[Na+].[Ar].[Na+] JHZICVAIDBTSOQ-UHFFFAOYSA-N 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
150000001409 amidines Chemical class 0.000 description 1
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
230000006986 amnesia Effects 0.000 description 1
239000003708 ampul Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000000049 anti-anxiety effect Effects 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
239000008365 aqueous carrier Substances 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
238000003556 assay Methods 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
229940090012 bentyl Drugs 0.000 description 1
RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
UUZYBYIOAZTMGC-UHFFFAOYSA-M benzyl(trimethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CC1=CC=CC=C1 UUZYBYIOAZTMGC-UHFFFAOYSA-M 0.000 description 1
KTLFENNEPHBKJD-UHFFFAOYSA-K benzyl(trimethyl)azanium;tribromide Chemical compound [Br-].[Br-].[Br-].C[N+](C)(C)CC1=CC=CC=C1.C[N+](C)(C)CC1=CC=CC=C1.C[N+](C)(C)CC1=CC=CC=C1 KTLFENNEPHBKJD-UHFFFAOYSA-K 0.000 description 1
125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
HBWDWGMBZIFBQE-UHFFFAOYSA-N benzylboronic acid Chemical compound OB(O)CC1=CC=CC=C1 HBWDWGMBZIFBQE-UHFFFAOYSA-N 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
IFVTZJHWGZSXFD-UHFFFAOYSA-N biphenylene Chemical group C1=CC=C2C3=CC=CC=C3C2=C1 IFVTZJHWGZSXFD-UHFFFAOYSA-N 0.000 description 1
229910052797 bismuth Inorganic materials 0.000 description 1
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
229910021538 borax Inorganic materials 0.000 description 1
239000011449 brick Substances 0.000 description 1
SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 description 1
SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
WOBLPDAWNVAVAS-UHFFFAOYSA-N butyl carboxy carbonate Chemical compound CCCCOC(=O)OC(O)=O WOBLPDAWNVAVAS-UHFFFAOYSA-N 0.000 description 1
LUZSPGQEISANPO-UHFFFAOYSA-N butyltin Chemical compound CCCC[Sn] LUZSPGQEISANPO-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
150000003857 carboxamides Chemical class 0.000 description 1
239000006285 cell suspension Substances 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
125000003901 ceryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
238000002512 chemotherapy Methods 0.000 description 1
210000000038 chest Anatomy 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
238000010276 construction Methods 0.000 description 1
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
125000000392 cycloalkenyl group Chemical group 0.000 description 1
230000002950 deficient Effects 0.000 description 1
238000002242 deionisation method Methods 0.000 description 1
230000003111 delayed effect Effects 0.000 description 1
210000004268 dentin Anatomy 0.000 description 1
LNNWVNGFPYWNQE-GMIGKAJZSA-N desomorphine Chemical compound C1C2=CC=C(O)C3=C2[C@]24CCN(C)[C@H]1[C@@H]2CCC[C@@H]4O3 LNNWVNGFPYWNQE-GMIGKAJZSA-N 0.000 description 1
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 1
229960003529 diazepam Drugs 0.000 description 1
150000001990 dicarboxylic acid derivatives Chemical class 0.000 description 1
HJSJHFXDUMCZEC-UHFFFAOYSA-N dichloroarsenic Chemical compound Cl[As]Cl HJSJHFXDUMCZEC-UHFFFAOYSA-N 0.000 description 1
GUBNMFJOJGDCEL-UHFFFAOYSA-N dicyclomine hydrochloride Chemical group [Cl-].C1CCCCC1C1(C(=O)OCC[NH+](CC)CC)CCCCC1 GUBNMFJOJGDCEL-UHFFFAOYSA-N 0.000 description 1
125000006001 difluoroethyl group Chemical group 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
235000014632 disordered eating Nutrition 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
230000001882 diuretic effect Effects 0.000 description 1
230000004064 dysfunction Effects 0.000 description 1
239000008157 edible vegetable oil Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
RHMXXJGYXNZAPX-UHFFFAOYSA-N emodin Chemical compound C1=C(O)C=C2C(=O)C3=CC(C)=CC(O)=C3C(=O)C2=C1O RHMXXJGYXNZAPX-UHFFFAOYSA-N 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
LNYNHRRKSYMFHF-UHFFFAOYSA-K europium(3+);triacetate Chemical compound [Eu+3].CC([O-])=O.CC([O-])=O.CC([O-])=O LNYNHRRKSYMFHF-UHFFFAOYSA-K 0.000 description 1
229960002089 ferrous chloride Drugs 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
238000005187 foaming Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000003205 fragrance Substances 0.000 description 1
PZJSZBJLOWMDRG-UHFFFAOYSA-N furan-2-ylboronic acid Chemical compound OB(O)C1=CC=CO1 PZJSZBJLOWMDRG-UHFFFAOYSA-N 0.000 description 1
238000002309 gasification Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000003292 glue Substances 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 0.000 description 1
YRBKSJIXFZPPGF-UHFFFAOYSA-N hexazine Chemical compound N1=NN=NN=N1 YRBKSJIXFZPPGF-UHFFFAOYSA-N 0.000 description 1
229960002050 hydrofluoric acid Drugs 0.000 description 1
IIXGBDGCPUYARL-UHFFFAOYSA-N hydroxysulfamic acid Chemical compound ONS(O)(=O)=O IIXGBDGCPUYARL-UHFFFAOYSA-N 0.000 description 1
230000002631 hypothermal effect Effects 0.000 description 1
238000011534 incubation Methods 0.000 description 1
229940097275 indigo Drugs 0.000 description 1
COHYTHOBJLSHDF-UHFFFAOYSA-N indigo powder Natural products N1C2=CC=CC=C2C(=O)C1=C1C(=O)C2=CC=CC=C2N1 COHYTHOBJLSHDF-UHFFFAOYSA-N 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000003978 infusion fluid Substances 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000011630 iodine Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
229960001317 isoprenaline Drugs 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
210000003127 knee Anatomy 0.000 description 1
229910052743 krypton Inorganic materials 0.000 description 1
DNNSSWSSYDEUBZ-UHFFFAOYSA-N krypton atom Chemical compound [Kr] DNNSSWSSYDEUBZ-UHFFFAOYSA-N 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
239000003589 local anesthetic agent Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
230000002934 lysing effect Effects 0.000 description 1
235000020640 mackerel Nutrition 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
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
201000003102 mental depression Diseases 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
QSJNAFJALFWFMT-UHFFFAOYSA-N meridine Chemical compound N1C=CC(=O)C2=C1C(=O)C1=NC=CC3=C(C=CC=C4)C4=NC2=C13 QSJNAFJALFWFMT-UHFFFAOYSA-N 0.000 description 1
125000006178 methyl benzyl group Chemical group 0.000 description 1
210000004088 microvessel Anatomy 0.000 description 1
230000003020 moisturizing effect Effects 0.000 description 1
230000004899 motility Effects 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
ARBMSJKZZZWLOE-UHFFFAOYSA-N n-phenyl-1h-indole-2-carboxamide Chemical compound C=1C2=CC=CC=C2NC=1C(=O)NC1=CC=CC=C1 ARBMSJKZZZWLOE-UHFFFAOYSA-N 0.000 description 1
LYXWRHJFQAOPGN-UHFFFAOYSA-N n-phenyl-2-(2-phenylethenyl)aniline Chemical compound C=1C=CC=C(C=CC=2C=CC=CC=2)C=1NC1=CC=CC=C1 LYXWRHJFQAOPGN-UHFFFAOYSA-N 0.000 description 1
HQUBHIUZFKYGLE-UHFFFAOYSA-N n-phenyl-9h-fluorene-1-carboxamide Chemical compound C=1C=CC(C2=CC=CC=C2C2)=C2C=1C(=O)NC1=CC=CC=C1 HQUBHIUZFKYGLE-UHFFFAOYSA-N 0.000 description 1
RMHJJUOPOWPRBP-UHFFFAOYSA-N naphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CC=CC2=C1 RMHJJUOPOWPRBP-UHFFFAOYSA-N 0.000 description 1
125000005184 naphthylamino group Chemical group C1(=CC=CC2=CC=CC=C12)N* 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
230000009871 nonspecific binding Effects 0.000 description 1
238000011022 operating instruction Methods 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
VRAOQOFWZFIOSZ-UHFFFAOYSA-N osmium potassium Chemical compound [K].[Os] VRAOQOFWZFIOSZ-UHFFFAOYSA-N 0.000 description 1
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
125000005254 oxyacyl group Chemical group 0.000 description 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
230000021962 pH elevation Effects 0.000 description 1
MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 1
208000019906 panic disease Diseases 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
LTBUYQWITHXHBR-UHFFFAOYSA-N phenylphosphanylformic acid Chemical compound OC(=O)PC1=CC=CC=C1 LTBUYQWITHXHBR-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
OYEHPCDNVJXUIW-UHFFFAOYSA-N plutonium atom Chemical compound [Pu] OYEHPCDNVJXUIW-UHFFFAOYSA-N 0.000 description 1
208000028173 post-traumatic stress disease Diseases 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
208000020016 psychiatric disease Diseases 0.000 description 1
ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 description 1
229910052704 radon Inorganic materials 0.000 description 1
239000008678 sanqi Substances 0.000 description 1
238000003345 scintillation counting Methods 0.000 description 1
208000012672 seasonal affective disease Diseases 0.000 description 1
230000003248 secreting effect Effects 0.000 description 1
231100000872 sexual dysfunction Toxicity 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
208000019116 sleep disease Diseases 0.000 description 1
239000010802 sludge Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000004328 sodium tetraborate Substances 0.000 description 1
235000010339 sodium tetraborate Nutrition 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
230000000392 somatic effect Effects 0.000 description 1
238000005507 spraying Methods 0.000 description 1
PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
235000021286 stilbenes Nutrition 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
125000005504 styryl group Chemical group 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 description 1
229910052716 thallium Inorganic materials 0.000 description 1
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 1
QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl 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
NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
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 1
238000009827 uniform distribution Methods 0.000 description 1
210000005166 vasculature Anatomy 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
230000037303 wrinkles Effects 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- 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
- 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
- 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
- C07D401/10—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 aromatic rings
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Indole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

TW087105843A 1997-04-18 1998-04-17 Novel piperazine derivatives having combined 5HT1A, 5HT1B and 5HT1D recept or antagonist activity and their use for the treatment and prophylaxis of various CNS disorders TW509687B (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9707829.9A GB9707829D0 (en)	1997-04-18	1997-04-18	Novel compounds
GBGB9801882.3A GB9801882D0 (en)	1998-01-29	1998-01-29	Novel compounds

Publications (1)

Publication Number	Publication Date
TW509687B true TW509687B (en)	2002-11-11

Family

ID=26311401

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW087105843A TW509687B (en)	1997-04-18	1998-04-17	Novel piperazine derivatives having combined 5HT1A, 5HT1B and 5HT1D recept or antagonist activity and their use for the treatment and prophylaxis of various CNS disorders

Country Status (17)

Country	Link
EP (1)	EP0975593A1 (fr)
JP (1)	JP2001524116A (fr)
KR (1)	KR20010006487A (fr)
CN (1)	CN1260781A (fr)
AR (1)	AR013076A1 (fr)
AU (1)	AU732863B2 (fr)
BR (1)	BR9809092A (fr)
CA (1)	CA2288662A1 (fr)
CO (1)	CO4950608A1 (fr)
HU (1)	HUP0001123A3 (fr)
IL (1)	IL132409A0 (fr)
NO (1)	NO995065D0 (fr)
NZ (1)	NZ500252A (fr)
PL (1)	PL336317A1 (fr)
TR (1)	TR199902590T2 (fr)
TW (1)	TW509687B (fr)
WO (1)	WO1998050358A1 (fr)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB9725931D0 (en) *	1997-12-05	1998-02-04	Smithkline Beecham Plc	Novel compounds
WO2000006550A1 (fr) *	1998-07-31	2000-02-10	Nippon Soda Co., Ltd.	Composes phenylazole, procede de production desdits composes et medicaments pour le traitement de l'hyperlipidemie
GB9827882D0 (en) *	1998-12-17	1999-02-10	Smithkline Beecham Plc	Novel compounds
UA62015C2 (en)	1998-12-28	2003-12-15	Pfizer Prod Inc	Benzoizoxazol derivatives, a pharmaceutical composition (variants) based thereon (variants) and a method for treatment (variants)
GB9912417D0 (en)	1999-05-28	1999-07-28	Pfizer Ltd	Compounds useful in therapy
GB9912413D0 (en)	1999-05-28	1999-07-28	Pfizer Ltd	Compounds useful in therapy
WO2001005758A2 (fr) *	1999-07-15	2001-01-25	Nps Allelix Corp.	Composes heterocycliques destines au traitement de la migraine
TR200200795T2 (tr) *	1999-09-25	2002-07-22	Smithkline Beecham P. L. C.	5-HT1B antagonistleri olarak piperazin türevleri
JP2003513075A (ja) *	1999-11-05	2003-04-08	スミスクラインビーチャムパブリックリミテッドカンパニー	複合５ｈｔ１ａ、５ｈｔ１ｂおよび５ｈｔ１ｄ受容体活性を有するイソキノリンおよびキナゾリン誘導体
GB9926303D0 (en) *	1999-11-05	2000-01-12	Smithkline Beecham Plc	Novel compounds
DE10051981A1 (de)	2000-10-20	2002-05-02	Bayer Ag	Substituierte Phenyluracile
GB0106419D0 (en)	2001-03-15	2001-05-02	Smithkline Beecham Plc	Novel compounds
GB0106586D0 (en) *	2001-03-16	2001-05-09	Smithkline Beecham Plc	Novel compounds
BR0210929A (pt) *	2001-06-07	2004-06-08	Hoffmann La Roche	Derivados de indol com afinidade para o receptor 5-ht6
AU2003245773A1 (en)	2002-02-15	2003-09-04	Glaxo Group Limited	Vanilloid receptor modulators
PT1506179E (pt)	2002-05-13	2006-06-30	Hoffmann La Roche	Derivados de benzoxazina como moduladores de 5-ht6 e suas utilizacoes
ATE371653T1 (de)	2003-12-09	2007-09-15	Hoffmann La Roche	Benzoxazinderivate und deren verwendungen
AU2008335709A1 (en) *	2007-12-13	2009-06-18	Amgen Inc.	Gamma secretase modulators
CA2794153C (fr)	2010-03-25	2018-01-02	Glaxosmithkline Llc	Derives d'indoline substitue comme inhibiteurs de perk
GB201106817D0 (en)	2011-04-21	2011-06-01	Astex Therapeutics Ltd	New compound
CN102924330A (zh) *	2012-09-03	2013-02-13	华东理工大学	一种规模化制备5-氨基-1-萘腈的方法
GB201218850D0 (en)	2012-10-19	2012-12-05	Astex Therapeutics Ltd	Bicyclic heterocycle compounds and their uses in therapy
GB201218864D0 (en)	2012-10-19	2012-12-05	Astex Therapeutics Ltd	Bicyclic heterocycle compounds and their uses in therapy
GB201218862D0 (en)	2012-10-19	2012-12-05	Astex Therapeutics Ltd	Bicyclic heterocycle compounds and their uses in therapy
US9980973B2 (en)	2012-10-19	2018-05-29	Astex Therapeutics Limited	Bicyclic heterocycle compounds and their uses in therapy
CN103467374A (zh) *	2013-08-30	2013-12-25	江苏弘和药物研发有限公司	一种8-溴-4-羧基喹啉的合成方法
BR122022015241B1 (pt)	2013-12-20	2023-09-26	Astex Therapeutics Limited	Compostos heterocíclicos bicíclicos intermediários para a preparação de um composto de fórmula (i)
JP6693107B2 (ja) *	2015-12-04	2020-05-13	東ソー株式会社	ルチジン化合物の精製方法
CN115197099A (zh) *	2022-05-30	2022-10-18	安徽昊帆生物有限公司	N-Boc-1，4-苯二胺的制备方法
WO2025259929A1 (fr) *	2024-06-13	2025-12-18	Third Harmonic Bio, Inc.	Composés et compositions utilisés en tant qu'inhibiteurs de kinase c-kit

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PT533268E (pt) *	1991-09-18	2002-02-28	Glaxo Group Ltd	Derivados de benzanilida como antagonistas de 5-ht1d
GB9119920D0 (en) *	1991-09-18	1991-10-30	Glaxo Group Ltd	Chemical compounds
GB9119932D0 (en) *	1991-09-18	1991-10-30	Glaxo Group Ltd	Chemical compounds
WO1995004729A1 (fr) *	1993-08-06	1995-02-16	Smithkline Beecham Plc	Derives amides employes comme antagonistes du recepteur 5ht1d
US5905080A (en) *	1993-08-20	1999-05-18	Smithkline Beecham, P.L.C.	Amide and urea derivatives as 5HT1D receptor antagonists
JP3328936B2 (ja) *	1993-09-03	2002-09-30	スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー	５ｈｔ１ｄレセプター拮抗薬用インドールおよびインドリン誘導体

1998
- 1998-04-14 EP EP98921462A patent/EP0975593A1/fr not_active Withdrawn
- 1998-04-14 BR BR9809092-5A patent/BR9809092A/pt not_active IP Right Cessation
- 1998-04-14 KR KR1019997009577A patent/KR20010006487A/ko not_active Withdrawn
- 1998-04-14 NZ NZ500252A patent/NZ500252A/en unknown
- 1998-04-14 CN CN98806185A patent/CN1260781A/zh active Pending
- 1998-04-14 IL IL13240998A patent/IL132409A0/xx unknown
- 1998-04-14 AU AU74310/98A patent/AU732863B2/en not_active Ceased
- 1998-04-14 HU HU0001123A patent/HUP0001123A3/hu unknown
- 1998-04-14 PL PL98336317A patent/PL336317A1/xx unknown
- 1998-04-14 WO PCT/EP1998/002262 patent/WO1998050358A1/fr not_active Ceased
- 1998-04-14 TR TR1999/02590T patent/TR199902590T2/xx unknown
- 1998-04-14 JP JP54766098A patent/JP2001524116A/ja active Pending
- 1998-04-14 CA CA002288662A patent/CA2288662A1/fr not_active Abandoned
- 1998-04-16 AR ARP980101760A patent/AR013076A1/es not_active Application Discontinuation
- 1998-04-17 CO CO98021149A patent/CO4950608A1/es unknown
- 1998-04-17 TW TW087105843A patent/TW509687B/zh active
1999
- 1999-10-15 NO NO995065A patent/NO995065D0/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
NO995065L (no)	1999-10-15
HUP0001123A2 (hu)	2001-04-28
NZ500252A (en)	2001-07-27
CO4950608A1 (es)	2000-09-01
TR199902590T2 (xx)	2000-06-21
EP0975593A1 (fr)	2000-02-02
NO995065D0 (no)	1999-10-15
PL336317A1 (en)	2000-06-19
CA2288662A1 (fr)	1998-11-12
CN1260781A (zh)	2000-07-19
JP2001524116A (ja)	2001-11-27
AR013076A1 (es)	2000-12-13
HUP0001123A3 (en)	2002-04-29
BR9809092A (pt)	2002-01-22
WO1998050358A1 (fr)	1998-11-12
AU732863B2 (en)	2001-05-03
IL132409A0 (en)	2001-03-19
AU7431098A (en)	1998-11-27
KR20010006487A (ko)	2001-01-26

Publication	Publication Date	Title
TW509687B (en)	2002-11-11	Novel piperazine derivatives having combined 5HT1A, 5HT1B and 5HT1D recept or antagonist activity and their use for the treatment and prophylaxis of various CNS disorders
JP6528957B2 (ja)	2019-06-12	Ｔｒｋ阻害化合物
JP6689805B2 (ja)	2020-04-28	カテプシンｃの置換２−アザ−ビシクロ［２．２．１］ヘプタン−３−カルボン酸（ベンジル−シアノ−メチル）−アミド阻害剤
JP5977779B2 (ja)	2016-08-24	２−（２，４，５−置換−アニリノ）ピリミジン化合物
TW200829591A (en)	2008-07-16	Organic compounds
TW200813022A (en)	2008-03-16	Organic compounds
AU2016262572B2 (en)	2020-04-30	EBNA1 inhibitors and methods using same
TW200403223A (en)	2004-03-01	Novel compounds
TW200540169A (en)	2005-12-16	Mtp inhibiting aryl piperidines or piperazines substituted with 5-membered heterocycles
TWI583687B (zh)	2017-05-21	２－氧雜－５－氮雜雙環［２．２．１］庚－３－基衍生物
CA2877474A1 (fr)	2012-12-27	Composes et ses utilisations therapeutiques
TW200900068A (en)	2009-01-01	Novel N,N'-2,4-dianilinopyrimidine derivatives, the preparation thereof, their use as medicaments, pharmaceutical compositions and, in particular, as IKK inhibitors
TW200944520A (en)	2009-11-01	Spiro compounds as NPY Y5 receptor antagonists
EA019723B1 (ru)	2014-05-30	ИНГИБИТОРЫ cMET
TW201136918A (en)	2011-11-01	Novel substituted triazole derivatives as gamma secretase modulators
JPWO2004020434A1 (ja)	2005-12-15	含窒素芳香環誘導体
TW201204361A (en)	2012-02-01	Nitrogen-containing heterocyclic compound having kynurenine production inhibitory activity
CZ20021038A3 (cs)	2002-08-14	Piperazinové deriváty jako antagonisté 5-HT1B
TW200815397A (en)	2008-04-01	Substituted pyridyl amide compounds as modulators of the histamine H3 receptor
EP2888248B1 (fr)	2016-10-26	4-pyridones substituées et leur utilisation comme inhibiteurs de l'activité de l'élastase neutrophile
CA2974078A1 (fr)	2016-07-28	Composes quinazoline et quinoleine, et utilisations de ceux-ci
JP7688242B1 (ja)	2025-06-03	３－フェニルプロピルアミン誘導体
TW421649B (en)	2001-02-11	4-(1H-indol-1yl)-1-piperidinyl derivatives
US20130085161A1 (en)	2013-04-04	Piperidinyl substituted 1,3-dihydro-benzoimidazol-2-ylideneamine derivatives
TW200800194A (en)	2008-01-01	Kinase inhibitors