OA11441A - 2,3-Substituted indole compounds as COX-2inhibitors. - Google Patents

2,3-Substituted indole compounds as COX-2inhibitors. Download PDF

Info

Publication number: OA11441A
Authority: OA; OAPI
Prior art keywords: indol; chloro; acetic acid; carbonyl; alkyl
Prior art date: 1998-01-05

Application number

OA1200000195A

Other languages

English (en)

Inventor

Stephen Caron

Kiyoshi Kawamura

Hiroki Koike

Kazunari Nakao

Rodney William Stevens

Chikara Uchida

Original Assignee

Pfizer

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.)

1998-01-05

Filing date

2000-06-30

Publication date

2004-04-27

2000-06-30 Application filed by Pfizer filed Critical Pfizer

2004-04-27 Publication of OA11441A publication Critical patent/OA11441A/en

Links

150000002475 indoles Chemical class 0.000 title description 5
239000003255 cyclooxygenase 2 inhibitor Substances 0.000 title description 3
229940111134 coxibs Drugs 0.000 title description 2
125000005843 halogen group Chemical group 0.000 claims abstract description 187
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 128
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 125
150000001875 compounds Chemical class 0.000 claims abstract description 87
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 60
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 47
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 34
125000005842 heteroatom Chemical group 0.000 claims abstract description 31
229910052717 sulfur Inorganic materials 0.000 claims abstract description 29
229910052760 oxygen Inorganic materials 0.000 claims abstract description 27
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 23
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
239000001257 hydrogen Substances 0.000 claims abstract description 20
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 19
150000003180 prostaglandins Chemical class 0.000 claims abstract description 10
238000011282 treatment Methods 0.000 claims abstract description 10
229940094443 oxytocics prostaglandins Drugs 0.000 claims abstract description 9
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 8
244000052769 pathogen Species 0.000 claims abstract description 5
150000003839 salts Chemical class 0.000 claims abstract description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 3065
125000000217 alkyl group Chemical group 0.000 claims description 576
-1 -NH2S(O)2NR2R3 Chemical group 0.000 claims description 340
125000003545 alkoxy group Chemical group 0.000 claims description 272
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 215
125000001424 substituent group Chemical group 0.000 claims description 139
125000003282 alkyl amino group Chemical group 0.000 claims description 125
238000000034 method Methods 0.000 claims description 112
230000008569 process Effects 0.000 claims description 109
125000003118 aryl group Chemical group 0.000 claims description 84
239000002253 acid Substances 0.000 claims description 63
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 50
125000000753 cycloalkyl group Chemical group 0.000 claims description 48
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 47
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 46
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 46
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 36
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 34
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 28
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
229940093956 potassium carbonate Drugs 0.000 claims description 23
229910000027 potassium carbonate Inorganic materials 0.000 claims description 23
235000011181 potassium carbonates Nutrition 0.000 claims description 23
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 21
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 21
239000002904 solvent Substances 0.000 claims description 21
125000004429 atom Chemical group 0.000 claims description 20
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical group C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims description 19
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 17
125000004076 pyridyl group Chemical group 0.000 claims description 17
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 16
HQRJGLVSBRTHME-UHFFFAOYSA-N 2-(2-benzoyl-6-chloro-1h-indol-3-yl)acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=CC=C1 HQRJGLVSBRTHME-UHFFFAOYSA-N 0.000 claims description 14
KEJUQGPSVNKHSC-UHFFFAOYSA-N 2-(2-benzoyl-6-chloro-1h-indol-3-yl)propanoic acid Chemical compound N1C2=CC(Cl)=CC=C2C(C(C(O)=O)C)=C1C(=O)C1=CC=CC=C1 KEJUQGPSVNKHSC-UHFFFAOYSA-N 0.000 claims description 14
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 14
235000017550 sodium carbonate Nutrition 0.000 claims description 14
229940001593 sodium carbonate Drugs 0.000 claims description 14
229910000029 sodium carbonate Inorganic materials 0.000 claims description 14
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
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 claims description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 12
125000002541 furyl group Chemical group 0.000 claims description 12
229960005235 piperonyl butoxide Drugs 0.000 claims description 12
235000019260 propionic acid Nutrition 0.000 claims description 12
239000011734 sodium Substances 0.000 claims description 12
229910052708 sodium Inorganic materials 0.000 claims description 12
CYAAZZVFMHQIDN-UHFFFAOYSA-N 2-[6-chloro-2-(5-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound N1=CC(C)=CC=C1C(=O)C1=C(CC(O)=O)C2=CC=C(Cl)C=C2N1 CYAAZZVFMHQIDN-UHFFFAOYSA-N 0.000 claims description 11
125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 11
125000005956 isoquinolyl group Chemical group 0.000 claims description 11
125000006239 protecting group Chemical group 0.000 claims description 11
125000000168 pyrrolyl group Chemical group 0.000 claims description 11
125000001544 thienyl group Chemical group 0.000 claims description 11
MLZIULVXMJPQQB-UHFFFAOYSA-N 2-[5-chloro-2-(4-chlorobenzoyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)O)=C1C(=O)C1=CC=C(Cl)C=C1 MLZIULVXMJPQQB-UHFFFAOYSA-N 0.000 claims description 10
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
125000001153 fluoro group Chemical group F* 0.000 claims description 10
238000004519 manufacturing process Methods 0.000 claims description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 9
WZVXGBZLTRACHK-UHFFFAOYSA-N methyl 2-[6-chloro-2-(4-chloropyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC(Cl)=CC=N1 WZVXGBZLTRACHK-UHFFFAOYSA-N 0.000 claims description 9
239000011591 potassium Substances 0.000 claims description 9
229910052700 potassium Inorganic materials 0.000 claims description 9
125000000335 thiazolyl group Chemical group 0.000 claims description 9
RLFOJZHXUDIGJS-UHFFFAOYSA-N 2-[5-chloro-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CC1=CC=NC(C(=O)C2=C(C3=CC(Cl)=CC=C3N2)CC(O)=O)=C1 RLFOJZHXUDIGJS-UHFFFAOYSA-N 0.000 claims description 8
BDNUVQMJHCYXNX-UHFFFAOYSA-N 2-[6-chloro-2-(3-chlorobenzoyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=CC(Cl)=C1 BDNUVQMJHCYXNX-UHFFFAOYSA-N 0.000 claims description 8
UEMRRUGDDLKXAI-UHFFFAOYSA-N 2-[6-chloro-2-(pyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=CC=N1 UEMRRUGDDLKXAI-UHFFFAOYSA-N 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 8
229910052731 fluorine Inorganic materials 0.000 claims description 8
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
XVLQJDCWMUNWRE-UHFFFAOYSA-N 2-[2-(4-chlorobenzoyl)-5-fluoro-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC=C(F)C=C2C(CC(=O)O)=C1C(=O)C1=CC=C(Cl)C=C1 XVLQJDCWMUNWRE-UHFFFAOYSA-N 0.000 claims description 7
NBWDQAZRDWYIEX-UHFFFAOYSA-N 2-[5-chloro-2-(4-ethyl-3-fluoropyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CCC1=CC=NC(C(=O)C2=C(C3=CC(Cl)=CC=C3N2)CC(O)=O)=C1F NBWDQAZRDWYIEX-UHFFFAOYSA-N 0.000 claims description 7
RGLFGUMIFBYKFQ-UHFFFAOYSA-N 2-[6-chloro-2-(4-ethylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CCC1=CC=NC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)CC(O)=O)=C1 RGLFGUMIFBYKFQ-UHFFFAOYSA-N 0.000 claims description 7
125000002883 imidazolyl group Chemical group 0.000 claims description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
QMTMMRYOKQOECS-UHFFFAOYSA-N methyl 2-[2-(4-ethylpyridine-2-carbonyl)-5-(trifluoromethyl)-1h-indol-3-yl]acetate Chemical compound CCC1=CC=NC(C(=O)C2=C(C3=CC(=CC=C3N2)C(F)(F)F)CC(=O)OC)=C1 QMTMMRYOKQOECS-UHFFFAOYSA-N 0.000 claims description 7
RDCTWILJYCSIGQ-UHFFFAOYSA-N methyl 2-[5-chloro-2-(1,3-thiazole-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)OC)=C1C(=O)C1=NC=CS1 RDCTWILJYCSIGQ-UHFFFAOYSA-N 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 7
125000002950 monocyclic group Chemical group 0.000 claims description 7
239000011736 potassium bicarbonate Substances 0.000 claims description 7
235000015497 potassium bicarbonate Nutrition 0.000 claims description 7
229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 7
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 7
125000005493 quinolyl group Chemical group 0.000 claims description 7
235000011121 sodium hydroxide Nutrition 0.000 claims description 7
229940083608 sodium hydroxide Drugs 0.000 claims description 7
RGCXAYMJOQCZEO-UHFFFAOYSA-N 2-(2-benzoyl-4,5-dichloro-1h-indol-3-yl)acetic acid Chemical compound N1C2=CC=C(Cl)C(Cl)=C2C(CC(=O)O)=C1C(=O)C1=CC=CC=C1 RGCXAYMJOQCZEO-UHFFFAOYSA-N 0.000 claims description 6
QFIPOAGESQAQMM-UHFFFAOYSA-N 2-[2-(3-chlorobenzoyl)-5-fluoro-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC=C(F)C=C2C(CC(=O)O)=C1C(=O)C1=CC=CC(Cl)=C1 QFIPOAGESQAQMM-UHFFFAOYSA-N 0.000 claims description 6
UVHKKXATRFCHKH-UHFFFAOYSA-N 2-[2-(4-methylpyridine-2-carbonyl)-5-(trifluoromethyl)-1h-indol-3-yl]acetic acid Chemical compound CC1=CC=NC(C(=O)C2=C(C3=CC(=CC=C3N2)C(F)(F)F)CC(O)=O)=C1 UVHKKXATRFCHKH-UHFFFAOYSA-N 0.000 claims description 6
LROJUDNAHMMTRQ-UHFFFAOYSA-N 2-[6-chloro-2-(1-methylimidazole-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CN1C=CN=C1C(=O)C1=C(CC(O)=O)C2=CC=C(Cl)C=C2N1 LROJUDNAHMMTRQ-UHFFFAOYSA-N 0.000 claims description 6
YDQDBRSFDWZTGQ-UHFFFAOYSA-N 2-[6-chloro-2-(4-chlorobenzoyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=C(Cl)C=C1 YDQDBRSFDWZTGQ-UHFFFAOYSA-N 0.000 claims description 6
DIPIROZSUXXMDC-UHFFFAOYSA-N 2-[6-chloro-2-(4-chloropyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC(Cl)=CC=N1 DIPIROZSUXXMDC-UHFFFAOYSA-N 0.000 claims description 6
BPOHSYQWAARKKL-UHFFFAOYSA-N 2-[6-chloro-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CC1=CC=NC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)CC(O)=O)=C1 BPOHSYQWAARKKL-UHFFFAOYSA-N 0.000 claims description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
125000001188 haloalkyl group Chemical group 0.000 claims description 6
125000000842 isoxazolyl group Chemical group 0.000 claims description 6
VJIDCNNMSCMLIP-UHFFFAOYSA-N methyl 2-(2-benzoyl-6-chloro-1h-indol-3-yl)acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC=CC=C1 VJIDCNNMSCMLIP-UHFFFAOYSA-N 0.000 claims description 6
OTLKTDXZJMGTRZ-UHFFFAOYSA-N methyl 2-[5-chloro-2-(6-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)OC)=C1C(=O)C1=CC=CC(C)=N1 OTLKTDXZJMGTRZ-UHFFFAOYSA-N 0.000 claims description 6
ZFKCRNCLYPCFID-UHFFFAOYSA-N methyl 2-[6-chloro-2-(4-ethylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound CCC1=CC=NC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)CC(=O)OC)=C1 ZFKCRNCLYPCFID-UHFFFAOYSA-N 0.000 claims description 6
AWEROMAJRHRVJO-UHFFFAOYSA-N methyl 2-[6-chloro-2-(4-methoxypyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC(OC)=CC=N1 AWEROMAJRHRVJO-UHFFFAOYSA-N 0.000 claims description 6
229940094025 potassium bicarbonate Drugs 0.000 claims description 6
MVQGYQWCZHUOJM-UHFFFAOYSA-N 2-(2-benzoyl-5,6-dichloro-1h-indol-3-yl)acetic acid Chemical compound N1C2=CC(Cl)=C(Cl)C=C2C(CC(=O)O)=C1C(=O)C1=CC=CC=C1 MVQGYQWCZHUOJM-UHFFFAOYSA-N 0.000 claims description 5
ZDJRFRQLCMSGPP-UHFFFAOYSA-N 2-[2-(3-bromobenzoyl)-6-chloro-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=CC(Br)=C1 ZDJRFRQLCMSGPP-UHFFFAOYSA-N 0.000 claims description 5
MRLKUSHNICBCJA-UHFFFAOYSA-N 2-[6-chloro-2-(3-chloro-4-ethylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CCC1=CC=NC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)CC(O)=O)=C1Cl MRLKUSHNICBCJA-UHFFFAOYSA-N 0.000 claims description 5
OECDPNLTRYRKMK-UHFFFAOYSA-N 2-[6-chloro-2-(3-fluorobenzoyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=CC(F)=C1 OECDPNLTRYRKMK-UHFFFAOYSA-N 0.000 claims description 5
CBOZTEXMHUCFHN-UHFFFAOYSA-N 2-[6-chloro-2-(4-ethyl-3-fluoropyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CCC1=CC=NC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)CC(O)=O)=C1F CBOZTEXMHUCFHN-UHFFFAOYSA-N 0.000 claims description 5
OBOGPOWHCAHBJA-UHFFFAOYSA-N 2-[6-chloro-2-(4-fluorobenzoyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=C(F)C=C1 OBOGPOWHCAHBJA-UHFFFAOYSA-N 0.000 claims description 5
RFUDIMXRYHINIU-UHFFFAOYSA-N 2-[6-chloro-2-(4-methoxypyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound COC1=CC=NC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)CC(O)=O)=C1 RFUDIMXRYHINIU-UHFFFAOYSA-N 0.000 claims description 5
ZVWYMLHJDRBVDP-UHFFFAOYSA-N 2-[6-chloro-2-(5-chloropyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=C(Cl)C=N1 ZVWYMLHJDRBVDP-UHFFFAOYSA-N 0.000 claims description 5
YESINYJNRVODPJ-UHFFFAOYSA-N 2-[6-methyl-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CC1=CC=NC(C(=O)C2=C(C3=CC=C(C)C=C3N2)CC(O)=O)=C1 YESINYJNRVODPJ-UHFFFAOYSA-N 0.000 claims description 5
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
KIXZIIPOEDQDPE-UHFFFAOYSA-N methyl 2-[2-(4-chlorobenzoyl)-5-(trifluoromethyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(C(F)(F)F)C=C2C(CC(=O)OC)=C1C(=O)C1=CC=C(Cl)C=C1 KIXZIIPOEDQDPE-UHFFFAOYSA-N 0.000 claims description 5
CKEARHMPPKSQCH-UHFFFAOYSA-N methyl 2-[5-chloro-2-(4-ethylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound CCC1=CC=NC(C(=O)C2=C(C3=CC(Cl)=CC=C3N2)CC(=O)OC)=C1 CKEARHMPPKSQCH-UHFFFAOYSA-N 0.000 claims description 5
YYONNDLDBWXJTE-UHFFFAOYSA-N methyl 2-[5-chloro-2-(5-methyl-1,3-thiazole-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)OC)=C1C(=O)C1=NC=C(C)S1 YYONNDLDBWXJTE-UHFFFAOYSA-N 0.000 claims description 5
ZEQZTKODWNBFBB-UHFFFAOYSA-N methyl 2-[6-chloro-2-(4-chlorobenzoyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC=C(Cl)C=C1 ZEQZTKODWNBFBB-UHFFFAOYSA-N 0.000 claims description 5
ZOADIQYIWOFKES-UHFFFAOYSA-N methyl 2-[6-chloro-2-(4-methoxybenzoyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC=C(OC)C=C1 ZOADIQYIWOFKES-UHFFFAOYSA-N 0.000 claims description 5
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
125000003373 pyrazinyl group Chemical group 0.000 claims description 5
125000003226 pyrazolyl group Chemical group 0.000 claims description 5
125000002098 pyridazinyl group Chemical group 0.000 claims description 5
125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
125000003831 tetrazolyl group Chemical group 0.000 claims description 5
125000001425 triazolyl group Chemical group 0.000 claims description 5
125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 4
MZYCQNRHBIVTKU-UHFFFAOYSA-N 2-(2-benzoyl-4,6-dichloro-1h-indol-3-yl)acetic acid Chemical compound N1C2=CC(Cl)=CC(Cl)=C2C(CC(=O)O)=C1C(=O)C1=CC=CC=C1 MZYCQNRHBIVTKU-UHFFFAOYSA-N 0.000 claims description 4
VQLKXSHAOFDVGU-UHFFFAOYSA-N 2-[2-(4-chlorobenzoyl)-5-methyl-1h-indol-3-yl]acetic acid Chemical compound OC(=O)CC=1C2=CC(C)=CC=C2NC=1C(=O)C1=CC=C(Cl)C=C1 VQLKXSHAOFDVGU-UHFFFAOYSA-N 0.000 claims description 4
AIMJTNLASDKXRX-UHFFFAOYSA-N 2-[2-(4-ethylpyridine-2-carbonyl)-5-(trifluoromethyl)-1h-indol-3-yl]acetic acid Chemical compound CCC1=CC=NC(C(=O)C2=C(C3=CC(=CC=C3N2)C(F)(F)F)CC(O)=O)=C1 AIMJTNLASDKXRX-UHFFFAOYSA-N 0.000 claims description 4
BCWXTKUXLJZSTK-UHFFFAOYSA-N 2-[2-(4-methylpyridine-2-carbonyl)-6-(trifluoromethyl)-1h-indol-3-yl]acetic acid Chemical compound CC1=CC=NC(C(=O)C2=C(C3=CC=C(C=C3N2)C(F)(F)F)CC(O)=O)=C1 BCWXTKUXLJZSTK-UHFFFAOYSA-N 0.000 claims description 4
TZLPVLNZOJKCEX-UHFFFAOYSA-N 2-[5-chloro-2-(3-chlorobenzoyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)O)=C1C(=O)C1=CC=CC(Cl)=C1 TZLPVLNZOJKCEX-UHFFFAOYSA-N 0.000 claims description 4
VZEKGVPKLLSTGW-UHFFFAOYSA-N 2-[5-chloro-2-(4-ethylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CCC1=CC=NC(C(=O)C2=C(C3=CC(Cl)=CC=C3N2)CC(O)=O)=C1 VZEKGVPKLLSTGW-UHFFFAOYSA-N 0.000 claims description 4
OVWLTNXNSZARCP-UHFFFAOYSA-N 2-[5-chloro-2-(isoquinoline-3-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound C1=CC=C2C=NC(C(=O)C3=C(C4=CC(Cl)=CC=C4N3)CC(=O)O)=CC2=C1 OVWLTNXNSZARCP-UHFFFAOYSA-N 0.000 claims description 4
KSVMVQMNGVVAND-UHFFFAOYSA-N 2-[5-chloro-2-[4-(hydroxymethyl)pyridine-2-carbonyl]-1h-indol-3-yl]acetic acid Chemical compound OCC1=CC=NC(C(=O)C2=C(C3=CC(Cl)=CC=C3N2)CC(O)=O)=C1 KSVMVQMNGVVAND-UHFFFAOYSA-N 0.000 claims description 4
ABXKVHVCGDJWJE-UHFFFAOYSA-N 2-[6-chloro-2-(4-methoxybenzoyl)-1h-indol-3-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(CC(O)=O)C2=CC=C(Cl)C=C2N1 ABXKVHVCGDJWJE-UHFFFAOYSA-N 0.000 claims description 4
DSUAFFATXOUZKH-UHFFFAOYSA-N 2-[6-chloro-2-[4-(trifluoromethyl)benzoyl]-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=C(C(F)(F)F)C=C1 DSUAFFATXOUZKH-UHFFFAOYSA-N 0.000 claims description 4
MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 4
JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 4
108010081348 HRT1 protein Hairy Proteins 0.000 claims description 4
102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
125000000068 chlorophenyl group Chemical group 0.000 claims description 4
125000006378 chloropyridyl group Chemical group 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
GVJWORSWXAADOI-UHFFFAOYSA-N methyl 2-[5-chloro-2-(isoquinoline-3-carbonyl)-1h-indol-3-yl]acetate Chemical compound C1=CC=C2C=NC(C(=O)C3=C(C4=CC(Cl)=CC=C4N3)CC(=O)OC)=CC2=C1 GVJWORSWXAADOI-UHFFFAOYSA-N 0.000 claims description 4
HUVVRRBFGIXOAA-UHFFFAOYSA-N methyl 2-[5-ethyl-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound COC(=O)CC=1C2=CC(CC)=CC=C2NC=1C(=O)C1=CC(C)=CC=N1 HUVVRRBFGIXOAA-UHFFFAOYSA-N 0.000 claims description 4
NMTHUPOCGNUMEK-UHFFFAOYSA-N methyl 2-[6-chloro-2-(4-methyl-1,3-thiazole-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=NC(C)=CS1 NMTHUPOCGNUMEK-UHFFFAOYSA-N 0.000 claims description 4
XYQZXDXEEPSBPJ-UHFFFAOYSA-N methyl 2-[6-chloro-2-(5-methyl-1,3-thiazole-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=NC=C(C)S1 XYQZXDXEEPSBPJ-UHFFFAOYSA-N 0.000 claims description 4
MUKSXUCOPSOZLA-UHFFFAOYSA-N methyl 2-[6-methoxy-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(OC)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC(C)=CC=N1 MUKSXUCOPSOZLA-UHFFFAOYSA-N 0.000 claims description 4
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
235000011118 potassium hydroxide Nutrition 0.000 claims description 4
229940093932 potassium hydroxide Drugs 0.000 claims description 4
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 4
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
MXYBRVWAGAYMRD-UHFFFAOYSA-N 2-[2-(4-chlorobenzoyl)-5-(trifluoromethyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC=C(C(F)(F)F)C=C2C(CC(=O)O)=C1C(=O)C1=CC=C(Cl)C=C1 MXYBRVWAGAYMRD-UHFFFAOYSA-N 0.000 claims description 3
IIWDFIMVYFBIKL-UHFFFAOYSA-N 2-[2-(4-chlorobenzoyl)-6-methyl-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(C)=CC=C2C(CC(O)=O)=C1C(=O)C1=CC=C(Cl)C=C1 IIWDFIMVYFBIKL-UHFFFAOYSA-N 0.000 claims description 3
ZZJAAJNNPOFPLR-UHFFFAOYSA-N 2-[2-(4-methylpyridine-2-carbonyl)-5-propan-2-yl-1h-indol-3-yl]acetic acid Chemical compound OC(=O)CC=1C2=CC(C(C)C)=CC=C2NC=1C(=O)C1=CC(C)=CC=N1 ZZJAAJNNPOFPLR-UHFFFAOYSA-N 0.000 claims description 3
LDAHATKHGBUGKA-UHFFFAOYSA-N 2-[5-chloro-2-(4,5-dimethylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound C1=C(C)C(C)=CN=C1C(=O)C1=C(CC(O)=O)C2=CC(Cl)=CC=C2N1 LDAHATKHGBUGKA-UHFFFAOYSA-N 0.000 claims description 3
QJAKXUJCEPEDLE-UHFFFAOYSA-N 2-[5-chloro-2-(4-propylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CCCC1=CC=NC(C(=O)C2=C(C3=CC(Cl)=CC=C3N2)CC(O)=O)=C1 QJAKXUJCEPEDLE-UHFFFAOYSA-N 0.000 claims description 3
VCBDDETUJPLUQF-UHFFFAOYSA-N 2-[6-chloro-2-(4-propan-2-ylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CC(C)C1=CC=NC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)CC(O)=O)=C1 VCBDDETUJPLUQF-UHFFFAOYSA-N 0.000 claims description 3
YERXLEPFLRGTEC-UHFFFAOYSA-N 2-[6-chloro-2-(furan-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=CO1 YERXLEPFLRGTEC-UHFFFAOYSA-N 0.000 claims description 3
PCOWMZVUUCRSQV-UHFFFAOYSA-N 2-[6-chloro-2-[3-(methoxymethyl)furan-2-carbonyl]-1h-indol-3-yl]acetic acid Chemical compound C1=COC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)CC(O)=O)=C1COC PCOWMZVUUCRSQV-UHFFFAOYSA-N 0.000 claims description 3
WQWCZMUDOGVFDT-UHFFFAOYSA-N 2-[6-chloro-2-[4-(1-hydroxyethyl)pyridine-2-carbonyl]-1h-indol-3-yl]acetic acid Chemical compound CC(O)C1=CC=NC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)CC(O)=O)=C1 WQWCZMUDOGVFDT-UHFFFAOYSA-N 0.000 claims description 3
SGDBQSCWSGKGKR-UHFFFAOYSA-N 2-[6-chloro-2-[4-(trifluoromethoxy)benzoyl]-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=C(OC(F)(F)F)C=C1 SGDBQSCWSGKGKR-UHFFFAOYSA-N 0.000 claims description 3
BOMOMSZJWZTWMG-UHFFFAOYSA-N 2-[6-chloro-2-[5-(trifluoromethyl)pyridine-2-carbonyl]-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=C(C(F)(F)F)C=N1 BOMOMSZJWZTWMG-UHFFFAOYSA-N 0.000 claims description 3
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 3
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 3
VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 3
125000001041 indolyl group Chemical group 0.000 claims description 3
AZBILHAGGANXIZ-UHFFFAOYSA-N methyl 2-[5-chloro-2-(3-chloro-4-ethylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound CCC1=CC=NC(C(=O)C2=C(C3=CC(Cl)=CC=C3N2)CC(=O)OC)=C1Cl AZBILHAGGANXIZ-UHFFFAOYSA-N 0.000 claims description 3
ONWHWGCLUPWJEL-UHFFFAOYSA-N methyl 2-[5-chloro-2-(4,5-dimethylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)OC)=C1C(=O)C1=CC(C)=C(C)C=N1 ONWHWGCLUPWJEL-UHFFFAOYSA-N 0.000 claims description 3
NGQCMODJGDZYPG-UHFFFAOYSA-N methyl 2-[5-chloro-2-(4,6-dimethylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)OC)=C1C(=O)C1=CC(C)=CC(C)=N1 NGQCMODJGDZYPG-UHFFFAOYSA-N 0.000 claims description 3
TUIXRWUNIYZKSM-UHFFFAOYSA-N methyl 2-[5-chloro-2-(4-chloropyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)OC)=C1C(=O)C1=CC(Cl)=CC=N1 TUIXRWUNIYZKSM-UHFFFAOYSA-N 0.000 claims description 3
LQIXBCDBBLTNSJ-UHFFFAOYSA-N methyl 2-[5-chloro-2-(4-ethyl-3-fluoropyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound CCC1=CC=NC(C(=O)C2=C(C3=CC(Cl)=CC=C3N2)CC(=O)OC)=C1F LQIXBCDBBLTNSJ-UHFFFAOYSA-N 0.000 claims description 3
QSXVQLOWMJUHFZ-UHFFFAOYSA-N methyl 2-[5-chloro-2-(4-methoxypyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)OC)=C1C(=O)C1=CC(OC)=CC=N1 QSXVQLOWMJUHFZ-UHFFFAOYSA-N 0.000 claims description 3
WANHWOGHEHZADH-UHFFFAOYSA-N methyl 2-[5-chloro-2-(5-chloropyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)OC)=C1C(=O)C1=CC=C(Cl)C=N1 WANHWOGHEHZADH-UHFFFAOYSA-N 0.000 claims description 3
YDBSPIZAPVSXBP-UHFFFAOYSA-N methyl 2-[5-chloro-2-(5-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)OC)=C1C(=O)C1=CC=C(C)C=N1 YDBSPIZAPVSXBP-UHFFFAOYSA-N 0.000 claims description 3
HVECEOGUMBIZGR-UHFFFAOYSA-N methyl 2-[5-chloro-2-[4-(trifluoromethoxy)benzoyl]-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)OC)=C1C(=O)C1=CC=C(OC(F)(F)F)C=C1 HVECEOGUMBIZGR-UHFFFAOYSA-N 0.000 claims description 3
LPWYMMCSDUGWEC-UHFFFAOYSA-N methyl 2-[6-chloro-2-(3-methoxybenzoyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC=CC(OC)=C1 LPWYMMCSDUGWEC-UHFFFAOYSA-N 0.000 claims description 3
BFYIIMBAFCOCTH-UHFFFAOYSA-N methyl 2-[6-chloro-2-(4-chlorobenzoyl)-5-fluoro-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=C(F)C=C2C(CC(=O)OC)=C1C(=O)C1=CC=C(Cl)C=C1 BFYIIMBAFCOCTH-UHFFFAOYSA-N 0.000 claims description 3
LIFOJSQXTVEAAX-UHFFFAOYSA-N methyl 2-[6-chloro-2-(5-chloropyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC=C(Cl)C=N1 LIFOJSQXTVEAAX-UHFFFAOYSA-N 0.000 claims description 3
LNIJCVFQXWXLKY-UHFFFAOYSA-N methyl 2-[6-chloro-2-(6-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC=CC(C)=N1 LNIJCVFQXWXLKY-UHFFFAOYSA-N 0.000 claims description 3
PIXVHIRVGBWQHI-UHFFFAOYSA-N methyl 2-[6-chloro-2-(isoquinoline-3-carbonyl)-1h-indol-3-yl]acetate Chemical compound C1=CC=C2C=NC(C(=O)C3=C(C4=CC=C(Cl)C=C4N3)CC(=O)OC)=CC2=C1 PIXVHIRVGBWQHI-UHFFFAOYSA-N 0.000 claims description 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000002971 oxazolyl group Chemical group 0.000 claims description 3
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
229940083542 sodium Drugs 0.000 claims description 3
235000015424 sodium Nutrition 0.000 claims description 3
KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 2
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
IAWLTFIXJAHEPB-UHFFFAOYSA-N 2-(2-benzoyl-4-chloro-1h-indol-3-yl)acetic acid Chemical compound N1C2=CC=CC(Cl)=C2C(CC(=O)O)=C1C(=O)C1=CC=CC=C1 IAWLTFIXJAHEPB-UHFFFAOYSA-N 0.000 claims description 2
UAPYAWJXCXJOOH-UHFFFAOYSA-N 2-(2-benzoyl-7-chloro-1h-indol-3-yl)acetic acid Chemical compound N1C2=C(Cl)C=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=CC=C1 UAPYAWJXCXJOOH-UHFFFAOYSA-N 0.000 claims description 2
MUNCFAXGBGQJGQ-UHFFFAOYSA-N 2-[2-(4-bromobenzoyl)-6-chloro-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=C(Br)C=C1 MUNCFAXGBGQJGQ-UHFFFAOYSA-N 0.000 claims description 2
RCUWSHCBWXTKAZ-UHFFFAOYSA-N 2-[2-(4-chlorobenzoyl)-5-ethyl-1h-indol-3-yl]acetic acid Chemical compound OC(=O)CC=1C2=CC(CC)=CC=C2NC=1C(=O)C1=CC=C(Cl)C=C1 RCUWSHCBWXTKAZ-UHFFFAOYSA-N 0.000 claims description 2
HMXAVUIJTFAESJ-UHFFFAOYSA-N 2-[5,6-dichloro-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CC1=CC=NC(C(=O)C2=C(C3=CC(Cl)=C(Cl)C=C3N2)CC(O)=O)=C1 HMXAVUIJTFAESJ-UHFFFAOYSA-N 0.000 claims description 2
FHPMEIVAUMQJDE-UHFFFAOYSA-N 2-[5-chloro-2-(4-methoxybenzoyl)-1h-indol-3-yl]acetic acid Chemical compound C1=CC(OC)=CC=C1C(=O)C1=C(CC(O)=O)C2=CC(Cl)=CC=C2N1 FHPMEIVAUMQJDE-UHFFFAOYSA-N 0.000 claims description 2
LIEWVLGYSUZMPB-UHFFFAOYSA-N 2-[5-chloro-2-(4-methoxypyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound COC1=CC=NC(C(=O)C2=C(C3=CC(Cl)=CC=C3N2)CC(O)=O)=C1 LIEWVLGYSUZMPB-UHFFFAOYSA-N 0.000 claims description 2
RQLXLOPZXVMJFH-UHFFFAOYSA-N 2-[5-chloro-2-(5-chloropyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)O)=C1C(=O)C1=CC=C(Cl)C=N1 RQLXLOPZXVMJFH-UHFFFAOYSA-N 0.000 claims description 2
FTJUWQKJMWEILQ-UHFFFAOYSA-N 2-[5-ethyl-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound OC(=O)CC=1C2=CC(CC)=CC=C2NC=1C(=O)C1=CC(C)=CC=N1 FTJUWQKJMWEILQ-UHFFFAOYSA-N 0.000 claims description 2
IBOLAADZZHVSAR-UHFFFAOYSA-N 2-[5-methoxy-2-(3-methylbenzoyl)-1h-indol-3-yl]acetic acid Chemical compound OC(=O)CC=1C2=CC(OC)=CC=C2NC=1C(=O)C1=CC=CC(C)=C1 IBOLAADZZHVSAR-UHFFFAOYSA-N 0.000 claims description 2
ZXIRTFSPGPHKHH-UHFFFAOYSA-N 2-[5-methyl-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CC1=CC=NC(C(=O)C2=C(C3=CC(C)=CC=C3N2)CC(O)=O)=C1 ZXIRTFSPGPHKHH-UHFFFAOYSA-N 0.000 claims description 2
XHHKFYKUQVEIBW-UHFFFAOYSA-N 2-[6-chloro-2-(2,4-dimethoxybenzoyl)-1h-indol-3-yl]acetic acid Chemical compound COC1=CC(OC)=CC=C1C(=O)C1=C(CC(O)=O)C2=CC=C(Cl)C=C2N1 XHHKFYKUQVEIBW-UHFFFAOYSA-N 0.000 claims description 2
XOKAZAIZAKWWKK-UHFFFAOYSA-N 2-[6-chloro-2-(3-ethoxy-4-ethylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CCOC1=C(CC)C=CN=C1C(=O)C1=C(CC(O)=O)C2=CC=C(Cl)C=C2N1 XOKAZAIZAKWWKK-UHFFFAOYSA-N 0.000 claims description 2
FKVFYNCOVBCCRI-UHFFFAOYSA-N 2-[6-chloro-2-(3-methylbenzoyl)-1h-indol-3-yl]acetic acid Chemical compound CC1=CC=CC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)CC(O)=O)=C1 FKVFYNCOVBCCRI-UHFFFAOYSA-N 0.000 claims description 2
LUGZWOKPMJPQCG-UHFFFAOYSA-N 2-[6-chloro-2-(4-chlorobenzoyl)-5-fluoro-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=C(F)C=C2C(CC(=O)O)=C1C(=O)C1=CC=C(Cl)C=C1 LUGZWOKPMJPQCG-UHFFFAOYSA-N 0.000 claims description 2
NFJIBUCJDVLYSZ-UHFFFAOYSA-N 2-[6-chloro-2-(4-methylbenzoyl)-1h-indol-3-yl]acetic acid Chemical compound C1=CC(C)=CC=C1C(=O)C1=C(CC(O)=O)C2=CC=C(Cl)C=C2N1 NFJIBUCJDVLYSZ-UHFFFAOYSA-N 0.000 claims description 2
CDQGPNGXWXAMTJ-UHFFFAOYSA-N 2-[6-chloro-2-[3-(trifluoromethyl)benzoyl]-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=CC(C(F)(F)F)=C1 CDQGPNGXWXAMTJ-UHFFFAOYSA-N 0.000 claims description 2
PUNPGZCYHPEVOI-UHFFFAOYSA-N 2-[6-ethyl-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(CC)=CC=C2C(CC(O)=O)=C1C(=O)C1=CC(C)=CC=N1 PUNPGZCYHPEVOI-UHFFFAOYSA-N 0.000 claims description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 claims description 2
235000019270 ammonium chloride Nutrition 0.000 claims description 2
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
125000004799 bromophenyl group Chemical group 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000001207 fluorophenyl group Chemical group 0.000 claims description 2
125000006379 fluoropyridyl group Chemical group 0.000 claims description 2
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 2
XMVXNDOSEHYPJT-UHFFFAOYSA-N methyl 2-[2-(3-bromobenzoyl)-6-chloro-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC=CC(Br)=C1 XMVXNDOSEHYPJT-UHFFFAOYSA-N 0.000 claims description 2
PSBBVSOANYYNTM-UHFFFAOYSA-N methyl 2-[2-(4-chlorobenzoyl)-6-methyl-1h-indol-3-yl]acetate Chemical compound N1C2=CC(C)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC=C(Cl)C=C1 PSBBVSOANYYNTM-UHFFFAOYSA-N 0.000 claims description 2
GRKFHJQVUZJDLR-UHFFFAOYSA-N methyl 2-[2-(4-methylpyridine-2-carbonyl)-5-(trifluoromethoxy)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(OC(F)(F)F)C=C2C(CC(=O)OC)=C1C(=O)C1=CC(C)=CC=N1 GRKFHJQVUZJDLR-UHFFFAOYSA-N 0.000 claims description 2
PGABVTXVZQPFNL-UHFFFAOYSA-N methyl 2-[2-(4-methylpyridine-2-carbonyl)-5-propan-2-yl-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(C(C)C)C=C2C(CC(=O)OC)=C1C(=O)C1=CC(C)=CC=N1 PGABVTXVZQPFNL-UHFFFAOYSA-N 0.000 claims description 2
KMWIDMYXNFISRM-UHFFFAOYSA-N methyl 2-[5-chloro-2-(2-methyl-1h-imidazole-5-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)OC)=C1C(=O)C1=CNC(C)=N1 KMWIDMYXNFISRM-UHFFFAOYSA-N 0.000 claims description 2
HYGYCIODLZLYOM-UHFFFAOYSA-N methyl 2-[5-chloro-2-(3-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)OC)=C1C(=O)C1=NC=CC=C1C HYGYCIODLZLYOM-UHFFFAOYSA-N 0.000 claims description 2
YTRQJHAGAZVQRS-UHFFFAOYSA-N methyl 2-[5-chloro-2-(4-methoxybenzoyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)OC)=C1C(=O)C1=CC=C(OC)C=C1 YTRQJHAGAZVQRS-UHFFFAOYSA-N 0.000 claims description 2
BLOBRKIQTLOWAD-UHFFFAOYSA-N methyl 2-[5-ethyl-2-(4-ethylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound CCC1=CC=NC(C(=O)C2=C(C3=CC(CC)=CC=C3N2)CC(=O)OC)=C1 BLOBRKIQTLOWAD-UHFFFAOYSA-N 0.000 claims description 2
PASSHDSAHRZPPN-UHFFFAOYSA-N methyl 2-[6-chloro-2-(1h-imidazole-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=NC=CN1 PASSHDSAHRZPPN-UHFFFAOYSA-N 0.000 claims description 2
YTQICMLHOTVTGX-UHFFFAOYSA-N methyl 2-[6-chloro-2-(2-methoxybenzoyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC=CC=C1OC YTQICMLHOTVTGX-UHFFFAOYSA-N 0.000 claims description 2
QUCDPBGVAQJKOG-UHFFFAOYSA-N methyl 2-[6-chloro-2-(3-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=NC=CC=C1C QUCDPBGVAQJKOG-UHFFFAOYSA-N 0.000 claims description 2
GGIBSHMJJCSEDQ-UHFFFAOYSA-N methyl 2-[6-chloro-2-(4-cyanobenzoyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC=C(C#N)C=C1 GGIBSHMJJCSEDQ-UHFFFAOYSA-N 0.000 claims description 2
OGFYTEFXHMAWGJ-UHFFFAOYSA-N methyl 2-[6-chloro-2-(4-phenylbenzoyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 OGFYTEFXHMAWGJ-UHFFFAOYSA-N 0.000 claims description 2
UXXFHVKVHYEFMY-UHFFFAOYSA-N methyl 2-[6-chloro-2-(5-methyl-1,2-oxazole-3-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C=1C=C(C)ON=1 UXXFHVKVHYEFMY-UHFFFAOYSA-N 0.000 claims description 2
YKEKTHVZPNVZGE-UHFFFAOYSA-N methyl 2-[6-chloro-2-(cyclopropanecarbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1CC1 YKEKTHVZPNVZGE-UHFFFAOYSA-N 0.000 claims description 2
UTYMXLBNRBBWHU-UHFFFAOYSA-N methyl 2-[6-chloro-2-[3-(furan-2-yl)benzoyl]-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C(C=1)=CC=CC=1C1=CC=CO1 UTYMXLBNRBBWHU-UHFFFAOYSA-N 0.000 claims description 2
UCERSLPTIOPWFC-UHFFFAOYSA-N methyl 2-[6-chloro-2-[4-(1-hydroxyethyl)pyridine-2-carbonyl]-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC(C(C)O)=CC=N1 UCERSLPTIOPWFC-UHFFFAOYSA-N 0.000 claims description 2
AFENDVZTGBZOCS-UHFFFAOYSA-N methyl 2-[6-chloro-2-[4-(furan-2-yl)benzoyl]-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C(C=C1)=CC=C1C1=CC=CO1 AFENDVZTGBZOCS-UHFFFAOYSA-N 0.000 claims description 2
KGAHBJLQKSMKDP-UHFFFAOYSA-N methyl 2-[6-chloro-2-[5-(trifluoromethyl)pyridine-2-carbonyl]-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC=C(C(F)(F)F)C=N1 KGAHBJLQKSMKDP-UHFFFAOYSA-N 0.000 claims description 2
WNRATXBHHICZFJ-UHFFFAOYSA-N methyl 2-[6-chloro-5-fluoro-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=C(F)C=C2C(CC(=O)OC)=C1C(=O)C1=CC(C)=CC=N1 WNRATXBHHICZFJ-UHFFFAOYSA-N 0.000 claims description 2
125000006384 methylpyridyl group Chemical group 0.000 claims description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
125000006387 trifluoromethyl pyridyl group Chemical group 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 29
NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims 14
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 9
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims 9
235000003270 potassium fluoride Nutrition 0.000 claims 7
239000011698 potassium fluoride Substances 0.000 claims 7
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical group CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 4
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 4
239000012312 sodium hydride Substances 0.000 claims 4
229910000104 sodium hydride Inorganic materials 0.000 claims 4
NIVOIXNJFYAHEY-UHFFFAOYSA-N 2-[6-chloro-2-(4-propylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CCCC1=CC=NC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)CC(O)=O)=C1 NIVOIXNJFYAHEY-UHFFFAOYSA-N 0.000 claims 3
229910000024 caesium carbonate Inorganic materials 0.000 claims 3
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims 3
229940043279 diisopropylamine Drugs 0.000 claims 3
ULWOJODHECIZAU-UHFFFAOYSA-N n,n-diethylpropan-2-amine Chemical compound CCN(CC)C(C)C ULWOJODHECIZAU-UHFFFAOYSA-N 0.000 claims 3
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims 3
229910000105 potassium hydride Inorganic materials 0.000 claims 3
ZMUGLKQRLOVWJZ-UHFFFAOYSA-N 2-[2-(4-methylpyridine-2-carbonyl)-5-methylsulfanyl-1h-indol-3-yl]acetic acid Chemical compound OC(=O)CC=1C2=CC(SC)=CC=C2NC=1C(=O)C1=CC(C)=CC=N1 ZMUGLKQRLOVWJZ-UHFFFAOYSA-N 0.000 claims 2
GTTDZFUQPRBOIU-UHFFFAOYSA-N 2-[5-chloro-2-(3-methylbenzoyl)-1h-indol-3-yl]acetic acid Chemical compound CC1=CC=CC(C(=O)C2=C(C3=CC(Cl)=CC=C3N2)CC(O)=O)=C1 GTTDZFUQPRBOIU-UHFFFAOYSA-N 0.000 claims 2
ICZQBYYTECBHFE-UHFFFAOYSA-N 2-[5-chloro-2-(4,6-dimethylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CC1=CC(C)=NC(C(=O)C2=C(C3=CC(Cl)=CC=C3N2)CC(O)=O)=C1 ICZQBYYTECBHFE-UHFFFAOYSA-N 0.000 claims 2
SVWRECMQWQPKMV-UHFFFAOYSA-N 2-[5-chloro-2-(4-chloropyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)O)=C1C(=O)C1=CC(Cl)=CC=N1 SVWRECMQWQPKMV-UHFFFAOYSA-N 0.000 claims 2
CTPVZFGXLCCGCB-UHFFFAOYSA-N 2-[6-chloro-2-(2-nitrobenzoyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=CC=C1[N+]([O-])=O CTPVZFGXLCCGCB-UHFFFAOYSA-N 0.000 claims 2
YVHSHSNTRIAXKH-UHFFFAOYSA-N 2-[6-chloro-2-(5-methyl-1,2-oxazole-3-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound O1C(C)=CC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)CC(O)=O)=N1 YVHSHSNTRIAXKH-UHFFFAOYSA-N 0.000 claims 2
CDPAPELXWJAQSY-UHFFFAOYSA-N 2-[6-chloro-2-(6-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CC1=CC=CC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)CC(O)=O)=N1 CDPAPELXWJAQSY-UHFFFAOYSA-N 0.000 claims 2
SPBSENZPLJNKIP-UHFFFAOYSA-N 2-[6-chloro-2-(thiophene-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=CS1 SPBSENZPLJNKIP-UHFFFAOYSA-N 0.000 claims 2
YCABRYINYKIBLF-UHFFFAOYSA-N 2-[6-chloro-2-[4-(furan-2-yl)benzoyl]-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C(C=C1)=CC=C1C1=CC=CO1 YCABRYINYKIBLF-UHFFFAOYSA-N 0.000 claims 2
JIMWOCFAILHVTK-UHFFFAOYSA-N 2-[6-chloro-2-[4-(methanesulfonamido)benzoyl]-1h-indol-3-yl]acetic acid Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1C(=O)C1=C(CC(O)=O)C2=CC=C(Cl)C=C2N1 JIMWOCFAILHVTK-UHFFFAOYSA-N 0.000 claims 2
125000002672 4-bromobenzoyl group Chemical group BrC1=CC=C(C(=O)*)C=C1 0.000 claims 2
241000080590 Niso Species 0.000 claims 2
UEZFVZGSGFGLIF-UHFFFAOYSA-N methyl 2-[6-chloro-2-(3-chloro-4-ethylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound CCC1=CC=NC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)CC(=O)OC)=C1Cl UEZFVZGSGFGLIF-UHFFFAOYSA-N 0.000 claims 2
IRBMLUJBILFHQT-UHFFFAOYSA-N methyl 2-[6-chloro-2-[3-(methoxymethyl)furan-2-carbonyl]-1h-indol-3-yl]acetate Chemical compound C1=COC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)CC(=O)OC)=C1COC IRBMLUJBILFHQT-UHFFFAOYSA-N 0.000 claims 2
LIUFUQWEKBCFTN-UHFFFAOYSA-N methyl 2-[6-chloro-2-[4-(trifluoromethoxy)benzoyl]-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC=C(OC(F)(F)F)C=C1 LIUFUQWEKBCFTN-UHFFFAOYSA-N 0.000 claims 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims 2
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims 2
DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 1
QVCUKHQDEZNNOC-UHFFFAOYSA-N 1,2-diazabicyclo[2.2.2]octane Chemical compound C1CC2CCN1NC2 QVCUKHQDEZNNOC-UHFFFAOYSA-N 0.000 claims 1
GJLNHTUJBBNDLC-UHFFFAOYSA-N 2-(2-benzoyl-1h-indol-3-yl)acetic acid Chemical compound N1C2=CC=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=CC=C1 GJLNHTUJBBNDLC-UHFFFAOYSA-N 0.000 claims 1
IJKQRSQWFATMPA-UHFFFAOYSA-N 2-(2-benzoyl-6-chloro-1h-indol-3-yl)-1-morpholin-4-ylethanone Chemical compound C=1C=CC=CC=1C(=O)C=1NC2=CC(Cl)=CC=C2C=1CC(=O)N1CCOCC1 IJKQRSQWFATMPA-UHFFFAOYSA-N 0.000 claims 1
REPIIDDWHHDMRS-UHFFFAOYSA-N 2-[2-(4-chlorobenzoyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=C(Cl)C=C1 REPIIDDWHHDMRS-UHFFFAOYSA-N 0.000 claims 1
IVAUGGRLHAAOFW-UHFFFAOYSA-N 2-[5-chloro-2-(3-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CC1=CC=CN=C1C(=O)C1=C(CC(O)=O)C2=CC(Cl)=CC=C2N1 IVAUGGRLHAAOFW-UHFFFAOYSA-N 0.000 claims 1
UTFYAEXHTQANTC-UHFFFAOYSA-N 2-[6-chloro-2-(2-methylbenzoyl)-1h-indol-3-yl]acetic acid Chemical compound CC1=CC=CC=C1C(=O)C1=C(CC(O)=O)C2=CC=C(Cl)C=C2N1 UTFYAEXHTQANTC-UHFFFAOYSA-N 0.000 claims 1
UOCATRDNSWBSKC-UHFFFAOYSA-N 2-[6-chloro-2-(3,5-dimethylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CC1=CC(C)=CN=C1C(=O)C1=C(CC(O)=O)C2=CC=C(Cl)C=C2N1 UOCATRDNSWBSKC-UHFFFAOYSA-N 0.000 claims 1
KLMKJYYUYYUXHX-UHFFFAOYSA-N 2-[6-chloro-2-(3-hydroxybenzoyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=CC(O)=C1 KLMKJYYUYYUXHX-UHFFFAOYSA-N 0.000 claims 1
LIZBZHRWLFNNNY-UHFFFAOYSA-N 2-[6-chloro-2-(4,6-dimethylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CC1=CC(C)=NC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)CC(O)=O)=C1 LIZBZHRWLFNNNY-UHFFFAOYSA-N 0.000 claims 1
BFDZSIVADHPBDX-UHFFFAOYSA-N 2-[6-chloro-2-(4-pyridin-3-ylbenzoyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C(C=C1)=CC=C1C1=CC=CN=C1 BFDZSIVADHPBDX-UHFFFAOYSA-N 0.000 claims 1
ZNNURDZEITVFDY-UHFFFAOYSA-N 2-[6-chloro-2-(5-methyl-1,3-thiazole-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound S1C(C)=CN=C1C(=O)C1=C(CC(O)=O)C2=CC=C(Cl)C=C2N1 ZNNURDZEITVFDY-UHFFFAOYSA-N 0.000 claims 1
OIBLRFJTXXDCRU-UHFFFAOYSA-N 2-[6-chloro-2-(cyclopropanecarbonyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1CC1 OIBLRFJTXXDCRU-UHFFFAOYSA-N 0.000 claims 1
ONMIXEWCFUIZSY-UHFFFAOYSA-N 2-[6-chloro-2-(isoquinoline-3-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound C1=CC=C2C=NC(C(=O)C3=C(C4=CC=C(Cl)C=C4N3)CC(=O)O)=CC2=C1 ONMIXEWCFUIZSY-UHFFFAOYSA-N 0.000 claims 1
KYZGWLSHNXSPGV-UHFFFAOYSA-N 5-[3-(carboxymethyl)-5-chloro-1h-indole-2-carbonyl]-1,2-oxazole-3-carboxylic acid Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)O)=C1C(=O)C1=CC(C(O)=O)=NO1 KYZGWLSHNXSPGV-UHFFFAOYSA-N 0.000 claims 1
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims 1
IEMGWBMVQLVHEY-UHFFFAOYSA-N ethyl 2-(3-amino-6,7-dihydro-5h-cyclopenta[b]pyridin-7-yl)acetate Chemical compound NC1=CN=C2C(CC(=O)OCC)CCC2=C1 IEMGWBMVQLVHEY-UHFFFAOYSA-N 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 claims 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 1
LBVAKCYJWFZJLZ-UHFFFAOYSA-N methyl 2-[2-(4-chlorobenzoyl)-5-methoxy-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(OC)C=C2C(CC(=O)OC)=C1C(=O)C1=CC=C(Cl)C=C1 LBVAKCYJWFZJLZ-UHFFFAOYSA-N 0.000 claims 1
DAUFJSPPNBFXBV-UHFFFAOYSA-N methyl 2-[5-chloro-2-[4-(hydroxymethyl)pyridine-2-carbonyl]-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)OC)=C1C(=O)C1=CC(CO)=CC=N1 DAUFJSPPNBFXBV-UHFFFAOYSA-N 0.000 claims 1
SFRDUMXERLDSKX-UHFFFAOYSA-N methyl 2-[5-methoxy-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(OC)C=C2C(CC(=O)OC)=C1C(=O)C1=CC(C)=CC=N1 SFRDUMXERLDSKX-UHFFFAOYSA-N 0.000 claims 1
QAAUJTGQKZHHCI-UHFFFAOYSA-N methyl 2-[5-methyl-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(C)C=C2C(CC(=O)OC)=C1C(=O)C1=CC(C)=CC=N1 QAAUJTGQKZHHCI-UHFFFAOYSA-N 0.000 claims 1
BHTDMHWIOFGFNV-UHFFFAOYSA-N methyl 2-[6-chloro-2-(1-methylimidazole-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=NC=CN1C BHTDMHWIOFGFNV-UHFFFAOYSA-N 0.000 claims 1
XCUYTRJAUQQHLA-UHFFFAOYSA-N methyl 2-[6-chloro-2-(4,6-dimethylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC(C)=CC(C)=N1 XCUYTRJAUQQHLA-UHFFFAOYSA-N 0.000 claims 1
OEBIMKLPEBMLTA-UHFFFAOYSA-N methyl 2-[6-chloro-2-(4-ethyl-3-fluoropyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound CCC1=CC=NC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)CC(=O)OC)=C1F OEBIMKLPEBMLTA-UHFFFAOYSA-N 0.000 claims 1
NBZLKORWWGJUCW-UHFFFAOYSA-N methyl 2-[6-chloro-2-(4-nitrobenzoyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC=C([N+]([O-])=O)C=C1 NBZLKORWWGJUCW-UHFFFAOYSA-N 0.000 claims 1
PKWKTFRNRKQFMV-UHFFFAOYSA-N methyl 2-[6-chloro-2-(4-propan-2-yloxybenzoyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC=C(OC(C)C)C=C1 PKWKTFRNRKQFMV-UHFFFAOYSA-N 0.000 claims 1
GHWDSYRPKXPDOE-UHFFFAOYSA-N methyl 2-[6-chloro-2-(4-propylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound CCCC1=CC=NC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)CC(=O)OC)=C1 GHWDSYRPKXPDOE-UHFFFAOYSA-N 0.000 claims 1
XIFUHFKNCPWNAB-UHFFFAOYSA-N methyl 2-[6-chloro-2-(4-pyridin-3-ylbenzoyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C(C=C1)=CC=C1C1=CC=CN=C1 XIFUHFKNCPWNAB-UHFFFAOYSA-N 0.000 claims 1
KWKITUBBQQAKPI-UHFFFAOYSA-N methyl 2-[6-ethyl-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(CC)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC(C)=CC=N1 KWKITUBBQQAKPI-UHFFFAOYSA-N 0.000 claims 1
GJRYPVYGCLRKOO-UHFFFAOYSA-N methyl 2-[6-methyl-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(C)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC(C)=CC=N1 GJRYPVYGCLRKOO-UHFFFAOYSA-N 0.000 claims 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- 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
- 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
- C07D403/06—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 carbon chain containing only aliphatic carbon atoms
- 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
- C07D405/06—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 carbon chain containing only aliphatic carbon atoms
- 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
- C07D405/10—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 carbon chain containing aromatic rings
- 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
- C07D409/06—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 carbon chain containing only aliphatic carbon atoms
- 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
- C07D409/10—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 carbon chain containing aromatic rings
- 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
- C07D413/06—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 carbon chain containing only aliphatic carbon atoms
- 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
- C07D417/06—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 carbon chain containing only aliphatic carbon atoms
- 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
- C07D417/10—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 carbon chain containing aromatic rings

Landscapes

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

OA1200000195A 1998-01-05 2000-06-30 2,3-Substituted indole compounds as COX-2inhibitors. OA11441A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IB9800003		1998-01-05

Publications (1)

Publication Number	Publication Date
OA11441A true OA11441A (en)	2004-04-27

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ID=11004645

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Application Number	Title	Priority Date	Filing Date
OA1200000195A OA11441A (en)	1998-01-05	2000-06-30	2,3-Substituted indole compounds as COX-2inhibitors.

Country Status (39)

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US (1)	US6608070B1 (fr)
EP (1)	EP1045833B1 (fr)
JP (1)	JP3347136B2 (fr)
KR (1)	KR100404054B1 (fr)
CN (1)	CN1284064A (fr)
AP (1)	AP869A (fr)
AR (1)	AR016977A1 (fr)
AT (1)	ATE308519T1 (fr)
AU (1)	AU748107B2 (fr)
BG (1)	BG104643A (fr)
BR (1)	BR9813124A (fr)
CA (1)	CA2316863A1 (fr)
CO (1)	CO4970807A1 (fr)
DE (1)	DE69832200T2 (fr)
DZ (1)	DZ2700A1 (fr)
EA (1)	EA200000614A1 (fr)
ES (1)	ES2255190T3 (fr)
GT (1)	GT199800205A (fr)
HN (1)	HN1997000098A (fr)
HR (1)	HRP20000454A2 (fr)
HU (1)	HUP0102922A3 (fr)
ID (1)	ID24876A (fr)
IL (1)	IL136885A0 (fr)
IS (1)	IS5532A (fr)
MA (1)	MA24736A1 (fr)
NO (1)	NO20003451L (fr)
OA (1)	OA11441A (fr)
PA (1)	PA8466201A1 (fr)
PE (1)	PE20000055A1 (fr)
PL (1)	PL341696A1 (fr)
SA (1)	SA99191299A (fr)
SK (1)	SK9912000A3 (fr)
TN (1)	TNSN99001A1 (fr)
TR (1)	TR200001906T2 (fr)
TW (1)	TW436482B (fr)
UY (2)	UY25332A1 (fr)
WO (1)	WO1999035130A1 (fr)
YU (1)	YU41600A (fr)
ZA (1)	ZA9911B (fr)

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US6555540B1 (en) *	1999-06-30	2003-04-29	Pfizer Inc	Combinations of aldose reductase inhibitors and selective cyclooxygenase-2 inhibitors
MXPA00006605A (es) *	1999-07-02	2004-12-09	Pfizer	Compuestos de carbonil-indol biciclicos como agentes antiinflamatorios/analgesicos.
ATE225785T1 (de) *	1999-07-02	2002-10-15	Pfizer	Tetrazolylalkyl-indolderivate als entzündungshemmende und analgetische mittel
CO5261556A1 (es)	1999-12-08	2003-03-31	Pharmacia Corp	Composiciones inhibidoras de ciclooxigenasa-2 que tiene rapido acceso de efecto terapeutico
AU2003299757A1 (en) *	2002-12-19	2004-07-14	Elan Pharmaceuticals Inc.	Substituted n-phenyl sulfonamide bradykinin antagonists
US7098231B2 (en)	2003-01-22	2006-08-29	Boehringer Ingelheim International Gmbh	Viral polymerase inhibitors
US7223785B2 (en)	2003-01-22	2007-05-29	Boehringer Ingelheim International Gmbh	Viral polymerase inhibitors
ATE342722T1 (de)	2003-05-07	2006-11-15	Osteologix As	Behandlung von knorpel/knochen-erkrankungen mit wasserlöslichen strontiumsalzen
KR100795462B1 (ko)	2006-09-27	2008-01-16	한국생명공학연구원	인돌 유도체, 이의 제조방법 및 이를 유효성분으로함유하는 대사성 질환 예방 및 치료용 약학적 조성물
EP2114895A4 (fr)	2006-10-17	2011-06-22	Stiefel Laboratories	Métabolites de talarazole
US20120022121A1 (en) *	2007-11-29	2012-01-26	Dalton James T	Indoles, derivatives and analogs thereof and uses therefor
WO2011133442A1 (fr) *	2010-04-19	2011-10-27	Metabolic Solutions Development Company	Nouvelle synthèse de thiazolidinediones
JP5827326B2 (ja)	2010-07-07	2015-12-02	アーデリクス，インコーポレーテッド	リン酸輸送を阻害する化合物及び方法
EP2590656B1 (fr)	2010-07-07	2017-11-15	Ardelyx, Inc.	Composés et procédés permettant d'inhiber le transport du phosphate
EP2590965B1 (fr)	2010-07-07	2016-04-20	Ardelyx, Inc.	Composés et procédés pour l'inhibition du transport de phosphate
JP5827328B2 (ja)	2010-07-07	2015-12-02	アーデリクス，インコーポレーテッド	リン酸輸送を阻害する化合物及び方法
RU2594725C2 (ru)	2010-08-10	2016-08-20	МЕТАБОЛИК СОЛЮШНЗ ДЕВЕЛОПМЕНТ КОМПАНИ, ЭлЭлСи	Синтез соединений тиазолидиндиона
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1998
- 1998-12-17 AP APAP/P/1998/001423A patent/AP869A/en active
- 1998-12-18 CN CN98813530A patent/CN1284064A/zh active Pending
- 1998-12-18 US US09/355,494 patent/US6608070B1/en not_active Expired - Fee Related
- 1998-12-18 EA EA200000614A patent/EA200000614A1/ru unknown
- 1998-12-18 ES ES98959082T patent/ES2255190T3/es not_active Expired - Lifetime
- 1998-12-18 WO PCT/IB1998/002065 patent/WO1999035130A1/fr not_active Ceased
- 1998-12-18 KR KR10-2000-7007419A patent/KR100404054B1/ko not_active Expired - Fee Related
- 1998-12-18 ID IDW20001286A patent/ID24876A/id unknown
- 1998-12-18 AT AT98959082T patent/ATE308519T1/de not_active IP Right Cessation
- 1998-12-18 JP JP2000527531A patent/JP3347136B2/ja not_active Expired - Fee Related
- 1998-12-18 SK SK991-2000A patent/SK9912000A3/sk unknown
- 1998-12-18 HR HR20000454A patent/HRP20000454A2/hr not_active Application Discontinuation
- 1998-12-18 AU AU15005/99A patent/AU748107B2/en not_active Ceased
- 1998-12-18 TR TR2000/01906T patent/TR200001906T2/xx unknown
- 1998-12-18 YU YU41600A patent/YU41600A/sh unknown
- 1998-12-18 BR BR9813124-9A patent/BR9813124A/pt not_active IP Right Cessation
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- 1998-12-18 PL PL98341696A patent/PL341696A1/xx unknown
- 1998-12-18 CA CA002316863A patent/CA2316863A1/fr not_active Abandoned
- 1998-12-18 EP EP98959082A patent/EP1045833B1/fr not_active Expired - Lifetime
- 1998-12-18 HU HU0102922A patent/HUP0102922A3/hu unknown
- 1998-12-18 DE DE69832200T patent/DE69832200T2/de not_active Expired - Fee Related
- 1998-12-22 TW TW087120865A patent/TW436482B/zh active
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- 1998-12-28 PE PE1998001288A patent/PE20000055A1/es not_active Application Discontinuation
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- 1998-12-31 UY UY25332A patent/UY25332A1/es not_active IP Right Cessation
1999
- 1999-01-04 TN TNTNSN99001A patent/TNSN99001A1/fr unknown
- 1999-01-04 DZ DZ990001A patent/DZ2700A1/fr active
- 1999-01-04 AR ARP990100010A patent/AR016977A1/es not_active Application Discontinuation
- 1999-01-04 MA MA25414A patent/MA24736A1/fr unknown
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- 1999-01-05 PA PA19998466201A patent/PA8466201A1/es unknown
- 1999-04-13 SA SA99191299A patent/SA99191299A/ar unknown
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2000
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Also Published As

Publication number	Publication date
TNSN99001A1 (fr)	2005-11-10
HUP0102922A2 (hu)	2001-12-28
TW436482B (en)	2001-05-28
GT199800205A (es)	2000-06-21
IL136885A0 (en)	2001-06-14
DE69832200D1 (de)	2005-12-08
IS5532A (is)	2000-06-13
BG104643A (bg)	2001-02-28
SA99191299A (ar)	2005-12-03
BR9813124A (pt)	2000-10-10
AP869A (en)	2000-09-04
CO4970807A1 (es)	2000-11-07
WO1999035130A1 (fr)	1999-07-15
MA24736A1 (fr)	1999-10-01
PE20000055A1 (es)	2000-02-08
KR100404054B1 (ko)	2003-11-01
JP3347136B2 (ja)	2002-11-20
EA200000614A1 (ru)	2001-02-26
HUP0102922A3 (en)	2003-06-30
NO20003451D0 (no)	2000-07-04
ES2255190T3 (es)	2006-06-16
YU41600A (sh)	2003-08-29
ZA9911B (en)	2000-07-04
PL341696A1 (en)	2001-04-23
HN1997000098A (es)	1998-12-28
DE69832200T2 (de)	2006-04-20
JP2002500217A (ja)	2002-01-08
CA2316863A1 (fr)	1999-07-15
TR200001906T2 (tr)	2001-01-22
KR20010033859A (ko)	2001-04-25
AU748107B2 (en)	2002-05-30
SK9912000A3 (en)	2001-11-06
HRP20000454A2 (en)	2001-04-30
DZ2700A1 (fr)	2003-09-01
ID24876A (id)	2000-08-31
US6608070B1 (en)	2003-08-19
NO20003451L (no)	2000-09-01
UY25332A1 (es)	2001-01-31
EP1045833B1 (fr)	2005-11-02
CN1284064A (zh)	2001-02-14
AR016977A1 (es)	2001-08-01
PA8466201A1 (es)	2000-09-29
ATE308519T1 (de)	2005-11-15
UY25590A1 (es)	1999-09-27
AU1500599A (en)	1999-07-26
AP9801423A0 (en)	1998-12-31
EP1045833A1 (fr)	2000-10-25

Publication	Publication Date	Title
AU748107B2 (en)	2002-05-30	2,3-substituted indole compounds as COX-2 inhibitors
JP3333179B2 (ja)	2002-10-07	抗炎症／鎮痛薬としての二環式カルボニルインドール化合物
EP1104760B1 (fr)	2003-03-12	Composés de sulfamoylhétéroaryl-pyrazole comme analgésiques et agents anti-inflammatoires
EP0985666B1 (fr)	2003-11-05	Composés indoliques substitués en tant qu'inhibiteurs de COX-2
MXPA00011845A (es)	2002-08-20	Compuestos de heteroarilfenilpirazol como agentes antiinflamatorios/analgesicos.
EP1086097B1 (fr)	2004-05-19	Composes sulfonylbenzene utilises en tant qu'agents analgesiques/anti-inflammatoires
US6608095B2 (en)	2003-08-19	Sulfonylbenzene compounds as anti-inflammatory/analgesic agents
CZ20002455A3 (cs)	2001-03-14	2,3-Substituované indoly, farmaceutické kompozice na jejich bázi, způsob léčení a způsoby výroby
CA2313106C (fr)	2004-07-13	(alkyltetrazolyl)indoles comme agents anti-inflammatoires et analgesiques
US6727238B2 (en)	2004-04-27	Sulfonylbenzene compounds as anti-inflammatory/analgesic agents
HK1033670A (en)	2001-09-14	2,3-substituted indole compounds as cox-2 inhibitors