AP869A - 2,3-Substituted indole compounds as anti-inflammatory and analgesic agents. - Google Patents
2,3-Substituted indole compounds as anti-inflammatory and analgesic agents. Download PDFInfo
- Publication number
- AP869A AP869A APAP/P/1998/001423A AP9801423A AP869A AP 869 A AP869 A AP 869A AP 9801423 A AP9801423 A AP 9801423A AP 869 A AP869 A AP 869A
- Authority
- AP
- ARIPO
- Prior art keywords
- indol
- chloro
- acetic acid
- carbonyl
- alkyl
- Prior art date
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- 150000002475 indoles Chemical class 0.000 title description 6
- 230000003110 anti-inflammatory effect Effects 0.000 title description 4
- 239000002260 anti-inflammatory agent Substances 0.000 title description 3
- 239000000730 antalgic agent Substances 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 150
- 125000003545 alkoxy group Chemical group 0.000 abstract description 83
- 125000005843 halogen group Chemical group 0.000 abstract description 46
- 125000004414 alkyl thio group Chemical group 0.000 abstract description 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 31
- 150000001875 compounds Chemical class 0.000 abstract description 24
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 22
- 125000003118 aryl group Chemical group 0.000 abstract description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 18
- 125000005842 heteroatom Chemical group 0.000 abstract description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 14
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 10
- 150000003180 prostaglandins Chemical class 0.000 abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 9
- 239000001257 hydrogen Substances 0.000 abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 abstract description 9
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 8
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 6
- 150000003839 salts Chemical class 0.000 abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 121
- -1 N-substituted indole compounds Chemical class 0.000 description 97
- 125000001424 substituent group Chemical group 0.000 description 57
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 40
- 125000003282 alkyl amino group Chemical group 0.000 description 30
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 11
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 11
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 8
- 206010061218 Inflammation Diseases 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 125000002541 furyl group Chemical group 0.000 description 7
- 230000004054 inflammatory process Effects 0.000 description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- 125000004076 pyridyl group Chemical group 0.000 description 7
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 6
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 6
- 125000005956 isoquinolyl group Chemical group 0.000 description 6
- 125000000168 pyrrolyl group Chemical group 0.000 description 6
- 125000001544 thienyl group Chemical group 0.000 description 6
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 5
- 208000002193 Pain Diseases 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 125000002883 imidazolyl group Chemical group 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 125000000842 isoxazolyl group Chemical group 0.000 description 5
- 230000036407 pain Effects 0.000 description 5
- 125000000335 thiazolyl group Chemical group 0.000 description 5
- 102000001708 Protein Isoforms Human genes 0.000 description 4
- 108010029485 Protein Isoforms Proteins 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 201000008482 osteoarthritis Diseases 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- 125000005493 quinolyl group Chemical group 0.000 description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 3
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 3
- 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 description 3
- 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 description 3
- 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 description 3
- 206010037660 Pyrexia Diseases 0.000 description 3
- 206010003246 arthritis Diseases 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 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 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000002971 oxazolyl group Chemical group 0.000 description 3
- 244000052769 pathogen Species 0.000 description 3
- 125000003373 pyrazinyl group Chemical group 0.000 description 3
- 125000003226 pyrazolyl group Chemical group 0.000 description 3
- 125000002098 pyridazinyl group Chemical group 0.000 description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000003831 tetrazolyl group Chemical group 0.000 description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 description 3
- 125000001425 triazolyl group Chemical group 0.000 description 3
- 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 description 2
- 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 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 description 2
- 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 description 2
- 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 description 2
- 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 description 2
- 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 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 description 2
- 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 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 description 2
- SDAHUFUEJMCQRJ-UHFFFAOYSA-N 2-[5-chloro-2-(1,3-thiazole-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)O)=C1C(=O)C1=NC=CS1 SDAHUFUEJMCQRJ-UHFFFAOYSA-N 0.000 description 2
- MEAGKTRNERIYOR-UHFFFAOYSA-N 2-[5-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(Cl)=CC=C3N2)CC(O)=O)=C1Cl MEAGKTRNERIYOR-UHFFFAOYSA-N 0.000 description 2
- 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 description 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 description 2
- 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 description 2
- 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 description 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 description 2
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- 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 description 2
- 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 description 2
- 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 description 2
- CEXUHYCXEAOFGH-UHFFFAOYSA-N 2-[5-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(Cl)=CC=C3N2)CC(O)=O)=C1 CEXUHYCXEAOFGH-UHFFFAOYSA-N 0.000 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 description 2
- 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 description 2
- JBMBFPSWAHDWJN-UHFFFAOYSA-N 2-[5-chloro-2-[5-(trifluoromethyl)pyridine-2-carbonyl]-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)O)=C1C(=O)C1=CC=C(C(F)(F)F)C=N1 JBMBFPSWAHDWJN-UHFFFAOYSA-N 0.000 description 2
- DNIKRHXQZCTYOD-UHFFFAOYSA-N 2-[5-fluoro-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CC1=CC=NC(C(=O)C2=C(C3=CC(F)=CC=C3N2)CC(O)=O)=C1 DNIKRHXQZCTYOD-UHFFFAOYSA-N 0.000 description 2
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- 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 description 1
- 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 description 1
- NTBSAKHUYFTAQR-UHFFFAOYSA-N methyl 2-[2-(4-methylpyridine-2-carbonyl)-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)=CC=N1 NTBSAKHUYFTAQR-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- RGNIFRLJJHPDDX-UHFFFAOYSA-N methyl 2-[2-(4-methylpyridine-2-carbonyl)-6-(trifluoromethyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(C(F)(F)F)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC(C)=CC=N1 RGNIFRLJJHPDDX-UHFFFAOYSA-N 0.000 description 1
- ZTBBQMAVBBNDSU-UHFFFAOYSA-N methyl 2-[5,6-dichloro-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=C(Cl)C=C2C(CC(=O)OC)=C1C(=O)C1=CC(C)=CC=N1 ZTBBQMAVBBNDSU-UHFFFAOYSA-N 0.000 description 1
- JGOTXUXKJGOIQO-UHFFFAOYSA-N methyl 2-[5-chloro-2-(1,3-thiazole-5-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)OC)=C1C(=O)C1=CN=CS1 JGOTXUXKJGOIQO-UHFFFAOYSA-N 0.000 description 1
- UJIDTXABWKUPHM-UHFFFAOYSA-N methyl 2-[5-chloro-2-(1-methylpyrrole-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)OC)=C1C(=O)C1=CC=CN1C UJIDTXABWKUPHM-UHFFFAOYSA-N 0.000 description 1
- KONVFODCBRCJDU-UHFFFAOYSA-N methyl 2-[5-chloro-2-(1h-imidazole-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)OC)=C1C(=O)C1=NC=CN1 KONVFODCBRCJDU-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- HYYXMFSXWPERMY-UHFFFAOYSA-N methyl 2-[5-chloro-2-(3,4-dimethylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)OC)=C1C(=O)C1=NC=CC(C)=C1C HYYXMFSXWPERMY-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- SRIAHUPVRCEVHA-UHFFFAOYSA-N methyl 2-[5-chloro-2-(4-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)=CS1 SRIAHUPVRCEVHA-UHFFFAOYSA-N 0.000 description 1
- KDRYJJNBCUIKEJ-UHFFFAOYSA-N methyl 2-[5-chloro-2-(4-propan-2-ylpyridine-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)=CC=N1 KDRYJJNBCUIKEJ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- DXAVSTNJPVXKGJ-UHFFFAOYSA-N methyl 2-[5-chloro-2-(5-methyl-1,2-oxazole-3-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)OC)=C1C(=O)C=1C=C(C)ON=1 DXAVSTNJPVXKGJ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 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 description 1
- 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 description 1
- AHTDRLMOMCKOCQ-UHFFFAOYSA-N methyl 2-[5-chloro-2-[5-(trifluoromethyl)pyridine-2-carbonyl]-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)OC)=C1C(=O)C1=CC=C(C(F)(F)F)C=N1 AHTDRLMOMCKOCQ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- XJAPEIPSNZBWIZ-UHFFFAOYSA-N methyl 2-[5-fluoro-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(F)C=C2C(CC(=O)OC)=C1C(=O)C1=CC(C)=CC=N1 XJAPEIPSNZBWIZ-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
- 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 description 1
- 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 description 1
- YXOIYKJDXNVGMT-UHFFFAOYSA-N methyl 2-[6-chloro-2-(3,5-dimethylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=NC=C(C)C=C1C YXOIYKJDXNVGMT-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- USOVMTGSFDDXEK-UHFFFAOYSA-N methyl 2-[6-chloro-2-(3-hydroxybenzoyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC=CC(O)=C1 USOVMTGSFDDXEK-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- ILACFUSSEFWIQE-UHFFFAOYSA-N methyl 2-[6-chloro-2-(3-phenylmethoxybenzoyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C(C=1)=CC=CC=1OCC1=CC=CC=C1 ILACFUSSEFWIQE-UHFFFAOYSA-N 0.000 description 1
- JWNDXMDGOOWQBA-UHFFFAOYSA-N methyl 2-[6-chloro-2-(4,5-dimethylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC(C)=C(C)C=N1 JWNDXMDGOOWQBA-UHFFFAOYSA-N 0.000 description 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 description 1
- 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 description 1
- 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 description 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 description 1
- QVMSZGMBZYHKPZ-UHFFFAOYSA-N methyl 2-[6-chloro-2-(4-hydroxybenzoyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC=C(O)C=C1 QVMSZGMBZYHKPZ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 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 description 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 description 1
- HHVBWFNLRLXCNX-UHFFFAOYSA-N methyl 2-[6-chloro-2-(4-propan-2-ylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC(C(C)C)=CC=N1 HHVBWFNLRLXCNX-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- DCDHPFYJYZRESQ-UHFFFAOYSA-N methyl 2-[6-chloro-2-(pyridine-4-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC=NC=C1 DCDHPFYJYZRESQ-UHFFFAOYSA-N 0.000 description 1
- MJLJRGFWKBKDTF-UHFFFAOYSA-N methyl 2-[6-chloro-2-[3-(2-hydroxypropan-2-yl)furan-2-carbonyl]-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C=1OC=CC=1C(C)(C)O MJLJRGFWKBKDTF-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- SAIQWUFFXIPRSR-UHFFFAOYSA-N methyl 2-[6-chloro-2-[4-(1,3-thiazol-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=NC=CS1 SAIQWUFFXIPRSR-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- BFDQUFKESFGKKK-UHFFFAOYSA-N methyl 2-[6-chloro-2-[4-(methanesulfonamido)benzoyl]-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC=C(NS(C)(=O)=O)C=C1 BFDQUFKESFGKKK-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- WFUDNLGVIXCXQY-UHFFFAOYSA-N n-(2-aminoethyl)-2-[5-chloro-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetamide Chemical compound CC1=CC=NC(C(=O)C2=C(C3=CC(Cl)=CC=C3N2)CC(=O)NCCN)=C1 WFUDNLGVIXCXQY-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 201000009240 nasopharyngitis Diseases 0.000 description 1
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- 208000004296 neuralgia Diseases 0.000 description 1
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- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
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- 208000026440 premature labor Diseases 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 201000007183 prothrombin deficiency Diseases 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 230000016160 smooth muscle contraction Effects 0.000 description 1
- 239000011734 sodium Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 201000004595 synovitis Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000006387 trifluoromethyl pyridyl group Chemical group 0.000 description 1
- 230000005747 tumor angiogenesis Effects 0.000 description 1
- 230000004614 tumor growth Effects 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IB9800003 | 1998-01-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP9801423A0 AP9801423A0 (en) | 1998-12-31 |
| AP869A true AP869A (en) | 2000-09-04 |
Family
ID=11004645
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1998/001423A AP869A (en) | 1998-01-05 | 1998-12-17 | 2,3-Substituted indole compounds as anti-inflammatory and analgesic agents. |
Country Status (39)
| Country | Link |
|---|---|
| US (1) | US6608070B1 (de) |
| EP (1) | EP1045833B1 (de) |
| JP (1) | JP3347136B2 (de) |
| KR (1) | KR100404054B1 (de) |
| CN (1) | CN1284064A (de) |
| AP (1) | AP869A (de) |
| AR (1) | AR016977A1 (de) |
| AT (1) | ATE308519T1 (de) |
| AU (1) | AU748107B2 (de) |
| BG (1) | BG104643A (de) |
| BR (1) | BR9813124A (de) |
| CA (1) | CA2316863A1 (de) |
| CO (1) | CO4970807A1 (de) |
| DE (1) | DE69832200T2 (de) |
| DZ (1) | DZ2700A1 (de) |
| EA (1) | EA200000614A1 (de) |
| ES (1) | ES2255190T3 (de) |
| GT (1) | GT199800205A (de) |
| HN (1) | HN1997000098A (de) |
| HR (1) | HRP20000454A2 (de) |
| HU (1) | HUP0102922A3 (de) |
| ID (1) | ID24876A (de) |
| IL (1) | IL136885A0 (de) |
| IS (1) | IS5532A (de) |
| MA (1) | MA24736A1 (de) |
| NO (1) | NO20003451L (de) |
| OA (1) | OA11441A (de) |
| PA (1) | PA8466201A1 (de) |
| PE (1) | PE20000055A1 (de) |
| PL (1) | PL341696A1 (de) |
| SA (1) | SA99191299A (de) |
| SK (1) | SK9912000A3 (de) |
| TN (1) | TNSN99001A1 (de) |
| TR (1) | TR200001906T2 (de) |
| TW (1) | TW436482B (de) |
| UY (2) | UY25332A1 (de) |
| WO (1) | WO1999035130A1 (de) |
| YU (1) | YU41600A (de) |
| ZA (1) | ZA9911B (de) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6555540B1 (en) * | 1999-06-30 | 2003-04-29 | Pfizer Inc | Combinations of aldose reductase inhibitors and selective cyclooxygenase-2 inhibitors |
| PT1065206E (pt) * | 1999-07-02 | 2003-01-31 | Pfizer | Compostos de tetrazolilalquilindole e como agentes anti-inflamatorios e analgesicos |
| MXPA00006605A (es) * | 1999-07-02 | 2004-12-09 | Pfizer | Compuestos de carbonil-indol biciclicos como agentes antiinflamatorios/analgesicos. |
| MXPA01008058A (es) | 1999-12-08 | 2004-04-05 | Pharmacia Corp | Composiciones deinhibidor de cicloxigenasa-2 teniendo un rapido inicio de efecto terapeutico. |
| US20070093485A1 (en) * | 2002-12-19 | 2007-04-26 | Elan Pharmaceuticals, Inc. | Substituted n-phenyl sulfonamide bradykinin antagonists |
| US7223785B2 (en) | 2003-01-22 | 2007-05-29 | Boehringer Ingelheim International Gmbh | Viral polymerase inhibitors |
| US7098231B2 (en) | 2003-01-22 | 2006-08-29 | 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 (de) | 2006-10-17 | 2011-06-22 | Stiefel Laboratories | Talarazolmetaboliten |
| US20120022121A1 (en) * | 2007-11-29 | 2012-01-26 | Dalton James T | Indoles, derivatives and analogs thereof and uses therefor |
| MX2012012092A (es) * | 2010-04-19 | 2012-12-17 | Metabolic Solutions Dev Co Llc | Sintesis novedosa para compuestos de tiazolidinadiona. |
| ES2547890T3 (es) | 2010-07-07 | 2015-10-09 | Ardelyx, Inc. | Compuestos y métodos para inhibir el transporte de fosfato |
| 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 |
| JP5823514B2 (ja) | 2010-07-07 | 2015-11-25 | 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 |
| WO2012006474A2 (en) | 2010-07-07 | 2012-01-12 | Ardelyx, Inc. | Compounds and methods for inhibiting phosphate transport |
| CN103153991B (zh) | 2010-08-10 | 2016-06-29 | 新陈代谢解决方案开发公司 | 噻唑烷二酮化合物的合成方法 |
| NZ606574A (en) | 2010-08-10 | 2015-02-27 | Metabolic Solutions Dev Co Llc | Novel synthesis for thiazolidinedione compounds |
| WO2013138600A1 (en) * | 2012-03-16 | 2013-09-19 | Rosen Eliot M | Radioprotector compounds |
| US9808443B1 (en) | 2016-11-28 | 2017-11-07 | King Saud University | Cyclooxygenase inhibitors |
| CN111004121A (zh) * | 2019-12-09 | 2020-04-14 | 南京杰运医药科技有限公司 | 一种4-烷氧基乙酰乙酸酯类化合物的制备方法 |
| CN112409281B (zh) * | 2020-08-20 | 2022-11-18 | 上海大学 | (e)-3-(3-氯-2-氟-6-(1h-四氮唑-1-基)苯基)丙烯酸的合成方法 |
| US20240165148A1 (en) | 2021-03-15 | 2024-05-23 | Saul Yedgar | Hyaluronic acid-conjugated dipalmitoyl phosphatidyl ethanolamine in combination with non-steroidal anti-inflammatory drugs (nsaids) for treating or alleviating inflammatory diseases |
| EP4353262A4 (de) * | 2021-06-10 | 2025-05-21 | UIF (University Industry Foundation), Yonsei University | Neue verbindung mit hemmender wirkung gegen pendrin und pharmazeutische verwendungen davon |
| CN116262721A (zh) * | 2023-01-12 | 2023-06-16 | 浙江师范大学 | 一种二氢吲哚衍生物及吲哚衍生物的制备方法及产品 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5510368A (en) * | 1995-05-22 | 1996-04-23 | Merck Frosst Canada, Inc. | N-benzyl-3-indoleacetic acids as antiinflammatory drugs |
| WO1996037469A1 (en) * | 1995-05-22 | 1996-11-28 | Merck Frosst Canada Inc. | N-benzylindol-3-yl propanic acid derivatives as cyclooxygenase-2 inhibitors |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CO5190664A1 (es) * | 1999-06-30 | 2002-08-29 | Pfizer Prod Inc | Terapia de combinacion para el tratamiento de migrana administracion de un receptor 5ht, cafeina y un inhibidor de ciclooxigenasa-2 |
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1998
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- 1998-12-18 EP EP98959082A patent/EP1045833B1/de not_active Expired - Lifetime
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1999
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- 1999-01-04 MA MA25414A patent/MA24736A1/fr unknown
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- 1999-01-05 PA PA19998466201A patent/PA8466201A1/es unknown
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-
2000
- 2000-06-13 IS IS5532A patent/IS5532A/is unknown
- 2000-06-30 OA OA1200000195A patent/OA11441A/en unknown
- 2000-07-04 NO NO20003451A patent/NO20003451L/no unknown
- 2000-07-28 BG BG104643A patent/BG104643A/bg unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5510368A (en) * | 1995-05-22 | 1996-04-23 | Merck Frosst Canada, Inc. | N-benzyl-3-indoleacetic acids as antiinflammatory drugs |
| WO1996037469A1 (en) * | 1995-05-22 | 1996-11-28 | Merck Frosst Canada Inc. | N-benzylindol-3-yl propanic acid derivatives as cyclooxygenase-2 inhibitors |
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