HRP20000454A2 - 2,3-substituted indole compounds as cox-2 inhibitors - Google Patents
2,3-substituted indole compounds as cox-2 inhibitors Download PDFInfo
- Publication number
- HRP20000454A2 HRP20000454A2 HR20000454A HRP20000454A HRP20000454A2 HR P20000454 A2 HRP20000454 A2 HR P20000454A2 HR 20000454 A HR20000454 A HR 20000454A HR P20000454 A HRP20000454 A HR P20000454A HR P20000454 A2 HRP20000454 A2 HR P20000454A2
- Authority
- HR
- Croatia
- Prior art keywords
- indol
- chloro
- acetic acid
- carbonyl
- alkyl
- Prior art date
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- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 title description 7
- 150000002475 indoles Chemical class 0.000 title description 6
- 229940111134 coxibs Drugs 0.000 title description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 483
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 271
- 125000001424 substituent group Chemical group 0.000 claims description 259
- -1 -NH2S(O)2NR2R3 Chemical group 0.000 claims description 247
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 239
- 150000001875 compounds Chemical class 0.000 claims description 235
- 125000005843 halogen group Chemical group 0.000 claims description 225
- 238000000034 method Methods 0.000 claims description 210
- 125000004414 alkyl thio group Chemical group 0.000 claims description 151
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 149
- 125000003282 alkyl amino group Chemical group 0.000 claims description 121
- 125000003118 aryl group Chemical group 0.000 claims description 121
- 125000000217 alkyl group Chemical group 0.000 claims description 99
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 96
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 83
- 125000003545 alkoxy group Chemical group 0.000 claims description 81
- 230000008569 process Effects 0.000 claims description 65
- 125000005842 heteroatom Chemical group 0.000 claims description 62
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 61
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 60
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 58
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 58
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 58
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 54
- 239000002904 solvent Substances 0.000 claims description 53
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 52
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 48
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 48
- 235000011181 potassium carbonates Nutrition 0.000 claims description 48
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 46
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 45
- 238000006243 chemical reaction Methods 0.000 claims description 43
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 41
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 41
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 39
- 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 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 38
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 36
- 229910052760 oxygen Inorganic materials 0.000 claims description 33
- 229910052717 sulfur Inorganic materials 0.000 claims description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims description 32
- 238000011282 treatment Methods 0.000 claims description 30
- 125000000623 heterocyclic group Chemical group 0.000 claims description 29
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical group CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 28
- 150000003973 alkyl amines Chemical class 0.000 claims description 28
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 27
- 235000017550 sodium carbonate Nutrition 0.000 claims description 27
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 25
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 23
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 21
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 21
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 125000006239 protecting group Chemical group 0.000 claims description 20
- HQRJGLVSBRTHME-UHFFFAOYSA-N 2-(2-benzoyl-6-chloro-1h-indol-3-yl)acetic acid Chemical class N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=CC=C1 HQRJGLVSBRTHME-UHFFFAOYSA-N 0.000 claims description 19
- 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 19
- 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 18
- 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 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 18
- 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 17
- 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 17
- 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 description 17
- 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 17
- 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 17
- 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 17
- 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 17
- 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 17
- 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 claims description 17
- 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 17
- 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 17
- 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 17
- 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 17
- 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 17
- 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 17
- 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 17
- 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 description 17
- 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 17
- 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 description 17
- 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 17
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 17
- 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 16
- 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 16
- 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 16
- 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 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- 239000011698 potassium fluoride Substances 0.000 claims description 16
- 235000003270 potassium fluoride Nutrition 0.000 claims description 16
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 16
- 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 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 239000011734 sodium Chemical class 0.000 claims description 15
- 229910052708 sodium Inorganic materials 0.000 claims description 15
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
- 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 14
- 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 14
- 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 14
- 150000003180 prostaglandins Chemical class 0.000 claims description 14
- 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 13
- 239000002253 acid Substances 0.000 claims description 13
- 125000002541 furyl group Chemical group 0.000 claims description 13
- 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 13
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- 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 12
- 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 12
- 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 12
- 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 12
- 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 12
- 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 12
- 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 12
- 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 claims description 12
- MQSROOYLIQDQPL-UHFFFAOYSA-N 2-[5-chloro-2-(2-methyl-1h-imidazole-5-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound N1C(C)=NC(C(=O)C2=C(C3=CC(Cl)=CC=C3N2)CC(O)=O)=C1 MQSROOYLIQDQPL-UHFFFAOYSA-N 0.000 claims description 12
- 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 12
- 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 description 12
- QRPCOTHMNUSSAE-UHFFFAOYSA-N 2-[5-chloro-2-(4-methyl-1,3-thiazole-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CC1=CSC(C(=O)C2=C(C3=CC(Cl)=CC=C3N2)CC(O)=O)=N1 QRPCOTHMNUSSAE-UHFFFAOYSA-N 0.000 claims description 12
- RBDFSQQYFRTJJZ-UHFFFAOYSA-N 2-[5-chloro-2-[4-(trifluoromethoxy)benzoyl]-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)O)=C1C(=O)C1=CC=C(OC(F)(F)F)C=C1 RBDFSQQYFRTJJZ-UHFFFAOYSA-N 0.000 claims description 12
- 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 12
- PWSNKQDYXDTFKA-UHFFFAOYSA-N 2-[5-tert-butyl-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CC1=CC=NC(C(=O)C2=C(C3=CC(=CC=C3N2)C(C)(C)C)CC(O)=O)=C1 PWSNKQDYXDTFKA-UHFFFAOYSA-N 0.000 claims description 12
- 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 12
- JSHSAONBVOGQCR-UHFFFAOYSA-N 2-[6-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=C(Cl)C=C2N1 JSHSAONBVOGQCR-UHFFFAOYSA-N 0.000 claims description 12
- 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 description 12
- VEMVFTJSNATNQV-UHFFFAOYSA-N 2-[6-chloro-2-(4-methyl-1,3-thiazole-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CC1=CSC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)CC(O)=O)=N1 VEMVFTJSNATNQV-UHFFFAOYSA-N 0.000 claims description 12
- 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 12
- 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 description 12
- FEZIMDVJVWMTGO-UHFFFAOYSA-N 2-[6-chloro-2-(cyclohexanecarbonyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1CCCCC1 FEZIMDVJVWMTGO-UHFFFAOYSA-N 0.000 claims description 12
- 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 12
- 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 12
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 12
- 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 12
- 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 12
- 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 12
- 239000011736 potassium bicarbonate Substances 0.000 claims description 12
- 235000015497 potassium bicarbonate Nutrition 0.000 claims description 12
- 229910000028 potassium bicarbonate Inorganic materials 0.000 claims description 12
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 claims description 12
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 12
- 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 11
- 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 description 11
- 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 11
- QYHVJTBMBTUHLF-UHFFFAOYSA-N 2-[5-chloro-2-(6-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CC1=CC=CC(C(=O)C2=C(C3=CC(Cl)=CC=C3N2)CC(O)=O)=N1 QYHVJTBMBTUHLF-UHFFFAOYSA-N 0.000 claims description 11
- 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 claims description 11
- 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 11
- 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 11
- 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 11
- 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 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 11
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 11
- 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 11
- 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 11
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 11
- 125000000335 thiazolyl group Chemical group 0.000 claims description 11
- 125000001544 thienyl group Chemical group 0.000 claims description 11
- 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 10
- 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 10
- SPAHFOWWQPUGOE-UHFFFAOYSA-N 2-[5-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(Cl)=CC=C2N1 SPAHFOWWQPUGOE-UHFFFAOYSA-N 0.000 claims description 10
- 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 10
- 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 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 10
- AKBZGRBYTSHPNP-UHFFFAOYSA-N ethyl 2-(2-benzoyl-6-chloro-1h-indol-3-yl)acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OCC)=C1C(=O)C1=CC=CC=C1 AKBZGRBYTSHPNP-UHFFFAOYSA-N 0.000 claims description 10
- 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 10
- 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 10
- 229940094443 oxytocics prostaglandins Drugs 0.000 claims description 10
- 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 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000002883 imidazolyl group Chemical group 0.000 claims description 9
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 9
- 239000012312 sodium hydride Substances 0.000 claims description 9
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 9
- 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 8
- CTWYRHDFWKRRKA-UHFFFAOYSA-N 2-[2-(4-chlorobenzoyl)-5-(trifluoromethoxy)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC=C(OC(F)(F)F)C=C2C(CC(=O)O)=C1C(=O)C1=CC=C(Cl)C=C1 CTWYRHDFWKRRKA-UHFFFAOYSA-N 0.000 claims description 8
- 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 8
- 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 claims description 8
- 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 8
- RMXKBFBIJOCEEU-UHFFFAOYSA-N 2-[5-ethyl-2-(4-ethylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CCC1=CC=NC(C(=O)C2=C(C3=CC(CC)=CC=C3N2)CC(O)=O)=C1 RMXKBFBIJOCEEU-UHFFFAOYSA-N 0.000 claims description 8
- SCECXPYERIUNDX-UHFFFAOYSA-N 2-[5-methoxy-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound OC(=O)CC=1C2=CC(OC)=CC=C2NC=1C(=O)C1=CC(C)=CC=N1 SCECXPYERIUNDX-UHFFFAOYSA-N 0.000 claims description 8
- 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 description 8
- ABLJUXJPXHNJRV-UHFFFAOYSA-N 2-[6-chloro-2-(3-methoxybenzoyl)-1h-indol-3-yl]acetic acid Chemical compound COC1=CC=CC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)CC(O)=O)=C1 ABLJUXJPXHNJRV-UHFFFAOYSA-N 0.000 claims description 8
- 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 8
- JIRSXUHWEMMDHG-UHFFFAOYSA-N 2-[6-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=C(Cl)C=C2N1 JIRSXUHWEMMDHG-UHFFFAOYSA-N 0.000 claims description 8
- 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 description 8
- 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 8
- 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 8
- 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 8
- XXXVGINRZSHYHM-UHFFFAOYSA-N 2-[6-chloro-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)=C(Cl)C=C3N2)CC(O)=O)=C1 XXXVGINRZSHYHM-UHFFFAOYSA-N 0.000 claims description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 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 8
- 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 8
- 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 8
- 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 8
- 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 8
- 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 8
- 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 claims description 8
- 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 claims description 8
- 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 description 8
- 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 8
- 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 8
- 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 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 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 7
- DHIDFWSDRQOSCX-UHFFFAOYSA-N 2-[2-(4-tert-butylpyridine-2-carbonyl)-6-chloro-1h-indol-3-yl]acetic acid Chemical compound CC(C)(C)C1=CC=NC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)CC(O)=O)=C1 DHIDFWSDRQOSCX-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- 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 7
- BVLDTQOJHAZUMB-UHFFFAOYSA-N 2-[6-methoxy-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(OC)=CC=C2C(CC(O)=O)=C1C(=O)C1=CC(C)=CC=N1 BVLDTQOJHAZUMB-UHFFFAOYSA-N 0.000 claims description 7
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 7
- 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 7
- 229940043279 diisopropylamine Drugs 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
- 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
- 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 description 7
- 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 7
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 7
- ULWOJODHECIZAU-UHFFFAOYSA-N n,n-diethylpropan-2-amine Chemical compound CCN(CC)C(C)C ULWOJODHECIZAU-UHFFFAOYSA-N 0.000 claims description 7
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 7
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims description 7
- 229910000105 potassium hydride Inorganic materials 0.000 claims description 7
- 125000005493 quinolyl group Chemical group 0.000 claims description 7
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
- 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 description 6
- 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 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
- 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 6
- 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 6
- 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 claims description 6
- 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 6
- 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 claims description 6
- 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 claims description 6
- 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 6
- 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 6
- 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 6
- 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 claims description 6
- 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 6
- 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 6
- 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 6
- 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 6
- CEXBEBSAIJGUBG-UHFFFAOYSA-N methyl 2-[5-tert-butyl-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(C(C)(C)C)C=C2C(CC(=O)OC)=C1C(=O)C1=CC(C)=CC=N1 CEXBEBSAIJGUBG-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 6
- 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 description 6
- 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 description 6
- 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 6
- 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 6
- 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 6
- 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 description 6
- 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 6
- 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 description 6
- 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 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 235000011118 potassium hydroxide Nutrition 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 5
- IDIWDXHXQKDYOH-UHFFFAOYSA-N 2-[5-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(Cl)=CC=C2N1 IDIWDXHXQKDYOH-UHFFFAOYSA-N 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- 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 claims description 5
- 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 description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 244000052769 pathogen Species 0.000 claims description 5
- 235000019260 propionic acid Nutrition 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
- 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 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 5
- 125000001425 triazolyl group Chemical group 0.000 claims description 5
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 5
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 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 description 4
- 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 4
- AGVMPGOZKHQYKZ-UHFFFAOYSA-N 2-[2-(4-chlorobenzoyl)-5-methoxy-1h-indol-3-yl]acetic acid Chemical compound OC(=O)CC=1C2=CC(OC)=CC=C2NC=1C(=O)C1=CC=C(Cl)C=C1 AGVMPGOZKHQYKZ-UHFFFAOYSA-N 0.000 claims description 4
- MWJHRMDTJLPMNA-UHFFFAOYSA-N 2-[2-(4-chlorobenzoyl)-6-(trifluoromethyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(C(F)(F)F)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=C(Cl)C=C1 MWJHRMDTJLPMNA-UHFFFAOYSA-N 0.000 claims description 4
- HXTHBFZIZKGEHC-UHFFFAOYSA-N 2-[2-(4-chlorobenzoyl)-6-methoxy-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(OC)=CC=C2C(CC(O)=O)=C1C(=O)C1=CC=C(Cl)C=C1 HXTHBFZIZKGEHC-UHFFFAOYSA-N 0.000 claims description 4
- JXSPPEWQPDAQFQ-UHFFFAOYSA-N 2-[2-(4-ethylpyridine-2-carbonyl)-5-(trifluoromethoxy)-1h-indol-3-yl]acetic acid Chemical compound CCC1=CC=NC(C(=O)C2=C(C3=CC(OC(F)(F)F)=CC=C3N2)CC(O)=O)=C1 JXSPPEWQPDAQFQ-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- LGKDKGPYTHYCKN-UHFFFAOYSA-N 2-[2-(4-tert-butylpyridine-2-carbonyl)-5-chloro-1h-indol-3-yl]acetic acid Chemical compound CC(C)(C)C1=CC=NC(C(=O)C2=C(C3=CC(Cl)=CC=C3N2)CC(O)=O)=C1 LGKDKGPYTHYCKN-UHFFFAOYSA-N 0.000 claims description 4
- SMENJXNEXWHJSS-UHFFFAOYSA-N 2-[5-acetyl-2-(4-chlorobenzoyl)-1h-indol-3-yl]acetic acid Chemical compound OC(=O)CC=1C2=CC(C(=O)C)=CC=C2NC=1C(=O)C1=CC=C(Cl)C=C1 SMENJXNEXWHJSS-UHFFFAOYSA-N 0.000 claims description 4
- ABTBSQFGUWMFGT-UHFFFAOYSA-N 2-[5-chloro-2-(1,3-thiazole-5-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)O)=C1C(=O)C1=CN=CS1 ABTBSQFGUWMFGT-UHFFFAOYSA-N 0.000 claims description 4
- OULUBRHRDAHLSZ-UHFFFAOYSA-N 2-[5-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(Cl)=CC=C2N1 OULUBRHRDAHLSZ-UHFFFAOYSA-N 0.000 claims description 4
- IQDVZLRPPBNUQI-UHFFFAOYSA-N 2-[5-chloro-2-(1-methylpyrrole-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CN1C=CC=C1C(=O)C1=C(CC(O)=O)C2=CC(Cl)=CC=C2N1 IQDVZLRPPBNUQI-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- XHQGSUNBBZGFRK-UHFFFAOYSA-N 2-[5-chloro-2-(4-methylthiadiazole-5-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound N1=NSC(C(=O)C2=C(C3=CC(Cl)=CC=C3N2)CC(O)=O)=C1C XHQGSUNBBZGFRK-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 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 4
- HWEGSYUCJYLKEO-UHFFFAOYSA-N 2-[5-tert-butyl-2-(4-chlorobenzoyl)-1h-indol-3-yl]acetic acid Chemical compound OC(=O)CC=1C2=CC(C(C)(C)C)=CC=C2NC=1C(=O)C1=CC=C(Cl)C=C1 HWEGSYUCJYLKEO-UHFFFAOYSA-N 0.000 claims description 4
- QAMOOWGWIKTUMJ-UHFFFAOYSA-N 2-[6-chloro-2-(1h-imidazole-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=NC=CN1 QAMOOWGWIKTUMJ-UHFFFAOYSA-N 0.000 claims description 4
- KFKUCBZEFWIDMF-UHFFFAOYSA-N 2-[6-chloro-2-(2,4-dichlorobenzoyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=C(Cl)C=C1Cl KFKUCBZEFWIDMF-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- UGWKNVNCTSOSPC-UHFFFAOYSA-N 2-[6-chloro-2-(2,5-dimethoxybenzoyl)-1h-indol-3-yl]acetic acid Chemical compound COC1=CC=C(OC)C(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)CC(O)=O)=C1 UGWKNVNCTSOSPC-UHFFFAOYSA-N 0.000 claims description 4
- WQLYUKKMPCQWHO-UHFFFAOYSA-N 2-[6-chloro-2-(2-chlorobenzoyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=CC=C1Cl WQLYUKKMPCQWHO-UHFFFAOYSA-N 0.000 claims description 4
- RDZSLOZUFJIMIQ-UHFFFAOYSA-N 2-[6-chloro-2-(2-methoxybenzoyl)-1h-indol-3-yl]acetic acid Chemical compound COC1=CC=CC=C1C(=O)C1=C(CC(O)=O)C2=CC=C(Cl)C=C2N1 RDZSLOZUFJIMIQ-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 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 description 4
- BTJFKTMURWZAJV-UHFFFAOYSA-N 2-[6-chloro-2-(3-phenylmethoxybenzoyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C(C=1)=CC=CC=1OCC1=CC=CC=C1 BTJFKTMURWZAJV-UHFFFAOYSA-N 0.000 claims description 4
- AHFMJVAAHUQZDC-UHFFFAOYSA-N 2-[6-chloro-2-(4-chloro-3-fluorobenzoyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=C(Cl)C(F)=C1 AHFMJVAAHUQZDC-UHFFFAOYSA-N 0.000 claims description 4
- RDMSEDZQZOMHRP-UHFFFAOYSA-N 2-[6-chloro-2-(4-hydroxybenzoyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=C(O)C=C1 RDMSEDZQZOMHRP-UHFFFAOYSA-N 0.000 claims description 4
- YOQMNEYHUVOVPY-UHFFFAOYSA-N 2-[6-chloro-2-(4-methylthiadiazole-5-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound N1=NSC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)CC(O)=O)=C1C YOQMNEYHUVOVPY-UHFFFAOYSA-N 0.000 claims description 4
- OSKCEEYCWRBVKE-UHFFFAOYSA-N 2-[6-chloro-2-(4-nitrobenzoyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=C([N+]([O-])=O)C=C1 OSKCEEYCWRBVKE-UHFFFAOYSA-N 0.000 claims description 4
- LCSYYVIRAZLJEZ-UHFFFAOYSA-N 2-[6-chloro-2-(4-phenylbenzoyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C(C=C1)=CC=C1C1=CC=CC=C1 LCSYYVIRAZLJEZ-UHFFFAOYSA-N 0.000 claims description 4
- ATFMTASOJDFHRU-UHFFFAOYSA-N 2-[6-chloro-2-(4-propan-2-yloxybenzoyl)-1h-indol-3-yl]acetic acid Chemical compound C1=CC(OC(C)C)=CC=C1C(=O)C1=C(CC(O)=O)C2=CC=C(Cl)C=C2N1 ATFMTASOJDFHRU-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- JMUWFNFIDYAFKI-UHFFFAOYSA-N 2-[6-chloro-2-(4-thiophen-2-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=CS1 JMUWFNFIDYAFKI-UHFFFAOYSA-N 0.000 claims description 4
- RXESIXLBZIGNDS-UHFFFAOYSA-N 2-[6-chloro-2-(pyridine-3-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=CN=C1 RXESIXLBZIGNDS-UHFFFAOYSA-N 0.000 claims description 4
- JRNYJEFZKAFDOI-UHFFFAOYSA-N 2-[6-chloro-2-(pyridine-4-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=NC=C1 JRNYJEFZKAFDOI-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- BFUXULXWBWSQGU-UHFFFAOYSA-N 2-[6-chloro-2-[4-(1,3-thiazol-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=NC=CS1 BFUXULXWBWSQGU-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- 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 description 4
- 235000019270 ammonium chloride Nutrition 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
- 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 4
- KYYDRJQWKPOSCU-UHFFFAOYSA-N methyl 2-[2-(4-bromobenzoyl)-6-chloro-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC=C(Br)C=C1 KYYDRJQWKPOSCU-UHFFFAOYSA-N 0.000 claims description 4
- YYIYQWUXWIHDGP-UHFFFAOYSA-N methyl 2-[2-(4-chlorobenzoyl)-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(Cl)C=C1 YYIYQWUXWIHDGP-UHFFFAOYSA-N 0.000 claims description 4
- NDUQBKJUKWVOLT-UHFFFAOYSA-N methyl 2-[5-chloro-2-(1-methylimidazole-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)OC)=C1C(=O)C1=NC=CN1C NDUQBKJUKWVOLT-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 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 4
- SKZPHUUTOZJTSU-UHFFFAOYSA-N methyl 2-[5-chloro-2-(4-propylpyridine-2-carbonyl)-1h-indol-3-yl]acetate Chemical compound CCCC1=CC=NC(C(=O)C2=C(C3=CC(Cl)=CC=C3N2)CC(=O)OC)=C1 SKZPHUUTOZJTSU-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 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 description 4
- 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 4
- 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 4
- 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 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
- 125000006384 methylpyridyl group Chemical group 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
- 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
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 claims description 4
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- DWCCDPOQTMLZAY-UHFFFAOYSA-N 2-[2-(4-chlorobenzoyl)-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(Cl)C=C1 DWCCDPOQTMLZAY-UHFFFAOYSA-N 0.000 claims description 3
- GMYIEFGNSRBNET-UHFFFAOYSA-N 2-[5-chloro-2-(3,4-dimethylpyridine-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)=C1C GMYIEFGNSRBNET-UHFFFAOYSA-N 0.000 claims description 3
- SXNJXLBASRRSQG-UHFFFAOYSA-N 2-[5-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(Cl)=CC=C3N2)CC(O)=O)=N1 SXNJXLBASRRSQG-UHFFFAOYSA-N 0.000 claims description 3
- XDVJPEGYXRZAHA-UHFFFAOYSA-N 2-[6-chloro-2-(4-phenylmethoxybenzoyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C(C=C1)=CC=C1OCC1=CC=CC=C1 XDVJPEGYXRZAHA-UHFFFAOYSA-N 0.000 claims description 3
- TUGJBGFXDURIOG-UHFFFAOYSA-N 2-[6-chloro-2-[3-(furan-2-yl)benzoyl]-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C(C=1)=CC=CC=1C1=CC=CO1 TUGJBGFXDURIOG-UHFFFAOYSA-N 0.000 claims description 3
- AEAWHRHHBOTLKY-UHFFFAOYSA-N 2-[6-chloro-2-[4-(hydroxymethyl)pyridine-2-carbonyl]-1h-indol-3-yl]acetic acid Chemical compound OCC1=CC=NC(C(=O)C2=C(C3=CC=C(Cl)C=C3N2)CC(O)=O)=C1 AEAWHRHHBOTLKY-UHFFFAOYSA-N 0.000 claims description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
- LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 claims description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 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
- 125000001188 haloalkyl group Chemical group 0.000 claims description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
- 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 3
- KZTDXMVQAZALCQ-UHFFFAOYSA-N methyl 2-[2-(4-tert-butylpyridine-2-carbonyl)-6-chloro-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC(C(C)(C)C)=CC=N1 KZTDXMVQAZALCQ-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 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
- 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 3
- 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 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
- 235000015424 sodium Nutrition 0.000 claims description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- QXGLGNQMXTXNJS-UHFFFAOYSA-N (6-chloro-1h-indol-2-yl)-phenylmethanone Chemical compound N1C2=CC(Cl)=CC=C2C=C1C(=O)C1=CC=CC=C1 QXGLGNQMXTXNJS-UHFFFAOYSA-N 0.000 claims description 2
- ZNZUFZCXNCWVSW-UHFFFAOYSA-N 2-(2-benzoyl-6-chloro-1h-indol-3-yl)-1-(4-methylpiperazin-1-yl)ethanone Chemical compound C1CN(C)CCN1C(=O)CC1=C(C(=O)C=2C=CC=CC=2)NC2=CC(Cl)=CC=C12 ZNZUFZCXNCWVSW-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- VDOYJRHOWGHVDP-UHFFFAOYSA-N 2-(2-benzoyl-6-chloro-1h-indol-3-yl)-1-piperidin-1-ylethanone Chemical compound C=1C=CC=CC=1C(=O)C=1NC2=CC(Cl)=CC=C2C=1CC(=O)N1CCCCC1 VDOYJRHOWGHVDP-UHFFFAOYSA-N 0.000 claims description 2
- BOBHNBJTSRMAFB-UHFFFAOYSA-N 2-(2-benzoyl-6-chloro-1h-indol-3-yl)-n,n-dimethylacetamide Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)N(C)C)=C1C(=O)C1=CC=CC=C1 BOBHNBJTSRMAFB-UHFFFAOYSA-N 0.000 claims description 2
- BIAWHCUCMLAAPR-UHFFFAOYSA-N 2-(2-benzoyl-6-chloro-1h-indol-3-yl)-n-(2-cyanoethyl)acetamide Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)NCCC#N)=C1C(=O)C1=CC=CC=C1 BIAWHCUCMLAAPR-UHFFFAOYSA-N 0.000 claims description 2
- ANFKJYNQQBDFQQ-UHFFFAOYSA-N 2-(2-benzoyl-6-chloro-1h-indol-3-yl)-n-(2-hydroxyethyl)acetamide Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)NCCO)=C1C(=O)C1=CC=CC=C1 ANFKJYNQQBDFQQ-UHFFFAOYSA-N 0.000 claims description 2
- XYEOBYLFEHWXHW-UHFFFAOYSA-N 2-(2-benzoyl-6-chloro-1h-indol-3-yl)-n-methoxy-n-methylacetamide Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)N(C)OC)=C1C(=O)C1=CC=CC=C1 XYEOBYLFEHWXHW-UHFFFAOYSA-N 0.000 claims description 2
- DUPJOZOZJXDOIP-UHFFFAOYSA-N 2-(2-benzoyl-6-chloro-1h-indol-3-yl)-n-methylacetamide Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)NC)=C1C(=O)C1=CC=CC=C1 DUPJOZOZJXDOIP-UHFFFAOYSA-N 0.000 claims description 2
- UVLYQZVWHWTARZ-UHFFFAOYSA-N 2-(2-benzoyl-6-chloro-1h-indol-3-yl)acetamide Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)N)=C1C(=O)C1=CC=CC=C1 UVLYQZVWHWTARZ-UHFFFAOYSA-N 0.000 claims description 2
- MYDDXBOZCRRFSN-UHFFFAOYSA-N 2-[2-(4-chlorobenzoyl)-6-fluoro-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(F)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=C(Cl)C=C1 MYDDXBOZCRRFSN-UHFFFAOYSA-N 0.000 claims description 2
- XAVZMVCQMPSHMP-UHFFFAOYSA-N 2-[2-(4-methylpyridine-2-carbonyl)-5-(trifluoromethoxy)-1h-indol-3-yl]acetic acid Chemical compound CC1=CC=NC(C(=O)C2=C(C3=CC(OC(F)(F)F)=CC=C3N2)CC(O)=O)=C1 XAVZMVCQMPSHMP-UHFFFAOYSA-N 0.000 claims description 2
- RBOPJCFKQFIKPV-UHFFFAOYSA-N 2-[5-chloro-2-(1h-imidazole-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)O)=C1C(=O)C1=NC=CN1 RBOPJCFKQFIKPV-UHFFFAOYSA-N 0.000 claims description 2
- DNKJFSFXUTXMRH-UHFFFAOYSA-N 2-[5-chloro-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]-1-piperazin-1-ylethanone Chemical compound CC1=CC=NC(C(=O)C2=C(C3=CC(Cl)=CC=C3N2)CC(=O)N2CCNCC2)=C1 DNKJFSFXUTXMRH-UHFFFAOYSA-N 0.000 claims description 2
- PYUKAHNZANUIOQ-UHFFFAOYSA-N 2-[5-chloro-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]-n-(2-hydroxyethyl)acetamide Chemical compound CC1=CC=NC(C(=O)C2=C(C3=CC(Cl)=CC=C3N2)CC(=O)NCCO)=C1 PYUKAHNZANUIOQ-UHFFFAOYSA-N 0.000 claims description 2
- HDVZQJHVCWIRDQ-UHFFFAOYSA-N 2-[5-chloro-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]-n-methoxyacetamide Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)NOC)=C1C(=O)C1=CC(C)=CC=N1 HDVZQJHVCWIRDQ-UHFFFAOYSA-N 0.000 claims description 2
- CYYVGLKURAVGDF-UHFFFAOYSA-N 2-[6-chloro-2-(3,4-dichlorobenzoyl)-1h-indol-3-yl]acetic acid Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)O)=C1C(=O)C1=CC=C(Cl)C(Cl)=C1 CYYVGLKURAVGDF-UHFFFAOYSA-N 0.000 claims description 2
- WLYLIKHLRGEHAN-UHFFFAOYSA-N 2-[6-chloro-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]-n,n-dimethylacetamide Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)N(C)C)=C1C(=O)C1=CC(C)=CC=N1 WLYLIKHLRGEHAN-UHFFFAOYSA-N 0.000 claims description 2
- RFXXZTGUGKQIBZ-UHFFFAOYSA-N 2-[6-chloro-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]-n-methylacetamide Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)NC)=C1C(=O)C1=CC(C)=CC=N1 RFXXZTGUGKQIBZ-UHFFFAOYSA-N 0.000 claims description 2
- UTXSNSLGSDYHIB-UHFFFAOYSA-N 2-[6-chloro-2-[4-(difluoromethoxy)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)C=C1 UTXSNSLGSDYHIB-UHFFFAOYSA-N 0.000 claims description 2
- SZQLJRUPQGEKLC-UHFFFAOYSA-N 2-[6-fluoro-2-(4-methylpyridine-2-carbonyl)-1h-indol-3-yl]acetic acid Chemical compound CC1=CC=NC(C(=O)C2=C(C3=CC=C(F)C=C3N2)CC(O)=O)=C1 SZQLJRUPQGEKLC-UHFFFAOYSA-N 0.000 claims description 2
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 2
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 2
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- CQODGVQBRIGKLJ-UHFFFAOYSA-L [Na+].[Na+].[O-]OOO[O-] Chemical compound [Na+].[Na+].[O-]OOO[O-] CQODGVQBRIGKLJ-UHFFFAOYSA-L 0.000 claims description 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004799 bromophenyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- QHPIYOOXROCLBS-UHFFFAOYSA-N ethyl 5-[5-chloro-3-(2-methoxy-2-oxoethyl)-1h-indole-2-carbonyl]-1,2-oxazole-3-carboxylate Chemical compound O1N=C(C(=O)OCC)C=C1C(=O)C1=C(CC(=O)OC)C2=CC(Cl)=CC=C2N1 QHPIYOOXROCLBS-UHFFFAOYSA-N 0.000 claims description 2
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 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
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- GCTHRPQDTJSXQF-UHFFFAOYSA-N methyl 2-[2-(4-chlorobenzoyl)-5-ethyl-1h-indol-3-yl]acetate Chemical compound COC(=O)CC=1C2=CC(CC)=CC=C2NC=1C(=O)C1=CC=C(Cl)C=C1 GCTHRPQDTJSXQF-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- BDGXRHHBQPTYOS-UHFFFAOYSA-N methyl 2-[2-(4-chlorobenzoyl)-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(Cl)C=C1 BDGXRHHBQPTYOS-UHFFFAOYSA-N 0.000 claims description 2
- UZARKRUJHNRSHS-UHFFFAOYSA-N methyl 2-[2-(4-chlorobenzoyl)-6-methoxy-1h-indol-3-yl]acetate Chemical compound N1C2=CC(OC)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC=C(Cl)C=C1 UZARKRUJHNRSHS-UHFFFAOYSA-N 0.000 claims description 2
- USPPGUUYZTYASB-UHFFFAOYSA-N methyl 2-[2-(4-ethylpyridine-2-carbonyl)-5-(trifluoromethoxy)-1h-indol-3-yl]acetate Chemical compound CCC1=CC=NC(C(=O)C2=C(C3=CC(OC(F)(F)F)=CC=C3N2)CC(=O)OC)=C1 USPPGUUYZTYASB-UHFFFAOYSA-N 0.000 claims description 2
- FQVQQFDRSSGGSF-UHFFFAOYSA-N methyl 2-[2-(4-tert-butylpyridine-2-carbonyl)-5-chloro-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)OC)=C1C(=O)C1=CC(C(C)(C)C)=CC=N1 FQVQQFDRSSGGSF-UHFFFAOYSA-N 0.000 claims description 2
- DPVBXWDVIWZXSM-UHFFFAOYSA-N methyl 2-[5-acetyl-2-(4-chlorobenzoyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(C(C)=O)C=C2C(CC(=O)OC)=C1C(=O)C1=CC=C(Cl)C=C1 DPVBXWDVIWZXSM-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- 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 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
- LMVBAOMTFGSKAJ-UHFFFAOYSA-N methyl 2-[5-chloro-2-(4-methylthiadiazole-5-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(Cl)C=C2C(CC(=O)OC)=C1C(=O)C=1SN=NC=1C LMVBAOMTFGSKAJ-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 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 claims description 2
- JTFQNVZLKRYIFP-UHFFFAOYSA-N methyl 2-[5-tert-butyl-2-(4-chlorobenzoyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC=C(C(C)(C)C)C=C2C(CC(=O)OC)=C1C(=O)C1=CC=C(Cl)C=C1 JTFQNVZLKRYIFP-UHFFFAOYSA-N 0.000 claims description 2
- 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 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
- 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 claims description 2
- 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 claims description 2
- YUEJHYAVTIHQSI-UHFFFAOYSA-N methyl 2-[6-chloro-2-(4-chloro-3-fluorobenzoyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC=C(Cl)C(F)=C1 YUEJHYAVTIHQSI-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- RJRUUGYSMGYRCD-UHFFFAOYSA-N methyl 2-[6-chloro-2-(4-methylthiadiazole-5-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C=1SN=NC=1C RJRUUGYSMGYRCD-UHFFFAOYSA-N 0.000 claims description 2
- 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 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
- GWGBNGOIYZBSPD-UHFFFAOYSA-N methyl 2-[6-chloro-2-(4-phenylmethoxybenzoyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C(C=C1)=CC=C1OCC1=CC=CC=C1 GWGBNGOIYZBSPD-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- NHJAPVCXNMOQLP-UHFFFAOYSA-N methyl 2-[6-chloro-2-(4-thiophen-2-ylbenzoyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C(C=C1)=CC=C1C1=CC=CS1 NHJAPVCXNMOQLP-UHFFFAOYSA-N 0.000 claims description 2
- ZCCHGFIMHYCBLH-UHFFFAOYSA-N methyl 2-[6-chloro-2-(pyridine-3-carbonyl)-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC=CN=C1 ZCCHGFIMHYCBLH-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 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 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
- 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 claims description 2
- RIHOEVURDVXSQM-UHFFFAOYSA-N methyl 2-[6-chloro-2-[4-(hydroxymethyl)pyridine-2-carbonyl]-1h-indol-3-yl]acetate Chemical compound N1C2=CC(Cl)=CC=C2C(CC(=O)OC)=C1C(=O)C1=CC(CO)=CC=N1 RIHOEVURDVXSQM-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 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 claims description 2
- 239000011541 reaction mixture Substances 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
- 150000002431 hydrogen Chemical class 0.000 claims 7
- JBFKNMAMZZPTLN-UHFFFAOYSA-N 2-[6-chloro-2-[3-(2-hydroxypropan-2-yl)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)=C1C(C)(O)C JBFKNMAMZZPTLN-UHFFFAOYSA-N 0.000 claims 2
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Classifications
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- 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
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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]
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- A—HUMAN NECESSITIES
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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
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- 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)
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- Bioinformatics & Cheminformatics (AREA)
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- 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 (2)
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IB9800003 | 1998-01-05 | ||
PCT/IB1998/002065 WO1999035130A1 (en) | 1998-01-05 | 1998-12-18 | 2,3-substituted indole compounds as cox-2 inhibitors |
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HRP20000454A2 true HRP20000454A2 (en) | 2001-04-30 |
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HR20000454A HRP20000454A2 (en) | 1998-01-05 | 2000-07-05 | 2,3-substituted indole compounds as cox-2 inhibitors |
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JP (1) | JP3347136B2 (is) |
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US6555540B1 (en) * | 1999-06-30 | 2003-04-29 | Pfizer Inc | Combinations of aldose reductase inhibitors and selective cyclooxygenase-2 inhibitors |
ES2182755T3 (es) * | 1999-07-02 | 2003-03-16 | Pfizer | Compuestos de tetrazolilalquilindol como agentes antiinflamtorios y analgesicos. |
MXPA00006605A (es) * | 1999-07-02 | 2004-12-09 | Pfizer | Compuestos de carbonil-indol biciclicos como agentes antiinflamatorios/analgesicos. |
EP1572678A4 (en) * | 2002-12-19 | 2008-05-07 | Elan Pharm Inc | SUBSTITUTED N-PHENYL SULPHONAMIDES ALSBRADYKININ 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 |
EP1534305B9 (en) | 2003-05-07 | 2007-03-07 | Osteologix A/S | Treating cartilage / bone conditions with water-soluble strontium salts |
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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 |
PL2603498T3 (pl) | 2010-08-10 | 2017-06-30 | Octeta Therapeutics, Llc | Nowa synteza związków tiazolidynodionu |
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