JP4460830B2 - インドール誘導体 - Google Patents
インドール誘導体 Download PDFInfo
- Publication number
- JP4460830B2 JP4460830B2 JP2002551528A JP2002551528A JP4460830B2 JP 4460830 B2 JP4460830 B2 JP 4460830B2 JP 2002551528 A JP2002551528 A JP 2002551528A JP 2002551528 A JP2002551528 A JP 2002551528A JP 4460830 B2 JP4460830 B2 JP 4460830B2
- Authority
- JP
- Japan
- Prior art keywords
- indol
- amino
- acetyl
- methyl
- formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 2
- 150000002475 indoles Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 118
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 239000012453 solvate Substances 0.000 claims abstract description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 229910052736 halogen Inorganic materials 0.000 claims description 41
- 150000002367 halogens Chemical class 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 125000005529 alkyleneoxy group Chemical group 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 241001465754 Metazoa Species 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- HGJWZMCCQFUOMJ-UHFFFAOYSA-N 2-[[2-(5-methoxy-2-methyl-1h-indol-3-yl)acetyl]amino]-4-methylbenzoic acid Chemical compound C12=CC(OC)=CC=C2NC(C)=C1CC(=O)NC1=CC(C)=CC=C1C(O)=O HGJWZMCCQFUOMJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 230000001268 conjugating effect Effects 0.000 claims description 3
- ITKOIFDWZSLOQB-UHFFFAOYSA-N 2-[[2-(1h-indol-3-yl)acetyl]amino]-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C(NC(=O)CC=2C3=CC=CC=C3NC=2)=C1 ITKOIFDWZSLOQB-UHFFFAOYSA-N 0.000 claims description 2
- HDCRKLQNWRHCMQ-UHFFFAOYSA-N 2-[[2-(4-chloro-1h-indol-3-yl)acetyl]amino]-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C(NC(=O)CC=2C3=C(Cl)C=CC=C3NC=2)=C1 HDCRKLQNWRHCMQ-UHFFFAOYSA-N 0.000 claims description 2
- FIYIJHDRTWPPQL-UHFFFAOYSA-N 2-[[2-(5,6-dimethoxy-2-methyl-1h-indol-3-yl)acetyl]amino]-4-methylbenzoic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(C)=C1CC(=O)NC1=CC(C)=CC=C1C(O)=O FIYIJHDRTWPPQL-UHFFFAOYSA-N 0.000 claims description 2
- IDAFAJSDIFJITE-UHFFFAOYSA-N 2-[[2-(5,6-dimethoxy-2-methyl-1h-indol-3-yl)acetyl]amino]benzoic acid Chemical compound C1=2C=C(OC)C(OC)=CC=2NC(C)=C1CC(=O)NC1=CC=CC=C1C(O)=O IDAFAJSDIFJITE-UHFFFAOYSA-N 0.000 claims description 2
- PSOIEJAPNBAECL-UHFFFAOYSA-N 2-[[2-(5-bromo-1h-indol-3-yl)acetyl]amino]-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C(NC(=O)CC=2C3=CC(Br)=CC=C3NC=2)=C1 PSOIEJAPNBAECL-UHFFFAOYSA-N 0.000 claims description 2
- LICKWGSQVRUXLF-UHFFFAOYSA-N 2-[[2-(5-chloro-2-methyl-1h-indol-3-yl)acetyl]amino]-4-methylbenzoic acid Chemical compound CC=1NC2=CC=C(Cl)C=C2C=1CC(=O)NC1=CC(C)=CC=C1C(O)=O LICKWGSQVRUXLF-UHFFFAOYSA-N 0.000 claims description 2
- CSJQLCCHNWEPQN-UHFFFAOYSA-N 2-[[2-(5-fluoro-1h-indol-3-yl)acetyl]amino]-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C(NC(=O)CC=2C3=CC(F)=CC=C3NC=2)=C1 CSJQLCCHNWEPQN-UHFFFAOYSA-N 0.000 claims description 2
- LSYOSGRYCLKTMJ-UHFFFAOYSA-N 2-[[2-(5-methoxy-1h-indol-3-yl)acetyl]amino]-4-methylbenzoic acid Chemical compound C12=CC(OC)=CC=C2NC=C1CC(=O)NC1=CC(C)=CC=C1C(O)=O LSYOSGRYCLKTMJ-UHFFFAOYSA-N 0.000 claims description 2
- DJKRCHDIPIOARW-UHFFFAOYSA-N 2-[[2-(5-methoxy-2-methyl-1h-indol-3-yl)acetyl]amino]-4-(trifluoromethyl)benzoic acid Chemical compound C12=CC(OC)=CC=C2NC(C)=C1CC(=O)NC1=CC(C(F)(F)F)=CC=C1C(O)=O DJKRCHDIPIOARW-UHFFFAOYSA-N 0.000 claims description 2
- WPNDNXATAOOKRO-YRNVUSSQSA-N 2-[[2-(5-methoxy-2-methyl-1h-indol-3-yl)acetyl]amino]-4-[(e)-3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]benzoic acid Chemical compound C12=CC(OC)=CC=C2NC(C)=C1CC(=O)NC1=CC(\C=C\C(=O)OC(C)(C)C)=CC=C1C(O)=O WPNDNXATAOOKRO-YRNVUSSQSA-N 0.000 claims description 2
- FNMIJJWWXJLERI-UHFFFAOYSA-N 2-[[2-(5-methoxy-2-methyl-1h-indol-3-yl)acetyl]amino]-4-nitrobenzoic acid Chemical compound C12=CC(OC)=CC=C2NC(C)=C1CC(=O)NC1=CC([N+]([O-])=O)=CC=C1C(O)=O FNMIJJWWXJLERI-UHFFFAOYSA-N 0.000 claims description 2
- GFTXGCXFJYNRFP-UHFFFAOYSA-N 2-[[2-(5-methoxy-2-methyl-1h-indol-3-yl)acetyl]amino]-5-methylbenzoic acid Chemical compound C12=CC(OC)=CC=C2NC(C)=C1CC(=O)NC1=CC=C(C)C=C1C(O)=O GFTXGCXFJYNRFP-UHFFFAOYSA-N 0.000 claims description 2
- BRZLBRWSCCOJIA-UHFFFAOYSA-N 2-[[2-(5-methoxy-2-methyl-1h-indol-3-yl)acetyl]amino]benzoic acid Chemical compound C12=CC(OC)=CC=C2NC(C)=C1CC(=O)NC1=CC=CC=C1C(O)=O BRZLBRWSCCOJIA-UHFFFAOYSA-N 0.000 claims description 2
- SQISMQBXVFLPAV-UHFFFAOYSA-N 3,5-dichloro-2-[[2-(5-methoxy-2-methyl-1h-indol-3-yl)acetyl]amino]benzoic acid Chemical compound C12=CC(OC)=CC=C2NC(C)=C1CC(=O)NC1=C(Cl)C=C(Cl)C=C1C(O)=O SQISMQBXVFLPAV-UHFFFAOYSA-N 0.000 claims description 2
- MVQKHBXWGGNULF-UHFFFAOYSA-N 3-hydroxy-2-[[2-(5-methoxy-2-methyl-1h-indol-3-yl)acetyl]amino]benzoic acid Chemical compound C12=CC(OC)=CC=C2NC(C)=C1CC(=O)NC1=C(O)C=CC=C1C(O)=O MVQKHBXWGGNULF-UHFFFAOYSA-N 0.000 claims description 2
- AYBDSIMVRYVUOA-UHFFFAOYSA-N 4,5-difluoro-2-[[2-(5-methoxy-2-methyl-1h-indol-3-yl)acetyl]amino]benzoic acid Chemical compound C12=CC(OC)=CC=C2NC(C)=C1CC(=O)NC1=CC(F)=C(F)C=C1C(O)=O AYBDSIMVRYVUOA-UHFFFAOYSA-N 0.000 claims description 2
- BJHCCUGGQLTDFE-UHFFFAOYSA-N 4-bromo-2-[[2-(5-methoxy-2-methyl-1h-indol-3-yl)acetyl]amino]benzoic acid Chemical compound C12=CC(OC)=CC=C2NC(C)=C1CC(=O)NC1=CC(Br)=CC=C1C(O)=O BJHCCUGGQLTDFE-UHFFFAOYSA-N 0.000 claims description 2
- TXBXBRWVEBFKOP-UHFFFAOYSA-N 4-chloro-2-[[2-(5-methoxy-2-methyl-1h-indol-3-yl)acetyl]amino]benzoic acid Chemical compound C12=CC(OC)=CC=C2NC(C)=C1CC(=O)NC1=CC(Cl)=CC=C1C(O)=O TXBXBRWVEBFKOP-UHFFFAOYSA-N 0.000 claims description 2
- IFQDVXYTDNFVAL-UHFFFAOYSA-N 4-ethyl-2-[[2-(5-methoxy-2-methyl-1h-indol-3-yl)acetyl]amino]benzoic acid Chemical compound CCC1=CC=C(C(O)=O)C(NC(=O)CC=2C3=CC(OC)=CC=C3NC=2C)=C1 IFQDVXYTDNFVAL-UHFFFAOYSA-N 0.000 claims description 2
- XSNYJVFQDGTGCF-UHFFFAOYSA-N 4-fluoro-2-[[2-(5-methoxy-2-methyl-1h-indol-3-yl)acetyl]amino]benzoic acid Chemical compound C12=CC(OC)=CC=C2NC(C)=C1CC(=O)NC1=CC(F)=CC=C1C(O)=O XSNYJVFQDGTGCF-UHFFFAOYSA-N 0.000 claims description 2
- JMOHWYIBXMKFJP-UHFFFAOYSA-N 4-methyl-2-[[2-(2-methyl-1h-indol-3-yl)acetyl]amino]benzoic acid Chemical compound CC=1NC2=CC=CC=C2C=1CC(=O)NC1=CC(C)=CC=C1C(O)=O JMOHWYIBXMKFJP-UHFFFAOYSA-N 0.000 claims description 2
- MEVIZUQLAGMDLQ-UHFFFAOYSA-N 4-methyl-2-[[2-(2-phenyl-1h-indol-3-yl)acetyl]amino]benzoic acid Chemical compound CC1=CC=C(C(O)=O)C(NC(=O)CC=2C3=CC=CC=C3NC=2C=2C=CC=CC=2)=C1 MEVIZUQLAGMDLQ-UHFFFAOYSA-N 0.000 claims description 2
- LOOLFQOJXPDRSD-UHFFFAOYSA-N 4-methyl-2-[[2-(5-phenylmethoxy-1h-indol-3-yl)acetyl]amino]benzoic acid Chemical compound CC1=CC=C(C(O)=O)C(NC(=O)CC=2C3=CC(OCC=4C=CC=CC=4)=CC=C3NC=2)=C1 LOOLFQOJXPDRSD-UHFFFAOYSA-N 0.000 claims description 2
- HWTUNAPTDXGHOP-UHFFFAOYSA-N 4-methyl-2-[[2-(7-phenylmethoxy-1h-indol-3-yl)acetyl]amino]benzoic acid Chemical compound CC1=CC=C(C(O)=O)C(NC(=O)CC=2C3=CC=CC(OCC=4C=CC=CC=4)=C3NC=2)=C1 HWTUNAPTDXGHOP-UHFFFAOYSA-N 0.000 claims description 2
- HDSRNIXCERVTSZ-UHFFFAOYSA-N 5-chloro-2-[[2-(5-methoxy-2-methyl-1h-indol-3-yl)acetyl]amino]benzoic acid Chemical compound C12=CC(OC)=CC=C2NC(C)=C1CC(=O)NC1=CC=C(Cl)C=C1C(O)=O HDSRNIXCERVTSZ-UHFFFAOYSA-N 0.000 claims description 2
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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
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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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
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- Health & Medical Sciences (AREA)
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- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0031315.5A GB0031315D0 (en) | 2000-12-21 | 2000-12-21 | Indole derivatives |
| PCT/GB2001/005701 WO2002050031A1 (en) | 2000-12-21 | 2001-12-20 | Indole derivatives |
Publications (3)
| Publication Number | Publication Date |
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| JP2004517098A JP2004517098A (ja) | 2004-06-10 |
| JP2004517098A5 JP2004517098A5 (US07794700-20100914-C00152.png) | 2005-12-22 |
| JP4460830B2 true JP4460830B2 (ja) | 2010-05-12 |
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| JP2002551528A Expired - Fee Related JP4460830B2 (ja) | 2000-12-21 | 2001-12-20 | インドール誘導体 |
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| HN2001000224A (es) | 2000-10-19 | 2002-06-13 | Pfizer | Compuestos de imidazol condensado con arilo o heteroarilo como agentes anti - inflamatorios y analgesicos. |
| SE0301446D0 (sv) | 2003-05-16 | 2003-05-16 | Astrazeneca Ab | New Compounds |
| SE0402284D0 (sv) * | 2004-09-21 | 2004-09-21 | Astrazeneca Ab | New heterocyclic amides |
| JP2008518957A (ja) * | 2004-11-04 | 2008-06-05 | メルク エンド カムパニー インコーポレーテッド | ナイアシン受容体作動薬、そのような化合物を含んでいる組成物及び治療方法 |
| US8053454B2 (en) | 2005-10-06 | 2011-11-08 | Exelixis, Inc. | Pyridopyrimidinone inhibitors of PIM-1 and/or PIM-3 |
| AR058705A1 (es) * | 2005-12-23 | 2008-02-20 | Astrazeneca Ab | Compuestos de bencimidazol como inhibidores del receptor vaniloide 1 (vr1) |
| UY30121A1 (es) | 2006-02-03 | 2007-08-31 | Glaxo Group Ltd | Nuevos compuestos |
| CA2648729A1 (en) * | 2006-04-24 | 2007-11-01 | Merck Frosst Canada Ltd. | Indole amide derivatives as ep4 receptor antagonists |
| TWI433839B (zh) * | 2006-08-11 | 2014-04-11 | Neomed Inst | 新穎的苯并咪唑衍生物290 |
| US20100074896A1 (en) * | 2006-11-30 | 2010-03-25 | The Johns Hopkins University | Antagonists of pge2 ep3 receptors |
| KR20090089868A (ko) | 2006-12-15 | 2009-08-24 | 글락소 그룹 리미티드 | Ｅｐ４ 수용체 작동제로서 벤즈아미드 유도체 |
| GB0701970D0 (en) * | 2007-02-01 | 2007-03-14 | Wilson Stuart | Treatment of protein aggregation diseases |
| EP2460787A1 (en) * | 2007-07-03 | 2012-06-06 | Astellas Pharma Inc. | Amide compounds and their use as PGE2 antagonists. |
| GB0721611D0 (en) | 2007-11-02 | 2007-12-12 | Glaxo Group Ltd | Novel compounds |
| PT2565191E (pt) * | 2008-05-14 | 2014-12-04 | Astellas Pharma Inc | Derivados do ácido 4-(indol-7- ilcarbonilaminometil)ciclo-hexanocarboxílico como antagonistas de receptores ep4, úteis no tratamento de insuficiência renal crónica ou de nefropatia diabética |
| WO2010087425A1 (ja) | 2009-01-30 | 2010-08-05 | 国立大学法人京都大学 | 前立腺癌の進行抑制剤および進行抑制方法 |
| JP5758395B2 (ja) * | 2009-10-15 | 2015-08-05 | ザ チルドレンズ メディカル センター コーポレイション | 疼痛を治療するためのセピアプテリンレダクターゼ阻害薬 |
| US8889730B2 (en) | 2012-04-10 | 2014-11-18 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| US20140303121A1 (en) | 2013-03-15 | 2014-10-09 | Plexxikon Inc. | Heterocyclic compounds and uses thereof |
| NZ630875A (en) * | 2013-03-15 | 2017-12-22 | Plexxikon Inc | Heterocyclic compounds and uses thereof |
| US9394285B2 (en) | 2013-03-15 | 2016-07-19 | Pfizer Inc. | Indole and indazole compounds that activate AMPK |
| ES2954717T3 (es) * | 2017-05-22 | 2023-11-23 | Ono Pharmaceutical Co | Antagonista de EP4 |
| CN111194318B (zh) | 2017-10-13 | 2023-06-09 | Opna生物公司 | 用于调节激酶的化合物固体形式 |
| JPWO2022102731A1 (US07794700-20100914-C00152.png) | 2020-11-13 | 2022-05-19 |
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| US4251446A (en) * | 1977-03-01 | 1981-02-17 | Sterling Drug Inc. | Phthalide compounds, processes and marking systems |
| US4322352A (en) * | 1979-04-04 | 1982-03-30 | Sterling Drug Inc. | Indolyl phthalide compounds |
| JPS62138469A (ja) * | 1985-12-11 | 1987-06-22 | Yoshitomi Pharmaceut Ind Ltd | インド−ル誘導体 |
| US5075313A (en) * | 1990-09-13 | 1991-12-24 | Eli Lilly And Company | 3-aryl-4(3H)quinazolinone CCK antagonists and pharmaceutical formulations thereof |
| GB9022785D0 (en) * | 1990-10-19 | 1990-12-05 | Merck Sharp & Dohme | Therapeutic agents |
| CA2240115A1 (en) * | 1995-12-14 | 1997-06-19 | Wallace T. Ashton | Antagonists of gonadotropin releasing hormone |
| CA2264020A1 (en) * | 1996-08-26 | 1998-03-05 | Jean Bemis | Inhibitors of phospholipase enzymes |
| JPH1171336A (ja) * | 1997-06-25 | 1999-03-16 | Mitsubishi Chem Corp | アミド誘導体 |
| AU753360B2 (en) * | 1998-07-31 | 2002-10-17 | Nippon Soda Co., Ltd. | Phenylazole compounds, process for producing the same and drugs for hyperlipemia |
| US6437146B1 (en) | 1998-09-25 | 2002-08-20 | Fujisawa Pharmaceutical Co., Ltd. | Oxazole compounds as prostaglandin e2 agonists or antagonists |
| WO2000021532A1 (en) | 1998-10-15 | 2000-04-20 | Merck & Co., Inc. | Methods for inhibiting bone resorption |
| GB9902455D0 (en) * | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| WO2002016311A1 (fr) * | 2000-08-22 | 2002-02-28 | Ono Pharmaceutical Co., Ltd. | Derives d'acide carboxylique, procede de production de ceux-ci et medicaments contenant ceux-ci comme principe actif |
| EP1346982B1 (en) * | 2000-12-28 | 2011-09-14 | Daiichi Pharmaceutical Co., Ltd. | Vla-4 inhibitors |
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2000
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2001
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- 2001-12-20 AU AU2002217286A patent/AU2002217286A1/en not_active Abandoned
- 2001-12-20 ES ES01271354T patent/ES2282195T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US20040092569A1 (en) | 2004-05-13 |
| GB0031315D0 (en) | 2001-02-07 |
| US7288564B2 (en) | 2007-10-30 |
| DE60126652D1 (de) | 2007-03-29 |
| EP1343757B1 (en) | 2007-02-14 |
| ES2282195T3 (es) | 2007-10-16 |
| EP1343757A1 (en) | 2003-09-17 |
| ATE353875T1 (de) | 2007-03-15 |
| AU2002217286A1 (en) | 2002-07-01 |
| DE60126652T2 (de) | 2008-02-28 |
| WO2002050031A1 (en) | 2002-06-27 |
| JP2004517098A (ja) | 2004-06-10 |
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