TW200831089A - Substituted bicyclocarboxyamide compounds - Google Patents
Substituted bicyclocarboxyamide compounds Download PDFInfo
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- TW200831089A TW200831089A TW096143519A TW96143519A TW200831089A TW 200831089 A TW200831089 A TW 200831089A TW 096143519 A TW096143519 A TW 096143519A TW 96143519 A TW96143519 A TW 96143519A TW 200831089 A TW200831089 A TW 200831089A
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- Prior art keywords
- ethyl
- methyl
- compound
- pain
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
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Landscapes
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| CN114989546A (zh) * | 2022-07-05 | 2022-09-02 | 上海乐纯生物技术有限公司 | 一种用于细胞治疗储液袋生产的fep膜 |
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| MX2011011800A (es) | 2009-05-07 | 2012-01-27 | Gruenenthal Gmbh | Derivados de carboxamida y urea aromaticas sustituidas como ligandos del receptor de vanilloides. |
| ES2640257T3 (es) * | 2009-05-07 | 2017-11-02 | Medifron Dbt Inc. | Fenilureas y fenilamidas sustituidas como ligandos del receptor vanilloide |
| US8946204B2 (en) | 2009-05-07 | 2015-02-03 | Gruenenthal Gmbh | Substituted phenylureas and phenylamides as vanilloid receptor ligands |
| WO2012025469A1 (en) * | 2010-08-24 | 2012-03-01 | Solvay Sa | Improved process for the preparation of esters of 1-h-pyrazole-4-carboxylic acids |
| WO2012062463A1 (en) * | 2010-11-10 | 2012-05-18 | Grünenthal GmbH | Substituted bicyclic carboxamide and urea derivatives as vanilloid receptor ligands |
| JP5140776B1 (ja) * | 2012-09-05 | 2013-02-13 | タマ化学工業株式会社 | １−置換−３−フルオロアルキルピラゾール−４−カルボン酸エステルの製造方法 |
| EP3702355B1 (en) | 2015-05-18 | 2022-01-12 | Shenyang Sinochem Agrochemicals R&D Co., Ltd. | Substituted pyrazole compounds containing pyrimidine, the preparation and application thereof |
| AR112673A1 (es) | 2017-08-11 | 2019-11-27 | Syngenta Participations Ag | Derivados de pirazol activos como plaguicidas |
| WO2020164994A1 (en) | 2019-02-13 | 2020-08-20 | Syngenta Crop Protection Ag | Pesticidally active pyrazole derivatives |
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| CN110256342B (zh) * | 2019-07-16 | 2022-06-07 | 河南省科学院化学研究所有限公司 | 一种2-氰基喹啉衍生物的合成方法 |
| CN110734401A (zh) * | 2019-10-10 | 2020-01-31 | 长沙麓兴生物科技有限公司 | 一种氮未取代-4-甲酰基吡唑的制备方法 |
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Family Cites Families (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2671059B2 (ja) | 1990-11-30 | 1997-10-29 | 富士レビオ株式会社 | ナフトエ酸誘導体 |
| WO1994003432A1 (en) | 1992-08-07 | 1994-02-17 | The Government Of The United States As Represented By The Secretary, Department Of Health And Human Services | Polyhydroxylated naphthyl 2-carboxylate, and quinolyl and isoquinolyl 3-carboxylate derivatives as protein tyrosine kinase inhibitors |
| CA2150345A1 (en) | 1993-09-28 | 1995-04-06 | Makoto Komatsu | Quinoxaline derivative as antidiabetic agent |
| DE4423353A1 (de) | 1994-07-04 | 1996-01-11 | Bayer Ag | Verfahren zur Herstellung N-acylierter 2-Chlor-5-aminomethylpyridine |
| US5753700A (en) | 1994-12-28 | 1998-05-19 | Ono Pharmaceutical Co., Ltd. | Naphthyloxyacetic acid derivatives |
| US5585388A (en) | 1995-04-07 | 1996-12-17 | Sibia Neurosciences, Inc. | Substituted pyridines useful as modulators of acetylcholine receptors |
| US6979686B1 (en) | 2001-12-07 | 2005-12-27 | Pharmacia Corporation | Substituted pyrazoles as p38 kinase inhibitors |
| WO1999024442A1 (en) | 1997-11-12 | 1999-05-20 | Ariad Pharmaceuticals, Inc. | Novel signal transduction inhibitors, compositions containing them |
| CA2311131A1 (en) | 1997-11-21 | 1999-06-03 | Nps Pharmaceuticals, Inc. | Metabotropic glutamate receptor antagonists for treating central nervous system diseases |
| AU3208200A (en) | 1999-01-13 | 2000-08-01 | Research Foundation Of The State University Of New York, The | A novel method for designing protein kinase inhibitors |
| JP2002534512A (ja) | 1999-01-15 | 2002-10-15 | ノボ ノルディスク アクティーゼルスカブ | 非ペプチドｇｌｐ−１アゴニスト |
| CZ20013833A3 (cs) | 1999-04-28 | 2002-02-13 | Aventis Pharma Deutschland Gmbh | Deriváty kyselin se dvěma arylovými zbytky jako ligandy receptorů PPAR a farmaceutické prostředky, které je obsahují |
| CA2374820A1 (en) | 1999-05-24 | 2000-11-30 | Cor Therapeutics, Inc. | Inhibitors of factor xa |
| CA2376024A1 (en) | 1999-06-02 | 2000-12-07 | Nps Pharmaceuticals, Inc. | Metabotropic glutamate receptor antagonists and their use for treating central nervous system diseases |
| EP1192132B1 (en) | 1999-06-14 | 2005-09-07 | Eli Lilly And Company | Serine protease inhibitors |
| WO2000076970A2 (en) | 1999-06-14 | 2000-12-21 | Eli Lilly And Company | Serine protease inhibitors |
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| DE19963179B4 (de) | 1999-12-27 | 2009-02-05 | Grünenthal GmbH | Substituierte 1- und 2-Naphthol-Mannichbasen |
| WO2002000651A2 (en) | 2000-06-27 | 2002-01-03 | Bristol-Myers Squibb Pharma Company | Factor xa inhibitors |
| CN100439332C (zh) | 2000-08-21 | 2008-12-03 | 株式会社太平洋 | 硫脲衍生物以及包含该衍生物的药物组合物 |
| HU227197B1 (en) | 2000-10-24 | 2010-10-28 | Richter Gedeon Nyrt | Nmda receptor antagonist carboxylic acid amide derivatives and pharmaceutical compositions containing them |
| US7259157B2 (en) | 2001-04-03 | 2007-08-21 | Merck & Co., Inc. | N-substituted nonaryl-heterocyclo amidyl NMDA/NR2B Antagonists |
| EP1389209B1 (en) | 2001-04-24 | 2009-04-08 | Purdue Research Foundation | Folate mimetics and folate-receptor binding conjugates thereof |
| TWI239942B (en) | 2001-06-11 | 2005-09-21 | Dainippon Pharmaceutical Co | N-arylphenylacetamide derivative and pharmaceutical composition containing the same |
| FR2827599A1 (fr) | 2001-07-20 | 2003-01-24 | Neuro3D | Composes derives de quinoleine et quinoxaline,preparation et utilisations |
| AU2002325381A1 (en) | 2001-07-31 | 2003-02-24 | Bayer Healthcare Ag | Naphthylurea and naphthylacetamide derivatives as vanilloid receptor 1 (vr1) antagonists |
| WO2003029210A2 (en) | 2001-10-04 | 2003-04-10 | Merck & Co. Inc. | Heteroaryl substituted tetrazole modulators of metabotropic glutamate receptor-5 |
| EP1438973A4 (en) | 2001-10-05 | 2005-07-13 | Ono Pharmaceutical Co | MEANS FOR THE TREATMENT OF STRESS-RELATED DISEASES WITH MITOCHONDRIENE BENZODIAZEPINE RECEPTOR ANTAGONISTS |
| CA2464214C (en) | 2001-10-22 | 2011-02-08 | The Research Foundation Of State University Of New York | Protein kinase and phosphatase inhibitors, methods for designing them, and methods of using them |
| AU2002352868A1 (en) | 2001-11-27 | 2003-06-10 | Merck & Co., Inc. | 4-aminoquinoline compounds |
| JP2005526723A (ja) * | 2002-02-15 | 2005-09-08 | グラクソ グループ リミテッド | バニロイド受容体モジュレーター |
| US8163769B2 (en) | 2002-03-12 | 2012-04-24 | Abbott Laboratories | Antibacterial compounds |
| TW200306159A (en) | 2002-03-19 | 2003-11-16 | Du Pont | Bicyclic fused pyridinyl amides and advantageous compositions thereof for use as fungicides |
| GB0206876D0 (en) | 2002-03-22 | 2002-05-01 | Merck Sharp & Dohme | Therapeutic agents |
| GB2403474B (en) | 2002-04-18 | 2006-10-11 | Inst Med Molecular Design Inc | Amide derivatives |
| GB2405146A (en) | 2002-06-07 | 2005-02-23 | Cortical Pty Ltd | Napthalene derivatives which inhibit the cytokine or biological activity of macrophage migration inhibitory factor (MIF) |
| GB2389580A (en) | 2002-06-12 | 2003-12-17 | Bayer Ag | 2-Naphthamide PGI2 antagonists |
| US20040176366A1 (en) | 2002-08-30 | 2004-09-09 | Wathen Michael W | Method of preventing or treating atherosclerosis or restenosis |
| AU2003294441A1 (en) | 2002-11-22 | 2004-06-18 | Bristol-Myers Squibb Company | 1-aryl-2-hydroxyethyl amides as potassium channel openers |
| AU2003295782A1 (en) | 2002-11-22 | 2004-06-18 | Bristol-Myers Squibb Company | Pyridinyl, pyrimidinyl and pyrazinyl amides as potassium channel openers |
| US7179427B2 (en) * | 2002-11-25 | 2007-02-20 | Abb Lummus Global Inc. | Apparatus for countercurrent contacting of gas and solids |
| EP1572212A2 (en) | 2002-12-11 | 2005-09-14 | 7TM Pharma A/S | Quinoline compounds for use in mch receptor related disorders |
| EA011087B1 (ru) | 2002-12-20 | 2008-12-30 | Эмджен Инк. | Соединения и фармацевтические композиции для лечения воспалительных заболеваний |
| BR0317430A (pt) | 2002-12-20 | 2005-10-25 | Pharmacia Corp | Compostos inibidores de quinase-2 de proteìna ativada por quinase de proteìna ativada por mitógeno |
| ATE551324T1 (de) | 2003-02-03 | 2012-04-15 | Janssen Pharmaceutica Nv | Chinolin-amid-derivate als modulatoren von vanilloid-vr1-rezeptoren |
| CA2517166A1 (en) | 2003-02-28 | 2004-09-16 | Encysive Pharmaceuticals Inc. | Pyridine, pyrimidine, quinoline, quinazoline, and naphthalene urotensin-ii receptor antagonists |
| WO2004080463A1 (en) | 2003-03-10 | 2004-09-23 | Schering Corporation | Heterocyclic kinase inhibitors: methods of use and synthesis |
| JP2006528982A (ja) | 2003-05-14 | 2006-12-28 | エミスフェアー・テクノロジーズ・インク | ペプチドｙｙおよびｐｙｙ作用薬の送達用組成物 |
| US20050004133A1 (en) | 2003-06-05 | 2005-01-06 | Makings Lewis R. | Modulators of VR1 receptor |
| EP1638964B1 (en) | 2003-06-20 | 2011-07-27 | Galderma Research & Development | Novel compounds that modulate ppar-gamma type receptors, and use thereof in cosmetic or pharmaceutical compositions |
| KR100707123B1 (ko) | 2003-07-02 | 2007-04-16 | 그뤼넨탈 게엠베하 | 바닐로이드 수용체의 길항제로서 강력한 진통효과를나타내는 4-(메틸설포닐아미노)페닐 동족체 및 이를함유하는 약학적 조성물 |
| JP2007523870A (ja) | 2003-07-15 | 2007-08-23 | メルク エンド カムパニー インコーポレーテッド | ヒドロキシピリジンｃｇｒｐ受容体拮抗薬 |
| SE0302323D0 (sv) | 2003-08-28 | 2003-08-28 | Astrazeneca Ab | Novel compounds |
| JP2007504121A (ja) | 2003-08-29 | 2007-03-01 | ファイザー・インク | 新たな抗血管形成剤として有用なナフタレン・カルボキサミド及びその誘導体 |
| US20050232818A1 (en) * | 2003-09-19 | 2005-10-20 | Donald Sandell | Single sheet seal applicator and cartridge |
| EP1669348A4 (en) | 2003-09-30 | 2009-03-11 | Eisai R&D Man Co Ltd | NEW ANTIPILIC AGENT CONTAINING A HETEROCYCLIC COMPOUND |
| WO2005035526A1 (en) | 2003-10-09 | 2005-04-21 | Argenta Discovery Ltd. | Bicyclic compounds and their therapeutic use |
| US7544803B2 (en) | 2004-01-23 | 2009-06-09 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| US7553848B2 (en) | 2004-01-23 | 2009-06-30 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| JP2007524673A (ja) | 2004-01-23 | 2007-08-30 | アムジエン・インコーポレーテツド | バニロイド受容体リガンドと治療におけるその使用 |
| WO2005087742A1 (en) | 2004-03-08 | 2005-09-22 | Exelixis, Inc. | Metabolic kinase modulators and methods of use as pesticides |
| ZA200609259B (en) | 2004-04-30 | 2008-07-30 | Takeda Pharmaceutical | Heterocyclic amide compound and use thereof as an mmp-13 inhibitor |
| EP1782811A4 (en) | 2004-08-09 | 2010-09-01 | Eisai R&D Man Co Ltd | INNOVATIVE ANTIPALUDITIC AGENT CONTAINING A HETEROCYCLIC COMPOUND |
-
2007
- 2007-11-09 WO PCT/IB2007/003559 patent/WO2008059370A2/en not_active Ceased
- 2007-11-09 JP JP2009536817A patent/JP2010510202A/ja not_active Withdrawn
- 2007-11-09 CA CA2669915A patent/CA2669915C/en not_active Expired - Fee Related
- 2007-11-09 AT AT07825705T patent/ATE509925T1/de not_active IP Right Cessation
- 2007-11-09 US US12/063,159 patent/US7964732B2/en not_active Expired - Fee Related
- 2007-11-09 EP EP07825705A patent/EP2091944B1/en not_active Not-in-force
- 2007-11-15 CL CL200703289A patent/CL2007003289A1/es unknown
- 2007-11-15 PE PE2007001571A patent/PE20081504A1/es not_active Application Discontinuation
- 2007-11-16 UY UY30723A patent/UY30723A1/es not_active Application Discontinuation
- 2007-11-16 AR ARP070105111A patent/AR064253A1/es unknown
- 2007-11-16 TW TW096143519A patent/TW200831089A/zh unknown
- 2007-11-16 GT GT200700103A patent/GT200700103A/es unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114989546A (zh) * | 2022-07-05 | 2022-09-02 | 上海乐纯生物技术有限公司 | 一种用于细胞治疗储液袋生产的fep膜 |
| CN114989546B (zh) * | 2022-07-05 | 2023-07-28 | 上海乐纯生物技术有限公司 | 一种用于细胞治疗储液袋生产的fep膜 |
Also Published As
| Publication number | Publication date |
|---|---|
| US7964732B2 (en) | 2011-06-21 |
| GT200700103A (es) | 2008-11-04 |
| CL2007003289A1 (es) | 2008-06-20 |
| ATE509925T1 (de) | 2011-06-15 |
| WO2008059370A2 (en) | 2008-05-22 |
| EP2091944A2 (en) | 2009-08-26 |
| US20100267769A1 (en) | 2010-10-21 |
| PE20081504A1 (es) | 2008-10-30 |
| UY30723A1 (es) | 2008-07-03 |
| WO2008059370A8 (en) | 2009-06-04 |
| CA2669915A1 (en) | 2008-05-22 |
| JP2010510202A (ja) | 2010-04-02 |
| EP2091944B1 (en) | 2011-05-18 |
| AR064253A1 (es) | 2009-03-25 |
| CA2669915C (en) | 2012-02-07 |
| WO2008059370A3 (en) | 2008-07-24 |
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