JP2010510202A - 置換ビシクロカルボキシアミド化合物 - Google Patents
置換ビシクロカルボキシアミド化合物 Download PDFInfo
- Publication number
- JP2010510202A JP2010510202A JP2009536817A JP2009536817A JP2010510202A JP 2010510202 A JP2010510202 A JP 2010510202A JP 2009536817 A JP2009536817 A JP 2009536817A JP 2009536817 A JP2009536817 A JP 2009536817A JP 2010510202 A JP2010510202 A JP 2010510202A
- Authority
- JP
- Japan
- Prior art keywords
- pyrazol
- methyl
- ethyl
- quinoline
- carboxamide
- 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.)
- Withdrawn
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- MTPVUVINMAGMJL-UHFFFAOYSA-N trimethyl(1,1,2,2,2-pentafluoroethyl)silane Chemical compound C[Si](C)(C)C(F)(F)C(F)(F)F MTPVUVINMAGMJL-UHFFFAOYSA-N 0.000 description 1
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
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| US98334307P | 2007-10-29 | 2007-10-29 | |
| PCT/IB2007/003559 WO2008059370A2 (en) | 2006-11-17 | 2007-11-09 | Substituted bicyclocarboxyamide compounds |
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| JP2010510202A true JP2010510202A (ja) | 2010-04-02 |
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| TWI491595B (zh) * | 2009-05-07 | 2015-07-11 | 歌林達股份有限公司 | 作為香草類化合物受體之配體之經取代苯基尿素及苯基醯胺 |
| AR076753A1 (es) * | 2009-05-07 | 2011-07-06 | Gruenenthal Chemie | Derivados de carboxamida y urea aromaticas sustituidas como ligandos del receptor de vanilloides. |
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| 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 |
| WO2020164993A1 (en) | 2019-02-13 | 2020-08-20 | Syngenta Crop Protection Ag | Pesticidally active pyrazole derivatives |
| WO2020164994A1 (en) | 2019-02-13 | 2020-08-20 | Syngenta Crop Protection Ag | Pesticidally active pyrazole derivatives |
| 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 |
| 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 |
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Family Cites Families (63)
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| JP4865129B2 (ja) | 1999-01-13 | 2012-02-01 | ザ・リサーチ・ファウンデーション・オブ・ステイト・ユニバーシティ・オブ・ニューヨーク | タンパク質キナーゼ阻害剤を設計するための新規の方法 |
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| HU227197B1 (en) | 2000-10-24 | 2010-10-28 | Richter Gedeon Nyrt | Nmda receptor antagonist carboxylic acid amide derivatives and pharmaceutical compositions containing them |
| JP2005511478A (ja) | 2001-04-03 | 2005-04-28 | メルク エンド カムパニー インコーポレーテッド | Ｎ−置換非アリール複素環アミジル系ｎｍｄａ／ｎｒ２ｂ拮抗薬 |
| DE60231868D1 (de) | 2001-04-24 | 2009-05-20 | Purdue Research Foundation | Folat-mimetika und deren folatrezeptorbindende konjugate |
| 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 |
| JP2005501873A (ja) | 2001-07-31 | 2005-01-20 | バイエル・ヘルスケア・アクチェンゲゼルシャフト | アミン誘導体 |
| DE60226756D1 (de) | 2001-10-04 | 2008-07-03 | Merck & Co Inc | Heteroarylsubstituierte tetrazolmodulatoren des metabotropischen glutamatrezeptors-5 |
| US20050009812A1 (en) | 2001-10-05 | 2005-01-13 | Takuya Seko | Remedies for stress diseases comprising mitochondrial benzodiazepine receptor antagonists |
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| WO2003045920A1 (en) | 2001-11-27 | 2003-06-05 | Merck & Co., Inc. | 4-aminoquinoline compounds |
| AU2003245773A1 (en) * | 2002-02-15 | 2003-09-04 | Glaxo Group Limited | Vanilloid receptor modulators |
| 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 |
| US7598418B2 (en) | 2002-04-18 | 2009-10-06 | Institute Of Medicinal Molecular Design, Inc. | Amide derivatives |
| JP2006511445A (ja) | 2002-06-07 | 2006-04-06 | コーティカル・ピーティーワイ・リミテッド | マクロファージ遊走阻止因子（ｍｉｆ）のサイトカインまたは生物学的活性を阻害するナフタレン誘導体 |
| GB2389580A (en) | 2002-06-12 | 2003-12-17 | Bayer Ag | 2-Naphthamide PGI2 antagonists |
| AU2003262946A1 (en) | 2002-08-30 | 2004-03-19 | Pharmacia And Upjohn Company | Method of preventing or treating atherosclerosis or restenosis |
| WO2004047743A2 (en) | 2002-11-22 | 2004-06-10 | Bristol-Myers Squibb Company | 1-aryl-2-hydroxyethyl amides as potassium channel openers |
| US6900210B2 (en) | 2002-11-22 | 2005-05-31 | 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 |
| US20060111357A1 (en) | 2002-12-11 | 2006-05-25 | Frimurer Thomas M | Quinoline compounds for use in mch receptor related disorders |
| EP1585511B1 (en) | 2002-12-20 | 2013-01-23 | Amgen Inc. | Asthma and allergic inflammation modulators |
| MXPA05006568A (es) | 2002-12-20 | 2005-09-22 | Pharmacia Corp | Compuestos de pirazol aciclico para la inhibicion de proteina cinasa-2 activada por proteina cinasa activada por mitogenos. |
| EP2308848A1 (en) | 2003-02-03 | 2011-04-13 | Janssen Pharmaceutica NV | Quinoline-derived amide modulators of vanilloid VR1 receptor |
| JP2006519258A (ja) | 2003-02-28 | 2006-08-24 | エンサイシブ・ファーマシューティカルズ・インコーポレイテッド | ピリジン、ピリミジン、キノリン、キナゾリンおよびナフタレン系のウロテンシン−ｉｉ受容体拮抗薬 |
| EP1601357A4 (en) | 2003-03-10 | 2007-10-03 | Schering Corp | HETEROCYCLIC KINASE INHIBITORS: METHOD OF USE AND SYNTHESIS |
| WO2004104018A2 (en) | 2003-05-14 | 2004-12-02 | Emisphere Technologies, Inc. | Compositions for delivering peptide yy and pyy agonists |
| EP1628661A2 (en) | 2003-06-05 | 2006-03-01 | Vertex Pharmaceuticals Incorporated | Modulators of vr1 receptor |
| RU2401836C2 (ru) | 2003-06-20 | 2010-10-20 | Галдерма Ресерч энд Девелопмент, С.Н.С. | НОВЫЕ СОЕДИНЕНИЯ, КОТОРЫЕ МОДУЛИРУЮТ РЕЦЕПТОРЫ ТИПА PPARγ, И ИХ ПРИМЕНЕНИЕ В КОСМЕТИЧЕСКИХ И ФАРМАЦЕВТИЧЕСКИХ КОМПОЗИЦИЯХ |
| KR100707123B1 (ko) | 2003-07-02 | 2007-04-16 | 그뤼넨탈 게엠베하 | 바닐로이드 수용체의 길항제로서 강력한 진통효과를나타내는 4-(메틸설포닐아미노)페닐 동족체 및 이를함유하는 약학적 조성물 |
| AU2004259675A1 (en) | 2003-07-15 | 2005-02-03 | Merck & Co., Inc. | Hydroxypyridine CGRP receptor antagonists |
| SE0302323D0 (sv) * | 2003-08-28 | 2003-08-28 | Astrazeneca Ab | Novel compounds |
| CA2536788A1 (en) | 2003-08-29 | 2005-03-10 | Pfizer Inc. | Naphthalene carboxamides and their derivatives useful as new anti-angiogenic agents |
| US20050232818A1 (en) * | 2003-09-19 | 2005-10-20 | Donald Sandell | Single sheet seal applicator and cartridge |
| WO2005033079A1 (ja) | 2003-09-30 | 2005-04-14 | Eisai Co., Ltd. | ヘテロ環化合物を含有する新規な抗真菌剤 |
| WO2005035526A1 (en) | 2003-10-09 | 2005-04-21 | Argenta Discovery Ltd. | Bicyclic compounds and their therapeutic use |
| AU2005206561A1 (en) | 2004-01-23 | 2005-08-04 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| US7544803B2 (en) * | 2004-01-23 | 2009-06-09 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments |
| US20050165032A1 (en) | 2004-01-23 | 2005-07-28 | Norman Mark H. | Vanilloid receptor ligands and their use in treatments |
| WO2005087742A1 (en) | 2004-03-08 | 2005-09-22 | Exelixis, Inc. | Metabolic kinase modulators and methods of use as pesticides |
| AU2005238386A1 (en) | 2004-04-30 | 2005-11-10 | Takeda Pharmaceutical Company Limited | 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 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
- 2007-11-09 JP JP2009536817A patent/JP2010510202A/ja not_active Withdrawn
- 2007-11-15 PE PE2007001571A patent/PE20081504A1/es not_active Application Discontinuation
- 2007-11-15 CL CL200703289A patent/CL2007003289A1/es unknown
- 2007-11-16 GT GT200700103A patent/GT200700103A/es unknown
- 2007-11-16 AR ARP070105111A patent/AR064253A1/es unknown
- 2007-11-16 UY UY30723A patent/UY30723A1/es not_active Application Discontinuation
- 2007-11-16 TW TW096143519A patent/TW200831089A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US7964732B2 (en) | 2011-06-21 |
| ATE509925T1 (de) | 2011-06-15 |
| US20100267769A1 (en) | 2010-10-21 |
| AR064253A1 (es) | 2009-03-25 |
| WO2008059370A3 (en) | 2008-07-24 |
| WO2008059370A8 (en) | 2009-06-04 |
| PE20081504A1 (es) | 2008-10-30 |
| TW200831089A (en) | 2008-08-01 |
| UY30723A1 (es) | 2008-07-03 |
| EP2091944B1 (en) | 2011-05-18 |
| WO2008059370A2 (en) | 2008-05-22 |
| GT200700103A (es) | 2008-11-04 |
| CL2007003289A1 (es) | 2008-06-20 |
| EP2091944A2 (en) | 2009-08-26 |
| CA2669915C (en) | 2012-02-07 |
| CA2669915A1 (en) | 2008-05-22 |
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