KR101103143B1 - 테트라졸-치환된 아릴아마이드 - Google Patents

테트라졸-치환된 아릴아마이드 Download PDF

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KR101103143B1
KR101103143B1 KR1020087031545A KR20087031545A KR101103143B1 KR 101103143 B1 KR101103143 B1 KR 101103143B1 KR 1020087031545 A KR1020087031545 A KR 1020087031545A KR 20087031545 A KR20087031545 A KR 20087031545A KR 101103143 B1 KR101103143 B1 KR 101103143B1
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methyl
ethyl
tetrazol
biphenyl
carboxylic acid
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KR20090014221A (ko
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리 첸
마이클 패트릭 딜런
리춘 펭
로날드 찰스 홀리
민민 양
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에프. 호프만-라 로슈 아게
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Families Citing this family (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2091927B1 (en) * 2006-11-09 2011-07-20 F. Hoffmann-La Roche AG Thiazole and oxazole-substituted arylamides
US8501933B2 (en) 2006-11-09 2013-08-06 Roche Palo Alto Llc Thiazole and oxazole-substituted arylamides as P2X3 and P2X2/3 antagonists
MX2010003156A (es) * 2007-10-04 2010-04-01 Hoffmann La Roche Derivados de aril amida substituida con tetrazol y usos de los mismos.
AU2008319309B2 (en) * 2007-10-31 2012-09-06 Merck Sharp & Dohme Llc P2X3 receptor antagonists for treatment of pain
CA2703909A1 (en) * 2007-10-31 2009-05-07 Merck Sharp & Dohme Corp. P2x3, receptor antagonists for treatment of pain
CA2708791C (en) * 2007-12-17 2016-06-21 F. Hoffmann-La Roche Ag Imidazole-substituted arylamides and uses thereof as p2x receptor antagonists
AU2013273626B2 (en) * 2007-12-17 2016-04-28 F.Hoffmann-La Roche Ag Triazole-substituted arylamide derivatives and their use as P2X3 and /or P2X2/3 purinergic receptor antagonists
ES2417182T3 (es) 2007-12-17 2013-08-06 F. Hoffmann-La Roche Ag Nuevas arilamidas sustituidas con pirazol
ES2542245T3 (es) * 2007-12-17 2015-08-03 F. Hoffmann-La Roche Ag Derivados de arilamida sustituido con triazol y su utilización como antagonistas del receptor purinérgico P2x3 y/o P2x2/3
EP2234989B1 (en) * 2007-12-17 2014-08-13 F. Hoffmann-La Roche AG Tetrazole-substituted arylamide derivatives and their use as p2x3 and/or p2x2/3 purinergic receptor antagonists
MX2010009561A (es) 2008-02-29 2010-09-24 Renovis Inc Compuestos amida, composiciones y usos de los mismos.
CA2737038A1 (en) * 2008-09-18 2010-03-25 Evotec Ag Amide compounds, compositions and uses thereof
ES2534199T3 (es) * 2008-10-31 2015-04-20 Merck Sharp & Dohme Corp. Antagonistas del receptor P2X3 para el tratamiento del dolor
EP2379518B1 (en) 2008-12-16 2014-05-07 F. Hoffmann-La Roche AG Thiadiazole-substituted arylamides
AU2010229144B2 (en) 2009-03-23 2012-07-12 Merck Sharp & Dohme Corp. P2X3, receptor antagonists for treatment of pain
US8946231B2 (en) 2009-03-23 2015-02-03 Merck Sharp & Dohme Corp. P2X3, receptor antagonists for treatment of pain
WO2010111058A1 (en) 2009-03-23 2010-09-30 Merck Sharp & Dohme Corp. P2x3, receptor antagonists for treatment of pain
EP2246259B1 (en) 2009-04-29 2012-12-12 Eurocopter Deutschland GmbH Rotor wing with integrated tension-torque-transmission element and method for its production
EP2435407B1 (en) * 2009-05-29 2019-12-25 RaQualia Pharma Inc. Aryl substituted carboxamide derivatives as calcium or sodium channel blockers
AR077033A1 (es) * 2009-06-11 2011-07-27 Hoffmann La Roche Compuestos inhibidores de las quinasas de janus y su uso en el tratamiento de enfermedades inmunologicas
US8476457B2 (en) 2009-06-22 2013-07-02 Roche Palo Alto Llc Indole, indazole and benzimidazole arylamides as P2X3 and P2X2/3 antagonists
EP2445889B1 (en) * 2009-06-22 2016-08-10 F.Hoffmann-La Roche Ag Novel benzoxazolone -substituted arylamides
CN102574778B (zh) * 2009-06-22 2015-01-07 弗·哈夫曼-拉罗切有限公司 新的联苯基和苯基-吡啶酰胺类化合物
AU2011261375B2 (en) * 2010-06-04 2016-09-22 Albany Molecular Research, Inc. Glycine transporter-1 inhibitors, methods of making them, and uses thereof
US9598409B2 (en) * 2013-01-31 2017-03-21 Neomed Institute Imidazopyridine compounds and uses thereof
HUE058009T2 (hu) 2014-12-09 2022-06-28 Bayer Ag 1,3-Tiazol-2-il szubsztituált benzamid-származékok
US10183937B2 (en) 2014-12-09 2019-01-22 Bayer Aktiengesellschaft 1,3-thiazol-2-yl substituted benzamides
CN107207449B (zh) * 2015-04-23 2020-11-10 豪夫迈·罗氏有限公司 用于治疗精神障碍的四唑衍生物
JP6877359B2 (ja) * 2015-06-04 2021-05-26 エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ イミダゾール誘導体
CN108137566B (zh) * 2015-10-06 2021-05-25 豪夫迈·罗氏有限公司 三唑衍生物
EP3411365B1 (en) 2016-02-02 2019-11-20 H. Hoffnabb-La Roche Ag Pyrazol-pyridine derivatives as eaat3 inhibitors
TWI696615B (zh) * 2016-05-05 2020-06-21 瑞士商伊蘭科動物健康公司 雜芳基-1,2,4-三唑及雜芳基-三唑化合物
EP3464246B1 (en) 2016-05-27 2020-07-08 H. Hoffnabb-La Roche Ag Pyrazol compounds as eaat3 inhibitors
CN109563049B (zh) 2016-10-14 2022-11-29 豪夫迈·罗氏有限公司 作为eaat3抑制剂的咪唑化合物
TWI741040B (zh) * 2016-10-20 2021-10-01 德商拜耳作物科學公司 製備3-烷基硫基-2-氯-n-(1-烷基-1h-四唑-5-基)-4-三氟甲基苯甲醯胺之方法
RU2650780C1 (ru) 2016-12-06 2018-04-17 Общество с ограниченной ответственностью "Анальгетики будущего" Пептидный модулятор пуринергических рецепторов
CN114222741B (zh) 2019-05-31 2025-12-30 奇斯药制品公司 作为p2x3抑制剂的吡啶并嘧啶类衍生物
BR112021022099A2 (pt) 2019-05-31 2021-12-28 Chiesi Farm Spa Derivados de amino quinazolina como inibidores de p2x3
JP2023550830A (ja) 2020-11-27 2023-12-05 キエシ・フアルマチエウテイチ・ソチエタ・ペル・アチオニ Ｐ２ｘ３阻害剤としての（アザ）キノリン４－アミン誘導体
AU2021388923A1 (en) 2020-11-27 2023-05-25 Chiesi Farmaceutici S.P.A. Amino quinazoline derivatives as p2x3 inhibitors
KR20230113289A (ko) 2020-11-27 2023-07-28 키에시 파르마슈티시 엣스. 피. 에이. P2x3 억제제로서 프탈라진 유도체
AR131715A1 (es) * 2023-01-30 2025-04-23 Eurofarma Laboratorios S A AMIDAS BLOQUEADORAS DE Nav 1.7 Y/O Nav 1.8, SUS PROCESOS DE OBTENCIÓN, COMPOSICIONES, USOS, MÉTODOS DE TRATAMIENTO DE LOS MISMOS Y KITS

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994026709A1 (en) * 1993-05-17 1994-11-24 Fujisawa Pharmaceutical Co., Ltd. GUANIDINE DERIVATIVES AS INHIBITORS OF Na+/H+ EXCHANGE IN CELLS

Family Cites Families (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995033048A2 (en) * 1994-05-27 1995-12-07 Glaxo Group Limited P2x receptors (purinoceptor family)
US6133434A (en) * 1997-04-28 2000-10-17 Glaxo Group Limited Purinergic receptor
JP2000281664A (ja) * 1999-03-30 2000-10-10 Otsuka Pharmaceut Co Ltd チアゾール誘導体
ES2250126T3 (es) 1999-06-30 2006-04-16 H. Lundbeck A/S Antagonistas selectivos del npy(y5).
AU2001268711A1 (en) 2000-06-23 2002-01-08 Bristol-Myers Squibb Pharma Company Heteroaryl-phenyl substituted factor xa inhibitors
DE10055713A1 (de) 2000-11-10 2002-05-23 Dingwei Tim Yu Neue Klasse von Antifungimitteln
PA8557501A1 (es) * 2001-11-12 2003-06-30 Pfizer Prod Inc Benzamida, heteroarilamida y amidas inversas
AR037460A1 (es) * 2001-11-30 2004-11-10 Smithkline Beecham Plc Compuesto de hidroxietileno, composicion farmaceutica que lo comprende, uso del mismo para la fabricacion de un medicamento y procedimiento para su preparacion
WO2003063791A2 (en) 2002-01-30 2003-08-07 Entremed, Inc. Non-steroidal analogs of 2-methoxyestradiol
US20050154202A1 (en) * 2002-04-05 2005-07-14 Hagmann William K. Substituted aryl amides
US7078423B2 (en) * 2002-07-18 2006-07-18 Inotek Pharmaceuticals Corporation 5-Aryltetrazole compounds, compositions thereof, and uses therefor
JP2005533852A (ja) 2002-07-18 2005-11-10 セレテック エルエルシー Ｅｄｇ−１受容体に関連した症状の治療方法
DE10312963A1 (de) * 2003-03-24 2004-10-07 Aventis Pharma Deutschland Gmbh Substituierte 4-Phenyltetrahydroisochinoline, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament, sowie sie enthaltendes Medikament
EP1618099A4 (en) 2003-04-18 2008-07-16 Merck & Co Inc BIARYLSUBSTITUTED DIAZOLE, OXAZOLE AND IMIDAZOLE AS SODIUM CHANNEL BLOCKERS
AU2005259835B2 (en) * 2004-07-02 2011-07-07 The Walter And Eliza Hall Institute Of Medical Research Alpha-helical mimetics
CN102659774A (zh) * 2005-08-15 2012-09-12 弗·哈夫曼-拉罗切有限公司 作为p2x3拮抗剂的哌啶和哌嗪衍生物

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994026709A1 (en) * 1993-05-17 1994-11-24 Fujisawa Pharmaceutical Co., Ltd. GUANIDINE DERIVATIVES AS INHIBITORS OF Na+/H+ EXCHANGE IN CELLS

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