ZA200402754B - Benzamide and heteroarylamide as P2X7 receptor antagonists. - Google Patents
Benzamide and heteroarylamide as P2X7 receptor antagonists. Download PDFInfo
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- ZA200402754B ZA200402754B ZA200402754A ZA200402754A ZA200402754B ZA 200402754 B ZA200402754 B ZA 200402754B ZA 200402754 A ZA200402754 A ZA 200402754A ZA 200402754 A ZA200402754 A ZA 200402754A ZA 200402754 B ZA200402754 B ZA 200402754B
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- alkyl
- chloro
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- cycloalkyl
- dihydro
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Families Citing this family (73)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
PA8557501A1 (es) * | 2001-11-12 | 2003-06-30 | Pfizer Prod Inc | Benzamida, heteroarilamida y amidas inversas |
EP1581507A1 (en) * | 2002-12-31 | 2005-10-05 | Pfizer Products Inc. | Benzamide inhibitors of the p2x7 receptor |
PA8591801A1 (es) | 2002-12-31 | 2004-07-26 | Pfizer Prod Inc | Inhibidores benzamidicos del receptor p2x7. |
US7071223B1 (en) * | 2002-12-31 | 2006-07-04 | Pfizer, Inc. | Benzamide inhibitors of the P2X7 receptor |
SE0300480D0 (sv) | 2003-02-21 | 2003-02-21 | Astrazeneca Ab | Novel compounds |
EP1473367B1 (en) * | 2003-04-17 | 2007-06-27 | Affectis Pharmaceuticals AG | Means and methods for diagnosing and treating affective disorders |
BRPI0410349A (pt) * | 2003-05-12 | 2006-05-30 | Pfizer Prod Inc | inibidores de benzamida do receptor p2x7 |
EP1837330B1 (en) * | 2003-05-12 | 2012-10-24 | Pfizer Products Inc. | Benzamide inhibitors of the P2X7 receptor |
WO2004105796A1 (en) * | 2003-05-29 | 2004-12-09 | Astrazeneca Ab | A pharmaceutical composition containing a p2x7 receptor antagonist and methotrexate |
TW200507829A (en) * | 2003-05-29 | 2005-03-01 | Astrazeneca Ab | New combination |
US20070010497A1 (en) * | 2003-05-29 | 2007-01-11 | Nigel Boughton-Smith | Pharmaceutical composition comprising a p2x7 antagonist and sulfasalazine |
CN100525526C (zh) * | 2003-07-11 | 2009-08-05 | 汤姆森许可贸易公司 | 通用移动电话系统网络的覆盖微小区结构 |
WO2005019182A1 (en) * | 2003-08-20 | 2005-03-03 | Bayer Healthcare Ag | Pyrazolylmethylbenzamide derivatives as p2xt-receptor antagonists |
SE0302488D0 (sv) * | 2003-09-18 | 2003-09-18 | Astrazeneca Ab | New combination |
ZA200603515B (en) * | 2003-10-08 | 2007-11-28 | Vertex Pharma | Modulators of ATP-binding cassette transporters |
ITMI20040255A1 (it) * | 2004-02-17 | 2004-05-17 | Univ Degli Studi Milano | Sostanze ad attivita' antiangiogenica |
KR20070115583A (ko) * | 2004-06-29 | 2007-12-06 | 화이자 프로덕츠 인코포레이티드 | 루이스 산의 존재하에 트리아진의 4-위치에서 치환되지않은5-[4-(2-하이드록시-에틸)-3,5-다이옥소-4,5-다이하이드로-3h-[1,2,4]트리아진-2-일]-벤즈아마이드 유도체와옥시란과의 반응에 의해 p2x7 억제 활성을 갖는 상기유도체의 제조방법 |
WO2006003517A1 (en) * | 2004-06-29 | 2006-01-12 | Warner-Lambert Company Llc | Combination therapies utilizing benzamide inhibitors of the p2x7 receptor |
WO2006003500A1 (en) * | 2004-06-29 | 2006-01-12 | Pfizer Products Inc. | Method for preparing 5-`4-(2-hydroxy-propyl)-3,5-dioxo-4,5-dihydro-3h`1,2,4!triazin-2-yl!-benzamide derivatives by deprotecting the hydroxyl-protected precursers |
WO2006083214A1 (en) * | 2005-02-02 | 2006-08-10 | Astrazeneca Ab | Pharmaceutical composition comprising a p2x7 receptor antagonist and a hmg-coa reductase inhibitor |
WO2006104172A1 (ja) * | 2005-03-29 | 2006-10-05 | Kowa Co., Ltd. | 関節リウマチの予防及び/又は治療薬 |
WO2007008157A1 (en) * | 2005-07-11 | 2007-01-18 | Astrazeneca Ab | New combination 2 |
EP1906960A4 (en) * | 2005-07-11 | 2010-03-10 | Astrazeneca Ab | NEW COMBINATION 1 |
ES2439736T3 (es) | 2005-11-08 | 2014-01-24 | Vertex Pharmaceuticals Incorporated | Moduladores heterocíclicos de transportadores de casete de unión a ATP |
US20070117497A1 (en) * | 2005-11-22 | 2007-05-24 | Cabot Microelectronics Corporation | Friction reducing aid for CMP |
US7671221B2 (en) | 2005-12-28 | 2010-03-02 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-Binding Cassette transporters |
CA2654915C (en) * | 2006-06-29 | 2015-07-28 | F.Hoffmann-La Roche Ag | Tetrazole-substituted arylamides |
DE102006049618A1 (de) * | 2006-10-20 | 2008-05-08 | Tschesche, Harald, Prof. Dr. | Triazine und Ihre Verwendung als Metalloproteinase-Inhibitoren |
US7754739B2 (en) | 2007-05-09 | 2010-07-13 | Vertex Pharmaceuticals Incorporated | Modulators of CFTR |
CN104447716A (zh) | 2007-05-09 | 2015-03-25 | 沃泰克斯药物股份有限公司 | Cftr调节剂 |
AU2008271051C1 (en) | 2007-06-29 | 2012-10-04 | Acucela Inc. | Alkynyl phenyl derivative compounds for treating ophthalmic diseases and disorders |
PT2178865E (pt) * | 2007-07-19 | 2015-11-16 | Lundbeck & Co As H | Amidas heterocíclicas com 5 membros e compostos relacionados |
ES2615389T3 (es) | 2007-10-05 | 2017-06-06 | Acucela, Inc. | Alcoxifenilpropilaminas para el tratamiento de la degeneración macular relacionada con la edad |
US20100311749A1 (en) | 2007-10-26 | 2010-12-09 | Laura Jane Chambers | 4-benzoyl-1-substituted-piperazin-2-one derivatives as p2x7 modulators |
CA2704199C (en) * | 2007-11-01 | 2016-01-19 | Acucela Inc. | Amine derivative compounds for treating ophthalmic diseases and disorders |
CA2989620C (en) | 2007-12-07 | 2022-05-03 | Vertex Pharmaceuticals Incorporated | Processes for producing cycloalkylcarboxamido-pyridine benzoic acids |
CN101910156B (zh) | 2007-12-07 | 2013-12-04 | 沃泰克斯药物股份有限公司 | 3-(6-(1-(2,2-二氟苯并[d][1,3]间二氧杂环戊烯-5-基)环丙烷甲酰氨基)-3-甲基吡啶-2-基)苯甲酸的固体形式 |
GB0724625D0 (en) * | 2007-12-18 | 2008-01-30 | Glaxo Group Ltd | Novel compounds |
EP2271622B1 (en) | 2008-02-28 | 2017-10-04 | Vertex Pharmaceuticals Incorporated | Heteroaryl derivatives as CFTR Modulators |
PL2105164T3 (pl) | 2008-03-25 | 2011-05-31 | Affectis Pharmaceuticals Ag | Nowi antagoniści P2X7R i ich zastosowanie |
CA2736229C (en) * | 2008-09-05 | 2015-06-09 | Acucela Inc. | Sulfur-linked compounds for treating opthalmic diseases and disorders |
WO2010048332A2 (en) * | 2008-10-22 | 2010-04-29 | Acucela, Inc. | Compounds for treating ophthalmic diseases and disorders |
PL2243772T3 (pl) | 2009-04-14 | 2012-05-31 | Affectis Pharmaceuticals Ag | Nowi antagoniści p2x7r i ich zastosowanie |
US10471027B2 (en) | 2009-07-02 | 2019-11-12 | Acucela, Inc. | Pharmacology of visual cycle modulators |
EP2322149A1 (en) | 2009-11-03 | 2011-05-18 | Universidad del Pais Vasco | Methods and compositions for the treatment of ischemia |
JP2013516480A (ja) | 2010-01-07 | 2013-05-13 | セレクサゲン セラピューティクス,インク. | ヘッジホッグ阻害剤 |
WO2011085261A1 (en) * | 2010-01-08 | 2011-07-14 | Selexagen Therapeutics, Inc. | Hedgehog inhibitors |
US20130195919A1 (en) | 2010-03-05 | 2013-08-01 | President And Fellows Of Harvard College | Induced dendritic cell compositions and uses thereof |
DK3150198T3 (da) | 2010-04-07 | 2021-11-01 | Vertex Pharma | Farmaceutiske sammensætninger af 3-(6-(1-(2,2-difluorbenzo[d][1,3]dioxol-5-yl)-cyclopropancarboxamido)-3-methylpyriodin-2-yl)benzoesyre og indgivelse deraf |
WO2011141194A1 (en) | 2010-05-14 | 2011-11-17 | Affectis Pharmaceuticals Ag | Novel methods for the preparation of p2x7r antagonists |
WO2012110190A1 (en) | 2011-02-17 | 2012-08-23 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
CN103391923A (zh) | 2011-02-22 | 2013-11-13 | 埃科特莱茵药品有限公司 | 作为p2x7受体拮抗剂的苯甲酰胺衍生物 |
CA2833806A1 (en) * | 2011-04-28 | 2012-11-01 | Claire Mitchell | Method for treatment of macular degeneration by modulating p2y12 or p2x7 receptors |
WO2012163792A1 (en) | 2011-05-27 | 2012-12-06 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
WO2012163456A1 (en) | 2011-05-27 | 2012-12-06 | Affectis Pharmaceuticals Ag | Novel p2x7r antagonists and their use |
AR087274A1 (es) | 2011-07-22 | 2014-03-12 | Actelion Pharmaceuticals Ltd | Derivados de amidas heterociclicas como antagonistas de receptores p2x7 |
US9707235B1 (en) | 2012-01-13 | 2017-07-18 | University Of Kentucky Research Foundation | Protection of cells from degeneration and treatment of geographic atrophy |
WO2013108227A1 (en) | 2012-01-20 | 2013-07-25 | Actelion Pharmaceuticals Ltd | Heterocyclic amide derivatives as p2x7 receptor antagonists |
TWI598325B (zh) * | 2012-10-12 | 2017-09-11 | H 朗德貝克公司 | 苯甲醯胺類 |
TW201427947A (zh) | 2012-10-12 | 2014-07-16 | Lundbeck & Co As H | 環狀胺 |
AU2013356850B2 (en) | 2012-12-12 | 2018-02-01 | Idorsia Pharmaceuticals Ltd | Indole carboxamide derivatives as P2X7 receptor antagonists |
CN104854087B (zh) | 2012-12-18 | 2017-03-22 | 埃科特莱茵药品有限公司 | 作为p2x7受体拮抗剂的吲哚羧酰胺衍生物 |
CN104918617B (zh) | 2013-01-22 | 2017-05-10 | 埃科特莱茵药品有限公司 | 作为p2x7受体拮抗剂的杂环酰胺衍生物 |
CN104918946B (zh) | 2013-01-22 | 2017-03-29 | 埃科特莱茵药品有限公司 | 作为p2x7受体拮抗剂的杂环酰胺衍生物 |
WO2015004028A1 (de) | 2013-07-08 | 2015-01-15 | Bayer Cropscience Ag | Sechsgliedrige c-n-verknüpfte arylsulfid- und arylsulfoxid- derivate als schädlingsbekämpfungsmittel |
US10231932B2 (en) | 2013-11-12 | 2019-03-19 | Vertex Pharmaceuticals Incorporated | Process of preparing pharmaceutical compositions for the treatment of CFTR mediated diseases |
US9988373B2 (en) | 2013-12-26 | 2018-06-05 | Shionogi & Co., Ltd. | Nitrogen-containing six-membered cyclic derivatives and pharmaceutical composition comprising the same |
JP6494757B2 (ja) | 2014-11-18 | 2019-04-03 | バーテックス ファーマシューティカルズ インコーポレイテッドVertex Pharmaceuticals Incorporated | ハイスループット試験高速液体クロマトグラフィーを行うプロセス |
BR112017022654A2 (pt) | 2015-04-24 | 2018-07-10 | Shionogi & Co., Ltd. | derivado heterocíclico de 6 membros e composição farmacêutica compreendendo o mesmo |
KR102528627B1 (ko) | 2016-10-17 | 2023-05-03 | 시오노기 앤드 컴파니, 리미티드 | 2환성 함질소 헤테로환 유도체 및 그를 함유하는 의약 조성물 |
CN106674098B (zh) * | 2016-12-23 | 2019-07-02 | 中国医科大学 | N-(3-氰基-4-烷氧基苯基)吡啶甲酰胺类化合物及其用途 |
WO2020227159A2 (en) | 2019-05-03 | 2020-11-12 | Flagship Pioneering Innovations V, Inc. | Methods of modulating immune activity |
CN114315811B (zh) * | 2021-11-19 | 2024-04-30 | 江苏恒盛药业有限公司 | 一种三氮唑类似物化合物及其制备方法和应用 |
Family Cites Families (64)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US144170A (en) * | 1873-10-28 | Improvement in scarf-clasps | ||
US158883A (en) * | 1875-01-19 | Improvement in wax-thread sewing-machines | ||
US146200A (en) * | 1874-01-06 | Improvement in wind-wheels | ||
US142194A (en) * | 1873-08-26 | William w | ||
US123378A (en) * | 1872-02-06 | Improvement in time-locks | ||
US77018A (en) * | 1868-04-21 | Improvement in dove-tail mabkers | ||
US71509A (en) * | 1867-11-26 | mcclellan | ||
US74576A (en) * | 1868-02-18 | Adam myers | ||
US71529A (en) * | 1867-11-26 | John e | ||
US128498A (en) * | 1872-07-02 | Improvement in tile-molds | ||
US144213A (en) * | 1873-11-04 | Improvement in faucets | ||
AU542544B2 (en) * | 1980-03-12 | 1985-02-28 | Nippon Kayaku Kabushiki Kaisha | Tetrahydrophthalimide derivatives |
EP0077938A3 (en) * | 1981-10-23 | 1983-08-24 | Mitsubishi Kasei Corporation | N-(3-substituted aminophenyl) tetrahydrophthalimides and herbicidal composition |
US4766233A (en) | 1984-06-12 | 1988-08-23 | Fmc Corporation | Herbicidal 2-aryl-1,2,4-triazine-3,5(2H,4H)-diones and sulfur analogs thereof |
AU578708B2 (en) | 1984-06-12 | 1988-11-03 | Fmc Corporation | Herbicidal 2-aryl-1,2,4-triazine-3,5(2h,4h)-diones and sulfuranalogs thereof |
EP0333791A1 (de) * | 1987-09-23 | 1989-09-27 | Ciba-Geigy Ag | Heterocyclische verbindungen |
US5077409A (en) | 1990-05-04 | 1991-12-31 | American Cyanamid Company | Method of preparing bis-aryl amide and urea antagonists of platelet activating factor |
US5128351A (en) | 1990-05-04 | 1992-07-07 | American Cyanamid Company | Bis-aryl amide and urea antagonists of platelet activating factor |
JP3089621B2 (ja) * | 1990-12-17 | 2000-09-18 | 日産化学工業株式会社 | ウラシル誘導体 |
BR9107169A (pt) | 1990-12-17 | 1993-11-16 | Shell Int Research | Derivados de isoquinolina fungicidas |
GB9110679D0 (en) * | 1991-05-17 | 1991-07-10 | Sandoz Ltd | Improvements in or relating to organic compounds |
GB9119467D0 (en) | 1991-09-12 | 1991-10-23 | Smithkline Beecham Corp | Chemical compounds |
US5691376A (en) | 1994-02-17 | 1997-11-25 | American Home Products Corporation | Substituted biphenyl derivatives |
DE4405614A1 (de) * | 1994-02-22 | 1995-08-24 | Bayer Ag | Substituierte Triazolinone |
US5686061A (en) | 1994-04-11 | 1997-11-11 | The Board Of Regents Of The University Of Texas System | Particulate contrast media derived from non-ionic water soluble contrast agents for CT enhancement of hepatic tumors |
GB9412603D0 (en) * | 1994-06-23 | 1994-08-10 | Sandoz Ltd | Organic compounds |
JP3144624B2 (ja) | 1995-06-02 | 2001-03-12 | 杏林製薬株式会社 | N−ベンジルジオキソチアゾリジルベンズアミド誘導体及びその製造法 |
JP3906935B2 (ja) | 1995-12-18 | 2007-04-18 | 杏林製薬株式会社 | N−置換ジオキソチアゾリジルベンズアミド誘導体及びその製造法 |
JP2001502655A (ja) | 1995-12-21 | 2001-02-27 | デュポン ファーマシューティカルズ カンパニー | Xa因子阻害薬であるイソオキサゾリン、イソチアゾリンおよびピラゾリン |
JP2000506538A (ja) | 1996-03-29 | 2000-05-30 | ジー.ディー.サール アンド カンパニー | メタ―置換フェニレン誘導体 |
US6020357A (en) | 1996-12-23 | 2000-02-01 | Dupont Pharmaceuticals Company | Nitrogen containing heteroaromatics as factor Xa inhibitors |
IL130286A0 (en) | 1996-12-23 | 2000-06-01 | Du Pont Pharm Co | Nitrogen containing heteroaromatics as factor Xa inhibitors |
US6187797B1 (en) | 1996-12-23 | 2001-02-13 | Dupont Pharmaceuticals Company | Phenyl-isoxazoles as factor XA Inhibitors |
DE19701287A1 (de) * | 1997-01-16 | 1998-07-23 | Wernicke & Co Gmbh | Verfahren zum Erhöhen der Gebrauchsdauer von Schleifscheiben |
WO1998042669A1 (en) | 1997-03-25 | 1998-10-01 | Astra Pharmaceuticals Ltd. | Novel pyridine derivatives and pharmaceutical compositions containing them |
WO1998043973A1 (de) | 1997-03-27 | 1998-10-08 | Novartis Ag | Zwischenprodukte und verfahren zur herstellung von pyrimidinderivaten |
DE19719621A1 (de) | 1997-05-09 | 1998-11-12 | Hoechst Ag | Sulfonylaminocarbonsäuren |
US6297239B1 (en) | 1997-10-08 | 2001-10-02 | Merck & Co., Inc. | Inhibitors of prenyl-protein transferase |
SE9704272D0 (sv) | 1997-11-21 | 1997-11-21 | Astra Pharma Prod | Novel Compounds |
SE9704546D0 (sv) | 1997-12-05 | 1997-12-05 | Astra Pharma Prod | Novel compounds |
SE9704545D0 (sv) | 1997-12-05 | 1997-12-05 | Astra Pharma Prod | Novel compounds |
SE9704544D0 (sv) | 1997-12-05 | 1997-12-05 | Astra Pharma Prod | Novel compounds |
JPH11318492A (ja) | 1998-03-09 | 1999-11-24 | Aisin Seiki Co Ltd | 蛍光発生性基質を含有する組成物 |
US6320078B1 (en) | 1998-07-24 | 2001-11-20 | Mitsui Chemicals, Inc. | Method of producing benzamide derivatives |
FR2783519B1 (fr) | 1998-09-23 | 2003-01-24 | Sod Conseils Rech Applic | Nouveaux derives d'amidines, leur preparation, leur application a titre de medicaments et les compositions pharmaceutiques les contenant |
DE19851184A1 (de) | 1998-11-06 | 2000-05-11 | Aventis Pharma Gmbh | N-Arylsulfonyl-aminosäure-omega-amide |
ES2249059T3 (es) | 1998-12-16 | 2006-03-16 | Bayer Healthcare Ag | Nuevos compuestos de bifenilo y analogos de bifenilo como antagonista de integrina. |
NZ514477A (en) * | 1999-04-09 | 2003-04-29 | Astrazeneca Ab | Adamantane derivatives |
CA2382751A1 (en) | 1999-05-24 | 2000-11-30 | Cor Therapeutics, Inc. | Inhibitors of factor xa |
SE9901875D0 (sv) * | 1999-05-25 | 1999-05-25 | Astra Pharma Prod | Novel compounds |
EP1088821A1 (en) | 1999-09-28 | 2001-04-04 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active sulfonamide derivatives |
MXPA02005102A (es) | 1999-10-18 | 2003-09-25 | Alexipharma Inc | Retro-anandamidas, ligandos de receptor de canabinoide de alta afinidad y estabilidad. |
SE9904505D0 (sv) * | 1999-12-09 | 1999-12-09 | Astra Pharma Prod | Novel compounds |
TWI258462B (en) | 1999-12-17 | 2006-07-21 | Astrazeneca Ab | Adamantane derivative compounds, process for preparing the same and pharmaceutical composition comprising the same |
SE9904652D0 (sv) | 1999-12-17 | 1999-12-17 | Astra Pharma Prod | Novel Compounds |
SE9904738D0 (sv) | 1999-12-22 | 1999-12-22 | Astra Pharma Prod | Novel compounds |
DE10005284A1 (de) | 2000-02-07 | 2001-08-09 | Bayer Ag | Verfahren zur Herstellung von 1-Amino-3-aryl-uracilen |
PA8557501A1 (es) | 2001-11-12 | 2003-06-30 | Pfizer Prod Inc | Benzamida, heteroarilamida y amidas inversas |
WO2003042190A1 (en) | 2001-11-12 | 2003-05-22 | Pfizer Products Inc. | N-alkyl-adamantyl derivatives as p2x7-receptor antagonists |
PA8591801A1 (es) | 2002-12-31 | 2004-07-26 | Pfizer Prod Inc | Inhibidores benzamidicos del receptor p2x7. |
BRPI0410349A (pt) | 2003-05-12 | 2006-05-30 | Pfizer Prod Inc | inibidores de benzamida do receptor p2x7 |
KR20070115583A (ko) | 2004-06-29 | 2007-12-06 | 화이자 프로덕츠 인코포레이티드 | 루이스 산의 존재하에 트리아진의 4-위치에서 치환되지않은5-[4-(2-하이드록시-에틸)-3,5-다이옥소-4,5-다이하이드로-3h-[1,2,4]트리아진-2-일]-벤즈아마이드 유도체와옥시란과의 반응에 의해 p2x7 억제 활성을 갖는 상기유도체의 제조방법 |
WO2006003500A1 (en) | 2004-06-29 | 2006-01-12 | Pfizer Products Inc. | Method for preparing 5-`4-(2-hydroxy-propyl)-3,5-dioxo-4,5-dihydro-3h`1,2,4!triazin-2-yl!-benzamide derivatives by deprotecting the hydroxyl-protected precursers |
WO2006003517A1 (en) | 2004-06-29 | 2006-01-12 | Warner-Lambert Company Llc | Combination therapies utilizing benzamide inhibitors of the p2x7 receptor |
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