NO324776B1 - Okso-2H-pyridin-, okso-2H-kinolin- og okso-1H-isokinolinderivater, deres fremstilling, farmasoytiske sammensetninger inneholdende dem og deres anvendelse - Google Patents
Okso-2H-pyridin-, okso-2H-kinolin- og okso-1H-isokinolinderivater, deres fremstilling, farmasoytiske sammensetninger inneholdende dem og deres anvendelse Download PDFInfo
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- NO324776B1 NO324776B1 NO20022656A NO20022656A NO324776B1 NO 324776 B1 NO324776 B1 NO 324776B1 NO 20022656 A NO20022656 A NO 20022656A NO 20022656 A NO20022656 A NO 20022656A NO 324776 B1 NO324776 B1 NO 324776B1
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NO20074773A NO20074773L (no) | 1999-12-08 | 2007-09-19 | Caspaseinhibitorer og anvendelse derav |
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Families Citing this family (46)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR0009610A (pt) | 1999-04-09 | 2002-02-13 | Cytovia Inc | Inibidores de caspase e uso dos mesmos |
US6723711B2 (en) | 1999-05-07 | 2004-04-20 | Texas Biotechnology Corporation | Propanoic acid derivatives that inhibit the binding of integrins to their receptors |
CA2383002A1 (en) | 1999-08-27 | 2001-03-08 | Cytovia, Inc. | Substituted .alpha.-hydroxy acid caspase inhibitors and the use thereof |
US6545004B1 (en) | 1999-10-27 | 2003-04-08 | Cytokinetics, Inc. | Methods and compositions utilizing quinazolinones |
AR026748A1 (es) * | 1999-12-08 | 2003-02-26 | Vertex Pharma | Un compuesto inhibidor de caspasas, una composicion farmaceutica que lo comprende, un metodo para la sintesis del mismo y un compuesto intermediario paradicha sintesis |
PE20011350A1 (es) | 2000-05-19 | 2002-01-15 | Vertex Pharma | PROFARMACO DE UN INHIBIDOR DE ENZIMA CONVERTIDORA DE INTERLEUCINA-1ß (ICE) |
CA2447999C (en) * | 2001-05-23 | 2011-04-26 | Vertex Pharmaceuticals Incorporated | Caspase inhibitors and uses thereof |
AU2003225088A1 (en) | 2002-04-19 | 2003-11-03 | Vertex Pharmaceuticals Incorporated | Regulation of tnf-alpha |
AR040350A1 (es) | 2002-06-28 | 2005-03-30 | Vertex Pharma | Inhibidores de caspasa y usos de los mismos |
CA2511235A1 (en) * | 2002-12-20 | 2004-07-15 | Vertex Pharmaceuticals Incorporated | 4-oxo-3-(1-oxo-1h-isoquinolin-2-ylacetylamino)-pentanoic acid ester and amide derivatives and their use as caspase inhibitors |
PE20050159A1 (es) | 2003-05-27 | 2005-04-19 | Vertex Pharma | Derivados de acido 3-[2-(3-amino-2-oxo-2h-piridin-1-il)-acetilamino]-4-oxo-pentanoico como inhibidores de caspasa |
US7465738B2 (en) | 2003-06-16 | 2008-12-16 | Vertex Pharmaceuticals Incorporated | Compounds useful as promoters of SMN2 |
CN103467459A (zh) | 2004-03-12 | 2013-12-25 | 弗特克斯药品有限公司 | 制备化合物的方法 |
EP1750689A1 (en) * | 2004-05-15 | 2007-02-14 | Vertex Pharmaceuticals Incorporated | Treating seizures using ice inhibitors |
EP1778221A2 (en) | 2004-05-27 | 2007-05-02 | Vertex Pharmaceuticals Incorporated | Ice inhibitors for the treatment of autoinflammatory diseases |
ATE543803T1 (de) | 2004-11-24 | 2012-02-15 | Vertex Pharma | 3-ä2-(3-azylamino-2-oxo-2h-pyridin-1- yl)acetylaminoü-4-oxopentansäurederivate und deren verwendung als caspase-inhibitoren |
JP2009502922A (ja) * | 2005-07-28 | 2009-01-29 | 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 | カスパーゼ阻害剤プロドラッグ |
EP2001875A2 (en) * | 2006-03-08 | 2008-12-17 | Takeda San Diego, Inc. | Glucokinase activators |
AR063417A1 (es) * | 2006-11-01 | 2009-01-28 | Astrazeneca Ab | Compuestos inhibidores del activador de plasminogeno tipo 1(pai-1) |
WO2008079787A2 (en) * | 2006-12-20 | 2008-07-03 | Takeda San Diego, Inc. | Glucokinase activators |
US8173645B2 (en) | 2007-03-21 | 2012-05-08 | Takeda San Diego, Inc. | Glucokinase activators |
WO2009140765A1 (en) | 2008-05-21 | 2009-11-26 | New World Laboratories Inc. | Selective caspase inhibitors and uses thereof |
US8518942B2 (en) * | 2008-08-06 | 2013-08-27 | Buck Institute For Research On Aging | Caspase inhibitors and uses thereof |
WO2010039545A2 (en) * | 2008-09-23 | 2010-04-08 | Georgetown University | 1,2-benzisothiazolinone and isoindolinone derivatives |
CA2738313A1 (en) * | 2008-09-23 | 2010-04-08 | Georgetown University | Viral and fungal inhibitors |
WO2010133000A1 (en) | 2009-05-21 | 2010-11-25 | New World Laboratories Inc. | Selective caspase inhibitors and uses thereof |
WO2010138585A1 (en) * | 2009-05-29 | 2010-12-02 | Merck Sharp & Dohme Corp. | Pyrimidinones as pde10 inhibitors |
WO2011031486A1 (en) | 2009-08-25 | 2011-03-17 | Lasermax Roll Systems, Inc. | System and method for inline cutting and stacking of sheets for formation of books |
US8882099B2 (en) | 2009-08-25 | 2014-11-11 | Lasermax Roll Systems, Inc. | System and method for inline cutting and stacking of sheets for formation of books |
US9365612B2 (en) | 2010-01-29 | 2016-06-14 | United States Of America As Represented By The Secretary, Department Of Health And Human Services | Caspase inhibitors |
JP5980790B2 (ja) | 2010-11-05 | 2016-08-31 | ブランダイス ユニバーシティBrandeis University | バイオマーカーとしての、ice切断されたアルファ−シヌクレイン |
WO2012135299A1 (en) | 2011-03-28 | 2012-10-04 | Deuteria Pharmaceuticals Inc | 2',6'-dioxo-3'-deutero-piperdin-3-yl-isoindoline compounds |
US9944674B2 (en) | 2011-04-15 | 2018-04-17 | Genesis Technologies Limited | Selective cysteine protease inhibitors and uses thereof |
US9956260B1 (en) | 2011-07-22 | 2018-05-01 | The J. David Gladstone Institutes | Treatment of HIV-1 infection and AIDS |
US9428472B2 (en) | 2011-08-16 | 2016-08-30 | Georgetown University | Methods of treating bacterial infections with 1,2-benzisothiazolinone and isoindolinone derivatives |
EP2943201B2 (en) | 2013-01-14 | 2020-07-29 | Deuterx, LLC | 3-(5-substituted-4-oxoquinazolin-3(4h)-yl)-3-deutero-piperidine-2,6-dione derivatives |
WO2014152833A1 (en) * | 2013-03-14 | 2014-09-25 | Deuterx, Llc | 3-(substituted-4-oxo-quinazolin-3(4h)-yl)-3-deutero-piperidine-2,6-dione derivatives |
WO2014160592A2 (en) * | 2013-03-27 | 2014-10-02 | Merck Sharp & Dohme Corp. | FACTOR XIa INHIBITORS |
US9809603B1 (en) | 2015-08-18 | 2017-11-07 | Deuterx, Llc | Deuterium-enriched isoindolinonyl-piperidinonyl conjugates and oxoquinazolin-3(4H)-yl-piperidinonyl conjugates and methods of treating medical disorders using same |
TWI764977B (zh) | 2017-01-23 | 2022-05-21 | 大陸商正大天晴藥業集團股份有限公司 | 作爲caspase抑制劑的聯環化合物、含有其的藥物組合物及其應用 |
CN106749045B (zh) * | 2017-03-03 | 2020-02-14 | 上海交通大学 | 一种d-氨基酸氧化酶抑制剂及其制法和应用 |
US11345950B2 (en) * | 2017-10-04 | 2022-05-31 | Battelle Memorial Institute | Probe for selectively characterizing enzymes involved in xenobiotic metabolism and method of making and using the same |
CA3171430A1 (en) * | 2020-03-13 | 2021-09-16 | Brent R. Stockwell | Gpx4 compounds and compositions and methods of treatment using same |
JP7566405B2 (ja) * | 2020-08-05 | 2024-10-15 | エルジー・ケム・リミテッド | 変形性関節症の緩和又は治療するためのカスパーゼ阻害剤の使用 |
KR102670554B1 (ko) * | 2022-01-04 | 2024-05-30 | 주식회사 이노보테라퓨틱스 | 캐스파제 저해제로서의 신규한 이소인돌리논 유도체 화합물 |
WO2024073426A1 (en) * | 2022-09-26 | 2024-04-04 | Edgewise Therapeutics, Inc. | 1,4-dihydroquinazolinone compounds and uses thereof |
Family Cites Families (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6204261B1 (en) | 1995-12-20 | 2001-03-20 | Vertex Pharmaceuticals Incorporated | Inhibitors of interleukin-1β Converting enzyme inhibitors |
FR2582514B1 (fr) | 1985-05-30 | 1988-02-19 | Rhone Poulenc Sante | Medicaments a base d'amides, nouveaux amides et leur preparation |
ES2118940T3 (es) | 1992-02-21 | 1998-10-01 | Merck & Co Inc | Peptidil-derivados utiles como inhibidores de la enzima conversora de la interleucina-1 beta. |
US5714484A (en) * | 1993-12-08 | 1998-02-03 | Prototek, Inc. | α-(1,3-dicarbonylenol ether) methyl ketones as cysteine protease inhibitors |
US5756466A (en) * | 1994-06-17 | 1998-05-26 | Vertex Pharmaceuticals, Inc. | Inhibitors of interleukin-1β converting enzyme |
US5847135A (en) | 1994-06-17 | 1998-12-08 | Vertex Pharmaceuticals, Incorporated | Inhibitors of interleukin-1β converting enzyme |
GB2292149A (en) | 1994-08-09 | 1996-02-14 | Ferring Res Ltd | Peptide inhibitors of pro-interleukin-1beta converting enzyme |
US5618792A (en) * | 1994-11-21 | 1997-04-08 | Cortech, Inc. | Substituted heterocyclic compounds useful as inhibitors of (serine proteases) human neutrophil elastase |
EP0824543A1 (en) * | 1995-05-10 | 1998-02-25 | Chiroscience Limited | Peptide compounds which inhibit metalloproteinase and tnf liberation, and their therapeutic use |
US6252076B1 (en) * | 1996-05-04 | 2001-06-26 | Yuhan Corporation | Process for preparation of pyrimidine derivatives |
AU738341B2 (en) * | 1996-10-11 | 2001-09-13 | Abbott Gmbh & Co. Kg | Asparate ester inhibitors of interleukin-1beta converting enzyme |
JP2001508404A (ja) * | 1996-10-11 | 2001-06-26 | ワーナー―ランバート・コンパニー | スルホンアミドインターロイキン―1β変換酵素阻害剤 |
US6063794A (en) | 1996-10-11 | 2000-05-16 | Cor Therapeutics Inc. | Selective factor Xa inhibitors |
WO1998018781A2 (en) * | 1996-10-28 | 1998-05-07 | Versicor, Inc. | Fused 2,4-pyrimidinedione combinatorial libraries, their preparation and the use of fused 2,4-pyrimidinediones derivatives as antimicrobial agents |
DK1176956T3 (da) | 1999-05-07 | 2008-05-26 | Encysive Pharmaceuticals Inc | Carboxylsyrederivater, som inhiberer bindingen af integriner til deres receptorer |
IL146312A0 (en) * | 1999-05-07 | 2002-07-25 | Texas Biotechnology Corp | Propanoic acid derivatives that inhibit the binding of integrins to their receptors |
US6972296B2 (en) | 1999-05-07 | 2005-12-06 | Encysive Pharmaceuticals Inc. | Carboxylic acid derivatives that inhibit the binding of integrins to their receptors |
AR026748A1 (es) * | 1999-12-08 | 2003-02-26 | Vertex Pharma | Un compuesto inhibidor de caspasas, una composicion farmaceutica que lo comprende, un metodo para la sintesis del mismo y un compuesto intermediario paradicha sintesis |
AU2003211052A1 (en) * | 2002-02-11 | 2003-09-04 | Vertex Pharmaceuticals Incorporated | Phospholipids as caspase inhibitor prodrugs |
AU2003225088A1 (en) * | 2002-04-19 | 2003-11-03 | Vertex Pharmaceuticals Incorporated | Regulation of tnf-alpha |
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