TW200404783A - Caspase inhibitors and uses thereof - Google Patents
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39259202P | 2002-06-28 | 2002-06-28 | |
| US43507302P | 2002-12-20 | 2002-12-20 |
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| TW200404783A true TW200404783A (en) | 2004-04-01 |
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| TW092117681A TW200404783A (en) | 2002-06-28 | 2003-06-27 | Caspase inhibitors and uses thereof |
Country Status (19)
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| JP (2) | JP4616643B2 (enExample) |
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Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20011350A1 (es) | 2000-05-19 | 2002-01-15 | Vertex Pharma | PROFARMACO DE UN INHIBIDOR DE ENZIMA CONVERTIDORA DE INTERLEUCINA-1ß (ICE) |
| BR0312232A (pt) | 2002-06-28 | 2005-05-10 | Vertex Pharma | Inibidores de caspases e seus usos |
| JP4675628B2 (ja) * | 2002-12-20 | 2011-04-27 | 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 | ４−オキソ−３−（１−オキソ−１ｈ−イソキノリン−２−イルアセチルアミノ）−ペンタン酸のエステル誘導体およびアミド誘導体、ならびにカスパーゼインヒビターとしてのそれらの使用 |
| 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 |
| CA2559303C (en) | 2004-03-12 | 2013-09-10 | Vertex Pharmaceuticals Incorporated | Processes and intermediates for the preparation of aspartic acetal caspase inhibitors |
| CN102362867A (zh) | 2004-05-15 | 2012-02-29 | 沃泰克斯药物股份有限公司 | 使用ice抑制剂治疗癫痫发作 |
| EP1778221A2 (en) | 2004-05-27 | 2007-05-02 | Vertex Pharmaceuticals Incorporated | Ice inhibitors for the treatment of autoinflammatory diseases |
| CA2569763C (en) | 2004-06-08 | 2013-03-12 | Decode Chemistry, Inc. | 2,4-diaminoquinazolines for spinal muscular atrophy |
| AU2005272627A1 (en) * | 2004-08-13 | 2006-02-23 | Amgen Inc. | Substituted benzofused heterocycles |
| EP1796660B1 (en) | 2004-09-17 | 2016-11-23 | BioMAS Ltd. | Use of ammonium trichloro(dioxyethylene-o,o')tellurate (as101) for the inhibition of interleukin-1beta-converting enzyme |
| CN101098855B (zh) * | 2004-11-24 | 2012-06-06 | 沃泰克斯药物股份有限公司 | 3-[2-(3-酰氨基-2-氧代-2h-吡啶-1-基)-乙酰氨基]-4-氧代-戊酸衍生物及其作为天冬氨酸特异性半胱氨酸蛋白酶抑制剂的用途 |
| CA2593005A1 (en) * | 2005-01-03 | 2006-07-13 | Myriad Genetics Inc. | Pharmaceutical compounds as activators of caspases and inducers of apoptosis and the use thereof |
| EP1898940A4 (en) * | 2005-06-07 | 2010-05-26 | Univ Pennsylvania | Alpha2beta1 / GPIa IIA INTEGRIN INHIBITORS |
| US8987306B2 (en) * | 2005-06-07 | 2015-03-24 | The Trustees Of The University Of Pennsylvania | Inhibitors of integrin alpha2beta1 based on prolyl diaminopropionic acid scaffold |
| 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 |
| WO2007027742A2 (en) * | 2005-08-31 | 2007-03-08 | The Trustees Of The University Of Pennsylvania | SMALL MOLECULE INTEGRIN α2βl/GPIa-IIa ANTAGONISTS |
| WO2008016973A1 (en) | 2006-08-01 | 2008-02-07 | Families Of Spinal Muscular Atrophy | 2,4-diaminoquinazolines for spinal muscular atrophy |
| ATE523493T1 (de) * | 2006-09-11 | 2011-09-15 | Organon Nv | 2-(1-oxo-1h-isochinolin-2-yl) acetamid-derivate |
| WO2008073388A2 (en) * | 2006-12-11 | 2008-06-19 | Mutual Pharmaceutical Company, Inc. | Alfuzosin formulations, methods of making and methods of use |
| US20100092556A1 (en) * | 2006-12-11 | 2010-04-15 | Kristin Arnold | Alfuzosin formulations, methods of making, and methods of use |
| FR2923160B1 (fr) | 2007-11-02 | 2013-07-26 | Pasteur Institut | Composes destines a prevenir ou traiter une infection virale. |
| EP2635906A4 (en) | 2010-11-05 | 2014-04-02 | Univ Brandeis | Ice inhibiting compounds and uses thereof |
| US9956260B1 (en) | 2011-07-22 | 2018-05-01 | The J. David Gladstone Institutes | Treatment of HIV-1 infection and AIDS |
| CA2862084C (en) | 2012-01-26 | 2021-05-11 | Ptc Therapeutics, Inc. | 1h-isochromen-1-one derivatives and compositions thereof for treating spinal muscular atrophy |
| WO2015175381A1 (en) | 2014-05-12 | 2015-11-19 | Conatus Pharmaceuticals, Inc. | Treatment of the complications of chronic liver disease with caspase inhibitors |
| WO2017079566A1 (en) | 2015-11-05 | 2017-05-11 | Conatus Pharmaceuticals, Inc. | Caspase inhibitors for use in the treatment of liver cancer |
| JP2019500397A (ja) | 2015-12-31 | 2019-01-10 | クオナトウス ファーマシューティカルズ，インコーポレイテッド | カスパーゼ阻害剤を肝疾患の治療に使用する方法 |
| RU2019113150A (ru) | 2016-10-05 | 2020-11-06 | Новартис Аг | Комбинация композиций, содержащих агонисты fxr, предназначенная для лечения или предупреждения фиброзирующего, цирротического заболевания или нарушения |
| EP3935042B1 (en) * | 2019-03-07 | 2024-08-28 | NOBO Medicine Inc. | Caspase inhibitors and methods of use thereof |
| WO2022123062A1 (en) | 2020-12-11 | 2022-06-16 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Blocking caspase and/or fasl for preventing fatal outcome in covid-19 patients |
| KR102670554B1 (ko) * | 2022-01-04 | 2024-05-30 | 주식회사 이노보테라퓨틱스 | 캐스파제 저해제로서의 신규한 이소인돌리논 유도체 화합물 |
Family Cites Families (25)
| 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 |
| DD232699A1 (de) * | 1983-11-18 | 1986-02-05 | Adw Ddr | Verfahren zur herstellung von chinazolin-4-on-3-alkansaeuren und deren estern |
| FR2582514B1 (fr) * | 1985-05-30 | 1988-02-19 | Rhone Poulenc Sante | Medicaments a base d'amides, nouveaux amides et leur preparation |
| 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 |
| US6420522B1 (en) * | 1995-06-05 | 2002-07-16 | Vertex Pharmaceuticals Incorporated | Inhibitors of interleukin-1β converting enzyme |
| US5716929A (en) * | 1994-06-17 | 1998-02-10 | Vertex Pharmaceuticals, Inc. | Inhibitors of interleukin-1β converting enzyme |
| EP0761680A3 (en) | 1995-09-12 | 1999-05-06 | Ono Pharmaceutical Co., Ltd. | Tetrazole compounds having Interleukin-1beta converting enzyme inhibitory activity |
| US6063794A (en) * | 1996-10-11 | 2000-05-16 | Cor Therapeutics Inc. | Selective factor Xa inhibitors |
| AU738341B2 (en) | 1996-10-11 | 2001-09-13 | Abbott Gmbh & Co. Kg | Asparate ester inhibitors of interleukin-1beta converting enzyme |
| KR20000049047A (ko) | 1996-10-11 | 2000-07-25 | 로즈 암스트롱, 크리스틴 에이. 트러트웨인 | 술폰아미드 인터루킨-1β 전환 효소 억제제 |
| 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 |
| US6972296B2 (en) | 1999-05-07 | 2005-12-06 | Encysive Pharmaceuticals Inc. | Carboxylic acid derivatives that inhibit the binding of integrins to their receptors |
| ES2296625T3 (es) | 1999-05-07 | 2008-05-01 | Encysive Pharmaceuticals, Inc | Derivados del acido carboxilico que inhiben el enlace de las integrinas con sus receptores. |
| SI20876B (sl) | 1999-05-07 | 2009-08-31 | Texas Biotechnology Corp | Derivati propanojske kisline, ki inhibirajo vezavo integrinov na njihove receptorje |
| 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 |
| EP1289993B9 (en) | 2000-06-07 | 2008-08-20 | Vertex Pharmaceuticals Incorporated | Caspase inhibitors and uses thereof |
| AU2002348533A1 (en) * | 2001-10-09 | 2003-05-26 | Vertex Pharmaceuticals Incorporated | Process for synthesizing aspartic and glutamic acid derivatives and diazoketone intermediates thereof |
| 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 |
| BR0312232A (pt) | 2002-06-28 | 2005-05-10 | Vertex Pharma | Inibidores de caspases e seus usos |
| JP4675628B2 (ja) | 2002-12-20 | 2011-04-27 | 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 | ４−オキソ−３−（１−オキソ−１ｈ−イソキノリン−２−イルアセチルアミノ）−ペンタン酸のエステル誘導体およびアミド誘導体、ならびにカスパーゼインヒビターとしてのそれらの使用 |
| 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 |
| CN101098855B (zh) | 2004-11-24 | 2012-06-06 | 沃泰克斯药物股份有限公司 | 3-[2-(3-酰氨基-2-氧代-2h-吡啶-1-基)-乙酰氨基]-4-氧代-戊酸衍生物及其作为天冬氨酸特异性半胱氨酸蛋白酶抑制剂的用途 |
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2003
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- 2003-06-27 RU RU2005102094/04A patent/RU2005102094A/ru unknown
- 2003-06-27 NZ NZ537807A patent/NZ537807A/en unknown
- 2003-06-27 KR KR10-2004-7021300A patent/KR20050013260A/ko not_active Ceased
- 2003-06-27 AU AU2003248758A patent/AU2003248758A1/en not_active Abandoned
- 2003-06-27 PE PE2003000653A patent/PE20040728A1/es not_active Application Discontinuation
- 2003-06-27 US US10/609,147 patent/US7553852B2/en not_active Expired - Fee Related
- 2003-06-27 TW TW092117681A patent/TW200404783A/zh unknown
- 2003-06-27 AR ARP030102352A patent/AR040350A1/es unknown
- 2003-06-27 EP EP03762231A patent/EP1539701A1/en not_active Withdrawn
- 2003-06-27 JP JP2004518103A patent/JP4616643B2/ja not_active Expired - Fee Related
- 2003-06-27 CA CA002493646A patent/CA2493646A1/en not_active Abandoned
- 2003-06-27 MX MXPA05000069A patent/MXPA05000069A/es unknown
- 2003-06-27 IL IL16598603A patent/IL165986A0/xx unknown
- 2003-06-27 PL PL03374598A patent/PL374598A1/xx not_active Application Discontinuation
- 2003-06-27 WO PCT/US2003/020557 patent/WO2004002961A1/en not_active Ceased
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2009
- 2009-05-12 US US12/464,380 patent/US8129381B2/en not_active Expired - Fee Related
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2010
- 2010-02-04 JP JP2010023632A patent/JP2010143942A/ja active Pending
Also Published As
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|---|---|
| EP1539701A1 (en) | 2005-06-15 |
| IL165986A0 (en) | 2006-01-15 |
| NZ537807A (en) | 2007-05-31 |
| JP2010143942A (ja) | 2010-07-01 |
| AR040350A1 (es) | 2005-03-30 |
| AU2003248758A1 (en) | 2004-01-19 |
| US20040072850A1 (en) | 2004-04-15 |
| CN1675184A (zh) | 2005-09-28 |
| JP2005533825A (ja) | 2005-11-10 |
| JP4616643B2 (ja) | 2011-01-19 |
| RU2005102094A (ru) | 2006-02-27 |
| US20090281128A1 (en) | 2009-11-12 |
| WO2004002961A1 (en) | 2004-01-08 |
| CN100503572C (zh) | 2009-06-24 |
| BR0312232A (pt) | 2005-05-10 |
| KR20050013260A (ko) | 2005-02-03 |
| UY27872A1 (es) | 2003-12-31 |
| NO20050851L (no) | 2005-03-29 |
| MXPA05000069A (es) | 2005-04-11 |
| PE20040728A1 (es) | 2004-10-23 |
| US8129381B2 (en) | 2012-03-06 |
| PL374598A1 (en) | 2005-10-31 |
| CA2493646A1 (en) | 2004-01-08 |
| US7553852B2 (en) | 2009-06-30 |
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