AU2006285145A1 - 3,5-disubstituted pyrid-2-ones useful as inhibitors of Tec family of non-.receptor tyrosine kinases - Google Patents
3,5-disubstituted pyrid-2-ones useful as inhibitors of Tec family of non-.receptor tyrosine kinases Download PDFInfo
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- AU2006285145A1 AU2006285145A1 AU2006285145A AU2006285145A AU2006285145A1 AU 2006285145 A1 AU2006285145 A1 AU 2006285145A1 AU 2006285145 A AU2006285145 A AU 2006285145A AU 2006285145 A AU2006285145 A AU 2006285145A AU 2006285145 A1 AU2006285145 A1 AU 2006285145A1
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71245705P | 2005-08-29 | 2005-08-29 | |
| US60/712,457 | 2005-08-29 | ||
| PCT/US2006/033282 WO2007027528A2 (en) | 2005-08-29 | 2006-08-25 | 3,5-disubstituted pyrid-2-ones useful as inhibitors of tec family of non-.receptor tyrosine kinases |
Publications (1)
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| AU2006285145A1 true AU2006285145A1 (en) | 2007-03-08 |
Family
ID=37565557
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2006285145A Abandoned AU2006285145A1 (en) | 2005-08-29 | 2006-08-25 | 3,5-disubstituted pyrid-2-ones useful as inhibitors of Tec family of non-.receptor tyrosine kinases |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7786120B2 (https=) |
| EP (1) | EP1919905B1 (https=) |
| JP (2) | JP5112317B2 (https=) |
| CN (1) | CN101291926A (https=) |
| AT (1) | ATE499362T1 (https=) |
| AU (1) | AU2006285145A1 (https=) |
| CA (1) | CA2620631A1 (https=) |
| DE (1) | DE602006020293D1 (https=) |
| ES (1) | ES2361338T3 (https=) |
| WO (1) | WO2007027528A2 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2009506123A (ja) | 2005-08-29 | 2009-02-12 | 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 | 非受容体型チロシンキナーゼのｔｅｃファミリーの阻害剤として有用な３，５−二置換ピリド−２−オン |
| WO2007027594A1 (en) * | 2005-08-29 | 2007-03-08 | Vertex Pharmaceuticals Incorporated | 3,5-disubstituted pyrid-2-ones useful as inhibitors of tec family of non-receptor tyrosine kinases |
| WO2009053269A1 (en) | 2007-10-23 | 2009-04-30 | F. Hoffmann-La Roche Ag | Novel kinase inhibitors |
| US7683064B2 (en) | 2008-02-05 | 2010-03-23 | Roche Palo Alto Llc | Inhibitors of Bruton's tyrosine kinase |
| ES2552320T3 (es) | 2008-06-24 | 2015-11-27 | F. Hoffmann-La Roche Ag | Nuevas piridín-2-onas y piridazín-3-onas sustituidas |
| BRPI0913879A2 (pt) | 2008-07-02 | 2019-09-24 | Hoffmann La Roche | fenilpirazinonas como inibidores de quinase |
| AR082590A1 (es) | 2010-08-12 | 2012-12-19 | Hoffmann La Roche | Inhibidores de la tirosina-quinasa de bruton |
| WO2013153539A1 (en) | 2012-04-13 | 2013-10-17 | Glenmark Pharmaceuticals S.A. | Tricyclic compounds as tec kinase inhibitors |
Family Cites Families (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL98526A0 (en) * | 1990-06-18 | 1992-07-15 | Merck & Co Inc | Pyridones,processes for their preparation and pharmaceutical compositions containing them |
| US5308854A (en) * | 1990-06-18 | 1994-05-03 | Merck & Co., Inc. | Inhibitors of HIV reverse transcriptase |
| CN1034934C (zh) | 1990-06-19 | 1997-05-21 | 明治制果株式会社 | 血管紧张素ii拮抗性吡啶衍生物的制备方法 |
| IL99731A0 (en) | 1990-10-18 | 1992-08-18 | Merck & Co Inc | Hydroxylated pyridine derivatives,their preparation and pharmaceutical compositions containing them |
| DE4221583A1 (de) | 1991-11-12 | 1993-05-13 | Bayer Ag | Substituierte biphenylpyridone |
| US5290941A (en) * | 1992-10-14 | 1994-03-01 | Merck & Co., Inc. | Facile condensation of methylbenzoxazoles with aromatic aldehydes |
| DE4314963A1 (de) * | 1993-05-06 | 1994-11-10 | Bayer Ag | Substituierte Pyridine und 2-Oxo-1,2-dihydropyridine |
| DE4314964A1 (de) * | 1993-05-06 | 1994-11-10 | Bayer Ag | Pyridinylmethyl-substiutierte Pyridine und Pyridone |
| DE4316077A1 (de) * | 1993-05-13 | 1994-11-17 | Bayer Ag | Substituierte Mono- und Bihydridylmethylpyridone |
| US6979695B2 (en) | 1996-04-23 | 2005-12-27 | Targacept, Inc. | Compounds capable of activating cholinergic receptors |
| BR9909976A (pt) | 1998-04-27 | 2000-12-26 | Centre Nat Rech Scient | Composto, processo para a obtenção de compostos, derivado litiado, composições farmacêuticas, e, processos de tratamento de doenças relacionadas com hiv e de tratamento de infecção de hiv |
| US6774138B2 (en) | 1999-08-31 | 2004-08-10 | Merck & Co., Inc. | Thiazolyl(pyridyl)ethyne compounds |
| IL150650A0 (en) | 2000-01-20 | 2003-02-12 | Eisai Co Ltd | Piperidine derivatives and pharmaceutical compositions containing the same |
| IL152848A0 (en) * | 2000-06-12 | 2003-06-24 | Eisai Co Ltd | 1,2-dihydropyridine derivatives, pharmaceutical compositions containing the same and methods for the production thereof |
| ATE319706T1 (de) * | 2000-09-19 | 2006-03-15 | Centre Nat Rech Scient | Pyridinon und pyridinethion-derivate mit hiv- hemmenden eigenschaften |
| US6670380B2 (en) | 2000-11-20 | 2003-12-30 | Bristol-Myers Squibb Co. | Pyridone inhibitors of fatty acid binding protein and method |
| ES2330719T3 (es) | 2000-12-28 | 2009-12-15 | SHIONOGI & CO., LTD. | Derivados de 2-piridona con afinidad para el receptor cannabinoide de tipo 2. |
| CN1514833A (zh) | 2001-03-28 | 2004-07-21 | ����˹�ж�-����˹˹������˾ | 新型酪氨酸激酶抑制剂 |
| JP2002371078A (ja) * | 2001-06-12 | 2002-12-26 | Sankyo Co Ltd | キノリン誘導体及びキノロン誘導体 |
| GB0129260D0 (en) * | 2001-12-06 | 2002-01-23 | Eisai London Res Lab Ltd | Pharmaceutical compositions and their uses |
| US20030187026A1 (en) | 2001-12-13 | 2003-10-02 | Qun Li | Kinase inhibitors |
| RS52392B (sr) * | 2002-02-14 | 2013-02-28 | Pharmacia Corporation | Supstituisani piridinoni kao modulatori p38 map kinaze |
| JP4208512B2 (ja) | 2002-07-23 | 2009-01-14 | 株式会社クラレ | ５−（２’−ピリジル）−２−ピリドン誘導体の製造方法 |
| WO2004035563A1 (en) | 2002-10-17 | 2004-04-29 | Syngenta Participations Ag | 3-heterocyclylpyridine derivatives useful as herbicides |
| AU2003274025A1 (en) | 2002-10-17 | 2004-05-04 | Syngenta Participations Ag | Pyridine derivatives useful as herbicides |
| WO2004050657A2 (en) | 2002-11-27 | 2004-06-17 | Artesian Therapeutics, Inc. | COMPOUNDS WITH MIXED PDE-INHIBITORY AND β-ADRENERGIC ANTAGONIST OR PARTIAL AGONIST ACTIVITY FOR TREATMENT OF HEART FAILURE |
| US20070117978A1 (en) | 2002-12-23 | 2007-05-24 | Artesian Therapecutics, Inc | Cardiotonic compounds with inhibitory activity against beta-adrenergic receptors and phosphodiesterase |
| US20070010541A1 (en) | 2003-07-14 | 2007-01-11 | The General Hospital Corporation | Methods for treating vascular diseases |
| CL2004002050A1 (es) * | 2003-08-13 | 2005-06-03 | Pharmacia Corp Sa Organizada B | Compuestos derivados de piridinonas sustituidas; su uso en el tratamiento de afecciones causadas o exacerbadas por actividad p38 map kinasa y/o tnf no regulada, tales como inflamaciones, tumores, sida y otros. |
| PE20060285A1 (es) * | 2004-03-30 | 2006-05-08 | Aventis Pharma Inc | Piridonas sustituidas como inhibidores de pol(adp-ribosa)-polimerasa (parp) |
| BRPI0514094A (pt) | 2004-08-02 | 2008-05-27 | Osi Pharm Inc | composto, composição, e, método de tratamento de distúrbio hiperproliferativo |
| CA2591413A1 (en) * | 2004-12-16 | 2006-06-22 | Vertex Pharmaceuticals Incorporated | Pyrid-2-ones useful as inhibitors of tec family protein kinases for the treatment of inflammatory, proliferative and immunologically-mediated diseases |
| CA2601628C (en) | 2005-03-10 | 2014-05-13 | Cgi Pharmaceuticals, Inc. | Certain substituted amides, method of making, and method of use thereof |
| WO2007027594A1 (en) | 2005-08-29 | 2007-03-08 | Vertex Pharmaceuticals Incorporated | 3,5-disubstituted pyrid-2-ones useful as inhibitors of tec family of non-receptor tyrosine kinases |
| JP2009506123A (ja) | 2005-08-29 | 2009-02-12 | 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 | 非受容体型チロシンキナーゼのｔｅｃファミリーの阻害剤として有用な３，５−二置換ピリド−２−オン |
-
2006
- 2006-08-25 EP EP06813771A patent/EP1919905B1/en not_active Not-in-force
- 2006-08-25 CA CA002620631A patent/CA2620631A1/en not_active Abandoned
- 2006-08-25 JP JP2008529133A patent/JP5112317B2/ja not_active Expired - Fee Related
- 2006-08-25 US US11/510,126 patent/US7786120B2/en not_active Expired - Fee Related
- 2006-08-25 WO PCT/US2006/033282 patent/WO2007027528A2/en not_active Ceased
- 2006-08-25 CN CNA2006800393748A patent/CN101291926A/zh active Pending
- 2006-08-25 AU AU2006285145A patent/AU2006285145A1/en not_active Abandoned
- 2006-08-25 ES ES06813771T patent/ES2361338T3/es active Active
- 2006-08-25 DE DE602006020293T patent/DE602006020293D1/de active Active
- 2006-08-25 AT AT06813771T patent/ATE499362T1/de not_active IP Right Cessation
-
2012
- 2012-06-20 JP JP2012138966A patent/JP2012184260A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| ATE499362T1 (de) | 2011-03-15 |
| EP1919905A2 (en) | 2008-05-14 |
| JP2009507790A (ja) | 2009-02-26 |
| US20070185125A1 (en) | 2007-08-09 |
| CA2620631A1 (en) | 2007-03-08 |
| CN101291926A (zh) | 2008-10-22 |
| JP5112317B2 (ja) | 2013-01-09 |
| ES2361338T3 (es) | 2011-06-16 |
| DE602006020293D1 (de) | 2011-04-07 |
| US7786120B2 (en) | 2010-08-31 |
| WO2007027528A3 (en) | 2007-05-03 |
| JP2012184260A (ja) | 2012-09-27 |
| WO2007027528A2 (en) | 2007-03-08 |
| EP1919905B1 (en) | 2011-02-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |