JP2012502978A5 - - Google Patents
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- JP2012502978A5 JP2012502978A5 JP2011527463A JP2011527463A JP2012502978A5 JP 2012502978 A5 JP2012502978 A5 JP 2012502978A5 JP 2011527463 A JP2011527463 A JP 2011527463A JP 2011527463 A JP2011527463 A JP 2011527463A JP 2012502978 A5 JP2012502978 A5 JP 2012502978A5
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| WO1998037068A1 (en) * | 1997-02-21 | 1998-08-27 | Bristol-Myers Squibb Company | Benzoic acid derivatives and related compounds as antiarrhythmic agents |
| EP1396493A4 (en) | 2001-04-26 | 2005-08-03 | Ajinomoto Kk | HETEROCYCLIC COMPOUNDS |
| US7662826B2 (en) * | 2002-04-23 | 2010-02-16 | Shionogi & Co., Ltd. | Pyrazolo [1,5-a] pyrimidine derivative and nad (p) h oxidase inhibitor containing the same |
| AU2003267980A1 (en) | 2002-07-03 | 2004-01-23 | Janssen Pharmaceutica, N.V. | Substituted heteroaryl and heterocyclic compounds useful in treating inflammatory disorders |
| TW200533356A (en) | 2004-02-24 | 2005-10-16 | Mitsubishi Pharma Corp | Fused pyridazine derivatives |
| EP1809601B1 (en) | 2004-10-04 | 2014-09-10 | Manfredi, John | Compounds for alzheimer's disease |
| DE102005048897A1 (de) | 2005-10-12 | 2007-04-19 | Sanofi-Aventis Deutschland Gmbh | Diacylindazol-derivate als Inhibitoren von Lipasen und Phospholipasen |
| JP2009532501A (ja) * | 2006-04-04 | 2009-09-10 | ミリアド ジェネティクス， インコーポレイテッド | 疾患および障害のための化合物 |
| EP2002835A1 (en) * | 2007-06-04 | 2008-12-17 | GenKyo Tex | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| EP2000176A1 (en) | 2007-06-04 | 2008-12-10 | GenKyo Tex | Tetrahydroindole derivatives as NADPH Oxidase inhibitors |
| EP2166010A1 (en) * | 2008-09-23 | 2010-03-24 | Genkyo Tex Sa | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| EP2165707A1 (en) * | 2008-09-23 | 2010-03-24 | Genkyo Tex Sa | Pyrazolo pyridine derivatives as NADPH oxidase inhibitors |
| EP2166009A1 (en) | 2008-09-23 | 2010-03-24 | Genkyo Tex Sa | Pyrazolo pyridine derivatives as nadph oxidase inhibitors |
| WO2010059689A2 (en) * | 2008-11-18 | 2010-05-27 | Ligocyte Pharmaceuticals, Inc. | Rsv f vlps and methods of manufacture and use thereof |
| CA2743172A1 (en) * | 2008-11-19 | 2010-05-27 | Forest Laboratories Holdings Limited | Crystalline form of linaclotide |
| BRPI0921509A2 (pt) * | 2008-11-19 | 2016-03-08 | Vertex Pharma | inibidor triazolotiadiazol de proteína quinase c-met |
| EP2361912A1 (en) | 2010-02-18 | 2011-08-31 | GenKyoTex SA | Pyrazolo piperidine derivatives as NADPH oxidase inhibitors |
| EP2361911A1 (en) | 2010-02-18 | 2011-08-31 | GenKyoTex SA | Pyrazolo piperidine derivatives as NADPH oxidase inhibitors |
-
2008
- 2008-09-23 EP EP08164847A patent/EP2166008A1/en not_active Withdrawn
-
2009
- 2009-09-22 EP EP09815760.5A patent/EP2344493B1/en active Active
- 2009-09-22 JP JP2011527463A patent/JP5666454B2/ja not_active Expired - Fee Related
- 2009-09-22 WO PCT/IB2009/054148 patent/WO2010035217A1/en not_active Ceased
- 2009-09-22 KR KR1020117006129A patent/KR101703360B1/ko not_active Expired - Fee Related
- 2009-09-22 ES ES09815760.5T patent/ES2565436T3/es active Active
- 2009-09-22 CA CA2737457A patent/CA2737457C/en not_active Expired - Fee Related
- 2009-09-22 CN CN200980133740.XA patent/CN102137863B/zh not_active Expired - Fee Related
- 2009-09-22 AU AU2009298004A patent/AU2009298004B2/en not_active Ceased
- 2009-09-22 US US13/120,435 patent/US8481562B2/en not_active Expired - Fee Related
- 2009-09-22 BR BRPI0919329-4A patent/BRPI0919329A2/pt not_active Application Discontinuation
- 2009-09-22 RU RU2011116227/04A patent/RU2569303C2/ru active
-
2011
- 2011-03-23 IL IL211889A patent/IL211889A/en active IP Right Grant
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2013
- 2013-07-05 US US13/935,667 patent/US8940760B2/en not_active Expired - Fee Related
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