JP2005508978A - Ｐｄｅ９阻害薬によるインスリン抵抗性症候群及び２型糖尿病の治療 - Google Patents
Ｐｄｅ９阻害薬によるインスリン抵抗性症候群及び２型糖尿病の治療 Download PDFInfo
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- JP2005508978A JP2005508978A JP2003539771A JP2003539771A JP2005508978A JP 2005508978 A JP2005508978 A JP 2005508978A JP 2003539771 A JP2003539771 A JP 2003539771A JP 2003539771 A JP2003539771 A JP 2003539771A JP 2005508978 A JP2005508978 A JP 2005508978A
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- alkyl
- optionally substituted
- phenyl
- inhibitor
- halo
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Classifications
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Landscapes
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- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33698101P | 2001-11-02 | 2001-11-02 | |
| PCT/IB2002/003754 WO2003037432A1 (en) | 2001-11-02 | 2002-09-12 | Treatment of insulin resistance syndrome and type 2 diabetes with pde9 inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2005508978A true JP2005508978A (ja) | 2005-04-07 |
| JP2005508978A5 JP2005508978A5 (https=) | 2005-12-22 |
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| JP2003539771A Withdrawn JP2005508978A (ja) | 2001-11-02 | 2002-09-12 | Ｐｄｅ９阻害薬によるインスリン抵抗性症候群及び２型糖尿病の治療 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US6967204B2 (https=) |
| EP (1) | EP1444009A1 (https=) |
| JP (1) | JP2005508978A (https=) |
| KR (1) | KR20040053210A (https=) |
| CN (1) | CN1575191A (https=) |
| BR (1) | BR0213817A (https=) |
| CA (1) | CA2465632A1 (https=) |
| HU (1) | HUP0401998A2 (https=) |
| IL (1) | IL161155A0 (https=) |
| MX (1) | MXPA04004170A (https=) |
| PL (1) | PL370599A1 (https=) |
| WO (1) | WO2003037432A1 (https=) |
| ZA (1) | ZA200402173B (https=) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2005527565A (ja) * | 2002-03-28 | 2005-09-15 | ウスタフ エクスペリメンタルニ ボタニキ エーブイ シーアール （インスティチュート オブ エクスペリメンタル ボタニー アカデミー オブ サイエンシーズ オブ ザ チェコ リパブリック） | 新しいピラゾロ［４，３−ｄ］ピリミジン、その調整方法、及び治療方法 |
| WO2008018306A1 (en) * | 2006-08-08 | 2008-02-14 | Aska Pharmaceutical Co., Ltd. | Quinazoline derivative |
| WO2008072778A1 (ja) * | 2006-12-13 | 2008-06-19 | Aska Pharmaceutical Co., Ltd. | 尿路系疾患の処置剤 |
| JP2010526863A (ja) * | 2007-05-11 | 2010-08-05 | ファイザー・インク | アミノ複素環式化合物 |
| JP2011504913A (ja) * | 2007-11-30 | 2011-02-17 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | １，５−ジヒドロ−ピラゾロ［３，４−ｄ］ピリミジン−４−オン誘導体及びｃｎｓ障害の治療のためのｐｄｅ９ａモジュレーターとしてのそれらの使用 |
| JP2013540755A (ja) * | 2010-09-20 | 2013-11-07 | エンビボ・ファーマシューティカルズ・インコーポレイテッド | イミダゾトリアジノン化合物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP1575916B1 (en) | 2001-08-31 | 2013-05-22 | The Rockefeller University | Phosphodiesterase activity and regulation of phosphodiesterase 1-b-mediated signaling in brain |
| EP1444009A1 (en) * | 2001-11-02 | 2004-08-11 | Pfizer Products Inc. | Treatment of insulin resistance syndrome and type 2 diabetes with pde9 inhibitors |
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| US20130315891A1 (en) | 2012-05-25 | 2013-11-28 | Matthew Charles | Formulations of human tissue kallikrein-1 for parenteral delivery and related methods |
| EP2854841B1 (en) | 2012-06-04 | 2017-02-22 | Diamedica Inc. | Human tissue kallikrein 1 glycosylation isoforms |
| US9527875B2 (en) | 2012-08-02 | 2016-12-27 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| CN102786525B (zh) | 2012-08-08 | 2014-12-17 | 中山大学 | N-取代吡唑并[3,4-d]嘧啶酮类化合物、其制备方法及其应用 |
| WO2014024125A1 (en) | 2012-08-08 | 2014-02-13 | Celon Pharma S.A. | Pyrazolo[4,3-d]pyrimidin-7(6h)-one derivatives as pde9 inhibitors |
| RU2015140066A (ru) | 2013-02-22 | 2017-03-30 | Мерк Шарп И Доум Корп. | Противодиабетические бициклические соединения |
| WO2014139388A1 (en) | 2013-03-14 | 2014-09-18 | Merck Sharp & Dohme Corp. | Novel indole derivatives useful as anti-diabetic agents |
| WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| CR20160207A (es) | 2013-11-05 | 2016-08-10 | Ben Gurion Univ Of The Negev Res And Dev Authority | Compuestos para el tratamiento de la diabetes y las complicaciones que surgen de la misma enfermedad |
| US20170216296A1 (en) | 2014-04-18 | 2017-08-03 | Concert Pharmaceuticals, Inc. | Methods of treating hyperglycemia |
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| TW201811799A (zh) | 2016-09-09 | 2018-04-01 | 美商英塞特公司 | 吡唑并嘧啶化合物及其用途 |
| WO2018049214A1 (en) | 2016-09-09 | 2018-03-15 | Incyte Corporation | Pyrazolopyridine derivatives as hpk1 modulators and uses thereof for the treatment of cancer |
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| US11072602B2 (en) | 2016-12-06 | 2021-07-27 | Merck Sharp & Dohme Corp. | Antidiabetic heterocyclic compounds |
| WO2018118670A1 (en) | 2016-12-20 | 2018-06-28 | Merck Sharp & Dohme Corp. | Antidiabetic spirochroman compounds |
| US20180228786A1 (en) | 2017-02-15 | 2018-08-16 | Incyte Corporation | Pyrazolopyridine compounds and uses thereof |
| CN110446501A (zh) | 2017-03-09 | 2019-11-12 | 代阿麦迪卡股份有限公司 | 组织激肽释放酶1的剂型 |
| DK3630772T3 (da) * | 2017-05-26 | 2024-02-05 | Cardurion Pharmaceuticals Inc | Fremgangsmåder til fremstilling og anvendelse af pde9-hæmmere |
| RU2019144010A (ru) | 2017-06-08 | 2021-07-13 | Мерк Шарп И Доум Корп. | Пиразолопиримидиновые ингибиторы pde9 |
| US10722495B2 (en) | 2017-09-08 | 2020-07-28 | Incyte Corporation | Cyanoindazole compounds and uses thereof |
| WO2019164847A1 (en) | 2018-02-20 | 2019-08-29 | Incyte Corporation | Indazole compounds and uses thereof |
| US10800761B2 (en) | 2018-02-20 | 2020-10-13 | Incyte Corporation | Carboxamide compounds and uses thereof |
| US10745388B2 (en) | 2018-02-20 | 2020-08-18 | Incyte Corporation | Indazole compounds and uses thereof |
| US11299473B2 (en) | 2018-04-13 | 2022-04-12 | Incyte Corporation | Benzimidazole and indole compounds and uses thereof |
| FI3801526T3 (fi) | 2018-05-25 | 2024-03-20 | Cardurion Pharmaceuticals Inc | 6-[(3s,4s)-4-metyyli-1-(pyrimidin-2-yylimetyyli)pyrrolidin-3-yyli]-3-tetrahydropyran-4-yyli-7h-imidatso[1,5-a]pyratsin-8-onin monohydraattimuotoja ja kiteisiä muotoja |
| US10899755B2 (en) | 2018-08-08 | 2021-01-26 | Incyte Corporation | Benzothiazole compounds and uses thereof |
| EP3843737A4 (en) | 2018-08-31 | 2022-06-01 | Imara Inc. | PDE9 INHIBITORS FOR THE TREATMENT OF SICKLE CELL DISEASE |
| ES2973117T3 (es) | 2018-09-25 | 2024-06-18 | Incyte Corp | Compuestos de pirazolo[4,3-d]pirimidina como moduladores de ALK2 y/o FGFR |
| MX2022001562A (es) | 2019-08-06 | 2022-04-26 | Incyte Corp | Formas solidas de un inhibidor de la cinasa 1 del progenitor hematopoyetico (hpk1). |
| AU2021370658A1 (en) * | 2020-10-27 | 2023-06-08 | Cardurion Pharmaceuticals, Inc. | Pde9 inhibitors for treating cardiac failure |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4666908A (en) * | 1985-04-05 | 1987-05-19 | Warner-Lambert Company | 5-Substituted pyrazolo[4,3-d]pyrimidine-7-ones and methods of use |
| DE19541264A1 (de) * | 1995-11-06 | 1997-05-07 | Bayer Ag | Purin-6-on-derivate |
| AU722514B2 (en) * | 1995-12-28 | 2000-08-03 | Fujisawa Pharmaceutical Co., Ltd. | Benzimidazole derivatives |
| GB9722520D0 (en) * | 1997-10-24 | 1997-12-24 | Pfizer Ltd | Compounds |
| US6444816B1 (en) * | 1997-10-27 | 2002-09-03 | Dr. Reddy's Research Foundation | Fused 7-oxo-pyrimidinyl compounds, preparation, composition and use thereof |
| US5922595A (en) * | 1997-12-09 | 1999-07-13 | Incyte Pharmaceuticals, Inc. | Cyclic GMP phosphodiesterase |
| US6225456B1 (en) | 1998-05-07 | 2001-05-01 | University Technololy Corporation | Ras suppressor SUR-5 |
| JP2003526608A (ja) | 1998-10-15 | 2003-09-09 | バイオイメージ エイ／エス | 再分布及び／又は標的化での干渉によって得られる特異的治療の介入 |
| WO2002013798A2 (en) * | 2000-08-11 | 2002-02-21 | Pfizer Limited | Treatment of the insulin resistance syndrome with selective cgmp pde5 inhibitors |
| MXPA03006936A (es) * | 2001-02-02 | 2003-11-18 | Pfizer | Tratamiento de diabetes mellitus. |
| AUPR576801A0 (en) | 2001-06-19 | 2001-07-12 | University Of Tasmania | Methods and pharmaceuticals for treating muscle insulin resistance and related conditions |
| EP1444009A1 (en) * | 2001-11-02 | 2004-08-11 | Pfizer Products Inc. | Treatment of insulin resistance syndrome and type 2 diabetes with pde9 inhibitors |
| US20040220186A1 (en) * | 2003-04-30 | 2004-11-04 | Pfizer Inc. | PDE9 inhibitors for treating type 2 diabetes,metabolic syndrome, and cardiovascular disease |
-
2002
- 2002-09-12 EP EP02762720A patent/EP1444009A1/en not_active Withdrawn
- 2002-09-12 PL PL02370599A patent/PL370599A1/xx not_active Application Discontinuation
- 2002-09-12 CN CNA028211529A patent/CN1575191A/zh active Pending
- 2002-09-12 CA CA002465632A patent/CA2465632A1/en not_active Abandoned
- 2002-09-12 MX MXPA04004170A patent/MXPA04004170A/es unknown
- 2002-09-12 JP JP2003539771A patent/JP2005508978A/ja not_active Withdrawn
- 2002-09-12 IL IL16115502A patent/IL161155A0/xx unknown
- 2002-09-12 BR BR0213817-4A patent/BR0213817A/pt not_active IP Right Cessation
- 2002-09-12 WO PCT/IB2002/003754 patent/WO2003037432A1/en not_active Ceased
- 2002-09-12 HU HU0401998A patent/HUP0401998A2/hu unknown
- 2002-09-12 KR KR10-2004-7006251A patent/KR20040053210A/ko not_active Ceased
- 2002-10-29 US US10/283,814 patent/US6967204B2/en not_active Expired - Fee Related
-
2004
- 2004-03-18 ZA ZA200402173A patent/ZA200402173B/en unknown
- 2004-09-15 US US10/942,438 patent/US20050070557A1/en not_active Abandoned
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005527565A (ja) * | 2002-03-28 | 2005-09-15 | ウスタフ エクスペリメンタルニ ボタニキ エーブイ シーアール （インスティチュート オブ エクスペリメンタル ボタニー アカデミー オブ サイエンシーズ オブ ザ チェコ リパブリック） | 新しいピラゾロ［４，３−ｄ］ピリミジン、その調整方法、及び治療方法 |
| WO2008018306A1 (en) * | 2006-08-08 | 2008-02-14 | Aska Pharmaceutical Co., Ltd. | Quinazoline derivative |
| US8101624B2 (en) | 2006-08-08 | 2012-01-24 | Aska Pharmaceutical Co., Ltd. | Quinazoline derivatives |
| JP5193866B2 (ja) * | 2006-08-08 | 2013-05-08 | あすか製薬株式会社 | キナゾリン誘導体 |
| WO2008072778A1 (ja) * | 2006-12-13 | 2008-06-19 | Aska Pharmaceutical Co., Ltd. | 尿路系疾患の処置剤 |
| JP2010526863A (ja) * | 2007-05-11 | 2010-08-05 | ファイザー・インク | アミノ複素環式化合物 |
| JP2011504913A (ja) * | 2007-11-30 | 2011-02-17 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | １，５−ジヒドロ−ピラゾロ［３，４−ｄ］ピリミジン−４−オン誘導体及びｃｎｓ障害の治療のためのｐｄｅ９ａモジュレーターとしてのそれらの使用 |
| JP2013540755A (ja) * | 2010-09-20 | 2013-11-07 | エンビボ・ファーマシューティカルズ・インコーポレイテッド | イミダゾトリアジノン化合物 |
| JP2016104747A (ja) * | 2010-09-20 | 2016-06-09 | フォーラム・ファーマシューティカルズ・インコーポレイテッドＦｏｒｕｍ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃ． | イミダゾトリアジノン化合物 |
| JP2015067538A (ja) * | 2013-09-26 | 2015-04-13 | 株式会社アイエイアイ | 血糖値降下剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| BR0213817A (pt) | 2004-10-19 |
| IL161155A0 (en) | 2004-08-31 |
| US6967204B2 (en) | 2005-11-22 |
| CN1575191A (zh) | 2005-02-02 |
| CA2465632A1 (en) | 2003-05-08 |
| EP1444009A1 (en) | 2004-08-11 |
| US20040023989A1 (en) | 2004-02-05 |
| US20050070557A1 (en) | 2005-03-31 |
| MXPA04004170A (es) | 2004-09-06 |
| KR20040053210A (ko) | 2004-06-23 |
| ZA200402173B (en) | 2005-03-18 |
| WO2003037432A1 (en) | 2003-05-08 |
| PL370599A1 (en) | 2005-05-30 |
| HUP0401998A2 (hu) | 2005-01-28 |
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