CA2557320C - Fused heterocyclic derivatives for prevention or treatment of hyperglycemia - Google Patents
Fused heterocyclic derivatives for prevention or treatment of hyperglycemia Download PDFInfo
- Publication number
- CA2557320C CA2557320C CA2557320A CA2557320A CA2557320C CA 2557320 C CA2557320 C CA 2557320C CA 2557320 A CA2557320 A CA 2557320A CA 2557320 A CA2557320 A CA 2557320A CA 2557320 C CA2557320 C CA 2557320C
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- inhibitor
- alkyl
- alkoxy
- hydroxy
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- 150000003839 salts Chemical class 0.000 claims abstract description 48
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Molecular Biology (AREA)
- Obesity (AREA)
- Biochemistry (AREA)
- Heart & Thoracic Surgery (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Pulmonology (AREA)
- Vascular Medicine (AREA)
- Rheumatology (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2004-61429 | 2004-03-04 | ||
| JP2004061429 | 2004-03-04 | ||
| PCT/JP2005/004152 WO2005085265A1 (ja) | 2004-03-04 | 2005-03-03 | 縮合ヘテロ環誘導体、それを含有する医薬組成物およびその医薬用途 |
Publications (2)
| Publication Number | Publication Date |
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| CA2557320A1 CA2557320A1 (en) | 2005-09-15 |
| CA2557320C true CA2557320C (en) | 2013-02-05 |
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| CA2557320A Expired - Fee Related CA2557320C (en) | 2004-03-04 | 2005-03-03 | Fused heterocyclic derivatives for prevention or treatment of hyperglycemia |
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| Country | Link |
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| EP (1) | EP1724277A4 (enExample) |
| JP (1) | JP5078350B2 (enExample) |
| KR (1) | KR101214433B1 (enExample) |
| CN (1) | CN1934122B (enExample) |
| AU (1) | AU2005219777B2 (enExample) |
| CA (1) | CA2557320C (enExample) |
| IL (1) | IL177513A (enExample) |
| MA (1) | MA28512B1 (enExample) |
| NO (1) | NO20064412L (enExample) |
| NZ (1) | NZ549219A (enExample) |
| PL (1) | PL381247A1 (enExample) |
| RU (1) | RU2387663C2 (enExample) |
| TW (1) | TW200540167A (enExample) |
| WO (1) | WO2005085265A1 (enExample) |
| ZA (1) | ZA200606792B (enExample) |
Families Citing this family (50)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA011158B1 (ru) | 2004-03-16 | 2009-02-27 | Бёрингер Ингельхайм Интернациональ Гмбх | Замещённые глюкопиранозилом бензольные производные, содержащие эти соединения лекарственные средства, их применение и способ их получения |
| JP2008524162A (ja) | 2004-12-16 | 2008-07-10 | 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 | グルコピラノシル置換ベンゼン誘導体、該化合物を含む薬物、その使用及びその製造方法 |
| TW200637869A (en) | 2005-01-28 | 2006-11-01 | Chugai Pharmaceutical Co Ltd | The spiroketal derivatives and the use as therapeutical agent for diabetes of the same |
| JP5264183B2 (ja) | 2005-02-23 | 2013-08-14 | 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 | グルコピラノシル置換（（ヘテロ）アリールエチニル−ベンジル）−ベンゼン誘導体及びナトリウム依存性グルコース共輸送体２（ｓｇｌｔ２）インヒビターとしてのそれらの使用 |
| WO2006108842A1 (en) | 2005-04-15 | 2006-10-19 | Boehringer Ingelheim International Gmbh | Glucopyranosyl-substituted (heteroaryloxy-benzyl)-benzene derivatives as sglt inhibitors |
| US7723309B2 (en) | 2005-05-03 | 2010-05-25 | Boehringer Ingelheim International Gmbh | Crystalline forms of 1-chloro-4-(β-D-glucopyranos-1-yl)-2-[4-((R)-tetrahydrofuran-3-yloxy)-benzyl]-benzene, a method for its preparation and the use thereof for preparing medicaments |
| UA91546C2 (uk) | 2005-05-03 | 2010-08-10 | Бьорінгер Інгельхайм Інтернаціональ Гмбх | КРИСТАЛІЧНА ФОРМА 1-ХЛОР-4-(β-D-ГЛЮКОПІРАНОЗ-1-ИЛ)-2-[4-((S)-ТЕТРАГІДРОФУРАН-3-ІЛОКСИ)-БЕНЗИЛ]-БЕНЗОЛУ, СПОСІБ ЇЇ ОДЕРЖАННЯ ТА ЇЇ ЗАСТОСУВАННЯ ПРИ ПРИГОТУВАННІ ЛІКАРСЬКИХ ЗАСОБІВ |
| US7772191B2 (en) | 2005-05-10 | 2010-08-10 | Boehringer Ingelheim International Gmbh | Processes for preparing of glucopyranosyl-substituted benzyl-benzene derivatives and intermediates therein |
| EP1910390B1 (en) | 2005-07-27 | 2010-05-19 | Boehringer Ingelheim International GmbH | Glucopyranosyl-substituted ((hetero)cycloalyklethynyl-benzyl)-benzene derivatives and use thereof as sodium-dependent glucose cotransporter (sglt) inhibitors |
| JP5175191B2 (ja) | 2005-08-30 | 2013-04-03 | 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 | グリコピラノシル置換ベンジルベンゼン誘導体、該化合物を含有する医薬品及びその使用と製造方法 |
| BRPI0615882A2 (pt) | 2005-09-08 | 2011-05-31 | Boehringer Ingelheim Int | formas cristalinas de 1-cloro-4-(beta-d-glicopiranos-1-il)-2-(4-etinil-benzil)- benzeno, métodos para sua preparação e o uso para preparar medicamentos do mesmo |
| AR056195A1 (es) | 2005-09-15 | 2007-09-26 | Boehringer Ingelheim Int | Procedimientos para preparar derivados de (etinil-bencil)-benceno sustituidos de glucopiranosilo y compuestos intermedios de los mismos |
| AR059489A1 (es) | 2006-02-15 | 2008-04-09 | Boehringer Ingelheim Vetmed | Derivados de benzonitrilo sustituidos con glucopiranosilo, composiciones farmaceuticas que contienen compuestos de este tipo, su uso y procedimiento para su fabricacion |
| PE20080697A1 (es) | 2006-05-03 | 2008-08-05 | Boehringer Ingelheim Int | Derivados de benzonitrilo sustituidos con glucopiranosilo, composiciones farmaceuticas que contienen compuestos de este tipo, su uso y procedimiento para su fabricacion |
| PE20080251A1 (es) | 2006-05-04 | 2008-04-25 | Boehringer Ingelheim Int | Usos de inhibidores de dpp iv |
| TWI432446B (zh) | 2006-07-27 | 2014-04-01 | Chugai Pharmaceutical Co Ltd | 稠環螺酮縮醇衍生物、及其做為糖尿病治療藥之使用 |
| TWI403516B (zh) | 2006-07-27 | 2013-08-01 | Chugai Pharmaceutical Co Ltd | To replace spirocyclic alcohol derivatives, and its use as a therapeutic agent for diabetes |
| TWI499414B (zh) | 2006-09-29 | 2015-09-11 | Lexicon Pharmaceuticals Inc | 鈉與葡萄糖第２型共同運輸體（ｃｏ-ｔｒａｎｓｐｏｒｔｅｒ ２）的抑制物與其應用方法 |
| BRPI0719523A2 (pt) * | 2006-10-13 | 2015-06-16 | Chugai Pharmaceutical Co Ltd | Derivado de espirocetal de tioglicose e uso deste como agente terapêutico para diabetes |
| CN100586932C (zh) * | 2007-01-26 | 2010-02-03 | 中国医学科学院医药生物技术研究所 | 抗肿瘤化合物及其制备方法 |
| US7846945B2 (en) * | 2007-03-08 | 2010-12-07 | Lexicon Pharmaceuticals, Inc. | Piperdine-based inhibitors of sodium glucose co-transporter 2 and methods of their use |
| PE20090938A1 (es) | 2007-08-16 | 2009-08-08 | Boehringer Ingelheim Int | Composicion farmaceutica que comprende un derivado de benceno sustituido con glucopiranosilo |
| CL2008003653A1 (es) * | 2008-01-17 | 2010-03-05 | Mitsubishi Tanabe Pharma Corp | Uso de un inhibidor de sglt derivado de glucopiranosilo y un inhibidor de dppiv seleccionado para tratar la diabetes; y composicion farmaceutica. |
| ES2380408T3 (es) * | 2008-08-28 | 2012-05-11 | Pfizer Inc. | Derivados de dioxa-biciclo[3.2.1]octano-2,3,4-triol |
| KR20110118668A (ko) | 2009-02-13 | 2011-10-31 | 베링거 인겔하임 인터내셔날 게엠베하 | １형 당뇨병, ２형 당뇨병, 내당능 장애 또는 고혈당증을 치료하기 위한 ｓｇｌｔ２ 억제제 |
| MX339194B (es) | 2009-02-13 | 2016-05-16 | Boehringer Ingelheim Int | Composicion farmaceutica que comprende un inhibidor de sglt2, un inhibidor de dpp-iv y opcionalmente otro agente antidiabetico, y usos de la misma. |
| DK2486029T3 (en) | 2009-09-30 | 2015-08-24 | Boehringer Ingelheim Int | Methods of making of glucopyranosyl-substituted benzyl-benzene derivatives. |
| ES2596202T3 (es) | 2009-09-30 | 2017-01-05 | Boehringer Ingelheim International Gmbh | Método para la preparación de una forma cristalina de 1-cloro-4-(ß-D-glucopiranos-1-il)-2-[4-((S)-tetrahidrofuran-3-iloxi)-bencil]-benceno |
| US10610489B2 (en) | 2009-10-02 | 2020-04-07 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, pharmaceutical dosage form, process for their preparation, methods for treating and uses thereof |
| KR20120087950A (ko) | 2009-10-20 | 2012-08-07 | 노파르티스 아게 | 글리코시드 유도체 및 그의 용도 |
| US8163704B2 (en) | 2009-10-20 | 2012-04-24 | Novartis Ag | Glycoside derivatives and uses thereof |
| US8669380B2 (en) | 2009-11-02 | 2014-03-11 | Pfizer Inc. | Dioxa-bicyclo[3.2.1]octane-2,3,4-triol derivatives |
| AR079438A1 (es) | 2009-12-09 | 2012-01-25 | Panacea Biotec Ltd | Derivados de azucar, composiciones farmaceuticas y sus usos |
| AR085689A1 (es) | 2011-03-07 | 2013-10-23 | Boehringer Ingelheim Int | Composiciones farmaceuticas de metformina, linagliptina y un inhibidor de sglt-2 |
| US8614195B2 (en) | 2011-04-14 | 2013-12-24 | Novartis Ag | Glycoside derivatives and uses thereof |
| JP2014510782A (ja) | 2011-04-14 | 2014-05-01 | ノバルティス アーゲー | グリコシド誘導体およびその使用 |
| WO2013038429A2 (en) | 2011-09-13 | 2013-03-21 | Panacea Biotec Ltd. | Novel sglt inhibitors |
| US9555001B2 (en) | 2012-03-07 | 2017-01-31 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition and uses thereof |
| US9192617B2 (en) | 2012-03-20 | 2015-11-24 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| US8652527B1 (en) | 2013-03-13 | 2014-02-18 | Upsher-Smith Laboratories, Inc | Extended-release topiramate capsules |
| US9101545B2 (en) | 2013-03-15 | 2015-08-11 | Upsher-Smith Laboratories, Inc. | Extended-release topiramate capsules |
| US11813275B2 (en) | 2013-04-05 | 2023-11-14 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| CA2812519A1 (en) | 2013-04-05 | 2014-10-05 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| US20140303097A1 (en) | 2013-04-05 | 2014-10-09 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| HRP20190101T1 (hr) | 2013-04-05 | 2019-03-08 | Boehringer Ingelheim International Gmbh | Terapeutske uporabe empagliflozina |
| PL2986304T3 (pl) | 2013-04-18 | 2022-05-02 | Boehringer Ingelheim International Gmbh | Kompozycja farmaceutyczna, sposoby leczenia i jej zastosowania |
| CN104447893B (zh) * | 2013-09-25 | 2018-01-23 | 广东东阳光药业有限公司 | 吡喃葡萄糖基衍生物及其在医药上的应用 |
| WO2018087132A1 (en) | 2016-11-10 | 2018-05-17 | Boehringer Ingelheim International Gmbh | Pharmaceutical composition, methods for treating and uses thereof |
| LT3716979T (lt) | 2017-11-30 | 2025-07-10 | Idorsia Pharmaceuticals Ltd | 4-pirimidinsulfamido darinio derinys su sglt-2 inhibitoriumi, skirtas su endotelinu susijusių ligų gydymui |
| CN116283895A (zh) * | 2023-01-09 | 2023-06-23 | 怀化宝华生物科技有限公司 | 一种2-[2-(噻吩基)乙基]苯甲酸的制备方法 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5582837A (en) * | 1992-03-25 | 1996-12-10 | Depomed, Inc. | Alkyl-substituted cellulose-based sustained-release oral drug dosage forms |
| US5502187A (en) * | 1992-04-03 | 1996-03-26 | The Upjohn Company | Pharmaceutically active bicyclic-heterocyclic amines |
| PT633886E (pt) | 1992-04-03 | 2001-03-30 | Upjohn Co | Aminas biciclicas-heterociclicas farmaceuticamente activas |
| PH12000002657B1 (en) * | 1999-10-12 | 2006-02-21 | Bristol Myers Squibb Co | C-aryl glucoside SGLT2 inhibitors |
| US6515117B2 (en) * | 1999-10-12 | 2003-02-04 | Bristol-Myers Squibb Company | C-aryl glucoside SGLT2 inhibitors and method |
| DE60103203T2 (de) * | 2000-04-13 | 2005-05-04 | Pfizer Products Inc., Groton | Synergistische Wirkung von Glyburide und Milrinone |
| JP2002193948A (ja) | 2000-10-06 | 2002-07-10 | Sankyo Co Ltd | α−置換カルボン酸誘導体を含有する糖尿病治療剤 |
| US7271153B2 (en) | 2001-06-20 | 2007-09-18 | Kissei Pharmaceutical Co., Ltd. | Nitrogenous heterocyclic derivatives, medicinal compositions containing the same, medicinal uses thereof, and intermediates therefor |
| JP4115105B2 (ja) * | 2001-07-02 | 2008-07-09 | 協和醗酵工業株式会社 | ピラゾール誘導体 |
| DE60227421D1 (de) * | 2002-04-08 | 2008-08-14 | Council Scient Ind Res | Rmazeutische zusammensetzung und verwendung davon |
| TWI254635B (en) * | 2002-08-05 | 2006-05-11 | Yamanouchi Pharma Co Ltd | Azulene derivative and salt thereof |
| ATE510834T1 (de) * | 2003-03-14 | 2011-06-15 | Astellas Pharma Inc | C-glykosid-derivate zur behandlung von diabetes |
| JP2004300102A (ja) | 2003-03-31 | 2004-10-28 | Kissei Pharmaceut Co Ltd | 縮合複素環誘導体、それを含有する医薬組成物およびその医薬用途 |
| AU2005219779B2 (en) * | 2004-03-04 | 2011-04-14 | Kissei Pharmaceutical Co., Ltd. | Fused heterocycle derivative, medicinal composition containing the same, and medicinal use thereof |
-
2005
- 2005-03-03 CA CA2557320A patent/CA2557320C/en not_active Expired - Fee Related
- 2005-03-03 US US10/591,403 patent/US7732596B2/en not_active Expired - Fee Related
- 2005-03-03 AU AU2005219777A patent/AU2005219777B2/en not_active Ceased
- 2005-03-03 NZ NZ549219A patent/NZ549219A/en not_active IP Right Cessation
- 2005-03-03 KR KR1020067019362A patent/KR101214433B1/ko not_active Expired - Fee Related
- 2005-03-03 RU RU2006131552/04A patent/RU2387663C2/ru not_active IP Right Cessation
- 2005-03-03 ZA ZA200606792A patent/ZA200606792B/xx unknown
- 2005-03-03 PL PL381247A patent/PL381247A1/pl not_active Application Discontinuation
- 2005-03-03 CN CN2005800062115A patent/CN1934122B/zh not_active Expired - Fee Related
- 2005-03-03 JP JP2006510804A patent/JP5078350B2/ja not_active Expired - Fee Related
- 2005-03-03 WO PCT/JP2005/004152 patent/WO2005085265A1/ja not_active Ceased
- 2005-03-03 EP EP05720423A patent/EP1724277A4/en not_active Withdrawn
- 2005-03-04 TW TW094106585A patent/TW200540167A/zh not_active IP Right Cessation
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2006
- 2006-08-16 IL IL177513A patent/IL177513A/en not_active IP Right Cessation
- 2006-09-29 NO NO20064412A patent/NO20064412L/no not_active Application Discontinuation
- 2006-10-02 MA MA29361A patent/MA28512B1/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO20064412L (no) | 2006-12-04 |
| ZA200606792B (en) | 2007-12-27 |
| PL381247A1 (pl) | 2007-05-14 |
| IL177513A0 (en) | 2006-12-10 |
| AU2005219777B2 (en) | 2011-02-03 |
| NZ549219A (en) | 2010-08-27 |
| MA28512B1 (fr) | 2007-04-03 |
| CA2557320A1 (en) | 2005-09-15 |
| WO2005085265A1 (ja) | 2005-09-15 |
| EP1724277A4 (en) | 2012-05-02 |
| US7732596B2 (en) | 2010-06-08 |
| HK1099556A1 (zh) | 2007-08-17 |
| US20070197449A1 (en) | 2007-08-23 |
| JP5078350B2 (ja) | 2012-11-21 |
| KR101214433B1 (ko) | 2012-12-21 |
| TW200540167A (en) | 2005-12-16 |
| JPWO2005085265A1 (ja) | 2008-01-17 |
| AU2005219777A1 (en) | 2005-09-15 |
| EP1724277A1 (en) | 2006-11-22 |
| KR20060132737A (ko) | 2006-12-21 |
| CN1934122B (zh) | 2010-08-04 |
| IL177513A (en) | 2011-11-30 |
| RU2387663C2 (ru) | 2010-04-27 |
| RU2006131552A (ru) | 2008-03-10 |
| CN1934122A (zh) | 2007-03-21 |
| TWI361190B (enExample) | 2012-04-01 |
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| MKLA | Lapsed |
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