HUE035314T2 - Thiazolidinedione analogues for the treatment of a disease mediated by metabolic inflammation - Google Patents
Thiazolidinedione analogues for the treatment of a disease mediated by metabolic inflammation Download PDFInfo
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- HUE035314T2 HUE035314T2 HUE15151582A HUE15151582A HUE035314T2 HU E035314 T2 HUE035314 T2 HU E035314T2 HU E15151582 A HUE15151582 A HU E15151582A HU E15151582 A HUE15151582 A HU E15151582A HU E035314 T2 HUE035314 T2 HU E035314T2
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- treatment
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- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
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- Health & Medical Sciences (AREA)
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- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- General Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Neurology (AREA)
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- Diabetes (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pulmonology (AREA)
- Physical Education & Sports Medicine (AREA)
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- Cardiology (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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| US78289406P | 2006-03-16 | 2006-03-16 |
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| HUE035314T2 true HUE035314T2 (en) | 2018-05-02 |
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| CN (1) | CN101454005B (https=) |
| AU (1) | AU2007227581B2 (https=) |
| CA (1) | CA2646207C (https=) |
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| PL (2) | PL2902026T3 (https=) |
| RU (1) | RU2445957C2 (https=) |
| UA (1) | UA96441C2 (https=) |
| WO (1) | WO2007109024A2 (https=) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA96441C2 (ru) | 2006-03-16 | 2011-11-10 | Метаболик Солюшнз Девелопмент Компани | Фармацевтическая композиция, которая содержит аналог тиазолидиндиона митоглитазон, для лечения заболеваний, опосредованных метаболическим воспалением |
| CN101448500A (zh) * | 2006-03-16 | 2009-06-03 | 新陈代谢解决方案开发公司 | 噻唑烷二酮类似物和糖皮质激素激动剂的组合疗法 |
| WO2007109037A2 (en) | 2006-03-16 | 2007-09-27 | Metabolic Solutions Development Company | Thiazolidinedione analogues for the treatment of hypertension and for lowering lipids |
| US8304441B2 (en) | 2007-09-14 | 2012-11-06 | Metabolic Solutions Development Company, Llc | Thiazolidinedione analogues for the treatment of metabolic diseases |
| KR101537830B1 (ko) | 2007-09-14 | 2015-07-17 | 메타볼릭 솔루션스 디벨롭먼트 컴퍼니, 엘엘씨 | 고혈압 치료용 티아졸리딘디온 유사체 |
| US8722710B2 (en) | 2007-09-26 | 2014-05-13 | Deuterx, Llc | Deuterium-enriched pioglitazone |
| ME01898B (me) | 2008-08-12 | 2014-12-20 | Zinfandel Pharmaceuticals Inc | Metoda za identifikaciju faktora rizika od alchajmerove bolesti |
| US8846315B2 (en) | 2008-08-12 | 2014-09-30 | Zinfandel Pharmaceuticals, Inc. | Disease risk factors and methods of use |
| ES2617704T3 (es) * | 2009-12-15 | 2017-06-19 | Octeta Therapeutics, Llc | Tiazolidindionas ahorradoras de PPAR y combinaciones para el tratamiento de enfermedades neurodegenerativas |
| AU2014202074B2 (en) * | 2009-12-15 | 2016-01-07 | Cirius Therapeutics, Inc. | PPAR-sparing thiazolidinediones and combinations for the treatment of neurodegenerative diseases |
| RU2564661C2 (ru) | 2009-12-15 | 2015-10-10 | МЕТАБОЛИК СОЛЮШНЗ ДЕВЕЛОПМЕНТ КОМПАНИ, ЭлЭлСи | Соли тиазолидиндиона со сниженным сродством к ppar для лечения нарушений обмена веществ |
| JP2013514369A (ja) * | 2009-12-15 | 2013-04-25 | メタボリック ソリューションズ ディベロップメント カンパニー， エルエルシー | 糖尿病および他の代謝性疾患を処置するための、ｐｐａｒ温存チアゾリジンジオンおよび組み合わせ物 |
| GB201002224D0 (en) | 2010-02-10 | 2010-03-31 | Argenta Therapeutics Ltd | Respiratory disease treatment |
| GB2477743A (en) * | 2010-02-10 | 2011-08-17 | Argenta Therapeutics Ltd | Enantiomers of 5-methyl-thiazolidine-2,4-dione glitazone compounds |
| AU2011242955A1 (en) * | 2010-04-19 | 2012-11-01 | Metabolic Solutions Development Company, Llc | Novel synthesis for thiazolidinedione compounds |
| MX2012012092A (es) | 2010-04-19 | 2012-12-17 | Metabolic Solutions Dev Co Llc | Sintesis novedosa para compuestos de tiazolidinadiona. |
| KR101988203B1 (ko) | 2010-08-10 | 2019-06-11 | 씨리우스 테라퓨틱스, 엘엘씨 | 티아졸리딘디온 화합물의 신규한 합성법 |
| CA2807815C (en) * | 2010-08-10 | 2018-10-02 | Metabolic Solutions Development Company, Llc | Novel synthesis for thiazolidinedione compounds |
| AU2012205798B2 (en) | 2011-01-10 | 2016-02-25 | Takeda Pharmaceutical Company Limited | Methods and drug products for treating Alzheimer's disease |
| WO2012114204A2 (en) | 2011-02-15 | 2012-08-30 | Ecole Polytechnique Federale De Lausanne (Epfl) Epfl-Tto | Methods of treating mitochondrial dysfunction |
| WO2012149083A1 (en) * | 2011-04-28 | 2012-11-01 | Metabolic Solutions Development Company, Llc | Ppar-sparing thiazolidinediones for the treatment of kidney related diseases |
| KR20130015932A (ko) * | 2011-08-05 | 2013-02-14 | 연세대학교 산학협력단 | 저용량의 치아졸리딘다이온을 포함하는 알츠하이머 병 치료용 약학조성물 |
| KR101501375B1 (ko) | 2012-09-21 | 2015-03-10 | 가톨릭대학교 산학협력단 | 메트포민을 유효성분으로 함유하는 염증성 장질환의 예방 또는 치료용 조성물 |
| WO2014046474A2 (ko) * | 2012-09-21 | 2014-03-27 | 가톨릭대학교 산학협력단 | 메트포민을 유효성분으로 함유하는 염증성 장질환의 예방 또는 치료용 조성물 |
| EP2931274A1 (en) * | 2012-12-11 | 2015-10-21 | Metabolic Solutions Development Company LLC | Ppar-sparing thiazolidinediones and combinations for the treatment of neurodegenerative diseases |
| CA2941562C (en) | 2013-03-14 | 2021-09-21 | Deuterx, Llc | Deuterium-enriched 2,4-thiazolidinediones and methods of treatment |
| WO2015013187A1 (en) | 2013-07-22 | 2015-01-29 | Metabolic Solutions Development Co., Llc | Ppar-sparing compounds for the treatment of metabolic diseases |
| US10188639B2 (en) | 2014-01-15 | 2019-01-29 | Deuterx, Llc | Methods of treating neurological, metabolic, and other disorders using enantiopure deuterium-enriched pioglitazone |
| EP3125888B1 (en) | 2014-04-02 | 2018-05-23 | Minoryx Therapeutics S.L. | 2,4-thiazolidinedione derivatives in the treatment of central nervous system disorders |
| EP3548026B1 (en) | 2016-12-01 | 2021-01-20 | Minoryx Therapeutics S.L. | 5-[[4-[2-[5-(1-hydroxyethyl)pyridin-2-yl]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione for treating nonalcoholic fatty liver disease |
| US11767317B1 (en) | 2020-06-30 | 2023-09-26 | Poxel Sa | Methods of synthesizing enantiopure deuterium-enriched pioglitazone |
| US11319313B2 (en) | 2020-06-30 | 2022-05-03 | Poxel Sa | Crystalline forms of deuterium-enriched pioglitazone |
| GB202210503D0 (en) | 2022-07-18 | 2022-08-31 | Univ Court Univ Of Glasgow | Materials and methods for treatment of chronic myeloid leukemia (CML) |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5522636A (en) | 1978-08-04 | 1980-02-18 | Takeda Chem Ind Ltd | Thiazoliding derivative |
| WO1985004170A1 (fr) * | 1984-03-21 | 1985-09-26 | Takeda Chemical Industries, Ltd. | Derives de thiazolidinedione, leur procede de preparation et compositions medicinales les contenant |
| US4582839A (en) * | 1984-03-21 | 1986-04-15 | Takeda Chemical Industries, Ltd. | 2,4-thiazolidinediones |
| CN1003445B (zh) * | 1984-10-03 | 1989-03-01 | 武田药品工业株式会社 | 噻唑烷二酮衍生物，其制备方法和用途 |
| WO1986002073A1 (fr) | 1984-10-03 | 1986-04-10 | Takeda Chemical Industries, Ltd. | Derives de thiazolidinedione, procede de preparation et composition pharmaceutique les contenant |
| AR240698A1 (es) * | 1985-01-19 | 1990-09-28 | Takeda Chemical Industries Ltd | Procedimiento para preparar compuestos de 5-(4-(2-(5-etil-2-piridil)-etoxi)benzil)-2,4-tiazolidindiona y sus sales |
| US5167228A (en) * | 1987-06-26 | 1992-12-01 | Brigham And Women's Hospital | Assessment and modification of endogenous circadian phase and amplitude |
| US5304121A (en) | 1990-12-28 | 1994-04-19 | Boston Scientific Corporation | Drug delivery system making use of a hydrogel polymer coating |
| US5441971A (en) * | 1991-04-11 | 1995-08-15 | The Upjohn Company | Thiazolidinedione derivatives, production and use thereof |
| CA2106967C (en) * | 1991-04-11 | 2003-12-09 | Takashi Sohda | Thiazolidinedione derivatives, production and use thereof |
| NO302471B1 (no) | 1991-12-26 | 1998-03-09 | Sankyo Co | Tiazolidinforbindelser og farmasöytisk preparat |
| US5886026A (en) | 1993-07-19 | 1999-03-23 | Angiotech Pharmaceuticals Inc. | Anti-angiogenic compositions and methods of use |
| AU679572B2 (en) * | 1993-09-15 | 1997-07-03 | Daiichi Sankyo Company, Limited | Use of thiazolidinediones to prevent or delay onset of NIDDM |
| US6099562A (en) | 1996-06-13 | 2000-08-08 | Schneider (Usa) Inc. | Drug coating with topcoat |
| TWI238064B (en) | 1995-06-20 | 2005-08-21 | Takeda Chemical Industries Ltd | A pharmaceutical composition for prophylaxis and treatment of diabetes |
| US5798375A (en) | 1995-07-03 | 1998-08-25 | Sankyo Company, Limited | Treatment of arteriosclerosis and xanthoma |
| GB0030845D0 (en) * | 2000-12-18 | 2001-01-31 | Smithkline Beecham Plc | Novel treatment |
| US7009057B2 (en) | 2001-04-26 | 2006-03-07 | Zentiva A.S. | Method for obtaining pioglitazone as an antidiabetic agent |
| EP1690538A4 (en) * | 2003-12-02 | 2009-02-25 | Shionogi & Co | ISOXAZOLE DERIVATIVE AGONISTIC ACTION AGAINST PEROXISOM PROLIFERATOR ACTIVATED RECEPTOR |
| CN101448500A (zh) * | 2006-03-16 | 2009-06-03 | 新陈代谢解决方案开发公司 | 噻唑烷二酮类似物和糖皮质激素激动剂的组合疗法 |
| WO2007109037A2 (en) | 2006-03-16 | 2007-09-27 | Metabolic Solutions Development Company | Thiazolidinedione analogues for the treatment of hypertension and for lowering lipids |
| UA96441C2 (ru) | 2006-03-16 | 2011-11-10 | Метаболик Солюшнз Девелопмент Компани | Фармацевтическая композиция, которая содержит аналог тиазолидиндиона митоглитазон, для лечения заболеваний, опосредованных метаболическим воспалением |
| KR101537830B1 (ko) | 2007-09-14 | 2015-07-17 | 메타볼릭 솔루션스 디벨롭먼트 컴퍼니, 엘엘씨 | 고혈압 치료용 티아졸리딘디온 유사체 |
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2007
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- 2007-03-14 PL PL15151582T patent/PL2902026T3/pl unknown
- 2007-03-14 CA CA2646207A patent/CA2646207C/en active Active
- 2007-03-14 AU AU2007227581A patent/AU2007227581B2/en not_active Ceased
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- 2007-03-14 PL PL07752982T patent/PL2001468T3/pl unknown
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- 2007-03-14 HU HUE15151582A patent/HUE035314T2/en unknown
- 2007-03-14 EP EP07752982A patent/EP2001468B1/en not_active Not-in-force
- 2007-03-14 JP JP2009500436A patent/JP5269758B2/ja not_active Expired - Fee Related
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- 2007-03-14 EP EP15151582.2A patent/EP2902026B1/en not_active Not-in-force
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