CN101848901B - 用于治疗高血压的噻唑烷二酮类似物 - Google Patents
用于治疗高血压的噻唑烷二酮类似物 Download PDFInfo
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- CN101848901B CN101848901B CN2008801147383A CN200880114738A CN101848901B CN 101848901 B CN101848901 B CN 101848901B CN 2008801147383 A CN2008801147383 A CN 2008801147383A CN 200880114738 A CN200880114738 A CN 200880114738A CN 101848901 B CN101848901 B CN 101848901B
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- KQKPFRSPSRPDEB-UHFFFAOYSA-N sumatriptan Chemical compound CNS(=O)(=O)CC1=CC=C2NC=C(CCN(C)C)C2=C1 KQKPFRSPSRPDEB-UHFFFAOYSA-N 0.000 description 1
- 229960000658 sumatriptan succinate Drugs 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229960005187 telmisartan Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 239000010496 thistle oil Substances 0.000 description 1
- 229960002203 tilactase Drugs 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 125000004385 trihaloalkyl group Chemical group 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229940038773 trisodium citrate Drugs 0.000 description 1
- 229910052722 tritium Chemical group 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-M undecanoate Chemical compound CCCCCCCCCCC([O-])=O ZDPHROOEEOARMN-UHFFFAOYSA-M 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
- 229960001254 vildagliptin Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/34—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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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
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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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Immunology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Biomedical Technology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Pulmonology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Cardiology (AREA)
- Rheumatology (AREA)
- Psychology (AREA)
- Child & Adolescent Psychology (AREA)
- Pain & Pain Management (AREA)
- Transplantation (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US97263907P | 2007-09-14 | 2007-09-14 | |
| US60/972,639 | 2007-09-14 | ||
| PCT/US2008/010723 WO2009038681A1 (en) | 2007-09-14 | 2008-09-15 | Thiazolidinedione analogues for the treatment of hypertension |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101848901A CN101848901A (zh) | 2010-09-29 |
| CN101848901B true CN101848901B (zh) | 2012-11-21 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2008801147383A Active CN101848901B (zh) | 2007-09-14 | 2008-09-15 | 用于治疗高血压的噻唑烷二酮类似物 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US8067450B2 (enExample) |
| EP (1) | EP2203433B1 (enExample) |
| JP (1) | JP5371988B2 (enExample) |
| KR (1) | KR101537830B1 (enExample) |
| CN (1) | CN101848901B (enExample) |
| AU (1) | AU2008301905B2 (enExample) |
| BR (1) | BRPI0817096B8 (enExample) |
| CA (1) | CA2699289C (enExample) |
| ES (1) | ES2398313T3 (enExample) |
| IL (1) | IL204440A (enExample) |
| MX (1) | MX2010002820A (enExample) |
| NZ (2) | NZ597381A (enExample) |
| PL (1) | PL2203433T3 (enExample) |
| RU (1) | RU2486179C2 (enExample) |
| WO (1) | WO2009038681A1 (enExample) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP5149271B2 (ja) | 2006-03-16 | 2013-02-20 | 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 | 高血圧症を処置するためならびに脂質を下げるためのチアゾリジンジオン類似体 |
| RU2445957C2 (ru) | 2006-03-16 | 2012-03-27 | Метаболик Солюшнз Девелопмент Компани | Аналоги тиазолидиндиона |
| US8304441B2 (en) | 2007-09-14 | 2012-11-06 | Metabolic Solutions Development Company, Llc | Thiazolidinedione analogues for the treatment of metabolic diseases |
| AU2008301905B2 (en) | 2007-09-14 | 2013-06-27 | Cirius Therapeutics, Inc. | Thiazolidinedione analogues for the treatment of hypertension |
| US8722710B2 (en) | 2007-09-26 | 2014-05-13 | Deuterx, Llc | Deuterium-enriched pioglitazone |
| WO2010105048A1 (en) * | 2009-03-12 | 2010-09-16 | Metabolic Solutions Development Company | Thiazolidinedione analogues |
| NZ600421A (en) * | 2009-12-15 | 2014-06-27 | Metabolic Solutions Dev Co Llc | Ppar-sparing thiazolidinediones and combinations for the treatment of neurodegenerative diseases |
| AU2010340058A1 (en) * | 2009-12-15 | 2012-06-21 | Metabolic Solutions Development Company, Llc | PPAR-sparing thiazolidinediones and combinations for the treatment of diabetes mellitus and other metabolic diseases |
| KR20120092714A (ko) * | 2009-12-15 | 2012-08-21 | 메타볼릭 솔루션스 디벨롭먼트 컴퍼니, 엘엘씨 | 비만 및 다른 대사성 질환의 치료를 위한 ｐｐａｒ 절약형 티아졸리딘디온 및 복합제 |
| HUE038042T2 (hu) * | 2009-12-15 | 2018-09-28 | Cirius Therapeutics Inc | PPAR helyettesítõ tiazolidindion sók metabolikus betegségek kezelésére |
| AU2014202074B2 (en) * | 2009-12-15 | 2016-01-07 | Cirius Therapeutics, Inc. | PPAR-sparing thiazolidinediones and combinations for the treatment of neurodegenerative diseases |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| MX2012012092A (es) * | 2010-04-19 | 2012-12-17 | Metabolic Solutions Dev Co Llc | Sintesis novedosa para compuestos de tiazolidinadiona. |
| EP2560615A1 (en) * | 2010-04-21 | 2013-02-27 | Metabolic Solutions Development Company LLC | Thiazolidinedione analogues |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| HUE029488T2 (en) * | 2010-08-10 | 2017-02-28 | Metabolic Solutions Dev Co Llc | Synthesis of Thiazolidinedione Compounds |
| HUE031424T2 (en) | 2010-08-10 | 2017-07-28 | Octeta Therapeutics Llc | New synthesis of thiazolidinedione compounds |
| WO2012109495A1 (en) * | 2011-02-09 | 2012-08-16 | Metabolic Solutions Development Company, Llc | Cellular targets of thiazolidinediones |
| WO2012149083A1 (en) * | 2011-04-28 | 2012-11-01 | Metabolic Solutions Development Company, Llc | Ppar-sparing thiazolidinediones for the treatment of kidney related diseases |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013068486A1 (en) | 2011-11-08 | 2013-05-16 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for the diagnosis and treatment of male infertility |
| AU2014236510A1 (en) | 2013-03-14 | 2015-09-24 | Deuterx, Llc | Deuterium-enriched 2,4-thiazolidinediones and methods of treatment |
| MX2016000724A (es) | 2013-07-22 | 2016-04-13 | Metabolic Solutions Dev Co Llc | Compuestos de reserva de los receptores activados del proliferador de peroxisoma (ppar) para el tratamiento de enfermedades metabolicas. |
| US10188639B2 (en) | 2014-01-15 | 2019-01-29 | Deuterx, Llc | Methods of treating neurological, metabolic, and other disorders using enantiopure deuterium-enriched pioglitazone |
| US20210038566A1 (en) | 2018-02-08 | 2021-02-11 | Enyo Pharma | Use of modulators of neet proteins for the treatment of infection |
| US11319313B2 (en) | 2020-06-30 | 2022-05-03 | Poxel Sa | Crystalline forms of deuterium-enriched pioglitazone |
| US11767317B1 (en) | 2020-06-30 | 2023-09-26 | Poxel Sa | Methods of synthesizing enantiopure 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) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0008203A1 (en) * | 1978-08-04 | 1980-02-20 | Takeda Chemical Industries, Ltd. | Thiazolidine derivatives, preparing same and pharmaceutical compositions comprising same |
| EP0549365A1 (en) * | 1991-12-26 | 1993-06-30 | Sankyo Company Limited | Thiazolidine compounds, their preparation and their therapeutic uses |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5356913A (en) * | 1990-02-09 | 1994-10-18 | The Upjohn Company | Use of insulin sensitizing agents to treat hypertension |
| 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 |
| US5994341A (en) | 1993-07-19 | 1999-11-30 | Angiogenesis Technologies, Inc. | Anti-angiogenic Compositions and methods for the treatment of arthritis |
| NO305987B1 (no) * | 1994-04-11 | 1999-08-30 | Sankyo Co | Heterosykliske forbindelser med antidiabetisk aktivitet, deres anvendelse og farmasoeytisk preparat inneholdende disse |
| 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 |
| NZ286920A (en) | 1995-07-03 | 1997-06-24 | Sankyo Co | Use of combination of hmg-coa reductase inhibitors and of insulin sensitizers for the prevention/treatment of arteriosclerosis or xanthoma |
| CA2371391A1 (en) * | 1999-04-29 | 2000-11-09 | City Of Hope | Pentoxifylline, pioglitazone and metformin are inhibitors of formation of advanced glycation endproducts (age's) |
| DK1192137T3 (da) | 1999-06-30 | 2013-11-11 | Amgen Inc | Forbindelser til modulering af PPAR-gamma aktivitet |
| WO2001082916A2 (en) | 2000-05-03 | 2001-11-08 | Tularik Inc. | Combination therapeutic compositions and methods of use |
| US7009057B2 (en) | 2001-04-26 | 2006-03-07 | Zentiva A.S. | Method for obtaining pioglitazone as an antidiabetic agent |
| US7135485B2 (en) * | 2001-09-28 | 2006-11-14 | Teva Pharmaceutical Industries Ltd. | Pioglitazone hydrochloride |
| WO2004007490A2 (en) | 2002-07-16 | 2004-01-22 | Cadila Healthcare Limited | A process to prepare pioglitazone via several intermediates. |
| JPWO2004082715A1 (ja) * | 2003-03-20 | 2006-06-22 | エーザイ株式会社 | 炎症性腸疾患治療剤としての併用医薬 |
| US7230016B2 (en) | 2003-05-13 | 2007-06-12 | Synthon Ip Inc. | Pioglitazone salts, such as pioglitazone sulfate, and pharmaceutical compositions and processes using the same |
| JP2005015477A (ja) * | 2003-06-06 | 2005-01-20 | Takeda Chem Ind Ltd | 固形製剤 |
| US20070078170A1 (en) * | 2003-08-28 | 2007-04-05 | Khanduri Chandra H | Process for the preparation of pioglitazone |
| AR047541A1 (es) * | 2004-02-13 | 2006-01-25 | Sandoz Ag | Fosfato de 5-[[4-[2-metil-2-piridinil-amino-etoxi]fenil]metil]-2,4 tiazolidinadiona (rosiglitazona) y sus formas polimorficas |
| US7777038B2 (en) | 2004-09-28 | 2010-08-17 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril compound |
| CA2646170A1 (en) | 2006-03-16 | 2007-09-27 | Metabolic Solutions Development Company | Combination therapies of thiazolidinedione analogues and glucocorticoid agonists |
| RU2445957C2 (ru) | 2006-03-16 | 2012-03-27 | Метаболик Солюшнз Девелопмент Компани | Аналоги тиазолидиндиона |
| JP5149271B2 (ja) | 2006-03-16 | 2013-02-20 | 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 | 高血圧症を処置するためならびに脂質を下げるためのチアゾリジンジオン類似体 |
| AU2008301905B2 (en) | 2007-09-14 | 2013-06-27 | Cirius Therapeutics, Inc. | Thiazolidinedione analogues for the treatment of hypertension |
| WO2010105048A1 (en) | 2009-03-12 | 2010-09-16 | Metabolic Solutions Development Company | Thiazolidinedione analogues |
-
2008
- 2008-09-15 AU AU2008301905A patent/AU2008301905B2/en active Active
- 2008-09-15 BR BRPI0817096A patent/BRPI0817096B8/pt active IP Right Grant
- 2008-09-15 RU RU2010114727/04A patent/RU2486179C2/ru active
- 2008-09-15 JP JP2010524882A patent/JP5371988B2/ja active Active
- 2008-09-15 NZ NZ597381A patent/NZ597381A/xx unknown
- 2008-09-15 US US12/677,541 patent/US8067450B2/en active Active
- 2008-09-15 NZ NZ583889A patent/NZ583889A/en unknown
- 2008-09-15 CA CA2699289A patent/CA2699289C/en active Active
- 2008-09-15 MX MX2010002820A patent/MX2010002820A/es active IP Right Grant
- 2008-09-15 PL PL08832210T patent/PL2203433T3/pl unknown
- 2008-09-15 CN CN2008801147383A patent/CN101848901B/zh active Active
- 2008-09-15 WO PCT/US2008/010723 patent/WO2009038681A1/en not_active Ceased
- 2008-09-15 EP EP08832210A patent/EP2203433B1/en active Active
- 2008-09-15 KR KR1020107008064A patent/KR101537830B1/ko active Active
- 2008-09-15 ES ES08832210T patent/ES2398313T3/es active Active
-
2010
- 2010-03-11 IL IL204440A patent/IL204440A/en active IP Right Grant
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0008203A1 (en) * | 1978-08-04 | 1980-02-20 | Takeda Chemical Industries, Ltd. | Thiazolidine derivatives, preparing same and pharmaceutical compositions comprising same |
| EP0549365A1 (en) * | 1991-12-26 | 1993-06-30 | Sankyo Company Limited | Thiazolidine compounds, their preparation and their therapeutic uses |
Non-Patent Citations (4)
| Title |
|---|
| Pietro Gerber et al..Effects of pioglitazone on metabolic control and blood pressure: A randomised study in patients with type 2 diabetes mellius.《Current Medical Research and Opinion》.2003,第19卷(第6期),532-539. * |
| Steven P. Tanis, et al..Synthesis and Biological Activity of Metabolites of the Antidiabetic, Antihyperglycemic Agent Pioglitazone.《J. Med. Chem.》.1996,第39卷(第26期),5053-5063. * |
| StevenP.Tanis et al..Synthesis and Biological Activity of Metabolites of the Antidiabetic |
| Takashi Sohda, et al..Studies on Antidiabetic Agents. II. Synthesis of 5-[4-(1-Methylcyclohexylmethoxy)-benzyl] thiazolidine-2, 4-dione (ADD-3878) and Its Derivatives.《Chem. Pharm. Bull.》.1982,第30卷(第10期),3580-3600. * |
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0817096B1 (pt) | 2020-11-10 |
| BRPI0817096B8 (pt) | 2021-05-25 |
| CA2699289A1 (en) | 2009-03-26 |
| AU2008301905B2 (en) | 2013-06-27 |
| IL204440A (en) | 2013-05-30 |
| CN101848901A (zh) | 2010-09-29 |
| MX2010002820A (es) | 2010-04-01 |
| RU2010114727A (ru) | 2011-10-20 |
| BRPI0817096A2 (pt) | 2017-05-02 |
| NZ583889A (en) | 2012-01-12 |
| BRPI0817096A8 (pt) | 2017-10-10 |
| KR101537830B1 (ko) | 2015-07-17 |
| KR20100075915A (ko) | 2010-07-05 |
| PL2203433T3 (pl) | 2013-04-30 |
| RU2486179C2 (ru) | 2013-06-27 |
| AU2008301905A1 (en) | 2009-03-26 |
| CA2699289C (en) | 2016-01-19 |
| JP5371988B2 (ja) | 2013-12-18 |
| ES2398313T3 (es) | 2013-03-15 |
| HK1146484A1 (en) | 2011-06-10 |
| WO2009038681A1 (en) | 2009-03-26 |
| US8067450B2 (en) | 2011-11-29 |
| NZ597381A (en) | 2013-03-28 |
| JP2010539171A (ja) | 2010-12-16 |
| US20100222399A1 (en) | 2010-09-02 |
| EP2203433A1 (en) | 2010-07-07 |
| EP2203433B1 (en) | 2012-10-31 |
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