CN100439345C - 作为用于治疗 2型糠尿病和动脉硬化症的ppar调节剂的 3 - ( 2 -苯基 -噁唑-4-基甲氧基)环己基甲氧基乙酸衍生物和相关化合物 - Google Patents
作为用于治疗 2型糠尿病和动脉硬化症的ppar调节剂的 3 - ( 2 -苯基 -噁唑-4-基甲氧基)环己基甲氧基乙酸衍生物和相关化合物 Download PDFInfo
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- CN100439345C CN100439345C CNB2004800054379A CN200480005437A CN100439345C CN 100439345 C CN100439345 C CN 100439345C CN B2004800054379 A CNB2004800054379 A CN B2004800054379A CN 200480005437 A CN200480005437 A CN 200480005437A CN 100439345 C CN100439345 C CN 100439345C
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- methyl
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- oxazole
- cyclohexyl
- ylmethoxy
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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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
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- A—HUMAN NECESSITIES
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- 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
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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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
-
- 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
- A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
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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
- A61P9/10—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Diabetes (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
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| DE10308355A DE10308355A1 (de) | 2003-02-27 | 2003-02-27 | Aryl-cycloalkyl substituierte Alkansäurederivate, Verfahren zu ihrer Herstellung und ihre Anwendung als Arzneimittel |
| DE10308355.3 | 2003-02-27 |
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| CN1753879A CN1753879A (zh) | 2006-03-29 |
| CN100439345C true CN100439345C (zh) | 2008-12-03 |
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| CNB2004800054985A Expired - Fee Related CN100398526C (zh) | 2003-02-27 | 2004-02-19 | 作为用于治疗2型糖尿病和动脉粥样硬化的ppar调节剂的3－甲基－2－(3－(2－苯基－唑－4－基甲氧基)环己烷羰基－氨基)丁酸衍生物和相关化合物 |
| CNB2004800054769A Expired - Fee Related CN100439347C (zh) | 2003-02-27 | 2004-02-19 | 作为ppar调节剂用于治疗2型糖尿病和动脉粥样硬化的4-(3-(2-苯基噁唑-4-基甲氧基)-环己氧基)-丁酸衍生物及相关化合物 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
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| CNB2004800054985A Expired - Fee Related CN100398526C (zh) | 2003-02-27 | 2004-02-19 | 作为用于治疗2型糖尿病和动脉粥样硬化的ppar调节剂的3－甲基－2－(3－(2－苯基－唑－4－基甲氧基)环己烷羰基－氨基)丁酸衍生物和相关化合物 |
| CNB2004800054769A Expired - Fee Related CN100439347C (zh) | 2003-02-27 | 2004-02-19 | 作为ppar调节剂用于治疗2型糖尿病和动脉粥样硬化的4-(3-(2-苯基噁唑-4-基甲氧基)-环己氧基)-丁酸衍生物及相关化合物 |
Country Status (34)
Families Citing this family (17)
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| US6262118B1 (en) * | 1999-06-04 | 2001-07-17 | Metabolex, Inc. | Use of (-) (3-trihalomethylphenoxy) (4-halophenyl) acetic acid derivatives for treatment of insulin resistance, type 2 diabetes and hyperlipidemia |
| US7576131B2 (en) * | 1999-06-04 | 2009-08-18 | Metabolex, Inc. | Use of (-) (3-trihalomethylphenoxy) (4-halophenyl) acetic acid derivatives for treatment of insulin resistance, type 2 diabetes, hyperlipidemia and hyperuricemia |
| US7399777B2 (en) * | 2001-08-31 | 2008-07-15 | Sanofi-Aventis Deutschland Gmbh | Diarylcycloalkyl derivatives, processes for their preparation and their use as pharmceuticals |
| DE10308353A1 (de) * | 2003-02-27 | 2004-12-02 | Aventis Pharma Deutschland Gmbh | Diarylcycloalkylderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE102004038403B4 (de) * | 2004-08-07 | 2006-08-31 | Sanofi-Aventis Deutschland Gmbh | Verfahren zur Herstellung der enantiomeren Formen von cis-konfigurierten 3-Hydroxycyclohexancarbonsäure-Derivaten |
| DE102004039509B4 (de) * | 2004-08-14 | 2006-09-21 | Sanofi-Aventis Deutschland Gmbh | Aryl-cycloalkyl substituierte Alkansäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| DE102004039533B4 (de) * | 2004-08-14 | 2006-09-28 | Sanofi-Aventis Deutschland Gmbh | Essigsäurederivate mit Cyclohexylmethoxy-Substituenten, Verfahren zu ihrer Herstellung und ihre Anwendung als Arzneimittel |
| DE102004039532B4 (de) * | 2004-08-14 | 2006-09-21 | Sanofi-Aventis Deutschland Gmbh | Cyclohexyl-methyloxy substituierte Essigsäurederivate, Verfahren zu ihrer Herstellung und ihre Anwendung als Arzneimittel |
| DE102004060227B3 (de) * | 2004-12-15 | 2006-07-20 | Sanofi-Aventis Deutschland Gmbh | Verfahren zur Herstellung von Oxazolen durch Kondensation von aromatischen Aldehyden mit α-Ketoximen zu N-Oxiden und nachfolgende Reaktion mit aktivierten Säurederivaten |
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| CA2624102A1 (en) | 2005-09-29 | 2007-04-12 | Sanofi-Aventis | Phenyl- and pyridinyl- 1, 2 , 4 - oxadiazolone derivatives, processes for their preparation and their use as pharmaceuticals |
| KR101398715B1 (ko) | 2006-08-10 | 2014-05-27 | 가부시키가이샤 미모잭스 | 아카시아속 나무 껍질 유래물을 함유하는 혈당 강하 조성물 |
| JP5340287B2 (ja) | 2007-08-16 | 2013-11-13 | ソルヴェイ（ソシエテ アノニム） | ４−フルオロ置換３−オキソ−アルカン酸のエステル類の調製方法 |
| ES2574159T3 (es) | 2008-02-29 | 2016-06-15 | Nissan Chemical Industries, Ltd. | Proceso para la producción de compuesto de tiofeno e intermedio del mismo |
| US7615661B2 (en) * | 2008-03-12 | 2009-11-10 | International Flavors & Fragrances Inc. | Thioester compounds and their use in fragrance or flavor applications |
| BR112020011659A2 (pt) | 2017-12-13 | 2020-11-17 | Canon Kabushiki Kaisha | cartucho e aparelho de formação de imagem |
| CN109810071B (zh) * | 2019-03-28 | 2023-04-21 | 中国科学院成都生物研究所 | 一种miRNA生物合成抑制剂 |
Citations (2)
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| WO2000064876A1 (en) * | 1999-04-28 | 2000-11-02 | Aventis Pharma Deutschland Gmbh | Tri-aryl acid derivatives as ppar receptor ligands |
| EP1067109A1 (en) * | 1998-03-10 | 2001-01-10 | Ono Pharmaceutical Co., Ltd. | Carboxylic acid derivatives and drugs containing the same as the active ingredient |
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| FR2663336B1 (fr) | 1990-06-18 | 1992-09-04 | Adir | Nouveaux derives peptidiques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| FR2663464B1 (fr) * | 1990-06-19 | 1992-09-11 | Commissariat Energie Atomique | Circuit integre en technologie silicium sur isolant comportant un transistor a effet de champ et son procede de fabrication. |
| IL108633A (en) | 1993-02-15 | 1998-07-15 | Wellcome Found | History of Benzothiazepine Hypolipidemic Preparation and Pharmaceutical Preparations Containing Them |
| IL108634A0 (en) | 1993-02-15 | 1994-05-30 | Wellcome Found | Hypolipidaemic heterocyclic compounds, their prepatation and pharmaceutical compositions containing them |
| JP3144624B2 (ja) | 1995-06-02 | 2001-03-12 | 杏林製薬株式会社 | Ｎ−ベンジルジオキソチアゾリジルベンズアミド誘導体及びその製造法 |
| IL125071A0 (en) | 1996-01-17 | 1999-01-26 | Novo Nordisk As | Fused 1,2,4-thiadiazine and fused 1,4-thiazine derivatives their preparation and use |
| HU227021B1 (en) | 1996-08-30 | 2010-05-28 | Novo Nordisk As | Glp-1 derivatives |
| TW492957B (en) | 1996-11-07 | 2002-07-01 | Novartis Ag | N-substituted 2-cyanopyrrolidnes |
| JP4339402B2 (ja) | 1996-12-31 | 2009-10-07 | ドクター・レディーズ・ラボラトリーズ・リミテッド | 新規なヘテロ環化合物、これらの製造方法及びこれらを含有する薬学的組成物、並びに糖尿病及び関連疾患の治療におけるこれらの使用 |
| DE19726167B4 (de) * | 1997-06-20 | 2008-01-24 | Sanofi-Aventis Deutschland Gmbh | Insulin, Verfahren zu seiner Herstellung und es enthaltende pharmazeutische Zubereitung |
| CA2294830A1 (en) | 1997-07-16 | 1999-01-28 | John Bondo Hansen | Fused 1,2,4-thiadiazine derivatives, their preparation and use |
| CO4970713A1 (es) | 1997-09-19 | 2000-11-07 | Sanofi Synthelabo | Derivados de carboxamidotiazoles, su preparacion, composiciones farmaceuticas que los contienen |
| DE19823831A1 (de) | 1998-05-28 | 1999-12-02 | Probiodrug Ges Fuer Arzneim | Neue pharmazeutische Verwendung von Isoleucyl Thiazolidid und seinen Salzen |
| SE9801992D0 (sv) | 1998-06-04 | 1998-06-04 | Astra Ab | New 3-aryl-2-hydroxypropionic acid derivative I |
| MA26634A1 (fr) | 1998-06-04 | 2004-12-20 | Astra Ab | Nouveaux derives de l'acide 3-aryl propionique et analogues |
| US6221897B1 (en) * | 1998-06-10 | 2001-04-24 | Aventis Pharma Deutschland Gmbh | Benzothiepine 1,1-dioxide derivatives, a process for their preparation, pharmaceuticals comprising these compounds, and their use |
| DE19828113A1 (de) | 1998-06-24 | 2000-01-05 | Probiodrug Ges Fuer Arzneim | Prodrugs von Inhibitoren der Dipeptidyl Peptidase IV |
| DE19828114A1 (de) | 1998-06-24 | 2000-01-27 | Probiodrug Ges Fuer Arzneim | Produgs instabiler Inhibitoren der Dipeptidyl Peptidase IV |
| KR100613175B1 (ko) * | 1998-08-27 | 2006-08-17 | 오노 야꾸힝 고교 가부시키가이샤 | 카르복실산 유도체 및 그 유도체를 유효 성분으로서함유하는 약제 |
| DE19845405C2 (de) * | 1998-10-02 | 2000-07-13 | Aventis Pharma Gmbh | Arylsubstituierte Propanolaminderivate und deren Verwendung |
| GB9900416D0 (en) | 1999-01-08 | 1999-02-24 | Alizyme Therapeutics Ltd | Inhibitors |
| DE19916108C1 (de) * | 1999-04-09 | 2001-01-11 | Aventis Pharma Gmbh | Mit Zuckerresten substituierte 1,4-Benzothiazepin-1,1-dioxidderivate, Verfahren zu deren Herstellung und deren Verwendung |
| WO2000063208A1 (en) | 1999-04-16 | 2000-10-26 | Novo Nordisk A/S | Substituted imidazoles, their preparation and use |
| US6908926B1 (en) * | 1999-04-16 | 2005-06-21 | Novo Nordisk A/S | Substituted imidazoles, their preparation and use |
| DK1177187T3 (da) | 1999-04-28 | 2007-10-15 | Sanofi Aventis Deutschland | Diarylsyrederivater som PPAR-receptorligander |
| AU4808300A (en) | 1999-04-30 | 2000-11-17 | Neurogen Corporation | 9h-pyrimido(4,5-b)indole derivatives: crf1 specific ligands |
| GB9911863D0 (en) | 1999-05-21 | 1999-07-21 | Knoll Ag | Therapeutic agents |
| ATE333448T1 (de) | 1999-06-18 | 2006-08-15 | Merck & Co Inc | Arylthiazolidinedione und aryloxa zolidinedion- derivate |
| WO2001004146A2 (en) | 1999-07-09 | 2001-01-18 | Cohesion Technologies, Inc. | Ecarin polypeptides, polynucleotides encoding ecarin, and methods for use thereof |
| EP1204654B1 (en) | 1999-07-29 | 2003-07-23 | Eli Lilly And Company | Benzofurylpiperazines: 5-ht2c serotonin receptor agonists |
| IL148148A0 (en) * | 1999-09-01 | 2002-09-12 | Aventis Pharma Gmbh | Sulfonyl carboxamide derivatives, method for their production and their use as medicaments |
| TWI302149B (en) | 1999-09-22 | 2008-10-21 | Bristol Myers Squibb Co | Substituted acid derivatives useful as antiodiabetic and antiobesity agents and method |
| SE9904413D0 (sv) | 1999-12-03 | 1999-12-03 | Astra Ab | Comminuted form |
| WO2001040171A1 (en) | 1999-12-03 | 2001-06-07 | Astrazeneca Ab | Crystalline form of (s)-2 ethoxy-3-[4-(2-{4-methanesulfonyloxyphenyl} ethoxy) phenyl] propanoic acid |
| HU229042B1 (en) | 2000-03-31 | 2013-07-29 | Prosidion Ltd | Method for the improvement of islet signaling in diabetes mellitus and for its prevention |
| CZ20023502A3 (cs) | 2000-04-25 | 2003-06-18 | Kyorin Pharmaceutical Co., Ltd. | Nová stabilní krystalická forma thiazolidionového derivátu a způsob jeho přípravy |
| CN1430603A (zh) | 2000-04-28 | 2003-07-16 | 旭化成株式会社 | 新型双环化合物 |
| BR0110638A (pt) | 2000-05-11 | 2003-03-25 | Bristol Myers Squibb Co | Análogos de tetraidroisoquinolina úteis como secretagogos de hormÈnio do crescimento |
| JP2003534377A (ja) | 2000-05-30 | 2003-11-18 | メルク エンド カムパニー インコーポレーテッド | メラノコルチン受容体作働薬 |
| WO2001094300A1 (de) * | 2000-06-09 | 2001-12-13 | Aventis Pharma Deutschland Gmbh | Acylphenylharnstoffderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DE10038709A1 (de) | 2000-08-09 | 2002-02-28 | Aventis Pharma Gmbh | Substituierte und unsubstituierte Benzooxathiazole sowie daraus abgeleitete Verbindungen |
| EP1182251A1 (en) * | 2000-08-11 | 2002-02-27 | Yissum Research Development Company of the Hebrew University of Jerusalem | Methods for identifying compounds that inhibit ubiquitin-mediated proteolysis of IkB |
| US6982278B2 (en) | 2000-08-23 | 2006-01-03 | Eli Lilly And Company | Oxazolyl-aryloxyacetic acid derivatives and their use as ppar agonists |
| WO2002016331A1 (en) * | 2000-08-23 | 2002-02-28 | Eli Lilly And Company | Oxazolyl-arylpropionic acid derivatives and their use as ppar agonists |
| TWI243162B (en) | 2000-11-10 | 2005-11-11 | Taisho Pharmaceutical Co Ltd | Cyanopyrrolidine derivatives |
| JPWO2002046146A1 (ja) | 2000-12-05 | 2004-04-08 | 杏林製薬株式会社 | 置換カルボン酸誘導体 |
| GB0031103D0 (en) * | 2000-12-20 | 2001-01-31 | Glaxo Group Ltd | Chemical compounds |
| DE50111751D1 (de) | 2000-12-21 | 2007-02-08 | Sanofi Aventis Deutschland | Neue diphenzylazetidinone, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung zur behandlung von lipidstoffwechselstörungen |
| ATE370130T1 (de) * | 2000-12-25 | 2007-09-15 | Ono Pharmaceutical Co | Dihydronaphthalinderivat verbindungen und arzneimittel, die diese verbindungen als wirkstoff enthalten |
| WO2002064549A1 (en) * | 2001-02-15 | 2002-08-22 | Pfizer Products Inc. | Ppar agonists |
| PE20021091A1 (es) | 2001-05-25 | 2003-02-04 | Aventis Pharma Gmbh | Derivados de fenilurea sustituidos con carbonamida y procedimiento para su preparacion |
| EA200400011A1 (ru) * | 2001-06-07 | 2004-06-24 | Эли Лилли Энд Компани | Модуляторы рецепторов, активируемых пролифераторами пероксисом (prar) |
| DE10154689A1 (de) | 2001-11-09 | 2003-05-22 | Probiodrug Ag | Substituierte Aminoketonverbindungen |
| WO2003005025A1 (en) | 2001-07-03 | 2003-01-16 | Biovitrum Ab | Methods for identifying compounds modulating the activity of ppar-gamma |
| FR2827859B1 (fr) | 2001-07-30 | 2005-09-23 | Lipha | Derives 4-(arylthio) - ou 4-(heteroarylthio) -butyrique dans la preparation de medicaments destines au traitement du diabete |
| EE05418B1 (et) | 2001-08-31 | 2011-06-15 | Aventis Pharma Deutschland Gmbh | Diarltskloalklderivaadid, nende kasutamine ravimite valmistamiseks ning neid sisaldav ravim |
| EP1474385B1 (en) | 2002-02-05 | 2009-06-10 | Eli Lilly And Company | Urea linker derivatives for use as ppar modulators |
| DE10215908B4 (de) | 2002-04-11 | 2005-08-18 | Aventis Pharma Deutschland Gmbh | Acyl-3-carboxyphenyl-harnstoffderivate und deren Verwendung als Arzneimittel |
| DE10215907A1 (de) | 2002-04-11 | 2003-11-06 | Aventis Pharma Gmbh | Acyl-4-carboxyphenyl-harnstoffderivate, Verfahren zu deren Herstellung und deren Verwendung |
| DE10225635C1 (de) | 2002-06-07 | 2003-12-24 | Aventis Pharma Gmbh | N-Benzoylureido-Zimtsäurederivate, Verfahren zu deren Herstellung und deren Verwendung |
| PL374860A1 (en) | 2002-07-09 | 2005-11-14 | Bristol-Myers Squibb Company | Substituted heterocyclic derivatives useful as antidiabetic and antiobesity agents and method |
| US7148246B2 (en) * | 2003-02-27 | 2006-12-12 | Sanofi-Aventis Deutschland Gmbh | Cycloalkyl derivatives having bioisosteric carboxylic acid groups, processes for their preparation and their use as pharmaceuticals |
-
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1067109A1 (en) * | 1998-03-10 | 2001-01-10 | Ono Pharmaceutical Co., Ltd. | Carboxylic acid derivatives and drugs containing the same as the active ingredient |
| WO2000064876A1 (en) * | 1999-04-28 | 2000-11-02 | Aventis Pharma Deutschland Gmbh | Tri-aryl acid derivatives as ppar receptor ligands |
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