CN100439347C - 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 - Google Patents
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 Download PDFInfo
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- CN100439347C CN100439347C CNB2004800054769A CN200480005476A CN100439347C CN 100439347 C CN100439347 C CN 100439347C CN B2004800054769 A CNB2004800054769 A CN B2004800054769A CN 200480005476 A CN200480005476 A CN 200480005476A CN 100439347 C CN100439347 C CN 100439347C
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- oxazole
- methyl
- cyclohexyloxy
- ylmethoxy
- compound
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
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- 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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- 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
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- 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
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
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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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| CN1753881A CN1753881A (zh) | 2006-03-29 |
| CN100439347C true CN100439347C (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 |
| CNB2004800054379A Expired - Fee Related CN100439345C (zh) | 2003-02-27 | 2004-02-19 | 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 |
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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 |
| CNB2004800054379A Expired - Fee Related CN100439345C (zh) | 2003-02-27 | 2004-02-19 | 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 |
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| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| GT200600218A (es) * | 2005-06-10 | 2007-03-28 | Formulación y proceso de compresión directa | |
| EP1931337B1 (en) | 2005-09-29 | 2013-10-23 | Sanofi | Phenyl- and pyridinyl- 1, 2 , 4 - oxadiazolone derivatives, processes for their preparation and their use as pharmaceuticals |
| US8128969B2 (en) | 2006-08-10 | 2012-03-06 | Mimozax Co., Ltd. | Hypoglycemic composition containing acacia bark derivative |
| 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 |
| EP2246343B1 (en) | 2008-02-29 | 2016-05-18 | Nissan Chemical Industries, Ltd. | Process for production of thiophene compound and intermediate thereof |
| US7615661B2 (en) * | 2008-03-12 | 2009-11-10 | International Flavors & Fragrances Inc. | Thioester compounds and their use in fragrance or flavor applications |
| CN116184784A (zh) | 2017-12-13 | 2023-05-30 | 佳能株式会社 | 盒与图像形成装置 |
| 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 |
Family Cites Families (64)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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. |
| ZA941003B (en) | 1993-02-15 | 1995-08-14 | Wellcome Found | Hypolipidaemic compounds |
| 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 |
| AU727775B2 (en) | 1996-01-17 | 2000-12-21 | Novo Nordisk A/S | Fused 1,2,4-thiadiazine and fused 1,4-thiazine derivatives, their preparation and use |
| DK0944648T3 (da) | 1996-08-30 | 2007-07-02 | Novo Nordisk As | GLP-1 derivater |
| TW492957B (en) | 1996-11-07 | 2002-07-01 | Novartis Ag | N-substituted 2-cyanopyrrolidnes |
| ES2199366T3 (es) | 1996-12-31 | 2004-02-16 | Dr. Reddy's Laboratories Ltd. | Compuestos heterociclicos, procedimiento para su preparacion y composiciones farmaceuticas que los contienen y su uso en el tratamiento de diabetes y enfermedades relacionadas. |
| DE19726167B4 (de) * | 1997-06-20 | 2008-01-24 | Sanofi-Aventis Deutschland Gmbh | Insulin, Verfahren zu seiner Herstellung und es enthaltende pharmazeutische Zubereitung |
| BR9810592A (pt) | 1997-07-16 | 2000-09-12 | Novo Nordisk As | Composto, processos para preparar um composto, para tratar ou prevenir doenças do sistema endócrino e para a fabricação de um medicamento, composição farmacêutica, e, uso de um composto |
| CO4970713A1 (es) | 1997-09-19 | 2000-11-07 | Sanofi Synthelabo | Derivados de carboxamidotiazoles, su preparacion, composiciones farmaceuticas que los contienen |
| WO1999046232A1 (fr) * | 1998-03-10 | 1999-09-16 | Ono Pharmaceutical Co., Ltd. | Derives d'acide carboxylique et medicaments contenant ces derives comme principe actif |
| 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 |
| DE19828114A1 (de) | 1998-06-24 | 2000-01-27 | Probiodrug Ges Fuer Arzneim | Produgs instabiler Inhibitoren der Dipeptidyl Peptidase IV |
| DE19828113A1 (de) | 1998-06-24 | 2000-01-05 | Probiodrug Ges Fuer Arzneim | Prodrugs von Inhibitoren der Dipeptidyl Peptidase IV |
| WO2000012491A1 (fr) * | 1998-08-27 | 2000-03-09 | Ono Pharmaceutical Co., Ltd. | Derives d'acide carboxylique et medicaments dont ils sont le principe actif |
| 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 |
| EP1177187B1 (en) | 1999-04-28 | 2007-07-25 | Sanofi-Aventis Deutschland GmbH | Di-aryl acid derivatives as ppar receptor ligands |
| RU2278860C2 (ru) * | 1999-04-28 | 2006-06-27 | Санофи-Авентис Дойчланд Гмбх | Производные триарил-содержащих кислот в качестве лигандов рецепторов ппар |
| CA2371271A1 (en) | 1999-04-30 | 2000-11-09 | Neurogen Corporation | 9h-pyrimido[4,5-b]indole derivatives: crf1 specific ligands |
| GB9911863D0 (en) | 1999-05-21 | 1999-07-21 | Knoll Ag | Therapeutic agents |
| ES2265952T3 (es) | 1999-06-18 | 2007-03-01 | MERCK & CO., INC. | Derivados de ariltiazolidindiona y ariloxazolidindiona. |
| US6413737B1 (en) | 1999-07-09 | 2002-07-02 | Cohesion Technologies, Inc. | Ecarin prothrombin protease and methods |
| ES2203498T3 (es) | 1999-07-29 | 2004-04-16 | Eli Lilly And Company | Benzofurilpiperazinas: agonistas de receptor 5-ht2c de la serotonina. |
| CA2383781A1 (en) * | 1999-09-01 | 2001-03-08 | Aventis Pharma Deutschland Gmbh | Sulfonyl carboxamide derivatives, method for their production and their use as medicaments |
| TW200528436A (en) | 1999-09-22 | 2005-09-01 | 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 |
| IL151368A0 (en) | 2000-03-31 | 2003-04-10 | Probiodrug Ag | Use of a dipeptidyl peptidase iv enzyme activity effector for the production of pharmaceutical compositions |
| MXPA02010545A (es) | 2000-04-25 | 2004-05-14 | Kyorin Seiyaku Kk | Cristal estable novedoso de derivado de tiazolidinediona y proceso para producir el mismo. |
| CN1430603A (zh) | 2000-04-28 | 2003-07-16 | 旭化成株式会社 | 新型双环化合物 |
| AU5959201A (en) | 2000-05-11 | 2001-11-20 | Bristol Myers Squibb Co | Tetrahydroisoquinoline analogs useful as growth hormone secretagogues |
| EP1289526A4 (en) | 2000-05-30 | 2005-03-16 | Merck & Co Inc | MELANOCORTIN RECEPTOR AGONISTS |
| EE200200634A (et) * | 2000-06-09 | 2004-04-15 | Aventis Pharma Deutschland Gmbh | Atsüülfenüülkarbamiidi derivaadid, nende saamine ja kasutamine veresuhkrut alandava ravimi valmistamiseks ning neid sisaldav ravim |
| 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 |
| IL154110A0 (en) * | 2000-08-23 | 2003-07-31 | Lilly Co Eli | Oxazolyl-arylpropionic acid derivatives and their use as ppar agonists |
| EP1313715B1 (en) | 2000-08-23 | 2007-08-01 | Eli Lilly And Company | Oxazolyl-aryloxyacetic acid derivatives and their use as ppar agonists |
| TWI243162B (en) | 2000-11-10 | 2005-11-11 | Taisho Pharmaceutical Co Ltd | Cyanopyrrolidine derivatives |
| AU2002222573A1 (en) | 2000-12-05 | 2002-06-18 | Kyorin Pharmaceutical Co. Ltd. | Substituted carboxylic acid derivatives |
| GB0031103D0 (en) * | 2000-12-20 | 2001-01-31 | Glaxo Group Ltd | Chemical compounds |
| PT1345895E (pt) | 2000-12-21 | 2007-02-28 | Sanofi Aventis Deutschland | Novas difenilazetidinonas, processo para a sua preparação, fármacos contendo estes compostos e sua utilização para o tratamento de distúrbios do metabolismo lipídico |
| US7220864B2 (en) * | 2000-12-25 | 2007-05-22 | Ono Pharmaceutical Co., Ltd. | Dihydronaphthalene derivative compounds and agent comprising the derivative as active ingredient |
| BR0207285A (pt) * | 2001-02-15 | 2004-02-10 | Pfizer Producs Inc | Agonistas de ppar |
| PE20021091A1 (es) | 2001-05-25 | 2003-02-04 | Aventis Pharma Gmbh | Derivados de fenilurea sustituidos con carbonamida y procedimiento para su preparacion |
| BR0210167A (pt) * | 2001-06-07 | 2004-04-06 | Lilly Co Eli | Composto, composição farmacêutica, métodos para modular um receptor ativado com proliferador de peroxissoma, para tratar ou prevenir uma doença ou condição e para abaixar a glicose no sangue, e, uso de um composto |
| DE10154689A1 (de) | 2001-11-09 | 2003-05-22 | Probiodrug Ag | Substituierte Aminoketonverbindungen |
| WO2003004458A1 (en) | 2001-07-03 | 2003-01-16 | Biovitrum Ab | New compounds |
| 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 |
| OA12656A (en) | 2001-08-31 | 2006-06-19 | Aventis Pharma Gmbh | Diaryl cycloalkyl derivatives, method for producing the same and the use thereof as PPAR activators. |
| US6984661B2 (en) | 2002-02-05 | 2006-01-10 | 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 |
| AU2003259131A1 (en) | 2002-07-09 | 2004-01-23 | 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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