WO2004076427A1 - 3-(2-phenyl-oxazol-4- ylmethoxy)-cyclohexylmethoxy -essigsäure derivate und verwandte verbindungen als ppar modulatoren zur behandlung von typ 2 diabetes und atherosklerose - Google Patents
3-(2-phenyl-oxazol-4- ylmethoxy)-cyclohexylmethoxy -essigsäure derivate und verwandte verbindungen als ppar modulatoren zur behandlung von typ 2 diabetes und atherosklerose Download PDFInfo
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- WO2004076427A1 WO2004076427A1 PCT/EP2004/001579 EP2004001579W WO2004076427A1 WO 2004076427 A1 WO2004076427 A1 WO 2004076427A1 EP 2004001579 W EP2004001579 W EP 2004001579W WO 2004076427 A1 WO2004076427 A1 WO 2004076427A1
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- WIPO (PCT)
- Prior art keywords
- cis
- methyl
- alkyl
- phenyl
- tert
- Prior art date
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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)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
Priority Applications (12)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
MXPA05008988A MXPA05008988A (es) | 2003-02-27 | 2004-02-19 | Derivados de acido 3-(2-fenil-oxazol-4-ilmetoxi) ciclohexilmetoxiacetico y compuestos relacionados utilizados como moduladores de ppar para tratar diabetes de tipo 2 y arterioesclerosis. |
DK04712490T DK1599452T3 (da) | 2003-02-27 | 2004-02-19 | 3- (2-phenyloxazol- 4-ylmethoxy) - cyclohexylmethoxyeddikesyrederivater og beslægtede forbindelser som PPAR modulatorer til behandling af type 2 diabetes og atherosklerosw |
JP2006501886A JP2006519194A (ja) | 2003-02-27 | 2004-02-19 | 2型糖尿病およびアテローム性動脈硬化症の治療のためのpparモジュレーターとしての3−(2−フェニル−オキサゾール−4−イルメトキシ)シクロヘキシルメトキシ酢酸誘導体および関連化合物 |
CA002517381A CA2517381A1 (en) | 2003-02-27 | 2004-02-19 | 3-(2-phenyl-oxazol-4-yl methoxy) cyclohexylmethoxy acetic acid derivatives and related compounds used as ppar modulators for treating type 2 diabetes and arteriosclerosis |
DE502004004139T DE502004004139D1 (de) | 2003-02-27 | 2004-02-19 | 3-(2-phenyl-oxazol-4- ylmethoxy)-cyclohexylmethoxy -essigsäure derivate und verwandte verbindungen als ppar modulatoren zur behandlung von typ 2 diabetes und atherosklerose |
BRPI0407758-0A BRPI0407758A (pt) | 2003-02-27 | 2004-02-19 | derivados de 3-(2-fenil-oxazol-4-ilmetóxi)-ciclohexilmetóxi-acético e compostos afins como modula-dores de ppar para o tratamento de diabetes do tipo 2 e aterosclerose. |
AU2004215673A AU2004215673B2 (en) | 2003-02-27 | 2004-02-19 | 3-(2-Phenyl-oxazol-4-yl methoxy) cyclohexylmethoxy acetic acid derivatives and related compounds used as PPAR modulators for treating type 2 diabetes and arteriosclerosis |
EP04712490A EP1599452B1 (de) | 2003-02-27 | 2004-02-19 | 3-(2-phenyl-oxazol-4- ylmethoxy)-cyclohexylmethoxy -essigsäure derivate und verwandte verbindungen als ppar modulatoren zur behandlung von typ 2 diabetes und atherosklerose |
IL170316A IL170316A (en) | 2003-02-27 | 2005-08-16 | Cycloalkyl-methoxy substituted acetic acid derivatives and pharmaceutical compositions comprising them |
TNP2005000204A TNSN05204A1 (en) | 2003-02-27 | 2005-08-26 | 3-2-phenyl-oxazol-4-ylmethoxy)cyclohexylmethoxy acetic acid derivatives and related compounds used as ppar modulators for treating type 2 diabetes and arteriosclerosis |
HR20050743A HRP20050743A2 (en) | 2003-02-27 | 2005-08-26 | 3-(2-phenyl-oxazol-4-yl methoxy) cyclohexylmethoxy acetic acid derivates and related compounds used as ppar modulators for treating type 2 diabetes and arteriosclerosis |
NO20054408A NO20054408L (no) | 2003-02-27 | 2005-09-22 | 3(2-fenyl-oksazol-4-yl-metoksy)-cykloheksylmetoksyeddiksyrederivater og lignende forbindelser som PPAR-modulatorer for behandling av type 2 diabetes og arterosklerose |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10308355.3 | 2003-02-27 | ||
DE10308355A DE10308355A1 (de) | 2003-02-27 | 2003-02-27 | Aryl-cycloalkyl substituierte Alkansäurederivate, Verfahren zu ihrer Herstellung und ihre Anwendung als Arzneimittel |
Publications (1)
Publication Number | Publication Date |
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WO2004076427A1 true WO2004076427A1 (de) | 2004-09-10 |
Family
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Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2004/001586 WO2004076428A1 (de) | 2003-02-27 | 2004-02-19 | 4-(3- (2-phenyl-oxazol-4-ylmethoxy)-cyclohexyloxy)-butansäure derivate und verwandte verbindungen als ppar modulatoren zur behandlung von typ 2 diabetes und atherosklerose |
PCT/EP2004/001578 WO2004076426A1 (de) | 2003-02-27 | 2004-02-19 | 3-methyl-2- (3- (2-phenyl-oxazol-4-ylmethoxy)-cyclohexancarbonyl-amino)-buttersäurederivate und verwandte verbindungen als ppar modulatoren zur behandlung von typ 2 diabetes und atherosklerose |
PCT/EP2004/001579 WO2004076427A1 (de) | 2003-02-27 | 2004-02-19 | 3-(2-phenyl-oxazol-4- ylmethoxy)-cyclohexylmethoxy -essigsäure derivate und verwandte verbindungen als ppar modulatoren zur behandlung von typ 2 diabetes und atherosklerose |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2004/001586 WO2004076428A1 (de) | 2003-02-27 | 2004-02-19 | 4-(3- (2-phenyl-oxazol-4-ylmethoxy)-cyclohexyloxy)-butansäure derivate und verwandte verbindungen als ppar modulatoren zur behandlung von typ 2 diabetes und atherosklerose |
PCT/EP2004/001578 WO2004076426A1 (de) | 2003-02-27 | 2004-02-19 | 3-methyl-2- (3- (2-phenyl-oxazol-4-ylmethoxy)-cyclohexancarbonyl-amino)-buttersäurederivate und verwandte verbindungen als ppar modulatoren zur behandlung von typ 2 diabetes und atherosklerose |
Country Status (34)
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006018115A1 (de) * | 2004-08-14 | 2006-02-23 | Sanofi-Aventis Deutschland Gmbh | 2-{-3-`2 (phenyl) -oxazol-4 ylmethoxy!-cyclohexylmethoxy} - propionsäure derivate als ppar liganden (peroxisomen-proliferatoren-aktivierte rezeptoren) zur behandlung von hyperlipidämie und diabetes |
WO2006018116A1 (de) * | 2004-08-14 | 2006-02-23 | Sanofi-Aventis Deutschland Gmbh | N-(phenyl-oxazol-4-ylmethoxymethyl)-cyclohexyl-bernsteinsäureamid derivate und werwandte verbindungen als ppar-liganden (peroxisomen-proliferatoren-aktivierte rezeptoren) zur behandlung von hyperlipidämie und diabetes |
WO2006018118A1 (de) * | 2004-08-14 | 2006-02-23 | Sanofi-Aventis Deutschland Gmbh | 2-{-3-`2-(phenyl)-oxazol-4-ylmethoxymethyl!-cyclohexylmethoxy}-propionsäure derivate als ppar-liganden (peroxisomen-proliferatoren-aktivierte rezeptoren) zur behandlung von hyperlipidämie und diabetes |
WO2007039177A2 (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 |
US8481778B2 (en) | 2007-08-16 | 2013-07-09 | Solvay (Societe Anonyme) | Process for the preparation of esters of 4-fluorosubstituted 3-oxo-alcanoic acids |
Families Citing this family (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
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 | |
AU2006347121B2 (en) | 2006-08-10 | 2013-06-06 | Acacia-No-Ki Co., Ltd. | Hypoglycemic composition containing component originating in the bark of tree belonging to the genus Acacia |
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 |
JP6971959B2 (ja) | 2017-12-13 | 2021-11-24 | キヤノン株式会社 | カートリッジ及び画像形成装置 |
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 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
EP1108713A1 (en) * | 1998-08-27 | 2001-06-20 | Ono Pharmaceutical Co., Ltd. | Carboxylic acid derivatives and drugs containing the same as the active ingredient |
WO2002016331A1 (en) * | 2000-08-23 | 2002-02-28 | Eli Lilly And Company | Oxazolyl-arylpropionic acid derivatives and their use as ppar agonists |
WO2002051820A1 (fr) * | 2000-12-25 | 2002-07-04 | Ono Pharmaceutical Co., Ltd. | Composes derives de dihydronaphtalene et medicaments utilisant ces composes comme ingredient actif |
Family Cites Families (59)
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 |
BR9707003A (pt) | 1996-01-17 | 1999-07-20 | Novo Nordisk As | Composto processos para preparar o mesmo para tratamento ou de prevenção de doenças do sistema endócrino e para a manufatura de medicamento coposção farmacêutica e utilização de um composto |
BRPI9711437B8 (pt) | 1996-08-30 | 2021-05-25 | Novo Nordisk As | derivados de glp-1 |
TW492957B (en) | 1996-11-07 | 2002-07-01 | Novartis Ag | N-substituted 2-cyanopyrrolidnes |
IL142649A (en) | 1996-12-31 | 2004-12-15 | Reddy Research Foundation | Azole derivatives |
DE19726167B4 (de) | 1997-06-20 | 2008-01-24 | Sanofi-Aventis Deutschland Gmbh | Insulin, Verfahren zu seiner Herstellung und es enthaltende pharmazeutische Zubereitung |
EP1000066A1 (en) | 1997-07-16 | 2000-05-17 | Novo Nordisk A/S | 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 |
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 |
US6908926B1 (en) * | 1999-04-16 | 2005-06-21 | Novo Nordisk A/S | Substituted imidazoles, their preparation and use |
AU3956900A (en) | 1999-04-16 | 2000-11-02 | Boehringer Ingelheim International Gmbh | 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 |
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 |
CA2376919C (en) | 1999-06-18 | 2008-11-04 | Merck & Co., Inc. | Arylthiazolidinedione and aryloxazolidinedione derivatives |
EP1196610A2 (en) | 1999-07-09 | 2002-04-17 | Cohesion Technologies, Inc. | Ecarin polypeptides, polynucleotides encoding ecarin, and methods for use thereof |
ES2203498T3 (es) | 1999-07-29 | 2004-04-16 | Eli Lilly And Company | Benzofurilpiperazinas: agonistas de receptor 5-ht2c de la serotonina. |
EE200200095A (et) * | 1999-09-01 | 2003-04-15 | Aventis Pharma Deutschland Gmbh | Sulfonüülkarboksamiidi derivaadid, nende kasutamine, ravim ja nende valmistamismeetod |
TWI260321B (en) | 1999-09-22 | 2006-08-21 | Bristol Myers Squibb Co | Substituted acid derivatives useful as antidiabetic and antiobesity agents and method |
SE9904413D0 (sv) | 1999-12-03 | 1999-12-03 | Astra Ab | Comminuted form |
AU773777B2 (en) | 1999-12-03 | 2004-06-03 | Astrazeneca Ab | Crystalline form of (S)-2 ethoxy-3-(4-(2-(4-methanesulfonyloxyphenyl) ethoxy) phenyl) propanoic acid |
EP2055302B1 (en) | 2000-03-31 | 2014-09-10 | Royalty Pharma Collection Trust | Method for the improvement of islet signaling in diabetes mellitus and for its prevention |
EA004244B1 (ru) | 2000-04-25 | 2004-02-26 | Киорин Фармасьютикал Ко., Лтд. | Новый стабильный кристалл производного тиазолидиндиона и способ его получения |
DK1277736T3 (da) | 2000-04-28 | 2007-10-01 | Asahi Kasei Pharma Corp | Hidtil ukendte bicykliske forbindelser |
AU5959201A (en) | 2000-05-11 | 2001-11-20 | Bristol Myers Squibb Co | Tetrahydroisoquinoline analogs useful as growth hormone secretagogues |
AU2001264977B2 (en) | 2000-05-30 | 2005-04-14 | 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 |
ATE368653T1 (de) | 2000-08-23 | 2007-08-15 | Lilly Co Eli | Oxazolylaryloxyessigsäure derivate und ihre verwendung als ppar agonisten |
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 |
DK1345895T3 (da) | 2000-12-21 | 2007-05-07 | Sanofi Aventis Deutschland | Hidtil ukendt diphenylazetidioner, fremgangsmåde til deres fremstilling, lægemidler indeholdende disse forbindelser og deres anvendelse til behandling af lipidstofskifteforstyrrelser |
EP1360172A1 (en) * | 2001-02-15 | 2003-11-12 | 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 |
HUP0400268A2 (hu) * | 2001-06-07 | 2004-07-28 | Eli Lilly And Co. | Peroxiszóma proliferátorral aktivált receptorokat (PPAR) módosító hatóanyagok, alkalmazásuk és ezeket tartalmazó gyógyszerkészítmények |
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 |
MXPA04001850A (es) | 2001-08-31 | 2004-06-15 | Aventis Pharma Gmbh | Derivados de diarilcicloalquilo, procedimientos para su preparacion y su utilizacion como agentes activadores de ppar. |
AU2003207432A1 (en) | 2002-02-05 | 2003-09-02 | Eli Lilly And Company | Urea linker derivatives for use as ppar modulators |
DE10215907A1 (de) | 2002-04-11 | 2003-11-06 | Aventis Pharma Gmbh | Acyl-4-carboxyphenyl-harnstoffderivate, Verfahren zu deren Herstellung und deren Verwendung |
DE10215908B4 (de) | 2002-04-11 | 2005-08-18 | Aventis Pharma Deutschland Gmbh | Acyl-3-carboxyphenyl-harnstoffderivate und deren Verwendung als Arzneimittel |
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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- 2003-02-27 DE DE10308355A patent/DE10308355A1/de not_active Withdrawn
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-
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- 2007-08-16 US US11/839,950 patent/US20080015238A1/en not_active Abandoned
-
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- 2008-01-14 US US12/013,806 patent/US7872034B2/en not_active Expired - Fee Related
Patent Citations (6)
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 |
EP1108713A1 (en) * | 1998-08-27 | 2001-06-20 | 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 |
WO2002016331A1 (en) * | 2000-08-23 | 2002-02-28 | Eli Lilly And Company | Oxazolyl-arylpropionic acid derivatives and their use as ppar agonists |
WO2002051820A1 (fr) * | 2000-12-25 | 2002-07-04 | Ono Pharmaceutical Co., Ltd. | Composes derives de dihydronaphtalene et medicaments utilisant ces composes comme ingredient actif |
EP1354879A1 (en) * | 2000-12-25 | 2003-10-22 | Ono Pharmaceutical Co., Ltd. | Dihydronaphthalene derivative compounds and drugs containing these compounds as the active ingredient |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
WO2006018115A1 (de) * | 2004-08-14 | 2006-02-23 | Sanofi-Aventis Deutschland Gmbh | 2-{-3-`2 (phenyl) -oxazol-4 ylmethoxy!-cyclohexylmethoxy} - propionsäure derivate als ppar liganden (peroxisomen-proliferatoren-aktivierte rezeptoren) zur behandlung von hyperlipidämie und diabetes |
WO2006018118A1 (de) * | 2004-08-14 | 2006-02-23 | Sanofi-Aventis Deutschland Gmbh | 2-{-3-`2-(phenyl)-oxazol-4-ylmethoxymethyl!-cyclohexylmethoxy}-propionsäure derivate als ppar-liganden (peroxisomen-proliferatoren-aktivierte rezeptoren) zur behandlung von hyperlipidämie und diabetes |
DE102004039532A1 (de) * | 2004-08-14 | 2006-03-02 | Sanofi-Aventis Deutschland Gmbh | Cyclohexyl-methyloxy substituierte Essigsäurederivate, Verfahren zu ihrer Herstellung und ihre Anwendung als Arzneimittel |
DE102004039533A1 (de) * | 2004-08-14 | 2006-03-02 | Sanofi-Aventis Deutschland Gmbh | Essigsäurederivate mit Cyclohexylmethoxy-Substituenten, Verfahren zu ihrer Herstellung und ihre Anwendung als Arzneimittel |
DE102004039509A1 (de) * | 2004-08-14 | 2006-03-23 | Sanofi-Aventis Deutschland Gmbh | Aryl-cycloalkyl substituierte Alkansäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
WO2006018116A1 (de) * | 2004-08-14 | 2006-02-23 | Sanofi-Aventis Deutschland Gmbh | N-(phenyl-oxazol-4-ylmethoxymethyl)-cyclohexyl-bernsteinsäureamid derivate und werwandte verbindungen als ppar-liganden (peroxisomen-proliferatoren-aktivierte rezeptoren) zur behandlung von hyperlipidämie und diabetes |
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 |
US7538131B2 (en) | 2004-08-14 | 2009-05-26 | Sanofi-Aventis Deutschland Gmbh | 2-{-3-′2-(phenyl)-oxazol-4-ylmethoxymethyl-cyclohexylmethoxy}-propionic acid derivatives useful as peroxisome proliferator-activated receptor (PPAR) ligands for the treatment of hyperlipidemia and diabetes |
US7956077B2 (en) | 2004-08-14 | 2011-06-07 | Sanofi-Aventis Deutschland Gmbh | 2-{-3,′2-(phenyl)-oxazol-4-ylmethoxyl-cyclohexyl methoxy}-propionic acid derivatives used as peroxisome proliferator-activated receptor (PPAR) ligands for the treatment of hyperlipidemia and diabetes |
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 |
US7598281B2 (en) | 2004-08-14 | 2009-10-06 | Sanofi-Aventis Deutschland Gmbh | Arylcycloakyl-substituted alkanoic acid derivatives useful as peroxisome proliferator-activated receptor (PPAR) ligands for the treatment of hyperlipidemia and diabetes |
WO2007039177A2 (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 |
US8481778B2 (en) | 2007-08-16 | 2013-07-09 | Solvay (Societe Anonyme) | Process for the preparation of esters of 4-fluorosubstituted 3-oxo-alcanoic acids |
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