KR20050106462A - 2형 당뇨병 및 죽상동맥경화증 치료용 ｐｐａｒ조절제로서의3-메틸-2-(3-(2-페닐-옥사졸-4-일메톡시)-사이클로헥산카보닐-아미노 부티르산 유도체 및 관련 화합물 - Google Patents
2형 당뇨병 및 죽상동맥경화증 치료용 ｐｐａｒ조절제로서의3-메틸-2-(3-(2-페닐-옥사졸-4-일메톡시)-사이클로헥산카보닐-아미노 부티르산 유도체 및 관련 화합물 Download PDFInfo
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- KR20050106462A KR20050106462A KR1020057016023A KR20057016023A KR20050106462A KR 20050106462 A KR20050106462 A KR 20050106462A KR 1020057016023 A KR1020057016023 A KR 1020057016023A KR 20057016023 A KR20057016023 A KR 20057016023A KR 20050106462 A KR20050106462 A KR 20050106462A
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- Prior art keywords
- alkyl
- methyl
- phenyl
- formula
- compound
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- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 239000012096 transfection reagent Substances 0.000 description 1
- 238000003146 transient transfection Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
- 229960001641 troglitazone Drugs 0.000 description 1
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
- 210000000626 ureter Anatomy 0.000 description 1
- 210000003462 vein Anatomy 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
Classifications
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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
-
- 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)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (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)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20050106462A true KR20050106462A (ko) | 2005-11-09 |
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| Application Number | Title | Priority Date | Filing Date |
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| KR1020057015851A KR20050105492A (ko) | 2003-02-27 | 2004-02-19 | 2형 당뇨병 및 아테롬성경화증 치료용 ｐｐａｒ조절제로서의4-(3-(2-페닐옥사졸-4-일메톡시)-사이클로헥실옥시)-부탄산유도체 및 관련 화합물 |
| KR1020057016023A KR20050106462A (ko) | 2003-02-27 | 2004-02-19 | 2형 당뇨병 및 죽상동맥경화증 치료용 ｐｐａｒ조절제로서의3-메틸-2-(3-(2-페닐-옥사졸-4-일메톡시)-사이클로헥산카보닐-아미노 부티르산 유도체 및 관련 화합물 |
| KR1020057015995A KR20050106461A (ko) | 2003-02-27 | 2004-02-19 | 타입 2 당뇨병과 죽상동맥경화증 치료에 ｐｐａｒ 조절제로사용되는 3-(2-페닐-옥사졸-4-일 메톡시)사이클로헥실메톡시 아세트산 유도체 및 이와 관련된화합물 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
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| KR1020057015851A KR20050105492A (ko) | 2003-02-27 | 2004-02-19 | 2형 당뇨병 및 아테롬성경화증 치료용 ｐｐａｒ조절제로서의4-(3-(2-페닐옥사졸-4-일메톡시)-사이클로헥실옥시)-부탄산유도체 및 관련 화합물 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
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| KR1020057015995A KR20050106461A (ko) | 2003-02-27 | 2004-02-19 | 타입 2 당뇨병과 죽상동맥경화증 치료에 ｐｐａｒ 조절제로사용되는 3-(2-페닐-옥사졸-4-일 메톡시)사이클로헥실메톡시 아세트산 유도체 및 이와 관련된화합물 |
Country Status (34)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
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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 |
| 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 |
| 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 |
| 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 | |
| AU2006299091A1 (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 |
| CN101801906A (zh) | 2007-08-16 | 2010-08-11 | 索尔维公司 | 制备4-氟取代的3-氧代-烷酸酯的方法 |
| HUE027833T2 (en) | 2008-02-29 | 2016-11-28 | Nissan Chemical Ind Ltd | Process for the preparation of a thiophene derivative and its intermediate |
| US7615661B2 (en) * | 2008-03-12 | 2009-11-10 | International Flavors & Fragrances Inc. | Thioester compounds and their use in fragrance or flavor applications |
| CN116184782A (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. |
| IL108634A0 (en) | 1993-02-15 | 1994-05-30 | Wellcome Found | Hypolipidaemic heterocyclic compounds, their prepatation and pharmaceutical compositions containing them |
| ZA941003B (en) | 1993-02-15 | 1995-08-14 | Wellcome Found | Hypolipidaemic compounds |
| 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 |
| EP0876379A1 (en) | 1996-01-17 | 1998-11-11 | Novo Nordisk A/S | Fused 1,2,4-thiadiazine and fused 1,4-thiazine derivatives, their preparation and use |
| PT944648E (pt) | 1996-08-30 | 2007-06-26 | Novo Nordisk As | Derivados do glp-1. |
| TW492957B (en) | 1996-11-07 | 2002-07-01 | Novartis Ag | N-substituted 2-cyanopyrrolidnes |
| CN1190434C (zh) | 1996-12-31 | 2005-02-23 | 雷迪实验室有限公司 | 新的杂环化合物、其制备方法和含有它们的药物组合物及其在治疗糖尿病和相关疾病中的应用 |
| DE19726167B4 (de) * | 1997-06-20 | 2008-01-24 | Sanofi-Aventis Deutschland Gmbh | Insulin, Verfahren zu seiner Herstellung und es enthaltende pharmazeutische Zubereitung |
| RU2215004C2 (ru) | 1997-07-16 | 2003-10-27 | Ново Нордиск А/С | Конденсированное производное 1,2,4-тиадиазина, фармацевтическая композиция и способ получения лекарственного препарата |
| CO4970713A1 (es) | 1997-09-19 | 2000-11-07 | Sanofi Synthelabo | Derivados de carboxamidotiazoles, su preparacion, composiciones farmaceuticas que los contienen |
| KR100620337B1 (ko) * | 1998-03-10 | 2006-09-13 | 오노 야꾸힝 고교 가부시키가이샤 | 카르복실산 유도체와 그 유도체를 유효 성분으로서함유하는 약제 |
| 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 |
| AU5443499A (en) * | 1998-08-27 | 2000-03-21 | Ono Pharmaceutical Co. Ltd. | Carboxylic acid derivatives and drugs containing the same as the active ingredient |
| 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 |
| JP2002543065A (ja) * | 1999-04-28 | 2002-12-17 | アベンティス・ファーマ・ドイチユラント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | Ｐｐａｐ受容体リガンドとしてのトリアリール酸誘導体 |
| HUP0201291A3 (en) | 1999-04-28 | 2002-11-28 | Sanofi Aventis Deutschland | Di-aryl acid derivatives as ppar receptor ligands and pharmaceutical compositions containing them |
| US6284766B1 (en) | 1999-04-30 | 2001-09-04 | Neurogen Corporation | 9H-pyrimido [4,5-b] indole derivatives: CRF1 specific ligands |
| GB9911863D0 (en) | 1999-05-21 | 1999-07-21 | Knoll Ag | Therapeutic agents |
| DE60029446T2 (de) | 1999-06-18 | 2007-02-08 | Merck & Co., Inc. | Arylthiazolidindione und aryloxazolidindion-derivate |
| US6413737B1 (en) | 1999-07-09 | 2002-07-02 | Cohesion Technologies, Inc. | Ecarin prothrombin protease and methods |
| MXPA02000973A (es) | 1999-07-29 | 2002-07-30 | Lilly Co Eli | Benzofurilpiperazinas y benzofurilhomopiperazinas: agonistas de serotonina. |
| ATE302754T1 (de) | 1999-09-01 | 2005-09-15 | Aventis Pharma Gmbh | Sulfonylcarboxamidderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| 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 |
| US6500804B2 (en) | 2000-03-31 | 2002-12-31 | Probiodrug Ag | 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 |
| AU2001252574B2 (en) | 2000-04-28 | 2005-03-17 | Asahi Kasei Pharma Corporation | Novel bicyclic compounds |
| WO2001085695A1 (en) | 2000-05-11 | 2001-11-15 | Bristol-Myers Squibb Co. | Tetrahydroisoquinoline analogs useful as growth hormone secretagogues |
| CA2410597A1 (en) | 2000-05-30 | 2001-12-06 | Merck & Co., Inc. | Melanocortin receptor agonists |
| NZ523034A (en) | 2000-06-09 | 2004-07-30 | Aventis Pharma Gmbh | Acylphenyl urea derivatives, methods for the production thereof and use thereof as a medicament |
| 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 |
| DE60128239T2 (de) * | 2000-08-23 | 2008-01-10 | Eli Lilly And Co., Indianapolis | Oxazolylarylpropionsäure derivate und ihre verwendung als ppar agonisten |
| 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 |
| SK7822003A3 (en) | 2000-12-21 | 2003-12-02 | Aventis Pharma Gmbh | Novel 1,2-diphenzylazetidinones, method for producing the same, medicaments containing said compounds, and the use thereof for treating disorders of the lipid metabolism |
| CZ20031772A3 (cs) * | 2000-12-25 | 2003-11-12 | Ono Pharmaceutical Co., Ltd. | Derivát dihydronaftalenu a činidlo obsahující tento derivát jako účinnou složku |
| MXPA03007284A (es) | 2001-02-15 | 2003-12-04 | Pfizer Prod Inc | Agonistas de receptor activador del proliferador de peroxisomas. |
| PE20021091A1 (es) | 2001-05-25 | 2003-02-04 | Aventis Pharma Gmbh | Derivados de fenilurea sustituidos con carbonamida y procedimiento para su preparacion |
| CZ20033328A3 (cs) * | 2001-06-07 | 2004-06-16 | Eli Lilly And Company | Modulátory receptorů aktivovaných proliferátory peroxisomů (PPAR) |
| 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 |
| IL160556A0 (en) | 2001-08-31 | 2004-07-25 | Aventis Pharma Gmbh | Diaryl cycloalkyl derivatives, method for producing the same and the use thereof as ppar activators |
| ATE433440T1 (de) | 2002-02-05 | 2009-06-15 | Lilly Co Eli | Harnstoff-linker verbindungen und ihre verwendung als ppar regulatoren |
| 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 |
| EP1656368A4 (en) | 2002-07-09 | 2009-08-26 | Bristol Myers Squibb Co | SUBSTITUTED HETEROCYCLIC DERIVATIVES USEFUL AS ANTIDIABETIC AGENTS AND ANTIABESITY AND THEIR MANUFACTURING PROCESS |
| 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
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2004
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2007
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