ZA200109804B - Thiazole and oxazole derivatives and their pharmaceutical use. - Google Patents
Thiazole and oxazole derivatives and their pharmaceutical use. Download PDFInfo
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- ZA200109804B ZA200109804B ZA200109804A ZA200109804A ZA200109804B ZA 200109804 B ZA200109804 B ZA 200109804B ZA 200109804 A ZA200109804 A ZA 200109804A ZA 200109804 A ZA200109804 A ZA 200109804A ZA 200109804 B ZA200109804 B ZA 200109804B
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- South Africa
- Prior art keywords
- methyl
- phenyl
- agonist
- composition
- thiazol
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Classifications
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- 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
- C07D277/22—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/26—Radicals substituted by sulfur atoms
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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
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- 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
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
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- 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
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- 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
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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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
-
- 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
-
- 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
- C07D277/22—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9914977.5A GB9914977D0 (en) | 1999-06-25 | 1999-06-25 | Chemical compounds |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200109804B true ZA200109804B (en) | 2003-02-28 |
Family
ID=10856125
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200109804A ZA200109804B (en) | 1999-06-25 | 2001-11-28 | Thiazole and oxazole derivatives and their pharmaceutical use. |
Country Status (29)
Country | Link |
---|---|
US (2) | US6710063B1 (cs) |
EP (1) | EP1189895B8 (cs) |
JP (2) | JP3490704B2 (cs) |
KR (1) | KR100668026B1 (cs) |
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Families Citing this family (143)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB0024361D0 (en) * | 2000-10-05 | 2000-11-22 | Glaxo Group Ltd | Medicaments |
GB0024362D0 (en) * | 2000-10-05 | 2000-11-22 | Glaxo Group Ltd | Medicaments |
UA82048C2 (uk) | 2000-11-10 | 2008-03-11 | Эли Лилли Энд Компани | Агоністи альфа-рецепторів, активованих проліфератором пероксисом |
US20040072838A1 (en) * | 2000-12-20 | 2004-04-15 | Pierette Banker | Thiazole and oxazole derivatives as activators of human peroxisome proliferator activated receptors |
US7105551B2 (en) | 2000-12-20 | 2006-09-12 | Smithkline Beecham Corporation | Thiazole derivatives for treating PPAR related disorders |
GB0031109D0 (en) * | 2000-12-20 | 2001-01-31 | Glaxo Group Ltd | Chemical compounds |
GB0031103D0 (en) * | 2000-12-20 | 2001-01-31 | Glaxo Group Ltd | Chemical compounds |
WO2002050047A1 (en) * | 2000-12-20 | 2002-06-27 | Glaxo Group Limited | Substitued oxazoles and thiazoles as hppar alpha agonists |
GB0031107D0 (en) * | 2000-12-20 | 2001-01-31 | Glaxo Group Ltd | Chemical compounds |
US6982251B2 (en) | 2000-12-20 | 2006-01-03 | Schering Corporation | Substituted 2-azetidinones useful as hypocholesterolemic agents |
EP1911462A3 (en) | 2001-01-26 | 2011-11-30 | Schering Corporation | Compositions comprising a sterol absorption inhibitor |
BR0206654A (pt) | 2001-01-26 | 2004-02-25 | Schering Corp | Combinações de ativador(es) de receptor ativado por proliferação de peroxisoma (ppar) e inibidor(es) de absorção de esterol e tratamentos para indicações vasculares |
WO2002058696A2 (en) | 2001-01-26 | 2002-08-01 | Schering Corporation | The use of substituted azetidinone compounds for the treatment of sitosterolemia |
US7071181B2 (en) | 2001-01-26 | 2006-07-04 | Schering Corporation | Methods and therapeutic combinations for the treatment of diabetes using sterol absorption inhibitors |
EP1357914A2 (en) * | 2001-02-02 | 2003-11-05 | SmithKline Beecham Corporation | Treatment of ppar mediated diseases |
US7078422B2 (en) * | 2001-03-23 | 2006-07-18 | Nippon Chemiphar Co., Ltd. | Activator for peroxisome proliferator-activated receptor |
US20030077298A1 (en) * | 2001-04-13 | 2003-04-24 | The Regents Of The University Of California, A California Corporation | Activators and ligands of PPAR-beta/delta for the treatment of skin conditions |
AU2002342244B2 (en) * | 2001-05-15 | 2005-06-16 | F. Hoffmann-La Roche Ag | Carboxylic acid substituted oxazole derivatives for use as PPAR-alpha and -gamma activators in the treatment of diabetes |
GB0113231D0 (en) | 2001-05-31 | 2001-07-25 | Glaxo Group Ltd | Chemical compounds |
KR101021817B1 (ko) * | 2001-07-17 | 2011-03-17 | 데이진 가부시키가이샤 | PPAR δ활성화 작용을 측정하는 것을 특징으로 하는 물질의 선택방법 및 약제 |
US7067530B2 (en) | 2001-07-30 | 2006-06-27 | Novo Nordisk A/S | Compounds, their preparation and use |
US6869967B2 (en) | 2001-07-30 | 2005-03-22 | Novo Nordisk A/S | Peroxisome proliferator-activated receptor (PPAR) active vinyl carboxylic acid derivatives |
MXPA04001258A (es) * | 2001-08-10 | 2005-06-06 | Nippon Chemiphar Co | Activador para el receptor d que responde al proliferador de peroxisoma. |
CA2460313C (en) | 2001-09-14 | 2011-03-08 | Tularik Inc. | Bisphenylsulfanyl and sulphonate compounds and use thereof for elevating hdl cholesterol levels |
US7056906B2 (en) | 2001-09-21 | 2006-06-06 | Schering Corporation | Combinations of hormone replacement therapy composition(s) and sterol absorption inhibitor(s) and treatments for vascular conditions in post-menopausal women |
US7053080B2 (en) | 2001-09-21 | 2006-05-30 | Schering Corporation | Methods and therapeutic combinations for the treatment of obesity using sterol absorption inhibitors |
DE60216300T2 (de) | 2001-09-21 | 2007-06-28 | Schering Corp. | Behandlung von xanthom mittels azetidinon-derivate als hemmer der sterol absorption |
US7220877B2 (en) | 2001-10-17 | 2007-05-22 | Novo Nordisk A/S | Compounds, their preparation and use |
ATE415160T1 (de) | 2002-02-25 | 2008-12-15 | Lilly Co Eli | Modulatoren von peroxisome proliferator- aktivierten rezeptoren |
JP2005529077A (ja) * | 2002-02-25 | 2005-09-29 | イーライ・リリー・アンド・カンパニー | ペルオキシソーム増殖因子活性化受容体調節物質 |
JP2005530702A (ja) * | 2002-02-28 | 2005-10-13 | スミスクライン ビーチャム コーポレーション | フェニルチオメチル−チアゾールまたはオキサゾールを製造するための方法および中間体 |
WO2003074495A1 (en) * | 2002-03-01 | 2003-09-12 | Smithkline Beecham Corporation | Hppars activators |
US6867224B2 (en) * | 2002-03-07 | 2005-03-15 | Warner-Lambert Company | Compounds that modulate PPAR activity and methods of preparation |
US20030207924A1 (en) * | 2002-03-07 | 2003-11-06 | Xue-Min Cheng | Compounds that modulate PPAR activity and methods of preparation |
US6833380B2 (en) | 2002-03-07 | 2004-12-21 | Warner-Lambert Company, Llc | Compounds that modulate PPAR activity and methods of preparation |
US6875780B2 (en) | 2002-04-05 | 2005-04-05 | Warner-Lambert Company | Compounds that modulate PPAR activity and methods for their preparation |
US6716842B2 (en) | 2002-04-05 | 2004-04-06 | Warner-Lambert Company, Llc | Antidiabetic agents |
KR100474202B1 (ko) * | 2002-05-04 | 2005-03-08 | 강헌중 | 티아졸 유도체의 제조방법 및 이를 제조하기 위한 중간체 |
JP2004277397A (ja) * | 2002-05-24 | 2004-10-07 | Takeda Chem Ind Ltd | 1,2−アゾール誘導体 |
CA2487315A1 (en) * | 2002-05-24 | 2003-12-04 | Takeda Pharmaceutical Company Limited | 1,2-azole derivatives with hypoglycemic and hypolipidemic activity |
BR0312452A (pt) * | 2002-07-03 | 2005-04-19 | Hoffmann La Roche | Composto; processo para a preparação de um composto; composição farmacêutica; uso de um composto; e método para o tratamento e/ou profilaxia de doenças que são moduladas por agonistas de ppar(alfa) e/ou ppar(gama) |
US6875782B2 (en) | 2002-07-09 | 2005-04-05 | Bristol-Myers Squibb Company | Substituted heterocyclic derivatives useful as antidiabetic and antiobesity agents and method |
US7232828B2 (en) | 2002-08-10 | 2007-06-19 | Bethesda Pharmaceuticals, Inc. | PPAR Ligands that do not cause fluid retention, edema or congestive heart failure |
WO2004020420A1 (en) * | 2002-08-30 | 2004-03-11 | F.Hoffmann-La Roche Ag | Novel 2-arylthiazole compounds as pparalpha and ppargama agonists |
JP4638229B2 (ja) | 2002-09-05 | 2011-02-23 | ハイ・ポイント・ファーマスーティカルズ、エルエルシー | 新規ビニルカルボン酸誘導体およびその治療的使用 |
US7368578B2 (en) | 2002-09-10 | 2008-05-06 | Takeda Pharmaceutical Company Limited | Five-membered heterocyclic compounds |
JP2004123732A (ja) * | 2002-09-10 | 2004-04-22 | Takeda Chem Ind Ltd | 5員複素環化合物 |
JP4286782B2 (ja) | 2002-09-12 | 2009-07-01 | エフ.ホフマン−ラ ロシュ アーゲー | 糖尿病の治療に有用な、pparアゴニストとしてのn−置換−1h−インドール−5−プロピオン酸化合物 |
US7162262B2 (en) | 2002-09-23 | 2007-01-09 | Telefonaktiebolaget Lm Ericsson (Publ) | Methods, systems and computer program products for requesting received power levels based on received block error rates utilizing an anti-windup and/or emergency procedure |
US20050080115A1 (en) | 2002-10-28 | 2005-04-14 | Lone Jeppesen | Novel compounds, their preparation and use |
BR0315667A (pt) | 2002-10-28 | 2005-09-06 | Novo Nordisk As | Composto, uso de um composto, composição farmacêutica, e, método para o tratamento |
US7129268B2 (en) | 2002-10-28 | 2006-10-31 | Novo Nordisk A/S | Peroxisome proliferator activated receptor-active arylene acetic acid derivatives |
AU2003273783C1 (en) | 2002-10-28 | 2010-08-12 | Vtv Therapeutics Llc | Novel compounds and their use as PPAR-modulators |
US7560449B2 (en) | 2002-11-06 | 2009-07-14 | Schering Corporation | Methods and therapeutic combinations for the treatment of demyelination |
US7960369B2 (en) | 2002-11-08 | 2011-06-14 | Takeda Pharmaceutical Company Limited | Receptor function regulator |
PL377320A1 (pl) | 2002-11-25 | 2006-01-23 | F. Hoffmann-La Roche Ag | Pochodne indolilowe |
US7816385B2 (en) | 2002-12-20 | 2010-10-19 | High Point Pharmaceuticals, Llc | Dimeric dicarboxylic acid derivatives, their preparation and use |
CA2509202A1 (en) | 2003-01-06 | 2004-07-29 | Eli Lilly And Company | Fused heterocyclic derivatives as ppar modulators |
DE10308354A1 (de) * | 2003-02-27 | 2004-12-23 | Aventis Pharma Deutschland Gmbh | Cycloalkylderivate mit biosteren Carbonsäure-Gruppen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
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 |
ES2311806T3 (es) | 2003-03-07 | 2009-02-16 | Schering Corporation | Compuesto de azetidinona sustituidos, fornulaciones y usos de los mismos para el tratamiento de hipercolesterolemia. |
ES2318274T3 (es) | 2003-03-07 | 2009-05-01 | Schering Corporation | Compuestos de azetidinona sustituida, formulaciones y uso de los mismos para el tratamiento de hipercolesterolemia. |
US7459442B2 (en) | 2003-03-07 | 2008-12-02 | Schering Corporation | Substituted azetidinone compounds, processes for preparing the same, formulations and uses thereof |
MXPA05009502A (es) | 2003-03-07 | 2005-10-18 | Schering Corp | Compuestos de azetidinona sustituidos, formulaciones y usos de los mismos para el tratamiento de hipercolesterolemia. |
US7244763B2 (en) | 2003-04-17 | 2007-07-17 | Warner Lambert Company Llc | Compounds that modulate PPAR activity and methods of preparation |
US6987118B2 (en) * | 2003-05-21 | 2006-01-17 | Pfizer Inc. | Tetrahydroisoquinoline derivatives as PPAR-alpha activators |
CA2539446C (en) | 2003-09-19 | 2013-12-03 | Janssen Pharmaceutica, N.V. | 4-((phenoxyalkyl)thio)-phenoxyacetic acids and analogs |
HUE028213T2 (en) | 2003-09-19 | 2016-12-28 | Janssen Pharmaceutica Nv | 4 - ((Phenoxyalkyl) thio) -phenoxyacetic acid for use in the treatment of PPAR-delta-mediated conditions |
WO2005028453A1 (ja) | 2003-09-22 | 2005-03-31 | Ono Pharmaceutical Co., Ltd. | フェニル酢酸誘導体、その製造方法および用途 |
EP1688138A4 (en) | 2003-11-26 | 2008-01-16 | Takeda Pharmaceutical | AGENT FOR REGULATING THE FUNCTION OF A RECEIVER |
US20050203151A1 (en) * | 2003-12-19 | 2005-09-15 | Kalypsys, Inc. | Novel compounds, compositions and uses thereof for treatment of metabolic disorders and related conditions |
US7456218B2 (en) | 2003-12-25 | 2008-11-25 | Takeda Pharmaceutical Company Limited | 3-(4-benzyloxyphenyl) propanoic acid derivatives |
US7585880B2 (en) | 2003-12-26 | 2009-09-08 | Takeda Pharmaceutical Company Limited | Phenylpropanoic acid derivatives |
CN1946666A (zh) * | 2004-02-27 | 2007-04-11 | 埃姆艮股份有限公司 | 用于治疗代谢性疾病的化合物、药物组合物和方法 |
DE602004004631D1 (de) | 2004-04-01 | 2007-03-22 | Sanofi Aventis Deutschland | Oxadiazolone, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Pharmazeutika |
CA2561230A1 (en) | 2004-04-01 | 2005-10-20 | Aventis Pharmaceuticals Inc. | 1,3,4-oxadiazol-2-ones as ppar delta modulators and their use thereof |
BRPI0509540A (pt) * | 2004-04-01 | 2007-09-18 | Aventis Pharma Inc | uso de agonistas do receptor delta ativado pelo proliferador de peroxissoma para o tratamento de ms e outras doenças desmielinizantes |
AU2005230837A1 (en) | 2004-04-01 | 2005-10-20 | Aventis Pharmaceuticals Inc. | 1,3,4-oxadiazol-2-ones as PPAR delta modulators |
JP2007536343A (ja) | 2004-05-05 | 2007-12-13 | ノボ ノルディスク アクティーゼルスカブ | Pparアゴニストとしてのフェノキシ酢酸誘導体 |
EP1745014B1 (en) | 2004-05-05 | 2011-07-06 | High Point Pharmaceuticals, LLC | Novel compounds, their preparation and use |
PE20060315A1 (es) * | 2004-05-24 | 2006-05-15 | Irm Llc | Compuestos de tiazol como moduladores de ppar |
EP1749000A4 (en) * | 2004-05-25 | 2009-12-30 | Metabolex Inc | BICYCLIC SUBSTITUTED TRIAZOLE AS PPAR MODULATORS AND METHOD FOR THE PRODUCTION THEREOF |
MXPA06013581A (es) * | 2004-05-25 | 2007-03-15 | Metabolex Inc | Triazoles sustituidos como moduladores de ppar y metodos para su preparacion. |
JP2007269630A (ja) * | 2004-06-23 | 2007-10-18 | Toudai Tlo Ltd | インスリン分泌促進剤 |
MY147518A (en) | 2004-09-15 | 2012-12-31 | Janssen Pharmaceutica Nv | 4-((phenoxyalkyl)thio)-phenoxyacetic acids and analogs |
WO2006043797A1 (en) * | 2004-10-22 | 2006-04-27 | Heonjoong Kang | Process for alkyl aryl sulfide derivatives and new sulfide compounds |
ATE439347T1 (de) * | 2004-11-23 | 2009-08-15 | Warner Lambert Co | 7-(2h-pyrazol-3-yl)-3,5-dihydroxy-heptansäure- derivate als hmg-co-a-reductase-inhibitoren zur behandlung von lipidemia |
WO2006057448A1 (ja) * | 2004-11-26 | 2006-06-01 | Takeda Pharmaceutical Company Limited | アリールアルカン酸誘導体 |
ATE539066T1 (de) * | 2004-12-31 | 2012-01-15 | Seoul Nat Univ Ind Foundation | Organoselenhaltige verbindungen und deren verwendung |
CA2598821C (en) * | 2004-12-31 | 2011-05-31 | Heonjoong Kang | Organoselenium containing compounds and their use |
FR2880886B1 (fr) * | 2005-01-14 | 2007-04-06 | Merck Sante Soc Par Actions Si | Derives de l'acide 6-phenylhex-5-enoique, procedes pour leur preparation, compositions pharmaceutiques les contenant et applications en therapeutique |
RU2392274C2 (ru) * | 2005-02-25 | 2010-06-20 | Сеул Нэшнл Юниверсити Индастри Фаундейшн | Тиазольные производные в качестве лигандов ppar-дельта и способ их получения |
JP4869338B2 (ja) * | 2005-05-07 | 2012-02-08 | ソウル ナショナル ユニバーシティー インダストリー ファンデーション | ペルオキシソーム増殖因子活性化受容体δリガンドの製造方法及びこれを製造するための中間体 |
US7465804B2 (en) * | 2005-05-20 | 2008-12-16 | Amgen Inc. | Compounds, pharmaceutical compositions and methods for their use in treating metabolic disorders |
EP1889613A4 (en) * | 2005-05-27 | 2010-11-24 | Shionogi & Co | PHARMACEUTICAL COMPOSITION COMPRISING VITAMIN K |
WO2006126514A1 (ja) | 2005-05-27 | 2006-11-30 | Shionogi & Co., Ltd. | イソキサゾール骨格を有するアリール酢酸誘導体 |
US7943669B2 (en) | 2005-06-30 | 2011-05-17 | High Point Pharmaceuticals, Llc | Phenoxy acetic acids as PPAR delta activators |
CA2621949A1 (en) * | 2005-09-14 | 2007-03-22 | Amgen Inc. | Conformationally constrained 3- (4-hydroxy-phenyl) - substituted-propanoic acids useful for treating metabolic disorders |
JO3006B1 (ar) | 2005-09-14 | 2016-09-05 | Janssen Pharmaceutica Nv | املاح ليسين مبتكرة من مشتقات حامض 4-((فينوكسي الكيل)ثيو) فينوكسي الخليك |
PL1931660T3 (pl) * | 2005-09-29 | 2012-12-31 | Sanofi Sa | Pochodne fenylo-[1,2,4]-oksadiazol-5-onu z grupą fenylową, sposoby ich wytwarzania i ich zastosowanie jako środków farmaceutycznych |
KR20080048504A (ko) | 2005-09-29 | 2008-06-02 | 사노피-아벤티스 | 페닐- 및 피리디닐-1,2,4-옥사디아졸론 유도체, 이의제조방법 및 약제로서의 이의 용도 |
ES2386734T3 (es) | 2005-12-22 | 2012-08-28 | High Point Pharmaceuticals, Llc | Ácidos fenoxiacéticos como activadores de PPAR-DELTA |
CN101400663A (zh) * | 2006-01-10 | 2009-04-01 | 史密丝克莱恩比彻姆公司 | {2-甲基-4-[4-甲基-2-(4-三氟甲基苯基)噻唑-5-基甲硫基]苯氧基}-乙酸的多晶型 |
CN101007790B (zh) * | 2006-01-27 | 2011-03-30 | 北京摩力克科技有限公司 | 草氨酸衍生物、其制备方法和医药用途 |
CA2640476A1 (en) * | 2006-02-03 | 2007-08-16 | Eli Lilly And Company | Compounds and methods for modulating fx-receptors |
JP2009132620A (ja) * | 2006-03-07 | 2009-06-18 | Astellas Pharma Inc | フェニルチアゾール誘導体 |
JP2009529512A (ja) | 2006-03-09 | 2009-08-20 | ハイ ポイント ファーマシューティカルズ,リミティド ライアビリティ カンパニー | 新規な化合物、それらの製造法、及び使用法 |
JP2009530281A (ja) * | 2006-03-14 | 2009-08-27 | アムジエン・インコーポレーテツド | 代謝障害の治療に有用である二環式カルボン酸誘導体 |
RU2435764C2 (ru) * | 2006-04-18 | 2011-12-10 | Ниппон Кемифар Ко., Лтд. | АГЕНТ, АКТИВИРУЮЩИЙ РЕЦЕПТОР, АКТИВИРУЕМЫЙ ПРОЛИФЕРАТОРАМИ ПЕРОКСИСОМ δ |
PE20080188A1 (es) | 2006-04-18 | 2008-03-10 | Janssen Pharmaceutica Nv | Derivados del acido benzoazepin-oxi-acetico como agonistas de ppar-delta usados para aumentar hdl-c, reducir ldl-c y reducir colesterol |
US20100197950A1 (en) * | 2006-06-08 | 2010-08-05 | Kaare Gyberg Rasmussen | Process for preparing phenoxy acetic acid derivatives |
US20080004281A1 (en) * | 2006-06-28 | 2008-01-03 | Kalypsys, Inc. | Methods for the modulation of crp by the selective modulation of ppar delta |
JPWO2008016175A1 (ja) * | 2006-08-03 | 2009-12-24 | 日本ケミファ株式会社 | ペルオキシソーム増殖剤活性化受容体の活性化剤 |
AU2007292816B2 (en) * | 2006-09-07 | 2011-11-17 | Amgen Inc. | Benzo-fused compounds for use in treating metabolic disorders |
WO2008030520A1 (en) * | 2006-09-07 | 2008-03-13 | Amgen Inc. | Heterocyclic gpr40 modulators |
US9308198B2 (en) | 2006-09-08 | 2016-04-12 | Rhode Island Hospital | Treatment, prevention, and reversal of alcohol-induced brain disease |
EP2061484B1 (en) | 2006-09-08 | 2012-11-07 | Rhode Island Hospital | Treatment, prevention, and reversal of alcohol-induced liver disease |
CN101595089A (zh) | 2006-12-02 | 2009-12-02 | 财团法人首尔大学校产学协力财团 | 作为ppar配体的芳基化合物及其用途 |
AU2007341981A1 (en) | 2006-12-29 | 2008-07-10 | The Salk Institute For Biological Studies | Methods for enhancing exercise performance |
KR100954237B1 (ko) | 2007-01-08 | 2010-04-21 | 재단법인서울대학교산학협력재단 | 퍼록시솜 증식자 활성화 수용체 델타 리간드 티아졸 화합물및 이를 함유하는 의약, 화장품 및 건강식품 조성물 |
KR20090113901A (ko) * | 2007-02-22 | 2009-11-02 | 아이알엠 엘엘씨 | G 단백질-커플링된 수용체를 조절하기 위한 화합물 및 방법 |
US7572934B2 (en) | 2007-04-16 | 2009-08-11 | Amgen Inc. | Substituted biphenyl GPR40 modulators |
WO2008154023A1 (en) * | 2007-06-11 | 2008-12-18 | Cerenis Therapeutics S.A. | Novel uses of ppar delta agonists |
GB0712653D0 (en) | 2007-06-28 | 2007-08-08 | Syngenta Ltd | Novel herbicides |
GB0717082D0 (en) | 2007-09-03 | 2007-10-10 | Syngenta Ltd | Novel herbicides |
WO2009048527A1 (en) | 2007-10-10 | 2009-04-16 | Amgen Inc. | Substituted biphenyl gpr40 modulators |
AU2008338963A1 (en) * | 2007-12-13 | 2009-06-25 | Sri International | PPAR-delta ligands and methods of their use |
AU2009220163B2 (en) * | 2008-03-06 | 2011-10-06 | Amgen Inc. | Conformationally constrained carboxylic acid derivatives useful for treating metabolic disorders |
BRPI0911197A2 (pt) | 2008-04-15 | 2015-10-13 | Nippon Chemiphar Co | composto, ativador de receptor ativado pelo proliferador de peroxissoma, e, medicamento para o tratamento e /ou profilaxia de uma doença. |
CN101643451B (zh) | 2008-08-07 | 2013-03-06 | 浙江海正药业股份有限公司 | 过氧化物酶增殖物激活受体亚型δ类激动剂化合物及其制备方法 |
ES2450567T3 (es) | 2008-10-15 | 2014-03-25 | Amgen, Inc | Moduladores de GPR40 espirocíclicos |
ES2712052T3 (es) | 2008-10-17 | 2019-05-09 | Cymabay Therapeutics Inc | Métodos para reducir partículas de LDL pequeñas y densas |
JP2013525267A (ja) * | 2010-02-25 | 2013-06-20 | エスエヌユー アール&ディービー ファウンデーション | ペルオキシソーム増殖剤活性化受容体リガンドのセレナゾール誘導体、その製造方法及びその化合物の用途 |
CN102285933B (zh) * | 2010-06-18 | 2016-03-09 | 浙江海正药业股份有限公司 | 一种对亚型过氧化物酶增殖物激活受体具有激动作用的化合物、其制备方法和应用 |
US20130156720A1 (en) | 2010-08-27 | 2013-06-20 | Ironwood Pharmaceuticals, Inc. | Compositions and methods for treating or preventing metabolic syndrome and related diseases and disorders |
BR112013004882A2 (pt) * | 2010-08-31 | 2016-05-03 | Snu R&Db Foundation | utilização de reprogramação fetal de agonista ppar delta |
US9695137B2 (en) * | 2013-03-14 | 2017-07-04 | The University Of Toledo | Analogs of peroxisome proliferator activated receptor (PPAR) agonists, and methods of using the same |
US10181018B2 (en) * | 2013-03-14 | 2019-01-15 | The University Of Toledo | Analogs of proxisome proliferator activated receptor (PPAR) agonists and methods of using the same |
CA2923422C (en) | 2013-09-09 | 2021-09-07 | Vtv Therapeutics Llc | Use of a ppar-delta agonist for treating muscle atrophy |
US12268672B2 (en) | 2018-10-23 | 2025-04-08 | Japan Science And Technology Agency | PPARδ activator |
US11634387B2 (en) | 2019-09-26 | 2023-04-25 | Abionyx Pharma Sa | Compounds useful for treating liver diseases |
WO2022189856A1 (en) * | 2021-03-08 | 2022-09-15 | Abionyx Pharma Sa | Compounds useful for treating liver diseases |
WO2023147309A1 (en) | 2022-01-25 | 2023-08-03 | Reneo Pharmaceuticals, Inc. | Use of ppar-delta agonists in the treatment of disease |
Family Cites Families (21)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS644688A (en) * | 1987-06-26 | 1989-01-09 | Tokuyama Soda Kk | Photochromic composition |
JPH0793082B2 (ja) * | 1987-09-07 | 1995-10-09 | 株式会社明電舎 | 真空インタラプタの化成方法 |
JP2551151B2 (ja) * | 1989-06-22 | 1996-11-06 | 神鋼電機株式会社 | 潜熱回収方式の給湯装置における放熱装置 |
JP3039009B2 (ja) * | 1991-06-25 | 2000-05-08 | ソニー株式会社 | 固体撮像素子の駆動装置 |
TW268952B (cs) | 1993-02-26 | 1996-01-21 | Takeda Pharm Industry Co Ltd | |
US5591862A (en) * | 1993-06-11 | 1997-01-07 | Takeda Chemical Industries, Ltd. | Tetrazole derivatives, their production and use |
JP3466273B2 (ja) | 1993-06-11 | 2003-11-10 | 武田薬品工業株式会社 | テトラゾール誘導体、その製造法およびそれを含んでなる医薬 |
JP3836521B2 (ja) | 1994-08-10 | 2006-10-25 | 武田薬品工業株式会社 | 2,4−チアゾリジンジオン誘導体、その製造法およびそれを含んでなる医薬組成物 |
JP2850809B2 (ja) | 1994-11-02 | 1999-01-27 | 武田薬品工業株式会社 | 2,4−オキサゾリジンジオン誘導体およびそれを含んでなる医薬組成物 |
JP3880108B2 (ja) | 1994-11-02 | 2007-02-14 | 武田薬品工業株式会社 | 2,4−オキサゾリジンジオン誘導体、その製造法およびそれを含んでなる医薬組成物 |
JPH08325250A (ja) | 1995-05-31 | 1996-12-10 | Sumitomo Metal Ind Ltd | 新規置換フェノール誘導体 |
JPH08325263A (ja) * | 1995-05-31 | 1996-12-10 | Sumitomo Metal Ind Ltd | 新規2−アミノ−3−フェニルプロピオン酸誘導体 |
US5847008A (en) * | 1996-02-02 | 1998-12-08 | Merck & Co., Inc. | Method of treating diabetes and related disease states |
WO1997028149A1 (en) * | 1996-02-02 | 1997-08-07 | Merck & Co., Inc. | Method for raising hdl cholesterol levels |
US5859051A (en) * | 1996-02-02 | 1999-01-12 | Merck & Co., Inc. | Antidiabetic agents |
GB9604242D0 (en) * | 1996-02-28 | 1996-05-01 | Glaxo Wellcome Inc | Chemical compounds |
JP3215048B2 (ja) | 1996-04-03 | 2001-10-02 | 日本たばこ産業株式会社 | プロピオン酸誘導体及びその用途 |
RU2174121C2 (ru) * | 1996-08-19 | 2001-09-27 | Джапан Тобакко Инк. | Производные пропионовой кислоты и фармацевтическая композиция на их основе |
WO1999004815A1 (fr) * | 1997-07-24 | 1999-02-04 | Yamanouchi Pharmaceutical Co., Ltd. | Compositions medicinales hypocholesterolemiantes |
WO1999046232A1 (fr) * | 1998-03-10 | 1999-09-16 | Ono Pharmaceutical Co., Ltd. | Derives d'acide carboxylique et medicaments contenant ces derives comme principe actif |
KR102220553B1 (ko) * | 2015-03-10 | 2021-02-26 | 한국전자통신연구원 | 표시 패널 및 그것을 포함하는 표시 장치 |
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