CN1751037A - 作为ppar调节剂的磺酰胺衍生物 - Google Patents
作为ppar调节剂的磺酰胺衍生物 Download PDFInfo
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- CN1751037A CN1751037A CNA2004800042507A CN200480004250A CN1751037A CN 1751037 A CN1751037 A CN 1751037A CN A2004800042507 A CNA2004800042507 A CN A2004800042507A CN 200480004250 A CN200480004250 A CN 200480004250A CN 1751037 A CN1751037 A CN 1751037A
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- alkyl
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
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- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/12—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
- C07C311/13—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/17—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/19—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102336689A (zh) * | 2011-08-29 | 2012-02-01 | 天津市筠凯化工科技有限公司 | 4-氯-3-(三氟甲基)苯磺酰氯的制备及其精制方法 |
| CN119405633A (zh) * | 2024-11-25 | 2025-02-11 | 浙江大学 | 2,6-dmhq在抗心脏和肝脏缺血再灌注损伤中的应用 |
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| US7517884B2 (en) | 1998-03-30 | 2009-04-14 | Kalypsys Inc. | Sulfonyl-substituted bicyclic compounds as modulators of PPAR |
| KR100761615B1 (ko) | 2003-11-05 | 2007-10-04 | 에프. 호프만-라 로슈 아게 | Ppar 활성화제로서 헤테로아릴 유도체 |
| EP1745014B1 (en) | 2004-05-05 | 2011-07-06 | High Point Pharmaceuticals, LLC | Novel compounds, their preparation and use |
| WO2005105726A1 (en) | 2004-05-05 | 2005-11-10 | Novo Nordisk A/S | Novel compounds, their preparation and use |
| BRPI0516435B1 (pt) | 2004-10-29 | 2021-09-21 | Kalypsys , Inc | Composto, e composição farmacêutica |
| WO2007005455A2 (en) * | 2005-06-30 | 2007-01-11 | Bayer Cropscience Ag | Improved process for preparing (disubstitutedpropenyl) phenylalkyl substituted heterocycles |
| US7943669B2 (en) | 2005-06-30 | 2011-05-17 | High Point Pharmaceuticals, Llc | Phenoxy acetic acids as PPAR delta activators |
| US7915316B2 (en) * | 2005-08-22 | 2011-03-29 | Allergan, Inc | Sulfonamides |
| EP1939175B1 (en) * | 2005-09-27 | 2017-03-01 | Shionogi&Co., Ltd. | Sulfonamide derivative having pgd2 receptor antagonistic activity |
| CN101273013B (zh) * | 2005-09-27 | 2013-06-12 | 盐野义制药株式会社 | 具有pgd2受体拮抗活性的磺酰胺衍生物 |
| AU2006305769B2 (en) | 2005-10-25 | 2012-06-14 | Kalypsys, Inc. | Salts of modulators of PPAR and methods of treating metabolic disorders |
| US7943613B2 (en) | 2005-12-22 | 2011-05-17 | High Point Pharmaceuticals, Llc | Compounds, their preparation and use |
| CA2645719A1 (en) | 2006-03-09 | 2007-09-13 | High Point Pharmaceuticals, Llc | Compounds that modulate ppar activity, their preparation and use |
| JP5189345B2 (ja) * | 2006-11-06 | 2013-04-24 | 東ソー株式会社 | トリフルオロメチル化用反応試剤 |
| US20080176861A1 (en) | 2007-01-23 | 2008-07-24 | Kalypsys, Inc. | Sulfonyl-substituted bicyclic compounds as ppar modulators for the treatment of non-alcoholic steatohepatitis |
| KR101152659B1 (ko) * | 2009-10-09 | 2012-06-15 | 한국과학기술연구원 | 세로토닌 수용체 길항 작용과 세로토닌 트랜스포터 억제 작용을 동시에 가지는 설폰아마이드 화합물 |
| CA2809958A1 (en) | 2010-08-31 | 2012-03-08 | Snu R & Db Foundation | Use of the fetal reprogramming of a ppar ? agonist |
| JP5767458B2 (ja) * | 2010-11-09 | 2015-08-19 | スガイ化学工業株式会社 | ポリオキシエチレン付加カリックスアレーン誘導体の製造方法 |
| KR20140099546A (ko) | 2012-01-10 | 2014-08-12 | 일라이 릴리 앤드 캄파니 | 류코트리엔 b4 길항제 화합물 |
| ES2811087T3 (es) | 2013-09-09 | 2021-03-10 | Vtv Therapeutics Llc | Uso de agonistas de PPAR-delta para tratar la atrofia muscular |
| WO2016057322A1 (en) | 2014-10-08 | 2016-04-14 | Salk Institute For Biological Studies | Ppar agonists and methods of use thereof |
| US10188627B2 (en) | 2014-10-08 | 2019-01-29 | Mitobridge, Inc. | PPAR agonists, compounds, pharmaceutical compositions, and methods of use thereof |
| US10103402B2 (en) * | 2015-12-01 | 2018-10-16 | University Of Kentucky Research Foundation | Liquid phenothiazine catholytes for non-aqueous redox flow batteries |
| WO2023147309A1 (en) | 2022-01-25 | 2023-08-03 | Reneo Pharmaceuticals, Inc. | Use of ppar-delta agonists in the treatment of disease |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5084466A (en) * | 1989-01-31 | 1992-01-28 | Hoffmann-La Roche Inc. | Novel carboxamide pyridine compounds which have useful pharmaceutical utility |
| US5089514A (en) | 1990-06-14 | 1992-02-18 | Pfizer Inc. | 3-coxazolyl [phenyl, chromanyl or benzofuranyl]-2-hydroxypropionic acid derivatives and analogs as hypoglycemic agents |
| JPH05125038A (ja) * | 1991-03-07 | 1993-05-21 | Tanabe Seiyaku Co Ltd | フエノキシアルカン酸誘導体及びその製法 |
| JPH05194370A (ja) * | 1992-01-22 | 1993-08-03 | Taisho Pharmaceut Co Ltd | スルホンアミド誘導体 |
| US5232945A (en) | 1992-07-20 | 1993-08-03 | Pfizer Inc. | 3-aryl-2-hydroxypropionic acid derivatives and analogs as antihypertensives |
| JPH0672867A (ja) * | 1992-08-27 | 1994-03-15 | Tanabe Seiyaku Co Ltd | 抗脂血剤 |
| US5902726A (en) | 1994-12-23 | 1999-05-11 | Glaxo Wellcome Inc. | Activators of the nuclear orphan receptor peroxisome proliferator-activated receptor gamma |
| US6062509A (en) | 1994-12-23 | 2000-05-16 | Hexcel Corporation | Retrofit centerline luggage bin assemblies compatible with existing aircraft bin supports |
| WO1996025926A1 (en) * | 1995-02-21 | 1996-08-29 | Nippon Suisan Kaisha, Ltd. | Glutamic acid receptor agonist |
| WO1997028115A1 (en) | 1996-02-02 | 1997-08-07 | Merck & Co., Inc. | Antidiabetic agents |
| GB9604242D0 (en) | 1996-02-28 | 1996-05-01 | Glaxo Wellcome Inc | Chemical compounds |
| US6200995B1 (en) * | 1998-01-29 | 2001-03-13 | Tularik Inc. | PPAR-γ modulators |
| KR100620337B1 (ko) | 1998-03-10 | 2006-09-13 | 오노 야꾸힝 고교 가부시키가이샤 | 카르복실산 유도체와 그 유도체를 유효 성분으로서함유하는 약제 |
| GB9822473D0 (en) * | 1998-10-16 | 1998-12-09 | Glaxo Group Ltd | Chemical compounds |
| US6248781B1 (en) | 1998-10-21 | 2001-06-19 | Novo Nordisk A/S | Compounds useful in the treatment of conditions mediated by peroxisome proliferator-activated receptors (PPAR) |
| RU2219172C2 (ru) | 1999-04-06 | 2003-12-20 | Санкио Компани, Лимитед | α-ЗАМЕЩЕННЫЕ ПРОИЗВОДНЫЕ КАРБОНОВЫХ КИСЛОТ |
| PT1177187E (pt) * | 1999-04-28 | 2007-09-03 | Sanofi Aventis Deutschland | Derivados ácidos de di-arilo como ligados do receptor ppar. |
| AU5886900A (en) | 1999-06-25 | 2001-01-31 | Institutes For Pharmaceutical Discovery, Llc, The | Substituted phenoxyacetic acids |
| AU7073400A (en) | 1999-08-27 | 2001-03-26 | Eli Lilly And Company | Biaryl-oxa(thia)zole derivatives and their use as ppars modulators |
| TWI262185B (en) | 1999-10-01 | 2006-09-21 | Eisai Co Ltd | Carboxylic acid derivatives having anti-hyperglycemia and anti-hyperlipemia action, and pharmaceutical composition containing the derivatives |
| AU7995300A (en) * | 1999-10-05 | 2001-05-10 | Bethesda Pharmaceuticals, Inc. | Dithiolane derivatives |
| PE20011010A1 (es) * | 1999-12-02 | 2001-10-18 | Glaxo Group Ltd | Oxazoles y tiazoles sustituidos como agonista del receptor activado por el proliferador de peroxisomas humano |
| JP4316787B2 (ja) | 2000-01-11 | 2009-08-19 | 壽製薬株式会社 | エーテル又はアミド誘導体、その製法並びにそれを含有する糖尿病治療剤、 |
| US7176224B2 (en) | 2000-08-23 | 2007-02-13 | Eli Lilly And Company | Oxazolyl-aryloxyacetic acid derivatives and their use as PPAR agonists |
| CA2420178A1 (en) | 2000-08-23 | 2002-03-07 | Eli Lilly And Company | Oxazolyl-aryloxyacetic acid derivatives and their use as ppar agonists |
| US7071220B2 (en) * | 2000-09-18 | 2006-07-04 | Toa Eiyo Ltd. | N-substituted benzothiophenesulfonamide derivatives |
| US6852738B2 (en) * | 2001-01-30 | 2005-02-08 | Merck & Co., Inc. | Acyl sulfamides for treatment of obesity, diabetes and lipid disorders |
| EP1372632A1 (en) * | 2001-02-15 | 2004-01-02 | Pfizer Products Inc. | Proliferative activator receptor (ppar) compounds |
| IL158873A0 (en) | 2001-06-07 | 2004-05-12 | Lilly Co Eli | Modulators of peroxisome proliferator activated receptors |
| ATE375350T1 (de) * | 2002-02-21 | 2007-10-15 | Lilly Co Eli | Modulatoren von peroxisome proliferator- aktivierten rezeptoren |
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2004
- 2004-02-10 BR BR0407180-8A patent/BRPI0407180A/pt not_active Application Discontinuation
- 2004-02-10 JP JP2006502992A patent/JP2006520755A/ja active Pending
- 2004-02-10 MX MXPA05008581A patent/MXPA05008581A/es active IP Right Grant
- 2004-02-10 CN CNA2004800042507A patent/CN1751037A/zh active Pending
- 2004-02-10 CA CA002512883A patent/CA2512883A1/en not_active Abandoned
- 2004-02-10 AU AU2004212887A patent/AU2004212887A1/en not_active Abandoned
- 2004-02-10 ES ES04709806T patent/ES2297382T3/es not_active Expired - Lifetime
- 2004-02-10 DE DE602004010889T patent/DE602004010889T2/de not_active Expired - Fee Related
- 2004-02-10 EP EP04709806A patent/EP1597248B1/en not_active Expired - Lifetime
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- 2004-02-10 AT AT04709806T patent/ATE382043T1/de not_active IP Right Cessation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102336689A (zh) * | 2011-08-29 | 2012-02-01 | 天津市筠凯化工科技有限公司 | 4-氯-3-(三氟甲基)苯磺酰氯的制备及其精制方法 |
| CN119405633A (zh) * | 2024-11-25 | 2025-02-11 | 浙江大学 | 2,6-dmhq在抗心脏和肝脏缺血再灌注损伤中的应用 |
| CN119405633B (zh) * | 2024-11-25 | 2025-12-02 | 浙江大学 | 2,6-dmhq在抗心脏和肝脏缺血再灌注损伤中的应用 |
Also Published As
| Publication number | Publication date |
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| EP1597248B1 (en) | 2007-12-26 |
| MXPA05008581A (es) | 2005-11-04 |
| WO2004073606A3 (en) | 2005-03-31 |
| CA2512883A1 (en) | 2004-09-02 |
| JP2006520755A (ja) | 2006-09-14 |
| US7655641B2 (en) | 2010-02-02 |
| US20060217433A1 (en) | 2006-09-28 |
| WO2004073606A2 (en) | 2004-09-02 |
| ES2297382T3 (es) | 2008-05-01 |
| DE602004010889D1 (de) | 2008-02-07 |
| BRPI0407180A (pt) | 2006-02-07 |
| DE602004010889T2 (de) | 2008-12-11 |
| ATE382043T1 (de) | 2008-01-15 |
| AU2004212887A1 (en) | 2004-09-02 |
| EP1597248A2 (en) | 2005-11-23 |
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