ZA200508362B - Alpha substituted carboxylic acid as PPAR modulators - Google Patents
Alpha substituted carboxylic acid as PPAR modulators Download PDFInfo
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- ZA200508362B ZA200508362B ZA200508362A ZA200508362A ZA200508362B ZA 200508362 B ZA200508362 B ZA 200508362B ZA 200508362 A ZA200508362 A ZA 200508362A ZA 200508362 A ZA200508362 A ZA 200508362A ZA 200508362 B ZA200508362 B ZA 200508362B
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- South Africa
- Prior art keywords
- acid
- methyl
- oxazol
- ethoxy
- phenyl
- Prior art date
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Classifications
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/65—One oxygen atom attached in position 3 or 5
- C07D213/66—One oxygen atom attached in position 3 or 5 having in position 3 an oxygen atom and in each of the positions 4 and 5 a carbon atom bound to an oxygen, sulphur, or nitrogen atom, e.g. pyridoxal
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- 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
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C—CHEMISTRY; METALLURGY
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- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
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- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
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- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- 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
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
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US46321303P | 2003-04-15 | 2003-04-15 |
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JP (1) | JP2006523671A (ja) |
KR (1) | KR20060009846A (ja) |
CN (1) | CN1805943A (ja) |
AP (1) | AP2005003418A0 (ja) |
AR (1) | AR044514A1 (ja) |
AU (1) | AU2004230316A1 (ja) |
BR (1) | BRPI0409429A (ja) |
CA (1) | CA2521915A1 (ja) |
CL (1) | CL2004000800A1 (ja) |
EA (1) | EA200501462A1 (ja) |
EC (1) | ECSP056105A (ja) |
IS (1) | IS8033A (ja) |
MA (1) | MA27764A1 (ja) |
MX (1) | MXPA05010967A (ja) |
NL (1) | NL1025946C2 (ja) |
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Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7323480B2 (en) * | 2004-05-25 | 2008-01-29 | Metabolex, Inc. | Substituted triazoles as modulators of PPAR and methods of their preparation |
AU2006244203B2 (en) | 2005-05-09 | 2012-05-03 | Achillion Pharmaceuticals, Inc. | Thiazole compounds and methods of use |
EA017198B1 (ru) | 2006-10-30 | 2012-10-30 | Хрома Терапьютикс Лтд. | Гидроксаматы в качестве ингибиторов гистон-деацетилазы |
CN101790512A (zh) | 2007-03-08 | 2010-07-28 | 阿尔比里奥公司 | 2-取代-3-苯基丙酸衍生物及其在炎性肠病治疗中的用途 |
CN101801964A (zh) | 2007-05-22 | 2010-08-11 | 艾其林医药公司 | 杂芳基取代的噻唑及其作为抗病毒剂的用途 |
US8106209B2 (en) | 2008-06-06 | 2012-01-31 | Achillion Pharmaceuticals, Inc. | Substituted aminothiazole prodrugs of compounds with anti-HCV activity |
US8344018B2 (en) | 2008-07-14 | 2013-01-01 | Gilead Sciences, Inc. | Oxindolyl inhibitor compounds |
AU2009271019A1 (en) | 2008-07-14 | 2010-01-21 | Gilead Sciences, Inc. | Fused heterocyclyc inhibitors of histone deacetylase and/or cyclin-dependent kinases |
WO2010009139A2 (en) | 2008-07-14 | 2010-01-21 | Gilead Colorado, Inc. | Imidazolyl pyrimidine inhibitor compounds |
MX2011001090A (es) | 2008-07-28 | 2011-03-15 | Gilead Sciences Inc | Compuestos de inhibidor de desacetilasa de histona de cicloalquilideno y heterocicloalquilideno. |
EP2440519A1 (en) | 2009-06-08 | 2012-04-18 | Gilead Sciences, Inc. | Alkanoylamino benzamide aniline hdac inihibitor compounds |
MX2011013166A (es) | 2009-06-08 | 2012-01-30 | Gilead Sciences Inc | Compuestos inhibidores de hdac de cicloalquilcarbamatobenzamida-an ilina. |
DE102010055499A1 (de) * | 2010-12-22 | 2011-06-16 | W.C. Heraeus Gmbh | Prozess zur Herstellung von Bendamustinalkylester, Bendarmustin sowie Derivaten davon |
US9630929B2 (en) | 2011-10-31 | 2017-04-25 | Xenon Pharmaceuticals Inc. | Benzenesulfonamide compounds and their use as therapeutic agents |
WO2013064984A1 (en) | 2011-10-31 | 2013-05-10 | Xenon Pharmaceuticals Inc. | Biaryl ether sulfonamides and their use as therapeutic agents |
FR2982858B1 (fr) * | 2011-11-18 | 2013-11-29 | Rhodia Operations | Procede de fabrication de composes comprenant des fonctions nitriles |
FR2984322B1 (fr) * | 2011-12-16 | 2013-12-20 | Rhodia Operations | Procede de fabrication de composes comprenant des fonctions nitriles |
EA026393B1 (ru) | 2012-05-22 | 2017-04-28 | Дженентек, Инк. | N-замещенные бензамиды и их применение в лечении боли |
KR101663436B1 (ko) | 2012-07-06 | 2016-10-06 | 제넨테크, 인크. | N-치환된 벤즈아미드 및 이의 사용 방법 |
EP2968280A4 (en) | 2013-03-14 | 2016-08-10 | Genentech Inc | SUBSTITUTED TRIAZOLOPYRIDINES AND METHOD OF USE THEREOF |
WO2014144545A2 (en) | 2013-03-15 | 2014-09-18 | Genentech, Inc. | Substituted benzoxazoles and methods of use thereof |
EP3450428A1 (en) | 2013-11-27 | 2019-03-06 | Genentech, Inc. | Substituted benzamides and methods of use thereof |
US10005724B2 (en) | 2014-07-07 | 2018-06-26 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
KR20180008761A (ko) | 2015-05-22 | 2018-01-24 | 제넨테크, 인크. | 치환된 벤즈아미드 및 이의 이용 방법 |
WO2017035271A1 (en) | 2015-08-27 | 2017-03-02 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
CA2999769A1 (en) | 2015-09-28 | 2017-04-06 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
EP3380466A1 (en) | 2015-11-25 | 2018-10-03 | Genentech, Inc. | Substituted benzamides useful as sodium channel blockers |
JP2019513714A (ja) | 2016-03-30 | 2019-05-30 | ジェネンテック, インコーポレイテッド | 置換ベンズアミド及びその使用方法 |
CA3039853A1 (en) | 2016-10-17 | 2018-04-26 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
JP2020511511A (ja) | 2017-03-24 | 2020-04-16 | ジェネンテック, インコーポレイテッド | ナトリウムチャネル阻害剤としての4−ピペリジン−n−(ピリミジン−4−イル)クロマン−7−スルホンアミド誘導体 |
TW202000651A (zh) | 2018-02-26 | 2020-01-01 | 美商建南德克公司 | 治療性組成物及其使用方法 |
CN111936494A (zh) | 2018-03-30 | 2020-11-13 | 豪夫迈·罗氏有限公司 | 作为钠通道抑制剂的取代的氢-吡啶并-吖嗪 |
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EP1088824B1 (en) * | 1999-09-30 | 2004-01-07 | Pfizer Products Inc. | Bicyclic pyrrolyl amides as glycogen phosphorylase inhibitors |
BR0207227A (pt) * | 2001-02-15 | 2004-02-10 | Pfizer Prod Inc | Compostos receptores ativados proliferadores ppar |
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Also Published As
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BRPI0409429A (pt) | 2006-04-18 |
TNSN05262A1 (fr) | 2007-07-10 |
MXPA05010967A (es) | 2005-11-28 |
WO2004092145A8 (en) | 2005-05-12 |
TW200510353A (en) | 2005-03-16 |
IS8033A (is) | 2005-09-15 |
EP1615899A1 (en) | 2006-01-18 |
JP2006523671A (ja) | 2006-10-19 |
CA2521915A1 (en) | 2004-10-28 |
NL1025946A1 (nl) | 2004-10-18 |
ECSP056105A (es) | 2006-03-01 |
AP2005003418A0 (en) | 2005-12-31 |
WO2004092145A1 (en) | 2004-10-28 |
EA200501462A1 (ru) | 2006-04-28 |
AR044514A1 (es) | 2005-09-14 |
MA27764A1 (fr) | 2006-02-01 |
CN1805943A (zh) | 2006-07-19 |
NO20055370L (no) | 2006-01-12 |
AU2004230316A1 (en) | 2004-10-28 |
OA13157A (en) | 2006-12-13 |
KR20060009846A (ko) | 2006-02-01 |
PE20050415A1 (es) | 2005-06-13 |
NO20055370D0 (no) | 2005-11-14 |
PA8600201A1 (es) | 2005-02-04 |
NL1025946C2 (nl) | 2005-02-01 |
CL2004000800A1 (es) | 2005-03-04 |
UY28266A1 (es) | 2004-11-30 |
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