ZA200410061B - Phenylalkanoic acid and phenyloxyalkanoic acid derivatives as hPPAR acivators - Google Patents
Phenylalkanoic acid and phenyloxyalkanoic acid derivatives as hPPAR acivators Download PDFInfo
- Publication number
- ZA200410061B ZA200410061B ZA200410061A ZA200410061A ZA200410061B ZA 200410061 B ZA200410061 B ZA 200410061B ZA 200410061 A ZA200410061 A ZA 200410061A ZA 200410061 A ZA200410061 A ZA 200410061A ZA 200410061 B ZA200410061 B ZA 200410061B
- Authority
- ZA
- South Africa
- Prior art keywords
- pyridinyl
- oxy
- phenyl
- acid
- acetic acid
- Prior art date
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Classifications
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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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- 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
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- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/32—Sulfur atoms
- C07D213/34—Sulfur atoms to which a second hetero atom is attached
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Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB0214149.7A GB0214149D0 (en) | 2002-06-19 | 2002-06-19 | Chemical compounds |
Publications (1)
Publication Number | Publication Date |
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ZA200410061B true ZA200410061B (en) | 2006-07-26 |
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Application Number | Title | Priority Date | Filing Date |
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ZA200410061A ZA200410061B (en) | 2002-06-19 | 2004-12-13 | Phenylalkanoic acid and phenyloxyalkanoic acid derivatives as hPPAR acivators |
Country Status (26)
Country | Link |
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US (1) | US7338960B2 (xx) |
EP (1) | EP1513526B1 (xx) |
JP (1) | JP2005534672A (xx) |
KR (1) | KR20050030624A (xx) |
CN (1) | CN1674897A (xx) |
AT (1) | ATE377420T1 (xx) |
AU (1) | AU2003245962B2 (xx) |
BR (1) | BR0311931A (xx) |
CA (1) | CA2487909A1 (xx) |
CY (1) | CY1107168T1 (xx) |
DE (1) | DE60317326T2 (xx) |
DK (1) | DK1513526T3 (xx) |
ES (1) | ES2295601T3 (xx) |
GB (1) | GB0214149D0 (xx) |
HK (1) | HK1076712A1 (xx) |
IL (1) | IL165476A0 (xx) |
IS (1) | IS7574A (xx) |
MX (1) | MXPA04012857A (xx) |
NO (1) | NO20045328L (xx) |
NZ (1) | NZ537210A (xx) |
PL (1) | PL375148A1 (xx) |
PT (1) | PT1513526E (xx) |
RU (1) | RU2323929C2 (xx) |
SI (1) | SI1513526T1 (xx) |
WO (1) | WO2004000315A1 (xx) |
ZA (1) | ZA200410061B (xx) |
Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7244763B2 (en) | 2003-04-17 | 2007-07-17 | Warner Lambert Company Llc | Compounds that modulate PPAR activity and methods of preparation |
JP4928941B2 (ja) | 2003-09-19 | 2012-05-09 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 4−((フェノキシアルキル)チオ)−フェノキシ酢酸および類似化合物 |
WO2005049573A1 (en) | 2003-11-05 | 2005-06-02 | F. Hoffmann-La Roche Ag | Phenyl derivatives as ppar agonists |
TW200523247A (en) | 2003-12-25 | 2005-07-16 | Takeda Pharmaceutical | 3-(4-benzyloxyphenyl) propanoic acid derivatives |
EP1737809B1 (en) * | 2004-02-27 | 2013-09-18 | Amgen, Inc | Compounds, pharmaceutical compositions and methods for use in treating metabolic disorders |
AR048523A1 (es) * | 2004-04-07 | 2006-05-03 | Kalypsys Inc | Compuestos con estructura de aril sulfonamida y sulfonilo como moduladores de ppar y metodos para tratar trastornos metabolicos |
WO2005105736A1 (en) | 2004-05-05 | 2005-11-10 | Novo Nordisk A/S | Novel compounds, their preparation and use |
ES2352085T3 (es) | 2004-05-05 | 2011-02-15 | High Point Pharmaceuticals, Llc | Nuevos compuestos, su preparación y uso. |
MY147518A (en) * | 2004-09-15 | 2012-12-31 | Janssen Pharmaceutica Nv | 4-((phenoxyalkyl)thio)-phenoxyacetic acids and analogs |
US7465804B2 (en) | 2005-05-20 | 2008-12-16 | Amgen Inc. | Compounds, pharmaceutical compositions and methods for their use in treating metabolic disorders |
BRPI0612730A2 (pt) | 2005-06-30 | 2010-11-30 | Novo Nordisk As | compostos, suas preparações e uso |
JO3006B1 (ar) | 2005-09-14 | 2016-09-05 | Janssen Pharmaceutica Nv | املاح ليسين مبتكرة من مشتقات حامض 4-((فينوكسي الكيل)ثيو) فينوكسي الخليك |
WO2007033002A1 (en) * | 2005-09-14 | 2007-03-22 | Amgen Inc. | Conformationally constrained 3- (4-hydroxy-phenyl) - substituted-propanoic acids useful for treating metabolic disorders |
US7943613B2 (en) | 2005-12-22 | 2011-05-17 | High Point Pharmaceuticals, Llc | Compounds, their preparation and use |
WO2007101864A2 (en) | 2006-03-09 | 2007-09-13 | High Point Pharmaceuticals, Llc | Compounds that modulate ppar activity, their preparation and use |
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 |
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 |
CN101591227B (zh) * | 2006-06-23 | 2012-09-05 | 赵昱 | 一类肉桂醇类衍生物及其制备方法和药物用途 |
US7687526B2 (en) * | 2006-09-07 | 2010-03-30 | Amgen Inc. | Benzo-fused compounds for use in treating metabolic disorders |
WO2008030520A1 (en) | 2006-09-07 | 2008-03-13 | Amgen Inc. | Heterocyclic gpr40 modulators |
CN102584685A (zh) * | 2006-12-02 | 2012-07-18 | 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 |
US7572934B2 (en) * | 2007-04-16 | 2009-08-11 | Amgen Inc. | Substituted biphenyl GPR40 modulators |
EP2184277B1 (en) * | 2007-07-25 | 2015-07-01 | Institute Of Pharmacology And Toxicology Academy Of Military Medical Sciences P.L.A. China | Aryl pyrimidine derivatives, preparation methods and pharmaceutical uses thereof |
WO2009048527A1 (en) | 2007-10-10 | 2009-04-16 | Amgen Inc. | Substituted biphenyl gpr40 modulators |
JP2011515341A (ja) | 2008-03-06 | 2011-05-19 | 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な立体配座的に制限されたカルボン酸誘導体 |
AU2009303475B2 (en) | 2008-10-15 | 2012-09-13 | Amgen Inc. | Spirocyclic GPR40 modulators |
WO2012145617A2 (en) * | 2011-04-22 | 2012-10-26 | Jasco Pharmaceuticals, LLC | Aminopyrimidine kinase inhibitors |
TW201341356A (zh) | 2012-02-28 | 2013-10-16 | 皮拉馬爾企業有限公司 | 作為gpr促效劑之苯基烷酸衍生物 |
KR101569522B1 (ko) | 2013-04-18 | 2015-11-17 | 현대약품 주식회사 | 신규한 3-(4-(벤질옥시)페닐)헥스-4-이노익 산 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 대사성 질환의 예방 또는 치료용 약학적 조성물 |
CA2923422C (en) | 2013-09-09 | 2021-09-07 | Vtv Therapeutics Llc | Use of a ppar-delta agonist for treating muscle atrophy |
CN108503581A (zh) * | 2018-04-12 | 2018-09-07 | 苏州康润医药有限公司 | 一种3-溴-6-氟-2-吡啶乙酮的合成方法 |
WO2023147309A1 (en) | 2022-01-25 | 2023-08-03 | Reneo Pharmaceuticals, Inc. | Use of ppar-delta agonists in the treatment of disease |
Family Cites Families (10)
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CS175831B1 (xx) * | 1974-12-17 | 1977-05-31 | ||
FR2401459A1 (fr) * | 1977-08-26 | 1979-03-23 | Cii Honeywell Bull | Support d'information portatif muni d'un microprocesseur et d'une memoire morte programmable |
DE4038335A1 (de) * | 1990-12-01 | 1992-06-04 | Boehringer Mannheim Gmbh | Neue pyridinderivate, verfahren zu ihrer herstellung und verwendung als arzneimittel |
GB9604242D0 (en) * | 1996-02-28 | 1996-05-01 | Glaxo Wellcome Inc | Chemical compounds |
AU8750298A (en) * | 1997-08-28 | 1999-03-22 | Ono Pharmaceutical Co. Ltd. | Peroxisome proliferator-activated receptor controllers |
ATE451346T1 (de) * | 1998-03-10 | 2009-12-15 | Ono Pharmaceutical Co | Carbonsäurederivate und medikamente die diese als aktiven wirkstoff enthalten |
US6586475B1 (en) * | 1998-11-20 | 2003-07-01 | Takeda Chemical Industries, Ltd. | β-amyloid protein production/secretion inhibitors |
WO2000064876A1 (en) * | 1999-04-28 | 2000-11-02 | Aventis Pharma Deutschland Gmbh | Tri-aryl acid derivatives as ppar receptor ligands |
US6677473B1 (en) * | 1999-11-19 | 2004-01-13 | Corvas International Inc | Plasminogen activator inhibitor antagonists |
CN1251671C (zh) * | 2000-05-19 | 2006-04-19 | 武田药品工业株式会社 | β分泌酶抑制剂 |
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2002
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2003
- 2003-06-18 NZ NZ537210A patent/NZ537210A/en unknown
- 2003-06-18 DE DE60317326T patent/DE60317326T2/de not_active Expired - Fee Related
- 2003-06-18 ES ES03738056T patent/ES2295601T3/es not_active Expired - Lifetime
- 2003-06-18 SI SI200331089T patent/SI1513526T1/sl unknown
- 2003-06-18 CA CA002487909A patent/CA2487909A1/en not_active Abandoned
- 2003-06-18 RU RU2004135539/04A patent/RU2323929C2/ru not_active IP Right Cessation
- 2003-06-18 AU AU2003245962A patent/AU2003245962B2/en not_active Ceased
- 2003-06-18 JP JP2004514761A patent/JP2005534672A/ja active Pending
- 2003-06-18 MX MXPA04012857A patent/MXPA04012857A/es active IP Right Grant
- 2003-06-18 WO PCT/EP2003/006415 patent/WO2004000315A1/en active IP Right Grant
- 2003-06-18 PL PL03375148A patent/PL375148A1/xx not_active Application Discontinuation
- 2003-06-18 EP EP03738056A patent/EP1513526B1/en not_active Expired - Lifetime
- 2003-06-18 AT AT03738056T patent/ATE377420T1/de not_active IP Right Cessation
- 2003-06-18 DK DK03738056T patent/DK1513526T3/da active
- 2003-06-18 US US10/518,679 patent/US7338960B2/en not_active Expired - Fee Related
- 2003-06-18 PT PT03738056T patent/PT1513526E/pt unknown
- 2003-06-18 IL IL16547603A patent/IL165476A0/xx unknown
- 2003-06-18 BR BR0311931-9A patent/BR0311931A/pt not_active IP Right Cessation
- 2003-06-18 CN CNA03819290XA patent/CN1674897A/zh active Pending
- 2003-06-18 KR KR1020047020583A patent/KR20050030624A/ko not_active Application Discontinuation
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2004
- 2004-11-30 IS IS7574A patent/IS7574A/is unknown
- 2004-12-03 NO NO20045328A patent/NO20045328L/no not_active Application Discontinuation
- 2004-12-13 ZA ZA200410061A patent/ZA200410061B/en unknown
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2005
- 2005-09-08 HK HK05107902A patent/HK1076712A1/xx not_active IP Right Cessation
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- 2008-01-31 CY CY20081100116T patent/CY1107168T1/el unknown
Also Published As
Publication number | Publication date |
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DK1513526T3 (da) | 2008-03-17 |
GB0214149D0 (en) | 2002-07-31 |
ES2295601T3 (es) | 2008-04-16 |
MXPA04012857A (es) | 2005-02-24 |
EP1513526A1 (en) | 2005-03-16 |
IL165476A0 (en) | 2006-01-15 |
WO2004000315A1 (en) | 2003-12-31 |
KR20050030624A (ko) | 2005-03-30 |
AU2003245962A1 (en) | 2004-01-06 |
RU2323929C2 (ru) | 2008-05-10 |
RU2004135539A (ru) | 2005-08-10 |
CY1107168T1 (el) | 2012-10-24 |
PT1513526E (pt) | 2008-02-12 |
DE60317326D1 (de) | 2007-12-20 |
JP2005534672A (ja) | 2005-11-17 |
DE60317326T2 (de) | 2008-08-28 |
BR0311931A (pt) | 2005-04-05 |
SI1513526T1 (sl) | 2008-04-30 |
CN1674897A (zh) | 2005-09-28 |
US20060089394A1 (en) | 2006-04-27 |
IS7574A (is) | 2004-11-30 |
CA2487909A1 (en) | 2003-12-31 |
US7338960B2 (en) | 2008-03-04 |
ATE377420T1 (de) | 2007-11-15 |
NO20045328L (no) | 2005-03-09 |
NZ537210A (en) | 2006-09-29 |
PL375148A1 (en) | 2005-11-28 |
EP1513526B1 (en) | 2007-11-07 |
AU2003245962B2 (en) | 2008-07-03 |
HK1076712A1 (en) | 2006-01-27 |
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