FR2917086B1 - Nouveaux derives d'acide 3-phenyl acrylique activateurs des recepteurs de type ppar, leur methode de preparation et leur utilisation dans des compositions cosmetiques ou pharmaceutiques. - Google Patents

Nouveaux derives d'acide 3-phenyl acrylique activateurs des recepteurs de type ppar, leur methode de preparation et leur utilisation dans des compositions cosmetiques ou pharmaceutiques.

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Publication number
FR2917086B1
FR2917086B1 FR0755478A FR0755478A FR2917086B1 FR 2917086 B1 FR2917086 B1 FR 2917086B1 FR 0755478 A FR0755478 A FR 0755478A FR 0755478 A FR0755478 A FR 0755478A FR 2917086 B1 FR2917086 B1 FR 2917086B1
Authority
FR
France
Prior art keywords
cosmetic
novel
preparation
pharmaceutical compositions
acid derivatives
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
FR0755478A
Other languages
English (en)
Other versions
FR2917086A1 (fr
Inventor
Jean Guy Boiteau
Laurence Clary
Jean Claude Pascal
Sandrine Chambon
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Galderma Research and Development SNC
Original Assignee
Galderma Research and Development SNC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to FR0755478A priority Critical patent/FR2917086B1/fr
Application filed by Galderma Research and Development SNC filed Critical Galderma Research and Development SNC
Priority to CA002688241A priority patent/CA2688241A1/fr
Priority to PCT/FR2008/050997 priority patent/WO2008152334A2/fr
Priority to AU2008263669A priority patent/AU2008263669A1/en
Priority to KR1020097025434A priority patent/KR20100028550A/ko
Priority to CN200880018941A priority patent/CN101679228A/zh
Priority to MX2009012713A priority patent/MX2009012713A/es
Priority to JP2010510859A priority patent/JP2010529099A/ja
Priority to EP08805937A priority patent/EP2164827A2/fr
Priority to RU2009149610/04A priority patent/RU2009149610A/ru
Priority to ARP080102389A priority patent/AR068975A1/es
Publication of FR2917086A1 publication Critical patent/FR2917086A1/fr
Application granted granted Critical
Publication of FR2917086B1 publication Critical patent/FR2917086B1/fr
Priority to US12/632,257 priority patent/US8404836B2/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63Esters of sulfonic acids
    • C07C309/64Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/185Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19Carboxylic acids, e.g. valproic acid
    • A61K31/192Carboxylic acids, e.g. valproic acid having aromatic groups, e.g. sulindac, 2-aryl-propionic acids, ethacrynic acid 
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365Hydroxycarboxylic acids; Ketocarboxylic acids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42Amides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/46Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
    • A61K8/466Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfonic acid derivatives; Salts
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P3/06Antihyperlipidemics
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    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • A61P37/08Antiallergic agents
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    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61P9/10Drugs 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
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/10Washing or bathing preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/02Preparations for cleaning the hair
    • CCHEMISTRY; METALLURGY
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    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/76Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings and etherified hydroxy groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00Carboxylic acid amides
    • C07C233/01Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/24Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
    • C07C233/25Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/56Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63Esters of sulfonic acids
    • C07C309/64Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C07C309/66Methanesulfonates
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63Esters of sulfonic acids
    • C07C309/64Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/67Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00Amides 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
    • C07C311/01Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/08Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00Amides 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
    • C07C311/01Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/12Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
    • C07C311/13Sulfonamides 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C59/00Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C59/40Unsaturated compounds
    • C07C59/58Unsaturated compounds containing ether groups, groups, groups, or groups
    • C07C59/64Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
    • C07C59/66Unsaturated 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
    • C07C59/68Unsaturated 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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    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/21Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
    • C07C65/28Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups having unsaturation outside the aromatic rings
FR0755478A 2007-06-05 2007-06-05 Nouveaux derives d'acide 3-phenyl acrylique activateurs des recepteurs de type ppar, leur methode de preparation et leur utilisation dans des compositions cosmetiques ou pharmaceutiques. Expired - Fee Related FR2917086B1 (fr)

Priority Applications (12)

Application Number Priority Date Filing Date Title
FR0755478A FR2917086B1 (fr) 2007-06-05 2007-06-05 Nouveaux derives d'acide 3-phenyl acrylique activateurs des recepteurs de type ppar, leur methode de preparation et leur utilisation dans des compositions cosmetiques ou pharmaceutiques.
EP08805937A EP2164827A2 (fr) 2007-06-05 2008-06-04 Nouveaux dérivés d'acide 3-phenyl acrylique activateurs des récepteurs de type ppar, leur méthode de préparation et leur utilisation dans des compositions cosmétiques ou pharmaceutiques
AU2008263669A AU2008263669A1 (en) 2007-06-05 2008-06-04 Novel derivatives of 3-phenyl acrylic acid activating PPAR-type receptors, method for preparing same and use thereof in cosmetic or pharmaceutical compositions
KR1020097025434A KR20100028550A (ko) 2007-06-05 2008-06-04 Ppar 유형의 수용체를 활성화시키는 신규 3-페닐 아크릴산의 유도체, 이의 제조 방법 및 화장 또는 약학 조성물에서의 이의 용도
CN200880018941A CN101679228A (zh) 2007-06-05 2008-06-04 为ppar型受体的活化剂的新型3-苯基丙烯酸衍生物、其制备方法和其在化妆品或者药物组合物中的用途
MX2009012713A MX2009012713A (es) 2007-06-05 2008-06-04 Nuevos derivados de acido 3-fenil acrilico de receptores de tipo ppar, su metodo de preparacion y su uso en composiciones cosmeticas o farmaceuticas.
CA002688241A CA2688241A1 (fr) 2007-06-05 2008-06-04 Nouveaux derives d'acide 3-phenyl acrylique activateurs des recepteurs de type ppar, leur methode de preparation et leur utilisation dans des compositions cosmetiques ou pharmaceutiques
PCT/FR2008/050997 WO2008152334A2 (fr) 2007-06-05 2008-06-04 Nouveaux dérivés d'acide 3-phenyl acrylique activateurs des récepteurs de type ppar, leur méthode de préparation et leur utilisation dans des compositions cosmétiques ou pharmaceutiques
RU2009149610/04A RU2009149610A (ru) 2007-06-05 2008-06-04 Новые производные 3-фенилакриловой кислоты в качестве активаторов рецепторов типа ppar, способ их получения и их применение в косметических или фармацевтических композициях
JP2010510859A JP2010529099A (ja) 2007-06-05 2008-06-04 Pparタイプ受容体の活性化剤である3‐フェニルアクリル酸の新規誘導体、その調製方法および化粧品組成物または医薬組成物におけるその使用
ARP080102389A AR068975A1 (es) 2007-06-05 2008-06-05 Derivados del acido 3-fenil acrilico activadores de los receptores del tipo ppar, y su utilizacion en composiciones cosmeticas o farmaceuticas
US12/632,257 US8404836B2 (en) 2007-06-05 2009-12-07 3-phenyl acrylic acid compound activators of type PPAR receptors and pharmaceutical/cosmetic compositions comprised thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR0755478A FR2917086B1 (fr) 2007-06-05 2007-06-05 Nouveaux derives d'acide 3-phenyl acrylique activateurs des recepteurs de type ppar, leur methode de preparation et leur utilisation dans des compositions cosmetiques ou pharmaceutiques.

Publications (2)

Publication Number Publication Date
FR2917086A1 FR2917086A1 (fr) 2008-12-12
FR2917086B1 true FR2917086B1 (fr) 2009-07-17

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FR0755478A Expired - Fee Related FR2917086B1 (fr) 2007-06-05 2007-06-05 Nouveaux derives d'acide 3-phenyl acrylique activateurs des recepteurs de type ppar, leur methode de preparation et leur utilisation dans des compositions cosmetiques ou pharmaceutiques.

Country Status (12)

Country Link
US (1) US8404836B2 (fr)
EP (1) EP2164827A2 (fr)
JP (1) JP2010529099A (fr)
KR (1) KR20100028550A (fr)
CN (1) CN101679228A (fr)
AR (1) AR068975A1 (fr)
AU (1) AU2008263669A1 (fr)
CA (1) CA2688241A1 (fr)
FR (1) FR2917086B1 (fr)
MX (1) MX2009012713A (fr)
RU (1) RU2009149610A (fr)
WO (1) WO2008152334A2 (fr)

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FR2917086B1 (fr) 2007-06-05 2009-07-17 Galderma Res & Dev Nouveaux derives d'acide 3-phenyl acrylique activateurs des recepteurs de type ppar, leur methode de preparation et leur utilisation dans des compositions cosmetiques ou pharmaceutiques.
WO2012177956A1 (fr) * 2011-06-23 2012-12-27 Metabolic Solutions Development Comapny, Llc Composés réduisant l'activité ou la liaison-de ppar et combinaisons pour le traitement du diabète et d'autres maladies métaboliques
WO2013041621A1 (fr) 2011-09-20 2013-03-28 Basf Se Modulateurs à faible masse moléculaire du récepteur sensible au froid et au menthol trpm8, et leur utilisation
FR2984730A1 (fr) * 2011-12-22 2013-06-28 Diverchim Nouvelles compositions cosmetiques anti-age et depigmentantes
KR101609323B1 (ko) * 2015-03-06 2016-04-05 충북대학교 산학협력단 2-메톡시-4-(3-(4-메톡시페닐)프로필-1-엔-1-일)페놀 및 이의 제조방법
CN114644560B (zh) * 2022-04-20 2024-02-02 朗捷睿(苏州)生物科技有限公司 一种苯基丙烯酸类化合物及其制备方法和应用

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SE9801990D0 (sv) * 1998-06-04 1998-06-04 Astra Ab New 3-aryl propionic acid derivatives and analogs
MA26634A1 (fr) * 1998-06-04 2004-12-20 Astra Ab Nouveaux derives de l'acide 3-aryl propionique et analogues
SE9904421D0 (sv) * 1999-12-03 1999-12-03 Astra Ab New compounds
FR2812876B1 (fr) * 2000-08-08 2002-09-27 Galderma Res & Dev Nouveaux composes bi-aromatiques activateurs des recepteurs de type ppar-gamma et leur utilisation dans des compositions cosmetiques ou pharmaceutiques
RU2315746C2 (ru) * 2001-08-09 2008-01-27 Оно Фармасьютикал Ко., Лтд. Производные карбоновых кислот и фармацевтическое средство, содержащее их в качестве активного ингредиента
FR2833949B1 (fr) * 2001-12-21 2005-08-05 Galderma Res & Dev NOUVEAUX LIGANDS ACTIVATEURS DES RECEPTEURS PPARy, LEUR PROCEDE DE PREPARATION ET LEUR UTILISATION EN MEDECINE HUMAINE AINSI QU'EN COSMETIQUE
FR2874379B1 (fr) * 2004-08-17 2006-10-27 Galderma Res & Dev Nouveaux composes bi-aromatiques activateurs des recepteurs de type ppar et leur utilisation dans des compositions cosmetiques ou pharmaceutiques
AU2006287521A1 (en) * 2005-09-07 2007-03-15 Plexxikon, Inc. PPARactive compounds
FR2892412B1 (fr) * 2005-10-26 2008-05-16 Galderma Res & Dev Composes biaromatiques modulateurs des ppars
JP5243696B2 (ja) * 2006-03-17 2013-07-24 田辺三菱製薬株式会社 ベンゼン誘導体
FR2917086B1 (fr) 2007-06-05 2009-07-17 Galderma Res & Dev Nouveaux derives d'acide 3-phenyl acrylique activateurs des recepteurs de type ppar, leur methode de preparation et leur utilisation dans des compositions cosmetiques ou pharmaceutiques.

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JP2010529099A (ja) 2010-08-26
FR2917086A1 (fr) 2008-12-12
AU2008263669A1 (en) 2008-12-18
US8404836B2 (en) 2013-03-26
WO2008152334A3 (fr) 2009-03-05
WO2008152334A2 (fr) 2008-12-18
AR068975A1 (es) 2009-12-23
KR20100028550A (ko) 2010-03-12
CA2688241A1 (fr) 2008-12-18
MX2009012713A (es) 2009-12-08
RU2009149610A (ru) 2011-07-20
EP2164827A2 (fr) 2010-03-24
US20100144884A1 (en) 2010-06-10
CN101679228A (zh) 2010-03-24

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