Oxazole-aryl-carboxylic acids useful in the treatment of...

C - Chemistry – Metallurgy – 07 – D

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C07D 263/32 (2006.01) A61K 31/42 (2006.01) A61K 31/425 (2006.01) C07D 277/24 (2006.01) C07D 413/04 (2006.01) C07D 413/10 (2006.01) C07D 413/12 (2006.01) C07D 417/04 (2006.01) C07D 417/12 (2006.01)

Patent

CA 2331118

This invention provides compounds of Formula (I) having the structure (I) wherein R is (a) or (b); A is OR5, or (c); R1 is alkyl of 1-6 carbon atoms, cycloalkyl of 3-8 carbon atoms, thienyl, furyl, pyridyl, (d) or (e) R2 is hydrogen, alkyl of 1-6 carbons atoms, or aryl of 6 to 10 carbon atoms; R3 and R4 are independently halogen, hydrogen, alkyl of 1-12 carbon atoms, aryl of 6 to 10 carbon atoms; halogen, trifluoromethyl of 1-6 carbon atoms, alkoxyaryl of 7-14 carbon atoms; nitro, amino, carboalkoxy, carbamide, carbamate, urea, alkylsulfoamide, -NR7(CH2)mO2H, arylsulfoamide, cycloalkyl of 3-8 carbon atoms, or heterocycle of 5 to 7 atom rings containing from 1 to 3 heteroatoms selected from oxygen, nitrogen, or sulfur; R5 is hydrogen, alkyl of 1-6 carbon atoms, -CH(R8)R9, -C(CH2)nCO2R10, -C(CH3)2CO2R10, -CH(R8)(CH2)nCO2R10, - CH(R8)C6H4CO2R10, or -CH2-tetrazole; R6 is hydrogen, alkyl of 1-6 carbon atoms, halogen, alkyoxy of 1-6 carbon atoms, trifluoroalkyl of 1-6 carbon atoms or trifluoroalkoxy of 1-6 carbon atoms; or a pharmaceutically acceptable salt thereof, which are useful in treating metabolic disorders related to insulin resistance or hyperglycemia.

L'invention concerne des composés de la formule structurelle (I) dans laquelle R représente un groupe (a) ou un groupe (b), A représente OR?5¿ ou un groupe (c), R?1¿ représente alkyle C¿1-6?, cycloalkyle C¿3-8?, thiényle, furyle, pyridyle, un groupe (d) ou (e), R?2¿ représente hydrogène, alkyle C¿1-6?, ou aryle C¿1-6?, R?3¿ et R?4¿ représentent indépendamment halogène, hydrogène, alkyle C¿1-12?, aryle C¿6-10?, halogène, trifluorométhyle C¿1-6?, alcoxyaryle C¿7-14?, nitro, amino, carboalcoxy, carbamide, carbamate, urée, alkylsulfoamide, -NR?7¿(CH¿2?)¿m?CO¿2?H, arylsulfoamide, cycloalkyle C¿3-8?, ou hétérocycle contenant 5 à 7 chaînons contenant de 1 à 3 hétéroatomes choisis parmi oxygène, azote, ou soufre, R?5¿ représente hydrogène, alkyle C¿1-6?, -CH(R?8¿)R?9¿, -C(CH¿2?)¿n?CO¿2?R?10¿, -C(CH¿3?)¿2?CO¿2?R?10¿, -CH(R?8¿)(CH¿2?)¿n?CO¿2?R?10¿, -CH(R?8¿)C¿6?H¿4?CO¿2?R?10¿, ou CH¿2?-tétrazole, R?6¿ représente hydrogène, alkyle C¿1-6?, halogène, alkyoxy C¿1-6?, trifluoroalkyle C¿1-6?, ou trifluoroalcoxy C¿1-6?. L'invention concerne également un sel de ces composés, acceptable sur le plan pharmacologique. Ces composés et ce sel sont utiles dans le traitement de troubles métaboliques associés à l'insulinorésistance ou à l'hyperglycémie.

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