Naphtho[2,3-b]heteroar-4-yl derivatives

Details Naphtho[2,3-b]heteroar-4-yl derivatives Naphtho[2,3-b]heteroar-4-yl derivatives

C - Chemistry, Metallurgy

07

D

C07D 333/74 (2006.01) A61K 31/34 (2006.01) A61K 31/38 (2006.01) A61K 31/465 (2006.01) A61K 31/505 (2006.01) C07D 307/92 (2006.01) C07D 409/12 (2006.01) C07D 409/14 (2006.01)

Patent

CA 2330555

This invention provides compounds of structural Formula (I), wherein R1 and R2 are each, independently, hydrogen, nitrile, nitro, amino, alkylamino of 1-6 carbon atoms, dialkylamino of 1-6 carbon atoms per alkyl group, cycloalkylamino of 3-8 carbon atoms, alkyl of 1-6 carbon atoms, perfluoroalkyl of 1-6 carbon atoms, halogen, cycloalkyl of 3-8 carbon atoms, thienyl, furyl, phenyl or phenyl mono-, di-, or tri-substituted with halogen, hydroxy, alkyl of 1-6 carbon atoms, perfluoroalkyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, or perfluoroalkoxy of 1-6 carbon atoms; R3 and R4 are each, independently, hydrogen, alkyl of 1-6 carbon atoms, perfluoroalkyl of 1-6 carbon atoms, hydroxyalkyl of 1-6 carbon atoms, aminoalkyl of 1-6 carbon atoms, acyl of 2-7 carbon atoms; R5 is hydrogen, halogen, alkyl of 1-6 carbon atoms, perfluoroalkyl of 1-6 carbon atoms, nitrile, alkoxy of 1-6 carbon atoms, aryloxy, arylalcoxy of 2-12 carbon atoms, arylsulfanyl; W is S, O, or NR9; R9 is hydrogen or alkyl of 1-6 carbon atoms; X is O, -NR6-, or -(CH2)pNR6- ; R6 is hydrogen, or alkyl of 1-6 carbon atoms; p is 1 to 4; Y is methylene, carbonyl, -SO2-, or -SO-; Z is phenyl, heteroaryl, or naphthyl; R7 and R8 are each, independently, hydrogen, carboxyl, acyl of 2-7 carbon atoms, hydroxyl, hydroxyalkyl of 1-6 carbon atoms, hydroxyalkanoyl of 1-6 carbon atoms, alkoxy of 1-6 carbon atoms, perfluoroalkoxy of 1-6 carbon atoms, alkoxycarbonyl of 2- 7 carbon atoms, perfluoroalkoxycarbonyl of 2-7 carbon atoms, alkyl of 1-6 carbon atoms, perfluoroalkyl of 1-6 carbon atoms, aryl, aryloxy, aryloxycarbonyl, heteroaryloxycarbonyl, arylalkoxy of 6-12 carbon atoms, heteroaryl, alkanoyloxy of 1-6 carbon atoms, perfluoroalkanoyloxy of 1-6 carbon atoms, heteroaroyloxy, aroyloxy, tetrazolyl, mercapto, nitrile, amino, carbamoy, aminoalkyl of 1-6 carbon atoms, -NHSO2CF3, carboxyaldehyde, halogen, nitro, acylamino, or pyrimidyl optionally substituted with mercapto, 3-hydroxy- cyclobut-3-ene-4-yl-1,2-dione, or tetronic acid; 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?1¿ et R?2¿ représentent chacun indépendamment, hydrogène, nitrile, nitro, amino, alkylamino C¿1-6?, dialkylamino comprenant 1 à 6 atomes de carbone par groupe alkyle, cycloalkyl-amino C¿3-8?, alkyle C¿1-6?, perfluoroalkyle C¿1-6?, halogène, cycloalkyle C¿3-8?, thiényle, furyle, phényle ou phényle mono-, di- ou tri-substitué par halogène, hydroxy, alkyle C¿1-6?, perfluoroalkyle C¿1-6?, alcoxy C¿1-6?, ou perfluoroalcoxy C¿1-6?; R?3¿ et R?4¿ représentent chacun indépendamment hydrogène, alkyle C¿1-6?, perfluoroalkyle C¿1-6?, hydroxyalkyle C¿1-6?, aminoalkyle C¿1-6?, acyle C¿2-7?; R?5¿ représente hydrogène, halogène, alkyle C¿1-6?, perfluoroalkyle C¿1-6?, nitrile, alcoxy C¿1-6?, aryloxy, arylalcoxy C¿2-12?, arylsulfanyle; W représente S, O ou NR?9¿; R?9¿ représente hydrogène ou alkyle C¿1-6?, X représente O, -NR?6¿-, ou (CH¿2?)¿p?NR?6¿-; R?6¿ représente hydrogène, ou alkyle C¿1-6?; p vaut 1 à 4; Y représente méthylène, carbonyle, -SO¿2?-, ou SO-; Z représente phényle, hétéroaryle ou naphtyle; R?7¿ et R?8¿ représentent chacun indépendamment hydrogène, carboxyle, acyle C¿2-7?, hydroxyle, hydroxyalkyle C¿1-6?, hydroxyalcanoyle C¿1-6?, alcoxy C¿1-6?, perfluoroalcoxy C¿1-6?, alcoxycarbonyle C¿2-7?, perfluoroalcoxycarbonyle C¿2-7?, alkyle C¿1-6?, perfluoroalkyle C¿1-6?, aryle, aryloxy, aryloxycarbonyle, hétéroaryloxycarbonyle, arylalcoxy C¿6-12?, héréroaryle, alcanoyloxy C¿1-6?, perfluoroalcanoyloxy C¿1-6?, hétéroaroyloxy, aroyloxy, tétrazolyle, mercapto, nitrile, amino, carbamoyle, aminoalkyle C¿1-6?, -NHSO¿2?CF¿3?, carboxyaldéhyde, halogène, nitro, acylamino, ou pyrimidyle éventuellement substitué par mercapto, 3-hydroxy-cyclobut-3-ène-4-yl-1,2-dione, ou acide tétronique. L'invention concerne également des sels de ces composés, acceptables sur le plan pharmacologique. Ces sels et composés sont utiles dans le traitement de troubles métaboliques associés à l'insulinorésistance ou à l'hyperglycémie.

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