Substituted benzo[1,4]dioxanes as antiobesity agents

C - Chemistry – Metallurgy – 07 – D

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C07D 319/20 (2006.01) C07D 413/06 (2006.01)

Patent

CA 2271885

This invention relates to novel substituted 1,4-benzodioxane compounds having antidiabetic, antihyperglycemic, and antiobesity properties represented by formula (II) wherein R1 and R6 are independently hydrogen, C1 to C6 alkyl, trifluoromethyl, cyano, C1 to C6 alkoxy, or halogen; R2 is hydrogen or C1 to C6 trialkylsilyl; R3 is hydrogen or C1 to C6 alkoxycarbonyl; or R2 and R3 are joined to form the oxazolidinone ring (III); R4 and R5 are independently hydrogen or C1 to C6 alkyl; R7 and R8 are independently OR9 or NR10R11; R9 is hydrogen, C1 to C12 alkyl, C1 to C12 cycloalkyl, C1 to C12 silylalkyl, phenyl, naphthyl, phenyl C1 to C6 alkyl, C1 to C6 alkoxy C1 to C6 alkyl, pyridyl, thiophenyl, furanyl, imidazolyl, oxazolyl, -CHR12COOR13, -CHR12C(O)R13, - CHR12CONR10R11, -CHR12OCOOR13, or -CHR12OC(O)R13; R10 and R11 are independently hydrogen, C1 to C12 alkyl, phenyl, naphthyl, phenyl-C1 to C6 alkyl, furanylalkyl, or alkoxycarbonylalkyl; R12 and R13 are independently hydrogen, C1 to C12 alkyl, phenyl, naphthyl, or phenyl-C1 to C6 alkyl; and the pharmaceutically acceptable salts thereof, a salt thereof; an enantiomer thereof, the racemic mixtures thereof, and the diastereomeric mixtures thereof.

Nouveaux composés 1,4-benzodioxannes substitués présentant des propriétés anti-diabétiques, antihyperglycémiques et anti-obésité, représentés par la formule (II) dans laquelle R?1¿ et R?6¿ représentent indépendamment hydrogène, alkyle C¿1? à C¿6?, trifluorométhyle, cyano, alcoxy C¿1? à C¿6?, ou halogène; R?2¿ représente hydrogène ou trialkylsilyle C¿1? à C¿6?; R?3¿ représente hydrogène ou alcoxycarbonyle C¿1? à C¿6?; ou R?2¿ et R?3¿ sont liés pour former le cycle oxazolidinone (III); R?4¿ et R?5¿ représentent indépendamment hydrogène ou alkyle C¿1? à C¿6?; R?7¿ et R?8¿ sont indépendamment OR?9¿ ou NR?10¿R?11¿; R?9¿ représente hydrogène, alkyle C¿1? à C¿12?, cycloalkyle C¿1? à C¿12?, silylalkyle C¿1? à C¿12?, phényle, naphtyle, phényl-alkyle C¿1? à C¿6?, alcoxy C¿1? à C¿6?-alkyle C¿1? à C¿6?, pyridyle, thiophényle, furanyle, imidazolyle, oxazolyle, -CHR?12¿COOR?13¿, -CHR?12¿C(O)R?13¿, -CHR?12¿CONR?10¿R?11¿, -CHR?12¿OCOOR?13¿, ou -CHR?12¿OC(O)R?13¿; R?10¿ et R?11¿ représentent indépendamment hydrogène, alkyle C¿1? à C¿12?, phényle, naphtyle, phényl-alkyle C¿1? à C¿6?, furanylalkyle, ou alcoxycarbonylalkyle; R?12¿ et R?13¿ représentent indépendamment hydrogène, alkyle C¿1? à C¿12?, phényle, naphtyle ou phényl-alkyle C¿1? à C¿6?; et les sels pharmaceutiquement acceptables de ces composés, un sel de ceux-ci; un énantiomère, les conglomérats racémiques et les mélanges diastéréoisomères de ces composés.

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