Substituted 1, 3-benzodioxoles

C - Chemistry – Metallurgy – 07 – D

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Details

C07D 317/46 (2006.01) A61K 31/36 (2006.01) A61K 31/42 (2006.01) A61K 31/695 (2006.01) C07D 407/14 (2006.01) C07D 409/14 (2006.01) C07D 413/06 (2006.01) C07F 7/10 (2006.01) C07F 7/18 (2006.01)

Patent

CA 2254120

The present invention provides new compounds having anti-diabetic and/or antihyperglycemia and/or anti-obesity activity, as well as pharmaceutical compositions and methods of treatment utilizing the compounds and processes for making the compounds, the compounds having 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 a ring (a): wherein R' is hydrogen, C1 to C6 alkyl or aryl; 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, aryl, arylakyl, alkoxyalkyl, heteroaryl, -CHR12COOR13, - CHR12C(O)R13, -CHR12CONR10R11, -CHR12OCOOR13, or -CHR12OC(O)R13, with the provision that R9 is not hydrogen in both R7 and R8; R10 and R11 are independently hydrogen, C1 to C12 alkyl, aralkyl, aryl, furanylalkyl, or alkoxycarbonylalkyl; R12 and R13 are independently hydrogen, C1 to C12 alkyl, aryl, or aralkyl; and their pharmaceutically acceptable salts thereof, the enantiomers thereof, the racemic mixtures thereof, and the diastereomeric mixtures thereof.

Nouveaux composés présentant une activité antidiurétique et/ou antihyperglycémique et/ou anti-obésité, et compositions pharmaceutiques et méthodes de traitement utilisant les composés et procédés de fabrication de ces composés, qui sont de formule (II), dans laquelle R¿1? et R¿6? sont indépendamment hydrogène, alkyle en C¿1?-C¿6?, trifluorométhyle, cyano, alcoxy en C¿1?-C¿6?, ou halogène; R¿2? est hydrogène ou trialkylsilyle en C¿1?-C¿6?; R¿3? est hydrogène ou alcoxycarbonyle en C¿1?-C¿6?; ou R¿2? et R¿3? ensemble forment un noyau (a) dans lequel R' est hydrogène, alkyle en C¿1?-C¿6? ou aryle; R¿4? et R¿5? sont indépendamment hydrogène ou alkyle en C¿1?-C¿6?; R¿7? et R¿8? sont indépendamment OR¿9? ou NR¿10?R¿11?; R¿9? est hydrogène, alkyle en C¿1?-C¿12?, cycloalkyle en C¿1?-C¿12?, silylalkyle en C¿1?-C¿12?, aryle, arylakyle, alcoxyalkyle, hétéroaryle, -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?, à condition que R¿9? ne soit pas hydrogène à la fois dans R¿7? et R¿8?; R¿10? et R¿11? sont indépendamment hydrogène, alkyle en C¿1?-C¿12?, aralkyle, aryle, furanylalkyle, ou alcoxycarbonylalkyle; R¿12? et R¿13? sont indépendamment hydrogène, alkyle en C¿1?-C¿12?, aryle, ou aralkyle; leurs sels pharmaceutiquement acceptables, leurs énantiomères, les mélanges racémiques correspondants et les mélanges diastéréomériques correspondants.

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