N'-alkyl-spiro-isoquinoline-pyrrolidine tetrones and analogs...

C - Chemistry – Metallurgy – 07 – D

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C07D 471/10 (2006.01) A61K 31/47 (2006.01) C07D 217/26 (2006.01)

Patent

CA 2042112

N'-alkyl-spiro-isoquinoline-pyrrolidine tetrones of structural formula (I) (SEE FORMULA I) wherein R1 and R2 are independently hydrogen, alkyl containing 1 to 6 carbon atoms, halogen, lower alkoxy containing 1 to 6 carbon atoms, trifluoromethyl, nitro, aryl or aryl(lower alkyl)oxy wherein aryl contains 6 to 10 carbon atoms and lower alkyl contains 1 to 6 carbon atoms; R3 is hydrogen, lower alkyl containing 1 to 6 carbon atoms, aryl, aryl(lower alkyl) or halogen substituted aryl(lower alkyl) wherein aryl contains 6 to 10 carbon atoms and lower alkyl contains 1 to 6 carbon atoms, or benzothiazole of structural formula (SEE FORMULA II) wherein R5 is hydrogen, alkyl containing 1 to 6 carbon atoms, lower alkoxy containing 1 to 6 carbon atoms, trifluoromethyl, nitro, aryl or aryl(lower alkyl)oxy wherein aryl contains 6 to 10 carbon atoms and lower alkyl contains 1 to 5 carbon atoms; and R4 is alkyl containing 1 to 12 carbon atoms, aryl, aryl(lower alkyl) wherein aryl contains 6 to 10 carbon atoms and lower alkyl contains 1 to 6 carbon atoms, acyl, carboalkoxy, or - (CH2) n CO2H, - (CH2) n OH, wherein n is 1 to 6; and their pharmaceutically acceptable salts thereof. The compounds have pharmaceutical properties which render them beneficial for the prevention or treatment of diabetes mellitus associated complications. 2

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