Benzopyran derivatives

Details Benzopyran derivatives Benzopyran derivatives

C - Chemistry, Metallurgy

07

D

167/244, 260/356

C07D 311/58 (2006.01) A61K 31/35 (2006.01) C07D 311/72 (2006.01) C07D 311/92 (2006.01) C07D 405/02 (2006.01)

Patent

CA 2011899

A B S T R A C T Benzopyran Derivatives benzopyran derivatives of the formula: Image (IA) wherein R1a is hydrogen, C1-4 alkyl or C1-4 alkoxy; or two R1a taken together with 7th- and 8th-carbon to which they are attached form C6 carbocyclic ring; R2a is hydrogen, C1-4 alkyl or C1-4 alkoxy; R3a is hydrogen, C2-4 acyl or benzoyl; na is 1-3; Ya is C1-7 alkylene, C2-7 alkenylene or C2-7 alkynylene; Ma is i) bond or ii) a group of the formula:-Da-Ba-; Da is i) -O-or ii) -S-; Ba is i) C1-4 alkylene or ii) a group of the formula: Image , Za is i) bond, ii) -OCO-, iii) -CONR9a-, iv) -COO-, v ) -NR9aCO-, vi) -O-or vii) -NH-CO-NH-; Wa is a group of the formula: -Wla-Aa-W2a-; Aa is i ) bond or ii) a group of the formula: Image , Ea is i) bond, ii) -O-or iii)-S-; Image is C4-10 carbocyclic or heterocyclic ring; or C4-10 carbocyclic or heterocyclic ring substituted by one to three C1-4 alkyl, C1-4 alkoxy, halogen, a group of the formula: -COOR7a, trihalomethyl or acetamido; W1a and W2a each, independently, is i) bond ii) C1-4 alkylene, iii) C2-4 alkenylene or iv) C2-4 alkynylene; R4a is hydrogen or C1-4 alkyl; R5a is hydrogen, C1-4 alkyl or amino; R6a is hydrogen, C1-4 alkyl, C1-4 alkoxy, halogen, a group of the formula: -COOR8a, trihalomethyl or acetoamido; R7a is hydrogen or C1-4 alkyl; R8a is hydrogen or C1-4 alkyl; R9a is hydrogen, C1-4 alkyl or benzyl; with the proviso that: i) Da is bonded to Ya and Ba is bonded to Za; ii) Ea is bonded to W1a and Image is bonded to W2a; iii) a double or triple bond in alkenylene or alkynylene is not directly bonded to oxygen; iv) when Aa represents Image or Image , W1a does not represent a bond; v) the following compound is excluded: wherein R1a attached to the 5th-carbon is hydrogen or C1- 4 alkyl; R1a attached to the 7th-carbon is hydrogen, C1-4 alkyl or C1-4 alkoxy; R1a attached to the 8th-carbon is hydrogen or C1-4 alkyl; R2a is methyl; R3a is hydrogen; R4a is hydrogen; R5a is hydrogen; -Ya-Ma-Za-Wa- is C1-3 straight chain alkylene; and the pharmaceutically acceptable acid addition salts thereof possess the inhibitory activity on Maillard reaction and an antioxidizing effect, and therefore, are useful for the prevention and treatrnent of several diabetic complications, diseases induced by aging and several diseases caused by formation of peroxidized fat.

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