GB1352380A - Quinone derivatives - Google Patents

Abstract

1352380 2 - Methyl - 3 - (3 - carboxypropyl)- 1,4-benzoquinones TAKEDA YAKUHIN KOGYO KK 19 April 1971 [17 March 1970 18 March 1970 30 July 1970] 24176/71 Heading C2C Novel 2 - methyl - 3 - (3 - carboxypropyl)- 1,4-benzoquinones of the general formula wherein each X is a methyl group or both Xs together form a -CH = CH-CH = CH- group, one of A and A<SP>1</SP> is a hydrogen atom and the other is a C 1-4 alkyl group and R is a hydrogen atom or an alkyl, alkenyl or cycloalkyl group, and when R is a hydrogen atom, pharmaceutically acceptable base addition salts thereof are prepared (a) by reaction of a 2-methyl-1,4- benzoquinone of the general formula with a peroxide of the general formula (b) when R is a hydrogen atom, by reaction of a m-phenol and succinic acid anhydride of the respective general formulae wherein R 1 is a hydrogen atom or a C 1-4 alkyl group and R 2 is a C 1-4 alkyl group corresponding to the C 1-4 alkyl group represented by A or A<SP>1</SP>, followed by reduction of the resulting 3-(2- hydroxy - 6 - methylbenzoyl) - propionic acid of the general formula and oxidation of the resulting 4-(2-hydroxy-6- methyl-phenyl)-butyric acid (the reduction and oxidation steps may also be effected in the reverse order); (c) when R is a hydrogen atom, by hydrolysis of the corresponding compound wherein R is other than a hydrogen atom; and (d) when R is other than a hydrogen atom, by esterification of the corresponding compound wherein R is a hydrogen atom; followed optionally, when R is a hydrogen atom, by salification of the product. Peroxides of the third general formula above are prepared by reaction of compounds of formulae ROOC-CHA<SP>1</SP>-CA=CH 2 and CN-CH 2 -COOR<SP>1</SP>, wherein R<SP>1</SP> is a lower alkyl group, hydrolysis of the resulting nitrile of the general formula halogenation of the resulting glutaric acid of the general formula and treatment of the resulting acid halide of the general formula wherein Y is a halogen atom, with an alkali metal peroxide. Pharmaceutical compositions having Vitamin E, Vitamin K and anti-inflammatory activity comprise, as active ingredient, a 2-methyl-3-(3- carboxypropyl)-1,4-benzoquinone of the first general formula above or, when R is a hydrogen atom, a pharmaceutically acceptable base addition salt thereof, together with a pharmaceutically acceptable carrier and/or diluent.