GB1304664A - - Google Patents

Abstract

1304664 Aryl bicyclo[2,2.2]-octanecarboxylates DAIICHI SEIYAKU CO Ltd 19 April 1971 [25 March 1970] 25324/71 Heading C2C Novel compounds of Formula I wherein R is H, carboxy, #-carboxyalkyl, #-carboxyalkenyl, #-carboxyalkylcarbonyl, #-carboxyalkoxy or #-carboxyaminoalkyl in which the alkyl group has 1 to 6 carbon atoms, and R<SP>1</SP> is H or optionally carboxy when R is 4<SP>1</SP>-carboxy and mineral acid salts thereof, are prepared by removal of protecting groups from an intermediate of Formula V wherein -COOZ is a protective group, R<SP>11</SP> is the same as R or is a group R in which the terminal carboxy group is protected and R<SP>111</SP> is the same as R<SP>1</SP> or is a protected carboxy group, which is prepared by reaction of a phenol of Formula IV with a compound of formula wherein X is halogen. Intermediates of Formula IV above are prepared from the free acid and benzyl chloride. N-Benzyloxycarbonylaminomethylbicyclo- [2,2,2] - octane - 1 - carboxylic acid chloride is prepared by action of thionyl chloride on the carboxylic acid which is obtained by action of benzyloxycarbonyl chloride on the sodium salt of the amino-acid and acidification. Pharmaceutical compositions having antithrombin activity comprise an above novel compound and a pharmaceutical carrier.