Collect. Czech. Chem. Commun. 1994, 59, 2705-2713

4-(2',4'-Difluorobiphenyl-4-yl)-2-methyl-4-oxobutanoic Acid and Its Derivatives

Miroslav Kuchař, Marie Poppová, Hana Zůnová, Eva Knězová, Václav Vosátka and Marek Příhoda

Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3, Czech Republic


Friedel Crafts reaction of itaconic anhydride (III) with 2,4-difluorobiphenyl (II) afforded unsaturated acid IV which was hydrogenated to give 4-(2',4'-difluorobiphenyl-4-yl)-2-methyl-4-oxobutanoic acid (I). A series of functional derivatives and salts of the acid I has been prepared. The antiinflammatory effect of these compounds was compared with that of acid I using selected experimental inflammation models. The analgesic activity in the intraperitoneal irritation test was also evaluated. In the case of (R)-(+)-1-phenylethylamide Vf the ratio of the diastereoisomers was determined by HPLC.