PHARMACOLOGICALLY ACTIVE COMPOUNDS, METHODS FOR THE PREPARATION THEREOF AND COMPOSITIONS CONTAINING THE SAME

摘要

Disclosed and claimed are pharmacologically active catechol derivatives of formula (I): (I) <IMG> or a salt thereof, in which R1 and R2 independently represent hydrogen, optionally substituted acyl or aroyl, lower alkylcarbamoyl, X represents an electronegative substituent such as halogen, nitro, cyano, aldehyde and trifluoromethyl; and R3 represents alkyl substituted by lower alkoxy lower alkoxy, carboxy lower alkyl, thio or pyrrole group, or a group selected from: <IMG> <IMG> (A) or wherein R4 represents cyano or acyl and R5 represents cyano, alkoxycarbonyl, carboxyalkenyl, nitro, acyl, hydroxyalkyl, carboxyalkyl, one of the following optionally substituted groups: carbamoyl, aroyl or heteroaroyl, or R4 and R5 form together a five to seven membered, optionally substituted cycloalkanone ring; (B) (CH2)m-COR wherein m is 2-7 and R represents hydroxy, alkyl, carboxyalkyl, optionally substituted alkene, alkoxy or optionally substituted amino; (C) <IMG> wherein R8 represents hydrogen and R9 represents an optionally substituted adamantyl group. These new derivatives of formula (I) are active as catechol-0-methyl-transferase (COMT) inhibitors and can be used as such or as pharmaceutical compositions in the treatment of depression, heart failure and/or hypertension.