IMIDAZO (5,1-D) TETRAZIN-1,2,3,5 ONE-DERIVATIVES AND RELATED PRODUCTS, PROCESSES FOR THEIR PREPARATION AND COMPOSITION CONTAINING SAID DERIVATIVES

摘要

NEW TETRAZINE DERIVATIVES Tetrazine derivatives of the general formula: ¢wherein R1 represents a (C3-C8)cycloalkyl group, or a (C1-C4)alkyl, (C2-C6)alkenyl or (C2-C6)alkynyl group, each such alkyl, alkenyl or alkynyl group being unsubstituted or substituted by from 1 to 3 substituents selected from halogen atoms, (C1-C4)alkoxy, -alkylthio, -alkylsulphinyl and -alkylsulphonyl groups, and optionally substituted phenyl groups, A1 represents a nitrogen atom or a group -CR3= wherein R3 represents hydrogen or a substituent R4 wherein R4 represents a halogen atom, or a (C1-C6)-alkyl or -alkenyl group, which may carry up to 3 substituents selected from halogen atoms, optionally substituted phenyl groups, and (C1-C3)-alkoxy, -alkylthio and -alkylsulphonyl groups or R4 represents a (C3-C8)cycloalkyl group, a cyano, hydroxy, nitro or optionally substituted phenoxy group, or a group , -COR5 (wherein R5 represents a (C1-C4)-alkyl or -alkoxy group, a hydroxy group, or an optionally substituted phenyl group) or a (C1-C6)alkanoylamino group, or R4 represents a group -S(O)nR6, -SO2NR7R8 or -CZ2NR7R8 (wherein n represents 0; 1 or 2, R6 represents a (C1-C4)alkyl or (C2-C4)alkenyl group, which may carry an optionally substituted phenyl substituent, a (C3-C8)cyclo-alkyl group or an optionally substituted phenyl group, R7 and R8 each represents hydrogen or a (C1-C4)alkyl or (C2-C4)alkenyl group, which may carry an optionally substituted phenyl substituent, or a (C3-C8)cycloalkyl group or an optionally substituted phenyl group, or the group -NR7R8 represents a heterocyclic group, and Z2 represents an oxygen or sulphur atom), A2 represents a nitrogen atom or, when A1 represents a nitrogen atom, A2 represents a nitrogen atom or a group -CR3= wherein R3 is as hereinbefore defined, Z1 represents an oxygen or sulphur atom, and R2 represents a group of the formula -S(O)nR6, -SO2NR7R8, -CSNR7R8, -CONR7R9 or -CZ2NHNO2, wherein n, R6, R7, R8 and Z2 are as hereinbefore defined, and the group -NR7R9 represents a heterocyclic group, or R7 is as hereinbefore defined and R9 represents a (C1-C4)alkyl or (C2-C4)alkenyl group which carries an optionally substituted phenyl substituent, or an optionally substituted phenyl group or, when A1 represents a nitrogen atom or a group -CR4= wherein R4 is as hereinbefore defined and Z1 and A2 are as hereinbefore defined or, when Al represents a group -CH= and Z1 represents a sulphur atom and A2 is as hereinbefore defined, R2 represents a group of the formula -S(O)nR6, -SO2NR7R8, -CZ2NR7R8 or CZ2NHNO2 wherein n, R6, R7, R8 and Z2 are as hereinbefore defined! are new therapeutically useful compounds possessing antineoplastic activity. Processes for the preparation of the tetrazine derivatives are inter alia described.