ES357877A1 - 3,5-diamino-6-halo-pyrazinamide derivatives - Google Patents

Abstract

3,5 - Diamino - 6 - halo - pyrazinamide derivatives of the general formula wherein R1 is a hydrogen atom or a C 1-5 alkyl, C 3-5 alkenyl, C 3-5 alkynyl, C 3-6 cycloalkyl, C 3-6 cycloalkyl-C 1-3 alkyl, di(C 1-3 alkyl)amino-methyl-C 1-3 alkyl, (hydroxy-C 1-5 alkyl)methyl, (polyhydroxy - C 1-5 alkyl) - methyl, #, #, # - trifluoro-C 1-3 alkyl, phenyl-C 1-3 alkyl, halophenyl- C 1-3 alkyl, heterocyclic-C 1-3 alkyl in which the heterocyclic moiety is a 5- or 6-membered ring containing oxygen or nitrogen or both, phenyl, halophenyl, C 1-3 alkyl-phenyl, C 1-3 alkoxy, phenyl-C 1-3 alkoxy or amino group and R2 is a hydrogen atom or a C 1-5 alkyl group or R1 and R2 are alkylene groups linked together directly or through a hetero atom to form a heterocyclic structure with the nitrogen atom to which they are attached Y is a chlorine, bromine or iodine atom and R6 is a C 1-5 alkyl, C 1-3 alkoxymethyl-C 1-5 alkyl, cyano.C 1-5 alkyl, (C 1-3 alkoxy)carbonyl-C 1-5 alkyl, phenyl-C 1-5 alkyl, di-(C 1-3 alkyl)aminomethyl-C 1-5 alkyl, 2 - (2 - imidazolinyl) - amino - methyl - C 1-5 alkyl, 1-pyrrolidinyl-C 1-5 alkyl, piperidino-C 1-5 alkyl, hexahydro-1-azepinyl-C 1-5 alkyl, morpholino-C 1-5 alkyl, 4-(C 1-3 alkyl)-1 -piperazinyl-C 1-5 alkyl, pyridyl-C 1-5 alkyl, faryl-C 1-5 alkyl, tetrahydropyranyl-C 1-5 alkyl, C 3-5 alkenyl, C 3-5 alkynyl, phenyl, halophenyl, C 1-3 alkyl-phenyl, C 1-3 alkoxy-phenyl, cyano, amino, di(C 1-3 alkyl)- amino, N-C 1-3 alkyl-N-(phenyl - C 1-3 alkyl)- amino, di[phenyl- (C 1-3 alkyl)]amino, pyridylamino, pyrimidinylamino, quinolinylamino, pyrrolidino, piperidino, hexahydro-1-azepinyl, morpholino or 4-(3,5-diamino- 1,2,4-triazolyl) group a group of the formula in which R7 is a C 1-5 alkyl, phenyl, halophenyl, C 1-3 alkyl-phenyl or C 1-3 alkoxy-phenyl group a group of the formula in which R8 is a hydrogen atom or a phenyl or C 1-5 alkyl group, R9 is a hydrogen atom or a C 1-5 alkyl, hydroxy-C 1-5 alkyl, phenyl-C 1-5 alkyl, halophenyl-C 1-5 alkyl, (C 1-3 alkyl)-phenyl- C 1-5 alkyl, (C 1-3 alkoxy)-phenyl-C 1-5 alkyl, naphthyl-C 1-5 alkyl, balonaphthyl-C 1-5 alkyl, (C 1-3 alkyl) - naphthyl - C 1-5 alkyl, (C 1-3 alkoxy) - naphthyl - C 1-5 alkyl, pyridyl - C 1-5 alkyl, morpholino-C 1-5 alkyl, furyl-C 1-5 alkyl, 1 - pyrrolidyl - C 1-5 alkyl, C 1-3 alkoxy-C 1-5 alkyl, C 3-5 alkenyl, C 2-5 alkylideneamino, (phenyl - C 2-5 alkylidene)amino, hydroxy, phenyl, C 1-3 alkyl-phenyl, C 1-3 alkoxy-phenyl, halophenyl, C 1-3 alkoxy or phenyl-C 1-3 alkoxy group and R10 is a hydrogenation or a C 1-5 alkyl group, or R9 and R10 are alkylene groups linked together to form, with the nitrogen atom to which they are attached, a heterocyclic ring containing from 5 to 8 atoms, optionally including a further heteroatom, or R8 and R9 are alkylene groups linked together to form, with the nitrogen atom to which they are attached, a heterocyclic ring containing from 5 to 7 ring atoms a group of the formula in which R11 is an hydrogen atom or a C 1-5 alkyl group, R12 is a hydrogen atom or a C 1-5 alkyl, hydroxy-C 1-5 alkyl, phenyl-C 1-5 alkyl, halophenyl-C 1-5 alkyl, (C 1-3 alkyl)-phenyl-C 1-5 alkyl, phenyl, halophenyl, C 1-3 alkyl-phenyl, C 1-3 alkoxy-phenyl or amino group and R13 is a hydrogen atom, or R11 and R13 are alkylene groups linked together to form a diazacyclic ring containing from 5 to 7 ring atoms with the nitrogen atoms to which they are attached are prepared by reaction of a 3,5-diamino-6-halopyrazinoyloxyacrylamide of the general formula wherein R3 is a methyl, ethyl, n-propyl, isopropyl, phenyl, (C 1-3 alkyl)-phenyl or sulphophenyl group, in which case an internal salt is formed with an amino group and R4 is a hydrogen atom or R3 and R4 are linked to form an o-phenylene group with the carbon atom to which R3 and R4 are attached R5 is a C 1-5 alkyl group with an amine of the general formula R6NH 2 . Certain of the 3,5-diamino-6- halo-pyrazinamide derivatives of the first general formula above are novel.