GB1108578A - 5-aminomethyl-4,5,6,7-tetrahydro-4-oxoindoles - Google Patents

Abstract

Novel compounds of the general formula <FORM:1108578/C2/1> wherein R1 is hydrogen, a lower alkyl group containing up to 4 carbon atoms or a benzyl, phenyl or 2-, 3- or 4-pyridyl group; R2 and R3 are alkyl, alkenyl or cycloalkyl groups each containing up to 8 carbon atoms or a phenyl, halogenophenyl or lower alkoxyphenyl group or together with the carbon atoms to which they are attached constitute an alicyclic ring containing up to 8 carbon atoms; R4 is hydrogen or a lower alkyl group containing up to 4 carbon atoms which is attached to the 6 or 7 position of the indole nucleus; X and Y are lower alkyl, hydroxy lower alkyl, lower acyloxyalkyl, carbamyloxy lower alkyl or phenyl lower alkyl groups or together constitute, with the nitrogen atom, an optionally substituted heterocyclic ring having a maximum of 8 members, for example a piperidyl, (lower alkyl)-piperidyl, di(lower alkyl) - piperidyl, (lower alkoxy)-piperidyl, hydroxy - piperidyl, (lower acyloxy)-piperidyl, hydroxy - piperidyl, (lower acyloxy)-piperidyl, pyrrolidyl, (lower alkoxy) - pyrrolidyl, (lower alkyl) - pyrrolidyl, hydroxy-pyrrolidyl, morpholino, (lower alkyl) - morpholino, di(lower alkyl) - morpholino, (lower alkoxy) - morpholino, thiamorpholino, (lower alkyl) - thiamorpholino, di(lower alkyl) - thia-morpholino, (lower alkoxy) - thiamorpholino, piperazino, (lower alkyl) - piperazino, di(lower alkyl) - piperazino, (lower alkoxy) - piperazino, phenyl - piperazino, hydroxyalkyl - piperazino, lower acyloxy-lower alkyl piperazino or a carbamyloxy-lower alkyl-piperazino radical, are prepared by reaction of a compound of the general formula <FORM:1108578/C2/2> a compound of formula <FORM:1108578/C2/3> and formaldehyde or acid addition salts of the above compounds. ("Lower" designates groups containing up to 5 carbon atoms.) Compounds of the second general formula above (a) where R1 = H, are prepared by reaction of a compound of formula <FORM:1108578/C2/4> with a compound of formula <FORM:1108578/C2/5> and Zn and acetic acid; (b) where R1 is aryl or heterocyclic, by reaction of R1NH2 and a compound of formula <FORM:1108578/C2/6> Pharmaceutical compositions in conventional forms such as tablets, capsules, syrups, suppositories and sterile solutions for parenteral use, comprise a compound of the first general formula above and an inert carrier.