Verfahren zur Herstellung von neuen N, N'-substituierten Diaminoaethylenverbindungenoder deren Salzen mit physiologisch vertraeglichen Saeuren

摘要

1,050,132. N,N1-Disubstituted diaminoethanes. FARBWERKE HOECHST A.G. Feb. 26, 1964 [March 1, 1963], No. 8062/64. Heading C2C. Novel diaminoethanes of the formula in which R 1 = H or CH 3 , R 2 and R 3 are each H or CH 3 O, and Z may be absent or, if present, represents a single bond or an -O-, -S-, -CH 2 or -C 2 H 4 - bridge, and their physiologically tolerable acid addition salts, are made by (a) condensing the appropriate N,N-diphenyl-diaminoethane with a phenyl acetone compound and simultaneously or subsequently hydrogenating the product; (b) condensing the appropriate N,N-diphenyl-diaminoethane, optionally bearing a methyl substituent on the N1- atom with a 1-phenyl-2-halo-propane or propene compound and, if a product containing a double bond is obtained, hydrogenating; (c) reacting the appropriate N,N-diphenyl-2-aminoethyl halide with a 2-amino-3-phenyl-propane, preferably in the presence of a hydrogen halide binding agent; (d) condensing the appropriate diphenylamine compound with an N-(2-haloethyl)-N- (2-phenylisopropyl)-amine, preferably in the presence of a hydrogen halide binding agent; (e) condensing an appropriate N,N-diphenyl acetaldehyde with a 2-amino-3-phenyl-propane and simultaneously or subsequently hydrogenating the product; or (f) reducing the appropriate diphenylaminoacetamide or phenylisopropylaminoacetyl diphenylamide to the amine. In these processes the appropriate N,N-diphenylamino compounds referred to include compounds wherein the phenyl rings are linked by a single bond or an -O-, -S-, -CH 2 - or -C 2 H 4 - bridge. In processes (b), (c), (d) and (f) the starting materials may bear a benzyl substituent on the N atom, corresponding to R 1 in the product which is finally removed by catalytic hydrogenation. N - [1 - Phenylpropyl - (2)] - aminoacetic diphenylamide hydrochloride is made by reaction of chloroacetyl - diphenylamine with 1 - phenyl - 2-amino-propane. 1 (31,41 - Dimethoxyphenyl) - 2 - (N - chloroethyl-N-methylamino)-propane is made by reacting 3,4 - dimethoxyphenyl acetone with aminoethanol, hydrogenating the resulting Schiffs base, methylating with formic acid and formaldehyde and reacting the product with thionyl chloride. 1 - Phenyl - 2 - chloroethylamino - propane is made by reacting 1-phenyl-2-aminopropane with ethylene chlorohydrin and reacting the resulting basic alcohol with thionyl chloride. Pharmaceutical preparations having a beneficial effect on the heart and blood circulation, comprise the above compounds of the invention, in admixture or conjunction with a carrier adapted to oral or parenteral administration.