Verfahren zur Herstellung von neuen pharmakologisch wirksamen Alkylendiamin-Derivaten

摘要

The invention comprises compounds of the formula wherein R1 represents a possibly substituted phenyl, benzyl, pyridyl or pyrimidyl group, R2 represents a hydrogen atom or a C1-6 alkyl group, R3 represents an N-heterocyclic 5- or 6-membered ring, n1 represents 2 or 3, n2 represents 1, 2, 3 or 4, and X represents a hydrogen or halogen atom or an alkoxy group; acid addition and quaternary ammonium salts thereof; and processes for their preparation comprising (a) reacting a compound of the formula with a compound of the formula R3-(CH2)n2-NHR2 and reducing the resulting amide, or (b) reacting a compound of the formula with a compound of the formula and reducing the resulting amide, or (c) reacting a compound of the formula with a compound of the formula R3-(CH2)n2-NHR2 and reducing the resulting amide, or (d) reacting a compound of the formula with a compound of the formula R3-(CH2)n2-2CH=CH2 in which Y in reactions (a) and (b) represents a halogen atom or an alkoxy group and Z in reaction (c) represents a chlorine or bromine atom. N - p - chloro - phenyl - N - benzyl - glycine methyl ester is prepared by reacting N-benzylp-chloro-aniline with monochloroacetic acid in the presence of sodium acetate and esterifying with methanol the resulting N-p-chlorophenyl-N-benzyl-glycine. N - benzyl - N - p - (chloro or bromo) - phenylchloro-acetamides are prepared by reacting the appropriately substituted N-benzyl-aniline with chloroacetyl chloride. N - benzyl - N - p - bromo - phenyl - N1methyl - ethylene - diamine is prepared by reacting methylamine with N-benzyl-N-pbromo-phenyl-chloro-acetamide to form Nmethyl - glycine - N1 - benzyl - N1 - p -bromophenyl-amide and treating this compound with diborane. N-benzyl-N-p-chloro-phenyl-N1-ethylethylene diamine is prepared by reacting ethylamine with N-benzyl-N-p-chloro-phenyl-chloroacetamide to form N1-ethyl-glycine-N-benzyl-Np-chloro-phenyl-amide and treating this compound with diborane.