Aminobenzyl-amines and salts thereof

Abstract

Compounds of the formula ##STR1## wherein R 1 is hydrogen or aliphatic or aromatic carboxylic acyl, R 2 is hydrogen, chlorine or bromine, R 3 is fluorine, alkyl of 1 to 4 carbon atoms, trifluoromethyl, cyano, carbamoyl, carboxyl, carbalkoxy, alkoxy, acetyl, 1-hydroxyethyl or ##STR2## where R 6 and R 7 are each alkyl, cycloalkyl, hydroxy-cycloalkyl or, together with each other and the nitrogen atom to which they are attached, pyrrolidino, piperidino or morpholino, and R 4 and R 5 are each hydrogen, alkyl of 1 to 5 carbon atoms, mono- or di-hydroxy (alkyl of 1 to 5 carbon atoms), alkenyl of 2 to 4 carbon atoms, cycloalkyl of 5 to 7 carbon atoms, mono- or di-hydroxy(cycloalkyl of 5 to 7 carbon atoms), benzyl, morpholinocarbonylmethyl or, together with each other and the nitrogen atom to which they are attached, pyrrolidino, piperidino, hexamethyleneimino, morpholino, N-methyl-piperazino or camphidino, and non-toxic, pharmacologically acceptable acid addition salts thereof; the compounds as well as their salts are useful as anti-ulcerogenics, secretolytics, .[.antitussive,.]. .Iadd.antitussives .Iaddend.and stimulants of the production of the surfactant or antiatelectasis factor of the alveoli.

We claim: .[.1. A compound of the formula ##STR13## wherein R 1  is hydrogen, lower alkanoyl, benzoyl or halobenzoyl, R 2  is hydrogen, chlorine or bromine, 
     
        pharmacologically acceptable acid addition salt thereof..]. 2. A compound of claim .[.1.]..Iadd.4.Iaddend., which is 2-amino-3-bromo-5-carbethoxy-N,N-diethyl-benzylamine or a non-toxic, 
     
     
        pharmacologically acceptable acid addition salt thereof. 3. A compound of claim .[.1.]..Iadd.4.Iaddend., which is 2-amino-3-bromo-5-carboxy-N-cyclohexyl-N-ethyl-benzylamine or a non-toxic, pharmacologically acceptable acid addition salt thereof. .Iadd. 4. A compound of the formula ##STR14## wherein R 1  is hydrogen, lower alkanoyl, benzoyl or halobenzoyl; R 2  is chlorine or bromine;   R 3  is carboxyl or lower carbalkoxy; and   R 4  and R 5  are each hydrogen, alkyl of 1 to 5 carbon atoms, mono- or di-hydroxy(alkyl of 1 to 5 carbon atoms), alkenyl of 2 to 4 carbon atoms, cycloalkyl of 5 to 7 carbon atoms, mono- or di-hydroxy(cycloalkyl of 5 to 7 carbon atoms) or benzyl; or a non-toxic, pharmacologically acceptable acid addition salt     
     
     
        thereof..Iaddend..Iadd. 5.  A compound according to claim 4, where   R 1  is hydrogen, lower alkanoyl, benzoyl or halobenzoyl;   R 2  is chlorine or bromine;   R 3  is carboxyl or lower carbalkoxy; and   R 4  and R 5  are each alkyl of 1 to 5 carbon atoms, mono- or di-hydroxy(alkyl of 1 to 5 carbon atoms), alkenyl of 2 to 4 carbon atoms, cycloalkyl of 5 to 7 carbon atoms, mono- or di-hydroxy(cycloalkyl of 5 to 7 carbon atoms) or benzyl; or a non-toxic, pharmacologically acceptable acid addition salt thereof..Iaddend. .Iadd. 6. A compound of claim 4,   where     R 1  is hydrogen;   R 2  is chlorine or bromine;   R 3  is carboxyl or lower carbalkoxy; and   R 4  and R 5  are each alkyl of 1 to 5 carbon atoms or cycloalkyl of 5 to 7 carbon atoms; or a non-toxic, pharmacologically acceptable acid addition salt thereof..Iaddend.