3-Aminopropoxyaryl derivatives, their preparation and pharmaceutical compositions containing them

Abstract

Abstract The compounds of formula I <IMAGE> I wherein R1 is hydrogen or methyl, R3 is hydrogen, methyl, hydroxymethyl, carboxyl, alkoxycarbonyl of 2 to 5 carbon atoms, carbamoyl or cyano and R2 is a group (a) to (i), groups (a) to (i) having the following significances: <IMAGE> (a) wherein n is 0 or 1 and Ra, Rb, Rc and Rd independently are hydrogen or alkyl of 1 to 4 carbon atoms; <IMAGE> (b) wherein Re is hydrogen or alkyl of 1 to 4 carbon atoms; <IMAGE> (c) <IMAGE> (d) wherein Rh is halogen of atomic number of from 9 to 35; <IMAGE> (e) NHC(CH2OH)3; (f) <IMAGE> (g) <IMAGE> (h) <IMAGE> (i) wherein Ri together with Rn is o-phenylene optionally substituted by alkyl of 1 to 4 carbon atoms, alkoxy of 1 to 4 carbon atoms or halogen of atomic number of from 9 to 35 and, when R3 is cyano, Ri together with Rn additionally is lower alkylene separating by 2 or 3 carbon atoms the nitrogen atom to which Ri is bound from the nitrogen atom to which Rn is bound and Rm is hydrogen or an aliphatic, cycloaliphatic, cycloaliphatic-aliphatic, araliphatic or aromatic moiety or an acyl moiety, with the provisos that, (A) when R1 is hydrogen and R2 is a group (b), R3 is methyl, hydroxymethyl, carbamoyl or cyano and (B) when R2 is a group (h), R3 is hydrogen, carbamoyl or cyano. The compounds are useful as antiarrhythmic, alpha -adrenergic blocking and antihypertensive agents and, when a cyano or carbamoyl group is attached in the 2-position of the indole nucleus, additionally as beta -adrenergic blocking agents.

Inventors

• 👤 Richard Berthold

Bibliographic Details