Compounds of the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are hydrogen or substituents of various types; R.sub.4 is hydrogen; alkyl of 1 to 5 carbon atoms; or optionally substituted aralkyl of 7 to 14 carbon atoms; R.sub.5 is a heterocycle; D is alkylene of 1 to 12 carbon atoms; and A is hydrogen or acyl; and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as .alpha.- and .beta.-adrenergic receptor blocking agents and antidepressants.
Physiologically-acceptable substituted 1,2-ethylenediamines and 1,3-propylenediamines, in free-base and in acid-addition-salt form, have highly pronounced and cardioselective .beta.-adrenolytic action, antiarrhythmic action and hypotensive action on administration to humans. The diamines are, more specifically, N-[3-aryloxy-2-hydroxypropyl]-N'-[1,3-(di-R.sup.3)-2,4-dioxypyrimid-6-yl] (ethylene or propylene)diamines wherein R.sup.3 is --H or lower alkyl and the aryl nucleus is either further unsubstituted, further monosubstituted or further disubstituted. The compounds are prepared, e.g, by reacting a corresponding N-[3-phenoxy-2-hydroxypropyl] (ethylene or propylene)diamine with a corresponding 6-chloropyrimidine-2,4-dione in a suitable medium containing an acid-binding agent. Such compounds are administered orally or parenterally in effective, but substantially non-toxic, doses either in substantially pure form, in virtually any standard dosage form or in combination with one or more other pharmacologically- and chemically-compatible drugs.
1-Phenoxy-3-[(3-indolyl)-tert.-butyl]amino-2-propanols and related 1-aryloxy compounds are antihypertensive agents having vasodilator and adrenergic .beta.-receptor blocking action. Preferred compounds bear an ortho-substituent in the phenoxy group, and most preferably the cyano group.
Compounds of the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are each hydrogen or a substituent of various types; R.sub.4 is hydrogen, alkyl of 1 to 5 carbon atoms, or optionally substituted aralkyl of 7 to 14 carbon atoms; R.sub.5 is a heterocycle; D is a alkylene of 1 to 12 carbon atoms; and A is hydrogen or acyl, and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as .alpha.- and .beta.-adrenergic receptor blocking agents and antidepressants.
Compounds of the formula ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are hydrogen or substituents of various types; R.sub.4 is hydrogen; alkyl of 1 to 5 carbon atoms; or optionally substituted aralkyl or 7 to 14 carbon atoms; R.sub.5 is a heterocycle; D is alkylene of 1 to 12 carbon atoms; and A is hydrogen or acyl; and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as their salts are useful as .alpha.- and .beta.-adrenergic receptor blocking agents and antidepressants.