Boehringer Ingelheim Gmbh

Albrecht Engelhardt

Herbert Koppe

Karl Zeile

Werner Kummer

Helmut Stahle

Werner Traunecker

Werner Taunecker

A compound selected from the group consisting of racemates of 1-phenoxy-2-hydroxy-3-tert.-butylamino propanes of the formula ##STR1## wherein R is selected from the group consisting of alkynyloxy of 2 to 4 carbon atoms, and R.sub.1 is selected from the group consisting of hydrogen, halogen and alkoxy of 1 to 4 carbon atoms, their optically active isomers and their non-toxic, pharmaceutically acceptable acid addition salts of said racemates and said optically active isomers which compounds possess bradycardia activity and isoproterenol antagonistic activity and also antiarrhythmic activity.

1-Phenoxy-2-hydroxy-3-tert.-butylamino propane antiarrhythmic compounds

A composition having bradycardia and isoproterenol activity comprising at least one compound selected from the group consisting of racemates of 1-phenoxy-2-hydroxy-3-tert.-butylamino propanes of the formula ##STR1## wherein R is --(CH.sub.2).sub.x --NH.sub.2, where x is an integer from 0 to 3, preferably 0, R.sub.1 and R.sub.2 are halogen, their optically active isomers and their non-toxic, pharmaceutically acceptable acid addition salts of said racemates and said optically active isomers and a major amount of a pharmaceutical carrier and a method of producing bradycardia and suppressing tachycardia effects of N-isopropyl-noradrenaline in warm-blooded animals.

Therapeutic compositions and method

Pharmaceutical compositions containing as an active ingredient a compound of the formula ##STR1## wherein n is 4 or 5, or a non-toxic, pharmacologically acceptable acid addition salt thereof; and a method of using the same as .beta.-adrenergic receptor blockers.

Pharmaceutical compositions containing a

Compounds of the formula ##STR1## wherein R is secondary butyl or tertiary butyl, and their non-toxic, pharmacologically acceptable acid addition salts; the compounds as well as their salts are useful as .beta.-adrenergic receptor blocking agents and hypotensives.

1-(2'-Ethynyl-phenoxy)-2-hydroxy-3-butylamino-propanes and salts

A composition having bradycardia and isoproterenol antagonistic activity comprising at least one compound selected from the group consisting of racemates of 1-phenoxy-2-hydroxy-3-tert.-butylamino propanes of the formula ##SPC1## Wherein R is selected from the group consisting of --(CH.sub.2).sub. x --CN where x is an integer from 0 to 3, COOH and COOR' where R' is alkyl of 1 to 4 carbon atoms; R.sub.1 is selected from the group consisting of hydrogen, alkoxy and alkylthio of 1 to 4 carbon atoms,--CN and alkenyl and alkynyl of 2 to 4 carbon atoms and R.sub.2 is selected from the group consisting of hydrogen, halogen and alkyl and alkoxy of 1 to 4 carbon atoms, their optically active isomers and their non-toxic, pharmaceutically acceptable acid addition salts of said racemates and said optically active isomers and a major amount of a pharmaceutical carrier and a method of producing bradycardia and suppressing tachycardia effects of N-isopropyl-noradrenaline in warm-blooded animals.

A composition having bradycardia and isoproterenol antagonistic activity comprising at least one compound selected from the group consisting of racemates of 1-phenoxy-2-hydroxy-3-tert.-butylamino propanes of the formula ##EQU1## wherein R is selected from the group consisting of --(CH.sub.2).sub.x --CN where x is an integer from 0 to 3, COOH and COOR' where R' is alkyl of 1 to 4 carbon atoms; R.sub.1 is selected from the group consisting of hydrogen, alkoxy and alkylthio of 1 to 4 carbon atoms, --CN and alkenyl and alkynyl of 2 to 4 carbon atoms and R.sub.2 is selected from the group consisting of hydrogen, halogen and alkyl and alkoxy of 1 to 4 carbon atoms, their optically active isomers and their non-toxic, pharmaceutically acceptable acid addition salts of said racemates and said optically active isomers and a major amount of a pharmaceutical carrier and a method of producing bradycardia and suppressing tachycardia effects of N-isopropyl-noradrenaline in warm-blooded animals.

Compounds of the formula ##EQU1## wherein n is 4 or 5, and non-toxic, pharmacologically acceptable acid addition salts thereof; the compounds as well as their salts are useful as .beta.-adrenergic receptor blocking agents.

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Mainz, Germany

Albrecht Engelhardt