Boehringer Ingelheim Gmbh

Karl Zeile

Herbert Koppe

Albrecht Engelhardt

Werner Kummer

Helmut Stahle

Kurt Schromm

Anton Mentrup

Peter Danneberg

Otto Thoma

Werner Traunecker

Werner Taunecker

Pharmaceutical compositions containing as an active ingredient a compound of the formula ##STR1## wherein R.sub.1 is alkyl of 1 to 5 carbon atoms,

Pharmaceutical compositions containing a

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 R is hydrogen or alkyl of 1 to 3 carbon atoms, and R.sub.1 is hydrogen or methyl, or a non-toxic, pharmacologically acceptable acid addition salt thereof; and a method of using the same as anticonvulsives and antiarrhythmics.

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.

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

Compounds of the formula ##SPC1## Wherein

1-(2'-Alkyl-3',4'-dihydroxy-phenyl)-2-(phenylalkyl-amino)-alkanols-(1)

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.

Compounds of the formula ##EQU1## wherein R is hydrogen or alkyl of 1 to 3 carbon atoms, and

1-(2',6'-Dimethyl-phenoxy)-2-amino-alkanes and salts thereof

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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Ingelheim am Rhein, Germany

Karl Zeile