Ciba-geigy Corporation

C-g Corp.

Herbert Schroter

Franz Ostermayer

Knut A Jaeggi

Kurt Eichenberger

Hans Kuhnis

Max Wilhelm

Jorg Frei

Christian Egli

Oswald Schier

Jurg Frei

Franz Ostsewrmayer

Heterocyclic compounds of the formula ##STR1## wherein Het denotes optionally substituted pyridazinyl, pyrimidinyl, pyrazinyl or substituted pyridyl, R.sub.1 is hydrogen or methyl and R.sub.2 is lower alklyl, optionally substituted phenyl-lower alkyl, carboxy-lower alkyl or functionally modified carboxy-lower alkyl, their condensation products with aldehydes, ketones or carbonic acid and their N-oxides, which are valuable (cardioselective) .beta.-receptor blocking agents, and/or (cardioselective) .beta.-receptor-stimulants.

2-(3-Amino-2-hydroxy-propoxy)-mono-and diazines

A compound of the formula ##STR1## in which R.sub.1 denotes optionally substituted lower alkyl which is optionally branched at the linking carbon atom, R.sub.2 represents hydrogen or lower alkanoyl and R.sub.3 is a group of the formula --R.sub.3.sup.a --(R.sub.3.sup.b).sub.n -- (Ia), in which R.sub.3.sup.a represents the radical of the formula --N(R.sub.4)-- or --O-- and R.sub.4 represents hydrogen or lower alkyl, R.sub.3.sup.b denotes the radical of the formula --CH.sub.2 -- or, if R.sub.3.sup.a represents --N(R.sub.4)--, denotes the radical of the formula --C(.dbd.O)-- and n represents nought or 1, and a group of the formula Ia, in which n represents 1, can be linked to the carbonyl group of the carbamoyl grouping either via the group R.sub.3.sup.a or the group R.sub.3.sup.b, or acid addition salts thereof, which can be used pharmaceutically can be used as beta-receptor blocking agents for the treatment of disorders in the cardiac rhythm and coronary heart diseases. These compounds also possess a cardio-stimulating action; some of them also display alpha-receptor-blocking properties.

Etherified hydroxy quinazolone compounds

Piperidines of the formula ##STR1## in which R.sub.1 is a substituted or unsubstituted heteroaryl radical, alk.sub.1 and alk.sub.2 independently of one another are lower alkylene radicals, each of which separates by 2 carbon atoms the nitrogen atom bonded thereto from the methane group bonded thereto, R.sub.2 is a free or acylated hydroxyl group, Ph is a substituted or unsubstituted o-phenylene radical, n is 0 or 1, R.sub.3 is a hydrogen atom, a lower alkyl radical or a hydroxyl group and R.sub.5 is a lower alkyl radical or a hydrogen atom, or R.sub.3 and R.sub.5 together are a second bond and R.sub.4 and R.sub.6 are each a hydrogen atom, or R.sub.4 together with R.sub.3 is an oxo group, R.sub.5 is a lower alkyl radical or a hydrogen atom and R.sub.6 is a hydrogen atom, or R.sub.6 together with R.sub.5 is an oxo group, R.sub.3 is a hydrogen atom, a lower alkyl radical or a hydroxyl group and R.sub.4 is a hydrogen atom, or salts thereof are antihypertensive and antiarrhythmic agents.

Piperidine derivatives

The invention relates to novel piperidino-propanols, especially 1-(3-heterocyclyloxy-2-hydroxy-propanol)-4-(N-diazcyclyl)-piperidines of the formula ##STR1## in which R.sub.1 is a substituted or unsubstituted heteroaryl radical, R.sub.2 is hydrogen or a substituted or unsubstituted aliphatic, cycloaliphatic, cycloaliphatic-aliphatic or araliphatic hydrocarbon radical or an acyl radical and alk is lower alkylene which separates the two nitrogen atoms from one another by 2 or 3 carbon atoms, or is a substituted or unsubstituted 1,2-phenylene radical, and salts thereof, as well as processes for their preparation, and also to pharmaceutical preparations containing these compounds and the use thereof, preferably in the form of pharmaceutical preparations as antihypertensive agents, antitachycardiac agents and .alpha.-sympathicolytic agents.

Piperidino-propanols

A process known per se for the manufacture of oxygenated N-aryl-diazacyclic compounds of the formula ##STR1## wherein each of R.sub.1 and R.sub.2 represents a substituted or unsubstituted aryl group and alk represents a lower alkylene group which separates both nitrogen atoms from each other by 2 or 3 carbon atoms, or salts thereof. The novel compounds can be used as antihypertensives, antitachycardiac agents and .alpha.-receptor blockers.

Oxygenated N-aryl-diazacyclic compounds

Heterocyclic compounds of the formula ##STR1## wherein Het denotes optionally substituted pyridazinyl, pyrimidinyl, pyrazinyl or substituted pyridyl, R.sub.1 is hydrogen or methyl and R.sub.2 is lower alkyl, optionally substituted phenyl-lower alkyl, carboxy-lower alkyl or functionally modified carboxy-lower alkyl, their condensation products with aldehydes, ketones or carbonic acid and their N-oxides, which are valuable (cardioselective) .beta.-rezeptor blocking agents, and/or (cardioselective) .beta.-rezeptor-stimulants.

2-(3-Amino-2-hydroxy-propoxy)pyridine derivatives and pharmaceutical

A process known per se for the manufacture of oxygenated N-aryl-diazacyclic compounds of the formula ##STR1## wherein EACH OF R.sub.1 and R.sub.2 represents a substituted or unsubstituted aryl group and alk represents a lower alkylene group which separates both nitrogen atoms from each other by 2 or 3 carbon atoms, or salts thereof. The novel compounds can be used as antihypertensives, antitachycardiac agents and .alpha.-receptor blockers.

Antihypertensive 1-substituted-4-(2-oxo-1-imidazolidinyl) piperidines

A compound of the formula ##STR1## in which R.sub.1 denotes optionally substituted lower akyl which is optionally branched at the linking carbon atom, R.sub.2 represents hydrogen or lower alkanoyl and R.sub.3 is a group of the formula --R.sub.3.sup.a -(R.sub.3.sup.b).sub.n -- (Ia), in which R.sub.3.sup.1 represents the radical of the formula --N(R.sub.4)-- or --O-- and R.sub.4 represents hydrogen or lower alkyl, R.sub.3.sup.b denotes the radical of the formula --CH.sub.2 -- or, if R.sub.3.sup.a represents --N(R.sub.4)--, denotes the radical of the formula --C(.dbd.O)-- and n represents nought or 1, and a group of the formula Ia, in which n represents 1, can be linked to the carbonyl group of the carbamoyl grouping either via the group R.sub.3.sup.a or the group R.sub.3.sup.b, or acid addition salts thereof, which can be used pharmaceutically can be used as beta-receptor blocking agents for the treatment of disorders in the cardiac rhythm and coronary heart diseases. These compounds also possess a cardio-stimulating action; some of them also display alpha-receptor-blocking properties.

Etherified hydroxy-benzodiheterocyclic compounds

Compounds of the formula ##STR1## WHEREIN Ar.sub.1 and Ar.sub.2 denote an optionally substituted aromatic hydrocarbon radical or a monocyclic, monoazacyclic or diazacyclic radical of aromatic character and Alk represents lower alkylene, or salts thereof, exhibit .beta.-receptor-blocking, blood pressure-lowering and vasodilatory effects and are useful for example in the treatment of arrythmias and angina pectoris, and as blood pressure-lowering agents.

Cyclic-substituted derivatives of 1-amino-2-propanol

2-(3-Amino-2-hydroxy-propoxy)-pyrazines

Piperidines of the formula ##STR1## in which R.sub.1 stands for optionally substituted aryl, R.sub.2 for hydrogen, lower alkyl, lower alkenyl, acyl or .alpha.-aryl-lower alkyl, R.sub.3 for a free or substituted hydroxyl group, alk for lower alkylene which separates the two nitrogen atoms by 2 or 3 carbon atoms, R.sub.4 represents hydrogen or lower alkyl and n represents an integer from 1 to 4, and their salts as well as processes for their manufacture and pharmaceutical compositions comprising such compounds, and a process for lowering the blood pressure wherein such compositions are administered to a warm-blooded host.

1-Substituted-4-(2-oxo-hexahydro-1-pyrimidinyl)-piperidine

Pharmaceutical piperidine derivatives

1-Phenoxy-2-hydroxy-3-amino-propanes of the formula I ##STR1## wherein R.sub.1 is a sugar residue and R.sub.2 is isopropyl, tert.-butyl or .alpha.-methyl-phenethyl optionally substituted in the phenyl part, and salts thereof are useful as positively inotropic agents, especially in the treatment of insufficiency of the cardiac muscle.

Composition and method for treatment of heart and circulatory ailments

Amines of the formula ##STR1## wherein R.sub.1 is lower alkyl, lower alkoxy or amino, R.sub.2 is hydrogen or lower alkyl, R.sub.3 is hydrogen, lower alkyl, carboxyl or lower alkoxycarbonyl, R.sub.4 is hydrogen or lower alkyl, R.sub.5 is lower alkyl, aryl-lower alkyl or optionally functionally modified carboxy-lower alkyl and R.sub.6 denotes halogen, trifluoromethyl, lower alkyl, lower alkenyl, lower alkoxy, lower alkenyloxy, nitro, lower alkoxymethyl, carbamoyl, N-lower alkylcarbamoyl, nitrile, lower alkinyloxy or hydrogen, and their salts block cardiac and vascular .beta.-receptors the are useful in the treatment of arrhythenias and angina pectoris and as intermediates for, especially for pharmaceutically active substances.

Growing community of inventors

Fullinsdorf, Switzerland

Herbert Schroter