Boehringer Mannheim Gmbh

Fritz Wiedemann

Gisbert Sponer

Karl Dietmann

Wolfgang Kampe

Max Thiel

Walter-Gunar Friebe

Wolfgang Bartsch

Egon Roesch

Helmut Michel

Kurt Stach

Carl H Ross

Wolfgang Schaumann

Klaus Strein

Wolfgang Weckerle

Ewald Rieger

New N-heteroarylalkylenediamine ##STR1## wherein R.sub.1 and R.sub.2 each independently is hydrogen, an alkyl radical containing up to 6 carbon atoms, or a benzyl radical,

N-Pyrazolylalkylenediamine intermediates

Carbazolyl-(4)-oxypropanolamine compounds of the formula ##STR1## wherein R.sub.1 is hydrogen, lower alkanoyl or aroyl;

Carbazolyl-(4)-oxypropanolamine compounds and therapeutic compositions

The present invention provides heteroaryloxypropanolamines and pharmaceutical compositions containing them, for combating, and for the prophylaxis of, cardiac and circulatory diseases. The heteroaryloxypropanolamines of the present invention are of the general formula: ##STR1## wherein A is a bi- or tricyclic heteroaromatic radical, which is optionally partly hydrogenated, X is a straight-chained or branched alkylene chain containing 2 to 6 carbon atoms, R.sub.1 and R.sub.2, which can be the same or different, are hydrogen atoms or lower alkyl or benzyl radicals, R.sub.3, R.sub.4 and R.sub.5, which can be the same or different, are hydrogen atoms or lower alkyl, benzyl, formyl, lower alkanoyl, cyano, hydroxymethyl, lower alkoxycarbonyl or carbamoyl radicals or the divalent substituents sulfur or oxygen and R.sub.6, R.sub.7 and R.sub.8, which can be the same or different, are hydrogen or halogen atoms, lower alkyl, nitro, amino, lower alkylthio or lower alkoxy radicals or R.sub.6 and R.sub.7 together represent an optionally unsaturated trimethylene chain; and the pharmacologically acceptable salts thereof. The present invention also provides processes for the preparation of these compounds, as well as pharmaceutical compositions containing them.

Indazoloxypropanolamine derivatives and use in combating, and for the

The present invention provides aryloxypropanolamines of the general formula: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4, which may be the same or different, are hydrogen or halogen atoms or lower alkyl, cyano, carboxamido, hydroxyl, lower acyloxy, lower alkoxy, lower alkenyloxy or aryl lower alkoxy radicals, R.sub.5 and R.sub.6, which may be the same or different, are hydrogen atoms or lower alkyl radicals, X is a straight or branched alkylene chain containing 2 to 6 carbon atoms, A is a mono-, bi- or tricyclic heteroaromatic or hydroheteroaromatic radical or, when at least one of the symbols R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is other than a hydrogen atom, may also be a phenyl radical, with the proviso that when A is a uracil-6-yl radical, the 5-position of the uracil moiety does not contain a hydrogen atom, R.sub.7, R.sub.8, R.sub.9, R.sub.10 and R.sub.11, which may be the same or different, are mono- or divalent substituents selected from hydrogen, halogen, nitro, hydroxylamino, amino, lower acylamino, lower alkylamino, di-(lower alkyl)-amino, hydroxyethylamino, di-(hydroxyethyl)-amino, hydroxyl, lower alkoxy, allyloxy, methoxy lower alkoxy, cyano, carboxamido, carboxy, lower alkoxycarbonyl, hydroxymethyl, lower alkoxymethyl, halomethyl, aminomethyl, lower acylaminomethyl, di-(lower alkyl)-aminomethyl, pyrrolidinomethyl, piperidinomethyl, di-(hydroxyethyl)-aminomethyl, morpholinomethyl, piperazinomethyl, 4-lower acylpiperazinomethyl, 4-lower alkylpiperazinomethyl, lower alkyl, lower alkenyl, 2-cyanoethyl, 2-(lower alkoxycarbonyl)-ethyl, 2-carboxyethyl, 2-hydroxyethyl, phenyl lower alkyl and phenyl, the phenyl radicals being optionally substituted with 1 or 2 hydroxyl or methoxy radicals, or from oxygen or sulphur; the optically-active forms and the racemic mixtures thereof, and the pharmacologically compatible salts thereof. The present invention also provides processes for the preparation of these compounds and pharmaceutical compositions containing them.

Cardioactive aryloxypropanolamines

The present invention provides heterocyclic oxypropanol derivatives of the general formula: ##STR1## wherein R.sub.1 is a hydrogen atom or a lower alkyl, aralkyl or lower alkanoyl radical, R.sub.2 and R.sub.3, which can be the same or different, are hydrogen atoms or lower alkyl, hydroxyalkyl, alkoxycarbonyl or alkanoyloxyalkyl radicals or together represent an alkylene radical, R.sub.4 is a hydrogen atom or a lower alkanoyl radical or an aroyl radical, R.sub.5 is a hydrogen atom or a lower alkyl radical or an aralkyl radical, R.sub.6 is a hydrogen atom or a lower alkyl radical, R.sub.7 is a hydrogen atom, a hydroxyl group or a lower alkyl radical, Z is a valency bond, a methylene radical or an oxygen or sulphur atom, Ar is a carbocyclic aryl radical or a pyridyl radical, R.sub.8, R.sub.9 and R.sub.10, which can be the same or different, are hydrogen or halogen atoms, hydroxyl groups, lower alkanoyl radicals, lower alkyl radicals, lower alkenyl radicals, lower alkoxy radicals, aralkoxy radicals, allyloxy radicals, lower alkylthio radicals, aminocarbonyl radicals, aminosulphonyl radicals or lower alkanoylamino radicals or R.sub.8 and R.sub.9 together represent a lower alkylenedioxy radical or R.sub.7 and R.sub.8 together represent a --CH.sub.2 --O-- radical and A is --X.sub.1 --Y.sub.1, in which X.sub.1 is a methylene or --NR.sub.11 -- radical, R.sub.11 being a hydrogen atom or a lower alkyl radical, and Y.sub.1 is a methylene radical or .dbd.C.dbd.Q, Q being an oxygen or sulphur atom; or A is --X.sub.2 .dbd.Y.sub.2 --, in which X.sub.2 and Y.sub.2, which can be the same or different and signify nitrogen atoms or .dbd.C(R.sub.12)-- groups, R.sub.12 being a hydrogen atom or a lower alkyl or an alkoxycarbonyl radical, and when --X.sub.2 .dbd.Y.sub.2 -- represents a --CH.dbd.N-- group and R.sub.1 is an alkyl or aralkyl radical, because of the ability of indazole to tautomerise, this can also be localized on the nitrogen atom represented by Y.sub.2, with the proviso that Y.sub.1 or Y.sub.2 is joined to .dbd.N--R.sub.1 in general formula (I), and, when Q is an oxygen atom or --X.sub.2 .dbd.Y.sub.2 -- represents --CR.sub.12 .dbd.CR.sub.12 -- and Z is a valency bond or when --X.sub.1 --Y.sub.1 -- represents ##STR2## and Z is an oxygen atom or a valency bond, either the two symbols R.sub.2 and R.sub.3 do not simultaneously represent hydrogen atoms or R.sub.7 and R.sub.8 together must form a --CH.sub.2 --O-- radical; and the pharmacologically acceptable salts thereof. The present invention also provides processes for the preparation of these compounds and pharmaceutical compositions containing them. Furthermore, the present invention is concerned with the use of these compounds for the treatment of cardiac and circulatory diseases.

Heterocyclic oxypropanolamine compounds and pharmaceutical compositions

A piperidinopropyl derivative of the formula ##STR1## in which R.sub.1 and R.sub.2 each independently is hydrogen or a lower alkyl radical, or together are an alkylene radical,

Inhibiting adrenergic .beta.-receptors with piperidinopropyl derivatives

Indazole compounds of the formula ##STR1## wherein R.sub.1 is hydrogen or lower alkyl,

Indazole compounds

A 3-(4-phenoxymethylpiperidino)-propyl-phenyl-ether of the formula ##STR1## wherein R.sub.1 and R.sub.2 each independently is hydrogen, lower alkyl, hydroxyalkyl, lower alkanoyloxyalkyl or --CO--Z,

Blood pressure lowering and adrenergic .beta.-receptor inhibiting

New indazolyl-(4)-oxypropanolamine compounds of the formula ##STR1## wherein R.sub.1 is hydrogen or lower alkyl; and

Indazolyl-(4)-oxypropanolamine compounds and therapeutic compositions

New N-substituted 1-amino-3-phenoxy-propan-2-ol compounds of the formula: ##STR1## wherein R.sub.1 and R.sub.2 are, individually, hydrogen or, taken together, represent a sulfur linkage, an ethylene radical or a valency bond;

N-substituted 1-amino-3-phenoxy-propan-2-ol compounds and therapeutic

New N-substituted 1-amino-3-phenoxy-propan-2-ol compounds of the formula: ##EQU1## wherein R.sub.1 and R.sub.2 are, individually, hydrogen or, taken together, represent a sulfur linkage, an ethylene radical or a valency bond;

Growing community of inventors

Weinheim-Lutzelsachsen, Germany

Fritz Wiedemann