Cassella Farbwerke Mainkur Aktiengesellschaft

Cassella Aktiengesellschaft

Eckhard Schraven

Josef Scholtholt

Thomas Raabe

Otto Grawinger

Rolf-Eberhard Nitz

Karl Schonafinger

Ursula Schindler

Klaus Resag

Rudi Beyerle

Adolf Stachel, Deceased

Ingeburg Lydia Stachel, Heiress

The invention relates to the use of 2-(N-(2-aminoethyl)amino)acetic acid derivatives of the formula I ##STR1## in which R denotes, for example, phenyl or thienyl, and their pharmacologically acceptable acid addition salts as pharmacological active compounds.

Use of 2- (N-(2-aminoethyl)amino) acetic acid derivatives

2-(N-(2-aminomethyl)amino)acetic acid derivatives to inhibit advanced

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.

N-Aryloxypropyl-N'-dioxopyrimidyl-.alpha.,.omega.-alkylenediamines

The present invention relates to new pharmacologically valuable derivatives of 1-phenoxy-3-amino-propan-2-ol having the formula ##STR1## Wherein A denotes -CH.sub.2 -alkoxy, -O-alkoxyalkyl, -O-hydroxyalkyl, or ##STR2## R.sub.1 denotes hydrogen or methyl, Het denotes the radical of a pyrrole, pyrazole, imidazole, furane, thiophene, thiazole, pyridine, pyridazine, pyrimidine or pyrazine, which can additionally be substituted by one or more methyl groups, said radical is linked through a C atom, and R.sub.2 and R.sub.3 denote hydrogen, alkyl, alkenyl or cycloalkyl or conjointly with the N atom to which they are linked, and optionally with a further oxygen or sulfur hetero-atom, denote a saturated, 5-membered or 6-membered, monocyclic, heterocyclic structure, and alkyl radicals contain 1 to 4 carbon atoms, alkoxy radicals contain 1 to 4 carbon atoms, alkenyl radicals contain 3 or 4 carbon atoms and cycloalkyl radicals contain 5 to 7 carbon atoms; and aldehyde condensation products and acid addition salts thereof.

Pharmaceutically active derivatives of 1-phenoxy-3-amino-propan-2-ol

The present invention relates to new pharmacologically valuable derivatives of 1-phenoxy-3-amino-propan-2-ol having the formula ##STR1## wherein X denotes ##STR2## A denotes --CH.sub.2 --alkoxy, --O--alkoxyalkyl, --O--hydroxyalkyl or ##STR3## AN AROMATIC OR QUASI-AROMATIC, 5-MEMBERED OR 6-MEMBERED, MONOCYCLIC RING WHICH IS LINKED THROUGH A C atom which has one or 2 nitrogen, oxygen and/or sulphur hetero-atoms and which can be substituted additionally by one or more methyl groups, and R.sub.2 and R.sub.3 denote hydrogen, alkyl, alkenyl or cycloalkyl or, conjointly with the N atom to which they are linked, and optionally with a further oxygen or sulphur hetero-atom, denote a saturated, 5-membered or 6-membered, monocyclic, heterocyclic structure, and alkyl radicals contain 1 to 4 carbon atoms, alkoxy radicals contain 1 to 4 carbon atoms, alkenyl radicals contain 3 to 4 carbon atoms and cycloalkyl radicals contain 5 to 7 carbon atoms; and aldehyde condensation products and acid addition salts thereof and to the production thereof by a method selected from (A) reacting a compound having the formula ##STR4## with a compound of the general formula Y -- X wherein X has the meanings indicated above and Y represents halogen and, if X denotes ##STR5## ALSO REPRESENTS --OH, --OK and --ONa; (B) reacting a compound having the formula ##STR6## with a compound of the formula H.sub.2 N--X wherein X has the meanings indicated above and Z represents ##STR7## AND Hal denotes halogen; (C) reacting a phenol of the formula ##STR8## with a compound of the formula Z--CH.sub.2 NH--X wherein X has the meanings indicated above and Z denotes ##STR9## WHEREIN Hal represents a halogen atom; and that the resulting compound is optionally reacted with an aldehyde of the formula R.sub.4 --CHO, wherein R.sub.4 denotes hydrogen or a lower alkyl radical having up to 4 C atoms, to form an oxyzolidine of the formula ##STR10## or is optionally reacted with an acid to form an acid addition salt.

Derivatives of 1-phenoxy-3-amino-propan-2-ol

The present invention relates to new pharmacologically valuable derivatives of 1-phenoxy-3-amino-propan-2-ol having the formula ##STR1## and the aldehyde condensation products and acid addition salts thereof wherein X is selected from the group consisting of ##STR2## wherein the phenyl ring I may have attached to it up to three similar or different substituents selected from the group consisting of alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, alkoxy, alkenyloxy, alkinyloxy, benzyloxy, phenyl, halogen and --NR.sub.1 R.sub.2, wherein R.sub.1 is selected from alkyl and acyl, and R.sub.2 is selected from hydrogen and alkyl; and to the production thereof by a method selected from (A) reacting 1-phenoxy-3-amino-propan-2-ol having the formula ##STR3## with a compound having the formula Y-X, wherein X has the above-defined meaning and Y is selected from halogen, --OH, --OK or --ONa; (B) reacting a compound of the formula ##STR4## with a compound of the formula H.sub.2 N--X, wherein X has the above-defined meaning and Z is selected from ##STR5## and ##STR6## (C) reacting a phenol ##STR7## wherein X and Z have the meaning defined above.

The present invention relates to new pharmacologically valuable derivatives of 1-phenoxy-3-amino-propan-2-ol having the formula ##EQU1## and the aldehyde condensation products and acid addition salts thereof wherein X is selected from the group consisting of ##EQU2## wherein the phenyl ring I may have attached to it up to three similar or different substituents selected from the group consisting of alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, alkoxy, alkenyloxy, alkinyloxy, benzyloxy, phenyl, halogen and --NR.sub.1 R.sub.2, wherein R.sub.1 is selected from alkyl and acyl, and R.sub.2 is selected from hydrogen and alkyl and n is 1, 2 or 3; and to the production thereof by a method selected from (A) reacting 1-phenoxy-3-amino-propan-2-ol having the formula ##EQU3## with a compound having the formula Y-X, wherein X has the above defined meaning and Y is selected from halogen, --OH, --OK or --ONa; (B) reacting a compound of the formula ##EQU4## with a compound of the formula H.sub.2 N--X, wherein X has the above-defined meaning and Z is selected from ##EQU5## and ##EQU6## (C) reacting a phenol ##EQU7## with Z--CH.sub.2 --NH--X, wherein X and Z have the meaning defined above.

Derivatives of 1-phenoxy-3-amino-propan-2-ol and process for their

The present invention relates to new coumarin compounds useful as coronary dilators and having the formula ##SPC1## Or the hydrochloric acid addition salts thereof, and to methods of preparing same either by acylating, in the presence of acid-binding agents, if desired, coumarin derivatives having the formula ##SPC2## With acylating agents selected from the group consisting of alkoxybenzoic acid having the formula ##SPC3## And functional derivatives thereof, or by condensing, in the presence of acid-binding agents, if desired, coumarin derivatives having the formula ##SPC4## With an amine having the formula RH, wherein R is piperazino which is free of acyloxy groups and is bound via a nitrogen atom; R.sub.1 is selected from the group consisting of alkyl radicals having 1-4 carbon atoms and phenyl; R.sub.2 is selected from the group consisting of 5,7-, 6,7- and 7,8-positioned alkoxy groups having 1-4 carbon atoms; R.sub.3 is selected from alkoxy groups having 1-4 carbon atoms; R.sub.4 is selected from the group consisting of chlorine and bromine; R' is piperazino which is free of hydroxy groups and is bound via a nitrogen group; and m is selected from the group consisting of 1, 2, and 3.

Growing community of inventors

Frankfurt-am-Main, Germany

Eckhard Schraven