Cassella Farbwerke Mainkur Aktiengesellschaft

Cassella Aktiengesellschaft

Otto Grawinger

Josef Scholtholt

Thomas Raabe

Eckhard Schraven

Rolf-Eberhard Nitz

Rudi Beyerle

Ernst Heinrich

Karl Hintermeier

Horst Kindler

Adolf Stachel, Deceased

By Ingeburg Stachel, Heiress

Hanswilli Von Brachel

Heinz Bender

A 1-acyl-8-[2,3-epoxypropoxy]- and/or 1-acyl-8-[3-halo-2-hydroxypropoxy]-1,2,3,4-tetrahydroquinoline are reacted with primary and secondary amines to obtain corresponding physiologically-active 1-acyl-8-[3-amino-2-hydroxypropoxy]-1,2,3,4-tetrahydroquinolines and pharmacologically-acceptable acid-addition salts thereof. These compounds are useful as such or in conventional medicament compositions for treating those afflicted with heart ailments and/or hypertension.

1-Acyl-8-(3-amino-2-hydroxypropoxy)-1,2,3,4-tetrahydroquinolines,

Water-insoluble monoazo dyes of the formula ##STR1## produced by reacting a diazotized amine of the benzene, naphthalene, diphenyl, diphenylmethane or heterocyclic series which is free from water solubilizing groups with the appropriate 6-hydroxy-2-pyridone and the utility thereof for the dyeing and printing of synthetic fabric materials to yellow to red shades having excellent fastness to light and sublimation.

Water-insoluble monoazo pyridone dye

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, basically substituted heterocyclic compounds of the formula ##EQU1## wherein X represents

Basically substituted heterocyclic compounds

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

Water-insoluble monoazo dyes of the formula ##SPC1## Produced by reacting a diazotized amine of the benzene, naphthalene, diphenyl, diphenylmethane or heterocyclic series which is free from water solubilizing groups with the appropriate 6-hydroxy-2-pyridone and the utility thereof for the dyeing and printing of synthetic fabric materials to yellow to red shades having excellent fastness to light and sublimation.

Growing community of inventors

Frankfurt-am-Main, Germany

Otto Grawinger