20,21-dinor-eburnamenines
AssigneeAventis Pharma S.A.
InventorsFrançois Clemence, Jean-Luc Haesslein, Claude Oberlander
Life of this patent
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Abstract
A compound selected from the group consisting of all possible isomers or racemates of a compound of the formula wherein the various substituents are as defined in the specification and its non-toxic, pharmaceutically acceptable salts with acids or bases having anti-anoxic, anti-ischemic and neuronal protective anti-depressant activities.
Claims10
A compound selected from the group consisting of all possible isomers or racemates of a compound of the formula
- wherein X1, X2 and X3 are individually selected from the group consisting of hydrogen, halogen, alkyl of 1 to 18 carbon atoms, alkenyl and alkynyl of 2 to 18 carbon atoms, alkoxy of 1 to 7 carbon atoms, —OH, —CF3, —NO2, —NH2, mono and dialkylamino of 1 to 4 alkyl carbon atoms and phenyl;
- wherein
- R is selected from the group consisting of alkyl of 1 to 7 carbon atoms optionally substituted with a member of the group consisting of hydroxy, amino, mono and dialkylamino, 1 to 3 halogens, —CN, carbamoyl and acyl of an organic carboxylic acid of 1 to 6 carbon atoms, alkynyl of 2 to 7 carbon atoms and phenyl, R1 is
- or ═C═CH—R10, R10 is hydrogen or alkyl of 1 to 6 carbon atoms, one of R8 and R9 is selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms and cyano and the other is hydrogen or alkyl of 1 to 6 carbon atoms and its pharmaceutically acceptable salts with acid or bases.
The method of treating cerebral insufficiencies of anoxic or ischemic origin in warm-blooded animals comprising administering to warm-blooded animals an amount of an active compound selected from the group consisting of [16α, (±)]-15-(1-propynyl)-20,21-dinoreburnamenine oxalate, [16α, (±)]-15-methyl-20-21,dinoreburnamenine, [16α, (±)]-14,15-dihydro-15-methylene-20,21-dinoreburnamenine acid maleate, [16α, (±)]-20,21-dinoreburnamenine-15-methanol acid maleate and [16α, (±)]-N,N-dimethyl-20-21-dinoreburnamenine-15-methanamine acid maleate to treat cerebral insufficiences of anoxic or ischemic origin.
A compound selected from the group consisting of [16α, (±)]-15-(1-propynyl)-20,21-dinoreburnamenine oxylate, [16α, (±)]-14,15-dihydro-15-methylene-20,21-dinoreburnamenine acid maleate, [16α, (±)]-2,21-dinoreburnamenine-15-methanol acid maleate and [16α, (±)]-N,N-dimethyl-20,21-dinoreburnamenine-15-methanamine acid maleate.
An anti-depressant composition comprising an anti-depressantively effective amount of a compound selected from the group consisting of [16α, (±)]-15-(1-propynyl)-20,21-dinoreburnamenine oxylate, [16α, (±)]-14,15-dihydro-15-methylene-20,21-dinoreburnamenine acid maleate, [16α, (±)]-2-,21-dinoreburnamenine-15-methanol acid maleate and [16α, (±)]-N,N-dimethyl-20,21-dinoreburnamenine-15-methanamineacid maleate and an inert pharmaceutical carrier.
A method of treating depression in warm-blooded animals comprising administering to warm-blooded animals an anti-depressively effective amount of a compound selected from the group consisting of [16α,(±)]-15-(1-propynyl)-20,21-dinoreburnamenine oxylate, [16α, (±)]-14,15-dihydro-15-methylene-20,21-dinoreburnamenine acid maleate, [16α, (±)]-2-,21-dinoreburnamenine-15-methanol acid maleate and [16α, (±)]-N,N-dimethyl-20,21-dinoreburnamenine-15-methenamine acid maleate.
Dependencies are inferred from the claim text.