Novel process for preparing (+)-cis-sertraline
AssigneeTeva Pharmaceutical Industries Ltd.
InventorsMarioara Mendelovici, Tamar Nidam, Gideon Pilarsky, Neomi Gershon
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Abstract
The present invention is directed to (+)-cis-sertraline hydrochloride and methods of preparation. The present invention also includes processes for making sertraline having a cis/trans ratio greater than 3:1, greater than or equal to 8:1, or between about 8:1 and about 12:1, from the Schiff base of sertralone, sertraline-1-imine.
Claims47
A process for making (±)-sertraline having a cis/trans ratio of greater than about 3:1 comprising the step of hydrogenating sertraline-1-imine at a temperature of at least about 40° C. using a catalyst selected from the group consisting of palladium and platinum.
A process for making (+)-cis-sertraline hydrochloride from (±)-sertraline base comprising the steps of:
- (a) reacting an optically active selective precipitant with (±)-sertraline base wherein the (±)-sertraline base has a cis/trans ratio of greater than about 3:1 to form a (+)-cis-sertraline-precipitant;
- (b) reacting the (+)-sertraline-precipitant with a basic solution to facilitate the formation of the (+)-sertraline base;
- (c) reacting the (+)-sertraline base with hydrochloric acid to facilitate the precipitation of (+)-cis-sertraline hydrochloride;
- and
- (d) isolating (+)-cis-sertraline hydrochloride.
A process for making (+)-cis-sertraline hydrochloride from (±)-sertraline hydrochloride having a cis/trans ratio of greater than 3:1 comprising the steps of:
- (a) generating (±)-sertraline base by addition of an aqueous base to (±) sertraline hydrochloride with a cis/trans ratio of greater than 3:1;
- (b) resolving the (±)-sertraline base so generated to form (+)-sertraline base;
- (c) reacting the (+)-sertraline base with hydrochloric acid to facilitate the precipitation of (+)-cis-sertraline hydrochloride;
- and
- (d) isolating (+)-cis-sertraline hydrochloride.
A process for making (+)-cis-sertraline hydrochloride from (±)-sertraline hydrochloride comprising the steps of:
- (a) generating (±)-sertraline base by addition of a solid base to (±)-sertraline hydrochloride;
- (b) resolving the (±)-sertraline base so generated to form (+)-sertraline base;
- (c) reacting the (+)-sertraline base with hydrochloric acid to facilitate the precipitation of (+)-cis-sertraline hydrochloride;
- and
- (d) isolating (+)-cis-sertraline hydrochloride
Dependencies are inferred from the claim text.