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Substantially pure O-desmethylvenlafaxine and processes for preparing it

a technology of odesmethylvenlafaxine and odesmethylvenlafaxine, which is applied in the field of substantial pure odesmethylvenlafaxine, can solve problems such as harm to patients

Inactive Publication Date: 2008-01-17
TEVA PHARM USA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0013] In one embodiment the present invention provides substantially pure O-desmethylvenlafaxine containing less than about 5% area

Problems solved by technology

Impurities in O-desmethylvenlafaxine or any active pharmaceutical ingredient (API) are undesirable and, in extreme cases, might even be harmful to a patient being treated with a dosage form containing the API.
The product mixture of a chemical reaction is rarely a single compound with sufficient purity to comply with pharmaceutical standards.
The API need not be absolutely pure, as absolute purity is a theoretical ideal that is typically unattainable.

Method used

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  • Substantially pure O-desmethylvenlafaxine and processes for preparing it
  • Substantially pure O-desmethylvenlafaxine and processes for preparing it
  • Substantially pure O-desmethylvenlafaxine and processes for preparing it

Examples

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Effect test

example 1

Preparation of O-Desmethylvenlafaxine in NMP

[0104] Venlafaxine (50 g, 180 mmol), thiophenol (20 ml, 195 mmol), K2CO3 (1 g, 6 mmol), and NMP (90 ml) were charged in a 500 ml 3 necks flask equipped with stirrer, condenser and thermometer. The mixture was heated to 190° C. After 5 hours at 190° C. the heating bath was removed. (less than 1.5% VNL). At 80° C. IPA (300 ml) was added. The solution was cooled to 0-5° C. overnight. The solid was filtered under reduced pressure and washed with IPA and water. The solid was then dried overnight at 50° C. under vacuum to get pure ODV base. ODV was obtained with a purity of 97% and an Assay of 93.5%.

example 2

Preparation of O-Desmethylvenlafaxine in NMP

[0105] To one neck flask equipped with magnetic stirrer, dean stark, condenser and thermometer were added at room temperature under flow of nitrogen VNL (5 g, 18.2 mmol), Na2S Hydrate (1.58 g, 12 mmol, assay >60%) and NMP (12 ml). The reaction mixture was heated to 150° C. in 1 hour and kept at this temperature for 7.5 hours. Then the reaction mixture was cooled to room temperature and stirred overnight at this temperature. Afterwards Na2S hydrate (0.71 g, 5.4 mmol, assay >60%) was added. The mixture was heated to 165° C. in 1 hour and kept at this temperature for 5 hours. After this time the reaction was cooled to 40° C., EPA (30 ml) and a 10% aqueous solution of citric acid (20 ml) were added slowly through a dropping funnel until light precipitation was observed (pH 10). The suspension was stirred over weekend at room temperature and the solid was filtered under reduced pressure and washed with IPA (20 ml). The solid was dried overnigh...

example 3

Preparation of O-Desmethylvenlafaxine Under Pressure

[0106] A 250 ml autoclave is charged with 5 g VNL (0.0182 mol), 3.81 g Sodium Ethanethiolate (0.0458 mol, 2.5 eq) and NMP (10 ml). The reaction mixture is stirred from 30° C. to 220° C. and 1-20 bar pressure for 4 h. The mixture is then cooled to room temperature. At ambient temperature IPA (10 ml) and water (10 ml) are added. To this mixture a 10% aqueous solution of citric acid is added in order to reach pH about 12. A solid begins to precipitate and is stirred at RT for 2.5 h. The solid is then filtered under reduced pressure and washed with solvent. The wet cake is dried in a vacuum oven at 50° C. to obtain pure ODV.

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Abstract

Methods for preparing substantially pure O-desmethylvenlafaxine are described.

Description

CROSS REFERENCE TO RELATED APPLICATIONS [0001] The present application claims the benefit of the following U.S. Provisional Patent Application Nos. 60 / 792,801, filed Apr. 17, 2006; 60 / 796,739, filed May 1, 2006; 60 / 899,166, filed Feb. 1, 2007; 60 / 902,418, filed Feb. 20, 2007; 60 / 872,955, filed Dec. 4, 2006; and 60 / 903,988, filed Feb. 27, 2007. The contents of these applications are incorporated herein by reference.FIELD OF THE INVENTION [0002] The invention encompasses substantially pure O-desmethylvenlafaxine. BACKGROUND OF THE INVENTION [0003] Venlafaxine, (±)-1-[2-(Dimethylamino)-1-(4-ethyoxyphenyl)ethyl]cyclo-hexanol is the first of a class of anti-depressants. Venlafaxine acts by inhibiting re-uptake of norepinephrine and serotonin, and is an alternative to the tricyclic anti-depressants and selective re-uptake inhibitors. Venlafaxine has the following chemical formula, Formula I: [0004] O-desmethylvenlafaxine, 4-[2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl]phenol, is a maj...

Claims

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Application Information

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IPC IPC(8): C07C211/27A61K31/135C07C209/00
CPCC07B2200/13C07C213/00C07C213/10C07C215/64C07C2101/14C07C2601/14A61P25/24A61P43/00C07C217/74
Inventor NIDDAM-HILDESHEIM, VALERIE
Owner TEVA PHARM USA INC
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