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Crystalline venlafaxine base and novel polymorphs of venlafaxine hydrochlorid, processes for preparing thereof

A technology of venlafaxine hydrochloride and solvate, which is applied in the field of venlafaxine and can solve problems such as not describing venlafaxine

Inactive Publication Date: 2007-12-26
TEVA PHARMA IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the '186 patent does not describe whether its obtained venlafaxine is a solid

Method used

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  • Crystalline venlafaxine base and novel polymorphs of venlafaxine hydrochlorid, processes for preparing thereof
  • Crystalline venlafaxine base and novel polymorphs of venlafaxine hydrochlorid, processes for preparing thereof
  • Crystalline venlafaxine base and novel polymorphs of venlafaxine hydrochlorid, processes for preparing thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Aqueous 32% sodium hydroxide (10.0 g, 80.0 mmol) was added to a stirred solution of venlafaxine hydrochloride (20.0 g, 63.7 mmol) in water (100 mL) in an ice-water bath. The mixture was stirred in an ice / water bath for about 30 minutes and extracted with ethyl acetate (3 x 30ml). The combined organic layers were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure at about 50-60°C (water bath). The residue was dissolved in boiling hexane (50ml) and cooled in a refrigerator (-18°C).

[0057] The resulting crystals were filtered off, washed with cold hexane (20 ml), and dried under reduced pressure to obtain 15.5 g (87.7%) of white venlafaxine crystals, whose purity was about 99.3% by HPLC, mp 78.3-79.5°C.

Embodiment 2

[0059] Preparation of crystalline venlafaxine free base from N,N-didesmethylvenlafaxine hydrochloride

[0060]

[0061] Aqueous 32% sodium hydroxide (2.75 g, 0.022 mol) was added to a stirred solution of N,N-didesmethylvenlafaxine hydrochloride (5.72 g, 0.02 mol) in water (13 ml) at room temperature. 88.5% aqueous formic acid (4.16 g, 0.08 mol) and 35.8% aqueous formaldehyde (3.7 g, 0.044 mol) were added to the emulsion. The resulting mixture was stirred at reflux for 8 hours, cooled to room temperature, adjusted to pH~11 with 32% aqueous sodium hydroxide solution, and extracted with heptane (100 ml).

[0062] The organic extract was washed with water (20ml), dried over sodium sulfate and evaporated to two volumes, and filtered to give crystalline venlafaxine base.

[0063] II) Venlafaxine Hydrochloride

[0064] The invention provides a method for purifying venlafaxine hydrochloride, which comprises alkalizing venlafaxine hydrochloride.

[0065] The invention provide...

Embodiment 3

[0119] Preparation of Type III and Type I with Solvents / Antisolvents

[0120] Ratio: 0.7ml water: 9.7ml acetone: 3 grams venlafaxine hydrochloride

[0121] Under reflux conditions, venlafaxine hydrochloride was dissolved in water and acetone was added. The resulting suspension was refluxed for a further 10 minutes and left overnight at room temperature. Afterwards, the suspension was filtered and washed with about 2 ml of the same solvent mixture. The resulting solid crystallized out as type III. Form I was obtained by further drying under reduced pressure (~10 mbar) for about 45 minutes (or more) in a rotary evaporator at about 60°C.

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Abstract

The present invention relates to novel essentially pure venlafaxine and the process of preparation thereof. The present invention also relates to novel solvate forms of venlafaxine hydrochloride and the process of preparation thereof. Furthermore, the present invention provides a novel process for preparing venlafaxine hydrochloride from venlafaxine; the process comprises the steps of: i) preparing a mixture of venlafaxine with acetone; and ii) exposing the mixture in gaseous hydrochoric acid.

Description

[0001] This application is an invention patent with an application date of October 19, 2001, an application number of 01820818.5, and an invention title of "Crystalline Venlafaxine Base and New Polymorphs of Venlafaxine Hydrochloride and Their Preparation Methods" Divisional application of the application. [0002] Cross-references to related applications [0003] This application claims provisional application serial numbers 60 / 241,577 (filed October 19, 2000), 60 / 258,861 (filed December 29, 2000), 60 / 278,721 (filed March 26, 2001), and 60 / 292,469 (filed Submitted on May 21, 2009) priority. The content of the aforementioned application is hereby incorporated by reference in its entirety. Background of the invention [0004] Venlafaxine (Venlafaxine), (±)-1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol having the structure of the following formula I is the first A class of antidepressants. Venlafaxine acts by inhibiting the reuptake of norepinephrine and seroto...

Claims

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Application Information

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IPC IPC(8): C07C213/10C07C217/74C07C217/60C07C209/84C07C215/42
Inventor B・－Z・多利茨基J・阿伦希梅S・维策尔G・尼斯内维斯
Owner TEVA PHARMA IND LTD
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