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Process for the preparation of O-desmethylvenlafaxine

A technology for desvenlafaxine and methanol, which is applied in chemical instruments and methods, preparation of organic compounds, preparation of aminohydroxyl compounds, etc., and can solve problems such as long processing time, inconvenient needs, long reaction time, etc.

Inactive Publication Date: 2011-08-24
GENERICS UK LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method has the disadvantage of requiring an inconveniently long reaction time of about 30 hours
[0014] Therefore, the methods disclosed in the prior art have some disadvantages, such as moderate to low yields; impurity of ODV(II) obtained; very high temperatures; long processing times; Expensive, toxic and / or hazardous reagents such as tri-sec-butyl lithium borohydride, ethanethiol, boron tribromide and n-butyl lithium are not recommended in

Method used

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  • Process for the preparation of O-desmethylvenlafaxine
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  • Process for the preparation of O-desmethylvenlafaxine

Examples

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Embodiment 1

[0084] Example 1: Preparation of ODV bases from venlafaxine bases using thiourea

[0085] Thiourea (13.7 g, 0.18 mol) was added to a suspension of potassium hydroxide (20.2 g, 0.36 mol) in polyethylene glycol 400 (50 mL) at 25-30°C. Venlafaxine base (10 g, 0.04 mol) was added to the suspension with stirring and the reaction mixture was heated to 170-180°C. After completion of the reaction (16-20 hours), the reaction mixture was cooled to 60-70° C., and water (40 mL) was added, followed by 35% aqueous hydrochloric acid (15-20 mL). The solution was washed with dichloromethane (2x50 mL). To this aqueous solution was added 25% aqueous ammonia to adjust the pH of the solution to >9.5. A solid precipitated out and was filtered to give crude ODV base. Additional crude ODV base was added to methanol (250 mL), refluxed for 1 h, then cooled to 10-15 °C. The crystallized pure ODV base was filtered off and dried at 50-55°C. Instead of crystallization in methanol, the crude ODV base ...

Embodiment 2

[0089] Example 2: Preparation of ODV base from venlafaxine hydrochloride using thiourea

[0090] Thiourea (12.1 g, 0.16 mol) was added to a suspension of potassium hydroxide (17.8 g, 0.32 mol) in polyethylene glycol 400 (50 mL) at 25-30°C. Venlafaxine hydrochloride (10.0 g, 0.03 mol) was added to the suspension with stirring, and the reaction mixture was heated to 170-180°C. After the reaction was complete (16-20 hours), the reaction mixture was cooled to 60-70°C and water (40 mL) was added, followed by 35% aqueous hydrochloric acid (15-20 mL). The solution was washed with dichloromethane (2x50 mL). To this aqueous solution was added 25% aqueous ammonia to adjust the pH of the solution to >9.5. A solid precipitated out and was filtered to give crude ODV base. The crude ODV base was crystallized in methanol and dried to give pure ODV base as an off-white solid. Instead of crystallization in methanol, the crude ODV base was purified by acid / base purification in methanol by...

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Abstract

The present invention provides a convenient and efficient process for the preparation of O-desmethylvenlafaxine (ODV) or a salt thereof, comprising the reaction of venlafaxine, or a salt thereof, with a thiourea or a mixture of thioureas.

Description

technical field [0001] The present invention provides a convenient and effective method for preparing O-desvenlafaxine (ODV) or its salt, comprising reacting venlafaxine or its salt with thiourea or a mixture of thioureas. Background technique [0002] The chemical name of O-desmethylvenlafaxine (ODV, II) is 1-[1-(4-hydroxyphenyl)-2-(dimethylamino)ethyl]-cyclohexanol, which is the The major metabolite of farxine. ODV is known to inhibit norepinephrine and serotonin uptake and has antidepressant activity. It has been further reported that oral administration of ODV succinate, especially oral administration of sustained-release ODV succinate, can induce nausea, vomiting, diarrhea, abdominal pain, headache, vaso-vagal discomfort (vaso-vagal discomfort) compared with oral administration of venlafaxine. -vagal malaise) and / or trismus were less common. ODV is known to be effective in treating patients with depression, anxiety and panic disorders. [0003] Various prior art pat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C213/08C07C215/64A61K31/135A61P25/24
CPCC07C215/64C07C213/08A61P13/00A61P13/10A61P15/00A61P15/10A61P21/00A61P25/00A61P25/14A61P25/16A61P25/18A61P25/22A61P25/24A61P25/30A61P25/32A61P25/36A61P3/04A61P9/00
Inventor 维纳亚克·戈雷维纳伊·库玛·舒克拉马杜卡尔·帕蒂尔
Owner GENERICS UK LTD
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