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A process for the preparation of solifenacin or a salt thereof

A technology of solifenacin and its compound, which is applied in the field of preparing high-purity solifenacin or its salt, can solve the problems of long reaction time, harmfulness, increased production cost, etc., and achieve the effect of high purity and high yield

Inactive Publication Date: 2015-03-11
PHARMATHEN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The above-mentioned method for the preparation of solifenacin base or its salt involves long reaction time, hazardous reagents and solvent distillation at high temperature, which leads to higher impurity formation and increased production cost

Method used

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  • A process for the preparation of solifenacin or a salt thereof
  • A process for the preparation of solifenacin or a salt thereof
  • A process for the preparation of solifenacin or a salt thereof

Examples

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preparation example Construction

[0057] Phase I) Preparation of Solifenacin Free Base

[0058] The reaction of a compound of formula II with a compound of formula III is carried out in a solvent, wherein R and R' are as defined above, selected from polar aprotic solvents such as dichloromethane, acetonitrile, dimethylformamide, tetrahydrofuran , ethyl acetate and a non-polar solvent such as toluene, cyclohexane or mixtures thereof, preferably acetonitrile. The reaction mixture is stirred at ambient temperature for about 3-6 hours, preferably for about 3-4 hours, more preferably until the reaction is complete. The completion of the reaction is monitored by any suitable technique such as thin layer chromatography (TLC) or high performance liquid chromatography (HPLC) or gas chromatography. Compounds of formula A or compounds of formula B can optionally be isolated by conventional techniques such as acid-base treatment, solvent extraction, column chromatography and crystallization or used directly in the next...

Embodiment 1

[0084] N,N'-Disuccinimidyl carbonate (14.4mmol, 3.69g) was added to (R)-3-quinribol (11.5mmol, 1.46g) in acetonitrile (50ml) stirred at ambient temperature in solution. The resulting mixture was stirred at ambient temperature for 4 hours. (1S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline (9.6mmol, 2.0g, chromatographic purity: 99.93%, chiral purity: 98.65%) in acetonitrile (25ml) The solution was added to the reaction mass and then stirred overnight. The reaction mixture was concentrated under reduced pressure. The residue was then diluted with toluene (10ml) and 1N hydrochloric acid (20ml) was added thereto. The reaction mixture was stirred and the phases were separated. The separated aqueous layer was basified with 20% sodium carbonate (20ml) solution, followed by extraction with ethyl acetate (20ml). The aqueous layer was re-extracted with ethyl acetate (10ml). The organic layers were combined and washed with water (10 ml), and the solvent therein was distilled off. To th...

Embodiment 2

[0086](R)-3-Quinuclear alcohol (110 mmol, 14 g) was added to a stirred solution of N,N'-disuccinimidyl carbonate (143 mmol, 36.8 g) in acetonitrile (60 ml) at ambient temperature. The resulting mixture was stirred at ambient temperature for 4 hours. (1S)-1-Phenyl-1,2,3,4-tetrahydroisoquinoline (95.6mmol, 20g, chromatographic purity: 99.99%, chiral purity: 99.0%) was added to the reaction mass and heated at 25 Stir at -35°C until the reaction is complete. The reaction mass was concentrated under reduced pressure. The residue was then diluted with toluene (100ml) and 1N hydrochloric acid (200ml) was added thereto. The reaction mixture was stirred and the phases were separated. The separated aqueous layer was basified with potassium carbonate to pH 9-10, followed by extraction with ethyl acetate (100ml). The aqueous layer was re-extracted with ethyl acetate (40ml). The organic layers of ethyl acetate were combined, washed with water (60 ml) and the solvent was distilled off....

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Abstract

The present invention relates to an improved process for the preparation of Solifenacin or its salt of formula I, more particularly the present invention relates to an economically viable and industrially advantageous process for the preparation of highly pure Solifenacin or its salt of formula I.

Description

field of invention [0001] The present invention relates to a kind of method that is used for the improvement of preparation Solifenacin (Solifenacin) or its salt, more particularly the present invention relates to a kind of method that is used to prepare high-purity Solifenacin or its salt economically feasible and industrially Favorable method. Background of the invention [0002] Solifenacin salts of formula I, especially solifenacin succinate as a muscarine M 3 - receptor antagonist and for the symptomatic treatment of urgency incontinence and / or increased frequency of urination and urgency of urination in patients with hyperactive bladder. Solifenacin is chemically known as (1S,3′R)-quinuclidin-3′-yl-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid ester. Commercially, solifenacin succinate is known under the trade name is available. [0003] [0004] EP0801067 discloses a process for the preparation of solifenacin, its racemic mixture or its biological...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D217/06C07D401/12C07D453/02
CPCC07D401/12C07D217/06C07D453/02A61P13/10A61P43/00
Inventor T·V·科夫提斯R·R·索尼B·B·博达R·C·古迪卡V·S·帕特尔
Owner PHARMATHEN
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