Preparation method for impurity of Solifenacin succinate

A solifenacin succinate impurity technology, which is applied in the field of preparation of solifenacin succinate impurity [Formula (I)], can solve the problems of compound preparation methods without literature reports, etc., and achieve high product purity and excellent reaction operation simple effect

Active Publication Date: 2016-02-24
天津市医药集团技术发展有限公司 +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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  • Preparation method for impurity of Solifenacin succinate
  • Preparation method for impurity of Solifenacin succinate

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Embodiment 1

[0027] Get 5g of solifenacin succinate, stir and dissolve in the mixed solvent of 50ml of water and 5ml of acetone. Add 5.6g of potassium permanganate, stir at 20-25°C for 8h, and let stand overnight. The conversion rate of [2-(2-benzoyl-phenyl)-ethyl]-carbamic acid 1-aza-bicyclo[2.2.2]oct-3-yl ester was 45% by HPLC the next day. Filter, add 25ml of ethyl acetate for layering, adjust the pH to 9~10 with saturated potassium carbonate solution, and extract the aqueous layer with 25ml×2 ethyl acetate. The organic layers were combined and dried over anhydrous magnesium sulfate for 2 h. The desiccant was filtered off and concentrated under reduced pressure to obtain 3.4 g of a yellow oil. Separation by column chromatography (dichloromethane / methanol=15 / 1), TLC (dichloromethane / methanol=10 / 1) to monitor the separation process, collect the eluent, and concentrate under reduced pressure to dryness to obtain a white solid [2-(2 -Benzoyl-phenyl)-ethyl]-carbamic acid 1-aza-bicyclo[2.2...

Embodiment 2

[0030] Get 10g of solifenacin succinate, stir and dissolve in a mixed solvent of 100ml of water and 10ml of acetone. Add 11.2g of potassium permanganate, stir at 20-25°C for 8h, and leave overnight. The conversion rate of [2-(2-benzoyl-phenyl)-ethyl]-carbamic acid 1-aza-bicyclo[2.2.2]oct-3-yl ester was 54.6% by HPLC the next day. Filter, add 50ml of dichloromethane and 5% sodium hydroxide solution to adjust the pH to 9~10, separate the water layer, extract the water layer with 50ml×2 dichloromethane, combine the organic layers and dry with anhydrous magnesium sulfate for 2h. The desiccant was filtered off and concentrated under reduced pressure to obtain 6.5 g of a yellow oil. Separation by column chromatography (dichloromethane / methanol=15 / 1), TLC (dichloromethane / methanol=10 / 1) to monitor the separation process, collect the eluent, and concentrate under reduced pressure to dryness to obtain a white solid [2-(2 -Benzoyl-phenyl)-ethyl]-carbamic acid 1-aza-bicyclo[2.2.2]oct-3...

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Abstract

The invention relates to a preparation method for an impurity of Solifenacin succinate, i.e., [2-(2-benzoyl-phenyl)-ethyl]-1-aza-bicyclo[2.2.2]octyl-3-carbamate. The impurity is prepared through carrying out oxidation ring-opening on Solifenacin succinate and then carrying out separation and purification. According to the preparation method, through preparing the impurity of Solifenacin succinate, a reference substance for qualitative and quantitative analysis on Solifenacin succinate is provided, the quality of Solifenacin succinate is effectively controlled, and thus the safety of clinical medication is guaranteed.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry and relates to a preparation method of solifenacin succinate impurity [formula (I)]. Background technique [0002] Solifenacin succinate [Formula (Ⅱ)], English name: Solifenacinsuccinate, trade name: Vesicare, is a new generation of highly selective M-receptor inhibitor developed by Japan Astellas Pharmaceutical Co., Ltd. (formerly Yamanouchi Pharmaceutical Co., Ltd.) Intervention is a drug used to treat symptoms of urinary incontinence and / or urinary frequency and urgency in patients with overactive bladder (OAB). The drug first went on the market in Europe in August 2004, and is currently on the market in more than 50 countries around the world. It was approved for marketing in China in 2009. [0003] [0004] The compound of the present invention [2-(2-benzoyl-phenyl)-ethyl]-carbamic acid 1-aza-bicyclo[2.2.2]oct-3-yl ester [formula (I)] is Japanese Ann A kind of ring-opening me...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D453/02
Inventor 杨汉跃郑家通陈学民陈琛孟庆礼李瑞敏
Owner 天津市医药集团技术发展有限公司
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