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Chiral resolution method for four isomers in raceanisodamine

A technology for anisodamine and chiral separation, applied in the field of medicine, can solve the problems of inapplicability to large-scale industrial production, small preparation amount, and long time consumption, and achieve reasonable design, reduced separation cost, and high product yield Effect

Active Publication Date: 2018-10-26
HARBIN MEDICAL UNIVERSITY
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  • Description
  • Claims
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Problems solved by technology

The patent application with the publication number CN107991367A tries to use capillary electrophoresis to separate the four optical isomers of anisodamine, but due to the defects of long time consumption and small preparation amount, the method is limited to laboratory preparation and cannot be applied to industrial mass production

Method used

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  • Chiral resolution method for four isomers in raceanisodamine
  • Chiral resolution method for four isomers in raceanisodamine
  • Chiral resolution method for four isomers in raceanisodamine

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Embodiment 1

[0026] The chiral resolution of four isomers in embodiment 1 racemic anisodamine

[0027] 1. Sample preparation

[0028] The racemic anisodamine sample (sample concentration: 100 mg / mL) was completely dissolved in an aqueous solution containing 45% (v / v) methanol, passed through a 0.22 μm microporous membrane for use.

[0029] 2. HPLC chromatographic separation

[0030] Mobile phase: a mixed solution of methanol, water and diethylamine, wherein the volume ratio of methanol:water:diethylamine=45:55:0.02.

[0031] Chromatographic conditions: the detection wavelength is 210nm, the chromatographic column is an Agilent Prep C18 column (250mm×9.4mm), the column temperature is 20°C, the injection volume is 1mL, and the flow rate is 5mL / min.

[0032] The separated product was analyzed by HPLC under the following conditions: the mobile phase methanol: water: diethylamine volume ratio was 50:50:0.02, the chromatographic column was a cosmosil MS-II C18 column, the column temperature wa...

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Abstract

The invention discloses a chiral resolution method for four isomers in raceanisodamine. According to the chiral resolution method, di-p-toluoyl-D-tartaric acid or di-p-toluoyl-L-tartaric acid is usedas a resolving agent and the raceanisodamine is resolved by utilizing a preparation type HPLC (High Performance Liquid Chromatography) combined chemical resolution method. The method is reasonable indesign and is practicable and feasible; a product has relatively great yield and high purity and the purity of the obtained four isomers including 6R,2'R, 6R,2'S, 6S,2'S and 6S,2'R of anisodamine is greater than 95 percent; the method is a relatively effective method for industrially producing four optical isomers of the anisodamine. According to the method disclosed by the invention, the resolution of the four optical isomers is successfully realized and the resolution cost of the four optical isomers of the anisodamine can be effectively reduced; the method has wide social benefits, great economic benefits and a wide application prospect.

Description

technical field [0001] The invention relates to a chiral resolution method for four isomers in racemic anisodamine, through which the chiral resolution of four optical isomers in racemic anisodamine can be realized. The invention belongs to the technical field of medicine. Background technique [0002] Anisodamine can compete with acetylcholine to antagonize M receptors, and is used for the treatment of smooth muscle spasm, neuralgia, fulminant meningitis, bacterial meningitis, toxic dysentery and circulatory disorders caused by vasospasm. Racemic anisodamine is a synthetic product of anisodamine (654-2), which contains four optical isomers, respectively 6R, 2'S, 6S, 2'R, 6R, 2'R, 6S, 2'S configurations. Relevant animal experiments have proved that the 6S, 2'S isomer exhibits the strongest pharmacological activity in terms of the relaxation effect of the isolated rat trachea. On the relaxation effect of isolated rat small intestinal smooth muscle, 6R, 2'S isomer showed the...

Claims

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Application Information

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IPC IPC(8): C07D451/10
CPCC07D451/10
Inventor 杨宝峰李畅朱久新王立波韩维娜黄健王金辉
Owner HARBIN MEDICAL UNIVERSITY
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