Method for splitting pinocembrin enantiomers through simulated moving bed chromatography

A technique of simulating moving bed and pinocerine, which is applied in the field of separation of chiral drugs, can solve problems such as no public reports, and achieve the effect of simple process and stable product quality

Inactive Publication Date: 2014-05-14
JIANGSU HANBON SCI & TECH CO
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  • Summary
  • Abstract
  • Description
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  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In recent years, simulated moving bed chromatography technology has achieved rapid development in the separation of ...

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0028] 1. Sample preparation: The sample is dissolved in methanol to a concentration of 5g / L, filtered through a 0.45um organic filter membrane for use;

[0029] 2. Selection of simulated moving bed parameters: The parameters are determined as follows: injection flow rate 0.3mL / min, elution flow rate 2.0mL / min, extract flow rate 1.2mL / min, raffinate flow rate 1.1mL / min, switching time 13min, The temperature is controlled at 20-30℃;

[0030] 3. Product collection: After the simulated moving bed system is operating stably, collect the products from the two outlets respectively, and obtain the final product after concentration under reduced pressure and recrystallization;

[0031] 4. Finished product inspection: After the obtained product is dissolved in the mobile phase, the purity of the two export products R-pinocerin and S-pinocerin are 97.3% and 98.1%, respectively;

[0032] Each kilogram of stationary phase can produce 0.55kg of R-pinoselin and S-pinoselin each day, the consumption...

example 2

[0035] 1. Sample preparation: the sample is dissolved in methanol to a concentration of 10g / L, filtered through a 0.45um organic filter membrane for use;

[0036] 2. Selection of simulated moving bed parameters: Determine the parameters as follows: injection flow rate 0.6mL / min, elution flow rate 4.2mL / min, extract flow rate 2.6mL / min, raffinate flow rate 2.2mL / min, switching time 12min, The temperature is controlled at 20-30℃;

[0037] 3. Product collection: After the simulated moving bed system runs stably, collect the products from the two outlets respectively, and obtain the final product after concentration under reduced pressure and recrystallization;

[0038] 4. Finished product inspection: After the obtained product is dissolved in the mobile phase, the purity of the two export products R-pinocerin and S-pinocerin is 97.3% and 97.9%, respectively;

[0039] Each kilogram of stationary phase can produce 1.26kg of R-pinocerin and S-pinocerin each day, the mobile phase consumption...

example 3

[0042] 1. Sample preparation: the sample is dissolved in methanol to a concentration of 20g / L, filtered through a 0.45um organic filter membrane for use;

[0043] 2. Selection of simulated moving bed parameters: Determine the parameters as follows: injection flow rate 1.2mL / min, elution flow rate 6.8mL / min, extract flow rate 4.2mL / min, raffinate flow rate 3.8mL / min, switching time 11min, The temperature is controlled at 20-30℃;

[0044] 3. Product collection: After the simulated moving bed system runs stably, collect the products from the two outlets respectively, and obtain the final product after concentration under reduced pressure and recrystallization;

[0045] 4. Finished product inspection: After the obtained product is dissolved in the mobile phase, the purity of the two export products R-pinoselin and S-pinoseline are 97.3% and 98.3% respectively;

[0046] Each kilogram of stationary phase can produce 2.32kg of R-pinocerin and S-pinocerin each day, the mobile phase consumptio...

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PUM

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Abstract

The invention discloses a method for splitting pinocembrin enantiomers through simulated moving bed chromatography. The method is characterized in that a simulated moving bed chromatographic system is adopted, a filler is amylase-tri(3,5-dimethylphenylcarbamate), a mobile phase is methanol, and the naproxen pinocembrin are split under normal phase conditions to obtain highly pure R-pinocembrin and S-pinocembrin. The simulated moving bed chromatographic system has the advantages of continuous production, high automation degree and high production efficiency.

Description

Technical field [0001] The invention relates to a separation technology of chiral drugs, in particular to a simulated moving bed chromatographic separation method of pinoseline. Background technique [0002] Pinocembrin, its chemical name is 2,3-dihydro-5,7-dihydroxy-2-phenyl-4H-1-benzopyran-4-one (2,3-dihydro- 5,7-d ihydroxy-2-phenyl-4H-1-benzopyran-4-one), originally a flavanone compound with multiple biological activities obtained from propolis. In the process of pharmacological screening, it was discovered for the first time that racemic pinoxerine has significant protective activity on the neurovascular unit (NVU) of acute cerebral ischemia rats, which can significantly reduce the percentage of cerebral edema and cerebral infarction volume, and improve neurobehavioral It has the characteristics of treating acute cerebral ischemia and has good development prospects. The molecular structure of pinocerin contains a chiral center, there is a pair of optical isomers, the natura...

Claims

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Application Information

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IPC IPC(8): C07D311/32
CPCC07D311/32
Inventor 张大兵张宁刘玉明罗军侠王亚辉
Owner JIANGSU HANBON SCI & TECH CO
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