Method for separating chiral drug azelnidipine enantiomer through simulated moving bed chromatography technique

A technology of simulating moving bed and azedipine, which is applied in the field of separation of chiral drugs, can solve the problems of unsatisfactory large-scale industrial production and small preparation volume, and achieve the effect of low cost, less pollution and continuous production

Inactive Publication Date: 2016-08-03
WENZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This method has a good separation degree to the enantiomers of Azedipine, and the preparation amount is small, which cannot meet the industrialized large-scale production
At present, there is no domestic manufacturer of R-Azedipine, so it is necessary to realize the continuous production of Azedipine enantiomers by using simulated moving bed chromatography technology

Method used

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  • Method for separating chiral drug azelnidipine enantiomer through simulated moving bed chromatography technique
  • Method for separating chiral drug azelnidipine enantiomer through simulated moving bed chromatography technique

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Experimental program
Comparison scheme
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Embodiment 1

[0035] a. Operating conditions

[0036] Injection concentration: racemate Azeldipine concentration 20g / L

[0037] Injection liquid flow rate: U F =3.1ml / min

[0038] Eluent flow rate: U D =12.0ml / min raffinate flow rate: U R =6.9ml / min

[0039] Extraction flow rate: U E =5.8ml / min

[0040] Switching time: t s =1.5min

[0041] b. Separation step

[0042](1) Fully dissolve the racemate Azedipine in the prepared mobile phase, the concentration is 20g / L, as the feed liquid, the sample solution and the eluent are sequentially injected into the chromatographic system from the sample inlet and the eluent inlet , by simulating the controller of the moving bed chromatography system, the opening and closing of the pneumatic valve is regularly controlled, so that the eluting port, sample inlet, extract and raffinate outlets are regularly changed along the direction of the mobile phase, and the switching time is 1.5s. The two single enantiomers of Azedipine flow out of the syste...

Embodiment 2

[0049] a. Operating conditions

[0050] Injection concentration: racemate Azeldipine concentration 40g / L

[0051] Injection liquid flow rate: U F =2.4ml / min

[0052] Eluent flow rate: U D =18.0ml / min raffinate flow rate: U R =8.7ml / min

[0053] Extraction flow rate: U E =7.1ml / min

[0054] Switching time: t s =0.9min

[0055] b. Separation step

[0056] (1) Fully dissolve the racemate Azedipine in the prepared mobile phase, the concentration is 40g / L, as the feed liquid, the sample solution and the eluent are sequentially injected into the chromatographic system from the sample inlet and the eluent inlet , by simulating the controller of the moving bed chromatography system, the opening and closing of the pneumatic valve is regularly controlled, so that the eluting port, sample inlet, extract and raffinate outlets are regularly changed along the direction of the mobile phase, and the switching time is 0.9s, so that The two single enantiomers of Azedipine flow out of ...

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Abstract

A method for separating the enantiomers of the chiral drug Azedipine by simulated moving bed chromatography, using simulated moving bed chromatography to separate, and the product with a purity of 98% R-enantiomer can be obtained at the extraction port of one of the two outlets solution, the separation process is a continuous process. After simulated moving bed chromatographic separation, under suitable operating conditions, the purity of R-enantiomer can reach more than 98%, and the yield can reach 95%. The solvent can be recovered, the cost is low, and the pollution is less. Continuous production can be realized, which is beneficial to guarantee the product stable quality.

Description

technical field [0001] The invention relates to the technical field of separation technology of chiral drugs, in particular to a method for separating enantiomers of chiral drug azedipine by simulated moving bed chromatography. Background technique [0002] Azelnidipine ((±)-3-(1-diphenylmethyl-3-azetidinyl)-5-isopropyl-2-amino-1,4-dihydro -6-Methyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylate), English chemical name is 3-(1-(Diphenylmethyl)-3-azetidinyl)-5-isopropyl( ±)-2-amino-1,4-dihydro-6-methyl-4-(m-nitrophenyl)-3,5-pyridinedicarboxylate, the molecular structure formula is: [0003] [0004] It is a 1,4-dihydropyridine calcium ion antagonist jointly developed by Sankyo Company of Japan and Ube Company. It is a class of drugs currently used for the treatment of cardiovascular diseases. As a new generation of dihydropyridine drugs, azedipine can selectively act on L-type calcium channels, can effectively reduce the concentration of plasma inflammatory mediators in pat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12
CPCC07D401/12C07B2200/07
Inventor 徐进余卫芳陈永涛方瑛瑛
Owner WENZHOU UNIVERSITY
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