Simulated moving bed chromatography separating method of omeprazole antimer

A simulated moving bed and omeprazole technology, which is applied in the field of simulated moving bed chromatography separation of omeprazole enantiomers, can solve the problem of unavailable raw materials for preparation of chiral stationary phases, expensive commercial stationary phases, and high production costs. problems, to achieve the effect of stable product quality, continuous production and simple process

Inactive Publication Date: 2005-10-19
NINGBO INST OF TECH ZHEJIANG UNIV ZHEJIANG
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  • Application Information

AI Technical Summary

Problems solved by technology

The raw materials for the preparation of the chiral stationary phase (amylose-[tri(S)-methylphenylcarbamate]) used in th

Method used

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  • Simulated moving bed chromatography separating method of omeprazole antimer
  • Simulated moving bed chromatography separating method of omeprazole antimer
  • Simulated moving bed chromatography separating method of omeprazole antimer

Examples

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example 1

[0039] a. Operating conditions

[0040] Mobile phase: pure ethanol

[0041] Injection concentration: racemic omeprazole concentration 20mg / ml

[0042] Injection liquid flow rate: U F =5ml / min

[0043] Eluent flow rate: U E =23.5ml / min

[0044] Raffinate flow rate: U R =10ml / min

[0045] Extraction flow rate: U X =18.5ml / min

[0046] Switching time: t S =0.89min

[0047] b. Finished product analysis

[0048] The raffinate and extract compositions were analyzed with a Chiralpak AD column. The purity of S-(-)-omeprazole in the raffinate was 99.48, and the purity of R-(+)-omeprazole in the extract was 98.65%. Each kilogram of stationary phase can produce 1.3kg of S-(-)-omeprazole and R-(+)-omeprazole per day, and the mobile phase consumption is 0.578m 3 / Kg, the recovery rate of S-(-)-omeprazole is 98.64%.

example 2

[0050] a. Operating conditions

[0051] Mobile phase: pure ethanol / diethylamine (100 / 1)

[0052] Injection concentration: racemic omeprazole concentration 40mg / ml

[0053] Injection liquid flow rate: U F =4ml / min

[0054] Eluent flow rate: U E =11.2ml / min

[0055] Raffinate flow rate: U R =5.4ml / min

[0056] Extraction flow rate: U X =9.8ml / min

[0057] Switching time: t s =1.04min

[0058] b. Finished product analysis

[0059] The raffinate and extract compositions were analyzed with a Chiralpak AD column. The purity of S-(-)-omeprazole in the raffinate was 98.84%, and the purity of R-(+)-omeprazole in the extract was 99.45%. Each kilogram of stationary phase can produce 2.1kg of S-(-)-omeprazole per day, and the mobile phase consumption is 0.25m 3 / Kg, the recovery rate of S-(-)-omeprazole is 99.45%.

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Abstract

The present invention discloses the chromatographic separation process of omeprazole antimer in simulated mobile bed. In a simulated mobile bed chromatographic system with chiral fixed phase of cellulose triphenyl carbomate and flow phase of the mixture of ethanol, n-hexane and diethylamine, mixture of R-(+)-omeprazole and S-(-)-omeprazole is separated to obtain high purity S-(-)-omeprazole. Said separation process is a continuous process, so that the present invention has high automation, high production efficiency, low solvent consumption and no toxic solvent.

Description

technical field [0001] The invention relates to the separation technology of chiral drugs, in particular to a simulated moving bed chromatographic separation method of omeprazole enantiomers. Background technique [0002] Omeprazole, namely 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzene And imidazole, the English chemical name is 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole, the molecular structure formula is: [0003] [0004] It is a novel proton pump inhibitor (Propton pump inhibitors, PPIs) antiulcer drug synthesized by Sweden Haessel Company and produced by Sweden Astra Company, which is used for the treatment of duodenal ulcer, gastric ulcer and reflux esophagitis, and It can eliminate the phenomenon of refractory ulcer, and is also very effective for Zoller-Ellison syndrome, and has few adverse reactions. At present, it has become the best-selling drug with the largest annual sales of a single dr...

Claims

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Application Information

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IPC IPC(8): A61P1/04C07D401/12
Inventor 危凤沈波刘本陈明杰陆雄鹰
Owner NINGBO INST OF TECH ZHEJIANG UNIV ZHEJIANG
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