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A kind of method of reactive extraction separation pantoprazole enantiomer

A technology for pantoprazole and enantiomers, applied in the field of chemical separation engineering, can solve the problem of low selectivity, and achieve the effects of simple process, low cost and reduced production cost

Inactive Publication Date: 2016-04-20
HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] Aiming at the problem of low selectivity of conventional chiral extraction methods, this patent proposes a new method for extracting and separating the enantiomers of pantoprazole using dual-phase recognition chiral extraction technology

Method used

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  • A kind of method of reactive extraction separation pantoprazole enantiomer

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Experimental program
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Effect test

Embodiment 1

[0015] Dissolve an appropriate amount of R, S-pantoprazole and an appropriate amount of HP-β-CD in 0.1mol / L NaH 2 PO 4 / Na 2 HPO 4 In the buffer solution (pH=8.0), the concentration of the enantiomer of pantoprazole was controlled to be 5 mmol / L, and the concentration of HP-β-CD was 30 mmol / L to obtain an aqueous phase. At the same time, D-isobutyl tartrate, D-n-butyl tartrate, and D-isoamyl tartrate with a concentration of 0.4 mol / L were dissolved in 1,2-dichloroethane respectively, and the organic phase was obtained after thorough stirring. Take 10 mL each of the aqueous phase and the organic phase and put them into test tubes, shake in a constant temperature shaker in a water bath for 9 to 14 hours, and control the constant temperature at 25 °C. Thereafter, the two phases were kept at constant temperature for more than 24 hours. After the two phases are completely separated, the organic phase is extracted, and the water phase is analyzed by HPLC to obtain the concentrat...

Embodiment 2

[0017] Dissolve a certain amount of R,S-pantoprazole in 0.1mol / L NaH 2 PO 4 / Na 2 HPO 4 Buffer solution (pH = 8.5), and then dissolved in a certain concentration of hydroxypropyl-β-cyclodextrin (HP-β-CD), sulfobutyl ether-β-cyclodextrin (SBE-β-CD) , hydroxyethyl-β-cyclodextrin (HE-β-CD) and methyl β-cyclodextrin (Me-β-CD), the concentration of the control pantoprazole enantiomer is 10mmol / L, the ring The concentration of dextrin derivatives is maintained at 60mmol / L to obtain an aqueous phase, while a certain amount of D-isobutyl tartrate is dissolved in 1,2-dichloroethane and the concentration of D-isobutyl tartrate is kept at 0.1mol / L, the organic phase was obtained after thorough stirring. Take 10 mL each of the aqueous phase and the organic phase and put them into test tubes, shake in a constant temperature shaker in a water bath for 9 to 14 hours, and control the constant temperature at 25 °C. Thereafter, the two phases were kept at constant temperature for more tha...

Embodiment 3

[0019] Take appropriate amount of HP-β-CD dissolved in 0.1mol / L NaH 2 PO 4 / Na 2 HPO 4 In buffer solution, pH=6.5, HP-β-CD concentration is 35mmol / L. Control the enantiomeric concentration of pantoprazole in the above-mentioned solution respectively to be 2mmol / L, 4mmol / L, 6mmol / L, 8mmol / L, 10mmol / L, 12mmol / L, obtain six groups of solutions as the water phase. At the same time, a certain amount of isobutyl D-tartrate was dissolved in 1,2-dichloroethane to keep the concentration of isobutyl D-tartrate at 0.25 mol / L, and the organic phase was obtained after thorough stirring. Take 10 mL of the organic phase obtained above and place 10 mL of each of the six groups of water phases into different test tubes, and perform extraction operation in a constant temperature oscillator in a water bath (the constant temperature is controlled at 5°C). Mix well and let stand to separate the layers, so that the two phases reach equilibrium, then detect the extraction effect. The results sh...

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Abstract

The invention discloses a new method for separating pantoprazole enantiomers by reaction extraction, and a preparation method of new chiral pure pantoprazole. Racemic pantoprazole can be separated by biphasic recognition chiral extraction technology, and water soluble beta-cyclodextrin and tartaric acid ester are respectively used as chiral extractants in aqueous and organic phases. The invention discloses preparation methods of the aqueous and organic phases and repeated usage methods of the aqueous and organic phases. The extraction system has a very good separation performance on the racemic pantoprazole, distribution coefficients (kR and kS) are respectively 1.56 and 2.15, and separation factor (alpha) can reach 1.38.

Description

technical field [0001] The invention relates to a novel method for preparatively separating the enantiomers of pantoprazole, which belongs to the technical field of chemical separation engineering. The specific method is: using water-soluble β-cyclodextrin and tartrate as chiral extractant, and separating the enantiomers of pantoprazole through a two-phase recognition reaction extraction process. Background technique [0002] Pantoprazole (Pantoprazole) is the third-generation proton pump inhibitors (PPIs) developed and produced by BykGulden Pharmaceuticals in Germany in the late 1990s and first launched in Germany. Its full name is 5-difluoromethoxy- 2-[(3,4-Dimethoxy-2-pyridyl)methyl]sulfinyl-1H-benzimidazole sodium salt. It is clinically used to treat duodenal ulcer, gastric ulcer, Zoller-Ellison syndrome, and relieve moderate to severe reflux esophagitis, esophageal reflux disease (GEDR), erosive esophagitis, gastric and ten Duodenal ulcer, acute peptic ulcer bleeding ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12
CPCC07D401/12
Inventor 唐课文张盼良刘昶罗菁菁周从山华杰阎建辉候朝辉杨长安
Owner HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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