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Esomeprazole and its preparation method and application

A technology for esomeprazole and ufiprazole, applied in the field of medicine, can solve problems such as poor economy, inability to achieve energy saving and consumption reduction, and achieve the effects of high product yield, high utilization rate of raw materials, and low temperature

Inactive Publication Date: 2019-08-16
JIAXING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The first object of the present invention is to provide a kind of preparation method of esomeprazole, to improve the economical efficiency of the preparation method of existing esomeprazole is relatively poor and can't reach the technical problem of saving energy and reducing consumption, green environmental protection requirement

Method used

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  • Esomeprazole and its preparation method and application

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preparation example Construction

[0027] According to one aspect of the present invention, an embodiment of the present invention provides a method for preparing esomeprazole, comprising the following steps: under the action of a functional chiral ionic liquid with (D)-(-)-tartaric acid as an anion, Cooperate with catalyst, oxidant, organic solvent and pH adjuster to selectively oxidize prochiral thioether Ufprazole to generate esomeprazole.

[0028] Compared with the prior art, the preparation method of esomeprazole provided in the embodiment of the present invention has the following beneficial effects:

[0029] The preparation method of esomeprazole provided by the embodiment of the present invention can ensure that the raw material can be dissolved at a lower temperature with less solvent, and the method uses (D)-(-)-tartaric acid as an anionic functional As a chiral inducer, chiral ionic liquid not only retains the three-dimensional structure necessary for the catalytic oxidation of (D)-(-)-tartaric acid,...

Embodiment 1

[0078] Under the protection of nitrogen, 80mL of toluene, prochiral thioether Ufeprazole (6.6g, 20mmol), (D)-(-)-tartaric acid-N- n-Butyl-N-methylimidazole (2.9g, 10mmol) and Ti(O-iPr) 4 (1.7g, 6mmol), stirred and dissolved at room temperature, added diisopropylethylamine (0.77g, 6mmol), added dropwise cumene hydroperoxide (30.4g, 20mmol), and reacted at 25°C for 1.5h End, get esomeprazole.

[0079] In order to detect esomeprazole, continue to add methanol solution of sodium methoxide after the reaction and stir overnight (stirring time 6-12h), filter with suction, wash the filter cake with methanol, and dry to obtain white solid esomeprazole sodium 7.01 g, yield 95.4%. Esomeprazole sodium was analyzed by liquid chromatography: the purity was 86.8%, and the ee value was 84.3%.

Embodiment 2

[0081] Under the protection of nitrogen, 80 mL of toluene, prochiral thioether Ufeprazole (6.6 g, 20 mmol), (D)-(-)-tartaric acid-N- n-Butyl-N-methylimidazole (5.8g, 20mmol) and Ti(O-iPr) 4 (1.7g, 6mmol), stirred and dissolved at room temperature, added diisopropylethylamine (0.77g, 6mmol), added dropwise cumene hydroperoxide (30.4g, 20mmol), and reacted at 25°C for 1.5h End, get esomeprazole.

[0082] In order to detect esomeprazole, continue to add methanol solution of sodium methoxide after the reaction and stir overnight (stirring time 6-12h), filter with suction, wash the filter cake with methanol, and dry to obtain white solid esomeprazole sodium 7.05g, yield 95.9%. Esomeprazole sodium was analyzed by liquid chromatography: the purity was 85.9%, and the ee value was 85.2%.

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Abstract

The invention discloses esomeprazole as well as a preparation method and application thereof, relates to the technical field of medicines and aims to solve the technical problems that the existing preparation method of esomeprazole is low in economy and cannot meet the requirements of energy economization, consumption reduction, green and environment protection. The preparation method of the esomeprazole comprises a step of selectively oxidizing prochiral thioether ufiprazole into esomeprazole with cooperation of catalysts, oxidants, organic solvents and pH regulators under the action of functional chiral ionic liquid taking (D)-(-)-tartaric acid as anion. After the functional chiral ionic liquid taking (D)-(-)-tartaric acid as anion is added, the dissoluvability of the prochiral sulfide ufiprazole used as the raw material is obviously improved; the higher raw material utilization rate and selectivity can be ensured. The method has the advantages of simple step, easy operation, low consumption of solvents and low raw material dissolving temperature, so that the method is low in energy consumption, can meet the requirements of energy economization, consumption reduction, green and environment protection, and is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to a kind of esomeprazole and its preparation method and application. Background technique [0002] Esomeprazole is the first single optical isomer in the proton pump inhibitor family, which can inhibit the H + / K + -ATPase to reduce gastric acid secretion and prevent the formation of gastric acid, mainly used in the treatment of acid-related diseases such as peptic ulcer and gastroesophageal reflux disease. As a proton pump inhibitor with a single stereoisomer, esomeprazole is widely recognized for its relatively unique metabolic pathway, efficient and long-lasting acid-suppressing effect, good safety and low incidence of adverse reactions. More and more attention has become the drug of choice for clinically resistant peptic ulcer patients. [0003] In the prior art, the preparation methods of esomeprazole are usually the racemate resolution methods such as inclusion resolution...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12C07B53/00A61K31/4439A61P1/04
CPCA61K31/4439C07B53/00C07B2200/07C07D401/12
Inventor 张洋
Owner JIAXING UNIV
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