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Preparation method of esomeprazole and magnesium salt thereof

A technology of esomeprazole magnesium and compounds, which is applied in the field of pharmaceutical chemical synthesis, can solve the problems of less application and instability, and achieve the effects of improving the reaction system, being easy to realize, and reducing production costs

Active Publication Date: 2016-01-20
KAIFENG MINGREN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Generally, esomeprazole magnesium refers to esomeprazole magnesium (trihydrate), in addition to esomeprazole magnesium (dihydrate), but due to its instability, it is less used in daily production

Method used

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  • Preparation method of esomeprazole and magnesium salt thereof
  • Preparation method of esomeprazole and magnesium salt thereof
  • Preparation method of esomeprazole and magnesium salt thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] b. Add methanol to the obtained compound II, the amount of methanol added is 3 times the mass of compound II, add methanol and stir and mix evenly to obtain compound II methanol solution;

[0043] Add methanol and sodium hydroxide solution to 5-methoxy-2-mercaptobenzimidazole, compound III, stir and mix evenly to obtain a compound III solution; the amount of methanol added is 3 times the mass of compound III, and the hydroxide The amount of sodium added is twice the molar number of compound III; the sodium hydroxide is formulated into a solution with a concentration of 50% by mass;

[0044] c. At 25°C, add the compound II methanol solution obtained in step b to the compound III solution dropwise. The volume ratio between the compound III solution and the compound II methanol solution is 1.5:1. Finally, the reaction was carried out at 25°C for 1.5 hours. After the reaction, crystallization, filtration, water washing and drying were carried out in sequence. After drying, ...

Embodiment 2

[0055] In step b: the amount of methanol added is twice the mass of compound II;

[0056] The amount of methanol added is twice the mass of compound III, and the amount of sodium hydroxide added is 1.5 times the molar number of compound III;

[0057] In step c: at 10°C, the compound II methanol solution obtained in step b is added dropwise to the compound III solution, the volume ratio between the compound III solution and the compound II methanol solution is 1.8:1, dropwise After completion, the reaction was carried out at 10°C, and the reaction time was 2 hours;

[0058] In step d: Stir evenly, raise the temperature to 50°C, keep warm at this temperature for 3h, then cool to room temperature, then add 1,3-propylenediamine, lower the temperature to -5~0°C, then slowly add peroxide After the tert-amyl benzoate and tert-amyl peroxybenzoate are added dropwise, the temperature is raised to 5-10°C for reaction, and the reaction lasts for 1.5 hours. After the reaction, the obtaine...

Embodiment 3

[0063] In step b: the amount of methanol added is 4 times the mass of compound II;

[0064] Add methanol and potassium hydroxide solution to 5-methoxy-2-mercaptobenzimidazole, i.e. compound III, the amount of methanol added is 4 times the mass of compound III, and the amount of potassium hydroxide added is the number of moles of compound III 3 times;

[0065] In step c: under the condition of 30°C, add the compound II methanol solution obtained in step b to the compound III solution dropwise, the volume ratio between the compound III solution and the compound II methanol solution is 1.2:1, drop After the addition, the reaction was carried out at 30°C, and the reaction time was 0.5h;

[0066] In step d: Stir evenly, raise the temperature to 70°C, keep warm at this temperature for 1.5h, then cool to room temperature, then add methylamine, lower the temperature to -15~-10°C, then slowly add disuccinic acid peroxide dropwise , After adding disuccinic acid peroxide dropwise, the ...

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Abstract

The invention discloses a preparation method of esomeprazole and its magnesium salt. Using 4-methoxy-2-hydroxymethyl-3,5-lutidine as raw material, react with hydrobromic acid to obtain 4-methoxy-2-bromomethyl-3,5-lutidine Compound II; compound II methanol solution was added dropwise to compound III methanol solution to react to obtain 5-methoxy-2-(4-methoxy-3,5-dimethyl-2-pyridyl)methylthio- 1H-benzimidazole is compound IV; compound IV is dissolved in dichloromethane, adding D-diethyl tartrate, tetrabutyl titanate and water to react to obtain esomeprazole; reacting esomeprazole with magnesium methanol Get esomeprazole magnesium. Utilizing the technical scheme of the invention to prepare esomeprazole and its magnesium salt can effectively reduce the production cost.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical chemical synthesis, in particular to a preparation method of esomeprazole and its magnesium salt. Background technique [0002] Esomeprazole is a proton pump inhibitor that reduces gastric acid secretion and prevents the formation of gastric acid by inhibiting the H+ / K+-ATPase of gastric parietal cells. The chemical name of esomeprazole is 5-methoxy-2-((S)-((4-methoxy-3,5-dimethyl-2-pyridyl)methyl)sulfinyl) -1H-benzimidazole. [0003] The chemical name of esomeprazole magnesium is 5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]benzimidazole-1 - Base Magnesium. Esomeprazole magnesium is suitable for the treatment of gastroesophageal reflux disease, erosive reflux esophagitis, long-term maintenance treatment of cured esophagitis patients to prevent recurrence and other diseases. Generally, esomeprazole magnesium refers to esomeprazole magnesium (trihydrate), in addition t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12
CPCC07D401/12
Inventor 王艳侨翟腾李沁沁王国强杨晓霞张亚慧
Owner KAIFENG MINGREN PHARMA
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