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New S-omeprazole salts

A technology for omeprazole potassium salt and omeprazole is applied in the field of novel S-omeprazole salt, can solve problems such as poor crystallinity, and achieve the effects of easy processing and storage, and easy large-scale preparation

Inactive Publication Date: 2011-11-16
CHENGDU ORGANIC CHEM CO LTD CHINESE ACAD OF SCI
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  • Abstract
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Problems solved by technology

In 2004, U.S. Patent US20040242642 described a magnesium salt solid obtained by distilling off the methanol in the methanol solution of esomeprazole magnesium salt, then adding water and stirring, and then mixing acetone and water at 0-5°C Method for preparing esomeprazole trihydrate with specific crystal form by stirring and recrystallizing esomeprazole magnesium salt in solvent, but we have confirmed esomeprazole magnesium salt with specific crystal form through examples. Stirring in a mixed solvent of acetone and water at ~5°C will not change its crystal form, so the crystal form described in this patent should be stirred in a mixed solvent of acetone and water at 0-5°C before the recrystallization step form, and in view of the peak position resolution and peak intensity of the X-RD pattern of the magnesium salt trihydrate obtained by this method, its crystallinity is not good

Method used

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Examples

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Embodiment Construction

[0042] Example 1: Preparation of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole

[0043] 0.348 g (1.5 mmol) of D-di-n-propionamide tartrate was added to the reactor, 7.5 ml of toluene was added, the temperature was raised to 60°C under stirring, and 0.225 ml (0.75 mmol) of Ti(Oi-Pr) was added 4 After 60 minutes, 0.0068 ml (0.375 mmol) of water was added and stirred for another 60 minutes. Cool down to 30°C, add 0.822 g (2.5 mmol) omeprazole precursor thioether, after stirring for 10 minutes, add 0.5 ml (2.7 mmol) 80% CHP dropwise, keep the reaction for 5 hours, the product is not separated, take A small amount of reaction solution is measured by HPLC and enantioselectivity is 80%, by 1 The yield calculated by H NMR internal standard method was 50%.

[0044] Example 2: Preparation of 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole

[0045] 0.348 g (1.5 mmol) of D-di-n-propionamide tartrate was added to the ...

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Abstract

The invention provides new S-omeprazole salts in special crystal forms, namely an S-omeprazole potassium salt di-ethanol adduct and an S-omeprazole magnesium salt trihydrate. The invention also relates to a method for preparing the S-omeprazole magnesium salt trihydrate with a special crystal form from the S-omeprazole potassium salt di-ethanol adduct. The invention aims to provide a simple method for preparing the S-omeprazole magnesium salt hydrate in the special form by utilizing water, a magnesium source and a cheap organic solvent on the basis of a simple and cheap enantioselectivity oxidation method for preparing new optically pure omeprazole potassium salts.

Description

technical field [0001] The present invention relates to novel S-5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole The potassium salt diethanolate and the magnesium salt hydrate. More specifically, the present invention relates to S-omeprazole potassium salt diethanolate and magnesium salt hydrate with specific crystal forms. In addition, the present invention also relates to a method for preparing S-omeprazole magnesium salt hydrate with specific crystal form by using S-omeprazole potassium salt diethanolate. Background technique [0002] Compound 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-1H-benzimidazole (commonly known as Ogilvy meprazole) and pharmaceutically acceptable salts thereof are described in EP5129. Specific alkali metal salts of omeprazole are described in EP124495. Omeprazole inhibits H + , K + - The activity of ATPase (also known as proton pump), which inhibits gastric acid secretion, has been widely...

Claims

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Application Information

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IPC IPC(8): C07D401/12A61K31/4439A61P1/04
Inventor 邓金根田添朱槿廖建黄晴菲
Owner CHENGDU ORGANIC CHEM CO LTD CHINESE ACAD OF SCI
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