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Omeprazole sodium and preparation method

A technology of omeprazole and sodium iodide, applied in the field of medicine, can solve the problems of poor purity, low yield, long reaction time and the like, and achieve the effects of good product purity, shortened reaction time and improved product yield

Active Publication Date: 2014-06-25
CHENGDU TIANTAISHAN PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] At present, many patents have reported the preparation method of omeprazole sodium, most of which adopt omeprazole and sodium hydroxide, sodium alkoxide or sodium acetoacetate to react, and the preparation of omeprazole is through multi-step Reaction preparation, finally the prepared intermediate 2-mercapto-5-methoxy-1H-benzimidazole and 2-chloromethyl-3,5-dimethyl-4-methoxypyridine hydrochloride in hydrogen Butt docking in an organic solvent of sodium oxide, the yield has been between 70-80%, the reaction time is longer, and the sulfide intermediate 5-methoxy-2-[(4-methoxy-3,5- Dimethylpyridin-2-yl)methylthio]-1-benzimidazole is oxidized to product omeprazole with poor purity and low yield

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0066] Example 1: Preparation of 5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylthio]-1H-benzimidazole

[0067] 180 grams (1mol) of 2-mercapto-5-methoxyl-1H-benzimidazole and 222 grams (1mol) of 2-chloromethyl-3,5-dimethyl-4-methoxypyridinium acid salt was added to 5 liters of ethanol and acetone mixed solvent (V:V=3:1), which contained 80 grams (2mol) of sodium hydroxide, while adding 5 grams (0.033mol) of sodium iodide, the reaction mixture was Heat to reflux for 1.5 hours, cool to room temperature, filter to remove insoluble matter, distill off most of the solvent from the filtrate under reduced pressure, add 3 liters of ethyl acetate to the residue to dissolve, wash twice with 1 liter of water, and dry the organic phase with anhydrous sodium sulfate , filtered, concentrated, and 400ml of acetone was added to the residue. The organic phase was frozen to 0°C, and a solid precipitated overnight, and was filtered to obtain 315.8 g of off-white solid 5-methoxy-2-[(4-...

Embodiment 2

[0068] Embodiment 2: preparation omeprazole

[0069] 5-methoxyl-2-[(4-methoxyl-3,5-dimethylpyridin-2-yl)methylthio]-1H-benzimidazole prepared in Example 1 was added to 1500ml of Ethyl acetate, cool the reaction system to -25°C, maintain the reaction temperature, slowly add peracetic acid (the amount is 5-methoxy-2-[(4-methoxy-3,5-dimethyl 1.2 times the molar weight of pyridin-2-yl)methylthio]-1H-benzimidazole) and lactic acid (the amount is 5-methoxy-2-[(4-methoxy-3,5-dimethyl basepyridin-2-yl)methylthio]-1H-benzimidazole molar weight of 0.2 times) of the mixture, continue to react for 0.5 hours after adding, while adjusting the pH value of the reaction system with 10% sodium hydroxide, maintain At pH=8, a precipitate precipitated, filtered, washed the filter cake with water, dried, and then recrystallized with methanol to obtain omeprazole as a white solid, yield: 94.8%.

[0070] [HPLC method B] of the present invention is used to measure the content of impurity C (unoxid...

Embodiment 21

[0071] Example 21: Preparation of Omeprazole

[0072] With reference to the method of Example 2 above, the difference is that the amount of lactic acid is 5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylthio]-1H- 0.1 times the molar amount of benzimidazole. 【HPLC method B】Measurement results: the impurity C content is 0.004%, the impurity D content is 0.016%, and the HPLC purity is greater than 99.7%.

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Abstract

The invention relates to omeprazole sodium and a preparation method, and in particular relates to a method for preparing omeprazole or a salt thereof. The method comprises the following steps of: (1) reacting 2-chlorinated methyl-3,5-dimethyl-4-methoxypyridine or a salt thereof and 2-mercapto-5-methoxy-1H-benzimidazole to generate 5-methoxy-2-[(4-methoxy-3,5-dimethylpyridine-2-yl)methylmercapto]-1H-benzimidazole; and (2) oxidizing 5-methoxy-2-[(4-methoxy-3,5-dimethylpyridine-2-yl)methylmercapto]-1H-benzimidazole to generate omeprazole. The invention further relates to omeprazole prepared by the invention or a sodium salt thereof. A product prepared by the method has high purity.

Description

technical field [0001] The invention belongs to the technical field of medicine and relates to omeprazole sodium which can be used for treating stomach diseases. The omeprazole sodium of the invention has good properties. Background technique [0002] Digestive system disease is a common and frequently-occurring disease, and it is also a chronic disease that is very easy to relapse. So far, there is no effective way to completely cure it. This has become one of the key topics in the field of pharmaceutical research. Statistical analysis shows that the incidence rate of digestive system diseases in the world accounts for 10-12% of human beings, and the incidence rate of digestive system diseases in cities and towns in my country is 11.43%, which is basically similar to many developed countries in Europe and America. Due to the characteristics of diet structure, the prevalence rate of residents in southern cities and southwestern regions is relatively high, and the incidence r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12
Inventor 赵东明方专王敬江威董国明
Owner CHENGDU TIANTAISHAN PHARMA
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