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Preparation method of lansoprazole

A technology of lansoprazole and solvent, applied in the field of preparation of lansoprazole, can solve the problems of difficult purification and low yield, and achieve the effect of simple process and easy control of impurities

Inactive Publication Date: 2018-04-27
JIANGSU HAICI BIOLOGICAL PHARMA CO LTD OF YANGTZE RIVER PHARMA GRP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] And once impurity A and impurity B produce more than 0.1%, due to the similarity in structure, it will bring great difficulties to subsequent purification, resulting in low yield

Method used

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  • Preparation method of lansoprazole
  • Preparation method of lansoprazole
  • Preparation method of lansoprazole

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Embodiment 1 Lansoprazole preparation

[0032] Add 44.8g of sodium hydroxide (1.12mol), 500ml of ethanol, and 640ml of water into a 3L reaction flask. After stirring and dissolving, add 100g of compound M1 (0.28mol), control the temperature at -5 to 10°C, and slowly add sodium hypochlorite solution (0.36 mol, the available chlorine content is 3.0%), after the dropwise addition is completed, it is incubated at -5 to 10°C for 1 hour, after the reaction is completed, add 10% sodium thiosulfate solution to quench the reaction, and use 20% acetic acid Adjust the pH to 7-9, then control the temperature and stir for 1 hour at 0°C, filter, wash with purified water, and dry the wet product in a vacuum oven to obtain 84.5 g of light yellow solid, which is the crude product of lansoprazole. Yield 81%, impurity A: <0.1%, impurity B: <0.1%, purity: 99.58%.

[0033] Add 80g of lansoprazole crude product into 800ml of acetone, heat and reflux until dissolved, filter the insoluble mat...

Embodiment 2

[0034] Embodiment 2 Lansoprazole preparation

[0035] Add 5.6g of sodium hydroxide (0.14mol), 50ml of isopropanol, and 60ml of water into a 250mL reaction flask, stir and dissolve, add 10g of compound M1 (0.028mol), control the temperature at -5~10°C, and slowly add sodium hypochlorite solution dropwise (0.039mol, available chlorine content 3.5%), after the dropwise addition was completed, it was incubated and reacted at -5~10°C for 1 hour, HPLC detected M1<0.5%, stopped the reaction, added 10% sodium thiosulfate solution to quench the reaction, and detected After no oxidation, use 20% acetic acid to adjust the pH to 7-9. After the adjustment, control the temperature and stir at 0°C for 1 hour, filter, wash with purified water, and dry the wet product in a vacuum oven to obtain 8.7g of light yellow The solid is crude lansoprazole, with a yield of 83%, impurity A: <0.1%, impurity B: <0.1%, and purity: 99.71%.

[0036] Add 6.0g of crude lansoprazole into 60ml of acetone, heat a...

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Abstract

The invention provides a preparation method of lansoprazole. The structural formula of the lansoprazole compound is shown in a formula (I), and the method comprises the following steps: (1) a compoundM1, inorganic base and purified water are added into a solvent A, and a sodium hypochlorite solution of a certain concentration is added at a low temperature condition; after the reaction ends, a reducing agent is added and a quenching reaction is carried out, acid is adjusted and pH value is adjusted to 7-9, and stirring and crystallization, filtering, washing and drying are carried out in orderto obtain a lansoprazole crude product; wherein, the mol ratio of the compound M1 to sodium hypochlorite to alkali is 1:1.0-1.5:2.5-5.0; the sodium hypochlorite solution of a certain concentration employs available chlorine to calculate content (w / w) and the content is 1.0-7.0%; (2) a solvent B is used in order to carry out refining of the lansoprazole crude product obtained in the step (1), andlansoprazole is obtained. The technology has the advantages of simple operation, low cost, high yield, safety and environmental protection, high purity of the product, and the like, and the method issuitable for industrial large-scale production.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a preparation method of lansoprazole. Background technique [0002] Lansoprazole, chemical name: 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methanol [0003] Base] sulfinyl] -1H-benzimidazole, CAS number: 103577-45-3, chemical structural formula such as formula (I): [0004] [0005] Lansoprazole (Lansoprazole) is the benzimidazole derivatives with acid secretion inhibitory effect developed by Takeda Corporation in Japan in the late 1980s, and is also the second novel proton pump inhibitor known after the development of omeprazole. Inhibits gastric acid secretion and acts as an antiulcer agent. [0006] At present, the method for preparing lansoprazole is known, and in the synthetic preparation method of report all relate to use the lansoprazole precursor with thioether group at last, then make thioether group oxidation into sulfoxide group, as follows : [0007] ...

Claims

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Application Information

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IPC IPC(8): C07D401/12
CPCC07D401/12
Inventor 刘宏远王庆辉牛明玉倪晶
Owner JIANGSU HAICI BIOLOGICAL PHARMA CO LTD OF YANGTZE RIVER PHARMA GRP
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