Lansoprazole preparation method

A technology for lansoprazole and compounds, which is applied in the field of "one-pot method" for preparation of lansoprazole compounds, can solve the problems of unfavorable energy saving, consumption reduction and link protection, difficult removal of oxidant impurities, and difficult control of reaction conditions, etc. Short production cycle, low solvent toxicity, mild and controllable reactions

Active Publication Date: 2015-04-22
JIANGSU AOSAIKANG PHARMA CO LTD +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The two reactions of the preparation method are carried out step by step, and each step requires complicated post-treatments such as extraction, washing, and recrystallization, which is not conducive to energy saving and link protection; and sodium methoxide is generally used in the first condensation reaction step, and the reaction is violent. It is easy to generate impurities; in the second oxidation reaction step, m-chloroperoxybenzoic acid is used to oxidize, the reaction conditions are severe and difficult to control, and peroxide impurities are generated that are difficult to remove. At the same time, oxidant impurities are difficult to remove, requiring multiple extractions, recrystallization and other purification operations It is possible to increase the content of lansoprazole

Method used

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Experimental program
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Effect test

Embodiment 1

[0026] Add 500ml of 95% ethanol to the reaction flask, add 120g of 2-chloromethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine hydrochloride under stirring, and control the temperature at 25-35°C Add dropwise the solution of 65.16g 2-mercaptobenzimidazole and 43.56g sodium hydroxide in 350ml95% ethanol, control temperature reaction 2-3h, TLC monitoring reaction is complete (developing agent: dichloromethane: ethyl acetate=9: 1) Add 10% hydrochloric acid dropwise to adjust the pH to 6-7, a large amount of solids are precipitated, stirred and cooled to room temperature and then left to stand for 30 minutes, the reaction liquid is removed, and the solids in the reaction bottle are sampled to detect that the HPLC content is 99.8%. Then add 1000ml of ethanol to the reaction bottle, start stirring to dissolve all the solids, control the temperature at 10-20°C, slowly add 180g of 10% hydrogen peroxide dropwise, and then add 500ml of purified water after the reaction, a large amount of s...

Embodiment 2

[0028] Add 600ml of 90% ethanol to the reaction flask, add 120g of 2-chloromethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine hydrochloride under stirring, and control the temperature at 25-35°C Add dropwise the solution of 65.16g 2-mercaptobenzimidazole and 43.56g sodium hydroxide in 350ml90% ethanol, control the temperature and react for 2-3h, TLC monitors that the reaction is complete (developing solvent: dichloromethane: ethyl acetate=9: 1), add dropwise 5% hydrochloric acid to adjust the pH to 6-7, a large amount of solids are precipitated, stirred and cooled to room temperature and then left to stand for 30 minutes, the reaction liquid is removed, and the solid in the reaction bottle is sampled to detect that the HPLC content is 99.8%. Then add 900ml of ethanol to the reaction bottle, start stirring to dissolve all the solids, control the temperature at 10-20°C, slowly add 180g of 10% hydrogen peroxide dropwise, and then add 900ml of purified water after the reaction, a la...

Embodiment 3

[0030] Add 600ml of 95% ethanol to the reaction flask, add 120g of 2-chloromethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine hydrochloride under stirring, and control the temperature at 25-35°C Add dropwise the solution of 65.16g 2-mercaptobenzimidazole and 43.56g sodium hydroxide in 350ml95% methanol, control the temperature and react for 2-3h, and TLC monitors that the reaction is complete (developing solvent: dichloromethane: ethyl acetate=9: 1), adding 5% sulfuric acid dropwise to adjust the pH to 6-7, a large amount of solids were precipitated, stirred and cooled to room temperature, and the reaction clear liquid was removed, and the solids in the reaction flask were sampled to detect that the HPLC content was 99.8%. Then add 1000ml of ethanol to the reaction bottle, start stirring to dissolve all the solids, control the temperature at 10-20°C, slowly add 180g of 10% hydrogen peroxide dropwise, and then add 800ml of purified water after the reaction, a large amount of soli...

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Abstract

The invention relates to a preparation method of lansoprazole compounds, in particular to a one-pot preparation method of the lansoprazole compounds. By means of the preparation method, the process is easy and convenient, operation is simple, and the lansoprazole compounds are suitable for large-scale industrial production. Lansoprazole prepared through the method is high in total yield and content, and the quantity of related substances is low.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a "one-pot" preparation method of lansoprazole compound. Background technique [0002] Lansoprazole (lansoprazole), the chemical name is 2-[[[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridyl]methyl]sulfinyl]- 1H-benzimidazole, whose structure is shown in formula I, is a proton pump inhibitor developed by Takeda Corporation of Japan, mainly used for gastric ulcer, duodenal ulcer, reflux esophagitis, Zollinger-Ellison syndrome (Zollinger-Ai syndrome). Ellison syndrome), treatment of anastomotic ulcers. [0003] [0004] Generally, lansoprazole is first condensed to obtain the compound shown in formula II from the compound shown in formula III and the compound shown in formula IV, and the compound shown in formula II is oxidized to obtain lansoprazole shown in formula I. The two reactions of the preparation method are carried out step by step, and each step requires c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12
CPCC07D401/12
Inventor 陈庆财林国强赵俊宗在伟李谢刘汉泉李建国
Owner JIANGSU AOSAIKANG PHARMA CO LTD
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