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Method for preparing pantoprazole nitrogen oxide

A technology for nitrogen oxides and pantoprazole, which is applied in the field of preparation of pantoprazole nitrogen oxides, can solve the problems of increasing manpower, resource costs, input of large manpower and material resources, and inability to guarantee the time limit, and achieves the preparation of The method is simple and easy to operate, saves production costs, and improves the effect of cheapness

Pending Publication Date: 2020-05-05
BEIJING XINLINGXIAN MEDICAL TECH DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] The way to obtain impurity reference substances has a significant impact on the development of quality research and the cost control of drug development, especially to measure the impurities produced under certain process conditions. Conventional column chromatography or crystallization, preparative liquid phase separation and preparation , often requires a large investment of manpower and material resources, which greatly increases the cost of manpower and resources, and the unit that provides the impurity reference substance may not be able to guarantee the time limit, or greatly increase the cost of research and development
At present, some impurity reference substances are difficult to prepare, or the yield is low. It is very difficult to obtain a high-purity reference substance. As pantoprazole nitrogen oxide, there is currently no particularly good preparation method, and it is difficult to meet the requirements of the consistency evaluation. In view of this situation, the present invention proposes a high-efficiency and green preparation method, which is simple, has few steps, mild conditions, high yield and good purity

Method used

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  • Method for preparing pantoprazole nitrogen oxide
  • Method for preparing pantoprazole nitrogen oxide
  • Method for preparing pantoprazole nitrogen oxide

Examples

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Embodiment 1

[0039] (1) Add 20% sodium hydroxide compound (10ml, 5mmol) to a 25ml reaction flask, add 2-chloromethyl-3,4-dimethoxypyridine hydrochloride (1g, 4.4mmol), and stir for 30 minutes , standing for stratification, discarding the upper aqueous phase, and retaining the lower layer of light yellow oil;

[0040] (2) Dissolve the oily matter in step (1) with dichloromethane (20ml), cool down to 2°C, add m-chloroperoxybenzoic acid (1.5g, 7.4mmol) in batches, after addition, 0-10°C React for 2 hours. After the reaction was completed, the reaction solution was washed with sodium metabisulfite solution, and the layers were separated. Dichloromethane was distilled off under reduced pressure to obtain a brown oil;

[0041](3) Add methanol (20ml) to the brown oil in step (2), stir to dissolve, add 5-difluoromethoxy-2-mercapto-1H-benzimidazole, cool to 0-10°C, add 20% aqueous sodium hydroxide solution (22ml) was added and reacted at 0-10°C for 2 hours. After the reaction, adjust the pH to ...

Embodiment 2

[0044] (1) Add 10% potassium carbonate aqueous solution (10ml) to the 25ml reaction bottle, add 2-chloromethyl-3,4-dimethoxypyridine hydrochloride (0.5g, 2.2mmol), stir for 30 minutes, static Separate the layers, discard the upper aqueous phase, and keep the lower layer of light yellow oil;

[0045] (2) Dissolve the oil in step (1) with tetrahydrofuran (15ml), cool down to 5°C, add m-chloroperoxybenzoic acid (0.8g, 3.9mmol) in batches, after addition, react at 0-10°C for 2 Hour. After the reaction was completed, the reaction solution was washed with sodium thiosulfate solution, and the layers were separated. Tetrahydrofuran was distilled off under reduced pressure to obtain a light yellow oil;

[0046] (3) Add tetrahydrofuran (15ml) to the light yellow oil in step (2), stir to dissolve, add 5-difluoromethoxy-2-mercapto-1H-benzimidazole, add 20% sodium hydroxide aqueous solution (11ml), after the addition, react at 20-30°C for 2 hours. After the reaction was completed, the ...

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Abstract

The invention provides a preparation method of pantoprazole nitrogen oxide, which is implemented according to the following steps: reacting 2-chloromethyl-3, 4-dimethoxypyridine hydrochloride servingas a raw material with m-chloroperoxybenzoic acid, and carrying out oxidization to prepare pyridine nitrogen oxide; and enabling the pyridine nitrogen oxide to react with 5-difluoromethoxy-2-mercapto-1H-benzimidazole to generate 5-difluoromethoxy-2-[(3, 4-dimethoxy-2-pyridyl) methyl] thio-1H-benzimidazole nitrogen oxide. The genetically toxic impurity pantoprazole nitrogen oxide of the pantoprazole sodium sesquihydrate is prepared by an economical and green method, the operation is simple and convenient, the condition is mild, and the product purity is high.

Description

technical field [0001] The invention provides a preparation method of pantoprazole nitrogen oxide. This method reacts with 5-difluoromethoxy-2-mercapto-1H-benzimidazole to generate 5- Difluoromethoxy-2-[(3,4-dimethoxy2-pyridyl)methyl]thio-1H-benzimidazole nitrogen oxide. Background technique [0002] Pantoprazole Sodium Sesquihydrate (Pantoprazole Sodium Sesquihydrate), the chemical name is 5-(difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridyl)methyl]benzene Sulfinyl]-1H-benzimidazole sodium, its chemical structural formula is: [0003] [0004] Pantoprazole sodium is a drug developed by German Becton Pharmaceuticals for the treatment of gastrointestinal ulcers. It is the third proton pump inhibitor after omeprazole and lansoprazole. It was first listed in South Africa in 1994, and was approved by the FDA in February 2000. The applicant is Wyeth Pharmaceutical Co., Ltd., and the dosage form is oral sustained-release tablets. At present, this product has been approved for m...

Claims

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Application Information

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IPC IPC(8): C07D401/12
CPCC07D401/12
Inventor 何杰王辉刘昆高世静陶新华
Owner BEIJING XINLINGXIAN MEDICAL TECH DEV CO LTD
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