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Preparation method of high-purity amino sugar drug impurity

A technology of amino sugar and purification method, applied in the field of medicine, can solve the problems of unfriendly environment, cumbersome process, application limitation and the like

Active Publication Date: 2021-07-13
SHANGHAI TECHWELL BIOPHARMACEUTICALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation method involves multi-step reactions, and the various raw and auxiliary materials used are still not commercialized materials, which need to be prepared in advance, and the process is cumbersome
And using benzyl as the hydroxyl protecting group requires heavy metal palladium to catalyze the removal of the protecting group, which is not friendly to the environment
In addition, the preparation product of this patent is the hydrochloride salt of amino sugar drug impurities, which cannot be directly used for the detection of voglibose-related substances, and its application is subject to certain restrictions

Method used

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  • Preparation method of high-purity amino sugar drug impurity
  • Preparation method of high-purity amino sugar drug impurity
  • Preparation method of high-purity amino sugar drug impurity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Add 5.0g of mycophenolamine, 0.5g of 1,3-dihydroxyacetone (0.2 equivalent), N,N-dimethylformamide (240ml) into a stirred three-neck flask, and stir for 5-10min. After adding 0.2 g of tartaric acid, 2.5 g of sodium triacetylborohydride was added in three batches. After 10 minutes, it was heated to 40°C for 10 hours. After the reaction, the HPLC purity of the aminosugar drug impurity in the reaction product was 20%.

Embodiment 2

[0069] Add 5.0 g of mycosamine, 1.4 g of 1,3-dihydroxyacetone (0.6 equivalent), and dimethyl sulfoxide (240 ml) into the reaction flask, and stir for 5 minutes to dissolve it. Then add 0.3 g of formic acid, stir for 1 min, and add 2.4 g of sodium borohydride in five batches. After reacting for 20min, heat to 80°C and react for 1h. After the reaction, the HPLC purity of the aminosugar drug impurity in the reaction product was 28%.

Embodiment 3

[0071] Add 5.0 g of mycophenolamine, 2.3 g of 1,3-dihydroxyacetone (1.0 equivalent), and acetonitrile (240 ml) into the stirred reaction flask, and stir to dissolve it. Add 0.3g of citric acid, stir for 60min, and add 0.8g of zinc powder. After 10 minutes, it was heated to 45°C for 8 hours. After the reaction, the HPLC purity of the aminosugar drug impurity in the reaction product was 42%.

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Abstract

The invention discloses a preparation method of a high-purity amino sugar drug impurity, the amino sugar drug impurity has a structure as shown in formula (I): weak acid is used for catalyzing valiolamine to react with 1, 3-dihydroxy acetone to prepare the amino sugar drug impurity, and the HPLC (high performance liquid chromatography) purity in a reaction product is greater than 20%. The method is high in yield, environment-friendly and suitable for industrial production of amino sugar drug impurities. The invention further discloses a method for purifying the amino sugar drug impurities from the reaction liquid, and the optimal HPLC purity of the purified amino sugar drug impurities is 98% or above.

Description

technical field [0001] The present invention relates to the field of medical technology, and provides a method for preparing high-purity amino sugar drug impurities. The amino sugar drug impurities in the present invention refer to the voglibose quality standards included in the "Chinese Pharmacopoeia" 2020 edition The voglibose impurity I. Background technique [0002] Japan's Takeda (Takeda) company successfully developed voglibose, trade name Basen (Beixin). Voglibose is widely used in the prevention, treatment and combined medicine of type I and type II diabetes. Compared with sulfonylureas and acarbose, it has lower side effects and has a broad market prospect. [0003] At present, industrialized synthesis of voglibose basically adopts a semi-synthetic method, and the voglibose semi-synthesis process synthesizes voglibose (US 4777294; US 4803303; USP4701559; EP0056194; J. Med.Chem.1986,29,6), the Jinggang mycosamine and 1,3-dihydroxyacetone are reacted in an equivalen...

Claims

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Application Information

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IPC IPC(8): C07C213/08C07C213/10C07C215/44C07C249/02C07C251/08
CPCC07C213/08C07C213/10C07C215/44C07C249/02C07C2601/14C07C251/08Y02P20/55
Inventor 石荣国陈敏郭玉姗李严季晓铭
Owner SHANGHAI TECHWELL BIOPHARMACEUTICALS CO LTD
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