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Preparation method of high-purity 16 alpha-hydroxyprednisolone

A technology of hydroxyprednisolone and hydroxyprednisolone acetate, which is applied in the field of preparation of high-purity 16α-hydroxyprednisolone, can solve problems such as difficult refining and difficult removal of impurities, and achieve improved purity and operating costs The effect of low, mild reaction conditions

Inactive Publication Date: 2020-12-25
ZHEJIANG SHENZHOU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] In order to solve the problems of difficult removal of impurities and difficulty in refining in the existing 16α-hydroxyprednisolone process using tetraenyl acetate as the starting material, the present invention provides a simple operation, short reaction route, and high-purity 16α-hydroxy prednisolone The preparation method of prednisolone

Method used

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  • Preparation method of high-purity 16 alpha-hydroxyprednisolone
  • Preparation method of high-purity 16 alpha-hydroxyprednisolone
  • Preparation method of high-purity 16 alpha-hydroxyprednisolone

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Embodiment 1

[0026] The preparation of embodiment 1 high-purity 16α-hydroxyprednisolone

[0027] 50 grams of 16α-hydroxyprednisolone acetate crude product was dissolved in 700 milliliters of dichloromethane and 700 milliliters of ethanol, then 1.5 milliliters of formic acid was added, 24 milliliters of 5% sodium hypochlorite aqueous solution was added dropwise, and the temperature was controlled at 15°C to stir the reaction to obtain the preliminary treatment product ;

[0028] Add 150 milliliters of 5% sodium bisulfite aqueous solution to the above-mentioned preliminary treatment product, concentrate to remove the solvent, add water for water analysis, and filter to obtain 45 grams of 16α-hydroxyprednisolone acetate fine product;

[0029] Dissolve 45 grams of 16α-hydroxyprednisolone acetate refined product obtained above in a mixed organic solvent of 250 milliliters of dichloromethane and 250 milliliters of methanol, stir and cool to 0° C., add 90 milliliters of 10% sodium sulfite aqueous...

Embodiment 2

[0030] The preparation of embodiment 2 high purity 16α-hydroxy prednisolone

[0031] 50 grams of 16α-hydroxyprednisolone acetate crude product was dissolved in 200 milliliters of dichloromethane and 300 milliliters of methanol, then added 4.8 milliliters of propionic acid, 12 milliliters of 10% sodium hypochlorite aqueous solution was added dropwise, and the temperature was controlled to stir at 25°C to obtain preliminary treatment Taste;

[0032] Add 100 milliliters of 15% sodium bisulfite aqueous solution to the above-mentioned preliminary treatment product, concentrate to remove the solvent, add water for water analysis, and filter to obtain 46 grams of 16α-hydroxyprednisolone acetate fine product;

[0033] Dissolve 46 grams of 16α-hydroxyprednisolone acetate refined product obtained above in a mixed solvent of 600 milliliters of dichloroethane and 350 milliliters of isopropanol, stir and cool to -10°C, add 80 milliliters of 20% sodium sulfite aqueous solution, stir After ...

Embodiment 3

[0034] The preparation of embodiment 3 high-purity 16α-hydroxyprednisolone

[0035] 50 grams of crude product of 16α-hydroxyprednisolone acetate was dissolved in 500 milliliters of dichloromethane and 400 milliliters of isopropanol, then 3 milliliters of glacial acetic acid was added, 5 milliliters of 13% sodium hypochlorite aqueous solution was added dropwise, and the temperature was controlled at 40° C. to stir the reaction, get primary treatment;

[0036] Add 25 milliliters of 30% sodium bisulfite aqueous solution to the above-mentioned preliminary treatment product, concentrate to remove the solvent, add water for water analysis, and filter to obtain 45.5 grams of 16α-hydroxyprednisolone acetate fine product;

[0037] 45.5 grams of 16α-hydroxyprednisolone acetate fines obtained above were dissolved in 850 milliliters of ethanol and 500 milliliters of tetrahydrofuran mixed organic solvent, stirred and cooled to 10 ℃, added 70 milliliters of 30% sodium sulfite aqueous soluti...

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Abstract

The invention discloses a preparation method of high-purity 16 alpha hydroxyl prednisolone, and belongs to the technical field of medicine preparation and processing. The method comprises the following steps: completely dissolving a 16 alpha hydroxyl prednisolone acetate crude product in a mixed solvent of dichloromethane and alcohol, adding an organic acid, dropwise adding a hypochlorite aqueoussolution, controlling the temperature to be 15-40 DEG C, carrying out a stirring reaction to obtain a primary treatment product, removing the impurity through a hydration refining method, and hydrolyzing to obtain the high-purity 16 alpha hydroxyl prednisolone. The method is simple to operate, mild in reaction condition and short in reaction route, the purity of the final product prepared by the method is higher than 99.5%, the content of the impurity H is lower than 0.02%, and the requirement of the market on high-purity 16 alpha hydroxyl prednisolone can be easily met.

Description

technical field [0001] The invention relates to the technical field of preparation and processing of medicines, in particular to a preparation method of high-purity 16α-hydroxyprednisolone. Background technique [0002] 16α-Hydroxyprednisolone, chemical name 11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione, molecular formula C 21 h 28 o 6 , is an important pharmaceutical intermediate of halogen-free nedd steroid adrenocorticosteroids. 16α-Hydroxyprednisolone is mainly used in the clinical treatment of severe asthma and allergic rhinitis, and has broad market prospects. [0003] According to bibliographical reports, at present synthetic 16α-hydroxy prednisolone mainly contains following three kinds of starting materials, and they are respectively: 1) take prednisolone as starting material; 2) take prednisone as starting material; 3 ) using tetraenyl acetate as the starting raw material, wherein the synthesis of 16α-hydroxyprednisolone with tetraenyl acetate as the s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J5/00
CPCC07J5/0092
Inventor 邵振平王荣王炳乾王洪福黄橙橙雷灵芝王友富
Owner ZHEJIANG SHENZHOU PHARMA
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