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Method for preparing 16 alpha-hydroxyprednisolone

A technology of hydroxyprednisolone and hydroxyl, which is applied in the field of preparing 16α-hydroxyprednisolone, can solve the problems of being unsuitable for industrial production, high price of prednisolone, multiple side reaction impurities, etc., and is suitable for industrial production , good market prospects, high reactivity effect

Active Publication Date: 2020-06-09
ZHEJIANG SHENZHOU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] There are too many reaction steps in this method, and more side reaction impurities will be generated when the hydroxyl group is eliminated to prepare 16,17-ene compounds, and the yield is low
Simultaneously, prednisolone price is higher, is not suitable for industrialized production

Method used

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  • Method for preparing 16 alpha-hydroxyprednisolone
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  • Method for preparing 16 alpha-hydroxyprednisolone

Examples

Experimental program
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example 116

[0030] The preparation of example 1 16α-hydroxyprednisolone

[0031] 1. Oxidation reaction: 50 grams of 21-hydroxypregna-1,4,9(11),16-tetraene-3,20-dione-21-acetate (1) was dissolved in 2000 milliliters of acetone, and 10 Milliliter of formic acid, stirred and cooled to -10°C, added 300 ml of 8% potassium permanganate aqueous solution, stirred and reacted, after the reaction was completed, added 200 ml of 10% sodium bisulfite aqueous solution, filtered to collect the filtrate, concentrated to remove acetone, water analysis, Filter and dry to obtain 50 g of intermediate (2).

[0032] 2. Bromohydrin reaction: dissolve 50 grams of intermediate (2) in 2000 milliliters of butanone, add 120 milliliters of fluoroboric acid with a mass concentration of 2%, stir and cool down to 5° C., add 50 grams of dibromohydantoin and stir to react. After completion, 70 ml of 15% sodium sulfite aqueous solution was added to concentrate the butanone, water analysis, filtration, and drying to obtain...

example 216

[0035] The preparation of example 2 16α-hydroxyprednisolone

[0036] 1. Oxidation reaction: 50 grams of 21-hydroxypregna-1,4,9(11),16-tetraene-3,20-dione-21-acetate (1) was dissolved in 1500 milliliters of butanone, added 20 milliliters of oxalic acid, stirring and cooling to -5°C, adding 350 milliliters of 6% potassium permanganate aqueous solution, stirring and reacting, after the reaction was completed, adding 400 milliliters of 5% sodium bisulfite aqueous solution, collecting the filtrate by filtration, concentrating butanone, water Analysis, filtration, drying, to obtain 50.5 grams of intermediate (2).

[0037] 2. Bromohydrin reaction: dissolve 50.5 grams of intermediate (2) in 1500 milliliters of acetone, add 70 milliliters of perchloric acid with a mass concentration of 5%, stir and cool to 0°C, add 45 grams of N-bromosuccinimide and stir After the reaction was completed, 50 ml of 20% sodium sulfite aqueous solution was added, the acetone was concentrated, the water was ...

example 316

[0040] The preparation of example 3 16α-hydroxyprednisolone

[0041] 1. Oxidation reaction: 50 grams of 21-hydroxypregna-1,4,9(11),16-tetraene-3,20-dione-21-acetate (1) was dissolved in 1500 milliliters of dichloromethane, Add 15 ml of glacial acetic acid, stir and cool down to -20°C, add 320 ml of 7% potassium permanganate aqueous solution, stir for reaction, after the reaction is completed, add 100 ml of 20% sodium bisulfite aqueous solution, collect the filtrate by filtration, and concentrate to remove the organic solvent , water analysis, filtration, and drying to obtain 50.1 g of intermediate (2).

[0042] 2. Bromo-hydroxyl reaction: dissolve 50.1 grams of intermediate (2) in 2000 milliliters of acetone, add 50 milliliters of 10% methanesulfonic acid, stir and cool to -10°C, add 48 grams of N-bromosuccinimide Stir the reaction, after the reaction is completed, add 80 ml of 5% sodium sulfite aqueous solution, concentrate the organic solvent, water analysis, filtration, an...

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Abstract

The invention discloses a method for preparing 16 alpha-hydroxyprednisolone, belonging to the technical field of medicine preparation and processing. According to the method, 21-hydroxypregna-1,4,9(11),16-tetraene-3,20-dione 21-acetate is used as an initial raw material and subjected to oxidation, bromo-hydroxylation, debromination and alcoholysis to prepare 16 alpha-hydroxyprednisolone. Accordingto the method for preparing 16 alpha-hydroxyprednisolone, generation of impurities in the reaction process can be effectively controlled by improving the defects of a traditional process, reaction process is mild, and an overall conversion rate is high; and the method disclosed by the invention has the advantages of low requirements on a reaction device, low operation cost, simplicity and convenience in operation, suitability for industrial production and higher market prospects.

Description

technical field [0001] The invention relates to the technical field of preparation and processing of medicines, in particular to a method for preparing 16α-hydroxyprednisolone. Background technique [0002] 16α-hydroxyprednisolone (molecular formula C 21 h 28 o 6 ), English name 16alpha-hydroxyprednisolone, chemical name 11β, 16α, 17α, 21-tetrahydroxypregna-1,4-diene-3,20-dione, is a halogen-free Ned steroid Important pharmaceutical intermediates of adrenocortical hormone drugs. Using it as a raw material, glucocorticoid drugs such as budesonide, ciclesonide and desononide can be synthesized, and nedide-like glucocorticoid drugs are widely used in the treatment of intractable asthma and inflammation, especially budesonide and ciclesonide Sonide has the advantages of small dosage, strong local anti-inflammatory effect, and small systemic side effects. What is more prominent is that it can be applied to children, so it has become the first choice for clinical treatment of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J7/00
CPCC07J7/006C07J13/005C07J5/0092C07B35/06
Inventor 邵振平王荣陈克纲王炳乾王友富
Owner ZHEJIANG SHENZHOU PHARMA
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