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Method for synthesizing 16 alpha-hydroxy prednisolone

A technology of hydroxyprednisolone and its synthetic method, applied in the direction of steroids, organic chemistry, etc., can solve the problems that the key technology needs to be broken through and cannot form industrial production, and achieve the effect of low difficulty, easy control and good stability

Active Publication Date: 2014-04-16
浙江东晖药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Method 2: Using prednisolone as the starting material, 16α-hydroxyprednisolone is directly produced through microbial fermentation technology, but this method is currently only in the experimental stage, and the key technology needs to be broken through, and industrial production cannot be formed at present

Method used

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  • Method for synthesizing 16 alpha-hydroxy prednisolone
  • Method for synthesizing 16 alpha-hydroxy prednisolone
  • Method for synthesizing 16 alpha-hydroxy prednisolone

Examples

Experimental program
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Effect test

Embodiment 1

[0029] This example introduces a synthetic method for 16α-hydroxyprednisolone. The synthetic steps are as follows: firstly, add 40 g of prednisone, 240 ml of pyridine, and 100 ml of acetone into the reaction bottle successively, and keep the temperature below 0°C for the reaction. It can be detected under 254nm ultraviolet light, and when the raw material point is less than 1%, it is analyzed in ice water, left standing overnight, filtered with suction, washed with water, dried, and recrystallized to obtain 31.2g of intermediate I. The chemical formula of intermediate I is:

[0030] ;

[0031] Take 20g of intermediate Ⅰ, 11g of potassium permanganate, 2ml of triethylamine, and 1000ml of acetone, and put them into the reaction bottle in turn, and react at low temperature to achieve detection under 254nm ultraviolet lamp. After the raw material point is less than 1%, add 5g of sulfite , terminate the reaction, filter, concentrate under reduced pressure, cool, filter with sucti...

Embodiment 2

[0040] This example introduces a synthesis method of 16α-hydroxyprednisolone. The synthesis steps are as follows: firstly, add 40 g of prednisone, 240 ml of collidine, and 100 ml of acetone into the reaction flask in sequence, Insulation reaction, detection under 254nm ultraviolet light, when the raw material point is less than 1%, water analysis in ice water, standing overnight, suction filtration, washing with water, drying, recrystallization to obtain 31.2g of intermediate Ⅰ, the chemical formula of intermediate Ⅰ is :

[0041] ;

[0042] Take 20g of intermediate Ⅰ, 11g of osmium tetroxide, 2ml of pyridine, and 1000ml of acetone in turn, and put them into the reaction bottle in turn, and react at low temperature until it can be detected under a 254nm ultraviolet lamp. When the raw material point is less than 1%, add 5g of sulfite to terminate the reaction , filtered, concentrated under reduced pressure, cooled, filtered with suction, and dried to obtain 20 g of intermedi...

Embodiment 3

[0051] This embodiment has introduced a kind of synthetic method of 16α-hydroxyprednisolone, and its synthetic steps are: first add 40g prednisone, 120ml pyridine, 120ml collidine, 100ml acetone in the reaction flask successively, Insulate and react below 0°C to achieve detection under a 254nm ultraviolet lamp. After the raw material point is less than 1%, analyze in ice water, stand overnight, filter with suction, wash with water, dry, and recrystallize to obtain 31.2g of intermediate I. Intermediate The chemical formula of I is:

[0052] ;

[0053] Take 20g of intermediate Ⅰ, 5g of potassium permanganate, 5g of osmium tetroxide, 2ml of collidine, and 1000ml of acetone, and put them into the reaction bottle in turn, and react at low temperature to achieve detection under a 254nm ultraviolet lamp. After the raw material point is less than 1% , add 5 g of sulfite, terminate the reaction, filter, concentrate under reduced pressure, cool, filter with suction, and dry to obtain...

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Abstract

The invention relates to a method for synthesizing 16 alpha-hydroxy prednisolone, and belongs to the field of chemical technologies. In the method, prednisone is taken as an initiative raw material, and subjected to five-step reaction of elimination, oxidation, condensation, reduction and hydrolysis to form the 16 alpha-hydroxy prednisolone; the prednisone is taken as the raw material, organic weak base is taken as a retarder to inhibit the oxidation rate of potassium permanganate to reactants, a three-phase acid solvent is taken as a solvent, ketoxime is hydrolyzed by adding aqueous solution of nitrite, and refining is carried out by a multiphase separation crystallization technology. The method has the advantages of simple operation, mild reaction conditions, readily available raw material, low cost and light environmental pollution.

Description

Technical field [0001] The invention relates to a synthesis method of 16α-hydroxyprednisolone and belongs to the field of chemical technology. Background technique [0002] 16α-Hydroxyprednisolone is an important pharmaceutical intermediate for halogen-free adrenocortical hormone drugs. It is used in the manufacture of desonide, budesonide, ciclesonide and other drugs for the treatment of bronchial inflammation and asthma. Basic raw materials, the market prospect is very broad. [0003] At present, there are two reports on the synthesis of 16α-hydroxyprednisolone in the literature. Method one: using prednisolone as the starting material, it is prepared through reactions such as cyclic ester, hydrolysis, acylation, elimination and oxidation, but The price of the starting raw material prednisone in this method is relatively high, the reaction steps are long and the reactions are repeated, and the cost is high. Method 2: Using prednisolone as the starting material, 16α-hydrox...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J5/00
Inventor 王勇
Owner 浙江东晖药业有限公司
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