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Preparation method of prednisolone

A technology of prednisolone and reaction, applied in the field of chemical pharmacy, can solve the problems of difficult separation and purification in the post-treatment process, low concentration of substrate feeding, long production cycle, etc., achieve novel process route, shorten production cycle, and low production cost Effect

Inactive Publication Date: 2016-03-09
HUAZHONG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] This preparation method has disadvantages such as high cost of substrate hydrocortisone, low substrate feeding concentration, long production cycle, and difficulty in separation and purification in the post-treatment process.

Method used

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  • Preparation method of prednisolone
  • Preparation method of prednisolone
  • Preparation method of prednisolone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Add 750ml of acetone, 30g of prednisolone intermediate reduction, 12g of sodium acetate, 50ml of acetic anhydride, and 8ml of acetic acid into the reaction flask in sequence, and heat up and reflux for 4 hours. TLC showed that the reaction was complete. Most of the solvent was recovered by atmospheric distillation, and then evaporated to dryness under reduced pressure, cooled to below 5°C, stirred for 30 minutes, left to stand for more than 2 hours, filtered, and dried to obtain 32.0 g of esterified product.

[0046] Put 30g of the esterified product into a solution prepared by 150ml of 36% hydrochloric acid, 240ml of water, and 15ml of chloroform, and stir at 25°C to 30°C for 30 minutes to dissolve. Cool down, and add dropwise a solution prepared from 30 g of sodium nitrite and 1050 ml of water at 18°C ​​to 22°C. After the addition was complete, the reaction was continued at 18°C ​​to 22°C for 3 hours. TLC showed that the reaction was complete, lower the temperature t...

Embodiment 2

[0049] Add 750ml of acetone, 30g of prednisolone intermediate reduced product, 15g of potassium acetate, 51ml of acetic anhydride, and 9ml of acetic acid into the reaction flask in sequence, and heat up and reflux for 4.5 hours. TLC showed that the reaction was complete, most of the solvent was recovered by atmospheric distillation, and then the solvent was evaporated under reduced pressure, cooled to below 5°C, stirred for 30 minutes, left to stand for more than 2 hours, filtered, and dried to obtain 31.9g of esterified product.

[0050] Put 30g of the esterified product into a solution prepared by 150ml of 36% hydrochloric acid, 240ml of water, and 15ml of chloroform, and stir at 25°C to 30°C for 30 minutes to dissolve. Cool down, and add dropwise a solution prepared from 30 g of sodium nitrite and 1050 ml of water at 18°C ​​to 22°C. After the addition was complete, the reaction was continued at 18°C ​​to 22°C for 3 hours. TLC showed that the reaction was complete, lower th...

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Abstract

The invention relates to a preparation method of prednisolone. The preparation method comprises the steps of sequentially carrying out 3, 20-keto protective reaction, 11-keto reduction reaction, 21-hydroxyl esterification reaction, 3, 20-keto deprotection reaction and 21-acetic ester hydrolysis reaction by taking prednisone acetate as a raw material to obtain prednisolone. The invention provides a novel synthesis route sequentially comprising the steps of esterifying and deprotecting; nitrosification quenching reaction and resin hydrolysis reaction are omitted in the deprotection process; and ester hydrolysis reaction is finished under the protection of a mixed solvent and inert gases, so that the condition that byproducts are produced by hydrolysis reaction is avoided. The preparation method is novel in process route, simple and rapid in operation process, low in production cost and suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the field of chemical pharmacy, and in particular relates to a preparation method of prednisolone. Background technique [0002] The structural formula of prednisolone (11β, 17α, 21-trihydroxypregna-1,4-diene-3,20-dione) is: [0003] [0004] Prednisolone is an adrenocortical hormone drug, mainly used for allergic and autoimmune inflammatory diseases, collagen diseases, such as rheumatism, rheumatoid arthritis, lupus erythematosus, severe bronchial asthma, nephrotic syndrome, platelet Reduced purpura, neutropenia, acute lymphoblastic leukemia, various adrenal insufficiency, exfoliative dermatitis, pemphigus, neurodermatitis, eczema, etc. Prednisolone is an important intermediate for the synthesis of 16α-hydroxyprednisolone, triamcinolone acetonide and other steroidal drugs, and is widely used in the field of steroidal drugs. [0005] The traditional preparation method of prednisolone is divided into biotransformation and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J5/00
Inventor 廖俊付林曾建华李桂莲赵成安
Owner HUAZHONG PHARMA
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