Methylprednisolone chemical synthesis method

A technology of methylprednisolone and chemical synthesis, applied in organic chemistry, steroids, etc., can solve the problems of many reaction by-products, incomplete methylation transposition, large synthesis reaction side reactions, etc. The effects of improved efficiency and quality, easy industrialization, and mild reaction conditions

Inactive Publication Date: 2006-04-26
台州百大药业有限公司
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  • Abstract
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Problems solved by technology

In this method, the three key reaction processes of 11-position reduction, 1-2-position dehydrogenation reaction, and 6-position methylation are technically difficult, and the side reactions are difficult to control, resulting in poor product quality, low yield, and high cost. It is suitable for industrialization and industrial production without research and development
[0005] The specific problems in the process are: A. 11-position reduction There are two problems in this step reaction. One is that while the 11-position reduction is being carried out, the ketone groups at the 3 and 20 positions are also reduced, and there are many reaction by-products; the other is that the 11-position Incomplete bit reduction, thus affecting the yield and product quality
B

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  • Methylprednisolone chemical synthesis method
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Embodiment 1

[0018] Pregnene dienolone acetate starting material 30 kg, 4-pregnene-3,11,20- 24 kilograms of triketone-17α-alcohol-21--base acetate; Add 160 kilograms of dichloromethane, 50 kilograms of triethyl formate, 30 kilograms of ethylene glycol, 1.5 kilograms of p-toluenesulfonic acid, and carry out at room temperature for 3 , the 20-position ketone group protection reaction; then add 15 kg of potassium borohydride, 300 kg of pyridine, add 1-2 times of water, and carry out the 11-position reduction reaction for 15-30 hours; add 19.5 kg of benzoquinone and p-toluenesulfonic acid to the reaction product 1.7 kilograms react under 350 kilograms of methyl alcohol: chloroform=6: 5 mixed solvents; Add 80 kilograms of dimethylformamides and make solvent in the reaction product, 4.5 kilograms of palladium charcoals are made catalysts, and 20 kilograms of cyclohexenes are made reaction aids, 100 The product obtained after reacting at ℃ for 2-3 hours was hydrolyzed to obtain 12.5 kg of methylp...

Embodiment 2

[0020] Pregnene dienolone acetate starting material 30 kg, 4-pregnene-3,11,20- 24 kilograms of triketone-17α-alcohol-21--base acetate; Add 160 kilograms of dichloromethane, 25 kilograms of triethyl formate, 30 kilograms of ethylene glycol, 1.5 kilograms of p-toluenesulfonic acid, and carry out at room temperature for 3 , the 20-position ketone group protection reaction; then add 15 kg of potassium borohydride, 300 kg of pyridine, add 1-2 times of water, and carry out the 11-position reduction reaction for 15-30 hours; add 19.5 kg of benzoquinone and p-toluenesulfonic acid to the reaction product 1.7 kilograms react under 350 kilograms of methyl alcohol: chloroform=6: 5 mixed solvents; Add 80 kilograms of dimethylformamides and make solvent in the reaction product, 4.5 kilograms of palladium charcoals are made catalysts, and 20 kilograms of cyclohexenes are made reaction aids, 100 The product obtained after reacting at ℃ for 2-3 hours was hydrolyzed to obtain 11.3 kg of methylp...

Embodiment 3

[0022] Pregnene dienolone acetate starting material 30 kg, 4-pregnene-3,11,20- 24 kilograms of triketone-17α-alcohol-21--base acetate; Add 160 kilograms of dichloromethane, 30 kilograms of triethyl formate, 30 kilograms of ethylene glycol, 1.5 kilograms of p-toluenesulfonic acid, and carry out at room temperature for 3 , the 20-position ketone group protection reaction; then add 15 kg of potassium borohydride, 300 kg of pyridine, add 1-2 times of water, and carry out the 11-position reduction reaction for 15-30 hours; add 19.5 kg of benzoquinone and p-toluenesulfonic acid to the reaction product 1.7 kilograms react under 350 kilograms of methyl alcohol: chloroform=6: 5 mixed solvents; Add 80 kilograms of dimethylformamides and make solvent in the reaction product, 4.5 kilograms of palladium charcoals are made catalysts, and 20 kilograms of cyclohexenes are made reaction aids, 100 The product obtained after reacting at ℃ for 2-3 hours was hydrolyzed to obtain 11.8 kg of methylp...

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Abstract

The present invention discloses the chemical synthesis process of methyl prednisoline. By using pregnenolone acetate as initial material, the present invention prepares methyl prednisoline through the steps of: epoxidation, mildew oxidation, place-11 reduction, place I and II dehydrogenation, place VI methylation and other reaction steps. The process of the present invention has mild reaction condition, high product purity, stable product quality, high product yield and low production cost, and is suitable for industrial production of methyl prednisoline.

Description

technical field [0001] The invention relates to a method for synthesizing methylprednisolone (1,4-pregnadiene-3,20-dione-11β, 17α, 21-triol-6α-methyl), which is based on Pregnidine dienolone acetate was used as starting material to prepare methylprednisolone. Background technique [0002] Methylprednisolone is the key intermediate for the production of the highly efficient glucocorticoid methylprednisolone sodium succinate. It has anti-inflammatory, anti-cellular immune effects and good curative effect. It is the first choice commonly used in the treatment of nephrotic syndrome medicine. [0003] At present, methylprednisolone is exclusively produced by U.S. Upjohn Company in foreign countries, and it has been monopolized by U.S. Upjohn Company for many years. There is no domestic industrialized manufacturer of methylprednisolone except our company, so downstream products and preparations have long relied on imports. [0004] Using pregnandienolone acetate as the starting...

Claims

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Application Information

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IPC IPC(8): C07J5/00
Inventor 汪家振
Owner 台州百大药业有限公司
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