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Preparation method of betamethasone intermediate

A technology of betamethasone and intermediates, which is applied in the field of preparation of steroid drug intermediates, can solve the problems of long steps and high costs, and achieve the effect of simple reaction operation and high yield

Active Publication Date: 2016-03-16
JIANGSU YUANDA XIANLE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the synthetic route steps provided by the above-mentioned documents are all relatively long, and the cost is relatively high.

Method used

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  • Preparation method of betamethasone intermediate

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Effect test

Embodiment 1

[0034] A preparation method of a betamethasone intermediate, the betamethasone intermediate is 16β-methyl-17α-hydroxypregna-4,9-diene-3,20-dione, the structural formula is as shown in formula VI Shown, described preparation method comprises:

[0035] (1) Cyanide reaction

[0036] Under nitrogen protection, put 100g of the compound of formula I into a clean four-necked reaction flask, add 200ml of methanol, stir, then add 50ml of acetone cyanohydrin, stir to raise the temperature to 40-45°C, and dropwise add 100ml of carbonic acid with a mass concentration of 5%. Potassium aqueous solution, the dropwise addition time is about 30 minutes, after the dropwise addition is completed, keep warm and stir for 24 hours, take samples for TLC tracking, until the raw materials are completely reacted. Dilute the reaction solution into 1000ml of water, stir for 1 hour, let stand for 2 hours, filter with suction, wash the filter cake with a large amount of water until it is neutral, and dry ...

Embodiment 2

[0046] A preparation method of a betamethasone intermediate, the betamethasone intermediate is 16β-methyl-17α-hydroxypregna-4,9-diene-3,20-dione, the structural formula is as shown in formula VI Shown, described preparation method comprises:

[0047] (1) Cyanide reaction

[0048] Under nitrogen protection, put 100g of the compound of formula I into a clean four-necked reaction flask, add 100ml of methanol, stir, then add 150ml of acetone cyanohydrin, stir to raise the temperature to 45-50°C, and dropwise add 200ml of carbonic acid with a mass concentration of 5%. Potassium aqueous solution, the dropwise addition time is about 30 minutes, after the dropwise addition is completed, keep warm and stir for 24 hours, take samples for TLC tracking, until the raw materials are completely reacted. Dilute the reaction solution into 1000ml of water, stir for 1 hour, let stand for 2 hours, filter with suction, wash the filter cake with a large amount of water until neutral, and dry the f...

Embodiment 3

[0058] A preparation method of a betamethasone intermediate, the betamethasone intermediate is 16β-methyl-17α-hydroxypregna-4,9-diene-3,20-dione, the structural formula is as shown in formula VI Shown, described preparation method comprises:

[0059] (1) Cyanide reaction

[0060] Under the protection of nitrogen, put 100g of the compound of formula I into a clean four-necked reaction flask, add 300ml of methanol, stir, then add 250ml of acetone cyanohydrin, stir to raise the temperature to 40-45°C, and dropwise add 250ml of carbonic acid with a mass concentration of 5%. Potassium aqueous solution, the dropwise addition time is about 30 minutes, after the dropwise addition is completed, keep warm and stir for 24 hours, take samples for TLC tracking, until the raw materials are completely reacted. Dilute the reaction solution into 1000ml of water, stir for 1 hour, let stand for 2 hours, filter with suction, wash the filter cake with a large amount of water until neutral, and dr...

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Abstract

The invention relates to a preparation method of a steroid drug intermediate, and concretely relates to a preparation method of a betamethasone intermediate which is 16beta-methyl-17alpha-hydroxypregna-4,9-diene-3,20-dione. The method comprises the following steps: carrying out a cyanidation reaction on 9alpha-hydroxy-4-ene-pregna-3,17-dione, carrying out a ketal protection reaction, carrying out a double elimination reaction, carrying out an epoxy reaction, and carrying out a Grignard addition hydrolysis reaction to prepare the target product. The method is a brand preparation technology for producing the betamethasone intermediate, and has the characteristics of cheap and easily available initial raw material, simple operations of all above reactions, high yield, suitableness for industrial massive production, and realization of the yield and the quality reaching satisfactory levels.

Description

technical field [0001] The present invention relates to a preparation method of a steroid drug intermediate, in particular to a betamethasone intermediate (i.e. 16β-methyl-17α-hydroxypregna-4,9-diene-3,20-dione) method of preparation. Background technique [0002] Betamethasone, chemical name: 16β-methyl-11β,17α,21-trihydroxy-9α-fluoropregna-1,4-diene-3,20-dione, molecular formula: C 22 h 29 FO 5 , molecular weight: 392.47. Betamethasone is a glucocorticoid drug with multiple pharmacological effects such as anti-inflammatory, anti-allergic and immune suppression. Its effect is the same as that of dexamethasone, but its anti-inflammatory effect is stronger than that of dexamethasone and triamcinolone. Clinical application is very extensive, mainly used for collagen diseases, such as rheumatoid arthritis, lupus erythematosus, rheumatic heart disease, myocarditis, etc., and rescue dying patients. At present, there are many types of preparations of betamethasone and its der...

Claims

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Application Information

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IPC IPC(8): C07J7/00
Inventor 冯永华姚庆旦杜艳杨科杨晓章
Owner JIANGSU YUANDA XIANLE PHARMA
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