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Preparation of hydrocortisone

A technology for hydrocortisone and a compound, which is applied to a preparation field of steroid compounds, can solve the problems of low degree of industrialization, high cost, long route and the like, and achieves reduction of production cost and industrialization conditions, high feasibility and high yield. high rate effect

Inactive Publication Date: 2009-04-01
TIANJIN PHARMA GROUP CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Secondly, in the part of chemical synthesis method, in the document 1 J.Am.Chem.Soc.72, 5793 (1950), the chemical method 4,5 dehydrogenation is used, the cost is high, and the pollution is relatively large
Document 2 The route of ZL92110286.0 is longer, and more expensive ethanedithiol is used to protect the 3-ketone, the cost is high, and the degree of industrialization is not high

Method used

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  • Preparation of hydrocortisone
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  • Preparation of hydrocortisone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Bromination reaction: 9α-bromo-11β, 17α-dihydroxy-4-pregnene-3,20-dione;

[0036] Add 10g of 17-hydroxy-4,9-diene-pregna-3,20-dione (CN1896090) and 50ml of tetrahydrofuran into the reaction flask, stir, cool down to 0°C, and add dibromocyanide within 30 minutes Acetamide 6.5g, kept at 5-10°C for 1 hour, added 10% sodium bicarbonate aqueous solution to neutralize to PH=6.5, diluted in water, filtered, dried to obtain 11.5g of 9α-bromo-11β, 17α -Dihydroxy-4-pregnene-3,20-dione.

[0037] Debromination reaction: 11β, 17α-dihydroxy-4-pregnene-3,20-dione;

[0038] Add 11.5g of 9α-bromo-11β, 17α-dihydroxy-4-pregnene-3,20-dione, 100ml of DMF to the reaction flask, blow nitrogen, heat and control the temperature at 80-90°C, quickly drop 20ml of reducing agent for hydrogenation Tributyltin, after reacting for 1 hour, lower the temperature to 30°C, pour into 800ml saturated sodium chloride solution for dilution, stir for 1 hour, let stand for 1 hour, filter, wash with water unti...

Embodiment 2

[0046] Bromination reaction: 9α-bromo-11β, 17α-dihydroxy-4-pregnene-3,20-dione;

[0047] Add 10g of 17-hydroxy-4,9-diene-pregna-3,20-dione (CN1896090), 100ml of acetone into the reaction flask, stir, cool down to 0°C, and add N-bromine within 30 minutes 9g of substituted succinimide, kept at 5-10°C for 1 hour, added 10% aqueous sodium bicarbonate solution to neutralize to pH=6.5, diluted in water, filtered, and dried to obtain 11.2g of 9α-bromo-11β, 17α-Dihydroxy-4-pregnene-3,20-dione.

[0048] Debromination reaction: 11β, 17α-dihydroxy-4-pregnene-3,20-dione;

[0049] Prepare the reducing agent: take 10g of chromium particles in the reaction bottle, pass nitrogen, add 10ml of concentrated hydrochloric acid, react at room temperature for 30 minutes, and set aside.

[0050] In another reaction flask, add 12.5g of 9α-bromo-11β, 17α-dihydroxy-4-pregnene-3,20-dione, 60ml of dimethylformamide, blow nitrogen, cool down to 10°C, and slowly add The prepared chromium reducing agent w...

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Abstract

The invention relates to a preparation method of a steroid compound, in particular to the preparation of hydrocortisone, which takes 17-hydroxyl-4, 9-diene-pregna-3, 20-diketone as the initiator and is improved by 16, 17-grignard, 9, 11 th and 21st to obtain the hydrocortisone and a hydrocortisone-21st esterified ester thereof. As the production process adopts the existing intermediate of the company as the initiator, the line is concise, the material is easy to obtain, expensive auxiliary materials are saved, a line can be used for obtaining a plurality of products, and the yield and the cost are obviously superior to the historical synthetic method of the hydrocortisone and the derivative thereof; in addition, the adoption of the existing intermediate realizes the doubling production of the triamcinolone products, the hydrocortisone products and the anecortave acetate products, thus greatly reducing the production cost and industrial conditions, wherein, R is equal to -OCOR1, R1 is equal to the alkyl with less than 11carbon atoms.

Description

technical field [0001] The present invention relates to a kind of preparation method of steroid compound, especially relates to the preparation of hydrocortisone. Background technique [0002] Hydrocortisone and its derivatives are intermediate-acting adrenal cortex hormone drugs and are widely used clinically. Their products include: hydrocortisone and hydrocortisone acetate. Hydrocortisone Sodium Phosphate etc. Its curative effect is equivalent to that of prednisone, and its anti-inflammatory effect is stronger, which is 3 to 5 times that of cortisone. However, its water-salt metabolism effect is very weak, and it is generally not easy to cause side effects such as water and electrolyte disorders. At present, the products are oral and injection, and can also be applied externally to the skin. [0003] Synthetic technology of hydrocortisone and its derivatives has existed a long time ago, and the earliest hydrocortisone is taken out from animal adrenal gland, sees documen...

Claims

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Application Information

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IPC IPC(8): C07J5/00
Inventor 孙亮陈立营
Owner TIANJIN PHARMA GROUP CORP
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