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Preparation method of intermediate of steroidal drug with 16-beta-methyl

A technology of methyl steroids and intermediates, which is applied in the field of preparation of 16-β-methyl steroid drug intermediates, and can solve the problems of increasing the difficulty of refining and purifying in subsequent stages, difficult impurities, and affecting the quality of final products, etc. , to achieve the effect of easy access, high feasibility and strong operability

Inactive Publication Date: 2010-10-06
GUANGXI WANDE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are important intermediates of 16-β-methyl steroid drugs. In terms of the preparation of pregna-16β-methyl-3β, 17a-diol-20-one, we have not retrieved relevant patent documents. In the relevant literature In terms of reports, we retrieved [Title] my country's research progress on the use of sisal saponin to synthesize steroidal drugs, [Author] Han Guangdian Ma Zhaoyang, [Institution] Beijing Dongfang Huaya Institute of Chiral Medicine, Beijing 100024, [Title 】China Pharmaceutical Industry Journal. 2002, 33(9).-459-464, [Abstract] introduced 5a-pregna-16-en-3-ol-20-ketone-3-acetate as the starting material, After methylation, esterification, epoxidation and hydrolysis, the 16-methyl-17-hydroxy compound with the same structure as pregna-16β-methyl-3β, 17a-diol-20-one can be obtained, but difficult Refined impurities increase the difficulty of refining and purifying in subsequent sections and affect the quality of the final product

Method used

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  • Preparation method of intermediate of steroidal drug with 16-beta-methyl
  • Preparation method of intermediate of steroidal drug with 16-beta-methyl
  • Preparation method of intermediate of steroidal drug with 16-beta-methyl

Examples

Experimental program
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Effect test

Embodiment 1

[0025] Preparation of pregna-16β-methyl-3β, 17a-diol-20-one from 5-a-pregna-16-ene-3β-ol-20-one-3-acetate, the reaction principle is as follows image 3 Shown, the specific reaction steps are as follows:

[0026] Epoxidation reaction:

[0027] Add 50g of 5a-pregn-16-en-3-ol-20-one-3-acetate (sisalomonene) into 500ml of methanol solvent, and stir to make it uniform. Control the temperature below 40°C, add 19ml H 2 o 2 , and 30 ml of 25% (w / w) NaOH solution. After the addition, stir and keep warm for 5 to 24 hours. After the reaction is complete, add sodium bisulfite solution (10%) under stirring until the starch-potassium iodide test paper is negative. Adjust the pH of the solution to 6-7 with acetic acid (appropriate amount). Add 350ml of water, then distill under reduced pressure until the reaction liquid is about 200ml, and cool to room temperature. The reaction solution was slowly poured into 600ml of cold water and stirred for 60min. Filter and dry the filter cake t...

Embodiment 2

[0035] Preparation of pregna-16β-methyl-3β, 17a-diol-20-one from 5-a-pregna-16-ene-3β-ol-20-one, the reaction principle is as follows Figure 4 Shown, the specific reaction steps are as follows:

[0036] Epoxidation reaction:

[0037] Add 25 g of 5-a-pregn-16-en-3β-ol-20-one into 250 ml of methanol and stir to make it uniform. Control the temperature below 40°C, add 10ml H2O2, and 15ml 25% (w / w) NaOH solution. After the addition, stir and keep warm for 5 to 24 hours. After the reaction is complete, add sodium bisulfite solution (10%) under stirring until the starch-potassium iodide test paper is negative. Adjust the pH of the solution to 6-7 with acetic acid (appropriate amount). Add 150ml of water, then distill under reduced pressure until the reaction liquid is about 100ml, and cool to room temperature. The reaction solution was slowly poured into 300ml of cold water and stirred for 60min. Filter and dry the filter cake to obtain 24.6 g of dry product (5a-pregna-16α-17α...

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Abstract

The invention provides a preparation method of an intermediate of a steroidal drug with a 16-beta-methyl. In the method, a steroidal compound I is used as a starting material, and a steroidal compound II of the intermediate of the steroidal drug with the 16-beta-methyl can be prepared through epoxy reaction, ketal reaction, addition reaction and hydrolysis reaction for transformation of Position 3, Position 16, Position 17 and Position 20 or Position 16, Position 17 and Position 20. The steroidal compound II with the 16-beta-methyl is generally applied in preparation of the glucocorticoid drugs commonly used in clinical operation, such as betamethasone, betamethasone sodium phosphate, betamethasone acetate, clobetasol propionate, beclometasone dipropionate, betamethasone valerate and the like. In the formulas of the steroidal compound I and the steroidal compound II, R represents OH or OCOCH3, R1 represents OH, R2 represents CH3, and R3 represents CH3.

Description

technical field [0001] The invention relates to a preparation method of a steroid compound, in particular to a preparation method of a steroid drug intermediate with 16-beta-methyl. Background technique [0002] Glucocorticoids are necessary to maintain life. Glucocorticoids in the human body are synthesized and secreted by the cells of the adrenal cortex zona fascicularis, which have an important impact on protein, sugar, fat, water, electrolytic metabolism and the functions of various tissues and organs. Glucocorticoids in super-physiological amounts have various pharmacological effects such as anti-inflammation, anti-infection, anti-endotoxin, anti-allergy, anti-shock and suppression of immune response, and are often used to treat various stress reactions, immune diseases and inflammatory states . At present, it is mainly used for the treatment of active rheumatism, rheumatoid arthritis, lupus erythematosus, severe bronchial asthma, severe dermatitis, acute leukemia, etc...

Claims

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Application Information

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IPC IPC(8): C07J7/00
Inventor 王远秋王远宏杨冰
Owner GUANGXI WANDE PHARMA
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