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Impurity removal method of progesterone

A progesterone and impurity technology, which is applied in the field of preparation and processing of steroid hormone drugs, can solve the problem of reducing to less than 0.6%, and achieve the effects of low equipment requirements, mild reaction, and low cost input

Pending Publication Date: 2022-01-21
ZHEJIANG SHENZHOU PHARMA
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Because the above-mentioned bisnoraldehyde impurities (2) and (3) are close to the physical and chemical properties of progesterone, it is impossible to reduce the impurity content to below 0.6% with conventional refining methods such as recrystallization and adsorption, which is an important step for obtaining high purity in industrial production. Progesterone creates an insurmountable hurdle

Method used

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  • Impurity removal method of progesterone

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Experimental program
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Effect test

Embodiment 1

[0024] The impurity removal method of embodiment 1 progesterone

[0025] Completely dissolve 50g of progesterone crude product (containing 2% impurity aldehyde) in 150ml of methanol, add 0.25g of p-toluenesulfonic acid, control the temperature at 60°C and stir for reaction. Thin layer chromatography shows that the reaction of aldehyde impurities is complete, add 0.25ml of triethylamine Neutralize the amine, concentrate the methanol, add 250ml methyl tert-butyl ether, cool down to -20°C, filter, and dry to obtain 46.3g of high-purity progesterone, the product yield is 92.6%, the product melting point is 129.2~130.0°C, HPLC Content 99.7%, impurity aldehyde content 0.12%.

Embodiment 2

[0026] The impurity removal method of embodiment 2 progesterone

[0027] 50g of crude progesterone (containing 3% impurity aldehyde) was completely dissolved in 500ml of methanol, 0.5g of malonic acid was added, and the temperature was controlled at 40°C to stir the reaction. Thin layer chromatography showed that the reaction of aldehyde impurities was complete, and 0.5ml of pyridine was added to neutralize , concentrated methanol, added 50ml ethyl acetate, cooled to 5°C, filtered, dried to obtain 45.5g of high-purity progesterone, product yield 91.0%, product melting point 128.8~130.0°C, HPLC content 99.5%, impurity aldehyde content 0.17%.

Embodiment 3

[0028] The impurity removal method of embodiment 3 progesterone

[0029] 50g of crude progesterone (containing 2.5% impurity aldehyde) was completely dissolved in 1500ml of ethanol, 2.5g of pyridinium hydrobromide was added, and the temperature was controlled at 20°C to stir the reaction. Thin layer chromatography showed that the reaction of aldehyde impurities was complete, and 2.5ml of piperidine was added. Neutralize with pyridine, concentrate to remove ethanol, add 25ml of acetone, cool to -10°C, filter and dry to obtain 45.8g of high-purity progesterone, product yield 91.6%, product melting point 129.1-130.2°C, HPLC content 99.6%, impurity Aldehyde content 0.15%.

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Abstract

The invention discloses an impurity removal method of progesterone, and belongs to the technical field of preparation and processing of steroid hormone drugs. According to the method, aldehyde impurities in a progesterone crude product react with an alcohol organic solvent to generate an acetal compound, solubility difference between the acetal compound and progesterone is achieved, then the acetal compound is removed through refining, and high-purity progesterone with the content higher than 99.5% and the total content of impurity aldehyde lower than 0.2% is obtained. The impurity removal method disclosed by the invention is simple and convenient in reaction process operation and low in cost investment; the reaction process is mild and safe, conditions are easy to control, and the product refining rate is high; and the used reagent is pollution-free and environment-friendly.

Description

technical field [0001] The invention relates to the technical field of preparation and processing of steroid hormone medicines, in particular to a method for removing impurities of progesterone, in particular to a method for removing impurities of progesterone containing aldehyde impurities. Background technique [0002] Progesterone is a natural progesterone secreted by the corpus luteum of the ovary. It has a significant morphological effect on the endometrium stimulated by estrogen in the body. It is necessary for maintaining pregnancy and is also an important intermediate for the synthesis of other steroid drugs. , has a very important application in clinical medicine. [0003] There are many methods for the synthesis of progesterone reported in the open literature, but due to the influence of starting materials, reaction conditions and reaction devices, there is no ideal method for improving the purity of progesterone that has been publicly reported. The European Pharm...

Claims

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Application Information

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IPC IPC(8): C07J7/00
CPCC07J7/002
Inventor 邵振平王荣王炳乾王洪福黄橙橙雷灵芝王友富
Owner ZHEJIANG SHENZHOU PHARMA
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