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Synthetic method of dehydroprogesterone

A technique for dehydroprogesterone and its synthetic method, which is applied in the fields of steroids and organic chemistry, can solve problems such as low yield, limited technology, and difficult scale-up of production, and achieve high product yield, short synthetic steps, The effect of less isomer impurities

Active Publication Date: 2021-02-26
厦门欧瑞捷生物科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] The existing method for synthesizing dehydroprogesterone has problems such as low yield, technical limitations, and difficulty in enlarging production.

Method used

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  • Synthetic method of dehydroprogesterone

Examples

Experimental program
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Effect test

Embodiment 1

[0043] provided as Figure 1-4 The synthetic method of dehydroprogesterone shown in embodiment 1, concrete steps are as follows:

[0044] S100: Add ring A degradation products (200g, 0.9mol), THF (2000mL, 10v / w) into a 5L four-necked flask equipped with a dropping funnel, a thermometer and mechanical stirring, respectively, under nitrogen protection, then start stirring and cool down to ≤-50°C, then add 0.5M ethynylmagnesium bromide tetrahydrofuran solution (1.9L, 0.95mol, 1.05eq) dropwise to the above reaction system, control the reaction temperature not to exceed -45°C, after the addition is complete, then stir at constant temperature 30min. After the reaction is monitored by TLC, the above reaction solution is poured into a saturated ammonium chloride solution to quench, and the water phase is extracted once again after standing for stratification, and the combined organic phase is washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and f...

Embodiment 2

[0063] Based on Example 1, in this example, ethynylmagnesium chloride is used as the Grignard reagent at S100 to react, and other conditions remain unchanged, and the yield of compound II is 85%, and the reaction conditions of other S200-S700 remain unchanged, and its The yield of each step of S200-S700 does not change. Then the total yield of pure dehydroprogesterone is 29.6%.

Embodiment 3

[0065] Based on Example 1, in this example, DIPEA is used instead of TEA at S300, and other conditions remain unchanged, and the yield of compound IV is 60%. The reaction conditions of other S100-S200 and S400-S700 remain unchanged, and the above steps yield remains unchanged. Then the total yield of pure dehydroprogesterone is 29.1%.

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Abstract

The invention relates to the field of medicine preparation, in particular to a synthetic method of dehydroprogesterone, The synthetic method comprises the following steps: by using an A-ring degradation product as a raw material, carrying out addition reaction, dehydroxylation reaction, bromination reaction, elimination reaction, Grignard reaction, Mitsunobu reaction, twice Robinson ring-increasing reaction and water addition rearrangement reaction to generate a dehydroprogesterone product. The method has the advantages of cheap and easily available initial raw materials, few isomer impuritiesin the reaction process, easy purification, high product yield and the like, and has the advantages of short steps, simple operation, low equipment requirements, simple and easily available reagentsand easy realization of industrial production.

Description

technical field [0001] The invention relates to the field of medicine preparation, in particular to a synthesis method of dehydroprogesterone. Background technique [0002] Dehydroprogesterone, also known as dydrogesterone, the English name is: Dydrogesterone, the chemical name is 9β, 10α-pregna-4,6-diene-3,20-dione, mainly used in female fertility and reproductive health care, etc. On the one hand, it is not only widely used in miscarriage protection and prevention of miscarriage, but also widely used in the treatment of various diseases caused by endogenous progesterone deficiency, such as: dysmenorrhea, endometriosis, secondary amenorrhea, irregular menstrual cycle, Dysfunctional uterine bleeding, premenstrual syndrome, threatened or habitual abortion caused by progesterone deficiency, infertility caused by corpus luteum insufficiency, etc. [0003] The products currently on the market are all from Solvay, except for those manufacturers at home and abroad that cannot car...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J7/00
CPCC07J7/002
Inventor 郑飞剑李刚万明赵哲峰郑扶桑王萍魏积福周健高伟蔡金柱陈思涵张立军李娟
Owner 厦门欧瑞捷生物科技有限公司
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