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Didrogesterone and preparation method thereof

A technology of dydrogesterone and ethyl, applied in the field of dydrogesterone, dydrogesterone and its preparation, can solve the problems of short yield, low yield and lengthy synthesis process, etc.

Pending Publication Date: 2022-05-06
西安国康瑞金制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Nowadays, there are few reports about the preparation method of dydrogesterone. Patent CN110818760A discloses a production process for industrially synthesizing dydrogesterone. , light ring-opening, deprotection and isomerization, finally synthesized dydrogesterone, although progesterone is relatively easy to get, but the synthesis process is tedious and the yield is low, so there is an urgent need for a shorter synthesis process and higher yield Preparation method of dydrogesterone

Method used

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  • Didrogesterone and preparation method thereof
  • Didrogesterone and preparation method thereof
  • Didrogesterone and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] 1) Add 126kg of methanol to the dry reaction kettle, pass through 42kg of hydrogen chloride to prepare an acid-alcohol solution, add 20kg of 3,20-bis(ethyldioxy)-9β-10α-pregna-5,7-diene , react at room temperature for 50 minutes; add 40 kg of water to the reaction solution, add 180 kg of ammonia water, add time for 2 hours to crystallize, and grow the crystal for 2 hours, filter and wash to obtain 15 kg of deprotection group intermediate;

[0031] 2) Add 100 kg of toluene to the transposition tank, put in the deprotection group intermediate, stir and add 2.88 kg of acetic acid, heat to reflux for transposition, add 50 kg of water for extraction after the reaction, collect the toluene phase, and evaporate the toluene to dryness;

[0032] 3) Add 193 kg of ethanol, keep stirring for 2.5 hours for crystallization, centrifuge, and dry to obtain the dydrogesterone product with a product yield of 44.5%.

[0033] The dydrogesterone obtained in embodiment 1 is analyzed by a chro...

Embodiment 2

[0040] 1) Add 118.8kg of ethanol to the dry reaction kettle, pass through 29.5kg of hydrogen chloride to prepare an acid-alcohol solution, add 3,20-bis(ethyldioxy)-9β-10α-pregna-5,7-bis 20 kg of alkene was reacted at room temperature for 60 minutes; 35 kg of water was added to the reaction solution, 160 kg of ammonia was added, the feeding time was 2 hours to crystallize, the crystal growth time was 2 hours, filtered, washed, and 13 kg of deprotected intermediate was obtained;

[0041] 2) Add 61.2 kg of toluene to the indexing tank, put in the deprotection intermediate, stir and add 1.8 kg of acetic acid, heat to reflux to remove the protecting group, add 40 kg of water for extraction after the reaction, collect the toluene phase, and evaporate the toluene to dryness;

[0042] 3) Add 177 kg of acetone, keep stirring for 2 hours for crystallization, centrifuge, and dry to obtain dydrogesterone product with a product yield of 45.2%.

[0043] The dydrogesterone obtained in embodi...

Embodiment 3

[0050] 1) Add 108kg of isopropanol to a dry reaction kettle, pass through 21.6kg of hydrogen chloride to prepare an acid-alcohol solution, add 3,20-bis(ethyldioxy)-9β-10α-pregna-5,7- 20 kg of diene, reacted at room temperature for 70 minutes; 30 kg of water was added to the reaction solution, 120 kg of aqueous ammonia was added, the feeding time was 4 hours to crystallize, the crystal growth time was 1 hour, filtered, washed, and 10 kg of the deprotected intermediate was obtained;

[0051] 2) Add 100 kg of toluene to the transposition tank, put in the deprotected intermediate, stir and add 2.88 kg of acetic acid, heat to reflux for transposition, add 50 kg of water for extraction after the reaction, collect the toluene phase, and evaporate the toluene to dryness;

[0052] 3) Add 177 kg of acetone, keep stirring for 2 hours for crystallization, centrifuge, and dry to obtain the dydrogesterone product with a product yield of 46%.

[0053] The dydrogesterone obtained in embodimen...

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Abstract

The invention provides didrogesterone and a preparation method thereof, which comprises the following steps: carrying out deprotection reaction on a prepared acid alcohol solution and 3, 20-bis (ethyldioxy)-9beta-10alpha-pregna-5, 7-diene, neutralizing with alkaline water, and crystallizing to obtain a deprotecting intermediate; heating and refluxing with acetic acid in a hydrophobic solvent for transposition, adding water into reaction liquid for extraction and impurity removal, collecting an oil phase, concentrating and desolventizing the oil phase under reduced pressure, and adding a hydrophilic solvent for crystallization, thereby obtaining the product didrogesterone. The preparation method provided by the invention has the advantages of single solvent, simple reaction conditions, easiness in operation, high yield of the didrogesterone, good quality and the like, and has a very good industrial application prospect.

Description

【Technical field】 [0001] The invention belongs to the technical field of medicine and relates to dydrogesterone, in particular to dydrogesterone and a preparation method thereof. 【Background technique】 [0002] Dydrogesterone is an oral progestogen with the chemical name 9β,10α-pregnane-4,6-diene-3,20-dione, which has no estrogen, androgen and adrenocortical hormone effects, and does not produce heat , and had no effect on lipid metabolism. As a synthetic progestin, dydrogesterone is used to treat diseases caused by endogenous progesterone deficiency, such as dysmenorrhea, endometriosis, secondary amenorrhea, irregular menstrual cycle, dysfunctional Uterine bleeding, premenstrual syndrome, threatened miscarriage or habitual miscarriage due to progesterone deficiency, infertility due to corpus luteum insufficiency. [0003] Nowadays, there are few reports about the preparation method of dydrogesterone. Patent CN110818760A discloses a production process for industrially synt...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J7/00
CPCC07J7/002Y02P20/55
Inventor 严捷王培文刘伟李娜蒲飞飞侯丽英
Owner 西安国康瑞金制药有限公司
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