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Synthesis method of dydrogesterone

A synthetic method, pregnant technology, applied in the field of drug synthesis, can solve the problems of many steps, low yield, lengthy synthetic route steps, etc.

Pending Publication Date: 2021-11-19
JIANGXI BAISIKANGRUI PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there are a few documents and patented technologies reporting the synthesis of dydrogesterone. For example, the British patent GB929271 reports a synthetic method of dydrogesterone. The method is photosteroid-4,7,22-triene-3- Ketones are used as raw materials through isomerization, ozonation, dehydration, and oxidation in sodium dichromate acidic solution. The synthesis route is tedious and the yield is low.
[0004] Chinese patent CN 110818760A discloses a dydrogesterone synthesized by using progesterone as a starting material through 6 steps of carbonyl protection, bromination, elimination, light ring opening, deprotection and isomerization. starting material, but the synthesis process is lengthy and the overall yield is low
In summary, the preparation of dydrogesterone in the prior art has the problems of many steps and low yield

Method used

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  • Synthesis method of dydrogesterone
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  • Synthesis method of dydrogesterone

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preparation example Construction

[0024] The invention provides a kind of synthetic method of dydrogesterone, comprising the following steps:

[0025] Dissolve progesterone and perform photochemical reaction to obtain 9β,10α-pregna-4-ene-3,20-dione;

[0026] mixing the 9β,10α-pregn-4-ene-3,20-dione, an organic solvent and a benzoquinone oxidizing agent, and performing a dehydrogenation reaction to obtain dydrogesterone;

[0027] The organic solvents include alcohol organic solvents, ether organic solvents and aromatic hydrocarbon organic solvents.

[0028] In the present invention, unless otherwise specified, the raw materials used in the present invention are preferably commercially available products.

[0029] The invention dissolves the progesterone and performs photochemical reaction to obtain 9β, 10α-pregna-4-ene-3,20-dione.

[0030] In the present invention, the dissolved reagent preferably includes a polar organic solvent, and the polar organic solvent preferably includes one or more of tetrahydrofura...

Embodiment 1

[0059] Under the protection of nitrogen, mix 1.6g of progesterone and 250mL of tetrahydrofuran to carry out the first photochemical reaction and the second photochemical reaction. The condition of the first photochemical reaction is to use a high-pressure mercury lamp for 1h, and the wavelength is 200-400nm; The condition of the photochemical reaction is to place the pyrex glass tube around the high-pressure mercury lamp, filter out the light with a wavelength less than 300nm, and continue to irradiate for 3h.

[0060] Evaporate the solvent in the system after the photochemical reaction to dryness, add 150 mL of ethanol / acetonitrile = 3:1 mixed solvent to the obtained solid to redissolve, heat and reflux for 10 min at a temperature of 75 ° C, and obtain the solution at a temperature of -5 ° C Cool down for 1 hour, and after the solid precipitates, perform suction filtration, and vacuum-dry the product obtained by suction filtration at a vacuum degree of -0.07MPa and a temperatu...

Embodiment 2

[0071] Example 2 According to the synthesis method of Example 1, the only difference is that the light source is replaced by a xenon lamp, and finally 0.98g of dydrogesterone is obtained, with a total yield of 82.3%.

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Abstract

The invention belongs to the technical field of compound synthesis, and particularly provides a synthetic method of dydrogesterone. The preparation method provided by the invention comprises the following steps: dissolving progesterone, and carrying out a photochemical reaction, so as to obtain 9beta, 10alpha-pregnane-4-ene-3, 20-dione; and mixing the 9beta, 10alpha-pregnane-4-ene-3, 20-dione, an organic solvent and a benzoquinone oxidizing agent, and carrying out a dehydrogenation oxidation reaction, so as to obtain the dydrogesterone. The organic solvent comprises an alcohol organic solvent, an ether organic solvent and an aromatic hydrocarbon organic solvent. The initial raw materials are cheap and easy to obtain, the number of reaction steps is small, and the target product dydrogesterone can be obtained only through two steps. Moreover, due to the fact that the number of reaction steps is small, the loss of raw materials is small, and the yield of the finally obtained dydrogesterone is high. The data of the embodiment shows that the yield of the dydrogesterone can reach 82.3% according to the synthesis method provided by the invention.

Description

technical field [0001] The invention belongs to the technical field of drug synthesis, in particular to a method for synthesizing dydrogesterone. Background technique [0002] Dydrogesterone, also known as dehydroprogesterone, has a chemical name of 9β,10α-pregna-4,6-diene-3,20-dione, and is a white powder at room temperature. As a synthetic progestin, dydrogesterone has obvious advantages and safety compared with other similar drugs because it does not have the side effects of estrogen, androgen, corticosteroids and other hormones, and can be used to treat endogenous Diseases caused by progesterone deficiency, such as dysmenorrhea, secondary amenorrhea, endometriosis, dysfunctional uterine bleeding, premenstrual syndrome, threatened or habitual abortion due to progesterone deficiency, and insufficient corpus luteum infertility etc. Therefore, dydrogesterone is currently the most ideal progestin drug. [0003] At present, there are a few documents and patented technologie...

Claims

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Application Information

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IPC IPC(8): C07J7/00
CPCC07J7/002
Inventor 秦元成钱建武倪彩玲冯荣伟张学良钟宗海
Owner JIANGXI BAISIKANGRUI PHARMA
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