Preparation method of dydrogesterone intermediate

A technology for dydrogesterone and intermediates, which is applied in the field of dydrogesterone intermediates, can solve the problems of harsh reaction conditions, difficult to obtain raw materials, low yield and the like, and achieves high utilization rate of raw materials, shortened illumination time, and preparation process. short effect

Active Publication Date: 2020-05-19
上海璟兆实业有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the traditional synthetic method of dydrogesterone product, as reported by Royal Netherlands Chemical Society (1960,79, P771), Solvay Pharmaceutical Company of Holland produces the bulk drug of dehydroprogesterone product, and the processing route that adopts is: The by-product of vitamin D production - photosterol is used to produce dehydroprogesterone products through chemical reactions such as Woshi oxidation, rearrangement, lithium ammonia reduction, ozonation, 20-position complexation, oxidation, and dehydrogenation, with a total yield of about 3 %, its defect is that the reaction steps are longer, the yield is lower, and the cost is higher, and it uses poisonous

Method used

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  • Preparation method of dydrogesterone intermediate
  • Preparation method of dydrogesterone intermediate
  • Preparation method of dydrogesterone intermediate

Examples

Experimental program
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Effect test

Embodiment 1

[0042] Uniformly mix 1 g of ergosterol and 20 mL of tetrahydrofuran to obtain solution A; irradiate solution A with an LED ultraviolet lamp with a model of DL-UVB-UV315-40W at 10-15°C, and the illumination time is 700 min, and solution B is obtained after the illumination ends; The solvent was distilled off under reduced pressure from solution B, and 0.25 g of photosterol L2 was obtained by preparative column separation. In this example, the yield of photosterol L2 was 25%.

Embodiment 2

[0044]Mix 1 g of ergosterol and 20 mL of tetrahydrofuran evenly to obtain solution A; at 10-15 ° C, first use LED ultraviolet lamp with model DL-UVC-UV254-30W to irradiate solution A, and the illumination time is 200min, and then use model DL- UVB-UV315-40W LED ultraviolet lamp irradiation, the irradiation time is 200min, and the solution B is obtained after the irradiation; the solvent B is distilled off under reduced pressure, and 0.25 g of photosterol L2 is obtained by preparative column separation. In this example, the yield of photosterol L2 was 25%.

Embodiment 3

[0046] Mix 1 g of 7-dehydropregnenolone acetate and 40 mL of tetrahydrofuran uniformly to obtain solution A; at 10-15 °C, irradiate solution A with an LED ultraviolet lamp with a model of DL-UVB-UV315-40W, and the illumination time is 750 min , solution B was obtained after irradiation; the solvent was distilled off under reduced pressure for solution B, and 0.22 g of pregnansterol acetate was obtained by preparative column separation. The yield of pregnansterol acetate in this example was 22%.

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Abstract

The invention discloses a preparation method of a dydrogesterone intermediate. The preparation method is characterized by comprising the following steps: dissolving 5,7-diene steroid compound in an organic solvent to obtain a solution as a raw material; and carrying out a photocatalytic reaction and separating to obtain the dydrogesterone intermediate, wherein the 5,7-diene steroid compound is 7-dehydropregnenolone acetate, pregna-5,7-diene-3,20-diketodivinyl ketal, 7-dehydropregnenolone, ergosterol or pregna-5,7-diene-3,20-diketo-3-vinyl ketal, and a lamp used in the photocatalytic reaction comprises an LED ultraviolet lamp with the wavelength range of 295-335 nm. The preparation method of the dydrogesterone intermediate is high in yield, low in cost, safer in preparation and friendlier to environment.

Description

technical field [0001] The present invention relates to the technical field of dydrogesterone intermediates, in particular to a preparation method of a dydrogesterone intermediate. Background technique [0002] Dydrogesterone (Dydrogesterone), also known as dehydroprogesterone, CAS 152-62-5, chemical name is 9β,10α-pregnant-4,6-diene-3,20-dione. Dydrogesterone is a highly potent progesterone that is clinically used to treat amenorrhea, endometriosis, prevent functional bleeding and threatened abortion. [0003] Pregnantyl Photosterol Acetate (CAS 1788-02-5), 9β,10α-Pregnant-5,7-diene-3,20-dione diethylketal (CAS 5488-51-7), Pregnant Photosterol (CAS 1819-14-3), Photosterol L 2 (CAS 494-69-1), 9β,10α-pregna-5,7-diene-3,20-dione-3-ethylene ketal (CAS 32164-72-0) are synthetic dydrogesterone, respectively key intermediates of different synthetic routes. [0004] In the traditional synthetic method of dydrogesterone products, as reported by the Royal Netherlands Society of C...

Claims

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Application Information

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IPC IPC(8): C07J21/00C07J9/00C07J7/00
CPCC07J21/006C07J7/002C07J9/00Y02P20/584
Inventor 郑坚应园
Owner 上海璟兆实业有限公司
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