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Dydrogesterone synthesis methodand compound

A technology of chemical reaction and photochemical reaction, applied in the direction of steroids, organic chemistry, etc., can solve the problems of increased product impurities, low yield of target products, low photochemical yield, etc.

Pending Publication Date: 2021-09-14
SUZHOU LANXITE BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] The patent CN101318982A published in 2008 by Taizhou Wanfu Pharmaceutical Co., Ltd. uses the photochemical reaction of 3-acetoxy-pregna-5,7-dien-20-one, and the photochemical yield is relatively low (30-35%). The reason may be It is because the carbonyl group in the molecule will undergo Norrish type I and / or Norrish type II reactions (translated by Wu Lizhu, Tong Zhenhe, etc. in "Modern Molecular Photochemistry"), which will increase the impurities of the product under light irradiation, and the yield of the target product will be low.

Method used

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  • Dydrogesterone synthesis methodand compound
  • Dydrogesterone synthesis methodand compound
  • Dydrogesterone synthesis methodand compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035]

[0036] Add 500g DG-7, 500g ethylene glycol, 500g triethyl orthoformate, 5g p-toluenesulfonic acid and 5000ml dichloromethane into the reaction flask, stir at room temperature and complete the reaction, add 1000ml water and stir to separate the liquid, organic The phase was concentrated under reduced pressure to obtain solid DG-8.1 with a yield of 95.2%.

[0037] ESI-HRMS theoretical value: C 23 h 34 o 3 [M+H] + 359.2508, found 359.2510.

[0038] 1H-NMR (δ, ppm, CDCl 3 ):5.70-5.55(m,1H);5.39-5.38(m,1H);4.02-3.84(m,4H);3.66-3.59(m,1H);2.48-2.43(m,1H);2.30-2.24 (m,1H);2.16-2.12(m,1H);1.98-1.94(m,1H);1.89-1.87(m,4H);1.83-1.66(m,4H);1.61-1.53(m,1H) ;1.51-1.41(m,2H);1.32-1.22(m,5H);0.94(s,3H);0.71(s,3H).

Embodiment 2

[0040]

[0041] Add 500g DG-7, 114g triethyl orthoformate, 1.4g p-toluenesulfonic acid and 540ml methanol into the reaction flask, react at 50℃~60℃ for three hours, reduce pressure, add 500mL ethyl acetate to extract, then use 500mL Washed with saturated sodium bicarbonate, washed with 500 mL saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated to obtain DG-8.2 with a yield of 93.7%.

[0042] ESI-HRMS theoretical value: C 23 h 36 o 3 [M+H] + 361.2664, found 361.2669.

[0043] 1H-NMR (δ, ppm, CDCl 3):5.74-5.58(m,1H); 5.40-5.37(m,1H); 4.05(s,3H); 3.84(s,3H); 3.70-2.45(m,2H); );1.90-1.86(m,4H);1.72-1.67(m,4H);1.60-1.43(m,3H);1.35-1.19(m,5H);0.89(s,3H);0.74(s,3H ).

[0044] Synthesis of Compound DG-9 Series

Embodiment 3

[0046]

[0047] Add 100g of DG-8.1, 100g of triethylamine into 10L of absolute ethanol and stir to dissolve, then add 0.5g of 2,6-di-tert-butyl-p-cresol, add an internal light with quartz cold hydrazine (transmitting wavelength 200-300nm) photochemical reactor. Turn on the stirring, control the temperature at 10-15°C to circulate the freezing liquid, and turn on the 500W high-pressure mercury lamp to irradiate for 8 hours. Turn off the high-pressure mercury lamp, filter the reaction solution, collect the filtrate, add the filtrate to the internally illuminated photochemical reactor with high borosilicate glass cold hydrazine (transmissible wavelength 310nm-400nm), turn on the stirring, and turn on the 500W high-pressure mercury lamp After irradiating for 16 hours, turn off the high-pressure mercury lamp, concentrate the reaction solution under reduced pressure at 35°C, freeze and crystallize to obtain DG-9.1 as a white solid with a purity of 99.3% and a yield of 70.6%.

[...

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Abstract

The invention provides a novel dydrogesterone synthesis method. The method comprises the following steps: preparing carbonyl-protected dehydropregnenolone by taking dehydropregnenolone as a starting material, then obtaining a methyl configuration reversing compound through a photocatalytic reaction, and further obtaining the dydrogesterone through deprotection, hydroxyl oxidation and double-bond rearrangement reaction. The method provided by the invention has the advantages of easily available raw materials, high yield and simple and mild reaction conditions, and is suitable for industrial production of the dydrogesterone.

Description

technical field [0001] The invention belongs to the field of medicine synthesis, in particular to a new synthesis method of dydrogesterone. Background technique [0002] Dydrogesterone is a synthetic progestin that can be used to treat diseases caused by endogenous progesterone deficiency, such as dysmenorrhea, endometriosis, secondary amenorrhea, irregular menstrual cycle, dysfunctional uterus Bleeding, premenstrual syndrome, threatened miscarriage or habitual miscarriage caused by progesterone deficiency, and infertility caused by corpus luteum insufficiency are currently ideal progesterone drugs. [0003] Document Recueil des Travaux Chimiques des Pays-Bas (1961), 80:43-46 reported that 3-hydroxy-pregn-5,7-dien-20-one was used as raw material to carry out steroid in tetrahydrofuran with high-pressure mercury lamp. After the body B switching ring reaction is completed, the 10-position angle methyl group is reversed by conformational isomerization, and the product is dydro...

Claims

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Application Information

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IPC IPC(8): C07J7/00C07J17/00
CPCC07J7/002C07J7/007C07J17/00
Inventor 杨映权袁海涛刘常仁王飞
Owner SUZHOU LANXITE BIOTECH
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