Synthesis method of ancopristone

A synthetic method and technology of angopristone, applied in the field of preparation of steroidal compounds, can solve the problems of difficult industrial production of angopristone synthetic method, achieve the effects of reducing production cost, avoiding preparation, and increasing reaction scale

Pending Publication Date: 2022-03-18
ZHEJIANG XIANJU JUNYE PHARM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In order to solve the problems in the prior art that the synthetic method of angopristone is difficult to industrialized production and needs to use expensive palladium catalyst, the technical scheme we provide is:

Method used

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  • Synthesis method of ancopristone
  • Synthesis method of ancopristone

Examples

Experimental program
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Effect test

Embodiment 1

[0018] Dissolve mifepristone (50.0 g) in ethanol (500 mL) solution, add Lindella catalyst (15.0 g), add quinoline (10 g), replace hydrogen 3 times, and stir for 6 hours. TLC detects that the reaction is complete, stops the reaction, and filters. The filtrate was spin-dried until it became a paste, and methanol (200 mL) was added to reflux to dissolve, cooled naturally to room temperature, stirred and crystallized, filtered, and dried to obtain 47 grams of light yellow solid powder.

Embodiment 2

[0020] Dissolve mifepristone (1.0 kg) in methanol (8 L) solution, add Lindella catalyst (300.0 g), add quinoline (100 g), replace with hydrogen three times, and stir for 12 hours under 1 atmosphere of hydrogen. TLC detected that the reaction was complete, stopped the reaction, filtered, spin-dried the filtrate to a paste, added methyl tert-butyl ether (5 L) to reflux to dissolve, cooled naturally to room temperature, stirred and crystallized, filtered, and dried to obtain a light yellow solid powder 0.95 kg.

Embodiment 3

[0022] Dissolve mifepristone (30.0 kg) in ether (300 L) solution, add Lindella catalyst (6 kg), add quinoline (2 kg), replace hydrogen 3 times, and stir for 12 hours. TLC detected that the reaction was complete, stopped the reaction, filtered, spin-dried the filtrate to a paste, added methyl tert-butyl ether (120 L) to reflux to dissolve, cooled naturally to room temperature, stirred and crystallized, filtered, and dried to obtain a light yellow solid powder 28.6 kg.

[0023] The H NMR spectrum and carbon spectrum data of gained Angopristone are as follows:

[0024] 1 H NMR (400 MHz, CDCl 3 ) δ 7.02 (d, J = 8.6 Hz, 1H), 6.67 (d, J = 8.2Hz, 1H), 5.74 (s, 1H), 5.65 – 5.55 (m, 1H), 5.50 (d, J = 12.0 Hz, 1H), 4.30(d, J = 7.0 Hz, 1H), 2.91 (s, 6H), 2.78 – 2.66 (m, 1H), 2.56 (m, 2H), 2.51 –2.22 (m, 5H), 2.15 – 1.96 (m, 3H), 1.88 ( d, J = 7.0 Hz, 3H), 1.85 – 1.78 (m,1H), 1.77 – 1.66 (m, 1H), 1.59 – 1.20 (m, 5H), 0.94 – 0.76 (m, 1H), 0.62 (s, 3H);

[0025] 13 C NMR (101 ...

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Abstract

The invention relates to a synthesis method of ancopristone, which comprises the following steps: uniformly mixing mifepristone as a reaction substrate, a lindla catalyst, quinoline and an organic solvent, introducing hydrogen, and reacting in a hydrogen atmosphere; the reaction temperature is-20 DEG C to 50 DEG C, and the reaction time is 1-24 hours; and after the reaction is finished, filtering and concentrating to obtain the ancopristone.

Description

technical field [0001] The invention relates to a preparation method of a steroid compound, in particular to a synthesis method of angopristone. Background technique [0002] Angopristone (Aglepristone) is a steroidal drug that is a competitive progesterone antagonist approved for pregnancy termination in bitches in early, middle, and third trimesters. Angopristone can also be used to terminate pregnancy in cats and ruminants such as cattle. [0003] At present, there is no systematic report on the synthesis of angopristone, and only a very small amount of literature mentions the synthesis of this compound. In 1987, F. Zumstein et al reported the preparation of gram-level angopristone through column chromatography. In 2018, J.Garcia-Calvo et al. reported that the milligram-level synthesis was completed using a self-made expensive palladium catalyst. The above reports are far from industrial application. Therefore, the synthesis of angopristone has attracted great attenti...

Claims

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Application Information

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IPC IPC(8): C07J41/00
CPCC07J41/0033
Inventor 张峥斌李纯尹金玉张杰锋
Owner ZHEJIANG XIANJU JUNYE PHARM CO LTD
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