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A kind of synthetic method of cyproterone acetate dehydrogenate

A technology of cyproterone acetate and a synthesis method, applied in the directions of steroids, organic chemistry, etc., can solve the problems of serious environmental pollution, high consumption of auxiliary materials, low synthesis yield and the like, and achieves reduction of environmental pollution, reduction of production costs, The effect of shortening the reaction cycle

Active Publication Date: 2016-03-02
ZHEJIANG XIANJU XIANLE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Cyproterone orthoacetate dehydrogenation product is obtained through 2-step dehydrogenation reaction of raw materials and 2-step drying of the material. The reaction process consumes a lot of auxiliary materials, and the highly toxic 4-chlorobenzoquinone is used, which seriously pollutes the environment. 2-step synthesis The yield is low, only 65%

Method used

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  • A kind of synthetic method of cyproterone acetate dehydrogenate

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Put in 25g of 17α-OH progesterone, 40g of absolute ethanol, and 15.75g of triethyl orthoformate, stir for 30 minutes (incompletely dissolved, white suspension), quickly add 0.88g of pyridinium p-toluenesulfonate, heat up to 38°C, keep warm After 6.5 hours of reaction, the TLC detection was almost complete (developing agent: benzene: acetone = 6: 1), lower the temperature below 25°C, add 0.88g of triethylamine to neutralize to acidity (PH = 7-8), and stir for 10 minutes.

[0021] Drop into 216.5g toluene in the above-mentioned reactant, and pass into N 2 Protect, stir for 10 minutes, then add 30g of dichlorodicyanoquinone, stir to raise the temperature to 90°C, and keep stirring at a constant temperature of 85°C for 3.5h, sample TLC to analyze the complete reaction of raw materials (developer: acetone: chloroform = 1:20).

[0022] Cool down to 60°C, filter while hot, and wash the filter cake with a small amount of hot toluene; combine the filtrate and lotion, wash with 5...

Embodiment 2

[0025] Add 25g of 17-OH progesterone, 41.25g of absolute ethanol, and 17g of triethyl orthoformate, stir for 30 minutes (incompletely dissolved, white suspension), quickly add 1.0g of pyridinium p-toluenesulfonate, heat up to 40°C, and keep warm After 6.5 hours of reaction, the TLC detection is basically complete (developing agent: benzene: acetone = 6: 1), lower the temperature below 25 °C, add 1.0 g of triethylamine to neutralize to acidity (PH = 7-8), and stir for 10 min.

[0026] Drop into 217.75g toluene in the above-mentioned reactant, and pass into N 2 Protect and stir for 10 minutes; then add 31.3g of dichlorodicyanoquinone, stir to raise the temperature to 90°C, and stir at a constant temperature of 88°C for 3.5h, sample TLC to analyze the complete reaction of raw materials (developer: acetone: chloroform = 1:20).

[0027] Cool down to 60°C, filter while hot, and wash the filter cake with a small amount of hot toluene; combine the filtrate and lotion, wash with 50ml o...

Embodiment 3

[0030] Add 25g of 17α-OH progesterone, 30g of absolute ethanol, and 10g of triethyl orthoformate, stir for 30 minutes (incompletely dissolved, white suspension), quickly add 0.25g of pyridinium p-toluenesulfonate, heat up to 42°C, and keep warm for reaction After 6.5 hours, the TLC detection was almost complete (developer: benzene:acetone = 6:1), lower the temperature below 25°C, add 0.3g triethylamine to neutralize to acidity (PH=7-8), and stir for 10 minutes.

[0031] Drop into 150g toluene in the above-mentioned reactant, and pass into N 2 Protect, stir for 10 minutes, then add 20g of dichlorodicyanoquinone, stir to raise the temperature to 90°C, and keep stirring at 90°C for 3.5h, sample TLC to analyze the complete reaction of raw materials (developer: acetone: chloroform = 1:20).

[0032] Cool down to 60°C, filter while hot, and wash the filter cake with a small amount of hot toluene; combine the filtrate and lotion, wash with 50ml of water, and concentrate the toluene fe...

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Abstract

The invention provides a synthetic method of cyproterone acetate dehydrogenized substance, and belongs to the technical field of synthetic technologies of steroid agents. The synthetic method comprises the following processing steps of: 1) carrying out etherification reaction on 17 alpha-hydroxyl progesterone, absolute ethyl alcohol and triethyl orthoformate which serve as the raw materials, and carrying out acid-base neutralization after the reaction until reaching acidity; and 2) adding toluene to the reactant obtained in step 1) to be used as a reaction solvent; charging N2 for protecting; adding 2,3-fichloro-5,6-dicyano-1,4-benzoquinone to carry out dehydrogenation reaction; and sequentially filtering, concentrating and drying after the reaction, so as to obtain the cyproterone acetate dehydrogenized substance. According to the synthetic method, an efficient one-pot synthetic method is adopted, the double discharges in the conventional method are combined into one to be carried out, and 6s hydrogen ion in the raw materials is activated in the etherification process, so that the dual dehydrogenation reaction can be accomplished in one step, the product yield reaches 80 to 83%, the reaction period is shortened, the labor productivity is increased, the investment on equipment is decreased as well as the varieties and amount of used solvents, the environmental pollution is reduced, and the production cost of a plant is decreased.

Description

technical field [0001] The invention belongs to the technical field of steroid drug synthesis, in particular to a method for synthesizing cyproterone acetate dehydrogenate. Background technique [0002] Cyproterone acetate dehydrogenate, whose structural formula is shown in formula (1), belongs to the prophase intermediate of progesterone cyproterone acetate. Cyproterone acetate is an antiandrogen drug that can treat inoperable prostate cancer and inhibit the influence of androgen produced by the female body, thereby treating diseases caused by excessive androgen production or special sensitivity to androgen. Inhibits the increase in the function of the sebaceous glands that play an important role in the occurrence of acne and seborrhea. [0003] At present, it is widely used clinically, and has been very popular in the international market, ranking among the top hormones. Cyproterone orthoacetate dehydrogenation product is obtained through 2-step dehydrogenation reaction ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J7/00
Inventor 张和明
Owner ZHEJIANG XIANJU XIANLE PHARMA
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