Preparation method of progesterone

A technology of progesterone and androstenedione, applied in the direction of steroids, organic chemistry, etc., can solve the problems of easy side reactions, long reaction time, troublesome routes, etc., to avoid the use of highly toxic, stable production raw materials, The effect of easy operation

Inactive Publication Date: 2020-11-27
YUEYANG HUANYU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The hydrogenation reaction of dienolone acetate in the above process uses ethanol as a solvent and active nickel as a catalyst, and the hydrogenation reaction is carried out at a temperature of 34~36°C for 3.5 hours, and some manufacturers increase the hydrogenation temperature to 50±3°C Reaction for 5 hours, this kind of high-temperature hydrogenation reaction, the reaction time is long, side reactions are prone to occur, and the route in the preparation process is relatively troublesome, and the cost in industrial production is high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] A kind of preparation method of progesterone, take 4-androstenedione as main raw material, make progesterone through condensation, etherification, reduction, methylation, hydrolysis successively, and its preparation method comprises the following steps:

[0021] S1, condensation reaction: under the action of alkali, 4-androstenedione and sulfonylmethyl isocyanate undergo condensation reaction to generate 4-androst-3-17-formamidosulfonylmethylene compound;

[0022] S2, etherification reaction: the 4-androst-3-17-formamidosulfonylmethylene compound prepared above is etherified with the C3 carbonyl under the catalysis of an acid to obtain 4-androst-3- Alkoxy-3,5-diene-17-carboxamidosulfonylmethylene compounds;

[0023] S3, reduction reaction: the 4-androst-3-alkoxy-3,5-diene-17-formamidosulfonyl methylene compound obtained in S2 is reduced to 4-androstol under the action of a reducing agent - 3-alkoxy-3,5-diene-17-carboxamidosulfonylmethyl compound;

[0024] S4, methylat...

Embodiment 2

[0033] A kind of preparation method of progesterone, take 4-androstenedione as main raw material, make progesterone through condensation, etherification, reduction, methylation, hydrolysis successively, and its preparation method comprises the following steps:

[0034] S1, condensation reaction: under the action of alkali, 4-androstenedione and sulfonylmethyl isocyanate undergo condensation reaction to generate 4-androst-3-17-formamidosulfonylmethylene compound;

[0035] S2, etherification reaction: the 4-androst-3-17-formamidosulfonylmethylene compound prepared above is etherified with the C3 carbonyl under the catalysis of an acid to obtain 4-androst-3- Alkoxy-3,5-diene-17-carboxamidosulfonylmethylene compounds;

[0036] S3, reduction reaction: the 4-androst-3-alkoxy-3,5-diene-17-formamidosulfonyl methylene compound obtained in S2 is reduced to 4-androstol under the action of a reducing agent - 3-alkoxy-3,5-diene-17-carboxamidosulfonylmethyl compound;

[0037] S4, methylat...

Embodiment 3

[0046] A kind of preparation method of progesterone, take 4-androstenedione as main raw material, make progesterone through condensation, etherification, reduction, methylation, hydrolysis successively, and its preparation method comprises the following steps:

[0047] S1, condensation reaction: under the action of alkali, 4-androstenedione and sulfonylmethyl isocyanate undergo condensation reaction to generate 4-androst-3-17-formamidosulfonylmethylene compound;

[0048] S2, etherification reaction: the 4-androst-3-17-formamidosulfonylmethylene compound prepared above is etherified with the C3 carbonyl under the catalysis of an acid to obtain 4-androst-3- Alkoxy-3,5-diene-17-carboxamidosulfonylmethylene compounds;

[0049] S3, reduction reaction: the 4-androst-3-alkoxy-3,5-diene-17-formamidosulfonyl methylene compound obtained in S2 is reduced to 4-androstol under the action of a reducing agent - 3-alkoxy-3,5-diene-17-carboxamidosulfonylmethyl compound;

[0050] S4, methylat...

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PUM

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Abstract

The invention discloses a preparation method of progesterone. According to the invention, 4-androstenedione is used as a main raw material and is subjected to condensation, etherification, reduction,methylation and hydrolysis reactions sequentially to prepare the progesterone. According to the preparation method of the progesterone in the invention, an acid reagent, an alkali reagent, a methylation reagent and the like are selected in a preparation process, production raw materials are stable, preparation is simple, cost is low, the independence of each step in the preparation process is strong, operation is simple, and the method is suitable for industrial operation; a compound generated in the preparation process is stable in performance and is not easy to decompose, so influence of thedecomposition of the compound on preparation efficiency is avoided; and in addition, a route selected for preparation is composed of condensation, etherification, reduction, methylation and hydrolysis, extra dehydration treatment is not needed, and the neutralization effect of acid and alkali is achieved, so the method is economical and environmentally friendly, is beneficial for industrial production and avoids usage of highly toxic substances.

Description

technical field [0001] The invention belongs to the technical field of progesterone preparation, and in particular relates to a preparation method of progesterone. Background technique [0002] Progesterone (Progesterone) is the most important natural progesterone, which was isolated from pregnant urine in 1934, and its structure was determined as Δ4-3-ketopregnane. Progesterone plays an important role in the secretion transformation of endometrium, decidualization process, maintenance of sexual cycle and maintenance of pregnancy. It is also the main component of female steroidal oral contraceptives and has very important clinical uses; Progesterone is also the precursor of corticosteroids, androgens and estrogens, which promotes the research of steroid hormone drugs. [0003] At present, the industrialized production process of progesterone is to use dienolone acetate as raw material, and undergoes steps such as hydrogenation, hydrolysis, Woshi oxidation, pretreatment and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J7/00
CPCC07J7/002
Inventor 徐润星
Owner YUEYANG HUANYU PHARMA
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