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Chemical synthesis of free megestrol

A technology for chemical synthesis and megestrol, applied in the fields of organic chemistry, steroids, etc., can solve the problems of incomplete methylation transposition, poor quality of reaction products, long reaction time, etc., to achieve easy industrialization, reduce Generation of by-products, the effect of simple operation

Inactive Publication Date: 2008-07-02
TAIZHOU TAIFA PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Obtain megestrol acetate by this method and then hydrolyze to obtain free megestrol. The disclosed technology is limited to laboratory conditions. The palladium carbon catalyst is not active in the alcohol solvent reaction system, causing the reactant to stay in the The 6-7 position is in the state of a double bond conjugated system, which makes the transposition of methylation incomplete, the reaction time is longer, the quality of the reaction product is poor, and the yield is low

Method used

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  • Chemical synthesis of free megestrol

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Experimental program
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Effect test

Embodiment 1

[0020] 17α-Hydroxyprogesterone 30KG is subjected to methine reaction to obtain 23KG of methine. 260L of dimethylformamide was pumped into the reaction tank, dropped into 23KG of methine, 12KG of 5% palladium-carbon catalyst, 1200ml of cyclohexene, was incubated at 70 DEG C for 1.5 hours, filtered, and concentrated while filtering. The weight is 1.5 times the weight of the input methine, cooled to below 5°C for centrifugation, rinsed with warm water at 50°C for 1 hour, and dried to obtain crude free megestrol, which was purified to obtain 16.1KG with a yield of 70.0%.

Embodiment 2

[0022] 17α-Hydroxyprogesterone 30KG is subjected to methine reaction to obtain 23KG of methine. 240L of dimethylformamide was pumped into the reaction tank, dropped into 23KG of methine, 12KG of 5% palladium-carbon catalyst, 1200ml of cyclohexene, was incubated at 60 DEG C for 3 hours, filtered, and concentrated while filtering. The weight is 1.5 times the weight of the input methine, cooled to below 5°C for centrifugation, rinsed with 50°C warm water for 0.5 hours, and dried to obtain a crude free megestrol.

Embodiment 3

[0024] 17α-Hydroxyprogesterone 30KG is subjected to methine reaction to obtain 23KG of methine. 260L of dimethylformamide was pumped into the reaction tank, dropped into methine 23KG, 5% palladium-carbon catalyst 12KG, cyclohexene 1100ml, was incubated at 55 DEG C for 2.5 hours, filtered, concentrated while filtering, the mother liquor after the concentration was concentrated. The weight is 1.5 times the weight of the input methine, cooled to below 5°C for centrifugation, rinsed with 50°C warm water for 0.5 hours, and dried to obtain a crude free megestrol, which was purified to obtain 16.4KG with a yield of 71.3%.

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Abstract

The present invention discloses chemical synthesis of free megestrol. The initial material 17alpha-hydroxyprogesterone is first methenylated to form methenylated substance, the methenylated substance is then mixed with Pd / C catalyst, dimethylformamide and cyclohexene and reacted at 50-70 deg.c for 1-3 hr, and the product is post-treated to obtain free megestrol. The improved synthesis process of the present invention has complete methylation, less side product, high product purity, high quality stability, high yield and low production cost, and may be used in industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing free megestrol (6-methyl-4,6-diene-3,20-dione-17α-hydroxypregnant), which starts from 17α-hydroxyprogesterone starting material to prepare free megestrol. Background technique [0002] Free megestrol is an important intermediate of hormone APIs. [0003] In the prior art, 17α-hydroxyprogesterone acetate is mostly used as the starting material, and megestrol acetate is obtained through methineization reaction, 6-position methylation, decolorization and purification, and then hydrolyzed to obtain free megestrol. At the same time, the key reaction technology of the 6-position methylation is difficult, and the side reactions are difficult to control. [0004] The U.S. invention patents with the patent numbers of US3117966 and US1020493 disclose the synthesis of megestrol acetate structural compounds, wherein methylation has been a conventional production method. But in the methylation process at the 6th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J7/00
Inventor 汪家振
Owner TAIZHOU TAIFA PHARMA
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