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Chemical synthesis of free megestrol

A chemical synthesis, megestrol technology, applied in the direction of organic chemistry, steroids, etc., can solve the problems of incomplete methylation translocation, 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: 2007-01-03
TAIZHOU TAIFA PHARMA
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  • Abstract
  • Description
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  • 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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Effect test

Embodiment 1

[0020] 30KG of 17α-hydroxyprogesterone was subjected to methylation reaction to obtain 23KG of methine. Pump 260L of dimethylformamide into the reaction tank, put in 23KG of methine, 12KG of 5% palladium-carbon catalyst, and 1200ml of cyclohexene, keep warm at 70°C for 1.5 hours, filter, concentrate while filtering, and concentrate the mother liquor The weight is 1.5 times the weight of the input methine, cooled to below 5°C, centrifuged, rinsed with 50°C warm water for 1 hour, and dried to obtain the crude free megestrol, which was purified to obtain 16.1KG with a yield of 70.0%.

Embodiment 2

[0022] 30KG of 17α-hydroxyprogesterone was subjected to methylation reaction to obtain 23KG of methine. Pump 240L of dimethylformamide into the reaction tank, put in 23KG of methine, 12KG of 5% palladium carbon catalyst, and 1200ml of cyclohexene, keep warm at 60°C for 3 hours, filter, concentrate while filtering, and the mother liquor after concentration The weight is 1.5 times the weight of the input methine, cooled to below 5°C, centrifuged, rinsed with 50°C warm water for 0.5 hour, and dried to obtain free crude megestrol, which was purified to 16.6KG with a yield of 72.2%.

Embodiment 3

[0024] 30KG of 17α-hydroxyprogesterone was subjected to methylation reaction to obtain 23KG of methine. Pump 260L of dimethylformamide into the reaction tank, put in 23KG of methine, 12KG of 5% palladium-carbon catalyst, and 1100ml of cyclohexene, keep warm at 55°C for 2.5 hours, filter, concentrate while filtering, and concentrate the mother liquor The weight is 1.5 times the weight of the input methine, cooled to below 5°C, centrifuged, rinsed with 50°C warm water for 0.5 hour, and dried to obtain the 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 present invention relates to a method for synthesizing free megestrol (6-methyl-4,6-diene-3,20-dione-17α-hydroxypregna), which starts with 17α-hydroxyprogesterone starting materials to prepare free megestrol. Background technique [0002] Free megestrol is an important intermediate of hormone APIs. [0003] Most of the prior art uses 17α-hydroxyprogesterone acetate as the starting material, undergoes methylation reaction, 6-position methylation, decolorization and refining to obtain megestrol acetate, and then hydrolyzes to obtain free megestrol. At the same time, the key reaction process of the 6-position methylation step is technically difficult, and the side reactions are difficult to control. [0004] Patent Nos. US3117966 and US1020493 disclose the synthesis of megestrol acetate structural compounds, wherein hypomethylation has been a conventional production method. However, in the methylation process at position 6, although palladium carbo...

Claims

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Application Information

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