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Method for preparing finasteride intermediate

A finasteride and intermediate technology, applied in the field of chemical drug synthesis, can solve the problems of increased raw material cost and environmental protection, achieve high production application and economic value, easy control, increase solubility and reactivity

Active Publication Date: 2015-09-30
HUBEI GEDIAN HUMANWELL PHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In order to solve the problems caused by the increasing cost of raw materials and environmental protection, the present invention proposes a method for preparing finasteride intermediates starting from 4-androstenedione (4AD), a raw material with cleaner sources and more price advantages

Method used

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  • Method for preparing finasteride intermediate
  • Method for preparing finasteride intermediate
  • Method for preparing finasteride intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038]

[0039] Put 30 g of methanol, 10 g of acetone cyanohydrin and 10 g of raw material 4AD into the reaction vessel, then add potassium carbonate aqueous solution (1.0 g of potassium carbonate + 20 g of water), and react at 40-45° C. for about 20 hours. After the reaction, the temperature is lowered to 0~10℃, the pH is adjusted to 4~5 with 10% dilute hydrochloric acid, washed into cold water for crystallization, filtered and washed with water until the filter cake is neutral to obtain the crude product, which is refined with acetone water to obtain 17-hydroxycyanide- 4-Androsten-3-one (Compound 1), dried to obtain 10.4g. The HPLC content is 96.4%, with 3.2% isomers.

[0040]

[0041] 10g of compound 1, 70g of pyridine, and 15g of phosphorus oxychloride are added to the reaction vessel, and the temperature is raised to 100-110°C for 0.5 hour. After the reaction, the temperature is lowered to below 40°C, quickly washed into ice water for crystallization, filtered and washed wi...

Embodiment 2

[0049] Put 120 g of methanol, 32 g of acetone cyanohydrin and 40 g of raw material 4AD into the reaction vessel, and then add potassium carbonate aqueous solution (4.8 g of potassium carbonate + 80 g of water), and react at 40-45° C. for about 24 hours. After the reaction, the temperature is lowered to 0~10℃, the pH is adjusted to 4~5 with 10% dilute hydrochloric acid, washed into cold water for crystallization, filtered and washed with water until the filter cake is neutral to obtain the crude product, which is refined with acetone water to obtain 17-hydroxycyanide- 4-Androsten-3-one (Compound 1), dried to obtain 41.5g. HPLC content is 96.8%, containing 2.9% isomer.

[0050] 40 g of compound 1, 160 g of pyridine, and 32 g of phosphorus oxychloride were added to the reaction vessel, and the temperature was raised to 100-110° C. to react for 1 hour. After the reaction, the temperature is lowered to below 40°C, quickly washed into ice water for crystallization, filtered and washed...

Embodiment 3

[0055] Put 500g methanol, 225g acetone cyanohydrin and 150g raw material 4AD into the reaction vessel, then add potassium carbonate aqueous solution (9g potassium carbonate+300g water), keep the temperature at 40-45°C for about 16 hours. After the reaction, the temperature is lowered to 0~10℃, the pH is adjusted to 4~5 with 10% dilute hydrochloric acid, washed into cold water for crystallization, filtered and washed with water until the filter cake is neutral to obtain the crude product, which is refined with acetone water to obtain 17-hydroxycyanide- 4-Androsten-3-one (Compound 1) was dried to obtain 159g. The HPLC content is 96.1%, with 3.7% isomer.

[0056] 150g of compound 1, 750g of pyridine, and 150g of phosphorus oxychloride were added to the reaction vessel, and the temperature was raised to 100-110°C for 0.75 hours. After the reaction, the temperature is lowered to below 40°C, quickly washed into ice water for crystallization, filtered and washed with water until the fi...

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Abstract

The invention relates to a method for preparing a finasteride intermediate. 4AD is adopted as the raw material and sequentially subjected to cyaniding, dehydration, amidation, ketalation and hydrogenation hydrolysis reaction to prepare the finasteride intermediate. The technology is simple, the product quality is excellent, the yield is higher, and the total weight yield can reach 70%; the adopted raw material 4AD is cheap, available and low in preparation cost. The process route is reasonable and optimized in overall design, and the synthesized product is excellent in quality and higher in yield. The total weight yield can reach 70%, the adopted manner is more convenient and more economical, and the reaction conditions are milder. In addition, the reaction of all steps is simple and convenient to operate, easy to control, and suitable for industrial production.

Description

Technical field [0001] The invention relates to a method for synthesizing chemical drugs, in particular to a method for preparing finasteride intermediates. The method takes 4-androstenedione (4AD) as a raw material, and sequentially undergoes cyanidation, ketal, dehydration, amidation, ketal, and hydrogenation hydrolysis reactions to prepare finasteride intermediates. Background technique [0002] Benign prostatic hyperplasia (BHP) is a common and frequently-occurring disease in elderly men. According to statistics, about 30% to 50% of men over the age of 50 have varying degrees of prostate hyperplasia. Among elderly men aged 70 to 79, the incidence of BHP is 70%, and as high as 90% for men over 80. BHP is the most common cause of dysuria in elderly men. At present, the representative drug used in clinical treatment of BHP is finasteride. Finasteride is produced by Merck and first marketed in Italy in 1991. It is a 5α-reductase inhibitor that can effectively reduce blood and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J41/00
CPCC07J41/0066
Inventor 刘林杨艳青代先华邱壮
Owner HUBEI GEDIAN HUMANWELL PHARMACEUTICAL CO LTD
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