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Method for synthesizing finasteride

A synthetic method and finasteride technology, applied in the field of preparation of finasteride, can solve the problems of many by-products, expensive reagents, high reflux temperature, etc., and achieve the effects of reducing the emission of "three wastes", reducing production costs, and mild reaction conditions

Inactive Publication Date: 2009-04-29
湖南玉新药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

limit its use in industrial production
[0006] J.Med.Chem., 1984,27(12), 1690 provides a kind of method, and this method is oxidant by 3-carbonyl-4-aza-5α-androst-17β-tert-butyl Amide dehydrogenation obtains 3-carbonyl-4-aza-5α-androst-1-ene-17β-tert-butylamide (finasteride). The method uses chlorobenzene as a solvent, and the reflux temperature is high, and byproducts are relatively high. Many, not only difficult to separate and purify, need to use chromatographic column separation, but also low yield, expensive reagents, high toxicity
Not suitable for large-scale industrial production

Method used

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  • Method for synthesizing finasteride
  • Method for synthesizing finasteride
  • Method for synthesizing finasteride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Add trifluoroacetamide (11.30g; Fw: 113.04; 100mmol), anhydrous triethylamine ( 24.29 g; Fw: 101.19; 240 mmol); then the system was stirred at room temperature for 10 min, and trimethylchlorosilane (20.64 g; Fw: 108.64; 190 mmol) was transferred to a constant pressure dropping funnel. Raise the temperature of the system to 50°C, slowly drop trimethylchlorosilane into the system, control the temperature of the system not to exceed 50°C, and complete the dropwise addition for about 2 hours. After the dropwise addition, the system continued to stir at 50° C. for 10 h. After the reaction was completed, a large amount of triethylamine hydrochloride would precipitate out of the system during the reaction.

[0029] After the reaction is complete and the system is cooled to room temperature, the system can be diluted with 50 mL of anhydrous toluene, filtered to remove triethylamine hydrochloride, and the filter cake is washed with 50 mL of anhydrous toluene, and the organic pha...

Embodiment 2

[0031] Add trifluoroacetamide (11.30g; Fw: 113.04; 100mmol), anhydrous triethylamine ( 50.60g; Fw: 101.19; 500mmol); toluene 1000mL, then the system was stirred at room temperature for 10min, and trimethylchlorosilane (54.32g; Fw: 108.64; 500mmol) was transferred to a constant pressure dropping funnel. Raise the temperature of the system to 50°C, slowly drop trimethylchlorosilane into the system, control the temperature of the system not to exceed 50°C, and complete the dropwise addition for about 2 hours. After the dropwise addition, the system continued to stir at 110° C. for 2 h. After the reaction was completed, a large amount of triethylamine hydrochloride would precipitate out of the system during the reaction.

[0032] After the reaction is complete and the system is cooled to room temperature, the system can be diluted with 50 mL of anhydrous toluene, filtered to remove triethylamine hydrochloride, and the filter cake is washed with 50 mL of anhydrous toluene, and the ...

Embodiment 3

[0034] Add trifluoroacetamide (11.30 g; Fw: 113.04; 100 mmol), 1,4-dioxo Hexacyclic 67 mL, anhydrous pyridine (7.91 g; Fw: 79.10; 100 mmol); then the system was stirred at room temperature for 10 min, and trimethylchlorosilane (10.86 g; Fw: 108.64; 100 mmol) was transferred to a constant pressure dropping funnel. Keep the system temperature at 20°C, slowly drop trimethylchlorosilane into the system, control the system temperature not to exceed 20°C, and complete the dropwise addition for about 2 hours. After the dropwise addition, the system continued to stir at 20° C. for 24 hours. After the reaction was completed, a large amount of pyridine hydrochloride was precipitated from the system during the reaction.

[0035] After the reaction is completed and the system is cooled to room temperature, the system can be diluted with 50 mL of 1,4-dioxane, filtered to remove pyridine hydrochloride, and the filter cake is washed with 50 mL of anhydrous 1,4-dioxane, and the organic phases...

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Abstract

The invention provides a method for synthesizing finasteride. The method comprises the following steps: (1) dissolving trifluoroacetamide in solvent, reacting the solvent with trimethylchlorosilane in the presence of organic alkali or inorganic alkali, filtering out solid from reaction products, and collecting filtrate; and (2) dissolving the filtrate obtained in step (1) in the solvent, adding 3-carbonyl-4-aza-5 alpha-androstane-17 belta-tert-butylformamide and dehydrogenation agent into the solvent for reaction, and collecting target products from reaction products. The method has the advantages that the method has higher yield, high selectivity, and is simple and safe; after simple purification, the purity of the finasteride can reach more than 99 percent; moreover, the method has easily obtained reagents used in the whole reaction, simultaneously having high reaction yield and mild reaction conditions, reclaiming the solvent and facilitating the industrialized production.

Description

technical field [0001] The invention relates to a method for preparing finasteride. Background technique [0002] Finasteride (finasteride, trade name Proscar, code name MK-906) is a drug for the treatment of benign prostatic hyperplasia developed by Merck & Co. of the United States, which was launched in 1992. Benign prostatic hyperplasia (BPH) is a common disease in older men and the most common cause of dysuria in men. Studies have found that elevated levels of dihydrotestosterone are the cause of BPH. 5α-reductase inhibitors can inhibit the conversion of testosterone into dihydrotestosterone to achieve the purpose of treating BPH. Make the proliferated prostate shrink without dihydrotestosterone, thus showing curative effect. The medicine has definite curative effect and few side effects. Its structural formula is as follows: [0003] [0004] At present, the key step in the existing technology is the dehydrogenation of 3-carbonyl-4-aza-5α-androst-17β-tert-butyla...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J73/00A61P13/08
Inventor 刘喜荣谢来宾胡爱国
Owner 湖南玉新药业有限公司
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