Synthetic method of A-nor-3,5-cracking-androstane-5-ketone-3,17 beta-diacid

A technology of androstene and diacid, which is applied in the preparation of ketene/polyketene, organic chemistry, etc., can solve the problems of unsuitability for large-scale industrial production, pollution of heavy metal ions, and difficulty in separation and purification, and achieve easy industrial implementation and three wastes ”Effect of reduced emission and high reaction yield

Active Publication Date: 2013-07-10
HUNAN KEREY BIOTECH
View PDF1 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] For example, Chinese Journal of Pharmaceutical Sciences 200439 (3) 226-228 provides a method for preparing finasteride. In its key step, 3-carbonyl-4-androstene-17-carboxylic acid is oxidized to obtain A-abortion-3, During the process of 5-cracking-androst-5-one-3,17β-diacid, a large amount of expensive sodium periodate and heavy metal oxide potassium permanganate are used. This method is not only difficult to separate and purify, but also requires the use of reagents Expensive, highly toxic, and cause problems such as heavy metal ion pollution
Not suitable for large-scale industrial production

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Synthetic method of A-nor-3,5-cracking-androstane-5-ketone-3,17 beta-diacid
  • Synthetic method of A-nor-3,5-cracking-androstane-5-ketone-3,17 beta-diacid
  • Synthetic method of A-nor-3,5-cracking-androstane-5-ketone-3,17 beta-diacid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Preparation of A-carbo-3,5-cleavage-androst-5-one-3,17β-diacid:

[0024] Add 3-carbonyl-4-androstene-17-carboxylic acid (31.64g; Fw: 316.43 ; 100mmol), then add 100mL acetone and hydrogen peroxide (30wt%H 2 o 2 , 100mmol). Then sodium tungstate (3.3 g; 10 mmol), 0.5 mL of 4M phosphoric acid were added. The system continued to stir for 1 h under reflux. After the reaction was completed, after the system was cooled to room temperature, a saturated solution of sodium bisulfite was added dropwise, followed by stirring for 10 minutes, the solid was removed by filtration, the filtrate was evaporated to dryness, added ice water and extracted with dichloromethane, the extract was washed and dried, and evaporated to dryness to obtain The crude product was then recrystallized from a solvent to obtain 31.96 g of the target product, yield: 95%, and HPLC content greater than 98%.

Embodiment 2

[0026] Preparation of A-carbo-3,5-cleavage-androst-5-one-3,17β-diacid:

[0027] Add 3-carbonyl-4-androstene-17-carboxylic acid (31.64g; Fw: 316.43 ; 100mmol), then add 100mL1,4-dioxane and hydrogen peroxide (30wt%H 2 o 2 , 150mmol). Then sodium tungstate (3.3 g; 10 mmol), 0.5 mL of 4M nitric acid were added. The system continued to stir for 1 h under reflux. After the reaction was completed, after the system was cooled to room temperature, a saturated solution of sodium bisulfite was added dropwise, followed by stirring for 10 minutes, the solid was removed by filtration, the filtrate was evaporated to dryness, added ice water and extracted with dichloromethane, the extract was washed and dried, and evaporated to dryness to obtain The crude product was then recrystallized from a solvent to obtain 31.96 g of the target product, yield: 95%, and HPLC content greater than 98%.

Embodiment 3

[0029] Preparation of A-carbo-3,5-cleavage-androst-5-one-3,17β-diacid:

[0030] Add 3-carbonyl-4-androstene-17-carboxylic acid (31.64g; Fw: 316.43 ; 100mmol), then add 150mL1,2-dichloroethane and hydrogen peroxide (30wt%H 2 o 2 , 200mmol). Then sodium tungstate (3.3 g; 10 mmol), p-toluenesulfonic acid (1.7 g; Fw: 172.20; 10 mmol) were added. The system continued to stir for 1 h under reflux. After the reaction was completed, after the system was cooled to room temperature, a saturated solution of sodium bisulfite was added dropwise, followed by stirring for 10 minutes, the solid was removed by filtration, the filtrate was evaporated to dryness, added ice water and extracted with dichloromethane, the extract was washed and dried, and evaporated to dryness to obtain The crude product was then recrystallized from a solvent to obtain 32.97 g of the target product, yield: 98%, and HPLC content greater than 98%.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention provides a synthetic method of A-nor-3,5-cracking-androstane-5-ketone-3,17 beta-diacid. The method comprises the following steps of: adding hydrogen peroxide and acid into 3-carbonyl-4-androstene-17-thiolic acid in a solvent in the presence of a metal catalyst for reacting; adding a reducing agent after reacting; and collecting A-nor-3,5-cracking-androstane-5-ketone-3,17 beta-diacidserving as a target product from a reaction product. By adopting the method, a high-purity product can be obtained at high yield and high selectivity. The used method is simple, safe and environmentally-friendly. The reaction condition is mild, the reaction is relatively complete, and the purity is over 99 percent by simple purification. All reagents used in the entire reaction are readily-available, and meanwhile, the reaction yield is high, the reaction condition is mild, the solvent can be recycled, and industrial implementation is convenient.

Description

technical field [0001] The invention relates to a method for preparing the synthetic method of finasteride important intermediate A-abortion-3,5-cracking-androst-5-one-3,17β-diacid. 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 (1): [0003] [0004] The important intermediate ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/757C07C67/46
Inventor 左前进羊向新吴来喜
Owner HUNAN KEREY BIOTECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap