Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method of 19-nor-4-androstenedione

A technology of androstenedione and demethylation, which is applied in the field of preparation of pharmaceutical intermediates, can solve the problems of low product reaction yield, unsuitability for large-scale production, low yield of alkali dereaction, etc., and achieve high product purity, The effect of low cost and simple preparation process

Inactive Publication Date: 2010-10-06
上海津力药业股份有限公司
View PDF0 Cites 10 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] There are many kinds of preparation methods of 19-desmethyl-4-androstenedione in the prior art, mainly divided into two kinds of acid removal and alkali removal, wherein the method usually used is: androst-4-ene-19- Methanol-3,17-dione is oxidized with chromic anhydride-concentrated sulfuric acid to generate thio-4-ene-19-carboxy-3,17-dione, which is decarboxylated and decarboxylated by heating in pyridine under nitrogen Obtain this product, although this method is simple in preparation process, alkali dereaction yield is low, and product reaction yield is low, is not suitable for large-scale 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
  • Preparation method of 19-nor-4-androstenedione
  • Preparation method of 19-nor-4-androstenedione
  • Preparation method of 19-nor-4-androstenedione

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] A preparation method of 19-desmethyl-4-androstenedione, the preparation process mainly consists of three parts: addition reaction, decarboxylation oxide purification, and alkali dereaction. The specific preparation method and steps are as follows:

[0033] 1) Addition reaction: In a 100ml three-necked flask, add 56g of acetone and 4g of rearrangements, stir to dissolve, turn on the refrigerator, cool to -34°C, add 6g of drinking water, and keep between -35--40°C, Add (1.2g trichloroisocyanuric acid + acetone 8g) solution dropwise, stir and keep warm for 45 minutes, pour into the pre-prepared (12g water + 2g sodium bisulfite) solution, stir, concentrate, add 80g drinking water after concentration, and pump Filter to obtain 3.3 g (82%) of off-white powder of the adduct, area content: 98.14%, purity (external standard method) 90.33%, MP: 217°C.

[0034] 2) Purification of decarboxylation oxides: In a 250ml three-necked flask, add 195g of water and 9.9g of sodium bicarbonat...

Embodiment 2

[0037] A preparation method of 19-desmethyl-4-androstenedione, the preparation process mainly consists of three parts: addition reaction, decarboxylation oxide purification, and alkali dereaction. The specific preparation method and steps are as follows:

[0038] 1) Addition reaction: In a 500ml three-necked flask, add 280g of acetone and 20g of rearrangement, stir to dissolve, turn on the refrigerator, cool to -34°C, add 30g of drinking water, between -35--40°C, Add (6g of trichloroisocyanuric acid + 40g of acetone) solution dropwise, stir and keep warm for 45 minutes, pour into the pre-prepared (60g of water + 10g of sodium bisulfite) solution, stir, concentrate, add 400g of drinking water after concentration, and filter with suction 17g (85%) of off-white powder of the adduct was obtained, the area content: 99.10%, the purity (external standard method) was 91.43%, MP: 221°C.

[0039] 2) Purification of decarboxylation oxides: In a 500ml three-necked flask, add 390g of water...

Embodiment 3

[0042] A preparation method of 19-desmethyl-4-androstenedione, the preparation process mainly consists of three parts: addition reaction, decarboxylation oxide purification, and alkali dereaction. The specific preparation method and steps are as follows:

[0043] 1) Addition reaction:

[0044] In a 1000ml three-neck flask, add 560g of acetone, 40g of rearrangement, stir to dissolve, turn on the freezer, cool to -34°C, add 60g of drinking water, drop (trichloroiso Cyanuric acid 12g + acetone 80g) solution, stirred and kept warm for 45 minutes, poured into the pre-prepared (120g water + 20g sodium bisulfite) solution, stirred, concentrated, concentrated and dried, added 800g drinking water, and suction filtered to obtain the adduct Off-white powder 34g (85%), area content: 98.87%, purity (external standard method) 92.27%, MP: 219°C.

[0045] 2) Purification of decarboxylation oxides: In a 1000ml three-necked flask, add 780g of water and 39.6g of sodium bicarbonate, stir to comp...

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 discloses a preparation method of 19-nor-4-androstenedione, which belongs to the technical field of medicine intermediate processing. The preparation process of the 19-nor-4-androstenedione includes three parts of addition reaction, decarboxylated oxide purification and alkali degreasing reaction, and the preparation method comprises the following steps of: firstly, with acetone as a solvent, dissolving a rearrangement product into the solvent, dropwise adding trichloroiminocyanuric acid, then concentrating to remove the acetone, adding water, and carrying out suction filtration to obtain an addition product; then adding the addition product of a decarboxylated oxide crude product by using the water as the solvent, enabling the addition product of the decarboxylated oxide crude product to become sodium salt through sodium bicarbonate, repeatedly washing off impurities with chloroform, and then enabling the sodium salt to become decarboxylated oxide through dilute hydrochloric acid; and finally, adding triethanolamine and a decarboxylated oxidation extract by using the acetone as the solvent, then adding the water for material precipitation, and carrying out suction filtration to obtain alkali degreasing white crystals. The invention has fewer adopted materials, low cost, simple preparation process, high reaction yield and high purity and quality of products and is suitable for large-scale industrial production.

Description

technical field [0001] The invention relates to a preparation method of a pharmaceutical intermediate, in particular to a preparation method of 19-desmethyl-4-androstenedione. Background technique [0002] 19-desmethyl-4-androstenedione is the main intermediate in the synthesis of norethindrone and nandrolone phenylpropionate, among which: norethindrone is a progestin drug, which mainly promotes and maintains pregnancy and pregnancy It can be used for functional uterine bleeding, dysmenorrhea, irregular menstruation, endometriosis and infertility, etc. It can be used as a contraceptive when combined with estrogen drugs. [0003] China Pharmaceutical Research, Volume 15, No. 15, 2006, also reported a synthesis of 6 using 19-desmethyl-4-androstenedione as a starting material through etherification, reduction, diesterification and dehydrogenation steps. The method of 6-dehydronandrolone acetate, 6-dehydronandrolone acetate is a key intermediate for synthesizing medicines for w...

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
IPC IPC(8): C07J1/00
Inventor 王建国戴龙华
Owner 上海津力药业股份有限公司
Features
  • Generate Ideas
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

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

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com