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Synthesis technology of dutasteride

A synthesis process, the technology of dutasteride, is applied in the field of chemical synthesis of drugs, can solve problems such as being unfavorable to large-scale production, complicated post-processing, long reaction time, etc., and achieve high-yield, high-purity, green, large-scale clean production, Easy purification and good product yield

Active Publication Date: 2012-04-18
HUBEI TIANSHENG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Long reaction time, high energy consumption, complex post-processing, not conducive to large-scale production

Method used

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  • Synthesis technology of dutasteride
  • Synthesis technology of dutasteride
  • Synthesis technology of dutasteride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 2

[0056] 1.3.2.1 Synthesis of I and II (salt formation reaction, dehydration reaction)

[0057] In a clean 1000ml reaction bottle equipped with distillation concentration and tail gas absorption device, put 600ml of ammonia water with a concentration of 20%, put 50.00g of DT4 under stirring, slowly raise the temperature to 80°C, and keep warm until the reaction solution changes from cloudy to clear gradually , continue to heat up and concentrate until a large amount of precipitation and thicken, cool to below 60°C, add 500ml of xylene, change the distillation and concentration device to a reflux water separation device, heat up to reflux, divide water until the distillate is clear, continue to heat up and concentrate to a large amount Precipitates and thickens. Cool down to room temperature, filter, wash the reaction bottle with 100ml xylene in stages, then wash the filter cake, filter dry, and vacuum-dry at 60-80°C to constant weight to obtain 49.55g of white II crystals with a...

Embodiment 3

[0061] 1.3.3.1 Synthesis of I and II (salt formation reaction, dehydration reaction)

[0062] In a clean 1000ml reaction bottle equipped with distillation concentration and tail gas absorption device, put 600ml of ammonia water with a concentration of 20%, put 50.00g of DT4 under stirring, slowly raise the temperature to 80°C, and keep warm until the reaction solution changes from cloudy to clear gradually , then continue to heat up and concentrate until a large amount of precipitation and thicken, cool to below 60°C, add 500ml of xylene, change the distillation and concentration device to a reflux water separation device, heat up to reflux, divide water until the distillate is clear, and then continue to heat up and concentrate To a large amount of precipitation and thick. Cool down to room temperature, filter, wash the reaction flask with 100ml of xylene in stages, wash the filter cake, filter to dryness, and vacuum-dry at 60°C to constant weight to obtain 49.46g of white II...

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Abstract

The invention discloses a synthesis technology of dutasteride, comprising the following steps of: using the acidity of DT4 carboxyl to directly react with ammonia to generate DT4-ammonium salt; dehydrating the obtained ammonium salt into DT4-amide, and performing an amino exchange reaction between amide and BTFMA in the presence of a catalyst so as to prepare dutasteride. With DT4 as a starting material, dutasteride is synthesized by three reactions of salt formation, dehydration and amino exchange. During the reactions, thionyl chloride, oxalyl chloride, pivaloyl chloride or methylsulfonyl chloride which is sensitive to the environment is avoided, special expensive catalysts such as DBU, copper powder and the like are not needed, and harmful and poisonous chemical materials are avoided. The product has good product yield and high purity, and is easy to refine. The synthesis technology has advantages of low cost and few ''three wastes'', is easy and simple to operate, conforms to green chemical synthesis requirements, and lays a good industrial foundation for realizing large-scale green clean production of high-yield and high-purity dutasteride.

Description

technical field [0001] The invention relates to the field of chemically synthesized drugs, in particular to a process for chemically synthesizing dutasteride. Background technique [0002] Dutasteride (Dutasteride, CAS#: 164656-23-9), chemical name (5α, 17β)-N-[2,5-bis(trifluoromethyl)phenyl]-3-keto-4- Aza-5α-androst-1-ene-l7β-carboxamide, developed by Glaxo History (GSK), was approved by the FDA in June 2003 and is listed in the United States as a type I and type II isoforms Selective inhibitors of steroidal 5α-reductase, an intracellular enzyme capable of converting testosterone to 5α-dihydrotestosterone (Frye S V. Bramson H N, Hermann D J, et al. Discovery and Development of GG745, a Potent Inhibitor of Both Isozymes of 5a-Reductase [J]. Pharm Biotechnol, 1998, 11: 393-422), is a new type of drug for the treatment of benign prostatic hyperplasia (BPH), which can reduce acute urinary retention and reduce BPH surgical treatment . Compared with finasteride, the effect is ...

Claims

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Application Information

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IPC IPC(8): C07J73/00
Inventor 刘龙成
Owner HUBEI TIANSHENG PHARMA
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