Triazole analogue compound as well as preparation method and application thereof

A technology of analogs and triazoles, which is applied in the field of preparation of triazole analogs, can solve the problems of unstable compounds, high toxicity of raw materials, cumbersome post-processing, etc., and achieve the effects of low toxicity, economical reliability, and simple operation

Pending Publication Date: 2022-04-12
JIANGSU HANSYN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The method for synthesizing the compound 3 is reported in the Journal of labeled compounds and radiopharmaceuticals, 1998, vol.41, #8, p.631–639, which uses formamidine analogs, which are unstable, poorly soluble and toxic , the raw material is highly toxic, the post-treatment is cumbersome and the yield is low, only 54%, and the purity is 97.1%

Method used

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  • Triazole analogue compound as well as preparation method and application thereof
  • Triazole analogue compound as well as preparation method and application thereof
  • Triazole analogue compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Add 5.0g of compound 1, 0.5g of compound 2, 0.46g of DMAP, 0.77g of imidazole, 6ml of DME and stir to dissolve, react at 25°C for 24h, drop the reaction solution into 50ml of water, extract with 100ml of dichloromethane, and concentrate under reduced pressure to obtain dark brown Oily liquid, column chromatography (using 18*160mm glass chromatography column, 300-400 mesh silica gel, petroleum ether and ethyl acetate volume ratio of 6:1 mixed solvent as eluent) was purified for 3 times to obtain a white solid (compound 3) 3.8g, yield 82.9%, purity 98.1%.

Embodiment 2

[0054] Add 5.0g of compound 1, 0.5g of compound 2, 0.46g of DMAP, 0.77g of imidazole, 6ml of MeOH and stir to dissolve, react at 25°C for 24h, drop the reaction liquid into 25ml of water, extract with 100ml of dichloromethane, and concentrate under reduced pressure to obtain dark brown Oily liquid, column chromatography (using 18*160mm glass chromatography column, 300-400 mesh silica gel, petroleum ether and ethyl acetate volume ratio of 6:1 mixed solvent as eluent) was purified for 3 times to obtain a white solid (compound 3) 3.82g, yield 83.1%, purity 98.5%.

Embodiment 3

[0056] Add 5.0g of compound 1, 0.5g of compound 2, 0.46g of DMAP, 0.77g of triethylamine, 6ml of MeOH and stir to dissolve, react at 25°C for 24h, drop the reaction liquid into 25ml of water, extract with 100ml of dichloromethane, and concentrate under reduced pressure to obtain Dark brown oily liquid, purified by column chromatography (using 18*160mm glass chromatography column, 300-400 mesh silica gel, petroleum ether and ethyl acetate with a volume ratio of 6:1 as eluent) 3 times to obtain a white solid (Compound 3) 3.48g, yield 75.8%, purity 98.1%.

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Abstract

The invention relates to the technical field of medicine production, in particular to a triazole analogue compound, a preparation method and application. A target compound is synthesized by reacting a compound 1 and a compound 2 in the presence of a catalyst and an organic weak base. The preparation method is simple, short in synthetic route, economical and reliable, the target compound, namely the triazole analogue compound 3, is obtained in one step, and the finally obtained product is high in purity. The compound 3 can be used for preparing a posaconazole intermediate impurity reference substance or a posaconazole impurity reference substance.

Description

technical field [0001] The invention relates to the technical field of pharmaceutical production, in particular to a triazole analog compound, a preparation method and an application. Background technique [0002] Posaconazole, English name: Posaconazole. The chemical name is 4-[4-[4-[4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1,2,4-triazol-1-yl Methyl)oxolan-3-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-2-[(2S,3S)-2-hydroxypent-3-yl]-1 , 2,4-triazol-3-one, the structure is as follows formula 1. [0003] [0004] Posaconazole was developed by Germany's Schering-Plough (now Merck), and was first approved for marketing in Ireland in October 2005. In September 2006, the U.S. FDA approved posaconazole oral suspension (specification: 40mg / ml); from November 2013 to March 2014, the U.S. FDA approved posaconazole sustained-release tablets (specification: 100mg / ml). / tablet) and injection (specification: 0.3g / 16.7ml). At present, it has been approved in more than 70 countries and r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14
Inventor 马难难胡振宇黄钰
Owner JIANGSU HANSYN PHARMA
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