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Optical antimer of a group of nitro imidazole derivatives, preparation method and uses thereof

A technology of nitroimidazoles and derivatives, applied in the field of optical enantiomers

Inactive Publication Date: 2006-06-21
西安新安医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are no reports on the preparation of optical enantiomers of such nitroimidazole derivatives

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1: Preparation of 1-[3-(4-hydroxyl-1-piperidinyl)-S-2-hydroxypropyl]-2-methyl-5-nitroimidazole

[0017] Mix 22g of 1-(3-chloro-2-S-hydroxypropyl)-2-methyl-5-nitroimidazole (ee value 0.99), 30g of sodium iodide, and 400ml of acetonitrile, stir and heat to reflux, and keep warm for reaction After 30min, cool to room temperature, then add 13g of 4-hydroxypiperidine and 20g of triethylamine, stir and heat to reflux, keep the temperature for 5h, after the reaction is complete, recover acetonitrile, add 150ml of distilled water, heat until completely dissolved, filter while hot, put Cold, filtered, washed with water, and dried to obtain 20.3 g of off-white solid, namely 1-[3-(4-hydroxy-1-piperidinyl)-S-2-hydroxypropyl]-2-methyl-5-nitrate Kimidazole. (ee value 0.99)

Embodiment 2

[0018] Example 2: Preparation of 1-[3-piperazinyl-S-2-hydroxypropyl]-2-methyl-5-nitroimidazole

[0019] Mix 22g of 1-(3-chloro-2-S-hydroxypropyl)-2-methyl-5-nitroimidazole (ee value 0.99), 30g of sodium iodide, and 400ml of acetonitrile, stir and heat to reflux, and keep warm for reaction After 30 minutes, cool to room temperature, then add 10 g of piperazine and 20 g of triethylamine, stir and heat to reflux, keep the temperature for 5 hours, after the reaction is complete, recover acetonitrile, add 150 ml of distilled water, heat until completely dissolved, filter while hot, let cool, and filter , washed with water, and dried to obtain 17.1 g of off-white solid, namely 1-[3-piperazinyl-S-2-hydroxypropyl]-2-methyl-5-nitroimidazole (ee value 0.99).

Embodiment 3

[0020] Example 3: Preparation of 1-[3-(methylpiperazinyl)-S-2-hydroxypropyl]-2-methyl-5-nitroimidazole

[0021] Mix 22g of 1-(3-chloro-2-S-hydroxypropyl)-2-methyl-5-nitroimidazole (ee value 0.99), 30g of sodium iodide, and 400ml of acetonitrile, stir and heat to reflux, and keep warm for reaction After 30 minutes, cool to room temperature, then add 12 g of methylpiperazinyl and 20 g of triethylamine, stir and heat to reflux, keep warm for 5 hours, after the reaction is complete, recover acetonitrile, add 150 ml of distilled water, heat until completely dissolved, filter while hot, and put Cold, filtered, washed with water, dried to obtain off-white solid 17.8g, i.e. 1-[3-(methylpiperazinyl)-S-2-hydroxypropyl]-2-methyl-5-nitroimidazole (ee value 0.99).

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PUM

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Abstract

The invention relates to a process for preparing optical enantiomers of nitroimidazole derivatives and the use of these compounds in preparing anti anaerobe medicaments.

Description

technical field [0001] The invention relates to a group of optical enantiomers of nitroimidazole derivatives, which can be used to prepare anti-anaerobe and anti-trichomonad drugs. technical background [0002] Nitroimidazole antibacterial drugs are powerful anti-anaerobic bacteria and anti-protozoal drugs. At present, there are mainly metronidazole, tinidazole, secnidazole and ornidazole on the market. China has the report of this kind of nitroimidazole derivatives and its preparation method (CN1605586). There are no reports on the preparation of optical enantiomers of such nitroimidazole derivatives. Only ornidazole and secnidazole optical antipodes and their preparation methods are reported. Contents of the invention [0003] The purpose of the present invention is exactly one group of nitroimidazole derivative optical antipodes, and the structural formula of this group of optical antipodes is: [0004] [0005] S-isomer R-isomer [0006] where R is [0007]...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/92A61K31/4164A61K31/4178A61K31/496A61K31/5355A61P31/04C07D403/06C07D413/06
Inventor 苏红军许红宝
Owner 西安新安医药科技有限公司
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