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Preparation and purification method for new ornidazole optical antimer

An ornidazole optics and purification method technology, applied in organic chemistry and other fields, can solve problems such as discomfort, low water solubility, autoimmune hepatitis, peripheral neuropathy, etc., and achieve the effects of reducing pollution, simple operation, and easier control of reaction conditions

Active Publication Date: 2012-08-22
HC SYNTHETIC PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is a metaphor for low water solubility, dizziness and gastrointestinal discomfort after taking it, and occasionally can cause liver cell damage, autoimmune hepatitis, peripheral neuropathy and other adverse reactions

Method used

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  • Preparation and purification method for new ornidazole optical antimer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1: Preparation of L-ornidazole

[0019] Add 3L of formic acid into a 5L reaction flask, add 171ml of concentrated sulfuric acid while stirring, and continue stirring for 1 hour. Add 540 g of 2-methyl-5-nitroimidazole, stir and lower the temperature to -5°C. Slowly add 1.08 L of S-(+)-epichlorohydrin dropwise, and control the reaction temperature below 5°C. After dropping, stir the reaction, control the temperature of the reaction solution at 10°C to 15°C, and monitor the reaction by HPLC. After the reaction was stopped (increase of reaction degree in 2 hours was less than 0.3%), the formic acid and excess S-(+)-epichlorohydrin in the reaction solution were evaporated under reduced pressure, and the residue was added to 2000ml of ice-water mixture to adjust the pH to 3-4, the filtrate was extracted with ethyl acetate (2L×3), the ethyl acetate was combined, dried with anhydrous sodium sulfate, filtered, 5L of water was added to the filtrate, and hydrochloric ...

Embodiment 2

[0022] Embodiment 2: Preparation of dex-ornidazole

[0023] Add 3L of acetic acid into the 5L reaction flask, add 171ml of concentrated sulfuric acid while stirring, and continue stirring for 1 hour. Add 540 g of 2-methyl-5-nitroimidazole, stir and lower the temperature to 15°C. Slowly add 1.08 L of R-(-)-epichlorohydrin dropwise, and control the reaction temperature to 15°C. After dropping, stir the reaction, control the temperature of the reaction solution at 10°C to 20°C, and monitor the reaction by HPLC. After the reaction was stopped (increase of reaction degree in 2 hours was less than 0.3%), the formic acid and excess R-(-)-epichlorohydrin in the reaction solution were evaporated under reduced pressure, and the residue was added to 2000ml of ice-water mixture to adjust the pH to 3-4, the filtrate was extracted with ethyl acetate (2L×3), the ethyl acetate was combined, dried with anhydrous sodium sulfate, filtered, 5L of water was added to the filtrate, and hydrochlori...

Embodiment 3

[0026] Embodiment 3: Preparation of L-ornidazole

[0027] Add 3L of formic acid into a 5L reaction flask, add 120ml of perchloric acid under stirring, and continue stirring for 1 hour. Add 540 g of 2-methyl-5-nitroimidazole, stir and lower the temperature to -5°C. Slowly add 1.08 L of S-(+)-epichlorohydrin dropwise, and control the reaction temperature below 5°C. After dropping, stir the reaction, control the temperature of the reaction solution at 10°C to 15°C, and monitor the reaction by HPLC. After the reaction was stopped (increase in the degree of reaction in 2 hours was less than 0.3%), the formic acid and excess S-(+)-epichlorohydrin in the reaction solution were evaporated under reduced pressure, and the residue was added to 2000ml of ice-water mixture to adjust the pH to 3-4, the filtrate was extracted with ethyl acetate (2L×3), the ethyl acetate was combined, dried with anhydrous sodium sulfate, filtered, 5L of water was added to the filtrate, and hydrochloric acid...

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Abstract

The invention provides a preparation and refining method for a new ornidazole optical antimer. The method comprises the following steps of: adding 2-methyl-5-nitroimidazole into an acid solution with a catalyst to react with chiral epoxy chloropropane to generate an ornidazole optical antimer, performing re-crystallization on the ornidazole optical antimer by using a mixed solution of an organic solvent and water, and thus obtaining the high-purity ornidazole optical antimer.

Description

Technical field: [0001] The invention relates to the preparation and purification method of a new ornidazole optical enantiomer. technical background: [0002] Nitroimidazole compounds have been used as anaerobic bacteria drugs for more than 40 years. From the original metronidazole and tinidazole to the current ornidazole, they all have good antibacterial activity. As a class of powerful anti-anaerobe and antiprotozoal infection drugs, it is also a newly developed nitroimidazole derivative with higher curative effect, shorter course of treatment, better tolerance and wider distribution in the body after metronidazole. The antimicrobial effect of ornidazole is through the reduction of the nitro group in its molecule to an amino group in an oxygen-free environment, or through the formation of free radicals to interact with cell components, resulting in the death of microorganisms. [0003] Ornidazole (ONZ) is a third-generation nitroimidazole antibiotic, which only targets a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/94
Inventor 杨成强建华刘晓鹏
Owner HC SYNTHETIC PHARMA CO LTD
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