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Ornidazole compound in new path

A technology of ornidazole and compound, applied in the field of drug synthesis, can solve the problems of high cost, low yield, unsuitable production and the like

Inactive Publication Date: 2010-01-27
HAINAN MEILAN SMITH KLINE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Aiming at the disadvantages of high cost, low yield and unsuitability for large-scale production in the preparation of ornidazole raw materials, the inventors tried to find a simple and efficient method to overcome the disadvantages of the prior art

Method used

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  • Ornidazole compound in new path

Examples

Experimental program
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Effect test

Embodiment 1

[0024] The synthesis of embodiment 1 ornidazole

[0025] In 1500ml of ethyl acetate, add 127 grams (1mol) of 2-methyl-5-nitroimidazole, cool to 2°C, slowly add 100ml of boron trifluoride ether solution, keep the temperature of the reaction system not exceeding 5°C, and then Add 139 grams (1.5 mol) of epichlorohydrin dropwise to the reaction system, while keeping the reaction temperature not exceeding 5°C, continue to react at this temperature for 5 hours after the addition, after the reaction, slowly add 600ml of ice-water mixture, Vigorously stir, the reaction temperature does not exceed 25°C, then use concentrated hydrochloric acid to adjust the pH of the system to 1, let it stand, and separate layers, adjust the water phase to pH = 7.3 with concentrated ammonia water, extract with 2000ml ethyl acetate, dry over anhydrous sodium sulfate, and filter , concentrated, and then recrystallized from toluene to obtain 187 g of the product, with a yield of 85%, and mp: 77°C.

[0026...

Embodiment 2

[0028] The synthesis of embodiment 2 ornidazole

[0029] In 3000ml of ethyl acetate, add 254 grams (2mol) of 2-methyl-5-nitroimidazole, cool to 5°C, slowly add 200ml of boron trifluoride ether solution, keep the temperature of the reaction system not exceeding 5°C, and then Add 278 grams (3 mol) of epichlorohydrin dropwise to the reaction system while keeping the reaction temperature not exceeding 5°C. After the addition, continue to react at this temperature for 5 hours. After the reaction, slowly add 1100ml of ice-water mixture, vigorously Stir, the reaction temperature does not exceed 25°C, then use concentrated hydrochloric acid to adjust the pH of the system to 1, let stand, separate layers, adjust the water phase to pH = 7.4 with concentrated ammonia water, extract with 3000ml ethyl acetate, dry over anhydrous sodium sulfate, filter, Concentrate, and then recrystallize with toluene to obtain 387 g of product, yield 88%, mp: 78°C.

[0030] Elemental analysis theoretical ...

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Abstract

The invention provides an ornidazole compound in new path. The preparation method comprises the following steps: allowing 2-methyl-5-nitromidazole to react with epichlorohydrin in solvent, adding an ice-water mixture, adjusting pH value, and recrystallizing to obtain the ornidazole. The preparation method can help obtain products with high yield up to more than 85%.

Description

technical field [0001] The invention relates to a nitroimidazole compound and a synthesis method, in particular to an ornidazole compound and a synthesis method, and belongs to the technical field of drug synthesis. Background technique [0002] Ornidazole was listed in Germany for the first time in 1977 by Swiss Roche Company, its chemical name is: 1-(3-chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole, molecular formula :C 7 h 10 ClN 3 o 3 , molecular weight: 219.6, structural formula: [0003] [0004] Ornidazole is a third-generation nitroimidazole derivative newly developed after metronidazole and tinidazole with higher curative effect, shorter course of treatment, better tolerance and wider distribution in the body. It has good anti-anaerobic bacteria And anti-trichomonad effect, the original drug and intermediate metabolites of ornidazole are active, acting on the DNA of anaerobic bacteria, amoeba, giardia and trichomonas cells, breaking or blocking the helica...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/94B01J27/12
Inventor 邱民
Owner HAINAN MEILAN SMITH KLINE PHARMA
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