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Onitrodazole precursor drug and its preparation process and use

A technology of prodrug and ornidazole, applied in the field of prodrug of ornidazole and its preparation and application

Inactive Publication Date: 2007-07-18
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

At present, there is no report on the prodrug research of ornidazole at home and abroad. The inventor discloses a prodrug of ornidazole ornidazole phosphate in Chinese patent CN200610041611.6

Method used

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  • Onitrodazole precursor drug and its preparation process and use
  • Onitrodazole precursor drug and its preparation process and use
  • Onitrodazole precursor drug and its preparation process and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: the preparation of L-ornidazole acetate

[0036] Dissolve 110g of L-ornidazole in 500ml of dry ethyl acetate solution, add 90ml of acetyl chloride dropwise, control the reaction temperature at 10-20°C, control the reaction in the liquid phase until there is almost no peak of L-ornidazole, and recover acetic acid under reduced pressure Ethyl ester, under cooling, slowly add 600ml of pure water, slowly add 10% sodium carbonate solution to adjust the pH value to 5.0, concentrate to dryness under reduced pressure, add 500ml of ethanol, filter, add 500ml of petroleum ether to the filtrate, freeze and crystallize, Filter to obtain 91 g of L-ornidazole acetate.

[0037] [purity: 98.8%, chromatographic conditions: mobile phase is methanol: potassium dihydrogen phosphate solution of 0.05mol / L (adjusting pH with triethylamine is 6.0)=35: 65; Chromatographic column: Kromasil C18 5u, 250 * 4.6mm ;]

Embodiment 2

[0038] Embodiment 2: Preparation of L-ornidazole propionate

[0039] Dissolve 110g of L-ornidazole in 500ml of dry ethyl acetate solution, add 100ml of propionyl chloride dropwise, control the reaction temperature at 10-20°C, control the reaction in the liquid phase until there is almost no peak of L-ornidazole, and recover acetic acid under reduced pressure Ethyl ester, under cooling, slowly add 600ml of pure water, slowly add 10% sodium carbonate solution to adjust the pH value to 5.0, concentrate to dryness under reduced pressure, add 500ml of ethanol, filter, add 500ml of petroleum ether to the filtrate, freeze and crystallize, After filtration, 97 g of levo-ornidazole propionate was obtained.

[0040] [Purity: 99.1%, chromatographic conditions: mobile phase is methanol: potassium dihydrogen phosphate solution of 0.05mol / L (adjusting pH with triethylamine is 6.0)=35: 65; Chromatographic column: Kromasil C18 5u, 250 * 4.6mm ;]

Embodiment 3

[0041] Embodiment 3: the preparation of L-ornidazole benzoate

[0042] Dissolve 110g of L-ornidazole in 500ml of dry ethyl acetate solution, add 120ml of benzoyl chloride dropwise, control the reaction temperature at 10-20°C, control the reaction in the liquid phase until there is almost no peak of L-ornidazole, and recover under reduced pressure Ethyl acetate, under cooling, slowly add 600ml of pure water, slowly add 10% sodium carbonate solution to adjust the pH value to 5.0, concentrate to dryness under reduced pressure, add 500ml of ethanol, filter, add 500ml of petroleum ether to the filtrate, freeze and crystallize , filtered to obtain L-ornidazole benzoate 109g.

[0043] [purity: 98.3%, chromatographic condition: mobile phase is methanol: 0.05mol / L potassium dihydrogen phosphate solution (adjusting pH with triethylamine is 6.0)=35: 65; Chromatographic column: Kromasil C18 5u, 250 * 4.6mm ;]

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PUM

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Abstract

This invention involves Ornidazole precursor drug and its preparation and use. Ornidazole precursor drugs is obtained by through chemical modification to its structure of the hydroxyl group, can be used in medicinal combination, can be used to treat anaerobic bacteria or protozoan infection diseases.

Description

Technical field: [0001] The invention relates to a prodrug of ornidazole, a preparation method thereof and an application thereof in the field of medicine. technical background: [0002] Ornidazole is ((±)1-(3-chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole (Ornidazole, CAS 16773-42-5). Ornidazole is nitroimidazole It is a powerful anti-anaerobe and antiprotozoal infection drug, and it is also the third-generation nitroimidazole newly developed after metronidazole with higher curative effect, shorter course of treatment, better tolerance and wider distribution in the body 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] Levo-ornidazole ((-)1-(3-chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole), Chinese patents (CN200510068478.9, CN200510083517.2) de...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/92C07F9/09A61K31/4164A61P31/04A61P33/02
Inventor 苏红军
Owner 西安新安医药科技有限公司
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