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Synthesis of benzoyl ornidazole

A technology of benzoyl ornidazole and ornidazole, which is applied in the field of synthesis of ornidazole derivatives, can solve problems such as difficulties in children's medication, and achieve timely and effective treatment of diseases

Inactive Publication Date: 2012-03-21
SHAANXI HONGFU YIYUE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, ornidazole tastes very bitter, and it is difficult for children to use it

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Example 1: Add ornidazole, fatty acid fatty alcohol ester, aliphatic tertiary amine or nitrogen-containing heterocyclic organic base in sequence in a three-neck flask at normal temperature and pressure, stir to dissolve and clarify. Raise the temperature to the reflux temperature, add benzoyl chloride dropwise, after the addition is complete, keep the reaction under normal pressure for 1-8 hours; cool down to 0°C±2°C, add water to separate the layers, wash the organic phase with water, cool and freeze to crystallize, filter, Wash and dry to obtain crude product. The crude product was recrystallized from ethanol to obtain benzoyl ornidazole.

Embodiment 2

[0021] Example 2: At normal temperature and pressure, 21.9 g of ornidazole, 100 mL of butyl acetate, and 10.1 g of triethylamine were sequentially added into a three-necked flask, stirred, dissolved and clarified. Under heating to reflux, 14.0 g of benzoyl chloride was added dropwise, and after the addition was completed, the reaction was kept for 3 hours. Cool to 0±2°C, add water and stir, let stand to separate layers, and wash the organic phase with water. Cool and freeze to crystallize, filter, wash, and dry to obtain the crude product. The crude product was recrystallized from ethanol to obtain 25.2 g of benzoyl ornidazole.

Embodiment 3

[0023] In a three-neck flask, sequentially add 21.9g of ornidazole, 100mL of ethyl acetate, and 10.1g of triethylamine, stir to dissolve and clarify. Under heating to reflux, 14.0 g of benzoyl chloride was added dropwise, and after the addition was completed, the reaction was kept for 4 hours. Cool to 0±2°C, add water and stir, let stand to separate layers, and wash the organic phase with water. Cool and freeze to crystallize, filter, wash, and dry to obtain the crude product. The crude product was recrystallized from ethanol to obtain 23.8 g of benzoyl ornidazole.

[0024] It should be noted:

[0025] 1. The acid-binding agent is an organic base such as aliphatic tertiary amine, nitrogen-containing heterocyclic compound, etc.

[0026] 2. The solvent used is the C1-C8 fatty alcohol ester of C1-C10 fatty acid, and the reaction temperature is the reflux temperature.

[0027] 3. The order of feeding is ornidazole, fatty alcohol ester of fatty acid, aliphatic tertiary amine or...

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PUM

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Abstract

The invention relates to a new method for synthesizing an ornidazole derivative, namely benzoyl ornidazole. At present, ornidazole is a third-generation novel nitroimidazole derivative after metronidazole and tinidazole, has high anaerobe resistance and protozoan resistance, but is difficultly applied to children because of bitter taste. The invention aims to provide a new method for synthesizing the ornidazole derivative. The synthesis method comprises the following steps of: adding ornidazole, fatty acid and fatty alcohol ester, and aliphatic tertiary amine or nitrogen heterocycle organic base in turn, stirring for dissolution and clarification, heating to refluxing temperature, dripping benzoyl chloride, and reacting by keeping temperature under normal pressure; cooling, adding water, stirring, standing for demixing, adding water to wash an organic phase, cooling and freezing for crystallization, filtering, washing, and drying to obtain a crude product; and recrystallizing the crude product by using ethanol to obtain the benzoyl ornidazole. The method has the advantages that: the obtained benzoyl ornidazole is a precursor medicine of ornidazole, the original bitter taste of the ornidazole is eliminated, and a method for industrially producing the benzoyl ornidazole is realized.

Description

1. Technical field [0001] The invention relates to a new synthetic method of ornidazole derivatives, namely the synthesis of benzoyl ornidazole. 2. Background technology [0002] Ornidazole is the third generation of new nitroimidazole derivatives following metronidazole and tinidazole, and has good anti-anaerobic and anti-protozoal effects. It is used for various diseases caused by anaerobic infection, prevention of infection before operation and treatment of anaerobic infection after operation. However, ornidazole tastes very bitter, and it is difficult for children to use it. 3. Contents of the invention [0003] The purpose of the invention is to propose a new synthetic method of ornidazole derivatives, i.e. the synthesis of benzoyl ornidazole, according to the problems existing in the above-mentioned prior art. Inspired by the listing of benzoyl metronidazole (odorless metronidazole) made by metronidazole at home and abroad, the applicant made benzoyl ornidazole fro...

Claims

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Application Information

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IPC IPC(8): C07D233/94A61P31/04A61P33/02A61P33/04
Inventor 王凌波苏敏温锦荣张敏
Owner SHAANXI HONGFU YIYUE PHARMA
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