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Ornidazole compound and novel preparation method thereof

A technology of ornidazole and compounds, applied in the field of ornidazole compounds, can solve problems affecting the quality of preparation products, unsuitable for industrial production, color enhancement, etc., and achieve the effect of improving clinical adverse reactions

Inactive Publication Date: 2013-04-03
HAINAN MEILAN SMITH KLINE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation method of a kind of ornidazole optical enantiomer introduced in Chinese patent CN1651415A is completed through six-step experiments, which is relatively complicated, uses more reagents, has high cost, and has low yield
[0007] Chinese patent CN1923817A discloses the synthetic method of ornidazole, uses Lewis acid to catalyze, and its productive rate is generally less than 60%
[0008] It can be seen that the methods in the prior art have many steps and are not suitable for industrial production; or the yield is low, a large amount of raw materials are consumed, resulting in high costs, or toxic solvents are used, resulting in toxic residues of the drug, which affects the preparation products quality
[0009] In addition, when the compound is improperly stored or stored for too long, the content of the active ingredient of the drug will decrease, the color will be enhanced, and the content of related substances such as 2-methyl-5-nitroimidazole will increase
In some cases, the purity of the drug did not meet the requirements due to improper control of the manufacturing process
The prior art does not disclose a special purification method for this, so it is necessary to further purify the unqualified product or crude to provide a high-purity compound with a high yield

Method used

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  • Ornidazole compound and novel preparation method thereof
  • Ornidazole compound and novel preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] The refining of embodiment 1 ornidazole

[0053] Dissolve 10g of crude ornidazole with a purity of 96.52% in 40ml of ethanol, stir to dissolve completely, then add 0.2g of activated carbon, stir and adsorb at 40°C for 15 minutes, filter for decarburization, and collect the filtrate; after concentration, add 10g of The aluminum is stirred evenly, and added to the upper end of the prepared chromatographic column after the solvent is evaporated, and then the filtrate is separated and purified with a preparative chromatographic column, wherein the mobile phase used in the chromatographic column is a mixed solution of acetonitrile and water with a volume ratio of 3:7, The flow rate is 0.1ml / min, the stationary phase filler is ICN allumina N neutral alumina with a particle size of 18-32μm and a pore size of 6nm, the column temperature is room temperature, and the wavelength is 312nm. The eluate is collected and concentrated under reduced pressure at 50°C; Pure water was added...

Embodiment 2

[0056] The refining of embodiment 2 ornidazole

[0057] Dissolve 10g of crude ornidazole with a purity of 96.52% in 100ml of ethanol, stir to dissolve completely, then add 0.1g of activated carbon, stir and adsorb at 50°C for 10 minutes, filter for decarburization, and collect the filtrate; add 10g of The aluminum is stirred evenly, and added to the upper end of the prepared chromatographic column after the solvent is evaporated, and then the filtrate is separated and purified with a preparative chromatographic column, wherein the mobile phase used in the chromatographic column is a mixed solution of acetonitrile and water with a volume ratio of 3:7, The flow rate is 2ml / min, the stationary phase filler is Baker column chromatography special neutral alumina with a particle size of 50-200μm and a pore size of 6nm, the column temperature is room temperature, and the wavelength is 312nm. The eluate is collected and concentrated under reduced pressure at 50°C; Pure water was added...

Embodiment 3

[0060] The refining of embodiment 3 ornidazole

[0061] Dissolve 15g of crude ornidazole with a purity of 96.52% in 120ml of ethanol, stir to dissolve it completely, then add 0.4g of activated carbon, stir and adsorb at 45°C for 10 minutes, filter for decarburization, and collect the filtrate; after concentration, add 15g of The aluminum is stirred evenly, and added to the upper end of the prepared chromatographic column after the solvent is evaporated, and then the filtrate is separated and purified with a preparative chromatographic column, wherein the mobile phase used in the chromatographic column is a mixed solution of acetonitrile and water with a volume ratio of 3:7, The flow rate is 1ml / min, the stationary phase filler is ICN allumina N neutral alumina with a particle size of 18-32μm and a pore size of 6nm, the column temperature is room temperature, and the wavelength is 312nm. The eluate is collected and concentrated under reduced pressure at 50°C; Pure water was add...

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Abstract

The invention relates to an ornidazole compound which is prepared in a method comprising the following steps: (1) a certain amount of ornidazole crude is dissolved in an organic solvent, active carbon is added for adsorption and filtration, filtrate is collected, pressure is reduced for concentration, and then primarily purified ornidazole is obtained; (2) the primarily purified ornidazole is separated and purified by a preparation type chromatographic column, eluent is collected, pressure is reduced for concentration, and then secondarily purified ornidazole is obtained; and (3) pure water is added into a concentrated solution, crystallization is carried out, and precipitated crystals are centrifugally washed and dried to obtain thirdly purified ornidazole. The ornidazole prepared in themethod has high purity, the toxic and side effects of anaerobic bacteria and trichomonad resisting drugs are reduced, the product quality of preparations is improved, and the method is suitable for industrial mass production.

Description

technical field [0001] The invention relates to an ornidazole compound, through which high-purity ornidazole can be obtained, and belongs to the technical field of medicine. Background technique [0002] Ornidazole, white or light yellow crystalline powder, chemical name: 1-(3-chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole, molecular formula: C 7 h 10 ClN 3 o 3 , molecular weight: 219.63, structural formula: [0003] [0004] Ornidazole is an anaerobic and anti-trichomonad drug that was first listed in Germany by the Swiss Roche Company in 1977 after metronidazole and tinidazole. The mechanism of its antimicrobial effect may be: through its molecule The nitro group is reduced to an amino group in an oxygen-free environment or interacts with cell components through the formation of free radicals, resulting in the death of microorganisms; clinically, ornidazole is used to treat bacteria caused by Bacteroides fragilis, Bacteroides dissimilarum, and Bacteroides ovale ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/94A61K31/4164A61P33/02A61P31/04
Inventor 杨明贵董林青
Owner HAINAN MEILAN SMITH KLINE PHARMA