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Preparation method of pefloxacin mesylate

A technology of pefloxacin mesylate and methanesulfonic acid, which is applied in the field of preparation of pefloxacin mesylate synthesized from solid formaldehyde, can solve the problems of uneconomical, reduced product yield, time-consuming and labor-intensive problems

Inactive Publication Date: 2014-03-26
HEZE CITY FANGMING PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] During the methylation reaction between formaldehyde and norfloxacin, since the liquid formaldehyde contains a large amount of water, it will affect the yield and reaction speed, so the actual amount of formaldehyde consumed in the reaction is much higher than the theoretical amount, which is uneconomical It is not environmentally friendly. In addition, the purification and separation process of intermediate products is time-consuming and labor-intensive in production, and will cause a reduction in product yield.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0009] Example 1: Add 95g of formic acid and 14g of solid formaldehyde into a 500ml reaction flask, add 98g of norfloxacin several times under stirring, slowly raise the temperature to 72°C and maintain reflux for 1.5h after 1h, then raise the temperature to 95°C and maintain reflux for 6.5h; After evaporating to dryness under reduced pressure, add water and distill 4 times, cool down to 25~30°C, add 450g of 83% ethanol, add 32.4g of methanesulfonic acid under stirring, heat up to 75°C and reflux for 1.5h, slowly cool down to 0-3°C and suction filter; Add 83% ethanol to the obtained product, raise the temperature until the material liquid is clear, add 5 g of medicinal carbon, heat filter after 1 hour, slowly cool the filtrate to 0-3°C for suction filtration, and dry at 40°C to obtain off-white crystalline powder 133g, the yield is 93.2%, the moisture content is 7.4%, and the pefloxacin mesylate content is 99.87%.

example 2

[0010] Example 2: Add 85g of formic acid and 13.9g of solid formaldehyde into the reaction kettle, add 94g of norfloxacin several times under stirring, slowly raise the temperature to 71°C and maintain reflux for 1h after 1h, raise the temperature to 96°C and maintain reflux for 6.5h; After pressure-evaporating to dryness, add water to distill three times, cool down to 25-30°C, add 450g of 83% ethanol, add 32.3g of methanesulfonic acid under stirring, heat up to 72°C and reflux for 1.5h, slowly cool down to 0-3°C and suction filter; Add 83% ethanol to the product, raise the temperature until the material liquid is clear, add 5 g of medicinal carbon, heat filter after 1 hour, slowly cool the filtrate to 0-3°C for suction filtration, and dry at 40°C. 123 g of off-white crystalline powder was obtained with a yield of 89.7%, a water content of 7.2%, and a pefloxacin mesylate content of 99.97%.

example 3

[0011] Example 3: Add 100g of formic acid and 20g of solid formaldehyde into the reaction kettle, add 100g of norfloxacin several times under stirring, slowly raise the temperature to 72°C and maintain reflux for 1h after 1h, raise the temperature to 91°C and maintain reflux for 6.5h; reduce pressure After evaporating to dryness, add water to distill 3 times, cool down to 25~30°C, add 450g of 83% ethanol, add 38g of methanesulfonic acid under stirring, heat up to 70°C and reflux for 1.5h, slowly cool down to 0-3°C and suction filter; the obtained product Add 83% ethanol, raise the temperature until the material liquid is clear, add 5 g of medicinal carbon, heat filter after 1 hour, slowly cool the filtrate to 0-3 °C for suction filtration, and dry at 40 °C. 133 g of off-white crystalline powder was obtained with a yield of 91.8%, a moisture content of 7.5%, and a pefloxacin mesylate content of 99.85%.

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PUM

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Abstract

The invention belongs to the technical field of pharmacy and discloses a method for synthesizing pefloxacin mesylate by utilizing solid formaldehyde instead of liquid formaldehyde. The method is characterized in that solid formaldehyde, methanoic acid and norfloxacin are methylated under a given temperature condition, an intermediate product is crystallized and re-crystallized in 83% ethanol solution after directly having the salt forming reaction with methanesulfonic acid without being separated to obtain the pefloxacin mesylate containing two crystal waters, and the yield can reach 93.2 percent. By adopting the solid formaldehyde, transportation and storage are simple and convenient, the consumption of the formaldehyde is reduced, and economical and environment-friendly effects are achieved; the separation process of the intermediate product is omitted, so that the loss of the intermediate product is reduced, the product yield is increased, the method is applicable to the industrial production, and the quality conforms to the pharmacopeia 2010 version.

Description

technical field [0001] The invention belongs to the technical field of pharmacy, and in particular relates to a preparation method for synthesizing pefloxacin mesylate by using solid formaldehyde. Background technique [0002] Pefloxacin mesylate (C 17 h 20 FN 3 o 3 ·CH 4 o 3 S·2H 2 O), the chemical name is 1-ethyl-6-fluoro-1,4-dihydro-7-(N-4-methyl-piperazinyl)-4-oxo-3-quinolinecarboxylic acid methanesulfonic acid Dihydrate, molecular weight: 465.49. It can treat various infections caused by pefloxacin-sensitive bacteria: urinary tract infection; respiratory tract infection; ear, nose and throat infection; gynecological and reproductive system infection; abdominal and liver and biliary system infection; bone and joint infection; skin Infection; sepsis and endocarditis; meningitis. [0003] During the methylation reaction between formaldehyde and norfloxacin, since the liquid formaldehyde contains a large amount of water, it will affect the yield and reaction speed,...

Claims

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Application Information

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IPC IPC(8): C07D215/56
CPCC07D215/56
Inventor 杨蕾孙洋涛王兴路朱文祥张允杰
Owner HEZE CITY FANGMING PHARMA
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