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Water-soluble sarafloxacin mesylate and preparation method thereof

A technology of sarafloxacin and methanesulfonic acid, which is applied to the preparation of sulfonate, resistance to vector-borne diseases, organic chemistry, etc., can solve the problems of poor water solubility of sarafloxacin and sarafloxacin hydrochloride, etc., to improve water solubility, The effect of strong antibacterial activity and good application prospects

Active Publication Date: 2015-09-09
XUZHOU TIANYI ANIMAL PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved in the present invention is that sarafloxacin and sarafloxacin hydrochloride have poor water solubility

Method used

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  • Water-soluble sarafloxacin mesylate and preparation method thereof
  • Water-soluble sarafloxacin mesylate and preparation method thereof
  • Water-soluble sarafloxacin mesylate and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] The preparation of embodiment 1 sarafloxacin mesylate

[0018] Dissolve sarafloxacin hydrochloride in water, adjust the pH to about 7.5 with sodium hydroxide, precipitate solids, filter, and collect sarafloxacin solids.

[0019] Dissolve the sarafloxacin (1mol) solid in a mixed solvent of ethanol and water (the weight ratio of ethanol to water is 1:0.05), add methanesulfonic acid whose molar number is 1 times that of sarafloxacin under heating to 80°C, and stir 2.0 hours, cooled for 10 hours to precipitate crystals, collected by filtration, washed with ethanol for 1 to 3 times, and dried in vacuum to obtain the target product. White crystals, yield 92%, fast atom bombardment mass spectrometry MS (FAB): m / e 481.39 (M + ), 385.37 (M + -CH 3 SO 3 H), consistent with the molecular weight theoretically calculated value of target product sarafloxacin mesylate 481.47.

Embodiment 2

[0020] The preparation of embodiment 2 sarafloxacin mesylate

[0021] Dissolve sarafloxacin hydrochloride in water, adjust the pH to about 7.5 with sodium hydroxide, precipitate solids, filter, and collect sarafloxacin solids.

[0022] Dissolve sarafloxacin (1mol) solid in a mixed solvent of isopropanol and water (the weight ratio of isopropanol to water is 1:0.1), add formazan with 1.2 times the mole number of sarafloxacin under the condition of heating to 90°C Sulfonic acid, stirred for 0.5 hours, cooled for 20 hours to precipitate crystals, collected by filtration, washed with acetonitrile for 1 to 3 times, and dried in vacuum to obtain the target product. White crystals, yield 91.5%, MS (FAB): m / e 481.43 (M + ), 385.28 (M + -CH 3 SO 3 H), consistent with the molecular weight theoretically calculated value of target product sarafloxacin mesylate 481.47.

Embodiment 3

[0023] The preparation of embodiment 3 sarafloxacin mesylate

[0024] Dissolve sarafloxacin hydrochloride in water, adjust the pH to about 7.5 with sodium hydroxide, precipitate solids, filter, and collect sarafloxacin solids.

[0025] Dissolve the solid of sarafloxacin (1mol) in acetonitrile solvent, add methanesulfonic acid whose molar number is 1.5 times that of sarafloxacin under heating to 65°C, stir for 0.5 hours, cool for 20 hours to precipitate crystals, collect the crystals by filtration, and use Wash with isopropanol for 1 to 3 times, and dry in vacuum to obtain the target product. White crystals, yield 88.4%, MS (FAB): m / e 482.02 (M + ), 385.44 (M + -CH 3 SO 3 H), consistent with the molecular weight theoretically calculated value of target product sarafloxacin mesylate 481.47.

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Abstract

The invention belongs to the technical field of chemical synthesis, and in particular relates to water-soluble sarafloxacin mesylate and a preparation method thereof. The sarafloxacin mesylate provided by the invention has the structure shown in the specification. The invention also provides the preparation method of the sarafloxacin mesylate, which comprises the following steps of: dissolving sarafloxacin hydrochloride into water and separating out sarafloxacin solid by adjusting pH; and dissolving the sarafloxacin solid into an organic solution and reacting with methanesulfonic acid to obtain the sarafloxacin mesylate target product. The water-soluble sarafloxacin mesylate and the preparation method thereof are used for solving the technical problem about low water dissolubility of the sarafloxacin and the sarafloxacin hydrochloride. The water solubility of the target product is obviously higher than that of the traditional sarafloxacin hydrochloride raw material; the target product has the advantages of wide antibacterial spectrum, high antimicrobial activity and the like; and the target product is stronger than the sarafloxacin hydrochloride in the aspects of prevention and treatment on mycoplasmosis and treatment on streptococcicosis and colibacillosis, and has a good application prospect.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to water-soluble sarafloxacin mesylate and a preparation method thereof. Background technique [0002] Sarafloxacin, also known as 6-fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinoline carboxy Acid; English: 6-Fluoro-1-(4-fluorophenyl)-1,4-dihydro-4-oxo-7-(1-piper-azinyl)-3-quinolinecarboxylic acid; developed by Abbott in 1995 And listed in the United States, it is the first fluoroquinolone drug approved by the U.S. FDA for food animals. It has the characteristics of broad antibacterial spectrum, strong antibacterial activity, and no cross-resistance with other antibacterial drugs (WOLFSON J S, HOOPER D C , The latest broad-spectrum quinolone antimicrobials [M], Jiang Suchun, Song Keyi, Beijing: People's Military Medical Publishing House, 1991, 26-45). It was approved as a national second-class new drug in 2001 by our country, and the m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/56C07C309/04C07C303/32A61P31/04
CPCC07D215/56Y02A50/30
Inventor 王建华乔书喜赵青森
Owner XUZHOU TIANYI ANIMAL PHARMA
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