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Levoulifloxacin mesylate crystal, its preparation method and application

A technology of ulifloxacin and methanesulfonic acid, which is applied in the direction of pharmaceutical formulations, medical preparations containing active ingredients, antibacterial drugs, etc., can solve problems such as unstable properties, strong moisture absorption, and insufficient stability of water content, and achieve Effect of good reproducibility, simple preparation method, and good potential for clinical application

Active Publication Date: 2012-04-25
GUANGZHOU PHARMACEUTICAL INDUSTRIAL RESEARCH INSTITUTE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] However, the above-mentioned L-ulifloxacin mesylate crystal A has obvious disadvantages such as the following in the field of pharmaceutical industry: poor stability, which is reflected in strong moisture absorption, and leads to insufficient stability of water content, which in turn leads to inaccurate stoichiometry in the preparation process, And unstable properties, easy to produce decomposition products; strong static electricity, resulting in some preparation process steps (such as sieving, bottling, etc.) are not easy to operate

Method used

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  • Levoulifloxacin mesylate crystal, its preparation method and application
  • Levoulifloxacin mesylate crystal, its preparation method and application
  • Levoulifloxacin mesylate crystal, its preparation method and application

Examples

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preparation example Construction

[0061] Specifically, the preparation method adopted in the present invention can exemplarily include:

[0062] 1. (S)-6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-1H,4H-[1,3]thiazetidine[3,2 -a] the preparation of quinoline-3-carboxylic acid (levo-ulifloxacin)

[0063] 105 grams of racemic ulifloxacin were dissolved in 1500 ml of dimethyl sulfoxide, and a dimethyl sulfoxide solution of 405 ml of D-tartaric acid (27 grams) was added dropwise with stirring, turbidity and precipitation occurred, and stirred at room temperature for 20 hours; Filtration, the obtained solid was dried under vacuum to obtain 86 g, and the solid was recrystallized and purified in dimethyl sulfoxide to obtain (S)-6-fluoro-1-methyl-4-oxo-7-(1- Piperazinyl)-1H, 4H-[1,3]thiazetidino[3,2-a]quinoline-3-carboxylic acid-D-tartrate 37 grams. Add this salt into water to form a suspension, adjust the pH value to 7-8 with 2% NaOH aqueous solution under stirring, and filter and dry the precipitate to obtain (S)-6-fl...

Embodiment 1

[0074]Preparation of L-ulifloxacin mesylate crystal A (prepared with reference to the method of Chinese invention patent application CN200810027211.9)

[0075] At room temperature 20°C, add 30ml of water to the reaction flask, add 2.1 grams of methanesulfonic acid under stirring, then add 5 grams of (S)-6-fluoro-1-methyl-4-oxo-7-(1- Piperazinyl)-1H,4H-[1,3]thiazetidino[3,2-a]quinoline-3-carboxylic acid, after stirring for 60 minutes to obtain a substantially clear solution, adding (S) -6-Fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-1H,4H-[1,3]thiazetidino[3,2-a]quinoline 5% of the weight of the 3-carboxylic acid was decolorized by activated carbon for 30 minutes and then filtered, and the filtrate was added dropwise with 200 ml of absolute ethanol within 1 hour under stirring, and a solid was precipitated at this time, and the stirring was continued for 2 hours, the solid was filtered, and vacuum-dried at 60°C to obtain 4.0 grams of (S)-6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-1H...

Embodiment 2

[0078] Preparation of L-ulifloxacin Mesylate Crystal B

[0079] At room temperature, add 150ml of water to the reaction flask, add 10 grams of methanesulfonic acid and 35 grams of (S)-6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl) under stirring )-1H, 4H-[1,3]thiazetidine[3,2-a]quinoline-3-carboxylic acid, adding (S)-6-fluoro-1-methyl-4-oxo Substitute-7-(1-piperazinyl)-1H, 4H-[1,3]thiazetidino[3,2-a]quinoline-3-carboxylic acid weight of 5% activated carbon 50 ℃ insulation Stir for 30 minutes to decolorize and filter, evaporate the filtrate to remove the solvent under reduced pressure, add 100ml of ethanol, filter, and dry the solid in vacuum at 60°C to obtain 34.3 grams of methanesulfonic acid (S)-6-fluoro-1-methyl-4-oxo- Crude 7-(1-piperazinyl)-1H,4H-[1,3]thiazetidino[3,2-a]quinoline-3-carboxylic acid.

[0080] 5 grams of methanesulfonic acid (S)-6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-1H,4H-[1,3]thiazetidine[ 3,2-a] quinoline-3-carboxylic acid crude product, 0.25 g of activa...

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Abstract

The invention provides a levoulifloxacin mesylate crystal. The Cu-Kalpha radiated X-ray powder diffraction pattern of the crystal has the following 2theta angel expressed peaks: 5.4-5.8 degrees, 18-18.4 degrees and 25.8-26.2 degrees. The invention also provides a preparation method of the crystal, a medical composition containing the crystal, as well as medical application of the crystal and the medical composition. The crystal provided in the invention has good reproducibility, as well as simple and rapid preparation method. Experiments prove that the crystal of the invention is better than existing crystals in terms of solubility, stability, hygroscopicity and treatment effects in vivo. The crystal in the invention can also be prepared into a plurality preparation forms for use and has good clinical application potential.

Description

technical field [0001] The present invention relates to a new crystal of levofloxacin mesylate, a preparation method thereof, a pharmaceutical composition containing the new crystal and their use in preparing medicines for treating infectious diseases. Background technique [0002] Levo-ulifloxacin mesylate is a fluoroquinolone drug, its chemical name is: (S)-6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl) methanesulfonate -1H, 4H-[1,3]thiazetidin[3,2-a]quinoline-3-carboxylic acid (structural formula 1), its bactericidal mechanism is to be the action target with the DNA of bacteria, by Hindering DNA topoisomerase prevents bacterial DNA from forming supercoils, which causes irreversible damage to chromosomes and prevents bacterial cells from dividing and multiplying. [0003] [0004] Compared with the racemate, levo-ulifloxacin has stronger activity and lower toxicity, so it has broad application prospects in the field of biomedicine. Levo-ulifloxacin mesylate has good water ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D513/04A61K31/496A61P31/04
Inventor 彭锋林丽薇王玉平应军倪庆纯郑浩君陈洁斌冯颂延
Owner GUANGZHOU PHARMACEUTICAL INDUSTRIAL RESEARCH INSTITUTE
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