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Lactic levorotatory ulifloxacin crystal, and preparation method and application thereof

A technology of ulifloxacin and lactic acid, which is applied in the field of Lactate L-ulifloxacin crystals and its preparation and application, can solve the problems of insufficient water content, unstable properties, difficult operation, etc., achieve good clinical application potential, and simple preparation method , good reproducible effect

Active Publication Date: 2014-08-20
GUANGZHOU PHARMACEUTICAL INDUSTRIAL RESEARCH INSTITUTE
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, the above-mentioned levofloxacin lactate crystal A (or called A crystal, hereinafter the same) has obvious disadvantages such as the following in the field of pharmaceutical industry: poor stability, which is reflected in strong hygroscopicity, and leads to insufficient stability of water content, which in turn leads to preparations Inaccurate stoichiometry and unstable properties in the process, easy to produce decomposition products; strong static electricity, which makes some preparation process steps (such as sieving, bottling, etc.) difficult to operate

Method used

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  • Lactic levorotatory ulifloxacin crystal, and preparation method and application thereof
  • Lactic levorotatory ulifloxacin crystal, and preparation method and application thereof
  • Lactic levorotatory ulifloxacin crystal, and preparation method and application thereof

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preparation example Construction

[0057] Specifically, the preparation method adopted in the present invention can exemplarily include:

[0058] 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)

[0059] 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

[0070] Preparation of L-ulifloxacin Lactate Crystal A (prepared with reference to the method of Chinese invention patent application CN200810027211.9)

[0071]At room temperature 20°C, add 30ml of water to the reaction flask, add 2.1 grams of lactic acid while stirring, and then add 5 grams of (S)-6-fluoro-1-methyl-4-oxo-7-(1-piperazine base)-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-3 5% of the weight of the 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, at this time, a solid was precipitated, and the stirring was continued for 2 hours, the solid was filtered, and vacuum-dried at 60°C to obtain 4.0 grams Lactic acid (S)-6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl...

Embodiment 2

[0074] Preparation of L-ulifloxacin Lactate Crystal B

[0075] At room temperature, add 150ml of water to the reaction flask, add 14.7 grams of lactic acid under stirring, and then add 35 grams of (S)-6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl) -1H, 4H-[1,3]thiazetidino[3,2-a]quinoline-3-carboxylic acid, add (S)-6-fluoro-1-methyl-4-oxo -7-(1-piperazinyl)-1H, 4H-[1,3]thiazetidin[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, collect the solid and dry it in vacuum at 60°C to obtain 34 grams of lactic acid (S)-6-fluoro-1-methyl-4-oxo-7 Crude -(1-piperazinyl)-1H,4H-[1,3]thiazetidino[3,2-a]quinoline-3-carboxylic acid.

[0076] 5 grams of lactic 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 activated carbon, 100 ml of ...

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Abstract

The invention provides a lactic levorotatory ulifloxacin crystal. According to the lactic levorotatory ulifloxacin crystal, an X-ray powder diffraction map of Cu-K alpha radiation has the following peaks expressed by 2 theta degrees: 5.1+ / -0.2 degrees, 10.3+ / -0.2 degrees and 15.5+ / -0.2 degrees. The invention also provides a method for preparing the lactic levorotatory ulifloxacin crystal, a medicinal composition containing the crystal and application of the lactic levorotatory ulifloxacin crystal and the medicinal composition to pharmacy. The lactic levorotatory ulifloxacin crystal has high reproducibility, and the preparation method is simple and quick. Experiments prove that the solubility, stability, hygroscopicity and an in-vivo treatment effect of the lactic levorotatory ulifloxacin crystal are superior to those of the conventional crystal of the compound, and the lactic levorotatory ulifloxacin crystal can also be prepared into various formulations, and has a good clinical application potential.

Description

technical field [0001] The present invention relates to a new crystal of L-ulifloxacin lactate and a preparation method thereof, as well as a pharmaceutical composition containing the new crystal and their use in preparing medicines for treating infectious diseases. Background technique [0002] Lactate L-ulifloxacin is a fluoroquinolone drug, its chemical name is: lactic acid (S)-6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-1H, 4H -[1,3]thiazetidino[3,2-a]quinoline-3-carboxylic acid (structural formula 1), its bactericidal mechanism is to take the DNA of bacteria as the target, by hindering the DNA topological Constructase prevents bacterial DNA from forming supercoils, further causing irreversible damage to chromosomes, resulting in the inability of bacterial cells to divide and reproduce. [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-uliflox...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D513/04C07C59/08C07C51/43A61K31/496A61P31/00
Inventor 彭锋应军王玉平倪庆纯林丽薇郑浩君陈洁斌冯颂延
Owner GUANGZHOU PHARMACEUTICAL INDUSTRIAL RESEARCH INSTITUTE
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