Application of novel stable Ulifloxacin mesylate in preparing anti-infective medicament

The technology of mesylate and medicine is applied in the application field of preparing an antibacterial infection medicine, which can solve the problems of difficult clinical treatment of bacterial drug resistance, and achieves the improvement of bioavailability, the expansion of the scope of indications, and the inhibition of bacteria. Highly active effect

Active Publication Date: 2011-09-28
HANGZHOU GUOGUANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these antibacterial drugs cannot meet the growing and refractory diseases in recent years, namely the treatment of chronic Pseudomonas aeruginosa infection and Gram-negative bacterial infection, and with the wide application of antibacterial drugs, bacterial drug resistance The production has become a difficult problem in clinical treatment

Method used

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  • Application of novel stable Ulifloxacin mesylate in preparing anti-infective medicament
  • Application of novel stable Ulifloxacin mesylate in preparing anti-infective medicament
  • Application of novel stable Ulifloxacin mesylate in preparing anti-infective medicament

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0044] Preparation 1: 6-fluoro-1-methyl-7-(1-piperazinyl)-4-oxo-4H-[1,3]thiazetidino[3,2-a]quinone Preparation of phen-3-methanesulfonate

[0045] 1) Preparation of 3,4-difluoro-dithioformic acid-aniline-triethylamine salt (A):

[0046] Under nitrogen protection, put 129g (1.00mol) of difluoroaniline in a 1L reaction flask, then add 202g (2.00mol) of triethylamine, cool to 5°C, slowly add 84g (1.10mol) of carbon disulfide dropwise, and complete the addition in 5 ~10°C, stirred and reacted overnight, filtered, rinsed the filter cake with diethyl ether, and dried under vacuum at room temperature to obtain 294.2 g of light yellow solid with a yield of 96.0%.

[0047] TLC developer: petroleum ether: ethyl acetate: 4:1, Rf=0.60

[0048] 2) Preparation of 3,4-difluorophenylisothiocyanate (B):

[0049] Under the protection of nitrogen, add 306g (1.00mol) of homemade A and 450mL of dichloromethane to a 1L reaction flask in sequence, stir evenly, cool to 5°C with ice water, add 119g...

Embodiment 1

[0066] a. Preparation of Ulifloxacin Mesylate

[0067] Add 10 g of the ulifloxacin prepared in Preparation Example 1 and 500 mL of acetonitrile into a 1 L three-necked flask, stir for half an hour under reflux to dissolve, then add 2.70 g of methanesulfonic acid under continuous stirring, stir for 30 minutes, add 50 mL of distilled water and 1.0 g of activated carbon, Gradually heat up to reflux and keep warm for 2h. The reaction was almost complete, the solution became clear, filtered while it was hot, and the filtrate was refrigerated overnight, a large number of crystals were precipitated, filtered with suction, and the filter cake was washed twice with ethanol, 25 mL each time. The obtained solid was dried under reduced pressure at 40° C. for 10 h to obtain 10.62 g of off-white or light yellow solid, with a yield of 83.3%.

[0068] b. Preparation of Ulifloxacin Mesylate for Injection

[0069] Take 50g of ulifloxacin mesylate raw material, put it in a suitable sterile con...

Embodiment 2

[0074] Example 2: The in vivo protective effect of prepared ulifloxacin mesylate on mice infected with Escherichia coli and Klebsiella pneumoniae

[0075] Using ulifloxacin as a control, the in vivo protective effect of ulifloxacin mesylate on mice infected with Escherichia coli and Klebsiella pneumoniae was compared. In this study, Kunming mice were used as the test object, and the test strains (Escherichia coli, Klebsiella pneumoniae) were isolated from the hospital. The animals were divided into 7 groups, and the doses of the test drug given to the animals in each group were 3.5, 2.45, 1.715, 1.20, 0.84, 0.59 and 0.41 mg / kg body weight (calculated as Ulifloxacin), respectively. , administered by subcutaneous injection. During the test period, the mice were fed under normal conditions, and the survival of the mice within 48 hours after administration was observed.

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Abstract

Because of poor solubility in water, Ulifloxacin has low bioavailability. The invention relates to a novel Ulifloxacin mesylate, a preparation thereof, a kit comprising the medical antibiotic preparation, and application of the novel Ulifloxacin mesylate in preparing an anti-infective medicament. The invention specifically relates to a novel medicinal preparation which is used for injection and remains stable in storage; the chemical name of the preparation is 6-fluorine-1-methyl-7-(1-piperazinyl)-4-oxo-4H-[1,3]thiadiazolebutane[3,2-a]quinoline-3-mesylate. In the invention, injection and administration are carried out directly in the form of Ulifloxacin mesylate, and therefore solubility and bioavailability of Ulifloxacin are enhanced, and treatment effects of the preparation are improved simultaneously.

Description

Technical field: [0001] The present invention relates to new ulifloxacin (Ulifloxacin) mesylate and its preparation, a test kit comprising the pharmaceutical antibiotic preparation, and the application of the new ulifloxacin mesylate in the preparation of an antibacterial infection drug . In particular, it relates to a new stable chemical name for injection: 6-fluoro-1-methyl-7-(1-piperazinyl)-4-oxo-4H-[1,3 ] Pharmaceutical preparations of thiazetidino[3,2-a]quinoline-3-methanesulfonate. Background technique: [0002] Microbial infection is the main factor that threatens human health. In the process of fighting against diseases, humans have discovered a variety of antibacterial drugs: β-lactams, macrolides, aminoglycosides, other antibiotics and synthetic drugs. Synthetic drugs include the largest class of antibacterial drugs: quinolones, among which ciprofloxacin, ofloxacin, levofloxacin, pefloxacin, etc. have been widely used in clinical practice and have become a clinic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/496A61P31/04C07D513/04
Inventor 单爱莲胡定国
Owner HANGZHOU GUOGUANG PHARMA
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