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Preparation method of ulifloxacin optical isomer

A technology of optical isomers and structural formulas, used in organic chemistry, anti-infective drugs, drug combinations, etc., can solve problems such as low yield, inability to apply industrial-scale production, and large equipment investment, achieve high purity, and facilitate industrial mass production. , the effect of the simple method

Active Publication Date: 2009-10-07
GUANGZHOU PHARMACEUTICAL INDUSTRIAL RESEARCH INSTITUTE +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Obviously, the above-mentioned method for preparing the optical isomers of Ulifloxacin has large equipment investment and low output, and is only suitable for academic research, but cannot be applied to industrial scale production

Method used

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  • Preparation method of ulifloxacin optical isomer
  • Preparation method of ulifloxacin optical isomer
  • Preparation method of ulifloxacin optical isomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0011] The preparation of embodiment 1 (S)-ulifloxacin

[0012] Dissolve 105 g of racemic ulifloxacin in 1500 mL of dimethyl sulfoxide, add dropwise a solution of 27 g of D-tartaric acid dissolved in 405 mL of dimethyl sulfoxide under stirring, turbidity and precipitation appear, and stir at room temperature for 20 hours , precipitated and filtered, and the resulting solid was dried under vacuum to obtain 86 grams. This solid was recrystallized in dimethyl sulfoxide to obtain 37 grams of L-ulifloxacin-D-tartrate. After elemental analysis, C49.08%, H5. 06%, N9.50%, S7.44% (molecular composition: C 16 h 16 FN 3 o 3 S·1 / 2C 4 h 6 o 6 ·H 2 O, calculated value C48.86%, H4.78, N9.50%, S7.25%); add this salt to water to form a suspension, adjust the pH value to 7-8 with 2% NaOH aqueous solution under stirring, precipitate and filter Dry to obtain (S)-ulifloxacin 24.5 grams, specific rotation (c=0.15, 0.1mol / LNaOH); 1 H-NMR (DMSO-d 6 )δ 2.11 (3H, d, j = 6.2Hz), 2.87 (4H, m)...

Embodiment 2

[0013] The preparation of embodiment 2 (R)-ulifloxacin

[0014] Dissolve 105 grams of racemic ulifloxacin in 1500 mL of DMSO, add dropwise a solution of 27 grams of L-tartaric acid dissolved in 405 mL of dimethyl sulfoxide under stirring, turbidity and precipitation appear, stir at room temperature for 20 hours, and filter to obtain The solid was dried under vacuum to obtain 82 grams, and the solid was recrystallized and purified in dimethyl sulfoxide to obtain 34 grams of dextro-ulifloxacin-L-tartrate. The salt was added to water to form a suspension, and stirred with 2% NaOH aqueous solution adjusted the pH value to 7-8, filtered and dried to obtain 22 grams of (R)-ulifloxacin, specific rotation (c=0.15, 0.1mol / LNaOH), optical purity e.e.>95%.

Embodiment 3

[0015] Embodiment 3 in vitro antibacterial test

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Abstract

The invention relates to a preparation method of a ulifloxacin optical isomer, in particular to a preparation method of a 6-fluorine-1-methyl-4-oxo-(1-piperazinyl)-1H and 4H-(1, 3) sulfur azetidine combined with (3, 2-a) quinoline-3-carboxylic acid optical isomer, which comprises the following steps: (+ / -) ulifloxacin is taken to be dissolved in dimethyl sulfoxide, a dimethyl sulfoxide solution of D-tartaric acid is dropped into the dimethyl sulfoxide to obtain (S)-ulifloxacin-D-tartrate precipitation, the pH value of the (S)-ulifloxacin-D-tartrate is regulated by a NaOH solution in water after the (S)-ulifloxacin-D-tartrate is recrystallized so as to obtain precipitates, the precipitates are filtered and dried to obtain (S)-ulifloxacin, and the optical purity e.e. of the (S)-ulifloxacin is more than 95 percent. The preparation method of the ulifloxacin optical isomer is simple and convenient without special equipment requests and is beneficial to industrialized batch production, and an obtained optically active body has high purity.

Description

technical field [0001] The invention relates to a preparation method in the field of chemical medicines, in particular to 6-fluoro-1-methyl-4-oxo-(1-piperazinyl)-1H, 4H-[1,3]thiazetidine [3,2-a] Preparation method of quinoline-3-carboxylic acid photoisomer. Background technique [0002] Ulifloxacin, known internationally as Ulifloxacin, is a quinolone drug with remarkable anti-infective effect, and its chemical name is (±) 6-fluoro-1-methyl-4-oxo-(1-piperazinyl) -1H, 4H-[1,3]thiazetidin[3,2-a]quinoline-3-carboxylic acid, its structural formula is as follows formula 1: [0003] [0004] Ulifloxacin has a broad-spectrum antibacterial effect on Gram-positive and Gram-negative bacteria, especially against Staphylococcus aureus, Streptococcus pneumoniae, Enterococcus faecalis, Serratia mucinus, Pseudomonas aeruginosa and other bacteria Effect. Both in vivo and in vitro experiments have shown that Ulifloxacin not only has a broad antibacterial spectrum and strong in vivo act...

Claims

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Application Information

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IPC IPC(8): C07D495/04A61P31/00
CPCC07D513/04A61P31/00
Inventor 朱少璇陈矛王玉平刘学斌彭锋杨威安穗伟曾琳玲
Owner GUANGZHOU PHARMACEUTICAL INDUSTRIAL RESEARCH INSTITUTE
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