Method for splitting ofloxacin chiral drug through liquid-liquid-solid extraction

A technology of ofloxacin and chiral drugs, applied in the field of chiral drug separation, can solve the problems of complex operation process, high equipment cost, low efficiency, etc., and achieves a high separation selectivity, simple equipment and high extraction efficiency. Effect

Inactive Publication Date: 2015-11-11
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Therefore, in view of the complex operation process, high energy consumption, high equipment cost and low efficiency in the existing process for splitting ofloxacin racemate, it is necessary to develop a new separation process

Method used

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  • Method for splitting ofloxacin chiral drug through liquid-liquid-solid extraction
  • Method for splitting ofloxacin chiral drug through liquid-liquid-solid extraction

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Embodiment 1: the concentration of ofloxacin aqueous solution is 1.0g / L extraction experiment

[0019] A. prepare 1.0g / L aqueous solution of ofloxacin, and the organic phase is n-hexane solution. Weigh 0.05375g D-DBTA (dibenzoyl tartaric acid) into a 50mL Erlenmeyer flask, then transfer 20mL each of the organic phase and the aqueous phase into the Erlenmeyer flask with a pipette. Seal the Erlenmeyer flask and place it in a THZ-82A digital display water bath constant temperature oscillator, shake at a speed of 220r / min for 40min, then place it in a centrifuge tube and centrifuge at a speed of 5000r / min for 10min in a centrifuge. The lower layer was filtered, concentrated, dried and purified to obtain ofloxacin crystals.

[0020] Use a disposable sterile syringe to draw 1ml of the aqueous phase clear liquid separated by centrifugation, filter through a 0.45μm filter head, inject 10μL into the high-performance liquid chromatography, and see the results in figure 1 ,Depen...

Embodiment 2

[0021] Embodiment 2: the extraction experiment that the concentration of ofloxacin feed liquid is 0.6g / L

[0022] Prepare 0.6g / L aqueous solution of ofloxacin as the water phase, and the organic phase as n-hexane solution. Weigh 0.0538g of D-DBTA, put it into a 50mL Erlenmeyer flask, transfer 20ml of n-hexane solution and 20mL ofloxacin aqueous solution with a concentration of 0.6g / L into the Erlenmeyer flask, seal the Erlenmeyer flask and place it in a digital display water bath for constant temperature The shaker THZ-82A oscillated at a speed of 220r / min for 40min, then placed in a centrifuge tube and centrifuged at a speed of 5000r / min for 10min in a centrifuge. The lower layer was filtered, concentrated, dried and purified to obtain ofloxacin crystals.

[0023] The aqueous phase clear liquid was analyzed by the same method as in Example 1, and the obtained separation factor was 3.052, and the ee value was 47.59%.

Embodiment 3

[0024] Embodiment 3: the extraction experiment that the concentration of ofloxacin feed liquid is 0.8g / L

[0025] Prepare 0.8g / L aqueous solution of ofloxacin as the water phase, and the organic phase as n-hexane solution. Weigh 0.0538g of D-DBTA, put it into a 50mL Erlenmeyer flask, transfer 20mL of n-hexane solution and 20mL ofloxacin aqueous solution with a concentration of 0.8g / L into the Erlenmeyer flask. Each Erlenmeyer flask was sealed and placed in a digital display water bath constant temperature oscillator THZ-82A, oscillating at a speed of 220r / min for 40min, then placed in a centrifuge tube and centrifuged at a speed of 5000r / min for 10min in a centrifuge. The lower layer was filtered, concentrated, dried and purified to obtain ofloxacin crystals.

[0026] Adopt the method with embodiment 1 to analyze aqueous phase clear liquid, experimental result shows that when feed liquid concentration is 0.8g / L, separation factor 4.175, ee value is 59.27%

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Abstract

The present invention provides a method for splitting an ofloxacin chiral drug through liquid-liquid-solid extraction. According to the present invention, the method is based on the chiral liquid-liquid extraction process, the water phase is an ofloxacin aqueous solution, the organic phase is alkane, and a dibenzoyltartaric acid derivative is adopted as solid phase particles to split the ofloxacin enantiomer through liquid-liquid-solid extraction; the method has advantages of simple operation, wide application range, low power consumption, simple equipment, continuous production and the like of the solvent extraction method, further has characteristics of good splitting effect and substantial extraction efficiency improving; with the application of the method to split the ofloxacin through the single extraction, the separation factor can be up to 5.298, and the ee value can achieve 65.61%; and with the method, the extraction distribution behaviors of the ofloxacin enantiomer in the organic phase containing the solid phase particles dibenzoyltartaric acid derivative and the water phase are researched, and a certain guide significance is provided for the development of the chiral drug splitting.

Description

technical field [0001] The invention belongs to the field of separation of chiral drugs, in particular to a method for separating ofloxacin by liquid-liquid-solid extraction using dibenzoyl tartaric acid derivatives as solid-phase particles. Background technique [0002] Chiral phenomena are very common in living organisms, and the human body itself is a large chiral environment, such as L-amino acids, D-DNA, L-monosaccharides that constitute human proteins, and many endogenous substances such as carrier enzymes and receptors. At present, more and more attention is paid to chiral drugs. There are many optically active synthetic drugs in the world, accounting for about 40% of clinically used drugs. It has the advantages of small dosage, less side effects and high curative effect. At present, the resolution methods of racemate include enzymatic method, crystallization method, chromatography and extraction resolution method. [0003] Ofloxacin [(±)-9-fluoro-2,3-dihydro-3-methy...

Claims

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Application Information

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IPC IPC(8): C07D498/06
CPCC07D498/06
Inventor 任钟旗曾勇和立超张卫东
Owner BEIJING UNIV OF CHEM TECH
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