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Preparation method for levofloxacin impurity

A technology of levofloxacin and fluorolevofloxacin, which is applied in the field of medicinal chemistry and can solve the problems of no reported preparation methods, etc.

Inactive Publication Date: 2012-11-14
ZHEJIANG STARRY PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But there is no report at home and abroad that levofloxacin also contains the levoform of ofloxacin impurity D and its preparation method

Method used

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  • Preparation method for levofloxacin impurity
  • Preparation method for levofloxacin impurity
  • Preparation method for levofloxacin impurity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment 1: Preparation of 10-fluorolevofloxacin formula (1) compound

[0021] Get 8L of levofloxacin crude product mother liquor material and place it in a 2L single-mouth rotary concentration bottle and concentrate it to dryness in stages to obtain 105g of mother liquor concentrate. Add 630ml of 95% ethanol to this concentrate and mechanically stir it, transfer it to a three-necked bottle and mechanically stir to fully reflux , hot filtration; the filter residue was repeated 5 times in this way, and the obtained filter residue was heated to reflux with 18ml of dichloromethane to dissolve and clarify, cooled and concentrated to a small volume of crystallization, filtered, and the filter residue was rinsed with absolute ethanol to obtain 500 mg of light yellow solid 10-fluorolevofloxacin, HPLC Its content was determined to be 99.5%. MS-ESI (m / z): 362[M+H] + ; 1 H NMR (400MHz, CDCl 3 :14.98(brs,1H,-COO H ,D 2 O exchange disappears), 8.71(s,1H,=C H -N-),7.49(d,J=8...

Embodiment 2

[0023] Example 2: Application of 10-fluorolevofloxacin formula (1) compound as a reference substance in HPLC

[0024] The HPLC method for analyzing the compound of 10-fluorolevofloxacin formula (1) in the raw material of levofloxacin uses a 280nm detector and a 4.0mm×15cm (3.0μm) C18 column. The mobile phase is composed of solution A: a mixed solution of buffer solution and acetonitrile (84:16) and solution B: a mixed solution of buffer solution, acetonitrile, and methanol (50:30:20).

[0025] Solution preparation:

[0026] Test solution: Accurately weigh about 10 mg of levofloxacin, place it in a 25 ml volumetric flask, dissolve it with 2 ml of acetonitrile, dissolve it by ultrasonication, dilute with water to the mark, and mix well.

[0027] Reference substance solution: Accurately weigh about 10mg of 10-fluorolevofloxacin, place it in a 25ml volumetric flask, dissolve it with 2ml of acetonitrile, dissolve it by ultrasonication, dilute to the mark with water, and mix well....

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Abstract

The invention relates to a preparation method for a levofloxacin impurity (S)-(-)-10-fluorine-2,3- dihydro-3-methyl-9-(4-methyl-1-piperazine)-7-oxo-7H- pyridine[1,2,3-de]-[1,4] benzoxazine-6-carboxylic acid in a formula (1). The prepared levofloxacin impurity provides a reference sample for qualitative and quantitative analysis of the levofloxacin impurity, and thus the quality standard of levofloxacin is improved and an important guiding significance is provided for safe medication of the levofloxacin.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and more specifically relates to an impurity (S)-(-)-10-fluoro-2,3-dihydro-3-methyl-9-(4-methanol) in the preparation process of levofloxacin The preparation method of -1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-[1,4]benzoxazine-6-carboxylic acid. Background technique [0002] Levofloxacin (levofloxacin) is a third-generation fluoroquinolone antibacterial drug, which has the characteristics of broad antibacterial spectrum, strong antibacterial effect and less toxic and side effects. Levofloxacin was developed and launched by Japan's Daiichi Pharmaceutical Co., Ltd. in 1993, and the product is now on the market in my country, Europe and the United States and many other countries. However, serious adverse reactions still occur from time to time, and the occurrence of adverse reactions is not only related to the pharmacological activity of levofloxacin itself, but also has a lot to do with the impu...

Claims

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Application Information

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IPC IPC(8): C07D498/06G01N30/02
Inventor 李奇彪石永根陈为飞应澄澄陈媛媛
Owner ZHEJIANG STARRY PHARMA