Moxifloxacin analogue as well as preparation method and application thereof

A technology of analogues and products, applied in the field of moxifloxacin analogues and their preparation and use

Inactive Publication Date: 2017-07-07
JIANGSU TIANYISHI PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] At present, there is no report on the preparation method of impurity Y with the following structure. The purpose

Method used

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  • Moxifloxacin analogue as well as preparation method and application thereof
  • Moxifloxacin analogue as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1 Preparation of moxifloxacin analogue Y.

[0026] Add 2.00g of moxifloxacin, 20.00ml of dichloromethane, 0.61g of triethylamine to a 100ml flask, (Boc) 2 O1.31g, stirred at room temperature for 3h, distilled off the solvent, and purified by column chromatography; the product was dissolved in 20ml of fresh dichloromethane, and 1 drop of DMF was added dropwise into SOCl 2 0.5ml, reflux reaction for 1h, spin dry the solvent; dissolve the residue with 15ml fresh dichloromethane, slowly drop the solution into a solution of 5ml dichloromethane+2ml absolute ethanol, reflux reaction for 1h, spin dry the solvent; The residue was added to 10ml of a mixture of trifluoroacetic acid: dichloromethane = 1:1, reacted at room temperature for 2 hours, separated by column chromatography, and the target product moxifloxacin analog Y was collected to obtain 0.89g.

Embodiment 2

[0027] Example 2 Preparation of moxifloxacin analogue Y.

[0028] Add moxifloxacin 2.00g, dichloromethane 20.00ml, triethylamine 0.70g, (Boc) to a 100ml flask 2 O1.31g, stirred at room temperature for 5h, evaporated the solvent under reduced pressure; dissolved the residue with 20ml of fresh dichloromethane, added 2 drops of DMF, the temperature dropped to 0°C, slowly added 1.00g of oxalyl chloride dropwise, and the dropwise To room temperature, stirred for 3h. The solvent was spin-dried under reduced pressure; the residue was dissolved with 15ml of fresh dichloromethane, the solution was slowly dropped into a solution of 5ml dichloromethane+2ml absolute ethanol, the reaction was refluxed for 1h, and the solvent was spin-dried; the residue was added to Add 2ml of concentrated hydrochloric acid dropwise to 10ml of methanol, heat up to 70°C for 4 hours, cool and filter, refine the wet product with 4ml of ethanol, filter for crystallization, and dry to obtain 0.71g of moxifloxac...

Embodiment 3

[0029] Example 3 HPLC separation of moxifloxacin analogues and moxifloxacin.

[0030] Chromatographic conditions.

[0031] project parameter project parameter chromatography Shimadzu HPLC chromatography system, LC-2010AHT, equipped with Class-VP workstation Column model Phenyl column, 250×4.6mm, 5μm flow rate 1.3ml / min pre-column Phenyl column Detection wavelength 293nm Column temperature 45℃ mobile phase Aqueous solution (0.5g / L tetrabutylammonium hydrogen sulfate, 1.0g / L potassium dihydrogen phosphate, 3.4g / L phosphoric acid)-methanol (72:28) Solvent A Aqueous solution of 0.5g / L tetrabutylammonium hydrogen sulfate, 1.0g / L potassium dihydrogen phosphate, 0.050g / L anhydrous sodium sulfite, 2ml / L phosphoric acid

[0032] Use solvent A to prepare samples of the test solution containing about 1 mg of moxifloxacin hydrochloride and 0.3 mg of moxifloxacin analogue Y per 1 ml, as attached figure 1 , the retention time of...

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PUM

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Abstract

The invention discloses a preparation method and application of a moxifloxacin analogue Y shown in a figure. The preparation method comprises the following steps: taking moxifloxacin as a raw material, firstly protecting a protection group on a secondary amino group on a 7-position side chain, then performing acyl chlorination and ethyl ester esterification on a 3-bit carboxyl group and removing an amino-group protective agent to obtain the moxifloxacin analogue Y. The preparation of the analogue Y provides a reference substance for moxifloxacin hydrochloride-related substances.

Description

technical field [0001] The invention discloses a moxifloxacin analogue Y as well as its preparation method and application. Background technique [0002] Moxifloxacin hydrochloride is the fourth generation of fluoroquinolones developed by Bayer AG in Germany. Its chemical name is 1-cyclopropyl-6-fluoro-7-([S,S]-2,8-diazabicyclo[4.3 .0] Non-8-yl)-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylate hydrochloride. This product was first launched in Germany in September 1999, and in the United States in December of the same year. It is used for the treatment of acute sinusitis, acute exacerbation of chronic bronchitis, community-acquired pneumonia, and uncomplicated skin infections and skin and soft tissue infections. This product is characterized by almost no photosensitivity reaction, and is a better drug for treating respiratory tract infections. [0003] The quality standards of moxifloxacin hydrochloride have been recorded in the European Pharmacopoeia and the United State...

Claims

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Application Information

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IPC IPC(8): C07D471/04G01N30/02
CPCC07D471/04G01N30/02Y02P20/55
Inventor 傅雪琦沈羽君
Owner JIANGSU TIANYISHI PHARMA
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