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Quinolone analogue as well as preparation method and application thereof

A technology of analogues and quinolones, which is applied in the field of medicinal chemistry, can solve the problems such as no one discloses the preparation method of the compound, impurity control, etc., and achieve the effect of simple and easy preparation method, improved quality and improved safety

Pending Publication Date: 2022-03-01
CHANGZHOU FANGYUAN PHARMA +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] However, the existing detection and analysis methods for moxifloxacin hydrochloride do not precisely control this impurity, and no one discloses the preparation method of the compound

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1）

[0036] The structural formula of the quinolone analog to be prepared in this embodiment is as follows:

[0037] ,

[0038] Name it 1-cyclopropyl-7-(S,S-2,8-diazo-bicyclo[4.3.0]nonan-2-yl)-6-fluoro-8-methoxy-1, 4-Dihydro-4-oxo-3-quinolinecarboxylic acid, see the synthetic route figure 1 , including the following steps:

[0039] ① Preparation of compound 1, the reaction formula is as follows:

[0040] .

[0041] In a reaction flask, 10 g of S,S-2,8-diazo-bicyclo[4.3.0]nonane was dissolved in 40 mL of ethyl acetate, and then 8.8 g of triethylamine was added to the ethyl acetate to disperse evenly.

[0042] Dissolve 19g of di-tert-butyl dicarbonate in 200mL of ethyl acetate, and then add it dropwise into the reaction flask under stirring. The reaction temperature is 30-40°C. After the reaction, concentrate under reduced pressure (temperature 40°C-50°C, pressure -0.08~-0.1MPa).

[0043] The concentrated product was dissolved in 50mL of dichloromethane, separated and purif...

Embodiment 2）

[0060] All the other preparation methods of the quinolone analogs of the present embodiment are the same as in Example 1, except that:

[0061] In step ①, in a reaction flask, dissolve 10 g of S,S-2,8-diazo-bicyclo[4.3.0]nonane in 50 mL of tetrahydrofuran, and add 6.4 g of diethylamine to disperse evenly.

[0062] After dissolving 19g of di-tert-butyl dicarbonate in 20mL of tetrahydrofuran, it was added dropwise to the reaction system under stirring. The reaction temperature was 30-40°C. After the dropwise addition, continue to stir and react at 30-40°C for 4-5h.

[0063] After purification, 4.0 g of compound 1 was obtained as a solid.

Embodiment 3）

[0065] All the other preparation methods of the quinolone analogs of the present embodiment are the same as in Example 1, except that:

[0066] In step ①, in a reaction flask, dissolve 20 g of S,S-2,8-diazo-bicyclo[4.3.0]nonane in 40 mL of ethyl acetate, and add 14.3 g of N-methylimidazole to disperse evenly.

[0067] After dissolving 41.5g of di-tert-butyl dicarbonate in 20mL of ethyl acetate, it was added dropwise to the reaction system while stirring. The reaction temperature was 30-40°C.

[0068] After purification, 8.3 g of compound 1 was obtained as a solid.

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Abstract

The invention discloses a quinolone analogue and a preparation method and application thereof.The preparation method comprises the steps that S, S-2, 8-diazo-bicyclo [4.3. 0] nonane is dissolved in an organic solvent, and organic alkali is added; dissolving di-tert-butyl dicarbonate in an organic solvent, and dropwise adding into the reaction system to react to obtain a compound 1; dissolving the compound 1, slowly adding sodium hydride at 0-10 DEG C, and uniformly dispersing; the preparation method comprises the following steps: adding a compound 1 into a reaction system, dropwise adding a 1-cyclopropyl-6, 7-difluoro-8-methoxy-1, 4-dihydro-4-oxo-3-quinoline carboxylic acid solution into the reaction system, and reacting to obtain a compound 2; and dissolving the compound 2, and adding acid for reaction to obtain a compound 3, namely the target quinolone analogue. The preparation method of the quinolone analogue is simple and easy to implement, and the quinolone analogue can be prepared on a large scale. When the quinolone analogue is used for detecting related substances of moxifloxacin hydrochloride and preparations thereof, the quality of moxifloxacin hydrochloride can be further improved, the safety is improved, and the risk of medication is reduced.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a quinolone analogue and a preparation method and application thereof. Background technique [0002] Moxifloxacin hydrochloride is the fourth-generation quinolone antibiotic developed by Bayer AG of Germany. It was launched in Germany in September 1999 and was approved by FDA in the United States in December of the same year. Its mechanism of action is a DNA topoisomerase inhibitor, and its antibacterial activity in vitro is significantly better than other third-generation fluoroquinolones. [0003] The chemical structure of moxifloxacin hydrochloride is obviously different from other fluoroquinolones in that a methoxy group is introduced on the 8-position carbon atom of its molecular structure. The antibacterial activity of negative bacteria also enhances the antibacterial activity against Gram-positive bacteria and atypical pathogens such as mycoplasma, chlamydia...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04G01N30/06G01N30/02
CPCC07D471/04G01N30/06G01N30/02
Inventor 刘昕钱军王海东蒋艳君曹清源陈敏
Owner CHANGZHOU FANGYUAN PHARMA
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