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The preparation method of zabufloxacin

A Zarbofloxacin and reaction technology, which is applied in organic chemistry, bulk chemical production, etc., can solve the problems that it is not suitable for the preparation of Zarbofloxacin, and achieve the effects of mild reaction conditions, high yield and high purity

Inactive Publication Date: 2021-03-02
沈阳林特制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But the preparation technology of above-mentioned disclosed chelation method is not suitable for preparing Zarbofloxacin

Method used

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  • The preparation method of zabufloxacin
  • The preparation method of zabufloxacin
  • The preparation method of zabufloxacin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid-O 3 ,O 4 -Preparation of diacetate boronic acid (main ring chelate shown in formula I)

[0036] The reaction equation is as follows:

[0037]

[0038] Feeding ratio:

[0039]

[0040] crafting process:

[0041] Under stirring, add 17.34g of acetic anhydride to the reaction bottle, raise the temperature to 50°C, control the temperature at 50°C, add 3.41g of boric acid to the reaction solution in batches, after the addition is complete, raise the temperature, control the temperature at 135°C, and react for 1.5 h, the temperature of the reaction solution was lowered, and when the temperature dropped to 65°C, 1.65g of tetraethylammonium chloride and 14.1g of the main ring shown in formula V were added to the reaction solution, the temperature was controlled at 65°C, and the reaction was carried out for 2h. Cool down to 5°C, add 100g of water at 0°C, react at 0°C for 0....

Embodiment 2

[0042] Example 2 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid-O 3 ,O 4 -Preparation of diacetate boronic acid (main ring chelate shown in formula I)

[0043] Feeding ratio:

[0044]

[0045] crafting process:

[0046] Under stirring, add 18.87g of acetic anhydride to the reaction flask, raise the temperature to 55°C, control the temperature at 55°C, add 3.72g of boric acid to the reaction solution in batches, after the addition is complete, raise the temperature, control the temperature at 140°C, and react for 1.5 h, the temperature of the reaction solution was lowered, and when the temperature dropped to 65°C, 2.475g of tetraethylammonium chloride and 14.1g of the main ring shown in formula V were added to the reaction solution, the temperature was controlled at 67°C, and the reaction was carried out for 1h. Cool down to 10°C, add 130g of water at 5°C, react at 5°C for 0.5h, filter, wash the filter cake with 130g of water at 5°C...

Embodiment 3

[0047]Example 3 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid-O 3 ,O 4 - the preparation of di-tert-butoxycarboxylic acid boronic acid (the main ring chelate shown in formula I)

[0048]

[0049] Feeding ratio:

[0050]

[0051] crafting process:

[0052] Under stirring, add 38.368g of di-tert-butyl dicarbonate to the reaction bottle, raise the temperature to 52°C, control the temperature at 52°C, add 3.41g of boric acid to the reaction solution in batches, after the addition is complete, raise the temperature, and control the temperature at 136°C ℃, reacted for 1.5h, lowered the temperature of the reaction solution, when the temperature dropped to 65 ℃, added 1.98g of tetraethylammonium chloride and 14.1g of the main ring shown in formula V to the reaction solution, controlled the temperature at 66 ℃, and reacted for 1.5 h, cool the reaction solution to 6°C, add 100g of water at 2°C, react at 3°C ​​for 0.5h, filter, wash the f...

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Abstract

The invention provides a preparation method of zabufloxacin, the preparation method comprising: after reacting the main ring chelate compound shown in formula I and the side chain shown in formula II in an aprotic solvent, dechelation part, generate the intermediate shown in formula III, remove the protective group from the intermediate shown in formula III, and generate zabofloxacin, the zabofloxacin prepared by the process route provided by the present invention does not need further purification, and the yield High, high purity, suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of antibacterial drug synthesis, in particular to a preparation method of zabufloxacin. Background technique [0002] Quinolones are a class of synthetic antibacterial drugs with quinoline or naphthyridine structures in their molecules. The common feature of this class of drugs is that they block DNA replication by inhibiting DNA gyrase to produce antibacterial effects, and have high selectivity for bacteria. , the safety of people is great, so the discovery and development of quinolones has created a new era of synthetic antibacterial drugs. [0003] Norfloxacin was successfully synthesized in 1979. The structural feature of this type of drug is that there is a fluorine atom at the -6 position of the quinolone mother nucleus. Subsequently, a series of new quinolones containing fluorine were synthesized, collectively called fluoroquinolones. Wide, strong antibacterial effect and good tolerance than other synthetic an...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/00
CPCC07D519/00Y02P20/55
Inventor 权奇哲林虎何镭徐明黄荣涛李军业
Owner 沈阳林特制药有限公司