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Marbofloxacin synthesizing method

A technology of marbofloxacin and a synthesis method, applied in the direction of organic chemistry and the like, can solve the problems of unfriendly environment, expensive reagents, low yield and the like, and achieve the effects of low price, improved one-time yield and high product purity

Active Publication Date: 2017-12-29
ZHEJIANG GUOBANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] There are three preparation methods involved in this method, the most commonly used preparation method is the first one, which is generally adopted by domestic enterprises, but the most prominent problems of the first one are that the three wastes are serious, the environment is extremely unfriendly, and the recycling Rate is around 32%
[0015] In summary, in the present marbofloxacin synthesis route, there are various problems, either the environment is unfriendly, the yield is low, the reagent is expensive, and the cost is high. In view of this, the inventor, through research, Invented a new synthetic route, and this case arose from it

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] In the four-necked flask, add 30.0g (0.1336mol) of 2,4,5-trifluoro-3-methoxy-benzoyl chloride (compound (2)) and 20.2g (0.2004mol) of triethylamine, add After completion, control at 47°C, add 21.2g (0.1480mol) of N,N-dimethylaminoethyl acrylate (compound 3) dropwise, after dropwise addition, control the internal temperature at 89°C to keep the reaction, keep warm for 1h, finish keeping warm, cool down to At 30°C, add 100g of ethyl acetate to raise the temperature and reflux, cool to 0°C, perform crystal suction filtration, and dry the filter cake to obtain compound (4), weighing 42.3g (95.6% yield, 98.3% chromatographic content).

Embodiment 2

[0042] In the four-neck flask, add 30.0g (0.1336mol) of 2,4,5-trifluoro-3-methoxy-benzoyl chloride (compound (2)) and 29.9g (0.1400mol) of tri-n-butylamine, After the addition, control the temperature at 11°C, add 22.9g (0.1600mol) of N,N-dimethylaminoethyl acrylate (compound 3) dropwise, after the dropwise addition, control the internal temperature at 53°C to keep the reaction, keep it warm for 1h, finish keeping it warm, and then cool down To 30°C, add 100g of ethyl acetate to raise the temperature and reflux, cool to 0°C, carry out suction filtration for crystallization, and dry the filter cake to obtain compound (4), 41.5g by weighing (93.8% yield, 99.0% chromatographic content).

Embodiment 3

[0044] Add 30.0g (0.1336mol) of 2,4,5-trifluoro-3-methoxy-benzoyl chloride (compound (2)) and 47.4g (0.1340mol) of tri-n-octylamine in the four-necked flask, After the addition, control the temperature at 21°C, add 19.3g (0.1350mol) of N,N-dimethylaminoethyl acrylate (compound 3) dropwise, after the dropwise addition, control the internal temperature at 72°C to keep the reaction, keep warm for 1h, finish keeping warm, then cool down To 30°C, add 100g of ethyl acetate to raise the temperature and reflux, cool to 0°C, carry out suction filtration for crystallization, and dry the filter cake to obtain compound (4), 42.1g by weighing (95.1% yield, 99.1% chromatographic content).

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Abstract

The invention belongs to the technical field of antibacterial heterocyclic compounds or pharmaceutical preparations with specific treatment activity and relates to a marbofloxacin synthesizing method. 2,4,5-trifluoro-3-methoxy-benzoyl chloride serves as a starting material for preparing marbofloxacin by grafting, amination, cyclization, piperazine condensation, hydrolysis, re-cyclization, alkali dissolution and acid regulation. The marbofloxacin synthesizing method applied to marbofloxacin preparation has advantages of high yield, mild reaction conditions, low pollution and the like.

Description

technical field [0001] The invention relates to a synthesis method of marbofloxacin, which belongs to the technical field of antibacterial heterocyclic compounds or pharmaceutical preparations with specific therapeutic activity. Background technique [0002] Marbofloxacin was developed by Roche in Switzerland and further developed by Vetoquinol. It was launched in Britain and France in 1995. Its structural formula is as follows: [0003] [0004] This product has strong antibacterial effect, long elimination half-life and close to 100% bioavailability. For dogs, cats and cows respiratory diseases and sow mastitis, metritis and agalactia syndrome. [0005] At present, there are mainly two types of methods for the synthesis of marbofloxacin, one using 2,3-difluoro6-nitrophenol as a raw material, and the other using 2,3,4,5-tetrafluorobenzoic acid as a raw material for the reaction preparation. [0006] In Bayer's world patent WO 2011061292 A1, there is a more detailed d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D498/06
CPCC07D498/06
Inventor 蒋狄锋邱家军姚礼高侯仲轲
Owner ZHEJIANG GUOBANG PHARMA
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