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Marbofloxacin preparation method

A technology for marbofloxacin and compound, which is applied in the field of medicinal chemistry, can solve the problems of unfavorable chemical reagents, excessively long reaction route, expensive chemical reagents and the like, and achieves the effects of novel synthesis method, high efficiency and simple operation.

Active Publication Date: 2017-11-24
WISDOM PHARM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] In summary, in the existing synthetic route of marbofloxacin, there are various deficiencies, such as expensive chemical reagents, long reaction route, use of chemical reagents that are unfavorable for industrialized production, etc., the inventors After research and experiments, a new method of preparing Marbofloxacin was invented

Method used

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Examples

Experimental program
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Effect test

Embodiment 1

[0026] Example 1: Preparation of 1,1,1-trichloro-4-(4-methylpiperazin-1-yl)but-3-en-2-one

[0027] (E)-1,1,1-trichloro-4-methoxybut-3-en-2-one (formula I, R=Me) (10.18g, 50mmol), 1-methylpiperazine (6.0 g, 60mmol) and mesitylene (50mL) was heated to reflux temperature and stirred for 6 hours, the system was naturally cooled to room temperature, the organic solvent was removed under high vacuum and reduced pressure, and the residue (14.2g, crude product, unpurified) was untreated purified and used directly in the next reaction.

Embodiment 2

[0028] Example 2: (6,8-difluoro-7-(4-methylpiperazin-1-yl)-4-oxo-3-(2,2,2-trichloroacetyl)quinoline-1 Preparation of (4H)-yl) ethyl carbamate (formula VII)

[0029] Under nitrogen protection, the product of Example 1 (14.2 g, not purified, directly used) was dissolved in toluene (120 mL), then triethylamine (72 mL, 514 mmol) was added to the system, and the system was heated to reflux temperature. At reflux temperature, a solution of 2,3,4,5-tetrafluorobenzoyl chloride (16 g, 75.3 mmol) in toluene (60 mL) was slowly added dropwise to the reaction system. After the dropwise addition, the system was refluxed for 30 minutes, and then the system was slowly cooled to 60°C, and filtered hot. Filtrate is transferred in the 500ml reaction bottle, then adds ethyl carbazate (formula V, R 2 = Et) (6.25 g, 60 mmol). After the addition, the system was reacted at a temperature of 60-65° C. for 12 hours. Slowly add H to the reaction system 2 O (150 mL) was used to quench the reaction, a...

Embodiment 3

[0030] Example 3: 1-amino-6-fluoro-8-hydroxyl-7-(4-methylpiperazin-1-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ( Preparation of formula VIII)

[0031] The solid obtained in Example 2 (21.2g) was placed in a 200ml reaction flask, ethanol (50mL) and water (50mL) were added to the reaction system, and the system was heated to reflux. Under the condition of reflux, an aqueous solution (30 mL) of KOH (7.0 g) was slowly added to the system, and after the dropwise addition, the system was kept under reflux for 96 hours. The system was naturally cooled to room temperature, and the system was added with H 2 O (100mL) and CH 2 Cl 2 (50ml), after stirring, let it stand to separate the organic phase, and then use CH 2 Cl 2 Extract twice (2 x 50 mL). Use hydrochloric acid to adjust the system to acidity (pH=3-4) in the water phase, and then use CH 2 Cl 2 Extracted twice (2×100 mL), combined the organic phases, and removed the organic solvent under reduced pressure to obtain ...

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Abstract

The invention relates to a marbofloxacin preparation method, a multi-step reaction is continuously carried out, the efficiency is high, and the preparation method has the advantages that the synthesis route is short, all the reagents are conventional and easy for commercial purchase, and the operation is simple.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry and relates to a preparation method of veterinary drug marbofloxacin. Background technique [0002] Marbofloxacin (Marbofloxacin) is a veterinary fluoroquinolone antibacterial drug, the chemical name is 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2, 3-dihydro-7H-pyridine[3,2,1-ij][4,1,2]benzoxadiazine-6-carboxylic acid, first developed by Roche, and manufactured by Vetoquinol (France Weilong) The company developed it further and launched it in Europe in 1995. Marbofloxacin is another third-generation quinolone antibacterial drug following Enrofloxacin, Danofloxacin, Sarafloxacin, etc., which has a wide range of antibacterial activities and has Very good kinetic characteristics, strong bactericidal power, fast absorption, wide distribution in the body, no cross-resistance with other antibacterial drugs, easy to use, and small adverse reactions. Pharmacokinetic studies have shown that m...

Claims

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Application Information

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IPC IPC(8): C07D498/06C07D295/145C07D215/58
CPCC07D215/58C07D295/145C07D498/06
Inventor 邹平储玲玲王平张新刚邱小龙胡林苟少华王东辉邓贤明游正伟江中兴彭陟辉
Owner WISDOM PHARM CO LTD
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