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Stable moxifloxacin hydrochloride compound and preparation method thereof

A technology of moxifloxacin hydrochloride and its compound, which is applied in the field of pharmaceuticals in the field of medicine, can solve the problems of unfavorable industrial production, low adoption yield, cumbersome operation, etc., and achieve the effect of simplified operation, simple operation, and simplified process operation

Inactive Publication Date: 2012-08-01
TIANJIN HANKANG PHARMA BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its yield is not high and the operation is cumbersome, and it uses poisonous boric acid and anhydride as reaction reagents
CN101830921 uses phenylboronic acid to directly form a chelate with compound 6, although the operation is simplified, but its cost is high, which is not conducive to industrial production

Method used

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  • Stable moxifloxacin hydrochloride compound and preparation method thereof
  • Stable moxifloxacin hydrochloride compound and preparation method thereof
  • Stable moxifloxacin hydrochloride compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0083] Add 187g of 3-methoxy-2,4,5-trifluorobenzonitrile, 97.5g of zinc and 1L of tetrahydrofuran into a 3L three-necked flask, add 8.6g of p-toluenesulfonic acid under stirring, and stir at room temperature for 0.5h. Heated to reflux, and slowly added dropwise 217.1 g of ethyl bromoacetate. React under reflux for 2 hours, cool to room temperature, add 500mL 6M hydrochloric acid and 100mL water successively, stir for 2h, cool to 5°C, a large amount of solid precipitates, filter, rinse with 100mL ethanol, and blow dry at 40°C to obtain 223.5g3- Methoxy-2,4,5-trifluorobenzoyl ethyl acetate, yield 80.9%, purity 98.5%.

Embodiment 2

[0085] Add 220g of ethyl 3-methoxy-2,4,5-trifluorobenzoylacetate, 1.1L of methanol and 142.8g of N,N-dimethylformamide dimethyl acetal into a 3L three-necked flask, and react at room temperature for 2h. TLC showed that the reaction was complete, and concentrated under reduced pressure to obtain 270 g of ethyl 3-dimethylamine-2-(3-methoxy-2,4,5-trifluorobenzoyl)acrylate. Dissolve 270g of ethyl 3-dimethylamine-2-(3-methoxy-2,4,5-trifluorobenzoyl)acrylate in 1.35L of dichloromethane for later use.

Embodiment 3

[0087] Add 54.7g cyclopropylamine and 1L dichloromethane into a 5L three-necked flask, add 3-dimethylamine-2-(3-methoxy-2,4,5-trifluorobenzoyl)acrylic acid dropwise at room temperature The dichloromethane solution of ethyl ester was stirred for 1 h, and the reaction was stopped as detected by TLC that the reaction was complete. Add 2L of water to the reaction solution, stir for 20 minutes, let stand for liquid separation, wash the organic phase with 1L of 10% aqueous sodium bicarbonate solution, and separate the liquids. The aqueous phases were combined, and the aqueous phase was extracted with 1L of dichloromethane, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to dryness to obtain 280.5g of 3-cyclopropylamine-2-(3-methoxy-2,4, 5-Trifluorobenzoyl) ethyl acrylate. Dissolve ethyl 3-cyclopropylamine-2-(3-methoxy-2,4,5-trifluorobenzoyl)acrylate in 3 L of DMSO for later use.

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PUM

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Abstract

The invention discloses a moxifloxacin hydrochloride compound, which is prepared by the steps of: performing Reformatsky reaction on 3-methoxyl-2,4,5-trifluoro benzonitrile to obtain ethyl 3-methoxyl-2,4,5-trifluoro benzoyl acetate, performing enamine formation, amine exchange, nucleophilic substitution, hydrolysis and chelating to obtain (8-methoxyl-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate) boron difluoride, and performing nucleophilic substitution reaction to obtain moxifloxacin hydrochloride. The preparation method of moxifloxacin hydrochloride compound has the benefits that the operation is easy and simple, and the intermediates obtained in each step are high in purity; the reaction is sufficient, the subsidiary reactions are few, and the purification is easy; and the reaction steps are reduced and the industrialized production is easy to realize.

Description

technical field [0001] The invention relates to medicines in the field of medicine, in particular to a moxifloxacin hydrochloride compound with good stability and a preparation method thereof. Background technique [0002] With the widespread use and even abuse of antibacterial agents, bacterial drug resistance is increasing year by year. Drug-resistant bacterial infections not only seriously endanger human health, but also become a thorny problem worldwide. It is reported that about 2 million nosocomial infections occur annually among hospitalized patients in the United States, and about 90,000 of them die. More than 70% of hospital-acquired infections have developed resistance to commonly used antibacterial drugs in clinical practice. Therefore, accelerating research and development can effectively deal with severe infections and drug resistance caused by Gram-positive bacteria, especially methicillin-resistant Staphylococcus aureus (MRSA). Oral antibacterial drugs for no...

Claims

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Application Information

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IPC IPC(8): C07D471/04
Inventor 严洁王华
Owner TIANJIN HANKANG PHARMA BIOTECH
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