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Preparing method of moxifloxacin or slat thereof

A technology of star ester and cyclopropyl, which is applied in the field of medicinal chemistry, can solve the problems of many preparation steps, low yield, and low product yield, and achieve the effects of simple and easy-to-control process, low manufacturing cost, and high yield

Inactive Publication Date: 2012-09-19
苏州中科天马肽工程中心有限公司 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The above method has more or less disadvantages: patent EP1992626 has the problem of low product yield and needs chiral resolution; patent US5157117 and WO2008059223A2 first make the mother core into a borate chelate and then condense with the side chain reaction, the preparation process is too many, and the product yield is not high; the preparation process of the patent CN101941969 has low product purity and low yield
The deficiencies of the above-mentioned several methods increase the manufacturing cost of moxifloxacin and restrict the industrialized production of moxifloxacin

Method used

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  • Preparing method of moxifloxacin or slat thereof
  • Preparing method of moxifloxacin or slat thereof

Examples

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Effect test

Embodiment 1

[0032] Take 700 milliliters of ethanol, add 32.3 grams of 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid ethyl ester and 13.2 grams S, S-2,8-diazabicyclo[4.3.0]nonane, add 0.4 gram of anhydrous aluminum chloride catalyst, stir, add 2.5 gram of triethylamine, stir reaction at 45 ℃ of temperature control, TLC (thin layer Chromatography) to judge the reaction to the end point, cool slightly, adjust the pH value to 2-3 with 35% to 37% concentrated hydrochloric acid, control the temperature at 70°C and stir the reaction for 2 to 3 hours, cool to below 10°C to crystallize, filter, and vacuum dry The obtained product-moxifloxacin hydrochloride was 39.8 grams, with a yield of 91% and a purity of 99.2%.

Embodiment 2

[0034] Get 1300 milliliters of methanol, add 61.8 grams of 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid methyl ester and 26.4 grams S, S-2,8-diazabicyclo[4.3.0]nonane, add 0.4 g of anhydrous aluminum chloride / 0.8 g of zinc chloride catalyst, stir, add 5.0 g of triethylamine, stir at 45°C Reaction, TLC judged that the reaction reached the end point, cooled slightly, adjusted the pH value to 2~3 with 35%~37% concentrated hydrochloric acid, controlled the temperature at 70°C and stirred for 2 to 3 hours, cooled to below 10°C to crystallize, filtered, vacuum The product was dried to obtain 78.0 grams of moxifloxacin hydrochloride, with a yield of 89.0% and a purity of 99.1%.

Embodiment 3

[0036] Take 700 milliliters of ethanol, add 32.3 grams of 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid ethyl ester and 12.5 grams S, S-2,8-diazabicyclo[4.3.0]nonane, add 0.4 g of anhydrous aluminum chloride catalyst, stir, add 2.5 g of triethylamine, stir at 45°C for reaction, TLC judges the reaction to At the end point, cool slightly, use 35% to 37% concentrated hydrochloric acid to adjust the pH value to 2 to 3, control the temperature at 70°C and stir for two to three hours, cool to below 10°C to crystallize, filter, and vacuum dry to obtain the product - molybdenum hydrochloride Cifloxacin 39.5 g, yield 90.2%, purity 99.4%.

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Abstract

A preparing method of moxifloxacin or slat thereof includes that: 1-cyclopropyl-6,7-difluoro-8-methoxyl-4-oxo-1,4-dihydro-3-quinoline carboxylic acid ester and S,2-2,8-diazabicyclo(4.3.0) nonane are used as raw materials, catalysts are added into the raw materials for condensation reaction in mild condition, and before separation, condensation product moxifloxacin ester can be directly added with hydrolysis of ester group for separation to obtain moxifloxacin or slat thereof. By adopting the method, product purity is high, yield is high, the process is simple and can be controlled easily, and product manufacture cost is low. The preparing method is suitable for large-scale industrial production.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a method for preparing moxifloxacin or a salt thereof. Background technique [0002] Moxifloxacin hydrochloride (English name is moxifloxacin hydrochloride, chemical name is 1-cyclopropyl-7-(S,S-2,8diazabis[4.3.0]nonan-8-yl)-6-fluoro -8-methoxy-4-oxo-1,4-dihydro-3-quinoline carboxylic acid hydrochloride) is the fourth generation of fluoroquinolone antibacterial drugs. It has a broad-spectrum antibacterial effect and has been used as an antibacterial drug for humans and animals to effectively treat infections caused by various bacteria. Its structural formula is as follows: [0003] [0004] US5157117 and CN101514201 disclose 1-cyclopropyl-6,7-difluoro-8-methoxy-4-oxo-1,4-dihydro-3-quinoline carboxylic acid ethyl ester in the presence of zinc chloride The preparation process of preparing the corresponding ethyl borate chelate by reacting with boric acid and ace...

Claims

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Application Information

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IPC IPC(8): C07D471/04
Inventor 何达云刘世领陆晓刘中华刘俊徐国良蒋勇谢宏徐敏
Owner 苏州中科天马肽工程中心有限公司
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