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A kind of synthetic method of levofloxacin isomer compound

A levofloxacin and synthetic method technology, applied in the field of medicinal chemistry, can solve problems such as chemical synthesis methods of compounds that have not been reported in the literature, and achieve the effects of improving quality standards, easy-to-obtain starting materials, and simple processes

Active Publication Date: 2019-03-22
JIANGSU HAICI BIOLOGICAL PHARMA CO LTD OF YANGTZE RIVER PHARMA GRP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, there is no chemical synthesis method of this compound reported in the literature

Method used

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  • A kind of synthetic method of levofloxacin isomer compound
  • A kind of synthetic method of levofloxacin isomer compound
  • A kind of synthetic method of levofloxacin isomer compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Preparation of Example 1 Compound M1

[0044] Add (-)-(S)-9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de] into a 250mL three-neck flask - 4.5g (14.5mmol) of ethyl 1,4-benzoxazine-6-carboxylate, 10mL of concentrated sulfuric acid, control the reaction temperature not to exceed 0°C, and slowly add 2.21g (21.8mmol) of potassium nitrate. Keep the temperature at 0-25° C. for 2 hours. After the reaction, add 100 mL of water to the reaction solution, the solid precipitates and is filtered. After drying, 4.8 g of the product is obtained as a light yellow solid with a yield of 93%.

Embodiment 2

[0045] The preparation of embodiment 2 compound M1

[0046] Add (-)-(S)-9,10-difluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de] into a 250mL three-neck flask 4.0 g (14.5 mmol) of methyl 1,4-benzoxazine-6-carboxylate, 10 mL of concentrated sulfuric acid, and 1.68 g (21.8 mmol) of sodium nitrate was added slowly while the reaction temperature was controlled not to exceed 0°C. Keep the temperature at 0-25° C. for 1 hour. After the reaction is monitored by LCMS, 100 mL of water is added to the reaction solution. The solid precipitates and is filtered. After drying, 4.5 g of the product is obtained as a light yellow solid with a yield of 87%.

Embodiment 3

[0047] The preparation of embodiment 3 compound M2

[0048] Add 3.4 g of compound M1 (9.6 mmol), 20 mL of DMF, and 2.88 g (28.80 mmol) of N-methylpiperazine into a 250 mL three-necked flask. Heated to 30°C and kept at this temperature for 12 hours. After the reaction was completed, 100 mL of water was poured into the reaction solution, filtered and the filter cake was washed with water. After vacuum drying, 3.6 g of the product was obtained as a light yellow solid with a yield of 86%.

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Abstract

The invention provides a synthesis method of a levofloxacin isomer (-)-(S)-3-methyl-10-chloro-2, 3-dihydro-9-(4-methyl-1-piperazinyl)-7-oxo-7H-pyridino-[1, 2, 3-de]-[1, 4] benzoxazine-6-carboxylic acid. The method comprises the following steps: a, preparation of a compound M1: taking levofloxacin acid ester as a raw material, and performing nitratlon reaction in a concentrated sulfuric acid, nitric acid or nitrate condition; b, preparation of a compound M2: adding N-methyl piperazine into the compound M1, so as to perform piperazine retraction reaction; c, preparation of a compound M3: reducing nitro in the compound M2 into amino with a reducing agent; d, preparation of a compound M4: converting the amino in the compound M3 into hydrogen atom; e, preparation of the levofloxacin isomer: performing esterolysis on the compound M4 in an acidic or alkaline condition. The invention provides a novel synthesis method of the levofloxacin isomer, thereby providing a preparation method of a comparison product for the quality research of levofloxacin, and further providing important guiding significance for the safe medication of levofloxacin.

Description

technical field [0001] The present invention relates to the field of medicinal chemistry, in particular to a (-)-(S)-3-methyl-10-fluoro-2,3-dihydro-9-(4-methyl-1-piperazinyl) -Synthetic method of 7-oxo-7H-pyrido[1,2,3-de]-[1,4]benzoxazine-6-carboxylic acid. Background technique [0002] Fluoroquinolones have achieved great success in clinical anti-infection therapy due to their broad-spectrum, high-efficiency, and low-toxicity antibacterial properties. Among them, ofloxacin, levofloxacin, and levofloxacin hydrochloride are excellent representatives. [0003] Levofloxacin developed by Japan's Daiichi Sankyo Pharmaceutical Co., Ltd. is an excellent variety with a wide market share. Its chemical name is: (-)-(S)-3-methyl-9-fluoro-2,3-dihydro-10 -(4-Methyl-1-piperazinyl)-7-oxo-7H-pyrido[1,2,3-de]-[1,4]benzoxazine-6-carboxylic acid), for half Hydrate, the structure is as follows: [0004] [0005] The synthesis process of levofloxacin is very mature, and there are many rep...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D498/06
CPCC07D498/06
Inventor 刘宏远王庆辉牛明玉刘文超周如彬
Owner JIANGSU HAICI BIOLOGICAL PHARMA CO LTD OF YANGTZE RIVER PHARMA GRP
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