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Method for preparing Moxifloxacin impurity C

A moxifloxacin and impurity technology, applied in the field of medicinal chemistry, can solve problems such as no efficient synthesis method of moxifloxacin impurity C, and achieve the effect of short synthesis route, simple operation and high purity of impurity products

Active Publication Date: 2015-09-30
NANJING YOUKE BIOLOGICAL MEDICAL RES +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In the above quality standards, the mixed control method was used for the system suitability test of the five impurities to control the impurities, but the impurity reference method was not used for quantitative control
There is no efficient synthetic method for the preparation of moxifloxacin impurity C in the existing literature

Method used

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  • Method for preparing Moxifloxacin impurity C
  • Method for preparing Moxifloxacin impurity C
  • Method for preparing Moxifloxacin impurity C

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Dissolve moxifloxacin impurity E (20.0g, 0.052mol) in 220mL of a mixed solvent of 1,4-dioxane / water with a volume ratio of 1:1, add sodium hydroxide (1.0g, 0.026mol), and wait Lower the internal temperature to 0°C, slowly add di-tert-butyl dicarbonate (Boc) dropwise 2 O (12.4g, 0.057mol) in 1,4-dioxane solution, after dropping, keep the internal temperature at 0°C for 2 hours, slowly rise to the internal temperature of 30°C, continue to stir for 12 hours, after the reaction is completed, cool down to 0 ℃, add 0.5mol / L citric acid aqueous solution dropwise to pH = 3, add dichloromethane, stir and extract, stand and separate layers, take the dichloromethane layer, concentrate to dryness, and obtain 21.4g of the compound of formula III, with a yield of 85% .

[0034] Dissolve the compound of formula III (21.4g, 0.04mol) in 100mL of anhydrous THF, add potassium hydroxide (8.9g, 0.16mol), stir evenly, wait until the internal temperature drops to 0-5°C, slowly add the ethyla...

Embodiment 2

[0040] Dissolve moxifloxacin impurity E (15g, 0.038mol) in 150mL of 1,4-dioxane / water mixed solvent with a volume ratio of 1:1, add sodium hydroxide (2.3g, 0.057mol), and wait for The temperature dropped to 5°C, and slowly added dropwise (Boc) 2 O (10.7g, 0.049mol) in 1,4-dioxane solution, after dripping, keep the internal temperature at 5°C for 2-3 hours, slowly rise to the internal temperature of 35°C, continue stirring for 12-14 hours, after the reaction is completed , cooled to 5°C, added dropwise 0.5mol / L citric acid aqueous solution to pH = 3, added dichloromethane, stirred and extracted, stood to separate layers, took the dichloromethane layer, concentrated to dryness, and obtained 15.6g of the compound of formula III, The yield is 83%.

[0041] Dissolve the compound of formula III (15.6g, 0.032mol) in 95mL of anhydrous THF, add sodium hydride (5.1g, content 60%, 0.128mol), stir evenly, wait until the internal temperature drops to 0-5°C, slowly add Ethylating reagent ...

Embodiment 3

[0047] Dissolve moxifloxacin impurity E (10 g, 0.026 mol) in 95 mL of a mixed solvent of 1,4-dioxane / water with a volume ratio of 1:1, add sodium hydroxide (1.4 g, 0.036 mol), and wait for Lower the temperature to 0~5℃, slowly add (Boc) 2 O (6.7g, 0.031mol) of 1,4-dioxane solution, after dropping, keep the internal temperature at 3°C ​​for 2.5h, slowly rise to the internal temperature of 33°C, continue stirring for 13h, after the reaction is complete, cool down to 0~5°C, add 0.5mol / L citric acid aqueous solution dropwise to pH=3, add dichloromethane, stir and extract, stand and separate layers, take the dichloromethane layer, concentrate to dryness, and obtain 10.2g of the compound of formula III. The rate is 81%.

[0048] Dissolve the compound of formula III (10.2g, 0.021mol) in 100mL of anhydrous THF, add sodium ethoxide (5.7g, 0.084mol), stir evenly, wait until the internal temperature drops to 0-5°C, slowly add the ethylating reagent dropwise Bromoethane (9.1g, 0.084mol)...

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Abstract

The invention relates to a method for preparing Moxifloxacin impurity C. The method specifically comprises the steps of enabling a Moxifloxacin impurity E, which serves as a starting raw material, to be subjected to reaction of four steps, i.e., amino Boc protection, ethylation, esterolysis and Boc protection removal in all, and finally, carrying out recrystallization operation once, thereby obtaining the high-purity Moxifloxacin impurity C refined product. The method has the characteristics that the synthesis route is short, the operation is simple, the obtained impurity product is relatively high in purity and can be applied to reference research, and the like.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method of moxifloxacin impurity C. Background technique [0002] Moxifloxacin hydrochloride (Moxifloxacin hydrochloride) chemical name: 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4αS,7αS)-octahydro-6H-pyrrole [3,4-b]pyridin-6-yl]-4-oxo-3-quinoline carboxylic acid hydrochloride, Cas No.: 151096-09-2, has the chemical structure shown in the following formula: [0003] [0004] Moxifloxacin hydrochloride is an extended-spectrum quinolone antibiotic developed by Bayer Pharmaceutical Company of Germany. It was first launched in Germany in September 1999 and was approved by FDA in December of the same year. Moxifloxacin hydrochloride has broad-spectrum antibacterial activity, especially the activity against Gram-positive, mycoplasma, chlamydia, Legionella, etc. is much better than ciprofloxacin, and is effective against anaerobic bacteria. It has ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 闵涛陆晨光车晓明张峰薛峪泉
Owner NANJING YOUKE BIOLOGICAL MEDICAL RES
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