Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

A method for preparing moxifloxacin impurity b and impurity d

A technology for moxifloxacin and impurities, which is applied in the field of medicinal chemistry, can solve problems such as an efficient synthesis method for impurity B of moxifloxacin, which is not seen, and achieve the effects of short synthesis route and reduction of by-products.

Active Publication Date: 2016-05-04
NANJING YOUKE BIOLOGICAL MEDICAL RES +2
View PDF4 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In the above-mentioned standards, the system adaptability test of the 5 kinds of impurities was carried out in the way of mixed control to control the impurities, but the impurity reference method was not used for quantitative control
There is no efficient synthesis method for preparing moxifloxacin impurity B and impurity D in the existing literature

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A method for preparing moxifloxacin impurity b and impurity d
  • A method for preparing moxifloxacin impurity b and impurity d
  • A method for preparing moxifloxacin impurity b and impurity d

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0039] The preparation of embodiment 1 formula III compound

[0040] Stir and heat the mixture of 2,3,4-trifluoro-5-methoxybenzoic acid (82.5g, 0.4mol) and 350mL of thionyl chloride, and add about 1mL of catalytic amount of dimethylformamide DMF dropwise. Reflux at 90-95°C for 2.5 hours, concentrate the reaction solution to dryness, and obtain 86.6 g of a yellow oil (Formula III), which is dissolved by adding about 80 mL of anhydrous toluene to obtain an acid chloride solution, which will be used in the next reaction.

Embodiment 2

[0041] The preparation of embodiment 2 formula IV compound

[0042] In the mixture of magnesium chips (14.4g, 0.6mol) and absolute ethanol 56mL, add 7.2g of carbon tetrachloride and stir evenly; when there are bubbles in the mixture, slowly add diethyl malonate ( 76.8g, 0.48mol) mixed with toluene 180mL and absolute ethanol 50mL, control the temperature at 55-60°C for 2-3 hours, cool down to 0-5°C, slowly add the acid chloride (Formula III) solution in the step dropwise, After dropping, raise the temperature to 30-35°C to react for 2 hours. After the reaction is completed, slowly add 100 mL of 1 mol / L dilute hydrochloric acid dropwise, stir for 0.5 hours, let stand to separate layers, take the toluene layer, remove the toluene after drying, and obtain 123 g of oil (formula IV compound). MS (ESI+): 349.3 [M+H] +

Embodiment 3

[0043] The preparation of embodiment 3 formula V compound

[0044] Dissolve 123g of the compound of formula IV in 100mL of DMF, add 600mL of 1.5% p-toluenesulfonic acid aqueous solution, stir at 100-110°C for 10h, after the reaction is completed, cool down to room temperature, add 300mL of ethyl acetate and stir for 0.5h, let stand to separate layers, take acetic acid The ethyl acetate layer was dried and the ethyl acetate was removed to obtain 107 g of an oil (compound of formula V).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a method for preparing moxifloxacin impurities B and D. The method comprises that 2,3,4-trifluoro-5-methoxybenzoic acid as an initial raw material undergoes a series of reactions to produce the moxifloxacin impurity D, the moxifloxacin impurity D is transformed into the moxifloxacin impurity B, the moxifloxacin impurity B is subjected to a recrystallization process to form the high-purity moxifloxacin impurity B pure solid. The method has a short synthesis route and simple processes, can produce high-purity impurity products (having HPLC purity of 99.6-99.7%) and can be used for reference substance research.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a method for preparing moxifloxacin impurity B and impurity D. Background technique [0002] Moxifloxacinhydrochloride (Moxifloxacinhydrochloride) chemical name: 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[(4αS,7αS)-octahydro-6H-pyrrolo [3,4-b]pyridin-6-yl]-4-oxo-3-quinolinecarboxylic acid hydrochloride, CasNo.: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 bacteri...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 闵涛车晓明陆晨光朱素华薛峪泉张峰
Owner NANJING YOUKE BIOLOGICAL MEDICAL RES
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com