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

1,4-dioxo-2-(1-ethoxy)-3-hydroxymethyl-sulfaquinoxaline and preparation method and application thereof

A technology of ethoxycarbonyloxymethyl and quinoxaline, which is applied in the field of 1,4-dioxo-2--3-hydroxymethyl-quinoxaline and preparation, can solve rough detection and cannot accurately reflect acetomethyl Quine metabolism, adverse pharmacokinetics of methaquine and its residue elimination rules, etc., to achieve the effects of high purity, high reaction yield, and cheap and easy-to-obtain raw materials

Inactive Publication Date: 2012-07-04
GENIFARM LAB INC +1
View PDF1 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, relying solely on the detection results of a primary metabolite cannot accurately reflect the residual content of acemethaquine. Therefore, the existing technology can only roughly detect the metabolism and residue of acemethaquine in animals, and cannot accurately reflect the acemetquine residue. The metabolism in animals is not conducive to people's research on the pharmacokinetics of acemethaquine in animals and its residue elimination rules.

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
  • 1,4-dioxo-2-(1-ethoxy)-3-hydroxymethyl-sulfaquinoxaline and preparation method and application thereof
  • 1,4-dioxo-2-(1-ethoxy)-3-hydroxymethyl-sulfaquinoxaline and preparation method and application thereof
  • 1,4-dioxo-2-(1-ethoxy)-3-hydroxymethyl-sulfaquinoxaline and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] Dissolve 25 grams of acetylmethaquine in 200 ml of methanol, add 3 grams of sodium borohydride (completely added within 20 minutes) at 0°C under stirring, then control the reaction temperature and continue the reaction at 30°C for 8 hours, TLC spotting End of follow-up reaction. Then the solid precipitate was collected by filtration to obtain the product 1,4-dioxo-3-methyl-2-(1-hydroxyethyl)-quinoxaline, the filtrate was concentrated to 50 ml, placed at 0°C, and the precipitate was collected by filtration 14 grams of 1,4-dioxo-3-methyl-2-(1-hydroxyethyl)-quinoxaline product were obtained after merging, with a yield of 56%;

[0053] Mix 3.1 g of 1,4-dioxo-3-methyl-2-(1-hydroxyethyl)-quinoxaline, 50 ml of pyridine, and 1.6 g of acetic anhydride at 0°C, and then continue to stir at room temperature for 5 hours , concentrated under reduced pressure to 5-10 ml, then added 50 ml of ice water, then extracted three times with 50 ml of ethyl acetate, combined the organic phases...

Embodiment 2

[0058] Dissolve 25 grams of acemethaquine in 100 milliliters of 95% by volume ethanol aqueous solution, add 5 grams of potassium borohydride at 10°C under stirring (completely added within 20 minutes), then control the reaction temperature and continue the reaction at 20°C for 1 hour , TLC spot plate tracking reaction ended. Then the solid precipitate was collected by filtration to obtain the product 1,4-dioxo-3-methyl-2-(1-hydroxyethyl)-quinoxaline, the filtrate was concentrated to 50 ml, placed at 0°C, and the precipitate was collected by filtration , combined to obtain 1,4-dioxo-3-methyl-2-(1-hydroxyethyl)-quinoxaline with a yield of 63%;

[0059] Mix 3.1 g of 1,4-dioxo-3-methyl-2-(1-hydroxyethyl)-quinoxaline, 10 ml of pyridine, and 5 g of acetic anhydride at 0°C, then continue to stir at 30°C for 1 hour , concentrated under reduced pressure to 5-10 ml, then added 50 ml of water, then extracted three times with 50 ml of ethyl acetate, combined the organic phases, dried, an...

Embodiment 3

[0068] After 6 hours of intramuscular injection of acemethaquine in healthy pigs, blood samples were collected, extracted with organic solvents, blown dry with nitrogen, and added mobile phase to make a sample solution; in addition, the blood of untreated healthy pigs was taken to make a blank control sample according to the aforementioned method; Take compound (I) and add mobile phase to make 1mg / mL reference substance solution.

[0069] High performance liquid chromatograph, Diana Corporation, USA; chromatographic conditions: Hypersil BDS C 18 Chromatographic column, 250 mm×4.6 mm×5 μm, column temperature: 30 ℃; mobile phase: methanol (B) / water (containing 0.01% formic acid) (A), gradient elution: 0-40 min, 20%-35 % B; 40-45 min, 35%-60% B; 45-57 min, 60% B; 57-60 min, 60%-20% B; 60-65 min, 20% B; flow rate: 1 mL / min, detection wavelength: 241 nm.

[0070] The retention time of compound (I) was 8.33min, the sample solution peaked at 8.27min, and the blank sample did no...

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 1,4-dioxo-2-(1-ethoxy)-3-hydroxymethyl-sulfaquinoxaline and a preparation method and an application thereof. The 1,4-dioxo-2-(1-ethoxy)-3-hydroxymethyl-sulfaquinoxaline is shown as a formula (1). The preparation method of a product (I) comprises the following steps of: reducing mequindox serving as a raw material to obtain 1,4-dioxo-3-methyl-2-(1-hydroxymethyl)sulfaquinoxaline; mixing and reacting with acetic anhydride and pyridine to obtain 1,4-dioxo-3-methyl-2-(1-hydroxymethyl)sulfaquinoxaline; reacting an obtained product with acetic anhydride to obtain 1-oxy-2-(1-ethoxycarbonyl oxygen ethyl)-3-(1-ethoxycarbonyl oxygen ethyl)-sulfaquinoxaline; oxidizing to obtain 1,4-dioxo-2-(1-ethoxycarbonyl oxygen ethyl)-3-(1-ethoxycarbonyl oxygen ethyl)-sulfaquinoxaline; and performing hydrolysis through an alkali liquor to obtain the product (I). The product (I) can be taken as a residual marker of maquindox in target animal in-vivo metabolism or a standard product or a reference product for detecting maquindox residue in an animal-derived food.

Description

technical field [0001] The invention belongs to the technical field of veterinary pharmacology, toxicology and chemical synthesis, and specifically relates to 1,4-dioxo-2-(1-hydroxyethyl)-3-hydroxymethyl-quinoxaline, its preparation method and application. Background technique [0002] Acetylmethylquine is commonly known as "Shibajing", and its chemical name is 1,4-dioxo-3-methyl-2-acetyl-quinoxaline. It is a carbadox analog and is the first therapeutic antibacterial drug to be marketed in China. , has a strong inhibitory effect on a variety of bacteria, especially on Gram-negative bacteria, such as Pasteurella, Escherichia coli, Salmonella, and Listeria. The first-choice drug and specific drug for chronic dysentery (swine dysentery). Through large-scale popularization and application and clinical observation, it is proved that the drug has the characteristics of small dosage, quick effect, high curative effect, safety and reliability, low cost and convenient use in the tre...

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 Applications(China)
IPC IPC(8): C07D241/52G01N30/02
Inventor 王永东曾振灵祝诗发操基元刘迎春丁焕中曾东平方炳虎
Owner GENIFARM LAB INC
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