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

Acetamido glucose devicative of indomethacin and its synthetic method and use

A technology of glucose derivatives and acetamido, which can be used in sugar derivatives, drug combinations, medical preparations containing active ingredients, etc., and can solve problems such as inhibiting etiology

Inactive Publication Date: 2005-05-18
OCEAN UNIV OF CHINA
View PDF0 Cites 13 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the treatment of osteoarthritis, non-steroidal anti-inflammatory drugs can only play an analgesic and anti-inflammatory role, but cannot fundamentally inhibit the cause of disease.

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
  • Acetamido glucose devicative of indomethacin and its synthetic method and use
  • Acetamido glucose devicative of indomethacin and its synthetic method and use
  • Acetamido glucose devicative of indomethacin and its synthetic method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0010] Example 1: 1-O-[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-3-indole-acetoxy]-2-acetylamino-2-deoxy - Synthesis of α-D-glucose (hereinafter referred to as compound 1)

[0011] Step 1: Benzyl Protection

[0012]

[0013] Compound 3 Compound 4 Compound 5

[0014]

[0015] Compound 6 Compound 7

[0016] Dissolve 1mmol of acetylglucosamine (hereinafter referred to as compound 3) in 10mL of N,N-dimethylformamide (hereinafter referred to as DMF), react in ice bath for 30min, add 6mmol of benzyl bromide, stir for 10min, then add 9.3mmol of barium oxide , 1.7 mmol of barium hydroxide octahydrate and a catalytic amount of tetrabutylammonium iodide. The reaction was carried out in an ice bath for 5 h and at room temperature overnight. Add 15 mL of dichloromethane to dilute, filter with diatomaceous earth to remove insoluble matter, and wash the filter cake several times with dichloromethane. The filtrate was evaporated to dryness, dissolved in dichloromethane, washed twice...

Embodiment 2

[0028] Example 2: 6-O-[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-3-indole-acetoxy]-2-acetylamino-2-deoxy - Synthesis of α-D-glucose (hereinafter referred to as compound 2)

[0029] Step 1: Benzyl Protection

[0030]

[0031] Compound 3 Compound 9

[0032] Stir the mixture of 0.01 mol of compound 3 and 20 mL of benzyl alcohol evenly, then add 0.1 mL of boron trifluoride ether, and heat to reflux. After the reaction was detected by TLC, the reaction solution was cooled to 0° C., and 120 mL of ether was slowly added, and a large amount of precipitates precipitated out. After standing overnight at 4°C, filter, wash the filter cake with ether, and dry to obtain 2.60 g of white solid 1-O-benzyl-2-acetylamino-2-deoxy-D-glucose (hereinafter referred to as compound 9). Rate 83.6%, R f 0.30 (chloroform:methanol=6:1). When the feeding amount of compound 3 is 0.01mol, the feeding amount of the benzyl alcohol is 5-50ml, and the feeding amount of the boron trifluoride ether i...

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

PropertyMeasurementUnit
boiling pointaaaaaaaaaa
Login to View More

Abstract

The present invention relates to acetamido glucose derivatives of indomethacin and their synthesis process and use. The kinds of acetamido glucose derivatives of indomethacin prepared with indomethacin and acetamido glucose are 1-O-[1-(4-chloro-benzoyl)-5 -methoxy-2-methyl-3-indolyl-acetoxy]-2-acetylamino-2-deoxy-alpha-D-glucose and 6-O-[1-(4-chloro-benzoyl)-5-methoxy-2-methyl-3-indolyl-acetoxy]-2-acetylamino-2-deoxy-alpha-D-glucose. The derivatives of the present invention has the activity of inhibiting mouse ear dropsy caused by croton oil and may be used in preparing antiphlogistic medicine.

Description

technical field [0001] The invention relates to an acetylglucosamine derivative of indomethacin and its synthesis method and application. The derivative has physiological activity and can be used to prepare anti-inflammatory drugs. Background technique [0002] Indomethacin is a non-steroidal anti-inflammatory drug, which has a significant effect on the treatment of rheumatism and rheumatoid arthritis. However, like most other non-steroidal anti-inflammatory drugs, indomethacin has relatively strong side effects such as gastrointestinal mucosal damage, and has problems such as low bioavailability. In recent years, a variety of methods have been used to reduce its toxic side effects and improve bioavailability, and the synthesis of ester derivatives of non-steroidal anti-inflammatory drugs is one of them. Recently, Borowiecka et al. synthesized 2-bromosugar derivatives of NSAIDs including indomethacin, aspirin, and diclofenac, and RainerK.Uhrig et al. synthesized the compou...

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): A61K31/7056A61P19/02A61P29/00C07H15/26
Inventor 李英霞张一纯宋妮李春霞
Owner OCEAN UNIV OF CHINA
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