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Acetamido glucose devicative of indomethacin and its synthetic method and use

A technology of glucose derivatives and acetylamino, which is applied in the direction of sugar derivatives, drug combinations, medical preparations containing active ingredients, etc., and can solve the problem of inhibiting etiology

Inactive Publication Date: 2006-05-17
OCEAN UNIV OF CHINA
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  • 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

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  • 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

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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...

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 is 0...

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Abstract

The invention relates to an acetylglucosamine derivative of indomethacin and its synthesis method and application. Starting from indomethacin and acetylglucosamine, two acetylglucosamine derivatives of indomethacin, whose chemical name is 1-O-[1-(4-chloro-benzoyl)-5-methanol, were prepared Oxy-2-methyl-3-indole-acetoxy]-2-acetylamino-2-deoxy-α-D-glucose and 6-O-[1-(4-chloro-benzoyl)- 5-Methoxy-2-methyl-3-indole-acetoxy]-2-acetylamino-2-deoxy-α-D-glucose. The derivatives involved in the invention have inhibitory activity on mouse ear edema caused by croton oil, and can be used for preparing anti-inflammatory drugs.

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

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/26A61K31/7056A61P29/00A61P19/02
Inventor 李英霞张一纯宋妮李春霞
Owner OCEAN UNIV OF CHINA
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