Ethyl salicylate glycosides and synthetic method and application thereof

A technology of ethyl salicylate glycosides and compounds, which is applied in the fields of analgesic, anti-inflammatory, and thrombosis-inhibiting drugs, and can solve problems such as many adverse reactions

Active Publication Date: 2012-05-16
INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Salicylic acid drugs are common non-steroidal anti-inflammatory drugs, which are widely used as antipyretic, analgesic, anti-inflammatory and anti-rheumatic drugs. There are also many adverse reactions caused by long-term use, especially gastrointestinal irritation

Method used

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  • Ethyl salicylate glycosides and synthetic method and application thereof
  • Ethyl salicylate glycosides and synthetic method and application thereof
  • Ethyl salicylate glycosides and synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0139] Example 1 Synthesis of ethyl 2-O-β-D-galactopyranosylbenzoate (1)

[0140] (1) Add 100.0mmol (9.5ml) of acetic anhydride and 1.0mmol (80.0ul) of perchloric acid into a 50ml three-necked flask as a catalyst, stir at room temperature and add 20.0mmol (3.6g) of D-galactose in batches, and control the temperature Lower than 40°C, finish adding within about 30 minutes, continue stirring for about 1 hour, after acetylation is completed, add phosphorus tribromide 10.0mmol (1.1ml) dropwise to the above reaction solution, add about 15 minutes, control the temperature below 20°C , then add 0.2ml of water dropwise, continue stirring for 2-3h, the reaction is completed, pour into ice water, stir, a white solid appears, filter, dissolve in ethyl acetate, wash with water, and dry over anhydrous sodium sulfate to obtain 6.4g of white solid, The yield is about 77.5%.

[0141] (2) A 100ml three-necked flask was placed in an oil bath at 40°C, and 26.0mmol (20.8ml) of 1.25N aqueous sodiu...

Embodiment 2

[0145] Example 2 Synthesis of ethyl 2-O-α-D-mannopyranosylbenzoate (1)

[0146] (1) Add 100.0mmol (9.5ml) of acetic anhydride and 1.0mmol (80.0ul) of perchloric acid into a 50ml three-necked flask as a catalyst, stir at room temperature and add 20.0mmol (3.6g) of D-mannose in batches, and control the temperature Lower than 40°C, finish adding within about 30 minutes, continue stirring for about 1 hour, after acetylation is completed, add phosphorus tribromide 10.0mmol (1.1ml) dropwise to the above reaction solution, add about 15 minutes, control the temperature below 20°C , then add 0.2ml of water dropwise, continue to stir for 2-3h, the reaction is completed, pour into ice water, stir, a white solid appears, filter, ethyl acetate dissolves, wash with water, and dry over anhydrous sodium sulfate to obtain 6.0g of white solid, The yield is about 73.0%.

[0147] (2) A 100ml three-necked flask was placed in an oil bath at 40°C, and 26.0mmol (20.8ml) of 1.25N aqueous sodium hydro...

Embodiment 3

[0151] Example 3 Synthesis of ethyl 2-O-β-D-xylopyranosylbenzoate (3)

[0152] (1) Add 100.0mmol (9.5ml) of acetic anhydride and 1.0mmol (80.0ul) of perchloric acid into a 50ml three-necked flask as a catalyst, stir at room temperature and add 20.0mmol (3.0g) of D-mannose in batches, and control the temperature Lower than 40°C, finish adding within about 30 minutes, continue stirring for about 1 hour, after acetylation is completed, add phosphorus tribromide 10.0mmol (1.1ml) dropwise to the above reaction solution, add about 15 minutes, control the temperature below 20°C , then add 0.2ml of water dropwise, continue to stir for 2-3h, the reaction is completed, pour into ice water, stir, a white solid appears, filter, dissolve in ethyl acetate, wash with water, and dry over anhydrous sodium sulfate to obtain 4.7g of white solid, The yield is about 70.0%.

[0153] (2) Place a 100ml three-necked flask in an oil bath at 40°C, add 26.0mmol (31.2ml) of 1.25N aqueous sodium hydroxide...

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PUM

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Abstract

The invention relates to new ethyl salicylate glycosides, a synthetic method thereof, pharmaceutical compositions containing the ethyl salicylate glycosides, and applications of ethyl salicylate glycosides as medicaments, in particular antipyretic, analgesic, antiphlogistic and thrombosis inhibiting medicaments. The structural formula of the ethyl salicylate glycosides is as shown in the specification, wherein R is monosaccharide or disaccharide. The synthetic method provided by the invention has the advantages of simplicity, low synthesis cost and small environmental pollution; shown by activity evaluation, the ethyl salicylate glycosides have obvious antiphlogistic, analgesic and anti-platelet agglutination effects, the action time is prolonged, the adverse reaction is obviously reduced compared with salicylic acid medicaments, and mainly the stimulation to the gastrointestinal tract is reduced, therefore, the ethyl salicylate glycosides can be hopefully developed into new analgesic, antiphlogistic and thrombosis inhibiting medicaments with competitive power.

Description

technical field [0001] The present invention relates to new ethyl salicylate glycoside compounds, their synthesis method, pharmaceutical composition containing them, and their application as medicine, especially medicine for anti-inflammation, analgesia and thrombus formation inhibition. technical background [0002] Salicylic acid drugs are common non-steroidal anti-inflammatory drugs, which are widely used as antipyretic, analgesic, anti-inflammatory and anti-rheumatic drugs. There are also many adverse reactions caused by long-term use, especially gastrointestinal irritation. In order to reduce the side effects of salicylic acid drugs, while retaining the good activity of salicylic acid drugs, making them suitable for long-term administration, we have modified the structure of ethyl salicylate, synthesized five new derivatives, and carried out The activity evaluation showed that they have obvious anti-inflammatory and analgesic effects, and the synthesis method is simple...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/203C07H1/00A61K31/7034A61P29/00A61P7/02
Inventor 张东明杜冠华王超张天泰
Owner INST OF MATERIA MEDICA CHINESE ACAD OF MEDICAL SCI
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