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Method for preparing novel nonsteroidal anti-inflammatory drug and anti-inflammatory and analgesic effects thereof

A technology for non-steroidal anti-inflammatory drugs and compounds, which can be used in anti-inflammatory agents, anti-infective drugs, pharmaceutical formulations, etc., and can solve the problems of unstable room temperature storage, easy volatility, poor water solubility and low melting point.

Inactive Publication Date: 2011-06-01
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because the paeonol molecule contains phenolic hydroxyl groups, and has a low melting point, is volatile and has poor water solubility, it is very unstable at room temperature.

Method used

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  • Method for preparing novel nonsteroidal anti-inflammatory drug and anti-inflammatory and analgesic effects thereof
  • Method for preparing novel nonsteroidal anti-inflammatory drug and anti-inflammatory and analgesic effects thereof
  • Method for preparing novel nonsteroidal anti-inflammatory drug and anti-inflammatory and analgesic effects thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: Synthesis of the synthesis of 5-methoxy-2-acetylphenyl ibuprofen ester (AXC 1 )

[0024] In a 25mL three-necked flask, add ibuprofen (1.03g, 5.0mmol) and thionyl chloride (1.5mL, 20.0mmol), reflux for 2h, and distill off the thionyl chloride under reduced pressure. The residue was dissolved in 10 mL of anhydrous dichloromethane, cooled to 0°C in an ice bath, paeonol (0.83 g, 5.0 mmol) and pyridine (0.8 mL, 10.0 mmol) were added, stirred for 2 h under ice bath, and then 10 mL of water was added , dichloromethane extraction (10mL × 3), combined organic phase, successively with saturated NaHCO 3 solution, distilled water and saturated saline solution, anhydrous MgSO 4 dry. After filtration, the filtrate was concentrated and subjected to column chromatography, and the eluent was petroleum ether:ethyl acetate (v:v)=6:1. The eluents were combined, the solvent was evaporated, and the oil pump was pumped to dryness to obtain a light yellow solid with a yield o...

Embodiment 2

[0025] Embodiment 2: the synthesis (AXC 2 )

[0026] In a 25ml round bottom flask, add ketoprofen (1.0g, 4.0mmol), thionyl chloride (1.2mL, 16.0mmol), pyridine 1.0mL, and reflux for 1h. Evaporate excess thionyl chloride under reduced pressure, dissolve the residue in 10 mL of anhydrous dichloromethane, cool in an ice bath, add paeonol (0.60 g, 3.0 mmol) and triethylamine (1.4 mL, 10.0 mL), Stir at room temperature for 3h. Add 0.5N sodium hydroxide solution, continue to stir for 20min, extract with dichloromethane (15mL×3), combine the organic phases, anhydrous MgSO 4 dry. After filtration, the filtrate was concentrated and subjected to column chromatography, and the eluent was petroleum ether:ethyl acetate (v:v)=9:1. The eluents were combined, and the solvent was evaporated to obtain an oily product with a yield of 68.2%. IR (cm -1 , KBr): 1759.2 (C=O), 1643.5 (C=O); 1 HNMR (400MHz, CDCl 3 , TMS), δ: 1.71 (d, 3H, CH 3 ), 2.42 (s, 3H, CH 3 ), 3.80 (s, 3H, CH 3), 4.14...

Embodiment 3

[0027] Embodiment 3: 3-hydroxyl-4-acetylphenyl ibuprofen ester (AXC 3 )

[0028] In a 25mL round bottom flask, 2,4-dihydroxyacetophenone (0.76g, 5.0mmol) was dissolved in 8mL of anhydrous dichloromethane, then added ibuprofen (1.03g, 5.0mmol), DCC (1.03g , 5.0mmol) and several grains of DMAP were stirred until dissolved. After 2h, filter, concentrate the filtrate, and perform column chromatography. The eluent is petroleum ether:ethyl acetate (v:v)=9:1. The eluents are combined, the solvent is evaporated, and the oil pump is drained to obtain an oily substance. Yield 71.25%. IR (cm -1 , KBr): 3500~3100 (OH), 1766.9 (C=O), 1643.5 (C=O); 1 HNMR (400MHz, CDCl 3 , TMS), δ: 0.80 (d, 6H, CH 3 ), 1.60 (d, 3H, CH 3 ), 1.90(m, 1H, CH), 2.55(d, 2H, CH 2 ), 2.72 (s, 3H, CH 3 ), 3.80(m, 1H, CH), 6.59(m, 2H, ArH), 7.16(d, 2H, J=7.2Hz, ArH), 7.27(d, 2H, J=7.6Hz, ArH), 7.80( d, 1H, J=8.0Hz, ArH), 12.40(s, 1H, OH); HR-MS: m / z Calcd for C 21 h 24 o 4 340.1675, Found: 340.1651 (M +...

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Abstract

The invention relates to a compound obtained by esterifying carboxylic acid-containing nonsteroidal anti-inflammatory drugs with paeonol and nor-paeonol, a preparation method and application thereof. The compound is obtained by taking the carboxylic acid-containing nonsteroidal anti-inflammatory drugs such as ibuprofen and the like as a raw material and esterifying the raw material with the paeonol through sulfonyl chlorination or with the nor-paeonol by a carbimide method. The compound has anti-inflammatory, and antipyretic and analgesic effects.

Description

technical field [0001] The invention relates to a class of ester-forming compounds containing carboxylic acid non-steroidal anti-inflammatory drugs, paeonol and norpaeonol and a preparation method thereof. The present invention also relates to pharmaceutical compositions containing these compounds with antipyretic, analgesic and anti-inflammatory effects. Background technique [0002] Inflammation is an extremely complex pathophysiological process mediated by various inflammatory mediators. Nonsteroidal anti-inflammatory drugs (NSAIDs) can inhibit prostaglandins (PGs), leukotrienes (LTs) and other inflammatory mediators, have excellent anti-inflammatory, analgesic and antipyretic effects, and their clinical application is extremely Widely used: It is widely used in rheumatoid arthritis, osteoarthritis and other rheumatic diseases; it can also be used for pain caused by trauma, toothache and tumor; it can also be used for reducing fever; small doses of aspirin can also resis...

Claims

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Application Information

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IPC IPC(8): C07C69/612C07C69/738C07C229/42C07C69/84C07D209/28C07C317/44C07D207/337C07D491/052C07C69/65C07C69/736C07C69/734C07D333/24C07D207/20C07D209/46C07C229/58C07D213/80C07C67/14C07C67/08C07C227/18C07C315/04C07D213/803A61K31/216A61K31/618A61K31/405A61K31/40A61K31/407A61K31/381A61K31/402A61K31/4035A61K31/24A61K31/455A61P29/00A61P19/02A61P19/04A61P31/00
Inventor 敖桂珍崔京浩
Owner SUZHOU UNIV
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