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Sulfonyl diphenylethyllene endocompound and its preparation method and pharmaceutical uses

A compound, methanesulfonyl technology, applied in the field of ethylene bridge compounds, can solve the problems that have not yet been seen, and achieve the effect of good anti-inflammatory activity

Inactive Publication Date: 2006-04-26
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, after searching: based on the compound skeleton of ferulic acid, the active ingredient of traditional Chinese medicine, and according to the research on the structure-activity relationship of cyclooxygenase inhibitors, a series of diaryl ring compounds connected by ethylene bridges, especially those containing sulfonyl diphenyl In the existing literature, there has not been seen so far

Method used

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  • Sulfonyl diphenylethyllene endocompound and its preparation method and pharmaceutical uses
  • Sulfonyl diphenylethyllene endocompound and its preparation method and pharmaceutical uses
  • Sulfonyl diphenylethyllene endocompound and its preparation method and pharmaceutical uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] Embodiment 1: the preparation of 4-methylsulfide acetophenone

[0069]

[0070] In a 1L four-necked bottle, add AlCl 3 130.0g (0.97mol) and 650mL of chloroform, cooled in an ice-water bath to about 5°C, stirred and added dropwise 76g (0.97mol) of acetyl chloride, after the dropwise addition, kept the temperature at 5°C, and added dropwise under stirring within 1hr Thioanisole 100g (0.81mol), dropwise completed, removed from the ice-water bath, stirred at room temperature for 2hr, poured into a mixture of 1000mL water, 250mL concentrated HCl and 500g ice, stirred, separated the chloroform layer, and extracted with 100mL chloroform The aqueous layer was combined with the chloroform layer, dried with anhydrous sodium sulfate, evaporated in an oil bath at 100°C to remove chloroform, and then evaporated to dryness under reduced pressure to obtain a light yellow liquid, which was removed from the oil bath and cooled to become a solid with a weight of 127.0 g, yield 95.0%...

Embodiment 2

[0072] Embodiment 2: the preparation of 4-methylsulfoneacetophenone

[0073]

[0074]In a 500mL four-neck flask, add 83.1g (0.5mol) of 4-methylsulfide acetophenone, 180mL of acetic acid and 1.0mL of 85% phosphoric acid, put it in an oil bath at 110°C, heat and stir, and drop Add 30%H 2 o 2 A mixture of 130mL (1.1mol) and 0.7mL of 85% phosphoric acid, after the dropwise addition, was stirred in an oil bath for 1hr, then poured into a mixture of 600mL of water and 300g of ice, stirred to precipitate a white solid, cooled and filtered to obtain a white solid , washed twice with water, then twice with ethanol, and dried to obtain 95.0 g of white solid with a yield of 96.0%. Recrystallized with ethanol to obtain white prismatic crystals, m.p.126.2-126.5°C. (Literature melting point 124-126°C).

[0075] IR(KBr)(v / cm -1 ): 3356.33, 3095.29, 3072.47, 3017.05, 3004.23, 2922.78, 1687.69 (υ c＝o ), 574.31, 1395.36, 1356.83, 1310.57, 1296.21, 1258.55, 1172.40, 1148.46.1089.72

Embodiment 3

[0076] Embodiment 3: the preparation of 4-methylsulfone phenylacetic acid

[0077]

[0078] In a 1L four-neck flask, add 80g (0.4mol) of 4-methylsulfoneacetophenone, 12.8g (0.4mol) of sublimed sulfur and 56.0mL of morphineline, then heat to 130°C and reflux for 10hr, cool to 50°C, and Add 80mL of ethyl acetate, stir evenly, then add 40mL of petroleum ether, stir for about 20 minutes, it becomes solid, then add 80g of NaOH in 800mL of water solution, place in an oil bath at 85°C and stir overnight, remove from the oil bath , cooled to room temperature, filtered, added 160mL of concentrated hydrochloric acid, adjusted the pH to about 4-5, precipitated a light yellow solid, and recrystallized the solid with ethyl acetate to obtain 43.0 g of colorless needle crystals, yield 50.2%, m.p.134-136 ℃. (Literature melting point 137°C).

[0079] IR(KBr)(v / cm -1 ): 3095.17, 3070.50, 3030.96, 3016.14, 2930.92, 2732.30, 1699.96 (υ c＝o ), 1409.51, 1297.81, 1240.15, 1145.54, 1090.27, 96...

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PUM

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Abstract

The present invention relates to vinyl bridge compound containing sulfonyl radical and diphenyl radical and in the general expression as shown. The present invention also relates to its preparation process and application in preparing medicine for inhibiting epoxy synthase 2 and medicine for treating inflammation and pain of mammal.

Description

technical field [0001] The present invention relates to the vinyl bridge compound that contains sulfonyl diphenyl group, particularly relate to the compound of general formula (I) and preparation method thereof, and the composition containing one or more these compounds, and this compound is in the preparation inhibition and epoxy Drug use for synthase 2-related diseases. [0002] Background technique [0003] Non-steroidal anti-inflammatory drugs (NSAIDs) are widely used in the treatment of rheumatic diseases, inflammatory diseases, pain, soft tissue diseases and sports injuries due to their definite anti-inflammatory and analgesic effects. Disease and tumor prevention. Gastrointestinal complications are the most common side effects of long-term use of NSAIDs. The newly developed cyclooxygenase (COX-2) inhibitor can significantly reduce the occurrence of gastrointestinal complications while treating inflammation and pain. [0004] The pharmacological effects of NSAIDs...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/44A61K31/19A61K31/215A61P29/00C07C317/24
Inventor 冉祥凯毛近隆庞华陈丽焦波
Owner SHANDONG UNIV
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