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P-hydroxybenzene acrylic acid derivative and uses thereof

A technology of hydroxyphenylacrylic acid and derivatives, which is applied in the direction of drug combinations, medical preparations containing active ingredients, organic active ingredients, etc., and can solve problems such as osteoarthritis and rheumatoid arthritis without giving up

Inactive Publication Date: 2009-05-13
毛近隆
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In fact, Big Pharma isn't giving up on developing new drugs for osteoarthritis and rheumatoid arthritis

Method used

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  • P-hydroxybenzene acrylic acid derivative and uses thereof
  • P-hydroxybenzene acrylic acid derivative and uses thereof
  • P-hydroxybenzene acrylic acid derivative and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0168] Embodiment 1: Preparation of (E)-2-(4-sulfonamidophenyl)-3-(3-methoxy-4-acetoxyphenyl)acrylic acid

[0169]

[0170] In a four-neck flask, add 0.25g (0.0013mol) of acetylvanillin to 10mL of acetonitrile solvent, add 0.4mL of triethylamine, stir to dissolve, then add 0.22g (0.001mol) of p-sulfonamide phenylacetic acid, and stir to react After 1 hour, DBU was added, the reaction was stirred for another 1 hour, and the reaction was stopped. About 10 mL of 1N hydrochloric acid was added, extracted with ethyl acetate, and the layers were separated. The ethyl acetate solution was washed with saturated brine, dried, and concentrated to obtain a yellow solid. Weight 0.06g. Thin layer, Rf is 0.3.

[0171] 1 H-NMR (DMSO) δ (ppm): 1.94 (3H, s, COCH 3 ), 3.72 (3H, s, OCH 3 ), 7.33 (2H, NH 2 ), 7.14-7.80 (7H, m, hydrogen on the benzene ring), 7.58 (1H, -C=C-H), 12.36 (1H, s, COOH);

[0172] MS(m / z): 392.3[M+H] + , 409.4[M+NH 4 ] + ;

[0173] IR (KBr) (v / cm-1): 3434, 323...

Embodiment 2

[0174] Example 2: Preparation of 3(4-sulfonamidophenyl)-4-(3-methoxy 4-hydroxyphenyl)-2(5H)-furanone

[0175]

[0176] In a four-necked flask, add 0.37 g (0.0015 mol) of 3-methoxy 4-hydroxybromoacetophenone into 10 mL of acetonitrile solvent, add 0.4 mL of triethylamine, and then add 0.22 g of p-sulfonamidophenylacetic acid (0.001mol), stirred and reacted for 1 hour, then added DBU, stirred and reacted for 2 hours, stopped the reaction, added about 10 mL of 1N hydrochloric acid, extracted with ethyl acetate, separated layers, washed the ethyl acetate solution with water, dried, and concentrated to obtain yellow solid. Thin layer, Rf is 0.4.

[0177] 1 H-NMR (DMSO) δ (ppm): 5.44 (2H, s, CH 2 ), 7.24-7.73 (7H, m, benzene ring hydrogen), 7.45 (2H, NH 2 );

[0178] MS(m / z): 362.2[M+H] + ;

[0179] IR (KBr) (v / cm-1): 3431, 3230 (NH 2 ); 3010 (benzene ring hydrogen); 2940 (OCH 3 ); 1740 (furanone); 1192, 1141 (SO 2 ).

Embodiment 3

[0180] Embodiment 3: Preparation of (E)-2-(4-sulfonamidophenyl)-3-(3-methoxyl-4-hydroxylphenyl)acrylic acid

[0181]

[0182] In a four-neck flask, add 0.23g (0.0015mol) of vanillin to 10mL of acetonitrile solvent, add 0.40mL of triethylamine, stir to dissolve, then add 0.22g (0.001mol) of p-sulfonamide phenylacetic acid, and stir to react 1 After 2 hours, DBU was added, and the reaction was stirred for another 2 hours. The reaction was stopped, and about 10 mL of 1N hydrochloric acid was added, extracted with ethyl acetate, and the layers were separated. The ethyl acetate solution was washed with water, dried, and concentrated to obtain a yellow solid. Thin layer, Rf is 0.15.

[0183] MS(m / z): 350.3[M+H] + , 367.4[M+NH 4 ] + ;

[0184] IR (KBr) (v / cm-1): 3433, 3230 (NH 2 , COOH); 3020, 2977 (benzene ring hydrogen); 2942 (OCH 3 ); 1677(υ C＝0 ,—CH=CCOOH); 1190,1154 (SO 2 ).

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Abstract

The invention discloses a p-hydroxy phenyl acrylic acid derivative, which has a chemical structure expressed by general formula (I). The invention also discloses application of the p-hydroxy phenyl acrylic acid derivative to preparing COX-2 selective inhibitor medicament, and a pharmaceutical composition for treating and preventing pain, inflammation, rheumatoid arthritis, osteoarthritis or dysmenorrheal diseases, or antiviral and antibacterial pharmaceutical composition for treating and preventing virus and bacterial infection, or pharmaceutical composition for treating and preventing atherosclerosis, thrombosis, apoplexy or ischemia cerebrovascular diseases, wherein the pharmaceutical composition contains the p-hydroxy phenyl acrylic acid derivative or medicinal salt thereof with curative effective dose.

Description

technical field [0001] The present invention relates to a p-hydroxyphenylacrylic acid derivative and its application, in particular to a compound of general formula (I), a pharmacologically acceptable salt and hydrate, a preparation method thereof, and a composition containing one or more of these compounds , and the application of the compound in the preparation of COX-2 selective inhibitor drugs. Background technique [0002] Nonsteroidal 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, but gastrointestinal complications are long-term The most common side effect of taking NSAIDs drugs, the newly developed cyclooxygenase (COX2) inhibitor can significantly reduce the occurrence of gastrointestinal complications while treating inflammation and pain. [0003] Vioxx, a widely used cyclooxygenase inhibitor, ...

Claims

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Application Information

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IPC IPC(8): C07D307/58C07D317/50C07C311/29A61K31/341A61K31/357A61P29/00A61P31/10A61P35/00
CPCC07D207/30A61K31/216A61K31/4015C07C311/51C07D307/58A61K31/341C07C317/44C07C311/29A61K31/222A61K31/365A61P29/00A61P31/10A61P35/00
Inventor 毛近隆王文菊冉祥凯田景振张萍
Owner 毛近隆
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