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Oxazole analog derivative and its preparation method and its anti-inflammatory and analgesic uses

A technology of oxazoles and drugs, applied in the field of active compounds with anti-inflammatory and analgesic properties, can solve problems such as long half-life and unsatisfactory COX-2 selectivity

Inactive Publication Date: 2006-11-22
北京上地新世纪生物医药研究所有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The drug has a longer half-life and better analgesic effect, but its COX-2 selectivity is not ideal

Method used

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  • Oxazole analog derivative and its preparation method and its anti-inflammatory and analgesic uses
  • Oxazole analog derivative and its preparation method and its anti-inflammatory and analgesic uses
  • Oxazole analog derivative and its preparation method and its anti-inflammatory and analgesic uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] The preparation of step 1, m-fluorophenylacetyl chloride:

[0026] In a 250ml three-neck flask, add m-fluorophenylacetic acid (10g, 0.065mol) and thionyl chloride (9.2ml, 0.13mol), stir and dissolve at room temperature, add DMF (0.4ml), react at room temperature for 24 hours, evaporate under reduced pressure Thionyl chloride was removed, and then the fraction at 65°C was collected to obtain 7.2 g of the product.

[0027] Step 2, the preparation of (1-(4-fluorophenyl)-2-(3-fluorophenyl)ethanone:

[0028] Add aluminum trichloride (12.0g, 0.09mol) and fluorobenzene (7.65ml, 0.082mol) into a dry 500ml three-necked flask, stir at room temperature and add m-fluorophenylacetyl chloride (14.1g, 0.082mol) dropwise, Complete, continue to react for 30 minutes, slowly add ethyl acetate (200ml), then pour the reaction solution into ice water, separate layers, wash the organic phase with saturated sodium bicarbonate solution, dry over anhydrous magnesium sulfate, evaporate the solve...

Embodiment 2

[0043] Analgesic Effect-Mouse Writhing Test Induced by Glacial Acetic Acid

[0044]60 mice (half male and half female) weighing 18-22 g were randomly divided into control group, positive drug (oxaprozine 100mg / kg and Celebrex 30mg / kg) group and this product 25, 50 and 100mg / kg doses Group, 10 in each group. This product was intragastrically administered once a day, 0.1ml / 10g for 3 consecutive days, the positive drug group was intragastrically administered oxaprozine and Celebrex, and the control group was intragastrically administered an equivalent amount of 0.5% sodium carboxymethylcellulose. One hour after the last dose, each mouse was injected intraperitoneally with 0.2ml of 1% glacial acetic acid to induce pain, and the number of writhing times of each mouse within 15 minutes after the injection of 1% glacial acetic acid was recorded, and the writhing reaction inhibition rate was calculated according to the following formula. The temperature of the whole experiment was co...

Embodiment 3

[0049] Anti-inflammation effect-xylene-inflammation test on auricle of mice

[0050] 60 mice (male) with body weight of 25~30g were randomly divided into control group, positive drug (oxaprozine 100mg / kg and Celebrex 30mg / kg) group and this product 25, 50 and 100mg / kg dose groups, 10 in each group. This product was intragastrically administered once a day, 0.1ml / 10g for 3 consecutive days, the positive drug group was intragastrically administered oxaprozine and Celebrex, and the control group was intragastrically administered an equivalent amount of 0.5% sodium carboxymethylcellulose. One hour after the last dose of medicine, 0.05ml of xylene was applied to the right ear of mice in each group. The left ear was used as a control. The scale weighs, and the difference between the weight of the left and right ear piece is used as the degree of swelling. The degree of swelling in each group was calculated to obtain the swelling inhibition rate (%).

[0051] The high-dose group o...

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Abstract

The invention relates to a group of oxazoles having a formula (I), their medicinal salts or their solvolytes, the invention also relates to the process for preparing the compounds of formula (I), the antiphlogistic and analgetic compositions containing the compounds and the use of the compounds (I) in preparing antiphlogistic and analgesic medicaments.

Description

technical field [0001] The invention belongs to the field of organic chemistry and medicinal chemistry, in particular, the invention relates to active compounds with anti-inflammatory and analgesic properties. Background technique [0002] Nonsteroidal anti-inflammatory drugs (NSAIDs) are a class of drugs with anti-inflammatory and analgesic effects, which can improve the inflammatory symptoms of rheumatic diseases and relieve pain, and are the most widely used drugs in the world. a class of prescription drugs. The mechanism of action of NSAIDs is to exert their pharmacological effects by inhibiting the activity of cyclooxygenase (COX). However, side effects may occur during use, especially when taken for a long time and in large quantities, the most common of which is damage to the gastrointestinal tract. NSAIDs can cause indigestion, gastrointestinal mucosal erosion, peptic ulcer and bleeding, and even be life-threatening. [0003] NSAIDs currently available on the mark...

Claims

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Application Information

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IPC IPC(8): C07D263/32A61K31/421A61P29/00
Inventor 李晶周小平
Owner 北京上地新世纪生物医药研究所有限公司