SU991716A1 - 8-(n-methoxyphenyl)-1,3-dimethylimidazo-4/4',5'-c/-imidazo /1,2-a/ pyridine-2-on possessing analgetic and antiinflammatory activity - Google Patents

Abstract

8- (p-Methoxyphenyl) -I, 3-dimethylimidazo 4, 5-c imidazo-GI, 2-aJ pyridine-2-OH of the formula -N ChSh CHjO with analgesic and anti-inflammatory action. Soo Od

Description

A novel compound of the imidazon-imidazopyridine series is proposed, namely, 8- (p-methoxyphenyl) -1,3-dimethylchmidazo 4,5-c-imidazoG1,2-aZpyridine2-OR, which has an analgesic and anti-inflammatory effect.

It is widely used in medicine as an analgesic, anti-inflammatory and antipyretic drug analgin.

The aim of the invention is to expand the arsenal of means of influence on a living organism.

This goal is achieved by absorbing 8- (p-methoxyphenyl) -1,3-dimethylimidazo 4, 5-sZimidazo. 1, pyridin-2-one formula

xn

9

x /

-lg ".,.

sn

l

CHjO

This compound is obtained by reacting 4-amino-1,3-dimethylimidazo 4, 5-c pyridin-2-one with p-methoxyphenate-bromide in boiling alcohol

The resulting 8- (p-methoxyphenyl) 1, 3-dimethylimidazo 4,5-c-imidazo 1,2-a pyridin-2-one is a colorless crystalline substance, readily soluble in water, alcohol.

Example. A mixture of 1.26 g (7.0 mmol) of 4-amino-1,3-dimethylimidazo 4, 5-c 1-pyridin-2-one and 0.81 g (3.5 mmol) of p-methoxyphenacyl bromide is heated in 30 ml of boiling water. alcohol for 2.5 hours and left overnight, after which the precipitate is filtered off, washed with acetone, ether and dried. 1.57 g (72%) of 8-p-methoxyphenyl-1, 3-dimethyllimidazo G4,5-c imidazoG, 2-a} pyridin-2-one with t are obtained. From 262-263 C (from ethanol).

Found,%: N 17.82; Calculated,%: N 18,17; IR spectrum (liquid paraffin): Jj.yp 1730 cm.

Anesthetic activity was studied in experiments on white mice (weight

20 + 2 g). Pain irritation was caused by mechanically squeezing the root of the tail using Diffenbach clips. The substance was administered intramuscularly at a dose of 0.2 mmol 30 minutes before pain irritation was applied.

Anti-inflammatory activity was studied in experiments on white outbred rats weighing 180 + 20 g. Inflammation was caused by subplantar administration of 0.1 ml of a 3.5% formaldehyde solution. The substance was injected into the stomach (2.5% starch suspension) at a dose of 0.2 mmol 24 and 2 hours prior to the introduction of the formaldehyde solution. The limb volume was measured 3 hours after the formaldehyde solution was injected.

0 The obtained results were compared with the data with the administration of analgin in equimolar concentration.

The results of the determination of the analgesic and anti-inflammatory activity of the studied compound, as well as data on its toxicity, are given in the table.

Thus, 8- (p-methoxyphenyl) - 0 1,3-dimethylimidazo 4,5-c-imidazo 1,2-a pyridin-2-one has analgesic and anti-inflammatory activity that is superior to analgin.

Claims (1)

<claim-text> <table border = "1"> <tbody> <tr> <td> Substance </ td> <td> • OD 60 "mg / kg </ td> <td> AU <sub> HS </ sub> when overlaid clamping mg / kg </ td> <td colspan = "2"> Anti-inflammatory activity of the formalin model, % </ td> </ tr> <tr> <td> </ td> <td> </ td> <td> </ td> <td> per t day </ td> <td> in 1 day </ td> </ tr> </ tbody> </ table> <claim-text> 8- (p-Methoxyphenyl) I, 3-dimethylimidazo [4, 5'-s] imidazo </ claim-text> <claim-text> {1,2-a] pyridin-2-one Over 400 175 + 45 73 84 </ claim-text> <claim-text> Analgin </ claim-text> <claim-text> Over 400 247 + 60 48 </ claim-text>