SU686318A1 - 4-(3,3-dimethyltriazeno)-n-acetylbenzenesulfamide displaying anti-inflammatory activity - Google Patents

Abstract

four-

Description

The invention relates to the field of synthesis of biologically active compounds, specifically, to the synthesis of 4- (3,3-dimethyltriazeno) -H-acetylbenzenesulfamide, which has an anti-inflammatory effect.

Derivatives of triazenes of the general formula II are known:

J VN-N-KC,

 R.

where R is alkyl, alLyl,

R-alkyl, allyl, chloroethyl

or R, + Ri-CH2.-CHj, Rc-capGoxy, carbamal, carbalko-c, methoxy, pyrimid-1-2-sulfamoyl, exhibiting anti-inflammatory activity, but they have a limited spectrum of action pj.

The aim of the invention is new members of the class triazenov, showing anti-inflammatory activity, as well as the expansion of the means of influence on a living organism.

These properties are determined by the new chemical structure of 4- (3,3-dimethyltriazeno) -H-acetylbenzenesup'amide, which is expressed by the formula - {.,.

(Y)

n /

.x SOjNHCOCHa

Hj /

The proposed compound is obtained by reacting 4- (3, 3-dimethyltriazeno) benzenesulfamide with acetyl chloride in an organic solvent in the presence of potash.

P r and m er. 9.12 g (0.04 mol) of 4- (3,3-dimethyltriazeno) benzene sulphamide is dissolved in 250. ml of acetone and 30% g (0.21 mol) of potash is added. Under stirring at a constant temperature of 20 ° C, 4 ml (0.056 mol) of acetyl chloride are added dropwise to the suspension obtained. The reaction mixture is stirred for 30 minutes at room temperature and boiled for 6 hours. You are; The precipitated 4- (3,3-dimeshtriazeno) -Y-acetylbenzenesulfamide and the excess is filtered, washed with acetone and dissolved in 300 ml of water. The potash is neutralized with concentrated hydrochloric acid. The filtered product is filtered, washed with water, dried, and recrystallized from benzene. 8 g (70%) of 4- (3,3-dimethyltriazeno) -Y-acetylbenzenesulfamide are obtained with a melting point of 155-157 s.

PMR spectrum (ppm, (); 1.97; AND (CH3) 4 3.25, 3.57 j CgE4 7.48, 7.93.

Found,%: C 44.36; H 5.27; if 20.50; S 11.34.

C, (, H, bH4 OjS.

Calculated,%: C, 44.43; H, 5.22; H, 20.73; S, 11.86.

The anti-inflammatory activity of the proposed compound of the formula I was studied in rats, in which adjuvant-arthritis was reproduced by injecting 0.1 ml of adjouvant Freund into the sole of the left hind foot. In a day. The reproduction process started the treatment. The test group intragastrically injected the test compound in suspension

in starch paste (10

animals), control animals

(10 rats) - starch paste; Treatment was carried out daily, except weekends, for 17 days (13 injections altogether). The daily dose of the drug - 20 mg / kg of the body. For comparison, the treatment of rats with adjuvant

arthritis with phenylbutazone (a drug successfully used in clinical practice).

During the experiment, the dynamics of body weight and limb swelling of animals were monitored. Limb volume was determined by the amount of water displaced when immersed in a graduated tube to determine the swelling of the joints from the volume of the affected limb. The volume of the normal rat leg was read. At the end of the test, after bleeding, the activity indicators were measured and the internal organs were weighed. Deviation percentage

5 joints from control were calculated by the formula:

% deviation X 100 where

About |. - average swelling of the limbs

in the control group, O- - moderate swelling of the limbs

in experimental rats. Similarly, the percent deviation from the control of other indicators was calculated.

The results of biological tests are presented in the table;

As shown by the results of biological tests, the proposed 4 (3,3-dimethyltriazeno) -H-acetylbenzenesulfamide has a more pronounced anti-inflammatory effect, than the well-known active drug phenylbutazone, as used in a lower daily dose, suppresses the swelling of the joints of rats with adiovascular arthritis in such the same degree as the latter, and, moreover, has an immunosuppressive effect, since the weight of the spleen of rats with adjuvant is statistically significantly reduced. arthritis.

Claims (1)

4- (3,3-dimethyltriazeno) -Nacetylbenzenesu. Chfamide of formula I CH ₃ ^ ciV N-NN ^ - S0 ₂ NHCOCH ₃ exhibiting anti-inflammatory effect.