CS254605B1 - 2,3-bis (2-methoxy-5-chlorobenzamido) phenazine-5,10-dioxide - Google Patents

Abstract

The solution relates to 2,3-bis(2-methoxy-5-chlorobenzamido)phenazine-5,10-dioxide of formula I och3 This new substance exhibits anthelmintic activity against the model helminth Hymenolepis nana and Nippostrongylus brasiliensis.

Description

The invention relates to 2,3-bis (2-methoxy-5-chlorobenzamido) phenazine-5,10-dioxide of the formula I

This novel compound, which has not yet been described, exhibits useful anthelmintic activity, in particular against the model helminth of Hymenolepis nana and Nippostrongylus brasiliensis.

The compound of formula I can be prepared by reacting 2,3-bis (2-methoxy-5-chlorobenzamido) phenazine (No. AO No. 254 604) with 30% hydrogen peroxide in glacial acetic acid at 60 ° C to 70 ° C .

Evaluation of anthelmintic efficacy against model helmet Hymenolepis nana.

The tests were performed on male H strain mice weighing 10-13 g in groups of 6 each. Two of the three control groups were invaded untreated, the third invaded, treated with a standard formulation - niclosamide piperazine salt - against which efficacy was compared. Invasion was performed by probing orally with 500 mature Hymenolepis nana eggs in a volume of 0.25 ml / mouse. The compound of formula I was administered orally by gavage at 150 mg / kg ¹ µl on days 13 and 14 after invasion. hm. (live weight) as a homogenate in Dorfman ' s reagent. Mice were killed on day 3 and, after the total number of tapeworms with scolexes at complete helmintological autopsy of the small intestine of mice, an average of 60% anthelmintic activity was evaluated by the Steward indirect activity method.

Evaluation of anthelmintic activity against model helminth Nippostrongylus brasiliensis.

Tests were performed on male Black head rats weighing 120-140 g in groups of 6 each. Two of the three control groups were invaded untreated, the third invaded treated with the standard levamisole to which efficacy was compared. Rats were invaded by 500 moving larvae of Nippostrongylus brasiliensis subcutaneously into the dorsal landscape between the shoulder blades. On day 8 after invasion, the compound of formula I was administered in a single dose

150 mg.kg ^-1 b. hm. The compound was orally administered to rats as a homogenate in Dorfman ' s reagent and was terminated on day 12 by killing the animals and performing a small intestinal helminth dissection.

From the observed total number of worms in the intestine and calculation by the indirect activity method according to Steward, the anthelmintic activity of the evaluated compound of formula I was determined on average 59.7 *.

The process for the preparation of the compound of the formula I according to the invention is simple; This example is merely illustrative, not limiting.

Example

To a suspension of 5.47 g (0.01 mol) of 2,3-bis (2-methoxy-5-chlorobenzamido) phenazine in 200 ml of glacial acetic acid was added dropwise with stirring 40 ml of 30% hydrogen peroxide and the mixture was further stirred for 15 h at 60-70 ° C. The cold reaction mixture was filtered off with suction and the crude product was recrystallized from dimethylformamide. 3.93 g (67.9%) of the substance with mp 248-249 ° C and composition C ₂ gH _{2 ()} Cl ₂ N ₄ O _{6 were obtained} .

Claims (2)

SUBJECT OF THE INVENTION 2,3-Bis (2-methoxy-5-chlorobenzamido) phenazine-5,10-dioxide of formula I OCH, NHCO NHCO Cl 'Cl OCH,