CS254544B1 - 2,3-bis/benzamido/phenazines - Google Patents

Abstract

wherein R is hydrogen and R is chlorine or nitro or R 1 is hydrogen and R 1 nitrogroup. These new, not yet described substances show anthelmintic activity against model helmint Hymenolepi

Description

254544 2

The invention relates to 2,3-bis (benzamido) phenazines of the formula I

Where R is hydrogen and R is chlorine or nitro or R is hydrogen and R is nitro.

These novel compounds, which have not yet been described, exhibit useful anthelmintic activity, in particular against the Hymenolepis nana model helminth.

Compounds of formula I may be prepared by reacting 2,3-diaminophenazine with 4-chlorobenzoic acid chloride or 3-nitrobenzoic acid or 4-nitrobenzoic acid in pyridine at 20-30 ° C.

Evaluation of anthelmintic activity against model Hymenolepis nana helminth:

Tests were performed on male H mice weighing 10-13 g in groups of 6 pieces. Two of the three control groups were invaded, untreated, third invaded, treated with the standard formulation - piperazine niclosamide salt - against which the efficacy of the compounds was compared.

Invasion was performed by probing orally with 500 mature Hymenolepis nana eggs at a volume of 0.25 ml / mouse. Compounds of formula I were administered on days 13 and 14 after peroral invasion at a dose of 150 mg / kg body weight (w / w). The standard was also applied on the 13th and 14th day after the invasion at a dose of 150 mg / kg. wt., calculated as niclosamide means a dose of 4.58.10-4.. wt.

The anthelmintic activity of the compounds of formula I as a percentage of the indirect activity according to the Steward is given below.

Substituent in Formula I is a dose of 1 kg. wt. efficiency in% by indirect activity example design example R1 R2 H Cl 3.07.10-4 94.4 1 NO 2 H 2.86.10-4 67.2 2 HN ° 2 2.95.10-4 61.4 3

The process for preparing the compounds of the invention is simple and provides the desired products in satisfactory yields. Further details are given in the following examples. The examples are merely illustrative, not limiting. Example 1 2,3-bis (4-chlorobenzamido) phenazine To a suspension of 10.51 g (0.05 mol) 2,3-diaminophenazine in 100 ml pyridine was added 17.53 g dropwise with stirring at 20 to 30 ° C. (0.1 mol) 4-chlorobenzoyl chloride and stirred for 6 h at rt

Claims (1)

3 254544 at 20 ° C. Then the reaction mixture was poured into 800 ml of water, the precipitated product was filtered off with suction and recrystallized from dimethylformamide. 10.42 g (42.8%) of a compound of m.p. 321 to 322 ° C and the composition C 26 H 16 C 12 N 4 O 2. Example 2 2.3- bis (3-nitrobenzamido) phenazine A crude substance was prepared from 10.51 g (0.05 mol) of 2,3-diaminophenazine and 18.58 g (0.1 mol) of 3-nitrobenzoyl chloride as described in Example 1. which was recrystallized from 90% aqueous dimethylformamide. 18.69 g (71.3%) of the product of m.p. 325 to 326 ° C and composition C-, Η., Ν, Ο, .Η.Ο. EXAMPLE 3 2.3- Bis (4-Nitrobenzamido) Phenazine The method described in Example 1 was from 10.51 g (0.05 mol) of 2,3-diaminophenazine and 18.58 g (0.1 mol) of 4. -nitrobenzoyl chloride was prepared crude which was recrystallized from dimethylformamide. 15.61 g (61.4%) of the product of m.p. From 356 to 357 ° C and a composition of C2gHgNgOg. BACKGROUND OF THE INVENTION 2,3-Bis (benzamido) phenazines of Formula I group.