CS276317B6 - 6-salicylideneamino-2-benzotiazolíntion - Google Patents

Abstract

The previously unknown 6-salicylideneamino-2-benzothiazolinethione was prepared. The synthesis of the above compound is carried out by the reaction of 6-amino-2-benzothiazolinethione with salicylaldehyde in a mixture of dimethyl sulfoxide and ethanol at boiling temperature.

Description

The present invention provides 6-salicylideneamino-2-benzothiazolinethione.

Until now, 2-isopentylthio-6-salicylideneaminobenzothiazole has been known to show anthelmintic activity against the model helminth Hymenolepis nana. / Sidóová, E. and Daněk, J ,, CS 271 547 /.

We have now found that a hitherto unknown compound of the formula

is anthelmintically effective against the relatively resistant model helmint Nippostrngylus brasiliensis.

At the same time, a process for the preparation of said compound by reacting 6-amino-2-benzothiazolinethione and salicylaldehyde was found, which is characterized in that 6-amino-2-benzothiazolinethione is reacted with salicylaldehyde in a mixture of dimethyl sulfoxide and ethanol under boiling.

The following examples illustrate, but do not limit, the preparation and properties of the compound of the invention.

Example 1

Preparation of 6-salicylideneamino-2-benzothiazolinethione

6-Amino-2-benzothiazolinethione (3.65 g, 0.02 mol) was dissolved in dimethyl sulfoxide (7 cm ³ ). Ethanol (42 cm ³ ) was added to the solution, then salicylaldehyde (3.6 g, 0.03 mol) and the mixture was heated to reflux for 5 minutes. The orange crystalline product, isolated after cooling to 5 ° C, was thoroughly washed with ethanol cooled to 5 ° C. The yield of 6-salicylideneamino-2-benzothiazolinethione, mp 276-278 ° C, was 5.5 g (96%). '

MW = 286.38 for C ₁₄ H ₁₀ N ₂ 0S _2% calculated C 58.72 H 3.52 H 9.78 S 22.39 Found%: 58.85 3.43 9.78 22.24

Example 2

The anthelmintic activity of the compound of the invention against the model helminth Nippostrongylus brasiliensis

Anthelmintic efficacy was determined in male rats aged 4 to 6 weeks and weighing 120 to 140 g. The experimental group always consisted of 6 rats. 2 groups were control-invaded, untreated, one group was treated with a standard Levamisole preparation and another group was administered a compound of the invention. The invasion was performed with fresh larvae of Nippostrongylus brasiliensis III. invasive stage of 500 larvae per rat. The first application was performed on the 3rd day after the invasion / day 4 of the experiment /, the second application on the 6th day after the invasion. The dose size was 2 times and 150 mg kg ^-1 live weight. The application was performed without a previous hunger strike. The substances were suspended in Dorfman's reagent and applied by weight in a volume of 0.65 to 12 cm ³ . Rats in the control untreated groups were orally administered Dorfman's reagent alone. Corpological examination of faeces was performed on day 6 after invasion / 7. day of experiment / before the second application of test substance or Dorfman's reagent in control groups. The experiment was terminated by fasting on day 7 after invasion and by killing rats on day 8 after invasion / 9. day of experiment. You have been evaluated more effectively

CS 276 317 B6 by performing a helmintological autopsy of the first two thirds of the small intestine. Treatment efficacy was expressed as a percentage by Steward's indirect activity method.

The compound of the invention showed an activity corresponding to 27.1% of the activity of the standard (levamisole).

Significantly, the hitherto unknown compound of the new structure showed activity against the model helmint of Nippostrongylus brasiliensis, which represents 27.1% of the standard preparation of levamisole (in said model helmint it is considered to be a remarkable activity above%).

The compound of the invention can be used as an active ingredient in anthelmintic preparations, or as an intermediate for further syntheses.

Claims (2)

PATENT CLAIMS Salicylideneamino-2-benzothiazolidinone of formula 2. A process for the preparation of a compound according to item 1, characterized in that 6-amino-2-benzothiazolinethione is reacted with salicylaldehyde under boiling in a 1: 6 mixture of dimethyl sulfoxide and ethanol.