CS257399B1 - B-Formainido2 benzotiaw) líntión - Google Patents

Abstract

The solution concerns a previously unknown 6- -formamido-2-benzothiazolinethione of the formula HCG"nh lf C= s and a method of its preparation. The reaction is carried out by formylation of 6- -amino-2-benzothiazolinethione with 85% formic acid at boiling temperature. The new compound is antimycobacterially effective against tuberculous mycobacteria, especially against atypical strains of M. avium, M. fortuitum and M. kansasii; it can be used as an active ingredient of antimycobacterial preparations, or as an intermediate for further syntheses.

Description

The solution relates to the hitherto unknown 6-formamido-2-benzothiazolinothione of the formula HCO "nh 1jc = and the process for its preparation.

The reaction is performed by formylation of 6-amino-2-benzothiazolinothione with 85% formic acid at boiling point. The new compound is antimycohacterially effective against tuberculous mycobacteria, especially against atypical M. avium strains, M. fortuitum and M. kansasii; it can be used as an active ingredient of antimycobacterial preparations, or as an intermediate for further syntheses. 257399 257399

The present invention provides 6-formamido-2-benzothiazolinothione. 2-Benzothiazolinothione is an antimicrobial active compound. As a fungicide, it is an effective component of the established Dermacid formulation, and is also effective as an antimycobacterial.

It has now been found that the now unknown compound of the formula is effective against typical tuberculous mycobacteria Mycobacterium (M.) tuberculosis H37RV, as well as against atypical M. kansasii mycobacterial mycobacteria. M. avium and M. fortuitum. At the same time, a method for preparing said 6-amino-2-benzothiazolinothione-based compound was found. The reaction is carried out by acylating 6-amino-2-benzothiazolinothione with 85% formic acid in a 1: 4 to 1: 12 molar ratio at 70-101 ° C for 1 to 30 minutes.

MIC fabric tbc.

H37RV

The following examples illustrate, but do not limit, the preparation and properties of the compound of the invention. Example 1 Preparation of 6-formamido-2-benzothiazolinothione 6-Amino-2-benzothiazolynthion (5.45 g, 0.03 mol) and 85% formic acid (7.5 cm 3, 9 g, 0.166 mol) were heated together to boil. After two minutes of boiling, the mixture was left to stand for 30 minutes, then poured into cold water (300 cm 3). Pure 6-formamido-2-benzothiazolinothione was obtained, m.p. 257-259.5 ° C with decomposition, which did not require further purification in addition to a neutral wash with water. The yield was 5.7 g (89.5%).

For C8H6N2OS2 (212.29) calculated: 45.26% C, 3.80% H, 13.20% N, 30.21% O / S, found: 45.56% C, 3.67% H, 13 N, 30.32%. Example 2

The antimycobacterial activity of the compound of the invention compared to that of known antituberculotics versus Mycobacterium (^ g-cm-3) kansasii avium fortuitum PKG 8 16/18 No. 1,021

Compound of the Invention 25 25 25 50 Isoniazid (INH) 1 5 50 25 Etionamide (ETA) 5 25 25 50 MIC - Minimum inhibitory concentration in pg. cm-3

Antimycobacterial efficacy against tuberculous mycobacteria was observed in liquid Sula under the dilution test. Dimethylsulfoxide was used as solvent. The final concentration of substances in the pod was 0.5, 1, 5, 10, 25, 50 and 100 µg. cm'3. Significant is the fact that the compound of the invention is a new, hitherto unknown structure and its antimycobacterial activity, especially against atypical tuberculous mycobacteria, is comparable to the known antituberculotics Isoniazid and Etionamide. The compound of the invention may be used as an active ingredient of antimycobacterial preparations or as an intermediate for further syntheses.

Claims (2)

SUBJECT 1. 6-Formamido-2-benzothiazolinothione of the formula INVENTION 2. A process for the preparation of a compound as claimed in claim 1, which comprises reacting 6-amino-2-benzotlazolithione with 85% formic acid in a molar ratio of 1: 4 to 1: 12 at 70 to 101 ° C for 1 to 4 ° C. 30 minutes.