Anthelmintic benzimidazol-carbamates

Details Anthelmintic benzimidazol-carbamates Anthelmintic benzimidazol-carbamates

C - Chemistry, Metallurgy

07

D

260/314.3

C07D 235/04 (2006.01) A61K 31/415 (2006.01) C07D 235/32 (2006.01)

Patent

CA 1104142

ABSTRACT OF THE DISCLOSURE: A process for preparing new benzimidazol-(2)-methyl-car- bamates substituted in the 5(6) position and having the gene- ral formula (I): Image wherein: x=s or SO; and n=0; 1; or 2, which comprises reducing 2-nitro 4-thiocyanoaniline with sodium borohydride in dimethylformamide to obtain the alkaline mercap- tate of orthonitro-aniline; adding to the so-obtained mercap- tate, a halide of the general formula: X - CH2-(CH2-CH2)n - CH=CCl2 in which x is halogen and n is 0; 1; or 2; to obtain 4 ?.omega.,.omega.- dihaloalkyl-(.omega.-1)-en-1-yl)-thio? -orthonitroaniline in which .omega. is 3,5 or 7; reducting the so-obtained product with hydro- sulfite to obtain the corresponding phenylenediamine; reacting the latter with 1,3-bis-dimethoxy-carboxyl-S-methyl-isothiourea to obtain the thiol of the formula I' Image (I') and, if desired, oxidizing this thiol of formula (I') in which X=S, with m-chloroperbenzoic acid to obtain the corresponding sulfoxide of formula (I'') Image (I'') The substituted carbamates according to the invention can be used, in a suitable form, for combating intestinal, pulmonary and hapa- tic parasites, particularly Helminthes in animals.

301605

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