Benzimidazole derivatives, compositions thereof and method of use as anthelmintics

Abstract

Benzimidazolederivatives are provided having the structure ##STR1## wherein R 1 is lower alkyl, phenyl-lower alkyl, halo-lower alkyl, mono-lower alkylaminoalkyl, di-lower alkylaminoalkyl, and alkyl pyridinium halide, R 2 and R 3 may be the same or different and are hydrogen or lower alkyl, R 4 is cycloalkyl or cycloalkenyl, and m is 0 to 3, n is 0 to 3, m+n being ≦5. These compounds are useful as anthelmintic agents.

What is claimed is: .[.1. A compound of the structure ##STR53## wherein R 1  is lower alkyl, phenyl-lower alkyl, halo-lower alkyl, mono lower alkylaminoalkyl, and alkyl pyridinium halide, R 2  and R 3  are the same or different and are selected from the group consisting of hydrogen or lower alkyl, and R 4  is cycloalkyl containing 3 to 12 carbons or cycloalkenyl containing 3 to 10 carbons, m is 0 to 3, n is 0 to 3 and m+n is ≦5, and physiologically acceptable salts thereof where 
     
        R 1  includes an amino function..]. .[.2.  The compound as defined in claim 1 wherein R 1  is lower alkyl or benzyl..]. .[.3. The compound as defined in claim 1 wherein R 2  and R 3  are hydrogen or methyl..]. .[.4. The compound as defined in claim 1 wherein m is 0 and n is 0, and R 2  and R 3  are hydrogen..]. .[.5. The compound as defined in claim 1 having the name [5-[(cyclopropylmethyl)thio]-1H-benzimidazol-2-yl]-carbamic acid, methyl ester..]. .[.6. The compound as defined in claim 1 having the name [5-[(cyclohexylmethyl)thio]-1H-benzimidazol-2-yl]-carbamic acid, methyl 
     
     
        ester..]. 7. .[.The.]. .Iadd.A .Iaddend.compound .[.as defined in claim 1.]. having the name [5-[(2,2-dichlorocyclopropylmethyl)thio]-1H-benzimidazol-2-yl]carbamic 
     
     
        acid, methyl ester. .[.8.  The compound as defined in claim 1 having the name [5-[(cyclohexen-3-yl methyl)thio]-1H-benzimidazol-2-yl]-carbamic 
     
     
        acid, 3-dimethyl-aminopropyl ester..]. 9. A pharmaceutical composition for use in treating helminthiasis comprising a therapeutically effective amount of a compound as defined in claim .[.1.]. .Iadd.7 .Iaddend.and a 
     
     
        pharmaceutically acceptable carrier therefor. 10. A method for treating helminthiasis which comprises administering to a mammalian host a therapeutically effective amount of the composition as defined in claim 9.