2-Amino- and 2-hydroxymethylbenzimidazolium bromides as protein tyrosine phosphatase 1В (PTP1В) inhibitors and other targets associated with diabetes mellitus

New 2-amino- and 2-hydroxymethylbenzimidazoles were synthesized and used to prepare the previously unknown 1,2,3-tri- and 1,2,3,5-tetrasubstituted benzimidazolium bromides with a biphenyl-containing substituent at the imidazole nitrogen atom. In some cases, these bromides exhibit activity against targets associated with diabetes mellitus. These compounds are strong protein tyrosine phosphatase 1B (PTP1B) inhibitors, exhibit chelating and antiglycation activity, but have no significant AT1 receptor antagonist activity. Hence, biphenyl-containing benzimidazolium derivatives can be considered as a basis for the development of new promising agents for the treatment of type 2 diabetes mellitus (DM2) and other diseases mediated by high phosphatase PTP1B activity.