Co-crystal of 4,4' -sulfonyldianiline and hexamethylenetetramine: Supramolecular interactions and thermal stability studies

摘要

Co-crystal containing 1:1 ratio of 4,4'-sulfonyldianiline (dapsone, a sulfonamide antibiotic) and hexamethylenetetramine (HMTA) has been prepared. Herein, we report the synthesis, characterization of the drug-drug co-crystal and its thermal stability. This co-crystal can be prepared by means of solvent evaporation and solid state synthesis (neat ball milling). Single crystal structural characterization of the co-crystal revealed that the co-crystal structure is secured by hydrogen bonds -NH2 center dot center dot center dot N and multiple weak interactions, including C-H center dot center dot center dot pi and C-H center dot center dot center dot O, between the co-formers. Moreover, thermal gravimetric analysis showed that the co-former HMTA demonstrates higher thermal stability after co-crystallized with dapsone. These investigations proved that DAP is an ideal parent drug to prepare drug-drug co-crystal. The case study expands the pharmaceutically acceptable solid forms of DAP. (C) 2017 Elsevier B.V. All rights reserved.