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DB-6, with an IUPAC name of (Z)-5-(2,4-di-tert-butyl-6-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-5'-methyl-7,7'-dimethoxy-[4,4'-bibenzo[d][1,3]dioxole]-5,5'-dicarboxylate, is an investigational agent for acute liver failure. The focus of this study is the identification and characterization of major unknown impurities in DB-6 bulk drug samples. Four major impurities of DB-6 were detected by a high-performance liquid chromatography (HPLC) method and designated as IMP-I, IMP-II, IMP-III and IMP-IV. Accurate masses of these impurities were determined by using a Q-TOF mass spectrometer. Based on chromatographic, spectrometric data and plausible chemical transformation mechanism, the structures of IMP-I, IMP-II, IMP-III and IMP-IV were identified, respectively, as bifendate, (E)-5-(2,4-di-tert-butyl-6-((2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-5'-methyl-7,7'-dimethoxy-[4,4'-bibenzo[d][1,3]dioxole]-5,5'-dicarboxylate, (Z)-5-(3,5-di-tert-butyl-2-hydroxybenzylidene) thiazolidine-2,4-dione and bis(2,4-di-tert-butyl-6-((Z)-(2,4-dioxothiazolidin-5-ylidene)methyl)phenyl)-7,7'-dimethoxy-[4,4'-bibenzo[d][1,3]dioxole]-5,5'-icarboxylate. The impurities were isolated by preparative-HPLC or preparative high-speed counter-current chromatography and their structures were confirmed by NMR spectroscopy.

journal of chromatographic science

Identification, Separation and Characterization of Process-Related Impurities of Bifendate Derivative (DB-6), an Investigational Agent Combating Acute Liver Failure