Six
potential process related impurities were detected during the
impurity profile study of an antiarrhythmic drug substance, Dronedarone
(1). Simple high performance liquid chromatography and
liquid chromatography–mass spectrometry methods were used for
the detection of these process impurities. Based on the synthesis
and spectral data (MS, IR, 1H NMR, 13C NMR,
and DEPT), the structures of these impurities were characterized as
5-amino-3-[4-(3-di-n-butylaminopropoxy)benzoyl]-2-n-butylbenzofuran (impurity I); N-(2-butyl-3-(4-(3-(dibutylamino)propoxy)benzoyl)benzofuran-5-yl)-N-(methylsulfonyl)methanesulfonamide (impurity II); N-(2-butyl-3-(4-(3-(dibutylamino)propoxy)benzoyl)benzofuran-5-yl)-1-chloromethanesulfonamide
(impurity III); N-{2-propyl-3-[4-(3-dibutylaminopropoxy)benzoyl]benzofuran-5-yl}methanesulfonamide
(impurity IV); N-(2-butyl-3-(4-(3-(dibutylamino)propoxy)benzoyl)benzofuran-5-yl)formamide
(impurity V); and (2-butyl-5-((3-(dibutylamino)propyl)amino)benzofuran-3-yl)(4-(3-(dibutylamino)propoxy)phenyl)methanone
(impurity VI). The synthesis and characterization of these impurities
are discussed in detail.
Tartrate salt of carbocyclic amine 2 is one of the key starting materials for the synthesis of Ticagrelor 1. During the synthesis of 1, the isomers of 2 also need to be considered as potential impurities and characterized before establishing the specification of product. In the present work, detailed study has been carried out to synthesize the related substances of 2, and their structure characterization has been discussed.
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