Identification, synthesis and structure assignment of two impurities of Erlotinib, a drug used for the treatment of some types of cancer.
Keywords:Eritronib, Cancer, Isomers, Impurity
In the synthesis and industrial production of Erlotinib, the formation of organic impurities has been detected, so the identification and control of these is a critical point within the process. Standards for the consumption of pharmaceutical products are well established for active substances. In this sense, the synthesis and unequivocal identification of two impurities of Erlotinib as structural isomers was developed in the present study. The structural characterization of both isomers was confirmed by 1H and 13C-NMR as well as by their X-ray diffraction study.
Harris, C.; Hennequin, L.; Willerval, O. Tetrahedron Lett.2009, 50, 1600-1602.
Chandregowda, V.; Rao, V. G.; Reddy, G. C. Org. Process Res. Dev. 2007, 11, 813-816.
Zhang, G.; Zha, L. Res. Chem. Intermed. 2013, 39, 2303–2309.
Bridjes, A. J. Chem. Rev. 2001, 101, 2541-2572.
Bagul, C.; Rao, G. K.; Makani, V. K. K.; Tamboli, J. R.; Pal-Bhadra, M.; Kamal, A. Med. Chem. Commun. 2017, 8, 1810-1816.
Schnur, R. C.; Arnold, L. D. from PCT Int. Appl. (1996), WO 9639347 A1 Oct 03, 1996.
Q3A(R2) Impurities in New Drug Substances, ICH Tripartite Guideline.
Volk, B.; Dancsó, A.; Bakó, T.; Peltz, C.; Simig, G. Org. Process Res. Dev. 2011, 15, 339-342.
Crystallographic data was deposited at Cambridge Crystallographic Data Center (CCDC 1535571 for 4 and 1535572 for 5).
Crossland, R. K.; Servis, K. L. J. Org. Chem. 1970, 35, 3195-3196.
Authors who publish with this journal agree to the following terms:
- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.