Current Issues of Pharmacy and Medical Sciences

Synthesis and characterization of related substances of Azilsartan Kamedoxomil

Curr Issues Pharm Med Sci., Vol. 30, No. 1, 31-35

N V D Harikiran Maddi1,2, Srinivas Garaga1,2, Ambati V. Raghava Reddy1,
Paul Douglas Sanasi2, Raghubabu Korupolu2

1 Chemical Research and Development Department, Aurobindo Pharma Ltd, Survey No:71&72, Indrakaran Village, Sangareddy Mandal, Medak district, Hyderabad – 502329, Andhra Pradesh, India
2 Department of Engineering Chemistry, A. U. College of Engineering (A), Andhra University, Visakhapatnam – 530 003, Andhra Pradesh, India

DOI: https://doi.org/10.1515/cipms-2017-0007

Abstract

Azilsartan Kamedoxomil is an AT1-subtype angiotensin II receptor blocker (ARB). During the laboratory synthesis of Azilsartan Kamedoxomil, four related substances of Azilsartan Kamedoxomil were observed and identified. These were 2-Ethoxy-3-[[4-[2-[4-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl]-5-oxo-1,2,4-oxadiazol-3-yl]phenyl]phenyl]methyl] benzimidazole-4-carboxylic acid (azilsartan N-medoxomil, 9), (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 2-ethoxy-3-[[4-[2-[4-[(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl]-5-oxo-1,2,4-oxadiazol-3-yl]phenyl]phenyl] methyl] benzimidazole-4-carboxylate (azilsartan dimedoxomil, 10), (5-methyl-2-oxo-1,3-dioxo-4-yl)methyl 1-[2’-(4,5-dihydro-5-oxo-4H-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl]-2-methoxy-1H-benzimidazole-7-carboxylate (methoxy analogue of azilsartan medoxomil, 11), Methyl 1-((2’-amidobiphenyl-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate (amide methyl ester, 12). The present work describes the origin, synthesis and characterization of these related substances.

 

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Keywords

Azilsartan Kamedoxomil, related substances, synthesis, characterization.

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