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Evaluation of WO2014121383 A1: a process for preparation of rufinamide and intermediates.
Expert Opinion on Therapeutic Patents 2018 November 16
INTRODUCTION: There is great potential in the synthetic development of rufinamide to treat childhood onset epilepsy known as Lennox-Gastaut syndrome (LGS). Areas covered: 1,4-disubstituted triazole ring formed by 1,3-dipolar cycloaddition reaction is an important structural motif widely used to construct diverse chemotypes in chemical, biological and material fields. 1,2,3-triazole ring containing rufinamide, an antiepileptic drug developed by Novartis is useful in combination with other antiepileptic medicaments for the treatment of childhood onset epilepsy known as Lennox-Gastaut syndrome (LGS). There are numerous synthetic methods used to construct the rufinamide through 1,3-dipolar cycloaddition. The application claims processes for the preparation of rufinamide and their intermediates. The synthetic strategy covered for the synthesis of rufinamide using activated acetylenic esters. The activation is done using N-hydroxy succinimide, N-hydroxyphthalimide, 1-hydroxy benzotriaole and 4-nitro phenol. Expert opinion: The manufacturing route appears to follow the regioselective Cu catalyzed cycloaddtion of 2,6-difluro benzyl azide with or without isolated activated acetylenic esters in 3 steps that provides a good lead for new synthetic strategy for the rufinamide synthesis.
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