Abstract
Oxcarbazepine (OXC), the active ingredient of Trileptal® (Novartis Pharma), has become the most widely prescribed drug for the treatment of epilepsy and other CNS diseases, due to its improved side-effect profile and relevant anticonvulsant activity compared to the parent drug, carbamazepine (CBZ). Given its importance and well-established therapeutic applications, much effort has been devoted to the improvement of its original synthetic protocol, searching for shorter, milder and more efficient routes, employing not only classical transformations but also modern synthetic tools, such as palladium-catalysed arylation reactions. In this article it is intended to resume the applications and features of OXC as an anticonvulsant drug, as well as to compile for the first time all the reported routes to OXC, from the originally-developed protocol to the latest methodology, which allowed for the synthesis of a family of structural analogues. Such synthetic sequences will be discussed and comprehensively classified according to whether the approach to OXC is based on either modifications on the iminodibenzyl ring or coupling reactions.
Keywords: Carbamoylation, Iminostilbene, Metalation, Intramolecular Friedel-Crafts Acylation, arylation reaction
Current Organic Chemistry
Title: Applications and Synthesis of the Antiepileptic Drug Oxcarbazepine and Related Structures
Volume: 11 Issue: 15
Author(s): M. Carril, R. SanMartin and E. Dominguez
Affiliation:
Keywords: Carbamoylation, Iminostilbene, Metalation, Intramolecular Friedel-Crafts Acylation, arylation reaction
Abstract: Oxcarbazepine (OXC), the active ingredient of Trileptal® (Novartis Pharma), has become the most widely prescribed drug for the treatment of epilepsy and other CNS diseases, due to its improved side-effect profile and relevant anticonvulsant activity compared to the parent drug, carbamazepine (CBZ). Given its importance and well-established therapeutic applications, much effort has been devoted to the improvement of its original synthetic protocol, searching for shorter, milder and more efficient routes, employing not only classical transformations but also modern synthetic tools, such as palladium-catalysed arylation reactions. In this article it is intended to resume the applications and features of OXC as an anticonvulsant drug, as well as to compile for the first time all the reported routes to OXC, from the originally-developed protocol to the latest methodology, which allowed for the synthesis of a family of structural analogues. Such synthetic sequences will be discussed and comprehensively classified according to whether the approach to OXC is based on either modifications on the iminodibenzyl ring or coupling reactions.
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Cite this article as:
Carril M., SanMartin R. and Dominguez E., Applications and Synthesis of the Antiepileptic Drug Oxcarbazepine and Related Structures, Current Organic Chemistry 2007; 11 (15) . https://dx.doi.org/10.2174/138527207782023148
DOI https://dx.doi.org/10.2174/138527207782023148 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Chemistry and Biology of Carbohydrates
Carbohydrates are one of the most abundant natural products and are considered to be extremely important biomolecules for their ever-increasing impact on chemistry and biology. Their role in several important biological processes, notably energy storage, transport, modulation of protein function, intercellular adhesion, malignant transformation, signal transduction, viral, and bacterial cell ...read more
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