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Three-Step Synthesis of the Antiepileptic Drug Candidate Pynegabine.


ABSTRACT: Pynegabine, an antiepileptic drug candidate in phase I clinical trials, is a structural analog of the marketed drug retigabine with improved chemical stability, strong efficacy, and a better safety margin. The reported shortest synthetic route for pynegabine contains six steps and involves the manipulation of highly toxic methyl chloroformate and dangerous hydrogen gas. To improve the feasibility of drug production, we developed a concise, three-step process using unconventional methoxycarbonylation and highly efficient Buchwald-Hartwig cross coupling. The new synthetic route generated pynegabine at the decagram scale without column chromatographic purification and avoided the dangerous manipulation of hazardous reagents.

SUBMITTER: Sun YJ 

PROVIDER: S-EPMC10343641 | biostudies-literature | 2023 Jun

REPOSITORIES: biostudies-literature

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Three-Step Synthesis of the Antiepileptic Drug Candidate Pynegabine.

Sun Yi-Jing YJ   Gong Ya-Ling YL   Lu Shi-Chao SC   Zhang Shi-Peng SP   Xu Shu S  

Molecules (Basel, Switzerland) 20230621 13


Pynegabine, an antiepileptic drug candidate in phase I clinical trials, is a structural analog of the marketed drug retigabine with improved chemical stability, strong efficacy, and a better safety margin. The reported shortest synthetic route for pynegabine contains six steps and involves the manipulation of highly toxic methyl chloroformate and dangerous hydrogen gas. To improve the feasibility of drug production, we developed a concise, three-step process using unconventional methoxycarbonyla  ...[more]

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