Pregabalin

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Overview Progablin is a blockbuster anticonvulsat drug, marketed as Lyrica, used to treat neuralgiac pain. A difficulty in its synthesis is ensuring that the right chiral enantiomer is formed. Trinity researchers have developed a new method to selectively synthesise the appropriate enatiomer of an immediate precursor to the drug using a highly efficient catalyst. The product yields and ‘enantio-selectiveness’ of the new process are uniformly excellent and the catalyst can be used under very mild and scalable conditions. Advantages The synthesis of ‘enantiopure’ pregabalin has the requirement for a step which discards 50% of the product which is inefficient and wasteful. The technology on offer here modifies the synthesis process to preferentially create the desired enantiomer. This invention is based on a desymmetrisation step – a meso starting material is converted to a chiral enantioenriched product in a highly selective manner. Thus the need for a costly resolution step has been removed. Other similar attempts to create a enanatiomer sensitive catalyst have proved impractical due to a requirement for large amounts of catalyst (quinine or quinidine) and the need for low reaction temperatures (50 and -78 °C). The catalyst presented here is efficient to the point where it can be used at low levels of 1-2 mol%. In addition this catalyst functions at ambient temperatures (or lower, if required). Development Stage The catalyst has been reduced to practice and the efficiency of its enantiomer selectiveness is known. Principal Inventor(s) Dr. Stephen Connon, Aldo Peschiulli, Lyn Markey Patent A patent application has been filed in Europe TCD Ref: SC01-181-01