| Identification | Back Directory | [Name]
perampanel 3/4 hydrate | [CAS]
1571982-04-1 | [Synonyms]
4 hydrate
perampanel 3
Perampanel 3/4H2O
Perampanel Hydrate
perampanel 3/4 hydrate
Perampanel hydrate (4:3)
3-(2-CYANOPHENYL)-1-PHENYL-5-(2-PYRIDYL)-1,2-DIHYDROPYRIDIN-2-ONE 3/4 HYDRATE
2-(1',6'-Dihydro-6'-oxo-1'-phenyl[2,3'-bipyridin]-5'-yl)benzonitrile hydrate (4:3) | [Molecular Formula]
C23H17N3O2 | [MOL File]
1571982-04-1.mol | [Molecular Weight]
367.41 |
| Hazard Information | Back Directory | [Definition]
ChEBI:Perampanel hydrate is a hydrate obtained by combining four molecules of perampanel with three molecules of water. Used as an adjunctive therapy for the treatment of partial-onset seizures in patients with epilepsy. It has a role as an AMPA receptor antagonist and an anticonvulsant. It contains a perampanel. | [Clinical Use]
Perampanel is a selective, non-competitive α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid
receptor (AMPAR) antagonist approved for partial-onset seizures in patients with epilepsy. Perampanel was discovered and developed by Eisai. | [Synthesis]
A number of synthetic routes to perampanel have
been reported and the process scale route is described herein.Bromination of commercial 2-methoxypyridine (120) gave 5-bromo-2-methoxypridine 121 in 86%
yield (the scheme). Lithium halogen exchange was then accomplished by treating 121 with nbutyllithium
followed by reaction with 2-benzenesulfonylpyridine (122) to provide bi-aryl 123 which
was hydrolyzed under acidic conditions to give pyridine 124 in 60% overall yield. N-Arylation with
triphenylboroxine (125) in the presence of copper acetate afforded N-aryl pyridine 126 in 91% yield.
Pyridone 126 was reacted with N-bromosuccinimide to give bromopyridine 127 which was coupled
with 2-(1,3,2-dioxaborinan-2-yl)benzonitrile (128) under palladium catalyzed conditions to give
perampanel hydrate (XIX) in 86% yield after recrystallization from acetone/H2O.
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