- NOVEL PROCESS FOR THE PREPARATION OF PERAMPANEL AND ITS INTERMEDIATES THEREOF
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The present invention provides novel process for preparation of 3-(2-cyanophenyl)-5-(2- pyridyl)-1-phenyl-1,2-dihydropyridin-2-one, commonly known as perampanel having the formula I. The present invention also provides novel intermediate compound of formula VI and process for the preparation of intermediate compound of formula VI. The present invention also provides purification of perampanel.
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- PROCESS FOR THE PREPARATION OF PERAMPANEL
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The present invention relates to processes for the preparation of perampanel and its intermediates.
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- A practical, laboratory-scale synthesis of Perampanel
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The orally active, noncompetitive, selective AMPA receptor antagonist Perampanel, 2-[1,6-dihydro-6-oxo-1-phenyl-(2,3-bipyridin)-5-yl]benzonitrile, has been prepared from readily available, relatively inexpensive starting materials. The synthesis was carried out on a laboratory scale with no specialized equipment, and involved only two chromatographic purifications. Georg Thieme Verlag Stuttgart. New York.
- McElhinny Jr., Charles J.,Carroll,Lewin, Anita H.
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- Discovery of 2-(2-Oxo-1-phenyl-5-pyridin-2-yl-1,2-dihydropyridin-3-yl) benzonitrile (Perampanel): A novel, noncompetitive α-amino-3-hydroxy-5- methyl-4-isoxazolepropanoic acid (AMPA) receptor antagonist
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Dysfunction of glutamatergic neurotransmission has been implicated in the pathogenesis of epilepsy and numerous other neurological diseases. Here we describe the discovery of a series of 1,3,5-triaryl-1H-pyridin-2-one derivatives as noncompetitive antagonists of AMPA-type ionotropic glutamate receptors. The structure-activity relationships for this series of compounds were investigated by manipulating individual aromatic rings located at positions 1, 3, and 5 of the pyridone ring. This culminated in the discovery of 2-(2-oxo-1-phenyl-5- pyridin-2-yl-1,2-dihydropyridin-3-yl)benzonitrile (perampanel, 6), a novel, noncompetitive AMPA receptor antagonist that showed potent activity in an in vitro AMPA-induced Ca2+ influx assay (IC50 = 60 nM) and in an in vivo AMPA-induced seizure model (minimum effective dose of 2 mg/kg po). Perampanel is currently in regulatory submission for partial-onset seizures associated with epilepsy.
- Hibi, Shigeki,Ueno, Koshi,Nagato, Satoshi,Kawano, Koki,Ito, Koichi,Norimine, Yoshihiko,Takenaka, Osamu,Hanada, Takahisa,Yonaga, Masahiro
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p. 10584 - 10600
(2013/02/23)
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- CRYSTAL OF 1,2-DIHYDROPYRIDINE COMPOUND (TYPE IV)
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A crystal of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one characterized in having a diffraction peak at a diffraction angle (2θ±0.2°) of 15.4° in a powder X-ray diffraction or others.
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Page/Page column 4
(2009/04/24)
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- AMORPHOUS FORM OF 1,2-DIHYDROPYRIDINE COMPOUND
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An amorphous form of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridine-2-one.
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Page/Page column 5
(2008/12/08)
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- CRYSTAL OF 1,2-DIHYDROPYRIDINE COMPOUND AND METHOD FOR PRODUCING SAME
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The invention provides crystals of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one and production processes therefor.
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Page/Page column 10
(2008/06/13)
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- 1,2-DIHYDROPYRIDINE COMPOUNDS, PROCESS FOR PREPARATION OF THE SAME AND USE THEREOF
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The present invention provides a novel compound having an excellent AMPA receptor inhibitory action and/or kainate inhibitory action. A compound represented by the following formula, a salt thereof or hydrates thereof. In the formula, Q indicates NH, O or S; and R1, R2, R3, R4 and R5 are the same as or different from each other and each indicates hydrogen atom, a halogen atom, a C1-6 alkyl group or a group represented by the formula -X-A (wherein X indicates a single bond, an optionally sbutituted C1-6 alkylene group etc.; and A indicates an optionally substituted C6-14 aromatic hydrocarbocyclic group or 5- to 14-membered aromatic heterocyclic group etc.).
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