381248-06-2

Basic information

• Product Name: 5'-broMo-1'-phenyl-[2,3'-bipyridin]-6'(1'H)-one
• Synonyms: 5'-broMo-1'-phenyl-[2,3'-bipyridin]-6'(1'H)-one;3-BroMo-1-phenyl-5-(pyridin-2-yl)pyridin-2(1H)-one;3-Bromo-1-phenyl-5-(pyridin-2-yl)-1,2-dihydropyridin-2-one;3-Bromo-1-phenyl-5-(pyridin-2-yl)-2(1H)-pyridone;3-Bromo-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one
• CAS NO: 381248-06-2
• Molecular Formula: C₁₆H₁₁BrN₂O
• Molecular Weight: 327.17534
• Mol File: 381248-06-2.mol

Chemical Properties

• Boiling Point: 461.7±45.0 °C(Predicted)
• Appearance: /
• Density: 1.539±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), DMSO (Slightly)
• PKA: 4.73±0.19(Predicted)
• Stability: Light Sensitive
• CAS DataBase Reference: 5'-broMo-1'-phenyl-[2,3'-bipyridin]-6'(1'H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5'-broMo-1'-phenyl-[2,3'-bipyridin]-6'(1'H)-one(381248-06-2)
• EPA Substance Registry System: 5'-broMo-1'-phenyl-[2,3'-bipyridin]-6'(1'H)-one(381248-06-2)

Safety Data

• Hazardous Substances Data: 381248-06-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5'-broMo-1'-phenyl-[2,3'-bipyridin]-6'(1'H)-one is used as an intermediate in the synthesis of Perampanel (P285522), an antiepileptic drug. It plays a crucial role in the development of this medication, which is designed to help control seizures and improve the quality of life for patients suffering from epilepsy. 5'-broMo-1'-phenyl-[2,3'-bipyridin]-6'(1'H)-one's unique structure allows it to be a key component in the creation of Perampanel, making it an essential part of the pharmaceutical industry's efforts to combat epilepsy and related conditions.

Upstream product

• 381725-50-4 1-phenyl-5-(pyridin-2-yl)-2(1H)-pyridone 
• 624-28-2 2,5-dibromopyridine 
• 13472-85-0 2-methoxy-5-bromopyridine 
• 381233-78-9 5-(2-Pyridyl)-1,2-dihydropyridin-2-one 
• 17997-47-6 2-tri-n-butylstannylpyridine 
• 381725-49-1 2-methoxy-5-(pyridin-2-yl)pyridine 
• 98-80-6 phenylboronic acid 
• 163105-89-3 2-methoxy-pyridine-5-boronic acid 
• 381233-79-0 3-bromo-5-(2-pyridyl)-1,2-dihydropyridin-2-one 
• 197958-29-5 pyridin-2-ylboronic acid 

Downstream Products

• 380917-97-5 [14C]-Perampanel 
• 380918-50-3 C₂₃H₁₈N₂O 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF PERAMPANEL

The present invention relates to processes for the preparation of perampanel and its intermediates.

NOVEL PROCESS FOR THE PREPARATION OF PERAMPANEL AND ITS INTERMEDIATES THEREOF

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.

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

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.

A practical, laboratory-scale synthesis of Perampanel

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.

CRYSTAL OF 1,2-DIHYDROPYRIDINE COMPOUND (TYPE IV)

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.

AMORPHOUS FORM OF 1,2-DIHYDROPYRIDINE COMPOUND

An amorphous form of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridine-2-one.

CRYSTAL OF 1,2-DIHYDROPYRIDINE COMPOUND AND METHOD FOR PRODUCING SAME

The invention provides crystals of 3-(2-cyanophenyl)-5-(2-pyridyl)-1-phenyl-1,2-dihydropyridin-2-one and production processes therefor.

1,2-DIHYDROPYRIDINE COMPOUNDS, PROCESS FOR PREPARATION OF THE SAME AND USE THEREOF

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.).