10368. Telcagepant

Nomenclature

CAS number: 781649-09-0
N-[(3R,6S)-6-(2,3-Difluorophenyl)hexahydro-2-oxo-1-(2,2,2-trifluoroethyl)-1H-azepin-3-yl]-4-(2,3-dihydro-2-oxo-1H-imidazo[4,5-b]pyrindin-1-yl)-1-piperidinecarboxamide; N-[(3R,6S)-6-(2,3-difluorophenyl)-2-oxo-1-(2,2,2-trifluoroethyl)azepan-3-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide; MK-0974.
C26H27F5N6O3; mol wt 566.52.
C 55.12%, H 4.80%, F 16.77%, N 14.83%, O 8.47%.

Description and references

Calcitonin gene-related peptide (CGRP) receptor antagonist. Prepn: C. S. Burgey et al., WO 04092168; eidem, US 6953790 (2004, 2005 both to Merck & Co.); D. V. Paone et al., J. Med. Chem. 50, 5564 (2007) DOI PubMed. Improved synthesis: C. S. Burgey et al., Org. Lett. 10, 3235 (2008) DOI PubMed. Determn by HTLC-MS/MS in plasma and urine: Y. Xu et al., J. Chromatogr. B 863, 64 (2008) DOI PubMed. Determn of isomers by LC-MS/MS in plasma: Y. Xu, D. G. Musson, ibid. 873, 195 (2008) DOI. Pharmacology: C. A. Salvatore et al., J. Pharmacol. Exp. Ther. 324, 416 (2008) DOI PubMed. Clinical evaluation in migraine: T. W. Ho et al., Neurology 70, 1304 (2008) DOI PubMed.

Chemical structure

Properties

[α]D20 18.5° (c = 1.0 in CHCl3). Sol in acetonitrile/water.

Derivative

Potassium salt monoethanolate.

Nomenclature

CAS number: 953077-35-5
Telcagepant potassium.
C26H26F5KN6O3.CH3OH; mol wt 636.66.
C 50.94%, H 4.75%, F 14.92%, K 6.14%, N 13.20%, O 10.05%.

Description and references

Prepn: K. Belyk, WO 07120592 (2007 to Merck & Co.).

Properties

White powder.

Therapeutic Category

Antimigraine.

Keywords

Antimigraine