9090. Tebanicline
Nomenclature
CAS number: 198283-73-7
5-[(2R)-2-Azetidinylmethoxy]-2-chloropyridine; ABT-594. C9H11ClN2O; mol wt 198.65.
C 54.42%, H 5.58%, Cl 17.85%, N 14.10%, O 8.05%.
Description and references
Non-opioid 3-pyridyl ether analgesic acting acting via a neuronal nicotinic acetylcholine receptor mediated mechanism. Prepn: M. W. Holladay et al., WO 9640682; M. A. Abreo et al., US 5948793 (1996, 1999 both to Abbott); as hydrochloride: M. W. Holladay et al., J. Med. Chem. 41, 407 (1998). Asymmetric synthesis: J. K. Lynch et al., Tetrahedron: Asymmetry 9, 2791 (1998). Analgesic activity and receptor affinity: A. W. Bannon et al., Science 279, 77 (1998). Pharmacology in vitro: D. L. Donnelly-Roberts et al., J. Pharmacol. Exp. Ther. 285, 777 (1998); in vivo: A. W. Bannon et al., ibid. 787. Efficacy in neuropathic pain models: idem et al., Brain Res. 801, 158 (1998).
Derivative
Hydrochloride.Nomenclature
CAS number: 203564-54-9
Properties
mp 116-117°. [α]23D +8.6° (c = 0.52 in methanol).Derivative
Tosylate.Nomenclature
CAS number: 198283-74-8
C9H11ClN2O.C7H8O3S; mol wt 370.85.
C 51.82%, H 5.16%, Cl 9.56%, N 7.55%, O 17.26%, S 8.65%.