title: Synthesis of novel IP agonists via N-aminoethyl cyclic amines prepared by decarboxylative ring-opening reactions.
abstract: An efficient synthesis of a highly potent and selective IP (PGI(2) receptor) agonist that is not structurally analogous to PGI(2) is described. This synthesis is accomplished through the following key steps: Nucleophilic ring-opening of 3-(4-chlorophenyl)-oxazolidin-2-one prepared by a one-pot procedure with 4-piperidinol and selective O-alkylation of 1-(2-(4-chlorophenylamino)ethyl)piperidin-4-ol. The obtained compound is a potent and selective IP agonist displaying a long duration of action.
authors.affiliation: Pharmaceutical Research Laboratories, Toray Industries Inc., 6-10-1 Tebiro, Kamakura, Kanagawa 248-8555, Japan.
authors.forename: Yasuhiro
authors.initials: Y
authors.lastname: Morita
authors.forename: Takeshi
authors.initials: T
authors.lastname: Ishigaki
authors.forename: Kuniaki
authors.initials: K
authors.lastname: Kawamura
authors.forename: Ryoji
authors.initials: R
authors.lastname: Hayashi
authors.forename: Masafumi
authors.initials: M
authors.lastname: Isogaya
authors.forename: Mika
authors.initials: M
authors.lastname: Kitsukawa
authors.forename: Mitsuko
authors.initials: M
authors.lastname: Miyamoto
authors.forename: Masashi
authors.initials: M
authors.lastname: Uchida
authors.forename: Katsuhiko
authors.initials: K
authors.lastname: Iseki
mesh_terms: D000478:Alkylation; D000588:Amines / Q000737:chemistry*; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D044006:Receptors, Epoprostenol / Q000819:agonists*; D016339:Spectrometry, Mass, Fast Atom Bombardment
chemical_list: D000588:Amines; D044006:Receptors, Epoprostenol