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Molecules 2012, 17(2), 1233-1246; doi:10.3390/molecules17021233
Article

Synthesis of Novel IP Agonists via N-Aminoethyl Cyclic Amines Prepared by Decarboxylative Ring-Opening Reactions

, , , , , , ,  and *
Pharmaceutical Research Laboratories, Toray Industries Inc., 6-10-1 Tebiro, Kamakura, Kanagawa 248-8555, Japan
* Author to whom correspondence should be addressed.
Received: 7 December 2011 / Revised: 20 January 2012 / Accepted: 21 January 2012 / Published: 31 January 2012
(This article belongs to the Special Issue Heterocycles)
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Abstract

An efficient synthesis of a highly potent and selective IP (PGI2 receptor) agonist that is not structurally analogous to PGI2 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.
Keywords: amines; anilines; piperidines; heterocycles; IP agonists amines; anilines; piperidines; heterocycles; IP agonists
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Morita, Y.; Ishigaki, T.; Kawamura, K.; Hayashi, R.; Isogaya, M.; Kitsukawa, M.; Miyamoto, M.; Uchida, M.; Iseki, K. Synthesis of Novel IP Agonists via N-Aminoethyl Cyclic Amines Prepared by Decarboxylative Ring-Opening Reactions. Molecules 2012, 17, 1233-1246.

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