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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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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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