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

doi:10.3390/molecules17021233

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

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

Yasuhiro Morita, Takeshi Ishigaki, Kuniaki Kawamura, Ryoji Hayashi, Masafumi Isogaya, Mika Kitsukawa, Mitsuko Miyamoto, Masashi Uchida and Katsuhiko Iseki*

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; in revised form: 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

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Cite This Article

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.

AMA 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(2):1233-1246.

Chicago/Turabian Style

Morita, Yasuhiro; Ishigaki, Takeshi; Kawamura, Kuniaki; Hayashi, Ryoji; Isogaya, Masafumi; Kitsukawa, Mika; Miyamoto, Mitsuko; Uchida, Masashi; Iseki, Katsuhiko. 2012. "Synthesis of Novel IP Agonists via N-Aminoethyl Cyclic Amines Prepared by Decarboxylative Ring-Opening Reactions." Molecules 17, no. 2: 1233-1246.

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