Volume 31, Issue 51
Heterocyclic Compounds
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ChemInform Abstract: Synthesis of (1S,3aS)-8- (2,3,3a,4,5,6-Hexahydro-1H-phenalen-1-yl)-1-phenyl-1,3,8-triaza-spiro [4.5]decan-4-one, a Potent and Selective Orphanin FQ (OFQ) Receptor Agonist with Anxiolytic-Like Properties.

Juergen Wichmann

Juergen Wichmann

Pharma Div., Chem. Technol., F. Hoffmann-La Roche AG, CH-4070 Basel, Switz.

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Geo Adam

Geo Adam

Pharma Div., Chem. Technol., F. Hoffmann-La Roche AG, CH-4070 Basel, Switz.

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Stephan Roever

Stephan Roever

Pharma Div., Chem. Technol., F. Hoffmann-La Roche AG, CH-4070 Basel, Switz.

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Michael Hennig

Michael Hennig

Pharma Div., Chem. Technol., F. Hoffmann-La Roche AG, CH-4070 Basel, Switz.

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Michelangelo Scalone

Michelangelo Scalone

Pharma Div., Chem. Technol., F. Hoffmann-La Roche AG, CH-4070 Basel, Switz.

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Andrea M. Cesura

Andrea M. Cesura

Pharma Div., Chem. Technol., F. Hoffmann-La Roche AG, CH-4070 Basel, Switz.

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Frank M. Dautzenberg

Frank M. Dautzenberg

Pharma Div., Chem. Technol., F. Hoffmann-La Roche AG, CH-4070 Basel, Switz.

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Francois Jenck

Francois Jenck

Pharma Div., Chem. Technol., F. Hoffmann-La Roche AG, CH-4070 Basel, Switz.

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First published: 31 May 2010
Citations: 1

Abstract

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ChemInform Abstract

The synthesis of title compound (XII) and its diastereoisomers is achieved via a Stobbe-type condensation, an asymmetric hydrogenation, and a Strecker-reaction. Within this series full agonists of the opioid (μ, ϰ, δ) receptors are identified. The most selective compound (XII) is evaluated for its behavioral effects with specific attention for effects on emotional reactivity and anxiolytic-like properties in the elevated plus-maze test.

chemical structure image

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