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A range of heterocycle fused azepines were synthesized in order to find a CNS penetrant, selective 5-HT(2C) agonist for the treatment of incontinence. The pyridazo-azepines such as compound 11 were shown to be potent 5-HT(2C) agonists and have potential for CNS penetration and good in vitro ADME properties but lacked selectivity against 5-HT(2B). Fusing a further heterocycle gave the selective triazolopyrimido-azepines. An example of this series, compound 36, was shown to be potent, selective, metabolically stable in vitro and efficacious in an in vivo model of stress urinary incontinence.

Original publication

DOI

10.1016/j.bmcl.2009.07.063

Type

Journal article

Journal

Bioorg Med Chem Lett

Publication Date

01/09/2009

Volume

19

Pages

4999 - 5003

Keywords

Animals, Azepines, CHO Cells, Cell Line, Cricetinae, Cricetulus, Dogs, Drug Discovery, Humans, Pyrimidines, Receptor, Serotonin, 5-HT2B, Receptor, Serotonin, 5-HT2C, Recombinant Proteins, Serotonin 5-HT2 Receptor Agonists, Serotonin Receptor Agonists, Transfection, Urinary Incontinence