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Bioorg Med Chem Lett. 2012 Dec 1;22(23):7087-91. doi: 10.1016/j.bmcl.2012.09.085. Epub 2012 Oct 2.

Tyrosine urea muscarinic acetylcholine receptor antagonists: achiral quaternary ammonium groups.

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  • 1GlaxoSmithKline, 709 Swedeland Road, PO Box 1539, King of Prussia, PA 19406-0939, USA.


Tyrosine ureas had been identified as potent muscarinic receptor antagonists with promising in vivo activity. Controlling the stereochemistry of the chiral quaternary ammonium center had proved to be a serious issue for this series, however. Herein we describe the preparation and SAR of tyrosine urea antagonists containing achiral quaternary ammonium centers. The most successful such moiety was the 2-methylimidazo[2,1-b][1,3]thiazol-7-ium group which yielded highly potent antagonists with long duration of action in an inhaled animal model of bronchoconstriction.

Copyright © 2012 Elsevier Ltd. All rights reserved.

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