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A physical properties based approach for the exploration of a 4-hydroxybenzothiazolone series of ß2-adrenoceptor agonists as inhaled long-acting bronchodilators

journal contribution
posted on 2023-06-08, 19:46 authored by David Beattie, Michelle Bradley, Andrew Brearley, Steven J Charlton, Bernard M Cuenoud, Robin A Fairhurst, Peter Gedeck, Martin Gosling, Diana Janus, Darryl Jones, Christine Lewis, Clive McCarthy, Helen Oakman, Rowan Stringer, Roger J Taylor, Andrew Tuffnell
The chiral synthesis of a 4-hydroxybenzothiazolone based series of ß2-adrenoceptor agonists is described. Using this methodology a library of N-substituted analogues were prepared for the rapid identification of leads with the potential to be fast onset and long-acting inhaled bronchodilators with improved therapeutic margins. The design of the library to achieve the targeted profile was based upon lipophilicity and metabolism based hypotheses. This approach identified ß-phenethyl, a-substituted cyclopentyl and monoterpene N-substituents to be of particular interest for further evaluation, as exemplified by structures 19, 29 and 33, respectively. © 2010 Elsevier Ltd. All rights reserved.

History

Publication status

  • Published

Journal

Bioorganic and Medicinal Chemistry Letters

ISSN

0960-894X

Publisher

Elsevier

Issue

17

Volume

20

Page range

5302-5307

Department affiliated with

  • Chemistry Publications

Full text available

  • No

Peer reviewed?

  • Yes

Legacy Posted Date

2015-01-27

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