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A Physical Properties Based Approach for the Exploration of a 4-Hydroxybenzothiazolone Series of Beta2-Adrenoceptor Agonists as Inhaled Long-Acting Bronchodilators

Beattie, David and Bradley, Michelle and Brearley, Andrew and Charlton, Steven and Cuenoud, Bernard and Fairhurst, Robin and Gedeck, Peter and Gosling, Martin and Janus, Diana and Jones, Darryl and Lewis, Christine and Mccarthy, Clive and Oakman, Helen and Stringer, Rowan and Taylor, Roger and Tuffnell, Andrew (2010) A Physical Properties Based Approach for the Exploration of a 4-Hydroxybenzothiazolone Series of Beta2-Adrenoceptor Agonists as Inhaled Long-Acting Bronchodilators. Bioorganic and Medicinal Chemistry Letters, 20 (17). pp. 5302-5307.

Abstract

The chiral synthesis of a 4-hydroxybenzothiazolone based series of beta2-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 beta-phenethyl, alpha-substituted cyclopentyl and monoterpene N-substituents to be of interest for further evaluation, as exemplified by structures 19, 29 and 33 respectively.

Item Type: Article
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Additional Information: author can archive post-print (ie final draft post-refereeing); Publisher's version/PDF cannot be used
Keywords: Bronchodilator; b2-Adrenoceptor agonist; 4-Hydroxybenzothiazolone
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Date Deposited: 13 Oct 2015 13:16
Last Modified: 13 Oct 2015 13:16
URI: https://oak.novartis.com/id/eprint/2601

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