182251-92-9Relevant articles and documents
Practical chemoenzymatic synthesis of a 3-pyridylethanolamino β3 adrenergic receptor agonist
Chung, John Y. L.,Ho, Guo-Jie,Chartrain, Michel,Roberge, Chris,Zhao, Dalian,Leazer, John,Farr, Roger,Robbins, Micheal,Emerson, Kateeta,Mathre, David J.,McNamara, James M.,Hughes, David L.,Grabowski, Edward J. J.,Reider, Paul J.
, p. 6739 - 6743 (2007/10/03)
A chemoenzymatic synthesis of β3 agonist 1 suitable for large scale preparation is described. The key chiral 3-pyridylethanolamine intermediate (R)-7 was prepared via an improved Neber rearrangement and a yeast-mediated asymmetric reduction. The tetrazolone fragment of the molecule was constructed via a dipolar cycloaddition between 1-(cyclopentyl)-3-propylazide and p-chlorosulfonyl phenylisocyanate. Sulfonamide coupling of these two intermediates under Shotten-Baumann conditions, followed by a borane reduction of the amide afforded 1 in 20-32% overall yield from 3-acetylpyridine.
L-770,644: A potent and selective human β3 adrenergic receptor agonist with improved oral bioavailability
Shih, Thomas L.,Candelore, Mari R.,Cascieri, Margaret A.,Chiu, Shuet-Hing L.,Colwell Jr., Lawrence F.,Deng, Liping,Feeney, William P.,Forrest, Michael J.,Hom, Gary J.,Macintyre, D. Euan,Miller, Randall R.,Stearns, Ralph A.,Strader, Catherine D.,Tota, Laurie,Wyvratt, Matthew J.,Fisher, Michael H.,Weber, Ann E.
, p. 1251 - 1254 (2007/10/03)
L-770,644 (9c) is a potent and selective agonist of the human β3 adrenergic receptor (EC50 = 13 nM). It shows good oral bioavailability in both dogs and rats (%F = 27), and is a full agonist for glycerolemia in the rhesus monkey (ED50 = 0.21 mg/kg). Based on its desirable in vitro and in vivo properties, L-770,644 was chosen for further preclinical evaluation.
SUBSTITUTED SULFONAMIDES AS SELECTIVE BETA3 AGONISTS FOR THE TREATMENT OF DIABETES AND OBESITY
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, (2008/06/13)
Substituted sulfonamides are selective β 3 adrenergic receptor agonists with very little β 1 and β 2 adrenergic receptor activity and as such the compounds are capable of increasing lipolysis and energy expenditure in cells. The compounds thus have potent
