227963-15-7Relevant articles and documents
Thermodynamic Understanding of an Aza-Michael Reaction Enables Five-Step Synthesis of the Potent Integrin Inhibitor MK-0429
Gupta, Anya,Condakes, Matthew L.
, p. 17523 - 17527 (2021/11/18)
We describe a general strategy for the aza-Michael addition of nucleophilic heterocycles into β-substituted acrylates using potassium tert-butoxide as catalyst. Demonstrating that the reaction is under thermodynamic control underpins optimization efforts and enables rapid exploration of the substrate scope, with yields ranging from 55% to 94%. We further leverage these lessons in a significantly shortened synthesis of MK-0429, a potent pan-integrin inhibitor previously taken into human clinical trials for the treatment of prostate cancer and osteoporosis.
An efficient synthesis of an alphavbeta3 antagonist.
Yasuda, Nobuyoshi,Hsiao,Jensen, Mark S,Rivera, Nelo R,Yang, Chunhua,Wells, Kenneth M,Yau, James,Palucki, Michael,Tan, Lushi,Dormer, Peter G,Volante, Ralph P,Hughes, David L,Reider, Paul J
, p. 1959 - 1966 (2007/10/03)
A practical preparation of an alpha(v)beta(3) antagonist is reported. The antagonist consists of three key components, a tetrahydronaphthyridine moiety, a beta-alanine moiety, and a central imidazolidone moiety. The tetrahydronaphthyridine component was p
Process and intermediates for the preparation of imidazolidinone αv integrin antagonists
-
, (2008/06/13)
A novel process is provided for the preparation of imidazolidinone αvβ3/αvβ5 integrin antagonists, and the useful intermediates obtained therein. These compounds are antagonists of αvβ3/αvβ5 integrin receptors and thus useful for inhibiting bone resorption and treating and preventing osteoporosis. Also disclosed is 3-{2-oxo-3-[3-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-propyl]imidazolidin-1-yl}-3(S)-(6-methoxy-pyridin-3-yl)-propionic acid in the form of a hemihydrate.