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Hantzsch Synthesis of Pyrazolo[1‘,2‘:1,2]pyrazolo[3,4-b]pyridines:  Partial Agonists of the Calcitonin Receptor

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journal contribution
posted on 24.06.2005, 00:00 by Eric E. Boros, David J. Cowan, Richard F. Cox, Makda M. Mebrahtu, Michael H. Rabinowitz, James B. Thompson, Lawrence A. Wolfe
Small molecule calcitonin receptor agonists are of potential utility in the treatment and prevention of osteoporosis. Bicycloeneamine 1 was a useful intermediate in the synthesis of pyrazolopyridine calcitonin receptor partial agonists 2af. Dihydropyridines 10ac were conveniently prepared by reaction of 1 with Knoevenagel adducts 9ac, or in the case of 10d, by a three component reaction with 1, β-ketoester 7b, and aldehyde 8c. Oxidation of 10ad to pyridines 11ad and subsequent amide formation afforded the title compounds.