Hantzsch synthesis of pyrazolo[1′,2′:1,2]pyrazolo[3,4-b]pyridines:: Partial agonists of the calcitonin receptor

被引:18
作者
Boros, EE [1 ]
Cowan, DJ [1 ]
Cox, RF [1 ]
Mebrahtu, MM [1 ]
Rabinowitz, MH [1 ]
Thompson, JB [1 ]
Wolfe, LA [1 ]
机构
[1] GlaxoSmithKline Res & Dev Ltd, Res Triangle Pk, NC 27709 USA
关键词
D O I
10.1021/jo050370b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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 2a-f. Dihydropyridines 10a-c were conveniently prepared by reaction of 1 with Knoevenagel adducts 9a-c, or in the case of 10d, by a three component reaction with 1, β-ketoester 7b, and aldehyde 8c. Oxidation of 10a-d to pyridines 11a-d and subsequent amide formation afforded the title compounds. © 2005 American Chemical Society.
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页码:5331 / 5334
页数:4
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