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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 13期

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.

引用

页码：5331 / 5334

页数：4

共 17 条

[1] Salmon calcitonin in the prevention and treatment of osteoporosis [J].

Avioli, LV .

TRENDS IN ENDOCRINOLOGY AND METABOLISM, 1997, 8 (03) :89-92

[2]

Bhandari A, 1999, SYNTHESIS-STUTTGART, P1951

[3]

BHANDARI A, 2003, Patent No. 03076440

[4] A convenient synthesis of pyrazolidine and 3-amino-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazol-1-one [J].

Boros, EE ;

Bouvier, F ;

Randhawa, S ;

Rabinowitz, MH .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (03) :613-616

[5] Expression cloning and receptor pharmacology of human calcitonin receptors from MCF-7 cells and their relationship to amylin receptors [J].

Chen, WJ ;

Armour, S ;

Way, J ;

Chen, G ;

Watson, C ;

Irving, P ;

Cobb, J ;

Kadwell, S ;

Beaumont, K ;

Rimele, T ;

Kenakin, T .

MOLECULAR PHARMACOLOGY, 1997, 52 (06) :1164-1175

[6] DISCOVERY OF A NOVEL CLASS OF POTENT HIV-1 PROTEASE INHIBITORS CONTAINING THE (R)-(HYDROXYETHYL) UREA ISOSTERE [J].

GETMAN, DP ;

DECRESCENZO, GA ;

HEINTZ, RM ;

REED, KL ;

TALLEY, JJ ;

BRYANT, ML ;

CLARE, M ;

HOUSEMAN, KA ;

MARR, JJ ;

MUELLER, RA ;

VAZQUEZ, ML ;

SHIEH, HS ;

STALLINGS, WC ;

STEGEMAN, RA .

JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (02) :288-291

[7]

GREENWALD RB, 1978, Patent No. 4128425

[8]

HONGBIN YY, 2004, J AM CHEM SOC, V126, P14720

[9]

Jones G., 1967, ORGANICREACTIONS, V15, P204, DOI [DOI 10.1002/0471264180.OR015.02, 10.1002/0471264180.or015.02]

[10] Contribution of conformationally constrained calcitonin (Ct) analogs to the understanding of the structural and conformational requirements of calcitonin bioactivity and to the design of potent agonists [J].

Kapurniotu, A .

CURRENT MEDICINAL CHEMISTRY, 2004, 11 (21) :2845-2865

← 1 2 →