Bone-targeted Src kinase inhibitors: Novel pyrrolo- and pyrazolopyrimidine analogues

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 18, 2003, Pages 3063-3066

  Sundaramoorthi, Raji ^a   Shakespeare, William C ^a   Keenan, Terence P ^a   Metcalf III, Chester A ^a   Wang, Yihan ^a   Mani, Ukti ^a   Taylor, Merry ^a   Liu, Shuangying ^a   Bohacek, Regine S ^a   Narula, Surinder S ^a   Dalgarno, David C ^a   Van Schravandijk, Marie Rose ^a   Violette, Sheila M ^a   Liou, Shuenn ^a   Adams, Susan ^a   Ram, Mary K ^a   Keats, Jeffrey A ^a   Weigele, Manfred ^a   Sawyer, Tomi K ^a  

^a ARIAD PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PROTEIN TYROSINE KINASE INHIBITOR; PYRAZOLOPYRIMIDINE DERIVATIVE; PYRROLOPYRIMIDINE DERIVATIVE;

ANIMAL CELL; ARTICLE; BONE DISEASE; BONE TISSUE; CONTROLLED STUDY; ENZYME REGULATION; KNOCKOUT GENE; NONHUMAN; OSTEOBLAST; OSTEOCLAST; OSTEOPOROSIS; RABBIT; STRUCTURE ACTIVITY RELATION; VALIDATION PROCESS;

EID: 12444283696     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00647-4     Document Type: Article

References (26)

1. Rodan G.A., Martin T.J. Science. 289:2000;1508.
2. Boyce B.F., Hughes D.E., Wright K.R., Xing L., Dai A. Lab. Invest. 79:1999;83.
3. Ducy P., Schinke T., Karsenty G. Science. 289:2000;1501.
4. Teitelbaum S.L. Science. 289:2000;1504.
5. Soriono P., Montgomery C., Geske R., Bradley A. Cell. 64:1991;693.
6. Lowe C., Yoneda E., Boyce B.F., Chen H., Mundy G.R., Soriono P. Proc. Natl. Acad. Sci. U.S.A. 90:1993;4485.
7. Marzia M., Sims N.A., Voit S., Migliaccio S., Taranta A., Bernardini S., Faraggiana T., Yoneda T., Mundy G.R., Boyce B.F., Baron R., Teti A. J. Cell. Biol. 151:2000;311.
8. Sawyer T.K., Bohacek R.S., Eyermann C.J., Kawahata N., Metcalf C.A. III, Shakespeare W.C., Sundaramoorthi R., Wang Y., Yang M.G. Mini-Rev. Med. Chem. 2:2002;475 Shakespeare W., Yang M., Bohacek R., Cerasoli F., Stebbins K., Sundaramoorthi R., Vu C., Pradeepan S., Metcalf C., Haroldson C., Merry T., Dalgarno D., Narula S., Hatada M., Lu X., van Schravendijk M.R., Adams S., Violette S., Smith J., Guan W., Bartlett C., Herson J., Iuliucci J., Weigele M., Sawyer T. Proc. Natl. Acad. Sci. U.S.A. 97:2000;9373 Metcalf C.A., van Shravandijk M.R., Dalgarno D.C., Sawyer T.K. Curr. Pharma. Des. 8:2002;2049.
9. Sawyer T.K., Bohacek R.S., Eyermann C.J., Kawahata N., Metcalf C.A. III, Shakespeare W.C., Sundaramoorthi R., Wang Y., Yang M.G. Mini-Rev. Med. Chem. 2:2002;475 Shakespeare W., Yang M., Bohacek R., Cerasoli F., Stebbins K., Sundaramoorthi R., Vu C., Pradeepan S., Metcalf C., Haroldson C., Merry T., Dalgarno D., Narula S., Hatada M., Lu X., van Schravendijk M.R., Adams S., Violette S., Smith J., Guan W., Bartlett C., Herson J., Iuliucci J., Weigele M., Sawyer T. Proc. Natl. Acad. Sci. U.S.A. 97:2000;9373 Metcalf C.A., van Shravandijk M.R., Dalgarno D.C., Sawyer T.K. Curr. Pharma. Des. 8:2002;2049.
10. Sawyer T.K., Bohacek R.S., Eyermann C.J., Kawahata N., Metcalf C.A. III, Shakespeare W.C., Sundaramoorthi R., Wang Y., Yang M.G. Mini-Rev. Med. Chem. 2:2002;475 Shakespeare W., Yang M., Bohacek R., Cerasoli F., Stebbins K., Sundaramoorthi R., Vu C., Pradeepan S., Metcalf C., Haroldson C., Merry T., Dalgarno D., Narula S., Hatada M., Lu X., van Schravendijk M.R., Adams S., Violette S., Smith J., Guan W., Bartlett C., Herson J., Iuliucci J., Weigele M., Sawyer T. Proc. Natl. Acad. Sci. U.S.A. 97:2000;9373 Metcalf C.A., van Shravandijk M.R., Dalgarno D.C., Sawyer T.K. Curr. Pharma. Des. 8:2002;2049.
11. Missbach M., Jeshke M., Feyen J., Muller K., Glatt M., Green J., Susa M. Bone. 24:1999;437 Kniessel M., Gamse R., Missbach M., Wilder L., Beerli R., Susa S., Green J. Calcif. Tissue Int. 64(Suppl 1):1999;S75 Missbach M., Altmann E., Susa M. Curr. Opin. Drug Discov. Dev. 3:2000;54.
12. Missbach M., Jeshke M., Feyen J., Muller K., Glatt M., Green J., Susa M. Bone. 24:1999;437 Kniessel M., Gamse R., Missbach M., Wilder L., Beerli R., Susa S., Green J. Calcif. Tissue Int. 64(Suppl 1):1999;S75 Missbach M., Altmann E., Susa M. Curr. Opin. Drug Discov. Dev. 3:2000;54.
13. Missbach M., Jeshke M., Feyen J., Muller K., Glatt M., Green J., Susa M. Bone. 24:1999;437 Kniessel M., Gamse R., Missbach M., Wilder L., Beerli R., Susa S., Green J. Calcif. Tissue Int. 64(Suppl 1):1999;S75 Missbach M., Altmann E., Susa M. Curr. Opin. Drug Discov. Dev. 3:2000;54.
14. Hanke J.H., Gardner J.P., Dow R.L., Changelian P.S., Brissette W.H., Weringer E.J., Pollack B.A., Connelly P.A. J. Biol. Chem. 271:1996;695.
15. Xu W., Harrison S.C., Eck M.J. Nature. 385:1997;595 Yamaguchi H., Hendrickson W.A. Nature. 384:1996;484 Hubbard S.R. EMBO J. 16:1997;5572.
16. Xu W., Harrison S.C., Eck M.J. Nature. 385:1997;595 Yamaguchi H., Hendrickson W.A. Nature. 384:1996;484 Hubbard S.R. EMBO J. 16:1997;5572.
17. Xu W., Harrison S.C., Eck M.J. Nature. 385:1997;595 Yamaguchi H., Hendrickson W.A. Nature. 384:1996;484 Hubbard S.R. EMBO J. 16:1997;5572.
18. Xu W., Doshi A., Lei M., Eck M.J., Harrison S.C. Mol. Cell. 3:1999;629.
19. Shakespeare, W. C.; Sawyer, T. K.; Metcalf, C. A., III; Wang, Y.; Bohacek, R.; Sundaramoorthi, R. US Patent Application US 19632, 2002; Chem. Abstr. 2001, 138, 56075. Gray N.S., Wodicka L., Thunnissen A.W.H., Norman T.C., Kwon S., Espinoza F.H., Morgan D.O., Barnes G., LeClerc S., Meijer L., Kim S.-H., Lockhart D.J., Schultz P.G. Science. 281:1998;533.
20. Shakespeare, W. C.; Sawyer, T. K.; Metcalf, C. A., III; Wang, Y.; Bohacek, R.; Sundaramoorthi, R. US Patent Application US 19632, 2002; Chem. Abstr. 2001, 138, 56075. Gray N.S., Wodicka L., Thunnissen A.W.H., Norman T.C., Kwon S., Espinoza F.H., Morgan D.O., Barnes G., LeClerc S., Meijer L., Kim S.-H., Lockhart D.J., Schultz P.G. Science. 281:1998;533.
21. Shakespeare, W. C.; Sawyer, T. K.; Metcalf, C. A., III; Wang, Y.; Bohacek, R.; Sundaramoorthi, R. US Patent Application US 19632, 2002; Chem. Abstr. 2001, 138, 56075. Gray N.S., Wodicka L., Thunnissen A.W.H., Norman T.C., Kwon S., Espinoza F.H., Morgan D.O., Barnes G., LeClerc S., Meijer L., Kim S.-H., Lockhart D.J., Schultz P.G. Science. 281:1998;533.
22. Hartel C., Gobel M.W. Helv. Chim. Acta. 83:2000;2541 Uludag H. Curr. Pharma. Des. 8:2002;1929.
23. Hartel C., Gobel M.W. Helv. Chim. Acta. 83:2000;2541 Uludag H. Curr. Pharma. Des. 8:2002;1929.
24. Detailed description of the following assays: Anti-resorptive rabbit osteoclast assay, SPA Src kinase assay and hydroxyapatite assay can each be found in: Weigele, M.; Dalgarno, D.; Luke, G. P.; Sawyer, T. K.; Bohacek, R. S. ; Shakespeare, W. C.; Sundaramoorthi, R.; Wang, Y.; Metcalf, C. A.; Vu, C. B.; Kawahata, N. H. PCT Intl. Patent Application WO O1/44258, 2001.
25. Weigele, M.; Dalgarno, D. C.; Luke, G. P.; Sawyer, T. K.; Bohacek, R. S. ; Shakespeare, W. C.; Sundaramoorthi, R.; Wang, Y.; Metcalf, C. A.; Vu, C. B.; Kawahata, N. H. US Patent WO 0144259, 2001; Chem. Abstr. 2001, 135, 46048.
26. Weigele, M.; Dalgarno, D. C.; Luke, G. P.; Sawyer, T. K.; Bohacek, R. S. ; Shakespeare, W. C.; Sundaramoorthi, R.; Wang, Y.; Metcalf, C. A.; Vu, C. B.; Kawahata, N. H. US Patent WO 0144259, 2001; Chem. Abstr. 2001, 135, 46048.