Pyrazolo[1,5-a]pyridines: Synthetic approaches to a novel class of antiherpetics

Tetrahedron

Volumn 59, Issue 45, 2003, Pages 9001-9011

  Johns, Brian A ^a   Gudmundsson, Kristjan S ^a   Turner, Elizabeth M ^a   Allen, Scott H ^a   Jung, David K ^a   Sexton, Connie J ^a   Boyd Jr , F Leslie ^a   Peel, Michael R ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

Alkynyl ketone; HSV; Pyrazolo 1,5 a pyridine; Pyrimidine synthesis

Indexed keywords

7 AMINO 3 PYRIMIDINYLPYRAZOLO[1,5 A]PYRIDINE; ANTIVIRUS AGENT; AZIRINE DERIVATIVE; KETONE DERIVATIVE; PYRIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 0142217504     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.02.003     Document Type: Article

References (21)

1. Corey L., Spear P. New Engl. J. Med. 314:1986;686.
2. Corey L., Handsfield H.H. J. Am. Med. Assoc. 283:2000;791.
3. (a) Elion G.B., Furman P.A., Fyfe J.A., De Miranda P., Beauchamp L., Schaeffer H.J. Proc. Natl Acad. Sci. USA. 74:1977;5716
4. (b) Elion G.B. J. Med. Virol. Suppl. 1:1993;2.
5. Corey, L.; Tyring, S.; Sacks, S.; Warren, T.; Beutner, K.; Patel, R.; Wald, A.; Mertz, G.; Paavonen, J. Abstract of papers, 42nd Interscience Conference on Antimicrobial Agents and Chemotherapy, San Diego, CA; American Society for Microbiology: Washington, DC. 2002, LB3.
6. Sexton, C. J.; Selleseth, D. W.; Jansen, R.W. Unpublished results.
7. Alberti, M. J.; Baldwin, I. R.; Cheung, M.; Cockerill, S.; Flack, S.; Harris, P. A.; Jung, D. K.; Peckham, G.; Peel, M. R.; Stanford, J. B.; Stevens, K.; Veal, J. M. WO 02/16359, 2002; Chem Abstr. 2002, 136, 200184.
8. Discussions of the biological profiles of these compounds will be the subject of future publications.
9. For some leading references on pyrazolo[1,5-a]pyridines see (a) Miki Y., Nakamura N., Hachiken H., Takemura S. J. Heterocycl. Chem. 26:1989;1739 (b) Awano K., Suzue S. Chem. Pharm. Bull. 40:1992;631 (c) Akahane A., Katayama H., Mitsunaga T., Kita Y., Kusunoki T., Terai T., Yoshida K., Shiokawa Y. Bioorg. Med. Chem. Lett. 6:1996;2059 (d) Zanka A., Uematsu R., Morinaga Y., Yasuda H., Yamazaki H. Org. Proc. Res. Dev. 3:1999;389.
10. For some leading references on pyrazolo[1,5-a]pyridines see (a) Miki Y., Nakamura N., Hachiken H., Takemura S. J. Heterocycl. Chem. 26:1989;1739 (b) Awano K., Suzue S. Chem. Pharm. Bull. 40:1992;631 (c) Akahane A., Katayama H., Mitsunaga T., Kita Y., Kusunoki T., Terai T., Yoshida K., Shiokawa Y. Bioorg. Med. Chem. Lett. 6:1996;2059 (d) Zanka A., Uematsu R., Morinaga Y., Yasuda H., Yamazaki H. Org. Proc. Res. Dev. 3:1999;389.
11. For some leading references on pyrazolo[1,5-a]pyridines see (a) Miki Y., Nakamura N., Hachiken H., Takemura S. J. Heterocycl. Chem. 26:1989;1739 (b) Awano K., Suzue S. Chem. Pharm. Bull. 40:1992;631 (c) Akahane A., Katayama H., Mitsunaga T., Kita Y., Kusunoki T., Terai T., Yoshida K., Shiokawa Y. Bioorg. Med. Chem. Lett. 6:1996;2059 (d) Zanka A., Uematsu R., Morinaga Y., Yasuda H., Yamazaki H. Org. Proc. Res. Dev. 3:1999;389.
12. For some leading references on pyrazolo[1,5-a]pyridines see (a) Miki Y., Nakamura N., Hachiken H., Takemura S. J. Heterocycl. Chem. 26:1989;1739 (b) Awano K., Suzue S. Chem. Pharm. Bull. 40:1992;631 (c) Akahane A., Katayama H., Mitsunaga T., Kita Y., Kusunoki T., Terai T., Yoshida K., Shiokawa Y. Bioorg. Med. Chem. Lett. 6:1996;2059 (d) Zanka A., Uematsu R., Morinaga Y., Yasuda H., Yamazaki H. Org. Proc. Res. Dev. 3:1999;389.
13. Fitzgerald, R. N.; Jung, D. K.; Eaddy, J. F. WO 01/83479, 2001; Chem Abstr. 2001, 135, 357918.
14. (a) Wolfe J.P., Wagaw S., Buchwald S.L. J. Am. Chem. Soc. 118:1996;7215.
15. (b) Harris M.C., Geis O., Buchwald S.L. J. Org. Chem. 64:1999;6019
16. (c) Wolfe J.P., Buchwald S.L. J. Org. Chem. 65:2000;1144
17. (d) Hartwig J.F. Angew. Chem. Int. Ed. 37:1998;2046.
18. Guanidine 11 was made via a modification of methods described in Bannard R.A.B., Casselman A.A., Cockburn W.F., Brown G.M. Can. J. Chem. 36:1958;1541.
19. Numerous guanidines and amidines have been condensed with vinylogous amides such as 10 and will be discussed in future SAR publications.
20. (a) Adlington R.M., Baldwin J.E., Catterick D., Pritchard G.J. J. Chem. Soc. Chem. Commun. 1997;1757
21. (b) Adlington R.M., Baldwin J.E., Catterick D., Pritchard G.J. J. Chem. Soc. Perkin Trans. 1. 1999;855-866.