170
B. M. Mathes et al. / Bioorg. Med. Chem. Lett. 14 (2004) 167–170
receptor agonist that may have potential as a ther-
apeutic for acute treatment of migraine.
C.; Zgombick, J. M. 8th Congress of the International
Headache Society. Amsterdam, 10–14 June 1997.
. Filla, S. A.; Mathes, B. M.; Johnson, K. W.; Phebus,
L. A.; Cohen, M. L.; Nelson, D. L.; Zgombick, J. M.;
Erickson, J. A.; Schenck, K. W.; Wainscott, D. B.;
Branchek, T. A.; Schaus, J. M. J. Med. Chem., in
press.
0. Xu, Y.-C.; Johnson, K. W.; Phebus, L. A.; Cohen, M.;
Nelson, D. L.; Schenck, K.; Walker, C. D.; Fritz, J. E.;
Kaldor, S. W.; LeTourneau, M. E.; Murff, R. E.; Zgom-
bick, J. M.; Calligaro, D. O.; Audia, J. E.; Schaus, J. M.
J. Med. Chem. 2001, 44, 4031.
9
Acknowledgements
The authors would like to thank Mr. Steven Henry of
Eli Lilly and Company for helpful discussions regarding
the preparation of this manuscript, as well as Dr. Jeffrey
Schkeryantz of Eli Lilly for his scientific insights.
1
1
1. Goldstein, D. J.; Roon, K. I.; Offen, W. W.; Ramadan,
N. M.; Phebus, L. A.; Johnson, K. W.; Schaus, J. M.;
Ferrari, M. D. Lancet 2001, 358, 1230.
References and notes
1
. Fuller, R. W. Adv. Drug Res. 1988, 17, 349. (b) Glennon,
R. A. Neurosci. Biobehav. Rev. 1990, 14, 35.
. Bradley, P. B.; Engle, G.; Feniuk, W.; Fozard, J. R.;
Humphrey, P. P. A.; Middlemiss, D. N.; Mylecharane,
E. J.; Richardson, B. P.; Saxena, P. R. Neuropharmacol-
ogy 1986, 25, 563. (b) Pertoutka, S. J. Trends Neurosci.
1988, 11, 496. (c) Hibert, M. F.; Mir, A. K.; Pozard, J. R.;
In Comprehensive Medicinal Chemistry; Hanch, C.;
Sammes, P.; Taylor, J., Eds.: Pergamon Press: Oxford,
1990; Vol. 3, Chapter 12.9; p 567. (d) Levy, F. O.;
12. Russell, M. G. N.; Castro, J. L.; Matassa, V. G.; Beer,
M. S.; Heald, A.; Scholey, K.; Stanton, J. A.; Broughton,
H. B. Bioorg. Med. Chem. Lett. 1994, 4, 1207.
13. Tomaszewski, Z.; Johnson, M. P.; Huang, X.; Nichols,
D. E. J. Med. Chem. 1992, 35, 2061.
14. Depreux, P.; Lesieur, D.; Mansour, H. A.; Morgan, P.;
Howell, H. E.; Renard, P.; Caignard, D.; Pfeiffer, B.;
Delagrange, P., et al. J. Med. Chem. 1994, 37, 3231.
15. Pinder, R. M.; Green, D. M.; Thompson, P. B. J. J. Med.
Chem. 1971, 14, 626.
2
Gudermann, T.; Birnbaymer, M.; Kaumann, A. J.; Birn-
baumer, L. FEBS Lett. 1992, 296, 201.
16. Mathes, B. M.; Filla, S. A. Tetrahedron Lett. 2003, 44,
725.
3
4
. Ferrari, M. D. Neurology 1983, 43 (Suppl. 3), S43. (b)
Plosker, G. L.; McTavish, D. Drugs 1994, 47, 622.
. Johnson, K. W.; Schaus, J. M.; Durkin, M. M.; Audia,
J. E.; Kaldor, S. W.; Flaugh, M. E.; Adham, N.; Zgom-
bick, J. M.; Cohen, M. L.; Branchek, T. A.; Phebus, L. A.
Neuroreport 1997, 8, 2237.
. Bouchelet, I.; Cohen, Z.; Case, B.; Seguela, P.; Hamel, E.
Mol. Pharmacol. 1996, 50, 219.
. Kaumann, A. J.; Frenken, M.; Posival, H.; Brown, A. M.
Circulation 1994, 90, 1141.
. Compounds with efficacy in the clinic for the treatment of
migraine pain, such as sumatriptan, zolmitriptan, riza-
triptan, LY334370, and classical migraine abortives such
as dihydroergotamine, inhibit neurogenic dural inflam-
mation following electrical stimulation: (a) ref 4. (b)
Buzzi, M. G.; Moskowitz, M. A. Br. J. Pharmacol. 1990,
17. Compound 7 was prepared in a two-step sequence that
included a Horner–Emmons reaction of 1-Boc-4-piper-
idone with triethylphosphonoacetate, followed by LiAlH
reduction of the ethyl ester to the primary hydroxyl
group.
18. Larock, R. C.; Stinn, D. E. Tetrahedron Lett. 1988, 29,
4687.
19. Wolfe, J. P.; Ahman, J.; Sadighi, J. P.; Singer, R. A.;
Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6367.
20. Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernandez-
Rivas, C. J. Am. Chem. Soc. 1998, 120, 827.
21. Adham, N.; Kao, H. T.; Schechter, L. E.; Bard, J.; Olsen,
M.; Urquhart, D.; Durkin, M.; Hartig, P. R.; Weinshank,
R. L.; Branchek, T. A. Proc. Natl. Aca. Sci. U.S.A. 1993,
90, 408.
22. Weinshank, R. L.; Zgombick, J. M.; Macchi, M. J.;
Branchek, T. A.; Hartig, P. R. Proc. Natl. Aca. Sci.
U.S.A. 1992, 89, 3630.
23. Zgombick, J. M.; Weinshank, R. L.; Macchi, M. J.;
Schechter, L. E.; Branchek, T. A.; Hartig, P. R. Mol.
Pharmacol. 1991, 40, 1036.
4
5
6
7
99, 202.
8
. Schaus, J. M.; Audia, J. E.; Dressman, B. A.; Kaldor, S.
W.; Krushinski, J. H.; Adham, N.; Benvenga, M. J.;
Brancheck, T. A.; Calligaro, D. O.; Fuller, R. W.; Hem-
rick-Luecke, S. K.; Johnson, K. W.; Leander, J. D.;
Lucaites, V. L.; Nelson, D. L. G.; Overshiner, C. C.;
Phebus, L. A.; Roush, M. E.; Wainscott, D. B.; Wolff, M.
24. Wainscott, D. B.; Johnson, K. W.; Phebus, L. A.; Schaus,
J. M.; Nelson, D. L. Eur. J. Pharmacol. 1998, 352, 117.