SAR development of a selective 5-HT1D antagonist/serotonin reuptake inhibitor lead using rapid parallel synthesis

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 10, 2004, Pages 2469-2472

  Timms, Graham H ^a   Boot, John R ^a   Broadmore, Richard J ^a   Carney, Steven L ^a   Cooper, Jane ^a   Findlay, Jeremy D ^a   Gilmore, Jeremy ^a   Mitchell, Stephen ^a   Moore, Nick A ^a   Pullar, Ian ^a   Sanger, Graham J ^a   Tomlinson, Rosemary ^a   Tree, Beverly B ^a   Wedley, Susan ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

5 HT1D antagonist; Rapid parallel synthesis; Serotonin reuptake inhibitor

Indexed keywords

ALPHA ADRENERGIC RECEPTOR; DOPAMINE 2 RECEPTOR; FLUOXETINE; N [4 METHOXY 3 (4 METHYL 1 PIPERAZINYL)PHENYL] 2' METHYL 4' (5 METHYL 1,2,4 OXADIAZOL 3 YL)[1,1' BIPHENYL] 4 CARBOXAMIDE; SEROTONIN 1D AGONIST; SEROTONIN 1D ANTAGONIST; SEROTONIN UPTAKE INHIBITOR;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; CROSS REACTION; DRUG ACTIVITY; DRUG SYNTHESIS; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

CELL LINE; CROSS REACTIONS; GUANOSINE 5'-O-(3-THIOTRIPHOSPHATE); HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; HUMANS; RECEPTOR, SEROTONIN, 5-HT1D; SEROTONIN ANTAGONISTS; SEROTONIN UPTAKE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 11144356460     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.03.003     Document Type: Article

References (31)

1. Thase M.E., Rush A.J. Bloom F.E., Kipper D.J. Psychopharmacology, The Fourth Generation of Progress. 1995;1081-1098 Raven, New York.
2. Facet J., Barking R.L. J. Clin. Psychiatry. 58:1997;32-39.
3. Fava M. J. Clin. Psychiatry. 61:2000;26-32.
4. Montgomery S.A. Bloom F.E., Kupfer D.J. Psychopharmacology, The Fourth Generation of Progress. 1995;451-461 Raven, New York.
5. Goodwin G.M. J. Clin. Psychiatry. 57:1996;9-13.
6. Leonard B.E. J. Clin. Psychiatry. 57:1996;26-33.
7. Glennon R.A., Westkaemper R.B. Drug News Perspect. 6:1993;390-405.
8. Briley M., Moret C. Clin. Neuropharmacol. 16:1993;387-400.
9. More C., Brimley M. Eur. J. Pharmacol. 404:2000;1-12.
10. Davidson C., Stamford J.A. Br. J. Pharmacol. 114:1995;1107-1109.
11. Rollema H., Clarke T., Sprouse J.S., Schulz D.W. J. Neurochem. 67:1996;2204-2207.
12. Ennis M.D., Ghazal N.B., Hoffman R.L., Smith M.W., Schlachter S.F., Lawson C.F., Im W.B., Pregenzer J.F., Svensson K.A., Lewis R.A., Hall E.D., Sutter D.M., Harris L.T., McCall R.B. J. Med. Chem. 41:1998;2180-2183.
13. Audia, J. E; Kock, D. J.; Mabry, T. E.; Nissen, J. S.; Rocco, V. P.; Xu, Y.-C. WO Patent 97/47302, 1997.
14. (a) Substituted 3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indoles, fluoro substituted-3-(4-piperidinyl)-1H-indoles and (3R)-6-fluoro-3-(3-pyrrolidinyl)- 1H-indole: Fairhurst, J.; Gallagher, P. T.; Miles, M. V.; Owton, W. M.; Smith, C. W. WO Patent 99/58525, 1999 and Niemala, K. WO Patent 00/02341, 2000
15. (b) Substituted and unsubstituted 4-(1-naphthyl)-1,2,3,6- tetrahydropyridines and 4-(1-naphthyl)-piperidines: Sloan, C. P.; Smith, D. W. U.S. Patent 5,472,966, 1995; Lavielle, G.; Laubie, M.; Colpaert, F. U.S. Patent 5,250,544, 1993 and Nishimura, M.; Toyofuku, K.; Takahashi, Y. U.S. Patent 5,292,711, 1994
16. (b) Substituted and unsubstituted 4-(1-naphthyl)-1,2,3,6- tetrahydropyridines and 4-(1-naphthyl)-piperidines: Sloan, C. P.; Smith, D. W. U.S. Patent 5,472,966, 1995; Lavielle, G.; Laubie, M.; Colpaert, F. U.S. Patent 5,250,544, 1993 and Nishimura, M.; Toyofuku, K.; Takahashi, Y. U.S. Patent 5,292,711, 1994
17. Substituted 4-(2-naphthyl) 1,2,3,6-tetrahydro-pyridine: Teitler M., Scheick C., Howard P., Sullivan J.E. III, Iwamura T., Glennon R.A. Med. Chem. Res. 7:1997;207-218.
18. (5) Substituted 4-(1-benzopyran-3-yl)-1,2,3,6-tetrahydropyridine: Lavielle, G.; Laubie, M.; Colpaert, F. EP-A Patent 0466585, 1992 or Kutoita, T.; Bogauchi, M.; Nishiyama, A.; Morio, Y. Japanese Patent JP 2000086603, 2000
19. (e) 6-Fluoro-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1,2-benzisoxazole: Bauer, V. J.; Fanshawe, W. J.; Wiegand, G. E. U.S. Patent 3,678,062, 1972
20. Substituted 4-(1-benzothiophen-3-yl)-1,2,3,6-tetrahydropyridine: Watanabe Y., Yoshiwara H., Kanab M. J. Heterocycl. Chem. 30:1993;445-451.
21. (g) Substituted 4-(1,2-benzisothiazol-3-yl)-1,2,3,6-tetrahydropyridine: McCort, G.; Hoornaert, C.; Cadilhac, C.; Duclos, O.; Guilpain, E.; Dellac, G. WO Patent 98/42710, 1998
22. (h) Substituted and unsubstituted 6-fluoro-1-3-(1,2,3,6-tetrahydro-4- pyridinyl)-1H-indazoles: Strupczewski, J. T. EP Patent 013578, 1985
23. (i) 4-(4-Fluoro-1-benzopyran-7-yl)-1,2,3,6-tetrahydropyridine: Hertel, L. W.; Kohlman, D. T.; Liang, S. X.; Wong, D. T.; Wu, Y. WO Patent 00/0019, 2000
24. (j) 5-Methoxy-3-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-indole was obtained from Tocris Cookson
25. Agejas-Chicharro, J.; Bueno Melendo, A. B.; Camp, N. P.; Gilmore, J.; Jimenez-Aguado, A. M.; Lamas-Peteira, C.; Marcos-Llorente, A.; Mazanetz, M. P.; Montero Salgado, C.; Timms, G. H.; Williams, A. C. WO Patent 02/50067, 2002.
26. Pullar I.A., Carney S.L., Colvin E.M., Lucaites V.L., Nelson D.L., Wedley S. Eur. J. Pharmacol. 407:2000;39-46.
27. Greengrass P., Bremner R. Eur. J. Pharmacol. 55:1979;323-326.
28. ® treatment (solid scintillation fluid) and counting using a Wallac β plate counter.
29. Pullar I.A., Boot J.R., Carney S.L., Cohen M.L., Colvin E.M., Conway R.G., Hardy C.H.L., Lucaites V.L., Nelson D.L., Schenck K.W., Tomlinson R., Wedley S. Eur. J. Pharmacol. 432:2001;9-17.
30. Mitchell S.N., Greenslade R.G., Cooper J. Eur. J. Pharmacol. 432:2001;19-27.
31. Agejas-Chicharro, J.; Bueno Melendo, A. B.; Camp, N. P.; Gilmore, J.; Lamas-Peteira, C.; Timms, G. H.; Williams, A. C. WO Patent 03/05394.