Synthesis of (±)-1-phenyl-2-azabicyclo[2.2.1]heptane derivatives - Novel NK1 receptor ligands

Synlett

Volumn , Issue 2, 2006, Pages 271-274

  Raubo, Piotr ^a   Kulagowski, Janusz J ^a   Chicchi, Gary G ^b  

^a NEUROSCIENCE RESEARCH CENTRE   (United Kingdom)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Bicyclic compounds; McMurry coupling; NK1 receptor; Opening of epoxides; Ring closing olefin metathesis

Indexed keywords

BICYCLO COMPOUND; ETHYLENE OXIDE DERIVATIVE; HEPTANE DERIVATIVE; HETEROCYCLIC COMPOUND; LIGAND; NEUROKININ 1 RECEPTOR ANTAGONIST;

ARTICLE; CATALYSIS; CYCLIZATION; DIASTEREOISOMER; DRUG BINDING SITE; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; IC 50; OXIDATION; QUANTUM YIELD; REACTION ANALYSIS; RECEPTOR AFFINITY; RING CLOSING METATHESIS; STEREOCHEMISTRY;

EID: 32344445280     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926221     Document Type: Article

References (16)

1. Seward, E. M.; Swain, C. J. Expert Opin. Ther. Pat. 1999, 9, 571.
2. Kramer, M. S.; Cutler, N.; Feighner, J.; Shrivastava, R.; Carman, J.; Sramek, J. J.; Reines, S. A.; Liu, G.; Snavely, D.; Wyatt-Knowles, E.; Hale, J. J.; Mills, S. G.; MacCoss, M.; Swain, C. J.; Harrison, T.; Hill, R. G.; Hefti, F.; Scolnick, E. M.; Cascieri, M. A.; Chicchi, G. G.; Sadowski, S.; Williams, A. R.; Hewson, L.; Smith, D.; Carlson, E. J.; Hargreaves, R. J.; Rupniak, N. M. J. Science 1998, 281, 1640.
3. Snider, R. M.; Constantine, J. W.; Lowe, J. A. III.; Longo, K. P.; Lebel, W. S.; Woody, H. A.; Drozda, S. E.; Desai, M. C.; Vinick, F. J.; Spencer, R. W.; Hess, H.-J. Science 1991, 257, 435.
4. For recent advances, see: (a) Shaw, D.; Chicchi, G. G.; Elliott, J. M.; Kurtz, M.; Morrison, D.; Ridgill, M. P.; Szeto, N.; Watt, A. P.; Williams, A. R.; Swain, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 3031.
5. (b) Elliott, J. M.; Castro, J. L.; Chicchi, G. G.; Cooper, L. C.; Dinnell, K.; Hollingworth, G. J.; Ridgill, M. P.; Rycroft, W.; Kurtz, M. M.; Shaw, D. E.; Swain, C. J.; Tsao, K.-L.; Yang, L. Bioorg. Med. Chem. Lett. 2002, 12, 1755.
6. (c) Cooper, L. C.; Carlson, E. J.; Castro, J. L.; Chicchi, G. G.; Dinnell, K.; Di Salvo, J.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Ridgill, M. P.; Rycroft, W.; Tsao, K.-L.; Swain, C. J. Bioorg. Med. Chem. Lett. 2002, 12, 1759.
7. (d) Seward, E. M.; Carlson, E.; Harrison, T.; Haworth, K. E.; Herbert, R.; Kelleher, F. J.; Kurtz, M. M.; Moseley, J.; Owen, S. N.; Owens, A. P.; Sadowski, S. J.; Swain, C. J.; Williams, B. J. Bioorg. Med. Chem. Lett. 2002, 12, 2515.
8. (e) Williams, B. J.; Cascieri, M. A.; Chicchi, G. G.; Harrison, T.; Owens, A. P.; Owen, S. N.; Rupniak, N. M. J.; Tattersall, F. D.; Williams, A.; Swain, C. J. Bioorg. Med. Chem. Lett. 2002, 12, 2719.
9. (f) Gale, J. D.; O'Neill, B. T.; Humphrey, J. M. Expert Opin. Ther. Pat. 2001, 11, 1837.
10. Harrison, T.; Wiliams, B. J.; Swain, C. J.; Ball, R. G. Bioorg. Med. Chem. Lett. 1994, 4, 2545.
11. (a) Fürstner, A. Angew. Chem. Int. Ed. 2000, 39, 3012.
12. (b) Grubbs, R. H. Tetrahedron 2004, 60, 7117.
13. McMurry, J. E. Chem. Rev. 1989, 89, 1513.
14. Vaultier, M.; Knouzi, N.; Carrie, R. Tetrahedron Lett. 1983, 24, 763.
15. 3): δ = 1.11 (9 H, s), 1.67 (1 H, m), 1.88 (1 H, br), 2.08-2.13 (3 H, m), 2.52 (1 H, m), 3.19 (1 H, dd, J = 1.6, 9.3 Hz), 3.50 (1 H, dt, J = 2.5, 9.4 Hz), 4.56 (1 H, d, J = 6.2 Hz), 7.25 (1 H, m), 7.32 (2 H, m), 7.58 (2 H, m).
16. Cascieri, M. A.; Ber, E.; Fong, T. M.; Sadowski, S.; Bansal, A.; Swain, C. J.; Seward, E. M.; Frances, B.; Burns, D.; Strader, C. D. Mol. Pharmacol. 1992, 47, 458.