Synthesis of new bridgehead substituted azabicyclo-[2.2.1]heptane and -[3.3.1]nonane derivatives as potent and selective α7 nicotinic ligands

Organic Letters

Volumn 12, Issue 21, 2010, Pages 5004-5007

  Slowinski, Franck ^a,b   Ayad, Omar Ben ^a,b   Vache, Julien ^a,c   Saady, Mourad ^a,b   Leclerc, Odile ^a,b   Lochead, Alistair ^a,c  

^a SANOFI   (France)

^b Exploratory Unit   (France)

^c TSU Aging ^*  (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; FUSED HETEROCYCLIC RINGS; HEPTANE; HETEROCYCLIC COMPOUND; LIGAND; NICOTINE; NONANE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALKANES; AZA COMPOUNDS; BICYCLO COMPOUNDS, HETEROCYCLIC; HEPTANES; LIGANDS; MOLECULAR STRUCTURE; NICOTINE;

EID: 78049489533     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102170q     Document Type: Article

References (21)

1. Martin, L. F.; Kem, W. R.; Freedman, R. Psychopharmacology 2004, 174, 54-64
2. Olincy, A.; Stevens, K. E. Biochem. Pharmacol. 2007, 74, 1192-1201
3. Dani, J. A. Biol. Psychiatry 2001, 49, 166-174
4. Sharma, G.; Vijayaraghavan, S. Curr. Med. Chem. 2008, 15, 2921-2932
5. For an overview of α7 nicotinic receptor ligands possessing an azabicyclic moiety, see
6. Romanelli, M. N.; Gratteri, P.; Guandalini, L.; Martini, E.; Bonaccini, C.; Gualtieri, F. ChemMedChem 2007, 2, 746-767
7. Broad, L. M.; Sher, E.; Asties, P. C.; Zwart, R.; O'Neill, M. J. Drug Future 2007, 32, 161-170
8. Mazurov, A.; Hauser, T.; Miller, C. H. Curr. Med. Chem. 2006, 13, 1657-1584
9. Orlek, B. S.; Blaney, F. E.; Brown, F.; Clark, M. S. G.; Hadley, M. S.; Hatcher, J.; Riley, G. J.; Rosenberg, H. E.; Wadsworth, H. J.; Wyman, P. J. Med. Chem. 1991, 34, 2726-2735
10. Jenkins, S. M.; Wadsworth, H. J.; Bromidge, S.; Orlek, B. S.; Wyman, P. A.; Riley, G. J.; Hawkins, J. J. Med. Chem. 1992, 35, 2392-2406
11. Orlek, B. S.; Cassidy, F.; Clark, M. S. G.; Faulkner, R. E.; Collings, E. J.; Hawkins, J.; Riley, G. J. Bioorg. Med. Chem. Lett. 1994, 4, 1411-1414
12. Badger, G. M.; Cook, J. W.; Walker, T. J. Chem. Soc. 1949, 1141-1144
13. Hazama, N.; Irie, H.; Mizutani, T.; Shingu, T.; Takada, M.; Uyeo, S.; Yoshitake, A. J. Chem. Soc. C 1968, 2947-2953
14. Su, D.-S.; Lim, J. L.; Markowitz, M. K.; Wan, B.-L.; Murphy, K. L.; Reiss, D. R.; Harrell, C. M.; O'Malley, S. S.; Ransom, R. W.; Chang, R. S. L.; Pettibone, D. J.; Tang, C.; Prueksaritanont, T.; Freidinger, R. M.; Bock, M. G. Bioorg. Med. Chem. Lett. 2007, 17, 3006-3009
15. Marks, M. J.; Collins, A. C. Mol. Pharmacol. 1982, 22, 554-564
16. Marks, M. J.; Stitzel, J. A.; Romm, E.; Wehner, J. M.; Collins, A. C. Mol. Pharmacol. 1986, 30, 427-436
17. For more informations on the SSR180711, see
18. Biton, B. Neuropsychopharmacology 2007, 32, 1-16
19. Pichat, P. Neuropsychopharmacology 2007, 32, 17-34
20. Anderson, D. J.; Arneric, S. P. Eur. J. Pharmacol. 1994, 253, 261-267
21. Hall, M.; Zerbe, L.; Leonard, S.; Freedman, R. Brain Res. 1993, 600, 127-133