Preparation and characterization of N-(3-pyridinyl) spirocyclic diamines as ligands for nicotinic acetylcholine receptors

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 6, 2009, Pages 1682-1685

  Sippy, Kevin B ^a   Anderson, David J ^a   Bunnelle, William H ^a   Hutchins, Charles W ^a   Schrimpf, Michael R ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

4 2; ABT 594; Acetylcholine; Diamines; nAChR; Nicotinic; Receptors

Indexed keywords

5 (2 AZETIDINYLMETHOXY) 2 CHLOROPYRIDINE; EPIBATIDINE; NICOTINE; NICOTINIC RECEPTOR; TEBANICLINE; UNCLASSIFIED DRUG;

ANALGESIA; ARTICLE; BINDING AFFINITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG DESIGN; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; LIGAND BINDING; NONHUMAN; PHARMACOPHORE; RAT;

ANIMALS; AZETIDINES; CHEMISTRY, PHARMACEUTICAL; DIAMINES; DRUG DESIGN; HUMANS; KINETICS; LIGANDS; MODELS, CHEMICAL; MOLECULAR CONFORMATION; PYRIDINES; RATS; RECEPTORS, NICOTINIC; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 61349115674     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2009.01.099     Document Type: Article

References (23)

1. Jain K.K. Curr. Opin. Inv. Drugs 5 (2004) 76
2. Meyer M.D. Drug Dev. Res. 67 (2006) 355
3. Bunnelle W.H., and Decker M.W. Exp. Opin. Ther. Pat. 13 (2003) 1003
4. Bitner R.S., Nikkel A.L., Curzon P., Donnelly-Roberts D.L., Puttfarcken P.S., Namovic M., Jacobs I.C., Meyer M.D., and Decker M.W. Brain Res. 871 (2000) 66
5. Marubio L.M., del Mar Arroyo-Jimenez M., Cordero-Erausquin M., Lena C., Le Novere N., de Kerchove d'Exaerde A., Huchet M., Damaj M.I., and Changeux J.-P. Nature 398 (1999) 8085
6. Sullivan J.P., and Bannon A.W. CNS Drug Rev. 2 (1996) 21
7. Spande T.F., Garraffo H.M., Edwards M.W., Yeh H.J.C., Pannell L., and Daly J.W. J. Am. Chem. Soc. 114 (1992) 3475
8. Bannon A.W., Decker M.W., Holladay M.W., Curzon P., Donnelly-Roberts D.L., Puttfarcken P.S., Bitner R.S., Diaz A., Dickenson A.H., Porsolt R.D., Williams M., and Arneric S.P. Science 279 (1998) 77
9. Holladay M.W., Wasicak J.T., Lin N.-H., He Y., Ryther K.B., Bannon A.W., Buckley M.J., Kim D.J.B., Decker M.W., Anderson D.J., Campbell J.E., Kuntzweiler T., Donnelly-Roberts D.L., Piattoni-Kaplan M., Briggs C.A., Williams M., and Arneric S.P. J. Med. Chem. 41 (1998) 407
10. Bunnelle W.H., Daanen J.F., Ryther K.B., Schrimpf M.R., Dart M.J., Gelain A., Meyer M.D., Frost J.M., Anderson D.J., Buckley M.J., Curzon P., Cao Y.-J., Puttfarcken P.S., Searle X., Ji J., Putman C.B., Surowy C.S., Toma L., and Barlocco D. J. Med. Chem. 50 (2007) 3627
11. Ji J., Schrimpf M.R., Sippy K.B., Bunnelle W.H., Li T., Anderson D.J., Faltynek C., Surowy C.S., Dyhring T., Ahring P.K., and Meyer M.D. J. Med. Chem. 50 (2007) 5493
12. The chiral amino acids were commercially available, but the stereogenic center is racemized during the synthesis.
13. Culbertson T.P., Sanchez J.P., Gambino L., and Sesnie J.S. J. Med. Chem. 32 (1990) 2270
14. Padwa A., and Dent W. Org. Synth. 67 (1989) 133
15. Anderson D.J., and Arneric S.P. Eur. J. Pharmacol. 253 (1994) 261
16. Kuntzweiler T.A., Arneric S.P., and Donnelly-Roberts D.L. Drug Dev. Res. 44 (1998) 14
17. Balboni G., Marastoni M., Merighi S., Borea P.A., and Tomatis R. Eur. J. Med. Chem. 35 (2000) 979
18. Abreo M.A., Lin N.-H., Garvey D.S., Gunn D.E., Hettinger A.-M., Wasicak J.T., Pavlik P.A., Martin Y.C., Donnelly-Roberts D.L., Anderson D.J., Sullivan J.P., Williams M., Arneric S.P., and Holladay M.W. J. Med. Chem. 39 (1996) 817
19. Data for bridged compound A is that of (1S,4S)-2-(3-pyridyl)-2,5-diazabicyclo[2.2.1]heptane taken from Ref. 10.
20. Data for fused compound B is that of (1S,5S)-3-(3-pyridyl)-3,6-diazabicyclo[3.2.0]heptane taken from Ref. 11.
21. Tønder J.E., and Olesen P.H. Curr. Med. Chem. 8 (2001) 651
22. Tønder J.E., Olesen P.H., Hansen J.B., Begtrup M., and Pettersson I. J. Comput. Aided Mol. Des. 15 (2001) 247
23. Ewig C.S., Berry R., Dinur U., Hill J.R., Hwang M.J., Li H., Liang C., Maple J., Peng Z., Stockfisch T.P., Thacher T.S., Yan L., Ni X., and Hagler A.T. J. Comput. Chem. 22 (2001) 1782