Syntheses of 1,2-diamino and 1,2-aminoalcohol derivatives in the piperidine and pyrrolidine series as anti-amnesic agents

Bioorganic and Medicinal Chemistry

Volumn 7, Issue 8, 1999, Pages 1647-1654

  Zhao, Shikai ^a   Freeman, Jeremiah P ^a   Bacon, C L ^b   Fox, G B ^b   O'Driscoll, E ^b   Foley, A G ^b   Kelly, J ^b   Farrell, U ^b   Regan, Ciaran ^b   Mizsak, Stephen A ^c   Szmuszkovicz, Jacob ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

^b UNIVERSITY COLLEGE DUBLIN   (Ireland)

^c PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHOLINESTERASE INHIBITOR; INDOLIZIDINE DERIVATIVE; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; QUINOLIZIDINE DERIVATIVE; TACRINE;

AMNESIA; ANIMAL EXPERIMENT; ANIMAL MODEL; CHOLINESTERASE INHIBITION; CONTROLLED STUDY; DRUG SYNTHESIS; NONHUMAN; RAT; SHORT SURVEY; STRUCTURE ACTIVITY RELATION;

EID: 0032811739     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(99)00079-6     Document Type: Article

References (24)

1. (a) Cacabelos, R.; Nordberg, A.; Caamaño, J.; Franco-Maside, A.; Fernandez-Novoa, L.; Gomez, M. J.; Alvarez, X. A.; Takedas, M.; Prous, J., Jr.; Nishimura, T.; Winblad, B. Drugs of Today 1994, 30, 295.
2. (b) Allain, H.; Bentue-Ferrer, D.; Belliard, S.; Derouesne, C. Prog. Med. Chem. 1997, 34, 46.
3. (c) Crimson, M. L.; Ann. Pharmacother. 1994, 28, 744.
4. (d) Hershenson, F. M.; Moos, W. H. J. Med. Chem. 1986, 29, 1125.
5. Hershenson, F. M. In New Leads and Targets in Drug Research. Alfred Benzon Symposium 33; Krogsgaard-Larsen, P.; Brogger, S.; Kofod, H., Eds; Munksgaard: Copenhagen, 1992; pp. 354-363.
6. (a) Inoue, A.; Kawai, T.; Wakita, M.; Iimura, Y.; Sugimoto, H.; Kawakami, Y. J. Med. Chem. 1996, 39, 4460.
7. (b) Kawakami, Y.; Inoue, A.; Kawai, T.; Wakita, M.; Sugimoto, H.; Hopfinger, A. J. Bioorg. Med. Chem. 1996, 4, 1429.
8. (c) Heydorn, W. E. Exp. Opin. Invest. Drugs 1997, 6, 1527.
9. Drugs Future 1994, 19, 656; 1996, 21, 766.
10. Drugs Future 1994, 19, 656; 1996, 21, 766.
11. Manning, F. C. American Family Physician 1994, 50, 819.
12. (a) Osterrieder, W. Br. J. Pharmac. 1987, 92, 521.
13. (b) Edwards, G.; Weston, E. H. In Receptor Data for Biological Experiments; Ellis Horwood: New York, NY, 1991; p 194.
14. (c) Evans, J. M.; Hamilton, T. C.; Longman, S. D.; Stemp, G., Eds. Potassium Channels and their Modulators: From Synthesis to Clinical Experience; Taylor and Francis, 1996.
15. (c) Glover, W. E. Gen. Pharmac. 1982, 13, 259.
16. (d) Drugs Future 1995, 20, 142.
17. O'Neill, P.M.; Bray, P. G.; Hawley, S. R.; Ward, S. A.; Park, B. K. Pharmacol. Ther. 1998, 77, 29.
18. Drugs Future 1991, 16, 33; 1994, 19, 343.
19. Drugs Future 1991, 16, 33; 1994, 19, 343.
20. Zhao, S.; Totleben, M. J.; Freeman, J. P.; Bacon, C. L.; Fox, G. B.; O'Driscoll, E.; Foley, A. G.; Kelly, J.; Farrell, U.; Regan, C.; Mizsak, S. A.; Szmuszkovicz, J. Bioorg. Med. Chem. 1999, 7, 1637.
21. Gonzalez, Trigo G.; Alvarez-Builla, J. An Quim, Ser C 1980, 76, 12: CA 94, 139584e.
22. cf. Morie, T.; Kato, S.; Haradsa, H.; Fujiwara, I.; Watanabe, K.; Matsumoto, J. J. Chem. Soc., Perkin Trans 1 1994, 2565. These authors describe the reaction of 1-benzyl-2-chloromethylpiperidine with NaN3, followed by reduction with sodium bis(2-methoxyethoxy)aluminum hydride and acetylation to give a mixture of 2-(acetylamino)methyl-1-benzylpiperidine and 3-acetylamino-1-benzylhexahydro-1H-azepine.
23. Cheeseman, R. S.; Kezaar, H. S. III.; Scribner, R. M. PCT Int. Appl. WO 92 12,128, 1992.
24. Solladie-Cavallo, A.; Bencheqroun, M. J. Org. Chem. 1992, 57, 5831.