Syntheses of piperidine and perhydroazepine derivatives, precursors of two selective antagonists of muscarinic M2 receptors: AF-DX 384 and its perhydroazepine isomer

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 24, 1996, Pages 2925-2932

  Perrio Huard, Cécile ^a   Ducandas, Christophe ^a   Lasne, Marie Claire ^a   Moreau, Bernard ^a  

^a GIP CYCERON   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748891971     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960002925     Document Type: Article

References (37)

1. R. K. Dieter, N. Deo, B. Lagu and J. W. Dieter, J. Org. Chem., 1992, 57, 1663 and references cited therein.
2. W. W. Engel, G. W. Eberlein, G. Mihm, G. Trummlitz, N. Mayer and A. De Jonge, Ger. Offen.. DE 3 643 666, 1988 (Chem. Abstr., 1989, 110, 39029f).
3. D. I. C. Scopes, N. F. Hayes, D. E. Bays, D. Belton, J. Brain, D. S. Brown, D. B. Judd, A. B. McElroy, C. A. Meerholz, A. Naylor, A. G. Hayes, M. J. Sheehan, P. J. Birch and M. B. Tyers, J. Med. Chem., 1992, 35, 490.
4. V. Vecchietti, A. Giordani, G. Giardina, R. Colle and G. D. Clarke, J. Med. Chem., 1991, 34, 397.
5. B. R. de Costa, C. Dominguez, X. S. He, W. Williams, L. Radesca and W. Bowen, J. Med. Chem., 1992, 35, 4334.
6. W. W. Engel, G. W. Eberlein, G. Mihm, R. Hammer and G. Trummlitz, J. Med. Chem., 1989, 32, 1718.
7. E. H. Banitt and G. J. Conard, J. Labelled Compd. Radiopharm., 1981, 18, 713.
8. T. R. Norton, A. A. Benson, R. A. Seibert and F. W. Bergstrom, J. Am. Chem. Soc., 1946, 68, 1330.
9. A. Terada, Y. Iizuka, K. Wachi and K. Fujibayashi, Eur. Pat. Appl., EP 356 247, 1990 (Chem. Abstr., 1990, 113, 7819q).
10. F. F. Blicke and J. L. Hughes, J. Org. Chem., 1961, 26, 3257.
11. M. Freifelder, R. M. Robinson and G. R. Stone, J. Org. Chem., 1962, 27, 284.
12. M. Freifelder and G. R. Stone, J. Org. Chem., 1961, 26, 3805.
13. V. Baliah, R. Jeyaraman and L. Chandrasekaran, Chem. Rev., 1983, 83, 379.
14. J. Perumattam, B. G. Shearer, W. L. Confer and R. M. Mathew, Tetrahedron Lett., 1991, 32, 7183.
15. M. C. Lasne, L. Barré, C. Huard, C. Ducandas and E. T. MacKenzie, J. Labelled Compd. Radiopliarm., 1994, 35, 425.
16. M. Entzeroth and N. Mayer, Biochem. Pliannacol., 1990, 40, 1674.
17. I. Aubert, D. Cécyre, S. Gauthier and R. Quirion, Eur. J. Pharmacol., 1992, 217, 1674.
18. P. Mickala, H. Boutin, C. Bellaner, C. Chevalier, E. T. MacKenzie and F. Dauphin, Nucl. Med. Biol., 1996, 23, 173.
19. E. Albertini, A. Barco, S. Benetti, C. De Risi, G. P. Pollini and V. Zanirato, Synlett, 1996, 29.
20. D. Alker, R. J. Bass and P. E. Cross, Eur. Pat. Appl, EP 404 359, 1990 (Chem. Abstr., 1991. 115, 29390f).
21. P. L. Ornstein, J. M. Schaus, J. W. Chambers, D. L. Huser, J. D. Leander, D. T. Wong, J. W. Paschal, N. D. Jones and J. B. Deeter, J. Med. Chem., 1989, 32, 827.
22. W. F. Minor, J. B. Hoekstra, D. Fisher and J. Sam, J. Med. Pharm. Chem., 1962, 5, 96.
23. N. Sperber, D. Papa, E. Schwenk, M. Sherlock and R. Fricano, J. Am. Chem. Soc., 1951, 73, 5752.
24. A. Benarab, S. Boyé, L. Savelon and G. Guillaumet, Tetrahedron Lett., 1993, 34, 7567.
25. M. Hudlicky, Reductions in Organic Chemistry, Ellis Horwood, Chichester, 1986, pp. 173 and 207.
26. J. March, Advanced Organic Chemistry, Wiley, Chichester, 4th edn., 1992, p. 411.
27. R. G. Weiss and E. I. Snyder, J. Org. Chem., 1971, 36, 403.
28. A. Gaucher, J. Ollivier and J. Salaün, Synlett, 1991, 151.
29. S. K. Hendrie and J. Leonard, Tetrahedron, 1987, 43, 3289.
30. H. R. Snyder and R. E. Meckert, J. Am. diem. Soc., 1952, 74, 2006.
31. G. A. Wiley, R. L. Hershkowitz, B. M. Rein and B. C. Chung, J. Am. Chem. Soc., 1964, 86, 964.
32. G. R. Brown, A. J. Foubister and B. Wright, J. Chem. Soc., Perkin Trans. 1, 1987, 553.
33. N. M. Deo and P. A. Crooks, Synth. Commun., 1995, 25, 691.
34. D. Berkes and B. Decroix, Bull. Soc. Chim. Fr., 1994, 131, 986.
35. T. Morie, S. Kato, H. Harada, I. Fujiwara, K. Watanabe and J. I. Matsumoto, J. Chem. Soc., Perkin Trans. 1, 1994, 2565.
36. L. Stella, B. Raynier and J. M. Surzur, Tetrahedron, 1981, 37, 2843.
37. L. E. Overman and J. Shim, J. Org. Chem., 1991, 56, 5005.