Synthesis of some nefopam analogues as potential analgesics

Australian Journal of Chemistry

Volumn 55, Issue 9, 2002, Pages 577-585

  Rosamilia, Anthony E ^a   Mayes, Penelope A ^a   Papadopoulos, Roslyn ^a   Campi, Eva M ^a   Jackson, W Roy ^a   Rash, Lachlan ^a   Jarrott, Bevyn ^a  

^a MONASH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0036431059     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/CH02097     Document Type: Article

References (41)

1. (a) Rexall Drug and Chemical Co., Neth. Appl., 6,606,390 (Chem. Abstr. 1967, 66, 55535).
2. (b) B.J. Baltes. U. S. Pat., 1969, 3,487,153 (Chem. Abstr. 1970, 72, 79124).
3. (c) M.W. Klohs, M.D. Draper, F.J. Petracek, K.H. Ginzel, O.N. Ré, Arzneim.-Forsch. (Drug Res.) 1972, 22, 132.
4. For a review, see R.C. Heel, R.N. Brogden, G.E. Pakes, T.M. Speight, G.S. Avery, Drugs 1980, 19, 249.
5. V. Minotti, L. Patoia, F. Roila, C. Basurto, M. Tonato, V. Pasqualucci, V. Maresca, A. Del Favero, Pain 1989, 36, 177.
6. W.R. Jackson, F.C. Copp, J.D. Cullen, F.J. Guyett, I.D. Rae, H. Pothoulackis, A.K. Serelis, M. Wong, Clinical and Exp. Pharmacol. Physiol. 1992, 19, 17.
7. W.R. Jackson, K.R. Subasinghe, A.L.A. Boura, PCT Int. Appl., 1999, WO 99 38869 (Chem. Abstr. 1999, 131, 144745).
8. S. Botros, A.W. Lipkowski, D.L. Larson, P.A. Stark, A.E. Takemori, P.S. Portoghese, J. Med. Chem. 1989, 32, 2068.
9. S.L. Olmsted, A.E. Takemori, P.S. Portoghese, J. Med. Chem. 1993, 36, 179.
10. J.B. Bremner, N. Thirasasana, Aust. J. Chem. 1982, 35, 2307.
11. P. Aeberli, W.J. Houlihan, J. Org. Chem. 1969, 34, 165.
12. P. Aeberli, W.J. Houlihan, J. Org. Chem. 1969, 34, 1720.
13. R.S. Garigipati, Tetrahedron Lett. 1990, 31, 1969.
14. M.S. Bernatowicz, Y. Wu, G.R. Matsueda, J. Org. Chem. 1992, 57, 2497.
15. J.A. Bell, C. Kenworthy, Synthesis 1971, 12, 650.
16. M.W. Klohs, F.J. Petracek, U. S. Pat., 1969, 3,446,820 (Chem. Abstr. 1969, 71, 50007).
17. K. Krowicki, J.W. Lown, J. Org. Chem. 1987, 52, 3493.
18. (a) V.S. Shklyaev, G.A. Veikhman, Y.M. Chupina, K.D. Potemkin, Zh. Obsch. Khim. 1984, 54, 919.
19. (b) J. General Chem. (U. S. S. R.) 1984, 54, 819.
20. (a) J. von Braun, Ber. 1907, 40, 3914.
21. (b) H.A. Hageman, Org. React. Vol. VII 1953, 198.
22. N.J. Tresnak-Rustad, M.E. Wood, Biochem. Pharmacol. 1981, 30, 2847.
23. P.F. Vonvoigtlander, R.A. Lewis, G.L. Neft, H.J. Triezenberg, Prog. Neuro-Psychopharmacol. Biol. Psychiat. 1983, 7, 651.
24. F. Guirimand, X. Dupont, D. Bouhassira, L. Brasseur, M. Chauvin, Pain 1999, 80, 399.
25. J.C. Gasser, J.W. Bellville, Clin. Pharmacol. Ther. 1975, 18, 175.
26. R.W. Fuller, H.D. Snoddy, Neuropharmacol. 1993, 32, 995.
27. O.B. Fasmer, O.-G. Berge, H.A. Jørgensen, K. Hole, J. Pharm. Pharmacol. 1987, 39, 508.
28. J.H. Rosland, K. Hole, J. Pharm. Pharmacol. 1990, 42, 437.
29. PALLAS Ver. 1. 2 Software 1994 (CompuDrug Chemistry Ltd.: Budapest, Hungary).
30. L. Busch, M. Wald, L. Sterin-Borda, E. Borda, Pharmacol. Res. 2000, 41, 39.
31. R. Glaser, S. Geresh, J. Blumenfeld, D. Donnell, N. Sugisaka, M. Drouin, A. Michel, J. Pharm. Sci. 1993, 82, 276.
32. J.W. Misner, J. Org. Chem. 1987, 52, 3166.
33. 'Collect' Data Collection Software 1998 (Nonius BV: Delft, The Netherlands).
34. Denzo-SMN Z. Otwinowski, W. Minor, Methods in Enzymology, Vol. 276: Macromolecular Crystallography, Part A (C.W. Carter, Jr, R.M. Sweet, Eds) 1997, p. 307-326 (Academic Press: London, U.K.).
35. S. Mackay, C.J. Gilmore, C. Edwards, M. Tremayne, N. Stewart, K. Shackland, maXus: a Computer Program for the Solution and Refinement of Crystal Structures from Diffraction Data 1998 (University of Glasgow: Scotland, UK; Nonius BV: Delft, The Netherlands; Mac Science Co. Ltd.: Yokohama, Japan).
36. P.T. Beurskens, G. Admiraal, G. Beurskens, W.P. Bosman, R. de Gelder, R. Israel, J.M.M. Smits, The DIRDIF-94 Program System; Technical Report of the Crystallography Laboratory 1994 (University of Nijmegen: The Netherlands).
37. D.T. Cromer, J.T. Waber, International Tables for X-Ray Crystallography, Vol. IV 1974, Table 2.2 A (The Kynoch Press: Birmingham, England).
38. J.A. Ibers, W.C. Hamilton, Acta Crystallogr. 1964, 17, 781.
39. D.C. Creagh, W.J. McAuley, International Tables for X-Ray Crystallography, Vol. C (A.J.C. Wilson, Ed.) 1992, Table 4.2.6.8, pp. 219-222 (Kluwer Academic Publishers: Boston).
40. D.C. Creagh, J.H. Hubbell, International Tables for X-Ray Crystallography, Vol. C (A.J.C. Wilson, Ed.) 1992, Table 4.2.4.3, pp. 200-206 (Kluwer Academic Publishers: Boston).
41. teXsan: Crystal Structure Analysis Package 1985 and 1992 (Molecular Structure Corporation).