4-Chlorobenzyl sulfonamide and sulfamide derivatives of histamine homologues: The design of potent histamine H3 receptor antagonists

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 21, 1999, Pages 3103-3108

  Tozer, Matthew J ^a   Buck, Ildiko M ^a   Cooke, Tracey ^a   Barret Kalindjian, S ^a   McDonald, Iain M ^a   Pether, Michael J ^a   Steel, Katherine I M ^a  

^a James Black Foundation   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

4 CHLOROBENZYLSULFAMIDE DERIVATIVE; 4 CHLOROPHENYLMETHANESULFONAMIDE DERIVATIVE; BENZYL DERIVATIVE; HISTAMINE; HISTAMINE H3 RECEPTOR ANTAGONIST; HISTAMINE RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; BIOASSAY; CHEMICAL MODIFICATION; DRUG DESIGN; DRUG SCREENING; GUINEA PIG; ILEUM; NONHUMAN; PARTIAL DRUG SYNTHESIS; RECEPTOR AFFINITY; STRUCTURE ANALYSIS;

ANIMALS; DRUG DESIGN; GUINEA PIGS; HISTAMINE; HISTAMINE ANTAGONISTS; ILEUM; MOLECULAR STRUCTURE; MUSCLE CONTRACTION; NAPHTHALENES; RECEPTORS, HISTAMINE H3; SULFONAMIDES;

ANIMALIA; CAVIA PORCELLUS; SUS SCROFA;

EID: 0033230996     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00535-1     Document Type: Article

References (25)

1. 3 receptor has recently been reported: Lovenberg, T. W.; Roland, B. L.; Wilson, S. J.; Jiang, X.; Pyati, J.; Huvar, A.; Jackson, M. R.; Erlander, M. G. Mol. Pharmacol. 1999, 55, 1101.
2. 3 receptor has recently been reported: Lovenberg, T. W.; Roland, B. L.; Wilson, S. J.; Jiang, X.; Pyati, J.; Huvar, A.; Jackson, M. R.; Erlander, M. G. Mol. Pharmacol. 1999, 55, 1101.
3. 3 receptor antagonists has been the subject of a recent review: Stark, H.; Schlicker, E.; Schunack, W. Drugs Fut. 1996, 21, 507.
4. Leurs, R.; Blandina, P.; Tedford, C.; Timmerman, H. TiPS 1998, 19, 177.
5. The results of phase I human trials have been reported for the Gliatech antagonist, GT2331: Gliatech Inc.; Press release 1st March 1999; http://www.gliatech.com/pages/corp-info/P_R_8.htm.
6. Tozer, M. J.; Harper, E. A.; Kalindjian, S. B.; Pether, M. J.; Shankley, N. P.; Watt, G. F. Bioorg. Med. Chem. Lett. 1999, 9, 1825.
7. Wolin, R.; Connolly, M.; Afonso, A.; Hey, J. A.; She, H.; Rivelli, M. A.; Williams, S. M.; West, Jr., R. E. Bioorg. Med. Chem. Lett. 1998, 8, 2157.
8. James Black Foundation patent publication number WO 97/29092, 1997.
9. van der Goot, H.; Schepers, M. J. P.; Sterk, G. J.; Timmerman, H. Eur. J. Med. Chem. 1992, 27, 511.
10. Clitherow, J. W.; Beswick, P.; Irving, W. J.; Scopes, D. I. C.; Barnes, J. C.; Clapham, J.; Brown, J. D.; Evans, D. J.; Hayes, A. G. Bioorg. Med. Chem. Lett. 1996, 6, 833.
11. Stark, H.; Lipp, R.; Arrang, J.-M.; Garbarg, M.; Schwartz, J.-C; Schunack, W. Eur. J. Med. Chem. 1994, 29, 695.
12. Stark, H.; Lipp, R.; Arrang, J.-M.; Garbarg, M.; Ligneau, X.; Schwartz, J.-C.; Schunack, W. Eur. J. Pharm. Sci. 1995, 3, 95.
13. Stark, H.; Ligneau, X.; Arrang, J.-M.; Schwartz, J.-C.; Schunack, W. Pharmazie 1997, 52, 419.
14. Dewynter, G.; Aouf, N.; Criton, M.; Montero, J.-L. Tetrahedron 1993, 49, 65.
15. Vollinga, R. C.; Menge, W. M. P. B.; Leurs, R.; Timmerman, H. J. Med. Chem. 1995, 38, 266.
16. For examples of Mitsunobu reactions with sulfamides: (a) Dewynter, G.; Aouf, N.; Regainia, Z.; Montero, J.-L. Tetrahedron 1996, 52, 993.
17. (b) Abdaoui, M.; Dewynter, G.; Montero, J.-L. Tetrahedron Lett. 1996, 37, 5695.
18. (c) Abdaoui, M.; Dewynter, G.; Aouf, N.; Favre, G.; Morère, A.; Montero, J.-L. Bioorg. Med. Chem. Lett. 1996, 4, 1227.
19. (a) Watt, G. F.; Hamilton, L. C.; Shankley, N. P.; Black, J. W. Br. J. Pharmacol. 1997, 122, 434P.
20. (b) Trzeciakowski, J. P. J. Pharmacol. Exp. Ther. 1987, 243, 874.
21. (a) Harper, E. A.; Shankley, N. P.; Black, J. W. Br. J. Pharmacol. 1997, 122, 430P.
22. (b) Harper, E. A.; Gardner, B.; Griffin, E. P.; Shankley, N. P.; Black, J. W. Br. J. Pharmacol. 1997, 122, 431P.
23. 20 compounds 6 and 17 were found to be inactive at 30μM in the guinea pig right atrium assay.
24. Watt, G. F.; Shankley, N. P.; Black, J. W. Br. J. Pharmacol. 1995, 114, 260P.
25. Angus, J. A.; Black, J. W. Circ. Res. 1980, 46, I-64.