Cyclic amine sulfonamides as linkers in the design and synthesis of novel human β3 adrenergic receptor agonists

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 13, 2003, Pages 2191-2194

  Sum, Fuk Wah ^a   Wong, Victoria ^a   Han, Stella ^b   Largis, Elwood ^b   Mulvey, Ruth ^b   Tillett, Jeff ^b  

^a WYETH RESEARCH   (United States)

^b PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; AZETIDINE DERIVATIVE; BETA 1 ADRENERGIC RECEPTOR; BETA 2 ADRENERGIC RECEPTOR; BETA 3 ADRENERGIC RECEPTOR; BETA 3 ADRENERGIC RECEPTOR STIMULATING AGENT; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE; SULFONAMIDE;

ANIMAL CELL; ARTICLE; CHO CELL; DRUG DESIGN; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG SYNTHESIS; HUMAN; NONHUMAN; RECEPTOR AFFINITY;

EID: 0038209328     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00387-1     Document Type: Article

References (25)

1. (a) Weyer C., Gautier J.F., Danforth E. Diabetes Metabolism. 25:1999;11
2. (b) Pietri-Rouxel F., Strosberg A.D. Fundam. Clin. Pharmacol. 9:1995;211.
3. Recent reviews: (a) Arch J.R.S. Eur. J. Pharmacol. 440:2002;99 (b) de Souza C.J., Burkey B.F. Curr. Pharm. Design. 7:2001;1433 (c) Kordik C.P., Reitz A.B. J. Med. Chem. 42:1999;181 (d) Webber A.E. Ann. Rep. Med. Chem. 33:1998;194 (e) Dow R.L. Exp. Opin. Invest. Drugs. 6:1997;1811.
4. Recent reviews: (a) Arch J.R.S. Eur. J. Pharmacol. 440:2002;99 (b) de Souza C.J., Burkey B.F. Curr. Pharm. Design. 7:2001;1433 (c) Kordik C.P., Reitz A.B. J. Med. Chem. 42:1999;181 (d) Webber A.E. Ann. Rep. Med. Chem. 33:1998;194 (e) Dow R.L. Exp. Opin. Invest. Drugs. 6:1997;1811.
5. Recent reviews: (a) Arch J.R.S. Eur. J. Pharmacol. 440:2002;99 (b) de Souza C.J., Burkey B.F. Curr. Pharm. Design. 7:2001;1433 (c) Kordik C.P., Reitz A.B. J. Med. Chem. 42:1999;181 (d) Webber A.E. Ann. Rep. Med. Chem. 33:1998;194 (e) Dow R.L. Exp. Opin. Invest. Drugs. 6:1997;1811.
6. Recent reviews: (a) Arch J.R.S. Eur. J. Pharmacol. 440:2002;99 (b) de Souza C.J., Burkey B.F. Curr. Pharm. Design. 7:2001;1433 (c) Kordik C.P., Reitz A.B. J. Med. Chem. 42:1999;181 (d) Webber A.E. Ann. Rep. Med. Chem. 33:1998;194 (e) Dow R.L. Exp. Opin. Invest. Drugs. 6:1997;1811.
7. Recent reviews: (a) Arch J.R.S. Eur. J. Pharmacol. 440:2002;99 (b) de Souza C.J., Burkey B.F. Curr. Pharm. Design. 7:2001;1433 (c) Kordik C.P., Reitz A.B. J. Med. Chem. 42:1999;181 (d) Webber A.E. Ann. Rep. Med. Chem. 33:1998;194 (e) Dow R.L. Exp. Opin. Invest. Drugs. 6:1997;1811.
8. Emorine L.J., Marullo S., Briend-Sutren M.-M., Patay G., Tate K., Delavier-Klutchko C., Strosberg A.D. Science. 245:1989;1118.
9. Liggett S.B. Mol. Pharmacol. 42:1992;634.
10. Van Baak M.A., Hul G.B.J., Toubro S., Astrup A., Gottesdiener K.M., DeSmet M., Saris W.H.M. Clin. Pharmacol. Ther. 71:2002;272.
11. (a) Yamanishi T., Chapple C.R., Yasuda K., Yoshida K., Chess-Williams R. Brit. J. Pharmacol. 135:2002;129 (b) Yamaguchi O. Urology. 59:2002;25 (c) Tanaka N., Tamai T., Mukaiyama H., Hirabayashi A., Muranaka H., Ishikawa T., Akahane S., Akahane M. Bioorg. Med. Chem. 9:2001;3265 (d) Morita T., Iizuka H., Iwata T., Kondo S.J. Smooth Muscle Res. 36:2000;21 (e) Longhurst P.A., Levendusky M. Brit. J. Pharmacol. 127:1999;1744.
12. (a) Yamanishi T., Chapple C.R., Yasuda K., Yoshida K., Chess-Williams R. Brit. J. Pharmacol. 135:2002;129 (b) Yamaguchi O. Urology. 59:2002;25 (c) Tanaka N., Tamai T., Mukaiyama H., Hirabayashi A., Muranaka H., Ishikawa T., Akahane S., Akahane M. Bioorg. Med. Chem. 9:2001;3265 (d) Morita T., Iizuka H., Iwata T., Kondo S.J. Smooth Muscle Res. 36:2000;21 (e) Longhurst P.A., Levendusky M. Brit. J. Pharmacol. 127:1999;1744.
13. (a) Yamanishi T., Chapple C.R., Yasuda K., Yoshida K., Chess-Williams R. Brit. J. Pharmacol. 135:2002;129 (b) Yamaguchi O. Urology. 59:2002;25 (c) Tanaka N., Tamai T., Mukaiyama H., Hirabayashi A., Muranaka H., Ishikawa T., Akahane S., Akahane M. Bioorg. Med. Chem. 9:2001;3265 (d) Morita T., Iizuka H., Iwata T., Kondo S.J. Smooth Muscle Res. 36:2000;21 (e) Longhurst P.A., Levendusky M. Brit. J. Pharmacol. 127:1999;1744.
14. (a) Yamanishi T., Chapple C.R., Yasuda K., Yoshida K., Chess-Williams R. Brit. J. Pharmacol. 135:2002;129 (b) Yamaguchi O. Urology. 59:2002;25 (c) Tanaka N., Tamai T., Mukaiyama H., Hirabayashi A., Muranaka H., Ishikawa T., Akahane S., Akahane M. Bioorg. Med. Chem. 9:2001;3265 (d) Morita T., Iizuka H., Iwata T., Kondo S.J. Smooth Muscle Res. 36:2000;21 (e) Longhurst P.A., Levendusky M. Brit. J. Pharmacol. 127:1999;1744.
15. (a) Yamanishi T., Chapple C.R., Yasuda K., Yoshida K., Chess-Williams R. Brit. J. Pharmacol. 135:2002;129 (b) Yamaguchi O. Urology. 59:2002;25 (c) Tanaka N., Tamai T., Mukaiyama H., Hirabayashi A., Muranaka H., Ishikawa T., Akahane S., Akahane M. Bioorg. Med. Chem. 9:2001;3265 (d) Morita T., Iizuka H., Iwata T., Kondo S.J. Smooth Muscle Res. 36:2000;21 (e) Longhurst P.A., Levendusky M. Brit. J. Pharmacol. 127:1999;1744.
16. 4-Hexylureidobenzenesulfonyl chloride was prepared according to: Chivers G.E., Cremlyn R.J., Guy R., Honeyman R., Reynolds P. Aust. J. Chem. 28:1975;413. All other sulfonyl chlorides used are from commercial sources.
17. 1H NMR, low- and high-resolution mass spectrometry. Except the pyrrolidine derivatives, all compounds described are single isomers. For experimental details, see: Sum, F.-W.; Hu, B. PCT Int. Appl., WO 0206221.
18. (a) . For the synthesis of 6a-6d: Siegel M.G., Shuker A.J., Droste C.A., Hahn P.J., Jesudason C.D., Mcdonald J.H. III, Matthews D.P., Rito C.J., Thorpe A. J. Mol. Div. 3:1998;113 (b) Berridge M.S., Cassidy E.H., Terris A.H., Vesselle J.-M. Nucl. Med. Biol. 19:1992;563 (c) Bell, M. G.; Crowell, T. A.; Matthews, D. P.; Mcdonald, J. H., III; Nee, D. A.; Shuker, A. J.; Winter, M. A. UA Patent 5,786,356. (d) Hu B., Ellingboe J., Gunawan I., Han S., Largis E., Li Z., Malamas M., Mulvey R., Oliphant A., Sum F.-W., Tillett J., Wong V. Bioorg. Med. Chem. Lett. 11:2001;757.
19. (a) . For the synthesis of 6a-6d: Siegel M.G., Shuker A.J., Droste C.A., Hahn P.J., Jesudason C.D., Mcdonald J.H. III, Matthews D.P., Rito C.J., Thorpe A. J. Mol. Div. 3:1998;113 (b) Berridge M.S., Cassidy E.H., Terris A.H., Vesselle J.-M. Nucl. Med. Biol. 19:1992;563 (c) Bell, M. G.; Crowell, T. A.; Matthews, D. P.; Mcdonald, J. H., III; Nee, D. A.; Shuker, A. J.; Winter, M. A. UA Patent 5,786,356. (d) Hu B., Ellingboe J., Gunawan I., Han S., Largis E., Li Z., Malamas M., Mulvey R., Oliphant A., Sum F.-W., Tillett J., Wong V. Bioorg. Med. Chem. Lett. 11:2001;757.
20. (a) . For the synthesis of 6a-6d: Siegel M.G., Shuker A.J., Droste C.A., Hahn P.J., Jesudason C.D., Mcdonald J.H. III, Matthews D.P., Rito C.J., Thorpe A. J. Mol. Div. 3:1998;113 (b) Berridge M.S., Cassidy E.H., Terris A.H., Vesselle J.-M. Nucl. Med. Biol. 19:1992;563 (c) Bell, M. G.; Crowell, T. A.; Matthews, D. P.; Mcdonald, J. H., III; Nee, D. A.; Shuker, A. J.; Winter, M. A. UA Patent 5,786,356. (d) Hu B., Ellingboe J., Gunawan I., Han S., Largis E., Li Z., Malamas M., Mulvey R., Oliphant A., Sum F.-W., Tillett J., Wong V. Bioorg. Med. Chem. Lett. 11:2001;757.
21. (a) . For the synthesis of 6a-6d: Siegel M.G., Shuker A.J., Droste C.A., Hahn P.J., Jesudason C.D., Mcdonald J.H. III, Matthews D.P., Rito C.J., Thorpe A. J. Mol. Div. 3:1998;113 (b) Berridge M.S., Cassidy E.H., Terris A.H., Vesselle J.-M. Nucl. Med. Biol. 19:1992;563 (c) Bell, M. G.; Crowell, T. A.; Matthews, D. P.; Mcdonald, J. H., III; Nee, D. A.; Shuker, A. J.; Winter, M. A. UA Patent 5,786,356. (d) Hu B., Ellingboe J., Gunawan I., Han S., Largis E., Li Z., Malamas M., Mulvey R., Oliphant A., Sum F.-W., Tillett J., Wong V. Bioorg. Med. Chem. Lett. 11:2001;757.
22. Liu H.J., Nyangulu J.M. Tetrahedron Lett. 29:1988;3167.
23. Olofson R.A., Martz J.T., Senet J.-P., Piteau M., Malfroot T. J. Org. Chem. 49:1984;2081.
24. Van S.A., Nahmias D.K.S., Briend-Sutren M.M., Strosberg A.D., Emorine L.J. Eur. J. Biochem. 213:1993;1117.
25. Tate K.M., Briend-Sutren M.M., Emorine L.J., Delavier-Klutchko C., Marullo S., Strosberg A.D. Eur. J. Biochem. 196:1993;357.