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Volumn 41, Issue 1, 2006, Pages 114-120

Structural-activity relationship study on C-4 carbon atom of the CB 1 antagonist SR141716: Synthesis and pharmacological evaluation of 1,2,4-triazole-3-carboxamides

(11) Jagerovic, Nadine a Hernandez Folgado, Laura a Alkorta, Ibon a Goya, Pilar a Martín, María Isabel b Dannert, María Teresa c Alsasua, Ángela c Frigola, Jordi d Cuberes, María Rosa d Dordal, Alberto d Holenz, Jörg d

a INSTITUTO DE QUÍMICA MÉDICA (Spain)

b UNIVERSIDAD REY JUAN CARLOS (Spain)

c UNIVERSIDAD COMPLUTENSE DE MADRID (Spain)

d Laboratorios Dr Esteve SA (Spain)

Author keywords

1,2,4 Triazole; Cannabinoid; Mouse vas deferens; SR141716

Indexed keywords

1,2,4 TRIAZOLE 3 CARBOXAMIDE; AMIDE; CANNABINOID 1 RECEPTOR; CANNABINOID RECEPTOR ANTAGONIST; CARBON; NITROGEN; RIMONABANT; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; DRUG BINDING; DRUG SYNTHESIS; MALE; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION; VAS DEFERENS;

ANIMALS; BINDING SITES; CYCLOHEXANOLS; MALE; MICE; PIPERIDINES; PYRAZOLES; RECEPTOR, CANNABINOID, CB1; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES; VAS DEFERENS;

EID: 33244484802 PISSN: 02235234 EISSN: None Source Type: Journal
DOI: 10.1016/j.ejmech.2005.06.012 Document Type: Article

Times cited : (25)

References (47)

1
- 0033921628
- Expert Opin
- R.G. Pertwee Expert Opin Invest. Drugs 9 2000 1553 1571
- (2000) Invest. Drugs , vol.9 , pp. 1553-1571
- Pertwee, R.G.¹

2
- 0036019382
- R.G. Pertwee, and R.A. Ross Prostaglandins Leukot. Essent. Fatty Acids 66 2002 101 121
- (2002) Prostaglandins Leukot. Essent. Fatty Acids , vol.66 , pp. 101-121
- Pertwee, R.G.¹ Ross, R.A.²

3
- 18444376760
- A.C. Howlett, F. Barth, T.I. Bonner, G. Cabral, P. Casellas, W.A. Devane, C.C. Felder, M. Herkenham, K. Mackie, B.R. Martin, R. Mechoulam, and R.G. Pertwee Pharmacol. Res. 54 2002 161 202
- (2002) Pharmacol. Res. , vol.54 , pp. 161-202
- Howlett, A.C.¹ Barth, F.² Bonner, T.I.³ Cabral, G.⁴ Casellas, P.⁵ Devane, W.A.⁶ Felder, C.C.⁷ Herkenham, M.⁸ MacKie, K.⁹ Martin, B.R.¹⁰ Mechoulam, R.¹¹ Pertwee, R.G.¹²

4
- 4644331847
- A.C. Howlett, C.S. Breivogel, S.R. Childers, S.A. Deadwyler, R.E. Hampson, and L.J. Porrino Neuropharmacology 47 Suppl 1 2004 345 358
- (2004) Neuropharmacology , vol.47 , Issue.1 SUPPL. , pp. 345-358
- Howlett, A.C.¹ Breivogel, C.S.² Childers, S.R.³ Deadwyler, S.A.⁴ Hampson, R.E.⁵ Porrino, L.J.⁶

5
- 0033815067
- P. Goya, and N. Jagerovic Expert Opin. Ther. Pat. 10 2000 1529 1538
- (2000) Expert Opin. Ther. Pat. , vol.10 , pp. 1529-1538
- Goya, P.¹ Jagerovic, N.²

6
- 4644262320
- J.H. Lange, and C.G. Kruse Curr. Opin. Drug Discov. Dev. 7 2004 498 506
- (2004) Curr. Opin. Drug Discov. Dev. , vol.7 , pp. 498-506
- Lange, J.H.¹ Kruse, C.G.²

7
- 33244456478
- H.P. Reggio Curr. Pharm. Des. 2003 1607 1633
- (2003) Curr. Pharm. Des. , pp. 1607-1633
- Reggio, H.P.¹

8
- 0028129936
- M. Rinaldi-Carmona, F. Barth, M. Heaulme, D. Shire, B. Calandra, C. Congy, and S. Martinez S. FEBS Lett. 350 1994 240 244
- (1994) S. FEBS Lett. , vol.350 , pp. 240-244
- Rinaldi-Carmona, M.¹ Barth, F.² Heaulme, M.³ Shire, D.⁴ Calandra, B.⁵ Congy, C.⁶ Martinez, S.⁷

9
- 3042571675
- Expert Opin
- S.C. Black Expert Opin Invest. Drugs 5 2004 389 394
- (2004) Invest. Drugs , vol.5 , pp. 389-394
- Black, S.C.¹

10
- 3042534848
- Expert Opin
- J.R. Fernandez, and D.B. Allison Expert Opin Invest. Drugs 5 2004 430 435
- (2004) Invest. Drugs , vol.5 , pp. 430-435
- Fernandez, J.R.¹ Allison, D.B.²

11
- 0037142337
- M.E. Francisco, H.H. Seltzman, A.F. Gilliam, R.A. Mitchell, S.L. Rider, R.G. Pertwee, L.A. Stevenson, and B.F. Thomas J. Med. Chem. 45 2002 2708 2719
- (2002) J. Med. Chem. , vol.45 , pp. 2708-2719
- Francisco, M.E.¹ Seltzman, H.H.² Gilliam, A.F.³ Mitchell, R.A.⁴ Rider, S.L.⁵ Pertwee, R.G.⁶ Stevenson, L.A.⁷ Thomas, B.F.⁸

12
- 0035129579
- J.L. Wiley, R.G. Jefferson, M.C. Grier, A. Mahadevan, R.K. Razdan, and B.R. Martin J. Pharmacol. Exp. Ther. 296 2001 1013 1022
- (2001) J. Pharmacol. Exp. Ther. , vol.296 , pp. 1013-1022
- Wiley, J.L.¹ Jefferson, R.G.² Grier, M.C.³ Mahadevan, A.⁴ Razdan, R.K.⁵ Martin, B.R.⁶

13
- 0033602129
- R. Lan, Q. Liu, P. Fan, S. Lin, S.R. Fernando, D. McCallion, R.G. Pertwee, and A. Makriyannis J. Med. Chem. 42 1999 769 776
- (1999) J. Med. Chem. , vol.42 , pp. 769-776
- Lan, R.¹ Liu, Q.² Fan, P.³ Lin, S.⁴ Fernando, S.R.⁵ McCallion, D.⁶ Pertwee, R.G.⁷ Makriyannis, A.⁸

14
- 0031981037
- B.F. Thomas, A.F. Gilliam, D.F. Burch, M.J. Roche, and H.H. Seltzman J. Pharmacol. Exp. Ther. 285 1998 285 292
- (1998) J. Pharmacol. Exp. Ther. , vol.285 , pp. 285-292
- Thomas, B.F.¹ Gilliam, A.F.² Burch, D.F.³ Roche, M.J.⁴ Seltzman, H.H.⁵

15
- 0037434591
- R. Katoch-Rouse, O.A. Pavlova, T. Caulder, A.F. Hoffman, A.G. Mukhin, and A.G. Horti J. Med. Chem. 46 2003 642 645
- (2003) J. Med. Chem. , vol.46 , pp. 642-645
- Katoch-Rouse, R.¹ Pavlova, O.A.² Caulder, T.³ Hoffman, A.F.⁴ Mukhin, A.G.⁵ Horti, A.G.⁶

16
- 0346059508
- M. Krishnamurthy, W. Li, and B.M. Moore Bioorg. Med. Chem. 12 2004 393 404
- (2004) Bioorg. Med. Chem. , vol.12 , pp. 393-404
- Krishnamurthy, M.¹ Li, W.² Moore, B.M.³

17
- 1842832439
- J.M. Mussinu, S. Ruiu, A.C. Mule, A. Pau, M.A. Carai, G. Loriga, G. Murineddu, and G.A. Pinna Bioorg. Med. Chem. 11 2003 251 263
- (2003) Bioorg. Med. Chem. , vol.11 , pp. 251-263
- Mussinu, J.M.¹ Ruiu, S.² Mule, A.C.³ Pau, A.⁴ Carai, M.A.⁵ Loriga, G.⁶ Murineddu, G.⁷ Pinna, G.A.⁸

18
- 33244489947
- Patent WO03082833 (2003).
- N. Jagerovic, P. Goya, L. Hernández-Folgado, I. Alkorta, M.I. Martín, M. Suardíaz, M.T. Dannert, Patent WO03082833 (2003).
- Jagerovic, N.¹ Goya, P.² Hernández-Folgado, L.³ Alkorta, I.⁴ Martín, M.I.⁵ Suardíaz, M.⁶ Dannert, M.T.⁷

19
- 2442651556
- N. Jagerovic, L. Hernandez-Folgado, I. Alkorta, P. Goya, M. Navarro, A. Serrano, F. Rodriguez de Fonseca, M.T. Dannert, A. Alsasua, M. Suardiaz, D. Pascual, and M.I. Martin J. Med. Chem. 47 2004 2939 2942
- (2004) J. Med. Chem. , vol.47 , pp. 2939-2942
- Jagerovic, N.¹ Hernandez-Folgado, L.² Alkorta, I.³ Goya, P.⁴ Navarro, M.⁵ Serrano, A.⁶ Rodriguez De Fonseca, F.⁷ Dannert, M.T.⁸ Alsasua, A.⁹ Suardiaz, M.¹⁰ Pascual, D.¹¹ Martin, M.I.¹²

20
- 1242294357
- B. Dyck, V.S. Goodfellow, T. Phillips, J. Grey, M. Haddach, M. Rowbottom, G.S. Naeve, B. Brown, and J. Saunders Bioorg. Med. Chem. Lett. 14 2004 1151 1154
- (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 1151-1154
- Dyck, B.¹ Goodfellow, V.S.² Phillips, T.³ Grey, J.⁴ Haddach, M.⁵ Rowbottom, M.⁶ Naeve, G.S.⁷ Brown, B.⁸ Saunders, J.⁹

21
- 20144379406
- J.H.M. Lange, H.H. Van Stuivenberg, H.K. Coolen, T.J. Adolfs, A.C. McCreary, H.G. Keizer, H.C. Wals, W. Veerman, A.J.M. Borst, W. de Looff, P.C. Verveer, and C.G. Kruse J. Med. Chem. 48 2005 1823 1838
- (2005) J. Med. Chem. , vol.48 , pp. 1823-1838
- Lange, J.H.M.¹ Van Stuivenberg, H.H.² Coolen, H.K.³ Adolfs, T.J.⁴ McCreary, A.C.⁵ Keizer, H.G.⁶ Wals, H.C.⁷ Veerman, W.⁸ Borst, A.J.M.⁹ De Looff, W.¹⁰ Verveer, P.C.¹¹ Kruse, C.G.¹²

22
- 33244485973
- Patent WO04026301 (2004).
- J.H.M. Lange, C.G. Kruse, A.C. McCreary, H.H. Van Stuivenberg, M. Verhage Patent WO04026301 (2004).
- Lange, J.H.M.¹ Kruse, C.G.² McCreary, A.C.³ Van Stuivenberg, H.H.⁴ Verhage, M.⁵

23
- 0038181075
- A.H. Harhash, M.H. Elnagdi, and A.A. Elbanani Tetrahedron 31 1975 25 29
- (1975) Tetrahedron , vol.31 , pp. 25-29
- Harhash, A.H.¹ Elnagdi, M.H.² Elbanani, A.A.³

24
- 33244489245
- N.A. Kassab, A.H. Harhash, S.A. Elbahaii, and Z. Naturforsch B: Chem. Sci. 33 1978 1145 1149
- (1978) B: Chem. Sci. , vol.33 , pp. 1145-1149
- Kassab, N.A.¹ Harhash, A.H.² Elbahaii, S.A.³ Naturforsch, Z.⁴

25
- 31944439480
- A.M. Khalil, I. Abdelgaw, and H.M. Hassan Aust. J. Chem. 27 1974 2509 2510
- (1974) Aust. J. Chem. , vol.27 , pp. 2509-2510
- Khalil, A.M.¹ Abdelgaw, I.² Hassan, H.M.³

26
- 84971030531
- A.M. Khalil, I.I.A. Elgawad, and H.M. Hassan Aust. J. Chem. 29 1976 1627 1629
- (1976) Aust. J. Chem. , vol.29 , pp. 1627-1629
- Khalil, A.M.¹ Elgawad, I.I.A.² Hassan, H.M.³

27
- 12944298514
- G.W. Sawdey J. Am. Chem. Soc. 79 1957 1955 1956
- (1957) J. Am. Chem. Soc. , vol.79 , pp. 1955-1956
- Sawdey, G.W.¹

28
- 0030860775
- K. Tsuji, K. Nakamura, N. Konishi, T. Tojo, T. Ochi, H. Senoh, and M. Matsuo Chem. Pharm. Bull. (Tokyo) 45 1997 987 995
- (1997) Chem. Pharm. Bull. (Tokyo) , vol.45 , pp. 987-995
- Tsuji, K.¹ Nakamura, K.² Konishi, N.³ Tojo, T.⁴ Ochi, T.⁵ Senoh, H.⁶ Matsuo, M.⁷

29
- 0033007758
- N. Kudo, S. Furuta, M. Taniguchi, T. Endo, and K. Sato Chem. Pharm. Bull. (Tokyo) 47 1999 857 868
- (1999) Chem. Pharm. Bull. (Tokyo) , vol.47 , pp. 857-868
- Kudo, N.¹ Furuta, S.² Taniguchi, M.³ Endo, T.⁴ Sato, K.⁵

30
- 0000080443
- P.S.J. Canning, K. McCrudden, H. Maskill, and B. Sexton J. Chem. Soc., Perkin Trans. 2 1999 2735 2740
- (1999) J. Chem. Soc., Perkin Trans. 2 , pp. 2735-2740
- Canning, P.S.J.¹ McCrudden, K.² Maskill, H.³ Sexton, B.⁴

31
- 0025213032
- L. Czollner, G. Szilagyi, J. Lango, and J. Janaky Arch. Pharm. (Weinheim) 323 1990 225 227
- (1990) Arch. Pharm. (Weinheim) , vol.323 , pp. 225-227
- Czollner, L.¹ Szilagyi, G.² Lango, J.³ Janaky, J.⁴

32
- 0006683298
- A. Benderly, and S. Stavchansky Tetrahedron Lett. 29 1988 739 740
- (1988) Tetrahedron Lett. , vol.29 , pp. 739-740
- Benderly, A.¹ Stavchansky, S.²

33
- 0037187367
- J.Y. Shim, W.J. Welsh, E. Cartier, J.L. Edwards, and A.C. Howlett J. Med. Chem. 45 2002 1447 1459
- (2002) J. Med. Chem. , vol.45 , pp. 1447-1459
- Shim, J.Y.¹ Welsh, W.J.² Cartier, E.³ Edwards, J.L.⁴ Howlett, A.C.⁵

34
- 33244489027
- http://www.logp.com.

35
- 0026560734
- R.G. Pertwee, L.A. Stevenson, D.B. Elrick, R. Mechoulam, and A.D. Corbett Br. J. Pharmacol. 105 1992 980 984
- (1992) Br. J. Pharmacol. , vol.105 , pp. 980-984
- Pertwee, R.G.¹ Stevenson, L.A.² Elrick, D.B.³ Mechoulam, R.⁴ Corbett, A.D.⁵

36
- 0029081885
- R.G. Pertwee, G. Griffin, J.A. Lainton, and J.W. Huffman Eur. J. Pharmacol. 284 1995 241 247
- (1995) Eur. J. Pharmacol. , vol.284 , pp. 241-247
- Pertwee, R.G.¹ Griffin, G.² Lainton, J.A.³ Huffman, J.W.⁴

37
- 1642342100
- A. Thomas, R.A. Ross, B. Saha, A. Mahadevan, R.K. Razdan, and R.G. Pertwee Eur. J. Pharmacol. 487 2004 213 221
- (2004) Eur. J. Pharmacol. , vol.487 , pp. 213-221
- Thomas, A.¹ Ross, R.A.² Saha, B.³ Mahadevan, A.⁴ Razdan, R.K.⁵ Pertwee, R.G.⁶

38
- 0036892304
- D.P. Hurst, D.L. Lynch, J. Barnett-Norris, S.M. Hyatt, H.H. Seltzman, M. Zhong, Z.H. Song, J. Nie, D. Lewis, and P.H. Reggio Mol. Pharmacol. 62 2002 1274 1287
- (2002) Mol. Pharmacol. , vol.62 , pp. 1274-1287
- Hurst, D.P.¹ Lynch, D.L.² Barnett-Norris, J.³ Hyatt, S.M.⁴ Seltzman, H.H.⁵ Zhong, M.⁶ Song, Z.H.⁷ Nie, J.⁸ Lewis, D.⁹ Reggio, P.H.¹⁰

39
- 0242522905
- S.D. McAllister, G. Rizvi, S. Anavi-Goffer, D.P. Hurst, J. Barnett-Norris, D.L. Lynch, P.H. Reggio, and M.E. Abood J. Med. Chem. 46 2003 5139 5152
- (2003) J. Med. Chem. , vol.46 , pp. 5139-5152
- McAllister, S.D.¹ Rizvi, G.² Anavi-Goffer, S.³ Hurst, D.P.⁴ Barnett-Norris, J.⁵ Lynch, D.L.⁶ Reggio, P.H.⁷ Abood, M.E.⁸

40
- 12744258029
- R.G. Pertwee Life Sci. 76 2005 1307 1324
- (2005) Life Sci. , vol.76 , pp. 1307-1324
- Pertwee, R.G.¹

41
- 0035794019
- L.J. Sim-Selley, L.K. Brunk, and D.E. Selley Eur. J. Pharmacol. 414 2001 135 143
- (2001) Eur. J. Pharmacol. , vol.414 , pp. 135-143
- Sim-Selley, L.J.¹ Brunk, L.K.² Selley, D.E.³

42
- 0034948614
- C.S. Breivogel, G. Griffin, V. Di Marzo, and B.R. Martin Mol. Pharmacol. 60 2001 155 163
- (2001) Mol. Pharmacol. , vol.60 , pp. 155-163
- Breivogel, C.S.¹ Griffin, G.² Di Marzo, V.³ Martin, B.R.⁴

43
- 0037027935
- R.G. Pertwee, R.A. Ross, S.J. Craib, and A. Thomas Eur. J. Pharmacol. 456 2002 99 106
- (2002) Eur. J. Pharmacol. , vol.456 , pp. 99-106
- Pertwee, R.G.¹ Ross, R.A.² Craib, S.J.³ Thomas, A.⁴

44
- 0037423029
- E. Fride, A. Foox, E. Rosenberg, M. Faigenboim, V. Cohen, L. Barda, H. Blau, and R. Mechoulam Eur. J. Pharmacol. 461 2003 27 34
- (2003) Eur. J. Pharmacol. , vol.461 , pp. 27-34
- Fride, E.¹ Foox, A.² Rosenberg, E.³ Faigenboim, M.⁴ Cohen, V.⁵ Barda, L.⁶ Blau, H.⁷ Mechoulam, R.⁸

45
- 0032982010
- R.A. Ross, H.C. Brockie, L.A. Stevenson, V.L. Murphy, F. Templeton, A. Makriyannis, and R.G. Pertwee Br. J. Pharmacol. 126 1999 665 672
- (1999) Br. J. Pharmacol. , vol.126 , pp. 665-672
- Ross, R.A.¹ Brockie, H.C.² Stevenson, L.A.³ Murphy, V.L.⁴ Templeton, F.⁵ Makriyannis, A.⁶ Pertwee, R.G.⁷

46
- 0019061918
- P.J. Munson, and D. Robbard Anal. Biochem. 107 1980 220 239
- (1980) Anal. Biochem. , vol.107 , pp. 220-239
- Munson, P.J.¹ Robbard, D.²

47
- 0015861774
- Y. Cheng, and W.H. Prusoff Biochem. Pharmacol. 22 1973 3099 3108
- (1973) Biochem. Pharmacol. , vol.22 , pp. 3099-3108
- Cheng, Y.¹ Prusoff, W.H.²

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