Novel inhibitors of fatty acid amide hydrolase

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 12, 2007, Pages 3287-3291

  Sit, S Y ^a   Conway, Charlie ^a   Bertekap, Robert ^a   Xie, Kai ^a   Bourin, Clotilde ^a   Burris, Kevin ^b   Deng, Hongfeng ^c  

^a BRISTOL MYERS SQUIBB   (United States)

^b Palatin Technologies   (United States)

^c GLAXOSMITHKLINE   (United States)

Author keywords

Anandamide; Antineuropathic; Bisarylimidazole; Cannabinoid receptor; Chung model; Enzyme; FAAH; Fatty acid amide hydrolase; Formalin test; Gabapentin; Hargreaves test; Inhibitor; Morphine; Neuropathic; Pain; Persistent; SR141716A

Indexed keywords

ANANDAMIDE; CANNABINOID 1 RECEPTOR; CANNABINOID RECEPTOR ANTAGONIST; CARBAMIC ACID DERIVATIVE; FATTY ACID AMIDASE; FATTY ACID AMIDASE INHIBITOR; IMIDAZOLE DERIVATIVE; RIMONABANT;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINOCICEPTION; ARTICLE; CONTROLLED STUDY; DRUG ANTAGONISM; DRUG INHIBITION; DRUG MECHANISM; DRUG POTENTIATION; ENZYME ACTIVITY; ENZYME INHIBITION; ESCAPE BEHAVIOR; NEUROPATHIC PAIN; NONHUMAN; RAT;

AMIDOHYDROLASES; AMINES; ANALGESICS; ANIMALS; CYCLOHEXANECARBOXYLIC ACIDS; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME INHIBITORS; GAMMA-AMINOBUTYRIC ACID; HUMANS; IMIDAZOLES; MICE; MICE, KNOCKOUT; MORPHINE; PAIN MEASUREMENT; PIPERIDINES; PYRAZOLES; RATS; RECEPTOR, CANNABINOID, CB1;

ANIMALIA; RATTUS;

EID: 34249687699     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.04.009     Document Type: Article

References (32)

1. For general reviews:. Pacher P., Batkai S., and Kunos G. Pharmacol. Rev. 58 (2006) 389
2. Cravatt B.F., and Lichtman A.H. Curr. Opin. Chem. Biol. 7 (2003) 469
3. Boger D.L., Henriksen S.J., and Cravatt B.F. Curr. Pharm. Des. 44 (1998) 303
4. Pertwee R.G. Prog. Neurobiol. 63 (2001) 569
5. Cravatt B.F., and Lichtman A.H. J. Neurobiol. 61 (2004) 149
6. Lu D., Vemuri V., Kiran D., Richard Jr. I., and Makriyannis A. Curr. Top. Med. Chem. 6 (2006) 1401
7. Guindon J., LoVerme J., De Lean A., Piomelli D., and Beaulieu P. Eur. J. Pharmacol. 550 (2006) 68
8. Elphick M.R., and Egertova M. Philos. Trans. R. Soc. London Ser. B 356 (2001) 381
9. Cravatt B.F., and Lichtman A.H. Chem. Phys. Lipids 121 (2002) 135
10. Walker J.M., Huang S.M., Strangman N.M., Tsou K., and Sanudo-Pena M.C. Proc. Natl. Acad. Sci. U.S.A. 96 (1999) 12198
11. Desarnaud F., Cadas H., and Piomelli D. J. Biol. Chem. 270 (1995) 6030
12. Piomelli D., Beltramo M., Giuffrida A., and Stella N. Neurobiol. Dis. 5 (1998) 462
13. Cravatt B.F., Demarest K., Patricelli M.P., Bracey M.H., Giang D.K., Martin B.R., and Lichtman A.H. Proc. Natl. Acad. Sci. U.S.A. 98 (2001) 9371
14. Boger D.L., Miyauchi H., Du W., Hardouin C., Fecik R.A., Cheng H., Hwang I., Hedrick M.P., Leung D., Acevedo O., Guimaraes C.R.W., Jorgensen W.L., and Cravatt B.F. J. Med. Chem. 48 (2005) 1849
15. Leung D., Du W., Hardouin C., Cheng H., Hwang I., Cravatt B.F., and Boger D.L. Bioorg. Med. Chem. Lett. 15 (2005) 1423
16. Guimaraes C.R.W., Boger D.L., and Jorgensen W.L. J. Am. Chem. Soc. 127 (2005) 17377
17. Michaux C., Muccioli G.G., Lambert D.M., and Wouters J. Bioorg. Med. Chem. Lett. 16 (2006) 4772
18. Piomelli D., Tarzia G., Duranti A., Tontini A., Mor M., Compton T.R., Dasse O., Monaghan E.P., Parrott J.A., and Putman D. CNS Drug Reviews 12 (2006) 21
19. Seiler S.M., Brassard C.L., Federici M.E., Romine J., and Meanwell N.A. Prostaglandins 53 (1997) 21
20. Meanwell N.A., Romine J.L., and Seiler S.M. Drugs Fut. 19 (1994) 361
21. Meanwell N.A., Rosenfeld M.J., Trehan A.K., Romine J.L., Kim W.J.J., Brassard C.L., Buchanan J.O., Federici M.E., Fleming J.S., Gamberdella M., and Seiler S.M. J. Med. Chem. 35 (1992) 3498
22. Fox A., and Bevan S. Expert Opin. Invest. Drugs 14 (2005) 695
23. Sit, S. Y.; Xie, K. U.S. Patent 6,562,846, 2003; preliminary report disclosed as a Poster Presentation, Sit et al. 39th National Organic Chemistry symposium, Number D30, Salt Lake City, Utah, June 12-16, 2005; American Chemical Society, Division of Organic Chemistry.
24. Omeir R.L., Chin S., Hong Y., Ahern D.G., and Deutsch D.G. Life Sci. 56 (1995) 1999
25. 1(b), and Alexander, J. P.; Cravatt, B. F. Chem. Biol. (Cambridge, MA, U.S.) 2005, 12, 1179.
26. Hargreaves K., Dubner R., Brown F., Flores C., and Joris J. Pain 32 (1988) 77
27. Comparable, in vivo, analgesic properties have been demonstrated previously, for example, see Refs. 6a-e.
28. Hunskaar S., and Hole K. Pain 30 (1987) 103
29. Honore P. Drug Dev. Res. 67 (2006) 302
30. Joshi S.K., and Honore P. Expert Opin. Drug Discovery 14 (2006) 323
31. Lee K.L., Foley M.A., Chen L., Behnke M.L., Lovering F.E., Kirincich S.J., Wang W., Shim J., Tam S., Shen M.W.H., Khor S., Xu X., Goodwin D.G., Ramarao M.K., Nickerson-Nutter C., Donahue F., Ku M.S., Clark J.D., and McKew J.C. J. Med. Chem. 50 (2007) 1380
32. 3H]-CP55,940 in HEK-CB1 and CHO-CB2 preparations.