Tetrahydropyridine-4-carboxamides as novel, potent transient receptor potential vanilloid 1 (TRPV1) antagonists

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 18, 2008, Pages 8516-8525

  Brown, Brian S ^a   Keddy, Ryan ^a   Zheng, Guo Zhu ^a   Schmidt, Robert G ^a   Koenig, John R ^a   McDonald, Heath A ^a   Bianchi, Bruce R ^a   Honore, Prisca ^a   Jarvis, Michael F ^a   Surowy, Carol S ^a   Polakowski, James S ^a   Marsh, Kennan C ^a   Faltynek, Connie R ^a   Lee, Chih Hung ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

CNS; Pain; Tetrahydropyridine; TRPV1; Vanilloid

Indexed keywords

1 [3 (TRIFLUOROMETHYL)PYRIDIN 2 YL] N [4 (TRIFLUOROMETHYLSULFONYL)PHENYL] 1,2,3,6 TETRAHYDROPYRIDINE 4 CARBOXAMIDE; 1,2,3,6 TETRAHYDROPYRIDYL 4 CARBOXAMIDE; A 795614; ANALGESIC AGENT; CALCIUM ION; CAPSAICIN; CAPSAICIN DERIVATIVE; DOPAMINE DERIVATIVE; FREUND ADJUVANT; N ARACHIDONOYLDOPAMINE; UNCLASSIFIED DRUG; VANILLOID RECEPTOR 1; VANILLOID RECEPTOR 1 ANTAGONIST;

ALLODYNIA; ANALGESIA; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINOCICEPTION; ARTICLE; CALCIUM TRANSPORT; CELL STRAIN CACO 2; CENTRAL NERVOUS SYSTEM; CONTROLLED STUDY; DRUG EFFECT; DRUG EFFICACY; DRUG PENETRATION; DRUG POTENCY; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG SYNTHESIS; HYPERALGESIA; IN VITRO STUDY; IN VIVO STUDY; INCISION; MALE; NONHUMAN; OSTEOARTHRITIS; PAIN; PH; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; STRUCTURE ACTIVITY RELATION;

ADMINISTRATION, ORAL; ANALGESICS; ANIMALS; ARACHIDONIC ACIDS; CALCIUM; CAPSAICIN; DISEASE MODELS, ANIMAL; DOPAMINE; DOSE-RESPONSE RELATIONSHIP, DRUG; HYDROGEN-ION CONCENTRATION; HYPERALGESIA; PAIN MEASUREMENT; PYRIDINES; RATS; RATS, SPRAGUE-DAWLEY; STRUCTURE-ACTIVITY RELATIONSHIP; TRPV CATION CHANNELS;

ANIMALIA;

EID: 51449084658     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.08.005     Document Type: Article

References (26)

1. Caterina M. Science 288 (2000) 306-313
2. Benham C.D. Neuropharmacology 42 (2002) 873-888
3. Caterina M., Schumacher M.A., Tominaga M., Rosen T.A., Levine J.D., and Julius D. Nature 389 (1997) 816-824
4. Caterina M., and Julius D. Annu. Rev. Neurosci. 24 (2001) 487-517
5. Davis J.B., Gray J., Gunthorpe M.J., Hatcher J.P., Davey P.T., Overend P., Harries M.H., Latcham J., Clapham C., Atkinson K., Hughes S.A., Rance K., Grau E., Harper A.J., Pugh P.L., Rogers D.C., Bingham S., Randall A., and Sheardown S.A. Nature 405 (2000) 183-187
6. Kwak J.Y., Jung J.Y., Hwang S.W., Lee W.T., and Oh U. Neuroscience 86 (1998) 619-626
7. Valenzano K.J., Grant E.R., Wu G., Hachicha M., Schmid L., Tafesse L., Sun Q., Rotshteyn Y., Francis J., Limberis J., Malik S., Whittemore E.R., and Hodges D.J. Pharmacol. Exp. Ther. 306 (2002) 377-386
8. Brietenbucher G., Chaplan S.R., and Carrruthers N.I. Annu. Rep. Med. Chem. 40 (2005) 185-198
9. Szallasi A., Cortright D.N., Blum C.A., and Eid S.R. Nat. Rev. Drug Discovery 6 (2007) 357-372
10. In: Malmberg A.B., and Bley K.R. (Eds). Turning up the Heat on Pain: TRPV1 Receptors in Pain and Inflammation (2005), Springer, Berlin
11. Cui M., Honore P., Zhong C., Gauvin D., Mikusa J., Hernandez G., Chandran P., Gomtsyan A., Brown B., Bayburt E.K., Marsh K., Bianchi B., McDonald H., Niforatos W., Neelands T.R., Moreland R.B., Decker M.W., Lee C.-H., Sullivan J.P., and Faltynek C.R.J. Neuroscience 26 (2006) 9385-9393
12. Kim S.H., and Chung J.M. Pain 50 (1992) 355-363
13. Park H.-G., Choi J.-Y., Kim M.-H., Choi S.-H., Park M.-K., Lee J., Suh Y.-G., Cho H., Oh U., Kim H.-D., Joo Y.H., Shin S.S., Kim J.K., Jeong Y.S., Koh H.-Y., Park Y.-H., and Jew S.-S. Bioorg. Med. Chem. Lett. 5 (2005) 631-634
14. Zheng X., Hodgetts K.J., Brielmann H., Hutchison A., Burkamp F., Jones A.B., Blurton P., Clarkson R., Chandrasekhar J., Bakthavatchalam R., De Lombaert S., Crandall M., Cortright D., and Blum C.A. Bioorg. Med. Chem. Lett. 6 (2006) 5217-5221
15. Wagaw S., and Buchwald S.L.J. Org. Chem. 61 (1996) 7240-7241
16. For an analogous synthesis, see. Rohr M., Chayer S., Garrido F., Mann A., Taddei M., and Wermuth C.-G. Heterocycles 43 (1996) 2131-2138
17. Lipton M.F., Basha A., and Weinreb S.M. Org. Synth. 59 (1980) 49-52
18. Howard K.L., Stewart H.W., Conroy E.A., and Dentok J.J. J. Org. Chem. 18 (1953) 1484-1488
19. Saari W.S., Halczenko W., King S.W., Huff J.R., Guare Jr. J.P., Hunt C.A., Randall W.C., Anderson P.S., Lotti V.J., Taylor D.A., and Clineschmidt B.V.J. Med. Chem. 26 (1983) 1696-1701
20. Swanson D.M., Dubin A.E., Shah C., Nasser N., Chang L., Dax S.L., Jetter M., Breitenbucher J.G., Liu C., Mazur C., Lord B., Gonzales L., Hoey K., Rizzolio M., Bogenstaetter M., Codd E.E., Lee D.H., Zhang S.-P., Chaplan S.R., and Carruthers N.I.J. Med. Chem. 48 (2005) 1857-1872
21. Huth J.R., Mendoza R., Olejniczak E.T., Johnson Robert W., Cothron D.A., Liu Y., Lerner C.G., Chen J., and Hajduk P.J. J. Am. Chem. Soc. 127 (2005) 217-224
22. Kanai Y., Hara T., Imai A., and Sakakibara A.J. Pharm. Pharmacol. 59 (2007) 733-738
23. Pitcher M.H., Price T.J., Entrena J.M., and Cervero F. Mol. Pain 3 (2007) 17
24. Hargreaves K., Dubner R., Brown F., Flores C., and Joris J. Pain 32 (1988) 77-88
25. Brennan T.J., Vandermeulen E.P., and Gebhart G.F. Pain 64 (1996) 493-501
26. Axton C.A., Billingham M.E.J., Bishop P.M., Gallagher P.T., Hicks T.A., Kitchen E.A., Mullier G.W., Owton W.M., Parry M.G., Scott S., and Steggles D.J. J. Chem. Soc., Perkin Trans. 1 (1992) 2203-2213