N-substituted piperidinyl alkyl imidazoles: Discovery of methimepip as a potent and selective histamine H3 receptor agonist

Journal of Medicinal Chemistry

Volumn 48, Issue 6, 2005, Pages 2100-2107

  Kitbunnadaj, Ruengwit ^a,b   Hashimoto, Takeshi ^c   Poli, Enzo ^d   Zuiderveld, Obbe P ^a   Menozzi, Alessandro ^d   Hidaka, Ryoko ^c   De Esch, Iwan J P ^a   Bakker, Remko A ^a   Menge, Wiro M P B ^a   Yamatodani, Atsushi ^c   Coruzzi, Gabriella ^d   Timmerman, Henk ^a   Leurs, Rob ^a  

^a VU UNIVERSITY AMSTERDAM   (Netherlands)

^b NARESUAN UNIVERSITY   (Thailand)

^c OSAKA UNIVERSITY   (Japan)

^d UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

HISTAMINE H1 RECEPTOR; HISTAMINE H2 RECEPTOR; HISTAMINE H3 RECEPTOR; HISTAMINE H4 RECEPTOR; IMMEPIP; METHIMEPIP; UNCLASSIFIED DRUG; VUF 4929; VUF 5510;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG POTENCY; DRUG SELECTIVITY; GUINEA PIG; HUMAN; IN VIVO CULTURE; MALE; MICRODIALYSIS; NONHUMAN; RAT; RECEPTOR BINDING;

ANIMALS; BINDING, COMPETITIVE; CELL LINE; CERCOPITHECUS AETHIOPS; CRICETINAE; CRICETULUS; ELECTRIC STIMULATION; GUINEA PIGS; HISTAMINE; HISTAMINE AGONISTS; HUMANS; HYPOTHALAMUS; ILEUM; IMIDAZOLES; MALE; MICRODIALYSIS; MUSCLE CONTRACTION; MUSCLE, SMOOTH; PIPERIDINES; RADIOLIGAND ASSAY; RATS; RATS, WISTAR; RECEPTORS, HISTAMINE H3;

EID: 20144385213     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm049475h     Document Type: Article

References (39)

1. 1 receptor. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 11515-11519.
2. 2 receptor. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 429-433.
3. 3 receptor. Mol. Pharmacol. 1999, 55, 1101-1107.
4. Oda, T.; Morikawa, N.; Saito, Y.; Masuho, Y.; Matsumoto, S. Molecular cloning and characterization of a novel type of histamine receptor preferentially expressed in leukocytes. J. Biol. Chem. 2000, 275, 36781-36786.
5. Ash, A. S. F.; Schild, H. O. Receptor mediating some actions of histamine. Br. J. Pharmacol. 1966, 188, 219-227.
6. 2 receptors. Nature 1972, 236, 385-390.
7. Kaliner, M. A.; Check, W. A. Non-sedating antihistamines. Allergy Proc. 1988, 9, 649-663.
8. 1 receptor antagonist treatment. J. Allergy Clin. Immunol. 1990, 86, 995-999.
9. 2 receptor antagonists; a pharmacological dream come true. Aust. N. Z. J. Med. 1974, 4, 521-524.
10. 2 receptor antagonists. Bailliere's Clin. Gastroenterol. 1988, 2, 593-608.
11. 3 of histamine receptor. Nature 1983, 302, 832-837.
12. 3 receptor activation inhibits acetylcholine release from the guinea pig myenterie plexus. Agents Actions 1991, 33, 167-169.
13. + evoked release of acetylcholine from rat cortex in vivo. Inflammation Res. 1997, 46, S33-34.
14. 3 receptors? Eur. J. Pharmacol. 1990, 184, 135-142.
15. 3 receptors. Naunyn Schmiedeberg's Arch. Pharmacol. 1994, 349, 113-117.
16. 3 antagonist carboperamide (MR 16155) administration in rats. Neuropsychopharmacology 1996, 15, 31-35.
17. Nakamura, T.; Itadani, H.; Hidaka, Y.; Ohta, M.; Tanaka, K. Molecular cloning and characterization of a new human histamine receptor, HH4R. Biochem. Biophys. Res. Commun. 2000, 279, 615-620.
18. 4 receptor gene. Biochem. Biophys. Res. Commun. 2001, 284, 301-309.
19. 4 expressed in bone marrow. Mol. Pharmacol. 2001, 59, 420-426.
20. Zhu, Y.; Michalovich, D.; Wu, H.; Tan, K. B.; Dytko, G. M., Mannan, I. J.; Boyce, R.; Alston, J.; Tierney, L. A.; Li, X.; Herrity, N. C.; Vawter, L.; Sarau, H. M.; Ames, R. S.; Davenport, C. M.; Hieble, J. P.; Wilson, S.; Bergsma, D. J.; Fitzgerald, L. R. Cloning, expression, and pharmacological characterization of a novel human histamine receptor. Mol. Pharmacol. 2001, 59, 434-441.
21. Morse, K. L.; Behan, J.; Laz, T. M.; West, R. E., Jr.; Greenfeder, S. A.; Anthes, J. C.; Umland, S.; Wan, Y.; Hipkin, R. W.; Gonsiorek, W.; Shin, N.; Gustafson, E. L.; Qiao, X.; Wang, S.; Hedrick, J. A.; Greene, J.; Bayne, M.; Monsma, F. J., Jr. Cloning and characterization of a novel human histamine receptor. J. Pharmacol. Exp. Ther. 2001, 296, 1058-1066.
22. Nguyen, T.; Shapiro, D. A.; George, S. R.; Setola, V.; Lee, D. K.; Cheng, R.; Rauser, L.; Lee, S. P.; Lynch, K. R.; Roth, B. L.; O'Dowd, B. F. Discovery of a novel member of the histamine receptor family. Mol. Pharmacol. 2001, 59, 427-433.
23. 3 receptor agonist. J. Pharmacol. Exp. Ther. 1992, 263, 304-310.
24. 3 receptor agonist, 4-(1H-imidazol-4-ylmethyl)piperidine. J. Med. Chem. 1994, 37, 332-333.
25. 3 Receptor Agonists. J. Med. Chem. 2003, 46, 5445-5457.
26. 4 receptor antagonist. J. Med. Chem. 2003, 46, 3957-3960.
27. Newman, M. S.; Lloyd, H. A. The reaction of N-methylpiperidine with alkyl durenecarboxylates. J. Am. Chem. Soc. 1952, 74, 2672-2674.
28. Lee, S. S.; Wu, W. N.; Wilton, J. H.; Beal, J. L.; Doskotch, R. W. Longiberine and O-methyllongiberine, dimeric protoberberinebenzyl tetrahydroisoquinoline alkaloids from Thalictrum longistylum(1). J. Nat. Prod. 1999, 62, 1410-1414.
29. Abdel-Magid, A. F.; Maryanoff, C. A.; Carson, K. G. Reductive animation of aldehydes and ketones by using sodium triacetoxyborohydride. Tetrahedron Lett. 1990, 31, 5595-5598.
30. 1 receptor antagonists. J. Med. Chem. 2003, 46, 5812-5824.
31. S-coupled receptors. FEBS Lett. 1997, 419, 171-174.
32. 2+ channels. J. Pharmacol. Exp. Ther. 1994, 270, 788-794.
33. 3 receptor ligands, immepip and clobenpropit. Effects of intrahypothalamic and peripheral application. Eur. J. Pharmacol. 1998, 362, 149-155.
34. Shih, N. Y.; Green, M. J. Imidazolealkyl substituted with a six membered nitrogen containing heterocyclic ring. U.S. Patent 5,932,596, 1993.
35. 3 subtype. J. Pharmacol. Exp. Ther. 1987, 243, 874-880.
36. 3-receptor selective drugs on the mechanical activity of guinea-pig small and large intestine. Br. J. Pharmacol. 1991, 102, 179-185.
37. 3 receptors in the guinea pig ileum: evidence for a postjunctional location. J. Physiol. (Paris) 2000, 94, 1-4.
38. 3 receptor antagonists A-304121 and A-317920: I. In vitro pharmacological effects. J. Pharmacol. Exp. Ther. 2003, 305, 887-896.
39. 3 ligands. Synthesis 2002, 2002, 1072-1078.