New selective and potent 5-HT(1B/1D) antagonists: Chemistry and pharmacological evaluation of N-piperazinylphenyl biphenylcarboxamides and biphenylsulfonamides

Journal of Medicinal Chemistry

Volumn 43, Issue 3, 2000, Pages 517-525

  Liao, Yi ^a   Böttcher, Henning ^b   Harting, Jürgen ^b   Greiner, Hartmut ^b   Van Amsterdam, Christoph ^b   Cremers, Thomas ^a   Sundell, Staffan ^c   März, Joachim ^b   Rautenberg, Wilfried ^b   Wikström, Håkan ^a  

^a UNIVERSITY MEDICAL CENTER GRONINGEN   (Netherlands)

^b MERCK KGAA   (Germany)

^c UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

2,3,6,7 TETRAHYDRO 1' METHYL 5 [[2' METHYL 4' (5 METHYL 1,2,4 OXADIAZOL 3 YL) 4 BIPHENYLYL]CARBONYL]SPIRO[FURO[2,3 F]INDOLE 3,4' PIPERIDINE]; ACETYLCHOLINE; CITALOPRAM; N [4 METHOXY 3 (4 METHYL 1 PIPERAZINYL)PHENYL] 2' METHYL 4' (5 METHYL 1,2,4 OXADIAZOL 3 YL)[1,1' BIPHENYL] 4 CARBOXAMIDE; POTASSIUM; SEROTONIN; SEROTONIN 1B ANTAGONIST; SEROTONIN 1D ANTAGONIST; SEROTONIN UPTAKE INHIBITOR;

ACETYLCHOLINE RELEASE; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BRAIN CORTEX; CATTLE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; GUINEA PIG; HIPPOCAMPUS; IC 50; IN VITRO STUDY; IN VIVO STUDY; MALE; MICRODIALYSIS; NONHUMAN; RABBIT; RAT; SAPHENOUS VEIN; SEROTONIN RELEASE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS;

ACETYLCHOLINE; ANIMALS; BIPHENYL COMPOUNDS; CATTLE; CRYSTALLOGRAPHY, X-RAY; GUINEA PIGS; HIPPOCAMPUS; MALE; MICRODIALYSIS; MOLECULAR STRUCTURE; MUSCLE CONTRACTION; MUSCLE, SMOOTH, VASCULAR; PIPERAZINES; RABBITS; RADIOLIGAND ASSAY; RATS; RATS, WISTAR; RECEPTOR, SEROTONIN, 5-HT1B; RECEPTOR, SEROTONIN, 5-HT1D; RECEPTORS, SEROTONIN; SAPHENOUS VEIN; SEROTONIN; SEROTONIN ANTAGONISTS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONAMIDES;

EID: 0343550410     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm990397l     Document Type: Article

References (33)

1. 1D family genes. Trends Pharmacol. Sci. 1992, 13, 152-159.
2. 1D receptor subtypes. Trends Pharmacol. Sci. 1996, 17, 103-105.
3. 1B receptors. Nature 1992, 360, 161-163.
4. Hoyer, D.; Clarke, D. E.; Fozard, J. R.; Hartig, P. R.; Martin, G. R.; Mylecharane, E. J.; Saxena, P. R.; Humprey, P. P. A. International union of pharmacology classification of receptors for 5-hydroxytryptamine (serotonin). Pharmacol. Rev. 1994, 46, 157-203.
5. 1D receptor subfamily. J. Neurochem. 1997, 68, 410-418.
6. 3H]alniditan. Mol. Pharmacol. 1996, 50, 1567-1580.
7. Berg, S.; Larsson, L.-G.; Renyi, L.; Ross, S. B.; Thorberg, S.-O.; Thorell-Svantesson, G. (R)-(+)-2-[[3-(Morpholinomethyl)-2H-chromen-8-yl]oxymethyl]morpholine methanesulfonate: a new selective rat 5-hydroxytryptamine-1B receptor antagonist. J. Med. Chem. 1998, 41, 1934-1942.
8. 1D receptors: a serotonin receptor population for the 1990s. Drug News Perspect. 1993, 6, 390-405.
9. 1B/1D antagonists. Gen. Pharmacol. 1997, 29, 293-303.
10. Briley, M.; Moret, C. Neurological mechanism involved in antidepressant therapies. Clin. Neuropharmacol. 1993, 16, 387-400.
11. 1B/1D antagonists and depression. Exp. Opin. Ther. Patents. 1997, 7, 339-352.
12. Dolberg, O. T.; Sasson, Y.; Cohen, R.; Zohar, J. The relevance of behavioural probes in obsessive-compulsive disorders. Eur. Neuropsychopharmacol. 1995, 5, 161-162.
13. 1D antagonists. J. Med. Chem. 1994, 37, 2253-2257.
14. 1Dβ receptors. Eur. J. Pharmacol. 1996, 314, 365-372.
15. 1B receptor inverse agonist 1′-methyl-5-[[2′-methyl-4′-(5-methyl-1,2,4-oxadiazole-3-yl) biphenyl-4-yl]-carbonyl]-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4′- piperidine] (SB224289) potently blocks terminal 5-HT autoreceptor function both in vitro and in vivo. J. Med. Chem. 1998, 41, 1218-1235.
16. Jorand-Lebrun, C.; Pauwels. P. J.; Palmier, C.; Chantal, M.; Chopin, P.; Perez, M.; Marien, M.; Halazy, S. 5-HT1B receptor antagonist properties of novel arylpiperazine derivatives of 1-naphthylpiperazine. J. Med. Chem. 1997, 40, 3974-3978.
17. 1B receptor selectivity for 5-HT terminal autoreceptor activity: an in vivo microdialysis study in the freely moving guinea-pig. Neuropharmacology 1997, 36, 549-557.
18. 1D receptor antagonist GR127935 on extracellular levels of 5-HT in the guinea-pig frontal cortex as measured by microdialysis. Neuropharmacology 1995, 34, 377-382.
19. 1D receptor antagonist, GR127935, on in vivo 5-HT release, synthesis and turnover in the guinea-pig frontal cortex. Br. J. Pharmacol. 1994, 112, 489P.
20. 1D receptor antagonist, on brain metabolism, extracellular 5-HT concentration and behavior in the guinea-pig. Neuropharmacology 1995, 34, 383-392.
21. 1D antagonist and a 5-HT reuptake inhibitor synergistically increases 5-HT release in guinea-pig hypothalamus in vivo. J. Neurochem. 1996, 67, 2204-2207.
22. 1D antagonists. Eur. Pat. Appl. 0 533 268 A1, March 1993; Chem. Abstr. 1993, 119, 117270e.
23. Lipinski, C. A.; Lombardo, F.; Dominy, B. L.; Feeney, P. L. Experimental and computational approaches to estimate solubility in drug discovery and development settings. Adv. Drug Delivery Rev. 1997, 23, 3-25.
24. 125I]-Iodocyanopindolol. Eur. J. Pharmacol. 1985, 118, 1-12.
25. 1D, binding sites in human brain membranes. Synapse 1989, 3, 61-66.
26. 3H)-5-methoxy-3-(din-propylamino)chroman. Eur. J. Pharmacol. 1987, 740, 143-155.
27. Razzaque, Z.; Longmore, J.; Hill, R. G. Differences in the effects of kataserin and GR127935 on 5-HT receptor mediated responses in rabbit saphenous vein and guinea-pig jugular vein Eur. J. Pharmacol. 1995, 283, 199-206.
28. 3H]-hydroxytrptamine release from guinea-pig cortical slices. Eur. J. Pharmacol.-Mol. Pharmacol. Sec. 1993, 244, 189-192.
29. Wong, D. T.; Bymaster, F. P.; Mayle, D. A.; Reid, L. R.; Krushinski, J. H.; Robertson, D. W. LY248686, a New Inhibitor of Serotonin and Norephinephrine Uptake. Neuropharmacology 1993, 8, 23-33.
30. 1A receptor enhances acetylcholine release in conscious rats. J. Neurochem. 1994, 62, 1804-1808.
31. 1B presynaptic heteroreceptors inhibiting acetylcholine release. Neuropharmacology 1994, 33, 77-81.
32. J. März, unpublished results. For discussion, please contact: Joachim.Maerz@merck.de.
33. Meyland, W. M.; Howard, P. H. Atom/fragment contribution method for estimating octanol-water coefficients. J. Pharm. Sci. 1995, 84, 83-92.