Development of fluorine-18-labeled 5-HT(1A) antagonists

Journal of Medicinal Chemistry

Volumn 42, Issue 9, 1999, Pages 1576-1586

  Lang, Lixin ^a   Jagoda, Elaine ^a   Schmall, Bernard ^a   Vuong, Bik Kee ^a   Adams, H Richard ^a   Nelson, David L ^b   Carson, Richard E ^a   Eckelman, William C ^a  

^a NATIONAL INSTITUTES OF HEALTH   (United States)

^b ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 NITRO 4 (FLUOROMETHYL)BENZOIC ACID; 4 (FLUOROMETHYL) N [2 [4 (2 METHOXYPHENYL)PIPERAZINO]ETHYL] 3 METHYL N (2 PYRIDINYL)BENZAMIDE; 4 (FLUOROMETHYL)BENZOIC ACID; 4 FLUORO 3 METHYLBENZOIC ACID; 4 FLUORO N [2 [4 (2 METHOXYPHENYL)PIPERAZINO]ETHYL]3 METHYL N (2 PYRIDINYL)BENZAMIDE; 4 FLUORO N [2 [4 (2 METHOXYPHENYL)PIPERAZINO]ETHYL]N (2 PYRIDINYL)BENAZIMDE; 4 FLUOROBENZOIC ACID; 4 FLUOROCYCLOHEXANECARBOXYLIC ACID; CYCLOHEXANECARBOXYLIC ACID DERIVATIVE; FLUORINE 18; N [2 [4 (2 METHOXYPHENYL) 1 PIPERAZINYL]ETHYL] N (2 PYRIDYL)CYCLOHEXANECARBOXAMIDE; SEROTONIN 1A ANTAGONIST; UNCLASSIFIED DRUG;

ARTICLE; AUTORADIOGRAPHY; DRUG BLOOD LEVEL; DRUG CLEARANCE; DRUG HALF LIFE; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; SEROTONINERGIC SYSTEM;

ANIMALS; BENZAMIDES; BRAIN; FLUORINE RADIOISOTOPES; ISOTOPE LABELING; LIGANDS; PIPERAZINES; PYRIDINES; RATS; RECEPTORS, SEROTONIN; RECEPTORS, SEROTONIN, 5-HT1; SEROTONIN ANTAGONISTS; STRUCTURE-ACTIVITY RELATIONSHIP; TISSUE DISTRIBUTION;

EID: 0033529043     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980456f     Document Type: Article

References (31)

1. 1A receptor antagonists: utility as research tools and therapeutic agents. TIPS 1993, 141, 441-448.
2. Alexander, S. P. H.; Peters, J. A. 1998 Receptor and Ion Channel Nomenclature Supplement. TIPS 1998.
3. Crouzel, C.; Guillaume, M.; Barre, L.; Lemaire, C.; Pike, V. W. Ligands and tracers for PET studies of the 5-HT system-current status. Nucl. Med. Biol. 1992, 19, 857-879.
4. 1A receptors. Eur. J. Pharmacol. 1993, 237, 283-291.
5. 3H] WAY100635, a novel 5-hydroxytryptamine 1a receptor antagonist, to rat brain. J. Neurochem. 1995, 64, 2716-2726.
6. 1A receptors in rat brain. Synapse 1994, 18, 359-366.
7. 3H] WAY 100635 in the mouse. Eur. J. Pharmacol. 1994, 271, 505-514.
8. 1A receptors in rat brain. Eur. J. Pharmacol. 1994, 271, 515-523.
9. 1A receptors with positron emission tomography. Life Sci. 1994, 55, 403-407.
10. 11C] WAY100635, in monkey and human plasma by HPLC: comparison behavior of an identified radioactive metabolite with parent radioligand in monkey using PET. Nucl. Med. Biol. 1996, 23, 627-634.
11. 11C]WAY-100635. Eur. J. Pharmacol. 1995, 283, R1-R3.
12. 11C]WAY-100635. Eur. J. Pharmacol. 1996, 301, R5-R7.
13. Carson, R. E.; Schmall, B.; Endres, C. J.; Lang, L.; Der, M. G.; Adams, H. R.; Jagoda, E.; Herscovitch, P.; Eckelman, W. C. Kinetic analysis of the 5-HT1a antagonist [carbonyl-C11]WAY100635. J. Nucl. Med. 1997, 38, 80P-81P.
14. Zhuang, Z.-P.; Kung, M.-P.; Kung, H. F. Synthesis and evaluation of 4-(2′-methoxyphenyl)-1-[2′-[N-(2′-pyridinyl)-p-iodobenzamido] ethyl]piperazine (p-MPPI): a new iodinated 5-HT1a ligand. J. Med. Chem. 1994, 37, 1406-1407.
15. Schmall, B.; Lang, L.; Jagoda, E.; Channing, M.; Sassaman, M.; Eckelman, W. C. Antagonists for 5HT1a and 5HT2a receptors. J. Nucl. Med. 1996, 37, 204P.
16. Thielen, R. J.; Frazer, A. Effects of novel 5-HT1A receptor antagonists on measures of postsynaptic 5-HT1A receptor activation in vivo. Life Sci. 1995, 56, 163-168.
17. Forster, E. A.; Cliffe, I. A.; Bill, D. J.; Dover, G. M.; Jones, D.; Reilly, Y.; Fletcher, A. A pharmacological profile of the selective silent 5-HT1A receptor anatagonist, WAY-100635. Eur. J. Pharmacol. 1995, 281, 81-88.
18. Pike, V. W.; McCarron, J. A.; Hume, S. P. Pre-clinical development of a radioligand for studies of central 5-HT1a receptors in vivo-[11C]WAY-100635. Med. Chem. Res. 1995, 5, 208-227.
19. 18F]-N-succinimidyl 4-(fluoromethyl)benzoate for protein labeling. Appl. Radiat. Isot. 1994, 45, 1155-1163.
20. Kilbourn, M. Fluorine-18 labeling of radiopharmaceuticals; Nuclear Science Series, NAS-NS-3203; National Academy Press: Washington, DC, 1990.
21. Shiue, C.-Y.; Shiue, G. G.; Zhuang, Z. P.; Kung, M.-P.; Kung, H. F. Synthesis of no-carrier-added 4-(2′-methoxyphenyl)-1-[2′-(N-2′-pyridinyl)-p-[F-18]fluoro- benzamido]ethylpiperazine as a potential 5-HT1a receptor ligand for PET studies. J. Nucl. Med. 1994, 35, 252P.
22. Wagner, J. Fundamentals of Clinical Pharmacokinetics; Drug Intelligence Publications Inc.: Hamilton, IL, 1981.
23. Carson, R. E.; Schmall, B.; Endres, C. J.; Lang, L.; Der, M. G.; Adams, H. R.; Jagoda, E.; Herscovitch, P.; Eckelman, W. C. Kinetic modeling of the 5-HT1A antagonist [carbonyl-C-11]WAY-100635. J. Cereb. Flow Metab. 1997, 17, S327.
24. Zhuang, Z. P.; Kung, M.-P.; Mu, M.; Kung, H. F. Cyclic amide derivatives of 4-(2′-methoxyphenyl)-1-[2′-(N-2′-pyridinyl)-p- iodobenzamidolethylpiperazine (p-MPPIO) as 5-HT 1a receptor ligands. J. Labelled Compd. Radiopharm. 1997, 88-90.
25. Wilson, A. A.; DaSilva, J. N.; Inaba, T.; Fischer, N.; Houlew, S. Analogues of WAY 100635 as potential radiotracers for imaging 5-HT1A receptors by positron emision tomography (PET). J. Labelled Compd. Radiopharm. 1997, 531-533.
26. Pike, V. W.; McCarron, J. A.; Lundkvist, C.; et al. [Carbonyl-11C]desmethyl-WAY-100635 a new potent and selective radioligand for brain 5-HT1a receptors in vivo. J. Labelled Compd. Radiopharm. 1997, 568-570.
27. 1A receptor antagonist. Brain Res. 1995, 673, 217-225.
28. Eckelman, W. C.; Grissom, M.; Conklin, J.; Rzeszotaraki, W. J.; Gibson, R. E.; Francis, B. E.; Jagoda, E. M.; Eng, R.; Reba, R. C. In vivo competition studies with analogues of 3-quinuclidinyl benzilate. J. Pharm. Sci. 1984, 73, 529-534.
29. Buu-Hoi, N. P.; Jacquignon, P. Carcinogenic nitrogen Compounds: part XII. Fluorine containing 1:2- and 3:4-Benzacridines. J. Chem. Soc. 1962, 4173-4175.
30. Brewster, D.; Jones, R. S.; Parke, D. V. The metabolism of cyclohexanecarboxylate in the rat. Biochem. J. 1977, 764: 595-600.
31. 35S]Guanosine-5′-O-(3-thio)triphosphate binding as a measure of efficacy at human recombinant dopamine D4.4 receptors: actions of antiparkinsonian and antipsychotic agents. J. Pharmacol. Exp. Ther. 1997, 282, 181-191.