Synthesis and pharmacology of the enantiomers of the potential atypical antipsychotic agents 5-OMe-BPAT and 5-OMe-(2,6-di-OMe)-BPAT

Bioorganic and Medicinal Chemistry

Volumn 7, Issue 7, 1999, Pages 1263-1271

  Homan, Evert J ^a   Copinga, Swier ^b   Unelius, Lena ^b   Jackson, David M ^b   Wikström, H̊kan V ^a   Grol, Cor J ^a  

^a UNIVERSITY MEDICAL CENTER GRONINGEN   (Netherlands)

^b R and D Laboratories   (Sweden)

Author keywords

2 Aminotetralins; Atypical antipsychotics; Benzamides; Dopamine; Serotonin

Indexed keywords

5 METHOXY 2 [N (2 BENZAMIDOETHYL) N N PROPYLAMINO]TETRALIN; 5 METHOXY 2 {N [2 (2,6 DIMETHOXY)BENZAMIDOETHYL] N N PROPYLAMINO}TETRALIN; BENZAMIDE DERIVATIVE; BUSPIRONE; CHLORPROMAZINE; CLOZAPINE; DEXAMPHETAMINE; DOPAMINE 2 RECEPTOR; FLESINOXAN; HALOPERIDOL; IPSAPIRONE; MAZAPERTINE; NEUROLEPTIC AGENT; RACLOPRIDE; RECEPTOR SUBTYPE; REMOXIPRIDE; RISPERIDONE; SEROTONIN 1A RECEPTOR; THIORIDAZINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CATALEPSY; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; ENANTIOMER; EXTRAPYRAMIDAL SYMPTOM; LOCOMOTION; MALE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RAT; REACTION ANALYSIS; RECEPTOR AFFINITY; STEREOCHEMISTRY;

AMPHETAMINE; ANIMALS; ANTIPSYCHOTIC AGENTS; BENZAMIDES; CATALEPSY; CELLS, CULTURED; CYCLIC AMP; DOPAMINE AGENTS; HUMANS; INHIBITORY CONCENTRATION 50; ISOMERISM; MALE; MOTOR ACTIVITY; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, ADRENERGIC, ALPHA-1; RECEPTORS, ADRENERGIC, ALPHA-2; RECEPTORS, ADRENERGIC, BETA; RECEPTORS, DOPAMINE D1; RECEPTORS, DOPAMINE D2; RECEPTORS, DOPAMINE D3; RECEPTORS, SEROTONIN; RECEPTORS, SEROTONIN, 5-HT1; REMOXIPRIDE; SEROTONIN AGENTS; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAHYDRONAPHTHALENES; VASOACTIVE INTESTINAL PEPTIDE;

EID: 0033004807     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(99)00073-5     Document Type: Article

References (46)

1. Broekkamp C.L.E., Oosterloo S.K., Berendsen H.H.G., Van Delft A.M.L. Naunyn Schmiedebergs Arch. Pharmacol. 338:1988;191.
2. McMillen B.A., Scott S.M., Davano E.A. J. Pharm. Pharmacol. 40:1988;885.
3. Invernizzi R.W., Cervo L., Samanin R. Neuropharmacology. 27:1988;515.
4. Elliot P.J., Walsh D.M., Close S.P., Higgins G.A., Hayes A.G. Neuropharmacology. 29:1990;949.
5. Hicks P.B. Life Sci. 47:1990;1609.
6. Wadenberg M.L., Ahlenius S. J. Neural Transm. Gen. Sect. 83:1991;43.
7. Neal-Beliveau B.S., Joyce J.N., Lucki I. J. Pharmacol. Exp. Ther. 265:1993;207.
8. Lucas G., Bonhomme N., De Deurwaerdere P., Le Moal M., Spampinato U. Psychopharmacology Berl. 131:1997;57.
9. Liebman J.M., Gerhardt S.C., Gerber R. Psychopharmacology Berl. 97:1989;456.
10. Christoffersen C.L., Meltzer L.T. Neuropsychopharmacology. 18:1998;399.
11. Wadenberg M.L., Ahlenius S. J. Neural. Transm. 74:1988;195.
12. Hillegaart V., Wadenberg M.L., Ahlenius S. Pharmacol. Biochem. Behav. 32:1989;797.
13. Rollema H., Lu Y., Schmidt A.W., Zorn S.H. Eur. J. Pharmacol. 338:1997;3.
14. Joyce J.N. Psychopharmacology Berl. 112:1993;S16.
15. Hashimoto T., Nishino N., Nakai H., Tanaka C. Life Sci. 48:1991;355.
16. Hashimoto T., Kitamura N., Kajimoto Y., Shirai Y., Shirakawa O., Mita T., Nishino N., Tanaka C. Psychopharmacology Suppl. 112:1993;35.
17. Sumiyoshi T., Stockmeier C.A., Overholser J.C., Dilley G.E., Meltzer H.Y. Brain Res. 708:1996;209.
18. Taylor D.P., Eison M.S., Riblet L.A., Vandermaelen C.P. Pharmacol. Biochem. Behav. 23:1985;687.
19. Wood P.L., Nair N.P., Lai S., Etienne P. Life Sci. 33:1983;269.
20. McMillen B.A. J. Neural. Transm. 64:1985;1.
21. Goff D.C., Midha K.K., Brotman A.W., McCormick S., Waites M., Amico E.T. J. Clin. Psychopharmacol. 11:1991;193.
22. Luchins D.J., Dojka D.M., Hanrahan P. Am. J. Ment. Retard. 98:1993;165.
23. D'Mello D.A., McNeil J.A., Harris W. J. Clin. Psychopharmacol. 9:1989;151.
24. Norman M.H., Navas III F., Thompson J.B., Rigdon G.C. J. Med. Chem. 39:1996;4692.
25. Reitz A.B., Bennett D.J., Blum P.S., Codd E.E., Maryanoff C.A., Ortegon M.E., Renzi M.J., Scott M.K., Shank R.P., Vaught J.L. J. Med. Chem. 37:1994;1060.
26. 2 antagonistic activity Soc. Neurosci. Abstr. 22:1996;841.
27. 1A agonistic properties Soc. Neurosci. Abstr. 23:1997;530.
28. Wustrow D., Belliotti T., Glase S., Ross Kesten S., Johnson D., Colbry N., Rubin R., Blackburn A., Akunne H., Corbin A., Davis M.D., Georgic L., Whetzel S., Zoski K., Heffner T., Pugsley T., Wise L. J. Med. Chem. 41:1998;760.
29. Homan E.J., Copinga S., Elfström L., Van der Veen T., Hallema J.-P., Mohell N., Unelius L., Johansson R., Wikström H., Grol C.J. Bioorg. Med. Chem. 6:1998;2111.
30. Hacksell U., Jackson D.M., Mohell N. Pharmacol. Toxicol. 76:1995;320.
31. Fowler C.J., Ahlgren P.C., Brännström G. Br. J. Pharmacol. 107:1992;141.
32. Karlsson A., Björk L., Pettersson C., Andén N.-E., Hacksell U. Chirality. 2:1990;90.
33. Fargin A., Raymond J.R., Regan J.W., Coteccia S., Lefkowitz R.J., Caron M.G. J. Biol. Chem. 264:1989;14848.
34. Dorflinger L.J., Schonbrunn A. Endocrinology. 113:1983;1541.
35. Malmberg Å., Nordvall G., Johansson A.M., Mohell N., Hacksell U. Mol. Pharmacol. 46:1994;299.
36. Grol C.J., Nordvall G., Johansson A.M., Hacksell U. J. Pharm. Pharmacol. 43:1991;481.
37. Van Vliet L.A., Tepper P.G., Dijkstra D., Damsma G., Wikstrm H., Pugsley T.A., Akunne H.C., Heffner T.G., Glase S.A., Wise L.D. J. Med. Chem. 39:1996;4233.
38. Hoffman D.C., Donovan H. Psychopharmacology Berl. 120:1995;128.
39. Niemegeers C.J.E., Janssen P.A.J. Life Sci. 24:1979;2201.
40. Wikström H., Andersson B., Sanchez D., Lindberg P., Arvidsson L.-E., Johansson A.M., Nilsson J.L., Svensson K., Hjorth S., Carlsson A. J. Med. Chem. 28:1985;215.
41. Malmberg Å., Jackson D.M., Eriksson A., Mohell N. Mol. Pharmacol. 43:1993;749.
42. Jackson D.M., Ryan C., Evenden J., Mohell N. Acta Psychiatr. Scand. Suppl. 380:1994;41.
43. Johansson L., Sohn D., Thorberg S.-O., Jackson D.M., Kelder D., Larsson L.-G., Rényi L., Ross S.B., Wallsten C., Eriksson H., Hu P.-S., Jerning E., Mohell N., Westlind-Danielsson A. J. Pharmacol. Exp. Ther. 283:1997;216.
44. Brown B.L., Ekins P. Adv. Cyclic Nucleotide Res. 2:1972;25.
45. Nordstedt C., Fredholm B.B. Anal. Biochem. 89:1990;231.
46. Ericson E., Samuelsson J., Ahlenius S. J. Pharmacol. Methods. 25:1991;111.