Synthesis and pharmacological evaluation of 2-(3-piperidyl)-1,2,3,4- tetrahydroisoquinoline derivatives as specific bradycardic agents

Chemical and Pharmaceutical Bulletin

Volumn 51, Issue 4, 2003, Pages 390-398

  Kakefuda, Akio ^a   Watanabe, Toshihiro ^a   Taguchi, Yasuko ^a   Masuda, Noriyuki ^a   Tanaka, Akihiro ^b   Yanagisawa, Isao ^a  

^a ASTELLAS PHARMA INC   (Japan)

^b Yamanouchi House   (United Kingdom)

Author keywords

1,2,3,4 tetrahydroisoquinoline; Dimethoxy; Specific bradycardic agent; Zatebradine

Indexed keywords

1 [1 (2 AMINOBENZYL) 3 PIPERIDYL] 6,7 DIMETHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE SESQUIOXALATE; 2 (1 BENZYL 3 PIPERIDYL) 1,2,3,4 TETRAHYDROISOQUINOLINE; 2 (1 BENZYL 3 PIPERIDYL) 6 METHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE; 2 (1 BENZYL 3 PIPERIDYL) 6,7 DIMETHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE; 2 (1 BENZYL 3 PIPERIDYL) 7 METHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE; 2 (1 BENZYL 3 PIPERIDYL) 7 NITRO 1,2,3,4 TETRAHYDROISOQUINOLINE; 2 (1 BENZYL 3 PIPERIDYL) 8 METHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE; 2 (1 BENZYL 3 PYRROLIDYL) 6,7 DIMETHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE; 2 (1 BENZYL 4 PIPERIDYL) 6,7 DIMETHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE; 2 [1 [(1 ACETYL 4 PIPERIDYL)METHYL] 3 PIPERIDYL] 6,7 DIMETHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE DIOXALATE; 2 [1 [(1 TERT BUTOXYCARBONYL 4 PIPERIDYL)METHYL] 3 PIPERIDYL] 6,7 DIMETHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE; 2 [[3 (6,7 DIMETHOXY 1,2,3,4 TETRAHYDRO 2 ISOQUINOLYL)PIPERIDINO]METHYL] ACETANILIDE DIOXALATE; 2 [[3 (6,7 DIMETHOXY 1,2,3,4 TETRAHYDRO 2 ISOQUINOLYL)PIPERIDINO]METHYL] ACETANILIDE MONOOXALATE; 6,7 DIMETHOXY 2 (3 PIPERIDYL) 1,2,3,4 TETRAHYDROISOQUINOLINE; 6,7 DIMETHOXY 2 [1 (2 NITROBENZYL) 3 PIPERIDYL] 1,2,3,4 TETRAHYDROISOQUINOLINE DIOXALATE; 6,7 DIMETHOXY 2 [1 (4 PIPERIDYLMETHYL) 3 PIPERIDYL] 1,2,3,4 TETRAHYDROISOQUINOLINE; 6,7 DIMETHOXY 2 [1 [(4 INDOLYL)METHYL] 3 PIPERIDYL] 1,2,3,4 TETRAHYDROISOQUINOLINE SESQUIOXALATE; AMINE; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG; VERAPAMIL; ZATEBRADINE; 1,2,3,4-TETRAHYDROISOQUINOLINE; CARDIOTONIC AGENT; ISOQUINOLINE DERIVATIVE; TETRAHYDROISOQUINOLINE;

ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; BLOOD PRESSURE; DRUG POTENCY; DRUG SYNTHESIS; HEART ATRIUM; MALE; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION; ANIMAL; BRADYCARDIA; CHEMICALLY INDUCED DISORDER; CHEMISTRY; DOSE RESPONSE; DRUG EFFECT; DRUG SCREENING; GUINEA PIG; HEART RATE; IN VITRO STUDY; METHODOLOGY; PHYSIOLOGY; SYNTHESIS; WISTAR RAT;

ANIMALS; BRADYCARDIA; CARDIOTONIC AGENTS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG EVALUATION, PRECLINICAL; GUINEA PIGS; HEART RATE; ISOQUINOLINES; MALE; RATS; RATS, WISTAR; STRUCTURE-ACTIVITY RELATIONSHIP; TETRAHYDROISOQUINOLINES;

EID: 0242286043     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.51.390     Document Type: Article

References (25)

1. Laurent D., Bolene-Williams C., Williams F. L., Katz N. L., Am. J. Physiol., 185, 355-364 (1956).
2. Sonnenblick F. H., Ross J., Braunwald E., Am. J. Cardiol., 32, 328-336 (1968).
3. Buckberg G. D., Fixler D. E., Archie J. P., Hoffman J. I. E., Circ. Res., 30, 67-81 (1972).
4. Buckberg G. D., Fixler D. E., Archie J. P., Henney R. P., Hoffman J. I. E., Cardiovasc. Res., 9, 1-11 (1975).
5. Opie L. H., Cardiovasc. Drugs Ther., 3, 257-270 (1989).
6. Kern M. J., Deligonul U., Labovitz A., Am. Heart J., 118, 361-380 (1989).
7. Kobinger W., Lillie C., Eur. Heart J., 8 (Suppl. L), 7-15 (1987).
8. Raberger G., Krumpl G., Schneider W., Int. J. Cardiol., 14, 343-354 (1987).
9. Krumpl G., Winkler M., Schneider W., Raberger G., Br. J. Pharmacol., 94, 55-64 (1988).
10. Franke H., Su C. A. P. F., Schumacher K., Seiberling M., Eur. Heart J., 8 (Suppl. L), 91-98 (1987).
11. Van Woerkens L. J., Van Der Giessen W. J., Verdouw P. D., Cardiovasc. Drugs Ther., 6, 1, 59-65 (1992).
12. Harron D. W. G., Jady K., Riddell J. G., Shanks R. G., J. Cardiovasc. Pharmacol., 4, 1, 213-220 (1982).
13. Raberger G., Krumpl G., Schneider W., Mayer N., Eur. Heart J., 8, (Suppl. L), 53-59 (1987).
14. Indolfi C., Guth B. D., Miura T., Miyazaki S., Schulz R., Ross J., Jr., Circulation, 80, 983-993 (1989).
15. Kobinger W., Lillie C., Eur. J. Pharmacol., 104, 9-18 (1984).
16. Soward A., Vanhaleweyk G. L., Serruys P. W., Drugs, 32, 66-82 (1986).
17. Reiffen M., Eberlein W., Muller P., Psiorz M., Noll K., Heider J., Lillie C., Kobinger W., Luger P., J. Med. Chem., 33, 1496-1504 (1990).
18. Sall D. J., Grunewald G. L., J. Med. Chem., 30, 2208-2216 (1987).
19. Ajao. J. F., Bird C. W., J. Heterocyclic Chem., 22, 329-331 (1985).
20. Abdel-Magid A. F., Maryanoff C. A., Carson K. G., Tetrahedron Lett., 31, 5595-5598 (1990).
21. Zheng Q., Yang Y., Martin A. R., Tetrahedron Lett., 34, 2235-2238 (1993).
22. Mancuso A. J., Swern D., Synthesis, 1981, 165-185 (1981).
23. Bernet B., Piantini U., Vasella A., Carbohydr. Res., 204, 11-25 (1990).
24. Selnick H. G., Claremon D. A., Liverton N. J., WO9712876 (1997).
25. Perez O., Gay P., Franqueza L., Carron R., Valenzuela C., Delpon E., Tamargo J., Br. J. Pharmacol., 115, 787-794 (1995).