Synthesis and pharmacological evaluation of novel arylpiperazine derivatives as nonsteroidal androgen receptor antagonists

Chemical and Pharmaceutical Bulletin

Volumn 52, Issue 11, 2004, Pages 1330-1333

  Kinoyama, Isao ^a   Taniguchi, Nobuaki ^a   Yoden, Toru ^a   Koutoku, Hiroshi ^a   Furutani, Takashi ^a   Kudoh, Masafumi ^a   Okada, Minoru ^a  

^a ASTELLAS PHARMA INC   (Japan)

Author keywords

Androgen receptor; Antagonist; Antiandrogen; Prostate cancer

Indexed keywords

4 [4 CYANO (3 TRIFLUOROMETHYL)PHENYL] N (4 FLUOROPHENYL)PIPERAZINE 1 CARBOXAMIDE; ANTIANDROGEN; BICALUTAMIDE; PIPERAZINE DERIVATIVE; UNCLASSIFIED DRUG; YM 92088; ANDROGEN RECEPTOR;

ARTICLE; DRUG ACTIVITY; DRUG POTENCY; DRUG SYNTHESIS; EVALUATION; HIGH THROUGHPUT SCREENING; STRUCTURE ACTIVITY RELATION; ANIMAL; BIOSYNTHESIS; CHO CELL; DRUG ANTAGONISM; DRUG SCREENING; HAMSTER; HUMAN; METHODOLOGY; SYNTHESIS;

ANIMALS; CHO CELLS; CRICETINAE; DRUG EVALUATION, PRECLINICAL; HUMANS; PIPERAZINES; RECEPTORS, ANDROGEN;

EID: 21144448834     PISSN: 00092363     EISSN: None     Source Type: Journal    
DOI: 10.1248/cpb.52.1330     Document Type: Article

References (37)

1. Evans R. M., Science, 240, 889-895 (1988).
2. Chang C. S., Kokontis J., Liao S. T., Science, 240, 324-326 (1988).
3. Tsai M. J., O'Malley B. W., Annu. Rev. Biochem., 63, 451-486 (1994).
4. Kokontis J. M., Liao S., Vitam. Horm., 55, 219-307 (1999).
5. Zhi L., Martinborough E., Ann. Rep. Med. Chem., 36, 169-180 (2001).
6. Mooradian A. D., Morley J. E., Korenman S. G., Endocr. Rev., 8, 1-28 (1987).
7. Sciarra F., Toscano G., Concolino G., Di Silverio F., J. Steroid Biochem. Molec. Biol., 37, 349-362 (1990).
8. Ideyama Y., Kudoh M., Tanimoto K., Susaki Y., Nanya T., Nakahara T., Ishikawa H., Yoden T., Okada M., Fujikura T., Akaza H., Shikama H., Prostate, 37, 10-18 (1998).
9. Brogden R. N., Buckley M. M.-T., Ward A., Drugs, 39, 399-437 (1990).
10. Oesterling J. E., N. Engl. J. Med., 332, 99-109 (1995).
11. Lucky A. W., Am. J. Med., 98 (Suppl. 1A), 89S-94S (1995).
12. Mahler C., Verhelst J., Denis L., Clin. Pharmacokinet., 34, 405-417 (1998).
13. Singh S. M., Gauthier S., Labrie F., Curr. Med. Chem., 7, 211-247 (2000).
14. Neumann F., Exp. Clin. Endocrinol., 102, 1-32 (1994).
15. Labrie F., Cancer, 72, 3816-3827 (1993).
16. Koch H., Drugs Today, 20, 561-574 (1984).
17. Wysowski D. K., Freiman J. P., Tourtelot J. B., Horton M. L., Ann. Intern. Med., 118, 860-864 (1993).
18. Kuhn J. M., Billebaud T., Navratil H., Moulonguet A., Friet J., Grise P., Louis J. F., Costa P., Husson J. M., Dahan R., Bertagna C., Edelstein R., N. Engl. J. Med., 321, 413-418 (1989).
19. Kolvenbag G. J. C. M., Blackledge G. R. P., Urology, 47 (Suppl. 1A), 70-79 (1996).
20. Tucker H., Crook J. W., Chesterson G. J., J. Med. Chem., 31, 954-959 (1988).
21. Verhelst J., Denis L., Van Vliet P., Van Poppel H., Braeckman J., Van Cangh P., Mattelaer J., D'Hulster D., Mahler C., Clin. Endocrinol., 41, 525-530 (1994).
22. Dawson L. A., Chow E., Morton G., Urology, 49, 283-284 (1997).
23. Ishioka T., Tanatani A., Nagasawa K., Hashimoto Y., Bioorg. Med. Chem. Lett., 13, 2655-2658 (2003).
24. Hashimoto Y., Bioorg. Med. Chem., 10, 461-479 (2002).
25. Ishioka T., Kubo A., Koiso Y., Nagasawa K., Itai A., Hashimoto Y., Bioorg. Med. Chem., 10, 1555-1566 (2002).
26. Takahashi H., Ishioka T., Koiso Y., Sodeoka M., Hashimoto Y., Biol. Pharm. Bull., 23, 1387-1390 (2000).
27. Miyachi H., Azuma A., Kitamoto T., Hayashi K., Kato S., Koga M., Sato B., Hashimoto Y., Bioorg. Med. Chem. Lett., 7, 1483-1488 (1997).
28. Ohtsu H., Xiao Z., Ishida J., Nagai M., Wang H.-K., Itokawa H., Su C.-Y., Shih C., Chiang T., Chang E., Lee Y., Tsai M.-Y., Chang C., Lee K.-H., J. Med. Chem., 45, 5037-5042 (2002).
29. Ohtsu H., Itokawa H., Xiao Z., Su C.-Y., Shih C. C.-Y., Chiang T., Chang E., Lee Y., Chiu S.-Y., Chang C., Lee K.-H., Bioorg. Med. Chem., 11, 5083-5090 (2003).
30. Toney J. H., Chen Y., Rutledge S.-J., Schmidt A., Elbrecht A., J. Steroid Biochem. Molec. Biol., 60, 131-136 (1997).
31. Labrie F., Dupont A., Belanger A., Cusan L., Lacourciere Y., Monfette G., Laberge J. G., Emond J. P., Fazekas T. A., Raynaud J. P., Husson J. M., Clin. Invest. Med., 5, 267-275 (1982).
32. Simard J., Luthy I., Guay J., Belanger A., Labrie F., Mol. Cell. Endocrinol., 44, 261-270 (1986).
33. Sustic A., Vogl O., Polymer, 36, 3401-3408 (1995).
34. Kremer C. B., Meltsner M., Greenstein L., J. Am. Chem. Soc., 61, 2552 (1939).
35. Cerkovnikov E., Stern P., Arh. Kem., 18, 12-36 (1946).
36. Cretcher L. H., Pittenger W. H., J. Am. Chem. Soc., 47, 163-166 (1925).
37. Kotsuki H., Kobayashi S., Matsumoto K., Suenaga H., Nishizawa H., Synthesis, 12, 1147-1148 (1990).