Benzopyran selective estrogen receptor modulators (SERMS): Pharmacological effects and structural correlation with raloxifene

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 7, 1996, Pages 903-908

  Grese, Timothy A ^a   Sluka, James P ^a   Bryant, Henry U ^a   Cole, Harlan W ^a   Kim, John R ^a   Magee, David E ^a   Rowley, Ellen R ^a   Sato, Masahiko ^a  

^a ELI LILLY AND COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

7 HYDROXY 3 (4 HYDROXYPHENYL) 2 [4 (2 PIPERIDINOETHOXY)PHENYL]BENZOPYRAN; BENZOPYRAN DERIVATIVE; CHOLESTEROL; ESTROGEN RECEPTOR; ETHINYLESTRADIOL; RALOXIFENE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; BONE DENSITY; CONTROLLED STUDY; DRUG DESIGN; DRUG SYNTHESIS; ESTROGEN ACTIVITY; FEMALE; MOLECULAR MODEL; NONHUMAN; ORAL DRUG ADMINISTRATION; OSTEOPOROSIS; OVARIECTOMY; RAT; STRUCTURE ACTIVITY RELATION; UTERUS WEIGHT;

ANIMALIA;

EID: 0029876149     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00141-2     Document Type: Article

References (23)

1. Lindsay, R. In Osteoporosis: Etiology, Diagnosis, and Management; Riggs, B. L.; Melton, L. J., Eds.; Raven: New York, 1988; p 333.
2. Ross, R. K.; Pike, M. C.; Mack, T. M.; Henderson, B. E. In HRT and Osteoporosis; Drife, J. O.; Studd, J. W. W., Eds.; Springer-Verlag: London, 1990; p 209.
3. Cust, M. P.; Gangar, K. F.; Whitehead, M. I. In HRT and Osteoporosis; Drife, J. O.; Studd, J. W. W., Eds.; Springer-Verlag: London, 1990; p 177.
4. Colditz, G. A.; Hankinson, S. E.; Hunter, D. J.; Willett, W. C.; Manson, J. E.; Stampfer, M. J.; Hennekens, C.; Rosner, B.; Speizer, F. E. New Eng. J. Med. 1995, 332, 1589.
5. Black, L. J.; Sato, M.; Rowley, E. R.; Magee, D. E.; Bekele, A.; Williams, D. C.; Cullinan, G. J.; Bendele, R.; Kauffman, R. F.; Bensch, W. R.; Frolik, C. A.; Termine, J. D.; Bryant, H. U. J. Clin. Invest. 1994, 93, 63.
6. Willson, T. M.; Henke, B. R.; Momtahen, Charifson, P. S.; Batchelor K. W.; Lubahn, D. B.; Moore, L. B.; Oliver, B. B.; Sauls, H. R.; Triantafillou, J. A.; Wolfe, S. G.; Baer, P. G. J. Med. Chem. 1994, 37, 1550.
7. Ke, H. Z.; Simmons, H. A.; Pirie, C. M.; Crawford, T.; Thompson, D. D. Endocrinology 1995,136, 2435.
8. Termine, J. D. Presented at American Society of Bone and Mineral Research, 16th Annual Meeting, Kansas City, MO, 1994, Minisymposia A: Estrogens and Anti-Estrogens.
9. Draper, M. W.; Flowers, D. E.; Huster, W. J.; Neild, J. A. Proceedings of the Fourth International Symposium on Osteoporosis 1993, 119.
10. Sharma, A. P.; Saeed, A.; Durani, S.; Kapil, R. S. J. Med. Chem. 1990, 33, 3222; and references therein.
11. Labrie, F.; Merand, Y. U.S. Patent 5 395 842, 1995; Chem. Abstr. 1995,123, 83209..
12. Sreenivasulu, S.; Singh, M. M.; Setty, B. S.; Kamboj, V. P. Contraception 1993, 48, 597.
13. Grese, T. A.; Pennington, L. D. Tetrahedron Lett. 1995, 36, 8913.
14. Bryant, H. U.; Bendele, A. M.; Magee, D. E.; Cole, H. W.; Spaethe, S. W. Pharmacologist 1992, 34, 194.
15. Wronski, T. J.; Yen, C.-F. Cells Mater. 1991, Suppl. 1, 69.
16. Westerlind, K. C.; Wakley, G. K.; Evans, G. L.; Turner, R. T. Endocrinology 1993, 133, 2924.
17. Turner, R. T.; Wakley, G. K.; Hannon, K. S.; Bell, N. H. J. Bone Min. Res. 1987, 2, 449.
18. Love, R. R.; Wiebe, D. A.; Newcomb, P. A.; Cameron, L.; Leventhal, H.; Jordan, V. C.; Feyzi, J.; DeMets, D. L. Ann. Intern. Med. 1991, 115, 860.
19. Dodge, J. A.; Stocksdale, M. G.; Black, L. J.; Rowley, E. R.; Bekele, A.; Cole, H. W.; Brown, C. E.; Magee, D. E.; Dehoney, G. A.; Bryant, H. U. J. Bone. Min. Res. 1993, 8, S278, abstract 648.
20. McDonnell, D. P.; Clemm, D. L.; Hermann, T.; Goldman, M. E.; Pike, J. W. Mol. Endocrinology 1995, 9, 659.
21. By James J. P. Stewart, Frank J. Seller Research Laboratory, U.S. Air Force Academy, Colorado 80840. QCPE #455 and references therein.
22. Previous studies have demonstrated that the conversion of the dimethylamino moiety to piperidino is not sufficient to account for this effect: Robertson, D. W.; Katzenellenbogen, J. A.; Hayes, J. R.; Katzenellenbogen, B. S. J. Med. Chem. 1982, 25,167. Jones, C. D.; Jevnikar, M. G.; Pike, A. J.; Peters, M. K.: Black, L. J.: Thompson, A. R.: Falcone, J. F.: Clemens, J. A. J. Med. Chem. 1984, 27, 1057.
23. Previous studies have demonstrated that the conversion of the dimethylamino moiety to piperidino is not sufficient to account for this effect: Robertson, D. W.; Katzenellenbogen, J. A.; Hayes, J. R.; Katzenellenbogen, B. S. J. Med. Chem. 1982, 25,167. Jones, C. D.; Jevnikar, M. G.; Pike, A. J.; Peters, M. K.: Black, L. J.: Thompson, A. R.: Falcone, J. F.: Clemens, J. A. J. Med. Chem. 1984, 27, 1057.