Phenyl quinolines and their use as estrogenic agents

Details Phenyl quinolines and their use as estrogenic agents Phenyl quinolines and their use as estrogenic agents

2006-08-01

2006-08-01

Seaman, D. Margaret (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C546S179000, C514S311000

Reexamination Certificate

active

07084276

ABSTRACT:
This invention provides estrogen receptor modulators of formula I, having the structurewherein,R1, R2, R3, R4, R5, and R6are as defined in the specification, or a N-oxide thereof or a pharmaceutically acceptable salt thereof or a prodrug thereof.

REFERENCES:
patent: 4418068 (1983-11-01), Jones
patent: 5126351 (1992-06-01), Luzzio et al.
patent: 5998402 (1999-12-01), Miller et al.
patent: 0 835 867 (1998-04-01), None
patent: WO 01/24785 (2001-04-01), None
patent: WO 02/04418 (2002-01-01), None
patent: WO 02/094268 (2002-11-01), None
patent: WO 02/094788 (2002-11-01), None
patent: WO 03/051805 (2003-06-01), None
patent: WO 03/051860 (2003-06-01), None
Mendelsohn, M. E. et al., “The Protective Effects of Estrogen on the Cardiovascular System,” New England Journal of Medicine 340: 1801-1811 (1999).
Epperson, C. N. et al., “Gonadal Steroids in the Treatment of Mood Disorders,” Psychosomatic Medicine 61: 676-697 (1999).
Crandall, C. J., “Estrogen Replacement Therapy and Colon Cancer: A Clinical Review,” Journal of Womens Health & Gender Based Medicine 8: 1155-1166 (1999).
Monk, D. et al., “Use of Estrogens for the Prevention and Treatment of Alzhimer's Disease,” Dementia & Geriatric Cognitive Disorders 11: 1-10 (2000).
Hurn, P. D. et al., “Estrogen as a Neuroprotectant in Stroke,” Journal of Cerebral Blood Flow & Metabolism 20: 631-652 (2000).
Calvin, M., “Oestrogens and Wound Healing,” Maturitas 34: 195-210 (2000).
Finking, G. et al., “Die Wirkungen von Östrogen im kardiovaskulären System,” Zeitschrift fur Kardiologie 89: 442-453 (2000) (English abstract included).
Brincat, M. P., “Hormone replacement therapy and the skin,” Maturitas 35: 107-117 (2000).
Al-Azzawi, F., “The menopause and its treatment in perspective,” Postgraduate Medical Journal 77: 292-304 (2001).
Moggs, J. G. et al., “Estrogen receptors: orchestrators of pleiotropic cellular responses,” EMBO Reports 2: 775-781 (2001).
Hall, J. M. et al., “The Multifaceted Mechanisms of Estradiol and Estrogen Receptor Signaling,” Journal of Biological Chemistry 276: 36869-36872 (2001).
McDonnell, D. P., Principles Of Molecular Regulation, Ch. 20, Humana Press, pp. 351-361(2000) Totowa, New Jersey.
McKenna, N. J. et al., “Nuclear Receptor Coregulators: Cellular and Molecular Biology,” Endocrine Reviews 20: 321-344 (1999).
Quaedackers, M. E. et al., “4-Hydroxytamoxifen Trans-Represses Nuclear Factor-κB Activity in Human Osteoblastic U2-OS Cells through Estrogen Receptor (ER)α, and Not through ERβ,” Endocrinology 142: 1156-1166 (2001).
Bhat, R. A. et al., “A Novel Human Estrogen Receptor β: Identification and Functional Analysis of Additional N-terminal Amino Acids,” Journal of Steroid Biochemistry & Molecular Biology 67: 233-240 (1998).
Pelzer, T. et al., “Estrogen Effects in the Myocardium: Inhibition of NF- κB DNA Binding by Estrogen Receptor-α and -β,” Biochemical & Biophysical Research Communications 286: 1153-7 (2001).
Levin, E. R., “Genome and Hormones: Gender Differences in PhysiologyInvited Review: Cell localization, physiology, and nongenomic actions of estrogen receptors,” Journal of Applied Physiology 91: 1860-1867 (2001).
Levin, E. R., “Cellular Functions of the Plasma Membrane Estorgen Receptor,” Trends in Endocrinology & Metabolism 10: 374-377 (1999).
Green, S. et al., “Human oestrogen receptor cDNA: sequence, expression and homology to v-erb-A,” Nature 320: 134-9 (1986).
Kuiper, G. et al., “Cloning of a novel estrogen receptor expressed in rat prostate and ovary,” Proceedings of the National Academy of Sciences of the United States of America 93: 5925-5930 (1996).
Couse, J. F. et al., “Tissue Distribution and Quantitative Analysis of Estrogen Receptor-α (ERα) and Estrogen Receptor-β (ERβ) Messenger Ribonucleic Acid in the Wild-Type and ERα-Knockout Mouse,” Endocrinology 138: 4613-4621 (1997).
Kuiper, G. et al., “Comparison of the Ligand Binding Specificity and Transcript Tissue Distribution of Estrogen Receptors α and β,” Endocrinology 138: 863-870 (1997).
Sar, M. et al., “Differential Expression of Estrogen Receptor- β and Esrogen Receptor-α in the Rat Ovary,” Endocrinology 140: 963-971 (1999).
Fitzpatrick, S. L. et al., “Expression of Estrogen Receptor- β Protein in Rodent Ovary,” Endocrinology 140: 2581-2591 (1999).
Cowley, S. M. et al., “Estrogen Receptors α and β Form Heterodimers on DNA,” Journal of Biological Chemistry 272: 19858-19862 (1997).
McDonnell, D. P., “Selective Estrogen Receptor Modulators (SERMs): A First Step in the Development of Perfect Hormone Replacement Therapy Regimen,” Journal of the Society for Gynecologic Investigation 7: S10-S15 (2000).
Goldstein, S. R. et al., “A Pharmacological review of selective oestrogen receptor modulators,” Human Reproduction Update 6: 212-224 (2000).
Pike, A. C. W. et al., “Structure of the ligand-binding domain of oestrogen receptor beta in the presence of a partial agonist and a full antagonist,” Embo 18: 4608-4618 (1999).
Shiau, A. K. et al., “The Structural Basis of Estrogen Receptor/Coactivator Recognition and the Antagonism of This Interaction by Tamoxifen,” Cell 95: 927-937 (Dec. 23, 1998).
Paige, et al., “Estrogen receptor (ER) modulators each induce distinct conformational changes in ER α and ER β,” Proceedings of the National Academy of Sciences of the United States of America 96: 3999-4004 (1999).
Meyers, Marvin J, et al., “Estrogen Receptor Subtype-Selective Ligands: Asymmetric Synthesis and Biological Evaluation of cis- and trans-5,11-Dialkyl-5,6,11,12-tetrahydrochrysenes,”J. Med. Chem.(1999), 42(13), 2456-2468.
Black, L. J. et al., “Uterine Bioassay of Tamoxifen, Trioxifene and a New Estrogen Antagonist (LY117018) in Rats and Mice,” Life Sciences, 26, 1453 (1980).
Yagi K., “Short Communications—A Simple Fluorometric Assay for Lipoperoxide in Blood Plasma,” Biochem Med 15:212-216 (1976).
Peele, D. B. et al., “Effects of Selection Delays on Radial Maze Performance: Acquisition and Effects of Scopolamine,” Pharmacology, Biochemistry, and Behavior, 29:143-150, (1988).
Monyer, H. et al., “Glucose deprivation neuronal injury in cortical culture,” 1989, Brain Research 483:347-354.
Wroblewski, F. et al. “Lactic Dehydrogenase Activity in Blood,” 1955, Proc. Soc. Exp. Biol. Med. 90:210-213.
Wallace, O. B. et al., “Tetrahydroquinoline-Based Selective Estrogen Receptor Modulators (SERMs),”Bioorganic&Medicinal Chemistry Letters, 2003, 13(11): 1907-1910.
Swenson, R. E. et al., “Synthesis of Substituted Quinolines Using the Dianion Addition ofN-Boc-anilines and α-Tolylsulfonyl- α,β-unsaturated Ketones,”Journal of Organic Chemistry, 2002, 67(26): 9182-9185.
Syeda Huma, H. Z. et al., “Cu(I)-catalyzed three component coupling protocol for the synthesis of quinoline derivatives,”Tetrahedron Letters, 2002, 43(36): 6485-6488.
Chemical Abstract Service; Lakhani, R. R. et al., Database Accession No. 1992:448192; RN 141853-28-3; 141853-36-3; 141853-44-3; 141853-52-3 abstract &Acta Ciencia Indica, Chemistry, 1991, 17C(1): 47-54.
Chemical Abstracts Service; Lakhani, R. R. et al., Database Accession No. 1998:549419; RN 116720-97-9; 116721-05-2; 116721-13-2; 116721-21-2 abstract &Journal of the Indian Chemical Society, 1988, 65(3): 197-9.
Chemical Abstracts Service; Lakhani, R. R. et al., Database Accession No. 1988:549314; RN 116734-27-1; 116734-35-1 abstract &Journal of the Institution of Chemists(India), 1987, 59(5): 230-2.
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