Therapeutically active triazoles and their use

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Cyclopentanohydrophenanthrene ring system doai

Reexamination Certificate

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C514S825000, C514S826000, C514S863000, C514S866000, C514S903000, C540S108000

Reexamination Certificate

active

08080540

ABSTRACT:
Estratrien-triazoles corresponding to formula (I) (shown below) which are useful in therapy, especially for the treatment and/or prevention or inhibition of a steroid hormone dependent disorder, preferably a steroid hormone dependent disease or disorder requiring the inhibition of a 17β-hydroxysteroid dehydrogenase (17β-HSD) such as 17β-HSD type 1, type 2 or type 3 enzyme.

REFERENCES:
patent: 3347878 (1967-10-01), Boswell
patent: 3413321 (1968-11-01), Boswell, Jr.
patent: 5993856 (1999-11-01), Ragavan et al.
patent: 6416778 (2002-07-01), Ragavan et al.
patent: 6541463 (2003-04-01), Labrie et al.
patent: 6652874 (2003-11-01), Ragavan et al.
patent: 6903102 (2005-06-01), Guzi et al.
patent: 2003/0170292 (2003-09-01), Yong et al.
patent: 2006/0009434 (2006-01-01), Hillisch et al.
patent: 2006/0052461 (2006-03-01), Hillisch et al.
patent: 2006/0271710 (2006-11-01), Chang et al.
patent: 0 367 576 (1990-05-01), None
patent: 0 977 555 (1998-07-01), None
patent: 0902022 (2006-06-01), None
patent: WO 99/46279 (1999-09-01), None
patent: WO 00/07996 (2000-02-01), None
patent: WO 01/42181 (2001-06-01), None
patent: WO 02/26706 (2002-04-01), None
patent: WO 03/017973 (2003-03-01), None
patent: WO 03/022835 (2003-03-01), None
patent: WO 03/033487 (2003-04-01), None
patent: WO 03/101972 (2003-12-01), None
patent: WO 2004/046111 (2004-06-01), None
patent: WO 2004/060488 (2004-07-01), None
patent: WO 2004/080271 (2004-09-01), None
patent: WO 2004/085345 (2004-10-01), None
patent: WO 2004/085457 (2004-10-01), None
patent: WO 2004/110459 (2004-12-01), None
patent: WO 2005/032527 (2005-04-01), None
patent: WO 2005/047303 (2005-05-01), None
patent: WO 2005/084295 (2005-09-01), None
patent: WO 2006/003012 (2006-01-01), None
patent: WO 2006/003013 (2006-01-01), None
patent: WO 2006/027347 (2006-03-01), None
patent: WO 2006/032885 (2006-03-01), None
patent: WO 2006/063585 (2006-06-01), None
patent: WO2006/063615 (2006-06-01), None
patent: WO 2006/125800 (2006-11-01), None
Souillac, et al., Characterization of Delivery Systems, Differential Scanning Calorimetry, pp. 217-218 (in Encyclopedia of Controlled Drug Delivery, 1999, John Wiley & Sons, pp. 212-227).
Vippagunta et al. (Advanced Drug Delivery Reviews, 48 (2001), pp. 3-26).
Deluca et al., “Inhibitory effects of fluorine-substituted estrogens on the activity of 17beta-hydroxysteroid dehydrogenases.” Molecular and Cellular Endocrinology, vol. 248, pp. 218-224, 2006.
“Lessons learned from marketed and investigational pro-drugs”, J.Med.Chem., 47, 2393-2404, 2004, Ettmayer et al.
Andersen, S.; (1995) “Molecular genetics of androgenic 17β-Hydroxysteroid Dehydrogenases”; J. Steroid Biochem. Molec. Biol., 55(5-6):533-534.
Andersen, J et al.; (2005) “Efficient One-Pot Synthesis of 1-Aryl 1,2,3-Triazoles from Aryl Halides and Terminal Alkynes in the Presence of Sodium Azide” Synlett, 2005, 19:2941.
Burow, Me et al.; “Phytochemical glyceollins, isolated from soy, mediate antihormonal effects through estrogen receptor alpha and beta”;J. Clin. Endocrinol. Metab. 86 (2001) (4), pp. 1750-1758.
Dong, Y et al. (1998) “17β-hydroxysteroid dehydrogenases in human bone cells”; J. Bone Min. Res., 13:1539-1546.
Einspanier, A. et al.; “Induction of endometriosis in the marmoset monkey (Callithrix jacchus)”; Mol Hum Reprod. May 2006;12(5):291-9. Epub Apr. 11, 2006.
Geissler WM et al. (1994) “Male pseudohermaphroditism caused by mutations of testicular 17beta-hydroxysteroid dehydrogenase 3.”; Nat Genet., 7:34-9.
Gruemmer, R. et al.; “Peritoneal endometriosis: validation of an in vivo model”;Hum. Reprod. 16 (2001) (8), pp. 1736-1743.
Husen, B. et al.; (2006) “Evaluation of inhibitors for 17β-hydroxysteroid dehydrogenase type 1 in vivo in immunodeficient mice inoculated with MCF-7 cells stably expressing the recombinant human enzyme”; Mol Cell Endocrinol. Mar. 27, 2006;248(1-2):109-13. Epub Jan. 10, 2006.
Koffmann B et al. (1991) “Evidence for involvement of tyrosine in estradiol binding by rat uterus estrogen receptor.” J. Steroid. Biochem. Mol. Biol. 38(2):135-139.
Labaree et al. (2003] “Synthesis and Evaluation of B-, C- and D-ring substituted estradiol carboxylic acid esters as locally active estrogens” J. Med. Chem. 46:1886-1904.
Labrie F et al. (1997) “The key role of 17 beta-hydroxysteroid dehydrogenases in sex steroid biology.” Steroids, 62:148-58.
Labrie et al. (2000) “Role of 17 beta-hydroxysteroid dehydrogenases in sex steroid formation in peripheral intracrine tissues” Trends Endocrinol Metab., 11:421-7.
Lawrence et al (2005) “Novel and potent 17beta-hydroxysteroid dehydrogenase type 1 inhibitors.” J Med Chem. 48(8):2759-62.
Liu et al (1992) “Synthesis of high affinity fluorine-substituted ligands for the androgen receptor. Potential agents for imaging prostatic cancer by positron emission tomography.” J Med Chem. 35(11):2113-29.
Medicinal Chemistry: Principles and Practice, 1994, ISBN 0-85186-494-5, Ed.: F. D. King, p. 215.
Oefelein, MG & Cornum, R (2000) “Failure to achieve castrate levels of testosterone during luteinizing hormone releasing hormone agonist therapy: the case for monitoring serum testosterone and a treatment decision algorithm.” J Urol.; 164(Iss. 3, Pt. 1):726-9.
Pelletier & Poirier (1996) “Synthesis and evaluation of estradiol derivatives with 16α-(bromoalkylamide), 16α-(bromoalkyl) or 16α-(bromoalkynyl) side chain as inhibitors of 17β-hydroxysteroid dehydrogenase type 1 without estrogenic activity” Bioorg Med Chem, 4(10):1617-1628.
Poirier et al. (1991) “Synthesis of 17β-estradiol derivatives with N-Butyl, N-methyl alkylamide side chain at position 15.” Tetrahedron, 47(37):7751-7766.
Poirier et al. (1996) “D-Ring alkylamine derivatives of estradiol: effect on ER-binding affinity and antiestrogenic activity” Bioorg Med Chem Lett 6(21):2537-2542.
Poirier et al. (1998) “A 6β-(Thiaheptanamide) Derivative of Estradiol as inhibitor of 17β-Hydroxysteroid Dehydrogenase Type 1”, J. Steroid Biochem. Molec. Biol., 64:83-90.
Poirier, D.; (2003) “Inhibitors of 17 beta-hydroxysteroid dehydrogenases” Curr Med Chem. 10:453-77.
Rostovtsev, VV. et al.; “A Stepwise Huisgen Cycloaddition Process: Copper(I)-Catalyzed Regioselective Ligation of Azides and Terminal Alkynes” Angew. Chem., 2002, 41(14), 2596-2599.
Sam et al. (1998) “C16 and C17 Derivatives of Estradiol as Inhibitors of 17β-Hydroxysteroid Dehydrogenase Type 1: Chemical Synthesis and Structure-Activity Relationships”, Drug Design and Discovery, 15(3):157-180.
Stella, J; “Pro-drugs as therapeutics”, Expert Opin. Ther. Patents, 14(3), 277-280, 2004.
Suginome et al. (1989), J. Org. Chem, 54(25) 5945.
Tamaya et al. (1985) “Comparison of cellular levels of steroid receptors in uterine leiomyoma and myometrium.” Acta Obstet Gynecol Scand., 64:307-9.
Tremblay & Poirier (1998) “Overview of a Rational Approach to Design Type I 17β- Hydroxysteroid Dehydrogenase inhibitors Without Estrogenic Activity: Chemical Synthesis and Biological Evaluation”, J. Steroid Biochem. Molec. Biol., 66:179-191.
Chetrite and Pasqualini (2001) “The selective estrogen enzyme modulator (SEEM) in breast cancer” Journal of Steroid Biochemistry & Molecular Biology 76: 95-104.
Smith et al. (2001) “Inhibitors of steroidogenesis as agents for the treatment of hormone-dependent cancers” Exp. Opin. Ther. Patents 11(5): 789-824.
Blomquist et al. (2002) “Androgenic and estrogenic 17beta-hydroxysteroid dehydrogenase/17-ketosteroid reductase in human ovarian eipthelial tumors: evidence for the type 1, 2, and 5 isoforms” Journal of Steroid Biochemistry & Molecular Biology, 153: 453-464.
Zeitoun and Bulun (1999) ȁ

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