17βHSD type 5 inhibitor

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

Reexamination Certificate

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C548S492000

Reexamination Certificate

active

07855225

ABSTRACT:
To provide a novel and excellent method for treating and/or preventing prostatic cancer, benign prostatic hyperplasia, acne, seborrhea, hirsutism, baldness, alopecia, precocious puberty, adrenal hypertrophy, polycystic ovary syndrome, breast cancer, lung cancer, endometriosis, leiomyoma and the like based on selective inhibitory activity against 17βHSD type 5.It was found that an N-sulfonylindole derivative, where the indole ring is substituted by a carboxy group, a carboxy-substituted lower alkyl group or a carboxy-substituted lower alkenyl group at its carbon atom, has potent selective inhibitory activity against 17βHSD type 5 and may become a therapeutic agent and/or preventive agent for benign prostatic hyperplasia, prostatic cancer and the like without accompanying adverse drug reactions due to a decrease in testosterone, and the present invention has thus been completed.

REFERENCES:
patent: 5283251 (1994-02-01), Okada et al.
patent: 5464863 (1995-11-01), Nagamine et al.
patent: 5728712 (1998-03-01), Montana et al.
patent: 6207693 (2001-03-01), Setoi et al.
patent: 6255306 (2001-07-01), Macor
patent: 6288103 (2001-09-01), Faull et al.
patent: 6333323 (2001-12-01), Fujishita et al.
patent: 6469046 (2002-10-01), Daines et al.
patent: 6737435 (2004-05-01), Kettle et al.
patent: 2003/0069297 (2003-04-01), Cui et al.
patent: 2004/0167160 (2004-08-01), Gardinier et al.
patent: 2005/0154023 (2005-07-01), Spinks et al.
patent: 2006/0035884 (2006-02-01), Neitzel et al.
patent: 2006/0074076 (2006-04-01), Termin et al.
patent: 2009/0155903 (2009-06-01), Slade et al.
patent: 0 902 022 (1999-03-01), None
patent: 5-506010 (1993-09-01), None
patent: 6-340647 (1994-12-01), None
patent: 6-511238 (1994-12-01), None
patent: 9-104675 (1997-04-01), None
patent: 9-508137 (1997-08-01), None
patent: 2000-136182 (2000-05-01), None
patent: 2000-509719 (2000-08-01), None
patent: 2001-505193 (2001-04-01), None
patent: 2001-512716 (2001-08-01), None
patent: 2002-506077 (2002-02-01), None
patent: 2002-511852 (2002-04-01), None
patent: 2002-536359 (2002-10-01), None
patent: 2003-502367 (2003-01-01), None
patent: 2004-518669 (2004-06-01), None
patent: 2004-529855 (2004-09-01), None
patent: 2004-532194 (2004-10-01), None
patent: 2005-526033 (2005-09-01), None
patent: WO 93/03012 (1993-02-01), None
patent: WO 96/03400 (1996-02-01), None
patent: WO 96/36611 (1996-11-01), None
patent: WO 97/48697 (1997-12-01), None
patent: WO 98/24771 (1998-06-01), None
patent: WO 98/50356 (1998-11-01), None
patent: WO 99/46279 (1999-09-01), None
patent: WO 99/50245 (1999-10-01), None
patent: WO 02/30895 (2002-04-01), None
patent: WO 02/055517 (2002-07-01), None
patent: WO 02/071827 (2002-09-01), None
patent: WO 03/068220 (2003-08-01), None
patent: WO 2004/064735 (2004-08-01), None
patent: WO 2004/110459 (2004-12-01), None
patent: WO 2005/009958 (2005-02-01), None
patent: WO 2005/040112 (2005-05-01), None
patent: WO 2005/113542 (2005-12-01), None
patent: WO 2006/010008 (2006-01-01), None
patent: WO 2007/030559 (2007-03-01), None
patent: WO 2007/030574 (2007-03-01), None
Mouaddib et al. Synthesis, 2000, 4, 549-556.
Luo et al. (Cell, 2009, 136, pp. 823-837).
Sundberg et al. J. Org. Chem. 1973, 33, 3324-3330.
Kettle, et al., “N-Benzylindole-2-carboxylic acids: potent functional antagonists of the CCR2b chemokine receptor”, Bioorganic & Medicinal Chemistry Letters 14, pp. 405-408, (2004).
Hopkins, et al., “Design, synthesis, and biological activity of potent and selective inhibitors of mast cell tryptase”, Bioorganic & Medicinal Chemistry Letters 15, pp. 2734-2737, (2005).
Mahboobi, et al., “Bis(1H-2-indolyl) methanones as a Novel Class of Inhibitors of the Platelet-Derived Growth Factor Receptor Kinase”, J. Med. Chem. 45, pp. 1002-1018, (2002).
Mcconnell, et al., “The Long-Term Effect of Doxazosin, Finasteride, and Combination Therapy on the Clinical Progression of Benign Prostatic Hyperplasia”, The New Englad Journal of Medicine, vol. 349, No. 25, pp. 2387-2398, (Dec. 18, 2003).
Labrie, et al., “DHEA and Its Transformation into Androgens and Estrogens in Peripheral Target Tissues: Intracrinology”, Frontiers in Neuroendocrinolgy 22, pp. 185-212, (2001).
Span, et al., “Selectivity of Finasteride as an in Vivo Inhibitor of 5α-Reductase Isozyme Enzymatic Activity in the Human Prostate”, The Journal of Urology, vol. 61, pp. 332-337, (Jan. 1999).
Crawford, et al., “Therapeutic Controversies: Endocrine Therapy of Prostate Cancer: Optimal form and Appropriate Timing”, Journal of Clinical Endoctrinology and Metabolism, vol. 80, No. 4, pp. 1062-1078, (1995).
Mohler, et al., “The Adrogen Axis in Recurrent Prostate Cancer”, Clinical Cancer Research, vol. 10, pp. 440-448, (Jan. 15, 2004).
Lin, et al., “Characterization of a monoclonal antibody for human aldo-keto reductase AKR1C3 (type 2 3-α-hydoxysteroid dehydrogenase/type 5 17β-hydroxysteroid dehydrogenase); immunohistochemical detection in breast and prostate”, Steroids 69, pp. 795-801, (2004).
Geissler, et al., “Male pseudohermaphroditism caused by mutations of testicular 17β-hydroxysteroid dehydrogenase 3”, Nature Genetics, vol. 7, pp. 34-39, (May 1994).
Labrie, et al., “Endocrine and Intracine Sources of Androgens in Women: Inhibition of Breast Cancer and Other Roles of Androgens and Their Percursor Dehydroepiandrosterone”, Endocrine Reviews 24(2), pp. 152-182, (2003).
Palackal, et al., “Activation of Polycyclic Aromatic Hydrocarbontrans-Dihydrodiol Proximate Carcinogens by Human Aldo-keto Reductase (AKR1C) Enzymes and Their Functional Overexpression in Human Lung Carcinoma (A549) Cells”, The Journal of Biological Chemistry, vol. 277, No. 27, pp. 24799-24808, (2002).
Lan, et al., “Oxidative damage-related geneseAKR1C3andOGG1modulate risks for lung cancer due to exposure to PAH-rich coal combustion emissions”, Carcinogenesis, vol. 25, No. 11, pp. 2177-2181, (2004).
Lovering, et al., “Crystal Structures of Prostaglandin D211-Ketereductase (AKR1C3) in Complex with the Nonsteroidal Anti-Inflammatory Drugs Flufenamic Acid and Indomethacin”, Cancer Research 64, pp. 1802-1801, (Mar. 1, 2004).
Mouaddib, et al., “Synthesis of Indolo[3,2-c]quinoline and Pyrido[3′,2′:4,5][3,2-c]quinoline Derivatives”, Synthesis, No. 4, pp. 549-556, (2000).
Clark, et al., “OptDesign: Extending Optimizablek-Dissimilarity Selection to Combinatorial Library Design”, J. Chem. Inf. Comput. Sci, No. 43, pp. 829-836, (2003).
Stanbrough, et al., “Increased Expression of Genes Convering Adrenal Androgens to Testosterone in Androgen-Independent Prostate Cancer”, Cancer Res., No. 66, (5), pp. 2815-2825, (Mar. 1, 2006).
Bro{hacek over (z)}i{hacek over (c)}, et al., “Cinnamic acids as new inhibitors of 17β-hydroxysteroid dehydrogenase type 5 (AKR1C3)”, Molecular and Cellular Endocrinology 248, pp. 233-235, (2006).
Passarella, et al., “Cyclodimerization of indol-2-ylacetylenes. An example of intermolecular enyne-alkyne cycloaddition”, J. Chem. Soc. Perkin Trans. 1, pp. 127-129, (2001).
Rare Chemicals Catalogue, 1H-Indole-3-Carboxylic Acid, 1-[(4-Methylphenyl)Sulfonyl] Order No. AL BE 0453, SciFinder, p. 1 of 1, (Oct. 6, 2008).
Muratake, et al., “Preparation of Alkyl-Substituted Indoles in the Benzene Portion, Part 2”, Heterocycles, vol. 29, No. 4, pp. 783-794, (1989).
Nicolaou, et al., “Synthesis of N-Protected 1H-Indole-5-Carboxylic Acids With Aldose Reductase Inhibitory Potential”, Oppi Briefs, vol. 34, No. 5, pp. 511-514, (2002).
Andreani, et al., “Indole Derivatives Related to Lonidamine”, Arch. Pharm., No. 317, pp. 847-814, (1984).
Miki, et al., “Reaction of Indole-2,3-Dicarboxylic Anhydride With Grignard Reagents: Synthesis of 2-Acylindoles”, Heterocycles, vol. 45, No. 6, pp. 1143-1150, (1997).
Conway, et al., “Approaches to the G

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