Title:
17β HSD type 5 INHIBITOR
Document Type and Number:
WIPO Patent Application WO/2007/100066
Kind Code:
A1
Abstract:
It is intended to provide a novel and excellent method of treating and/or preventing prostate cancer, prostate enlargement, acne, seborrhea, hypertrichosis, calvities, alopecia, sexual precocity, adrenal hypertrophy, multilocular ovary syndrome, breast cancer, lung cancer, endometriosis, leiomyoma and so on based on an effect of selectively inhibiting 17β HSD type 5. It is found out that an N-sulfonylindole derivative, in which a carbon atom in the indole group is substituted by a carboxy group, a carboxy-substituted lower alkyl group or a carboxy-substituted lower alkenyl group, has a potent activity of selectively inhibiting 17β HSD type 5 and is usable as a remedy and/or a preventive for diseases, in which 17β HSD type 5 participates, such as prostate enlargement and prostate cancer without showing any side effect caused by a decrease in testosterone.
Inventors:
NIIMI TATSUYA (JP)
KAMIKAWA AKIO (JP)
AMANO YASUSHI (JP)
YAMAGUCHI TOMOHIKO (JP)
SUZUMURA KENICHI (JP)
ENJO KENTARO (JP)
FURUTANI TAKASHI (JP)
KAKEFUDA AKIO (JP)
KONDOH YUTAKA (JP)
HIRANO MASAAKI (JP)
KAMIKAWA AKIO (JP)
AMANO YASUSHI (JP)
YAMAGUCHI TOMOHIKO (JP)
SUZUMURA KENICHI (JP)
ENJO KENTARO (JP)
FURUTANI TAKASHI (JP)
KAKEFUDA AKIO (JP)
KONDOH YUTAKA (JP)
HIRANO MASAAKI (JP)
Application Number:
PCT/JP2007/053976
Publication Date:
September 07, 2007
Filing Date:
March 01, 2007
Export Citation:
Assignee:
ASTELLAS PHARMA INC (JP)
NIIMI TATSUYA (JP)
KAMIKAWA AKIO (JP)
AMANO YASUSHI (JP)
YAMAGUCHI TOMOHIKO (JP)
SUZUMURA KENICHI (JP)
ENJO KENTARO (JP)
FURUTANI TAKASHI (JP)
KAKEFUDA AKIO (JP)
KONDOH YUTAKA (JP)
HIRANO MASAAKI (JP)
NIIMI TATSUYA (JP)
KAMIKAWA AKIO (JP)
AMANO YASUSHI (JP)
YAMAGUCHI TOMOHIKO (JP)
SUZUMURA KENICHI (JP)
ENJO KENTARO (JP)
FURUTANI TAKASHI (JP)
KAKEFUDA AKIO (JP)
KONDOH YUTAKA (JP)
HIRANO MASAAKI (JP)
International Classes:
C07D209/42; A61K31/404; A61K31/407; A61K31/4155; A61K31/4178; A61K31/4245; A61K31/427; A61K31/428; A61K31/433; A61K31/4439; A61K31/538; A61P5/24; A61P5/38; A61P13/08; A61P15/00; A61P15/08; A61P17/08; A61P17/10; A61P17/14; A61P35/00; A61P43/00; C07D209/08; C07D401/12; C07D401/14; C07D403/12; C07D405/12; C07D409/12; C07D413/12; C07D413/14; C07D417/12; C07D491/056
Domestic Patent References:
| WO2005040112A1 | 2005-05-06 | |||
| WO2005113542A2 | 2005-12-01 | |||
| WO1996036611A1 | 1996-11-21 | |||
| WO1999050245A1 | 1999-10-07 | |||
| WO2006010008A1 | 2006-01-26 | |||
| WO2007030574A2 | 2007-03-15 | |||
| WO2007030559A2 | 2007-03-15 | |||
| WO2004110459A1 | 2004-12-23 | |||
| WO1996036611A1 | 1996-11-21 | |||
| WO1999050245A1 | 1999-10-07 | |||
| WO1997048697A1 | 1997-12-24 | |||
| WO2004064735A2 | 2004-08-05 |
Foreign References:
| JP2004529855A | 2004-09-30 | |||
| JP2001512716A | 2001-08-28 | |||
| JP2002536359A | 2002-10-29 | |||
| JP2003502367A | 2003-01-21 | |||
| JPH05506010A | 1993-09-02 | |||
| JP2002511852A | 2002-04-16 | |||
| JP2004518669A | 2004-06-24 | |||
| JP2004532194A | 2004-10-21 | |||
| JP2000136182A | 2000-05-16 | |||
| JPH09508137A | 1997-08-19 | |||
| JPH06340647A | 1994-12-13 | |||
| JP2005526033A | 2005-09-02 | |||
| JP2001505193A | 2001-04-17 | |||
| JP2000509719A | 2000-08-02 | |||
| JPH09104675A | 1997-04-22 | |||
| JPH06511238A | 1994-12-15 | |||
| JP2002506077A | 2002-02-26 | |||
| EP0902022A1 | 1999-03-17 | |||
| JPH09104675A | 1997-04-22 |
Other References:
KETTLE J.G. ET AL.: "N-Benzylindole-2-carboxylic acids: potent functional antagonists of the CCR2b chemokine receptor", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 14, no. 2, 2004, pages 405 - 408, XP002393948
MAHBOOBI S. ET AL.: "Bis(1H-2-indolyl)methanones as a Novel Class of Inhibitors of the Platelet-Derived Growth Factor Receptor Kinase", JOURNAL OF MEDICINAL CHEMISTRY, vol. 45, no. 5, 2002, pages 1002 - 1018, XP002374958
PASSARELLA D. ET AL.: "Cyclodimerization of indol-2-ylacetylenes. An example of intermolecular enyne-alkyne cycloaddition", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, no. 2, 2001, pages 127 - 129, XP003017354
MIKI Y. ET AL.: "Reaction of indole-2,3-dicarboxylic anhydride with Grignard reagents: synthesis of 2-acylindoles", HETEROCYCLES, vol. 45, no. 6, 1997, pages 1143 - 1150, XP003017355
CONWAY S.C. ET AL.: "Approaches to the generation of 2,3-indolyne", HETEROCYCLES, vol. 34, no. 11, 1992, pages 2095 - 2108, XP003017356
MOUADDIB A. ET AL.: "Synthesis of indolo[3,2-c]quinoline and pyrido[3',2':4,5]pyrrolo[3,2-c]quinoline derivatives", SYNTHESIS, no. 4, 2000, pages 549 - 556, XP001148027
HOPKINS C.R. ET AL.: "Design, synthesis, and biological activity of potent and selective inhibitors of mast cell tryptase", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 15, no. 11, 2005, pages 2734 - 2737, XP004906885
CLARK R.D. ET AL.: "OptDesign: Extending Optimizable kappa-Dissimilarity Selection to Combinatorial Libarary Design", JOURNAL OF CHEMICAL INFORMATION AND COMPUTER SCIENCES, vol. 43, no. 3, 2003, pages 829 - 836, XP003017357
NICOLAOU I. ET AL.: "Synthesis of N-protected 1H-indole-5-carboxylic acids with aldose reductase inhibitory potential", ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, vol. 34, no. 5, 2002, pages 511 - 514, XP003017358
See also references of EP 1990335A4
THE NEW ENGLAND JOURNAL OF MEDICINE, vol. 349, 2003, pages 2387 - 2398
FRONTIER IN NEUROENDOCRINOLOGY, vol. 22, 2003, pages 185 - 212
JOURNAL OF UROLOGY, vol. 161, 1999, pages 332 - 337
THE JOURNAL OF CLINICAL ENDOCRINOLOGY AND METABOLISM, vol. 80, 1995, pages 1066 - 1071
CLINICAL CANCER RESEARCH, vol. 10, 2004, pages 440 - 448
STEROIDS, vol. 69, 2004, pages 795 - 801
NATURE GENETICS, vol. 7, 1994, pages 34 - 39
ENDOCRINE REVIEWS, vol. 24, 2003, pages 152 - 182
THE JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 277, no. 27, 2002, pages 24799 - 24808
CARCINOGENESIS, vol. 25, no. 11, 2004, pages 2177 - 2181
CANCER RESEARCH, vol. 64, 2004, pages 1802 - 1810
SYNTHESIS, vol. 4, 2000, pages 549 - 556
"Rare Chemicals Catalogue", RARE CHEMICALS GMBH, ORDER NO. AL BE 0453
HETEROCYCLES, vol. 29, no. 4, 1989, pages 783 - 794
JOURNAL OF CHEMICAL INFORMATION AND COMPUTER SCIENCES, vol. 43, no. 3, 2003, pages 829 - 836
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, vol. 34, no. 5, 2002, pages 511 - 514
CANCER RESEARCH, vol. 66, 2006, pages 2815 - 2825
ARCHIV DER PHARMAZIE - PHARMACEUTICAL AND MEDICINAL CHEMISTRY, vol. 317, 1984, pages 847 - 851
MOLECULAR AND CELLULAR ENDOCRINOLOGY, vol. 248, 2006, pages 233 - 235
PROG. MED, vol. 5, 1985, pages 2157 - 2161
"Pharmaceutical Research and Development", vol. 7, 1990, HIROKAWA PUBLISHING CO., article "Drug Design", pages: 163 - 198
T. W. GREENE AND P. G. M. WUTS: "Protective Groups in Organic Synthesis", 3rd ed.", 1999
T.W. GREENE AND P.G.M. WUTS: "Protective Groups in Organic Synthesis" (3rd Edition", JOHN WILEY & SONS, INC.
TETRAHEDRON LETTERS, vol. 30, no. 16, 1989, pages 2129 - 2132
HETEROCYCLES, vol. 26, no. 5, 1987, pages 1173 - 1176
MARUZEN: "Experimental Chemistry Series,4th ed.", vol. 23, 1992, THE CHEMICAL SOCIETY OF JAPAN
""Compendium of Organic Synthetic Methods ,5th. ed.,", vol. 17, 2005
MARUZEN: "Experimental Chemistry Series,4th ed.", vol. 20, 1992, THE CHEMICAL SOCIETY OF JAPAN
""Compendium of Organic Synthetic Methods,5th ed.", vol. 14, 2005
MARUZEN: "Experimental Chemistry Series,4th ed.", vol. 22, 1992, THE CHEMICAL SOCIETY OF JAPAN
""Compendium of Organic Synthetic Methods,5th ed.", vol. 16, 2005
., MARUZEN: "Experimental Chemistry Series,4th ed.", vol. 19, 1992, THE CHEMICAL SOCIETY OF JAPAN
""Comprehensive Organic Synthesis", vol. 2, 1991, PERGAMON PRESS
BIOORGANIC AND MEDICINAL CHEMISTRY LETTERS, vol. 15, 2005, pages 2734 - 2737
JOURNAL OF THE CHEMICAL SOCIETY, 1954, pages 3842 - 3845
MARUZEN: "Experimental Chemistry Series,4th ed.", vol. 23, 1992, THE CHEMICAL SOCIETY OF JAPAN
"Protective Groups in Organic Synthesis", 1999
MANIATIS,T. ET AL.: "Molecular Cloning-A Laboratory Manual", COLD SPRING HARBOR LABORATORY,NY
MOL. ENDOCRINOL, vol. 11, no. 13, 1997, pages 1971 - 1984
TREVOR M. PENNING ET AL., BIOCHEM. J., vol. 351, 2000, pages 67 - 77
MAHBOOBI S. ET AL.: "Bis(1H-2-indolyl)methanones as a Novel Class of Inhibitors of the Platelet-Derived Growth Factor Receptor Kinase", JOURNAL OF MEDICINAL CHEMISTRY, vol. 45, no. 5, 2002, pages 1002 - 1018, XP002374958
PASSARELLA D. ET AL.: "Cyclodimerization of indol-2-ylacetylenes. An example of intermolecular enyne-alkyne cycloaddition", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, no. 2, 2001, pages 127 - 129, XP003017354
MIKI Y. ET AL.: "Reaction of indole-2,3-dicarboxylic anhydride with Grignard reagents: synthesis of 2-acylindoles", HETEROCYCLES, vol. 45, no. 6, 1997, pages 1143 - 1150, XP003017355
CONWAY S.C. ET AL.: "Approaches to the generation of 2,3-indolyne", HETEROCYCLES, vol. 34, no. 11, 1992, pages 2095 - 2108, XP003017356
MOUADDIB A. ET AL.: "Synthesis of indolo[3,2-c]quinoline and pyrido[3',2':4,5]pyrrolo[3,2-c]quinoline derivatives", SYNTHESIS, no. 4, 2000, pages 549 - 556, XP001148027
HOPKINS C.R. ET AL.: "Design, synthesis, and biological activity of potent and selective inhibitors of mast cell tryptase", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 15, no. 11, 2005, pages 2734 - 2737, XP004906885
CLARK R.D. ET AL.: "OptDesign: Extending Optimizable kappa-Dissimilarity Selection to Combinatorial Libarary Design", JOURNAL OF CHEMICAL INFORMATION AND COMPUTER SCIENCES, vol. 43, no. 3, 2003, pages 829 - 836, XP003017357
NICOLAOU I. ET AL.: "Synthesis of N-protected 1H-indole-5-carboxylic acids with aldose reductase inhibitory potential", ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, vol. 34, no. 5, 2002, pages 511 - 514, XP003017358
See also references of EP 1990335A4
THE NEW ENGLAND JOURNAL OF MEDICINE, vol. 349, 2003, pages 2387 - 2398
FRONTIER IN NEUROENDOCRINOLOGY, vol. 22, 2003, pages 185 - 212
JOURNAL OF UROLOGY, vol. 161, 1999, pages 332 - 337
THE JOURNAL OF CLINICAL ENDOCRINOLOGY AND METABOLISM, vol. 80, 1995, pages 1066 - 1071
CLINICAL CANCER RESEARCH, vol. 10, 2004, pages 440 - 448
STEROIDS, vol. 69, 2004, pages 795 - 801
NATURE GENETICS, vol. 7, 1994, pages 34 - 39
ENDOCRINE REVIEWS, vol. 24, 2003, pages 152 - 182
THE JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 277, no. 27, 2002, pages 24799 - 24808
CARCINOGENESIS, vol. 25, no. 11, 2004, pages 2177 - 2181
CANCER RESEARCH, vol. 64, 2004, pages 1802 - 1810
SYNTHESIS, vol. 4, 2000, pages 549 - 556
"Rare Chemicals Catalogue", RARE CHEMICALS GMBH, ORDER NO. AL BE 0453
HETEROCYCLES, vol. 29, no. 4, 1989, pages 783 - 794
JOURNAL OF CHEMICAL INFORMATION AND COMPUTER SCIENCES, vol. 43, no. 3, 2003, pages 829 - 836
ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, vol. 34, no. 5, 2002, pages 511 - 514
CANCER RESEARCH, vol. 66, 2006, pages 2815 - 2825
ARCHIV DER PHARMAZIE - PHARMACEUTICAL AND MEDICINAL CHEMISTRY, vol. 317, 1984, pages 847 - 851
MOLECULAR AND CELLULAR ENDOCRINOLOGY, vol. 248, 2006, pages 233 - 235
PROG. MED, vol. 5, 1985, pages 2157 - 2161
"Pharmaceutical Research and Development", vol. 7, 1990, HIROKAWA PUBLISHING CO., article "Drug Design", pages: 163 - 198
T. W. GREENE AND P. G. M. WUTS: "Protective Groups in Organic Synthesis", 3rd ed.", 1999
T.W. GREENE AND P.G.M. WUTS: "Protective Groups in Organic Synthesis" (3rd Edition", JOHN WILEY & SONS, INC.
TETRAHEDRON LETTERS, vol. 30, no. 16, 1989, pages 2129 - 2132
HETEROCYCLES, vol. 26, no. 5, 1987, pages 1173 - 1176
MARUZEN: "Experimental Chemistry Series,4th ed.", vol. 23, 1992, THE CHEMICAL SOCIETY OF JAPAN
""Compendium of Organic Synthetic Methods ,5th. ed.,", vol. 17, 2005
MARUZEN: "Experimental Chemistry Series,4th ed.", vol. 20, 1992, THE CHEMICAL SOCIETY OF JAPAN
""Compendium of Organic Synthetic Methods,5th ed.", vol. 14, 2005
MARUZEN: "Experimental Chemistry Series,4th ed.", vol. 22, 1992, THE CHEMICAL SOCIETY OF JAPAN
""Compendium of Organic Synthetic Methods,5th ed.", vol. 16, 2005
., MARUZEN: "Experimental Chemistry Series,4th ed.", vol. 19, 1992, THE CHEMICAL SOCIETY OF JAPAN
""Comprehensive Organic Synthesis", vol. 2, 1991, PERGAMON PRESS
BIOORGANIC AND MEDICINAL CHEMISTRY LETTERS, vol. 15, 2005, pages 2734 - 2737
JOURNAL OF THE CHEMICAL SOCIETY, 1954, pages 3842 - 3845
MARUZEN: "Experimental Chemistry Series,4th ed.", vol. 23, 1992, THE CHEMICAL SOCIETY OF JAPAN
"Protective Groups in Organic Synthesis", 1999
MANIATIS,T. ET AL.: "Molecular Cloning-A Laboratory Manual", COLD SPRING HARBOR LABORATORY,NY
MOL. ENDOCRINOL, vol. 11, no. 13, 1997, pages 1971 - 1984
TREVOR M. PENNING ET AL., BIOCHEM. J., vol. 351, 2000, pages 67 - 77
Attorney, Agent or Firm:
MORITA, Hiroshi et al. (3-11 Nihonbashi-Honcho 2-chome, Chuo-ku Tokyo 11, JP)
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