Title:
NAPHTHALENE DERIVATIVE
Document Type and Number:
WIPO Patent Application WO/2012/014994
Kind Code:
A1
Abstract:
Provided is a compound which can regulate a VCP activity.
Specifically provided is a compound represented by formula (I) (wherein R is as defined in the description) or an oxide, ester, prodrug, pharmaceutically acceptable salt or solvate thereof. The compound can regulate a VCP activity and is therefore useful for the treatment of VCP-mediated disorders such as neurodegenerative diseases.
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Inventors:
KAKIZUKA AKIRA (JP)
HORI SEIJI (JP)
SHUDO TOSHIYUKI (JP)
FUCHIGAMI TOMOHIRO (JP)
HORI SEIJI (JP)
SHUDO TOSHIYUKI (JP)
FUCHIGAMI TOMOHIRO (JP)
Application Number:
PCT/JP2011/067320
Publication Date:
February 02, 2012
Filing Date:
July 28, 2011
Export Citation:
Assignee:
DAITO CHEMIX CORP (JP)
UNIV KYOTO (JP)
KAKIZUKA AKIRA (JP)
HORI SEIJI (JP)
SHUDO TOSHIYUKI (JP)
FUCHIGAMI TOMOHIRO (JP)
UNIV KYOTO (JP)
KAKIZUKA AKIRA (JP)
HORI SEIJI (JP)
SHUDO TOSHIYUKI (JP)
FUCHIGAMI TOMOHIRO (JP)
International Classes:
A61K31/655; C07C309/47; A61P1/00; A61P1/04; A61P1/08; A61P1/18; A61P3/06; A61P9/10; A61P9/12; A61P11/00; A61P13/02; A61P13/08; A61P13/12; A61P17/00; A61P19/00; A61P19/02; A61P19/10; A61P21/00; A61P25/00; A61P25/06; A61P25/14; A61P25/16; A61P25/18; A61P25/22; A61P25/24; A61P25/28; A61P29/00; A61P31/12; A61P35/00; A61P35/02; A61P37/02; A61P37/06; A61P37/08; A61P43/00; C07C323/36; C07D213/76; C07D213/78; C07D215/38; C07D217/14; C07D333/38; C07D401/04; C07D401/12; C07D405/04; C07D405/12; C07D409/04; C07D409/14; C07D413/04
Domestic Patent References:
| WO2006025304A1 | 2006-03-09 |
Foreign References:
| CN101633796A | 2010-01-27 | |||
| US7387667B1 | 2008-06-17 | |||
| CN1746229A | 2006-03-15 | |||
| JP2004075921A | 2004-03-11 | |||
| CN86105522A | 1988-02-24 | |||
| DE3417237A1 | 1985-11-14 | |||
| JPS58174463A | 1983-10-13 | |||
| DE2436257A1 | 1976-02-12 | |||
| US2865916A | 1958-12-23 | |||
| US5607915A | 1997-03-04 |
Other References:
RUDYK, H. ET AL.: "Synthesis and evaluation of analogues of congo red as potential compounds against transmissible spongiform encephalopathies", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, vol. 38, no. 6, 2003, pages 567 - 579, XP004433576, DOI: doi:10.1016/S0223-5234(03)00081-3
UEDA, T. ET AL.: "Researches on chemotherapeutic drugs against viruses. XI. Synthesis and antiviral effects of 3-alkylphenylazo-4- aminonaphthalenesulfonic acid and its sulfonamide derivatives", PHARMACEUTICAL BULLETIN, vol. 1, 1953, pages 271 - 274
HIYAMA, M.: "Studies on Naphthalenesulfonic acid derivatives. III. Naphthylazobenzene sulfonamide derivatives; syntheses and tests for their effect on bacteria and viruses", YAKUGAKU ZASSHI, vol. 72, 1952, pages 1374 - 1377
UEDA, T. ET AL.: "Researches on chemotherapeutic drugs against viruses. IV. Syntheses and antiviral effects of 3-phenylazonaphthionic acid and its derivatives", YAKUGAKU ZASSHI, vol. 72, 1952, pages 260 - 264
SEKAR, N. ET AL.: "Synthesis of azo reactive dyes containing aldehyde group", ASIAN JOURNAL OF CHEMISTRY, vol. 19, no. 4, 2007, pages 2565 - 2573
WANG, L. ET AL.: "Structure-properties relationships investigation on the azo dyes derived from benzene sulfonamide intermediates", DYES AND PIGMENTS, vol. 76, no. 3, 2008, pages 636 - 645, XP022260161, DOI: doi:10.1016/j.dyepig.2006.12.003
AKERMAN, D. ET AL.: "Interaction of oxidative bleach containing detergents with dyes. Part 1. Preparation and resistance of 1-amino-2- arylazonaphthalene-4-sulphonic acid dyes to hydrogen peroxide and m-chloroperbenzoic acid", DYES AND PIGMENTS, vol. 59, no. 3, 2003, pages 285 - 292, XP004454408, DOI: doi:10.1016/S0143-7208(03)00115-3
STOPA, B. ET AL.: "Supramolecular ligands: monomer structure and protein ligation capability", BIOCHIMIE, vol. 80, no. 12, 1998, pages 963 - 968
INOUE, Y. ET AL.: "Ultraviolet and visible absorption spectra of 1-amino-2-(1,3,5- triazinyl)azonaphthalene-4-sulfonic acids and of their metal complexes", SENRYO TO YAKUHIN, vol. 41, no. 2, 1996, pages 27 - 36
WATANABE, N. ET AL.: "The effect of substituent on absorption bands of sodium 2-(substituted phenylazo)-1-naphthylaminesulfonates", TOKYO KOGYO KOTO SENMON GAKKO KENKYU HOKOKUSHO, vol. 13, 1981, pages 67 - 70
ARCORIA, A. ET AL.: "Study on new direct azo dyes. Dyes from 2-(p-aminophenyl)-, 2,5-bis (p-aminophenyl)- and 2,5-bis(p-aminostyryl) thiophene: dyeing thermodynamics, metallization, CIE measurement", CHIMICA E L'INDUSTRIA, vol. 60, no. 12, 1978, MILAN, ITALY, pages 981 - 986
BARNI, E. ET AL.: "Acid dyes for wool and nylon from p-amino-a-methylcinnamaldehyde", TINCTORIA, vol. 72, no. 5, 1975, pages 147 - 151
FISICHELLA, S. ET AL.: "Substantivity of mono- and disazo direct dyes from trans-2-(4- aminostyryl)furan", TINCTORIA, vol. 71, no. 6, 1974, pages 189 - 191
MIKHAILOVA, N.N. ET AL.: "Effect of the nature of the complex-forming substituent on the stability of chromium-containing azo dyes", ZHURNAL OBSHCHEI KHIMII, vol. 36, no. 2, 1966, pages 333 - 336
BUDESINSKY, B.: "Complexes of metallochromic substances. IV. Metallochromic properties of 2-(o-carboxyphenylazo)naphthionic acid and 2-(o-arsonophenylazo)naphthionic acid", FRESENIUS' ZEITSCHRIFT FUER ANALYTISCHE CHEMIE, vol. 207, no. 4, 1965, pages 241 - 247
PERSHIN, N.G. ET AL.: "Some regularities in influenza virus control with synthetic drugs", FARMAKOLOGIYA I TOKSIKOLOGIYA(MOSCOW), vol. 24, 1961, pages 690 - 695
HARADA, K. ET AL.: "Azo dyes. XXI. Azo dyes from dehydrothio-p-toluidine", HIROSHIMA DAIGAKU KOGAKUBU KENKYU HOKOKU, vol. 11, 1962, pages 31 - 36
ROSEIRA, A.N. ET AL.: "The mechanism of color changes in acid solutions of secondary diazo dyes", ANAIS DA ACADEMIA BRASILEIRA DE CIENCIAS, vol. 30, 1958, pages 311 - 321
HOLMES, F.H.: "The absorption spectra and the substantivity to cotton of Congo red and related structures", TRANSACTIONS OF THE FARADAY SOCIETY, vol. 54, 1958, pages 1166 - 1171
TATSUOKA, S. ET AL.: "Studies on antimalarials. VIII. Syntheses of antimalarials with azo groups", ANN. REPT. TAKEDA RESEARCH LAB, vol. 10, 1951, pages 16 - 32
TAKAHASHI, T. ET AL.: "Pyridine derivatives containing sulfur. XXI. Synthesis of azopyridinesulfonic acids", YAKUGAKU ZASSHI, vol. 7, no. 8, 1946, pages 28 - 29
SAIKACHI, H.: "Pyridine derivatives containing sulfur. IX. Synthesis of azopyridines", YAKUGAKU ZASSHI, vol. 64, 1944, pages 328 - 330
SEITAI NO KAGAKU, vol. 60, no. 6, 2009, pages 579 - 584
CLINICAL NEUROSCIENCE, vol. 27, no. 9, September 2009 (2009-09-01), pages 964 - 965
T. HIGUCHI; V. STELLA: "Pro drugs as Novel Delivery Systems", vol. 14, A.C.S. SYMPOSIUM SERIES
"Bioreversible Carriers in Drug Design", 1987, AMERICAN PHARMACEUTICAL ASSOCIATION AND PERGAMON PRESS
"RECOMMENDATIONS FOR SECTION E, FUNDAMENTAL STEREOCHEMISTRY", PURE APPL. CHEM., vol. 45, 1974, pages 13 - 30
TRENDS GENET., vol. 14, 1998, pages 396 - 402
CELL DEATH DIFFER., vol. 8, 2001, pages 977 - 984
CELL DEATH DIFFER., vol. 9, 2002, pages 264 - 273
NEUROSCI. LETT., vol. 343, 2003, pages 77 - 80
J. BIOL. CHEM., vol. 279, 2004, pages 51376 - 51385
GENES CELLS, vol. 12, 2007, pages 889 - 901
FEBS LETT., vol. 580, 2006, pages 474 - 478
NAT. GENET., vol. 36, 2004, pages 377 - 381
J. BIOL. CHEM., vol. 273, 1998, pages 3562 - 3567
J. BIOL. CHEM., vol. 277, 2002, pages 47358 - 47365
NATURE, vol. 429, 2004, pages 841 - 847
CELL, vol. 82, 1995, pages 905 - 914
NATURE, vol. 450, 2007, pages 1258 - 1262
J. CELL. SCI., vol. 117, 2004, pages 281 - 292
ANN. ONCOL., vol. 15, 2004, pages 1432 - 1438
J. BIOL. CHEM., vol. 279, 2004, pages 38184 - 38193
BIOCHIM. BIOPHYS. ACTA, vol. 1793, 2009, pages 1710 - 1718
T. W. GREENE; G. M. WUTS: "Protecting Groups in Organic Synthesis", 1999, WILEY
"Fieser and Fieser's Reagents for Organic Synthesis", vol. 1-15, 1991, JOHN WILEY AND SONS
"Rodd's Chemistry of Carbon Compounds", vol. 1-5, 1989, ELSEVIER SCIENCE PUBLISHERS
"Organic Reactions", vol. 1-40, 1991, JOHN WILEY AND SONS
"March's Advanced Organic Chemistry", JOHN WILEY AND SONS
"Larock's Comprehensive Organic Transformations", 1989, VCH PUBLISHERS INC.
J. F. W. MCOMIE: "Protective Groups in Organic Chemistry", 1973, PLENUM PRESS
T. W. GREENE; P. G. M. WUTS: "Protective Groups in Organic Synthesis", 1999, WILEY
"The Peptides", vol. 3, 1981, ACADEMIC PRESS
HOUBEN WEYL: "Methoden der organischen Chemie", vol. 15, 1974, GEORG THIEME VERLAG
H.-D. JAKUBKE; H. JESCHKEIT: "Aminosaeuren, Peptide, Proteine", 1982, VERLAG CHEMIE
JOCHEN LEHMANN: "Chemie der Kohlenhydrate: Monosaccharide und Derivate", 1974, GEORG THIEME VERLAG
"Remington's Pharmaceutical Sciences", 1991, MACK PUB. CO.
T. HIGUCHI; V. STELLA: "Pro-drugs as Novel Delivery Systems", vol. 14, A.C.S. SYMPOSIUM SERIES
BERTOLINI, G. ET AL., J. MED. CHEM., vol. 40, 1997, pages 2011 - 2016
SHAN, D. ET AL., J. PHARM. SCI., vol. 86, no. 7, pages 765 - 767
BAGSHAWE K., DRUG DEV. RES., vol. 34, 1995, pages 220 - 230
BODOR, N., ADVANCES IN DRUG RES., vol. 13, 1984, pages 224 - 331
BUNDGAARD, H.: "Design of Prodrugs", 1985, ELSEVIER PRESS
LARSEN, I. K. ET AL.: "Design and Application of Prodrugs, Drug Design and Development", 1991, HARWOOD ACADEMIC PUBLISHERS
"Methods in Cell Biology", vol. XIV, 1976, ACADEMIC PRESS, pages: 33
"Remington's Pharmaceutical Sciences", 1990, MACK PUBLISHING COMPANY
See also references of EP 2599771A4
UEDA, T. ET AL.: "Researches on chemotherapeutic drugs against viruses. XI. Synthesis and antiviral effects of 3-alkylphenylazo-4- aminonaphthalenesulfonic acid and its sulfonamide derivatives", PHARMACEUTICAL BULLETIN, vol. 1, 1953, pages 271 - 274
HIYAMA, M.: "Studies on Naphthalenesulfonic acid derivatives. III. Naphthylazobenzene sulfonamide derivatives; syntheses and tests for their effect on bacteria and viruses", YAKUGAKU ZASSHI, vol. 72, 1952, pages 1374 - 1377
UEDA, T. ET AL.: "Researches on chemotherapeutic drugs against viruses. IV. Syntheses and antiviral effects of 3-phenylazonaphthionic acid and its derivatives", YAKUGAKU ZASSHI, vol. 72, 1952, pages 260 - 264
SEKAR, N. ET AL.: "Synthesis of azo reactive dyes containing aldehyde group", ASIAN JOURNAL OF CHEMISTRY, vol. 19, no. 4, 2007, pages 2565 - 2573
WANG, L. ET AL.: "Structure-properties relationships investigation on the azo dyes derived from benzene sulfonamide intermediates", DYES AND PIGMENTS, vol. 76, no. 3, 2008, pages 636 - 645, XP022260161, DOI: doi:10.1016/j.dyepig.2006.12.003
AKERMAN, D. ET AL.: "Interaction of oxidative bleach containing detergents with dyes. Part 1. Preparation and resistance of 1-amino-2- arylazonaphthalene-4-sulphonic acid dyes to hydrogen peroxide and m-chloroperbenzoic acid", DYES AND PIGMENTS, vol. 59, no. 3, 2003, pages 285 - 292, XP004454408, DOI: doi:10.1016/S0143-7208(03)00115-3
STOPA, B. ET AL.: "Supramolecular ligands: monomer structure and protein ligation capability", BIOCHIMIE, vol. 80, no. 12, 1998, pages 963 - 968
INOUE, Y. ET AL.: "Ultraviolet and visible absorption spectra of 1-amino-2-(1,3,5- triazinyl)azonaphthalene-4-sulfonic acids and of their metal complexes", SENRYO TO YAKUHIN, vol. 41, no. 2, 1996, pages 27 - 36
WATANABE, N. ET AL.: "The effect of substituent on absorption bands of sodium 2-(substituted phenylazo)-1-naphthylaminesulfonates", TOKYO KOGYO KOTO SENMON GAKKO KENKYU HOKOKUSHO, vol. 13, 1981, pages 67 - 70
ARCORIA, A. ET AL.: "Study on new direct azo dyes. Dyes from 2-(p-aminophenyl)-, 2,5-bis (p-aminophenyl)- and 2,5-bis(p-aminostyryl) thiophene: dyeing thermodynamics, metallization, CIE measurement", CHIMICA E L'INDUSTRIA, vol. 60, no. 12, 1978, MILAN, ITALY, pages 981 - 986
BARNI, E. ET AL.: "Acid dyes for wool and nylon from p-amino-a-methylcinnamaldehyde", TINCTORIA, vol. 72, no. 5, 1975, pages 147 - 151
FISICHELLA, S. ET AL.: "Substantivity of mono- and disazo direct dyes from trans-2-(4- aminostyryl)furan", TINCTORIA, vol. 71, no. 6, 1974, pages 189 - 191
MIKHAILOVA, N.N. ET AL.: "Effect of the nature of the complex-forming substituent on the stability of chromium-containing azo dyes", ZHURNAL OBSHCHEI KHIMII, vol. 36, no. 2, 1966, pages 333 - 336
BUDESINSKY, B.: "Complexes of metallochromic substances. IV. Metallochromic properties of 2-(o-carboxyphenylazo)naphthionic acid and 2-(o-arsonophenylazo)naphthionic acid", FRESENIUS' ZEITSCHRIFT FUER ANALYTISCHE CHEMIE, vol. 207, no. 4, 1965, pages 241 - 247
PERSHIN, N.G. ET AL.: "Some regularities in influenza virus control with synthetic drugs", FARMAKOLOGIYA I TOKSIKOLOGIYA(MOSCOW), vol. 24, 1961, pages 690 - 695
HARADA, K. ET AL.: "Azo dyes. XXI. Azo dyes from dehydrothio-p-toluidine", HIROSHIMA DAIGAKU KOGAKUBU KENKYU HOKOKU, vol. 11, 1962, pages 31 - 36
ROSEIRA, A.N. ET AL.: "The mechanism of color changes in acid solutions of secondary diazo dyes", ANAIS DA ACADEMIA BRASILEIRA DE CIENCIAS, vol. 30, 1958, pages 311 - 321
HOLMES, F.H.: "The absorption spectra and the substantivity to cotton of Congo red and related structures", TRANSACTIONS OF THE FARADAY SOCIETY, vol. 54, 1958, pages 1166 - 1171
TATSUOKA, S. ET AL.: "Studies on antimalarials. VIII. Syntheses of antimalarials with azo groups", ANN. REPT. TAKEDA RESEARCH LAB, vol. 10, 1951, pages 16 - 32
TAKAHASHI, T. ET AL.: "Pyridine derivatives containing sulfur. XXI. Synthesis of azopyridinesulfonic acids", YAKUGAKU ZASSHI, vol. 7, no. 8, 1946, pages 28 - 29
SAIKACHI, H.: "Pyridine derivatives containing sulfur. IX. Synthesis of azopyridines", YAKUGAKU ZASSHI, vol. 64, 1944, pages 328 - 330
SEITAI NO KAGAKU, vol. 60, no. 6, 2009, pages 579 - 584
CLINICAL NEUROSCIENCE, vol. 27, no. 9, September 2009 (2009-09-01), pages 964 - 965
T. HIGUCHI; V. STELLA: "Pro drugs as Novel Delivery Systems", vol. 14, A.C.S. SYMPOSIUM SERIES
"Bioreversible Carriers in Drug Design", 1987, AMERICAN PHARMACEUTICAL ASSOCIATION AND PERGAMON PRESS
"RECOMMENDATIONS FOR SECTION E, FUNDAMENTAL STEREOCHEMISTRY", PURE APPL. CHEM., vol. 45, 1974, pages 13 - 30
TRENDS GENET., vol. 14, 1998, pages 396 - 402
CELL DEATH DIFFER., vol. 8, 2001, pages 977 - 984
CELL DEATH DIFFER., vol. 9, 2002, pages 264 - 273
NEUROSCI. LETT., vol. 343, 2003, pages 77 - 80
J. BIOL. CHEM., vol. 279, 2004, pages 51376 - 51385
GENES CELLS, vol. 12, 2007, pages 889 - 901
FEBS LETT., vol. 580, 2006, pages 474 - 478
NAT. GENET., vol. 36, 2004, pages 377 - 381
J. BIOL. CHEM., vol. 273, 1998, pages 3562 - 3567
J. BIOL. CHEM., vol. 277, 2002, pages 47358 - 47365
NATURE, vol. 429, 2004, pages 841 - 847
CELL, vol. 82, 1995, pages 905 - 914
NATURE, vol. 450, 2007, pages 1258 - 1262
J. CELL. SCI., vol. 117, 2004, pages 281 - 292
ANN. ONCOL., vol. 15, 2004, pages 1432 - 1438
J. BIOL. CHEM., vol. 279, 2004, pages 38184 - 38193
BIOCHIM. BIOPHYS. ACTA, vol. 1793, 2009, pages 1710 - 1718
T. W. GREENE; G. M. WUTS: "Protecting Groups in Organic Synthesis", 1999, WILEY
"Fieser and Fieser's Reagents for Organic Synthesis", vol. 1-15, 1991, JOHN WILEY AND SONS
"Rodd's Chemistry of Carbon Compounds", vol. 1-5, 1989, ELSEVIER SCIENCE PUBLISHERS
"Organic Reactions", vol. 1-40, 1991, JOHN WILEY AND SONS
"March's Advanced Organic Chemistry", JOHN WILEY AND SONS
"Larock's Comprehensive Organic Transformations", 1989, VCH PUBLISHERS INC.
J. F. W. MCOMIE: "Protective Groups in Organic Chemistry", 1973, PLENUM PRESS
T. W. GREENE; P. G. M. WUTS: "Protective Groups in Organic Synthesis", 1999, WILEY
"The Peptides", vol. 3, 1981, ACADEMIC PRESS
HOUBEN WEYL: "Methoden der organischen Chemie", vol. 15, 1974, GEORG THIEME VERLAG
H.-D. JAKUBKE; H. JESCHKEIT: "Aminosaeuren, Peptide, Proteine", 1982, VERLAG CHEMIE
JOCHEN LEHMANN: "Chemie der Kohlenhydrate: Monosaccharide und Derivate", 1974, GEORG THIEME VERLAG
"Remington's Pharmaceutical Sciences", 1991, MACK PUB. CO.
T. HIGUCHI; V. STELLA: "Pro-drugs as Novel Delivery Systems", vol. 14, A.C.S. SYMPOSIUM SERIES
BERTOLINI, G. ET AL., J. MED. CHEM., vol. 40, 1997, pages 2011 - 2016
SHAN, D. ET AL., J. PHARM. SCI., vol. 86, no. 7, pages 765 - 767
BAGSHAWE K., DRUG DEV. RES., vol. 34, 1995, pages 220 - 230
BODOR, N., ADVANCES IN DRUG RES., vol. 13, 1984, pages 224 - 331
BUNDGAARD, H.: "Design of Prodrugs", 1985, ELSEVIER PRESS
LARSEN, I. K. ET AL.: "Design and Application of Prodrugs, Drug Design and Development", 1991, HARWOOD ACADEMIC PUBLISHERS
"Methods in Cell Biology", vol. XIV, 1976, ACADEMIC PRESS, pages: 33
"Remington's Pharmaceutical Sciences", 1990, MACK PUBLISHING COMPANY
See also references of EP 2599771A4
Attorney, Agent or Firm:
TANAKA, Mitsuo et al. (JP)
Mitsuo Tanaka (JP)
Mitsuo Tanaka (JP)
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