Title:
NOVEL ANTI-INFLAMMATORY METABOLITE DERIVED FROM OMEGA-3-TYPE FATTY ACID
Document Type and Number:
WIPO Patent Application WO/2012/023254
Kind Code:
A1
Abstract:
The purpose is to provide a compound which can overcomes the disadvantages of conventional steroid drugs and NSAID.
It is found that specific epoxy monohydroxy forms of eicosapentaenoic acid, docosahexaenoic acid and docosapentaenoic acid which are independently represented by formulae [chemical formula 1], [chemical formula 5] and the like have an inhibitory activity on neutrophils. This compound can inhibit the invasion of neutrophils into tissues and the activation of neutrophils which are observed in acute inflammations.
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Inventors:
ARITA MAKOTO (JP)
ARAI HIROYUKI (JP)
ISOBE YOSUKE (JP)
KUBOTA TADAFUMI (JP)
ARAI HIROYUKI (JP)
ISOBE YOSUKE (JP)
KUBOTA TADAFUMI (JP)
Application Number:
PCT/JP2011/004449
Publication Date:
February 23, 2012
Filing Date:
August 04, 2011
Export Citation:
Assignee:
UNIV TOKYO (JP)
ARITA MAKOTO (JP)
ARAI HIROYUKI (JP)
ISOBE YOSUKE (JP)
KUBOTA TADAFUMI (JP)
ARITA MAKOTO (JP)
ARAI HIROYUKI (JP)
ISOBE YOSUKE (JP)
KUBOTA TADAFUMI (JP)
International Classes:
C07D303/38; A61K31/336; A61P1/04; A61P1/16; A61P5/24; A61P9/10; A61P11/00; A61P11/06; A61P13/12; A61P15/00; A61P15/06; A61P15/08; A61P25/00; A61P29/00; A61P35/00; C12P7/64; G01N30/34; G01N30/88
Domestic Patent References:
| WO2001060778A2 | 2001-08-23 | |||
| WO2006055965A2 | 2006-05-26 | |||
| WO1996037476A1 | 1996-11-28 |
Foreign References:
| JP2010052509W | 2010-02-19 | |||
| JP2006055965A | 2006-03-02 | |||
| US5569769A | 1996-10-29 | |||
| US5242940A | 1993-09-07 |
Other References:
FER M. ET AL.: "Metabolism of eicosapentaenoic and docosahexaenoic acids by recombinant human cytochromes P450", ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, vol. 471, no. 2, 2008, pages 116 - 125, XP022503638
ARITA M. ET AL.: "The contributions of aspirin and microbial oxygenase to the biosynthesis of anti-inflammatory resolvins: Novel oxygenase products from o-3 polyunsaturated fatty acids", BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, vol. 338, no. 1, 2005, pages 149 - 157, XP027218274
KATO T. ET AL.: "Preparation of the enantiomers of 19-epoxy docosahexaenoic acids and their 4-hydroxy derivatives", TETRAHEDRON: ASYMMETRY, vol. 11, no. 4, 2000, pages 851 - 860, XP004192897
FER M. ET AL.: "Determination of polyunsatured (sic) fatty acid monoepoxides by high performance liquid chromatography-mass spectrometry", JOURNAL OF CHROMATOGRAPHY A, vol. 1115, no. 1-2, 2006, pages 1 - 7, XP024967407
SINGH G., AM. J. MED., vol. 105, 1998, pages 31S - 385
FUNK C.D.; FITZGERALD G.A., J. CARDIOVASC PHARMACOL, vol. 50, 2007, pages 470 - 479
SERHAN C.N. ET AL., PROSTAGLANDINS AND OTHER LIPID MEDIATORS, vol. 73, 2004, pages 155 - 172
E. TJONAHEN ET AL., CHEMISTRY, vol. 13, November 2006 (2006-11-01), pages 1193 - 1202
TETRAHEDRON ASYMMETRY, vol. 11, no. 4, 2000, pages 851 - 860
"Design of Prodrugs", 1985, ELSEVIER
"Physical and Biomedical Sciences", vol. 1, 1987, article "Labeled Compounds (Part A"
GREENE; WUTS: "rotective Groups in Organic Chemistry", 1999, JOHN WILEY & SONS
HARRISON ET AL.: "Compendium of Synthetic Organic Methods", vol. 1-8, 1971, JOHN WILEY & SONS
GREEN; WUTS: "Protecting Groups in Organic Synthesis", 1991, JOHN WILEY AND SONS
WUTS: "Protecting in Organic Synthesis", vol. 5, 7, 1991, JOHN WILEY AND SONS
CAPDEVILA JH; WEI S; HELVIG C; FALCK JR; BELOSLUDTSEV Y; TRUAN G; GRAHAM-LORENCE SE; PETERSON JA, J BIOL CHEM., vol. 271, no. 37, 13 September 1996 (1996-09-13)
REDDANNA P; WHELAN J; MADDIPATI KR; REDDY CC, METHODS ENZYMOL., vol. 187, 1990, pages 268 - 77
JISAKA M. ET AL., J BIOL CHEM, vol. 272, 1997, pages 24410 - 24416
YOSHIMOTO T. ET AL., PROSTAGLANDINS AND OTHER LIPID MEDIATORS, vol. 68-69, 2002, pages 245 - 262
H. ET AL., PROSTAGLANDINS AND OTHER LIPID MEDIATORS, vol. 68, no. 69, 2002, pages 263 - 290
OLIW E.H., PROSTAGLANDINS AND OTHER LIPID MEDIATORS, vol. 68, no. 69, 2002, pages 313 - 324
BROWN, CONTEMPORARY ORGANIC, 1997, pages 216
POPPINGER, ADV. DRUG RES., vol. 30, 1997, pages 111
BALKENHOHL ET AL., ANGEW. CHEM. INT. ED. ENGL., vol. 35, 1996, pages 2288
HERMKENS ET AL., TETRAHEDRON, vol. 52, 1996, pages 4527
HERMKENS ET AL.: "53", TETRAHEDRON, 1997, pages 5643
THOMPSON ET AL., CHEM. REV., vol. 96, 1996, pages 555
NEFZI ET AL., CHEM. REV., vol. 2, 1997, pages 449 - 472
GREENE; WUTS: "Protecting Groups in Organic Synthesis", 1991, JOHN WILEY AND SONS
BERGE S. M. ET AL.: "Pharmaceutical Salt", J. PHARM. SCI, 1977
TILG, H.; MOSCHEN, A.R., NAT. REV. IMMUNOL., vol. 6, 2006, pages 772 - 783
SAMBROOK J. ET AL.: "Molecular Cloning: A Laboratory Manual", 1989, COLD SPRING HARBOR
AUSUBEL, F.M.: "Current Protocols in Molecular Biology", 1987, GREENE PUB. ASSOCIATES AND WILEY-INTERSCIENCE
AUSUBEL, F.M.: "Short Protocols in Molecular Biology: A Compendium of Methods from Current Protocols in Molecular Biology", 1989, GREENE PUB. ASSOCIATES AND WILEY-INTERSCIENCE
INNIS M.A.: "PCR Protocols: A Guide to Methods and Applications", 1990, ACADEMIC PRESS
F.M.: "Short Protocols in Molecular Biology: A Compendium of Methods from Current Protocols in Molecular Biology", 1992, GREENE PUB. ASSOCIATES
F.M.: "Short Protocols in Molecular Biology: A Compendium of Methods from Current Protocols in Molecular Biology", 1995, GREENE PUB. ASSOCIATES
INNIS, M.A. ET AL.: "PCR Strategies", 1995, ACADEMIC PRESS
F.M., SHORT PROTOCOLS IN MOLECULAR BIOLOGY: A COMPENDIUM OF METHODS FORM CURRENT PROTOCOLS IN MOLECULAR BIOLOGY, 1999
SNINSKY, J.J. ET AL.: "PCR Applications: Protocols for Functional Genomics", 1999, ACADEMIC PRESS
"Experimental Medicine", 1997, YODOSHA, article "Gene Introduction & Expression Analysis Experimental Methods"
GAIT, M.J.: "Oligonucleotide Synthesis: A Practical Approach", 1985, IRL PRESS
GAIT, M.J.: "Oligonucleotide Synthesis: A Practical Approach", 1990, IRL PRESS
F.: "Analogues: A Practical Approach", 1991, IRL PRESS
ADAMS, R.L. ET AL.: "The Biochemistry of the Nucleic Acids", 1992, CHAPMAN & HALL
SHABAROVA, Z. ET AL., ADVANCED ORGANIC CHEMISTRY OF NUCLEIC ACIDS, 1994
BLACKBURN, G.M. ET AL.: "Nucleic Acids in Chemistry and Biology", 1996, OXFORD UNIVERSITY PRESS
HERMANSON, G.T.: "Bioconjugate Techniques", 1996, ACADEMIC PRESS
SERHAN C.N ET AL., BIOCHEMISTRY, vol. 34, 1995, pages 14609 - 14615
See also references of EP 2607358A4
ARITA M. ET AL.: "The contributions of aspirin and microbial oxygenase to the biosynthesis of anti-inflammatory resolvins: Novel oxygenase products from o-3 polyunsaturated fatty acids", BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, vol. 338, no. 1, 2005, pages 149 - 157, XP027218274
KATO T. ET AL.: "Preparation of the enantiomers of 19-epoxy docosahexaenoic acids and their 4-hydroxy derivatives", TETRAHEDRON: ASYMMETRY, vol. 11, no. 4, 2000, pages 851 - 860, XP004192897
FER M. ET AL.: "Determination of polyunsatured (sic) fatty acid monoepoxides by high performance liquid chromatography-mass spectrometry", JOURNAL OF CHROMATOGRAPHY A, vol. 1115, no. 1-2, 2006, pages 1 - 7, XP024967407
SINGH G., AM. J. MED., vol. 105, 1998, pages 31S - 385
FUNK C.D.; FITZGERALD G.A., J. CARDIOVASC PHARMACOL, vol. 50, 2007, pages 470 - 479
SERHAN C.N. ET AL., PROSTAGLANDINS AND OTHER LIPID MEDIATORS, vol. 73, 2004, pages 155 - 172
E. TJONAHEN ET AL., CHEMISTRY, vol. 13, November 2006 (2006-11-01), pages 1193 - 1202
TETRAHEDRON ASYMMETRY, vol. 11, no. 4, 2000, pages 851 - 860
"Design of Prodrugs", 1985, ELSEVIER
"Physical and Biomedical Sciences", vol. 1, 1987, article "Labeled Compounds (Part A"
GREENE; WUTS: "rotective Groups in Organic Chemistry", 1999, JOHN WILEY & SONS
HARRISON ET AL.: "Compendium of Synthetic Organic Methods", vol. 1-8, 1971, JOHN WILEY & SONS
GREEN; WUTS: "Protecting Groups in Organic Synthesis", 1991, JOHN WILEY AND SONS
WUTS: "Protecting in Organic Synthesis", vol. 5, 7, 1991, JOHN WILEY AND SONS
CAPDEVILA JH; WEI S; HELVIG C; FALCK JR; BELOSLUDTSEV Y; TRUAN G; GRAHAM-LORENCE SE; PETERSON JA, J BIOL CHEM., vol. 271, no. 37, 13 September 1996 (1996-09-13)
REDDANNA P; WHELAN J; MADDIPATI KR; REDDY CC, METHODS ENZYMOL., vol. 187, 1990, pages 268 - 77
JISAKA M. ET AL., J BIOL CHEM, vol. 272, 1997, pages 24410 - 24416
YOSHIMOTO T. ET AL., PROSTAGLANDINS AND OTHER LIPID MEDIATORS, vol. 68-69, 2002, pages 245 - 262
H. ET AL., PROSTAGLANDINS AND OTHER LIPID MEDIATORS, vol. 68, no. 69, 2002, pages 263 - 290
OLIW E.H., PROSTAGLANDINS AND OTHER LIPID MEDIATORS, vol. 68, no. 69, 2002, pages 313 - 324
BROWN, CONTEMPORARY ORGANIC, 1997, pages 216
POPPINGER, ADV. DRUG RES., vol. 30, 1997, pages 111
BALKENHOHL ET AL., ANGEW. CHEM. INT. ED. ENGL., vol. 35, 1996, pages 2288
HERMKENS ET AL., TETRAHEDRON, vol. 52, 1996, pages 4527
HERMKENS ET AL.: "53", TETRAHEDRON, 1997, pages 5643
THOMPSON ET AL., CHEM. REV., vol. 96, 1996, pages 555
NEFZI ET AL., CHEM. REV., vol. 2, 1997, pages 449 - 472
GREENE; WUTS: "Protecting Groups in Organic Synthesis", 1991, JOHN WILEY AND SONS
BERGE S. M. ET AL.: "Pharmaceutical Salt", J. PHARM. SCI, 1977
TILG, H.; MOSCHEN, A.R., NAT. REV. IMMUNOL., vol. 6, 2006, pages 772 - 783
SAMBROOK J. ET AL.: "Molecular Cloning: A Laboratory Manual", 1989, COLD SPRING HARBOR
AUSUBEL, F.M.: "Current Protocols in Molecular Biology", 1987, GREENE PUB. ASSOCIATES AND WILEY-INTERSCIENCE
AUSUBEL, F.M.: "Short Protocols in Molecular Biology: A Compendium of Methods from Current Protocols in Molecular Biology", 1989, GREENE PUB. ASSOCIATES AND WILEY-INTERSCIENCE
INNIS M.A.: "PCR Protocols: A Guide to Methods and Applications", 1990, ACADEMIC PRESS
F.M.: "Short Protocols in Molecular Biology: A Compendium of Methods from Current Protocols in Molecular Biology", 1992, GREENE PUB. ASSOCIATES
F.M.: "Short Protocols in Molecular Biology: A Compendium of Methods from Current Protocols in Molecular Biology", 1995, GREENE PUB. ASSOCIATES
INNIS, M.A. ET AL.: "PCR Strategies", 1995, ACADEMIC PRESS
F.M., SHORT PROTOCOLS IN MOLECULAR BIOLOGY: A COMPENDIUM OF METHODS FORM CURRENT PROTOCOLS IN MOLECULAR BIOLOGY, 1999
SNINSKY, J.J. ET AL.: "PCR Applications: Protocols for Functional Genomics", 1999, ACADEMIC PRESS
"Experimental Medicine", 1997, YODOSHA, article "Gene Introduction & Expression Analysis Experimental Methods"
GAIT, M.J.: "Oligonucleotide Synthesis: A Practical Approach", 1985, IRL PRESS
GAIT, M.J.: "Oligonucleotide Synthesis: A Practical Approach", 1990, IRL PRESS
F.: "Analogues: A Practical Approach", 1991, IRL PRESS
ADAMS, R.L. ET AL.: "The Biochemistry of the Nucleic Acids", 1992, CHAPMAN & HALL
SHABAROVA, Z. ET AL., ADVANCED ORGANIC CHEMISTRY OF NUCLEIC ACIDS, 1994
BLACKBURN, G.M. ET AL.: "Nucleic Acids in Chemistry and Biology", 1996, OXFORD UNIVERSITY PRESS
HERMANSON, G.T.: "Bioconjugate Techniques", 1996, ACADEMIC PRESS
SERHAN C.N ET AL., BIOCHEMISTRY, vol. 34, 1995, pages 14609 - 14615
See also references of EP 2607358A4
Attorney, Agent or Firm:
YAMAMOTO, Shusaku et al. (JP)
Shusaku Yamamoto (JP)
Shusaku Yamamoto (JP)
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