Title:
NEURAMINIDASE INHIBITOR
Document Type and Number:
WIPO Patent Application WO/2006/064914
Kind Code:
A1
Abstract:
This invention provides a novel compound having irreversible inhibitory activity against neuraminidase, and a therapeutic agent and a detecting agent for neuraminidase-related diseases. Specifically, there are provided a compound of formula (I) and its salt, production process and use: Chemical formula (I) wherein A1 represents an optionally substituted aryl group or an optionally substituted heteroaryl group; A2 represents -CX2R6 or -CHXR6 wherein X represents -F, -Cl, -Br, or -I; R1 represents a hydrogen atom or an optionally substituted alkyl group; R2, R3, R4, and R5 each independently represent -OC(=O)R6, -OR6, -N(R6)2, -N3, -NHC(=NH)NHR6, -NHCOR6, -OSO3R6, -OPO3(R6)2, F, Cl, Br, or I; and R6’s each independently represent a hydrogen atom, an optionally substituted alkyl group, an optionally substituted aryl group, or an optionally substituted heteroaryl group.
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Inventors:
NISHIMURA SHINICHIRO (JP)
HINOU HIROSHI
KONDO HIROSATO (JP)
FUJIWARA KAZUHIKO (JP)
HINOU HIROSHI
KONDO HIROSATO (JP)
FUJIWARA KAZUHIKO (JP)
Application Number:
PCT/JP2005/023162
Publication Date:
June 22, 2006
Filing Date:
December 16, 2005
Export Citation:
Assignee:
NAT INST OF ADVANCED IND SCIEN (JP)
Y NAT UNIVERSITY CORP HOKKAIDO (JP)
SHIONOGI & CO (JP)
SUMITOMO BAKELITE CO (JP)
NISHIMURA SHINICHIRO (JP)
HINOU HIROSHI
KONDO HIROSATO (JP)
FUJIWARA KAZUHIKO (JP)
Y NAT UNIVERSITY CORP HOKKAIDO (JP)
SHIONOGI & CO (JP)
SUMITOMO BAKELITE CO (JP)
NISHIMURA SHINICHIRO (JP)
HINOU HIROSHI
KONDO HIROSATO (JP)
FUJIWARA KAZUHIKO (JP)
International Classes:
C07H15/203; A61K31/7034; A61K31/7036; A61K31/7048; A61P1/04; A61P11/00; A61P31/04; A61P31/12; A61P31/14; A61P31/16; A61P33/02; A61P43/00; C07H15/26; C07H17/075; C12N9/99; C12Q1/04; C12Q1/34
Foreign References:
| JPH05505099A | 1993-08-05 |
Other References:
BARRERE B. ET AL.: "A novel synthetic reversible inhibitor of sialidase efficiently blocks secondary but not primary influenza virus infection of MDCK cells in culture", ARCHIVES OF VIROLOGY, vol. 142, no. 7, 1997, pages 1365 - 1380, XP002998797
DRIGUEZ P.A. ET AL.: "Synthesis of sodium salt of ortho-(difluoromethyl)phenyl-alpha-ketoside of N-acetylneuraminic acid: a mechanism-based inhibitor of Closdtridium perfringens neuraminidase", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 2, no. 11, 1992, pages 1361 - 1366, XP002998798
KUROGOCHI M. ET AL.: "Mechanism-based Fluorescent Labeling of beta-Galactosidases: An Efficient Method in Proteomics for Glycoside Hydrolases", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 279, no. 43, 22 October 2004 (2004-10-22), pages 44704 - 44712, XP002998799
ENGSTLER M. ET AL.: "Chemical synthesis of 4-trifluoromethylumbelliferyl-alpha-D-N-acetylneuraminic acid glycoside and its use for the fluorometric detection of poorly expressed natural and recombinant sialidases", ANALYTICAL BIOCHEMISTRY, vol. 250, no. 2, 1997, pages 176 - 180, XP002998800
DRIGUEZ P.A. ET AL.: "Synthesis of sodium salt of ortho-(difluoromethyl)phenyl-alpha-ketoside of N-acetylneuraminic acid: a mechanism-based inhibitor of Closdtridium perfringens neuraminidase", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 2, no. 11, 1992, pages 1361 - 1366, XP002998798
KUROGOCHI M. ET AL.: "Mechanism-based Fluorescent Labeling of beta-Galactosidases: An Efficient Method in Proteomics for Glycoside Hydrolases", JOURNAL OF BIOLOGICAL CHEMISTRY, vol. 279, no. 43, 22 October 2004 (2004-10-22), pages 44704 - 44712, XP002998799
ENGSTLER M. ET AL.: "Chemical synthesis of 4-trifluoromethylumbelliferyl-alpha-D-N-acetylneuraminic acid glycoside and its use for the fluorometric detection of poorly expressed natural and recombinant sialidases", ANALYTICAL BIOCHEMISTRY, vol. 250, no. 2, 1997, pages 176 - 180, XP002998800
Attorney, Agent or Firm:
Hiraki, Yusuke (3-20 Toranomon 4-chom, Minato-ku Tokyo, JP)
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