Azasugar compound

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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C548S541000, C514S424000

Reexamination Certificate

active

10726550

ABSTRACT:
The present invention provides a compound represented by the formula (I) or a salt thereof:wherein R1represents a hydrogen atom, a C1-10alkyl group optionally having a substituent, or a protecting group of N; R2represents a C1-10alkyl group optionally having a substituent or a C2-10alkenyl group optionally having a substituent; R3and R4independently represent a hydrogen atom or a protecting group of hydroxyl group; X represents —N(R5)R6or a residue of amino acid or of an amino group of a peptide wherein R5and R6independently represent a hydrogen atom, a C1-10alkyl group optionally having a substituent, or a C3-12cycloalkyl group optionally having a substituent; and Y represents a hydrogen atom, —CH2NH2, —CONH2, or —COOH. The compound of the present invention is useful as a specific inhibitor of sugar chain related enzymes such as glycosyltransferase and glycosidase, and is useful as, for example, a medicine for treating or preventing diseases associated with sugar chain related enzymes.

REFERENCES:
patent: 5348954 (1994-09-01), Almen et al.
patent: 5451679 (1995-09-01), Barta et al.
patent: 5663342 (1997-09-01), Barta et al.
patent: 4-502619 (1992-05-01), None
patent: 95/24392 (1995-09-01), None
patent: 00/68194 (2000-11-01), None
patent: 03/008379 (2003-01-01), None
Wrodnigg et al (1997): STN International HCAPLUS database, Columbus (OH), accession No. 1997: 530913.
Barta et al (1995): STN International HCAPLUS database, Columbus (OH), accession No. 1995: 994843.
T. M. Wordnigg et al., “Novel, Lipophilic Derivatives of 2,5-dideoxy-2,5-imino-D-mannitol (DMDP) are Powerful; β-Glucosidase Inhibitors,” Bioorganic and Medicinal Chemistry Letters, vol. 11, No. 8, pp. 1063-1064, 2001.
A. Hermetter et al., “Powerful Probes for Glycosidases: Novel, Fluorescently Tagged Glycosidase Inhibitors,” Bioorganic and Medicinal Chemistry Letters, vol. 11, No. 10, pp 1339-1342, 2001.
T. M. Wordnigg et al., “Biologically Active 1-aminodeoxy and 1-o-alkyl Derivatives of the Powerful D-glucosidase Inhibitor 2,5-dideoxy-2,5-imino-D-mannitol,” Journal of Carbohydrate Chemistry, vol. 19, No. 8, pp. 975-990, 2000.
I. McCort et al., “Synthesis and Evaluation as Glycosidase Inhibitors of 2,5-imino-D-glucitol and 1,5-Imino-D-mannitol Related Derivatives,” Bioorganic and Medicinal Chemistry, vol. 8, No. 1, pp. 135-143, 2000.
C. H. Wong et al, “Synthesis and Evaluation of Homoazasugars as Glycosidase Inhibitors,” Journal of Organic Chemistry, vol. 60, No. 6, 1492-1501, 1995.
R. C. Reynolds et al., “Ethambutol-sugar Hybrids as Potential Inhibitors of Mycobacterial Cell-wall Biosynthesis,” Carbohydrate Research, vol. 317, pp. 164-179, 1999.
I. McCort et al., “Synthesis of Ester- and Amide-Linked Pseudo-azadisaccharides via Coupling of D-glucose with 6-amino-6-deoxy-2,5-imino-D-glucitol,” Tetrahedron Letters, vol. 39, No. 25, pp. 4463-3366, 1998.
K. D. Janda et al., “Chemical Selection for catalysis in Combinatorial Antibody Libraries,” Science, vol. 275, No. 5302, pp. 945-948, 1997.
S. H. Kang et al., “Intramolecular Cyclization of C2Symmetric andmeso-Iodo Amino Alcohols: A Synthetic Approach to Azasugars,” Tetrahedron Letters, vol. 38, No. 4, pp. 607-610, 1997.
I. McCort et al., “Practical Route to D-Manno and D-Gluco Azasugars from C2Symmetric Bis-aziridines,” Tetrahedron Letters, vol. 37, No. 43, pp. 7717-7720, 1996.
L. Campanini et al., “One Step Synthesis of Sulfur and Nitrogen Linked Aza-disaccharide Precursors from D-Mannitol Derived Bis-aziridines,” Tetrahedron Letters, vol. 37, No. 29, pp. 5095-5098, 1996.
L. Campanini et al., “Concise Synthesis of New Homoazasugars. Fully Substituted, Functionally Diverse Pyrrolidines,” Tetrahedron Letters, vol. 36, No. 44, pp. 8015-8018, 1995.
J. Fitremann et al., “Regioselective Cyanide Ring Opening of C2Symmetric Bis-Aziridines by Cyanide,” Synlett, vol. 3, pp. 235-237, 1995.
M. H. M. G. Schumacher-Wandersleb et al., “Preparation of the N-Acetylglucosaminidase Inhibitor 1-Acetamido-1,2,5-trideoxy-2,5-imino-D-glucitol from Methyl α-D-Mannopyranoside,” Liebigs Ann. Chem., vol. 6, pp. 555-561, 1994.
J. Fitremann et al., “2,5-Disubstituted Pyrrolidines from D-Mannitol-Derived Bis-Aziridines,” Tetrahedron Letters, vol. 36, No. 8, pp. 1201-1204, 1994.
R. Kornfeld et all., Ann. Rev. Biochem., vol. 54, pp. 631-634, 1985.
I. Brockhausen, Biochimica et Biophysica Acta, vol. 1473, pp. 67-95, 1999.
T.D. Butters et al., Chem. Rev., vol. 100, pp. 4683-4696, 2000.
M. Sinnott et al., Chem. Rev., vol. 90, pp. 1171-1202, 1990.
C.S. Rye et al., Curr. Opin. Chem. Biol., vol. 4, pp. 573-580, 2000.
U.M. Unligil et al., Curr. Opin. Struct. Biol., vol. 10, pp. 510-517, 2000.
B. Winchester et al., Biochem. J., vol. 290, pp. 743-749, 1993.
G.W.J. Fleet et al., Tetrahedron Lett., vol. 26, pp. 3127-3130, 1985.
K.K.-C. Liu et al., J. Org. Chem., vol. 56, pp. 6280-6289, 1991.
A. Kato et al., Carbohydr. Res., vol. 316, pp. 95-103, 1999.
M. Takebayashi et al., J. Org. Chem., vol. 64, pp. 5280-5291, 1999.
C. Saotome et al., Bioorg. Med. Chem., vol. 8, pp. 2249-2261, 2000.
T. Kajimoto et al., J. Am. Chem. Soc., vol. 113, pp. 6187-6196, 1991.
Y. Ichikawa et al., J. Am. Chem. Soc., vol. 120, pp. 3007-3018, 1998.
G. Legler et al., Carbohydr. Res., vol. 155, pp. 119-129, 1986.
C.H. Wong et al., Angew. Chem. Int. Ed. Engl., vol. 34, pp. 412-432, 1995.
C.H. Wong et al., Angew. Chem. Int. Ed. Engl., Vol. 34, 521-546, 1995.
A.B. Hughes et al., Nat. Prod. Rep., pp. 135-162, 1994.
X. Qian et al., Glycotransferase Inhibitors, in Carbohydrates in Chemistry and Biology, B. Ernst et al. ed., vol. 3, pp. 293-312.
M. Takayanagi et al., J. Org. Chem., Vol. 65, pp. 3811-3815, 2000.
U.J. Nilsson et al. Bioorg. Med. Chem., vol. 6, pp. 1563-1575, 1998.
R. Wischnat et al., Bioorg. Med. Chem. Lett., vol. 8, pp. 3353-3358, 1998.
A. Lohse et al., Bioorg. Med. Chem., vol. 7, pp. 1965-1971, 1999.
A. Lohse et al., Tetrahedron Lett., vol. 40, pp. 3033-3036, 1999.
C. Malet, Carbohydrate Research, vol. 303, pp. 51-65, 1997.

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