Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Reexamination Certificate
2007-09-25
2007-09-25
Campell, Bruce R. (Department: 1648)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
Reexamination Certificate
active
10462211
ABSTRACT:
The invention is directed to compounds of formula (I)wherein X is O or NH; R′ is a hydrocarbon chain; R3and R4are hydrogen, OH or a monosaccharide; R5is hydrogen or a monosaccharide; Q′ is optionally present and may be a C1-10hydrocarbon; X′ is optionally present and may be O, S or NR8; and Q3may be a hydrocarbon or hydrogen. The invention is also directed to the use of the compounds for treating cancer, infectious diseases and autoimmune diseases. The invention is also directed to syntheses of the compounds of formula (I).
REFERENCES:
patent: 5780441 (1998-07-01), Higa et al.
patent: 5849716 (1998-12-01), Akimoto et al.
patent: 5936076 (1999-08-01), Higa et al.
patent: 6531453 (2003-03-01), Taniguchi et al.
patent: 6635622 (2003-10-01), Tomiyama et al.
patent: 2002/0032158 (2002-03-01), Tomiyama et al.
Marcaurelle et al. New Directions in the Synthesis of Glycopeptide Mimetics. Chem. Eur. J., 1999, vol. 5, No. 5, pp. 1384-1390.
Singh et al. Cutting Edge: Activation of NK T Cells by CD1d and alpha-Galactosylceramide Directes Conventnional T Cells to the Acquisition of a Th2 Phenotype. The Journal of Immunology, 1999, vol. 163, No. 5, pp. 2373-2377.
Smyth et al. Sequential production of interferon-gamma by NK1.1+T cells and natural killer cells is essential for the antimetastatic effect of alpha-galactosylceramide. Blood, Feb. 15, 2002, vol. 99, No. 4, 1259-1266.
Bertozzi et al. Synthesis of C-Glycosides; Stable Mimics of O-Glycosidic Linkages. In Modern methods in Carbohydrate synthesis (Eds. S. H. Khan, R. A. O'Neill), 1996, Harwood Academic Publishers, London, UK, 316-351.
Bertozzi et al. Carbon-linked galactosphingolipid analogs bind specifically to HIV-1 gp120. J. Am., Chem. Soc. 1992, vol. 114, 10639-10641.
Michael T. Wilson et al., “Immunotherapy with ligands of natural killer T cells,”Trends in Molecular Medicine8, 5: 225-231 (May 2002).
Gloria Gonzalez-Aseguinolaza et al., “Natural Killer T Cell Ligand α-Galactosylceramide Enhances Protective Immunity Induced by Malaria Vaccines,”J. Exp. Med.195, 5: 617-624 (Mar. 4, 2002).
Katsuichi Miyamoto et al., “A synthetic glycolipid prevents autoimmune encephalomyelitis by inducing TH2 bias of natural killer T cells,”Nature413: 531-534 (Oct. 2001).
Akihiro Shimosaka et al., “KRN7000: A Novel Dendritic Cell Activator.” Abstract Book, Instituto Superiore di Sanità, Rome (Oct. 15-17, 2001).
Seokmann Hong et al., “The natural killer T-cell ligand α-galactosylceramide prevents autoimmune diabetes in non-obese diabetic mice,”Nature Medicine7, 9: 1052-1056 (Sep. 2001).
Shayan Sharif, “Activation of natural killer T cells by α-galactosylceramide treatment prevents the onset and recurrance of autoimmune Type 1 diabetes,”Nature Medicine7: 1057-1062 (Sep. 2001).
Kazuyoshi Kawakami et al., “Activation of Vα14” Natural Killer T Cells by α-Galactosylceramide Results in Development of Th1 Response and Local Host Resistance in Mice Infected withCryptococcus neoformans, Infection and Immunity69: 213-220 (Jan. 2001).
Kazuhiro Kakimi et al., “Natural Killer T Cell Activation Inhibits Hepatitis B Virus Replication In Vivo,”J. Exp. Med.192, 7: 921-930 (Oct. 2, 2000).
Gloria Gonzalez-Asequinolaza et al., “α-Galactosylceramide-activated Vα14 natural killer T cells mediate protection against murine malaria,”PNAS97, 15: 8461-8466 (Jul. 18, 2000).
Takashi Nishimura et al., “The interface between innate and acquired immunity: glycolipid antigen presentation by CD1d-expressing dendritic cells to NKT cells induces the differentiation of antigen-specific cytotoxic T lymphocytes,”International Immunology12, 7: 987-994 (2000).
Tetsu Kawano et al., “Antitumor Cytotoxicity Mediated by Ligand-activated Human Vα24 NK5 Cells,”Cancer Research59: 5102-5105 (Oct. 15, 1999).
Junqing Cui, “Inhibition of T Helper Cell Type 2 Cell Differentiation and Immunoglobulin E Response by Ligand-activated Vα14 Natural Killer T Cells,”J. Exp. Med.190, 6: 783-792 (Sep. 20, 1999).
Nagendra Singh et al., “Cutting Edge: Activation of NK T Cells by CD1d and α-Galactosylceramide Directs Conventional T Cells to the Acquisition of a Th2 Phenotype,”The Journal of Immunology: 2373-2377 (1999).
Nakagawa et al. “Treatment of Hepatic Metasis of the Colon 26 Adenocarcinoma with an α-Galactosylceramide, KRN7000,”Cancer Research58: 1202-1207 (Mar. 15, 1998).
Eiichi Kobayashi et al., “KRN7000, A Novel Immunomodulator, and Its Antitumor Activities,”Oncology Research7: 529-534 (1995).
Akira Hasegawa et al., “Synthesis of cerebroside, lactosyl ceramide, and ganglioside GM, analogs containing β-thioglycosidically linked ceramide,”Carbohydrate Research214: 43-53 (1991).
Soichiro Ishihara et al., “α-Glycosylceramides Enhance the Antitumor Cytotoxicity of Hepatic Lymphocytes Obtained from Cancer Patients by Activating CD3−CD56+NK Cells In Vitro,”The Journal of Immunology, 165:1659-1664 (2000).
Hidemitsu Kitamura et al., “The Natural Killer T (NKT) Cell Ligand α-Galactosylceramide Demonstrates Its Immunopotentiating Effect by Inducing Interleukin (IL)-12 Production by Dendritic Cells and IL-12 Receptor Expression on NKT Cells,”J. Exp. Med.189(7):1121-1127 (Apr. 5, 1999).
Tsuji, M., “Glycolipids and phospholipids as natural CD1d-binding NKT cell ligands”, Cell. Mol. Life Sci., 2006, 63:1889-1898, Birkhäuser Verlag, Basel, 2006.
“Glycolipid α-C-galactosylceramide is a distinct inducer of dendritic cell function during innate and adaptive immune responses of mice,” Fujii et al., Proc. Natl. Academy of Sciences of the USA, 2006, 103(30): 11252-11257 (2006 by the National Academy of Sciences of the USA).
“Stereoselective Synthesis and Immunogenic Activity of the C-Analogue of Sulfatide,” Modica et al., Organic Letters, 2006, 8(15): 3255-3258 (American Chemical Society 2006).
Definitions of TH1 Cells and TH2 Cells, Illustrated Dictionary of Immunology, p. 292, Cruse et al. eds. CRC Press, Inc. 1995.
“Modulation of Cd1d-restricted NKT cell responses by using N-acyl variants of α-galactosylceramides,” Yu et al., Proc. Natl. Academy of Sciences of the USA, 2005, 102(9), 3383-3388 (2005 by the National Academy of Sciences of the USA).
“Two types of Murine Helper T Cell Clone, I. Definitions according to profiles of lymphokine activities and secreted proteins,” Mosmann, et al., The Journal of Immunology, 1996 136(7), 2348-2357 (1986) by the American Association of Immunologists).
“A synthetic glycolipid prevents autoimmune encephalomeyelitis by inducing TH2 bias of natural killer T cells,” Miyamoto et al., Letters to Nature 2001, vol. 413, 2001 531-534 (2001 MacMillan Magazines Ltd.).
“Helper T Cells and lymphocyte Activation,” Molecular Biology of the Cell, 4th ed., Ch. V(24), Alberts et al., eds., New York and London: Garland Science; 2002 available on-line at.
Chen Guangwu
Franck Richard
Tsuji Moriya
Yang Guangli
Campell Bruce R.
Darby & Darby
Le Emily M.
The Research Foundation of the City University of New York
LandOfFree
Synthetic C-glycolipid and its use for treating cancer,... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Synthetic C-glycolipid and its use for treating cancer,..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Synthetic C-glycolipid and its use for treating cancer,... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3721381