Glycopeptide conjugates and uses thereof

Drug – bio-affecting and body treating compositions – Antigen – epitope – or other immunospecific immunoeffector – Conjugate or complex

Reexamination Certificate

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C424S185100, C424S277100, C514S008100, C530S322000

Reexamination Certificate

active

07550146

ABSTRACT:
The present invention provides novel glycoconjugates such as glycopeptides, as well as convergent methods for the synthesis thereof. An exemplary preparative approach is exemplified by the synthesis of the mucin motif commonly found on epithelial tumor cell surfaces. The present invention further provides compositions and methods of treating cancer using the glycoconjugates of the invention.

REFERENCES:
patent: 5053489 (1991-10-01), Kufe
patent: 5212298 (1993-05-01), Rademacher et al.
patent: 5229289 (1993-07-01), Kjeldsen et al.
patent: 5280113 (1994-01-01), Rademacher et al.
patent: 5376531 (1994-12-01), Anderson et al.
patent: 5421733 (1995-06-01), Nudelman et al.
patent: 5491088 (1996-02-01), Hellstrom et al.
patent: 5625030 (1997-04-01), Williams et al.
patent: 5660834 (1997-08-01), Kjeldsen et al.
patent: 5679769 (1997-10-01), Danishefsky et al.
patent: 5683674 (1997-11-01), Taylor-Papadimitriou et al.
patent: 5747048 (1998-05-01), Kjeldsen et al.
patent: 5798090 (1998-08-01), Longnecker et al.
patent: 5807559 (1998-09-01), Jondal
patent: 5858994 (1999-01-01), Kretzschmar et al.
patent: 5871990 (1999-02-01), Clausen et al.
patent: 6013779 (2000-01-01), Wong et al.
patent: 6090789 (2000-07-01), Danishefsky et al.
patent: 6222020 (2001-04-01), Taylor-Papadimitriou et al.
patent: 6238668 (2001-05-01), Danishefsky et al.
patent: RE38046 (2003-03-01), Longenecker et al.
patent: 6660714 (2003-12-01), Danishefsky et al.
patent: 7160856 (2007-01-01), Danishefsky et al.
patent: 2002/0006900 (2002-01-01), Danishefsky et al.
patent: 2002/0038017 (2002-03-01), Danishefsky et al.
patent: 341252 (1997-11-01), None
patent: 8-319300 (1996-12-01), None
patent: WO 96/34005 (1996-10-01), None
patent: WO 96/40198 (1996-12-01), None
patent: WO 97/03995 (1997-02-01), None
patent: WO 98/30190 (1998-07-01), None
patent: WO 98/46246 (1998-10-01), None
patent: WO 99/15201 (1999-04-01), None
patent: WO 99/48515 (1999-09-01), None
patent: WO 01/14395 (2001-03-01), None
patent: WO 01/14395 (2001-03-01), None
U.S. Appl. No. 08/457,485, filed Jun. 1, 1995, Taylor-Papadimitriou et al.
Allen, et al., “A Second Generation Synthesis of the MBrl (Globo-H) Breast Tumor Antigen: New Application of the N-Pentenyl Glycoside Method for Achieving Complex Carbohydrate Protein Linkages”, Chem. Eur. J., 6(8): 1366-1375, 2000.
Allen et al., “Pursuit of optimal carbohydrate-based anticancer vaccines: preparation of a multiantigenic unimolecular glycopeptide containing the Tn, MBr1, and Lewisyantigens”,J. Am. Chem. Soc., 123:1890-1897, 2001.
Balcom, B.J. and Petersen, N.O., “Synthesis and Surfactant Behavior of an Unusual Cyclic Triester Based on acis, cis-1, 3, 5-Cyclohexanetriol Headgroup,”Langmuir, 7:2425-2427, 1991.
Bayle, et al., “O-(3-Butenyl) A Stable Blocking Group Removable by Ozonolysis”,Carbohydrate Research, 232: 375-380, 1992.
Bencomo et al., “Synthesis of glycopeptides having clusters ofO-glycosylic disaccharide chains . . . ,”Carbohydrate Research, 116, C9-C12, 1983.
Bilodeau, M.T., “Total Synthesis of a Human Breast Tumro Associated Antigen”,J. Am. Chem. Soc., 117:7840-7841, 1995.
Biswas et al., “Construction of carbohydrate-based antitumor vaccines: synthesis of glycosyl amino acids by olefin cross-metathesis”,Tetrahedron Letters, 43:6107-6110, 2002.
Blackwell et al., “New approaches to olefin cross-metathesis”,J. Am. Chem. Soc., 122:58-71, 2000.
Boehm T. et al., “Development of a Novel Silyl Ether Linker for Solid-Phase Organic Synthesis”J. Org. Chem., 61:6498-6499, 1996.
Boon, T., “Toward a Genetic Analysis of Tumor Rejection Antigens,”Adv. Can. Res., 58:177-211, 1992.
Bosse et al., “Linear synthesis of the tumor-associated carbohydrate antigens Globo-H, SSEA-3, and Gb3”,J. Org. Chem., 67:6659-6670, 2002.
Broddefalk, et al., “Preparation of a Glycopeptide Analogue of Type II Collagen—Use of Acid Labile Protective Groups for Carbohydrate Moieties in Solid Phase Synthesis of O-Linked Glycopeptides”,Tetrahedron Letters, NL, Elsevier Science, 37(17): 3011-3014, 1996.
Cabaret, et al., “Amphiphilic Liposaccharides. Synthesis and Reductive Cleavage of C-Allyl, O-Allyl, and O-Butenyl Glycosyl Derivatives”,Carbohydrate Research, 189: 341-348, 1989.
Chan et al., “Polymer-anchored Organosilyl Protecting Group in Organic Synthesis,”J. Chem. Soc., Chem. Commun., 909-911, 1985.
Collins and Ferrier Monosaccharides: Their Chemistry and Their Roles in Natural Products, Publ. by John Wiley & Sons, Ltd., p. 4, 1995.
Commissions on Nomenclature of Organic Chemistry and Physical Organic Chemistry, IUPAC,Pure and Applied Chemistry, 67, 1325 and 1334, 1995.
Danishefsky et al. “Glycals in Organic Synthesis: The Evolution of Comprehensive Strategies for the Assembly of Oligosaccharides and Glycoconjugates of Biological Consequence”Angew. Chem. Int. Ed. Engl., 35:1380-1419, 1996.
Danishefsky et al. “From the Laboratory to the Clinic: A Retrospective on Fully Synthetic Carbohydrate-Based Anticancer Vaccines”Angew. Chem. Int. Ed. Engl., 39:836-863, 2000.
Dermer, G.B., “Another Anniversary for the War on Cancer,”Bio/Technology, 12, 320, 1994.
Deshpande et al., “Strategy in Oligosaccharide Synthesis: An Application to a Concise Total Synthesis of the KH-1 (Adenocarcinoma) Antigen,”J. Am. Chem. Soc., 120, 1600-1614, 1998.
Elofsson and Kihlberg, “Synthesis of Tn and Sialyl Tn Building Blocks for Solid Phase Glycopeptide Synthesis,”Tetrahedron Letters, 36, 7499-7502, 1995.
Elofsson et al., “Preparation of Tn and Sialyl Tn Building Blocks . . . ,”Tetrahedron, 53, 369-390, 1997.
Ezzell, “Cancer “Vaccines”: An Idea Whose Time Has Come?” J. NIH Res, 7, 46-49, 1995.
Finn et al., “MUC-1 Epithelial Tumor Mucin-based Immunity and Cancer Vaccines”Immunol. Rev., 145, 61-89, 1995.
Freshney, R.I., Culture of Animal Cells, A Manual of Basic Techniques, Alan R. Liss, Inc., New York, p. 3-4, 1983.
Fung et al., “Active Specific Immunotherapy of Murine Mammary . . . ,”Cancer Research, 50, 4308-4314, 1990.
Garg et al., “Developments in the Synthesis of Glycopeptides Containing Glycosyl L-Asparagine, L-Serine, and L-Threonine”Adv. Carb. Chem. Biochem., 50, 277-310, 1994.
Gleiter et al., “Synthesis and Properties of Eight-and Ten-Membered Selenaradialenes,”Tetrahedron Letters, 35, 8779-8782, 1994.
Grice et al., “Tuning and Reactivity of Glycosides: Efficient One-pot Oligosaccharide Synthesis,”Synlett, 781-784, 1995.
Iijima, H. and Ogawa, T. “Synthesis of Mucin-type O-Glycosylated Amino Acid β-Gal-(1-3)-[α-Neu5Ac-2→6)]-GalNAc-(1→3)-Ser”Carbohydr. Res., 186, 95-106, 1989.
Kaizu et al., “Novel Fucolipids of Human Adenocarcinoma: Monoclonal Antibody Specific for Trifucosyl Ley(III3FucV3FucVI2FucnLc6) and a Possible Three-dimensional Epitope Structure,”J. Biol. Chem. 261, 11254-11258, 1986.
Kameyama et al., “Total Synthesis of Sialyl Lewis X†,”Carbohydrate Research, 209, c1-c4, 1991.
Keding et al., “Hydroxynorleucine as a glycosyl acceptor is an efficient means for introducing amino acid functionality into complex carbohydrates”,Tetrahedron Letters, 44:3413-3416, 2003.
Kim et al., “Expression of LeYand Extended LeYBlood Group-related Antigens in Human Maligmant, Premalignant, and Nonmaligmant Colonic Tissues,”Cancer Res., 46, 5985-5992, 1986.
Kim et al., “Effect of immunological adjuvant combinations on the antibody and T-cell response to vaccination with MUC1-KLH and GD3-KLH conjugates”,Vaccine, 19:530-537, 2001.
Koganty et al., “Glycopeptide- and Carbohydrate-based Synthetic Vaccines for the Immunotherapy of Cancer,”Drug Discovery Today, 5, 190-198, 1996.
Kondo et al., “In vitro action of Human and Porcine α-amylases . . . ,

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