Backbone modified oligonucleotide analogues

Details Backbone modified oligonucleotide analogues Backbone modified oligonucleotide analogues

2005-05-31

2005-05-31

Wilson, James O. (Department: 1623)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

C435S090000, C435S091200, C435S091500, C435S087000, C435S091100, C536S025340, C536S025300, C536S025310, C536S022100, C536S025600

Reexamination Certificate

active

06900301

ABSTRACT:
Therapeutic oligonucleotide analogues which have improved nuclease resistance and improved cellular uptake are provided. Replacement of the normal phosphorodiester inter-sugar linkages found in natural oligomers with four atom linking groups forms unique di- and poly-nucleosides and nucleotides useful in regulating RNA expression and in therapeutics. Methods of synthesis and use are also disclosed.

REFERENCES:
patent: 3687808 (1972-08-01), Merigan et al.
patent: 4469863 (1984-09-01), Ts'o et al.
patent: 4511713 (1985-04-01), Miller et al.
patent: 4591614 (1986-05-01), Miller et al.
patent: 5264562 (1993-11-01), Matteucci
patent: 5264564 (1993-11-01), Matteucci
patent: 5268464 (1993-12-01), Brill
patent: 5378825 (1995-01-01), Cook et al.
patent: 5580722 (1996-12-01), Foulkes et al.
patent: 5610289 (1997-03-01), Cook et al.
patent: 5658731 (1997-08-01), Sproat et al.
patent: 5665543 (1997-09-01), Foulkes et al.
patent: 5776502 (1998-07-01), Foulkes et al.
patent: 5863773 (1999-01-01), Gunawardana et al.
patent: 0 269 574 (1988-06-01), None
patent: 0287313 (1988-10-01), None
patent: 0378518 (1990-07-01), None
patent: 0 381 335 (1990-08-01), None
patent: 0417999 (1991-03-01), None
patent: WO 86/05518 (1986-09-01), None
patent: WO 89/11486 (1989-11-01), None
patent: WO 89/12060 (1989-12-01), None
patent: WO 90/08156 (1990-07-01), None
patent: WO 92/02534 (1992-02-01), None
patent: WO 92/03568 (1992-03-01), None
patent: WO 92/05186 (1992-04-01), None
patent: WO 92/20822 (1992-11-01), None
patent: WO 93/18052 (1993-09-01), None
Abdel-Magid, A.F. et al., “Reductive Amination of Aldehydes and Ketones by Using Sodium Triacetoxyborohydride”,Tetrahedron Letts., 1990, 31, 5595-5598.
Bankston, D.D. et al., “A Short Synthesis of 5′-O-Trityl-Protected threo- and erythro-3′-Cyano-3′-deoxythymidine Epimers Using Free-Radical Chemistry”,J. Heterocyclic Chem., 1992, 29, 1405-1407.
Barton, D.H.R. et al., “A ‘One-Pot’ Synthesis of Sulfenamides”,J. Org. Chem., 1991, 56, 6702-6704.
Barton, D.H.R. et al., “Stereoselectivity in Radical Reactions of 2′-Deoxynucleosides. A Synthesis of an Isotere of 3′-Azido-3′-Deoxythymidine-5′-Monophosphate (AZT-5′ Monophosphate)”,Tetrahedron Letts., 1989, 30, 4969-4972.
Baud, M.V. et al., “Improved Procedure for the Regiospecific Synthesis of 2′-Deoxyribonucleosides”,Tetrahedron Letts., 1990, 31, 4437-4440.
Beaucage, S.L. et al., “Advances in the Synthesis of Oligonucleotides by the Phosphoramidite Approach”,Tetrahedron, 1992, 48, 2223-2311.
Beaucage, S.L. et al., “The Synthesis of Modified Oligonucleotides by the Phosphoramidite Approach and their Applications”,Tetrahedron, 1993, 49, 6123-6194.
Bergstrom, D.E., “An Improved Synthesis of 3-Keto-5-O-Tritylthymidine”,Nucleosides and Nucleotides, 1989, 8(8), 1529-1523.
Bodenteich, M. et al., “Synthesis of Enantiomerically Pure Carbocyclic 3′-Azido-2′,3′-Dideoxythymidine. A Potential Anti-AIDS Drug”,Tetrahedron Letts., 1987, 28, 5311-5312.
Brown, T. et al., “Modern machine-aided methods of oligodeoxyribonucleotide synthesis”,Oligonucleotides and Analogs A Practical Approach, 1991, Chapter 1, Ekstein, F., ed., IRL Press, Oxford, 1-24.
Camarasa, M.J. et al., “Aldol Reaction of Nucleoside 5′-Carboxaldehydes with Acetone. Synthesis of 5′-C-Chain Extended Thymidine Derivatives”,Nucleosides&Nucleotides, 1990, 9, 533-546.
Cormier, J.F. et al., “Synthesis of hexanucleotide analogues containing diisopropylsilyl internucleotide linkages”,Nucl. Acids Res., 1988, 16, 4583-4594.
Cosstick, R. et al., “Synthesis and properties of dithymidine phosphate analogues containing 3′-thothymidine”,Nucl. Acids Res., 1989, 18, 829-835.
Coull, J.M. et al., “Synthesis and Characterization of a Carbamate-Linked Oligonucleoside”,Tetrahedron Letts., 1987, 28, 745-748.
Curran, D.P. et al., “Radical Addition Reactions”,Comprehensive Organic Synthesis, Trost, B.M. et al, eds., 1991, 4, Pergamon Press, Oxford, 715-831.
Debart, F. et al., “Intermolecular Radical C-C Bond Formation: Synthesis of a Novel Dinucleoside Linker for Non-anionic Antisense Oligonucleosides”,Tetrahedron Letts., 1992, 33, 2645-2648.
Egholm, M. et al., “Recognition of Guanine and Adenine inDNA by Cytosine and Thymine Containing Peptide Nucleic Acids (PNA)”,J. Am. Chem Soc., 1992, 114, 9677-9678.
Egholm, et al., “Peptide Nucleic Acids (PNA). Oligonucleotide Analogues with an Achiral Peptide Backbone”,J. Am. Chem. Soc., 1992, 114, 1895-1897.
Etzold, G. et al., “The Extension of the Sugar Chain of Thymidine: a New Route to 5′-Deoxyhexose Nucleosides”,Chem. Comm., 1968, 422.
Fiandor, J. et al., “Synthesis of 3′-Deoxy-3′(2-Propynyl) Thymidine and 3′-Cyanomethyl-3′-Deoxythymidine, Analogs of AZT”,Tetrahedron Letts., 1990, 21, 597-600.
Fikes, L.E. et al., “Preassociating α-Nucleophiles”,J. Am. Chem. Soc., 1992, 114, 1493-1495.
Fleet, G.W. et al., “Methyl 5-O-Tert-Butyldiphenylsilyl-2-Deoxy-αβ-D-Threo-Pentofuranoside as a Divergent Intermediate for the Synthesis of 3′-Substituted-2′,3′-Dideoxynuclesides: Synthesis of 3′-Azido-3′-Deoxythymidine, 3′-Deoxy-3′-Fluorothymidine and 3′-Cyano-3′-Deoxythymidine”,Tetrahedron, 1988, 44, 625-636.
Gait, M.J., ed., “Synthetic Analogues of polynucleotides. Part XII. Synthesis of Thymidine Derivatives containing an Oxyacetamido- or an Oxyformamid—linkage instead of a Phosphodiester Group”,J. C. S. Perkin I, 1974, 1684-1686.
Giannis, A. et al., “Fragmentation and Wittig Olefination of Glucosamine Derivatives—A Simple Route to Open Chain Amino Sugars and Chiral Glycerols”,Tetrahedron, 1988, 44, 7177-7180.
Goodchild, J., “Conjugtes of Oligonucleotides and Modified Oligonucleotides: A Review of their synthesis and Properties”,Bioconjugate Chem., 1990, 1, 165-187.
Goodchild, J., “Inhibition of Gene Expression by Oligonucleotides”,Oligodeoxynucleotides, 1989, CRC Press, Boca Raton, 53-78.
Greene et al., “Protection for the Carbonyl Group”,Protective Groups in Organic Synthesis, 1991, Chapter 4, John Wiley & Sons, 175-223.
Halford, M.H. et al., “Synthetic Analogues of Polynucleotides”,Nature, 1968, 217, 638-640.
Hanamoto, T. et al., “SmI2-Promoted Ketyl Radical Addition to O-Benyl Formaldoxime. A New Aminomethylation”,Tetrahedron Letts., 1991, 32, 3555-3556.
Hart, D.J. et al., “Bis(trimethylstannyl) benzopinacolate-Mediated Intermolecular Free-Radical Carbon-Carbon Bond-Forming Reactions: A New One-Carbon Homologation”,J. Am. Chem. Soc., 1988, 110, 1631-1633.
Hata, T., et al., “One-Step Synthesis of 5′-Azido-nucleosides”,J. Chem. Soc., Perkin I, 1980, p. 306.
Hill, J. et al., “3,4-Dihydro-2H-1,4-benzoxazines”, 1964, 3709-3713.
Hillgartner, H. et al., “Bis(trimethylzinn) benzpinakolat, sien reversible radikalische Dissoziation und Reaktinonen”,Liebigs Ann. Chem., 1975, 586-599.
Horwitz, H.P. et al., “Nucleosides. V. The Monomesylates of 1-(2′-Deoxy-β-D-lyxofuranoyl) thymine”,Notes, 1964, 29, 2076-2078.
Hronowski, L.J.J. et al., “Synthesis of New Carbocyclic Analogues of 3′-Azido-and 3′-Amino-2′,3′-dideoxynucleosides”, 1990, 1547-1548.
Huang, Z. et al., “Non-ionic antisense oligonucleotides containing sulfide and sulfone linkages in place of phosphodiester groups in natural oligonucleotides”,J. Cell. Biochem., 1991, Supp. 150, 19, Abstract CD 209.
Huang, Z. et al., “Building Blocks for Oligonucleotide Analogues with Dimethylene Sulfide, Sulfoxide, and Sulfone Group

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