Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1994-05-26
1996-11-05
Wilson, James O.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 253, 536 2531, 536 2533, 536 2534, 536 255, 536 256, C07H 100, C07H 2100, C12N 1511
Patent
active
055719023
ABSTRACT:
Synthetic processes are provided for the solution phase synthesis of oligonucleotides, especially phosphorothioate oligonucleotides, and intermediate compounds useful in the processes. Intermediates having structure ##STR1## are prepared in accord with preferred embodiments.
REFERENCES:
patent: 3687808 (1972-08-01), Merigan, Jr. et al.
patent: 4458066 (1984-07-01), Caruthers et al.
patent: 4725677 (1988-02-01), Koster et al.
patent: 4806463 (1989-02-01), Goodchild et al.
patent: 4845205 (1989-07-01), Huynh Dinh et al.
patent: 5113005 (1992-05-01), Celebuski
patent: 5159095 (1992-10-01), Celebuski
patent: 5264423 (1993-11-01), Cohen et al.
patent: 5276019 (1994-01-01), Cohen et al.
Beaucage, S. et al., "Advances in the Synthesis of Oligonucleotides by the Phosphoramidite Approach", Tetrahedron 1992, 48(12), 2223-2311.
Burch, R. et al., "Oligonucleotides Antisense to the Interleukin 1 Receptor mRNA Block the Effects of Interleukin 1 in Cultures Murine and Human Fibroblasts and in Mice", The Journal of Clinical Investigation, Inc. 1991, 88, 1190-1196.
Celebuski, J. et al, "Synthesis and Utility of a DNA Phosphrylating Agent Based on 2-(Triphenylsilyl)ethanol", J. Org. Chem. 1992, 57, 5535-5538.
Higgins, "Medical Sciences", PNAS USA1993, 90, 9903-9905.
Honda, S. et al., "2-Diphenylmethylsilylethyl Group as a New Protecting Group of Internucleotidic Phosphates in Oligonucleotide Synthesis", Tetrahedron Letters 1981, 2093-2096.
Iyer, R. et al., "3H-1, 2-Benzodithiole-3-one 1, 1-Dioxide as an Improved Sulfurizing Reagent in the Solid-Phase Synthesis of Oligodeoxyribonucleoside Phosphorothioates", J. Am. Chem. Soc. 1990, 112, 1253-1254.
Iyer, R. et al., "The Automated Synthesis of Sulfur-Containing Oligodeoxyribonucleotides Using 3H-1,2-Benzodithiol-3-one 1,1-Dioxide as a Sulfur-Transfer Reagent", J. Org. Chem. 1990, 55(15), 4693-4699.
Kamer, P. et al., "An Efficient Approach Toward the Synthesis of Phosphorothioate Diesters via the Schonberg Reaction", Tetrahedron Letters 1989, 30(48), 6757-6760.
Kitajima, I. et al., "Ablation of Transplanted HTLV-I Tax-Transformed Tumors in Mice by Antisense Inhibiton of NF-.kappa.B", Science 1992, 258, 1792-1795.
March, J., "Advanced Organic Chemistry", pp. 16-18, 237-239, John Wiley & Sons, New York, 1985.
Offensperger, W.-B. et al., "In vivo Inhibition of Duck Hepatitis B Virus Replication and Gene Expression by Phosphorothioate Modified Antisense Oligodoxynucleotides", The EMBO Journal 1993, 12(3), 1257-1262.
Rao, M. V. et al., "Dibenzoyl Tetrasulphide -A Rapid Sulphur Transfer Agent in the Synthesis of Phosphorothioate Analogues of Oligonucleotides", Tetrahedron Letters 1992, 33(33), 4839-4842.
Simons, M. et al., "Antisense c-myb Oligonucleotides Inhibit Intimal Arterial Smooth Muscle Cell Accumulation in vivo", Nature 1992, 359, 67-70.
Streitweiser, Jr., A. et al., "Introduction to Organic Chemistry", pp. 437-440, Macmillan Publishing Co., Inc., New York, 1981.
Takaku, H. et al., "Use of 1,1,1,3,3,3,-Hexafluoro-2-Propyl Protecting Group in the Synthesis of DNA Fragments via Phosphoramidite Intermediates", Tetrahedron Letters 1988, 29(1), 81-84.
Vu, H. et al., "Internucleotide Phosphite Sulfurization with Tetraethylthiuram Disulfide. Phosphorothioate Oligonucleotide Synthesis via Phosphoramidite Chemistry", Tetrahedron Letters 1991, 32(26), 3005-3008.
Vlassov, V., "Inhibition of Tick-Borne Viral Encephalitis Expression Using Covalently Linked Oligonucleotide Analogs", in Oligodeoxynucleotides as Antisense Inhibitors of Gene Expression: Therapeutic Implications, Jun. 18-21, 1989, Sheraton Potomac Inn, Rockville, MD.
Wright, P. et al., "Large Scale Synthesis of Oligonucleotides via Phosphoramidite Nucleosides and a High-loaded Polystyrene Support", Tetrahedron Letters 1993, 34(21), 3373-3376.
Wolter, A., et al., "Polymer Support Oligonucleotide Synthesis XX: Sysnthesis of Henhectacosa Deoxynucleotide by Use of a Dimeric Phosophoramidite Synthon", Nucleosides & Nucleotides 1986, 5(1), 65-77.
Bannwarth, W., "Synthesis of Oligodeoxynucleotides by the Phosphite-Triester Method Using Dimer Units and Different Phosphorous-Protecting Groups", Helvetica Chimica Acta.
Miura, K. et al., "Blockwise MEchanical Synthesis of Oligonucleotides by the Phosphoramidite Method", Chem. Pharm. Bull. 1987, 35(2), 833-836.
Kumar, G. et al., "Improvements in Oligodeoxyribonucleotide Synthesis: Methyl N,N-Dialkylphosphoramidite Dimer Units for Solid Support Phosphite Methodology", J. Org. Chem. 1984, 49, 4905-4912.
Wyatt, J. et al, "Combinatorially Selected Guanosine-Quartet Structure is a Potent Inhibitor of Human Immunodeficiency Virus Envelope-Mediated Cell Fusion", PNAS USA 1994, 91, 1356-1360.
Cole Douglas L.
Ravikumar Vasulinga
ISIS Pharmaceuticals Inc.
Wilson James O.
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