Oligomer phosphoramidite compositions and processes for...

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

Reexamination Certificate

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

C536S025310, C536S025330, C536S025100, C536S023100, C536S022100, C536S025300

Reexamination Certificate

active

06858722

ABSTRACT:
Synthetic processes are provided wherein oligomers are prepared using phosphoramidite compositions. Oligomers having phosphodiester, phosphorothioate, phosphorodithioate covalent linkages are prepared that can include other covalent linkages. Also provided are compositions useful in such processes.

REFERENCES:
patent: 3687808 (1972-08-01), Merigan et al.
patent: 4415732 (1983-11-01), Caruthers et al.
patent: 4458066 (1984-07-01), Caruthers et al.
patent: 4500707 (1985-02-01), Caruthers et al.
patent: 4668777 (1987-05-01), Caruthers et al.
patent: 4725677 (1988-02-01), Köster et al.
patent: 4816571 (1989-03-01), Andrus et al.
patent: 4973679 (1990-11-01), Caruthers et al.
patent: 5026838 (1991-06-01), Nojiri et al.
patent: 5132418 (1992-07-01), Caruthers et al.
patent: RE34069 (1992-09-01), Köster et al.
patent: 5153319 (1992-10-01), Caruthers et al.
patent: 5204455 (1993-04-01), Froehler et al.
patent: 5212295 (1993-05-01), Cook
patent: 5453496 (1995-09-01), Caruthers et al.
patent: 5614621 (1997-03-01), Ravikumar et al.
patent: 5670633 (1997-09-01), Cook et al.
patent: 5705621 (1998-01-01), Ravikumar
patent: 5760209 (1998-06-01), Cheruvallath et al.
patent: 5783690 (1998-07-01), Cheruvallath et al.
patent: 5808035 (1998-09-01), Usher et al.
patent: 6069243 (2000-05-01), Scozzari
patent: 6166197 (2000-12-01), Cook et al.
patent: 6172209 (2001-01-01), Manoharan et al.
patent: 6271358 (2001-08-01), Manoharan et al.
patent: 6610842 (2003-08-01), Ravikumar et al.
patent: 0 506 242 (1992-03-01), None
Agrawal et al. (eds.), “Methods of Molecular Biology”, inProtocols for Oligonucleotide Conjugates,Agrawal, S. (ed.), Humana Press, New Jersey, 1994, vol. 26, 1-72.
Alul, R.H. et al., “Oxalyl-CPG: a labile support for synthesis of sensitive oligonucleotide derivatives”,Nucl. Acid Res., 1991, 19, 1527-1532.
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 Specific Ribonucleotides and Unrelated Phosphorylated Biomolecules by the Phosphoramidite Method,”Tetrahedron, 1993, 49(46), 10441-10488.
Beaucage, S.L. et al., “The Functionalization of Oligonucleotides Via Phosphoramidite Derivatives,”Tetrahedron, 1993, 49(10), 1925-1963.
Bielinska, A. et al., “Regulation of Gene Expression with Double-Stranded Phosphorothioate Oligonucleotides”,Science, 1990, 250, 997-1000.
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.
Cook, P.D., “Medicinal Chemistry of Antisense Oligonucleotides—future opportunities”,Anti-Cancer Drug Design, 1991, 6, 585-607.
Crooke, S.T. et al., “Pharmacokinetic Properties of Several Novel Oligonucleotide Analogs in mice”,J. Pharmacol. Exp. Therapeutics, 1996, 277, 923-937.
Delgado, C. et al., “The Uses and Properties of PEG-Linked Proteins”,Crit. Rev. in Therapeutic Drug Carrier Sys., 1992, 9, 249-304.
Efimov, V.A. et al., “New efficient sulfurizing reagents for the preparation of oligodeoxyribonucleotide phosphorothioate analogues”,Nucl. Acids Res., 1995, 23, 4029-4033.
Englisch, U. et al., “Chemically Modified Oligonucleotides as Probes and Inhibitors”,Angew. Chem. Int. Ed. Eng., 1991, 30, 613-629.
Hamm, M. L. et al., “Incorporation of 2′-Deoxy-2′-mercaptocytidine into Oligonucleotides via Phosphoramidite Chemistry,”J. Org. Chem., 1997, 62, 3415-3420.
Iyer, R.P. et al., “The Automated Synthesis of Sulfur-Containing Oligodeoxyribonucleotides Using 3H-1,2-Benzodithiol-3-one 1, 1-Dioxide as Sulfur-Transfer Reagent”,J. Org. Chem., 1990, 55, 4693-4699.
Iyer, R.P. 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.
Kabanov, A.V., “A new class of antivirals: antisense olgonucleotides combined with a hydrophobic substituent effectively inhibit influenza virus reproduction and synthesis of virus-specific proteins in MDCK cells”,FEBS Letts., 1990, 259, 327-330.
Kamer, P.C.J. et al., “An Efficient Approach Toward the Synthesis of Phosphorothioate Diesters via the Schonberg Reaction”,Tetrahedron Letts., 1989, 30, 6757-6760.
Kroschwitz, J.I., “Polynucleotides”,Concise Encyclopedia of Polymer Science and Engineering, 1990, John Wiley & Sons, New York, 858-859.
Letsinger, R.L. et al., “Cholesteryl-conjugated oligonucleotides: Synthesis, properties and activity as inhibitors of replication of human immunodeficiency virus in cell culture”,Proc. Natl. Acad. Sci., 1989, 86, 6553-6556.
Monoharan, M. et al., “Lipidic Nucleic Acids”,Tetrahedron Letts., 1995, 36, 3651-3654.
Manoharan M. et al., “Cholic Acid-Oligonucliotide Conjugates for Antisense Applications”,Bioorganic Med. Chem. Letts., 1994, 4, 1053-1060.
Manoharan, M. et al., “Chemical Modifications to Improve Uptake and Bioavailability of Antisense Oligonucleotides”,Annals NY Acad. Sciences, 1992, 660, 306-309.
Manoharan, M. et al., “Introduction of a Lipophilic Thioether Tether in the Minor Groove of Nucleic Acids for Antisense Applications”,Bioorg. Med. Chem. Letts., 1993, 3, 2765-2770.
Monoharan M. et al., “Oligonucleotide Conjugates: Alteration of the Pharmacokinetic Properties of Antisense Agents”,Nucleosides and Nucleotides, 1995, 14, 969-973.
Marshall, W.S., et al., “Oligonucleotide synthesis as a tool in drug discovery research,”Drug Discovery Today, 1998, 3(1), 34-42.
Mishra, R.K. et al., “Improved leishmanicidal effect of phosphorotioate antisense oligonucleotides by LDL-medicated delivery”,Biochim. Et Biophysica, 1995, 1264, 229-237.
Oberhauser, B. et al., “Effective incorporation of 2′-O-methyl-oligonucleotides into liposomes and enhanced cell association through modification with thiocholesterol”,Nucl. Acids Res., 1992, 20, 533-538.
Ouchi, T. et al., “Synthesis and Antitumor Activity of Poly(Ethylene Glycol)s Linked to 5′-Fluorouracil via a Urethane or Urea Bond”,Drug Des.&Disc., 1992, 9, 93-105.
Polushin, N. N. et al., “Synthesis of Oligonucleotides Containing 2′-Azido-and 2′-Amino-2′-deoxyuridine Using Phosphotriester Chemistry,”Tetrahedron Letts., 1996, 37(19), 3227-3230.
Rao, M.V. et al., “Dibenzoyl Tetrasulphide-A Rapid Sulphur Transfer Agent in the Synthesis of Phosphorothioate Analogues of Oligonucleotides”,Tetrahedron Letts., 1992, 33, 4839-4842.
Ravasio, N. et al., “Selective Hydrogenations Promoted by Copper Catalysts. 1. Chemoselectivity, Regioselectivity, and Stereoselectivity in the Hydrogenation of 3-Substituted Steroids”,J. Org. Chem., 1991, 56, 4329-4333.
Saison-Behmoaras, T. et al., “Short modified antisense oligonucleotides directed against Ha-ras point mutation induce selective cleavage of the mRNA and inhibit T24 cells proliferation”,EMBO J., 1991, 10, 1111-1118.
Sanghvi, Y.S., “Heterocyclic Base Modifications in Nucleic acids and their Applications in Antisense Oligonucleotides”,Antisense Research and Applications, 1993, Chapter 15, CRC Press, Boca Raton, 273-288.
Secrist, J.A. et al., “Synthesis and Biological Activity of 4′-Thionucleosides”,10th International Roundtable: Nucleosides, Nucleotides and their Biological Applications, Sep. 16-20 1992, Abstract 21, Park City, Utah, 40.
Shea, R.G. et al., “Synthesis, hybridization properties and antiviral activity of lipid-oligodeoxynucletide conjugates”,Nucl. Acids Res., 1990, 18, 3777-3783.
Stec, W.J. et al., “Bis (O,O-Diisopropoxy Phosphinothioyl) Disulfide—A Highl

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Oligomer phosphoramidite compositions and processes for... does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Oligomer phosphoramidite compositions and processes for..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Oligomer phosphoramidite compositions and processes for... will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-3479028

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.