Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1998-08-04
2000-12-26
Wilson, James O.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 2713, 536 2761, 536 221, 536 231, 536 276, 536 2721, 536 278, 536 2781, C07H 1900, C07H 19167
Patent
active
061661996
ABSTRACT:
This invention presents novel purine-based compounds for inclusion into oligonucleotides. The compounds of the invention, when incorporated into oligonucleotides are especially useful as "antisense" agents--agents that are capable of specific hybridization with a nucleotide sequence of an RNA. Oligonucleotides are used for a variety of therapeutic and diagnostic purposes, such as treating diseases, regulating gene expression in experimental systems, assaying for RNA and for RNA products through the employment of antisense interactions with such RNA, diagnosing diseases, modulating the production of proteins, and cleaving RNA in site specific fashions. The compounds of the invention include novel heterocyclic bases, nucleosides, and nucleotides. When incorporated into oligonucleotides, the compounds of the invention can be useful for modulating the activity of RNA.
REFERENCES:
patent: 3654262 (1972-04-01), Walton et al.
patent: 4381344 (1983-04-01), Rideout et al.
patent: 4511713 (1985-04-01), Miller et al.
patent: 4689320 (1987-08-01), Kaji
patent: 4719295 (1988-01-01), Cook et al.
patent: 4760017 (1988-07-01), McCormick
patent: 4804748 (1989-02-01), Seela
patent: 4876335 (1989-10-01), Yamane et al.
patent: 4965350 (1990-10-01), Inoue et al.
patent: 5212295 (1993-05-01), Cook
patent: 5214135 (1993-05-01), Srivastava et al.
patent: 5216141 (1993-06-01), Benner
patent: 5359051 (1994-10-01), Cook et al.
patent: 5459255 (1995-10-01), Cook et al.
patent: 5587469 (1996-12-01), Cook et al.
patent: 5808027 (1998-09-01), Cook et al.
Agarwal, K.L. and Rifcina, "Synthesis and Enzymatic Properties of Deoxyribooligonucleotides Containing Methyl and Phenylphosphonate Linkages", Nucleic Acids Research, 1979, 6, 3009-3024.
Agrawal, S. et al., "Oligodeoxynucleoside Phosphoramidates and Phosphorothioates as Inhibitors of Human Immunodeficiency Virus" PNAS USA, 1988, 85, 7079-7083.
Agris, C.H. et al., "Inhibition of Vesicular Stomatitis Virus Protein Synthesis and Infection by Sequence-Specific Oligodeoxyribonucleoside Methylphosphonates", Biochemistry, 1986, 25, 6268-6275.
Arnott and Hukins, "Optimised Parameters for A-DNA and B-DNA" Biochemical and Biophysical Research Communication, 1970, 47, 1504-1510.
Beaucage, S. et al., "Deoxynucleoside phosphoramidites--A new class of key intermediates for deoxypolynucleotide synthesis", Tetrahedron Letters, 1981, 22, 1859-1862.
Bhat, V. et al., "A Simple and Convenient Method for the Selective N-Acylations of Cytosine Nucleosides", Nucleosides and Nucleotides, 1989, 8, 179-183.
Biggadike, K. et al., "Short convergent route to homochiral carbocylic 2'-deoxynucleosides and carbocyclic robonucleosides", J. Chem. Soc. Chem. Commun. 1987, 1083-1084.
Brill, W. et al., "Synthesis of oligodeoxynucleoside phosphorodithioates via thioamidites", Journal of the American Chemical Society, 1989, 111, 2321-2322.
Butke, G. et al., in "Nucleic Acid Chemistry," Part 3, pp. 149-152, Townsend, L.B. and Tipson, eds., J. Wiley and Sons, New York, 1986.
Caruthers, M., "Oligonucleotides. Antisense Inhibitors of Gene Expression", Cohen, J.S., ed., pp. 7-24, CRC Press, Inc., Boca Raton, FL, 1989.
Cazenave et al., "Enzymatic Amplification of Translation Inhibition of Rabbit .beta.-globin mRNA Mediated by Anti-Messenger Oligodeoxynucleotides Covalently Linked to Intercalating Agents", Nucleic Acid Research, 1987, 15, 4717-4736.
Chen, Y. and Wu, "Studies on Fluoroalkylation and Fluroalkoxylation. Part 33. Direct Trifluoromethylation of Aryl Halides with Fluorosulphonyldfluoromethyl Iodide in the Presence of Copper: an Electron Transfer Induced Process", Journal of Chemical Society Perkin Transactions, 1989, 2385-2387.
Chladek, S. et al., "Facile Synthesis of 2'-Amino-2'-Deoxyadenosine", Journal of Carbohydrates, Nucleosides & Nucleotides, 1980, 7, 63-75.
Cohen, "Oligonucleotides: Antisense Inhibitors of Gene Expression", CRC Press, Inc., Boca Raton, FL, 1989.
Constant, J.F. et al., "Heterodimeric Molecules Including Nucleic Acid Bases and 9-Aminoacridine Spectroscopic Studies, Conformations, and Interactions with DNA", Biochemistry, 1988, 27, 3997-4003.
Cook et al., "Synthesis and Antiviral and Enzymatic Studies of Certain 3-Deazaguanines and Their Imidazolecarboxamide Precursors", Journal of Medicinal Chemistry, 1978, 21, 1212-1218.
Daves, G. and Cheng, "The Chemistry and Biochemistry of C-Nucleosides", Progress in Medicinal Chemistry, 1976, 13, 304-349.
De las Heras, F. et al., "3'-C-Cyano-3'-Deoxythymidine", Tetrahedron Letters, 1988, 29, 941-944.
Le Doan, P.L. et al., "Sequence-Targeted Chemical Modification of Nucleic Acids by Complimentary Oligonucleotides Covalently Linked to Porphyrins", Nucleic Acids Research, 1987, 15, 8643-8659.
Dreyer, G. and Dervan, "Sequence-specific cleavage of single-stranded DNA: Oligodeoxynucleotide-EDTA-Fe (II)", PNAS USA, 1985, 82, 968-972.
Eckstein, F. et al., "Polynucleotides Containing2'-Chloro-2'-Deoxyribose", Biochemistry 1972, 11, 4336-4344.
Fox, J. et al., "Nucleosides. XVIII. Synthesis of 2'-Fluorothymidine, 2'-Fluorodeoxyuridine, and Other 2'-Halogeno-2'-Deoxy Nucleosides", Journal of Organic Chemistry, 1964, 29, 558-564.
Freskos, J., "Synthesis of 2' Deoxypyrimidine Nucleosides Via Copper (I) Iodide Catalysis", Nucleosides and Nucleotides, 1989, 8, 1075-1076.
Gaffney, B. and Jones, "A New Strategy for the Protection of Deoxyguanosine During Oligonucleotide Synthesis", Tetrahedron Letters, 1982, 23, 2257-2260.
Gait, M.J., "Oligonucleotide Synthesis", IRL Press, 1985.
Guschlbauer, W. and Jankowski, "Nucleoside conformation is Determined by the Electronegativity of the Sugar Substituent", Nucleic Acds Research, 1980, 8, 1421-1433.
Hertel, L.W. et al., "Synthesis of 2-Deoxy-2, 2-difluoro-D-ribose and 2-Deoxy-2, 2-difluoro-D-ribofuranosyl Nucleosides", Journal of Organic Chemistry, 1988, 53, 2406-2409.
Ikehara, M. et al., "Polynucleotides. LII.synthesis and properties of poly (2'-deox-2'-fluoroadenylic acid)", Nucleic Acids Research, 1978, 5, 1877-1887.
Ikehara, M. et al., "Polynucleotides. LVI. Synthesis and Properties of poly(2'-deoxy-2'-fluoroinosinic Acid)", Nucleic Acids Research, 1978, 5, 3315-3324.
Ikehara, M. et al., "A Linear Relationship Between Electronegativity of 2'-Substituents and conformation of Adenine Nucleosides", Tetrahedron Letters, 1979, 42, 4073-4076.
Ikehara, M. et al., "Recognition by Restriction Endonuclease EcoRI of Deoxyoctanucleotides Containing Modified Sugar Moieties", European J. of Biochem., 1984, 139, 447-450.
Ikehara, M. et al., "Polynucleotides. L. synthesis and properties of poly (2'chloro-2'-deoxyadenylic acid) and poly (2'-bromo-2'-deoxyadenylic acid)", Nucl. Acids Res., 1977, 4, 4249-4260.
Ikehara, M., "Studies of Nucleosides and Nucleotides-LXXXII. cyclonucleosides. (39)..sup.2 synthesis and properties of 2'halogen-2'-deoxyadenosines", Chemistry and Pharmaceutical Bulletin, 1978, 26, 2449-2453.
Ikehara, M., "Purine 8-Cyclonucleosides", Accounts of Chemical Research, 1969, 2, 47-53.
Ikehara, M. et al., "Studies of Nucleosides and Nucleotides-LXXXIV.sup.1 ", Tetrahedron, 1978, 34, 1133-1138.
Ikehara, M. et al., "Studies of Nucleosides and Nucleotides-LXXXIX., Purine cyclonucleosides. (43). synthesis and properties of 2'halogen-2'-deoxyguanosines.sup.1) ", Chem. and Pharm. Bull., 1981, 29, 3281-3285.
Ikehara, M. et al., "Improved Synthesis of 2'-Fluoro-2'-Deoxyadenosine and Synthesis and Carbon-13 NMR Spectrum of Its 3', 5'-Cyclic Phosphate Derivative", Nucleosides and Nucleotides, 1983, 2, 373-385.
Ikehara, M. et al., "Studies of Nucleosides and Nucleotides-LXXXVII..sup.1) , Purine cyclonulceosies. XLII. synthesis of 2' deoxy-2'fluorofunaosine", Chem. and Pharm. Bull., 1981, 29, 1034-1038.
Ikehara, "Studies of Nucleosides and Nucleotides-LXXIX.1), Purine cyclonucleosides. (37). The total synthesis of an antibiotic 2'-amino-2'deoxyguanosine2)", Chem. and Pharm. Bull., 1978, 26, 240-244.
Ikehara, M. et al., "Studies of Nucleosides and Nucleotides-LXV.sup.1 ", Tetrahedron, 1975, 31, 1369-1372.
Inoue, H. et al., "Synthesis and hybridization studies on two complementary nona(2'-O-methyl) ribonucleotides",
Cook Phillip Dan
Manoharan Muthiah
Ramasamy Kanda S.
Isis Pharmaceuticals, Inc
Wilson James O.
LandOfFree
N-2 substituted purines does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with N-2 substituted purines, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and N-2 substituted purines will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-996446