Bicyclonucleoside analogues

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

C536S027100, C536S027200, C536S027210, C536S028100, C536S028400

Reexamination Certificate

active

10054300

ABSTRACT:
Bicyclonucleoside analogues which exhibit anti-AIDS activity and intermediates to produce oligonucleotide analogues which have anti-sense or anti-gene activity as well as in vivo stability. Compounds of the following formula (1) or their pharmaceutically acceptable salts.wherein R1represents a hydrogen atom or a protecting group for a hydroxy group, R2represents an azido group or an optionally protected amino group or the like, B represents a purin-9-yl or a 2-oxo-1,2-dihydropyrimidin-1-yl group, which are optionally substituted with substituents selected from the group consisting of a halogen atom, an alkyl group having 1–6 carbon atoms, a hydroxy group, a mercapto group and an amino group.

REFERENCES:
patent: 3687808 (1972-08-01), Merigan, Jr. et al.
patent: 4689320 (1987-08-01), Kaji
patent: 4806463 (1989-02-01), Goodchild et al.
patent: 5004810 (1991-04-01), Draper
patent: 5166195 (1992-11-01), Ecker
patent: 5194428 (1993-03-01), Agrawal et al.
patent: 5242906 (1993-09-01), Pagano et al.
patent: 5248670 (1993-09-01), Draper et al.
patent: 5442049 (1995-08-01), Anderson et al.
patent: 5457189 (1995-10-01), Crooke et al.
patent: 5514577 (1996-05-01), Draper et al.
patent: 5523389 (1996-06-01), Ecker et al.
patent: 5580767 (1996-12-01), Cowsert et al.
patent: 5582972 (1996-12-01), Lima et al.
patent: 5582986 (1996-12-01), Monia et al.
patent: 5591600 (1997-01-01), Ecker
patent: 5591623 (1997-01-01), Bennett et al.
patent: 5591720 (1997-01-01), Anderson et al.
patent: 5607923 (1997-03-01), Cook et al.
patent: 5620963 (1997-04-01), Cook et al.
patent: 5658891 (1997-08-01), Draper et al.
patent: 5661134 (1997-08-01), Cook et al.
patent: 5681747 (1997-10-01), Boggs et al.
patent: 5681944 (1997-10-01), Crooke et al.
patent: 5691461 (1997-11-01), Ecker et al.
patent: 5877309 (1999-03-01), McKay et al.
patent: 5955443 (1999-09-01), Bennett et al.
patent: 5985558 (1999-11-01), Dean et al.
patent: 6111094 (2000-08-01), Bennett et al.
patent: 6127533 (2000-10-01), Cook et al.
patent: 6268490 (2001-07-01), Imanishi et al.
patent: 6670461 (2003-12-01), Wengel et al.
patent: 6794499 (2004-09-01), Wengel et al.
patent: 7034133 (2006-04-01), Wengel et al.
patent: 2002/0147332 (2002-10-01), Kaneko et al.
patent: 2003/0134808 (2003-07-01), Wengel et al.
patent: 2003/0144231 (2003-07-01), Wengel et al.
patent: 2003/0207841 (2003-11-01), Kaneko et al.
patent: 2005/0287566 (2005-12-01), Wengel et al.
patent: WO 94/08003 (1994-04-01), None
patent: WO 96/31557 (1996-10-01), None
patent: WO 98/39352 (1998-09-01), None
patent: WO 99/14226 (1999-03-01), None
Obika et al., “Synthesis of a conformationally locked AZT analogue, 3′-azido-3′-deoxy-2′-O,4′-C-methylene-5-methyluridine”, Tetrahedron Letters, 40, 6465-6468, 1999.
U.S. Appl. No. 09/925,673, Kaneko et al.
Griffiths and Nickoloff, “Keratinocyte Intercellular Adhesion Molecule-1 (ICAM-1) Expression Precedes Dermal T Lymphocytic Infiltration in Allergic Contact Dermatitis (Rhus dermatitis)”,Am. J. Pathology, 1989, 135, 1045-1053.
Thuong and Helene, “Sequence-Specific Recognition and Modification of Double-Helical DNA by Oligonucleotides”,Angew. Chem. Int. Ed. Engl., 1993, 32, 666-690.
Englisch and Gauss, “Chemically Modified Oligonucleotides as Probes and Inhibitors”,Angewandte Chemie, International Edition, 1991, 30, 613-722.
Manoharan et al., “Chemical Modifications to Improve Uptake and Bioavailability of Antisense Oligonucleotides”,Ann. N.Y. Acad. Sci., 1992, 660, 306-309.
Stetler-Stevenson et al., “Tumor Cell Interactions with the Extracellular Matrix During Invasion and Metastasis”,Annu. Rev. Cell Biol., 1993, 9, 541-573.
Cook, “Medicinal chemistry of antisense oligonucleotides- future opportunities”,Anti-Cancer Drug Design, 1991, 6, 585-607.
Morassutti et al., “Reduction ofmdrlGene Amplification in Human Multidrug-Resistant LoVo DX Cell Line Is Promoted by Triple Helix-Forming Oligonucleotides”,Antisense&Nucleic Acid Drug Development, 1999, 9, 261-270.
Sanghvi, “Heterocyclic Base Modifications in Nucleic Acids and their Applications in Antisense Oligonucleotides”,Antisense Research and Applications, Ed. S.T. Crooke and B. Lebleu, CRC Press, 1993, 273-288 (Chapter 25).
Shiohara et al., “Fixed Drug Eruption”,Arch. Dermatol., 1989, 125, 1371-1412.
Ebbinghaus et al., “Inhibition of Transcription Elongation in the HER-2
eu Coding Sequence by Triplex-Directed Covalent Modification of the Template Strand”,Biochemistry, 1999, 38, 619-628.
Catapano et al., “Inhibition of Gene Expression and Cell Proliferation by Triple Helix-Forming Oligonucleotides Directed to thec-mycGene”,Biochemistry, 2000, 39, 5126-5138.
Mishra et al., “Improved leishmanicidal effect of phosphorotioate antisense oligonucleiotides by LDL-mediated delivery”,Biochimica et Biophysica Acta, 1995, 1264, 229-237.
Svinarchuk et al., “Inhibition of HIV proliferation in MT-4 cells by antisense oligonucleotide conjugated to lipophilic groups”,Biochimie, 1993, 75, 49-54.
Manoharan et al., “Introduction of a lipophilic thioether tether in the minor groove of nucleic acids for antisense applications”,Bioorganic&Medicinal Chemistry Letters, 1993, 3, 2765-2770.
Manoharan et al., “Cholic Acid-Oligonucleotide Conjugates for Antisense Applications”,Bioorganic&Medicinal Chemistry Letters, 1994, 4, 1053-1060.
Yu et al., “Specific Inhibition of PCR by Non-Extendable Oligonucleotides Using a 5′ to 3′ Exonuclease-Deficient DNA Polymerase”,Biotechniques, 1997, 23, 714-720.
Lisby et al., “Intercellular adhesion molecule-I (ICAM-I) expression correlated to inflammation”,Brit. J. Dermatol., 1989, 120, 479-484.
Tam and Fraser-Reid, “A synthetic route to 4-C-methyl-xylo-furanose”,Can. J. Chem., 1979, 57, 2818-2822.
Resnicoff et al., “Inhibition of rat C6 glioblastoma tumor growth by expression of insulin-like growth factor I receptor antisense mRNA”,Cancer Immunol. Immunother., 1996, 42, 64-68.
Maher III, “Prospects for the Therapeutic Use of Antigene Oligonucleotides”,Cancer Investigation, 1996, 14(1), 66-82.
Resnicoff et al., “Rat Glioblastoma Cells Expressing an Antisense RNA to the Insulin-like Growth Factor-1 (IGF-1) Receptor are Nontumorigenic and Induce Regression of Wild-Type Tumors”,Cancer Research, 1994, 54, 2218-2222.
Pass et al., “Inhibition of Hamster Mesothelioma Tumorigenesis by an Antisense Expression Plasmid to the Insulin-like Growth Factor-1 Receptor”,Cancer Research, 1996, 56, 4044-4048.
Hua and Muschel, “Inhibition of Matrix Metalloproteinase 9 Expression by a Ribozyme Blocks Metastasis in a Rat Sarcoma Model System”,Cancer Research, 1996, 56, 5279-5284.
Brimacombe and Ching, “Nucleophilic Displacement Reactions in Carbohydrates”,Carbohydrate Research, 1968, 8, 82-88.
Boggemeyer et al., “Borrelia burgdorferiUpregulates the Adhesion Molecules E-selectin, P-selectin, ICAM-1 and VCAM-1 on Mouse Endothelioma Cells in vitro”,Cell Adhesion and Communication, 1994, 2, 145-157.
Kerr et al., “TGF-β1 Inhibition of Transin/Stromelysin Gene Expression is Mediated through a Fos Binding Sequence”,Cell, 1990, 61, 267-278.
Singh et al., “LNA (locked nucleic acids): synthesis and high-affinity nucleic acid recognition”,Chem. Commun., 1998, 4, 455-456.
Birkendal-Hansen, “Proteolytic remodeling of extracellular matrix”,Current Opinion in Cell Biology, 1995, 7, 728-735.
Leroith et al., “Molecular and Cellular Aspects of the Insulin-Like Growth Factor I Receptor”,Endocrine Reviews, 1995, 16, 143-163.
Kabanov et al., “A new class of antivirals: antisense oligonucleotides combined with a hydrophoic substitutent effectively inhibit influenza virus reproduction and synthesis of virus-specific proteins in MDCK cells”

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

Bicyclonucleoside analogues does not yet have a rating. At this time, there are no reviews or comments for this patent.

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

Rate now

     

Profile ID: LFUS-PAI-O-3817693

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