Chemistry: molecular biology and microbiology – Measuring or testing process involving enzymes or... – Involving nucleic acid
Reexamination Certificate
2005-05-18
2009-08-11
Riley, Jezia (Department: 1637)
Chemistry: molecular biology and microbiology
Measuring or testing process involving enzymes or...
Involving nucleic acid
C435S091100, C435S091200, C536S022100, C536S023100, C536S024300, C536S025300
Reexamination Certificate
active
07572582
ABSTRACT:
The present invention relates to novel bicyclic and tricyclic nucleoside and nucleotide analogues as well as to oligonucleotides comprising such elements. The nucleotide analogues, LNAs (Locked Nucleoside Analogues), are able to provide valuable improvements to oligonucleotides with respect to affinity and specificity towards complementary RNA and DNA oligomers. The novel type of LNA modified oligonucleotides, as well as the LNAs as such, are useful in a wide range of diagnostic applications as well as therapeutic applications. Among these can be mentioned antisense applications, PCR applications, strand displacement oligomers, as substrates for nucleic acid polymerases, as nucleotide based drugs, etc. The present invention also relates to such applications.
REFERENCES:
patent: 5502177 (1996-03-01), Matteucci et al.
patent: 5582981 (1996-12-01), Toole et al.
patent: 6268490 (2001-07-01), Imanishi et al.
patent: 6670461 (2003-12-01), Nielsen et al.
patent: 6794499 (2004-09-01), Wengel et al.
patent: 2003/0082807 (2003-05-01), Wengel et al.
patent: 2003/0087230 (2003-05-01), Wengel et al.
patent: 2003/0144231 (2003-07-01), Wengel et al.
patent: 0 538 194 (1993-04-01), None
patent: WO-91/06556 (1991-05-01), None
patent: WO-92/03568 (1992-03-01), None
patent: WO-93/07883 (1993-04-01), None
patent: WO-93/10820 (1993-06-01), None
patent: WO-95/14706 (1995-06-01), None
patent: 9 822 489 (1998-05-01), None
patent: 9 839 352 (1998-09-01), None
Abe et al., “Normonoterpenoids and Their Allopyranosides from the Leaves of Cerbera Species (Studies on Cerbera. VIII),” Chem. Pharm. Bull. (1989) 37(10):2639-2642.
Abe et al., “10-Carboxyloganin, Normonoterpenoid Gluosides and Dinormonoterpenoid Glucosides from the Leaves ofCerbera manghas(Studies on Cerbera. 10),” Chem. Pharma. Bull. (1996) 44(10)1797-1800.
Albaek et al., “Two Carbocyclic Locked Nucleic Acid Analogues Give Structural Information About the Role of Hydration in A-Type Duplexes,” Nucleosides, Nucleotides and Nucleic Acids (2007) 26:1529-1532.
Chattopadhyaya, Conformationally-2′, 4′-Locked Aza-ENA and Carbocyclicribo-Thymidine (2007) Nucleic Acids Symposium Series 51: 69-70.
Duncan et al., “Stereoselective Thermal Rearrangement of syn-7-(1,2-Butadienyl)-1-methylbicyclo[2.2.1]hept-2-3n3[syn-7-(3-Methylallenyl)-1-methylnorbornene],” J. Am. Chem. Soc. (1990) 112:8433-8442.
Ferles et al., “Mixed Electrolytic Reduction of 1,4-Dimethylpyridinium Methyl Sulfate with Acetone and of 1-Methylpyridiniummethyl Sulfate with Cyclopentanone,” Collection Czechoslov. Chem. Commun. (1975) 40:2183-2190.
Freier, Susan M., presentation in “Topological Recognition, Base/Backbone Modification, and DNA Stability” session of Purines, Pyrimidines and Related Substances section, 1997 Gordon Conference, Jun 29, 1997-Jul. 4, 1997, Newport RI.
Galan et al., “Diels-Alder Reactions with an α,β-Unsaturated Aldehydo-sugar. A Route to 6-Oxabicyclo[3.2.1]octanes,” Tetrahedron Letters (1993) 34(11):1811-1814.
Gavrilyuk et al., Zhurnal Organicheskol Khimil (1992) 28(8):1602-1614.
Griffey et al., “New Twists on Nucleic Acids: Structural Properties of Modified Nucleosides Incorporated into Oligonnucleotides,” Carbohydrate Modifications in Anti sense Research, Chapter 14, Sanghvi, Y.S., Cook, P.D. Eds.; Oxford University Press (1994) pp. 212-224.
Haaima et al., “Increased DNA binding and sequence discrimination of PNA oligomers containing 2,6-diaminopurine,” Nucleic Acids Research (1997) 25(22):4639-4643.
Hari et al., Synthesis and properties of oligonucleotides containing novel 2′, 4′-BNA analogues (2′, 4′-BNAcoc), Nucleic Acids Research, (2002), supp. 2: 147-148.
Jung et al., “An Intramolecular Prins Double Cyclization Catalyzed by Silyl Triflates,” J. Org. Chem. (1997) 62:9182-9187.
Kawasaki et al., “Synthesis and Biophysical Studies of 2′-dRIBO-2′-F Modified Oligonucleotides,” Conference on Nucleic Acid Therapeutics, Jan. 13, 1991.
Lee et al., “Synthesis and Reactions of 3-C-Branched-Chain Analogues of 3,6-Anhydrodeoxynojirimycin,” J. Carbohydrate Chem. (1997) 16(1):49-62.
Miyazawa et al., “Resolution of racemic 2,6,6-trimethyl-7-oxa-bicyclo[3.1.1]octan-2-ol and 1,6,6-trimethyl-7-oxa-bicyclo[3.1.1]octan-2-ol by microbial esterification,” Tetrahedron: Asymmetry (1997) 8(13):2131-2132.
Morita et al., “Synthesis and Properties of 2′-O,4′-C-Ethylene-Bridged Nucleic Acids (ENA) as Effective Antisense Oligonucleotides,” Bioorganic and Medicinal Chemistry (2003) 11:2211-2226.
Nielsen et al., “A novel class of conformationally restricted oligonucleotide analogues: synthesis of 2′,3′-bridged monomers and RNA-selective hybridisation,” Chem. Commun. (1997) 9:825-826.
Polovinka et al., Zhurnal Organicheskoi Khimil (1992) 28(1):2253-2267.
Rajwanshi et al., “LNA stereoisomers:xylo-LNA (β-D-xyloconfigured locked nucleic acid) and α-L-LNA (α-L-ribo configured locked nucleic acid),” Chem. Commun. (1999) 1395-1396.
Ruiz-Perez et al., “Structure of 5-Hydroxymethyl-7,7-dimethyl-6-oxabicyclo[3.2.1]octane-1-carboxylic Acid,” Acta Crystallographica (1990), C46:1507-1509.
Shibahara et al., “Site-directed cleavage of RNA,” Nucleic Acids Res. (1987) 15:4403-4415.
Uhlmann et al., “Antisense Oligonucleotides: A New Therapeutic Principle,” Chemical Reviews (1990) 90(4):544-584.
Zigeuner et al., Chemical Abstracts (1969) 70(1), abstract No. 3737b.
Zigeuner et al., “Heterocycles. XVI. 1,4-Dimethyl-3-acetoxy-7-acetamido-2-oxabicyclo[2.2.1]heptane,” Heterocyclic Compounds (1969) 70:343, col. 1.
Zigeuner et al., Monatsch. Chem. (1968) 99:2111-2120.
National Seminar on Perspectives in Interfacial Areas of Chemistry and Biology, University of Delhi, Jan. 20-22, 1998.
Declaration of Susan Freier regarding Gordon Conference presentations in 1997.
Imanishi, T., et al. “Synthesis And Property of Novel Conformationally Constrained Nucleoside And Oligonucleotide Analogs”, The Sixteenth International Congress Of Heterocyclic Chemistry, Aug. 10-15, 1997, 4 pages.
Tarkoy et al., “31. Nucelic-Acid Analogues with Constraint Conformational Flexibility in the Sugar-Phosphate Backbone (Bicyclo-DNA)”,Chim. Acta, 76:481-510, (1993).
Tarkoy et al., “Synthesis and pairing Properties of Decanucleotides from (3′S,5′R)-2,Deoxy-3′,5′-ethano-D-ribofuranosyladenine and -thymine**”,Angew. Chem. Int. Ed. Engl., 32 (10) 1432-1434, (1993).
Egil et al., “Crystal Structure of a Parallel-Stranded Duplex of a Deoxycytidylyl-(3′-5′)-deoxycytidine Analogue Containing Intranucleosidyl C(3′)-C(5′) Ethylene Bridges”,American Chemical Society, 115:5855-5856, 1993.
Tarkoy et al., “71. Nucleic-Acid Analogues with Restricted Conformational Flexibility in the Sugar-Phosphate Backbone (‘Bicyclo-DNA’)”,Helvetica Chimica Acta, 77:716-745, (1994).
Bolli et al., “Triple-Helix Formation of Oligodeoxynucleotides Containing [(3′S,5′R)-2′ -Deoxy-3′,5′-ethano-D-ribofuranosyl]nucleosides (“Bicyclo-deoxynucleosides”)**”,Angew. Chem. Int. Ed. Engl., 34 (6) 694-696 (1995).
Bolli et al., 157. Nucleic-Acid Analogswith Restricted Conforamtional Flexibility in the Sugar-Phosphate Backbone (‘Bicyclo-DNA’),Helvetica Chimica Acta, 78:2077-2095, (1995).
Litten et al., “Bicyclo-Oligonucleotides with Inverted Configuration at C(5′): Synthesis and Properties”Biooganic&Medicinal Chemistry Letters, 5 (12) 1231-1234, (1995).
Litten et al., 99. Nucleic-Acid Analogs with Restricted Conformational Flexibility in Sugar-Phosphate Backbone (‘Bicyclo-DNA’),Helvetica Chimica Acta, 79:1129-1147, (1996).
Bolli et al., “Bicyclo-DNA: a H
Nielsen Poul
Wengel Jesper
Corless Peter F.
Edwards Angell Palmer & & Dodge LLP
Exiqon A/S
Riley Jezia
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