CA2080231A1 - 2'-o-alkylnucleotides as well as polymers which contain such nucleotides - Google Patents

2'-o-alkylnucleotides as well as polymers which contain such nucleotides

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Publication number
CA2080231A1
CA2080231A1 CA2080231A CA2080231A CA2080231A1 CA 2080231 A1 CA2080231 A1 CA 2080231A1 CA 2080231 A CA2080231 A CA 2080231A CA 2080231 A CA2080231 A CA 2080231A CA 2080231 A1 CA2080231 A1 CA 2080231A1
Authority
CA
Canada
Prior art keywords
equals
denotes
well
oligonucleotides
atom
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA2080231A
Other languages
French (fr)
Other versions
CA2080231C (en
Inventor
Brian Sproat
Angus Lamond
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Europaisches Laboratorium fuer Molekularbiologie EMBL
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Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2080231A1 publication Critical patent/CA2080231A1/en
Application granted granted Critical
Publication of CA2080231C publication Critical patent/CA2080231C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16—Purine radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16—Purine radicals
    • C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Virology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Saccharide Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Fixing For Electrophotography (AREA)
  • Electrophotography Configuration And Component (AREA)
  • Color Electrophotography (AREA)

Abstract

Oligonucleotides having the general formula, in which B denotes an arbitrary nucleobase, A equals 0 or CH2;
X or Z equals O, S, NH or denotes CH2 whereby X and Z
can be the same or different, V and W denote O, S, Se, NH2 or an alkyloxy residue, or OH or SH whereby V and W can be the same or different in a monomer unit and L is a H atom or a partner of a binding pair and C equals -O-R and R is an alkyl group with at least 1 C
atom which may be modified if desired, or it denotes an alkenyl or alkinyl group with at least 2 C atoms which may be modified if desired, whereby the modification consists of a substitution by one or several halogen, cyano, carboxy, hydroxy, nitro or/and mercapto residues, and n is an arbitrary whole number, are stable antisense probes which bind specifically. Such oligonucleotides and polynucleotides may be used for the regulation of gene expression and as pharmaceutical agents. They are synthesized from the corresponding 2'-substituted monomers according to well-known methods, preferably on a solid phase.
CA002080231A 1990-04-09 1991-04-08 2'-o-alkylnucleotides as well as polymers which contain such nucleotides Expired - Fee Related CA2080231C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DEP4011473.2 1990-04-09
DE4011473 1990-04-09
PCT/EP1991/000665 WO1991015499A1 (en) 1990-04-09 1991-04-08 2'-o-alkyl nucleotides and polymers containing them

Publications (2)

Publication Number Publication Date
CA2080231A1 true CA2080231A1 (en) 1991-10-10
CA2080231C CA2080231C (en) 2000-10-10

Family

ID=6404077

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002080231A Expired - Fee Related CA2080231C (en) 1990-04-09 1991-04-08 2'-o-alkylnucleotides as well as polymers which contain such nucleotides

Country Status (8)

Country Link
EP (1) EP0524997B1 (en)
JP (1) JPH07103150B2 (en)
AT (1) ATE109788T1 (en)
CA (1) CA2080231C (en)
DE (2) DE4037363A1 (en)
DK (1) DK0524997T3 (en)
ES (1) ES2059132T3 (en)
WO (1) WO1991015499A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6087490A (en) * 1996-03-23 2000-07-11 Novartis Ag Dinucleotide and oligonucleotide analogues

Families Citing this family (43)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5859221A (en) * 1990-01-11 1999-01-12 Isis Pharmaceuticals, Inc. 2'-modified oligonucleotides
US7101993B1 (en) 1990-01-11 2006-09-05 Isis Pharmaceuticals, Inc. Oligonucleotides containing 2′-O-modified purines
US5914396A (en) * 1990-01-11 1999-06-22 Isis Pharmaceuticals, Inc. 2'-O-modified nucleosides and phosphoramidites
US5955589A (en) * 1991-12-24 1999-09-21 Isis Pharmaceuticals Inc. Gapped 2' modified oligonucleotides
US6358931B1 (en) 1990-01-11 2002-03-19 Isis Pharmaceuticals, Inc. Compositions and methods for modulating RNA
US6399754B1 (en) 1991-12-24 2002-06-04 Isis Pharmaceuticals, Inc. Sugar modified oligonucleotides
US5514786A (en) * 1990-01-11 1996-05-07 Isis Pharmaceuticals, Inc. Compositions for inhibiting RNA activity
US5670633A (en) * 1990-01-11 1997-09-23 Isis Pharmaceuticals, Inc. Sugar modified oligonucleotides that detect and modulate gene expression
US6005087A (en) * 1995-06-06 1999-12-21 Isis Pharmaceuticals, Inc. 2'-modified oligonucleotides
US5872232A (en) * 1990-01-11 1999-02-16 Isis Pharmaceuticals Inc. 2'-O-modified oligonucleotides
US5623065A (en) * 1990-08-13 1997-04-22 Isis Pharmaceuticals, Inc. Gapped 2' modified oligonucleotides
WO1994002501A1 (en) 1992-07-23 1994-02-03 Isis Pharmaceuticals, Inc. Novel 2'-o-alkyl nucleosides and phosphoramidites processes for the preparation and uses thereof
US7015315B1 (en) 1991-12-24 2006-03-21 Isis Pharmaceuticals, Inc. Gapped oligonucleotides
US5965722A (en) 1991-05-21 1999-10-12 Isis Pharmaceuticals, Inc. Antisense inhibition of ras gene with chimeric and alternating oligonucleotides
US7119184B2 (en) 1991-08-12 2006-10-10 Isis Pharmaceuticals, Inc. Oligonucleotides having A-DNA form and B-DNA form conformational geometry
US6307040B1 (en) 1992-03-05 2001-10-23 Isis Pharmaceuticals, Inc. Sugar modified oligonucleotides that detect and modulate gene expression
US6277603B1 (en) 1991-12-24 2001-08-21 Isis Pharmaceuticals, Inc. PNA-DNA-PNA chimeric macromolecules
US5700922A (en) * 1991-12-24 1997-12-23 Isis Pharmaceuticals, Inc. PNA-DNA-PNA chimeric macromolecules
EP1044987B1 (en) * 1991-12-24 2006-02-15 Isis Pharmaceuticals, Inc. Gapped 2'-modified oligonucleotides
US5856455A (en) * 1991-12-24 1999-01-05 Isis Pharmaceuticals, Inc. Gapped 2'-modified oligonucleotides
US6346614B1 (en) 1992-07-23 2002-02-12 Hybridon, Inc. Hybrid oligonucleotide phosphorothioates
US5652355A (en) * 1992-07-23 1997-07-29 Worcester Foundation For Experimental Biology Hybrid oligonucleotide phosphorothioates
TW244371B (en) * 1992-07-23 1995-04-01 Tri Clover Inc
GB9304618D0 (en) * 1993-03-06 1993-04-21 Ciba Geigy Ag Chemical compounds
ES2203635T3 (en) * 1994-04-27 2004-04-16 Novartis Ag NUCLEOSIDS AND OLIGONUCLEOTIDES WITH GROUPS 2'-ETER.
GB9417746D0 (en) * 1994-09-03 1994-10-19 Ciba Geigy Ag Chemical compounds
GB9417938D0 (en) * 1994-09-06 1994-10-26 Ciba Geigy Ag Compounds
ATE327244T1 (en) 1995-03-06 2006-06-15 Isis Pharmaceuticals Inc METHOD FOR SYNTHESIS OF 2'-0-SUBSTITUTED PYRIMIDINES AND OLIGOMERS THEREOF
US6166197A (en) * 1995-03-06 2000-12-26 Isis Pharmaceuticals, Inc. Oligomeric compounds having pyrimidine nucleotide (S) with 2'and 5 substitutions
US5856099A (en) * 1996-05-21 1999-01-05 Isis Pharmaceuticals, Inc. Antisense compositions and methods for modulating type I interleukin-1 receptor expression
US5898031A (en) 1996-06-06 1999-04-27 Isis Pharmaceuticals, Inc. Oligoribonucleotides for cleaving RNA
US7812149B2 (en) 1996-06-06 2010-10-12 Isis Pharmaceuticals, Inc. 2′-Fluoro substituted oligomeric compounds and compositions for use in gene modulations
US9096636B2 (en) 1996-06-06 2015-08-04 Isis Pharmaceuticals, Inc. Chimeric oligomeric compounds and their use in gene modulation
CA2256765A1 (en) 1996-06-06 1997-12-11 Novartis Ag 2'-substituted nucleosides and oligonucleotide derivatives
GB9612600D0 (en) 1996-06-13 1996-08-21 Ciba Geigy Ag Chemical compounds
US6172209B1 (en) 1997-02-14 2001-01-09 Isis Pharmaceuticals Inc. Aminooxy-modified oligonucleotides and methods for making same
US6127533A (en) * 1997-02-14 2000-10-03 Isis Pharmaceuticals, Inc. 2'-O-aminooxy-modified oligonucleotides
US6576752B1 (en) 1997-02-14 2003-06-10 Isis Pharmaceuticals, Inc. Aminooxy functionalized oligomers
AU2197600A (en) * 1998-12-30 2000-07-24 Oligos Etc. Inc. Acid stable backbone modified end-blocked nucleic acids and therapeutic uses thereof
WO2004044139A2 (en) 2002-11-05 2004-05-27 Isis Parmaceuticals, Inc. Modified oligonucleotides for use in rna interference
US8569474B2 (en) 2004-03-09 2013-10-29 Isis Pharmaceuticals, Inc. Double stranded constructs comprising one or more short strands hybridized to a longer strand
US8394947B2 (en) 2004-06-03 2013-03-12 Isis Pharmaceuticals, Inc. Positionally modified siRNA constructs
US7884086B2 (en) 2004-09-08 2011-02-08 Isis Pharmaceuticals, Inc. Conjugates for use in hepatocyte free uptake assays

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3788914T2 (en) * 1986-09-08 1994-08-25 Ajinomoto Kk Compounds for cleaving RNA at a specific position, oligomers used in the preparation of these compounds and starting materials for the synthesis of these oligomers.
JPH0723394B2 (en) * 1986-11-27 1995-03-15 日本臓器製薬株式会社 Novel adenosine derivative and pharmaceutical composition containing the compound as an active ingredient
FR2632955B1 (en) * 1988-06-20 1991-12-27 Oris Ind NUCLEOSIDE DERIVATIVES FOR USE IN THE SYNTHESIS OF MARKED OLIGONUCLEOTIDES, OLIGONUCLEOTIDES OBTAINED FROM SUCH DERIVATIVES AND THEIR SYNTHESIS
GB2226027B (en) * 1988-12-13 1992-05-20 Sandoz Ltd Adenosine derivatives,their production and use
JPH0372493A (en) * 1989-08-10 1991-03-27 Kikkoman Corp Production of 2'-o-substituted-adenosine-3',5'-cyclic phosphoric acid or its salt

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6087490A (en) * 1996-03-23 2000-07-11 Novartis Ag Dinucleotide and oligonucleotide analogues

Also Published As

Publication number Publication date
EP0524997A1 (en) 1993-02-03
DE59102512D1 (en) 1994-09-15
DE4037363A1 (en) 1991-10-10
CA2080231C (en) 2000-10-10
JPH07103150B2 (en) 1995-11-08
DK0524997T3 (en) 1995-01-02
ATE109788T1 (en) 1994-08-15
JPH05505197A (en) 1993-08-05
EP0524997B1 (en) 1994-08-10
ES2059132T3 (en) 1994-11-01
WO1991015499A1 (en) 1991-10-17

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