Oligonucleotide and nucleotide amine analogs, methods of synthesis and use

• US 6,828,434 B2
• Filed: 07/10/2002
• Issued: 12/07/2004
• Est. Priority Date: 09/11/1992
• Status: Expired due to Fees

• Current Assignee: ISIS Pharmaceuticals Incorporated
• Original Assignee: ISIS Pharmaceuticals Incorporated
• Inventors: Cook, P. Dan, Manoharan, Muthiah
• Primary Examiner(s): FREDMAN, JEFFREY NORMAN
• Application Number:
  US10/192,437
• Publication Number:
  US 20030153737A1
• Time in Patent Office: 881 Days
• Field of Search: 536/23.1, 536/22.1, 536/25.3, 536/24.3, 435/6
• US Class Current: 536/23.1
• CPC Class Codes: C07H 21/00 Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
• CPC Class Codes: C12Q 1/6813 Hybridisation assays

Abstract

Novel amine compounds are provided by the present invention. Methods of preparing and using said novel amine compounds are also provided.

Claims

1. A compound having the structure:

wherein

R₁ is an oligonucleotide;

R₂ is H; and

X is H, O—

R₁₁, S—

R₁₁, F, Cl, Br, CN, CF₃, OCF₃, OCN, SOCH₃, SO₂CH₃, aminoalkylamino, polyalkylamino, substituted silyl, a reporter molecule, an RNA cleaving group;

wherein R₁₁ is H, C₁ to C₁₀ straight or branched chain lower alkyl or substituted lower alkyl, C₂ to C₁₀ straight or branched chain lower alkenyl or substituted lower alkenyl, C₃ to C₁₀ straight or branched chain lower alkynyl or substituted lower alkynyl, a ¹⁴C containing lower alkyl, lower alkenyl or lower alkynyl, C₇ to C₁₄ substituted or unsubstituted alkaryl or aralkyl, a ¹⁴C containing C₇ to C₁₄ alkaryl or aralkyl, alicyclic, heterocyclic, a reporter molecule or an RNA cleaving group.

2. A compound having the structure:

wherein

R₁ is an oligonucleotide;

R₂ is H; and

X is O—

R₁₁, S—

R₁₁, F, Cl, Br, CN, CF₃. OCF₃, OCN, SOCH₃, SO₂CH₃, aminoalkylamino, polyalkylamino, substituted silyl, a reporter molecule, an RNA cleaving group;

wherein R₁₁ is H, C₁ to C₁₀ straight or branched chain lower alkyl or substituted lower alkyl, C₂ to C₁₀ straight or branched chain lower alkenyl or substituted lower alkenyl, C₃ to C₁₀ straight or branched chain lower alkynyl or substituted lower alkynyl, a ¹⁴C containing lower alkyl, lower alkenyl or lower alkynyl, C₇ to C₁₄ substituted or unsubstituted alkaryl or aralkyl, a ¹⁴C containing C₇ to C₁₄ alkaryl or aralkyl, alicyclic, heterocyclic, a reporter molecule or an RNA cleaving group.

3. A compound having the structure:

wherein

R₁ is an oligonucleotide;

R₂ is H; and

X is O—

R₁₁;

wherein R₁₁ is H.