Oligomeric compounds having pyrimidine nucleotide (S) with 2'and 5 substitutions

• US 6,166,197 A
• Filed: 03/06/1995
• Issued: 12/26/2000
• Est. Priority Date: 03/06/1995
• Status: Expired due to Term

• Current Assignee: Ionis Pharmaceuticals, Inc.
• Original Assignee: ISIS Pharmaceuticals Incorporated
• Inventors: Cook, Phillip Dan, Ross, Bruce S., Sprankle, Kelly G., Sanghvi, Yogesh S., Griffey, Rich H.
• Primary Examiner(s): Riley, Jezia
• Application Number:
  US08/398,901
• Time in Patent Office: 2,122 Days
• Field of Search: 435/6, 536/22.1, 536/23.1, 536/24.3, 536/25.3, 536/24.5
• US Class Current: 536/24.5
• CPC Class Codes: C07H 19/06 Pyrimidine radicals
• 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: Y02P 20/582 Recycling of unreacted starting or intermediate materials

Abstract

Oligonucleotide analogs are disclosed having pyrimidine monomeric sub-units therein that are modified at the 2'"'"' and 5 positions. Monomeric sub-units having these modifications may be further modified at the 2 position.

Claims

1. An oligomeric compound comprising at least one monomeric sub-unit of structure I:

##STR4## wherein;

X is amino;

R is methyl;

L is oxygen;

Z is --O--CH₃ ; and

one of Q₁ and Q₂ is attached via a phosphorothioate linking moiety to a nucleotide, oligonucleotide, nucleoside, or oligonucleoside and the other of said Q₁ and Q₂, is a hydroxyl, a protected hydroxyl, an activated solid support, a nucleotide, an oligonucleotide, a nucleoside, an oligonucleoside, an oligo-nucleotide/nucleoside, an activated phosphate, a phosphate, an activated phosphite, or a phosphite;

provided that said linking moiety is not a sulfamate group.

2. An oligomeric compound comprising at least one monomeric sub-unit of structure I:

##STR5## wherein;

X is amino;

R is methyl;

L is oxygen;

Z is O--R₁ X₁, where R₁ is C₁ -C₆ alkyl, and X₁ is H; and

one of Q₁ and Q₂ is attached via a phosphorothioate linking moiety to a nucleotide, oligonucleotide, nucleoside, or oligonucleoside and the other of said Q₁ and Q₂, is a hydroxyl, a protected hydroxyl, an activated solid support, a nucleotide, an oligonucleotide, a nucleoside, an oligonucleoside, an oligo-nucleotide/nucleoside, an activated phosphate, a phosphate, an activated phosphite, or a phosphite;

provided that said linking moiety is not a sulfamate group.

3. An oligomeric compound comprising at least one monomeric sub-unit of structure I:

##STR6## wherein;

X is amino;

R is methyl;

L is oxygen;

Z is O--R₁ X₁, where R₁ is substituted C₁ -C₆ alkyl, and X₁ is H; and

one of Q₁ and Q₂ is attached via a phosphorothioate linking moiety to a nucleotide, oligonucleotide, nucleoside, or oligonucleoside and the other of said Q₁ and Q₂, is a hydroxyl, a protected hydroxyl, an activated solid support, a nucleotide, an oligonucleotide, a nucleoside, an oligonucleoside, an oligonucleotide/nucleoside, an activated phosphate, a phosphate, an activated phosphite, or a phosphite;

provided that said linking moiety is not a sulfamate group.