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US5466786A Expired / Lapsed US ⏱️ 0.0 years remaining

2'modified nucleoside and nucleotide compounds

Assignee: Ionis Pharmaceuticals Inc
•
Filing: 1994-05-10
•
Granted: 1995-11-14
•
Expires: 2014-05-10
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Abstract

Abstract Oligomers which have substituents on the 2' position are resistant to oligonucleases and furthermore can be derivatized to deliver reagents or drugs, to carry label, or to provide other properties.

Inventors

  • 👤 Chris A. Buhr
  • 👤 Mark Matteucci

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-30 23:32
CPC Classifications
C; C12; C12N; C12N15/00; C12N15/09; C12N15/11; C12N15/113; C07; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/06; C07H19/10; C07H19/16; C07H19/20; C07H21/00; C12N2310/00; C12N2310/30; C12N2310/32; C12N2310/321; C12N2310/322; C12N2310/35; C12N2310/351; C12N2310/3517; C12N2310/352; C12N2310/3527; C12N2310/353; C12N2310/3535

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 197 words
A monomer having the formula: ##STR7## wherein B is a purine or pyrimidine moiety; W 1 is H, (PO 3 ) m -2 wherein m is an integer of 1-3; a protecting group, or an intermediate moiety in the formation of an internucleotide link which when reacted with the appropriate --OH results in Z wherein Z is selected from the group consisting of P(O)O -- , P(O)S, P(O)NR 2 , P(O)R, P(O)OR', CO, and CNR 2 , wherein R is H or alkyl (1-6 C) and R' is alkyl (1-6 C); W 2 is H, PO 3 -2 a protecting group or an intermediate moiety in the formation of an internucleotide link which when reacted with the appropriate --OH results in Z wherein Z is selected from the group consisting of P(O)O -- , P(O)S, P(O)NR 2 , P(O)R, P(O)OR', CO, and CNR 2 , wherein R is H or alkyl (1-6 C) and R' is alkyl (1-6 C); X is O, S, NR, or CR 2 wherein each R is independently H or alkyl (1-6 C); Y is a drug moiety selected from the group consisting of netropsin, anthramycin, quinoxaline antibiotics, actinomycin, and pyrrolo (1-4) benzodiazepine.
Claim 2
Dependent Claim 197 words
A monomer having the formula: ##STR7## wherein B is a purine or pyrimidine moiety; W 1 is H, (PO 3 ) m -2 wherein m is an integer of 1-3; a protecting group, or an intermediate moiety in the formation of an internucleotide link which when reacted with the appropriate --OH results in Z wherein Z is selected from the group consisting of P(O)O -- , P(O)S, P(O)NR 2 , P(O)R, P(O)OR', CO, and CNR 2 , wherein R is H or alkyl (1-6 C) and R' is alkyl (1-6 C); W 2 is H, PO 3 -2 a protecting group or an intermediate moiety in the formation of an internucleotide link which when reacted with the appropriate --OH results in Z wherein Z is selected from the group consisting of P(O)O -- , P(O)S, P(O)NR 2 , P(O)R, P(O)OR', CO, and CNR 2 , wherein R is H or alkyl (1-6 C) and R' is alkyl (1-6 C); X is O, S, NR, or CR 2 wherein each R is independently H or alkyl (1-6 C); Y is a drug moiety selected from the group consisting of netropsin, anthramycin, quinoxaline antibiotics, actinomycin, and pyrrolo (1-4) benzodiazepine.
Claim 3
Dependent Claim 11 words
The monomer of claim 1 wherein X is O or S.
Claim 4
Dependent Claim 9 words
The monomer of claim 1 wherein X is NR.
Claim 5
Dependent Claim 11 words
The monomer of claim 1 wherein X is CR 2 .
Claim 6
Dependent Claim 16 words
The monomer of claim 1 wherein W 2 is a phosphonate moiety or a salt thereof.
Claim 7
Dependent Claim 12 words
The monomer of claim 1 wherein W 1 is a protecting group.
Claim 8
Dependent Claim 12 words
The monomer of claim 5 wherein said salt is a triethylammonium salt.
Claim 9
Dependent Claim 252 words
A monomer having the formula: ##STR8## wherein B is a purine or pyrimidine moiety; W 1 is H, (PO 3 ) m -2 wherein m is an integer of 1-3; a protecting group, or an intermediate moiety in the formation of an internucleotide link which when reacted with the appropriate --OH results in Z wherein Z is selected from the group consisting of P(O)O -- , P(O)S, P(O)NR 2 , P(O)R, P(O)OR', CO, and CNR 2 , wherein R is H or alkyl (1-6 C) and R' is alkyl (1-6 C); W 2 is H, PO 3 -2 a protecting group, or an intermediate moiety in the formation of an internucleotide link which when reacted with the appropriate --OH results in Z wherein Z is selected from the group consisting of P(O)O -- , P(O)S, P(O)NR 2 , P(O)R, P(O)OR', CO, and CNR 2 , wherein R is H or alkyl (1-6 C) and R' is alkyl (1-6 C); X is O, S or CR 2 wherein each R is independently H or alkyl (1-6 C); Y is selected from the group consisting of substituted or unsubstituted alkyl (2-20 C), substituted or unsubstituted alkenyl (2-20 C), substituted or unsubstituted aryl (6-20 C), wherein the substituents are selected from the group consisting of a hydroxyl, an amino, a mercaptyl, a carboxy or a keto moiety, --CH 2 COOH, --CH 2 COONH 2 , --CH 2 COOEt, --CH 2 CONHCH 2 CH 2 NH 2 and SiR" 3 wherein R" is alkyl (2-6 C).
Claim 10
Dependent Claim 252 words
A monomer having the formula: ##STR8## wherein B is a purine or pyrimidine moiety; W 1 is H, (PO 3 ) m -2 wherein m is an integer of 1-3; a protecting group, or an intermediate moiety in the formation of an internucleotide link which when reacted with the appropriate --OH results in Z wherein Z is selected from the group consisting of P(O)O -- , P(O)S, P(O)NR 2 , P(O)R, P(O)OR', CO, and CNR 2 , wherein R is H or alkyl (1-6 C) and R' is alkyl (1-6 C); W 2 is H, PO 3 -2 a protecting group, or an intermediate moiety in the formation of an internucleotide link which when reacted with the appropriate --OH results in Z wherein Z is selected from the group consisting of P(O)O -- , P(O)S, P(O)NR 2 , P(O)R, P(O)OR', CO, and CNR 2 , wherein R is H or alkyl (1-6 C) and R' is alkyl (1-6 C); X is O, S or CR 2 wherein each R is independently H or alkyl (1-6 C); Y is selected from the group consisting of substituted or unsubstituted alkyl (2-20 C), substituted or unsubstituted alkenyl (2-20 C), substituted or unsubstituted aryl (6-20 C), wherein the substituents are selected from the group consisting of a hydroxyl, an amino, a mercaptyl, a carboxy or a keto moiety, --CH 2 COOH, --CH 2 COONH 2 , --CH 2 COOEt, --CH 2 CONHCH 2 CH 2 NH 2 and SiR" 3 wherein R" is alkyl (2-6 C).

References Cited (Backward Citations)

US4458066A Cited
US4476301A Cited
US4981957A Cited
US4828979A Cited
EP0267996A1 Cited
US4924624A Cited
US5109126A Cited

USPTO Annuity & Maintenance Windows

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3.5 Years (Year 4) 1998-11-13 1999-05-15 1999-11-14 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2002-11-13 2003-05-15 2003-11-14 $3760.00 Window Closed / Lapsed
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