US5596086A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Modified internucleoside linkages having one nitrogen and two carbon atoms
Assignee: Ionis Pharmaceuticals Inc
•
Filing: 1991-09-20
•
Granted: 1997-01-21
•
Expires: 2011-09-20
Abstract
Abstract Oligonucleotide analogs are disclosed wherein one or more phosphodiester linkages between adjacent nucleotides are replaced by a backbone linkage resistant to nucleases. The modified oligonucleotides are capable of strong hybridization to target RNA or DNA. The oligomers of the invention may be used as diagnostic reagents to detect the presence or absence of the target DNA or RNA sequences to which they bind.
Inventors
- 👤 Mark Matteucci
- 👤 Robert J. Jones
- 👤 John Munger
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 07:54
CPC Classifications
C; C07; C07D; C07D405/00; C07D405/02; C07D405/04; A; A61; A61P; A61P43/00; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/06; C07H19/10; C07H21/00
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
142 words
A dimer of the formula ##STR65## wherein R 3 is independently H, OH, OCH 3 , SCH 3 , OC 3 H 5 , OC 3 H 7 , SC 3 H 7 , or F; R 4 is hydrogen or a hydroxyl protecting group; R 5 is hydrogen, a solid support or a hydroxyl protecting group; B is independently a purine or pyrimidine residue or an analogous protected residue, and wherein Q is --N(R)--CH 2 --CH.sub. --, --CH 2 --N(R)--CH 2 -- or --CH 2 --CH 2 --N(R)-- wherein the left bond of each Q group is bonded to the 3' position of the structure (1) nucleotide and the right bond of each Q group is bonded to the 5' position of the adjacent structure (1.) nucleoside, wherein R is hydrogen, methyl, ethyl, FMOC, methoxymethyl or --C(O)--O--CH 2 --CH 3 .
Claim 2
Dependent Claim
142 words
A dimer of the formula ##STR65## wherein R 3 is independently H, OH, OCH 3 , SCH 3 , OC 3 H 5 , OC 3 H 7 , SC 3 H 7 , or F; R 4 is hydrogen or a hydroxyl protecting group; R 5 is hydrogen, a solid support or a hydroxyl protecting group; B is independently a purine or pyrimidine residue or an analogous protected residue, and wherein Q is --N(R)--CH 2 --CH.sub. --, --CH 2 --N(R)--CH 2 -- or --CH 2 --CH 2 --N(R)-- wherein the left bond of each Q group is bonded to the 3' position of the structure (1) nucleotide and the right bond of each Q group is bonded to the 5' position of the adjacent structure (1.) nucleoside, wherein R is hydrogen, methyl, ethyl, FMOC, methoxymethyl or --C(O)--O--CH 2 --CH 3 .
Claim 3
Dependent Claim
13 words
The dimer of claim 1 wherein Q is --CH 2 --CH 2 --N(R)--.
Claim 4
Dependent Claim
12 words
The dimer of claim 1 wherein R is hydrogen, methyl, or FMOC.
Claim 5
Dependent Claim
12 words
The dimer of claim 1 wherein R 4 is DMTO or phosphate.
Claim 6
Dependent Claim
16 words
The dimer of claim 1 wherein R 5 is a t-butyldimethylsilyl, phosphonate or a phosphoramidate group.
Claim 7
Dependent Claim
11 words
The dimer of claim 5 wherein the phosphonate group is H-phosphonate.
Claim 8
Dependent Claim
11 words
The dimer of claim 1 wherein B is a protected base.
Claim 9
Dependent Claim
171 words
An oligomer of the formula ##STR66## wherein each R 3 is independently H, OH, OCH 3 , SCH 3 , OC 3 H 5 (O-allyl), OC 3 H 7 (O-propyl), SC 3 H 7 , or F, and wherein each B is independently a purine or pyrimidine residue or an analogous residue, and wherein at least one Q is a modified internucleoside linkage of structure --N(R)--CH 2 --CH 2 --, --CH 2 --N(R)--CH 2 --or --CH 2 --CH 2 --N(R)-- wherein the left bond of each O group is bonded to the Y position of the structure (1) nucleoside and the right bond of each O group is bonded to the 5' position of the adjacent Structure (1) nucleoside, wherein R is hydrogen, methyl, ethyl, methoxymethyl, FMOC or --C(O)--O--CH 2 --CH 3 , and the remaining Q are a phosphodiester analog, wherein the modified internucleoside linkage alternates in a regular pattern comprising one modified internucleoside linkage followed by two phosphodiester analog linkages; and n is an integer between 1 and 200.
Claim 10
Dependent Claim
171 words
An oligomer of the formula ##STR66## wherein each R 3 is independently H, OH, OCH 3 , SCH 3 , OC 3 H 5 (O-allyl), OC 3 H 7 (O-propyl), SC 3 H 7 , or F, and wherein each B is independently a purine or pyrimidine residue or an analogous residue, and wherein at least one Q is a modified internucleoside linkage of structure --N(R)--CH 2 --CH 2 --, --CH 2 --N(R)--CH 2 --or --CH 2 --CH 2 --N(R)-- wherein the left bond of each O group is bonded to the Y position of the structure (1) nucleoside and the right bond of each O group is bonded to the 5' position of the adjacent Structure (1) nucleoside, wherein R is hydrogen, methyl, ethyl, methoxymethyl, FMOC or --C(O)--O--CH 2 --CH 3 , and the remaining Q are a phosphodiester analog, wherein the modified internucleoside linkage alternates in a regular pattern comprising one modified internucleoside linkage followed by two phosphodiester analog linkages; and n is an integer between 1 and 200.
Claim 11
Dependent Claim
13 words
The oligomer of claim 8 wherein the phosphodiester analog is a phosphorothioate linkage.
Claim 12
Dependent Claim
13 words
The oligomer of claim 8 wherein Q is --CH 2 --CH 2 --N(R)--.
Claim 13
Dependent Claim
11 words
The oligomer of claim 10 wherein R is hydrogen or FMOC.
Claim 14
Dependent Claim
66 words
An oligomer having the formula ##STR67## wherein each R 3 is independently H, OH, OCH 3 , SCH 3 , OC 3 H 5 (O-allyl), OC 3 H 7 (O-propyl), SC 3 H 7 , or F, and wherein each B is independently a purine or pyrimidine residue or an analogous residue; R is H or FMOC; and n is an integer between 1 and 200.
Claim 15
Dependent Claim
66 words
An oligomer having the formula ##STR67## wherein each R 3 is independently H, OH, OCH 3 , SCH 3 , OC 3 H 5 (O-allyl), OC 3 H 7 (O-propyl), SC 3 H 7 , or F, and wherein each B is independently a purine or pyrimidine residue or an analogous residue; R is H or FMOC; and n is an integer between 1 and 200.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 2000-01-21 | 2000-07-22 | 2001-01-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2004-01-21 | 2004-07-22 | 2005-01-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2008-01-21 | 2008-07-22 | 2009-01-21 | $7700.00 | Window Closed / Lapsed |