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US5223618A Expired / Lapsed US ⏱️ 0.0 years remaining

4'-desmethyl nucleoside analog compounds

Assignee: Ionis Pharmaceuticals Inc
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Filing: 1990-08-13
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Granted: 1993-06-29
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Expires: 2010-08-13
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Abstract

Abstract Novel oligonucleotide analogs are provided having improved cellular uptake, improved resistance to nucleases, and good hybridization to target RNA. Such analogs are provided having substantially non-chiral, non-ionic linking functionalities between the sugars and sugar analogs thereof. In accordance with preferred embodiments, the 4' position of a sugar or sugar analog at one nucleoside is linked to the 3' position of a second sugar or sugar analog of a second nucleoside by a linking function that comprises a two- or three- carbon backbone chain. In accordance with preferred embodiments, the linking functions comprise the formula)--R 1 --O where R 1 comprises a two or three carbon backbone. Such linking functions also, preferably comprise ether functionalities to effect such linkage. Processes for the automated synthesis of oligonucleotide analogs are also provided.

Inventors

  • 👤 Philip D. Cook
  • 👤 Yogesh S. Sanghvi

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-29 04:14
CPC Classifications
C; C07; C07D; C07D405/00; C07D405/02; C07D405/04; C07D405/14; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/06; C07H19/10; C07H19/16; C07H21/00

Claims Analysis

Total Claims: 7
Claim 1
Independent Claim 79 words
A composition of matter having the structure ##STR6## where: R 1 is selected from the group consisting of ethyl, ethylene, acetylene, cyclopropyl, cyclobutyl, ethyleneoxy, ethyl aziridine, and ethyl aziridine substituted with amino, hydroxyl or carboxylic acid groups, T is selected from the group consisting of tetrahydropyranyl, tert-butyl and bis-(p-methoxyphenyl)phenylemthyl, R 2 is selected from the group consisting of trifluoromethylsulfonyl, methylsulfonyl, halogen, o-trichloroacetimidates, acyloxy, and 2,4,6-trichlorophenyl, B x is a nucleosidic base, and R 3 is OH, halogen, or H.
Claim 2
Dependent Claim 79 words
A composition of matter having the structure ##STR6## where: R 1 is selected from the group consisting of ethyl, ethylene, acetylene, cyclopropyl, cyclobutyl, ethyleneoxy, ethyl aziridine, and ethyl aziridine substituted with amino, hydroxyl or carboxylic acid groups, T is selected from the group consisting of tetrahydropyranyl, tert-butyl and bis-(p-methoxyphenyl)phenylemthyl, R 2 is selected from the group consisting of trifluoromethylsulfonyl, methylsulfonyl, halogen, o-trichloroacetimidates, acyloxy, and 2,4,6-trichlorophenyl, B x is a nucleosidic base, and R 3 is OH, halogen, or H.
Claim 3
Dependent Claim 10 words
The composition of claim 1 wherein R 1 is ethyleneoxy.
Claim 4
Dependent Claim 9 words
The composition of claim 1 wherein T is tert-butyl.
Claim 5
Dependent Claim 12 words
The composition of claim 1 wherein R 2 is trifluoromethylsulfonyl or methylsulfonyl.
Claim 6
Dependent Claim 10 words
The composition of claim 1 wherein R 3 is hydroxyl.
Claim 7
Dependent Claim 24 words
The composition of claim 1 wherein R 1 is ethyleneoxy, T is tert-butyl, R 2 is trifluoromethylsulfonyl or methylsulfonyl, and R 3 is hydroxyl.

References Cited (Backward Citations)

US4591614A Cited
WO1989012060A1 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1996-06-28 1996-12-28 1997-06-29 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2000-06-28 2000-12-28 2001-06-29 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2004-06-28 2004-12-28 2005-06-29 $7700.00 Window Closed / Lapsed

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