US5130302A
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Boronated nucleoside, nucleotide and oligonucleotide compounds, compositions and methods for using same
Assignee: University of North Carolina at Chapel Hill
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Filing: 1989-12-20
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Granted: 1992-07-14
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Expires: 2009-12-20
Abstract
Abstract A novel class of pharmaceutically active boronated nucleosides are provided. The nucleosides are boronated at a ring nitrogen of the purine or pyrimidine or analogues thereof. Also provided are phosphate esters of these nucleosides and oligomers thereof. Methods of making and using the boronated nucleosides are also disclosed.
Inventors
- 👤 Bernard F. Spielvogel
- 👤 Anup Sood
- 👤 Iris H. Hall
- 👤 Barbara Ramsay Shaw
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 12:35
CPC Classifications
C; C07; C07D; C07D473/00; A; A61; A61P; A61P3/00; A61P3/08; A61P35/00; A61P37/00; A61P37/08; C07D473/02; C07D473/18; C07D473/26; C07D473/32; C07D473/34; C07F; C07F5/00; C07F5/02; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/06; C07H19/10; C07H19/16; C07H19/20; C07H21/00; C07H23/00
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
40 words
A boronated nucleoside comprising a nucleoside which is N-boronated on the nucleoside base with a boron-containing substituent selected from the group consisting of --BH 2 CN, --BH 3 , and --BH 2 COOR, wherein R is C1 to C18 alkyl.
Claim 2
Dependent Claim
40 words
A boronated nucleoside comprising a nucleoside which is N-boronated on the nucleoside base with a boron-containing substituent selected from the group consisting of --BH 2 CN, --BH 3 , and --BH 2 COOR, wherein R is C1 to C18 alkyl.
Claim 3
Dependent Claim
15 words
A boronated nucleotide comprising a 5' phosphate ester of a nucleoside according to claim 1.
Claim 4
Dependent Claim
24 words
A boronated oligonucleotide comprising a chain of ribonucleotides or deoxyribonucleotides, at least one nucleotide or said oligonucleotide comprising a nucleotide according to claim 2.
Claim 5
Dependent Claim
15 words
A boronated nucleoside according to claim 1 wherein the boron-containing substituent is --BH 2 CN.
Claim 6
Dependent Claim
25 words
A boronated nucleoside according to claim 1 wherein the base of said nucleoside is selected from the group consisting of adenine, cytosine, guanine, and inosine.
Claim 7
Dependent Claim
37 words
A boronated nucleoside according to claim 1 selected from the group consisting of: guanosine-N7-cyanoborane; inosine-N7-cyanoborane; adenosine-N1-cyanoborane; cytidine-N3-cyanoborane; guanosine-N7-borane; inosine-N7-borane; adenosine-N1-borane; cytidine-N3-borane; guanosine-N7-carbomethoxyborane; inosine-N7-carboethoxyborane; adenosine-N1-carbopropoxyborane; cytidine-N3-carbobutoxyborane; 2'-deoxyguanosine-N7-cyanoborane; 2'-deoxyinosine-N7-cyanoborane; 2'-deoxyadenosine-N1-cyanoborane; 2'-deoxycytidine-N3-cyanoborane; 2'-deoxyguanosine-N7-borane; 2'-deoxyinosine-N7-borane; 2'-deoxyadenosine-N1-borane; 2'-deoxycytidine-N3-borane; 2'-deoxyguanosine-N7-carbomethoxyborane; 2'-deoxyinosine-N7-carboethoxyborane; 2'-deoxyadenosine-N1-carbopropoxyborane; 2'-deoxycytidine-N3-carbobutoxyborane;
Claim 8
Dependent Claim
14 words
' . 3'-dideoxyguanosine-N7-cyanoborane; 2',3'-dideoxyinosine-N7-cyanoborane; 2',3'-dideoxyadenosine-N1-cyanoborane; 2',3'-dideoxycytidine-N3-cyanoborane; 2',3'-dideoxyguanosine-N7-borane; 2',3'-dideoxyinosine-N7-borane; 2',3'-dideoxyadenosine-N1-borane; 2',3'-dideoxycytidine-N3-borane; 2',3'-dideoxyguanosine-N7-carbomethoxyborane; 2',3'-dideoxyinosine-N7-carboethoxyborane; 2',3'-dideoxyadenosine-N1-carbopropoxyborane; 2',3'-dideoxycytidine-N3-carbobutoxyborane.
Claim 9
Dependent Claim
14 words
' . 3'-dideoxyguanosine-N7-cyanoborane; 2',3'-dideoxyinosine-N7-cyanoborane; 2',3'-dideoxyadenosine-N1-cyanoborane; 2',3'-dideoxycytidine-N3-cyanoborane; 2',3'-dideoxyguanosine-N7-borane; 2',3'-dideoxyinosine-N7-borane; 2',3'-dideoxyadenosine-N1-borane; 2',3'-dideoxycytidine-N3-borane; 2',3'-dideoxyguanosine-N7-carbomethoxyborane; 2',3'-dideoxyinosine-N7-carboethoxyborane; 2',3'-dideoxyadenosine-N1-carbopropoxyborane; 2',3'-dideoxycytidine-N3-carbobutoxyborane.
Claim 10
Dependent Claim
15 words
A boronated nucleoside selected from the group consisting of 2'-deoxyguanosine-N7-cyanoborane, 2'-deoxyinosine-N7-cyanoborane, 2'-deoxyadenosine-N1-cyanoborane, 2'-deoxycytidine-N3-cyanoborane, and 2',3'-dideoxycytidine-N3-cyanoborane.
Claim 11
Dependent Claim
15 words
A boronated nucleoside selected from the group consisting of 2'-deoxyguanosine-N7-cyanoborane, 2'-deoxyinosine-N7-cyanoborane, 2'-deoxyadenosine-N1-cyanoborane, 2'-deoxycytidine-N3-cyanoborane, and 2',3'-dideoxycytidine-N3-cyanoborane.
Claim 12
Dependent Claim
59 words
A pharmaceutical formulation comprising an effective anti-inflammatory or anti-tumor amount of a boronated nucleoside in a pharmaceutically acceptable carrier, said boronated nucleoside comprising a nucleoside which is N-boronated on the nucleoside base with a boron-containing substituent selected from the group consisting of --BH 2 CN, --BH 3 , and --BH 2 COOR, wherein R is C1 to C18 alkyl.
Claim 13
Dependent Claim
59 words
A pharmaceutical formulation comprising an effective anti-inflammatory or anti-tumor amount of a boronated nucleoside in a pharmaceutically acceptable carrier, said boronated nucleoside comprising a nucleoside which is N-boronated on the nucleoside base with a boron-containing substituent selected from the group consisting of --BH 2 CN, --BH 3 , and --BH 2 COOR, wherein R is C1 to C18 alkyl.
Claim 14
Dependent Claim
27 words
A pharmaceutical formulation according to claim 8 wherein the boronated nucleoside is selected from one or more of the group consisting of 2'-deoxyinosine-N7-cyanoborane, 2'-deoxyadenosine-N7-cyanoborane, 2'-deoxycytidine-N1-cyanoborane, and 2'-deoxycytidine-N3-cyanoborane.
Claim 15
Dependent Claim
27 words
A boronated oligonucleotide comprising a chain of 2 to 50 ribonucleotides or deoxyribonucleotides, at least one nucleotide of said oligonucleotide comprising a nucleotide according to claim 2.
Claim 16
Dependent Claim
27 words
A boronated oligonucleotide comprising a chain of 2 to 30 ribonucleotides or deoxyribonucleotides, at least one nucleotide of said oligonucleotide comprising a nucleotide according to claim 2.
Claim 17
Dependent Claim
27 words
A boronated oligonucleotide comprising a chain of 2 to 18 ribonucleotides or deoxyribonucleotides, at least one nucleotide of said oligonucleotide comprising a nucleotide according to claim 2.
Claim 18
Independent Claim
59 words
A method for treating a mammal suffering from inflammation comprising administering to said mammal an effective anti-inflammatory amount of a boronated nucleoside comprising a nucleoside which is N-boronated on the nucleoside base with a boron-containing substituent selected from the group consisting of --BH 2 CN, --BH 3 , and --BH 2 COOR, wherein R is C1 to C18 alkyl.
Claim 19
Independent Claim
59 words
A method for treating a mammal suffering from inflammation comprising administering to said mammal an effective anti-inflammatory amount of a boronated nucleoside comprising a nucleoside which is N-boronated on the nucleoside base with a boron-containing substituent selected from the group consisting of --BH 2 CN, --BH 3 , and --BH 2 COOR, wherein R is C1 to C18 alkyl.
Claim 20
Dependent Claim
22 words
A method according to claim 13, wherein the boronated nucleoside is selected from the group conssiting of 2'-deoxyguanosine-N7-cyanoborane, 2'-deoxyinosine-N7-cyanoborane, 2'-deoxyadenosine-N1-cyanoborane, and 2-'-deoxycytidine-N3-cyanoborane.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-07-14 | 1996-01-13 | 1996-07-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-07-14 | 2000-01-13 | 2000-07-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-07-14 | 2004-01-13 | 2004-07-14 | $7700.00 | Window Closed / Lapsed |