US4230698A
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2-Substituted arabinofuranosyl nucleosides and nucleotides
Assignee: Research Corp
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Filing: 1978-05-12
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Granted: 1980-10-28
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Expires: 1998-05-12
Abstract
Abstract Novel arabinofuranosyl nucleosides and nucleotides having 2'-azido, 2'-amino, or 2'-hydrocarbylamino substituents, which have antitumor, antiviral, and antimicrobial properties, are prepared by condensation of a pyrimidine, purine, or 1,3-oxazine base with an acylated 2-azido-2-deoxyarabinofuranosyl halide, followed by deblocking and catalytic hydrogenation, where appropriate, to convert the 2'-azido group to a 2'-amino group and, if desired, alkylation or the like to convert the 2'-amino group to a 2'-hydrocarbylamino group.
Inventors
- 👤 Miroslav V. Bobek
- 👤 Alexander Bloch
- 👤 Yung-Chi Cheng
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 01:01
CPC Classifications
C; C07; C07H; C07H9/00; C07H9/02; C07H9/04; A; A61; A61P; A61P31/00; A61P31/12; C07H19/00; C07H19/02; C07H19/04; C07H19/06; C07H19/16
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
81 words
A compound selected from the group consisting of arabinofuranosyl nucleosides of the formula ##STR12## wherein Z is a pyrimidinyl-1 or purinyl-9 moiety, X is selected from the group consisting of amino, azido, and hydrocarbylamino of 1 to 7 carbon atoms, and each of R and R 1 is selected from the group consisting of hydrogen, acetyl, propionyl, butyryl, valeryl, isovaleryl, hexanoyl, heptanoyl, octanoyl, nonanoyl, undecanoyl, lauroyl, benzoyl, phenylacetyl, phenylpropionyl, o-, m-, and p-methylbenzoyl, β-cyclopentylpropionyl, and dihydrocinnamoyl, and acid addition salts thereof.
Claim 2
Dependent Claim
81 words
A compound selected from the group consisting of arabinofuranosyl nucleosides of the formula ##STR12## wherein Z is a pyrimidinyl-1 or purinyl-9 moiety, X is selected from the group consisting of amino, azido, and hydrocarbylamino of 1 to 7 carbon atoms, and each of R and R 1 is selected from the group consisting of hydrogen, acetyl, propionyl, butyryl, valeryl, isovaleryl, hexanoyl, heptanoyl, octanoyl, nonanoyl, undecanoyl, lauroyl, benzoyl, phenylacetyl, phenylpropionyl, o-, m-, and p-methylbenzoyl, β-cyclopentylpropionyl, and dihydrocinnamoyl, and acid addition salts thereof.
Claim 3
Dependent Claim
20 words
A compound selected from the group consisting of 1-(2-amino-2-deoxy-β-D-arabinofuranosyl)cytosine of the formula: ##STR13## and pharmaceutically acceptable acid addition salts thereof.
Claim 4
Dependent Claim
20 words
A compound selected from the group consisting of 1-(2-amino-2-deoxy-β-D-arabinofuranosyl)cytosine of the formula: ##STR13## and pharmaceutically acceptable acid addition salts thereof.
Claim 5
Dependent Claim
20 words
A compound selected from the group consisting of 1-(2-azido-2-deoxy-β-D-arabinofuranosyl)cytosine of the formula: ##STR14## and pharmaceutically acceptable acid addition salts thereof.
Claim 6
Dependent Claim
20 words
A compound selected from the group consisting of 1-(2-azido-2-deoxy-β-D-arabinofuranosyl)cytosine of the formula: ##STR14## and pharmaceutically acceptable acid addition salts thereof.
Claim 7
Dependent Claim
11 words
The compound of claim 1 wherein X is amino or azido.
Claim 8
Dependent Claim
21 words
The compound of claim 1 wherein X is amido, R is hydrogen or benzoyl, and R 1 is hydrogen or acetyl.
Claim 9
Dependent Claim
30 words
The compound of claim 1 wherein X is amino or azido, each of R and R 1 is hydrogen, and the acid addition salts are pharmaceutically acceptable acid addition salts.
Claim 10
Dependent Claim
53 words
The compound of any of claims 4, 5, or 6 wherein Z is a pyrimidinyl-1 moiety from a pyrimidine base of the formula ##STR15## wherein R 4 is amino, hydroxy, thio, hydroxylamino, alkylamino, arylamino, or aralkylamino, and R 5 is fluoro, bromo, chloro, hydrogen, iodo, mercapto, nitro, nitrilo, thiocyanato, alkyl, alkenyl, or alkynyl.
Claim 11
Dependent Claim
50 words
The compound of any of claims 4, 5, or 6 wherein Z is a purinyl-9 moiety from a purine base of the formula ##STR16## wherein R 6 is amino, hydrogen, hydroxylamino, thio, chloro, alkylamino, arylamino, or aralkylamino, and R 7 is hydrogen, oxo, chloro, fluoro, amino, nitro, thio, or hydroxyalkyl.
Claim 12
Dependent Claim
26 words
The compound of any of claims 4, 5, or 6 wherein Z is selected from the group consisting of uracilyl-1, thyminyl-1, 5-fluorouracilyl-1, adeninyl-9, guaninyl-9, and 6-chloropurinyl-9.
Claim 13
Dependent Claim
105 words
A composition in dosage unit form comprising an arabinofuranosyl nucleoside of the formula ##STR17## wherein Z is a pyrimidinyl-1 or purinyl-9 moiety, X is selected from the group consisting of amino, azido, and hydrocarbylamino of 1 to 7 carbon atoms, and each of R and R 1 is selected from the group consisting of hydrogen, acetyl, propionyl, butyryl, valeryl, isovaleryl, hexanoyl, heptanoyl, octanoyl, nonanoyl, undecanoyl, lauroyl, benzoyl, phenylacetyl, phenylpropionyl, o-, m-, and p-methylbenzoyl, β-cyclopentylpropionyl, and dihydrocinnamoyl, said nucleoside being either in the free base form or in the form of a pharmaceutically acceptable acid addition salt, and a sterile, compatible, pharmaceutical carrier for said nucleoside.
Claim 14
Dependent Claim
105 words
A composition in dosage unit form comprising an arabinofuranosyl nucleoside of the formula ##STR17## wherein Z is a pyrimidinyl-1 or purinyl-9 moiety, X is selected from the group consisting of amino, azido, and hydrocarbylamino of 1 to 7 carbon atoms, and each of R and R 1 is selected from the group consisting of hydrogen, acetyl, propionyl, butyryl, valeryl, isovaleryl, hexanoyl, heptanoyl, octanoyl, nonanoyl, undecanoyl, lauroyl, benzoyl, phenylacetyl, phenylpropionyl, o-, m-, and p-methylbenzoyl, β-cyclopentylpropionyl, and dihydrocinnamoyl, said nucleoside being either in the free base form or in the form of a pharmaceutically acceptable acid addition salt, and a sterile, compatible, pharmaceutical carrier for said nucleoside.
Claim 15
Dependent Claim
31 words
The composition of claim 10 wherein the arabinofuranosyl nucleoside is a compound selected from the group consisting of 1-(2-amino-2-deoxy-β-D-arabinofuranosyl) cytosine of the formula: ##STR18## and pharmaceutically acceptable acid addition salts thereof.
Claim 16
Dependent Claim
31 words
The composition of claim 10 wherein the arabinofuranosyl nucleoside is a compound selected from the group consisting of 1-(2-azido-2-deoxy-β-D-arabinofuranosyl) cytosine of the formula: ##STR19## and pharmaceutically acceptable acid addition salts thereof.
References Cited (Backward Citations)
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US3501456A
Cited
US3755295A
Cited
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-10-28 | 1984-04-28 | 1984-10-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-10-28 | 1988-04-28 | 1988-10-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-10-28 | 1992-04-28 | 1992-10-28 | $7700.00 | Window Closed / Lapsed |