2-Substituted arabinofuranosyl nucleosides and nucleotides
AssigneeResearch Corporation
InventorsMiroslav V. Bobek, Alexander Bloch, Yung-Chi Cheng
Life of this patent
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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.
Claims12
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.sup.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, .beta.-cyclopentylpropionyl, and dihydrocinnamoyl, and acid addition salts thereof.
A compound selected from the group consisting of 1-(2-amino-2-deoxy-.beta.-D-arabinofuranosyl)cytosine of the formula:
- ##STR13## and pharmaceutically acceptable acid addition salts thereof.
A compound selected from the group consisting of 1-(2-azido-2-deoxy-.beta.-D-arabinofuranosyl)cytosine of the formula:
- ##STR14## and pharmaceutically acceptable acid addition salts thereof.
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.sup.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, .beta.-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.
Dependencies are inferred from the claim text.