US 2004/0167096 A1 · Anti-viral nucleoside analogs and methods for treating viral infections, especially HIV infections

Abstract

The present invention relates to novel compounds according to the to the general formulas I, II, III, IV or V: 1 wherein B is nucleoside base according to the structure: 2 R is H, F, Cl, Br, I, C1-C4 alkyl (preferably CH3), —C≡N, —C≡C—Ra, 3 X is H, C1-C4 alkyl (preferably, CH3), F, Cl, Br or I; Z is O or CH2, with the proviso that Z is CH2 and not O when the compound is according to general formula II, R3 is —C≡C—H and R2 is H or a phosphate, diphosphate, triphosphate or phosphotriester group; R1 is H, an acyl group, a C1-C20 alkyl or an ether group; R2 is H, an acyl group, a C1-C20 alkyl or ether group, a phosphate, diphosphate, triphosphate, phosphodiester group or a 4 group; Nu is a radical of a biologically active antiviral compound such that an amino group or hydroxyl group from said biologically active antiviral compound forms a phosphate, phosphoramidate, carbonate or urethane group with the adjacent moiety; R8 is H, or a C1-C20 alkyl or ether group, preferably a C1-C12 alkyl group; k is 0-12, preferably, 0-2; R3 is selected from a C1-C4 alkyl (preferably, CH3), —(CH2)n—C≡C—Ra, 5 R3a and R3b are independently selected from H, F, Cl, Br or I; R4 and R5 are independently selected from H, F, Cl, Br, I, OH, C1-C4 alkyl (preferably, CH3), —(CH2)n—C≡C—Ra, 6 with the proviso that R4 and R5 are not both H; Ra is H, F, Cl, Br, I, or —C1-C4 alkyl, preferably H or CH3; Y is H, F, Cl, Br, I or —C1-C4 alkyl, preferably H or CH3; and n is 0, 1, 2, 3, 4 or 5, preferably 0, 1 or 2; and their anomers, pharmaceutically acceptable salts, solvates, or polymorphs thereof.

Claims54

Dependent claims

A compound according to the formula I, II, III, IV or V:

15
wherein B is nucleoside base according to the structure:
16
R is H, F, Cl, Br, I, C1-C4 alkyl, —C≡N, —C≡C—Ra,
17
X is H, C1-C4 alkyl (preferably, CH3), F, Cl, Br or I;
Z is O or CH2, with the proviso that Z is CH2 and not O when the compound is according to general formula II, R3 is —C≡C—H and R2 is H or a phosphate, diphosphate, triphosphate or phosphotriester group;
R1 is H, an acyl group, a C1-C20 alkyl or an ether group;
R2 is H, an acyl group, a C1-C20 alkyl or ether group, a phosphate, diphosphate, triphosphate, phosphodiester group or a
18
group;
Nu is a radical of a biologically active antiviral compound such that an amino group or hydroxyl group from said biologically active antiviral compound forms a phosphate, phosphoramidate, carbonate or urethane group with the adjacent moiety;
R8 is a C1-C20 alkyl or ether group;
k is 0-12, preferably, 0-2;
R3 is selected from a C1-C4 alkyl (preferably, CH3), —CH2)n—C≡C—Ra,
19
with the proviso that R3 of compound formula II is not a —C≡C—H group when Z is O and R2 is H, a phosphate, diphosphate, triphosphate or phosphodiester;
R3a and R3b are independently selected from H, F, Cl, Br or I;
R4 and R5 are independently selected from H, F, Cl, Br, I, OH, C1-C4 alkyl (preferably, CH3), —(CH2)n—C≡C—Ra,
20
with the proviso that R4 and R5 are not both H;
Ra is H, F, Cl, Br, I, or —C1-C4 alkyl, preferably H or CH3;
Y is H, F, Cl, Br, I or —C1-C4 alkyl, preferably H or CH3;
and
n is 0, 1, 2, 3, 4 or 5, preferably 0, 1 or 2;
and their anomers, pharmaceutically acceptable salts, solvates, or polymorphs thereof.

23 more elements

The method according to claim 34 wherein said virus is HIV 1 or 2.

Dependencies are inferred from the claim text.

Anti-viral nucleoside analogs and methods for treating viral infections, especially HIV infections

Life of this patent

Anti-viral nucleoside analogs and methods for treating viral infections, especially HIV infections

Life of this patent

Abstract

Claims54