US2014323554A1PendingUtilityA1
Nucleotide and oligonucleotide prodrugs
Assignee: SPRING BANK PHARMACEUTICALS INCPriority: Dec 13, 2005Filed: Feb 21, 2014Published: Oct 30, 2014
Est. expiryDec 13, 2025(expired)· nominal 20-yr term from priority
A61P 31/20A61P 31/00A61P 43/00A61P 31/14A61K 31/7084C07H 19/20C07H 21/04A61K 31/7076C07J 43/003C07J 17/00
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Claims
Abstract
The present invention discloses compounds of formula (I): which exhibit antiviral properties. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject in need of anti-HBV treatment. The invention also relates to methods of treating a HBV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.
Claims
exact text as granted — not AI-modifiedWhat is claimed:
1 . A pronucleotide of formula (I):
or the racemates, enantiomers, diastereomers, geometric isomers, tautomers thereof,
wherein
X=absent, O, NH, NR, S;
X 1 =absent, O, NH;
A=absent, aryl, aralkyl;
n=0, 1, 2, 3, 4, 5;
R=alkyl, substituted alkyl, cycloalkyl, aryl, substituted aryl, aralkyl, heterocylic, O-alkyl, O-heteroaryl, steroidal;
R 1 , R 2 are independently, H, OH, O-alkyl, alkyl, substituted alkyl, cycloalkyl, aryl, substituted aryl, aralkyl, heterocyclic, O-aryl, O-heteroarylaryl, heterocyclic;
R 3 is selected from hydrogen, alkyl, substituted alkyl, C(O)-alkyl, C(O)O-alkyl, C(O)-aryl, C(O)O-aryl, C(O)NH-alkyl, and C(O)NH-aryl;
Y, Z are indendently, O and S;
B 1 , B 2 are independently adenine, guanine, thymine, cytosine, uracil or modified nucleosides;
m=1 to 40.
2 . A pronucleotide according to claim 1 , represented by the formula (II):
wherein m is 1, 2 or 3; and R, X, X 1 , A, n, R 1 , R 2 , R 3 , B 1 and B 2 are as previously defined in claim 1 .
3 . A pronucleotide according to claim 1 , represented by the formula (III):
wherein R, X, X 1 , A, n, R 3 , B 1 and B 2 are as previously defined in claim 1 .
4 . A pronucleotide according to claim 1 , represented by the formula (IV):
wherein R 4 is selected from hydrogen, hydrogen, C(O)-alkyl, C(O)O-alkyl, C(O)-aryl, C(O)O-aryl, C(O)NH-alkyl, and C(O)NH-aryl; and R, R 3 , X, X 1 , A and n are as previously defined in claim 1 .
5 . A compound of claim 4 having the Formula A1, selected from compounds 1-8 of Table 1:
wherein R, X 1 , R 3 and R 4 is delineated for each example in Table 1.
TABLE 1
Compound
No.
R
X 1
R 3
R 4
1
absent
H
H
2
O
H
H
3
absent
H
H
4
O
H
H
5
O
C(O)Ph
H
6
O
H
C(O)Ph
7
absent
H
H
8
O
H
H
6 . A pronucleotide according to claim 1 , represented by the formula (V):
wherein R, R 3 , R 4 , X, X 1 , A and n are as previously defined in claim 1 .
7 . A compound of claim 6 having the Formula B1, selected from compounds 9-16 of Table 2:
wherein R, X 1 , R 3 and R 4 is delineated for each example in Table 2.
TABLE 2
Compound
No.
R
X 1
R 3
R 4
9
absent
H
H
10
O
H
H
11
absent
H
H
12
O
H
H
13
O
C(O)Ph
H
14
O
H
C(O)Ph
15
absent
H
H
16
O
H
H
8 . A pronucleotide according to claim 1 , represented by the formula (VI):
wherein R, R 3 , X, X 1 , A and n are as previously defined in claim 1 .
9 . A method for treating HBV in a subject in need of such treatment comprising, administering to said subject a therapeutically effective amount of a compound according to claim 1 .
10 . A method for treating HBV in a subject in need of such treatment comprising, administering to said subject a therapeutically effective amount of a compound according to claim 1 , in combination with other agents.
11 . A method for treating HBV in a subject infected with resistant strains of HBV in need of such treatment comprising, administering to said subject a therapeutically effective amount of a compound according to claim 1 , alone or in combination with other agents.
12 . A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 1 in combination with a pharmaceutically acceptable carrier or excipient.
13 . A method for treating HBV in a subject in need of such treatment comprising, administering to said subject a therapeutically effective amount of a pharmaceutical composition of claim 7 .Join the waitlist — get patent alerts
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