Iminosugars useful for the treatment of viral diseases
Formula IA, and their use for treating viral infections.
1. A compound of formula IA:
or a pharmaceutically acceptable salt thereof, wherein R is
a)
wherein optionally, at least one CX group in
is replaced with N; or
b)
wherein X 6 is O or S; and
wherein each of W 1 -W 4 is independently H or a C 1 -C 3 alkyl group;
R 1 is a C 1 -C 12 alkyl group; and
wherein each of X 1 -X 5 is independently selected from the group consisting of H, N 3 , NO 2 , NH 2 ,
and a group comprising a heteroatom containing ring,
wherein each of R 2 and R 3 is independently selected from the group consisting of H, C 1 -C 3 alkyl, and C 1 -C 3 hydroxyalkyl; and R 4 and R 5 are each H, or R 4 and R 5 are together ═N—OH, provided that at least one of X 1 -X 5 is
or the group comprising a heteroatom containing ring; or
wherein each of X 1 -X 5 is independently selected from the group consisting of H, N 3 , NO 2 , and NH 2 , and wherein two of X 1 -X 5 , which are adjacent, form a heteroatom containing ring.
2. The compound of claim 1 , wherein R is
3. The compound of claim 2 , wherein one of X 1 -X 5 is
4. The compound of claim 3 , wherein R 2 and R 3 are each methyl and R 4 and R 5 are each H; or wherein R 2 is C 1 -C 3 hydroxyalkyl and each of R 3 , R 4 and R 5 is H; or wherein R 2 and R 3 are each H and R 4 and R 5 are together ═N—OH.
5. The compound of claim 2 , wherein one of X 1 -X 5 is the group comprising a heteroatom containing ring, wherein the heteroatom containing ring comprises at least one ring forming atom selected from N and O; wherein the heteroatom containing ring is directly bound to the ring of R or is bound to the ring of R through a C 1 -C 3 alkyl group; or wherein the heteroatom containing ring is a three, four, five, six or seven membered ring.
6. The compound of claim 5 , wherein the heteroatom containing ring is a conjugated ring.
7. The compound of claim 5 , wherein the heteroatom containing ring is a non-conjugated ring.
8. The compound of claim 2 , wherein the group comprising a heteroatom containing ring is selected from
9. The compound of claim 2 , wherein X 2 or X 3 is
or the group comprising a heteroatom containing ring.
10. The compound of claim 9 , wherein X 4 and X 5 are each independently H or NO 2 , wherein at least one of X 4 and X 5 is H.
11. The compound of claim 9 , wherein X 3 is
or the group comprising a heteroatom containing ring.
12. The compound of claim 11 , wherein X 5 is H or NO 2 .
13. The compound of claim 2 , wherein X 1 and X 2 , X 2 and X 3 , X 3 and X 4 , or X 4 and X 5 together form a heteroatom containing ring.
14. The compound of claim 13 , wherein R is
15. The compound of claim 13 , wherein any of X 1 -X 5 which do not form the heteroatom containing ring, are each H.
16. The compound of claim 1 , wherein R is
17. The compound of claim 16 , wherein R 1 is C 6 -C 10 alkyl.
18. The compound of claim 1 , which is
19. A pharmaceutical composition comprising i) the compound of claim 1 and ii) a pharmaceutically acceptable excipient.
20. The pharmaceutical composition of claim 19 , wherein the composition is an oral pharmaceutical composition.
21. A method of treating a Dengue virus viral infection or a togaviridae virus viral infection in a subject in need thereof, the method comprising administering an effective amount of a compound of claim 1 to the subject to treat the viral infection.