Thieno[3,2-d]pyrimidines derivatives for the treatment of viral infections

1. A compound of formula (I)

or a pharmaceutically acceptable salt, tautomer(s), stereo-isomeric form, or solvate thereof, wherein

R 1 is selected from the group consisting of hydrogen, halogen, —CH 3 and —CF 3 ;

R 2 is selected from the group consisting of hydrogen, halogen, C 1-6 alkyl and C 3-6 cycloalkyl;

R 3 is C 1-8 alkyl optionally substituted by one or more substituents independently selected from the group consisting of aryl, aryloxy, halogen, hydroxyl, alkylamino, dialkylamino, C 1-6 alkenyl, C 1-6 alkoxy, —CO 2 H, —CO 2 C 1-6 alkyl, —CO 2 NH 2 , —CN, —SO 2 NHC 1-3 alkyl, —NHSO 2 C 1-3 alkyl, —NH(SO 2 )NH 2 , and —SO 2 N(H)(COC 1-6 alkyl; or

R 3 is an alkylaryl optionally substituted by one or more substituents independently selected from the group consisting of aryl, aryloxy, halogen, alkylamino, dialkylamino, C 1-6 alkyl, C 1-6 alkenyl, C 1-6 alkoxy, —CO 2 H, —CO 2 C 1-6 alkyl, —CO 2 NH 2 , —CN, —SO 2 NHC 1-3 alkyl, —NHSO 2 C 1-3 alkyl, —NH(SO 2 )NH 2 , and —C(O)NHSO 2 C 1-3 alkyl.

2. A compound according to claim 1 wherein R 1 and R 2 are both hydrogen and wherein R 3 is C 1-8 alkyl substituted by hydroxyl.

3. A compound according to claim 2 having the structure

4. A pharmaceutical composition comprising a compound according to claim 1 together with one or more pharmaceutically acceptable excipients, diluents or carriers.

5. A method of treating a disorder in which the modulation of TLR 7 and/or TLR 8 is involved, comprising the administration of a therapeutically effective amount of at least one compound of claim 1 .

6. The method of claim 5 , wherein the disorder is a viral infection.

7. A compound according to claim 1 having the structure

8. A compound according to claim 1 , wherein R 2 is H, CH 3 or C(CH 3 ) 3 .

9. A compound according to claim 1 , wherein R 3 is selected from the group consisting of

10. A compound according to claim 1 wherein R 1 is H and R 2 is CH 3 .

11. A compound according to claim 1 wherein R 1 is CH 3 and R 2 is H.

12. A compound according to claim 1 wherein R 1 and R 2 are H.

13. A compound according to claim 1 , wherein R 3 is selected from the group consisting of

14. A compound according to claim 1 , wherein R 3 is

15. A compound according to claim 1 , wherein said compound is selected from the group consisting of

16. A compound as claimed in claim 15 , selected from the group consisting of

17. A pharmaceutical composition comprising a compound according to claim 15 together with one or more pharmaceutically acceptable excipients, diluents or carriers.

18. A method of treating a disorder in which the modulation of TLR 7 and/or TLR 8 is involved, comprising the administration of a therapeutically effective amount of at least one compound as claimed in claim 15 .

19. The method of claim 18 , wherein the disorder is a viral infection.

20. A method of preparing a compound of claim 1 , wherein said method comprises:

mixing intermediate I with cyanamide in a polar solvent containing acid to form intermediate II

and

mixing intermediate II with a peptide coupling reagent or a chlorinating agent in combination with a base and an amine in a polar solvent to form the compound of claim 1 .