Imidazopyridines as respiratory syncytial virus antiviral agents

1. A compound satisfying formula I, a prodrug, N-oxide, addition salt, quaternary amine, metal complex, or a stereochemically isomeric form thereof;

wherein each X independently is C or N;

each Y independently is C or N;

R 1 is present when X═C and R 1 is selected from the group of H, halogen, C 1 -C 6 alkyl, C 3 -C 7 cycloalkyl, C 1 -C 6 alkoxy, N(R 5 ) 2 , CO(R 6 ), CH 2 NH 2 , CH 2 OH, CN, C(═NOH)NH 2 , C(═NOCH 3 )NH 2 , C(═NH)NH 2 , CF 3 , OCF 3 , and B(OH) 2 ; B (O—C 1 -C 6 alkyl) 2 ;

R 1 is absent when X=N

R 2 is selected from the group consisting of halogen, —(CR 7 R 8 ) n —R 9 , C≡C—CH 2 —R 9 , C≡C—R 9 , and C═C—R 9

R 3 is selected from the group consisting of H, C 1 -C 10 alkyl, C 3 -C 7 cycloalkyl, C 2 -C 10 alkenyl, SO 2 —R 7 , or a 4 to 6 membered saturated ring containing an oxygen atom;

R 4 is present where Y is C and is selected from the group consisting of H, C 1 -C 6 alkyl, C 1 -C 6 cycloalkyl, C 1 -C 6 alkoxy, CO(R 7 ), CF 3 and halogen,

R 4 is absent when Y=N;

R 5 is selected from the group consisting of H, C 1 -C 6 alkyl, COOCH 3 , and CONHSO 2 CH 3 ;

R 6 is selected from the group consisting of OH, O(C 1 -C 6 alkyl), NH 2 , NHSO 2 N(C 1 -C 6 alkyl) 2 , NHSO 2 NHCH 3 , NHSO 2 (C 1 -C 6 alkyl), NHSO 2 (C 3 -C 7 cyclo-alkyl), and N(C 1 -C 6 -alkyl) 2 ;

R 7 and R 8 are each independently chosen from H, C 1 -C 10 alkyl, C 3 -C 7 cycloalkyl or R 7 and R 8 taken together form a 4 to 6 membered aliphatic ring that optionally contains at least one heteroatom selected from the group N, S, O;

R 9 is selected from the group consisting of H, C 1 -C 6 alkyl, C 1 -C 6 alkoxy, C 3 -C 7 cycloalkyl OH, CN, F, CF 2 H, CF 3 , CONR 7 R 8 , COOR 7 , CON(R 7 )SO 2 R 8 , CON(R 7 )SO 2 N(R 7 R 8 ), NR 7 R 8 , NR 7 COOR 8 , OCOR 7 , NR 7 SO 2 R 8 , SO 2 NR 7 R 8 , SO 2 R 7 or a 4 to 6 membered saturated ring containing an oxygen atom;

n is an integer from 2 to 6.

2. A compound according to claim 1 wherein R 2 is selected from the group consisting of halogen, —(CR 7 R 8 ) n —R 9 , C≡C—CH 2 —R 9 and C≡C—R 9 .

3. A compound according to claim 1 , wherein all X atoms are C.

4. A compound according to claim 1 , wherein X—R 1 at the para position to the N bridging the imidazole and pyridine ring, is selected from the group consisting of C—H, C—Cl, and C—Br, and all other R 1 are H.

5. A compound according to claim 1 , wherein R 7 and R 8 are H and n is 2-4.

6. A compound according to claim 1 , wherein R 9 is selected from the group consisting of OH, F, CF 2 H, CF 3 , and secondary C 1 -C 6 alkyl.

7. A compound according to claim 1 , wherein R 2 is C≡C—CH 2 —R 9 with R 9 being selected from the group consisting of C 1 -C 6 alkoxy, C 1 -C 6 straight-chain alkyl, and C 1 -C 6 branched alkyl.

8. A compound according to claim 1 , wherein R 3 is C 3 -C 7 cycloalkyl.

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

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

11. A compound according to claim 1 , wherein R 3 is oxetan-3-yl.

12. A compound according to claim 1 , wherein the Y in para position to N—R 3 is C and the R 4 on that Y is F.

13. A compound according to claim 1 , wherein one Y is N, and the other Y's are C, and wherein the one Y that is N is in para position to N—R 3 .

14. A compound according to claim 1 , wherein all R 4 are H.

15. A pharmaceutical composition comprising a pharmaceutically acceptable carrier, and as active ingredient a therapeutically effective amount of a compound as claimed in claim 1 .

16. A process for preparing a pharmaceutical composition, said process comprising intimately mixing a pharmaceutically acceptable carrier with a therapeutically effective amount of a compound as claimed in claim 1 .

17. A method of treating a respiratory syncytial viral (RSV) infection comprising administering to a subject in need thereof an anti-virally effective amount of a compound as claimed in claim 1 .