N-acyl-arylsulfonamide derivatives as aminoacyl-tRNA synthetase inhibitors

1. A compound selected from the following compounds and pharmaceutically acceptable salts thereof:

2. A compound selected from compounds of the following formula:

and pharmaceutically acceptable salts thereof,

wherein:

R1 is C 1-4 alkyl;

R2 is C 1-4 alkyl or H;

R3 is C 1-4 alkyl or H;

R1, R2 or R1, R3 together with the atoms to which they are attached may form cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;

provided that R2 and R3 are not both hydrogen;

wherein the radical:

wherein:

R9 is independently H, halo, C 1-6 alkyl, phenyl, or CN, wherein said alkyl is optionally substituted with 1 to 3 substituents selected from halo;

R10 is independently H, halo, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, pyridyl, pyrimidyl, triazinyl, tetrazolyl, purinyl, phenyl, CN, C(═O)R e , C(═O)OR e , C(═O)N(R e )R f , OR e , or S(O) 0-2 R e , wherein said alkyl is optionally substituted with 1 to 3 substituents selected from halo, and wherein said pyridyl, pyrimidyl, triazinyl, tetrazolyl, purinyl, and phenyl are optionally substituted with 1 or 2 substituents independently selected from OR e , N(R e )R f , halo, SR e , methyl, ethyl, and phenyl;

R11 is independently H, halo, C 2-6 alkyl, phenyl, or CN;

R12 is independently H or halo;

R13 is independently H, halo, or C 1-6 alkyl;

R e and R f are independently H, C 1-8 alkyl, or phenyl, wherein said alkyl is optionally substituted by 1 to 3 substituents selected from halo;

with the proviso that the compound is not:

3. A compound according to claim 2 , wherein R9 is independently H, halo, C 1-6 alkyl, or phenyl.

4. A compound according to claim 2 , wherein R9 is independently H, F, Cl, isopropyl, or phenyl.

5. A compound according to claim 2 , wherein R10 is independently H, halo, pyridyl, pyrimidyl, triazinyl, phenyl, or purinyl, wherein said pyridyl, pyrimidyl, triazinyl, purinyl, and phenyl are optionally substituted by 1 or 2 substituents independently selected from NH 2 , NMe 2 , SMe, methyl, ethyl, halo, OH, OC 1-4 alkyl, and phenyl.

6. A compound according to claim 2 , wherein R10 is independently halo, pyridyl, pyrimidyl, triazinyl, phenyl, or purinyl, wherein said pyridyl, pyrimidyl, triazinyl, purinyl, and phenyl are optionally substituted by 1 or 2 substituents independently selected from NH 2 , NMe 2 , SMe, methyl, ethyl, halo, OH, OC 1-4 alkyl, and phenyl.

7. A compound according to claim 2 , wherein R10 is halo.

8. A compound according to claim 2 , wherein R11 is independently H, C 2-6 alkyl, or phenyl.

9. A compound according to claim 2 , wherein R11 is independently H, butyl, isopropyl, or phenyl.

10. A compound according to claim 2 , wherein R12 is halo.

11. A compound according to claim 2 , wherein R13 is independently H or C 1-6 alkyl.

12. A compound according to claim 2 , wherein R13 is independently H, butyl, or isopropyl.

13. A compound according to claim 2 , wherein:

R9 is independently H, halo, C 1-6 alkyl, or phenyl;

R10 is independently H, halo, pyridyl, pyrimidyl, triazinyl, purinyl or phenyl, wherein said pyridyl, pyrimidyl, triazinyl, purinyl, and phenyl are optionally substituted by 1 or 2 substituents independently selected from NH 2 , NMe 2 , SMe, methyl, ethyl, halo, OH, OC 1-4 alkyl, and phenyl;

R11 is independently H, C 2-6 alkyl, or phenyl;

R12 is independently H or halo; and

R13 is independently H, halo, or C 1-6 alkyl.

14. A compound according to claim 2 , wherein:

R9 is independently H, halo, C 1-6 alkyl, or phenyl;

R10 is independently halo, pyridyl, pyrimidyl, triazinyl, purinyl or phenyl, wherein said pyridyl, pyrimidyl, triazinyl, purinyl, and phenyl are optionally substituted by 1 or 2 substituents independently selected from NH 2 , NMe 2 , SMe, methyl, ethyl, halo, OH, OC 1-4 alkyl, and phenyl;

R11 is independently H, C 2-6 alkyl, or phenyl;

R12 is independently H or halo; and

R13 is independently H, halo, or C 1-6 alkyl.

15. A compound according to claim 2 , wherein:

R9 is independently H, F, Cl, isopropyl, or phenyl;

R10 is independently H, halo, pyridyl, pyrimidyl, triazinyl, phenyl, or purinyl, wherein said pyridyl, pyrimidyl, triazinyl, purinyl and phenyl are optionally substituted by 1 or 2 substituents independently selected from NH 2 , NMe 2 , methyl, ethyl, halo, OH, OC 1-4 alkyl, and phenyl;

R11 is independently H, butyl, isopropyl, or phenyl;

R12 is independently H or halo; and

R13 is independently H, F, C, or isopropyl.

16. A compound according to claim 2 , wherein:

R9 is independently H, F, Cl, isopropyl, or phenyl;

R10 is independently halo, pyridyl, pyrimidyl, triazinyl, phenyl, or purinyl, wherein said pyridyl, pyrimidyl, triazinyl, purinyl and phenyl are optionally substituted by 1 or 2 substituents independently selected from NH 2 , NMe 2 , methyl, ethyl, halo, OH, OC 1-4 alkyl, and phenyl;

R11 is independently H, butyl, isopropyl, or phenyl;

R12 is independently H or halo; and

R13 is independently H, F, Cl, or isopropyl.

17. A compound according to claim 2 , wherein:

R9 is H;

R10 is halo;

R11 is H;

R12 is H; and

R13 is H.

18. A pharmaceutical composition comprising at least one compound according to claim 2 in admixture with one or more pharmaceutically acceptable carriers and/or excipients.

19. A pharmaceutical composition comprising at least one compound according to claim 1 in admixture with one or more pharmaceutically acceptable carriers and/or excipients.