Phenyl carboxamide-containing spleen tyrosine kinase (SYK) inhibitors

1. A compound of the Formula (I)

or a pharmaceutically acceptable salt thereof, wherein

B is pyridyl or quinolinyl;

wherein B is unsubstituted or substituted by 1 to 3 R 3 moieties, wherein each R 3 moiety is independently selected from the group consisting of: C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 fluoroalkyl, C 1 -C 3 hydroxyalkyl, halo, hydroxy, amino, (C 1 -C 3 alkyl)amino, di(C 1 -C 3 alkyl)amino, and E;

wherein E is phenyl, a 5- or 6-membered heteroaryl containing 1 to 3 N atoms, or a 6-membered heterocyclyl containing 1 to 2 heteroatoms selected from the group consisting of N and O;

wherein E is unsubstituted or substituted by 1 to 2 moieties independently selected from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 alkoxy, and halo;

A is

 wherein

Y is —CH 2 — or —O—;

R 11 and R 12 are independently H or F; and

n′ is 0 or 1.

2. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein B is substituted by no more than 2 R 3 moieties, and no more than 1 of said R 3 moieties is E.

3. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein B is substituted by 1 to 3 R 3 moieties, and one of said R 3 moieties is E.

4. The compound of claim 1 , or a pharmaceutically acceptable salt thereof wherein A is selected from the group consisting of

5. The compound of claim 4 , or a pharmaceutically acceptable salt thereof wherein A is

6. The compound of claim 1 having the Formula (IA)

or a pharmaceutically acceptable salt thereof, wherein

R 3a is H, halo, C 1 -C 3 alkyl, C 1 -C 3 alkoxy, C 1 -C 3 fluoroalkyl, or E a ;

wherein E a is phenyl, pyridyl, pyrazolyl, pyrrolyl, or morpholinyl wherein said phenyl, pyridyl, pyrazolyl, or pyrrolyl of E a is unsubstituted or substituted by 1 to 2 moieties selected from the group consisting of C 1 -C 3 alkyl, C 1 -C 3 alkoxy, and halo;

R 3b is H or halo;

or R 3a and R 3b together with the carbon atoms to which they are attached form a phenyl ring; and

R 3c is H or C 1 -C 3 alkyl.

7. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is selected from the group consisting of:

rel-4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-[(6-methoxypyridin-2-yl)amino]benzamide;

rel-4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-[(4,6-dimethylpyridin-2-yl)amino]benzamide;

rel-4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-{[6-(1H-pyrazol-1-yl)pyridin-2-yl]amino}benzamide;

rel-4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-[(5 -fluoro-6-methylpyridin-2-yl)amino]benzamide;

rel-4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-[(6-morpholin-4-ylpyridin-2-yl)amino]benzamide;

rel-4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-[(6-ethoxypyridin-2-yl)amino]benzamide;

rel-4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-[(6-phenylpyridin-2-yl)amino]benzamide;

rel-4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-(2,4′-bipyridin-6-ylamino)benzamide;

rel-4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-{[6-(3-methoxyphenyl)pyridin-2-yl]amino}benzamide;

rel-4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-{[6-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl]amino}benzamide;

rel-4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-{[6-(3-fluorophenyl)pyridin-2-yl]amino}benzamide;

rel-4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-{[6-(2-methoxyphenyl)pyridin-2-yl]amino}benzamide;

rel-4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-{[6-(4-methoxyphenyl)pyridin-2-yl]amino}benzamide;

rel-4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-{[6-(4-fluorophenyl)pyridin-2-yl]amino}benzamide;

rel-4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-(quinolin-2-ylamino)benzamide;

rel-4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-{[6-(3,4-difluorophenyl)pyridin-2-yl]amino}benzamide;

rel-4-{[(1R,2S)-2-aminocyclohexyl]amino}-2- {[6-(1H-pyrrol-1-yl)pyridin-2-yl]amino}benzamide; and

rel-4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-[(6-methylpyridin-2-yl)amino]benzamide.

8. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is selected from the group consisting of:

4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-[(6-methoxypyridin-2-yl)amino]benzamide;

4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-[(4,6-dimethylpyridin-2-yl)amino]benzamide;

4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-{[6-(1H-pyrazol-1-yl)pyridin-2-yl]amino}benzamide;

4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-[(5-fluoro-6-methylpyridin-2-yl)amino]benzamide;

4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-[(6-morpholin-4-ylpyridin-2-yl)amino]benzamide;

4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-[(6-ethoxypyridin-2-yl)amino]benzamide;

4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-[(6-phenylpyridin-2-yl)amino]benzamide;

4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-(2,4′-bipyridin-6-ylamino)benzamide;

4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-{[6-(3 -methoxyphenyl)pyridin-2-yl]amino}benzamide;

4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-{[6-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl]amino}benzamide;

4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-{[6-(3-fluorophenyl)pyridin-2-yl]amino}benzamide;

4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-{[6-(2-methoxyphenyl)pyridin-2-yl]amino}benzamide;

4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-{[6-(4-methoxyphenyl)pyridin-2-yl]amino}benzamide;

4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-{[6-(4-fluorophenyl)pyridin-2-yl]amino}benzamide;

4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-(quinolin-2-ylamino)benzamide;

4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-{[6-(3,4-difluorophenyl)pyridin-2-yl]amino}benzamide;

4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-{[6-(1H-pyrrol-1-yl)pyridin-2-yl]amino}benzamide; and

4-{[(1R,2S)-2-aminocyclohexyl]amino}-2-[(6-methylpyridin-2-yl)amino]benzamide.

9. A pharmaceutical composition comprising a therapeutically effective amount of the compound of claim 1 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

10. The pharmaceutical composition of claim 9 , further comprising an additional therapeutic agent.