Fused heteroaromatic pyrrolidinones

1. A method of treating a disease or condition by inhibiting SYK in a subject in need thereof, the method comprising administering to the subject an effective amount of a compound of Formula 1,

or a pharmaceutically acceptable salt thereof, wherein:

G is C(R 5 );

L 1 and L 2 are each independently selected from —NH— and a bond;

R 1 and R 2 are each independently selected from hydrogen, halo, C 1-3 alkyl, and C 1-3 haloalkyl, or R 1 and R 2 , together with the atom to which they are attached, form a C 3-6 cycloalkyl;

R 3 is selected from C 2-6 alkyl, C 3-8 cycloalkyl, C 2-5 heterocyclyl, and C 1-9 heteroaryl, each optionally substituted with from one to five substituents independently selected from halo, oxo, —NO 2 , —CN, R 6 , and R 7 ;

R 4 is selected from C 3-8 cycloalkyl, C 2-5 heterocyclyl, C 6-14 aryl, and C 1-9 heteroaryl, each optionally substituted with from one to five substituents independently selected from halo, oxo, —CN, R 6 , and R 7 ;

R 5 is selected from hydrogen, halo, —CN, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 2-5 heterocyclyl, C 1-5 heteroaryl, and R 10 , wherein the alkyl, alkenyl, alkynyl moieties are each optionally substituted with from one to five substituents independently selected from halo, —CN, oxo, and R 10 , and wherein the heterocyclyl moiety has 3 to 6 ring atoms and the heteroaryl moiety has 5 or 6 ring atoms, and the heterocyclyl and heteroaryl moieties are each optionally substituted with from one to four substituents independently selected from halo, —NO 2 , —CN, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 1-4 haloalkyl, and R 10 ;

each R 6 is independently selected from —OR 8 , —N(R 8 )R 9 , —NR 8 C(O)R 9 , —C(O)R 8 , —C(O)OR 8 , —C(O)N(R 8 )R 9 , —C(O)N(R 8 )OR 9 , —C(O)N(R 8 )S(O) 2 R 9 , —N(R 8 )S(O) 2 R 9 , —S(O) n R 8 , and —S(O) 2 N(R 8 )R 9 ;

each R 7 is independently selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-6 cycloalkyl-(CH 2 ) m —, C 6-14 aryl-(CH 2 ) m —, C 2-5 heterocyclyl-(CH 2 ) m —, and C 1-9 heteroaryl-(CH 2 ) m —, each optionally substituted with from one to five substituents independently selected from halo, oxo, —NO 2 , —CN, C 1-6 alkyl, C 1-6 haloalkyl, and R 10 ;

each R 8 and R 9 is independently selected from hydrogen or from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 3-6 cycloalkyl-(CH 2 ) m —, C 6-14 aryl-(CH 2 ) m —, C 2-5 heterocyclyl-(CH 2 ) m —, and C 1-9 heteroaryl-(CH 2 ) m —, each optionally substituted with from one to five substituents independently selected from halo, oxo, —NO 2 , —CN, C 1-6 alkyl, C 1-6 haloalkyl, and R 10 ;

each R 10 is independently selected from —OR 11 , —N(R 11 )R 12 , —N(R 11 )C(O)R 12 , —C(O)R 11 , —C(O)OR 11 , —C(O)N(R 11 )R 12 , —C(O) N(R 11 )OR 12 , —C(O)N(R 11 )S(O) 2 R 12 , —NR 11 S(O) 2 R 12 , —S(O) n R 11 , and —S(O) 2 N(R 11 )R 12 ;

each R 11 and R 12 is independently selected from hydrogen and C 1-6 alkyl;

each n is independently selected from 0, 1 and 2; and

each m is independently selected from 0, 1, 2, 3, and 4;

wherein each of the aforementioned heteroaryl moieties has one to four heteroatoms independently selected from N, O, and S, and each of the aforementioned heterocyclyl moieties is saturated or partially unsaturated and has one or two heteroatoms independently selected from N, O, and S.

2. A method according to claim 1 , wherein L 1 is —NH—.

3. A method according to claim 1 , wherein L 2 is a bond.

4. A method according to claim 1 , wherein G is C(R 5 ).

5. A method according to claim 1 , wherein R 1 and R 2 are both hydrogen.

6. A method according to claim 1 , wherein R 3 is C 3-8 cycloalkyl, optionally substituted with from one to five substituents independently selected from halo, oxo, —NO 2 , —CN, R 6 , and R 7 .

7. A method according to claim 6 , wherein R 3 is 2-amino-cyclohex-1-yl optionally substituted with from one to four substituents independently selected from halo, oxo, —NO 2 , —CN, R 6 , and R 7 .

8. A method according to claim 1 , wherein R 3 is C 2-5 heterocyclyl optionally substituted with from one to five substituents independently selected from halo, oxo, —NO 2 , —CN, R 6 , and R 7 .

9. A method according to claim 8 , wherein R 3 is 3-aminotetrahydro-2H-pyran-4-yl optionally substituted with from one to four substituents independently selected from halo, oxo, —NO 2 , —CN, R 6 , and R 7 .

10. A method according to claim 1 , wherein R 4 is C 1-9 heteroaryl optionally substituted with from one to five substituents independently selected from halo, oxo, —CN, R 6 , and R 7 .

11. A method according to claim 10 , wherein R 4 is a monocyclic C 2-4 heteroaryl optionally substituted with from one to four substituents independently selected from halo, —CN, R 6 , and R 7 .

12. A method according to claim 11 , wherein R 4 is selected from pyrrolyl, furanyl, thienyl, pyrazolyl, imidazolyl, isoxazolyl, oxazolyl, isothiazolyl, and thiazolyl, each optionally substituted with from one to three substituents independently selected from halo, —CN, R 6 , and R 7 .

13. A method according to claim 12 , wherein R 4 is selected from thienyl, pyrazolyl, isothiazolyl, and thiazolyl, each optionally substituted with from one to three substituents independently selected from halo, —CN, R 6 , and R 7 .

14. A method according to claim 13 , wherein R 4 is pyrazolyl optionally substituted with from one to three substituents independently selected from halo, —CN, R 6 , and R 7 .

15. A method according to claim 14 , wherein R 4 is pyrazol-4-yl optionally substituted with from one to three substituents independently selected from halo, —CN, R 6 , and R 7 .

16. A method according to claim 10 , wherein R 4 is substituted with methyl, ethyl, cyclopropyl or C 1-2 haloalkyl.

17. A method according to claim 1 , wherein R 5 is selected from hydrogen and halo.

18. A method according to claim 17 , wherein R 5 is selected from chloro and fluoro.

19. A method according to claim 1 , wherein the compound is selected from the following compounds:

6-((1R,2S)-2-Aminocyclohexylamino)-4-(m-tolylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

4-(1H-Indazol-6-ylamino)-6-((1R,2S)-2-aminocyclohexylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-4-(4-fluoro-3-methylphenylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-7-fluoro-4-(m-tolylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((3R,4R)-3-Aminotetrahydro-2H-pyran-4-ylamino)-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-7-chloro-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-7-fluoro-4-(pyrazolo[1,5-a]pyridin-3-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-4-(3-(methylsulfonyl)phenylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclopentylamino)-4-(3-(methylsulfonyl)phenylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

(R)-4-Methyl-2-(4-(3-(methylsulfonyl)phenylamino)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)pentanamide;

(R)-4-Methyl-2-(4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)pentanamide;

6-((1R,2S)-2-Aminocyclohexylamino)-4-(benzofuran-3-yl)-7-fluoro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-aminocyclohexylamino)-7-fluoro-4-(imidazo[1,2-a]pyridin-3-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-aminocyclohexylamino)-4-(benzo[b]thiophen-3-yl)-7-fluoro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1S,2R)-2-Aminocyclohexylamino)-7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

(R)-6-(2-Amino-3-ethoxypropylamino)-4-(m-tolylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

(R)-6-(2-Amino-3-ethoxypropylamino)-7-fluoro-4-(m-tolylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-(2-Amino-3,3,3-trifluoropropylamino)-4-(m-tolylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

(R)-4-Methyl-2-(3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)pentanamide;

6-(cis-4-Aminotetrahydrofuran-3-ylamino)-4-(m-tolylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-4-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-4-(1-ethyl-1H-pyrazol-4-yl)-7-fluoro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-4-(1-cyclopropyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-4-(1-(difluoromethyl)-1H-pyrazol-4-yl)-7-fluoro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-4-(1-cyclopropyl-1H-pyrazol-4-yl)-7-fluoro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

cis-6-(2-Aminocyclohexylamino)-7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((3R,4R)-3-Aminotetrahydro-2H-pyran-4-ylamino)-7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-(cis-2-Amino-4,4-difluorocyclopentylamino)-7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-(cis-2-Amino-3,3-difluorocyclohexylamino)-7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-(cis-2-Amino-3,3-difluorocyclohexylamino)-4-(1-(difluoromethyl)-1H-pyrazol-4-yl)-7-fluoro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-(cis-2-amino-3,3-difluorocyclohexylamino)-4-(1-cyclopropyl-1H-pyrazol-4-yl)-7-fluoro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

(R)-2-(7-Fluoro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamide;

(R)-2-(4-(1-(Difluoromethyl)-1H-pyrazol-4-yl)-7-fluoro-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamide;

(R)-2-(4-(1-Cyclopropyl-1H-pyrazol-4-yl)-7-fluoro-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamide;

(R)-2-(4-(Benzofuran-3-yl)-7-fluoro-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamide;

(R)-2-(7-Fluoro-3-oxo-4-(pyrazolo[1,5-a]pyridin-3-yl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamide;

6-((1R,2S)-2-Aminocyclohexylamino)-7-chloro-4-(m-tolylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitrile;

(R)-6-(2-Amino-3-methoxypropylamino)-4-(m-tolylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

(R)-6-(2-Amino-3-methoxypropylamino)-3-oxo-4-(m-tolylamino)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitrile;

(R)-6-(2-Amino-3-methoxypropylamino)-7-fluoro-4-(m-tolylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

7-Acryloyl-6-((1R,2S)-2-aminocyclohexylamino)-4-(m-tolylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-7-iodo-4-(m-tolylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-7-(1H-pyrazol-4-yl)-4-(m-tolylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-(cis-2-Amino-3,3-difluorocyclohexylamino)-4-(m-tolylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-7-(1-methyl-1H-pyrazol-5-yl)-4-(m-tolylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((3R,4R)-3-Aminotetrahydro-2H-pyran-4-ylamino)-4-(m-tolylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((3R,4R)-4-Aminotetrahydro-2H-pyran-3-ylamino)-4-(m-tolylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-7-methyl-4-(m-tolylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((3R,4R)-3-Aminotetrahydro-2H-pyran-4-ylamino)-7-fluoro-4-(m-tolylamino)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-7-methyl-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

(R)-6-(2-Amino-3-methoxypropylamino)-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((3R,4R)-3-Aminotetrahydro-2H-pyran-4-ylamino)-7-fluoro-4-(pyrazolo[1,5-a]pyridin-3-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((3R,4R)-3-Aminotetrahydro-2H-pyran-4-ylamino)-4-(1-(difluoromethyl)-1H-pyrazol-4-yl)-7-fluoro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((3R,4R)-3-Aminotetrahydro-2H-pyran-4-ylamino)-4-(benzofuran-3-yl)-7-fluoro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

(S)-6-(3-Aminopyrrolidin-1-yl)-7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

(S)-6-(3-Aminopiperidin-1-yl)-7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-7-fluoro-4-(1-isopropyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

7-Fluoro-4,6-bis(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-7-bromo-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

(R)-6-(2-Amino-3-methoxypropylamino)-7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((3R,4R)-3-Aminotetrahydro-2H-pyran-4-ylamino)-7-fluoro-4-(thiophen-3-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((3R,4R)-3-Aminotetrahydro-2H-pyran-4-ylamino)-7-fluoro-4-(4-methylthiophen-2-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-7-fluoro-4-(4-methylthiophen-2-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-7-fluoro-4-(thiophen-3-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

(R)-2-(7-Fluoro-4-(1-methyl-1H-pyrazol-4-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-N,4-dimethylpentanamide;

6-((1R,2S)-2-Aminocyclohexylamino)-7-fluoro-4-(5-methylthiophen-2-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

(R)-2-(7-Fluoro-4-(4-methylthiophen-2-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamide;

(R)-2-(7-Fluoro-3-oxo-4-(thiophen-3-yl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamide;

(R)-2-(7-Fluoro-4-(5-methylthiophen-2-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamide;

6-((1R,2S)-2-Aminocyclohexylamino)-4-(2-aminothiazol-5-yl)-7-fluoro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

(R)-2-(7-Fluoro-4-(furan-2-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamide;

(R)-2-(7-Fluoro-4-(furan-3-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamide;

(R)-2-(7-Fluoro-4-(5-methylfuran-2-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamide;

(R)-2-(4-(5-Cyanothiophen-2-yl)-7-fluoro-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamide;

(R)-2-(4-(4-Cyanothiophen-2-yl)-7-fluoro-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamide;

(R)-2-(7-Fluoro-3-oxo-4-(thiazol-5-yl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamide;

(R)-2-(7-Fluoro-4-(isothiazol-5-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamide;

6-((1R,2S)-2-Aminocyclohexylamino)-7-fluoro-1,1-dimethyl-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

((1R,2S)-2-Aminocyclohexylamino)-7-fluoro-4-(1-methyl-1H-pyrazol-3-yl)-1H -pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-7-fluoro-4-(2-methylthiazol-5-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((3R,4R)-3-Aminotetrahydro-2H-pyran-4-ylamino)-7-fluoro-4-(5-methylthiophen-2-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-7-fluoro-1-methyl-4-(1-methyl-1H-pyrazol-4-yl) -1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

(R)-2-(7-Fluoro-3-oxo-4-(thiophen-2-yl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamide;

6-((3R,4R)-3-Aminotetrahydro-2H-pyran-4-ylamino)-7-fluoro-4-(thiophen-2-yl)-1H -pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((3R,4R)-3-Aminotetrahydro-2H-pyran-4-ylamino)-7-fluoro-4-(thiazol-5-yl)-1H -pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-7-fluoro-4-(thiophen-2-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((3R,4R)-3-Aminotetrahydro-2H-pyran-4-ylamino)-7-fluoro-4-(4-(trifluoromethyl)-1H -imidazol-1-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((1R,2S)-2-Aminocyclohexylamino)-7-fluoro-4-(4-methyl-1H-imidazol-1-yl)-1H -pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((3R,4R)-3-Aminotetrahydro-2H-pyran-4-ylamino)-7-fluoro-4-(3-methylisothiazol-5-yl)-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((3R,4R)-3-Aminotetrahydro-2H-pyran-4-ylamino)-7-fluoro-4-(2-methylthiazol-5-yl) -1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

(R)-2-(7-Fluoro-4-(2-methylthiazol-5-yl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-6-ylamino)-4-methylpentanamide;

6-((3R,4R)-3-Aminotetrahydro-2H-pyran-4-ylamino)-4-(5-chlorothiophen-2-yl)-7-fluoro -1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

6-((3R,4R)-3-Aminotetrahydro-2H-pyran-4-ylamino)-4-(1-cyclopropyl-1H-pyrazol-4-yl) -7-fluoro-1H-pyrrolo[3,4-c]pyridin-3(2H)-one;

a stereoisomer of any of the aforementioned compounds; and

a pharmaceutically acceptable salt of any of the aforementioned compounds or stereoisomers.

20. A method according to claim 1 , wherein the compound is 6-((1R, 2S )-2-Aminocyclohexylamino)-7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[3,4-c]pyridin-3( 2H )-one or a pharmaceutically acceptable salt thereof.

21. A method according to claim 1 , wherein the compound is 6-((1S,2R)-2-Aminocyclohexylamino)-7-fluoro-4-(1-methyl-1H-pyrazol-4-yl) -1H-pyrrolo[3 ,4-c]pyridin-3( 2H )-one or a pharmaceutically acceptable salt thereof.

22. A method according to claim 1 , wherein the compound is 6-((1R,25)-2-Aminocyclohexylamino)-4-(1 -(difluoromethyl)-1H-pyrazol-4-yl)-7-fluoro-1H-pyrrolo [3,4-c]pyridin-3( 2H )-one or a pharmaceutically acceptable salt thereof.

23. A method according to claim 1 , wherein the compound is cis-6-(2-Aminocyclohexylamino)-7-fluoro-4-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo [3 ,4-c]pyridin-3( 2H ) -one or a pharmaceutically acceptable salt thereof.

24. A method according to claim 1 , wherein the compound is 6-((3R,4R)-3-Aminotetrahydro-2H-pyran-4-ylamino)-4-(1-(difluoromethyl)-1H-pyrazol-4-yl)-7-fluoro-1H -pyrrolo[3,4-c]pyridin-3( 2H )-one or a pharmaceutically acceptable salt thereof.

25. A method according to claim 1 , wherein the compound is 6-((3R,4R)-3-Aminotetrahydro-2H-pyran-4-ylamino)-7-fluoro-4-(3 -methylisothiazol-5-yl)-1H-pyrrolo[3,4-c]pyridin-3( 2H )-one or a pharmaceutically acceptable salt thereof.

26. A method of treating a disease or condition by inhibiting SYK in a subject in need thereof, the method comprising administering to the subject an effective amount of a compound of Formula 1,

or a pharmaceutically acceptable salt thereof, wherein:

G is C(R 5 );

L 1 and L 2 are each independently selected from -NH- and a bond;

R 1 and R 2 are each independently selected from hydrogen, halo, C 1-3 alkyl, and C 1-3 haloalkyl, or R 1 and R 2 , together with the atom to which they are attached, form a C 3-6 cycloalkyl;

R 3 is selected from C 2-6 alkyl, C 3-8 cycloalkyl, C 2-5 heterocyclyl, and C 1-9 heteroaryl, each optionally substituted with from one to five substituents independently selected from halo, oxo, -NO 2 , -CN, R 6 , and R 7 ;

R 4 is selected from C 3-8 cycloalkyl, C 2-5 heterocyclyl, C 6-14 aryl, and C 1-9 heteroaryl, each optionally substituted with from one to five substituents independently selected from halo, oxo, -CN, R 6 , and R 7 ;

R 5 is selected from hydrogen, halo, -CN, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 2-5 heterocyclyl,

C 1-5 heteroaryl, and R 10 , wherein the alkyl, alkenyl, alkynyl moieties are each optionally substituted with from one to five substituents independently selected from halo, -CN, oxo, and R 10 , and wherein the heterocyclyl moiety has 3 to 6 ring atoms and the heteroaryl moiety has 5 or 6 ring atoms, and the heterocyclyl and heteroaryl moieties are each optionally substituted with from one to four substituents independently selected from halo, -NO 2 , -CN, C 1-4 alkyl, C 2-4 alkenyl, C 2-4 alkynyl, C 1-4 haloalkyl, and R 10 ;

each R 6 is independently selected from -OR 8 , -N(R 8 )R 9 , -NR 8 C(O)R 9 , -C(O)R 8 , -C(O)OR 8 , -C(O)N(R 8 )R 9 , -C(O)N(R 8 )OR 9 , -C(O)N(R 8 )S(O) 2 R 9 , -N(R 8 )S(O) 2 R 9 , -S(O) n R 8 , and -S(O) 2 N(R 8 )R 9 ;

each R 7 is independently selected from C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl,

C 3-6 cycloalkyl-(CH 2 ) m -, C 6-14 aryl-(CH 2 ) m -, C 2-5 heterocyclyl-(CH 2 ) m -, and C 1-9 heteroaryl-(CH 2 ) m -, each optionally substituted with from one to five substituents independently selected from halo, oxo, -NO 2 , -CN, C 1-6 alkyl, C 1-6 haloalkyl, and R 10 ;

each R 8 and R 9 is independently selected from hydrogen or from C 1-6 alkyl, C 2-6 alkenyl,

C 2-6 alkynyl, C 3-6 cycloalkyl-(CH 2 ) m -, C 6-14 aryl-(CH 2 ) m -, C 2-5 heterocyclyl-(CH 2 ) m -, and C 1-9 heteroaryl-(CH 2 ) m -, each optionally substituted with from one to five substituents independently selected from halo, oxo, -NO 2 , -CN, C 1-6 alkyl, C 1-6 haloalkyl, and R 10 ; each R 10 is independently selected

from -OR 11 , -N(R 11 )R 12 ,-N(R 11 )C(O)R 12 , -C(O)OR 11 , -C(O)N(R 11 )R 12 , -C(O) N(R 11 )OR 12 , -C(O)N(R 11 )S(O) 2 R 12 , -NR 11 S(O) n R 11 , and -S(O) 2 N(R 11 )R 12 ; each R 11 and R 12 is independently selected from hydrogen and C 1-6 alkyl;

each n is independently selected from 0, 1 and 2; and

each m is independently selected from 0, 1, 2, 3, and 4;

wherein each of the aforementioned heteroaryl moieties has one to four heteroatoms independently selected from N, O, and S, and each of the aforementioned heterocyclyl moieties is saturated or partially unsaturated and has one or two heteroatoms independently selected from N, O, and S;

wherein the disease or condition is selected from allergic rhinitis, allergic asthma, atopic dermatitis, rheumatoid arthritis, multiple sclerosis, systemic lupus erythematosus, psoriasis, immune thrombocytopenic purpura, inflammatory bowel disease, chronic obstructive pulmonary disease, thrombosis, a hematological malignancy, and an epithelial cancer.

27. A method according to claim 26 , wherein the hematological malignancy is selected from acute myeloid leukemia, B-cell chronic lymphocytic leukemia, B-cell lymphoma, and T-cell lymphoma.

28. A method according to claim 26 , wherein the epithelial cancer is selected from lung cancer, pancreatic cancer, and colon cancer.

29. A method according to claim 26 , the method further comprising administering to the subject at least one additional pharmacologically active agent.

30. A method according to claim 29 , wherein the additional pharmacologically active agent is a DMARD.

31. A method according to claim 30 , wherein the DMARD is methotrexate.