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Abstract
A compound according to Formula I: or a pharmaceutically-acceptable salt thereof, wherein R1, R3, A, B and D are as defined in the specification; pharmaceutical compositions thereof, and methods of use thereof.
35 Citations
20 Claims
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1. A compound according to Formula I:
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 17, 18, 19, 20)
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2. A compound according to claim 1, according to Formula IA or Formula IB:
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3. The compound of Formula IA according to claim 2, or a pharmaceutically acceptable salt thereof, wherein R1 is selected from —
- NR4R5, —
(C1-C4)alky-NR8R9, —
O—
(C1-C4)alky-NR8R9, heteroaryl optionally substituted with amino, hydroxyl, alkoxyl or aryl-(C1-C3)alkyl, (5-6 membered)heterocycloalkyl optionally substituted with hydroxyl, amino, alkynyl substituted with hydroxyl or —
(CH2)0-3—
NR8R9, phenyl substituted with —
CF3 or cyano, and alkyl substituted with hydroxyl, wherein R4, R5, R8 and R9 are as defined in claim 1.
- NR4R5, —
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4. The compound of Formula IA according to claim 2, or a pharmaceutically acceptable salt thereof, wherein:
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R1 is selected from NR4R5, —
(C1-C4)alky-NR8R9, —
O—
(C1-C4)alky-NR8R9, triazolyl optionally substituted with phenylmethyl, 1H-pyrrolo[2,3-b]pyridinyl, 1H-indolyl, pyridinyl optionally substituted with amino or methoxy, pyrazolyl, pyrimidinyl optionally substituted with amino, (5-6 membered)heterocycloalkyl optionally substituted with hydroxyl, and amino;R3 is phenyl, pyridine or pyrimidine, wherein the phenyl, pyridine or pyrimidine is optionally substituted with 1 or 2 substituents independently selected from amine, alkoxy, hydroxyl, alkyl and aminocarbonyl; R4 is selected from H, alkyl optionally substituted with 1, 2 or 3 groups independently selected from hydroxyl, amino, halo, alkoxy, alkylamino, dialkylamino and dialkylaminoalkyl, alkoxycarbonyl, alkoxyalkyl, oxo, —
CN, dialkylaminocarbonylalkyl optionally substituted with hydroxyl, cycloalkyl optionally substituted with amine, aryl optionally substituted with amine, arylalkyl, heteroarylalkyl optionally substituted with alkyl, heterocycloalkylalkyl and heterocycloalkyl optionally substituted with 1, 2 or 3 substituents independently selected from alkyl, hydroxyl, amino, and hydroxyalkyl;R5 is selected from alkyl optionally substituted with 1, 2 or 3 groups independently selected from hydroxyl, amino, halo, alkoxy, alkylamino, dialkylamino and dialkylaminoalkyl, alkoxycarbonyl, alkoxyalkyl, oxo, —
CN, dialkylaminocarbonylalkyl optionally substituted with hydroxyl, cycloalkyl optionally substituted with amine, aryl optionally substituted with amine, arylalkyl, heteroarylalkyl optionally substituted with alkyl, heterocycloalkylalkyl and heterocycloalkyl optionally substituted with 1, 2 or 3 substituents independently selected from alkyl, hydroxyl, amino, and hydroxyalkyl;or R4 and R5, together with the nitrogen to which they are both attached, join together to form a heteroaryl group or a heterocycloalkyl group, wherein the heteroaryl group is selected from (1) isoindolinyl, (2) 1,2,3,4-tetrahydroisoquinolinyl optionally substituted with hydroxyl, and (3) indolinyl optionally substituted with hydroxyalkyl, and wherein the heterocycloalkyl group is selected from morpholinyl, piperidinyl, piperazinyl, pyrrolidinyl, imidazolidinyl, 3-azabicyclo[3.1.0]hexyl, 1,2,3,6-tetrahydropyridinyl, hexahydrocyclopenta[c]pyrrol-2(1H)-yl, hexahydrocyclopenta[c]pyrrol-5(1H)-yl, hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl), (4aR,8aR)-octahydro-1H-pyrido[3,4-b][1,4]oxazinyl, hexahydropyrrolo[3,4-b]pyrrol-2(1H)-yl), hexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl), thiazolidinyl, tetrahydro-3aH[1,3]dioxolo[4,5-c]pyrrolyl, hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl), azepanyl, 1,4-diazepanyl, (1S,4S)-2,5-diazabicyclo[2.2.1]heptanyl and azetanyl, wherein the heterocycloalkyl group is optionally substituted with 1, 2 or 3 substituents independently selected from halo, alkyl optionally substituted with 1-3 halo, carboxyalkyl, amino, hydroxyl, hydroxyalkyl, alkoxy optionally substituted with 1-3 halo, alkoxyalkyl optionally substituted with 1-3 halo, —
(CH2)0-3-heterocycloalkyl optionally substituted with alkyl, ═
N(H)—
OH, —
N(Boc)alkyl, spiroheterocycloalkyl optionally substituted with —
C(O)OR9 or —
NH2, (C1-C3)alkyl-O—
C(O)—
C(H)(NH2)—
(C1-C3)alkyl, —
(CH2)0-3—
O—
C(O)—
NR8R9, —
C(O)-aryl-R10, alkylcarbonylamino, alkoxyalkylcarbonylamino, heteroaryl optionally substituted with NR8R9, —
(CH2)0-3—
N(R8)R7, —
C(O)—
N(R8)R9, alkyl-C(O)N(H)(alkyl)-, aryl, arylalkyl optionally substituted with 1 or 2 groups selected from halo and alkyl, alkoxycarbonyl and aminoalkyl, provided that the optionally substituted heterocycloalkyl group cannot be substituted with more than one group selected from —
(CH2)0-3-heterocycloalkyl optionally substituted with alkyl, ═
N(H)—
OH, —
N(Boc)alkyl, spiroheterocycloalkyl optionally substituted with —
C(O)OR9 or —
NH2, —
(C1-C3)alkyl-O—
C(O)—
C(H)(NH2)—
(C1-C3)alkyl, —
(CH2)0-3—
O—
C(O)—
NR8R9, —
C(O)-aryl-R10, alkylcarbonylamino, alkoxyalkylcarbonylamino, heteroaryl optionally substituted with alkyl, (CH2)0-3—
N(R6)R7, —
C(O)—
N(R8)R9, alkyl-C(O)N(H)(alkyl)-, aryl, arylalkyl optionally substituted with 1 or 2 groups selected from halo and alkyl, and alkoxycarbonyl; andR6, R7, R8, R9, and R10 are as defined in claim 1.
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5. The compound of Formula IA according to claim 2, or a pharmaceutically acceptable salt thereof, wherein:
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R1 is selected from NR4R5, —
(C1-C4)alky-NR8R9, —
O—
(C1-C4)alky-NR8R9, triazolyl optionally substituted with phenylmethyl, 1H-pyrrolo[2,3-b]pyridinyl, 1H-indolyl, pyridinyl optionally substituted with amino or methoxy, pyrazolyl, pyrimidinyl optionally substituted with amino, (5-6 membered)heterocycloalkyl optionally substituted with hydroxyl, and amino;R3 is phenyl, pyridine or pyrimidine, wherein the phenyl, pyridine or pyrimidine is optionally substituted with 1 or 2 substituents independently selected from alkoxy, hydroxyl, amine, alkyl and aminocarbonyl; R4 is selected from H, 1-methylethyl, methyl, ethyl, propyl, 2-methylpropyl, phenylethyl, dimethylaminoethyl, methoxymethyl, piperidinyl optionally substituted with methyl, cyclopentyl, dimethylaminocarbonylmethyl, ethylpyrrolidinylmethyl, piperidinylethyl, methylaminoethyl, aminoethyl, pyrrolidinylethyl, 2-propane-1,3 diol, phenyl, carboxymethyl, dimethylaminopropyl, dimethylaminopropan-2-yl, dimethylaminopropan-1-ol-2-yl, methylaminopropyl, aminocyclohexyl, methoxyethyl, (2R)-pyrrolidinylmethyl, (2S)-pyrrolidinylmethyl, dimethylaminoethyl, pyrrolidinyl optionally substituted with methyl, propane-1,3-diol, hydroxymethyl, hydroxyethyl, aminomethyl, dimethylaminomethylcarbonylaminoethyl, dimethylamino, (R)-benzyl 2-amino-3-hydroxypropylcarbamate and methoxymethyl; R5 is selected from is selected from propyl, 1-methylethyl, methyl, ethyl, propyl, 2-methylpropyl, phenylethyl, dimethylaminoethyl, methoxymethyl, piperidinyl optionally substituted with methyl, cyclopentyl, dimethylaminocarbonylmethyl, ethylpyrrolidinylmethyl, piperidinylethyl, methylaminoethyl, aminoethyl, pyrrolidinylethyl, 2-propane-1,3 diol, phenyl, carboxymethyl, dimethylaminopropyl, dimethylaminopropan-2-yl, dimethylaminopropan-1-ol-2-yl, methylaminopropyl, aminocyclohexyl, methoxyethyl, (2R)-pyrrolidinylmethyl, (2S)-pyrrolidinylmethyl, dimethylaminoethyl, pyrrolidinyl optionally substituted with methyl, propane-1,3-diol, hydroxymethyl, hydroxyethyl, aminomethyl, dimethylaminomethylcarbonylaminoethyl, dimethylamino, (R)-benzyl 2-amino-3-hydroxypropylcarbamate and methoxymethyl; or R4 and R5, together with the nitrogen to which they are both attached, join together to form a heteroaryl group or a heterocycloalkyl group, wherein the heteroaryl group is selected from (1) isoindolinyl, (2) 1,2,3,4-tetrahydroisoquinolinyl optionally substituted with hydroxyl, and (3) indolinyl optionally substituted with hydroxyalkyl, and wherein the heterocycloalkyl group is selected from morpholinyl, piperidinyl, piperazinyl, pyrrolidinyl, imidazolidinyl, 3-azabicyclo[3.1.0]hexyl, 1,2,3,6-tetrahydropyridinyl, hexahydrocyclopenta[c]pyrrol-2(1H)-yl, hexahydrocyclopenta[c]pyrrol-5(1H)-yl, hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl), (4aR,8aR)-octahydro-1H-pyrido[3,4-b][1,4]oxazinyl, hexahydropyrrolo[3,4-b]pyrrol-2(1H)-yl), hexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl), thiazolidinyl, tetrahydro-3aH[1,3]dioxolo[4,5-c]pyrrolyl, hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl), azepanyl, 1,4-diazepanyl, (1S,4S)-2,5-diazabicyclo[2.2.1]heptanyl and azetanyl, wherein the heterocycloalkyl group is optionally substituted with 1, 2 or 3 substituents independently selected from halo, alkyl optionally substituted with 1-3 halo, carboxyalkyl, amino, hydroxyl, hydroxyalkyl, alkoxy optionally substituted with 1-3 halo, alkoxyalkyl optionally substituted with 1-3 halo, —
(CH2)0-3-heterocycloalkyl optionally substituted with alkyl, ═
N(H)—
OH, —
N(Boc)alkyl, spiroheterocycloalkyl optionally substituted with —
C(O)OR9 or —
NH2, (C1-C3)alkyl-O—
C(O)—
C(H)(NH2)—
(C1-C3)alkyl, —
(CH2)0-3—
O—
C(O)—
NR8R9, —
C(O)-aryl-R10, alkylcarbonylamino, alkoxyalkylcarbonylamino, heteroaryl optionally substituted with NR8R9, —
(CH2)0-3—
N(R6)R7, —
C(O)—
N(R8)R9, alkyl-C(O)N(H)(alkyl)-, aryl, arylalkyl optionally substituted with 1 or 2 groups selected from halo and alkyl, alkoxycarbonyl and aminoalkyl, provided that the optionally substituted heterocycloalkyl group cannot be substituted with more than one group selected from —
(CH2)0-3-heterocycloalkyl optionally substituted with alkyl, ═
N(H)—
OH, —
N(Boc)alkyl, spiroheterocycloalkyl optionally substituted with —
C(O)OR9 or —
NH2, —
(C1-C3)alkyl-O—
C(O)—
C(H)(NH2)—
(C1-C3)alkyl, —
(CH2)0-3—
O—
C(O)—
NR8R9, —
C(O)-aryl-R10, alkylcarbonylamino, alkoxyalkylcarbonylamino, heteroaryl optionally substituted with alkyl, (CH2)0-3—
N(R6)R7, —
C(O)—
N(R8)R9, alkyl-C(O)N(H)(alkyl)-, aryl, arylalkyl optionally substituted with 1 or 2 groups selected from halo and alkyl, and alkoxycarbonyl; andR6, R7, R8, R9, and R10 are as defined in claim 1.
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6. The compound according to claim 5, or a pharmaceutically acceptable salt thereof, wherein:
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R1 is a heterocycloalkyl group, wherein the heterocycloalkyl group is selected from morpholinyl, piperidinyl, piperazinyl, pyrrolidinyl, imidazolidinyl, 3-azabicyclo[3.1.0]hexyl, 1,2,3,6-tetrahydropyridinyl, hexahydrocyclopenta[c]pyrrol-2(1H)-yl, hexahydrocyclopenta[c]pyrrol-5(1H)-yl, hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl), (4aR,8aR)-octahydro-1H-pyrido[3,4-b][1,4]oxazinyl, hexahydropyrrolo[3,4-b]pyrrol-2(1H)-yl), hexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl), thiazolidinyl, tetrahydro-3aH[1,3]dioxolo[4,5-c]pyrrolyl, hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl), azepanyl, 1,4-diazepanyl, (1S,4S)-2,5-diazabicyclo[2.2.1]heptanyl and azetanyl, wherein the heterocycloalkyl group is optionally substituted with 1, 2 or 3 substituents independently selected from halo, alkyl optionally substituted with 1-3 halo, carboxyalkyl, amino, hydroxyl, hydroxyalkyl, alkoxy optionally substituted with 1-3 halo, alkoxyalkyl optionally substituted with 1-3 halo, —
(CH2)0-3-heterocycloalkyl optionally substituted with alkyl, ═
N(H)—
OH, —
N(Boc)alkyl, spiroheterocycloalkyl optionally substituted with —
C(O)OR9 or —
NH2, (C1-C3)alkyl-O—
C(O)—
C(H)(NH2)—
(C1-C3)alkyl, —
(CH2)0-3—
O—
C(O)—
NR8R9, —
C(O)-aryl-R10, alkylcarbonylamino, alkoxyalkylcarbonylamino, heteroaryl optionally substituted with NR8R9, —
(CH2)0-3—
N(R6)R7,—
C(O)—
N(R8)R9, alkyl-C(O)N(H)(alkyl)-, aryl, arylalkyl optionally substituted with 1 or 2 groups sele2cted from halo and alkyl, alkoxycarbonyl and aminoalkyl, provided that the optionally substituted heterocycloalkyl group cannot be substituted with more than one group selected from —
(CH2)0-3-heterocycloalkyl optionally substituted with alkyl, ═
N(H)—
OH, —
N(Boc)alkyl, spiroheterocycloalkyl optionally substituted with —
C(O)OR9 or —
NH2, —
(C1-C3)alkyl-O—
C(O)—
C(H)(NH2)—
(C1-C3)alkyl, —
(CH2)0-3—
O—
C(O)—
NR8R9, —
C(O)-aryl-R10, alkylcarbonylamino, alkoxyalkylcarbonylamino, heteroaryl optionally substituted with alkyl, (CH2)0-3—
N(R8)R7, —
C(O)—
N(R8)R9, alkyl-C(O)N(H)(alkyl)-, aryl, arylalkyl optionally substituted with 1 or 2 groups selected from halo and alkyl, and alkoxycarbonyl; andR8, R7, R8, R9, and R10 are as defined in claim 1.
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7. The compound of Formula IA according to claim 2, or a pharmaceutically acceptable salt thereof, wherein:
-
R1 is selected from NR4R5, —
(C1-C4)alky-NR8R9, —
O—
(C1-C4)alky-NR8R9, triazolyl optionally substituted with phenylmethyl, 1H-pyrrolo[2,3-b]pyridinyl, 1H-indolyl, pyridinyl optionally substituted with amino or methoxy, pyrazolyl, pyrimidinyl optionally substituted with amino, (5-6 membered)heterocycloalkyl optionally substituted with hydroxyl, and amino;R3 is phenyl, pyridine or pyrimidine, wherein the phenyl, pyridine or pyrimidine is optionally substituted with 1 or 2 substituents independently selected from amine, alkoxy, hydroxyl, alkyl and aminocarbonyl; R4 is selected from H, methyl, ethyl and propyl; R5 is selected from is selected from propyl, 1-methylethyl, methyl, ethyl, propyl, 2-methylpropyl, phenylethyl, dimethylaminoethyl, methoxymethyl, piperidinyl optionally substituted with methyl, cyclopentyl, dimethylaminocarbonylmethyl, ethylpyrrolidinylmethyl, piperidinylethyl, methylaminoethyl, aminoethyl, pyrrolidinylethyl, 2-propane-1,3 diol, phenyl, carboxymethyl, dimethylaminopropyl, dimethylaminopropan-2-yl, dimethylaminopropan-1-ol-2-yl, methylaminopropyl, aminocyclohexyl, methoxyethyl, (2R)-pyrrolidinylmethyl, (2S)-pyrrolidinylmethyl, dimethylaminoethyl, pyrrolidinyl optionally substituted with methyl, propane-1,3-diol, hydroxymethyl, hydroxyethyl, aminomethyl, dimethylaminomethylcarbonylaminoethyl, dimethylamino, (R)-benzyl 2-amino-3-hydroxypropylcarbamate and methoxymethyl; or R4 and R5, together with the nitrogen to which they are both attached, join together to form a heteroaryl group or a heterocycloalkyl group, wherein the heteroaryl group is selected from (1) isoindolinyl, (2) 1,2,3,4-tetrahydroisoquinolinyl optionally substituted with hydroxyl, and (3) indolinyl optionally substituted with hydroxyalkyl, and wherein the heterocycloalkyl group is selected from morpholinyl, piperidinyl, piperazinyl, pyrrolidinyl, imidazolidinyl, 3-azabicyclo[3.1.0]hexyl, 1,2,3,6-tetrahydropyridinyl, hexahydrocyclopenta[c]pyrrol-2(1H)-yl, hexahydrocyclopenta[c]pyrrol-5(1H)-yl, hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl), (4aR,8aR)-octahydro-1H-pyrido[3,4-b][1,4]oxazinyl, hexahydropyrrolo[3,4-b]pyrrol-2(1H)-yl), hexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl), thiazolidinyl, tetrahydro-3aH[1,3]dioxolo[4,5-c]pyrrolyl, hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl), azepanyl, 1,4-diazepanyl, (1S,4S)-2,5-diazabicyclo[2.2.1]heptanyl and azetanyl, wherein the heterocycloalkyl group is optionally substituted with 1, 2 or 3 substituents independently selected from halo, alkyl optionally substituted with 1-3 halo, carboxyalkyl, amino, hydroxyl, hydroxyalkyl, alkoxy optionally substituted with 1-3 halo, alkoxyalkyl optionally substituted with 1-3 halo, —
(CH2)0-3-heterocycloalkyl optionally substituted with alkyl, ═
N(H)—
OH, —
N(Boc)alkyl, spiroheterocycloalkyl optionally substituted with —
C(O)OR9 or —
NH2, (C1-C3)alkyl-O—
C(O)—
C(H)(NH2)—
(C1-C3)alkyl, —
(CH2)0-3—
O—
C(O)—
NR8R9, —
C(O)-aryl-R10, alkylcarbonylamino, alkoxyalkylcarbonylamino, heteroaryl optionally substituted with NR8R9, —
(CH2)0-3—
N(R6)R7, —
C(O)—
N(R8)R9, alkyl-C(O)N(H)(alkyl)-, aryl, arylalkyl optionally substituted with 1 or 2 groups selected from halo and alkyl, alkoxycarbonyl and aminoalkyl, provided that the optionally substituted heterocycloalkyl group is substituted cannot be substituted with more than one group selected from —
(CH2)0-3-heterocycloalkyl optionally substituted with alkyl, ═
N(H)—
OH, —
N(Boc)alkyl, spiroheterocycloalkyl optionally substituted with —
C(O)OR9 or —
NH2,—
(C1-C3)alkyl-O—
C(O)—
C(H)(NH2)—
(C1-C3)alkyl, —
(CH2)0-3—
O—
C(O)—
NR8R9, —
C(O)-aryl-R10, alkylcarbonylamino, alkoxyalkylcarbonylamino, heteroaryl optionally substituted with alkyl, (CH2)0-3—
N(R6)R7, —
C(O)—
N(R8)R9, alkyl-C(O)N(H)(alkyl)-, aryl, arylalkyl optionally substituted with 1 or 2 groups selected from halo and alkyl, and alkoxycarbonyl; andR6, R7, R8, R9, and R10 are as defined in claim 1.
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8. The compound of Formula IA according to claim 2, or a pharmaceutically acceptable salt thereof, wherein:
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R1 is a heterocycloalkyl group, wherein the heterocycloalkyl group is selected from morpholinyl, piperidinyl, piperazinyl, pyrrolidinyl, imidazolidinyl, 3-azabicyclo[3.1.0]hexyl, 1,2,3,6-tetrahydropyridinyl, hexahydrocyclopenta[c]pyrrol-2(1H)-yl, hexahydrocyclopenta[c]pyrrol-5(1H)-yl, hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl), (4aR,8aR)-octahydro-1H-pyrido[3,4-b][1,4]oxazinyl, hexahydropyrrolo[3,4-b]pyrrol-2(1H)-yl), hexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl), thiazolidinyl, tetrahydro-3aH[1,3]dioxolo[4,5-c]pyrrolyl, hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl), azepanyl, 1,4-diazepanyl, (1S,4S)-2,5-diazabicyclo[2.2.1]heptanyl and azetanyl, wherein the heterocycloalkyl group is optionally substituted with 1, 2 or 3 substituents independently selected from halo, alkyl optionally substituted with 1-3 halo, carboxyalkyl, amino, hydroxyl, hydroxyalkyl, alkoxy optionally substituted with 1-3 halo, alkoxyalkyl optionally substituted with 1-3 halo, —
(CH2)0-3-heterocycloalkyl optionally substituted with alkyl, ═
N(H)—
OH, —
N(Boc)alkyl, spiroheterocycloalkyl optionally substituted with —
C(O)OR9 or —
NH2, (C1-C3)alkyl-O—
C(O)—
C(H)(NH2)—
(C1-C3)alkyl, —
(CH2)0-3—
O—
C(O)—
NR8R9, —
C(O)-aryl-R10, alkylcarbonylamino, alkoxyalkylcarbonylamino, heteroaryl optionally substituted with NR8R9, —
(CH2)0-3—
N(R6)R7,—
C(O)—
N(R8)R9, alkyl-C(O)N(H)(alkyl)-, aryl, arylalkyl optionally substituted with 1 or 2 groups selected from halo and alkyl, alkoxycarbonyl and aminoalkyl, provided that the optionally substituted heterocycloalkyl group cannot be substituted with more than one group selected from —
(CH2)0-3-heterocycloalkyl optionally substituted with alkyl, ═
N(H)—
OH, —
N(Boc)alkyl, spiroheterocycloalkyl optionally substituted with —
C(O)OR9 or —
NH2, —
(C1-C3)alkyl-O—
C(O)—
C(H)(NH2)—
(C1-C3)alkyl, —
(CH2)0-3—
O—
C(O)—
NR8R9, —
C(O)-aryl-R10, alkylcarbonylamino, alkoxyalkylcarbonylamino, heteroaryl optionally substituted with alkyl, (CH2)0-3—
N(R6)R7, —
C(O)—
N(R8)R9, alkyl-C(O)N(H)(alkyl)-, aryl, arylalkyl optionally substituted with 1 or 2 groups selected from halo and alkyl, and alkoxycarbonyl; andR6, R7, R8, R9, and R10 are as defined in claim 1.
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9. The compound according to claim 1, or a pharmaceutically acceptable salt thereof, having Formula II, III, IV, V, VI or VII:
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10. The compound according to claim 9, or a pharmaceutically acceptable salt thereof, wherein:
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R4 is selected from H, 1-methylethyl, methyl, ethyl, propyl, 2-methylpropyl, phenylethyl, dimethylaminoethyl, methoxymethyl, piperidinyl optionally substituted with methyl, cyclopentyl, dimethylaminocarbonylmethyl, ethylpyrrolidinylmethyl, piperidinylethyl, methylaminoethyl, aminoethyl, pyrrolidinylethyl, 2-propane-1,3 diol, phenyl, carboxymethyl, dimethylaminopropyl, dimethylaminopropan-2-yl, dimethylaminopropan-1-ol-2-yl, methylaminopropyl, aminocyclohexyl, methoxyethyl, (2R)-pyrrolidinylmethyl, (2S)-pyrrolidinylmethyl, dimethylaminoethyl, pyrrolidinyl optionally substituted with methyl, propane-1,3-diol, hydroxymethyl, hydroxyethyl, aminomethyl, dimethylaminomethylcarbonylaminoethyl, dimethylamino, (R)-benzyl 2-amino-3-hydroxypropylcarbamate and methoxymethyl; R5 is selected from is selected from propyl, 1-methylethyl, methyl, ethyl, propyl, 2-methylpropyl, phenylethyl, dimethylaminoethyl, methoxymethyl, piperidinyl optionally substituted with methyl, cyclopentyl, dimethylaminocarbonylmethyl, ethylpyrrolidinylmethyl, piperidinylethyl, methylaminoethyl, aminoethyl, pyrrolidinylethyl, 2-propane-1,3 diol, phenyl, carboxymethyl, dimethylaminopropyl, dimethylaminopropan-2-yl, dimethylaminopropan-1-ol-2-yl, methylaminopropyl, aminocyclohexyl, methoxyethyl, (2R)-pyrrolidinylmethyl, (2S)-pyrrolidinylmethyl, dimethylaminoethyl, pyrrolidinyl optionally substituted with methyl, propane-1,3-diol, hydroxymethyl, hydroxyethyl, aminomethyl, dimethylaminomethylcarbonylaminoethyl, dimethylamino, (R)-benzyl 2-amino-3-hydroxypropylcarbamate and methoxymethyl; or R4 and R5, together with the nitrogen to which they are both attached, join together to form a heteroaryl group or a heterocycloalkyl group, wherein the heteroaryl group is selected from (1) isoindolinyl, (2) 1,2,3,4-tetrahydroisoquinolinyl optionally substituted with hydroxyl, and (3) indolinyl optionally substituted with hydroxyalkyl, and wherein the heterocycloalkyl group is selected from morpholinyl, piperidinyl, piperazinyl, pyrrolidinyl, imidazolidinyl, 3-azabicyclo[3.1.0]hexyl, 1,2,3,6-tetrahydropyridinyl, hexahydrocyclopenta[c]pyrrol-2(1H)-yl, hexahydrocyclopenta[c]pyrrol-5(1H)-yl, hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl), (4aR,8aR)-octahydro-1H-pyrido[3,4-b][1,4]oxazinyl, hexahydropyrrolo[3,4-b]pyrrol-2(1H)-yl), hexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl), thiazolidinyl, tetrahydro-3aH[1,3]dioxolo[4,5-c]pyrrolyl, hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl), azepanyl, 1,4-diazepanyl, (1S,4S)-2,5-diazabicyclo[2.2.1]heptanyl and azetanyl, wherein the heterocycloalkyl group is optionally substituted with 1, 2 or 3 substituents independently selected from halo, alkyl optionally substituted with 1-3 halo, carboxyalkyl, amino, hydroxyl, hydroxyalkyl, alkoxy optionally substituted with 1-3 halo, alkoxyalkyl optionally substituted with 1-3 halo, —
(CH2)0-3-heterocycloalkyl optionally substituted with alkyl, ═
N(H)—
OH, —
N(Boc)alkyl, spiroheterocycloalkyl optionally substituted with —
C(O)OR9 or —
NH2, (C1-C3)alkyl-O—
C(O)—
C(H)(NH2)—
(C1-C3)alkyl, —
(CH2)0-3—
O—
C(O)—
NR8R9, —
C(O)-aryl-R10, alkylcarbonylamino, alkoxyalkylcarbonylamino, heteroaryl optionally substituted with NR8R9, —
(CH2)0-3—
N(R6)R7, —
C(O)—
N(R8)R9, alkyl-C(O)N(H)(alkyl)-, aryl, arylalkyl optionally substituted with 1 or 2 groups selected from halo and alkyl, alkoxycarbonyl and aminoalkyl, provided that the optionally substituted heterocycloalkyl group cannot be substituted with more than one group selected from —
(CH2)0-3-heterocycloalkyl optionally substituted with alkyl, ═
N(H)—
OH,—
N(Boc)alkyl, spiroheterocycloalkyl optionally substituted with —
C(O)OR9 or —
NH2, —
(C1-C3)alkyl-O—
C(O)—
C(H)(NH2)—
(C1-C3)alkyl, —
(CH2)0-3—
O—
C(O)—
NR8R9, —
C(O)-aryl-R10, alkylcarbonylamino, alkoxyalkylcarbonylamino, heteroaryl optionally substituted with alkyl, (CH2)0-3—
N(R6)R7, —
C(O)—
N(R8)R9, alkyl-C(O)N(H)(alkyl)-, aryl, arylalkyl optionally substituted with 1 or 2 groups selected from halo and alkyl, and alkoxycarbonyl; andR6, R7, R8, R9, and R10 are as defined in claim 1.
-
-
11. The compound of Formula II, III, IV, V, VI or VII according to claim 9, or a pharmaceutically acceptable salt thereof, wherein:
-
R4 and R5, together with the nitrogen to which they are both attached, join together to form a heterocycloalkyl group, wherein the heterocycloalkyl group is selected from morpholinyl, piperidinyl, piperazinyl, pyrrolidinyl, imidazolidinyl, 3-azabicyclo[3.1.0]hexyl, 1,2,3,6-tetrahydropyridinyl, hexahydrocyclopenta[c]pyrrol-2(1H)-yl, hexahydrocyclopenta[c]pyrrol-5(1H)-yl, hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl), (4aR,8aR)-octahydro-1H-pyrido[3,4-b][1,4]oxazinyl, hexahydropyrrolo[3,4-b]pyrrol-2(1H)-yl), hexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl), thiazolidinyl, tetrahydro-3aH[1,3]dioxolo[4,5-c]pyrrolyl, hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl), azepanyl, 1,4-diazepanyl, (1S,4S)-2,5-diazabicyclo[2.2.1]heptanyl and azetanyl, wherein the heterocycloalkyl group is optionally substituted with 1, 2 or 3 substituents independently selected from halo, alkyl optionally substituted with 1-3 halo, carboxyalkyl, amino, hydroxyl, hydroxyalkyl, alkoxy optionally substituted with 1-3 halo, alkoxyalkyl optionally substituted with 1-3 halo, —
(CH2)0-3-heterocycloalkyl optionally substituted with alkyl, ═
N(H)—
OH, —
N(Boc)alkyl, spiroheterocycloalkyl optionally substituted with —
C(O)OR9 or —
NH2, (C1-C3)alkyl-O—
C(O)—
C(H)(NH2)—
(C1-C3)alkyl, —
(CH2)0-3—
O—
C(O)—
NR8R9, —
C(O)-aryl-R10, alkylcarbonylamino, alkoxyalkylcarbonylamino, heteroaryl optionally substituted with NR8R9, —
(CH2)0-3—
N(R6)R7,—
C(O)—
N(R8)R9, alkyl-C(O)N(H)(alkyl)-, aryl, arylalkyl optionally substituted with 1 or 2 groups selected from halo and alkyl, alkoxycarbonyl and aminoalkyl, provided that the optionally substituted heterocycloalkyl group cannot be substituted with more than one group selected from —
(CH2)0-3-heterocycloalkyl optionally substituted with alkyl, ═
N(H)—
OH, —
N(Boc)alkyl, spiroheterocycloalkyl optionally substituted with —
C(O)OR9 or —
NH2, —
(C1-C3)alkyl-O—
C(O)—
C(H)(NH2)—
(C1-C3)alkyl, —
(CH2)0-3—
O—
C(O)—
NR8R9, —
C(O)-aryl-R10, alkylcarbonylamino, alkoxyalkylcarbonylamino, heteroaryl optionally substituted with alkyl, (CH2)0-3—
N(R6)R7, —
C(O)—
N(R8)R9, alkyl-C(O)N(H)(alkyl)-, aryl, arylalkyl optionally substituted with 1 or 2 groups selected from halo and alkyl, and alkoxycarbonyl; andR6, R7, R8, R9, and R10 are as defined in claim 1.
-
-
12. The compound of Formula II, III, IV, V, VI or VII according to claim 9, or a pharmaceutically acceptable salt thereof, wherein:
-
R4 is H; and R5 is selected from —
(C1-C3)alkylamino optionally substituted with 1-2 substituents selected from halo, hydroxymethyl and hydroxyl, amino(C1-C3)alkylamino, pyrrolidinyl(C1-C4)alkylamino, pyridinyll (C1-C3)alkylamino, —
(C1-C3)alkylamino(C1-C3)alkylamino, —
(C1-C3)dialkylamino(C1-C3)alkylamino optionally substituted with hydroxymethyl, orR4 and R5, together with the nitrogen atom to which they are attached, join together to form piperidinyl, morpholinyl and pyrrolidinyl, wherein the piperidinyl, morpholinyl and pyrrolidinyl are optionally substituted with 1, 2 or 3 groups selected from —
(C1-C3)alkyl optionally substituted with 1-3 substituents selected from halo and hydroxyl, hydroxyl, hydroxyalkyl, alkylamino, methoxy, aminocarbonyl, amine, aminoalkyl, hydroxymethyl, aminomethyl, dimethylamino, dimethylaminoethoxy, and methoxymethyl.
-
-
13. The compound of Formula IB according to claim 2, or a pharmaceutically acceptable salt thereof, wherein
RXa is pyridinyl, 1H-isoindole, halo, phenyl optionally substituted with amine, hydroxyalkyl, aminocarbony, dialkylaminocarbonyl, — - S(O)2—
NH2, and alkylcarbonylamino;RXb is selected from (1) pyridine optionally substituted with halo or amine, (2) pyrimidiny optionally substituted with amine or dialkylaminoalkylcarbonylaminoalkylamino, (3) phenyl optionally substituted with —
S(O)2—
N(H)—
(C1-C3)alkyl-OH, —
S(O)2—
N(H)—
(C1-C3)alkyl-phenyl, or hydroxyallyl, (4) 1H-pyrazolo[3,4-b]pyridine, imidazolyl, —
S(O)2—
N(H)—
(C1-C3)alkyl-OH,- and imidazolyl.
- S(O)2—
-
14. The compound of Formula I according to claim 1, selected from one of the following compounds, or a pharmaceutically acceptable salt thereof:
-
4-[4-(4-ethylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 3-(2-aminopyrimidin-4-yl)-N,N-diethyl-1H-pyrrolo[2,3-b]pyridin-4-amine; 3-(2-aminopyrimidin-4-yl)-N-(2-methylpropyl)-1H-pyrrolo[2,3-b]pyridin-4-amine; 4-[4-(hexahydrocyclopenta[c]pyrrol-2(1H)-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 4-(methyloxy)-6-(4-piperidin-1-yl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine; 3-(2-aminopyrimidin-4-yl)-N-ethyl-1H-pyrrolo[2,3-b]pyridin-4-amine; 3-(2-aminopyrimidin-4-yl)-N-methyl-N-(1-methylpyrrolidin-3-yl)-1H-pyrrolo[2,3-b]pyridin-4-amine; 2-{1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]piperidin-3-yl}ethanol; N-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-N,N′
,N′
-trimethylethane-1,2-diamine;4-{4-[2-(aminomethyl)pyrrolidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; {1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidin-2-yl}methanol; 4-(4-pyrrolidin-1-yl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine; 4-[4-(1-methylhexahydropyrrolo[3,4-b]pyrrol-5(1H)-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 4-[4-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyridin-2-amine; 4-{4-[3-(methylamino)pyrrolidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 4-[4-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; ethyl 4-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]piperazine-1-carboxylate; 4-(4-morpholin-4-yl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine; 4-{4-[(3S)-3-aminopyrrolidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 4-[4-(5-methylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 4-[4-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyridin-2-ol; 4-[4-(4-phenylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 3-(2-aminopyrimidin-4-yl)-N-methyl-N-(1-methylethyl)-1H-pyrrolo[2,3-b]pyridin-4-amine; 3-(2-aminopyrimidin-4-yl)-N,N-dimethyl-1H-pyrrolo[2,3-b]pyridin-4-amine; 4-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine; 4-[4-(3-aminopyrrolidin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 4-[4-(4-methylpiperidin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 4-[4-(3,5-dimethylpiperidin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-amine; 4-(4-piperidin-1-yl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine; N-{1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidin-3-yl}-N-methylacetamide; 4-methyl-6-[4-(4-methylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidi2n-2-amine; 3-(2-aminopyrimidin-4-yl)-N-methyl-N-[2-(methyloxy)ethyl]-1H-pyrrolo[2,3-b]pyridin-4-amine; 4-{4-[4-(dimethylamino)piperidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 4-[4-(4-aminopiperidin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 4-[4-(3,4,5-trimethylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 6-(4-piperidin-1-yl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-2,4-diamine; N-{1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidin-3-yl}acetamide; 4-(4-{(2R)-2-[(methyloxy)methyl]pyrrolidin-1-yl}-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine; 3-(4-(piperidin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)benzamide; 4-[4-(3-aminopiperidin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 3-2(2-aminopyrimidin-4-yl)-N-methyl-N-(1-methylpiperidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-amine; 3-(2-aminopyrimidin-4-yl)-N-methyl-N-(2-phenylethyl)-1H-pyrrolo[2,3-b]pyridin-4-amine; (R)-(1-(3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl)pyrrolidin-2-yl)methanol; 4-[4-(3,5-dimethylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; (3R)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidin-3-ol; 4-{4-[3-(dimethylamino)pyrrolidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; (3S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidin-3-ol; 4-(4-azepan-1-yl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine; 3-(2-aminopyrimidin-4-yl)-N,N-dipropyl-1H-pyrrolo[2,3-b]pyridin-4-amine; 4-{4-[3-(methyloxy)pyrrolidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 4-{4-[(3R)-3-aminopyrrolidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 4-(4-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine; N-methyl-4-(4-piperidin-1-yl-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine; 5-(2-aminopyrimidin-4-yl)-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine; 4-(4-(hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine; 4-(4-{(2S)-2-[(methyloxy)methyl]pyrrolidin-1-yl}-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine; 4-[4-(3,4-dimethylpiperazin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 4-(4-piperazin-1-yl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)pyridin-2-amine; {(2S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidin-2-yl}methanol; 4-[4-(dimethylamino)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyridin-2-ol; 4-[4-(dimethylamino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]phenol; 4-[4-(hexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 4-[4-(4-methyl-1,4-diazepan-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 3-(2-aminopyrimidin-4-yl)-N,N-dimethyl-1H-pyrazolo[3,4-b]pyridin-4-amine; 4-[4-(3,3-dimethylpyrrolidin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 4-{4-[(3S)-3-fluoropyrrolidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]piperidin-4-ol; N′
-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-N,N-dimethylethane-1,2-diamine;3-(2-aminopyridin-4-yl)-N,N-dimethyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine; 3-(2-aminopyridin-4-yl)-N,N-dimethyl-1H-pyrazolo[3,4-b]pyridin-4-amine; 3-(2-aminopyrimidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine; 1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]piperidin-3-ol; 2-({(3S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidin-3-yl}amino)ethanol; {1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidin-3-yl}methanol; 3-(2-aminopyrimidin-4-yl)-N-cyclopentyl-1H-pyrrolo[2,3-b]pyridin-4-amine; 4-{4-[(3S,4R)-3-amino-4-phenylpyrrolidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; N-({1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidin-2-yl}methyl)-N2,N2-dimethylglycinamide; 4-(4-{4-[2-(methyloxy)ethyl]piperazin-1-yl}-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine; 4-{4-[(3S)-3-(ethylamino)pyrrolidin-1-yl}-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 3-(2-aminopyrimidin-4-yl)-N-pyrrolidin-3-yl-1H-pyrrolo[2,3-b]pyridin-4-amine; 4-{4-[3-(aminomethyl)pyrrolidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 2-{4-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-4-yl]piperazin-1-yl}ethanol; 4-[4-(2,7-diazaspiro[4.4]non-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 3-(2-aminopyrimidin-4-yl)-N-(1,2,2-trimethylpropyl)-1H-pyrrolo[2,3-b]pyridin-4-amine; 3-{[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-4-yl]amino}propane-1,2-diol; (3R,4R)-4-amino-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidin-3-ol; 3-(2-aminopyrimidin-4-yl)-N-piperidin-3-yl-1H-pyrrolo[2,3-b]pyridin-4-amine; (2S)-3-({(3S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidin-3-yl}amino)propane-1,2-diol; 4-{4-[4-(2-aminoethyl)piperazin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 4-{4-[4-(1-methylethyl)piperazin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 4-[4-(5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 2-{(2S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidin-2-yl}propan-2-ol; 4-{4-[(3S)-3-(methyloxy)pyrrolidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 4-{4-[(3R)-3-fluoropyrrolidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-L-prolinamide; 3-(2-aminopyrimidin-4-yl)-N-phenyl-1H-pyrrolo[2,3-b]pyridin-4-amine; 4-{4-[(3R)-3-(methyloxy)pyrrolidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 3-(2-aminopyrimidin-4-yl)-N-(1-methylpyrrolidin-3-yl)-1H-pyrrolo[2,3-b]pyridin-4-amine; 3-(2-aminopyrimidin-4-yl)-N-methyl-N-phenyl-1H-pyrrolo[2,3-b]pyridin-4-amine; {(3S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidin-3-yl}methanol; {4-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-methylpiperazin-2-yl}methanol; N-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-N-methylglycine; {(3R)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidin-3-yl}methanol; (3R,5S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-5-(hydroxymethyl)pyrrolidin-3-ol; (4S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-hydroxy-L-prolinamide; 4-(4-{(3S)-3-[(3,3,3-trifluoropropyl)amino]pyrrolidin-1-yl}-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine; {3-amino-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidin-3-yl}methanol; 4-{4-[(2S)-2-(fluoromethyl)pyrrolidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; (3S,4S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidine-3,4-diol; 1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]azetidin-3-ol; (3S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]piperidin-3-ol; 2-{(2S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidin-2-yl}acetamide; (3S,5S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-5-(hydroxymethyl)pyrrolidin-3-ol; 1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-N-methyl-L-prolinamide; (3R)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidine-3-carboxylic acid; (3R)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidine-3-carboxamide; {1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]piperidin-2-yl}methanol; 2-{(2S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidin-2-yl}ethanol; (3R,4S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidine-3,4-diol; (2S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]piperidine-2-carboxamide; (S)-{1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl}(4-chlorophenyl)methanol; ethyl (3S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidine-3-carboxylate; (3S)-1-[43-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-N-methylpyrrolidine-3-carboxamide; 4-{4-[(2R,6S)-2,6-dimethylmorpholin-4-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 4-[4-(3-morpholin-4-ylpyrrolidin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; (3R)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]piperidin-3-ol; (4S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-fluoro-L-prolinamide; {(2S,4S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-fluoropyrrolidin-2-yl}methanol; 4-{4-[(3R,4R)-3-(methylamino)-4-(methyloxy)pyrrolidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 3-(2-aminopyrimidin-4-yl)-N-(1,4-dioxan-2-ylmethyl)-1H-pyrrolo[2,3-b]pyridin-4-amine; (1R)-1-{(2S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidin-2-yl}ethanol; (3R,4R)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidine-3,4-diol; 4-[4-(1,3-dihydro-2H-isoindol-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; (3S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidine-3-carboxamide; 4-{4-[(3R)-3-phenylpyrrolidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-3-phenylpyrrolidin-3-ol; 4-{4-[3-(aminomethyl)azetidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; (3R,4S)-4-(aminomethyl)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidin-3-ol; (4R)-3-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1,3-thiazolidine-4-carboxamide; {(2S,4R)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-fluoropyrrolidin-2-yl}methanol; 4-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1-methylpiperazin-2-one; methyl 7-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-2,7-diazaspiro[4.4]nonane-2-carboxylate; 1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-3-methylpyrrolidin-3-ol; 4-[4-(3-aminoprop-1-yn-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 4-{4-[3-(dimethylamino)prop-1-yn-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; (2R,3S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-2-(hydroxymethyl)pyrrolidin-3-ol; (3R,4R)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-(methyloxy)pyrrolidin-3-ol; 4-[4-(3,3-difluoropyrrolidin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 4-{4-[3-(dimethylamino)propyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 4-[4-(3,4-dihydroisoquinolin-2(1H)-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 4-[4-(2,3-dihydro-1H-indol-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 3-(2-aminopyrimidin-4-yl)-N-(morpholin-2-ylmethyl)-1H-pyrrolo[2,3-b]pyridin-4-amine; (3S,4S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-fluoropyrrolidin-3-ol; (3R,4R)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-hydroxypyrrolidine-3-carbonitrile; [(2S,4S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-(methyloxy)pyrrolidin-2-yl]methanol; {(2S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4,4-difluoropyrrolidin-2-yl}methanol; 4-{4-[(3R,4R)-3-fluoro-4-(methyloxy)pyrrolidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 2-{[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]amino}ethanol; 7-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-2,7-diazaspiro[4.4]nonane-2-carboxamide; 4-{4-[3-(butyloxy)-3-methylpiperidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; (3S,5S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-5-(hydroxymethyl)-3-(trifluoromethyl)pyrrolidin-3-ol; [(2S,4S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-(methyloxy)-4-(trifluoromethyl)pyrrolidin-2-yl]methanol; (3S,4S)-4-amino-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]piperidin-3-ol; 4-{4-[(5aR,8aR)-5a,6,8,8a-tetrahydro-4H,7H-pyrrolo[3,4-b][1,2,3]triazolo[1,5-d][1,4]oxazin-7-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 4-{4-[1-(phenylmethyl)-1H-1,2,3-triazol-4-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; {(2S)-1-[3-(2-aminopyrimidin-4-yl)-5-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidin-2-yl}methanol; [(2R,3S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-3-(methyloxy)pyrrolidin-2-yl]methanol; 3-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]prop-2-yn-1-ol; 1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1,2,3,6-tetrahydropyridin-3-ol; 2-{1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl}propan-2-ol; 3-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]propan-1-ol; 4-{4-[3-(methylamino)prop-1-yn-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; {(2S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidin-2-yl}methyl L-valinate; 1,1-dimethylethyl N-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]glycinate; {(2R,3S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-3-fluoropyrrolidin-2-yl}methanol; {(3aR,4R,6aS)-5-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-4-yl}methanol; 4-{4-[(3R,4S)-3,4-bis(methyloxy)pyrrolidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 3-(2-aminopyrimidin-4-yl)-N-[2-(methyloxy)ethyl]-1H-pyrrolo[2,3-b]pyridin-4-amine; 4-{4-[(3S,4S)-3,4-difluoropyrrolidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; {(2S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidin-2-yl}methyl carbamate; {3-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]phenyl}methanol; 4-(4-{[2-(dimethylamino)ethyl]oxy}-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine; 4-[4-(3-azabicyclo[3.1.0]hex-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]imidazolidin-2-one; {1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]piperidin-4-yl}(4-chlorophenyl)methanone; 4-{4-[3-(3-methyl-1,2,4-oxadiazol-5-yl)pyrrolidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 4-[4-(3-phenylpyrrolidin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 4-{4-[(3R)-3-(ethyloxy)pyrrolidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 3-{[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]oxy}propan-1-ol; 2-{[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]oxy}ethanol; 4-(4-{[2-(methyloxy)ethyl]oxy}-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine N2-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-N,N-dimethylglycinamide; (3aR,6aS)-5-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]tetrahydro-3aH[1,3]dioxolo[4,5-c]pyrrol-2-one; N-{(3R,4R)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-hydroxypyrrolidin-3-yl}-2-(ethyloxy)acetamide; N-{(3R,4R)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-hydroxypyrrolidin-3-yl}acetamide; {(2S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-2,3-dihydro-1H-indol-2-yl}methanol; 4-[5-(methyloxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; {(2S)-1-[3-(6-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidin-2-yl}methanol; 4-{4-[2-(2-thienyl)pyrrolidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 4-[4-(2-phenylpyrrolidin-1-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 4-(4-{(3R)-3-[(2,2-difluoroethyl)oxy]pyrrolidin-1-yl}-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine; 4-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine; 3-(2-aminopyrimidin-4-yl)-N-[(1-ethylpyrrolidin-2-yl)methyl]-1H-pyrrolo[2,3-b]pyridin-4-amine; (4aR,8aR)-6-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]hexahydro-1H-pyrido[3,4-b][1,4]oxazin-2(3H)-one; 2-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]hexahydrocyclopenta[c]pyrrol-5(1H)-one oxime; 4-[4-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 4-{4-[6-(methyloxy)pyridin-3-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 3-(2-aminopyrimidin-4-yl)-N,N-dimethyl-5-(methyloxy)-1H-pyrrolo[2,3-b]pyridin-4-amine; 4-[4-chloro-5-(methyloxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 4-[5-(methyloxy)-4-pyrrolidin-1-yl-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 2-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1,2,3,4-tetrahydroisoquinolin-8-ol; 4-[4-(2-oxa-6-azaspiro[3.3]hept-6-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 4-{4-[2-(methyloxy)pyridin-4-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 4-(5-{[2-(methyloxy)ethyl]oxy}-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine; 1-(1H-pyrrolo[2,3-b]pyridin-3-ylmethyl)guanidine; 4-[4-(2,6-diazaspiro[3.3]hept-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 4-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyridin-2-ol; 4-[4-(6-methyl-2,6-diazaspiro[3.3]hept-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 4-{4-[(2R,5S)-2,5-dimethylpiperazin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 4-(5-{[2-(dimethylamino)ethyl]oxy}-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine; 4-(4-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-1,3-thiazol-2-amine; 3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-6-ol; (3R,4R)-3-amino-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]piperidin-4-ol; {2-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-2,3-dihydro-1H-isoindol-1-yl}methanol; 1,1-dimethylethyl[(3R,4R)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-(methyloxy)pyrrolidin-3-yl]methylcarbamate; 2-(1H-pyrrolo[2,3-b]pyridin-3-yl)-1,3-thiazol-4-amine; 4-[1-(phenylmethyl)-2-({2-[(phenylmethyl)oxy]ethyl}oxy)-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridin-8-yl]pyrimidin-2-amine; 3-(2-aminopyrimidin-4-yl)-N-(2-pyrrolidin-1-ylethyl)-1H-pyrrolo[2,3-b]pyridin-4-amine; N′
-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-N,N-diethylethane-1,2-diamine;N′
-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-N,N-dimethylpropane-1,3-diamine;3-(2-aminopyrimidin-4-yl)-N-(2-piperidin-1-ylethyl)-1H-pyrrolo[2,3-b]pyridin-4-amine; 4-{4-[2-(trifluoromethyl)phenyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; 2-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]benzonitrile; {(2R)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-3,3-difluoropyrrolidin-2-yl}methanol; N-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-H-methylethane-1,2-diamine; N-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]ethane-1,2-diamine; 3-(2-aminopyrimidin-4-yl)-N-(2-pyridin-2-ylethyl)-1H-pyrrolo[2,3-b]pyridin-4-amine; 4-(1H-pyrrolo[2,3-b]pyridin-4-yl)pyrimidin-2-amine; N-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]propane-1,3-diamine; 3-(2-aminopyrimidin-4-yl)-N-(2-fluoroethyl)-1H-pyrrolo[2,3-b]pyridin-4-amine; (2R)-2-{[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]amino}butan-1-ol; (2S)-2-{[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]amino}butan-1-ol; 3-(2-aminopyrimidin-4-yl)-N-(pyrrolidin-3-ylmethyl)-1H-pyrrolo[2,3-b]pyridin-4-amine; 3-(2-aminopyrimidin-4-yl)-N-(pyrrolidin-2-ylmethyl)-1H-pyrrolo[2,3-b]pyridin-4-amine; 3-(2-aminopyrimidin-4-yl)-N-(2-pyridin-4-ylethyl)-1H-pyrrolo[2,3-b]pyridin-4-amine; N-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-H-methylpropane-1,3-diamine; N-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]cyclohexane-1,3-diamine; N-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]benzene-1,3-diamine; (1R,2R)—
N-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]cyclohexane-1,2-diamine;N-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]benzene-1,2-diamine; 3-(2-aminopyrimidin-4-yl)-N-(2-methyl-2-pyrrolidin-1-ylpropyl)-1H-pyrrolo[2,3-b]pyridin-4-amine; N-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]benzene-1,4-diamine; 3-(2-aminopyrimidin-4-yl)-N-[(1-methyl-1H-imidazol-2-yl)methyl]-1H-pyrrolo[2,3-b]pyridin-4-amine; 3-(2-aminopyrimidin-4-yl)-N-[(2S)-pyrrolidin-2-ylmethyl]-1H-pyrrolo[2,3-b]pyridin-4-amine; 3-(2-aminopyrimidin-4-yl)-N-[(2R)-pyrrolidin-2-ylmethyl]-1H-pyrrolo[2,3-b]pyridin-4-amine; phenylmethyl[(2R)-2-{[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]amino}-3-hydroxypropyl]carbamate; N2-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-N1,N1-dimethylpropane-1,2-diamine; (2S)-2-{[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]amino}-3-(dimethylamino)propan-1-ol; 3-(2-aminopyrimidin-4-yl)-N-(2-piperidin-2-ylethyl)-1H-pyrrolo[2,3-b]pyridin-4-amine; 1H,1′
H-4,4′
-bipyrrolo[2,3-b]pyridine;N-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-N′
-ethylethane-1,2-diamine;4-(1H-indol-5-yl)-1H-pyrrolo[2,3-b]pyridine; 4-(1H-indol-4-yl)-1H-pyrrolo[2,3-b]pyridine; 4-(5-chloro-1H-pyrrolo[2,3-b]pyridin-4-yl)pyridin-2-amine; 4(7-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)aniline; N2,N2-dimethyl-N-[3({4-[4-(methyloxy)-1H-pyrrolo[2,3-b]pyridin-2-yl]pyrimidin-2-yl}amino)propyl]glycinamide; 2(6-chloropyridin-3-yl)-7-phenyl-3H-imidazo[4,5-b]pyridine; 4-[2-(2-aminopyridin-4-yl)-3H-imidazo[4,5-b]pyridin-7-yl]benzamide; 5(7-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amine; 4-[2-(6-aminopyridin-3-yl)-3H-imidazo[4,5-b]pyridin-7-yl]benzamide; 4(7-phenyl-3H-imidazo[4,5-b]pyridin-2-yl)pyridin-2-amine; 4-(4-phenyl-1H-pyrrolo[2,3-b]pyridin-2-yl)pyrimidin-2-amine; {3-[2-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]phenyl}methanol; 4(4-pyridin-4-yl-1H-pyrrolo[2,3-b]pyridin-2-yl)pyrimidin-2-amine; 4-bromo-2-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine; 3-[2-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-N,N-dimethylbenzamide; 4-{4-[3-(chloromethyl)phenyl]-1H-pyrrolo[2,3-b]pyridin-2-yl}pyrimidin-2-amine; 4(4-phenyl-1H-pyrrolo[2,3-b]pyridin-2-yl)pyridin-2-amine; 4-[2-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyridin-2-amine; 4-[4-(2-aminopyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-2-yl]pyrimidin-2-amine; 3-[4-(2-aminopyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-2-yl]benzenesulfonamide; 3,3′
-(1H-pyrrolo[2,3-b]pyridine-2,4-diyl)dibenzenesulfonamide;2-[4-(2-aminopyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-2-yl]acetamide; 4-[2-(1H-indazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyridin-2-amine; 3-[4-(1H-indol-4-yl)-1H-pyrrolo[2,3-b]pyridin-2-yl]benzenesulfonamide; 4,4′
-(1H-pyrrolo[2,3-b]pyridine-2,4-diyl)dipyridin-2-amine;N-(3-{2-[3-(aminosulfonyl)phenyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}phenyl)acetamide; 4-[4-(4-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]pyridin-2-amine; 4-(4-chloro-1H-pyrrolo[2,3-b]pyridin-2-yl)pyridin-2-amine; N-{3-[2-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]phenyl}acetamide; N-{3-[2-(1H-indazol-6-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]phenyl}acetamide; {3-[4-(2-aminopyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-2-yl]phenyl}methanol; 3-[4-(1H-indol-4-yl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-N-(phenylmethyl)benzenesulfonamide; 4-[4-(1H-indol-4-yl)-1H-pyrrolo[2,3-b]pyridin-2-yl]pyridin-2-amine; N-(3-hydroxypropyl)-3-[4-(1H-indol-4-yl)-1H-pyrrolo[2,3-b]pyridin-2-yl]benzenesulfonamide; 2-{4-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-2-oxopiperazin-1-yl}-N-(2-methylpropyl)acetamide; (4S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-fluoro-L-proline; 4-{4-[(2S)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; (3S)-1-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyrrolidine-3-carboxylic acid; 5-[3-(2-aminopyrimidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-4-yl]pyridin-2-ol; 4-{4-[4-(methyloxy)-1H-pyrrolo[3,2-c]pyridin-2-yl]-1H-pyrrolo[2,3-b]pyridin-3-yl}pyrimidin-2-amine; and 4-(4-{(3R)-3-[(1-methylethyl)oxy]pyrrolidin-1-yl}-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-2-amine.
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17. A pharmaceutical composition comprising a compound according to claim 1, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier, excipient or diluent.
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18. A method of modulating CDK in a cell, comprising contacting a cell in which inhibition of CDK is desired with a compound according to claim 1, or a pharmaceutically acceptable salt thereof.
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19. A method of treating a disease or condition that involves CDK, comprising administering to a mammal, in need of the treatment, a compound according to claim 1, or a pharmaceutically acceptable salt thereof.
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20. The method according to claim 19, wherein the disease or condition is selected from chronic lymphocytic lymphoma, Burkitts lymphoma mantle cell lymphoma, multiple myeloma, breast cancer, small cell lung carcinoma, eosophageal carcinoma, HIV, HTLV associated leukemia, rheumatoid arthritis, multiple sclerosis, transplant rejection and cardiac hypertrophy.
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2. A compound according to claim 1, according to Formula IA or Formula IB:
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15. A compound of Formula IC:
- View Dependent Claims (16)
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16. A compound according to claim 15 selected from one of the following compounds, or a pharmaceutically acceptable salt thereof:
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4-chloro-6-[4-(methyloxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]pyrimidin-2-amine; 4-(methyloxy)-3-[2-(4-methylpiperazin-1-yl)pyridin-4-yl]-1H-pyrrolo[2,3-b]pyridine; 2-fluoro-5-[4-(methyloxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]aniline;
4′
-chloro-4-(methyloxy)-1H,1′
H-3,5′
-bipyrrolo[2,3-b]pyridine;4-(methyloxy)-3-pyridin-4-yl-1H-pyrazolo[3,4-d]pyrimidine; 4-[4-(methyloxy)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]pyridin-2-amine; 4-(methyloxy)-3-pyridin-3-yl-1H-pyrazolo[3,4-d]pyrimidine; 4-[4-(methyloxy)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]pyridin-2-amine; and 4-[4-(ethyloxy)-1H-pyrrolo[2,3-b]pyridin-3-yl]-6-methylpyrimidin-2-amine.
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16. A compound according to claim 15 selected from one of the following compounds, or a pharmaceutically acceptable salt thereof:
Specification
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Current AssigneeExelixis Incorporated
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Original AssigneeExelixis Incorporated
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InventorsChan, Diva Sze-Ming, Jeong, Joon Won, Rao, Pallavi, Leahy, James W., Kelley, Ryan Michael, Franzini, Maurizio, Bahceci, Suleyman, Jones, Lisa Renee, Ridgway, Brian Hugh, Noguchi, Robin Tammie, Wang, Yong, Forsyth, Timothy Patrick, Mac, Morrison B., Jammalamadaka, Vasu, Xu, Wei, Kim, Moon Hwan, Chen, Jeff, Chan, Bryan
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Application NumberUS13/002,195Publication NumberTime in Patent OfficeDaysField of SearchUS Class Current514/217.06CPC Class CodesA61P 19/02 for joint disorders, e.g. a...A61P 25/00 Drugs for disorders of the ...A61P 29/00 Non-central analgesic, anti...A61P 31/18 for HIVA61P 35/00 Antineoplastic agentsA61P 35/02 specific for leukemiaA61P 37/00 Drugs for immunological or ...A61P 37/06 Immunosuppressants, e.g. dr...A61P 43/00 Drugs for specific purposes...A61P 9/00 Drugs for disorders of the ...C07D 471/04 Ortho-condensed systemsC07D 487/04 Ortho-condensed systemsC07D 519/00 Heterocyclic compounds cont...