COMPOUNDS AND COMPOSITIONS AS C-KIT KINASE INHIBITORS
First Claim
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1. A compound of Formula (I) or Formula (II), or a pharmaceutically acceptable salt thereof:
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Abstract
The invention provides compounds of formulae (I) and (II) and pharmaceutical compositions thereof, which are useful as protein kinase inhibitors, as well as methods for using such compounds to treat, ameliorate or prevent a condition associated with abnormal or deregulated kinase activity. In some embodiments, the invention provides methods for using such compounds to treat, ameliorate or prevent diseases or disorders that involve abnormal activation of c-kit or c-kit and PDGFR (PDGFRα, PDGFRβ) kinases.
5 Citations
35 Claims
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1. A compound of Formula (I) or Formula (II), or a pharmaceutically acceptable salt thereof:
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 16, 17, 18, 19, 22, 24, 25, 26)
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2. The compound of claim 1 wherein:
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m is 1 and R20 is selected from H, halo, C1-C6alkyl, C1-C6haloalkyl, C1-C6haloalkoxy, deuterium, deuterated C1-C6alkyl, —
CN, —
(CR92)nOR4, —
C(O)R4, —
(CR92)nC(═
O)OR4, R8, —
(CR92)nR8, —
((CR92)nO)tR4, —
(CR92)nO(CR92)nR6, —
(CR92)nC(═
O)R4, —
C(═
O)N(R4)2, —
(CR92)nOR4, —
OR4 and —
(CR92)nCN,or m is 4 and R20 is deuterium; R1 is selected from C1-C6alkyl and halo; each R11 is independently selected from H, halo and C1-C6alkyl; L1 is a bond, —
NH—
or —
C(O)NH—
;R2 is selected from C1-C6alkyl, C1-C6haloalkyl, C2-C8alkenyl, —
(CR92)nOR4, —
(CR92)nR6, —
(CR92)nS(═
O)2NR42, —
(CR92)nCN, —
(CR92)nC(═
O)R4, —
(CR92)nOC(═
O)R4, —
(CR92)nC(═
O)OR4, —
(CR92)nC(═
O)NR42, —
(CR92)nOC(═
O)NR4(CR92)nOR4, —
(CR92)nO(CR92)nOR4, —
(CR92)nO(CR92)nR6, —
(CR92)nO(CR92)nO(CR92)nR6, —
(CR92)nOCR9R6R6, —
(CR92)nCR9R5R6, —
(CR92)nCR5R6R6, —
CR9R5R6, —
CR9R9R5, —
CR9R6NR42, —
(CR92)nNR42, —
NR4(CR92)nOR4, —
NR4(CR92)nR6, —
NR4(CR92)nR4, —
(CR92)NR4C(═
O)R4, —
(CR92)nNR4C(═
O)OR4, —
(CR92)NR4C(═
O)NR42, —
(CR92)NR4C(═
O)R6, —
(CR92)nNR4S(═
O)2R4, —
(CR92)nNR4C(═
O)O(CR92)nOR4, —
(CR92)nNR4C(═
O)(CR92)nOR4, —
CR5R5NR4S(═
O)2R4, —
(CR92)nNR5C(═
O)R6, —
(CR92)nNR4C(═
O)(CR92)nR6, —
(CR92)nNR4C(═
O)O(CR92)nR11, —
(CR92)nNR4C(═
O)(CR92)nO(CR92)nR6, and —
(CR92)nNR4C(═
O)O(CR92)nR6;each R4 is independently selected from H and C1-C6alkyl; each R5 is independently selected from —
NHC(O)OR4, —
OR4 and —
(CR92)nOR4;each R6 is a C1-C6haloalkyl; each R9 is independently selected from H and C1-C6alkyl; R8 is selected from an unsubstituted phenyl, unsubstituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O or S, an unsubstituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, an unsubstituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O or S, an unsubstituted C3-C8cycloalkyl, a substituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O or S, a substituted phenyl, a substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, a substituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O or S, a substituted C3-C8cycloalkyl, a oxazolidin-2-one, pyrrolidinone and a pyrrolidin-2-one, wherein the substituted phenyl, the substituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O or S, the substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, substituted C3-C8cycloalkyl and substituted 4-6 membered heterocycloalkyl of R8 are substituted with 1-3 substituents independently selected from C1-C6alkyl, halo, —
(C(R9)2)nOR4, —
C(O)NR42—
NR42, —
R10, —
(C(R9)2)nR10, —
OR4, —
(C(R9)2)nC(O)OR4 and —
S(O)2R4;R10 is selected from an unsubstituted phenyl, unsubstituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O or S, an unsubstituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, an unsubstituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O or S, an unsubstituted C3-C8cycloalkyl, a substituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O or S, a substituted phenyl, a substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, a substituted 4-6 membered heterocycloalkyl with 1-2 heteroatoms independently selected from N, O or S, and a substituted C3-C8cycloalkyl, wherein the substituted phenyl, the substituted 5-6 membered heteroaryl with 1-2 heteroatoms independently selected from N, O or S, the substituted 5 membered heteroaryl with 1-4 heteroatoms selected from N, substituted C3-C8cycloalkyl and substituted 4-6 membered heterocycloalkyl of R10 are substituted with 1-3 substituents independently selected from C1-C6alkyl, and —
(C(R9)2)nOR4;t is 1, 2 or 3, and each n is independently selected from 1, 2, 3 and 4.
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3. The compound of claim 1, wherein the compound is a compound of Formula (Ia), Formula (IIa), Formula (Ib) or Formula (IIb):
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4. The compound of claim 1 wherein R1 is selected from —
- CH3 and F.
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5. The compound of claim 1, wherein R1 is —
- CH3.
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6. The compound of claim 1, wherein each R11 is independently selected from H, F and —
- CH3.
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7. The compound of claim 1, wherein each R11 is H.
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8. The compound of claim 1, wherein:
R2 is selected from —
(CR92)nCN, —
(CR92)nNR4C(═
O)OR4, —
(CR92)nOR4, —
(CR92)nC(═
O)NR42, —
(CR92)nC(═
O)R4, C1-C6alkyl, C2-C8alkenyl, —
(CR92)nCR5R6R6, —
CR5R5NR4S(═
O)2R4, —
(CR92)nNR4S(═
O)2R4, —
(CR92)NR4C(═
O)R6, —
(CR92)nO(CR92)nOR4, —
(CR92)nC(═
O)OR4, —
(CR92)nO(CR92)nR6, —
(CR92)nCR9R5R6, —
NR4(CR92)nR6, —
NR4(CR92)nR4, —
(CR92)nR6 and —
(CR92)nOCR9R6R6.
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9. The compound of claim 1, wherein:
R2 is selected from —
(CR92)nCR9R5R6 and —
(CR92)nOR4.
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10. The compound of claim 1, wherein each R4 is independently selected from H, methyl, ethyl, propyl, butyl, i-propyl and t-butyl.
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11. The compound of claim 1, wherein each R5 is independently selected from, —
- OR4 and —
(CR92)nOR4.
- OR4 and —
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12. The compound of claim 1, wherein each R5 is independently selected from OH and —
- CH2OH.
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13. The compound of claim 1, wherein each R6 is independently selected from —
- CH2F, —
CHF2, —
CH2CHF2, —
CH2CF3 and —
CF3.
- CH2F, —
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14. The compound of claim 1, wherein each R9 is independently selected from H, methyl and ethyl.
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16. The compound of claim 1, wherein R2 is —
- C(CH3)2CH2OH or —
CH2CH2C(CH3)OHCF3.
- C(CH3)2CH2OH or —
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17. The compound of claim 1 wherein m is 1 and R20 is selected from H, halo, C1-C6alkyl, C1-C6haloalkyl, deuterated C1-C6alkyl, —
- CN, —
(CR92)nOR4, —
R8, —
(CR92)nR8, —
(CR92)nO(CR92)nR6, —
(CR92)nC(═
O)R4, —
(CR92)nOR4 and —
OR4.
- CN, —
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18. The compound of claim 1, wherein m is 1 and R20 is selected from H, —
- F, —
CH3, —
CF3, —
CD3, —
CN, —
OCHF2, —
CH2CH2C(CH3)2OH, —
CH2OCH2CF3, —
CH2CH2C(═
O)CH3, —
CH2OCH3 and —
OCH3.
- F, —
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19. The compound of claim 1, wherein m is 1 and R20 is H or —
- CH3.
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22. The compound of claim 1, wherein:
R8 is selected from phenyl, morpholinyl, cyclopropyl, pyridinyl, pyridine-3-yl, pyridine-4-yl, pyrazolyl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrrolyl, triazolyl, 1H-1,2,3-triazol-4-yl, 4H-1,2,4-triazol-3-yl, 1H-1,2,4-triazol-5-yl, thiazolyl, thiazol-4-yl, thiazol-5-yl, isoxazolyl and isoxazol-4-yl, each of which is unsubstituted or each of which is substituted with 1-3 substituents independently selected from F, —
CH3, —
C(CH3)2CH2OH, —
CH2OCH3, —
C(O)NHCH3, —
NH2 and —
OCH3.
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24. The compound of claim 1 selected from:
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N-{5-[5-(2-cyanoethyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide; tert-butyl N-{2-[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]ethyl}carbamate; N-{5-[5-(3-methoxypropyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide; N-(5-{5-[2-(diethylcarbamoyl)ethyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide; N-{2-methyl-5-[5-(3-oxobutyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide; tert-butyl N-{[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]methyl}carbamate; ethyl 2-[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]acetate; N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide; N-{5-[5-(3-hydroxybutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide; N-{5-[5-(2-ethoxyethyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide; N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide; N-{5-[5-(ethoxymethyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide; tert-butyl N-[(1S)-1-[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]ethyl]carbamate; N-(5-{5-[(1R)-1-methoxyethyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide; N-{2-methyl-5-[5-(3,3,3-trifluoro-2-hydroxy-2-methylpropyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide; N-(2-methyl-5-{5-[3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide; N-{5-[5-(1,3-dihydroxy-2-methanesulfonamidopropan-2-yl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide; N-(5-{5-[(1R)-1-methanesulfonamidoethyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide; tert-butyl N-{[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]methyl}-N-methylcarbamate; N-{5-[5-(ethanesulfonamidomethyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide; tert-butyl N-ethyl-N-{[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]methyl}carbamate; N-(5-{5-[(N-ethylmethanesulfonamido)methyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide; methyl N-ethyl-N-{[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]methyl}carbamate; N-(2-methyl-5-{5-[(2,2,2-trifluoroacetamido)methyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide; N-{2-methyl-5-[5-(propane-2-sulfonamidomethyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide; N-(5-{5-[(2-methoxyethoxy)methyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide; tert-butyl 2-[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]acetate; N-(2-methyl-5-{5-[2-(2,2,2-trifluoroethoxy)ethyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide; ethyl N-{[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]methyl}carbamate; propan-2-yl N-{[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]methyl}carbamate; N-(2-methyl-5-{5-[(2R)-3,3,3-trifluoro-2-hydroxypropyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide; N-(5-{5-[(2-ethoxyethoxy)methyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide; N-[2-methyl-5-(5-{[2-(propan-2-yloxy)ethoxy]methyl}-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide; N-[5-(5-{[2-(tert-butoxy)ethoxy]methyl}-1,2,4-oxadiazol-3-yl)-2-methylphenyl]imidazo[1,2-a]pyridine-3-carboxamide; N-(2-methyl-5-{5-[(3,3,3-trifluoropropanamido)methyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide; 6-fluoro-N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide; 6-fluoro-N-(5-{5-[(2-methoxyethoxy)methyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide; ethyl N-{[3-(3-{6-fluoroimidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]methyl}carbamate; N-(2-methyl-5-{5-[(2,2,2-trifluoroethoxy)methyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide; 2,2-difluoroethyl N-{[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]methyl}carbamate; methyl N-({3-[4-methyl-3-(7-{1-[2-(morpholin-4-yl)ethyl]-1H-pyrazol-4-yl}imidazo[1,2-a]pyridine-3-amido)phenyl]-1,2,4-oxadiazol-5-yl}methyl)carbamate; N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}-7-(1-methyl-1H-pyrazol-3-yl)imidazo[1,2-a]pyridine-3-carboxamide; N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-6-(1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide; 6-(1-methyl-1H-pyrazol-4-yl)-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide; 6-[1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl]-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide; N-(5-{[5-(1-hydroxy-2-methylpropan-2-yl)-1,2,4-oxadiazol-3-yl]amino}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide; N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-6-(1,3-thiazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide; 6-(2,4-dimethyl-1,3-thiazol-5-yl)-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide; 6-(3,5-dimethyl-1,2-oxazol-4-yl)-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide; N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}-7-methylimidazo[1,2-a]pyridine-3-carboxamide; N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-6-{1-[2-(morpholin-4-yl)ethyl]-1H-pyrazol-4-yl}imidazo[1,2-a]pyridine-3-carboxamide; 5,6,7,8-tetradeutero-N-{2-methyl-5-[5-(3-methylbut-2-en-1-yl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide; 5,6,7,8-tetradeutero-N-(5-{5-[(2-methoxyethoxy)methyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide; 5,6,7,8-tetradeutero-N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide; propan-2-yl 3-[3-(3-{imidazo[1,2-a]pyridine-3-amido}-4-methylphenyl)-1,2,4-oxadiazol-5-yl]propanoate; N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}-6-methoxyimidazo[1,2-a]pyridine-3-carboxamide; N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl}-2-methylphenyl]-6-methylimidazo[1,2-a]pyridine-3-carboxamide; N-(5-{5-[(2-methoxyethoxy)methyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)-6-methylimidazo[1,2-a]pyridine-3-carboxamide; N-{2-methyl-5-[5-(pentan-2-yl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide; N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}-7-(morpholin-4-yl)imidazo[1,2-a]pyridine-3-carboxamide; N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}-7-(2-oxo-1,3-oxazolidin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide; N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}-7-(2-oxopyrrolidin-1-yl)imidazo[1,2-a]pyridine-3-carboxamide; N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}-7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide; 7-cyclopropyl-N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide; 7-fluoro-N-(5-{5-[(2-hydroxy-2-methylpropyl)(methyl)amino]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide; N-{2-methyl-5-[5-(4,4,4-trifluoro-3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide; 7-methyl-N-{2-methyl-5-[5-(4,4,4-trifluoro-3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide; N-(5-{5-[(2-fluoroethyl)amino]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)-7-methylimidazo[1,2-a]pyridine-3-carboxamide; 7-methyl-N-(2-methyl-5-{5-[(2-methylpropyl)amino]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide; 7-fluoro-N-{2-methyl-5-[5-(4,4,4-trifluoro-3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide; 6-fluoro-N-{2-methyl-5-[5-(4,4,4-trifluoro-3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide; 6-methyl-N-{2-methyl-5-[5-(4,4,4-trifluoro-3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide; 5,6,7,8-tetradeutero-N-{2-methyl-5-[5-(4,4,4-trifluoro-3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide; N-{2-methyl-5-[5-(3,3,3-trifluoropropyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide; 7-methyl-N-(2-methyl-5-{5-[(3S)-4,4,4-trifluoro-3-hydroxy-3-methylbutyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide; 7-methyl-N-(2-methyl-5-{5-[(3R)-4,4,4-trifluoro-3-hydroxy-3-methylbutyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide; 7-methyl-N-(2-methyl-5-{5-[(2,2,2-trifluoroethoxy)methyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide; 7-methyl-N-(2-methyl-5-{5-[(2,2,2-trifluoroethoxy)methyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide; 6-methyl-N-(2-methyl-5-{5-[(2,2,2-trifluoroethoxy)methyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide; N-{2-methyl-5-[5-(4,4,4-trifluorobutyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide; N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-6-(2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide; N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-6-(2-methylpyridin-3-yl)imidazo[1,2-a]pyridine-3-carboxamide; N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-6-(3-methylpyridin-4-yl)imidazo[1,2-a]pyridine-3-carboxamide; 6-methyl-N-(2-methyl-5-{5-[(3S)-4,4,4-trifluoro-3-hydroxy-3-methylbutyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide; 6-fluoro-N-(2-methyl-5-{5-[(3S)-4,4,4-trifluoro-3-hydroxy-3-methylbutyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide; 7-fluoro-N-(2-methyl-5-{5-[(3S)-4,4,4-trifluoro-3-hydroxy-3-methylbutyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide; 6-methyl-N-(2-methyl-5-{5-[(3R)-4,4,4-trifluoro-3-hydroxy-3-methylbutyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide; 6-fluoro-N-(2-methyl-5-{5-[(3R)-4,4,4-trifluoro-3-hydroxy-3-methylbutyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide; 7-fluoro-N-(2-methyl-5-{5-[(3R)-4,4,4-trifluoro-3-hydroxy-3-methylbutyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide; 7-methyl-N-{2-methyl-5-[5-(4,4,4-trifluoro-3-methoxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide; 6-(2,4-dimethyl-1,3-thiazol-5-yl)-N-(2-methyl-5-{5-[(2,2,2-trifluoroethoxy)methyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide; 6-(2-fluoropyridin-3-yl)-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide; N-methyl-5-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)pyridine-2-carboxamide; N-(5-{5-[(2,2-difluoroethoxy)methyl]-1,2,4-oxadiazol-3-yl}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide; N-{5-(5-{[(1,3-difluoropropan-2-yl)oxy]methyl}-1,2,4-oxadiazol-3-yl)-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide; N-[2-methyl-5-(5-{[(1,1,1-trifluoropropan-2-yl)oxy]methyl}-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide; 6-(4-methyl-1,3-thiazol-5-yl)-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide; 7-methyl-N-{2-methyl-5-[5-(4,4,4-trifluoro-3-hydroxybutyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide; 7-methyl-N-(2-methyl-5-{5-[(2R)-3,3,3-trifluoro-2-hydroxypropyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide; N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-6-(1,3,5-trimethyl-1H-pyrazol-4-yl)imidazo[1,2-a]pyridine-3-carboxamide; 6-(1-methyl-1H-pyrrol-2-yl)-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide; 6-(4-methoxypyridin-3-yl)-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide; 6-(2-aminopyridin-4-yl)-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide; tert-butyl 2-[3,5-dimethyl-4-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-1H-pyrazol-1-yl]acetate; 6-[5-(1-hydroxyethyl)-4-methyl-1,3-thiazol-2-yl]-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide; 6-(4,5-dimethyl-1,3-thiazol-2-yl)-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide; 6-(1-{[(2-hydroxyethyl)carbamoyl]methyl}-3,5-dimethyl-1H-pyrazol-4-yl)-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide; 6-[3,5-dimethyl-1-({[2-(morpholin-4-yl)ethyl]carbamoyl}methyl)-1H-pyrazol-4-yl]-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide; 6-carbamothioyl-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide; N-(2-hydroxyethyl)-4-methyl-2-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-5-carboxamide; 4-methyl-2-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-N-[2-(4-methylpiperazin-1-yl)ethyl]-1,3-thiazole-5-carboxamide; 4-methyl-2-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-N-[3-(4-methylpiperazin-1-yl)propyl]-1,3-thiazole-5-carboxamide; 4-methyl-2-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-N-[2-(morpholin-4-yl)ethyl]-1,3-thiazole-5-carboxamide; 8-amino-N-{5-[5-(3-hydroxy-3-methylbutyl)-1,2,4-oxadiazol-3-yl]-2-methylphenyl}imidazo[1,2-a]pyridine-3-carboxamide; 4-methyl-5-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-2-carboxylic acid; 4-methyl-5-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-N-[2-(4-methylpiperazin-1-yl)ethyl]-1,3-thiazole-2-carboxamide; 2-methyl-4-[3-(4-methyl-3-{7-methylimidazo[1,2-a]pyridine-3-amido}phenyl)-1,2,4-oxadiazol-5-yl]butan-2-yl2-aminoacetate; (2R)-1,1,1-trifluoro-2-methyl-4-[3-(4-methyl-3-{7-methylimidazo[1,2-a]pyridine-3-amido}phenyl)-1,2,4-oxadiazol-5-yl]butan-2-yl(2R)-2-amino-3-methylbutanoate; (2S)-1,1,1-trifluoro-2-methyl-4-[3-(4-methyl-3-{7-methylimidazo[1,2-a]pyridine-3-amido}phenyl)-1,2,4-oxadiazol-5-yl]butan-2-yl (2R)-2-amino-3-methylbutanoate; 7-methyl-N-{2-methyl-5-[5-(4,4,4-trifluoro-3-hydroxybutyl)-1,2,4-oxadiazol-3-yl]phenyl}imidazo[1,2-a]pyridine-3-carboxamide; 7-methyl-N-(2-methyl-5-{5-[3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide; 6-[1-(2-hydroxyethyl)-3,5-dimethyl-1H-pyrazol-4-yl]-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide; 6-(5-acetyl-4-methyl-1,3-thiazol-2-yl)-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide; 6-(3-methyl-1H-pyrazol-4-yl)-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide; N,4-dimethyl-2-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-5-carboxamide; 4-methyl-2-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-5-carboxamide; 6-{3,5-dimethyl-1-[(methylcarbamoyl)methyl]-1H-pyrazol-4-yl}-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide; ethyl 4-methyl-5-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-2-carboxylate; 4-methyl-5-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-N-[2-(morpholin-4-yl)ethyl]-1,3-thiazole-2-carboxamide; N-(2-hydroxyethyl)-4-methyl-5-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-2-carboxamide; 4-methyl-5-(3-{[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]carbamoyl}imidazo[1,2-a]pyridin-6-yl)-1,3-thiazole-2-carboxamide; 6-[2-(hydroxymethyl)-4-methyl-1,3-thiazol-5-yl]-N-[2-methyl-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]imidazo[1,2-a]pyridine-3-carboxamide; N-(2-methyl-5-{5-[1-(2,2,2-trifluoroethoxy)ethyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide; dimethyl (2R)-1,1,1-trifluoro-2-methyl-4-[3-(4-methyl-3-{7-methylimidazo[1,2-a]pyridine-3-amido}phenyl)-1,2,4-oxadiazol-5-yl]butan-2-yl phosphate; {[(2R)-1,1,1-trifluoro-2-methyl-4-[3-(4-methyl-3-{7-methylimidazo[1,2-a]pyridine-3-amido}phenyl)-1,2,4-oxadiazol-5-yl]butan-2-yl]oxy}phosphonic acid; dimethyl (2S)-1,1,1-trifluoro-2-methyl-4-[3-(4-methyl-3-{7-methylimidazo[1,2-a]pyridine-3-amido}phenyl)-1,2,4-oxadiazol-5-yl]butan-2-yl phosphate; {[(2S)-1,1,1-trifluoro-2-methyl-4-[3-(4-methyl-3-{7-methylimidazo[1,2-a]pyridine-3-amido}phenyl)-1,2,4-oxadiazol-5-yl]butan-2-yl]oxy}phosphonic acid, and 1,1,1-trifluoro-2-methyl-4-[3-(4-methyl-3-{7-methylimidazo[1,2-a]pyridine-3-amido}phenyl)-1,2,4-oxadiazol-5-yl]butan-2-yl (2S)-2-aminopropanoate.
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25. The compound of claim 1 selected from:
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N-(5-{[5-(1-hydroxy-2-methylpropan-2-yl)-1,2,4-oxadiazol-3-yl]amino}-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide; 7-methyl-N-(2-methyl-5-{5-[(3S)-4,4,4-trifluoro-3-hydroxy-3-methylbutyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide, and 7-methyl-N-(2-methyl-5-{5-[(3R)-4,4,4-trifluoro-3-hydroxy-3-methylbutyl]-1,2,4-oxadiazol-3-yl}phenyl)imidazo[1,2-a]pyridine-3-carboxamide.
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26. A pharmaceutical composition comprising a therapeutically effective amount a compound of claim 1 and a pharmaceutically acceptable carrier.
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2. The compound of claim 1 wherein:
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15. (canceled)
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27. (canceled)
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35. (canceled)
Specification
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Current AssigneeIRM LLC
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Original AssigneeIRM LLC
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InventorsLiu, Xiaodong, Li, Xiaolin, Loren, Jon, Molteni, Valentina, Nabakka, Juliet, Nguyen, Bao, Petrassi, Hank Michael James, Yeh, Vince
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Application NumberUS14/241,883Publication NumberTime in Patent OfficeDaysField of SearchUS Class Current514/80CPC Class CodesA61K 31/4245 OxadiazolesA61P 1/00 Drugs for disorders of the ...A61P 1/16 for liver or gallbladder di...A61P 11/00 Drugs for disorders of the ...A61P 11/02 Nasal agents, e.g. deconges...A61P 11/06 AntiasthmaticsA61P 17/00 Drugs for dermatological di...A61P 17/04 AntipruriticsA61P 29/00 Non-central analgesic, anti...A61P 3/00 Drugs for disorders of the ...A61P 3/10 for hyperglycaemia, e.g. an...A61P 37/06 Immunosuppressants, e.g. dr...A61P 37/08 Antiallergic agents antiast...A61P 43/00 Drugs for specific purposes...A61P 9/00 Drugs for disorders of the ...A61P 9/12 AntihypertensivesC07D 471/04 Ortho-condensed systemsC07F 9/6561 containing systems of two o...