Fused tri and tetra-cyclic pyrazole kinase inhibitors
2 Assignments
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Accused Products
Abstract
Compounds having the formula (I)
are useful for inhibiting protein kinases. Also disclosed are methods of making the compounds, compositions containing the compounds, and methods of treatment using the compounds.
25 Citations
32 Claims
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1. A compound of formula (I)
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28)
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2. The compound according to claim 1 wherein
X1, X3, and X4 are CH; -
X2 is CH(R7);
X5 is C;
R1 and R2 are independently selected from the group consisting of hydrogen, alkenyloxy, alkoxy, alkoxyalkyl, heterocyclealkyl, hydroxy, hydroxyalkyl, (NRARB)alkyl, and (NRARB)carbonyl;
R3 is hydrogen;
R4 is selected from the group consisting of hydrogen, alkoxycarbonyl, aryl, carboxy, cyano, heteroaryl, hydroxy, —
NRERF, and (NRERF)carbonyl;
R5 is selected from the group consisting of hydrogen and —
NRERF;
R6 is hydrogen;
R7 is hydrogen;
RA is selected from the group consisting of hydrogen and alkyl;
RB is selected from the group consisting of hydrogen, alkyl, cycloalkyl, heteroarylalkyl, heterocycle, and hydroxyalkyl;
RE is selected from the group consisting of hydrogen and alkyl; and
RF is selected from the group consisting of hydrogen, alkyl, and alkylcarbonyl.
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3. The compound according to claim 1 wherein
X1, X3, and X4 are CH; -
X2 is CH(R7);
X5 is C;
R1 and R2 are independently selected from the group consisting of hydrogen, alkenyloxy, alkoxy, alkoxyalkyl, hydroxy, hydroxyalkyl, (NRARB)alkyl, (NRARB)carbonyl, and heterocyclealkyl, wherein the heterocycle of heterocyclealkyl is selected from the group consisting of 4-morpholinyl and 4-hydroxy-1-piperidinyl;
R3 is hydrogen;
R4 is selected from the group consisting of hydrogen, alkoxycarbonyl, carboxy, cyano, heteroaryl, hydroxy, —
NRERF, (NRERF)carbonyl, and aryl, wherein the aryl is phenyl substituted with 1, 2, or 3 substituents selected from the group consisting of alkoxy, formyl, halogen, hydroxy, hydroxyalkyl, and —
NRGRH;
R5 is selected from the group consisting of hydrogen and —
NRERF;
R6 is hydrogen;
R7 is hydrogen;
RA is selected from the group consisting of hydrogen and alkyl;
RB is selected from the group consisting of hydrogen, alkyl, hydroxyalkyl, and cycloalkyl, wherein the cycloalkyl is cyclohexyl substituted with 1 substituent selected from the group consisting of alkyl and hydroxy;
RE is selected from the group consisting of hydrogen and alkyl; and
RF is selected from the group consisting of hydrogen, alkyl, and alkylcarbonyl.
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4. The compound according to claim 1 wherein
X1, X3, and X4 are CH X2 is CH(R7); -
X5 is C;
R1, R3, R5, and R6 are hydrogen;
R2 is selected from the group consisting of alkenyloxy, alkoxyalkyl, hydroxy, hydroxyalkyl, (NRARB)alkyl, (NRARB)carbonyl, and heterocyclealkyl, wherein the heterocycle of heterocyclealkyl is selected from the group consisting of 4-morpholinyl and 4-hydroxy-1-piperidinyl;
R4 is selected from the group consisting of alkoxycarbonyl, carboxy, cyano, hydroxy, and (NRERF)carbonyl;
R7 is hydrogen;
RA is selected from the group consisting of alkyl, hydroxyalkyl, and cycloalkyl, wherein the cycloalkyl is cyclohexyl substituted with 1 substituent selected from the group consisting of alkyl and hydroxy; and
RB, RE and RF are hydrogen.
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5. The compound according to claim 4 selected from the group consisting of
4-(6-{[(trans-4-methylcyclohexyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoic acid; -
4-(6-{[(cis-4-methylcyclohexyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoic acid;
ethyl 4-(6-{[(trans-4-methylcyclohexyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoate;
4-(6-{[(trans-4-hydroxycyclohexyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoic acid;
4-(6-{[(trans-4-hydroxycyclohexyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzamide;
4-[6-(4-morpholinylmethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzoic acid;
methyl 4-[6-(4-morpholinylmethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzoate;
4-[6-(4-morpholinylmethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzamide;
4-{6-[(4-hydroxy-1-piperidinyl)methyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}benzoic acid; and
4-{6-[(4-hydroxy-1-piperidinyl)methyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}benzamide;
4-{6-[(neopentylamino)methyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}benzoic acid;
4-{6-[(neopentylamino)methyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}benzamide;
4-(6-{[(3-hydroxy-2,2-dimethylpropyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoic acid;
4-(6-{[(3-hydroxy-2,2-dimethylpropyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzamide;
4-[6-(hydroxymethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzoic acid;
4-[6-(hydroxymethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzamide;
4-[6-(methoxymethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzoic acid;
4-[6-(allyloxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzoic acid;
methyl 4-[6-(allyloxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzoate;
4-[6-(allyloxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzamide;
methyl 4-(6-hydroxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoate;
4-(6-hydroxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoic acid;
4-(6-{[(trans-4-hydroxycyclohexyl)amino]carbonyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoic acid;
4-{6-[(neopentylamino)carbonyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}benzoic acid;
3-[4-(aminocarbonyl)phenyl]-N-neopentyl-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxamide; and
4-(6-{[(trans-4-methylcyclohexyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenol.
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6. The compound according to claim 1 wherein
X1, X3, and X4 are CH X2 is CH(R7); -
X5 is C;
R1, R3, R5, and R6 are hydrogen;
R2 is selected from the group consisting of hydrogen, alkenyloxy, alkoxyalkyl, hydroxy, hydroxyalkyl, (NRARB)alkyl, (NRARB)carbonyl, and heterocyclealkyl, wherein the heterocycle of heterocyclealkyl is selected from the group consisting of 4-morpholinyl and 4-hydroxy-1-piperidinyl;
R4 is aryl wherein the aryl is phenyl substituted with 1, 2, or 3 substituents selected from the group consisting of alkoxy, formyl, halogen, hydroxy, hydroxyalkyl, and —
NRGRH;
R7 is hydrogen;
RA is selected from the group consisting of alkyl, hydroxyalkyl, and cycloalkyl, wherein the cycloalkyl is cyclohexyl substituted with 1 substituent selected from the group consisting of alkyl and hydroxy; and
RB, RE, and RF are hydrogen.
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7. The compound according to claim 6 selected from the group consisting of
4′ - -(6-{[(cis-4-methylcyclohexyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
-biphenyl-4-ol;
4′
-(6-{[(trans-4-hydroxycyclohexyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-3-methoxy-1,1′
-biphenyl-4-ol;
4′
-(6-{[(trans-4-hydroxycyclohexyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-3-(hydroxymethyl)-1,1′
-biphenyl-4-ol;
3-methoxy-4′
-{6-[(neopentylamino)methyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
4′
-(6-{[(3-hydroxy-2,2-dimethylpropyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-3-methoxy-1,1′
-biphenyl-4-ol;
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-1,4-dihydroindeno[1,2-c]pyrazol-6-ol;
3-(4′
-hydroxy-3′
-methoxy-1,1′
-biphenyl-4-yl)-1,4-dihydroindeno[1,2-c]pyrazol-6-ol;
4′
-[6-(hydroxymethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
-biphenyl-4-ol;
4′
-[6-(hydroxymethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-3-methoxy-1,1′
-biphenyl-4-ol;
3-(3′
-fluoro-4′
-hydroxy-1,1′
-biphenyl-4-yl)-1,4-dihydroindeno[1,2-c]pyrazol-6-ol;
3-(3′
-amino-4′
-hydroxy-1,1′
-biphenyl-4-yl)-1,4-dihydroindeno[1,2-c]pyrazol-6-ol;
4-hydroxy-4′
-[6-(hydroxymethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-5-methoxy-1,1′
-biphenyl-2-carbaldehyde;
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-N-(trans-4-hydroxycyclohexyl)-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxamide; and
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-N-neopentyl-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxamide.
- -(6-{[(cis-4-methylcyclohexyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
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8. The compound according to claim 1 wherein
X1, X3, and X4 are CH; -
X2 is CH(R7);
X5 is C;
R1, R3, R5, and R6 are hydrogen;
R2 is selected from the group consisting of hydrogen, alkenyloxy, alkoxyalkyl, hydroxy, hydroxyalkyl, (NRARB)alkyl, (NRARB)carbonyl, and heterocyclealkyl, wherein the heterocycle of heterocyclealkyl is selected from the group consisting of 4-morpholinyl and 4-hydroxy-1-piperidinyl;
R4 is heteroaryl;
R7 is hydrogen;
RA is selected from the group consisting of alkyl, hydroxyalkyl, and cycloalkyl, wherein the cycloalkyl is cyclohexyl substituted with 1 substituent selected from the group consisting of alkyl and hydroxy; and
RB is selected from the group consisting of hydrogen and alkyl.
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9. The compound according to claim 8 that is 6-(allyloxy)-3-[4-(1H-tetraazol-5-yl)phenyl]-1,4-dihydroindeno[1,2-c]pyrazole.
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10. The compound according to claim 1 wherein
X1, X3, and X4 are CH; -
X2 is CH(R7);
X5 is C;
R1, R3, and R6 are hydrogen;
R2 is selected from the group consisting of alkenyloxy, alkoxyalkyl, hydroxy, hydroxyalkyl, (NRARB)alkyl, (NRARB)carbonyl, and heterocyclealkyl, wherein the heterocycle of heterocyclealkyl is selected from the group consisting of 4-morpholinyl and 4-hydroxy-1-piperidinyl;
R4 is selected from the group consisting of hydrogen, carboxy, and cyano;
R5 is selected from the group consisting of alkoxycarbonyl, carboxy, hydroxy, hydroxyalkyl, —
NRERF, and (NRERF)carbonyl;
R7 is hydrogen;
RA is selected from the group consisting of alkyl, hydroxyalkyl, and cycloalkyl, wherein the cycloalkyl is cyclohexyl substituted with 1 substituent selected from the group consisting of alkyl and hydroxy;
RB is selected from the group consisting of hydrogen and alkyl;
RE is selected from the group consisting of hydrogen and alkyl; and
RF is selected from the group consisting of hydrogen, alkyl, and alkylcarbonyl.
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11. The compound according to claim 10 selected from the group consisting of
N-[3-(6-{[(trans-4-hydroxycyclohexyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenyl]acetamide; -
N-{3-[6-(4-morpholinylmethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]phenyl}acetamide;
2-(acetylamino)-4-[6-(4-morpholinylmethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzoic acid; and
N-(3-{6-[(4-hydroxy-1-piperidinyl)methyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}phenyl)acetamide.
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12. The compound according to claim 1 wherein
X1, X3, and X4 are CH; -
X2 is CH(R7);
X5 is C;
R2, R3, R5, and R6 are hydrogen;
R1 is selected from the group consisting of alkenyloxy, alkoxyalkyl, hydroxy, hydroxyalkyl, (NRARB)alkyl, (NRARB)carbonyl, and heterocyclealkyl, wherein the heterocycle of heterocyclealkyl is selected from the group consisting of 4-morpholinyl and 4-hydroxy-1-piperidinyl;
R4 is selected from the group consisting of alkoxycarbonyl, carboxy, cyano, hydroxy, hydroxyalkyl, —
NRERF, and (NRERF)carbonyl;
R7 is hydrogen;
RA is selected from the group consisting of alkyl, hydroxyalkyl, and cycloalkyl, wherein the cycloalkyl is cyclohexyl substituted with 1 substituent selected from the group consisting of alkyl and hydroxy;
RB is selected from the group consisting of hydrogen and alkyl;
RE is selected from the group consisting of hydrogen and akyl; and
RF is selected from the group consisting of hydrogen, alkyl, and alkylcarbonyl.
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13. The compound according to claim 12 selected from the group consisting of
4-[7-(hydroxymethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzoic acid; -
4-[7-(hydroxymethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzamide;
4-[7-(4-morpholinylmethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzoic acid;
4-[7-(4-morpholinylmethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzamide;
4-(7-{[(2-hydroxyethyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoic acid;
4-{7-[(neopentylamino)methyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}benzamide;
4-{7-[(methylamino)carbonyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}benzoic acid;
3-[4-(aminocarbonyl)phenyl]-N-methyl-1,4-dihydroindeno[1,2-c]pyrazole-7-carboxamide;
4-{7-[(neopentylamino)carbonyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}benzoic acid; and
4-(7-{[(trans-4-hydroxycyclohexyl)amino]carbonyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoic acid.
-
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14. The compound according to claim 1 wherein
X1, X3, and X4 are CH; -
X2 is CH(R7);
X5 is C;
R2, R3, R5, and R6 are hydrogen;
R1 is selected from the group consisting of alkenyloxy, alkoxyalkyl, hydroxy, hydroxyalkyl, (NRARB)alkyl, (NRARB)carbonyl, and heterocyclealkyl, wherein the heterocycle of heterocyclealkyl is selected from the group consisting of 4-morpholinyl and 4-hydroxy-1-piperidinyl;
R4 is aryl wherein the aryl is phenyl substituted with 1, 2, or 3 substituents selected from the group consisting of alkoxy, formyl, halogen, hydroxy, hydroxyalkyl, and —
NRGRH;
R7 is hydrogen;
RA is selected from the group consisting of alkyl, hydroxyalkyl, and cycloalkyl, wherein the cycloalkyl is cyclohexyl substituted with 1 substituent selected from the group consisting of alkyl and hydroxy;
RB is selected from the group consisting of hydrogen and alkyl;
RE is selected from the group consisting of hydrogen and alkyl; and
RF is selected from the group consisting of hydrogen, alkyl, and alkylcarbonyl.
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15. The compound according to claim 14 selected from the group consisting of
4′ - -[7-(hydroxymethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-3-methoxy-1,1′
-biphenyl-4-ol;
4′
-[7-(hydroxymethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-{7-[(neopentylamino)methyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-N-methyl-1,4-dihydroindeno[1,2-c]pyrazole-7-carboxamide; and
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-N-neopentyl-1,4-dihydroindeno[1,2-c]pyrazole-7-carboxamide.
- -[7-(hydroxymethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-3-methoxy-1,1′
-
16. The compound according to claim 1 wherein
X1, X3, and X4 are CH; -
X2 is CH(R7);
X5 is C;
R2, R3, and R6 are hydrogen;
R1 is selected from the group consisting of alkenyloxy, alkoxyalkyl, hydroxy, hydroxyalkyl, (NRARB)alkyl, (NRARB)carbonyl, and heterocyclealkyl, wherein the heterocycle of heterocyclealkyl is selected from the group consisting of 4-morpholinyl and 4-hydroxy-1-piperidinyl;
R4 is selected from the group consisting of hydrogen, carboxy, and cyano;
R5 is selected from the group consisting of alkoxycarbonyl, carboxy, hydroxy, hydroxyalkyl, —
NRERF, and (NRERF)carbonyl;
R7 is hydrogen;
RA is selected from the group consisting of alkyl, hydroxyalkyl, and cycloalkyl, wherein the cycloalkyl is cyclohexyl substituted with 1 substituent selected from the group consisting of alkyl and hydroxy;
RB is selected from the group consisting of hydrogen and alkyl;
RE is selected from the group consisting of hydrogen and alkyl; and
RF is selected from the group consisting of hydrogen, alkyl, and alkylcarbonyl.
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17. The compound according to claim 16 that is N-{3-[7-(hydroxymethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]phenyl}acetamide.
-
18. The compound according to claim 1 wherein
X1, X3, and X4 are CH; -
X2 is CH(R7);
X5 is C;
R1 and R2 are alkoxy;
R3 and R6 are hydrogen;
R4 is selected from the group consisting of alkoxycarbonyl, carboxy, cyano, hydroxy, —
NRERF, and (NRERF)carbonyl;
R5 is selected from the group consisting of hydrogen and carboxy;
R7 is hydrogen;
RE is selected from the group consisting of hydrogen and alkyl; and
RF is selected from the group consisting of hydrogen, alkyl, and alkylcarbonyl.
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19. The compound according to claim 18 that is 4-(6,7-dimethoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoic acid.
-
20. The compound according to claim 1 wherein
X1, X3, and X4 are CH; -
X2 is CH(R7);
X5 is C;
R1 and R2 are alkoxy;
R3, R5, and R6 are hydrogen;
R4 is aryl wherein the aryl is phenyl substituted with 1, 2, or 3 substituents selected from the group consisting of alkoxy, formyl, halogen, hydroxy, hydroxyalkyl, and —
NRGRH;
R7 is hydrogen;
RE is selected from the group consisting of hydrogen and alkyl; and
RF is selected from the group consisting of hydrogen, alkyl, and alkylcarbonyl.
-
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21. The compound according to claim 20 that is 4′
- -(6,7-dimethoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
-biphenyl-4-ol.
- -(6,7-dimethoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
-
22. The compound according to claim 1 wherein
X1, X3, and X4 are CH; -
X2 is CH(R7);
X5 is C;
R1 and R2 are alkoxy;
R3, R5, and R6 are hydrogen;
R4 is heteroaryl; and
R7 is hydrogen.
-
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23. The compound according to claim 22 that is 6,7-dimethoxy-3-[4-(1H-tetraazol-5-yl)phenyl]-1,4-dihydroindeno[1,2-c]pyrazole.
-
24. The compound according to claim 1 wherein
X1, X3, and X4 are CH; -
X2 is CH(R7);
X5 is C;
R1, R2, R3, R5, and R6 are hydrogen;
R4 is selected from the group consisting of alkoxycarbonyl, carboxy, cyano, hydroxy, hydroxyalkyl, —
NRERF, and (NRERF)carbonyl; and
R7 is selected from the group consisting of alkoxy and hydroxy.
-
-
25. The compound according to claim 24 that is 4-(4-hydroxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoic acid.
-
26. The compound according to claim 1 wherein
X1 is CH; -
X2 is CH(R7);
X3 is N;
X4 is CH;
X5 is C;
R1, R3, R5, and R6 are hydrogen;
R2 is selected from the group consisting of alkenyloxy, alkoxyalkyl, hydroxy, hydroxyalkyl, (NRARB)alkyl, (NRARB)carbonyl, and heterocyclealkyl, wherein the heterocycle of heterocyclealkyl is selected from the group consisting of 4-morpholinyl and 4-hydroxy-1-piperidinyl;
R4 is selected from the group consisting of hydrogen, alkoxycarbonyl, carboxy, cyano, hydroxy, hydroxyalkyl, —
NRERF, and (NRERF)carbonyl;
R7 is hydrogen;
RA is selected from the group consisting of alkyl, hydroxyalkyl, and cycloalkyl, wherein the cycloalkyl is cyclohexyl substituted with 1 substituent selected from the group consisting of alkyl and hydroxy;
RB is selected from the group consisting of hydrogen and alkyl;
RE is selected from the group consisting of hydrogen and alkyl; and
RF is selected from the group consisting of hydrogen, alkyl, and alkylcarbonyl.
-
-
27. The compound according to claim 26 selected from the group consisting of
6-[6-(allyloxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]nicotinic acid; - and
6-(6-hydroxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)nicotinic acid.
- and
-
28. The compound according to claim 1 selected from the group consisting of
4′ - -[6-(morpholin-4-ylmethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-{5-[(neopentylamino)methyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
4′
-{6-[(neopentylamino)methyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
4′
-(5-{[(2-hydroxyethyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
-biphenyl-4-ol;
4′
-(6-{[(2-hydroxyethyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
-biphenyl-4-ol;
4′
-(7-{[(2-hydroxyethyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
-biphenyl-4-ol;
4′
-{6-[(butylamino)methyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
1-{[3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-1,4-dihydroindeno[1,2-c]pyrazol-6-yl]methyl}piperidin-4-ol;
4′
-{6-[(4-methylpiperazin-1-yl)methyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
4′
-{6-[(pyridin-4-ylamino)methyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
4′
-(6-{[(3-hydroxy-2,2-dimethylpropyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
-biphenyl-4-ol;
1-{[3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-1,4-dihydroindeno[1,2-c]pyrazol-6-yl]methyl}piperidine-4-carboxamide;
4′
-[6-({[(5-methylpyrazin-2-yl)methyl]amino}methyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-(6-{[(pyridin-2-ylmethyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
-biphenyl-4-ol;
4′
-(7-{[(2-pyrrolidin-1-ylethyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
-biphenyl-4-ol;
4′
-[6-(thiomorpholin-4-ylmethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
[3-(4′
-Hydroxy-biphenyl-4-yl)-1,4-dihydro-indeno[1,2-c]pyrazol-6-yl]-morpholin-4-yl-methanone4′
-[6-(morpholin-4-ylcarbonyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
N-cyclohexyl-3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxamide;
4′
-[7-(morpholin-4-ylcarbonyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-N-(2-hydroxyethyl)-1,4-dihydroindeno[1,2-c]pyrazole-7-carboxamide;
1-{[3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-1,4-dihydroindeno[1,2-c]pyrazol-6-yl]carbonyl}piperidin-4-ol;
4′
-[6-(piperazin-1-ylcarbonyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-{6-[(4-methylpiperazin-1-yl)carbonyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-N-(pyridin-4-ylmethyl)-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxamide;
1-{[3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-1,4-dihydroindeno[1,2-c]pyrazol-6-yl]carbonyl}piperidine-4-carboxamide;
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-N-[(5-methylpyrazin-2-yl)methyl]-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxamide;
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-N-(pyridin-2-ylmethyl)-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxamide;
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-N-{[6-(trifluoromethyl)pyridin-3-yl]methyl}-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxamide;
N-[2-(dimethylamino)ethyl]-3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxamide;
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-N-(pyridin-3-ylmethyl)-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxamide;
N-[3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-1,4-dihydroindeno[1,2-c]pyrazol-6-yl]-2-morpholin-4-ylacetamide;
N-[3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-1,4-dihydroindeno[1,2-c]pyrazol-5-yl]acetamide;
N-[3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-1,4-dihydroindeno[1,2-c]pyrazol-6-yl]-2-[(pyridin-4-ylmethyl)amino]acetamide;
N-[3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-1,4-dihydroindeno[1,2-c]pyrazol-6-yl]-2-[trans-(4-hydroxycyclohexyl)amino]acetamide;
2-(butylamino)-N-[3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-1,4-dihydroindeno[1,2-c]pyrazol-6-yl]acetamide;
N-[3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-1,4-dihydroindeno[1,2-c]pyrazol-6-yl]-2-[(2-hydroxyethyl)amino]acetamide;
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-7-methoxy-N-(pyridin-4-ylmethyl)-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxamide;
4′
-(6-{[(2-hydroxyethyl)amino]methyl}-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
-biphenyl-4-ol;
4′
-{7-methoxy-6-[(4-methylpiperazin-1-yl)carbonyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-N-(trans-4-hydroxycyclohexyl)-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxamide;
4′
-[7-methoxy-6-(morpholin-4-ylcarbonyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
1-{[3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-6-yl]carbonyl}piperidine-4-carboxamide;
1-{[3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-6-yl]carbonyl}piperidin-4-ol;
4′
-{7-methoxy-6-[(4-methylpiperazin-1-yl)methyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
4′
-(7-methoxy-6-{[(2-pyrrolidin-1-ylethyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
-biphenyl-4-ol;
4′
-(6-{[(trans-4-hydroxycyclohexyl)amino]methyl}-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
-biphenyl-4-ol;
4′
-{7-methoxy-6-[(pyridin-4-ylamino)methyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
1-{[3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-6-yl]methyl}piperidine-4-carboxamide;
1-{[3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-6-yl]methyl}piperidine-4-carboxamide;
3-fluoro-4′
-[6-(hydroxymethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
3-fluoro-4′
-(7-methoxy-6-{[(2-pyrrolidin-1-ylethyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
-biphenyl-4-ol;
3-fluoro-4′
-{6-[(4-methylpiperazin-1-yl)methyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
3-(3′
-fluoro-4′
-hydroxy-1,1′
-biphenyl-4-yl)-N-(pyridin-2-ylmethyl)-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxamide;
3-fluoro-4′
-(7-{[(2-pyrrolidin-1-ylethyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
-biphenyl-4-ol;
3-fluoro-4′
-[7-methoxy-6-(morpholin-4-ylcarbonyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
5-{6-[(4-methylpiperazin-1-yl)methyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}pyridine-2-carbonitrile;
3-(6-cyanopyridin-3-yl)-N-(pyridin-2-ylmethyl)-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxamide;
5-{6-[(4-hydroxypiperidin-1-yl)methyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}pyridine-2-carbonitrile;
5-(6-{[(pyridin-2-ylmethyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridine-2-carbonitrile;
5-(6-{[(trans-4-hydroxycyclohexyl)amino]methyl}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridine-2-carbonitrile;
3-(6-cyanopyridin-3-yl)-N-(trans-4-hydroxycyclohexyl)-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxamide;
3-(6-cyanopyridin-3-yl)-N-{[6-(trifluoromethyl)pyridin-3-yl]methyl}-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxamide;
5-[6-(hydroxymethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-{6-[(pyridin-3-yloxy)methyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}pyridine-2-carbonitrile;
5-{6-[(pyridin-4-yloxy)methyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}pyridine-2-carbonitrile;
3-(6-fluoropyridin-3-yl)-7-methoxy-4,4-dimethyl-1,4-dihydroindeno[1,2-c]pyrazol-6-ol;
5-(6-hydroxy-7-methoxy-4,4-dimethyl-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridine-2-carbonitrile;
5-[7-methoxy-4,4-dimethyl-6-(pyridin-3-ylmethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-[7-methoxy-4,4-dimethyl-6-(3-morpholin-4-ylpropoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-[7-methoxy-4,4-dimethyl-6-(tetrahydrofuran-3-yloxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-(6-{[(2R)-2,3-dihydroxypropyl]oxy}-7-methoxy-4,4-dimethyl-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridine-2-carbonitrile;
5-[7-methoxy-4,4-dimethyl-6-(pyridin-2-ylmethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-[7-methoxy-4,4-dimethyl-6-(3-piperidin-1-ylpropoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-(6,7-dimethoxy-4,4-dimethyl-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridine-2-carbonitrile;
5-[7-methoxy-6-(pyridin-2-ylmethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-{7-[(6-chloropyridin-3-yl)methoxy]-6-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}pyridine-2-carbonitrile;
5-[6-methoxy-7-(pyridin-2-ylmethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-[6-methoxy-7-(2-piperidin-1-ylethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-[6-methoxy-7-(pyridin-3-ylmethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-[6-methoxy-7-(2-morpholin-4-ylethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-{6-methoxy-7-[2-(4-methyl-1,3-thiazol-5-yl)ethoxy]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}pyridine-2-carbonitrile;
5-[6-methoxy-7-(2-pyrrolidin-1-ylethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-{6-methoxy-7-[2-(2-oxopyrrolidin-1-yl)ethoxy]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}pyridine-2-carbonitrile;
5-[7-(2-hydroxyethoxy)-6-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-{7-[(6-bromopyridin-2-yl)methoxy]-6-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}pyridine-2-carbonitrile;
5-[7-methoxy-6-(pyridin-3-ylmethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-[7-methoxy-6-(3-morpholin-4-ylpropoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-[7-methoxy-6-(tetrahydrofuran-3-yloxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-{6-[3-(dimethylamino)propoxy]-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}pyridine-2-carbonitrile;
5-{7-methoxy-6-[2-(4-methyl-1,3-thiazol-5-yl)ethoxy]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}pyridine-2-carbonitrile;
5-[6-(2-hydroxyethoxy)-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-{6-[(6-bromopyridin-2-yl)methoxy]-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}pyridine-2-carbonitrile;
5-{6-[(6-chloropyridin-3-yl)methoxy]-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}pyridine-2-carbonitrile;
5-[7-methoxy-6-(2-morpholin-4-ylethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-{6-[2-(5-ethylpyridin-2-yl)ethoxy]-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}pyridine-2-carbonitrile;
4′
-(6,7-dimethoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-3-methoxy-1,1′
-biphenyl-4-ol;
4-(6,7-dimethoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenol;
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-1,4-dihydroindeno[1,2-c]pyrazole-6,7-diol;
4-(6,7-dimethoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzonitrile;
3-(6-hydroxy-2-naphthyl)-1,4-dihydroindeno[1,2-c]pyrazol-6-ol;
6,7-dimethoxy-3-[4-(1H-pyrrol-2-yl)phenyl]-1,4-dihydroindeno[1,2-c]pyrazole;
6,7-dimethoxy-3-[4-(1H-pyrazol-4-yl)phenyl]-1,4-dihydroindeno[1,2-c]pyrazole;
3-(4-bromophenyl)-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-6-ol;
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-6-ol;
3-(4′
-hydroxy-3′
-methoxy-1,1′
-biphenyl-4-yl)-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-6-ol;
4′
-[7-methoxy-6-(pyridin-2-ylmethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-[7-methoxy-6-(pyridin-4-ylmethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-(7-methoxy-6-{3-[4-(2-methoxyphenyl)piperazin-1-yl]propoxy}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
-biphenyl-4-ol;
4′
-(6-{3-[4-(3-chlorophenyl)piperazin-1-yl]propoxy}-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
-biphenyl-4-ol;
4′
-{6-[2-(dimethylamino)ethoxy]-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
4′
-[7-methoxy-6-(2-piperidin-1-ylethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-[7-methoxy-6-(3-piperidin-1-ylpropoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-{6-[2-(dimethylamino)-1-methylethoxy]-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
4′
-{7-methoxy-6-[2-(1-methylpyrrolidin-2-yl)ethoxy]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
4′
-{6-[2-(1H-imidazol-1-yl)ethoxy]-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
4′
-[7-methoxy-6-(2-morpholin-4-ylethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-{6-[3-(dimethylamino)propoxy]-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
4′
-[7-methoxy-6-(2-pyrrolidin-1-ylethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-{6-[2-(diethylamino)ethoxy]-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
4′
-[7-methoxy-6-(pyridin-3-ylmethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-[7-methoxy-6-(2-pyridin-2-ylethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-{6-[2-(5-ethylpyridin-2-yl)ethoxy]-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
4′
-[7-methoxy-6-(2-pyridin-4-ylethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
2-{[3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-6-yl]oxy}propane-1,3-diol;
(2S)-3-{[3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-6-yl]oxy}propane-1,2-diol;
(2R)-3-{[3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-6-yl]oxy}propane-1,2-diol;
4′
-(7-methoxy-6-{2-[3-(6-methylpyridin-2-yl)propoxy]ethoxy}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
-biphenyl-4-ol;
4′
-{6-[3-chloro-2-(hydroxymethyl)-2-methylpropoxy]-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
N,N-diethyl-2-{[3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-6-yl]oxy}acetamide;
4′
-[7-methoxy-6-(tetrahydrofuran-3-ylmethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-[7-methoxy-6-(tetrahydro-2H-pyran-4-yloxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-[7-methoxy-6-(2-pyridin-3-ylethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-[7-methoxy-6-(tetrahydrofuran-3-yloxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-[6-(cyclohex-3-en-1-ylmethoxy)-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-[7-methoxy-6-(3-morpholin-4-ylpropoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4-(6-hydroxy-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzonitrile;
4-[7-methoxy-6-(pyridin-2-ylmethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzonitrile;
4-[7-methoxy-6-(pyridin-3-ylmethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzonitrile;
4-[7-methoxy-6-(pyridin-4-ylmethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzonitrile;
4-[7-methoxy-6-(tetrahydro-2H-pyran-4-yloxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzonitrile;
4-[7-methoxy-6-(3-morpholin-4-ylpropoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzonitrile;
4-(6-{[(2R)-2,3-dihydroxypropyl]oxy}-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzonitrile;
4-{6-[2-hydroxy-1-(hydroxymethyl)ethoxy]-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}benzonitrile;
4-{6-[2-(5-ethylpyridin-2-yl)ethoxy]-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}benzonitrile;
4-{7-methoxy-6-[2-(5-methyl-1,3-thiazol-4-yl)ethoxy]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}benzonitrile;
4-{6-[3-(dimethylamino)propoxy]-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}benzonitrile;
4-[7-methoxy-6-(tetrahydrofiuran-3-ylmethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzonitrile;
4-[7-methoxy-6-(tetrahydrofuran-3-yloxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzonitrile;
4-{6-[2-(2,5-dioxopyrrolidin-1-yl)ethoxy]-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}benzonitrile;
4-{6-[2-(3,5-dimethyl-1H-pyrazol-1-yl)ethoxy]-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}benzonitrile;
3-(4-cyanophenyl)-N-(4-hydroxycyclohexyl)-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxamide;
3-(4-cyanophenyl)-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxylic acid;
3-(4-cyanophenyl)-7-methoxy-N-(pyridin-2-ylmethyl)-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxamide;
3-(4-cyanophenyl)-7-methoxy-N-(pyridin-3-ylmethyl)-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxamide;
3-(4-cyanophenyl)-7-methoxy-N-(pyridin-4-ylmethyl)-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxamide;
3-(4-cyanophenyl)-7-methoxy-N-(4-morpholin-4-ylphenyl)-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxamide;
3-(4-cyanophenyl)-7-methoxy-N-(2-pyrrolidin-1-ylethyl)-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxamide;
3-(4-cyanophenyl)-7-methoxy-N-(2-piperidin-1-ylethyl)-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxamide;
3-(4-cyanophenyl)-7-methoxy-N-(2-morpholin-4-ylethyl)-1,4-dihydroindeno[1,2-c]pyrazole-6-carboxamide;
4-(6-{[(4-hydroxycyclohexyl)amino]methyl}-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzonitrile;
4-[6-(1H-imidazol-1-ylmethyl)-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzonitrile;
3-(6-chloropyridin-3-yl)-6,7-dimethoxy-1,4-dihydroindeno[1,2-c]pyrazole;
4-[5-(6,7-dimethoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridin-2-yl]phenol;
4-[5-(6,7-dimethoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridin-2-yl]-2-methoxyphenol;
4-[5-(6,7-dimethoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridin-2-yl]-2-fluorophenol;
5-(6,7-dimethoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridine-2-carbonitrile;
6-(6,7-dimethoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)nicotinonitrile;
3-(5-bromopyridin-2-yl)-6,7-dimethoxy-1,4-dihydroindeno[1,2-c]pyrazole;
4′
-[6-(1-hydroxy-1-methylethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4-[6-(1-hydroxy-1-methylethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzonitrile;
2-[3-(6-chloropyridin-3-yl)-1,4-dihydroindeno[1,2-c]pyrazol-6-yl]propan-2-ol;
4-{5-[6-(1-hydroxy-1-methylethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridin-2-yl}phenol;
3-(5,6-dichloropyridin-3-yl)-6,7-dimethoxy-1,4-dihydroindeno[1,2-c]pyrazole;
2-[3-(6-fluoropyridin-3-yl)-1,4-dihydroindeno[1,2-c]pyrazol-6-yl]propan-2-ol;
6,7-dimethoxy-3-pyrazin-2-yl-1,4-dihydroindeno[1,2-c]pyrazole;
6,7-dimethoxy-3-pyridin-3-yl-1,4-dihydroindeno[1,2-c]pyrazole;
6,7-dimethoxy-3-pyrimidin-5-yl-1,4-dihydroindeno[1,2-c]pyrazole;
3-(6-chloropyridin-3-yl)-7-ethyl-6-methoxy-1,4-dihydroindeno[1,2-c]pyrazole;
5-(7-ethyl-6-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridine-2-carbonitrile;
3-(6-chloropyridin-3-yl)-7-ethyl-6-(tetrahydro-2H-pyran-4-yloxy)-1,4-dihydroindeno[1,2-c]pyrazole;
4-{5-[7-ethyl-6-(tetrahydro-2H-pyran-4-yloxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridin-2-yl}phenol;
5-[7-ethyl-6-(3-morpholin-4-ylpropoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-[7-ethyl-6-(tetrahydrofuran-3-ylmethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-[7-ethyl-6-(tetrahydrofuran-3-yloxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-{7-ethyl-6-[(4-hydroxycyclohexyl)oxy]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}pyridine-2-carbonitrile;
5-[7-ethyl-6-(tetrahydro-2H-pyran-4-yloxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-[7-ethyl-6-(pyridin-2-ylmethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-(6,7-diethyl-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridine-2-carbonitrile;
3-(6-chloropyridin-3-yl)-6,7-bis(2-methoxyethoxy)-1,4-dihydroindeno[1,2-c]pyrazole;
5-[6,7-bis(2-methoxyethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
6-hydroxy-3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-7-methoxyindeno[1,2-c]pyrazol-4(1H)-one;
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-7-methoxy-6-(2-piperidin-1-ylethoxy)indeno[1,2-c]pyrazol-4(1H)-one;
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-7-methoxy-6-[(1-methylpiperidin-3-yl)methoxy]indeno[1,2-c]pyrazol-4(1H)-one;
6-{3-[4-(3-chlorophenyl)piperazin-1-yl]propoxy}-3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-7-methoxyindeno[1,2-c]pyrazol-4(1H)-one;
4-{6-[3-(dimethylamino)propoxy]-7-methoxy-4-oxo-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}benzonitrile;
4-(6-hydroxy-7-methoxy-4-oxo-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzonitrile;
4-[7-methoxy-4-oxo-6-(tetrahydrofuran-3-yloxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzonitrile;
4-[7-methoxy-6-(3-morpholin-4-ylpropoxy)-4-oxo-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzonitrile;
3-(6-chloropyridin-3-yl)-6,7-dimethoxy-4-methyl-1,4-dihydroindeno[1,2-c]pyrazol-4-ol;
4′
-[6-methoxy-7-(2-pyrrolidin-1-ylethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-[6-methoxy-7-(2-morpholin-4-ylethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-{7-[2-(diethylamino)ethoxy]-6-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
4′
-[6-methoxy-7-(pyridin-3-ylmethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-[6-methoxy-7-(pyridin-2-ylmethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-(7-{3-[4-(3-chlorophenyl)piperazin-1-yl]propoxy}-6-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
-biphenyl-4-ol;
4′
-[6-methoxy-7-(pyridin-4-ylmethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-{7-[2-(dimethylamino)ethoxy]-6-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
4′
-[6-methoxy-7-(2-piperidin-1-ylethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-{7-[3-(dimethylamino)propoxy]-6-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
4′
-[6-methoxy-7-(3-piperidin-1-ylpropoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4′
-{7-[2-(dimethylamino)-1-methylethoxy]-6-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
4′
-(7-{2-(dimethylamino)-1-[(dimethylamino)methyl]ethoxy}-6-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
-biphenyl-4-ol;
4′
-{7-[(1-ethylpiperidin-3-yl)oxy]-6-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
4′
-{7-[3-(dimethylamino)-2-methylpropoxy]-6-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
4′
-{6-methoxy-7-[2-(1-methylpyrrolidin-2-yl)ethoxy]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
4′
-{7-[2-(1H-imidazol-1-yl)ethoxy]-6-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
4′
-{6-methoxy-7-[3-(4-methylpiperazin-1-yl)propoxy]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-6-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-7-ol;
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-6-methoxy-N-[2-(4-methylpiperazin-1-yl)ethyl]-1,4-dihydroindeno[1,2-c]pyrazole-7-carboxamide;
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-6-methoxy-N-(pyridin-2-ylmethyl)-1,4-dihydroindeno[1,2-c]pyrazole-7-carboxamide;
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-6-methoxy-N-(pyridin-4-ylmethyl)-1,4-dihydroindeno[1,2-c]pyrazole-7-carboxamide;
N-[2-(diethylamino)ethyl]-3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-6-methoxy-1,4-dihydroindeno[1,2-c]pyrazole-7-carboxamide;
N-[3-(diethylamino)propyl]-3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-6-methoxy-1,4-dihydroindeno[1,2-c]pyrazole-7-carboxamide;
N-[4-(diethylamino)butyl]-3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-6-methoxy-1,4-dihydroindeno[1,2-c]pyrazole-7-carboxamide;
N-[2-(dimethylamino)ethyl]-3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-6-methoxy-1,4-dihydroindeno[1,2-c]pyrazole-7-carboxamide;
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-6-methoxy-N-(2-pyrrolidin-1-ylethyl)-1,4-dihydroindeno[1,2-c]pyrazole-7-carboxamide;
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-6-methoxy-N-(3-pyrrolidin-1-ylpropyl)-1,4-dihydroindeno[1,2-c]pyrazole-7-carboxamide;
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-6-methoxy-N-(2-piperidin-1-ylethyl)-1,4-dihydroindeno[1,2-c]pyrazole-7-carboxamide;
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-6-methoxy-N-(3-piperidin-1-ylpropyl)-1,4-dihydroindeno[1,2-c]pyrazole-7-carboxamide;
3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-6-methoxy-N-(2-morpholin-4-ylethyl)-1,4-dihydroindeno[1,2-c]pyrazole-7-carboxamide;
N-[2-(dimethylamino)ethyl]-3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-6-methoxy-N-methyl-1,4-dihydroindeno[1,2-c]pyrazole-7-carboxamide;
N-[3-(dimethylamino)propyl]-3-(4′
-hydroxy-1,1′
-biphenyl-4-yl)-6-methoxy-N-methyl-1,4-dihydroindeno[1,2-c]pyrazole-7-carboxamide;
4′
-{6-methoxy-7-[(4-methyl-1,4-diazepan-1-yl)carbonyl]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}-1,1′
-biphenyl-4-ol;
6-methoxy-3-{4-[3-(1-methylpyrrolidin-2-yl)propoxy]phenyl}-7-(2-piperidin-1-ylethoxy)-1,4-dihydroindeno[1,2-c]pyrazole;
1-{4-[6-methoxy-7-(2-piperidin-1-ylethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]phenoxy}acetone;
[4-(6,7-dimethoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenyl]methanol;
3-(4-cyanophenyl)-6-methoxy-N-(pyridin-4-ylmethyl)-1,4-dihydroindeno[1,2-c]pyrazole-7-carboxamide;
methyl 3-(4-cyanophenyl)-6-methoxy-1,4-dihydroindeno[1,2-c]pyrazole-7-carboxylate;
3-(4-cyanophenyl)-N-(trans-4-hydroxycyclohexyl)-6-methoxy-1,4-dihydroindeno[1,2-c]pyrazole-7-carboxamide;
4-[6-methoxy-7-(pyridin-3-ylmethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzonitrile;
4-{7-[2-(dimethylamino)ethoxy]-6-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}benzonitrile;
4-[6-methoxy-7-(pyridin-4-ylmethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzonitrile;
4′
-[6-methoxy-7-(trifluoromethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4-[(6,7-dimethoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)ethynyl]phenol;
4-[(6,7-dimethoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)ethynyl]-2-methoxyphenol;
4′
-(6-morpholin-4-yl-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
-biphenyl-4-ol;
3-methoxy-4′
-(6-morpholin-4-yl-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
-biphenyl-4-ol;
4-(6-morpholin-4-yl-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzonitrile;
4-[5-(6-morpholin-4-yl-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridin-2-yl]phenol;
3-(6-chloropyridin-3-yl)-6-morpholin-4-yl-1,4-dihydroindeno[1,2-c]pyrazole;
2-methoxy-4-[5-(6-morpholin-4-yl-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridin-2-yl]phenol;
5-(6-morpholin-4-yl-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridine-2-carbonitrile;
5-(6,7-diisopropoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridine-2-carbonitrile;
3-(6-chloropyridin-3-yl)-6,7-diisopropoxy-1,4-dihydroindeno[1,2-c]pyrazole;
4-[5-(6,7-diisopropoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridin-2-yl]phenol;
4-[5-(6,7-diisopropoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridin-2-yl]-2-methoxyphenol;
5-[6-(tetrahydro-2H-pyran-4-yloxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
3-(6-chloropyridin-3-yl)-6-(tetrahydro-2H-pyran-4-yloxy)-1,4-dihydroindeno[1,2-c]pyrazole;
4-{5-[6-(tetrahydro-2H-pyran-4-yloxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridin-2-yl}phenol;
2-methoxy-4-{5-[6-(tetrahydro-2H-pyran-4-yloxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridin-2-yl}phenol;
5-(6-isopropoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridine-2-carbonitrile;
5-(6-isopropoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridine-2-carbonitrile;
4-[5-(6-isopropoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridin-2-yl]phenol;
4-[5-(6-isopropoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridin-2-yl]-2-methoxyphenol;
5-(6,7-diethoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridine-2-carbonitrile;
3-(6-chloropyridin-3-yl)-6,7-diethoxy-1,4-dihydroindeno[1,2-c]pyrazole;
4-[5-(6,7-diethoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridin-2-yl]phenol;
4-[5-(6,7-diethoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridin-2-yl]-2-methoxyphenol;
5-[6,7-bis(difluoromethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
3-(6-chloropyridin-3-yl)-6,7-bis(difluoromethoxy)-1,4-dihydroindeno[1,2-c]pyrazole;
4-{5-[6,7-bis(difluoromethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridin-2-yl}phenol;
5-[6-(1H-1,2,4-triazol-1-ylmethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
3-(6-chloropyridin-3-yl)-6-(1H-1,2,4-triazol-1-ylmethyl)-1,4-dihydroindeno[1,2-c]pyrazole;
4-{5-[6-(1H-1,2,4-triazol-1-ylmethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridin-2-yl}phenol;
4-[6-(1H-1,2,4-triazol-1-ylmethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]benzonitrile;
3-(4-bromophenyl)-6-(1H-1,2,4-triazol-1-ylmethyl)-1,4-dihydroindeno[1,2-c]pyrazole;
4′
-[6-(1H-1,2,4-triazol-1-ylmethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-biphenyl-4-ol;
4-{5-[6-(diethylamino)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridin-2-yl}phenol;
3-(6-chloropyridin-3-yl)-N,N-diethyl-1,4-dihydroindeno[1,2-c]pyrazol-6-amine;
5-[6-(diethylamino)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
4-{5-[6-(diethylamino)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridin-2-yl}-2-methoxyphenol;
5-[6-(tetrahydrofiuran-3-ylmethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-{6-[(3-methylcyclohexyl)oxy]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}pyridine-2-carbonitrile;
5-[6-(cyclohexylmethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-[6-(pyridin-2-ylmethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-[6-(2-pyridin-2-ylethoxy)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-(6-{2-[4-(dimethylamino)phenyl]ethoxy}-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)pyridine-2-carbonitrile;
5-{6-[(4-hydroxycyclohexyl)oxy]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}pyridine-2-carbonitrile;
5-{6-[2-(4-methyl-1,3-thiazol-5-yl)ethoxy]-1,4-dihydroindeno[1,2-c]pyrazol-3-yl}pyridine-2-carboxamide;
5-[6-(2-hydroxyethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
5-[6-(difluoromethoxy)-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridine-2-carbonitrile;
3-(6-chloropyridin-3-yl)-6-(difluoromethoxy)-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazole; and
4-{5-[6-(difluoromethoxy)-7-methoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]pyridin-2-yl}phenol.
- -[6-(morpholin-4-ylmethyl)-1,4-dihydroindeno[1,2-c]pyrazol-3-yl]-1,1′
-
2. The compound according to claim 1 wherein
-
29. A compound that is 4′
- -(6,7-dimethoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
-biphenyl-4-yl 1,4′
-bipiperidine-1′
-carboxylate.
- -(6,7-dimethoxy-1,4-dihydroindeno[1,2-c]pyrazol-3-yl)-1,1′
-
30. A pharmaceutical composition comprising a compound of formula (I) or a therapeutically acceptable salt thereof in combination with a therapeutically acceptable carrier.
-
31. A method for inhibiting protein kinases in a patient in recognized need of such treatment comprising administering to the patient a therapeutically acceptable amount of a compound of formula (I) or a therapeutically acceptable salt thereof.
-
32. A method for treating cancer in a patient in recognized need of such treatment comprising administering to the patient a therapeutically acceptable amount of a compound of formula (I) or a therapeutically acceptable salt thereof.
Specification
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Current AssigneeAbbvie Incorporated
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Original AssigneeAbbott Laboratories Incorporated
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InventorsSham, Hing L., Lin, Nan-Horng, Tong, Yunsong, Sowin, Thomas J., Tao, Zhi-Fu, Li, Gaoquan, Claiborne, Akiyo K.
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Granted Patent
-
Time in Patent OfficeDays
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Field of Search
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US Class Current514/292
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CPC Class CodesC07D 231/12 with only hydrogen atoms, h...C07D 231/54 condensed with carbocyclic ...C07D 233/56 with only hydrogen atoms or...C07D 249/08 1,2,4-Triazoles; Hydrogenat...C07D 401/04 directly linked by a ring-m...C07D 401/06 linked by a carbon chain co...C07D 401/12 linked by a chain containin...C07D 401/14 containing three or more he...C07D 403/04 directly linked by a ring-m...C07D 403/10 linked by a carbon chain co...C07D 403/12 linked by a chain containin...C07D 405/12 linked by a chain containin...C07D 405/14 containing three or more he...C07D 409/14 containing three or more he...C07D 417/14 containing three or more he...