Indazoles
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Abstract
Herein are disclosed indazoles of formula (I)
where the various groups are defined herein, and which are useful for treating cancer.
6 Citations
9 Claims
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1. A compound of formula (I):
- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9)
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2. The compound according to claim 1 wherein:
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X and Z are selected independently from the group consisting of (C1-C8)alkyl, (C3-C8)cycloalkyl, aryl, —
NRaRb, and —
ORa;Y is H; R1 is (C1-C8)alkyl or (C3-C8)cycloalkyl; R3 is hydrogen, (C1-C8)alkyl, or halo; R6 is hydrogen, halo, cyano, trifluoromethyl, amino, (C1-C8)alkyl, (C3-C8)cycloalkyl, aryl, acylamino, (C2-C8)alkynyl, aryl(C2-C8)alkynyl, —
SO2Ra, —
SO2NRaRb, or —
NRaSO2Rb;wherein any (C1-C8)alkyl, (C3-C8)cycloalkyl, (C2-C8)alkynyl, or aryl(C2-C8)alkynyl group is optionally substituted by 1, 2, or 3 groups independently selected from halo, (C1-C6)alkyl, (C3-C8)cycloalkyl, (C5-C8)cycloalkenyl, (C1-C6)haloalkyl, cyano, —
CORa, —
CO2Ra, —
CONRaRb, —
SRa, —
SORa, —
SO2Ra, —
SO2NRaRb, nitro, —
NRaRb, —
NRaC(O)Rb, —
NRaC(O)NRaRb, —
NRaC(O)ORa, —
NRaSO2Rb, —
NRaSO2NRaRb, —
ORa, —
OC(O)Ra, —
OC(O)NRaRb, aryl, and aryl(C1-C4)alkyl; andRa and Rb are each independently hydrogen, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C3-C8)cycloalkyl, (C5-C8)cycloalkenyl, (C6-C10)bicycloalkyl, or aryl, wherein said (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, cycloalkyl, cycloalkenyl, bicycloalkyl, or aryl group is optionally substituted by 1, 2, or 3 groups independently selected from halo, hydroxyl, (C1-C4)alkoxy, amino, (C1-C4)alkylamino, ((C1-C4)alkyl)((C1-C4)alkyl)amino, —
CO2H, —
CO2(C1-C4)alkyl, —
CONH2, —
CONH(C1-C4)alkyl, —
CON((C1-C4)alkyl)((C1-C4)alkyl), —
SO2(C1-C4)alkyl, —
SO2NH2, —
SO2NH(C1-C4)alkyl, and —
SO2N((C1-C4)alkyl)((C1-C4)alkyl);or Ra and Rb taken together with the nitrogen to which they are attached represent a 5-8 membered saturated or unsaturated ring, optionally containing an additional heteroatom selected from oxygen, nitrogen, and sulfur, wherein said ring is optionally substituted by 1, 2, or 3 groups independently selected from (C1-C4)alkyl, (C1-C4)haloalkyl, amino, (C1-C4)alkylamino, ((C1-C4)alkyl)((C1-C4)alkyl)amino, hydroxyl, oxo, (C1-C4)alkoxy, and (C1-C4)alkoxy(C1-C4)alkyl, wherein said ring is optionally fused to a (C3-C8)cycloalkyl or aryl ring; or Ra and Rb taken together with the nitrogen to which they are attached represent a 6- to 10-membered bridged bicyclic ring system optionally fused to a (C3-C8)cycloalkyl or aryl ring; wherein any aryl is selected from the group consisting of phenyl and naphthyridine; or a pharmaceutically acceptable salt thereof.
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3. The compound according to claim 1 wherein:
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X is methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, trifluoromethyl, tetrahydropyran, hydroxymethyl, methoxymethyl, or benzyl; Y is H; Z is methyl, ethyl, n-propyl, isopropyl, trifluoromethyl, or benzyl; R1 is isopropyl, tert-butyl, cyclobutyl, cyclopentyl, cyclohexyl, or benzyl; R3 is H, methyl, or Br; and R6 is methyl, cyclopropyl, propyl, dimethylamino, ethylamino, (2-hydroxyethyl)amino, 2-propen-1-ylamino, phenylamino, (phenylmethyl)amino, (4-pyridinylmethyl)amino, 2-(dimethylamino)ethyl]amino, [4-(aminocarbonyl)phenyl]amino, 3-hydroxy-3-methyl-1-butyn-1-yl, phenylethynyl, 7-oxo-1,5,6,7-tetrahydro-1,8-naphthyridin-3-yl, phenyl, 2-methylphenyl, 2-nitrophenyl, 2-phenylethyl, 3-aminophenyl, 4-aminophenyl, 4-chlorophenyl, 4-fluorophenyl, 4-(methyloxy)phenyl, 3-(acetylamino)phenyl, 4-(acetylamino)phenyl, 4-(aminocarbonyl)phenyl, 4-(aminosulfonyl)phenyl, 4-(methylsulfonyl)phenyl, 4-[(dimethylamino)sulfonyl]phenyl, 4-[(methylamino)carbonyl]phenyl, 4-[(methylamino)sulfonyl]phenyl, or 4-[(methylsulfonyl)amino]phenyl; or a pharmaceutically acceptable salt thereof.
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4. The compound according to claim 1 wherein:
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X is (C1-C8)alkyl or (C3-C8)cycloalkyl; Y is H; Z is (C1-C3)alkyl; R1 is (C3-C8)alkyl or (C3-C8)cycloalkyl; R3 is hydrogen, (C1-C3)alkyl, or halo; R6 is selected from the group consisting of hydrogen, halo, cyano, trifluoromethyl, amino, (C1-C8)alkyl, (C3-C8)cycloalkyl, aryl, acylamino, (C2-C8)alkynyl, aryl(C2-C8)alkynyl, —
SO2Ra, —
SO2NRaRb, and —
NRaSO2Rb;wherein any (C1-C8)alkyl, (C3-C8)cycloalkyl, (C2-C8)alkynyl, or aryl(C2-C8)alkynyl group is optionally substituted by 1, 2, or 3 groups independently selected from —
O(C1-C6)alkyl(Rc)1-2, —
S(C1-C6)alkyl(Rc)1-2, —
(C1-C6)alkyl(Rc)1-2, halo, (C1-C6)alkyl, (C3-C8)cycloalkyl, (C5-C8)cycloalkenyl, (C1-C6)haloalkyl, cyano, —
CORa, —
CO2Ra, —
CONRaRb, —
SRa, —
SORa, —
SO2Ra, —
SO2NRaRb, nitro, —
NRaRb, —
NRaC(O)Rb, —
NRaC(O)NRaRb, —
NRaC(O)ORa, —
NRaSO2Rb, —
NRaSO2NRaRb, —
ORa, —
OC(O)Ra, —
OC(O)NRaRb, aryl, and aryl(C1-C4)alkyl;Ra and Rb are each independently hydrogen, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C3-C8)cycloalkyl, (C5-C8)cycloalkenyl, (C6-C10)bicycloalkyl, or aryl, wherein said (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, cycloalkyl, cycloalkenyl, bicycloalkyl, or aryl group is optionally substituted by 1, 2, or 3 groups independently selected from halo, hydroxyl, (C1-C4)alkoxy, amino, (C1-C4)alkylamino, ((C1-C4)alkyl)((C1-C4)alkyl)amino, —
CO2H, —
CO2(C1-C4)alkyl, —
CONH2, —
CONH(C1-C4)alkyl, —
CON((C1-C4)alkyl)((C1-C4)alkyl), —
SO2(C1-C4)alkyl, —
SO2NH2, —
SO2NH(C1-C4)alkyl, and —
SO2N((C1-C4)alkyl)((C1-C4)alkyl);or Ra and Rb taken together with the nitrogen to which they are attached represent a 5-8 membered saturated or unsaturated ring, optionally containing an additional heteroatom selected from oxygen, nitrogen, and sulfur, wherein said ring is optionally substituted by 1, 2, or 3 groups independently selected from (C1-C4)alkyl, (C1-C4)haloalkyl, amino, (C1-C4)alkylamino, ((C1-C4)alkyl)((C1-C4)alkyl)amino, hydroxyl, oxo, (C1-C4)alkoxy, and (C1-C4)alkoxy(C1-C4)alkyl; and each Rc is independently —
NRaSO2Rb, —
SORa, —
SO2Ra, —
NRaC(O)ORa, —
NRaRb, or —
CO2Ra;or a pharmaceutically acceptable salt thereof.
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5. The compound according to claim 1 wherein R6 is selected from the group consisting of:
- halo, cyano, trifluoromethyl, amino, (C1-C8)alkyl, (C3-C8)cycloalkyl, acylamino, (C2-C8)alkynyl, aryl(C2-C8)alkynyl, —
SO2Ra, —
SO2NRaRb, and —
NRaSO2Rb;
or a pharmaceutically acceptable salt thereof.
- halo, cyano, trifluoromethyl, amino, (C1-C8)alkyl, (C3-C8)cycloalkyl, acylamino, (C2-C8)alkynyl, aryl(C2-C8)alkynyl, —
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6. The compound according to claim 1 wherein R6 is aryl, wherein said aryl is optionally substituted by 1, 2, or 3 groups independently selected from —
- O(C1-C6)alkyl(Rc)1-2, —
S(C1-C6)alkyl(Rc)1-2, —
(C1-C6)alkyl(Rc)1-2, halo, (C1-C6)alkyl, (C3-C8)cycloalkyl, (C5-C8)cycloalkenyl, (C1-C6)haloalkyl, cyano, —
CORa, —
CO2Ra, —
CONRaRb, —
SRa, —
SORa, —
SO2Ra, —
SO2NRaRb, nitro, —
NRaRb, —
NRaC(O)Rb, —
NRaC(O)NRaRb, —
NRaC(O)ORa, —
NRaSO2Rb, —
NRaSO2NRaRb, —
ORa, —
OC(O)Ra, —
OC(O)NRaRb, aryl, and aryl(C1-C4)alkyl;Ra and Rb are each independently hydrogen, (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, (C3-C8)cycloalkyl, (C5-C8)cycloalkenyl, (C6-C10)bicycloalkyl, or aryl, wherein said (C1-C8)alkyl, (C2-C8)alkenyl, (C2-C8)alkynyl, cycloalkyl, cycloalkenyl, bicycloalkyl, or aryl group is optionally substituted by 1, 2, or 3 groups independently selected from halo, hydroxyl, (C1-C4)alkoxy, amino, (C1-C4)alkylamino, ((C1-C4)alkyl)((C1-C4)alkyl)amino, —
CO2H, —
CO2(C1-C4)alkyl, —
CONH2, —
CONH(C1-C4)alkyl, —
CON((C1-C4)alkyl)((C1-C4)alkyl), —
SO2(C1-C4)alkyl, —
SO2NH2, —
SO2NH(C1-C4)alkyl, and —
SO2N((C1-C4)alkyl)((C1-C4)alkyl); andeach Rc is independently —
NRaSO2Rb, —
SORa, —
SO2Ra, —
NRaC(O)ORa, —
NRaRb, or —
CO2Ra;or a pharmaceutically acceptable salt thereof.
- O(C1-C6)alkyl(Rc)1-2, —
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7. The compound according to claim 1 which is:
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6-chloro-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide; N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-fluoro-1-(1-methylethyl)-1H-indazole-4-carboxamide; 6-Bromo-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-indazole-4-carboxamide; 6-bromo-N-((4-ethyl-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-1H-indazole-4-carboxamide; 6-bromo-1-(1-methylethyl)-N-{[6-methyl-2-oxo-4-(phenylmethyl)-1,2-dihydro-3-pyridinyl]methyl}-1H-indazole-4-carboxamide; 6-bromo-1-(1-methylethyl)-N-[(6-methyl-2-oxo-1,2-dihydro-4,4′
-bipyridin-3-yl)methyl]-1H-indazole-4-carboxamide;1-(1-methylethyl)-N-{[6-methyl-2-oxo-4-(phenylmethyl)-1,2-dihydro-3-pyridinyl]methyl}-1H-indazole-4-carboxamide; N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(4-(2-(dimethylamino)ethoxy)phenyl)-1-isopropyl-1H-indazole-4-carboxamide; N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-[4-(1-piperazinyl)phenyl]-1H-indazole-4-carboxamide; 6-{4-[(dimethylamino)methyl]phenyl}-1-(1-methylethyl)-N-{[6-methyl-4-(1-methylethyl)-2-oxo-1,2-dihydro-3-pyridinyl]methyl}-1H-indazole-4-carboxamide; 6-(4-((dimethylamino)methyl)phenyl)-N-((4-ethyl-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-1H-indazole-4-carboxamide; 6-{3-[(dimethylamino)methyl]phenyl}-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-indazole-4-carboxamide; 6-{4-[(dimethylamino)methyl]phenyl}-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-indazole-4-carboxamide; 6-{4-[(dimethylamino)methyl]phenyl}-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide; 6-{3-[(dimethylamino)methyl]phenyl}-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide; N-((4-cyclohexyl-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-cyclopropyl-1-isopropyl-1H-indazole-4-carboxamide; 6-bromo-1-ethyl-1H-indazole-4-carboxylic acid (6-methyl-2-oxo-4-propyl-1,2-dihydro-pyridin-3-ylmethyl)-amide; 6-bromo-N-((6-methyl-2-oxo-4-propyl-1,2-dihydropyridin-3-yl)methyl)-1-propyl-1H-indazole-4-carboxamide; 6-bromo-1-cyclopentyl-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-indazole-4-carboxamide; 6-bromo-1-cyclopentyl-N-((4-ethyl-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-indazole-4-carboxamide; 1-cyclopentyl-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(3-(pyrrolidin-1-yl)phenyl)-1H-indazole-4-carboxamide; 1-cyclopentyl-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(3-(3-hydroxypropyl)phenyl)-1H-indazole-4-carboxamide; 1-cyclopentyl-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(3-(trifluoromethoxy)phenyl)-1H-indazole-4-carboxamide; 1-cyclopentyl-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(4-fluorophenyl)-1H-indazole-4-carboxamide; 1-cyclopentyl-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(4-((dimethylamino)methyl)phenyl)-1H-indazole-4-carboxamide; 6-chloro-1-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide; 6-chloro-1-cyclopentyl-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide; 6-cyano-1-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide; 6-(aminomethyl)-1-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide; 6-amino-1-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide; 1-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-[(phenylsulfonyl)amino]-1H-indazole-4-carboxamide; 1-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-(3-hydroxy-3-methyl-1-butyn-1-yl)-1H-indazole-4-carboxamide; 6-bromo-1-cyclopropyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide; 6-bromo-1-cyclopropyl-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide; 1-cyclopropyl-6-{4-[(dimethylamino)methyl]phenyl}-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide; 1-cyclopropyl-6-{4-[(dimethylamino)methyl]phenyl}-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide; 6-bromo-N-((1,2-dihydro-4,6-dimethyl-2-oxopyridin-3-yl)methyl)-1-isopropyl-3-methyl-1H-indazole-4-carboxamide; 6-bromo-1-isopropyl-3-methyl-N-((6-methyl-2-oxo-4-propyl-1,2-dihydropyridin-3-yl)methyl)-1H-indazole-4-carboxamide; 6-(3-((dimethylamino)methyl)phenyl)-N-((1,2-dihydro-4,6-dimethyl-2-oxopyridin-3-yl)methyl)-1-isopropyl-1H-indazole-4-carboxamide; N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(4-fluorophenyl)-1-isopropyl-3-methyl-1H-indazole-4-carboxamide; 6-(4-((dimethylamino)methyl)phenyl)-N-((1,2-dihydro-4,6-dimethyl-2-oxopyridin-3-yl)methyl)-1-isopropyl-3-methyl-1H-indazole-4-carboxamide; 6-{3-[(dimethylamino)methyl]phenyl}-3-methyl-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide; 6-{4-[(dimethylamino)methyl]phenyl}-3-methyl-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide; 6-cyano-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-3-methyl-1H-indazole-4-carboxamide; 1-cyclopentyl-6-(cyclopropylsulfonyl)-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1H-indazole-4-carboxamide; 6-(cyclopropylsulfonyl)-N-((4-ethyl-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-1H-indazole-4-carboxamide; N-((4-ethyl-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-6-(methylsulfonyl)-1H-indazole-4-carboxamide; N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(methylsulfonyl)-1H-indazole-4-carboxamide; N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(4-morpholinylsulfonyl)-1H-indazole-4-carboxamide; 6-[(cyclopropylamino)sulfonyl]-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-indazole-4-carboxamide; N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(1-pyrrolidinylsulfonyl)-1H-indazole-4-carboxamide; 6-({[3-(dimethylamino)propyl]amino}sulfonyl)-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-indazole-4-carboxamide; N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-6-((4-methylpiperazin-1-yl)sulfonyl)-1H-indazole-4-carboxamide; 6-bromo-N-((4-(sec-butyl)-6-methyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-1-isopropyl-1H-indazole-4-carboxamide; 6-Bromo-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide;
or6-Bromo-1-(1-methylethyl)-N-{[6-methyl-4-(1-methylethyl)-2-oxo-1,2-dihydro-3-pyridinyl]methyl}-1H-indazole-4-carboxamide; or a pharmaceutically acceptable salt thereof.
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8. The compound according to claim 1 which is:
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6-bromo-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-indazole-4-carboxamide; N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-phenyl-1H-indazole-4-carboxamide; N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-6-{4-[(methylamino)sulfonyl]phenyl}-1-(1-methylethyl)-1H-indazole-4-carboxamide; N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-[2-(trifluoromethyl)phenyl]-1H-indazole-4-carboxamide; 6-{4-[(dimethylamino)sulfonyl]phenyl}-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-indazole-4-carboxamide; N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(2-methylphenyl)-1H-indazole-4-carboxamide; 6-bromo-N-[(4-cyclohexyl-6-methyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-indazole-4-carboxamide; 6-bromo-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide; 1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide; 6-bromo-1-cyclopentyl-N-[(6-methyl-2-oxo-4-propyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide; 6-bromo-N-[(4-cyclopropyl-6-methyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-indazole-4-carboxamide; 6-bromo-1-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide; 6-bromo-1-(1-methylethyl)-N-{[6-methyl-4-(1-methylethyl)-2-oxo-1,2-dihydro-3-pyridinyl]methyl}-1H-indazole-4-carboxamide; 1-cyclopentyl-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide;
or6-bromo-1-(1-methylethyl)-N-[(6-methyl-2-oxo-4-phenyl-1,2-dihydro-3-pyridinyl)methyl]-1H-indazole-4-carboxamide; or a pharmaceutically acceptable salt thereof.
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9. A pharmaceutical composition comprising the compound or pharmaceutically acceptable salt thereof according to claim 1 and a pharmaceutically acceptable excipient.
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2. The compound according to claim 1 wherein:
Specification
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Current AssigneeGlaxoSmithKline LLC (GlaxoSmithKline PLC)
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Original AssigneeGlaxoSmithKline LLC (GlaxoSmithKline PLC)
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InventorsDuquenne, Celine, Johnson, Neil, Knight, Steven D., LaFrance, Louis, Miller, William H., Newlander, Kenneth, Romeril, Stuart, Rouse, Meagan B., Tian, Xinrong, Verma, Sharad Kumar
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Primary Examiner(s)Wilson, James O
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Assistant Examiner(s)MASHA, OLUWAFEMI L
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Application NumberUS14/458,305Publication NumberTime in Patent Office258 DaysField of Search546/256, 546/275.7, 548/361.1US Class Current546/256CPC Class CodesA61P 1/04 for ulcers, gastritis or re...A61P 1/16 for liver or gallbladder di...A61P 1/18 for pancreatic disorders, e...A61P 11/00 Drugs for disorders of the ...A61P 13/08 of the prostateA61P 13/10 of the bladderA61P 13/12 of the kidneysA61P 15/00 Drugs for genital or sexual...A61P 17/00 Drugs for dermatological di...A61P 19/00 Drugs for skeletal disordersA61P 21/00 Drugs for disorders of the ...A61P 25/00 Drugs for disorders of the ...A61P 35/00 Antineoplastic agentsA61P 35/02 specific for leukemiaA61P 43/00 Drugs for specific purposes...A61P 5/00 Drugs for disorders of the ...C07D 401/12 linked by a chain containin...C07D 401/14 containing three or more he...C07D 409/14 containing three or more he...C07D 471/04 Ortho-condensed systems