IP Library Granted Patent US 10,954,232
Granted Patent B2
US 10,954,232 · App. 16/313,948 · Granted Mar 23, 2021

Pyrazole derivative as ALK5 inhibitor and uses thereof

Inventors: Kyung Ik Lee (Hwaseong-si, KR); Young Hee Jung (Hwaseong-si, KR); Ji Young Song (Hwaseong-si, KR); Seung Ah Jun (Hwaseong-si, KR)
Assignee: HANMI PHARMACEUTICAL CO., LTD.
C07D471/04A61K31/4155A61K31/428A61K31/4725C07D401/14C07D403/04C07D405/14C07D413/14C07D417/14C07D495/04A61P11/00A61P17/02A61P19/04A61P19/10A61P35/00Y02A50/30
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Quick Facts
Patent No.
US 10,954,232
App. No.
16/313,948
Granted
Mar 23, 2021
Kind
B2
Abstract

The present disclosure relates to a novel substituted pyrazole derivative having an effect of inhibiting serine/threonine kinase activity targeting receptor ALK5 of TGF-β, and a pharmaceutical composition including the compound of the present disclosure as an active ingredient may be useful in preventing and/or treating cancers, autoimmune diseases, fibrotic diseases, inflammatory diseases, neurodegenerative diseases, infectious diseases, pulmonary diseases, cardiovascular diseases or metabolic diseases, or other diseases associated with a decrease in TGF family signaling activity.

Claims (250)

1. A compound of the following Chemical Formula 1 or a pharmaceutically acceptable salt thereof:

wherein, in Chemical Formula 1,

X is N or CH;

a ring A is C 3-6 cycloalkylene, C 6-10 arylene, C 5-10 heteroarylene containing 1 to 4 heteroatoms selected from among N, O and S atoms, or a non-aromatic fused heteropolycyclic ring containing 1 to 4 heteroatoms selected from among N, O and S;

R 1 s are each independently hydrogen, halogen, or linear or branched C 1-6 alkyl, or halo C 1-6 alkyl, and when there are a plurality of R 1 s, these are the same as or different from each other;

R 2 s are each independently

R 3 is hydrogen, halogen, linear or branched C 1-6 alkyl, linear or branched halo C 1-6 alkyl, C 3-10 cycloalkyl, C 3-10 heterocycloalkyl unsubstituted or substituted with R 4 , C 6-10 heterobicycloalkyl, linear or branched C 2-6 alkenyl, C 2-6 alkynyl, —(CH 2 ) a —R 4 , —(CH 2 ) a —OR 4 , —(CH 2 ) a —O—(CH 2 ) a —R 4 , —(CH 2 ) a —S—(CH 2 ) a —R 4 , —(CH 2 ) a —O—(CH 2 ) a —OR 4 , —(CH 2 ) a —NR 4 R 5 , —(CH 2 ) a —NO 2 , —(CH 2 ) a —CN, —(CH 2 ) a —COR 4 , —(CH 2 ) a —CO 2 R 4 , —(CH 2 ) a —CONR 4 R 5 , —(CH 2 ) a —NHCOR 4 , —(CH 2 ) a —SR 4 , —(CH 2 ) a —NHSO 2 R 4 , —(CH 2 ) a SOR 6 , —(CH 2 ) a —SO 2 R 6 , —(CH 2 ) a —SO 2 NHR 6 , —(CH 2 ) a —SO(NH)R 6 or —(CH 2 ) a —SO 2 NR 4 R 5 , or when there are a plurality of R 3 s and they are adjacent to each other, they are linked to each other to form a 5-membered or 6-membered ring with the ring A, one or more heteroatoms selected from among N, O and S atoms are included in the ring, and the heteroatoms are further oxidized;

R 4 and R 5 are each independently hydrogen, linear or branched C 1-6 alkyl, linear or branched halo C 1-6 alkyl, C 3-10 cycloalkyl, C 3-6 cycloalkenyl, C 1-6 carbonyl, C 6-12 aryl, —(CH 2 ) b —NR 6 R 7 , or saturated or partially unsaturated 5-membered to 10-membered monocyclic or bicyclic heterocycloalkyl or heteroaryl containing 1 to 4 heteroatoms selected from among N, O and S;

R 6 and R 7 are each independently hydrogen, hydroxy, C 1-6 alkyl, halo C 1-6 alkyl or C 3-6 cycloalkyl;

a and b are an integer of 0 to 4; and

l, m and n are each independently an integer of 0 to 4.

2. The compound or a pharmaceutically acceptable salt thereof of claim 1 , wherein X is N, and R 1 is C 1-6 alkyl.

3. The compound or a pharmaceutically acceptable salt thereof of claim 1 , wherein the ring A is phenyl, pyrazole, pyridinyl or benzo[d][1,3]dioxol.

4. The compound or a pharmaceutically acceptable salt thereof of claim 1 , wherein the compound of Chemical Formula 1 is a compound selected from the group consisting of the following compounds:

(1) 5-(benzo[d]thiazol-6-yl)-N-(4-methoxyphenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(2) 5-(benzo[d]thiazol-6-yl)-N-(4-ethoxyphenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(3) 5-(benzo[d]thiazol-6-yl)-N-(4-(cyclopropylmethoxy)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(4) 5-(benzo[d]thiazol-6-yl)-N-(4-(2-methoxyethoxy)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(5) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(4-(trifluoromethoxy)phenyl)-1H-pyrazole-3-carboxyamide;

(6) 5-(benzo[d]thiazol-6-yl)-N-(4-(benzyloxy)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(7) N-(benzo[d][1,3]dioxol-5-yl)-5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-1-H-pyrazole-3-carboxyamide;

(8) 5-(benzo[d]thiazol-6-yl)-N-(4-fluoro-3-methoxyphenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(9) 5-(benzo[d]thiazol-6-yl)-N-(2-fluoro-4-methoxyphenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(10) 5-(benzo[d]thiazol-6-yl)-N-(3-fluoro-4-methoxyphenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(11) 5-(benzo[d]thiazol-6-yl)-N-(3-aminophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(12) 5-(benzo[d]thiazol-6-yl)-N-(3-(methylamino)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(13) 5-(benzo[d]thiazol-6-yl)-N-(4-(dimethylamino)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(14) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(4-nitrophenyl)-1H-pyrazole-3-carboxyamide;

(15) 5-(benzo[d]thiazol-6-yl)-N-(4-((2-(dimethylamino)ethyl)(methyl)amino) phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(16) 5-(benzo[d]thiazol-6-yl)-N-(4-(3-(dimethylamino)pyrrolidin-1-yl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(17) 5-(benzo[d]thiazol-6-yl)-N-(3-chloro-4-(octahydro-6H-pyrrolo[3,4-b]pyridin-6-yl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(18) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-phenyl-1H-pyrazole-3-carboxyamide;

(19) 5-(benzo[d]thiazol-6-yl)-N-(3-tolyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(20) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(3-vinylphenyl)-1H-pyrazole-3-carboxyamide;

(21) 5-(benzo[d]thiazol-6-yl)-N-(3-(trifluoromethyl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(22) 5-(benzo[d]thiazol-6-yl)-N-(3-(cyanophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(23) 5-(benzo[d]thiazol-6-yl)-N-(3-acetylphenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(24) ethyl 3-(5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamido)benzoate;

(25) 5-(benzo[d]thiazol-6-yl)-N-(4-(methylcarbamoyl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(26) 5-(benzo[d]thiazol-6-yl)-N-(4-acetamidophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(27) 5-(benzo[d]thiazol-6-yl)-N-(2-fluorophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(28) 5-(benzo[d]thiazol-6-yl)-N-(3-fluorophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(29) 5-(benzo[d]thiazol-6-yl)-N-(4-fluorophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(30) 5-(benzo[d]thiazol-6-yl)-N-(3,4-difluorophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(31) 5-(benzo[d]thiazol-6-yl)-N-(2-chlorophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(32) 5-(benzo[d]thiazol-6-yl)-N-(3-chlorophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(33) 5-(benzo[d]thiazol-6-yl)-N-(4-chlorophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(34) 5-(benzo[d]thiazol-6-yl)-N-(4-bromophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(35) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(3-(methylthio)phenyl)-1H-pyrazole-3-carboxyamide;

(36) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(4-(methylthio)phenyl)-1H-pyrazole-3-carboxyamide;

(37) 5-(benzo[d]thiazol-6-yl)-N-(4-(cyclopropylthio)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(38) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(3-(methylsulfinyl)phenyl)-1H-pyrazole-3-carboxyamide;

(39) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(4-(methylsulfinyl)phenyl)-1H-pyrazole-3-carboxyamide;

(40) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(3-(methylsulfonyl)phenyl)-1H-pyrazole-3-carboxyamide;

(41) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(4-(methylsulfonyl)phenyl)-1H-pyrazole-3-carboxyamide;

(42) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(4-(propylsulfonyl)phenyl)-1H-pyrazole-3-carboxyamide;

(43) 5-(benzo[d]thiazol-6-yl)-N-(4-(cyclopropylsulfonyl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(44) 5-(benzo[d]thiazol-6-yl)-N-(2-fluoro-4-(methylsulfonyl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(45) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(3-sulfamoylphenyl)-1H-pyrazole-3-carboxyamide;

(46) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(4-sulfamoylphenyl)-1H-pyrazole-3-carboxyamide;

(47) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(3-(N-methylsulfamoyl)phenyl)-1H-pyrazole-3-carboxyamide;

(48) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(4-(N-methylsulfamoyl)phenyl)-1H-pyrazole-3-carboxyamide;

(49) 5-(benzo[d]thiazol-6-yl)-N-(3-(N-cyclopropylsulfamoyl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(50) 5-(benzo[d]thiazol-6-yl)-N-(4-(N-cyclopropylsulfamoyl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(51) 5-(benzo[d]thiazol-6-yl)-N-(3-(N,N-dimethylsulfamoyl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(52) 5-(benzo[d]thiazol-6-yl)-N-(4-(N,N-dimethylsulfamoyl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(53) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(3-(methylsulfonamido)phenyl)-1H-pyrazole-3-carboxyamide;

(54) 5-(benzo[d]thiazol-6-yl)-N-(3-(cyclopropanesulfonamido)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(55) 5-(benzo[d]thiazol-6-yl)-N-(4-(cyclopropanesulfonamido)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(56) 4-(5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamido)benzenesulfonic acid;

(57) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(4-((trifluoromethyl)sulfonyl)phenyl)-1H-pyrazole-3-carboxyamide;

(58) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(4-(N-(2,2,2-trifluoroethyl)sulfamoyl)phenyl)-1H-pyrazole-3-carboxyamide;

(59) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(4-((methylsulfonyl)methyl)phenyl)-1H-pyrazole-3-carboxyamide;

(60) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(3-(sulfamoylmethyl)phenyl)-1H-pyrazole-3-carboxyamide;

(61) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(4-(sulfamoylmethyl)phenyl)-1H-pyrazole-3-carboxyamide;

(62) 5-(benzo[d]thiazol-6-yl)-N-(4-fluoro-3-(sulfamoylmethyl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(63) 5-(benzo[d]thiazol-6-yl)-N-(4-((1,1-dioxidotetrahydrothiophen-3-yl)amino)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(64) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(pyridin-4-yl)-1H-pyrazole-3-carboxyamide;

(65) 5-(benzo[d]thiazol-6-yl)-N-(6-methoxypyridin-3-yl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(66) 5-(benzo[d]thiazol-6-yl)-N-(2-methoxypyridin-4-yl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(67) 5-(benzo[d]thiazol-6-yl)-N-(6-(methylthio)pyridin-3-yl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(68) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(6-(methylsulfonyl)pyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(69) 5-(benzo[d]thiazol-6-yl)-N-(6-(methylsulfonyl)pyridin-3-yl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(70) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(2-(methylsulfonyl)pyridin-4-yl)-1H-pyrazole-3-carboxyamide;

(71) 5-(benzo[d]thiazol-6-yl)-N-(6-fluoropyridin-3-yl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(72) 5-(benzo[d]thiazol-6-yl)-N-(2-fluoropyridin-4-yl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(73) 5-(benzo[d]thiazol-6-yl)-N-(6-chloropyridin-3-yl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(74) 5-(benzo[d]thiazol-6-yl)-N-(2-chloropyridin-4-yl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(75) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(thiazol-2-yl)-1H-pyrazole-3-carboxyamide;

(76) 5-(benzo[d]thiazol-6-yl)-N-benzyl-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(77) 5-(benzo[d]thiazol-6-yl)-N-(2-fluorobenzyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(78) 5-(benzo[d]thiazol-6-yl)-N-(3-fluorobenzyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(79) 5-(benzo[d]thiazol-6-yl)-N-(4-fluorobenzyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(80) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(1-(methylsulfonyl)-1H-pyrazol-4-yl)-1H-pyrazole-3-carboxyamide;

(81) 5-(benzo[d]thiazol-6-yl)-N-(1-(cyclopropylsulfonyl)-1H-pyrazol-4-yl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(82) 5-(benzo[d]thiazol-6-yl)-N-(3-hydroxyphenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(83) 5-(benzo[d]thiazol-6-yl)-N-(4-hydroxyphenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(84) 5-(benzo[d]thiazol-6-yl)-N-(3-(hydroxymethyl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(85) 5-(benzo[d]thiazol-6-yl)-N-(4-(hydroxymethyl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(86) N-(4-aminophenyl)-5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(87) 5-(benzo[d]thiazol-6-yl)-N-(4-(butylamino)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(88) 5-(benzo[d]thiazol-6-yl)-N-(4-(cyclopropylamino)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(89) 5-(benzo[d]thiazol-6-yl)-1-(6-methylpyridin-2-yl)-N-(4-(S-methylsulfonimidoyl)phenyl)-1H-pyrazole-3-carboxyamide;

(90) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(2-methoxyphenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(91) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(3-methoxyphenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(92) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(2-methoxyphenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(93) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-hydroxyphenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(94) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-isopropylphenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(95) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-(2-methoxyethoxy)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(96) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(benzo[d][1,3]dioxol-5-yl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(97) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(2-fluoro-4-methoxyphenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(98) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(3-fluoro-4-methoxyphenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(99) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-1-(6-methylpyridin-2-yl)-N-(2-(trifluoromethoxy)phenyl)-1H-pyrazole-3-carboxyamide;

(100) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-1-(6-methylpyridin-2-yl)-N-(3-(trifluoromethoxy)phenyl)-1H-pyrazole-3-carboxyamide;

(101) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-1-(6-methylpyridin-2-yl)-N-(4-(trifluoromethoxy)phenyl)-1H-pyrazole-3-carboxyamide;

(102) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(3-(dimethylamino)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(103) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-aminophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(104) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-(dimethylamino)phenyl)-1-(6-methylpyridin-2-yl)-1-H-pyrazole-3-carboxyamide;

(105) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-(pyrrolidin-1-yl)phenyl)1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(106) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-((2-(dimethylamino)ethyl)(methyl)amino)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(107) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-(4-methylpiperazin-1-yl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(108) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-(4-acetylpiperazin-1-yl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(109) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-((1,1-dioxidotetrahydrothiophen-3-yl)amino)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(110) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-acetamidophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(111) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-((dimethylamino)methyl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(112) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(2-(methylcarbamoyl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(113) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-(methylcarbamoyl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(114) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-1-(6-methylpyridin-2-yl)-N-phenyl-1H-pyrazole-3-carboxyamide;

(115) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-1-(6-methylpyridin-2-yl)-N-(o-tolyl)-1H-pyrazole-3-carboxyamide;

(116) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-1-(6-methylpyridin-2-yl)-N-(m-tolyl)-1H-pyrazole-3-carboxyamide;

(117) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-1-(6-methylpyridin-2-yl)-N-(p-tolyl)-1H-pyrazole-3-carboxyamide;

(118) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-1-(6-methylpyridin-2-yl)-N-(3-(trifluoromethyl)phenyl)-1H-pyrazole-3-carboxyamide;

(119) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-1-(6-methylpyridin-2-yl)-N-(4-vinylphenyl)-1H-pyrazole-3-carboxyamide;

(120) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(3-cyanophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(121) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-cyanophenyl)-1-(6-methylpyridin-2-yl)-1-H-pyrazole-3-carboxyamide;

(122) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(3-acetylphenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(123) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-acetylphenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(124) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(2-fluorophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(125) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(3-fluorophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(126) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-fluorophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(127) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(2-chlorophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(128) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(3-chlorophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(129) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-chlorophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(130) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(2-bromophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(131) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(3-bromophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(132) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-bromophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(133) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(2,3-difluorophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(134) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(2,4-difluorophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(135) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(2,5-difluorophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(136) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(3,4-difluorophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(148) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-sulfamoylphenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(149) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-(S-methylsulfonimidoyl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(150) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-(propylsulfonyl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(151) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-(propylsulfonyl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(152) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(6-fluoropyridin-3-yl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(153) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(6-chloropyridin-3-yl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(154) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(6-methoxypyridin-3-yl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(155) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(2-fluorobenzyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(156) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(3-fluorobenzyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(157) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-fluorobenzyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(158) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(3-methoxybenzyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(137) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(3,5-difluorophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(138) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(3-chloro-2-fluorophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(139) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-chloro-2-fluorophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(140) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(3-chloro-4-fluorophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(141) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(3,4-dichlorophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(142) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(2-bromo-4-fluorophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(143) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(3-(methoxythio)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(144) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-(methoxythio)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(145) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(3-(methylsulfinyl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(146) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-(methylsulfinyl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(147) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-(methylsulfonyl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(159) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-methoxybenzyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(160) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(4-(dimethylamino)benzyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(161) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(-acetamidobenzyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(162) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-1-(6-methylpyridin-2-yl)-N-(1-(methylsulfonyl)-1H-pyrazol-4-yl)-1H-pyrazole-3-carboxyamide;

(163) 5-([1,2,4]triazolo[1,5-α]pyridin-6-yl)-N-(1-cyclopropyl sulfonyl)-1H-pyrazol-4-yl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(164) N-(4-methoxyphenyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(165) N-(3-methoxyphenyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(166) N-(2-methoxyphenyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(167) N-(4-(2-methoxyethoxy)phenyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(168) N-(benzo[d][1,3]dioxol-5-yl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(169) N-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(170) N-(4-(dimethylamino)phenyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(171) 1-(6-methylpyridin-2-yl)-N-(4-morpholinophenyl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(172) N-(4-(4-methylpiperazin-1-yl)phenyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(173) N-(4-(4-acetylpiperazin-1-yl)phenyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(174) N-(4-cyanophenyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(175) N-(3-cyanophenyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(176) N-(2-cyanophenyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(177) 1-(6-methylpyridin-2-yl)-N-(4-(morpholinomethyl)phenyl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(178) N-(4-acetylphenyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(179) N-(3-acetylphenyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(180) 1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-N-(4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carboxyamide;

(181) 1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-N-(3-(trifluoromethyl)phenyl)-1H-pyrazole-3-carboxyamide;

(182) N-(4-(methylcarbamoyl)phenyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(183) N-(4-fluorophenyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(184) N-(3-fluorophenyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(185) N-(2-fluorophenyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(186) N-(3,4-difluorophenyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(187) N-(2,4-difluorophenyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(188) N-(2,3-difluorophenyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(189) N-(4-chlorophenyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(190) N-(2-chlorophenyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(191) N-(4-bromophenyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(192) N-(6-methoxypyridin-3-yl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(193) N-(4-methoxybenzyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(194) N-(4-cyanobenzyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(195) N-(3-acetylbenzyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(196) N-(4-fluorobenzyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(197) N-(3-fluorobenzyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(198) N-(2-fluorobenzyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(199) N-(4-chlorobenzyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(200) N-(3-chlorobenzyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(201) N-(2-chlorobenzyl)-1-(6-methylpyridin-2-yl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(202) N-(2-fluorophenyl)-5-(quinoxalin-6-yl)-1-(m-tolyl)-1H-pyrazole-3-carboxyamide;

(203) 1-(5-chloro-2-fluorophenyl)-N-(4-methoxyphenyl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(204) 1-(5-chloro-2-fluorophenyl)-N-(4-(dimethylamino)phenyl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(205) N-(4-methoxyphenyl)-5-(quinoxalin-6-yl)-1-(6-trifluoromethyl)pyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(206) N-(4-(dimethylamino)phenyl)-5-(quinoxalin-6-yl)-1-(6-trifluoromethyl)pyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(207) 1-(6-bromopyridin-2-yl)-N-(4-methoxyphenyl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(208) 1-(6-bromopyridin-2-yl)-N-(4-(dimethylamino)phenyl)-5-(quinoxalin-6-yl)-1H-pyrazole-3-carboxyamide;

(209) N-(2-fluorophenyl)-1-(6-methylpyridin-2-yl)-5-(quinolin-4-yl)-1H-pyrazole-3-carboxyamide;

(210) N-(4-methoxyphenyl)-1-(6-methylpyridin-2-yl)-5-(quinolin-4-yl)-1H-pyrazole-3-carboxyamide;

(211) 1-(6-methylpyridin-2-yl)-N-(4-(methylsulfonyl)phenyl)-5-(quinolin-4-yl)-1H-pyrazole-3-carboxyamide;

(212) N-(6-methoxypyridin-3-yl)-1-(6-methylpyridin-2-yl)-5-(quinolin-4-yl)-1H-pyrazole-3-carboxyamide;

(213) N-(6-chloropyridin-3-yl)-1-(6-methylpyridin-2-yl)-5-(quinolin-4-yl)-1H-pyrazole-3-carboxyamide;

(214) N-(benzo[d][1,3]dioxol-5-yl)-1-(6-methylpyridin-2-yl)-5-(quinolin-4-yl)-1H-pyrazole-3-carboxyamide;

(215) N-(3-fluoro-4-methoxyphenyl)-1-(6-methylpyridin-2-yl)-5-(quinolin-4-yl)-1H-pyrazole-3-carboxyamide;

(216) N-(2-fluoro-4-methoxyphenyl)-1-(6-methylpyridin-2-yl)-5-(quinolin-4-yl)-1H-pyrazole-3-carboxyamide;

(217) N-(4-(2-methoxyethoxy)phenyl)-1-(6-methylpyridin-2-yl)-5-(quinolin-4-yl)-1H-pyrazole-3-carboxyamide;

(218) 5-(benzo[c][1,2,5]oxadiazol-5-yl)-N-(4-(cyclopropyl sulfonyl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(219) 5-(benzo[d]oxazol-6-yl)-N-(2-fluorophenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(220) 5-(benzo[d]oxazol-6-yl)-N-(4-(cyclopropylsulfonyl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(221) N-cyclopropyl-5-(4-fluoro-3-(1-(2-hydroxyethyl)-1H-pyrazol-4-yl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(222) N-(1H-pyrazol-4-yl)-5-(4-fluoro-3-(1-(2-hydroxyethyl)-1H-pyrazol-4-yl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(223) N-(1-methyl-1H-pyrazol-4-yl)-5-(4-fluoro-3-(1-(2-hydroxyethyl)-1H-pyrazol-4-yl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(224) N-(1-(methylsulfonyl)-1H-pyrazol-4-yl)-5-(4-fluoro-3-(1-(2-hydroxyethyl)-1H-pyrazol-4-yl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(225) N-(4-chlorophenyl)-5-(4-fluoro-3-(1-(2-hydroxyethyl)-1H-pyrazol-4-yl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide;

(226) N-(4-(methylsulfonyl)phenyl)-5-(4-fluoro-3-(1-(2-hydroxyethyl)-1H-pyrazol-4-yl)phenyl)-1-(6-methylpyridin-2-yl)-1H-pyrazole-3-carboxyamide; and

(227) N-(2-fluorophenyl)-5-(thieno[3,2,c]pyridin-2-yl)-1-(m-tolyl)-1H-pyrazole-3-carboxyamide.

5. A pharmaceutical composition comprising the compound or pharmaceutically acceptable salt thereof of claim 1 in a pharmaceutically effective amount.

6. A pharmaceutical composition comprising the compound or pharmaceutically acceptable salt thereof of claim 4 in a pharmaceutically effective amount.

7. A method for inhibiting a TGF-β signaling pathway in a subject or a cell, the method comprising administering a pharmaceutically effective amount of the compound of claim 1 to the subject in need.

8. A method for inhibiting a TGF-β signaling pathway in a subject or a cell, the method comprising administering a pharmaceutically effective amount of the compound of claim 4 to the subject in need.

9. A method for inhibiting metastasis of cancer cells in a subject, the method comprising administering a pharmaceutically effective amount of the compound of claim 1 to the subject in need.

10. A method for treating a carcinoma mediated by overexpression of TGFβ, the method comprising administering a pharmaceutically effective amount of the compound of claim 1 to a subject in need of treatment of a carcinoma mediated by overexpression of TGFβ.

11. The method of claim 10 , wherein the carcinoma is selected from the group consisting of carcinomas of lung, breast, liver, biliary, gastrointestinal tract, head and neck, pancreas, prostate and cervix, multiple myeloma, melanoma, glioma and glioblastoma.

12. The pharmaceutical composition of claim 5 , which is for treating a cancer or a tumor.

13. The pharmaceutical composition of claim 12 , wherein the cancer is selected from the group consisting of liver cancer, hepatocellular carcinoma, thyroid cancer, colorectal cancer, testicular cancer, bone cancer, oral cancer, basal cell carcinoma, ovarian cancer, brain tumor, gallbladder carcinoma, biliary tract cancer, head and neck cancer, colorectal cancer, vesical carcinoma, tongue cancer, esophageal cancer, glioma, glioblastoma, renal cancer, malignant melanoma, gastric cancer, breast cancer, sarcoma, pharynx carcinoma, uterine cancer, cervical cancer, prostate cancer, rectal cancer, pancreatic cancer, lung cancer, skin cancer, fibrous cancer, and a metastatic tumor.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 25, 2019
From: LEE, KYUNG IK; JUNG, YOUNG HEE; SONG, JI YOUNG; JUN, SEUNG AH
To: HANMI PHARMACEUTICAL CO., LTD.
Reel/Frame 048138/0349 →
Priority Claims (3)
KR 10-2016-0082824 · Jun 30, 2016 · national
KR 10-2016-0180401 · Dec 27, 2016 · national
KR 10-2017-0082868 · Jun 29, 2017 · national
Continuity (1)
Related Publication 20190194198A1 · Jun 27, 2019