US 10,239,873 B2Granted

7-azaindole or 4,7-diazaindole derivatives as IKKϵ epsilon and TBK1 inhibitor and pharmaceutical composition comprising same

AssigneeThe Green Cross Corporation

InventorsSoongyu Choi, Kwang-Seop Song, Hee Jeong Seo, Sang-ho Ma, Eun-Jung Park, Younggyu Kong, So Ok Park, Kisoo Park, Ickhwan Son, Min Ju Kim, Man-Young Cha, Mi-Soon Kim, Sang Mi Kang, Dong Hyuk Jang, Jangwon Hong

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Abstract

Provided are 7-azaindole or 4,7-diazaindole derivatives as an IKKε (I-kappa-B kinase epsilon) and TBK1 (TANK-binding kinase 1) inhibitor. The 7-azaindole or 4,7-diazaindole derivative effectively inhibits IKKε and TBK1, and thus is useful not only as an anticancer agent for the treatment of various cancers including colorectal cancer, breast cancer, CNS cancer, colon cancer, non-small cell lung cancer, kidney cancer, prostate cancer, ovarian cancer, uterus cancer, stomach cancer, liver cancer, skin cancer, lung cancer, brain cancer, bladder cancer, esophageal cancer, pancreatic cancer, thyroid cancer, head and neck cancer, squamous cell carcinoma, osteosarcoma, B-cell or T-cell lymphoma, acute or chronic leukemia and multiple myeloma, but as a therapeutic agent for chronic inflammation.

Claims6

Dependent claims

A compound selected from the group consisting of a 7-azaindole or 4,7-diazaindole compound of formula (I), a pharmaceutically acceptable salt thereof, a hydrate thereof, and a solvate thereof:

wherein,
X is C or N,
ring A is unsaturated 5-membered heterocycle containing at least one N, or saturated or unsaturated 6- or 7-membered heterocycle containing at least one N;
R1 is halogen, substituted or unsubstituted C5-14 aryl, substituted or unsubstituted 5- to 13-membered heteroaryl, or -NHY wherein Y is substituted or unsubstituted C5-14 aryl, wherein when said C5-14 aryl or 5- to 13-membered heteroaryl is substituted, the substituent is one or more substituents selected from the group consisting of 5- to 10-membered heterocycloalkyl-C1-7 alkyl, C1-7 alkoxy, halogen, C1-7 alkyl, C1-7 alkylamido, C1-7 alkyl-5- to 10-membered heterocycloalkyl-C1-7 alkyl, C3-10 cycloalkyl-5- to 10-membered heterocycloalkyl-C1-7 alkyl, 5- to 10-membered heterocycloalkyl-C1-7 alkyl, C1-7 alkyl-5- to 10-membered heterocycloalkyl-carbonyl, 5- to 10-membered heterocycloalkyl-amino, 5- to 10-membered heterocycloalkyl-oxy, C1-7 alkyl-sulfonyl, C3-10 cycloalkyl-sulfonyl, sulfamoyl, C1-7 alkyl-sulfamoyl, 5- to 10-membered heterocycloalkyl-sulfonyl, amino, oxo, 5- to 13-membered heteroaryl-C1-7 alkyl-carbamoyl, 5- to 10-membered heterocycloalkyl-C1-7 alkoxy, 5- to 10-membered heterocycloalkyl-carbonyl, C1-7 alkoxy-carbonyl-5- to 10-membered heterocycloalkyl-C1-7 alkyl, 5- to 10-membered heterocycloalkyl, C1-7 alkyl-carbonyl, C1-7 alkoxy-carbonyl, cyano, C1-7 alkyl-5- to 13-membered heteroaryl, di C1-7 alkyl-sulfonyl, and C1-7 alkyl-amino-sulfonyl;
R2 is H or —NH2;
R3 is H or C1-7 alkyl;
R4 is C1-7 alkyl, —C(═O)—R7, —C(═O)—O—R8, —C(═O)—N(—R9)—R10, —CH2—C(═O)—NH—R11 or —CH2—C(═O)—R12;
R7 to R12 are each independently H, hydroxy, C1-7 alkyl, substituted or unsubstituted C3-10 cycloalkyl, substituted or unsubstituted 5- to 10-membered heterocycloalkyl or substituted or unsubstituted 5- to 13-membered heteroaryl;
and each of said cycloalkyl, heterocycloalkyl and heteroaryl is optionally substituted with C1-7 alkyl;
and
R5 and R6 are each independently H, halogen, C1-7 alkyl or substituted or unsubstituted C5-14 aryl;
when said R5 and R6 are C1-7 alkyl, said R5 and R6 are optionally connected to each other.

9 more elements

A compound selected from the group consisting of:

(1) 4-((5-(3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1 H-pyrrolo[2,3-b]pyridin-5-yl)thiophen-2-yl)methyl)morpholine;
(2) 5-(3,4-dimethoxyphenyl)-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)- 1H-pyrrolo[2,3-b]pyridine;
(3) 5-(3,4-dimethoxyphenyl)-3-(1-ethyl-1,2,3,6-tetrahydropyridin-4-yl)-1 H-pyrrolo[2,3 -b]pyridine;
(4) 5-(3,4-dimethoxyphenyl)-3-(1-propyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine;
(5) 5-(3,4-dimethoxyphenyl)-3-(1-isobutyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine;
(6) 4-((5-(3-(1-ethyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)thiophen-2-yl)methyl)morpholine;
(7) 4-((5-(3-(1-propyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)thiophen-2-yl)methyl)morpholine;
(8) 1-(4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydropyridin-1(2H)-yl)ethan-1-one;
(9) 1-(4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydropyridin-1(2H)-yl)pentan-1-one;
(10) 3-methyl-1-(4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydropyridin-1(2H)-yl)butan-1-one;
(11) N-isopropyl-4-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(12) N-isopropyl-4-(5-(4-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydropyridine-1(2H)-carboxamide;
(13) 4-(5-(4-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-isopropyl-3,6-dihydropyridine-1(2H)-carboxamide;
(14) N-isopropyl-4-(5-(3-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydropyridine-1(2H)-carboxamide;
(15) 4-(5-(3-fluorophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-isopropyl-3,6-dihydropyridine-1(2H)-carboxamide;
(16) N-isopropyl-4-(5-(p-tolyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydropyridine-1(2H)-carboxamide;
(17) 4-(5-(4-acetamidophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-isopropyl-3,6-dihydropyridine-1(2H)-carboxamide;
(18) 4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-isopropyl-5,6-dihydropyridine-1(2H)-carboxamide;
(19) 4-(5-(3-acetamidophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-isopropyl-3,6-dihydropyridine-1(2H)-carboxamide;
(20) 4-(5-(2-fluoro-4-(morpholinomethyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-isopropyl-3,6-dihydropyridine-1(2H)-carboxamide;
(21) 4-(5-(2-fluoro-5-(morpholinomethyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-isopropyl-3,6-dihydropyridine-1(2H)-carboxamide;
(22) 4-(5-(4-((4-ethylpiperazin-1-yl)methyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-isopropyl-3,6-dihydropyridine-1(2H)-carboxamide;
(23) 4-(5-(4-((4-cyclopropylpiperazin-1-yl)methyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-isopropyl-3,6-dihydropyridine-1(2H)-carboxamide;
(24) 4-(5-(3-((4-ethylpiperazin-1-yl)methyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-isopropyl-3,6-dihydropyridine-1(2H)-carboxamide;
(25) N-isopropyl-4-(5-(6-((4-methylpiperazin-1-yl)methyl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydropyridine-1(2H)-carboxamide;
(26) 4-(5-(5-((4-ethylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-isopropyl-3,6-dihydropyridine-1(2H)-carboxamide;
(27) N-isopropyl-4-(5-(5-(pyrrolidin-1-ylmethyl)furan-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(28) N-isopropyl-4-(5-(5-(pyrrolidin-1-ylmethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(29) N-isopropyl-4-(5-(3-(morpholinomethyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(30) N-isopropyl-4-(5-(4-(morpholinomethyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(31) N-isopropyl-4-(5-(3-(4-methylpiperazine-1-carbonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(32) N-isopropyl-4-(5-(4-(4-methylpiperazine-1-carbonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(33) N-isopropyl-4-(5-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(34) N-isopropyl-4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(35) N-isopropyl-4-(5-(5-((4-methylpiperazin-1-yl)methyl)furan-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(36) N-isopropyl-4-(5-(5-(morpholinomethyl)furan-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(37) N-isopropyl-4-(5-(4-((tetrahydro-2H-pyran-4-yl)amino)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydropyridine-1(2H)-carboxamide;
(38) N-isopropyl-4-(5-(4-((tetrahydro-2H-pyran-4-yl)oxy)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydropyridine-1(2H)-carboxamide;
(39) 4-(5-(7-amino-1-oxoisoindolidin-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-isopropyl-3,6-dihydropyridine-1(2H)-carboxamide;
(40) 4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pentan-3-yl) -3,6-dihydropyridine-1(2H)-carboxamide;
(41) 4-(5-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pentan-3-yl)-3,6-dihydropyridine-1(2H)-carboxamide;
(42) N-(sec-butyl)-4-(5-(54(4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(43) N-(sec-butyl)-4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl) -5,6-dihydropyridine-1(2H)-carboxamide;
(44) N-(sec-butyl)-4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(45) N-cyclopropyl-4-(5-(5-(piperazin-1-ylmethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide dihydrochloride;
(46) N-cyclopropyl-4-(5-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(47) N-cyclopropyl-4-(5-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(48) N-cyclopropyl-4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl) -5,6-dihydropyridine-1(2H)-carboxamide;
(49) N-cyclopentyl-4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(50) N-cyclopentyl-4-(5-(3-fluoro-4-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(51) N-cyclopentyl-4-(5-(4-(methylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(52) N-cyclopentyl-4-(5-(3-(methylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(53) N-cyclopentyl-4-(5-(4-(ethylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydropyridine-1(2H)-carboxamide;
(54) N-cyclopentyl-4-(5-(3-(ethylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydropyridine-1(2H)-carboxamide;
(55) N-cyclopentyl-4-(5-(4-(propylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(56) N-cyclopentyl-4-(5-(4-(cyclopropylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(57) N-cyclopentyl-4-(5-(3-sulfamoylphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(58) N-cyclopentyl-4-(5-(4-sulfamoylphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(59) N-cyclopentyl-4-(5-(3-(N-methylsulfamoyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(60) N-cyclopentyl-4-(5-(4-(N-methylsulfamoyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(61) N-cyclopentyl-4-(5-(4-(morpholinosulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(62) N-cyclopentyl-4-(5-(3-(morpholinosulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(63) N-cyclopentyl-4-(5-(4-methoxy-3-(morpholinosulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(64) N-cyclopentyl-4-(5-(4-(2-morpholinoethyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(65) 4-(5-(5-acetamido-2-aminophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-cyclopentyl-5,6-dihydropyridine-1(2H)-carboxamide;
(66) N-cyclopentyl-4-(5-(4-((furan-2-ylmethyl)carbamoyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(67) N-cyclopentyl-4-(5-(3-((furan-2-ylmethyl)carbamoyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(68) N-cyclopentyl-4-(5-(3-(2-morpholinoethoxy)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(69) N-cyclopentyl-4-(5-(4-(2-morpholinoethoxy)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(70) N-cyclopentyl-4-(5-(4-(3-morpholinopropoxy)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(71) N-cyclopentyl-4-(5-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(72) N-cyclopentyl-4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carbox amide;
(73) N-cyclopentyl-4-(5-(5-(morpholinomethyl)thiophen-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(74) N-cyclopentyl-4-(5-(5-(morpholine-4-carbonyl)thiophen-2-yl)-1H-pyrrolo[2,3 -b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(75) N-cyclopentyl-4-(5-(4-(morpholine-4-carbonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(76) 4-(5-(4-chloro-3-(morpholine-4-carbonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-cyclopentyl-3,6-dihydropyridine-1(2H)-carboxamide 2,2,2-trifluoroacetate;
(77) 4-(5 -(3-chloro-5-(morpholine-4-carbonyl)phenyl)-1 H-pyrrolo[2,3-b]pyridin-3-yl)-N-cyclopentyl-3,6-dihydropyridine-1(2H)-carboxamide 2,2,2-trifluoroacetate;
(78) 4-(5 -(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(oxetan-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(79) 4-(5-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(oxetan-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(80) 4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b] pyridin-3-yl)-N-(oxetan-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(81) 4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(tetrahydro furan-3 -yl)-5,6-dihydropyridine-1(2H)-carbox amide;
(82) 4-(5-(4-(methylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(tetrahydrofuran-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(83) 4-(5-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(tetrahydrofuran-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(84) 4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(tetrahydrofuran-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(85) 4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pyrrolidin-1-yl)-5,6-dihydropyridine-1(2H)-carboxamide 2,2,2-trifluoroacetate;
(86) N-isopropyl-2-methyl-4-(5-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(87) N-isopropyl-2-methyl-4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(88) N-isopropyl-2-methyl-4-(5-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(89) N-isopropyl-2-methyl-4-(5-(4-(4-methylpiperazine-1-carbonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(90) N-isopropyl-2-methyl-4-(5-(4-(morpholinomethyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(91) 6-methyl-4-(5-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pentan-3-yl)-3,6-dihydropyridine-1(2H)-carboxamide;
(92) 6-methyl-4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-(pentan-3-yl)-3,6-dihydropyridine-1(2H)-carboxamide;
(93) tert-butyl 4-((5-(3-(1-(cyclopropylcarbamoyl)-6-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)thiophen-2-yl)methyl)piperazine-1-carboxylate;
(94) N-cyclopropyl-2-methyl-4-(5-(4-(4-methylpiperazine-1-carbonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(95) N-cyclopropyl-2-methyl-4-(5-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(96) N-cyclopropyl-2-methyl-4-(5-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(97) N-cyclopropyl-2-methyl-4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(98) N-cyclobutyl-2-methyl-4-(5-(4-(4-methylpiperazine-1-carbonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(99) N-cyclobutyl-2-methyl-4-(5-(4-((4-methylpiperazin-1-yl)methyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(100) N-cyclobutyl-2-methyl-4-(5-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(101) N-cyclobutyl-2-methyl-4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(102) N-cyclopentyl-2-methyl-4-(5-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(103) N-cyclopentyl-6-methyl-4-(5-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(104) N-cyclopentyl-6-methyl-4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(105) N-cyclopentyl-2-methyl-4-(5-(4-(methylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(106) N-cyclopentyl-2-methyl-4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(107) N-cyclopentyl-2-methyl-4-(5-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(108) N-cyclopentyl-4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2-methyl-5,6-dihydropyridine-1(2H)-carboxamide;
(109) 2-ethyl-N-isopropyl-4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(110) 6-ethyl-N-isopropyl-4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(111) 2-ethyl-N-isopropyl-4-(5-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(112) 6-ethyl-N-isopropyl-4-(5-(4-(morpholinomethyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydropyridine-1(2H)-carboxamide;
(113) 6-ethyl-N-isopropyl-4-(5-(4-(4-methylpiperazine-1-carbonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydropyridine-1(2H)-carboxamide;
(114) N-isopropyl-2,2-dimethyl-4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(115) N-isopropyl-2,6-dimethyl-4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydropyridine-1(2H)-carboxamide;
(116) N-cyclopentyl-2,6-dimethyl-4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydropyridine-1(2H)-carboxamide;
(117) N-isopropyl-3-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-8-azabicyclo[3.2.1]oct-3-ene-8-carboxamide;
(118) N-isopropyl-3-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-9-azabicyclo[3.3.1]non-3-ene-9-carboxamide;
(119) 4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-isopropyl-2-phenyl-5,6-dihydropyridine-1(2H)-carboxamide;
(120) N-cyclopentyl-4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-methyl-5,6-dihydropyridine-1(2H)-carboxamide;
(121) N-cyclopentyl-5-methyl-4-(5-(4-(methylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(122) N-cyclopentyl-5-methyl-4-(5-(3-(methylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(123) N-cyclopentyl-5-methyl-4-(5-(3-sulfamoylphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(124) N-cyclopentyl-5-methyl-4-(5-(4-sulfamoylphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(125) N-isopropyl-5-methyl-4-(5-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(126) N-cyclopentyl-5-methyl-4-(5-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(127) N-cyclopentyl-5-methyl-4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(128) N-cyclopentyl-5-ethyl-4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(129) N-c yclopentyl-4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3-methyl-5,6-dihydropyridine-1(2H)-carboxamide;
(130) N-cyclopentyl-3-methyl-4-(5-(4-(methylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(131) N-cyclopentyl-3-methyl-4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(132) N-cyclopentyl-3-fluoro-4-(5-(4-(methylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(133) N-cyclopentyl-4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3-fluoro-5,6-dihydropyridine-1(2H)-carboxamide;
(134) N-cyclopentyl-3-fluoro-4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(144) cyclopentyl 4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(145) cyclopentyl 4-(5-(3-sulfamoylphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(146) isopropyl 4-(5-(3-sulfamoylphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(147) isopropyl 4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(148) isopropyl 4-(5-(4-(methylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(149) isopropyl 4-(5-(3-(methylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(150) isopropyl 4-(5-(4-sulfamoylphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(151) tert-butyl 4-(5-(3-sulfamoylphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(152) tert-butyl 4-(5-(4-sulfamoylphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(153) tert-butyl 4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(154) tert-butyl 4-(5-(4-(morpholinomethyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(155) tert-butyl 4-(5-(4-(morpholine-4-carbonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(156) tert-butyl 4-(5-(3-(morpholinomethyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(157) tert-butyl 4-(5-(6-morpholinopyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(158) tert-butyl 4-(5-(4-morpholinophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(159) tert-butyl 4-(5-(4-(piperidin-1-yl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(160) tert-butyl 4-(5-(benzo[d][1,3]dioxo1-5-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(161) tert-butyl 4-(5-(6-methoxypyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(162) tert-butyl 4-(5-(3-(methylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(163) tert-butyl 4-(5-(3-(N-methylsulfamoyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(164) tert-butyl 4-(5-(4-(methylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(165) tert-butyl 4-(5-(4-(N-methylsulfamoyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(166) tert-butyl 4-(5-(4-acetylphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(167) tert-butyl 4-(5-(4-(methoxycarbonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(168) tert-butyl 4-(5-(4-cyanophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(169) tert-butyl 4-(5-(3-cyanophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(170) tert-butyl 4-(5-(5-methyl-1,3,4-thiadiazol-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(171) cyclopentyl 4-(5-(3-fluoro-4-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(172) cyclopentyl 4-(5-(3-(methylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(173) cyclopentyl 4-(5-(4-(methylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(174) cyclopentyl 4-(5-(3-(ethylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(175) cyclopentyl 4-(5-(4-(cyclopropylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(176) cyclopentyl 4-(5-(4-sulfamoylphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(177) cyclopentyl 4-(5-(3-(N-methylsulfamoyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(178) cyclopentyl 4-(5-(4-(N-methylsulfamoyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(179) cyclopentyl 4-(5-(4-(N,N-dimethylsulfamoyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(180) cyclopentyl 4-(5-(3-(morpholinosulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(181) cyclopentyl 4-(5-(4-(morpholinosulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(182) cyclopentyl 4-(5-(4-methoxy-3-(morpholinosulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(183) cyclopentyl 4-(5-(4-(morpholine-4-carbonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(184) cyclopentyl 4-(5-(3-(morpholine-4-carbonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(185) cyclopentyl 4-(5-(5-(morpholinomethyl)thiophen-3-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(186) cyclopentyl 4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(187) tert-butyl 4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2,3,6,7-tetrahydro-1H-azepine-1-carboxylate;
(188) tert-butyl 5-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-2,3,4,7-tetrahydro-1H-azepine-1-carboxylate;
(189) (4-(5-(3,4-difluorophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone;
(190) (4-(5-(4-(morpholinosulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone;
(191) (4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone;
(192) (4-(5-(3-fluoro-4-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone;
(193) (4-(5-(3-(methylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone;
(194) (4-(5-(4-(methylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone;
(195) (4-(5-(3-(ethylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone;
(196) (4-(5-(4-(cyclopropylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone;
(197) 4-(3-(1-(thiophene-2-carbonyl)-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)benzensulfonamide;
(198) 3-(3-(1-(thiophene-2-carbonyl)-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)benzensulfonamide;
(199) N-methyl-3-(3-(1-(thiophene-2-carbonyl)-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)benzensulfonamide;
(200) N-methyl-4-(3-(1-(thiophene-2-carbonyl)-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)benzensulfonamide;
(201) N-(3-(3-(1-(thiophene-2-carbonyl)-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methansulfonamide;
(202) (44543-(morpholinosulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone;
(203) (4-(5-(4-methoxy-3-(morpholinosulfonyl)phenyl)-1H-pyrrolo[2,3-yl]p yridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone;
(204) (4-(5-(1H-indazol-5-yl)-1H-pyrrolo[2,3-Il]pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone;
(205) (4-(5-(5-((4-methylpiperazin-1-yl)methyl)thiophen-2-yl)-1H-pyrrolo[2,3-yl]pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone;
(206) (4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-p yrrolo [2,3-yl]pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone;
(207) (4-(5-(5-(morpholinomethyl)thiophen-3-yl)-1H-p yrrolo [2,3-yl]pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone;
(208) (44543-(morpholine-4-carbonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2- yl)methanone;
(209) (4-(5-(4-(morpholine-4-carbonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridin- 1(2H)-yl)(thiophen-2- yl)methanone;
(210) (4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-yl]pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)(5-methylthiophen-2-yl)methanone;
(211) (4-(5-(4-(methylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)(5-methylthiophen-2-yl)methanone;
(212) 4-(3-(1-(5-methylthiophene-2-c arbonyl)-1,2,3,6-tetrahydrop yridin-4-yl)-1H-pyrrolo[2,3-yl]pyridin-5-yl)benzensulfonamide;
(213) (4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-methyl-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone;
(214) (5-methyl-4-(5-(4-(methylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone;
(215) (4-(3-(3-methyl-1-(thiophene-2-carbonyl)-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)(morpholino)methanone;
(216) (5-methyl-4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone;
(217) N-cyclopentyl-N-methyl-4-(5-(3-(methylsulfonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(218) N-cyclopentyl-N-methyl-4-(5-(3-sulfamoylphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(219) N-cyclopentyl-N-methyl-4-(5-(4-sulfamoylphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(220) N-c yclopentyl-4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-methyl-5,6-dihydropyridine-1(2H)-carboxamide;
(221) N-c yclopentyl-4-(2-methyl-5-(4-sulfamoylphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(222) N-cyclopentyl-4-(2-methyl-5-(4-(N-methylsulfamoyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(223) N-cyclopenty 1-4-(2-methyl-5-(4-(morpholine-4-carbonyl)phenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(224) tert-butyl 4-(6-amino-5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(225) tert-butyl 4-(6-amino-5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(226) 4-(6-amino-5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-cyclopentyl-5,6-dihydropyridine-1(2H)-carboxamide;
(227) 4-(6-amino-5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-cyclopentyl-5,6-dihydropyridine-1(2H)-carboxamide;
(228) N-cyclopentyl-4-(2-(3-(methylsulfonyl)phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(229) N-cy clopentyl-4-(2-(5-(morpholinomethyl)thiophen-2-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-5,6-dihydropyridine-1(2H)-carboxamide;
(230) tert-butyl 4-(2-(3,4-dimethoxyphenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(231) tert-butyl 4-(2-(3-(methylsulfonyl)phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(232) (4-(2-(3-(methylsulfonyl)phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone;
(233) (4-(2-(5-(morpholinomethyl)thiophen-2-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone;
(234) tert-butyl 4-(2-(5-(morpholinomethyl)thiophen-2-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(235) 4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-isopropylpiperidine-1-carboxamide;
(236) tert-butyl 3-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylate;
(237) 3-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-isopropyl-2,5-dihydro-1H-pyrrol-1-carboxamide;
(238) 3-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-N-isopropylpyrrolidine-1-carboxamide;
(239) tert-butyl 4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(240) tert-butyl 4-(5-(3-acetamidophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(241) tert-butyl 4-(5-(4-acetamidophenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(242) tert-butyl 4-(5-(3-propoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(243) tert-butyl 4-(5-(4-propoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(244) tert-butyl 4-(5-(2-methoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate;
(245) tert-butyl 5-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-3,4-dihydropyridine-1(2H)-carboxylate;
(246) N-cyclopentyl-2-(4-(5-(3,4-dimethoxyphenyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)phenyl)acetamide 2,2,2-trifluoroacetate;
(247) 2-(4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)phenyl)acetic acid;
(248) N-cyclopentyl-2-(4-(5-(5-(morpholinomethyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)phenyl)acetamide 2,2,2-trifluoroacetate;
(249) N-cyclopentyl-2-(4-(5-(5-(morpholine-4-carbonyl)thiophen-2-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl)phenyl)acetamide;
and
(250) (4-(5-(4-(morpholinomethyl)phenylamino)-1H-pyrrolo[2,3-b]pyridin-3-yl)-5,6-dihydropyridin-1(2H)-yl)(thiophen-2-yl)methanone,
a pharmaceutically acceptable salt thereof, a hydrate thereof, or a solvate thereof.

240 more elements

Dependencies are inferred from the claim text.

Facts

Application: 15/080,068Filed 24 Mar 2016
Priority: KR 10-2015-00476933 Apr 2015
Published: US 2016/0297815 A113 Oct 2016
Granted: 26 Mar 2019
Term ends: Not estimatedThe source records don’t support an estimate.

Classification4 codes

C07D 471/04
In which the condensed system contains two hetero rings: ortho-condensed systems
C07D 487/04
In which the condensed system contains two hetero rings: ortho-condensed systems
C07D 519/00
Heterocyclic compounds containing more than one system of two or more relevant
C07D
Heterocyclic compounds