IP Library Granted Patent US 10,239,873
Granted Patent B2
US 10,239,873 · App. 15/080,068 · Granted Mar 26, 2019

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

Inventors: Soongyu Choi (Yongin-si, KR); Kwang-Seop Song (Yongin-si, KR); Hee Jeong Seo (Yongin-si, KR); Sang-ho Ma (Yongin-si, KR); Eun-Jung Park (Yongin-si, KR); Younggyu Kong (Yongin-si, KR); So Ok Park (Yongin-si, KR); Kisoo Park (Yongin-si, KR); Ickhwan Son (Yongin-si, KR); Min Ju Kim (Yongin-si, KR); Man-Young Cha (Yongin-si, KR); Mi-Soon Kim (Yongin-si, KR); Sang Mi Kang (Yongin-si, KR); Dong Hyuk Jang (Yongin-si, KR); Jangwon Hong (Yongin-si, KR)
Assignee: GREEN CROSS CORPORATION
C07D471/04C07D487/04C07D519/00
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Quick Facts
Patent No.
US 10,239,873
App. No.
15/080,068
Granted
Mar 26, 2019
Kind
B2
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.

Claims (258)

1. 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;

R 1 is halogen, substituted or unsubstituted C 5-14 aryl, substituted or unsubstituted 5- to 13-membered heteroaryl, or -NHY wherein Y is substituted or unsubstituted C 5-14 aryl, wherein when said C 5-14 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-C 1-7 alkyl, C 1-7 alkoxy, halogen, C 1-7 alkyl, C 1-7 alkylamido, C 1-7 alkyl-5- to 10-membered heterocycloalkyl-C 1-7 alkyl, C 3-10 cycloalkyl-5- to 10-membered heterocycloalkyl-C 1-7 alkyl, 5- to 10-membered heterocycloalkyl-C 1-7 alkyl, C 1-7 alkyl-5- to 10-membered heterocycloalkyl-carbonyl, 5- to 10-membered heterocycloalkyl-amino, 5- to 10-membered heterocycloalkyl-oxy, C 1-7 alkyl-sulfonyl, C 3-10 cycloalkyl-sulfonyl, sulfamoyl, C 1-7 alkyl-sulfamoyl, 5- to 10-membered heterocycloalkyl-sulfonyl, amino, oxo, 5- to 13-membered heteroaryl-C 1-7 alkyl-carbamoyl, 5- to 10-membered heterocycloalkyl-C 1-7 alkoxy, 5- to 10-membered heterocycloalkyl-carbonyl, C 1-7 alkoxy-carbonyl-5- to 10-membered heterocycloalkyl-C 1-7 alkyl, 5- to 10-membered heterocycloalkyl, C 1-7 alkyl-carbonyl, C 1-7 alkoxy-carbonyl, cyano, C 1-7 alkyl-5- to 13-membered heteroaryl, di C 1-7 alkyl-sulfonyl, and C 1-7 alkyl-amino-sulfonyl;

R 2 is H or —NH 2 ;

R 3 is H or C 1-7 alkyl;

R 4 is C 1-7 alkyl, —C(═O)—R 7 , —C(═O)—O—R 8 , —C(═O)—N(—R 9 )—R 10 , —CH 2 —C(═O)—NH—R 11 or —CH 2 —C(═O)—R 12 ; R 7 to R 12 are each independently H, hydroxy, C 1-7 alkyl, substituted or unsubstituted C 3-10 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 C 1-7 alkyl; and

R 5 and R 6 are each independently H, halogen, C 1-7 alkyl or substituted or unsubstituted C 5-14 aryl; when said R 5 and R 6 are C 1-7 alkyl, said R 5 and R 6 are optionally connected to each other.

2. The compound of claim 1 , wherein the ring A is a heterocycle ring selected from the group consisting of:

R 4 is substituted at N position; and

each of R 5 and R 6 is substituted at other positions.

3. The compound of claim 1 , wherein R 1 is halogen, substituted or unsubstituted phenyl, substituted or unsubstituted thiophenyl, substituted or unsubstituted isoindolinonyl, substituted or unsubstituted pyridinyl, substituted or unsubstituted furanyl, substituted or unsubstituted benzodioxolyl, substituted or unsubstituted thiadiazolyl, substituted or unsubstituted indazolyl or substituted or unsubstituted oxoisoindolinyl.

4. The compound of claim 3 , wherein the phenyl, thiophenyl, isoindolinonyl, pyridinyl, furanyl, benzodioxolyl, thiadiazolyl, indazolyl or oxoisoindolinyl is substituted with one or more substituents selected from the group consisting of fluoro, chloro, amino, tetrahydro-2H-pyran-amino, cyano, acetyl, acetamido, methylsulfonamido, methyl, morpholinomethyl, piperazinylmethyl, methylpiperazinylmethyl, ethylpiperazinylmethyl, pyrrolidinylmethyl, cyclopropylpiperazinylmethyl, tertbutyloxycarbonylpiperazinylmethyl, morpholinoethyl, methoxy, propoxy, morpholinoethoxy, morpholinopropoxy, tetrahydro-2H -pyran-oxy, methylpiperazinylcarbonyl, methoxycarbonyl, morpholinocarbonyl, methylsulfonyl, ethylsulfonyl, propylsulfonyl, cyclopropylsulfonyl, morpholinosulfonyl, sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, furanylmethylcarbamoyl, morpholino, piperidine, and sulfonamido.

5. The compound of claim 1 , wherein R 4 is methyl, ethyl, propyl, isobutyl, —C(═O)—R 7 , —C(═O)—O—R 8 , —C(═O)—N(—R 9 )—R 10 , —CH 2 —C(═O)—NH—R 11 or —CH 2 —C(═O)—R 12 ; said R 7 to R 12 are each independently H, hydroxy, methyl, ethyl, propyl, butyl, pentyl, isobutyl, isopropyl, isopentyl, isohexyl, tert-butyl, pentan-3-yl, sec-butyl, cyclopropyl, cyclopentyl, cyclohexyl, oxetan-3-yl, tetrahydrofuran-3-yl, pyrrolidin-1-yl, cyclobutyl, thiophen-2-yl or 5-methylthiophen-2-yl.

6. 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.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 28, 2016
From: CHOI, SOONGYU; SONG, KWANG-SEOP; SEO, HEE JEONG; MA, SANG-HO; PARK, EUN-JUNG; KONG, YOUNGGYU; PARK, SO OK; PARK, KISOO; SON, ICKHWAN; KIM, MIN JU; CHA, MAN-YOUNG; KIM, MI-SOON; KANG, SANG MI; JANG, DONG HYUK; HONG, JANGWON
To: GREEN CROSS CORPORATION
Reel/Frame 038111/0124 →
Priority Claims (1)
KR 10-2015-0047693 · Apr 3, 2015 · national
Continuity (1)
Related Publication 20160297815A1 · Oct 13, 2016
Cited By (3)
US 12,454,534 US 12,459,958 US 12,673,933