# US 2014/0194418 A1 · Bicyclic carboxamide inhibitors of kinases

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- Number: US 2014/0194418 A1
- Document ID: US20140194418A1
- Status: Published application
- Kind: A1
- Application number: 13/979,387
- Filed: 2012-01-20
- Published: 2014-07-10
- Earliest claimed: 2011-01-21
- Assignees: AbbVie Inc.
- Inventors: Anil Vasudevan; Thomas Dale Penning; Huanming Chen; Bo Liang; Shaohui Wang; Fengchun Wu; Yan Shen; Cuihua Liu; Zhenguang Zou; Marina Pliushchev
- Web page: https://patentgrep.com/patent/US20140194418A1

## CPC

- C07D 519/00: Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- A61K 31/4353: ortho- or peri-condensed with heterocyclic ring systems
- A61P 35/00: Antineoplastic agents
- A61P 35/02: specific for leukemia
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 471/04: Ortho-condensed systems
- C07D 487/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Compounds of formula (I) or pharmaceutical acceptable salts are provided, wherein X1˜X5, R1˜R3, A, B, Z and n are defined in the description. And compositions containing said compounds, and the uses for inhibitors of kinases such as ALK, and the uses for treating cancer thereof are provided.

## Claims

### Claim 1

A compound of formula (I):
wherein
X2 is N, X5 is C, X1, X3, and X4 are CH; or
X1 and X2 are N, X5 is C, and X3 and X4 are CR14; or
X1 and X3 are N, X2 and X5 are C, and X4 is CR14; or
X1, X2, and X4 are N, X5 is C, and X3 is CR14; or
X1, X2, X3, and X4 are N and X5 is C; or
X1 and X5 are N, X2 is C, and X3 and X4 are CH;
A is phenyl, naphthyl, indenyl, C3-8 cycloalkyl, 5-7 membered heterocycloalkyl, 5-7 membered heterocycloalkenyl, or 5-7 membered heteroaryl;
B is phenyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, or pyrazolinyl, wherein B is optionally substituted with one, two, three, or four R2 and is substituted with R3; or
B is 1,2,3,4-tetrahydroisoquinoline;
Z is a bond, C1-6 alkylene, or C2-6 alkenylene;
R1, at each occurrence, is independently selected from the group consisting of halo, CN, NO2, C1-6-alkyl, C1-6-haloalkyl, aryl, C3-8 cycloalkyl, heteroaryl, heterocycloalkyl, OR5, SR5, C(O)R5, C(O)NR6R7, C(O)OR5, OC(O)R5, OC(O)NR6R7, NR6R7, NR6C(O)R5, S(O)R5, S(O)NR6R7, S(O)2R5, NR6S(O)2R5, and S(O)2NR6R7; wherein the C3-8 cycloalkyl, aryl, heterocycloalkyl, and heteroaryl are optionally substituted with 1, 2, or 3 substituents independently selected from halo, C1-4 alkyl, C1-4 haloalkyl, CN, NO2, ORa, SRa, C(O)Ra, C(O)NRbRc, C(O)ORa, OC(O)Ra, OC(O)NRbRc, NRbRc, NRbC(O)Ra, S(O)Ra, S(O)NRbRc, S(O)2Ra, NRbS(O)2Ra, and S(O)2NRbRc;
R2, at each occurrence, is independently selected from the group consisting of halo, CN, OH, C1-4 alkyl, C1-4-haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, C1-4-thioalkoxy, —S(O)C1-4 alkyl; amino, C1-4 alkylamino, and C1-4 dialkylamino;
R3 is selected from the group consisting of aryl, C3-8 cycloalkyl, heteroaryl, heterocycloalkyl, aryl-C1-6-alkyl-, C3-8 cycloalkyl-C1-6-alkyl-, heteroaryl-C1-6-alkyl-, heterocycloalkyl-C1-6-alkyl-, OR8, C(O)R8, —CH2C(O)R8, C(O)NR9R10, C(O)OR8, OC(O)R8, OC(O)NR9R10, NR9R10, NR9C(O)R8, S(O)R8, S(O)NR9R10, S(O)2R8, NR9S(O)2R8, and S(O)2NR9R10, wherein the C3-8 cycloalkyl, aryl, heterocycloalkyl, and heteroaryl, alone or part of another moiety, are optionally substituted with one, two, or three R11;
R4 is H or C1-6-alkyl;
R5, R6, and R7, at each occurrence, are independently selected from H, C1-6 alkyl, C1-6 haloalkyl, aryl, C3-8 cycloalkyl, heteroaryl, and heterocycloalkyl, wherein the aryl, C3-8 cycloalkyl, heteroaryl, and heterocycloalkyl moiety are optionally substituted with 1, 2, or 3 substituents independently selected from halo, CN, OH, C1-4 alkyl, C1-4-haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, amino, C1-4 alkylamino, C1-4 dialkylamino, C(O)OH, C(O)C1-4 alkyl, C(O)NH2, C(O)NH(C1-4 alkyl), or C(O)N(C1-4 alkyl)2;
R8, R9, and R10, at each occurrence, are independently selected from H, C1-6 alkyl, C1-6 haloalkyl, heteroaryl-C1-6-alkyl-, heterocycloalkyl-C1-6-alkyl-, R12R13N—C1-6-alkyl-, aryl, C3-8 cycloalkyl, heteroaryl, and heterocycloalkyl, wherein the aryl, C3-8 cycloalkyl, heteroaryl, and heterocycloalkyl, alone or as part of another moiety, are optionally substituted with 1, 2, or 3 substituents independently selected from halo, CN, OH, C1-4 alkyl, C1-4-haloalkyl, C1-4 alkoxy, C1-4 haloalkoxy, amino, C1-4 alkylamino, C1-4 dialkylamino, C(O)OH, C(O)C1-4 alkyl, C(O)NH2, C(O)NH(C1-4 alkyl), or C(O)N(C1-4 alkyl)2;
R11, at each occurrence, is independently selected from the group consisting of halo, C1-4 alkyl, C1-4 haloalkyl, amino-C1-4-alkyl-, C1-4 alkylamino-C1-4 alkyl-, C1-4 dialkylamino-C1-4 alkyl-, hydroxy-C1-4-alkyl-, C1-4 alkyl-C1-4 alkoxy, aryl, C3-8 cycloalkyl, heteroaryl, heterocycloalkyl, aryl-(C1-2 alkyl)-, C3-8 cycloalkyl-(C1-2 alkyl)-, heteroaryl-(C1-2 alkyl)-, heterocycloalkyl-(C1-2 alkyl)-, CN, NO2, ORd, SRd, C(O)Rd, C(O)NReRf, C(O)ORd, OC(O)Rd, OC(O)NReRf, NReRf, NReC(O)Rd, S(O)Rd, S(O)NReRf, S(O)2Rd, NReS(O)2Rd, and S(O)2NReRf, wherein the aryl, C3-8 cycloalkyl, heteroaryl, and heterocycloalkyl, alone or as part of another moiety, are optionally substituted with one, two or three substituents independently selected from halo and C1-4 alkyl;
R12 and R13, at each occurrence, are independently selected from the group consisting of H, C1-6 alkyl, C1-6 haloalkyl, aryl, C3-8 cycloalkyl, heteroaryl, and heterocycloalkyl;
R14 is selected from the group consisting of H, C1-6 alkyl, C1-6 haloalkyl, —C1-6 alkyl-heterocycloalkyl, —C(O)OC1-6 alkyl, —C(O)OC1-6 haloalkyl, —C(O)NHC1-6 alkyl, —C(O)NHC1-6 haloalkyl;
Ra, at each occurrence, is independently selected from the group consisting of H, C1-6 alkyl, C1-6 haloalkyl, aryl, C3-8 cycloalkyl, heteroaryl, and heterocycloalkyl;
Rb and Rc, at each occurrence, are independently selected from the group consisting of H, C1-6 alkyl, C1-6 haloalkyl, aryl, C3-8 cycloalkyl, heteroaryl, heterocycloalkyl;
Rd, at each occurrence, is independently selected from the group consisting of H, C1-6 alkyl, C1-6 haloalkyl, aryl, C3-8 cycloalkyl, heteroaryl, and heterocycloalkyl;
Re and Rf, at each occurrence, are independently selected from the group consisting of H, C1-6 alkyl, C1-6 haloalkyl, aryl, C3-8 cycloalkyl, heteroaryl, and heterocycloalkyl; and
n is 0, 1, 2, or 3;
or a pharmaceutically acceptable salt or solvate thereof.

### Claim 2 (depends on 1)

The compound of claim 1 of formula (I) wherein X2 is N, X5 is C, X1, X3, and X4 are CH.

### Claim 3 (depends on 1)

The compound of claim 1 of formula (I) wherein X1 and X2 are N, X5 is C, and X3 and X4 are CR14.

### Claim 4 (depends on 1)

The compound of claim 1 of formula (I) wherein X1 and X3 are N, X2 and X5 are C, and X4 is CR14.

### Claim 5 (depends on 1)

The compound of claim 1 of formula (I) wherein X1, X2, and X4 are N, X5 is C, and X3 is CR14.

### Claim 6 (depends on 1)

The compound of claim 1 of formula (I) wherein X1, X2, X3, and X4 are N and X5 is C.

### Claim 7 (depends on 1)

The compound of claim 1 of formula (I) wherein Z is —CH2—, —CH2CH2—, —CH(CH3)—, or —C(CH3)2—.

### Claim 8 (depends on 1)

The compound of claim 1 of formula (I) wherein Z is —CH(═CH2)— or —CH═CH—.

### Claim 9 (depends on 1)

The compound of claim 1 of formula (I) wherein Z is a bond.

### Claim 10 (depends on 1)

The compound of claim 1 of formula (I) wherein A is phenyl.

### Claim 11 (depends on 10)

The compound of claim 10 of formula (I) wherein
n is 0, 1, or 2; and
R1 is halo, OR5, C1-6 alkyl, C1-6 haloalkyl, or CN.

### Claim 12 (depends on 10)

The compound of claim 10 of formula (I) wherein
n is 1,
R1 is C(O)NR6R7, C(O)OR5, NR6C(O)R5, NR6S(O)2R5, or S(O)2NR6R7.

### Claim 13 (depends on 1)

The compound of claim 1 of formula (I) wherein A is a 5-7 membered heteroaryl selected from the group consisting of include furanyl, thiophenyl, pyrrolyl, imidazolyl, pyrazoyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, thiodiazolyl, oxadiazolyl, oxatriazolyl, dioxazolyl, oxathiazolyl, oxathiolyl, pyridinyl, pyridazinyl, pyrimidinyl, and pyrazinyl.

### Claim 14 (depends on 1)

The compound of claim 1 of formula (I) wherein B is phenyl.

### Claim 15 (depends on 14)

The compound of claim 14 of formula (I) wherein R3 is heterocycloalkyl.

### Claim 16 (depends on 1)

The compound of claim 1 of formula (I) wherein B is

### Claim 17 (depends on 16)

The compound of claim 16 of formula (I) wherein
m is 0 or 1;
R2 is halo, C1-4 alkyl, or C1-4 alkoxy;
R3 is
and
R11 is C1-4 alkyl, C1-4 haloalkyl, amino-C1-4-alkyl-, C1-4 alkylamino-C1-4 alkyl-, C1-4 dialkylamino-C1-4 alkyl-, and hydroxy-C1-4-alkyl-, C1-4 alkyl-C1-4 alkoxy, aryl, cycloalkyl, heteroaryl, heterocycloalkyl, aryl-(C1-2 alkyl)-, cycloalkyl-(C1-2 alkyl)-, heteroaryl-(C1-2 alkyl)-, or heterocycloalkyl-(C1-2 alkyl)-, wherein the aryl, cycloalkyl, heteroaryl, and heterocycloalkyl, alone or as part of another moiety, are optionally substituted with 1, 2, or 3 substituents independently selected from halo and C1-4 alkyl.

### Claim 18 (depends on 1)

The compound of claim 1 of formula (I) or a salt or a solvate thereof selected from the group consisting of
5-(2,6-dichlorobenzyl)-7-{[2-methoxy-4-(piperazin-1-yl)phenyl]amino}imidazo[1,2-c]pyrimidine-8-carboxamide;
5-(2,6-dichlorobenzyl)-7-{[2-methoxy-4-(piperazin-1-yl)phenyl]amino}[1,2,4]triazolo[4,3-c]pyrimidine-8-carboxamide;
5-(2,6-dichlorobenzyl)-7-{[2-methoxy-4-(piperazin-1-yl)phenyl]amino}[1,2,4]triazolo[4,3-c]pyrimidine-8-carboxamide;
5-(2,6-dichlorobenzyl)-7-{[4-(piperazin-1-yl)phenyl]amino}[1,2,4]triazolo[4,3-c]pyrimidine-8-carboxamide;
5-(2,6-dichlorobenzyl)-7-{[2-methoxy-4-(piperazin-1-yl)phenyl]amino}tetrazolo[1,5-c]pyrimidine-8-carboxamide;
5-(2,6-dichlorobenzyl)-7-{[4-(piperazin-1-yl)phenyl]amino}tetrazolo[1,5-c]pyrimidine-8-carboxamide;
5-(2,6-dichlorobenzyl)-7-{[2-methoxy-4-(piperazin-1-yl)phenyl]amino}imidazo[1,2-a]pyridine-8-carboxamide;
5-(2,6-dichlorobenzyl)-7-{[4-(piperazin-1-yl)phenyl]amino}imidazo[1,2-a]pyridine-8-carboxamide;
4-(2,6-dichlorobenzyl)-6-{[2-methoxy-4-(piperazin-1-yl)phenyl]amino}-1H-imidazo[4,5-c]pyridine-7-carboxamide;
5-(2,6-dichlorobenzyl)-7-{[4-(piperazin-1-yl)phenyl]amino}imidazo[1,2-c]pyrimidine-8-carboxamide;
5-(2,6-dichlorobenzyl)-7-{[2-methoxy-4-(morpholin-4-ylcarbonyl)phenyl]amino}imidazo[1,2-c]pyrimidine-8-carboxamide;
5-(2,6-dichlorobenzyl)-7-[(2-methoxy-4-{[2-(piperidin-1-yl)ethyl]carbamoyl}phenyl)amino][1,2,4]triazolo[4,3-c]pyrimidine-8-carboxamide;
5-(2,6-dichlorobenzyl)-7-[(4-{[2-(dimethylamino)ethyl]carbamoyl}-2-methoxyphenyl)amino]imidazo[1,2-c]pyrimidine-8-carboxamide;
7-{[2-methoxy-4-(piperazin-1-yl)phenyl]amino}-5-(pyrrolidin-1-yl)imidazo[1,2-c]pyrimidine-8-carboxamide;
5-(2,6-dichlorobenzyl)-7-{[2-(methylsulfinyl)-4-(piperazin-1-yl)phenyl]amino}imidazo[1,2-c]pyrimidine-8-carboxamide;
5-(2,6-dichlorobenzyl)-7-{[2,5-difluoro-4-(piperazin-1-yl)phenyl]amino}[1,2,4]triazolo[4,3-c]pyrimidine-8-carboxamide;
5-(2,6-dichlorobenzyl)-7-{[2,6-difluoro-4-(piperazin-1-yl)phenyl]amino}[1,2,4]triazolo[4,3-c]pyrimidine-8-carboxamide;
7-{[2-methoxy-4-(piperazin-1-yl)phenyl]amino}-5-{[(1S)-1-phenylethyl]amino}imidazo[1,2-c]pyrimidine-8-carboxamide;
5-(2,6-dichlorobenzyl)-7-{[3-methyl-4-(piperazin-1-yl)phenyl]amino}[1,2,4]triazolo[4,3-c]pyrimidine-8-carboxamide;
6-{[3-chloro-4-(piperazin-1-yl)phenyl]amino}-4-(2,6-dichlorobenzyl)-1H-imidazo[4,5-c]pyridine-7-carboxamide;
5-(2-chlorobenzyl)-7-{[2-methoxy-4-(piperazin-1-yl)phenyl]amino}imidazo[1,2-c]pyrimidine-8-carboxamide;
4-(2,6-dichlorobenzyl)-6-{[2,5-difluoro-4-(piperazin-1-yl)phenyl]amino}-1H-imidazo[4,5-c]pyridine-7-carboxamide;
7-{[2-methoxy-4-(piperazin-1-yl)phenyl]amino}-5-(piperazin-1-yl)imidazo[1,2-c]pyrimidine-8-carboxamide;
7-{[2-methoxy-4-(piperazin-1-yl)phenyl]amino}-5-(piperidin-4-ylamino)imidazo[1,2-c]pyrimidine-8-carboxamide;
4-(2,6-dichlorobenzyl)-6-{[4-(piperazin-1-yl)-2-(trifluoromethyl)phenyl]amino}-1H-imidazo[4,5-c]pyridine-7-carboxamide;
5-(2,6-dichlorobenzyl)-7-({2-methoxy-4-[(4-methylpiperazin-1-yl)carbonyl]phenyl}amino)imidazo[1,2-c]pyrimidine-8-carboxamide;
5-(2,6-dichlorobenzyl)-7-[(2-methoxy-4-{[2-(4-methylpiperazin-1-yl)ethyl]carbamoyl}phenyl)amino]imidazo[1,2-c]pyrimidine-8-carboxamide;
5-(2,6-dichlorobenzyl)-7-{[3,5-dichloro-4-(piperazin-1-yl)phenyl]amino}[1,2,4]triazolo[4,3-c]pyrimidine-8-carboxamide;
4-(2,6-dichlorobenzyl)-6-{[2-methyl-4-(piperazin-1-yl)phenyl]amino}-1H-imidazo[4,5-c]pyridine-7-carboxamide;
7-{[3-chloro-4-(piperazin-1-yl)phenyl]amino}-5-(2,6-dichlorobenzyl)[1,2,4]triazolo[4,3-c]pyrimidine-8-carboxamide;
5-(2,6-dichlorobenzyl)-7-{[2-fluoro-4-(piperazin-1-yl)phenyl]amino}[1,2,4]triazolo[4,3-c]pyrimidine-8-carboxamide;
4-(2,6-dichlorobenzyl)-6-{[3-methyl-4-(piperazin-1-yl)phenyl]amino}-1H-imidazo[4,5-c]pyridine-7-carboxamide;
4-(2,6-dichlorobenzyl)-6-({2-methoxy-4-[2-oxo-2-(pyrrolidin-1-yl)ethyl]phenyl}amino)-1H-imidazo[4,5-c]pyridine-7-carboxamide;
4-(2,6-dichlorobenzyl)-6-[(4-{[2-(dimethylamino)ethyl]carbamoyl}-2-methoxyphenyl)amino]-1H-imidazo[4,5-c]pyridine-7-carboxamide;
5-(2,6-dichlorobenzyl)-7-[(2-methoxy-4-{[2-(pyrrolidin-1-yl)ethyl]carbamoyl}phenyl)amino]imidazo[1,2-c]pyrimidine-8-carboxamide;
5-(2,6-dichlorobenzyl)-7-[(2-methoxy-4-{[2-(piperidin-1-yl)ethyl]carbamoyl}phenyl)amino]imidazo[1,2-c]pyrimidine-8-carboxamide;
5-(2,6-dichlorobenzyl)-7-[(2-methoxy-4-{[3-(morpholin-4-yl)propyl]carbamoyl}phenyl)amino]imidazo[1,2-c]pyrimidine-8-carboxamide;
5-(2,6-dichlorobenzyl)-7-{[2-methoxy-4-(piperazin-1-ylcarbonyl)phenyl]amino}imidazo[1,2-c]pyrimidine-8-carboxamide;
4-(2,6-dichlorobenzyl)-6-({2-methoxy-4-[(4-methylpiperazin-1-yl)carbonyl]phenyl}amino)-1H-imidazo[4,5-c]pyridine-7-carboxamide;
4-(2,6-dichlorobenzyl)-6-{[2-fluoro-4-(piperazin-1-yl)phenyl]amino}-1H-imidazo[4,5-c]pyridine-7-carboxamide;
5-[(2-chlorophenyl)amino]-7-{[2-methoxy-4-(piperazin-1-yl)phenyl]amino}imidazo[1,2-c]pyrimidine-8-carboxamide;
4-(2,6-dichlorobenzyl)-6-{[2-methoxy-4-(piperazin-1-ylcarbonyl)phenyl]amino}-1H-imidazo[4,5-c]pyridine-7-carboxamide;
5-[(2,3-difluorophenyl)amino]-7-{[2-methoxy-4-(piperazin-1-yl)phenyl]amino}imidazo[1,2-c]pyrimidine-8-carboxamide;
4-(2,6-dichlorobenzyl)-6-{[3,5-dichloro-4-(piperazin-1-yl)phenyl]amino}-1H-imidazo[4,5-c]pyridine-7-carboxamide;
4-(2,6-dichlorobenzyl)-6-{[3,5-difluoro-4-(piperazin-1-yl)phenyl]amino}-1H-imidazo[4,5-c]pyridine-7-carboxamide;
6-{[2-chloro-4-(piperazin-1-yl)phenyl]amino}-4-(2,6-dichlorobenzyl)-1H-imidazo[4,5-c]pyridine-7-carboxamide;
4-(2,6-dichlorobenzyl)-6-{[3-fluoro-2-methoxy-4-(piperazin-1-yl)phenyl]amino}-1H-imidazo[4,5-c]pyridine-7-carboxamide;
4-(2,6-dichlorobenzyl)-6-{[4-(piperazin-1-yl)-3-(trifluoromethyl)phenyl]amino}-1H-imidazo[4,5-c]pyridine-7-carboxamide;
4-(2,6-dichlorobenzyl)-6-{[4-(piperazin-1-yl)-2-(trifluoromethoxy)phenyl]amino}-1H-imidazo[4,5-c]pyridine-7-carboxamide;
4-(2,6-dichlorobenzyl)-6-{[2-methoxy-5-(piperazin-1-yl)phenyl]amino}-1H-imidazo[4,5-c]pyridine-7-carboxamide;
4-(2,6-dichlorobenzyl)-6-{[4-(hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)-2-methoxyphenyl]amino}-1H-imidazo[4,5-c]pyridine-7-carboxamide;
4-[(2-chlorophenyl)amino]-6-{[2-methoxy-4-(piperazin-1-yl)phenyl]amino}pyrazolo[1,5-a]pyrazine-7-carboxamide;
4-(2,6-dichlorobenzyl)-6-{[2,3-dimethyl-4-(piperazin-1-yl)phenyl]amino}-1H-imidazo[4,5-c]pyridine-7-carboxamide;
4-(2,6-dichlorobenzyl)-6-{[2-methoxy-4-(pyrrolidin-1-ylmethyl)phenyl]amino}-1H-imidazo[4,5-c]pyridine-7-carboxamide;
7-{[2-bromo-4-(piperazin-1-yl)phenyl]amino}-5-(2,6-dichlorobenzyl) [1,2,4]triazolo[4,3-c]pyrimidine-8-carboxamide;
4-(2,6-dichlorobenzyl)-6-{[2-fluoro-5-methyl-4-(piperazin-1-yl)phenyl]amino}-1H-imidazo[4,5-c]pyridine-7-carboxamide;
4-(2,6-dichlorobenzyl)-6-{[3,5-difluoro-2-methoxy-4-(piperazin-1-yl)phenyl]amino}-1H-imidazo[4,5-c]pyridine-7-carboxamide;
4-(2,6-dichlorobenzyl)-6-[(6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-yl)amino]-1H-imidazo[4,5-c]pyridine-7-carboxamide;
6-{[2-chloro-4-(piperidin-4-yl)phenyl]amino}-4-(2,6-dichlorobenzyl)-1H-imidazo[4,5-c]pyridine-7-carboxamide;
7-(2-chloro-4-(piperidin-4-yl)phenylamino)-5-(2-chlorobenzyl)-3-ethyl-[1,2,4]triazolo[4,3-c]pyrimidine-8-carboxamide;
5-(2,6-dichlorobenzyl)-7-{[2-methoxy-4-(piperazin-1-yl)phenyl]amino}-3-methyl[1,2,4]triazolo[4,3-c]pyrimidine-8-carboxamide;
5-(2,6-dichlorobenzyl)-3-ethyl-7-{[2-methoxy-4-(piperazin-1-yl)phenyl]amino}[1,2,4]triazolo[4,3-c]pyrimidine-8-carboxamide;
5-(2-chlorobenzyl)-2-ethyl-7-{[2-methoxy-4-(piperazin-1-yl)phenyl]amino}imidazo[1,2-c]pyrimidine-8-carboxamide;
5-(2-chlorobenzyl)-7-{[2-chloro-4-(piperidin-4-yl)phenyl]amino}-2-ethylimidazo[1,2-c]pyrimidine-8-carboxamide;
5-(2-chlorobenzyl)-7-{[2-chloro-4-(piperidin-4-yl)phenyl]amino}[1,2,4]triazolo[4,3-c]pyrimidine-8-carboxamide;
5-(2-chlorobenzyl)-3-ethyl-7-{[2-methoxy-4-(piperazin-1-yl)phenyl]amino}[1,2,4]triazolo[4,3-c]pyrimidine-8-carboxamide;
5-(2,3-dichlorobenzyl)-7-{[2-methoxy-4-(piperidin-4-yl)phenyl]amino}[1,2,4]triazolo[4,3-c]pyrimidine-8-carboxamide;
5-(2-fluorobenzyl)-7-{[2-methoxy-4-(piperidin-4-yl)phenyl]amino}[1,2,4]triazolo[4,3-c]pyrimidine-8-carboxamide;
5-(2,3-difluorobenzyl)-7-{[2-methoxy-4-(piperidin-4-yl)phenyl]amino}[1,2,4]triazolo[4,3-c]pyrimidine-8-carboxamide;
5-(2,6-dichlorobenzyl)-7-{[2-methoxy-4-(piperazin-1-yl)phenyl]amino}-2-(morpholin-4-ylmethyl)imidazo[1,2-c]pyrimidine-8-carboxamide;
ethyl 8-carbamoyl-5-(2,6-dichlorobenzyl)-7-{[2-methoxy-4-(piperazin-1-yl)phenyl]amino}imidazo[1,2-c]pyrimidine-2-carboxylate;
5-(2,6-dichlorobenzyl)-N˜2˜-ethyl-7-{[2-methoxy-4-(piperazin-1-yl)phenyl]amino}imidazo[1,2-c]pyrimidine-2,8-dicarboxamide; and
5-(2,6-dichlorobenzyl)-7-{[2-methoxy-4-(piperazin-1-yl)phenyl]amino}-N˜2˜-(2,2,2-trifluoroethyl)imidazo[1,2-c]pyrimidine-2,8-dicarboxamide.

### Claim 19 (depends on 1)

A pharmaceutical composition comprising a compound or pharmaceutically acceptable salt of claim 1 and pharmaceutically acceptable excipient.

### Claim 20 (depends on 1)

A method of treating cancer in a mammal comprising administering thereto a therapeutically acceptable amount of a compound or pharmaceutically acceptable salt of claim 1.

### Claim 21 (depends on 1)

A method for decreasing tumor volume in a mammal comprising administering thereto a therapeutically acceptable amount of a compound or pharmaceutically acceptable salt of claim 1.