Substituted 3-cyanopyridines as protein kinase inhibitors

• US 7,781,591 B2
• Filed: 06/13/2007
• Issued: 08/24/2010
• Est. Priority Date: 06/13/2006
• Status: Active Grant

• Current Assignee: Wyeth (Pfizer Inc.)
• Original Assignee: Wyeth LLC (Pfizer Inc.)
• Inventors: Wu, Biqi, Dushin, Russell, Joseph-McCarthy, Diane Marie, Niu, Chuan S., Asselin, Magda, Cole, Derek Cecil, Chen, Joan, Wang, Yanong Daniel, Boschelli, Diane Harris, Prashad, Amarnauth Shastrie, Tumey, Lawrence Nathan, Wissner, Allan
• Primary Examiner(s): Andres; Janet L
• Assistant Examiner(s): O DELL, DAVID K
• Application Number:
  US11/818,119
• Publication Number:
  US 20070287708A1
• Time in Patent Office: 1,168 Days
• Field of Search: 546/277.4, 546/277.7, 546/278.1, 546/256, 546/268.4, 546/269.7, 546/270.4, 546/271.1, 546/271.4, 546/275.4, 546/281.7, 546/282.4, 546/270.7
• US Class Current: 546/277.4
• CPC Class Codes: C07D 213/85 in position 3
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 401/14 containing three or more hetero rings
• CPC Class Codes: C07D 403/14 containing three or more hetero rings
• CPC Class Codes: C07D 405/14 containing three or more hetero rings
• CPC Class Codes: C07D 409/14 containing three or more hetero rings
• CPC Class Codes: C07D 413/14 containing three or more hetero rings

Abstract

The present teachings provide compounds of formula I

and their pharmaceutically acceptable salts, hydrates, and esters, wherein R¹, R², and X are as defined herein. The present teachings also provide methods of making the compounds of formula I, and methods of treating autoimmune and inflammatory diseases by administering a therapeutically effective amount of a compound or compounds of formula I to a mammal including a human.

Claims

1. A compound of formula I or formula I′

;

2. The compound of claim 1 or a pharmaceutically acceptable salt, or ester thereof, wherein X is selected from —

NH—

, —

N(CH₃)—

, —

NH—

CH₂—

, —

NH—

CH₂CH₂—

, —

NH—

CH₂CH₂CH₂, —

O—

, and a covalent bond.

3. The compound of claim 1 or 2 or a pharmaceutically acceptable salt, or ester thereof, wherein R¹ is an indolyl group, wherein each group optionally is substituted with 1-4 groups selected from halogen, oxo, —

O—

Y—

R⁵, NR⁶Y—

R⁷, a C_1-10 alkyl group and a C_1-10 haloalkyl group.

4. The compound of claim 1 or 2 or a pharmaceutically acceptable salt, or ester thereof, wherein R¹ is an indolyl group, each of which optionally is substituted with 1-4 groups selected from halogen, —

O—

Y—

R⁵, NR⁶Y—

R⁷, a C_1-10 alkyl group and a C_1-10 haloalkyl group.

5. The compound of claim 1 or 2 or a pharmaceutically acceptable salt, or ester thereof, wherein R¹ is a 1H-indol-4-yl group, a 1H-indol-5-yl group, a 1H-indol-6-yl group, or a 1H-indol-7-yl group, wherein each group optionally is substituted with 1-4 groups independently selected from a halogen, a C_1-4 alkyl group, and a C_1-4 alkoxy group.

6. The compound of claims 1 or 2 or a pharmaceutically acceptable salt, or ester thereof, wherein R² is a phenyl group, a naphthyl group or a tetrahydronaphthyl group, wherein each group optionally is substituted with 1-4 groups independently selected from —

Y—

R⁴ and —

O—

Y—

R⁴.

7. The compound of claim 1 or 2 or a pharmaceutically acceptable salt, or ester thereof, wherein R² is:

8. The compound of claim 7 or a pharmaceutically acceptable salt, or ester thereof, wherein at least one of D¹, D², and D³ is a —

Y—

R⁴ group or an —

O—

Y—

R⁴ group, wherein Y, at each occurrence, independently is a divalent C_1-4 alkyl group or a covalent bond, and R⁴, at each occurrence, independently is selected from a halogen, CN, NO₂, —

O—

Y—

R⁵, NR⁶—

Y—

R⁷, —

S(O)₂—

Y—

R⁵, —

S(O)₂NR⁶—

Y—

R⁷, —

C(O)—

Y—

R⁵, —

C(O)O—

Y—

R⁵, —

C(O)NR⁶—

Y—

R⁷, a C_1-10 alkyl group, a C_1-10 haloalkyl group, a C_3-14 cycloalkyl group, a C_6-14 aryl group, a 3-14 membered cycloheteroalkyl group, and a 5-14 membered heteroaryl group, wherein each of the C_1-10 alkyl group, the C_1-10 haloalkyl group, the C_3-14 cycloalkyl group, the C_6-14 aryl group, the 3-14 membered cycloheteroalkyl group, and the 5-14 membered heteroaryl group is optionally substituted with 1-4-Y—

R⁸ groups.

9. The compound of claim 8 or a pharmaceutically acceptable salt, or ester thereof, wherein the —

Y—

R⁴ group and the —

O—

Y—

R⁴ group are selected from —

O—

(CH₂)_nNR⁶—

Y—

R⁷, —

(CH₂)_nNR⁶—

Y—

R⁷, an —

O—

(CH₂)_n-3-14 membered cycloheteroalkyl group, and a —

(CH₂)_n-3-14 membered cycloheteroalkyl group, wherein each of the 3-14 membered cycloheteroalkyl group optionally is substituted with 1-4-Y—

R⁸ groups, and n, at each occurrence, independently is 0, 1, 2, 3, or 4.

10. The compound of claim 9 or a pharmaceutically acceptable salt, or ester thereof, wherein the 3-14 membered cycloheteroalkyl group of the —

O—

(CH₂)_n-3-14 membered cycloheteroalkyl group and the (CH₂)_n-3-14 membered cycloheteroalkyl group is selected from a pyrrolidinyl group, a morpholinyl group, a piperazinyl group, a piperidinyl group, an azepanyl group, a diazepanyl group, and a thiomorpholinyl group.

11. The compound of claim 8 or a pharmaceutically acceptable salt, or ester thereof, wherein the —

Y—

R⁴ group and the —

O—

Y—

R⁴ group are

12. The compound of claim 8 or 9 or a pharmaceutically acceptable salt, or ester thereof, wherein at least one of D¹, D², and D³ is selected from a halogen, —

CN, —

NO₂, —

S(O)₂—

Y—

R⁵, —

S(O)₂NR⁸—

Y—

R⁷, —

C(O)O—

Y—

R⁵, —

C(O)NR⁸—

Y—

R⁷, a C_1-10 alkyl group, and a C_1-10 haloalkyl group.

13. The compound of claim 8 or 9 or a pharmaceutically acceptable salt, or ester thereof, wherein at least one of D¹, D², and D³ is a C_6-14 aryl group or a 5-14 membered heteroaryl group, wherein each group optionally is substituted with 1-4-Y—

R⁸ groups.

14. The compound of claim 13 or a pharmaceutically acceptable salt, or ester thereof, wherein at least one of D¹, D², and D³ is selected from a benzothienyl group, a benzofuryl group, a furyl group, a pyridyl group, a pyrimidinyl group, a pyrrolyl group, and a thienyl group, wherein each group optionally is substituted with 1-4-Y—

R⁸ groups, Y, at each occurrence, is independently a C_1-4 alkyl group or a covalent bond, and R⁸, at each occurrence, is independently selected from halogen, —

CN, —

NO₂, —

O—

Y—

R⁹, —

C(O)NR¹⁰—

Y—

R¹¹, —

S(O)₂—

Y—

R⁹, —

S(O)₂NR¹⁰—

Y—

R¹¹, and a 3-14 membered cycloheteroalkyl group optionally substituted with a C_1-4 alkyl group.

15. The compound of claim 1 or 2 or a pharmaceutically acceptable salt, or ester thereof, wherein R² is pyridyl group, a pyrimidyl group, a pyrazinyl group, a furyl group, a thienyl group, a thiazolyl group, an oxazolyl group, a benzofuranyl group, a benzothienyl group, an indolyl group, a benzodioxolyl group, a benzodioxanyl group, a dibenzofuranyl group, a dibenzothienyl group, an isothiazolyl group, a pyrazolyl group, an isoxazolyl group, a quinolinyl group or an imidazolyl group, wherein each group optionally is substituted with 1-4 groups independently selected from —

Y—

R⁴ and —

O—

Y—

R⁴.

16. The compound of claim 15 or a pharmaceutically acceptable salt, or ester thereof, wherein each R² optionally is substituted with 1-4 groups independently selected from —

(CH₂)_n—

R⁴ and —

O—

(CH₂)_n—

R⁴, wherein n, at each occurrence, independently is 0, 1, 2, 3, or 4, and R⁴, at each occurrence, independently is —

NR⁸—

Y—

R⁷ or a 3-14 membered cycloheteroalkyl group optionally substituted with a —

Y—

R⁸ group.

17. A compound of claim 1 selected from the following compounds:

5-(3,4-dimethoxyphenyl)-4-(1H-indol-5-ylamino)nicotinonitrile,

5-(3,4-dimethoxyphenyl)-4-(1H-indol-6-ylamino)nicotinonitrile,

5-(3,4-dimethoxyphenyl)-4-(1H-indol-4-ylamino)nicotinonitrile,

5-(3,4-dimethoxyphenyl)-4-[(2-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(3-bromophenyl)-4-(1H-indol-5-ylamino)nicotinonitrile,

5-(3-bromophenyl)-4-(1H-indol-4-ylamino)nicotinonitrile,

5-(2-bromophenyl)-4-(1H-indol-5-ylamino)nicotinonitrile,

5-(4-bromophenyl)-4-(1H-indol-5-ylamino)nicotinonitrile,

5-(3′

-aminobiphenyl-3-yl)-4-(1H-indol-5-ylamino)nicotinonitrile,

5-(4′

-cyanobiphenyl-3-yl)-4-(1H-indol-5-ylamino)nicotinonitrile,

5-(4′

-aminobiphenyl-3-yl)-4-(1H-indol-5-ylamino)nicotinonitrile,

N-{3′

-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]biphenyl-4-yl}acetamide,

4-(1H-indol-5-ylamino)-5-(3-pyridin-4-ylphenyl)nicotinonitrile,

3′

-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]-N,N-dimethylbiphenyl-4-carboxamide,

3′

-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]-N-cyclopentylbiphenyl-4-carboxamide,

4-(1H-indol-5-ylamino)-5-[3-(1H-pyrrol-3-yl)phenyl]nicotinonitrile,

5-(2-bromophenyl)-4-[(7-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(2-bromophenyl)-4-(1H-indol-4-ylamino)nicotinonitrile,

4-(1H-indol-5-ylamino)-5-(3′

-methylbiphenyl-3-yl)nicotinonitrile,

4-(1H-indol-5-ylamino)-5-(4′

-methylbiphenyl-3-yl)nicotinonitrile,

5-(2′

-chlorobiphenyl-3-yl)-4-(1H-indol-5-ylamino)nicotinonitrile,

5-(3′

-chlorobiphenyl-3-yl)-4-(1H-indol-5-ylamino)nicotinonitrile,

5-(4′

-chlorobiphenyl-3-yl)-4-(1H-indol-5-ylamino)nicotinonitrile,

5-(3′

-cyanobiphenyl-3-yl)-4-(1H-indol-5-ylamino)nicotinonitrile,

3′

-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]biphenyl-3-carboxylic acid,

3′

-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]biphenyl-4-carboxylic acid,

3′

-[5-cyano-4-(1H-indol-4-ylamino)pyridin-3-yl]biphenyl-4-carboxylic acid,

4-(1H-indol-5-ylamino)-5-[3-(2-thienyl)phenyl]nicotinonitrile,

4-(1H-indol-5-ylamino)-5-(3-pyridin-3-ylphenyl)nicotinonitrile,

4-(1H-indol-5-ylamino)-5-(3-pyrimidin-2-ylphenyl)nicotinonitrile,

4-(1H-indol-5-ylamino)-5-[3-(4-methyl-2-thienyl)phenyl]nicotinonitrile,

5-[3-(5-acetyl-2-thienyl)phenyl]-4-(1H-indol-5-ylamino)nicotinonitrile,

4-(1H-indol-5-ylamino)-5-[3-(3-thienyl)phenyl]nicotinonitrile,

5-[3-(3-furyl)phenyl]-4-(1H-indol-5-ylamino)nicotinonitrile,

5-(2′

-chlorobiphenyl-2-yl)-4-(1H-indol-5-ylamino)nicotinonitrile,

5-(3′

-chlorobiphenyl-2-yl)-4-(1H-indol-5-ylamino)nicotinonitrile,

5-(4′

-chlorobiphenyl-2-yl)-4-(1H-indol-5-ylamino)nicotinonitrile,

4-(1H-indol-5-ylamino)-5-[2-(3-thienyl)phenyl]nicotinonitrile,

4-(1H-indol-4-ylamino)-5-[3-(2-thienyl)phenyl]nicotinonitrile,

3′

-[5-cyano-4-(1H-indol-4-ylamino)pyridin-3-yl]-N-cyclopentylbiphenyl-4-carboxamide,

4-(1H-indol-4-ylamino)-5-[4′

-(pyrrolidin-1-ylcarbonyl)biphenyl-3-yl]nicotinonitrile,

5-[3-(5-formyl-2-thienyl)phenyl]-4-(1H-indol-5-ylamino)nicotinonitrile,

4-(1H-indol-5-ylamino)-5-(3-nitrophenyl)nicotinonitrile,

N-{3-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]phenyl}acetamide,

4-(1H-indol-4-ylamino)-5-[4-methoxy-3-(2-methoxyethoxy)phenyl]nicotinonitrile,

4-(1H-indol-5-ylamino)-5-[4-methoxy-3-(2-methoxyethoxy)phenyl]nicotinonitrile,

4-(1H-indol-6-ylamino)-5-[4-methoxy-3-(2-methoxyethoxy)phenyl]nicotinonitrile,

5-[4-methoxy-3-(2-methoxyethoxy)phenyl]-4-[(2-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-(1H-indol-4-ylamino)-5-[3-methoxy-4-(2-methoxyethoxy)phenyl]nicotinonitrile,

4-(1H-indol-5-ylamino)-5-[3-methoxy-4-(2-methoxyethoxy)phenyl]nicotinonitrile,

4-(1H-indol-6-ylamino)-5-[3-methoxy-4-(2-methoxyethoxy)phenyl]nicotinonitrile,

5-[3-methoxy-4-(2-methoxyethoxy)phenyl]-4-[(2-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-(1H-indol-4-ylamino)-5-[3-(2-methoxyethoxy)phenyl]nicotinonitrile,

5-[3-(2-chloroethoxy)phenyl]-4-(1H-indol-4-ylamino)nicotinonitrile,

5-[3-(2-chloroethoxy)phenyl]-4-(1H-indol-6-ylamino)nicotinonitrile,

5-[3-(2-chloroethoxy)phenyl]-4-(1H-indol-5-ylamino)nicotinonitrile,

4-(1H-indol-4-ylamino)-5-{3-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl}nicotinonitrile,

4-(1H-indol-4-ylamino)-5-[3-(2-pyrrolidin-1-ylethoxy)phenyl]nicotinonitrile,

4-(1H-indol-4-ylamino)-5-[3-(2-morpholin-4-ylethoxy)phenyl]nicotinonitrile,

4-(1H-indol-4-ylamino)-5-[3-(2-piperidin-1-ylethoxy)phenyl]nicotinonitrile,

4-(1H-indol-6-ylamino)-5-[3-(2-pyrrolidin-1-ylethoxy)phenyl]nicotinonitrile,

4-(1H-indol-6-ylamino)-5-[3-(2-morpholin-4-ylethoxy)phenyl]nicotinonitrile,

4-(1H-indol-5-ylamino)-5-[3-(2-pyrrolidin-1-ylethoxy)phenyl]nicotinonitrile,

4-(1H-indol-5-ylamino)-5-[3-(2-morpholin-4-ylethoxy)phenyl]nicotinonitrile,

5-(3-{2-[(2-hydroxyethyl)amino]ethoxy}phenyl)-4-(1H-indol-5-ylamino)nicotinonitrile,

4-(1H-indol-5-ylamino)-5-(3-{2-[(2-pyrrolidin-1-ylethyl)amino]ethoxy}phenyl)nicotinonitrile,

5-[3-(2-chloroethoxy)-4-methoxyphenyl]-4-(1H-indol-5-ylamino) nicotinonitrile,

5-{3-[2-(diethylamino)ethoxy]-4-methoxyphenyl}-4-(1H-indol-5-ylamino) nicotinonitrile,

5-{3-[2-(diisopropylamino)ethoxy]-4-methoxyphenyl}-4-(1H-indol-5-ylamino) nicotinonitrile,

5-{3-[2-(benzylamino)ethoxy]-4-methoxyphenyl}-4-(1H-indo-5-ylamino) nicotinonitrile,

4-(1H-indol-5-ylamino)-5-(4-methoxy-3-{2-[(2-methoxyethyl)amino]ethoxy}phenyl)nicotinonitrile,

4-(1H-indol-5-ylamino)-5-(4-methoxy-3-{2-[(5-methyl-1,3,4-thiadiazol-2-yl) amino]ethoxy}phenyl)nicotinonitrile,

4-(1H-indol-5-ylamino)-5-(3-{5-[(4-methylpiperazin-1-yl)methyl]-2-thienyl}phenyl)nicotinonitrile,

4-(1H-indol-5-ylamino)-5-{3-[5-(morpholin-4-ylmethyl)-2-thienyl]phenyl}nicotinonitrile,

4-(1H-indol-5-ylamino)-5-{3-[5-(piperidin-1-ylmethyl)-2-thienyl]phenyl}nicotinonitrile,

5-(3-{5-[(dimethylamino)methyl]-2-thienyl}phenyl)-4-(1H-indol-5-ylamino)nicotinonitrile,

5-(3-bromo-4-methoxyphenyl)-4-(1H-indol-5-ylamino)nicotinonitrile,

4-(1H-indol-5-ylamino)-5-[4-methoxy-3-(2-thienyl)phenyl]nicotinonitrile,

5-(4′

-chloro-6-methoxybiphenyl-3-yl)-4-(1H-indol-5-ylamino)nicotinonitrile,

5-(3′

-chloro-6-methoxybiphenyl-3-yl)-4-(1H-indol-5-ylamino)nicotinonitrile,

5′

-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]-N-cyclopentyl-2′

-methoxy biphenyl-4-carboxamide,

5-(2′

-chloro-6-methoxybiphenyl-3-yl)-4-(1H-indol-5-ylamino)nicotinonitrile,

5-[3-(benzyloxy)phenyl]-4-(1H-indol-5-ylamino)nicotinonitrile,

5-[4-(benzyloxy)phenyl]-4-(1H-indol-5-ylamino)nicotinonitrile,

3′

-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]-N-methylbiphenyl-4-carboxamide,

N-butyl-3′

-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]biphenyl-4-carboxamide,

3′

-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]-N-(1-ethylpropyl)biphenyl-4-carboxamide,

3′

-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]-N-(2-hydroxyethyl)biphenyl-4-carboxamide,

3′

-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]-N-(2-methoxyethyl)biphenyl-4-carboxamide,

3′

-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]-N-cyclopropylbiphenyl-4-carboxamide,

3′

-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]-N-cyclohexyl)biphenyl-4-carboxamide,

3′

-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]-N-(2-pyrrolidin-1-yl ethyl)biphenyl-4-carboxamide,

N-benzyl-3′

-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]biphenyl-4-carboxamide,

4-(1H-indol-5-ylamino)-5-[4′

-(pyrrolidin-1-ylcarbonyl)biphenyl-3-yl]nicotinonitrile,

4-(1H-indol-5-ylamino)-5-[4′

-(morpholin-4-ylcarbonyl)biphenyl-3-yl]nicotinonitrile,

4-(1H-indol-5-ylamino)-5-{4′

-[(4-methylpiperazin-1-yl)carbonyl]biphenyl-3-yl}nicotinonitrile,

3′

-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]-N-cyclopentylbiphenyl-3-carboxamide,

3′

-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]-N-(4-hydroxybutyl)biphenyl-4-carboxamide,

3′

-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]-N-(3-hydroxypropyl)biphenyl-4-carboxamide,

3′

-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]-N-[2-(methylamino)ethyl]biphenyl-4-carboxamide,

3′

-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]-N-(pyridin-2-ylmethyl) biphenyl-4-carboxamide,

3′

-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]-N-(pyridin-3-ylmethyl) biphenyl-4-carboxamide,

3′

-[5-cyano-4-(1H-indol-5-ylamino)pyridin-3-yl]-N-(pyridin-4-ylmethyl) biphenyl-4-carboxamide,

N-butyl-3′

-[5-cyano-4-(1H-indol-4-ylamino)pyridin-3-yl]biphenyl-4-carboxamide,

3′

-[5-cyano-4-(1H-indol-4-ylamino)pyridin-3-yl]-N-(2-hydroxyethyl)biphenyl-4-carboxamide,

5-(3,4-dimethoxyphenyl)-4-[(7-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(3,4-dimethoxyphenyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(3,4-dimethoxyphenyl)-4-[1H-indol-5-yl(methyl)amino]nicotinonitrile,

5-(3,4-dimethoxyphenyl)-4-(1H-indol-5-yloxy)nicotinonitrile,

5-(3,4-dimethoxyphenyl)-4-(1H-indol-5-yl)nicotinonitrile,

5-(1-benzofuran-2-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(5-formyl-1-benzothien-2-yl)-4-(1H-indol-4-ylamino)nicotinonitrile,

5-{5-[(dimethylamino)methyl]-1-benzothien-2-yl}-4-(1H-indol-4-ylamino nicotinonitrile,

5-(4-hydroxyphenyl)-4-(1H-indol-4-ylamino)nicotinonitrile,

5-(4-{[(2S)-2-amino-3-phenylpropyl]oxy}phenyl)-4-(1H-indol-4-ylamino) nicotinonitrile,

5-(5-formyl-1-benzothien-2-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-[5-(piperidin-1-ylmethyl)-1-benzothien-2-yl]nicotinonitrile,

5-[5-(hydroxymethyl)-1-benzothien-2-yl]-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-(1H-indol-5-ylamino)-5-[4-methoxy-3-(2-morpholin-4-ylethoxy)phenyl]nicotinonitrile,

4-(1H-indol-5-ylamino)-5-{4-methoxy-3-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl}nicotinonitrile,

4-(1H-indol-5-ylamino)-5-[4-methoxy-3-(2-piperazin-1-ylethoxy)phenyl]nicotinonitrile,

4-(1H-indol-5-ylamino)-5-[4-methoxy-3-(2-thiomorpholin-4-ylethoxy)phenyl]nicotinonitrile,

5-{3-[2-(4-ethylpiperazin-1-yl)ethoxy]-4-methoxyphenyl}-4-(1H-indol-5-ylamino)nicotinonitrile,

4-(1H-indol-5-ylamino)-5-[4-methoxy-3-(2-piperidin-1-ylethoxy)phenyl]nicotinonitrile,

5-{3-[2-(dimethylamino)ethoxy]-4-methoxyphenyl}-4-(1H-indol-5-ylamino) nicotinonitrile,

5-(3-{2-[bis(2-hydroxyethyl)amino]ethoxy}-4-methoxyphenyl)-4-(1H-indol-5-ylamino)nicotinonitrile,

5-{3-[2-(4-hydroxypiperidin-1-yl)ethoxy]-4-methoxyphenyl}-4-(1H-indol-5-ylamino)nicotinonitrile,

4-(1H-indol-5-ylamino)-5-(4-methoxy-3-{2-[(pyridin-3-ylmethyl)amino]ethoxy}phenyl)nicotinonitrile,

4-(1H-indol-5-ylamino)-5-(4-methoxy-3-{2-[(pyridin-4-ylmethyl)amino]ethoxy}phenyl)nicotinonitrile,

4-(1H-indol-5-ylamino)-5-(4-methoxy-3-{2-[(pyridin-2-ylmethyl)amino]ethoxy}phenyl)nicotinonitrile,

4-(1H-indol-5-ylamino)-5-(4-methoxy-3-{2-[(2-phenylethyl)amino]ethoxy}phenyl)nicotinonitrile,

5-{3-[2-(cyclopentylamino)ethoxy]-4-methoxyphenyl}-4-(1H-indol-5-yl amino) nicotinonitrile,

5-{3-[2-(cyclohexylamino)ethoxy]-4-methoxyphenyl}-4-(1H-indol-5-yl amino) nicotinonitrile,

5-(3-{2-[(2-furylmethyl)amino]ethoxy}-4-methoxyphenyl)-4-(1H-indol-5-yl amino)nicotinonitrile,

5-(2-bromo-4,5-dimethoxyphenyl)-4-(1H-indol-5-ylamino)nicotinonitrile,

5-(2-bromo-4,5-dimethoxyphenyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-(1H-indol-4-ylamino)-5-[4-methoxy-3-(2-piperidin-1-ylethoxy)phenyl]nicotinonitrile,

5-(3-{2-[(2-hydroxyethyl)amino]ethoxy}-4-methoxyphenyl)-4-(1H-indol-4-yl amino)nicotinonitrile,

4-(1H-indol-5-ylamino)-5-(4-methoxy-3-{2-[(3-phenylpropyl)amino]ethoxy}phenyl)nicotinonitrile,

4-(1H-indol-5-ylamino)-5-(4-methoxy-3-{2-[(2-pyridin-2-ylethyl)amino]ethoxy}phenyl)nicotinonitrile,

4-(1H-indol-5-ylamino)-5-(4-methoxy-3-{2-[(2-pyridin-3-ylethyl)amino]ethoxy}phenyl)nicotinonitrile,

4-(1H-indol-5-ylamino)-5-(4-methoxy-3-{2-[(2-pyridin-4-ylethyl)amino]ethoxy}phenyl)nicotinonitrile.

5-[3-(dimethylamino)phenyl]-4-(1H-indol-4-ylamino)nicotinonitrile,

4-(1H-indol-4-ylamino)-5-[3-(methylsulfonyl)phenyl]nicotinonitrile,

N-{3-[5-cyano-4-(1H-indol-4-ylamino)pyridin-3-yl]phenyl}methane sulfonamide,

4-(1H-indol-5-ylamino)-5-phenylnicotinonitrile,

4-(1H-indol-5-ylamino)-5-(3-thienyl)nicotinonitrile,

4-(1H-indol-5-ylamino)-3,3′

-bipyridine-5-carbonitrile,

5-(1,3-benzodioxol-5-yl)-4-(1H-indol-5-ylamino)nicotinonitrile,

4-(1H-indol-5-ylamino)-3,4′

-bipyridine-5-carbonitrile,

5-(3-furyl)-4-(1H-indol-5-ylamino)nicotinonitrile,

5-(1H-indol-5-yl)-4-(1H-indol-5-ylamino)nicotinonitrile,

5-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-(1H-indol-5-ylamino)nicotinonitrile,

4-(1H-indol-5-ylamino)-5-pyrimidin-5-ylnicotinonitrile,

4-(1H-indol-5-ylamino)-5-(2-methoxypyrimidin-5-yl)nicotinonitrile,

4-(1H-indol-5-ylamino)-5-(2-thienyl)nicotinonitrile,

5-(1-benzofuran-2-yl)-4-(1H-indol-5-ylamino)nicotinonitrile,

5-(3,5-dimethylisoxazol-4-yl)-4-(1H-indol-5-ylamino)nicotinonitrile,

5-[3-(hydroxymethyl)phenyl]-4-(1H-indol-4-ylamino)nicotinonitrile,

5-{3-(dimethylamino)methydphenyl}-4-(1H-indol-4-ylamino)nicotinonitrile,

4-(1H-indol-4-ylamino)-5-{5-[(prop-2-yn-1-ylamino)methyl]-1-benzothien-2-yl}nicotinonitrile,

5-{5-[(butylamino)methyl]-1-benzothien-2-yl}-4-(1H-indol-4-ylamino) nicotinonitrile,

5-(5-{[(2-hydroxyethyl)amino]methyl}-1-benzothien-2-O-4-(1H-indol-4-yl amino)nicotinonitrile,

5-(5-{[(3-hydroxypropyl)amino]methyl}-1-benzothien-2-yl)-4-(1H-indol-4-yl amino)nicotinonitrile,

4-(1H-indol-4-ylamino)-5-(5-{[(3-methoxypropyl)amino]methyl}-1-benzothien-2-yl)nicotinonitrile,

5-(5-{[(4-hydroxybutyl)amino]methyl}-1-benzothien-2-yl)-4-(1H-indol-4-ylamino)nicotinonitrile,

5-{5-[(cyclopropylamino)methyl]-1-benzothien-2-yl}-4-(1H-indol-4-ylamino) nicotinonitrile,

5-(5-{[(cyclopropylmethyl)amino]methyl}-1-benzothien-2-yl)-4-(1H-indol-4-ylamino)nicotinonitrile,

4-(1H-indol-4-ylamino)-5-[5-(pyrrolidin-1-ylmethyl)-1-benzothien-2-yl]nicotinonitrile,

4-(1H-indol-4-ylamino)-5-[5-(morpholin-4-ylmethyl)-1-benzothien-2-yl]nicotinonitrile,

4-(1H-indol-4-ylamino)-5-(5-{[(2-morpholin-4-ylethyl)amino]methyl}-1-benzothien-2-yl)nicotinonitrile,

4-(1H-indol-4-ylamino)-5-[5-(piperidin-1-ylmethyl)-1-benzothien-2-yl]nicotinonitrile,

5-(5-{[4-(hydroxymethyl)piperidin-1-yl]methyl}-1-benzothien-2-yl)-4-(1H-indol-4-ylamino)nicotinonitrile,

5-[5-(hydroxymethyl)-1-benzothien-2-yl]-4-(1H-indol-4-ylamino) nicotinonitrile,

5-{5-[(benzylamino)methyl]-1-benzothien-2-yl}-4-(1H-indol-4-ylamino) nicotinonitrile,

4-(1H-indol-4-ylamino)-5-(5-{[(2-phenylethyl)amino]methyl}-1-benzothien-2-yl)nicotinonitrile,

4-(1H-indol-4-ylamino)-5-(5-{[(pyridin-2-ylmethyl)amino]methyl}-1-benzothien-2-yl)nicotinonitrile,

4-(1H-indol-4-ylamino)-5-(5-{[(pyridin-3-ylmethyl)amino]methyl}-1-benzothien-2-yl)nicotinonitrile,

4-(1H-indol-4-ylamino)-5-(5-{[(pyridin-4-ylmethyl)amino]methyl}-1-benzothien-2-yl)nicotinonitrile,

5-(3-bromophenyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-(1H-indol-4-ylamino)-5-[4-methoxy-3-(2-morpholin-4-ylethoxy)phenyl]nicotinonitrile,

4-(1H-indol-4-ylamino)-5-{4-methoxy-3-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl}nicotinonitrile,

5-{3-[2-(dimethylamino)ethoxy]-4-methoxyphenyl}-4-(1H-indol-4-ylamino) nicotinonitrile,

5-{3-[2-(4-hydroxypiperidin-1H)ethoxy]-4-methoxyphenyl}-4-(1H-indol-4-ylamino)nicotinonitrile,

5-[3-(2-chloroethoxy)-4-methoxyphenyl]-4-(1H-indol-4-ylamino) nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-[3-(2-thienyl)phenyl]nicotinonitrile,

5-(3,4-dimethoxyphenyl)-4-[(4-ethyl-1H-indol-5-yl)amino]nicotinonitrile,

5-[3-{5-formyl-2-thienyl}phenyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(3-{5-[(dimethylamino)methyl]-2-thienyl}phenyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

3′

-[5-cyano-4-(1H-indol-4-ylamino)pyridin-3-yl]-N-(4-hydroxybutyl)biphenyl-4-carboxamide,

3′

-{5-cyano-4-[(4-methyl-1H-indol-5-yl)amino]pyridin-3-yl}-N-(4-hydroxy butyl)biphenyl-4-carboxamide,

4-(1H-indol-4-ylamino)-5-[3-(trifluoromethyl)phenyl]nicotinonitrile,

5-(3-cyanophenyl)-4-(1H-indol-4-ylamino)nicotinonitrile,

3-[5-cyano-4-(1H-indol-4-ylamino)pyridin-3-yl]-N,N-dimethylbenzamide,

3-[5-cyano-4-(1H-indol-4-ylamino)pyridin-3-yl]-N,N-dimethyl benzenesulfonamide,

3-[(5-cyano-4-(1H-indol-4-ylamino)pyridin-3-yl]benzamide,

5-(3-{5-[(dimethylamino)methyl]-2-thienyl}phenyl)-4-(1H-indol-4-yl amino)nicotinonitrile,

2-[5-cyano-4-(1H-indol-4-ylamino)pyridin-3-yl]-N,N-dimethyl benzenesulfonamide,

N-{4-[5-cyano-4-(1H-indol-4-ylamino)pyridin-3-yl]phenyl}methanesulfonamide,

5-(1-benzofuran-2-yl)-4-(1H-indol-4-ylamino)nicotinonitrile,

5-dibenzo[b,d]furan-4-yl-4-(1H-indol-4-ylamino)nicotinonitrile,

4-(1H-indol-4-ylamino)-5-{1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl}nicotinonitrile,

5-(1-benzothien-2-yl)-4-(1H-indol-4-ylamino)nicotinonitrile,

4-(1H-indol-4-ylamino)-5-(4-methoxyphenyl)nicotinonitrile,

4-(1H-indol-4-ylamino)-5-(2-methoxyphenyl)nicotinonitrile,

5-(1H-indol-2-yl)-4-(1H-indol-4-ylamino)nicotinonitrile,

4-[5-cyano-4-(1H-indol-4-ylamino)pyridin-3-yl]-N,N-dimethyl benzenesulfonamide,

3-[5-cyano-4-(1H-indol-4-ylamino)pyridin-3-yl]benzoic acid,

5-[3-(aminomethyl)phenyl]-4-(1H-indol-4-ylamino)nicotinonitrile,

5-(3,4-dimethoxyphenyl)-4-[(2-oxo-2,3-dihydro-1H-indol-4-yl)amino]nicotinonitrile,

4-[5-cyano-4-(1H-indol-4-ylamino)pyridin-3-yl]-N-(2-methoxyethyl)benzamide,

4-(1H-indol-4-ylamino)-5-(4-methoxy-3-{2-[(3-phenylpropyl)amino]ethoxy}phenyl)nicotinonitrile,

5-[4-(2-chloroethoxy)phenyl]-4-(1H-indol-4-ylamino)nicotinonitrile,

5-[3-(5-formyl-2-thienyl)phenyl]-4-(1H-indol-4-ylamino)nicotinonitrile,

4-(1H-indol-4-ylamino)-5-[(4-(2-morpholin-4-ylethoxy)phenyl]nicotinonitrile,

4-(1H-indol-4-ylamino)-5-{4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl}nicotinonitrile,

5-(3,4-dimethoxyphenyl)-4-[(5-methyl-1H-indol-4-yl]-amino)nicotinonitrile,

5-(2,4-dimethoxyphenyl)-4-(1H-indol-4-ylamino)nicotinonitrile,

4-(1H-indol-4-ylamino)-5-(4-methoxy-3-(2-[([3-(2-oxopyrrolidin-1-yl)propyl]amino}ethoxy)phenyl]nicotinonitrile,

5-[3-(2-{[2-(1H-imidazol-4-yl)ethyl]amino}ethoxy)-4-methoxyphenyl]-4-(1H-indol-4-ylamino)nicotinonitrile,

4-(1H-indol-4-ylamino)-5-(4-methoxy-3-{2-[(3-pyrrolidin-1-ylpropyl)amino]ethoxy}phenyl)nicotinonitrile,

4-(1H-indol-4-ylamino)-5-[4-methoxy-3-(2-{[2-(1-methylpyrrolidin-2-yl)ethyl]amino}ethoxy)phenyl]nicotinonitrile,

5-(4-methoxy-3-{2-[(3-phenylpropyl)amino]ethoxy}phenyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-{4-methoxy-3-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl}-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(3-methoxy-4-{2-[(3-phenylpropyl)amino]ethoxy}phenyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-{4-[2-(dimethylamino)ethoxy]-3-methoxyphenyl}-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(3-bromophenyl)-4-[(2-oxo-2,3-dihydro-1H-indol-4-yl)amino]nicotinonitrile,

4-(1H-indol-4-ylamino)-5-(4-{2-[(3-phenylpropyl)amino]ethoxy}phenyl)nicotinonitrile,

5-[4-(2-chloroethoxy)phenyl]-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(3,4-dimethoxyphenyl)-4-[(2-methyl-1H-indol-4-yl)amino]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl}nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-[4-(2-morpholin-4-ylethoxy)phenyl]nicotinonitrile,

5-(1-benzofuran-3-yl)-4-(1H-indol-4-ylamino)nicotinonitrile,

4-(1H-indol-4-ylamino)-5-(4-methoxy-3-{2-[(2-phenylethyl)amino]ethoxy}phenyl)nicotinonitrile,

4-(1H-indol-4-ylamino)-5-(4-methoxy-3-{2-[(2-pyridin-3-ylethyl)amino]ethoxy}phenyl)nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-(4-{2-[(3-phenylpropyl)amino]ethoxy}phenyl)nicotinonitrile,

6′

-[3-(dimethylamino)propoxy]-4-(1H-indol-4-ylamino)-3,3′

-bipyridine-5-carbonitrile,

6′

-[3-(dimethylamino)propoxy]-4-[(4-methyl-1H-indol-5-yl)amino]-3,3′

-bipyridine-5-carbonitrile,

5-(3-hydroxyphenyl)-4-(1H-indol-4-ylamino)nicotinonitrile,

4-(1H-indol-4-ylamino)-5-[5-(piperazin-1-ylmethyl)-1-benzothien-2-yl]nicotinonitrile,

N-({2-[5-cyano-4-(1H-indol-4-ylamino)pyridin-3-yl]-1-benzothien-5-yl}methyl)-b-alaninamide,

4-(1H-indol-4-ylamino)-6′

-[(2-morpholin-4-ylethyl)amino]-3,3′

-bipyridine-5-carbonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-6′

-[(2-morpholin-4-ylethyl)amino-1-3,3′

-bipyridine-5-carbonitrile,

5-{2-chloro-4-[2-(dimethylamino)ethoxy]phenyl}-4-[(4-methy-1H-indol-5-yl)amino]nicotinonitrile,

4-(1H-indol-4-ylamino)-5-(4-methoxy-3-{2-[(3-morpholin-4-ylpropyl)amino]ethoxy}phenyl)nicotinonitrile,

5-[3-(2-{[3-(1H-imidazol-1-yl)propyl]amino}ethoxy)-4-methoxyphenyl]-4-(1H-indol-4-ylamino)nicotinonitrile,

5-(3-{[(2S)-2-amino-3-phenylpropyl]oxy}phenyl)-4-(1H-indol-4-ylamino) nicotinonitrile,

5-{5-[(benzylamino)methyl]-1-benzothien-2-yl}-4-[(4-methyl-1H-indol-5-yl) amino]nicotinonitrile,

5-{4-[2-(4-butylpiperazin-1-yl)ethoxy]phenyl}-4-[(4-methyl-1H-indol-5-yl) amino]nicotinonitrile,

5-[5-(1,3-dioxan-2-yl)-1-benzofuran-2-yl]-4-(1H-indol-4-ylamino) nicotinonitrile,

5-[5-(1,3-dioxan-2-yl)-1-benzofuran-2-yl]-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(2-chloro-4-methoxyphenyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-[4-(2-chloroethoxy)-3-methoxyphenyl]-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(4-hydroxyphenyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(2-chloro-6-methoxyphenyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-[3-methoxy-4-(2-pipendin-1-ylethoxy)phenyl]-4-[(4-methyl-1H-indol-5-yl) amino]nicotinonitrile,

5-{3-methoxy-4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl}-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-[3-methoxy-4-(2-morpholin-4-ylethoxy)phenyl]-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(2,3-dichlorophenyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(4-bromo-2-fluorophenyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-{5-[(dimethylamino)methyl]-1-benzofuran-2-yl}-4-[(4-methyl-1H-indol-5-yl) amino]nicotinonitrile,

5-(5-{[(2-hydroxyethyl)amino]methyl}-1-benzofuran-2-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(5-{[(3-hydroxypropyl)amino]methyl}-1-benzofuran-2-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(5-{[(2,3-dihydroxypropyl)amino]methyl}-1-benzofuran-2-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(5-{[(2,3-dihydroxypropyl)(methyl)amino]methyl}-1-benzofuran-2-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-{5-[(cyclohexylamino)methyl]-1-benzofuran-2-yl}-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-[5-(morpholin-4-ylmethyl)-1-benzofuran-2-yl]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-[5-(pyrrolidin-1-ylmethyl)-1-benzofuran-2-yl]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-(5-{[(2-pyrrolidin-1-ylethyl) amino]methyl}-1-benzofuran-2-yl)nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-[5-({[(1-methylpiperidin-4-yl)methyl]amino}methyl)-1-benzofuran-2-yl]nicotinonitrile,

5-(5-}[4-(hydroxymethyl)piperidin-1-yl]methyl}-1-benzofuran-2-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{5-[(4-pyrrolidin-1-ylpiperidin-1H) methyl]-1-benzofuran-2-yl}nicotinonitrile,

5-[5-(1,4′

-bipiperidin-t-ylmethyl)-1-benzofuran-2-yl]-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{5-[(4-morpholin-4-ylpiperidin-1-yl) methyl]-1-benzofuran-2-yl}nicotinonitrile,

5-[5-({4-[2-(dimethylamino)ethyl]piperazin-1-yl}-methyl)-1-benzofuran-2-yl]-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{5′

[(4-pyridin-2-ylpiperazin-1-yl)methyl]-1-benzofuran-2-yl}nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-(5-{[(pyridin-2-ylmethyl)amino]methyl}-1-benzofuran-2-yl)nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-(5-{[(pyridin-3-ylmethyl)amino]methyl}-1-benzofuran-2-yl)nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-(5-{[(pyridin-4-ylmethyl)amino]methyl}-1-benzofuran-2-yl)nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-[5-(morpholin-4-ylmethyl)-2-furyl]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-[5-(piperidin-1-ylmethyl)-2-furyl]nicotinonitrile,

5-[5-(1,4′

-bipiperidin-1-ylmethyl)-2-furyl]-4-[(4-methyl-1H-indol-5-yl) amino]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{5-[(4-pyrrolidin-1-ylpiperidin-1-yl) methyl]-2-furyl}nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-[5-[(4-morpholin-4-ylpiperidin-1-yl) methyl]-2-furyl]nicotinonitrile,

5-{5-[(diethylamino)methyl]-2-furyl}-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-{5-[(dibutylamino)methyl]-2-furyl}-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-{5-[(benzylamino)methyl]-2-furyl}-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-(5-{[(3-phenylpropyl)amino]methyl}-2-furyl)nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-[5-(pyrrolidin-1-ylmethyl)-2-furyl]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-[5-(thiomorpholin-4-ylmethyl)-2-furyl]nicotinonitrile,

5-(3,4-dimethoxyphenyl)-4-[(6-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(1-benzofuran-2-yl)-4-[(6-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(4-{2-[(2-hydroxyethyl)amino]ethoxy}phenyl)-4-[(4-methyl-1H-indol-5-yl) amino]nicotinonitrile,

5-(4-{2-[(3-hydroxypropyl)amino]ethoxy}phenyl)-4-[(4-methyl-1H-indol-5-yl) amino]nicotinonitrile,

5-(4-{2-[(2-ethoxyethyl)amino]ethoxy}phenyl)-4-[(4-methyl-1H-indol-5-yl) amino]nicotinonitrile,

5-[4-(2-{[2-(dimethylamino)ethyl]amino}ethoxy)phenyl]-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-[4-(2-pyrrolidin-1-ylethoxy)phenyl]nicotinonitrile,

5-{-4-[2-(benzylamino)ethoxy]phenyl}-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)(amino]-5-(4-{2-[(1-methylpiperidin-4-yl)amino]ethoxy}phenyl)nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-[4-(2-{[(1-methylpiperidin-4-yl)methyl]amino}ethoxy)phenyl]nicotinonitrile,

5-(4-{2-[4-(hydroxymethyl)piperidin-1-yl]ethoxy}phenyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{4-[2-(4-pyrrolidin-1-ylpiperidin-1H) ethoxy]phenyl}nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{4-[2-(4-morpholin-4-ylpiperidin-1-yl) ethoxy]phenyl}nicotinonitrile,

5-{4-[2-(4-ethylpiperazin-1-yl)ethoxy]phenyl}-4-[(4-methyl-1H-indol-5-yl) amino]nicotinonitrile,

5-{4-[2-(4-methyl-1,4-diazepan-1-yl)ethoxy]phenyl}-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(4-{2-[4-(2-hydroxyethyl)piperazin-1-yl]ethoxy}phenyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-[4-(2-{4-[2-(dimethylamino)ethyl]piperazin-1-yl}ethoxy)phenyl]-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-[4-(2-{[3-(1H-imidazol-1-yl)propyl]amino}ethoxy)phenyl]-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{4-[2-(4-pyridin-2-ylpiperazin-1-yl) ethoxy]phenyl}nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{4-[2-(4-pyridin-4-ylpiperazin-1-yl) ethoxy]phenyl}nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-(4-{2-(pyridin-2-ylmethyl)amino]ethoxy}phenyl)nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-(4-{2-(pyridin-3-ylmethyl)amino]ethoxy}phenyl)nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino)-5-(4-{2-(pyridin-4-ylmethyl)amino]ethoxy}phenyl)nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{-4-[2-(4-phenylpiperidin-1-yl)ethoxy]phenyl}nicotinonitrile,

5-(5-{[4-(dimethylamino)piperidin-1-yl]methyl}-2-furyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-{5-[(4-isopropylpiperazin-1-yl)methyl]-2-furyl}-4-[(4-methyl-1H-indol-5-yl) amino]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{5-[2-(4-methylpiperazin-1-yl)ethoxy]-1-benzofuran-2-yl}nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{4-[4-methylpiperazin-1-yl)methyl]phenyl}nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-[4-(pyrrolidin-1-ylmethyl)phenyl]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-[4-(morpholin-4-ylmethyl)phenyl]nicotinonitrile,

5-{4-(dimethylamino)methyl]phenyl}-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-2′

-(morpholin-4-ylmethyl)-3,4′

-bipyridine-5-carbonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{3-[(4-methylpiperazin-1-yl)methyl]phenyl}nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-[3-(pyrrolidin-1-ylmethyl)phenyl]nicotinonitrile,

4-1(4-methyl-1H-indol-5-yl)amino)-5-{3-(morpholin-4-ylmethyl)phenyl}nicotinonitrile,

5-{3-[(dimethylamino)methyl]phenyl}-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(4-{[(2R)-2-amino-3-phenylpropyl]oxy}phenyl)-4-(1H-indol-4-ylamino) nicotinonitrile,

5-{2-fluoro-4-[(4-methylpiperazin-1-yl)methyl]phenyl}-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-[4-(3-chloropropoxy)phenyl]-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-[5-(piperidin-1-ylmethyl)-1-benzofuran-2-yl]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{(5-[(4-methylpiperazin-1-yl)methyl]-1-benzofuran-2-yl}nicotinonitrile,

5-(5-formyl-2-thienyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{5-[(4-methylpiperazin-1-yl)methyl]-2-thienyl}nicotinonitrile,

5-(5-formyl-1-benzofuran-2-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(3-methyl-1-benzofuran-2-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-3,4′

-bipyridine-5-carbonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{5-[(4-methylpiperazin-1-yl)methyl]-2-furyl}nicotinonitrile,

2′

-chloro-4-[(4-methyl-1H-indol-5-yl)amino]-3,4′

-bipyridine-5-carbonitrile,

5-{2-chloro-4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl}-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

2′

-chloro-4-[(4-methyl-1H-indol-5-yl)amino]-3,3′

-bipyridine-5-carbonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{4-[3-(4-methylpiperazin-1-yl)propoxy]phenyl}nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-[4-(3-morpholin-4-ylpropoxy)phenyl]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-[4-(3-piperidin-1-ylpropoxy)phenyl]nicotinonitrile,

5-{4-[3-(dimethylamino)propoxy]phenyl}-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-[3,4-bis(2-methoxyethoxy)phenyl]-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-[3-methoxy-4-(2-methoxyethoxy)phenyl]-4-[(4-methyl-1H-indol-5-yl) amino]nicotinonitrile,

5-[5-(hydroxymethyl)-1-benzofuran-2-yl]-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-[4-(2-methoxyethoxy)phenyl]-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-[3-(2-methoxyethoxy)phenyl]-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(5-formyl-1-benzofuran-2-yl)-4-(1H-indol-5-ylamino)nicotinonitrile,

4-(1H-indol-5-ylamino)-5-{5-[(4-methylpiperazin-1-yl)methyl]-1-benzofuran-2-yl}nicotinonitrile,

5-{5-[(4-cyclopentylpiperazin-1-yl)methyl]-2-furyl}-4-[(4-methyl-1H-indol-5-yl) amino]nicotinonitrile,

5-{5-[(1,1-dioxidothiomorpholin-4-yl)methyl]-2-furyl}-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-[(5-formyl-2-furyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-[4-(4-chlorobutoxy)phenyl]-4-[(4-methyl-1H-indol-5-yl]-amino]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{4-[4-(4-methylpiperazin-1-yl)butoxy]phenyl}nicotinonitrile,

5-[4-(2-chloroethoxy)phenyl]-4-[(6-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(5-formyl-1-benzofuran-2-yl)-4-[(6-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[(6-methyl-1H-indol-5-yl)amino]-5-{4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl}nicotinonitrile,

4-[(6-methyl-1H-indol-5-yl)amino]-5-{5-[(4-methylpiperazin-1-ylmethyl]-1-benzofuran-2-yl}nicotinonitrile,

4-[(7-chloro-4-methyl-1H-indol-5-yl)amino]-5-(3,4-dimethoxyphenyl)nicotinonitrile,

5-[5-(hydroxymethyl)-1-benzofuran-2-yl]-4-[(6-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-{5-[(diethylamino)methyl]-1-benzofuran-2-yl}-4-[(6-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-[3-(4-chlorobutoxy)phenyl]-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{3-[4-(4-methylpiperazin-1-yl)butoxy]phenyl}nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{5-[(4-methylpiperazin-1-ylmethyl]-3-furyl}nicotinonitrile,

4-[(6-methyl-1H-indol-5-yl)amino]-5-[4-(2-piperidin-1-ylethoxy)phenyl]nicotinonitrile,

5-{4-[2-(4-hydroxypiperidin-1-yl)ethoxy]phenyl}-4-[(6-methyl-1H-indol-5-yl) amino]nicotinonitrile,

4-[(6-methyl-1H-indol-5-yl)amino]-5-{4-[2-(4-pyrrolidin-1-ylpiperidin-1-yl)ethoxy]phenyl}nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-6′

-morpholin-4-yl-3,3′

-bipyridine-5-carbonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-6′

-piperidin-1-yl-3,3′

-bipyridine-5-carbonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-pyrimidin-5-ylnicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-(2-piperidin-1-ylpyrimidin-5-yl) nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-(2-morpholin-4-ylpyrimidin-5-yl) nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-(2-pyrrolidin-1-ylpyrimidin-5-yl) nicotinonitrile,

5-[2-(dimethylamino)pyrimidin-5-yl]-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(1-benzothien-2-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-[4-(2-chloroethoxy)phenyl]-4-(1H-indol-5-ylamino)nicotinonitrile,

5-(5-formyl-3-thienyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(4-formyl-2-furyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{5-[(4-methylpiperazin-1-yl)methyl]-3-thienyl}nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-3,3′

-bipyridine-5-carbonitrile,

4-(1H-indol-5-ylamino)-5-{4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl}nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{5-[(4-methylpiperazin-1-yl)methyl]-1-benzothien-2-yl}nicotinonitrile,

1-butyl-3-(4-{5-cyano-4-[(4-methyl-1H-indol-5-yl)amino]pyridin-3-yl}phenyl)urea,

methyl (4-{5-cyano-[4-[(4-methyl-1H-indol-5-yl)amino]pyridin-3-yl}phenyl)carbamate,

benzyl (4-{5-cyano-4-[(4-methyl-1H-indol-5-yl)amino]pyridin-3-yl}-2-fluorophenyl)carbamate,

4-methoxybenzyl (4-{5-cyano-4-[(4-methyl-1H-indol-5-yl)amino]pyridin-3-yl}-2-fluorophenyl)carbamate,

4-[(7-chloro-4-methyl-1H-indol-5-yl)amino]-5-{5-[(4-methylpiperazin-1-yl) methyl]-1-benzofuran-2-yl}nicotinonitrile,

5-(3,4-dimethoxyphenyl)-4-[(4-methyl-1H-indol-7-yl)amino]nicotinonitrile,

5-(1-benzofuran-2-yl)-4-[(7-chloro-4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[(7-chloro-4-methyl-1H-indol-5-yl)amino]-5-(5-formyl-1-benzofuran-2-yl) nicotinonitrile,

5-[4-(2-chloroethoxy)phenyl]-4-[(7-chloro-4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[(7-chloro-4-methyl-1H-indol-5-yl)amino]-5-{-4-[2-(dimethylamino)ethoxy]phenyl}nicotinonitrile,

4-[(7-chloro-4-methyl-1H-indol-5-yl)amino]-5-{4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl}nicotinonitrile,

tert-butyl 4-[(2-{5-cyano-4-[(4-methyl-1H-indol-5-yl)amino]pyridin-3-yl}-1-benzofuran-5-yl)methyl]piperazine-1-carboxylate,

5-(2-formyl-1-methyl-1H-imidazol-5-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[4-methyl-1H-indol-5-yl)amino]-5-(5-{[4-(methylsulfonyl)piperazin-1-yl]methyl}-1-benzofuran-2-yl)nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{1-methyl-2-[(4-methylpiperazin-1-yl)methyl]-1H-imidazol-5-yl}nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-[5-(piperazin-1-ylmethyl)-1-benzofuran-2-yl]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-(1,3-thiazol-2-yl)nicotinonitrile,

5-(1-methyl-1H-imidazol-2-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-(1,3-thiazol-4-yl)nicotinonitrile,

5-(3,4-dimethoxyphenyl)-4-(1H-indol-7-ylamino)nicotinonitrile,

5-(3,4-dimethoxyphenyl)-4-[(4-methoxy-1H-indol-5-yl)amino]nicotinonitrile,

5-(3,4-dimethoxyphenyl)-4-[(4-fluoro-1H-indol-5-yl)amino]nicotinonitrile,

4-[(7-chloro-4-methyl-1H-indol-5-yl)amino]-5-[5-(piperazin-1-ylmethyl)-1-benzofuran-2-yl]nicotinonitrile,

tert-butyl 4-[(2-{4-[(7-chloro-4-methyl-1H-indol-5-yl)amino]-5-cyanopyridin-3-yl}-1-benzofuran-5-yl)methyl]piperazine-1-carboxylate,

5-(3,4-dimethoxyphenyl)-4-[(2,4-dimethyl-1H-indol-5-yl]-amino]nicotinonitrile,

5-{2-(dimethylamino)methyl]phenyl}-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(5-formyl-2-methoxyphenyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-{2-methoxy-5-[(4-methylpiperazin-1-yl)methyl]phenyl}-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-{5-[(4-ethylpiperazin-1-yl)methyl]-1-benzofuran-2-yl}-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{5-[(4-methyl-4-oxidopiperazin-1-yl)methyl]-1-benzofuran-2-yl}nicotinonitrile,

5-(3,4-dimethoxyphenyl)-4-[(1,4-dimethyl-1H-indol-5-yl)amino]nicotinonitrile,

3-{5-cyano-4-[(4-methyl-1H-indol-5-yl)amino]pyridin-3-yl}benzoic acid,

5-(2-methoxyphenyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(3-methoxyphenyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(4-methoxyphenyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-phenylnicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-(2-thienyl)nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-(3-thienyl)nicotinonitrile,

5-(3-furyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

H-imidazol-5-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4′

-[(4-methyl-1H-indol-5-yl)amino]-2,3′

-bipyridine-5′

-carbonitrile,

1-(4-{5-cyano-4-[(4-methyl-1H-indol-5-yl)amino]pyridin-3-yl}phenyl)-3-cyclopropylurea,

1-(4-{5-cyano-4-[(4-methyl-1H-indol-5-yl)amino]pyridin-3-yl}phenyl)-3-methylurea,

3-(4-[5-cyano-4-[(4-methyl-1H-indol-5-yl)amino]pyridin-3-yl}phenyl)-1,1-dimethylurea,

N-(4-{5-cyano-4-[(4-methyl-1H-indol-5-yl)amino]pyridin-3-yl)phenyl) morpholine-4-carboxamide,

4-[(4-methyl-1H-indol-5-yl)amino]-5-(4-nitrophenyl)nicotinonitrile,

5-(4-aminophenyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(3-aminophenyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(2-aminophenyl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-[4-(dimethylamino)phenyl]-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-[3-(dimethylamino)phenyl]-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

N-(4-{5-cyano-4-[(4-methyl-1H-indol-5-yl)amino]pyridin-3-yl}phenyl)acetamide,

N-(2-{5-cyano-4-[(4-methyl-1H-indol-5-yl)amino]pyridin-3-yl}phenyl)acetamide,

N-(3-{5-cyano-4-[(4-methyl-1H-indol-5-yl)amino]pyridin-3-yl}phenyl)acetamide,

N-(4-{5-cyano-4-[(4-methyl-1H-indol-5-yl)amino]pyridin-3-yl}phenyl)-2-methylpropanamide,

4-{5-cyano-4-[(4-methyl-1H-indol-5-yl)amino]pyridin-3-yl}-N-methyl benzamide,

4-[(4-methyl-1H-indol-5-yl)amino]-5-(1-naphthyl)nicotinonitrile,

4-[4-methyl-1H-indol-5-yl)amino]-5-(2-naphthyl)nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-(1-methyl-1H-pyrazol-5-yl)nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-(1H-pyrazol-4-yl)nicotinonitrile,

5-(1-benzothiophen-3-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

H-indol-2-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(1H-indol-5-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

5-(1H-indol-6-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-quinolin-3-ylnicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-quinolin-8-ylnicotinonitrile,

5-(1-benzofuran-5-yl)-4-[(4-methyl-1H-indol-5-yl)amino]nicotinonitrile,

4-(4-methyl-1H-indol-5-ylamino)-5-(quinolin-5-yl)nicotinonitrile,

5-(dibenzo[b,d]thiophen-3-yl)-4-(4-methyl-1H-indol-5-ylamino)nicotinonitrile,

5-(benzo[b]thiophen-5-yl)-4-(4-methyl-1H-indol-5-ylamino)nicotinonitrile,

5-(1H-indol-4-yl)-4-(4-methyl-1H-indol-5-ylamino)nicotinonitrile,

4-[(2,4-dimethyl-1H-indol-5-yl)amino]-5-{5-[(4-methylpiperazin-1-yl)methyl]-1-benzofuran-2-yl}nicotinonitrile,

4-4(2,4-dimethyl-1H-indol-5-yl)amino-1-5-[5-(piperazin-1-ylmethyl)-1-benzofuran-2-yl]nicotinonitrile,

4-[4-methyl-1H-indol-5-yl)amino]-5-[6-[(4-methylpiperazin-1-yl)methyl]-1-benzofuran-2-yl}nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-[6-(piperazin-1-ylmethyl)-1-benzofuran-2-yl]nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl)amino]-5-{4-(piperazin-1-yl)methyl]phenyl}nicotinonitrile,

4-[(2,4-dimethyl-1H-indol-5-yl)amino]-5-{4-[(4-methylpiperazin-1-yl)methyl]phenyl}nicotinonitrile,

4-(2,4-dimethyl-1H-indol-5-ylamino)-5-{3-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl}nicotinonitrile,

5-{4-[2-(dimethylamino)ethoxy]-3-methoxyphenyl}-4-[(2,4-dimethyl-1H-indol-5-yl)amino]nicotinonitrile,

4-[(2,4-dimethyl-1H-indol-5yl)amino]-5-{4-[2-(4-methylpiperazin-1-yl)ethoxy]phenyl}nicotinonitrile,

4-[(4-methyl-1H-indol-5-yl]-amino]-5-{4-[2-(piperazin-1-yl]ethoxy]phenyl}nicotinonitrile,

4-(4-methyl-1H-indol-5-ylamino)-2′

-((4-methylpiperazin-1-yl)methyl)-3,4′

-bipyridine-5-carbonitrile,

4-(4-methyl-1H-indol-5-ylamino)-2′

-((piperazin-1-yl)methyl)-3,4′

-bipyridine-5-carbonitrile,

4′

-(4-methyl-1H-indol-5-ylamino)-5-((4-methylpiperazin-1-yl)methyl)-2,3′

-bipyridine-5-carbonitrile,

4′

-(4-methyl-1H-indol-5-ylamino)-5-(morpholinomethyl)-2,3′

-bipyridine-5′

-carbonitrile,

4′

-(4-methyl-1H-indol-5-ylamino)-5-((4(piperazin-1-yl)methyl)-2,3′

-bipyridine-5-carbonitrile,

4′

-(4-methyl-1H-indol-5-ylamino)-6-((4-methylpiperazin-1-yl)methyl)-2,3′

-bipyridine-5′

-carbonitrile,

4′

-(4-methyl-1H-indol-5-ylamino)-6-(morpholinomethyl)-2,3′

-bipyridine-5-carbonitrile,

4′

-(4-methyl-1H-indol-5-ylamino)-6-((piperazin-1-yl)methyl)-2,3′

-bipyridine-5′

-carbonitrile,

4′

-(4-methyl-1H-indol-5-ylamino)-4-(morpholinomethyl)-2,3′

-bipyridine-5-carbonitrile,

4′

-(4-methyl-1H-indol-5-ylamino)-4-((4-methylpiperazin-1-yl)methyl)-2,3′

-bipyridine-5-carbonitrile,

4′

-(4-methyl-1H-indol-5-ylamino)-4-((piperazin-1-ylmethyl)-2,3′

-bipyridine-5′

-carbonitrile,

4-(4-methyl-1H-indol-5-ylamino)-5-4(4-methylpiperazin-1-yl)methyl)-3,3′

-bipyridine-5-carbonitrile,

4-(4-methyl-1H-indol-5-ylamino)-5′

-((4(piperazin-1-yl)methyl)-3,3′

-bipyridine-5-carbonitrile,

4-(4-methyl-1H-indol-5-ylamino)-5-(morpholinomethyl)-3,3′

-bipyridine-5-carbonitrile,

4-(4-methyl-1H-indol-5-ylamino)-6′

-((4-methylpiperazin-1-yl)methyl)-3,3′

-bipyridine-5-carbonitrile.

4-(4-methyl-1H-indol-5-ylamino)-6′

-((piperazin-1-yl)methyl)-3,3′

-bipyridine-5-carbonitrile,

4-(4-methyl-1H-indol-5-ylamino)-6′

-(morpholinomethyl)-3,3′

-bipyridine-5-carbonitrile,

4-(4-methyl-1H-indol-5-ylamino)-5-(3-(piperazin-1-ylmethyl)phenyl)nicotinonitrile,

4-(4-methyl-1H-indol-5-ylamino)-5-(4-(piperazin-1-ylmethyl)phenyl)nicotinonitrile, and

5-(3,4-dimethoxyphenyl)-4-(1H-indol-5-ylamino)nicotinonitrile 1-oxide.

18. The compound of any one of claim 1, wherein the compound is in the form of an enantiomer.

19. A pharmaceutical composition comprising the compound of claim 1 and a pharmaceutically acceptable carrier or excipient.

20. The compound of claim 1 or 2 or a pharmaceutically acceptable salt, hydrate, or ester thereof, wherein X is NH or NCH₃;

R¹ is an indolyl group optionally substituted with 1-4 groups selected from halogen, —

O—

Y—

R⁵, —

NR⁶—

Y—

⁷, a C_1-10 alkyl group and a C_1-10 haloalkyl group; and

R² is a C_6-14 aryl group or a 5-14 membered heteroaryl group selected from furyl, thienyl, benzothienyl, benzofuranyl, pyrazolyl, pyridyl, indolyl, quinolinyl, pyrimidinyl, imidazolyl, thiazolyl isothiazolyl, oxazolyl, isoxazolyl, dibenzothienyl, dibenzofuranyl, benzodioxolyl and benzodioxanyl, wherein each group optionally is substituted with 1-4 groups independently selected from —

Y—

R⁴ or —

O—

Y—

R⁴.