IP Library Granted Patent US 7,312,341
Granted Patent B2
US 7,312,341 · App. 10/658,121 · Granted Dec 25, 2007

6-aryl-imidazo[1,2-a] pyrazin-8-ylamines, method of making, and method of use thereof

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Quick Facts
Patent No.
US 7,312,341
App. No.
10/658,121
Granted
Dec 25, 2007
Kind
B2
Abstract

A novel composition comprises a compound of Formula 1 the pharmaceutically acceptable salts, hydrates, solvates, crystal forms, diastereomers, prodrugs, or mixtures thereof. The composition is of particular utility in the treatment of kinase-implicated disorders.

Claims (129)

1. A compound having Formula 1:

a pharmaceutically acceptable salt, or mixture thereof, wherein

R 1 is hydrogen; cyclo-(C 3 –C 6 alkyl)-methyl; straight or branched chain C 1 –C 7 alkyl, in which the branched alkyl chains are allowed to also form a 3–7 member heteroalkyl or alkyl ring; sulfonamide; C 1 –C 6 alkoxy; (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy; (C 1 –C 6 )-alkyl-oxy -(C 1 –C 6 )alkyl; mono- or di(C 1 –C 6 alkyl)amino, mono- or di(C 1 –C 6 alkyl)amino(C 1 –C 6 alkyl); or phenyl which may be unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, sulfonamide, halogen, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, —S(C 1 –C 6 alkyl ), mono- or di (C 1 –C 6 alkyl)amino, mono-or di(C 1 –C 6 alkyl)amino(C 1 –C 6 alkyl), or ester;

R 2 is straight or branched chain C 1 –C 7 alkyl, in which the branched alkyl chains are allowed to also form a 3–7 member heteroalkyl or alkyl ring; cyclo-(C 3 –C 6 alkyl)-methyl; C 1 –C 6 alkoxy; (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy; (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 ) alkyl; phenyl or heteroaryl which may be unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkyl, mono- or di(C 1 –C 6 alkyl)amino, amino(C 1 –C 6 alkyl), —S(C 1 –C 6 alkyl ), or carboxylic acid or ester; phenyoxy phenyl where each phenyl may be independently unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, sulfonamide, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 ) alkyl, mono- or di(C 1 –C 6 alkyl)amino, amino(C 1 –C 6 alkyl), —S(C 1 –C 6 alkyl ), or carboxylic acid or ester; phenyl or heteroaryl piperazine where the phenyl or heteroaryl ring may be independently unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, sulfonamide, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 ) alkyl, mono- or di(C 1 –C 6 alkyl)amino, mono- or di(C 1 –C 6 alkyl)amino(C 1 –C 6 alkyl), —S (C 1 –C 6 alkyl ), or carboxylic acid or ester; and wherein R 2 can form a 3–7 heteroalkyl or alkyl with R 10 , R 11 , or R 12 ;

R 3 is hydrogen; carboxylic acid or ester; straight or branched chain C 1 –C 6 alkyl, in which the branched alkyl chains are allowed to also form a 3–7 member heteroalkyl or alkyl ring; phenyl or heteroaryl which may be unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy, (C 1 –C 6 )-alkyl-oxy -(C 1 –C 6 )alkyl, mono- or di(C 1 –C 6 alkyl)amino, amino(C 1 –C 6 alkyl), —S(C 1 –C 6 alkyl), or carboxylic acid or ester; phenyoxy phenyl where each phenyl may be independently unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, sulfonamide, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 ) alkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkyl, mono- or di(C 1 –C 6 alkyl) amino, amino(C 1 –C 6 alkyl), —S(C 1 –C 6 alkyl ), or carboxylic acid or ester; phenyl or heteroaryl piperazine where the phenyl or heteroaryl ring may be independently unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, sulfonamide, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 ) alkyl, mono- or di(C 1 –C 6 alkyl)amino, mono- or di(C 1 –C 6 alkyl)amino(C 1 –C 6 alkyl), —S(C 1 –C 6 alkyl ), or carboxylic acid or ester;

R 4 is hydrogen; straight or branched chain C 1 –C 6 alkyl, in which the branched alkyl chains are allowed to also form a 3–7 member heteroalkyl or alkyl ring; (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkyl; phenyl or heteroaryl which may be unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 ) alkyl, mono- or di(C 1 –C 6 alkyl)amino, amino(C 1 –C 6 alkyl), -S(C 1 –C 6 alkyl), or carboxylic acid or ester; phenyoxy phenyl where each phenyl may be independently unsubstituted, mono-,di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, sulfonamide, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 ) alkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkyl, mono- or di(C 1 –C 6 alkyl)amino, amino (C 1 –C 6 alkyl), —S(C 1 –C 6 alkyl), or carboxylic acid or ester; phenyl or heteroaryl piperazine where the phenyl or heteroaryl ring may be independently unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, sulfonamide, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 ) alkyl, mono- or di(C 1 –C 6 alkyl)amino, mono- or di(C 1 –C 6 alkyl)amino (C 1 –C 6 alkyl), —S(C 1 –C 6 alkyl), or carboxylic acid or ester; or form a 3–7 member heteroalkyl or alkyl with Z 1 or R 1 ;

X is CH

Z 1 is

wherein

each occurrence of R 5 and R 6 is independently hydrogen straight or branched chain C 1 –C 6 alkyl, sulfonamide, or halogen;

m is 0, 1, or 2; and

R 7 is hydrogen; straight or branched chain C 1 –C 6 alkyl; phenyl which may be unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkyl, mono- or di(C 1 –C 6 alkyl)amino, amino(C 1 –C 6 alkyl) , -S(C 1 –C 6 alkyl), or carboxylic acid or ester; or heteroaryl which may be unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy -(C 1 –C 6 )alkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkyl, mono- or di(C 1 –C 6 alkyl)amino, amino(C 1 –C 6 alkyl) , —S(C 1 –C 6 alkyl ), or carboxylic acid or ester; and

Z 2 is

wherein

each occurrence of R 8 and R 9 is independently straight or branched chain C 1 –C 6 alkyl, sulfonamide, or halogen;

n is 0, 1, or 2; and

R 10 –R 13 are each independently hydrogen; straight or branched chain C 1 –C 6 alkyl; phenyl which may be unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, (C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy, (C 1 –C 6 )-alkyl -oxy-C 1 –C 6 )alkyl, mono- or di(C 1 –C 6 alkyl)amino, amino(C 1 –C 6 alkyl), —S (C 1 –C 6 alkyl ), or carboxylic acid or ester; or heteroaryl which may be unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 ) alkyl, mono- or di(C 1 –C 6 alkyl)amino, amino(C 1 –C 6 alkyl) , —S(C 1 –C 6 alkyl), or carboxylic acid or ester;

and wherein, when R 3 is hydrogen and R 4 is hydrogen, or when R 3 and R 1 are hydrogen and Z 1 is

wherein m is 0, the combination of Z 2 —R 2 is not hydrogen, hydroxy, halogen, hydroxyamide, amino, hydroxyalkyl, aminoalkylamide, alkylamide, arylamide or alkoxy, or

wherein when R 3 is hydrogen, R 4 and Z 1 , or R 4 and R 1 do not form a morpholino, piperazinyl, or 1,4diazepanyl group when the combination of Z 2 —R 2 is hydrogen, hydroxy, halogen, hydroxyamide, amino, hydroxyalkyl, aminoalkylamide, alkylamide, arylamide or alkoxy.

2. A compound having Formula 2:

a pharmaceutically acceptable salt or mixtures thereof, wherein

R 1 is phenyl which may be unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, sulfonamide, halogen, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, —S(C 1 –C 6 alkyl ), mono- or di(C 1 –C 6 alkyl)amino, mono- or di(C 1 –C 6 alkyl)amino(C 1 –C 6 alkyl), or ester;

R 2 is phenyl or heteroaryl which may be unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 ) alkyl, mono- or di(C 1 –C 6 alkyl)amino, amino(C 1 –C 6 alkyl), -S(C 1 –C 6 alkyl ), or carboxylic acid or ester; phenyoxy phenyl where each phenyl may be independently unsubstituted, mono-,di - or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, sulfonamide, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfiucroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 ) alkoxy, (C 1 –C 6 )-alkyi-oxy-(C 1 –C 6 )alkyl, mono- or di(C 1 –C 6 alkyl)amino, amino (C 1 –C 6 alkyl), —S(C 1 –C 6 alkyl ), or carboxylic acid or ester; phenyl or heteroaryl piperazine where the phenyl or heteroaryl ring may be independently unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, sulfonamide, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 ) alkyl, mono- or di(C 1 –C 6 alkyl)amino, mono- or di(C 1 –C 6 alkyl)amino(C 1 –C 6 alkyl), —S(C 1 –C 6 alkyl), or carboxylic acid or ester; and wherein R 2 can form a 3–7 heteroalkyl or alkyl with R 10 , R 11 , or R 12 ;

R 3 is hydrogen; or carboxylic acid or ester;

R 4 is hydrogen; straight or branched chain C 1 –C 6 alkyl, in which the branched alkyl chains are allowed to also form a 3–7 member heteroalkyl or alkyl ring; or (C 1 –C 6 )-alkyl-oxy -C 1 –C 6 )alkyl;

Xis CH

Z 1 is

wherein

each occurrence of R 5 and R 6 is independently hydrogen straight or branched chain C 1 –C 6 alkyl, sulfonamide, or halogen;

m is 0, 1, or 2; and

Z 2 is

wherein

R 10 —R 13 are each independently hydrogen; straight or branched chain C 1 –C 6 alkyl; phenyl which may be unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, haiogen, C 1 –C 6 alkyl, C 1 –C 6 aikoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy, (C 1 –C 6 ) -alkyl-oxy-C 1 –C 6 )alkyl, mono- or di(C 1 –C 6 alkyl)amino, amino(C 1 –C 6 alkyl), —S (C 1 –C 6 alkyl ), or carboxylic acid or ester; or heteroaryl which may be unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkyl, mono- or di(C 1 –C 6 alkyl)amino, amino(C 1 –C 6 alkyl) , —S(C 1 –C 6 alkyl), or carboxylic acid or ester;

and wherein, when R 3 is hydrogen and R 4 is hydrogen, or when R 3 and R 1 are hydrogen and Z 1 is

wherein m is 0, the combination of Z 2 –R 2 is not hydrogen, hydroxy, halogen, hydroxyamide, amino, hydroxyalkyl, aminoalkylamide, alkylamide, arylamide or alkoxy, or

wherein when R 3 is hydrogen, R 4 and Z 1 , or R 1 and R 1 do not form a morpholino, piperazinyl, or 1 ,4-diazepanyl group when the combination of Z 2 —R 2 is hydrogen, hydroxy, halogen, hydroxyamide, amino, hydroxyalkyl, aminoalkylamide, alkylamide, arylamide or alkoxy.

3. A compound having Formula 3:

a pharmaceutically acceptable salt, or mixtures thereof, wherein

R 1 is hydrogen; cyclo-(C 3 –C 6 alkyl)-methyl; stralght or branched chain C 1 –C 7 alkyl, in which the branched alkyl chains are allowed to also form a 3–7 member heteroalkyl or alkyl ring; sulfonamide; (C 1 –C 6 alkoxy; (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy; (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 ); mono- or di(C 1 –C 6 alkyl)amino, mono- or di(C 1 –C 6 alkyl)amino(C 1 –C 6 alkyl); or phenyl which may be unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, sulfonamide, halogen, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, —S(C 1 –C 6 alkyl ), mono- or di(C 1 –C 6 alkyl) amino, mono-or di(C 1 –C 6 alkyl)amino(C 1 –C 6 alkyl), or ester;

R 2 is straight or branched chain C 1 –C 7 alkyl, in which the branched alkyl chains are allowed to also form a 3–7 member heteroalkyl or alkyl ring; cyclo-(C 3 –C 6 alkyl)-methyl; C 1 –C 6 alkoxy; (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy; (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 ) alkyl; phenyl or heteroar which may be unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 ) alkyl, mono- or di(C 1 –C 6 alkyl)amino, amino(C 1 –C 6 alkyl), —S(C 1 –C 6 alkyl), or carboxylic acid or ester; phenyoxy phenyl where each phenyl may be independently unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, sulfonamide, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, ( 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 ) alkyl, mono- or di(C 1 –C 6 alkyl)amino, amino(C 1 –C 6 alkyl), -S(C 1 –C 6 alkyl ), or carboxylic acid or ester; phenyl or heteroaryl piperazine where the phenyl or heteroaryl ring may be independently unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, ammo, halogen, sulfonamide, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy, (C 1 –C 6 )-alkyl-oxy -(C 1 –C 6 )alkyl, mono- or di(C 1 –C 6 alkyl)amino, mono- or di(C 1 –C 6 alkyl)amino(C 1 –C 6 alkyl), —S (C 1 –C 6 alkyl ), or carboxylic acid or ester; and wherein R 2 can form a 3–7 heteroalkyl or alkyl with R 12 ;

R 3 is hydrogen; carboxylic acid or ester; straight or branched chain C 1 –C 6 alkyl, in which the branched alkyl chains are allowed to also form a 3–7 member heteroalkyl or alkyl ring; phenyl or heteroaryl which may be unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy, (C 1 –C 6 )-alkyl-oxy -(C 1 –C 6 )alkyl, mono- or di(C 1 –C 6 alkyl)amiino, amino(C 1 –C 6 alkyl), —S(C 1 –C 6 alkyl ), or carboxylic acid or ester; phenyoxy phenyl where each phenyl may be independently unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, sulfonamide, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 ) -alkyl-oxy-(C 1 –C 6 )alkyl, mono- or di(C 1 –C 6 alkyl)amino, amino(C 1 –C 6 alkyl), —S(C 1 –C 6 alkyl), or carboxylic acid or ester; phenyl or heteroaryl piperazine where the phenyl or heteroaryl may be independently unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, sulfonamide, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-oxy-(C 1 –C 6 )-alkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 ) alkyl, mono- or di(C 1 –C 6 alkyl)amino, mono- or di(C 1 –C 6 alkyl)amino(C 1 –C 6 alkyl), —S(C 1 –C 6 alkyl), or carboxylic acid or ester;

R 4 is hydrogen; straight or branched chain C 1 –C 6 alkyl, in which the branched alkyl chahins are allowed to also form a 3–7 member heteroalkyl or alkyl ring; (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 ) alkyl; phenyl or heteroaryl which may be unsubstituted, mono-, di- or trisubstituted with one or more fo hydroxy, nitro, cyano, amino, halogen, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy, (C 1 –C 6)-alkyl-oxy-(C 1 –C 6 ) alkyl, mono-or di(C 1 –C 6 )amino, amino(C 1 –C 6 ), —S(C 1 –C 6 alkyl), or carboxylic acid or ester; phenyoxy phenyl where each phenylmay be independently unsubstituted, mono-,di - or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, sulfonamide. C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 ) -alkyl-oxy-(C 1 –C 6 ) alkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkyl, mono- or di(C 1 –C 6 )amino, amino (C 1 –C 6 ), —S(C 1 –C 6 ), or carboxylic acid or ester; phenyl or heteroaryl piperazine where the phenyl or heteroaryl ring may be independently unsubstituted, mono-,di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, sulfonamide, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 C 6 perfluoroalfoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy, (C 1 –C 6 ) alkyl-oxy-(C 1 –C 6 ) alkyl, mono- or di(C 1 –C 6 )amino, mono- or di(C 1 –C 6 )amino(ac 1 –C 6 ), —S (C 1 –C 6 alkyl), or carboxylic acid or ester; or form a 3–7 member heteroalkyl or alkyl with Z 1 or R 1 ;

X is CH

Z 1 is

wherein

each occurrence of R 5 and R 6 is independently hydrogen straight or branched chain C 1 –C 6 alkyl, sulfonamide, or halogen;

m is 0, 1, or 2; and

R 7 hydrohen; straight or branched chain C 1 –C 6 alkyl; phenyl which may be unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitrom, cyano, amono, halogen, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 ) alkyl, mono- or di(C 1 –C 6 )amino, amino(C 1 –C 6 ) , —S(C 1 –C 6 alkyl), or carbocylic acid or ester; or heteroaryl which may be unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 ) -alkyl-oxy -(C 1 –C 6 )alkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkyl, mono- or di(C 1 –C 6 alkyl)amino, amino(C 1 –C 6 ) , —S(C 1 –C 6 ), or carboxylic acid or ester; and

wherein R 12 and R 13 are each independently hydrogen; straight or btanched chain C 1 –C 6 alkyl; phenyl which may be unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, niteo, cyano, amino, halogen, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, (C 1 –C 6 )-alkyl-oxy -(C 1 –C 6 )alkoxy, mono- or di(C 1 –C 6 alkyl)amino, amino(C 1 –c 6 alkyl), —S(C 1 –C 6 ), or carboxylic acid or ester; or heteroaryl which may be unsubstituted, mono-, di- or trisubstituted with one or more of hydroxy, nitro, cyano, amino, halogen, C 1 –C 6 alkyl, C 1 –C 6 alkoxy, C 1 –C 6 perfluoroalkyl, C 1 –C 6 perfluoroalkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 )alkoxy, (C 1 –C 6 )-alkyl-oxy-(C 1 –C 6 ) alkyl, mono- or di(C 1 –C 6 alkyl)amino, amino(C 1 –C 6 ) , —S(C 1 –C 6 ), or carboxylic acid or ester.

4. A compound as in claim 1 or a pharmaceutically acceptable saly thereof, wherein the compound is 1-(4-{8-[(3-Chloro-benyl)-methyl-amino]-imidao[1,2-a]pyrain-6yl}-phenyl)-3-(2-chloro-phenyl)-urea.

5. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(4-{8-[(3-Chloro-benzyl)-methyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-(3-chloro-phenyl)-urea.

6. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(4-{8-[(3-Chloro-benzyl)-methyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-(2-methoxy-phenyl)-urea.

7. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(4-{8-[(3-Chloro-benzyl)-methyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-(4-chloro-phenyl)-urea.

8. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[(4-Chloro-benzyl)-methyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-(4-chloro-phenyl)-urea.

9. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(4-{8-[(3-Chloro-benzyl)-methyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-(4-trifluoromethyl-phenyl)-urea.

10. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(4-{8-[(3-Chloro-benzyl)-methyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-(4-trifluoromethoxy-phenyl)-urea.

11. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[(4-Chloro-benzyl)-methyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-(2-methylsulfanyl-phenyl)-urea.

12. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[Methyl-(4-methyl-benzyl)-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-(2-methylsulfanyl-phenyl)-urea.

13. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(4-Chloro-phenyl)-3-(3-{8-[methyl-(4-methyl-benzyl)-amino]-iniidazo[1,2-a]pyrazin-6-yl}-phenyl)-urea.

14. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[Methyl-(4-methyl-benzyl)-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-o-tolyl-urea.

15. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(4-Chloro-phenyl)-3-{3-[8-(3 ,4-dihydro- 1 H-isoquinolin-2-yl)-imidazo[1,2-a]pyrazin-6-yl]-phenyl}-urea.

16. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-{3-[8-(3 ,4-Dihydro- 1 H-isoquinolin-2-yl)-imidazo[1 ,2-a]pyrazin-6-yl]-phenyl}-3-(2-methylsulfanyl-phenyl)-urea.

17. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-{3-[8-(3 ,4-Dihydro- 1H-isoquinolin-2-yl)-imidazo[1 ,2-a]pyrazin-6-yl]-pheny}-3-o-tolyl-urea.

18. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-{3-[8-(3 ,4-Dihydro- 1 H-isoquinolin-2-yl)-imidazo[1 ,2-a]pyrazin -6-yl]-phenyl}-3-(2-methoxy-phenyl)-urea.

19. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 8-[(4-Chloro-benzyl)-methyl-amino]-6-{3-[3-(2-trifluoromethyl-phenyl)-ureido]-phenyl }-imidazo [1 ,2-a]pyrazine-3-carboxylic acid ethyl ester.

20. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 8-[(4-Chloro-benzyl)-methyl-amino]-6-[3-(3-o-tolyl-ureido)-phenyl]-imidazo[1,2-a]pyrazine-3-carboxylic acid ethyl ester.

21. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 8-[(4-Chloro-benzyl)-methyl-amino]-6-{3-[3-(4-chloro-phenyl)-ureido]-phenyl }-imidazo[1 ,2-a]pyrazine-3-carboxylic acid ethyl ester.

22. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-Chloro-4-fluoro-phenyl)-3-(3-{8-[methyl-(4-methyl-benzyl)-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl)-urea.

23. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[(4-Chloro-benzyl)-methyl-amino]-imidazo [1 ,2-a]pyrazin-6-yl}-phenyl) -3-(3-chloro-4-fluoro-phenyl)-urea.

24. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[(4-Chloro-benzyl)-methyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-benzyl) -3-(4-chloro-phenyl)-urea.

25. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[(4-Chloro-benzyl)-methyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-benzyl) -3-(3-chloro-4-fluoro-phenyl)-urea.

26. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[(4-Chloro-benzyl)-ethyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-tolyl-urea.

27. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[(4-Chloro-benzyl)-ethyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-(4-chloro-phenyl)-urea.

28. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[(4-Chloro-benzyl)-ethyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-(3-chloro-4-fluoro-phenyl)-urea.

29. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[(4-Chloro-benzyl)-propyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-o-tolyl-urea.

30. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[(4-Chloro-benzyl)-propyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-(3-chloro-4-fluoro-phenyl)-urea.

31. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[Butyl-(4-chloro-benzyl)-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-tolyl-urea.

32. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[(4-Chloro-benzyl)-propyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-(4-chloro-phenyl)-urea.

33. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[(4-Chloro-benzyl)-propyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-(3-trifluoromethyl-phenyl)-urea.

34. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[Butyl-(4-chloro-benzyl)-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-(4-chloro-phenyl)-urea.

35. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[Butyl-(4-chloro-benzyl)-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-(3-trifluoromethyl-phenyl)-urea.

36. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[Butyl-(4-chloro-benzyl)-aminol]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-(3-chloro-4-fluoro-phenyl)-urea.

37. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[(4-Chloro-benzyl)-methyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-(3-trifluoromethyl-phenyl)-urea.

38. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[(4-Chloro-benzyl)-methyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-o-tolyl-urea.

39. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-{3-[8-(Benzyl-methyl-amino)-imidazo[1 ,2-a]pyrazin-6-yl]-phenyl }-3-(4-chloro-phenyl) -urea.

40. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[(4-Chloro-benzyl)-methyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-(4-trifluoromethoxy-phenyl)-urea.

41. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[(4-Chloro-benzyl)-methyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-(5-fluoro-2-trifluoromethyl-phenyl)-urea.

42. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[(4-Chloro-benzyl)-methyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-(3 ,5-dichloro-phenyl)-urea.

43. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[(4-Chloro-benzyl)-methyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-(3,4-dichloro-phenyl)-urea.

44. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[(2-Chloro-benzyl)-methyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -3-(4-chloro-phenyl)-urea.

45. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(4-Chloro-benzyl)-3-(3-{8-[(4-chloro-benzyl)-methyl-amino]-imidazo[1,2-a]pyrazin-6-yl}-phenyl)-urea.

46. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[(4-Chloro-benzyl)-(2-methoxy-ethyl)-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyi)-3-(4-chloro-phenyl)-urea.

47. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8[(4-Chloro-benzyl)-(2-methoxy-ethyl)-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl)-3-(3-trifluoromethyl-phenyl)-urea.

48. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8[(4-Chloro-benzyl)-(2-methoxy-ethyl)-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl)-3-(4-chloro-3-fluoro-phenyl)-urea.

49. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[(4-Chloro-benzyl)-(2-methoxy-ethyl)-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl)-3[4-(4-methyl-piperazin-1-ylmethyl)-phenyl]-urea.

50. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is (2-Methoxy-benzyl)-{6-[3-(4-methoxy-benzylamino)-phenyl]-imidazo[1,2-a]pyrazin-8-yl }-amine.

51. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-{4-[8-(2-Methoxy-benzylamino)-imidazo[1 ,2-a]pyrazin-6-yl]-phenyl}-3-phenyl-urea.

52. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(2-Chloro-phenyl)-3-{4[8-(2-methoxy-benzylamino)-imidazo[1 ,2-a]pyrazin-6-yl]-phenyl }-urea.

53. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-{4-[8-(2-Methoxy-benzylamino)-imidazo[1 ,2-a]pyrazin-6-yl]-phenyl }-3-(2-methoxy-phenyl)-urea.

54. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-{4-[8-(2-Methoxy-benzylamino)-imidazo[1 ,2-a]pyrazin-6-yl]-phenyl}-3-(3-methoxy-phenyl)-urea.

55. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is N-(3-{8-[(4-Chloro-benzyl)-methyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -benzenesulfonamide.

56. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is N-(3-{8-[(4-Chloro-benzyl)-methyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -benzamide.

57. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 4-Chloro-N-(3-{8-[(4-chloro-benzyl)-methyl-amino]-imidazo[1 ,2-a]pyrazin -6-yl}-phenyl)-benzamide.

58. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 2-Chloro-N-(3-{8-[(4-chloro-benzyl)-methyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl)-benzamide.

59. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is (4-{8-[(3-Chloro-benzyl)-methyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -piperidin- 1 -yl-methanone.

60. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is (4-{8-[(4-Chloro-benzyl)-methyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl) -piperidin- 1 -yl-methanone.

61. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 4-{6-[4-(Piperidine-1-carbonyl)-phenyl]-imidazo[1 ,2-a]pyrazin-8-ylamino }-benzoic acid ethyl ester.

62. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 4-(6-{3-[3-(4-Chloro-phenyl)-ureido]-phenyl}1 -imidazo[1 ,2-a]pyrazin-8-ylamino) -benzoic acid ethyl ester.

63. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 4-(6-{3-[3-(2-Methylsulfanyl-phenyl)-ureido]-phenyl }-imidazo[1,2-a]pyrazin-8-ylamino)-benzoic acid ethyl ester.

64. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-{8-[(4-Chloro-benzyl)-methyl-amino]-imidazo[1 ,2-a]pyrazin-6-yl}-phenyl)-3-(2-methylsulfanyl-phenyl)-urea.

65. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is {4-[8-(4-Chloro-phenylamino)-imidazo[1 ,2-a]pyrazin-6-yl]-phenyl}-piperidin-1-yl -methanone.

66. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 3-Methoxy-N- {3-[8-(2-methoxy-benzylamino)-imidazo[1 ,2-a]pyrazin-6-yl]-phenyl}-benzamide.

67. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 2-Methoxy-N- {3-[8-(2-methoxy-benzylamino)-irnidazo[1 ,2-a]pyrazin-6-yl]-phenyl}-benzamide.

68. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-Chloro-4-fluoro-phenyl)-3[3-(8-phenylamino-imidazo[1 ,2-a]pyrazin-6-yl) -phenyl]-urea.

69. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(4-Chloro-phenyl)-3-[3-(8-phenylamino-imidazo[1 ,2-a]pyrazin-6-yl)-phenyl]-urea.

70. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-[3-(8-Phenylamino-iniidazo[1 ,2-a]pyrazin-6-yl)-phenyl]-3-(3-trifluoromethyl -phenyl)-urea.

71. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(2-Chloro-5-trifluoromethyl-phenyl)-3[3-(8-phenylamino-imidazo[1,2-a]pyrazin-6-yl)-phenyl]-urea.

72. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(4-Chloro-phenyl)-3-{3-[8-(4-chloro-phenylamino)-imidazo[1 ,2-a]pyrazin-6]-phenyl}-urea.

73. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-{3-[8-(4-Chloro-phenylamino)-imidazo[1 ,2-a]pyrazin-6-yl]-phenyl}-3 -(3-trifluoromethyl-phenyl)-urea.

74. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-Chloro-4-fluoro-phenyl)-3-{3[8-(3-chloro-phenylamino)-imidazo[1,2-a]pyrazin-6-yl]-phenyl}-urea.

75. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(4-Chloro-phenyl)-3-{3[8-(3-chloro-phenylamino)-imidazo[1 ,2-a]pyrazin -6-yl]-phenyl}-urea.

76. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-{3-[8-(3-Chloro-phenylamino)-imidazo[1 ,2-a]pyrazin-6-yl]-phenyl}-3-(3-trifluoromethyl-phenyl)-urea.

77. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(3-Chloro-4-fluoro-phenyl)-3-{3-[8-(2-chloro-phenylamino)-imidazo[1,2-a]pyrazin-6-yl]-phenyl}-urea.

78. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-[3-(8-Phenylamino-imidazo[1 ,2-a]pyrazin-6-yl)-phenyl]-3-(4-trifluoromethyl -phenyl) -urea.

79. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-(2-Methoxy-5-methyl-phenyl)-3-[3-(8-phenylamino-iniidazo[1 ,2-a]pyrazin-6-yl) -phenyl]-urea.

80. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-{3-[8-(3-Chloro-phenylamino)-imidazo[1 ,2-a]pyrazin-6-yl]-phenyl}-3-(2-methoxy-5-methyl-phenyl)-urea.

81. A compound as in claim 1 or a pharmaceutically acceptable salt thereof, wherein the compound is 1-{3-[8-(2-Chloro-phenylamino)-imidazo[1 ,2-a]pyrazin-6-yl]-phenyl}-3-(2-methoxy-5-methyl-phenyl)-urea.

82. A pharmaceutical composition comprising a compound or salt according to claims 1 to 44 , 45 to 78 , or 79 to 81 , combined with at least one pharmaceutically acceptable carrier or excipient.

Assignments (3)
AGREEMENT AND PLAN OF MERGER Recorded Oct 4, 2010
From: CGI PHARMACEUTICALS, INC.
To: GILEAD CONNECTICUT, INC.
Reel/Frame 025084/0218 →
CHANGE OF NAME Recorded Sep 6, 2005
From: CELLULAR GENOMICS INC.
To: CGI PHARMACEUTICALS, INC.
Reel/Frame 016736/0267 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 30, 2003
From: DESIMONE, ROBERT W.; PIPPIN, DOUGLAS A.; DARROW, JAMES W.; MITCHELL, SCOTT A.; CURRIE, KEVIN S.
To: CELLULAR GENOMICS, INC.
Reel/Frame 014092/0227 →