Methods, Compositions, and Uses of Novel FYN Kinase Inhibitors

Abstract

The present invention provides methods for inhibiting Fyn kinase, using 5-3-pyridin-2-amine, 6-3-imidazo[1,2-a] pyrazine, 6-3-imidazo[1,2-b] pyridazine, N-(5-imidazo [2,1-b][1,3,4] thiadiazol-2-yl)-amine, 4-3-1H-pyrazolo[3,4-b] pyridine, and N-(3-imidazo [1,2-b] pyridazin-6-yl) amine compounds and methods of treatment, prevention, inhibition or amelioration of diseases and conditions associated with Fyn kinase using such compounds.

Claims

1. A compound of structural formula (I): ##STR00717## wherein: R1 is selected from the group consisting of H, alkyl, alkenyl, alkylene, alkynyl, aryl, arylalkyl, alkylaryl, arylalkenyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, heterocyclenyl, wherein each of the alkyl, alkenyl, alkylene, alkynyl, alkynylalkyl, aryl, arylalkyl, alkylaryl, arylalkenyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclic moieties can be substituted with one or more moieties which can be the same or different, each moiety being independently selected from the group consisting of acyl, alcohol, alkyl, aryl, aroyl, alkoxy, aryloxy, arylalkyloxy, alkylthio, arylthio, aralkylthio, alkoxycarbonyl, aryloxycarbonyl, aralkoxycarbonyl, alkylsulfonyl, arylsulfonyl, cyano, hydroxyalkyl, amide, amine, thiol, thiophene, pyrrole, furan, alkylsulfate, arylsulfate, alkylphosphate and arylphosphate, and R2 is selected from the group consisting of H, alkyl, alkenyl, alkylene, alkynyl, aryl, arylalkyl, alkylaryl, arylalkenyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, heterocyclenyl, wherein each of the alkyl, alkenyl, alkylene, alkynyl, alkynylalkyl, aryl, arylalkyl, alkylaryl, arylalkenyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclic moieties can be substituted with one or more moieties which can be the same or different, each moiety being independently selected from the group consisting of acyl, alcohol, alkyl, aryl, aroyl, alkoxy, aryloxy, arylalkyloxy, alkylthio, arylthio, aralkylthio, alkoxycarbonyl, aryloxycarbonyl, aralkoxycarbonyl, alkylsulfonyl, arylsulfonyl, cyano, hydroxyalkyl, amide, amine, thiol, thiophene, pyrrole, furan, alkylsulfate, arylsulfate, alkylphosphate and arylphosphate.

2. A method of treating, or slowing progression of, a disease associated with Fyn kinase, said method comprising administering a therapeutically effective amount of at least one compound according to claim 1, or a pharmaceutically acceptable salt or solvate thereof to a patient in need thereof ##STR00718##

3. A compound according to claim 1 selected from the group consisting of 3-[2-amino-5-(3,4-dimethoxyphenyl)-3-pyridyl]phenol, 3-[6-amino-5-[3-(dimethylamino)phenyl]-3-pyridyl]-N-(2-hydroxyethyl)benzamide, 5-(3-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)pyridin-2-amine, 4-[2-amino-5-(4-methylsulfonylphenyl)-3-pyridyl]-2-methoxy-phenol, 4-[2-amino-5-(p-tolyl)-3-pyridyl]-2-methoxy-phenol, 4-[2-amino-5-(3-chlorophenyl)-3-pyridyl]-2-methoxy-phenol, 4-[2-amino-5-(3-fluorophenyl)-3-pyridyl]-2-methoxy-phenol, 4-(2-amino-5-phenyl-3-pyridyl)-2-methoxy-phenol, 4-[6-amino-5-(4-hydroxy-3-methoxy-phenyl)-3-pyridyl]-2,6-dimethyl-phenol, 4-[2-amino-5-(4-fluorophenyl)-3-pyridyl]-2-methoxy-phenol, 4-[2-amino-5-(3,4,5-trimethoxyphenyl)-3-pyridyl]-2-methoxy-phenol, 4-[6-amino-5-[4-(methoxymethoxy)phenyl]-3-pyridyl]benzamide, 3-[6-amino-5-[4-(methoxymethoxy)phenyl]-3-pyridyl]phenyl]methanol, 3-[6-amino-5-[4-(methoxymethoxy)phenyl]-3-pyridyl]benzamide, N-[3-[6-amino-5-[4-(methoxymethoxy)phenyl]-3-pyridyl]phenyl]acetamide, 4-[6-amino-5-[4-(hydroxymethyl)phenyl]-3-pyridyl]-2,6-dimethyl-phenol, 3-[4-(methoxymethoxy)phenyl]-5-(3,4,5-trimethoxyphenyl)pyridin-2-amine, 3-[2-amino-5-(4-morpholinophenyl)-3-pyridyl]phenol, N-[3-[6-amino-5-(4-hydroxyphenyl)-3-pyridyl]phenyl]acetamide, 4-[2-amino-5-(3,4,5-trimethoxyphenyl)-3-pyridyl]phenol, 4-[2-amino-5-[3-(dimethylamino)phenyl]-3-pyridyl]phenol, 3-[2-amino-5-(3,4,5-trimethoxyphenyl)-3-pyridyl]phenol, 4-[2-amino-5-(4-methylsulfonylphenyl)-3-pyridyl]phenol, 3-(3-aminophenyl)-5-(3,4,5-trimethoxyphenyl)pyridin-2-amine, 4-[2-amino-5-(3-methoxyphenyl)-3-pyridyl]phenol, 4-[6-amino-5-(4-pyridyl)-3-pyridyl]-2,6-dimethyl-phenol, 5-[6-[3-(dimethylamino)propoxy]-3-pyridyl]-3-(3,4,5-trimethoxyphenyl)pyridin-2-amine, 5-(3-fluorophenyl)-3-(3,4,5-trimethoxyphenyl)pyridin-2-amine, 4-[6-amino-5-(3,4,5-trimethoxyphenyl)-3-pyridyl]-2,6-dimethyl-phenol, N-[3-[6-amino-5-(3,4,5-trimethoxyphenyl)-3-pyridyl]phenyl]methanesulfonamide, 5-phenyl-3-(3,4,5-trimethoxyphenyl)pyridin-2-amine, 3-[6-amino-5-(3,4,5-trimethoxyphenyl)-3-pyridyl]-N-(2-hydroxyethyl)benzamide, 5-(4-aminophenyl)-3-(3,4,5-trimethoxyphenyl)pyridin-2-amine, 4-[6-amino-5-(3,4,5-trimethoxyphenyl)-3-pyridyl]phenol, 5-(4-fluorophenyl)-3-(3,4,5-trimethoxyphenyl)pyridin-2-amine, 4-[6-amino-5-(3,4,5-trimethoxyphenyl)-3-pyridyl]-N-cyclopropyl-benzamide, 5-(benzothiophen-2-yl)-3-(3,4,5-trimethoxyphenyl)pyridin-2-amine, 3-[6-amino-5-(3,4,5-trimethoxyphenyl)-3-pyridyl]phenol, 5-(6-methoxy-3-pyridyl)-3-(3,4,5-trimethoxyphenyl)pyridin-2-amine, 5-[3-(dimethylamino)phenyl]-3-(3,4,5-trimethoxyphenyl)pyridin-2-amine, [3-[6-amino-5-[3-(dimethylamino)phenyl]-3-pyridyl]phenyl]-(4-methylpiperazin-1-yl)methanone, 4-[6-amino-5-[3-(dimethylamino)phenyl]-3-pyridyl]-2-methoxy-phenol, 3-[3-(dimethylamino)phenyl]-5-(3,4,5-trimethoxyphenyl)pyridin-2-amine, 4-[6-amino-5-[3-(dimethylamino)phenyl]-3-pyridyl]-2,6-dimethyl-phenol, 3-[3-(dimethylamino)phenyl]-5-(3-pyridyl)pyridin-2-amine, [3-[6-amino-5-[3-(dimethylamino)phenyl]-3-pyridyl]phenyl]methanol, 3-[3-(dimethylamino)phenyl]-5-[6-[3-(dimethylamino)propoxy]-3-pyridyl]pyridin-2-amine, 3-[6-amino-5-[3-(dimethylamino)phenyl]-3-pyridyl]benzamide, 5-(3,4-dimethoxyphenyl)-3-[3-(dimethylamino)phenyl]pyridin-2-amine, 4-[2-amino-5-(3-chloro-4-fluoro-phenyl)-3-pyridyl]-2-methoxy-phenol, 5-(4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)pyridin-2-amine, 4-[2-amino-5-(4-methoxyphenyl)-3-pyridyl]-2-methoxy-phenol, 5-(3-furyl)-3-(3,4,5-trimethoxyphenyl)pyridin-2-amine, 5-(2-phenoxyphenyl)-3-(3,4,5-trimethoxyphenyl)pyridin-2-amine, 4-[6-amino-5-(3,4,5-trimethoxyphenyl)-3-pyridyl]benzamide, 4-[2-amino-5-(3-methoxyphenyl)-3-pyridyl]-2-methoxy-phenol, [4-[2-amino-5-(3,4-dimethoxyphenyl)-3-pyridyl]phenyl]methanol, 5-[4-(4-methylpiperazin-1-yl)phenyl]-3-(3,4,5-trimethoxyphenyl)pyridin-2-amine, 3-[6-amino-5-(3,4,5-trimethoxyphenyl)-3-pyridyl]benzamide, 1-[5-[6-amino-5-[3-(dimethylamino)phenyl]-3-pyridyl]-2-thienyl]ethanone, 5-(4-methylsulfonylphenyl)-3-(3,4,5-trimethoxyphenyl)pyridin-2-amine, 4-[6-amino-5-(4-hydroxyphenyl)-3-pyridyl]benzamide, 4-[2-amino-5-[4-(4-methylpiperazin-1-yl)phenyl]-3-pyridyl]phenol, 4-[2-amino-5-[4-(4-methylpiperazin-1-yl)phenyl]-3-pyridyl]-2-methoxy-phenol, 4-[6-amino-5-(4-hydroxy-3-methoxy-phenyl)-3-pyridyl]benzamide, 4-[2-amino-5-(4-piperazin-1-ylphenyl)-3-pyridyl]-2-methoxy-phenol, 3,5-bis(3,4,5-trimethoxyphenyl)pyridin-2-amine, 4-[2-amino-5-[4-(4-isopropylpiperazin-1-yl)phenyl]-3-pyridyl]-2-methoxy-phenol, 4-[2-amino-5-(4-morpholinophenyl)-3-pyridyl]-2-methoxy-phenol, and 5-[6-amino-5-[4-(4-methylpiperazin-1-yl)phenyl]-3-pyridyl]-2-methoxy-phenol.

4. A compound of structural formula (II): ##STR00719## wherein: R1 is selected from the group consisting of H, alkyl, alkenyl, alkylene, alkynyl, aryl, arylalkyl, alkylaryl, arylalkenyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, heterocyclenyl, wherein each of the alkyl, alkenyl, alkylene, alkynyl, alkynylalkyl, aryl, arylalkyl, alkylaryl, arylalkenyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclic moieties can be substituted with one or more moieties which can be the same or different, each moiety being independently selected from the group consisting of acyl, alcohol, alkyl, aryl, aroyl, alkoxy, aryloxy, arylalkyloxy, alkylthio, arylthio, aralkylthio, alkoxycarbonyl, aryloxycarbonyl, aralkoxycarbonyl, alkylsulfonyl, arylsulfonyl, cyano, hydroxyalkyl, amide, amine, thiol, thiophene, pyrrole, furan, alkylsulfate, arylsulfate, alkylphosphate and arylphosphate, and R2 is selected from the group consisting of H, alkyl, alkenyl, alkylene, alkynyl, aryl, arylalkyl, alkylaryl, arylalkenyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, heterocyclenyl, wherein each of the alkyl, alkenyl, alkylene, alkynyl, alkynylalkyl, aryl, arylalkyl, alkylaryl, arylalkenyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclic moieties can be substituted with one or more moieties which can be the same or different, each moiety being independently selected from the group consisting of acyl, alcohol, alkyl, aryl, aroyl, alkoxy, aryloxy, arylalkyloxy, alkylthio, arylthio, aralkylthio, alkoxycarbonyl, aryloxycarbonyl, aralkoxycarbonyl, alkylsulfonyl, arylsulfonyl, cyano, hydroxyalkyl, amide, amine, thiol, thiophene, pyrrole, furan, alkylsulfate, arylsulfate, alkylphosphate and arylphosphate.

5. A method of treating, or slowing progression of, a disease associated with Fyn kinase, said method comprising administering a therapeutically effective amount of at least one compound according to claim 4, or pharmaceutically acceptable salt or solvate thereof to a patient in need thereof ##STR00720##

6. A compound according to claim 4 selected from the group consisting of N-(2-hydroxyethyl)-4-[3-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-6-yl]benzamide, 3-[3-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-6-yl]-N,N-dimethyl-benzamide, 4-[6-[4-(4-isopropylpiperazin-1-yl)phenyl]imidazo[1,2-a]pyrazin-3-yl]phenol, 4-[6-(1-benzylpyrazol-4-yl)imidazo[1,2-a]pyrazin-3-yl]phenol, 4-[3-(2-thienyl)imidazo[1,2-a]pyrazin-6-yl]phenol, 3,6-bis(2-thienyl)imidazo[1,2-a]pyrazine, N-(2-hydroxyethyl)-3-[3-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-6-yl]benzamide, N-cyclopropyl-4-[3-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-6-yl]benzamide, 4-[6-[4-(4-methylpiperazin-1-yl)phenyl]imidazo[1,2-a]pyrazin-3-yl]phenol, 4-[6-(6-amino-3-pyridyl)imidazo[1,2-a]pyrazin-3-yl]phenol, 5-[3-(2-thienyl)imidazo[1,2-a]pyrazin-6-yl]pyridin-2-amine, 4-[3-(3-acetylphenyl)imidazo[1,2-a]pyrazin-6-yl]-N-(2-dimethylaminoethyl)benzamide, N-(2-dimethylaminoethyl)-4-[3-(2-thienyl)imidazo[1,2-a]pyrazin-6-yl]benzamide, 4-[3-(3,5-dimethoxyphenyl)imidazo[1,2-a]pyrazin-6-yl]-N-[3-(dimethylamino)propyl]benzamide, N-(2-dimethylaminoethyl)-4-[3-(4-pyridyl)imidazo[1,2-a]pyrazin-6-yl]benzamide, 4-[6-[2-(dimethylamino)phenyl]imidazo[1,2-a]pyrazin-3-yl]-2-methoxy-phenol, N-(2-hydroxyethyl)-3-[3-(4-hydroxy-3-methoxy-phenyl)imidazo[1,2-a]pyrazin-6-yl]benzamide, 2-methoxy-4-[6-(3-pyridyl)imidazo[1,2-a]pyrazin-3-yl]phenol, 4-[6-(2-chlorophenyl)imidazo[1,2-a]pyrazin-3-yl]-2-methoxy-phenol, 4-[6-(3-ethoxyphenyl)imidazo[1,2-a]pyrazin-3-yl]-2-methoxy-phenol, N-(2-dimethylaminoethyl)-4-[3-(4-hydroxy-3-methoxy-phenyl)imidazo[1,2-a]pyrazin-6-yl]benzamide, 4-[6-(6-amino-3-pyridyl)imidazo[1,2-a]pyrazin-3-yl]-2-methoxy-phenol, 2-methoxy-4-[6-[6-(4-methylpiperazin-1-yl)-3-pyridyl]imidazo[1,2-a]pyrazin-3-yl]phenol, 2-methoxy-4-[6-(1-methylpyrazol-4-yl)imidazo[1,2-a]pyrazin-3-yl]phenol, N-[3-[3-(3,4,5-trimethoxyphenyl)imidazo[1,2-a]pyrazin-6-yl]phenyl]methanesulfonamide, N-[3-(dimethylamino)propyl]-4-[3-(4-hydroxy-3-methoxy-phenyl)imidazo[1,2-a]pyrazin-6-yl]benzamide, 2-methoxy-4-[6-[6-(2-morpholinoethylamino)-3-pyridyl]imidazo[1,2-a]pyrazin-3-yl]phenol, 6-(1-methylpyrazol-4-yl)-3-(3-thienyl)imidazo[1,2-a]pyrazine, 6-phenyl-3-(3-thienyl)imidazo[1,2-a]pyrazine, [4-[3-(3-thienyl)imidazo[1,2-a]pyrazin-6-yl]phenyl]methanol, 4-[3-(4-methoxyphenyl)imidazo[1,2-a]pyrazin-6-yl]phenol, 6-(3-pyridyl)-3-(3-thienyl)imidazo[1,2-a]pyrazine, 3-(4-pyridyl)-6-(2-thienyl)imidazo[1,2-a]pyrazine, 4-[3-(3-thienyl)imidazo[1,2-a]pyrazin-6-yl]phenol, 6-(2-thienyl)-3-(3-thienyl)imidazo[1,2-a]pyrazine, N-[3-[3-(3-thienyl)imidazo[1,2-a]pyrazin-6-yl]phenyl]acetamide, N-[3-[3-(3-thienyl)imidazo[1,2-a]pyrazin-6-yl]phenyl]methanesulfonamide, 6-(2-furyl)-3-(3-thienyl)imidazo[1,2-a]pyrazine, 3-(6-phenylimidazo[1,2-a]pyrazin-3-yl)phenol, 3-[3-(3-hydroxyphenyl)imidazo[1,2-a]pyrazin-6-yl]benzamide, 4-[6-(3-pyridyl)imidazo[1,2-a]pyrazin-3-yl]phenol, [4-[3-(4-phenoxyphenyl)imidazo[1,2-a]pyrazin-6-yl]phenyl]methanol, 4-[6-(4-chlorophenyl)imidazo[1,2-a]pyrazin-3-yl]phenol, 3-[6-(2-thienyl)imidazo[1,2-a]pyrazin-3-yl]phenol, 6-(1-methylpyrazol-4-yl)-3-(4-phenoxyphenyl)imidazo[1,2-a]pyrazine, 3-[6-(2-furyl)imidazo[1,2-a]pyrazin-3-yl]phenol, 4-[6-(6-methoxy-3-pyridyl)imidazo[1,2-a]pyrazin-3-yl]phenol, 3-[6-[4-(hydroxymethyl)phenyl]imidazo[1,2-a]pyrazin-3-yl]phenol, 3-[6-(1-methylpyrazol-4-yl)imidazo[1,2-a]pyrazin-3-yl]phenol, 4-[6-(1-methylpyrazol-4-yl)imidazo[1,2-a]pyrazin-3-yl]phenol, 6-[6-(4-methylpiperazin-1-yl)-3-pyridyl]-3-(4-phenoxyphenyl)imidazo[1,2-a]pyrazine, N-(2-hydroxyethyl)-3-[3-(4-phenoxyphenyl)imidazo[1,2-a]pyrazin-6-yl]benzamide, N-(2-dimethylaminoethyl)-4-[3-(4-phenoxyphenyl)imidazo[1,2-a]pyrazin-6-yl]benzamide, N-(2-hydroxyethyl)-4-[3-(4-phenoxyphenyl)imidazo[1,2-a]pyrazin-6-yl]benzamide, 4-[3-(3-chlorophenyl)imidazo[1,2-a]pyrazin-6-yl]-N-[3-(dimethylamino)propyl]benzamide, 5-[3-(4-phenoxyphenyl)imidazo[1,2-a]pyrazin-6-yl]pyridin-2-amine, N-[3-(dimethylamino)propyl]-4-[3-(3-thienyl)imidazo[1,2-a]pyrazin-6-yl]benzamide, 3-(4-methoxyphenyl)-6-[4-(4-methylpiperazin-1-yl)phenyl]imidazo[1,2-a]pyrazine, N-(2-hydroxyethyl)-3-[3-(3-thienyl)imidazo[1,2-a]pyrazin-6-yl]benzamide, 6-[6-(4-methylpiperazin-1-yl)-3-pyridyl]-3-(3-thienyl)imidazo[1,2-a]pyrazine, 5-[3-(3-thienyl)imidazo[1,2-a]pyrazin-6-yl]pyridin-2-amine, 3,6-bis(3-thienyl)imidazo[1,2-a]pyrazine, N-(2-dimethylaminoethyl)-4-[3-(3-thienyl)imidazo[1,2-a]pyrazin-6-yl]benzamide, 3-(1-methylpyrazol-4-yl)-6-(2-phenoxyphenyl)imidazo[1,2-a]pyrazine, 3-[6-[6-(4-methylpiperazin-1-yl)-3-pyridyl]imidazo[1,2-a]pyrazin-3-yl]phenol, 3-[[5-[3-(1,3-benzodioxol-5-yl)imidazo[1,2-a]pyrazin-6-yl]-2-pyridyl]oxy]-N,N-dimethyl-propan-1-amine, 3-[6-(3-ethoxyphenyl)imidazo[1,2-a]pyrazin-3-yl]phenol, 3-(1,3-benzodioxol-5-yl)-6-[4-(4-methylpiperazin-1-yl)phenyl]imidazo[1,2-a]pyrazine, 3-[6-(3-thienyl)imidazo[1,2-a]pyrazin-3-yl]phenol, 3-[6-[4-(4-methylpiperazin-1-yl)phenyl]imidazo[1,2-a]pyrazin-3-yl]phenol, 4-[3-(4-chlorophenyl)imidazo[1,2-a]pyrazin-6-yl]-N-[3-(dimethylamino)propyl]benzamide, 4-[3-(1,3-benzodioxol-5-yl)imidazo[1,2-a]pyrazin-6-yl]-N-(2-dimethylaminoethyl)benzamide, 3-[6-(6-amino-3-pyridyl)imidazo[1,2-a]pyrazin-3-yl]phenol, N-(2-dimethylaminoethyl)-4-[3-(3-hydroxyphenyl)imidazo[1,2-a]pyrazin-6-yl]benzamide, 4-[3-(4-chlorophenyl)imidazo[1,2-a]pyrazin-6-yl]-N-(2-dimethylaminoethyl)benzamide, 3-[6-[6-(2-morpholinoethylamino)-3-pyridyl]imidazo[1,2-a]pyrazin-3-yl]phenol, N-[3-(dimethylamino)propyl]-4-[3-(3-hydroxyphenyl)imidazo[1,2-a]pyrazin-6-yl]benzamide, N-(2-hydroxyethyl)-4-[3-(3-hydroxyphenyl)imidazo[1,2-a]pyrazin-6-yl]benzamide, 4-[3-(1,3-benzodioxol-5-yl)imidazo[1,2-a]pyrazin-6-yl]-N-[3-(dimethylamino)propyl]benzamide, 6-[6-(4-methylpiperazin-1-yl)-3-pyridyl]-3-phenyl-imidazo[1,2-a]pyrazine, 3-[6-[4-(4-isopropylpiperazin-1-yl)phenyl]imidazo[1,2-a]pyrazin-3-yl]phenol, 5-[3-(1,3-benzodioxol-5-yl)imidazo[1,2-a]pyrazin-6-yl]pyridin-2-amine, 4-[6-[6-[3-(dimethylamino)propoxy]-3-pyridyl]imidazo[1,2-a]pyrazin-3-yl]phenol, 4-[6-[6-(2-morpholinoethylamino)-3-pyridyl]imidazo[1,2-a]pyrazin-3-yl]phenol, 4-[6-[6-(4-methylpiperazin-1-yl)-3-pyridyl]imidazo[1,2-a]pyrazin-3-yl]phenol, 3-[2-(cyclohexylamino)imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-N,N-dimethyl-benzamide, N-[2-(dimethylamino)ethyl]-4-[3-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-6-yl]benzamide, N-[2-(dimethylamino)ethyl]-4-[3-(4-phenoxyphenyl)imidazo[1,2-a]pyrazin-6-yl]benzamide, N-[3-(dimethylamino)propyl]-4-[3-(4-phenoxyphenyl)imidazo[1,2-a]pyrazin-6-yl]benzamide, N-[2-(dimethylamino)ethyl]-4-[3-(4-hydroxy-3-methoxy-phenyl)imidazo[1,2-a]pyrazin-6-yl]benzamide, and 4-[6-[[(1S)-1-(hydroxymethyl)-2-methyl-propyl]amino]imidazo[1,2-b]pyridazin-3-yl]-2-methoxy-phenol.

7. A compound of structural formula (III): ##STR00721## wherein: R1 is selected from the group consisting of H, alkyl, alkenyl, alkylene, alkynyl, aryl, arylalkyl, alkylaryl, arylalkenyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, heterocyclenyl, wherein each of the alkyl, alkenyl, alkylene, alkynyl, alkynylalkyl, aryl, arylalkyl, alkylaryl, arylalkenyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclic moieties can be substituted with one or more moieties which can be the same or different, each moiety being independently selected from the group consisting of acyl, alcohol, alkyl, aryl, aroyl, alkoxy, aryloxy, arylalkyloxy, alkylthio, arylthio, aralkylthio, alkoxycarbonyl, aryloxycarbonyl, aralkoxycarbonyl, alkylsulfonyl, arylsulfonyl, cyano, hydroxyalkyl, amide, amine, thiol, thiophene, pyrrole, furan, alkylsulfate, arylsulfate, alkylphosphate and arylphosphate, and R2 is selected from the group consisting of H, alkyl, alkenyl, alkylene, alkynyl, aryl, arylalkyl, alkylaryl, arylalkenyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, heterocyclenyl, wherein each of the alkyl, alkenyl, alkylene, alkynyl, alkynylalkyl, aryl, arylalkyl, alkylaryl, arylalkenyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclic moieties can be substituted with one or more moieties which can be the same or different, each moiety being independently selected from the group consisting of acyl, alcohol, alkyl, aryl, aroyl, alkoxy, aryloxy, arylalkyloxy, alkylthio, arylthio, aralkylthio, alkoxycarbonyl, aryloxycarbonyl, aralkoxycarbonyl, alkylsulfonyl, arylsulfonyl, cyano, hydroxyalkyl, amide, amine, thiol, thiophene, pyrrole, furan, alkylsulfate, arylsulfate, alkylphosphate and arylphosphate.

8. A method of treating, or slowing progression of, a disease associated with Fyn kinase, said method comprising administering a therapeutically effective amount of at least one compound according to claim 7, or pharmaceutically acceptable salt or solvate thereof to a patient in need thereof ##STR00722##

9. A compound according to claim 7 selected from the group consisting of N-[4-[3-(4-hydroxy-3-methoxy-phenyl)imidazo[1,2-b]pyridazin-6-yl]phenyl]acetamide, N-[3-[6-(1,3-benzodioxol-5-yl)imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide, N-[3-[3-(1,3-benzodioxol-5-yl)imidazo[1,2-b]pyridazin-6-yl]phenyl]acetamide, N-[3-[6-[3-(trifluoromethoxy)phenyl]imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide, 1-[3-[6-(3,4-dimethoxyphenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone, N-[3-[6-(4-methylsulfonylphenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide, N-[3-[3-(3-acetamidophenyl)imidazo[1,2-b]pyridazin-6-yl]phenyl]acetamide, N-[3-[3-(3-acetylphenyl)imidazo[1,2-b]pyridazin-6-yl]phenyl]acetamide, 4-[3-(3-acetamidophenyl)imidazo[1,2-b]pyridazin-6-yl]benzamide, N-[4-[3-(3-hydroxyphenyl)imidazo[1,2-b]pyridazin-6-yl]phenyl]acetamide, N-[3-[3-[3-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]phenyl]acetamide, N-[3-[6-(4-dimethylaminophenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide, N-[3-[3-(4-hydroxy-3-methoxy-phenyl)imidazo[1,2-b]pyridazin-6-yl]phenyl]acetamide, N-[3-[3-[4-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]phenyl]methanesulfonamide, 1-[3-[6-(3-hydroxyphenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone, [4-[3-[3-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]phenyl]methanol, 4-[3-[3-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]benzamide, N-(2-dimethylaminoethyl)-3-[6-[4-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-3-yl]benzamide, 3-[3-(3-hydroxyphenyl)imidazo[1,2-b]pyridazin-6-yl]benzamide, 4-[3-[4-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]-2-methoxy-phenol, [3-[6-(3-pyridyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanol, [3-[6-[(4-fluorophenyl)methyl]imidazo[1,2-b]pyridazin-3-yl]phenyl]methanol, [3-[6-(3-methoxyphenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanol, N-[3-[3-(4-pyridyl)imidazo[1,2-b]pyridazin-6-yl]phenyl]methanesulfonamide, 6-(2-methoxyphenyl)-3-(4-pyridyl)imidazo[1,2-b]pyridazine, 3-[3-(4-pyridyl)imidazo[1,2-b]pyridazin-6-yl]benzamide, N-[3-(6-phenylimidazo[1,2-b]pyridazin-3-yl)phenyl]acetamide, N-[3-[6-(3-hydroxyphenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide, 3-(3,4-dimethoxyphenyl)-6-(3-fluorophenyl)imidazo[1,2-b]pyridazine, N-[3-[6-[4-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide, [3-(6-phenylimidazo[1,2-b]pyridazin-3-yl)phenyl]methanol, 6-(3-chlorophenyl)-3-(4-pyridyl)imidazo[1,2-b]pyridazine, 4-[3-(3,4-dimethoxyphenyl)imidazo[1,2-b]pyridazin-6-yl]-2-methoxy-phenol, N-[3-[6-(2-methoxyphenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide, N-[3-[6-[3-(trifluoromethyl)phenyl]imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide, [3-[6-(2-methoxyphenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanol, 4-[3-[3-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]-2-methoxy-phenol, 3-phenyl-6-(4-pyridyl)imidazo[1,2-b]pyridazine, 3-[3-(4-pyridyl)imidazo[1,2-b]pyridazin-6-yl]phenol, 3-(3,4-dimethoxyphenyl)-6-phenyl-imidazo[1,2-b]pyridazine, 3-(3,4-dimethoxyphenyl)-6-(4-fluorophenyl)imidazo[1,2-b]pyridazine, N-[3-[6-(3,4,5-trimethoxyphenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide, N-[3-[6-(4-hydroxy-3-methoxy-phenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide, 3-phenyl-6-(3-pyridyl)imidazo[1,2-b]pyridazine, [4-[3-(4-pyridyl)imidazo[1,2-b]pyridazin-6-yl]phenyl]methanol, 3-(3,4-dimethoxyphenyl)-6-(2-methoxyphenyl)imidazo[1,2-b]pyridazine, 3-(3,4-dimethoxyphenyl)-6-(3-furyl)imidazo[1,2-b]pyridazine, N-[3-[6-(3-furyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide, [3-[6-(3-furyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanol, N,N-dimethyl-4-[3-(4-pyridyl)imidazo[1,2-b]pyridazin-6-yl]aniline, [3-[6-(4-methylsulfonylphenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanol, N-[3-(3-phenylimidazo[1,2-b]pyridazin-6-yl)phenyl]acetamide, 6-phenyl-3-(4-pyridyl)imidazo[1,2-b]pyridazine, 6-(3-fluorophenyl)-3-(4-pyridyl)imidazo[1,2-b]pyridazine, 3-(3,4-dimethoxyphenyl)-6-(3-methoxyphenyl)imidazo[1,2-b]pyridazine, N-[3-[6-(5-methoxy-3-pyridyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide, [3-[6-(5-methoxy-3-pyridyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanol, 6-(1,3-benzodioxol-5-yl)-3-(4-pyridyl)imidazo[1,2-b]pyridazine, 6-(3-furyl)-3-(4-pyridyl)imidazo[1,2-b]pyridazine, N-[3-[6-(3-chlorophenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide, N-[3-[6-(3-methoxyphenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide, 3-[3-[3-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]phenol, 4-(3-phenylimidazo[1,2-b]pyridazin-6-yl)benzamide, 3-[3-(1,3-benzodioxol-5-yl)imidazo[1,2-b]pyridazin-6-yl]phenol, 6-phenyl-3-(3-pyridyl)imidazo[1,2-b]pyridazine, 3-(3-pyridyl)-6-(2-thienyl)imidazo[1,2-b]pyridazine, N-[3-[6-(3-acetylphenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide, 3-[6-(3-methoxyphenyl)imidazo[1,2-b]pyridazin-3-yl]phenol, 4-[6-(3,4-dimethoxyphenyl)imidazo[1,2-b]pyridazin-3-yl]-2-methoxy-phenol, 1-[3-[6-(2-methoxyphenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone, 1-[3-[6-(1-methylpyrazol-4-yl)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone, N-[3-[3-(2-thienyl)imidazo[1,2-b]pyridazin-6-yl]phenyl]methanesulfonamide, 3-(1,3-benzodioxol-5-yl)-6-(3-pyridyl)imidazo[1,2-b]pyridazine, [4-[3-(3-pyridyl)imidazo[1,2-b]pyridazin-6-yl]phenyl]methanol, 6-benzyl-3-(3,4-dimethoxyphenyl)imidazo[1,2-b]pyridazine, 3-[6-[4-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-3-yl]phenol, [4-[6-(2-methoxyphenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanol, [4-[6-(3-methoxyphenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanol, 2-methoxy-4-[6-(3-methoxyphenyl)imidazo[1,2-b]pyridazin-3-yl]phenol, 1-[3-[6-(3-furyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone, 4-[3-(2-thienyl)imidazo[1,2-b]pyridazin-6-yl]benzamide, 3-[3-(1,3-benzodioxol-5-yl)imidazo[1,2-b]pyridazin-6-yl]-N-(2-hydroxyethyl)benzamide, [3-[3-(1,3-benzodioxol-5-yl)imidazo[1,2-b]pyridazin-6-yl]phenyl]methanol, N-[3-[6-(2-thienyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide, 3-(6-phenylimidazo[1,2-b]pyridazin-3-yl)phenol, 1-[3-[3-(3-hydroxyphenyl)imidazo[1,2-b]pyridazin-6-yl]phenyl]ethanone, [4-[6-(3-fluorophenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanol, 1-[3-[3-[3-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]phenyl]ethanone, 1-[3-[6-[3-(dimethylamino)phenyl]imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone, 1-[3-[6-(6-amino-3-pyridyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone, [4-[3-(2-thienyl)imidazo[1,2-b]pyridazin-6-yl]phenyl]methanol, N-[3-[3-(3,4-dimethoxyphenyl)imidazo[1,2-b]pyridazin-6-yl]phenyl]methanesulfonamide, 3-[3-(3-acetylphenyl)imidazo[1,2-b]pyridazin-6-yl]benzamide, N-[3-[3-(3-pyridyl)imidazo[1,2-b]pyridazin-6-yl]phenyl]methanesulfonamide, 3-[6-(4-pyridyl)imidazo[1,2-b]pyridazin-3-yl]phenol, 3-[6-(5-quinolyl)imidazo[1,2-b]pyridazin-3-yl]phenol, N-[3-[3-[3-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]phenyl]methanesulfonamide, 2-methoxy-4-[6-(2-methoxyphenyl)imidazo[1,2-b]pyridazin-3-yl]phenol, 3-[3-(3-acetylphenyl)imidazo[1,2-b]pyridazin-6-yl]-N-methyl-benzamide, [3-[3-(2-thienyl)imidazo[1,2-b]pyridazin-6-yl]phenyl]methanol, 6-(1-methylpyrazol-4-yl)-3-(2-thienyl)imidazo[1,2-b]pyridazine, 3-[3-(3,4-dimethoxyphenyl)imidazo[1,2-b]pyridazin-6-yl]-N-(2-hydroxyethyl)benzamide, 3-(1,3-benzodioxol-5-yl)-6-(1-methylpyrazol-4-yl)imidazo[1,2-b]pyridazine, 3-(3,4-dimethoxyphenyl)-6-(1-methylpyrazol-4-yl)imidazo[1,2-b]pyridazine, 3-[6-(3-fluorophenyl)imidazo[1,2-b]pyridazin-3-yl]phenol, 1-[3-[6-(3-aminophenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone, 6-(2-methoxyphenyl)-3-(3-pyridyl)imidazo[1,2-b]pyridazine, 3-(3,4-dimethoxyphenyl)-6-(4-pyridyl)imidazo[1,2-b]pyridazine, 3-[6-(3-pyridyl)imidazo[1,2-b]pyridazin-3-yl]phenol, 3-[6-(1-methylpyrazol-4-yl)imidazo[1,2-b]pyridazin-3-yl]phenol, [4-[6-(4-fluorophenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanol, 4-[6-(3-hydroxyphenyl)imidazo[1,2-b]pyridazin-3-yl]-2-methoxy-phenol, 6-(3,4-dimethoxyphenyl)-3-(4-pyridyl)imidazo[1,2-b]pyridazine, 6-(4-fluorophenyl)-3-(3-pyridyl)imidazo[1,2-b]pyridazine, [3-[3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl]phenyl]methanol, 3-[6-(4-fluorophenyl)imidazo[1,2-b]pyridazin-3-yl]phenol, 3-phenyl-6-(2-thienyl)imidazo[1,2-b]pyridazine, 3-(3,4-dimethoxyphenyl)-6-(3-pyridyl)imidazo[1,2-b]pyridazine, N-[3-[3-(3-hydroxyphenyl)imidazo[1,2-b]pyridazin-6-yl]phenyl]acetamide, 4-[6-[4-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-3-yl]-2-methoxy-phenol, 3-[3-(3,4-dimethoxyphenyl)imidazo[1,2-b]pyridazin-6-yl]-N-methyl-benzamide, N-[3-[3-(4-pyridyl)imidazo[1,2-b]pyridazin-6-yl]phenyl]acetamide, 6-(3-furyl)-3-(3-pyridyl)imidazo[1,2-b]pyridazine, N-[3-[6-(3,4-dimethoxyphenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide, 3-[6-(3-furyl)imidazo[1,2-b]pyridazin-3-yl]phenol, 1-[3-[6-(4-pyridyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone, 6-(m-tolylmethyl)-3-(4-pyridyl)imidazo[1,2-b]pyridazine, 3-(1,3-benzodioxol-5-yl)-6-(4-fluorophenyl)imidazo[1,2-b]pyridazine, 3,6-bis(3,4-dimethoxyphenyl)imidazo[1,2-b]pyridazine, 3-[6-(2-methoxyphenyl)imidazo[1,2-b]pyridazin-3-yl]phenol, [4-(6-phenylimidazo[1,2-b]pyridazin-3-yl)phenyl]methanol, N-[4-[3-[4-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]phenyl]acetamide, 4-[6-[3-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-3-yl]-2-methoxy-phenol, 1-[3-[6-[3-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone, 6-(4-pyridyl)-3-(2-thienyl)imidazo[1,2-b]pyridazine, 2-methoxy-4-[3-(2-thienyl)imidazo[1,2-b]pyridazin-6-yl]phenol, N-(2-hydroxyethyl)-3-(3-phenylimidazo[1,2-b]pyridazin-6-yl)benzamide, 6-benzyl-3-(4-pyridyl)imidazo[1,2-b]pyridazine, 4-[3-(3-pyridyl)imidazo[1,2-b]pyridazin-6-yl]benzamide, 1-[3-[6-(3-pyridyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone, 1-[3-[6-(3-methoxyphenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone, 6-[(4-fluorophenyl)methyl]-3-(4-pyridyl)imidazo[1,2-b]pyridazine, 3-[3-(1,3-benzodioxol-5-yl)imidazo[1,2-b]pyridazin-6-yl]aniline, 3-(1,3-benzodioxol-5-yl)-6-(3-furyl)imidazo[1,2-b]pyridazine, [4-[6-(3,4-dimethoxyphenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanol, 3-[3-(1,3-benzodioxol-5-yl)imidazo[1,2-b]pyridazin-6-yl]-N-(2-dimethylaminoethyl)benzamide, N-[3-[6-(3-chloro-4-fluoro-phenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide, 3-[3-[4-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]phenol, [3-[6-(3,4-dimethoxyphenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanol, 1-[3-[3-(3-acetylphenyl)imidazo[1,2-b]pyridazin-6-yl]phenyl]ethanone, N-(2-dimethylaminoethyl)-3-[3-(2-thienyl)imidazo[1,2-b]pyridazin-6-yl]benzamide, 3-(1,3-benzodioxol-5-yl)-6-phenyl-imidazo[1,2-b]pyridazine, 3-[3-(3-pyridyl)imidazo[1,2-b]pyridazin-6-yl]phenol, 3-(3,4-dimethoxyphenyl)-6-(2-thienyl)imidazo[1,2-b]pyridazine, 3-[3-(3-hydroxyphenyl)imidazo[1,2-b]pyridazin-6-yl]phenol, N-[3-[3-[4-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]phenyl]acetamide, 1-[3-[6-(4-fluorophenyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone, 3-[3-(3-acetamidophenyl)imidazo[1,2-b]pyridazin-6-yl]-N-methyl-benzamide, [3-(3-phenylimidazo[1,2-b]pyridazin-6-yl)phenyl]methanol, 6-(1-methylpyrazol-4-yl)-3-(4-pyridyl)imidazo[1,2-b]pyridazine, N-(2-dimethylaminoethyl)-3-[3-[3-(trifluoromethoxy)phenyl]imidazo[1,2-b]pyridazin-6-yl]benzamide, [4-[3-[4-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]phenyl]methanol, 4-[6-(1,3-benzodioxol-5-yl)imidazo[1,2-b]pyridazin-3-yl]-2-methoxy-phenol, 1-[3-[6-(2-thienyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone, 6-(5-methoxy-3-pyridyl)-3-(2-thienyl)imidazo[1,2-b]pyridazine, 3,6-bis(2-thienyl)imidazo[1,2-b]pyridazine, N-(2-dimethylaminoethyl)-3-[6-(1-methylpyrazol-4-yl)imidazo[1,2-b]pyridazin-3-yl]benzamide, 3-[6-(1,3-benzodioxol-5-yl)imidazo[1,2-b]pyridazin-3-yl]-N-(2-dimethylaminoethyl)benzamide, 3-[3-[3-(2-dimethylaminoethylcarbamoyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]benzamide, N-(2-hydroxyethyl)-3-[3-(3-hydroxyphenyl)imidazo[1,2-b]pyridazin-6-yl]benzamide, 2-methoxy-4-[6-(3,4,5-trimethoxyphenyl)imidazo[1,2-b]pyridazin-3-yl]phenol, [3-[3-(3-furyl)imidazo[1,2-b]pyridazin-6-yl]phenyl]methanol, 4-(6-benzylimidazo[1,2-b]pyridazin-3-yl)benzamide, 3-[6-(4-acetamidophenyl)imidazo[1,2-b]pyridazin-3-yl]-N-(2-dimethylaminoethyl)benzamide, 2-methoxy-4-[6-[3-(trifluoromethoxy)phenyl]imidazo[1,2-b]pyridazin-3-yl]phenol, N-(2-dimethylaminoethyl)-3-[6-[3-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-3-yl]benzamide, 4-[6-[(3,4-difluorophenyl)methyl]imidazo[1,2-b]pyridazin-3-yl]benzamide, 3-[6-(3-acetamidophenyl)imidazo[1,2-b]pyridazin-3-yl]-N-(2-dimethylaminoethyl)benzamide, 2-methoxy-4-[6-[3-(trifluoromethyl)phenyl]imidazo[1,2-b]pyridazin-3-yl]phenol, 6-benzyl-3-(5-methoxy-3-pyridyl)imidazo[1,2-b]pyridazine, 4-[6-(m-tolylmethyl)imidazo[1,2-b]pyridazin-3-yl]benzamide, N-(2-dimethylaminoethyl)-3-[6-(2-methoxyphenyl)imidazo[1,2-b]pyridazin-3-yl]benzamide, N-(2-dimethylaminoethyl)-3-[6-(3-phenoxyphenyl)imidazo[1,2-b]pyridazin-3-yl]benzamide, 3-(6-cyclopropylimidazo[1,2-b]pyridazin-3-yl)phenol, 4-[6-(3-fluorophenyl)imidazo[1,2-b]pyridazin-3-yl]-2-methoxy-phenol, 6-[(4-fluorophenyl)methyl]-3-(5-methoxy-3-pyridyl)imidazo[1,2-b]pyridazine, 4-[6-[(4-fluorophenyl)methyl]imidazo[1,2-b]pyridazin-3-yl]benzamide, N-(2-hydroxyethyl)-3-[3-[4-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]benzamide, 3-[3-(4-hydroxy-3-methoxy-phenyl)imidazo[1,2-b]pyridazin-6-yl]benzamide, 3-(1-methylpyrazol-4-yl)-6-(m-tolylmethyl)imidazo[1,2-b]pyridazine, 3-[3-(3-acetylphenyl)imidazo[1,2-b]pyridazin-6-yl]-N-(2-hydroxyethyl)benzamide, [4-(6-benzylimidazo[1,2-b]pyridazin-3-yl)phenyl]methanol, 4-[6-[(4-fluorophenyl)methyl]imidazo[1,2-b]pyridazin-3-yl]-2-methoxy-phenol, -[(4-fluorophenyl)methyl]-3-(1-methylpyrazol-4-yl)imidazo[1,2-b]pyridazine, N-(2-dimethylaminoethyl)-3-[6-(4-fluorophenyl)imidazo[1,2-b]pyridazin-3-yl]benzamide, 3-[3-(3-chlorophenyl)imidazo[1,2-b]pyridazin-6-yl]-N-(2-hydroxyethyl)benzamide, 3-[6-(m-tolylmethyl)imidazo[1,2-b]pyridazin-3-yl]benzamide, 1-[3-(6-benzylimidazo[1,2-b]pyridazin-3-yl)phenyl]ethanone, 5-(6-benzylimidazo[1,2-b]pyridazin-3-yl)pyridin-2-amine, N-(2-dimethylaminoethyl)-3-[6-(3-furyl)imidazo[1,2-b]pyridazin-3-yl]benzamide, 3-[3-[4-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]-N-methyl-benzamide, 2-methoxy-4-[6-(propylamino)imidazo[1,2-b]pyridazin-3-yl]phenol, 3-(4-pyridyl)-N-(2-thienylmethyl)imidazo[1,2-b]pyridazin-6-amine, 2-methoxy-4-[6-(tetrahydropyran-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenol, 2-methoxy-4-[6-(2-thienylmethylamino)imidazo[1,2-b]pyridazin-3-yl]phenol, N-propyl-3-(4-pyridyl)imidazo[1,2-b]pyridazin-6-amine, 2-methoxy-4-[6-(2-pyridylmethylamino)imidazo[1,2-b]pyridazin-3-yl]phenol, 3-(4-pyridyl)-N-tetrahydropyran-4-yl-imidazo[1,2-b]pyridazin-6-amine, 3-(3,4-dimethoxyphenyl)-N-propyl-imidazo[1,2-b]pyridazin-6-amine, 4-[6-[[(1S)-1-(hydroxymethyl)-2-methyl-propyl]amino]imidazo[1,2-b]pyridazin-3-yl]-2-methoxy-phenol, 3-(3,4-dimethoxyphenyl)-N-(2-pyridylmethyl)imidazo[1,2-b]pyridazin-6-amine, 3-[[3-(4-pyridyl)imidazo[1,2-b]pyridazin-6-yl]amino]propan-1-ol, (2S)-3-methyl-2-[[3-(4-pyridyl)imidazo[1,2-b]pyridazin-6-yl]amino]butan-1-ol, 1-[3-[6-(3-hydroxypropylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone, 3-(3,4-dimethoxyphenyl)-N-(2-thienylmethyl)imidazo[1,2-b]pyridazin-6-amine, 3-[[3-(3,4-dimethoxyphenyl)imidazo[1,2-b]pyridazin-6-yl]amino]propan-1-ol, N-[3-[6-(4-pyridyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide, 4-[6-(1,3-benzodioxol-5-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]-2-methoxy-phenol, 1-[3-[6-(1,3-benzodioxol-5-ylmethylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]ethanone, N-(1,3-benzodioxol-5-ylmethyl)-3-(3,4-dimethoxyphenyl)imidazo[1,2-b]pyridazin-6-amine, [3-[6-(4-pyridyl)imidazo[1,2-b]pyridazin-3-yl]phenyl]methanol, 2-methoxy-4-[6-(4-pyridyl)imidazo[1,2-b]pyridazin-3-yl]phenol, 3-(4-pyridyl)-N-(2-pyridylmethyl)imidazo[1,2-b]pyridazin-6-amine, 4-[3-(4-hydroxy-3-methoxy-phenyl)imidazo[1,2-b]pyridazin-6-yl]-2-methoxy-phenol, [3-[3-[3-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-6-yl]phenyl]methanol, N-[3-[6-[3-(hydroxymethyl)phenyl]imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide, 3-(4-fluorophenyl)-N-methyl-imidazo[1,2-b]pyridazin-6-amine, 3-(4-methoxyphenyl)-N-methyl-imidazo[1,2-b]pyridazin-6-amine, 2-[6-(methylamino)imidazo[1,2-b]pyridazin-3-yl]phenol, N-methyl-3-(3-thienyl)imidazo[1,2-b]pyridazin-6-amine, 3-[6-(methylamino)imidazo[1,2-b]pyridazin-3-yl]phenol, 3-(3,4-dimethoxyphenyl)-N-methyl-imidazo[1,2-b]pyridazin-6-amine, N,N-dimethyl-3-[6-(methylamino)imidazo[1,2-b]pyridazin-3-yl]benzamide, N-methyl-3-(1-methylpyrazol-4-yl)imidazo[1,2-b]pyridazin-6-amine, N-[3-[6-(methylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl]acetamide, 3-(6-methoxy-3-pyridyl)-N-methyl-imidazo[1,2-b]pyridazin-6-amine, and (Z)-5-[6-(methylamino)imidazo[1,2-b]pyridazin-3-yl]pent-4-en-1-ol.

10-24. (canceled)

25. The method of claim 2, wherein the disease associated with Fyn kinase is selected from the group of disorders consisting of Type I diabetes, Type II diabetes, pre-diabetes, breast cancer, prostate cancer, pancreatic cancer, esophageal cancer, gastric cancer, liver cancer, bowel cancer, melanoma, Multiple Sclerosis, Alzheimer's disease, and Parkinson's disease.

26.-28. (canceled)

Description

DETAILED DESCRIPTION OF THE INVENTION

[0107] Identifying FYN Kinase Inhibitors.

[0108] Individual compounds within a chemical library consisting of 600 potential kinase inhibitors were assayed with the ADP-Glo Kinase Assay kit (V9102, Promega UK Ltd., Southhampton, Hampshire, UK) to identify the most potent FYN kinase inhibitors within the collection. The chemical library was comprised of the SoftFocus ATP-competitive hinge binding compounds described by Harris, C. J., Hill, R. D., Sheppard, D. W., et al., The Design and Application of Target-Focused Compound Libraries. Combinatorial Chemistry and High Throughput Screening 14:521-31 (2011). The specific pharmacore chemistries included SFK52 comprising 6-[R2]-3-[R1]imidazo[1,2-b] pyridazine compounds, SFK33 comprising N-(3-[R2] imidazo [1,2-b] pyridazin-6-yl) [R1] amine compounds, SFK49 comprising N-(5-[R2] imidazo [2,1-b][1,3,4] thiadiazol-2-yl)[R1]-amine compounds, SFK 40 comprising 5-[R2]-3-[R1] pyridin-2-amine compounds, SFK43 comprising 6-[R2]-3-[R1]imidazo[1,2-a] pyrazine compounds, and SFK63. The scaffold structure of each pharmacore is shown in Table 2. The chemical structures of the initial 600 potential kinase inhibitors are presented in Table 3, with those chosen for additional analysis presented in Table 4. Comparison of the compounds presented in Table 1 and those of Tables 2, 3 and 4, illustrate the novelty of the chemical structures claimed herein.

[0109] FYN kinase (10 micrograms) was from the FYN A Kinase Enzyme System (V3571, Promega UK Ltd.), a full-length recombinant human FYN A containing an N-terminal GST tag of about 85 kDa, expressed by bacullovirus in S19 insect cells, supplied at a concentration of 0.1 microgram/microliter in 5 reaction buffer. The FYN substrate, a 12 amino acid peptide of the sequence EFGTYGTLSKKK, containing a single tyrosine phosphorylation site, was custom synthesized (Peptide Synthetics, Peptide Protein Research, Fareham, UK) and supplied as a 4 mg/ml aqueous solution. All other reagents were obtained from Sigma (Sigma-Aldrich, Gillingham, Dorset, UK), with the exception of UltraPure ATP (V9102, Promega UK Ltd.) and the ATP-competitive broad spectrum protein kinase inhibitor staurosporine (569397, Merck Millipore, Watford, Hertfordshire, UK), or as otherwise indicated.

[0110] The assay procedure determines the IC50 of each potential FYN kinase inhibitor by measuring the enzyme catalyzed ATP-dependent phosphorylation of the FYN substrate peptide. The ADP-Glo Kinase Assay is specifically designed to quantify kinase activity by measuring the ADP produced in the reaction The reaction buffer comprises 40 mM Tris.Math.HCl (pH 7.5), 20 mM MgCl.sub.2, 0.1 mg/ml BSA and 5 microM DTT. Individual compounds within the chemical library were dissolved in DMSO at known concentrations. Briefly, 2.5 microliters of reaction buffer containing 3 picograms of FYN kinase and serial dilutions of each potential FYN kinase inhibitor (9 3-fold dilutions of a 10 micromolar top sample) are placed into each well of a 384 well microtiter plate and incubated at room temperature for 30 minutes. An additional 2.5 microliters of reaction buffer containing 100 picograms of the FYN substrate and 12.5 picomoles of ATP are then added to each well and the reaction carried out for 90 minutes at room temperature. The reactions are terminated by addition of 5 microliters of the ADP-Glo Reagent component of the ADP-Glo Kinase Assay kit to each well. The ADP-Glo Reagent comprises an ATP-dependent adenylate cyclase, an inorganic pyrophosphatase and an excess of staurosporine. The adenylate cyclase converts the remaining ATP to cAMP and pyrophospahte, the pyrophosphatase converts the pyrophosphate to phosphate and the staurosporine inhibits the activity of the FYN kinase, the net effect is to remove all residual ATP while preserving the ADP produced by FYN kinase. The terminated reactions are incubated for 40 minutes at room temperature, prior to addition of the Kinase Detection Reagent component of the ADP-Glo Kinase Assay kit to each well. The Kinase Detection Reagent comprises pyruvate kinase, phosphoenol pyruvate (PEP), luciferin and luciferase. The pyruvate kinase converts PEP to pyruvate and in the process generates ATP from the residual ADP present in the terminated reaction. The ATP is then consumed by the luciferase catalyzed, light emitting conversion of luciferin to oxyluciferin producing AMP, pyrophosphate and CO2. The emitted light was measured on an Envion Luminometer to determine the relative activity of the FYN kinase in each well. A 10 point dose-response curve for each potential FYN kinase inhibitor dilution series was used to determine the IC50, of each compound. Details of the analysis, including assay procedures and representative dilution schema for measuring kinase inhibitors are presented in the Technical Manual accompanying the ADP-Glo Kinase Assay kit (Doc. TM313, Promega Corp.) as well as U.S. Pat. Nos. 8,183,007 and 8,802,411, the contents of which are incorporated herein, in their entirety.

[0111] The results of screening candidate libraries are presented in Table 3, which lists the structure of each compound, the standard IUPAC name of the compound, the observed IC50 and the calculated lipophilicity of the compound. The most potent FYN kinase inhibitors, generally those with the most favorable combination of IC50 and drugability were resynthesized and subjected to further testing and expansion. In general, the best candidate compounds exhibit an IC50 of less than 200 nM and drugability as measured by LLE (Ligand-lipophilicity efficiency) of greater than 2.5. LLE=(pIC50-cLogP) where pIC50 is the negative log of the observed IC50 and cLogP is a calculated consensus measure of the lipophilicity of the compound. In practice, this means a cLogP of less than 3.5, based on an average IC50 of less than or equal to 1 M, represents a favorable level of drugability (LLE>2.5). Candidate compounds selected for additional testing and expansion are listed in Table 4.

[0112] Cell Based Assay(s) of FYN Kinase Inhibitors

[0113] Test compounds exhibiting superior IC50 and LLE profiles are further tested for their ability to stimulate T cell proliferation and to inhibit production of Interleukin 2 by stimulated T-cells.

[0114] T-cell proliferation is analyzed by staining with carboxy-fluorescein diacetate succinimidyl ester (CFSE) at a final concentration 5 M (Molecular Probes, Invitrogen) according to the manufacturer's instructions. Briefly, cells are resuspended in warm PBS containing 5 M CFSE and incubated at 37 C. for 10 minutes. Subsequently, cells are washed twice and resuspended in culture media containing 10% FBS before the experimental treatments are initiated. Cells may be analyzed by flow cytometry after 5 days in culture. Alternatively, a 96-well plate is coated with a monoclonal antibody to CD3 (G19-4), the antibody is allowed to bind, and then the plate is washed. Normal human peripheral blood T cells are added to the wells, along with test compound and anti-CD28 antibody to provide co-stimulation. After 3 days, [.sup.3H]thymidine is added to the cells and incubated for 6 hours. The cells are harvested and counted in a liquid scintillation counter to measure proliferation.

[0115] To measure the ability of test compounds to block IL-2 production by Fyn mediated tyrosine phosphorylation induced by anti-CD3 and IL-2 stimulated T-cell proliferation, human T-cells, such as Jurkat cells are preincubated with various concentrations of test compound in serum-free medium at 37 C. for 10 min and then stimulated with plastic-immobilized anti-CD3 mAbs. Cells are cultured in complete media supplemented with 5% fetal bovine serum for 24 h in the presence of 10 g/ml of anti-human CD25 mAbs to prevent IL-2 autocrine consumption. The supernatants are then harvested and centrifuged, and the IL-2 in the supernatant measured in a bioassay using a murine IL-2-dependent cell line, such as CTLL-4, as described by Trevillyan, et al., J. Immunol. 145:3223-30 (1990). To avoid the influence of residual test compound in the supernatants on proliferation of CTLL-4 cells, the test compound is removed by extensive dialysis against phosphate-buffered saline (0.1 M, pH 7.4). A control supernatant harvested from anti-CD3-stimulated Jurkat cells lacking Lck is spiked with 200 M test compound is included along with the test compound dilution series to ascertain that all test compound is removed by the dialysis procedure. This dialysis control supernatant stimulates CTLL-4 proliferation as well as the positive control supernatant without added test compound, indicating the dialysis procedure has removed the test compound. Alternatively, IL-2 can be directly measured with an in vitro cytokine assays using labeled anti-IL2 mAbs, such as CisBio's Human IL2 Assay Kit (CisBio US, Bedford, Mass.) without requiring prior removal of test compound.

[0116] One of skill in the art will recognize that other assays may be devised to measure the efficacy of Fyn kinase inhibition by test compounds and that such assays are conventional in the art and known to those of ordinary skill.

TABLE-US-00002 TABLE 2 Representative scaffold structures of SoftFocus library pharmacores [00010] 5-[R2]-3-[R1]pyridin-2-amine Formula I (SFK40 pharmacore) [00011] 6-[R2]-3-[R1]imidazo[1,2-a]pyrazine Formula II (SFK43 pharmacore) [00012] 6-[R2]-3-[R1]imidazo[1,2-b]pyridazine Formula III (SFK52 pharmacore) [00013] N-(5-[R2]imidazo[2,1-b][1,3,4] thiadiazol-2-yl)[R1]amine Formula IV (SFK49 pharmacore) [00014] 4-[R2]-3-[R1]-1H-pyrazolo[3,4-b] pyridine Formula V (SFK63 pharmacore) [00015] N-(3-[R2]imidazo[1,2-b]pyridazin-6- yl)[R1]amine Formula VI (SFK33 pharmacore)

TABLE-US-00003 TABLE 3 Primary screen-initial compounds. IC50 FYN logP Structure IUPAC name (M) (consensus) Compound ID. [00016] N-[3-[6-(2- furylmethyl- amino) pyrazin-2- yl]phenyl] acetamide 11.18502 1.66 035_0144_0081 [00017] 4-[6-[1- (hydroxy- methyl) propylamino] pyrazin- 2-yl]phenol 15.34591 1.58 035_0153_0080 [00018] 2-[[6-(5- isopropyl-2- methoxy- phenyl) pyrazin-2- yl]amino]butan- 1-ol 11.79042 2.97 035_0153_0286 [00019] 6-(3- amino- phenyl)-N- benzyl- pyrazin-2- amine 6.67663 2.53 035_0232_0005 [00020] 2-[[6-(4- aminophenyl) pyrazin-2- yl]amino]butan- 1-ol 21.05663 1.06 035_0153_0333 [00021] 3-[5-(3- furylmethyl- amino)- 3- pyridyl]phenol 10.89609 2.44 081_0284_2069 [00022] N-[3-[5-(3,4,5- trimethoxy- anilino)- 3- pyridyl]phenyl] acetamide 0.3913 2.61 081_0087_0081 [00023] 3-[(3- methoxyphenyl) methyl]-5- (3,4,5- trimethoxy- phenyl)-1H- imidazo[4,5- b]pyrazin-2-one 23.44 3.07 170_4313_0087 [00024] N,N-dimethyl-3- [2-oxo-3-[(1S)- 1-phenylethyl]- 1H-imidazo[4,5- b]pyrazin-5- yl]benzamide 1.77669 3.42 170_0148_0349 [00025] 5-[3- (dimethylamino) phenyl]-N-(4- morpholino- phenyl) imidazo]1,2- a]pyrazin-8- amine 2.70242 3.14 184_0088_0135 [00026] N-(2- methoxyethyl)- 3-(3- thienyl)imidazo [1,2-b]pyridazin- 6-amine 5.2312 2.02 229_0033_0074 [00027] 3-(3,4- dimethoxy- phenyl)- N-(2- methoxyethyl) imidazo[1,2- b]pyridazin-6- amine 1.54534 1.93 229_0033_0079 [00028] 3-(4- fluorophenyl)-N- (2- methoxyethyl) imidazo[1,2- b]pyridazin-6- amine 4.00393 2.38 229_0033_0339 [00029] 4-[6-(2- furylmethyl- amino) imidazo[1,2- b]pyridazin-3- yl]benzoic acid 3.879 2.73 229_0144_0140 [00030] N-(2- furylmethyl)-3- (4- methoxyphenyl) imidazo[1,2- b]pyridazin-6- amine 3.67644 2.91 229_0144_0280 [00031] [4-[6-(2- furylmethyl- amino) imidazo[1,2- b]pyridazin-3- yl]phenyl] methanol 2.20497 2.30 229_0144_0285 [00032] [3-[6-(2- furylmethyl- amino) imidazo[1,2- b]pyridazin-3- yl]phenyl] methanol 3.85557 2.30 229_0144_0291 [00033] 1-[3-[6-(2- furylmethyl- amino) imidazo[1,2- b]pyridazin-3- yl]phenyl] ethanone 0.99711 2.63 229_0144_4145 [00034] [4-[6-(2- thienylmethyl- amino) imidazo[1,2- b]pyridazin-3- yl]phenyl] methanol 1.09479 3.16 229_0146_0285 [00035] 3-(4- aminophenyl)- N-(2- thienylmethyl) imidazo[1,2- b]pyridazin-6- amine 5.42153 3.10 229_0146_0333 [00036] 3-(4- fluorophenyl)-N- (2- thienylmethyl) imidazo[1,2- b]pyridazin-6- amine 3.28447 4.07 229_0146_0339 [00037] 3-(3- methoxyphenyl)- N-(2- thienylmethyl) imidazo[1,2- b]pyridazin-6- amine 2.94644 3.77 229_0146_4140 [00038] 1-[3-[6-(2- thienylmethyl amino)imidazo [1,2- b]pyridazin-3- yl]phenyl] ethanone 0.44073 3.48 229_0146_4145 [00039] 2-[[3-(3,4,5- trimethoxy- phenyl) imidazo[1,2- b]pyridazin-6- yl]amino]butan- 1-ol 1.2806 2.06 229_0153_0087 [00040] 2-[[3-(4- methoxyphenyl) imidazo[1,2- b]pyridazin-6- yl]amino]butan- 1-ol 1.27502 2.38 229_0153_0280 [00041] 2-[[3-[4- (hydroxymethyl) phenyl]imidazo [1,2-b]pyridazin- 6- yl]amino]butan- 1-ol 2.46631 1.77 229_0153_0285 [00042] 2-[[3-(6- methoxy-3- pyridyl)imidazo [1,2-b]pyridazin- 6- yl]amino]butan- 1-ol 2.36648 1.76 229_0153_0311 [00043] 2-[[3-(3- methoxyphenyl) imidazo[1,2- b]pyridazin-6- yl]amino]butan- 1-ol 1.55019 1.76 229_0153_4140 [00044] [3-[6-[(3- chlorophenyl) methylamino] imidazo[1,2- b]pyridazin-3- yl]phenyl] methanol 5.10524 3.85 229_0223_0291 [00045] 3-(4- aminophenyl)-N- [(3- chlorophenyl) methyl] imidazo[1,2- b]pyridazin-6- amine 3.41043 3.79 229_0223_0333 [00046] [4-[6-[(4- fluorophenyl) methylamino] imidazo[1,2- b]pyridazin-3- yl]phenyl] methanol 2.4449 3.39 229_0224_0285 [00047] N-(1,3- benzodioxol-5- ylmethyl)-3-(4- pyridyl)imidazo [1,2-b]pyridazin- 6-amine 0.37966 2.42 229_0236_0069 [00048] 4-[6-(1,3- benzodioxol-5- ylmethylamino) imidazo[1,2- b]pyridazin-3- yl]phenol 5.67256 3.33 229_0236_0080 [00049] 3-(benzofuran- 2-yl)-N-(4- pyridylmethyl) imidazo[1,2- b]pyridazin-6- amine 6.44995 2.87 229_0237_0073 [00050] 3-(3- aminophenyl)- N- tetrahydropyran- 4-yl- imidazo[1,2- b]pyridazin-6- amine 0.74599 1.42 229_0242_0005 [00051] 3-(3,4- dimethoxy- phenyl)-N- tetrahydropyran- 4-yl- imidazo[1,2- b]pyridazin-6- amine 0.54713 1.93 229_0242_0079 [00052] N-[3-[6- (tetrahydropyran- 4- ylamino)imidazo [1,2-b]pyridazin- 3- yl]phenyl] acetamide 0.58811 1.49 229_0242_0081 [00053] N- tetrahydropyran- 4-yl-3-(3,4,5- trimethoxy- phenyl) imidazo[1,2- b]pyridazin-6- amine 0.61737 1.78 229_0242_0087 [00054] 3-(1H-indol-5- yl)-N- tetrahydropyran- 4-yl- imidazo[1,2- b]pyridazin-6- amine 1.16563 2.35 229_0242_0204 [00055] 3-(3- methoxyphenyl)- N- tetrahydropyran- 4-yl-imidazo[1,2- b]pyridazin-6- amine 0.87042 2.09 229_0242_4140 [00056] 2-methoxy-4-[6- [(4- methoxyphenyl) methylamino] imidazo[1,2- b]pyridazin-3- yl]phenol 4.01326 3.39 229_0244_0314 [00057] 3-[[3-(1,3- benzodioxol-5- yl)imidazo[1,2- b]pyridazin-6- yl]amino] propan- 1-ol 0.9286 1.28 229_0248_0068 [00058] 3-[[3-(1H-indol- 5- yl)imidazo[1,2- b]pyridazin-6- yl]amino] propan- 1-ol 2.71742 1.76 229_0248_0204 [00059] 3-[[3-[3- (trifluoromethyl) phenyl]imidazo [1,2-b]pyridazin- 6- yl]amino] propan- 1-ol 3.41334 2.54 229_0248_0312 [00060] 4-[6-(3- hydroxypropyl- amino)imidazo [1, 2-b]pyridazin-3- yl]-2-methoxy- phenol 0.32856 1.20 229_0248_0314 [00061] 3-[[3-(4- phenoxyphenyl) imidazo[1,2- b]pyridazin-6- yl]amino] propan- 1-ol 5.54336 3.16 229_0248_1029 [00062] (2S)-2-[[3-(3- aminophenyl) imidazo[1,2- b]pyridazin-6- yl]amino]-3- methyl-butan-1- ol 1.80698 2.07 229_0254_0005 [00063] (2S)-2-[[3-(1,3- benzodioxol-5- yl)imidazo[1,2- b]pyridazin-6- yl]amino]-3- methyl-butan-1- ol 1.82017 2.52 229_0254_0068 [00064] (2S)-2-[[3-(3,4- dimethoxy- phenyl) imidazo[1,2- b]pyridazin-6- yl]amino]-3- methyl-butan-1- ol 0.7782 2.59 229_0254_0079 [00065] N-[3-[6-[[(1S)-1- (hydroxy- methyl)- 2-methyl- propyl]amino] imidazo[1,2- b]pyridazin-3- yl]phenyl] acetamide 0.80076 2.14 229_0254_0081 [00066] 4-[6-[[(1S)-1- (hydroxy- methyl)- 2-methyl- propyl]amino] imidazo[1,2- b]pyridazin-3- yl]benzonitrile 3.17911 2.76 229_0254_0086 [00067] (2S)-2-[[3-(4- aminophenyl) imidazo[1,2- b]pyridazin-6- yl]amino]-3- methyl-butan-1- ol 3.05172 2.07 229_0254_0333 [00068] 3-(1,3- benzodioxol-5- yl)-N-(2- pyridylmethyl) imidazo[1,2- b]pyridazin-6- amine 0.79705 2.50 229_4007_0068 [00069] N- (cyclopropyl- methyl)-3-(3- methoxyphenyl) imidazo[1,2- b]pyridazin-6- amine 3.29534 2.91 229_4051_4140 [00070] 3-[5-[(6- methoxy-3- pyridyl)amino] pyrazolo[1,5- a]pyrimidin-3- yl]phenol 3.39371 3.25 294_0042_0284 [00071] 3-(3- methoxyphenyl)- N-(6-methoxy- 3- pyridyl)pyrazolo [1,5-a]pyrimidin- 5-amine 5.3146 3.40 294_0042_4140 [00072] 1-[3-[5-[(6- methoxy-3- pyridyl)amino] pyrazolo[1,5- a]pyrimidin-3- yl]phenyl] ethanone 1.63557 3.11 294_0042_4145 [00073] N-[5-[[3-(3- hydroxyphenyl) pyrazolo[1,5- a]pyrimidin-5- yl]amino]-2- methyl- phenyl]methane- sulfonamide 3.17096 2.92 294_0123_0284 [00074] 3-(3,4- dimethoxy- phenyl)-N-(3- pyridylmethyl) pyrazolo[1,5- a]pyrimidin-5- amine 1.63605 2.56 294_4003_0079 [00075] N-(3- pyridylmethyl)- 3-(3,4,5- trimethoxy- phenyl) pyrazolo[1,5- a]pyrimidin-5- amine 2.35332 2.40 294_4003_0087 [00076] N-(4- isopropyl- phenyl)- 3-(4- methoxyphenyl) pyrazolo[1,5- a]pyrimidin-5- amine 4.17999 5.42 294_6937_0280 [00077] N-(2- furylmethyl)-3- phenyl- imidazo[1,2- b]pyridazin-6- amine 6.37501 3.07 229_0144_0061 [00078] N-(2- furylmethyl)-3- (3,4,5- trimethoxy- phenyl) imidazo[1,2- b]pyridazin-6- amine 4.89592 2.60 229_0144_0087 [00079] 3-(3- aminophenyl)- N-(2- thienylmethyl) imidazo[1,2- b]pyridazin-6- amine 1.79421 3.10 229_0146_0005 [00080] N-(2- thienylmethyl)- 3-(3,4,5- trimethoxy- phenyl) imidazo[1,2- b]pyridazin-6- amine 3.10009 3.45 229_0146_0087 [00081] 3-(4- methoxy- phenyl)- N-(2- thienylmethyl) imidazo[1,2- b]pyridazin-6- amine 5.3884 3.77 229_0146_0280 [00082] 3-[6-(2- thienylmethyl- amino)imidazo [1,2- b]pyridazin-3- yl]phenol 1.70365 3.62 229_0146_0284 [00083] 2-[[3-(2- thienyl)imidazo [1,2-b] pyridazin- 6- yl]amino]butan- 1-ol 3.96823 2.31 229_0153_4147 [00084] N-[(3- chlorophenyl) methyl]-3-(4- methoxyphenyl) imidazo[1,2- b]pyridazin-6- amine 10.74649 4.46 229 _ 0223 _0280 [00085] N-[(3- chlorophenyl) methyl]-3-(6- methoxy-3- pyridyl)imidazo [1,2-b]pyridazin- 6-amine 8.33916 3.84 229_0223_0311 [00086] 4-[6-[(3- chlorophenyl) methylamino] imidazo[1,2- b]pyridazin-3- yl]-2-methoxy- phenol 3.51753 4.15 229_0223_0314 [00087] 3-(3- aminophenyl)- N-propyl- imidazo[1,2- b]pyridazin-6- amine 0.93247 2.34 229_0226_0005 [00088] 3-(1,3- benzodioxol-5- yl)-N-propyl- imidazo[1,2- b]pyridazin-6- amine 2.05098 2.79 229_0226_0068 [00089] N-propyl-3-(3- thienyl)imidazo [1,2-b] pyridazin- 6-amine 4.03981 2.95 229_0226_0074 [00090] 3-(3,4- dimethoxyphen- yl)-N-propyl- imidazo[1,2- b]pyridazin-6- amine 0.51897 2.85 229_0226_0079 [00091] N-[3-[6- (propylamino) imidazo[1,2- b]pyridazin-3- yl]phenyl] acetamide 0.62919 2.40 229_0226_0081 [00092] 4-[6- (propylamino) imidazo[1,2- b]pyridazin-3- yl]benzoic acid 9.76838 2.82 229_0226_ 0140 [00093] 3-(4- methoxyphenyl)- N-propyl- imidazo[1,2- b]pyridazin-6- amine 5.42987 3.01 229_0226_0280 [00094] 3-[6- (propylamino) imidazo[1,2- b]pyridazin-3- yl]phenol 0.93003 2.86 229_0226_0284 [00095] 3-(3- methoxyphenyl)- N-propyl- imidazo[1,2- b]pyridazin-6- amine 2.21992 3.01 229_0226_4140 [00096] 1-[3-[6- (propylamino) imidazo[1,2- b]pyridazin-3- yl]phenyl] ethanone 0.36718 2.72 229_0226_4145 [00097] 4-[6-[(3,4- dichlorophenyl) methylamino] imidazo[1,2- b]pyridazin-3- yl]benzoic acid 1.00617 4.88 229_0227_0140 [00098] 3-phenyl-N-(4- pyridylmethyl) imidazo[1,2- b]pyridazin-6- amine 4.05638 2.79 229_0237_0061 [00099] 3-(4- aminophenyl)- N- tetrahydropyran- 4-yl- imidazo[1,2- b]pyridazin-6- amine 3.12587 1.42 229_0242_0333 [00100] 4-[6-[(2,4- dimethylphenyl) methylamino] imidazo[1,2- b]pyridazin-3- yl]-2-methoxy- phenol 5.30595 4.58 229_4319_0314 [00101] 3-(5-methoxy-3- pyridyl)-N-(4- morpholinophen- yl)pyrazolo[1,5- a]pyrimidin-5- amine 2.24998 2.85 294_0088_0196 [00102] 3-(3- aminophenyl)- N-(3- pyridylmethyl) pyrazolo[1,5- a]pyrimidin-5- amine 2.5122 2.05 294_4003_0005 [00103] 3-(2- methoxyphenyl)- N-(3- pyridylmethyl) pyrazolo[1,5- a]pyrimidin-5- amine 1.22114 2.72 294_4003_0083 [00104] N-[3- (dimethylamino) propyl]-3-[6-(4- methoxyphenyl) pyrazin-2- yl]benzamide 9.05883 2.60 035_0280_0302 [00105] 2-methoxy-4-[6- (4- methoxyphenyl) pyrazin-2- yl]phenol 5.17907 2.99 035_0280_0314 [00106] N-[3-[6-(4- methoxyphenyl) pyrazin-2- yl]phenyl] acetamide 3.50136 2.68 035_ 0081_0280 [00107] N-[3-[6-(3- hydroxyphenyl) pyrazin-2- yl]phenyl] acetamide 3.87844 2.54 035_0081_0284 [00108] N-[3- (dimethylamino) propyl]-4-[6-(2- fluoro-3- methoxy- phenyl)-1H- pyrazolo[3,4- b]pyridin-3- yl]benzamide 7.3354 3.65 267_0180_7936 [00109] 3-[2-amino-5- (3,4- dimethoxyphen yl)-3- pyridyl]phenol 2.00489 3.20 382_0284_0079 [00110] 3-[6-amino-5-[3- (dimethylamino) phenyl]-3- pyridyl]-N-(2- hydroxyethyl) benzamide 3.57159 2.31 382_0135_0192 [00111] 5-(3- methoxyphenyl)- 3-(3,4,5- trimethoxyphen- yl)pyridin-2- amine 9.5028 3.18 382_0087_4140 [00112] 4-[2-amino-5-(4- methylsulfonyl- phenyl)-3- pyridyl]-2- methoxy-phenol 0.34919 2.19 382_0314_0174 [00113] 4-[2-amino-5-(p- tolyl)-3-pyridyl]- 2-methoxy- phenol 4.3442 3.87 382_0314_4139 [00114] 4-[2-amino-5-(3- chlorophenyl)-3- pyridyl]-2- methoxy-phenol 3.5107 3.96 382_0314_0279 [00115] 4-[2-amino-5-(3- fluorophenyl)-3- pyridyl]-2- methoxy-phenol 2.02739 3.50 382_0314_0313 [00116] 4-(2-amino-5- phenyl-3- pyridyl)-2- methoxy-phenol 1.47705 3.35 382_0314_0061 [00117] 4-[6-amino-5-(4- hydroxy-3- methoxy- phenyl)-3- pyridyl]-2,6- dimethyl-phenol 0.52648 4.08 382_0314_0315 [00118] 4-[2-amino-5-(4- fluorophenyl)-3- pyridyl]-2- methoxy-phenol 3.24026 3.50 382_0314_0339 [00119] 4-[2-amino-5- (3,4,5- trimethoxyphen- yl)-3-pyridyl]-2- methoxy-phenol 0.08059 2.88 382_0314_0087 [00120] 4-[6-amino-5-[4- (methoxy- methoxy) phenyl]-3- pyridyl] benzamide 3.42268 2.57 382_0341_0346 [00121] [3-[6-amino-5- [4- (methoxy- methoxy) phenyl]-3- pyridyl]phenyl] methanol 4.62016 2.95 382_0341_0291 [00122] 3-[6-amino-5-[4- (methoxy- methoxy) phenyl]-3- pyridyl] benzamide 3.02265 2.57 382_0341_0347 [00123] N-[3-[6-amino- 5-[4- (methoxy- methoxy) phenyl]-3- pyridyl]phenyl] acetamide 1.5493 2.96 382_0341_0081 [00124] 4-[6-amino-5-[4- (hydroxymethyl) phenyl]-3- pyridyl]-2,6- dimethyl-phenol 4.64395 3.77 382_0285_0315 [00125] 3-[4- (methoxy- methoxy) phenyl]-5- (3,4,5- trimethoxy- phenyl) pyridin-2- amine 1.90467 3.25 382_0341_0087 [00126] 3-[2-amino-5-(4- morpholinophen- yl)-3- pyridyl]phenol 4.64154 3.40 382_0284_0001 [00127] N-[3-[6-amino- 5-(4- hydroxyphenyl)- 3- pyridyl]phenyl] acetamide 0.83784 2.75 382_7249_0081 [00128] 4-[2-amino-5- (3,4,5- trimethoxyphen- yl)-3- pyridyl]phenol 0.20886 3.04 382_7249_0087 [00129] 4-[2-amino-5-[3- (dimethylamino) phenyl]-3- pyridyl]phenol 2.19069 3.62 382_7249_0135 [00130] 3-[2-amino-5- (3,4,5- trimethoxyphen- yl)-3- pyridyl]phenol 1.01519 3.04 382_0284_0087 [00131] 4-[2-amino-5-(4- methylsulfonyl- phenyl)-3- pyridyl]phenol 1.25339 2.35 382_7249_0174 [00132] 3-(3- aminophenyl)-5- (3,4,5- trimethoxyphen- yl)pyridin-2- amine 2.96823 2.51 382_0005_0087 [00133] 4-[2-amino-5-(3- methoxyphenyl)- 3- pyridyl]phenol 3.49074 3.35 382_7249_4140 [00134] 4-[6-amino-5-(4- pyridyl)-3- pyridyl]-2,6- dimethyl-phenol 1.70457 3.32 382_0069_0315 [00135] 5-[6-[3- (dimethylamino) propoxy]-3- pyridyl]-3-(3,4,5- trimethoxyphen- yl)pyridin-2- amine 0.5304 2.64 382_0087_0002 [00136] 5-(3- fluorophenyl)-3- (3,4,5- trimethoxyphen- yl)pyridin-2- amine 1.5198 3.49 382_0087_0313 [00137] 4-[6-amino-5- (3,4,5- trimethoxyphen- yl)-3-pyridyl]- 2,6-dimethyl- phenol 0.71164 4.07 382_0087_0315 [00138] N-[3-[6-amino- 5-(3,4,5- trimethoxyphen- yl)-3- pyridyl]phenyl] methane- sulfonamide 0.5248 1.72 382_0087_6488 [00139] 5-phenyl-3- (3,4,5- trimethoxyphen- yl)pyridin-2- amine 0.8934 3.34 382_0087_0061 [00140] 3-[6-amino-5- (3,4,5- trimethoxyphen- yl)-3-pyridyl]-N- (2- hydroxyethyl) benzamide 0.48532 1.73 382_0087_0192 [00141] 5-(4- aminophenyl)-3- (3,4,5- trimethoxyphen- yl)pyridin-2- amine 0.97087 2.51 382_0087_0333 [00142] 4-[6-amino-5- (3,4,5- trimethoxyphen- yl)-3- pyridyl]phenol 1.72584 3.04 382_0087_7249 [00143] 5-(4- fluorophenyl)-3- (3,4,5- trimethoxyphen- yl)pyridin-2- amine 2.85921 3.49 382_0087_0339 [00144] 4-[6-amino-5- (3,4,5- trimethoxyphen- yl)-3-pyridyl]-N- cyclopropyl- benzamide 0.5072 2.88 382_0087_7489 [00145] 5- (benzothiophen- trimethoxyphen- yl)pyridin-2- amine 2.69043 4.22 382_0087_0076 [00146] 3-[6-amino-5- (3,4,5- trimethoxyphen- yl)-3- pyridyl]phenol 0.72322 3.04 382_0087_0284 [00147] 5-(6-methoxy-3- pyridyl)-3- (3,4,5- trimethoxyphen- yl)pyridin-2- amine 1.06095 2.56 382_0087_0311 [00148] 5-[3- (dimethylamino) phenyl]-3- (3,4,5- trimethoxyphen- yl)pyridin-2- amine 0.59506 3.45 382_0087_0135 [00149] [3-[6-amino-5- [3- (dimethylamino) phenyl]-3- pyridyl]phenyl]- (4- methylpiperazin- 1-yl)methanone 4.43871 3.07 382_0135_0200 [00150] 4-[6-amino-5-[3- (dimethylamino) phenyl]-3- pyridyl]-2- methoxy-phenol 2.10895 3.46 382_0135_0314 [00151] 3-[3- (dimethylamino) phenyl]-5- (3,4,5- trimethoxyphen- yl)pyridin-2- amine 3.13462 3.45 382_0135_0087 [00152] 4-[6-amino-5-[3- (dimethylamino) phenyl]-3- pyridyl]-2,6- dimethyl-phenol 4.20127 4.65 382_0135_0315 [00153] 3-[3- (dimethylamino) phenyl]-5-(3- pyridyl)pyridin- 2-amine 7.11159 2.71 382_0135_0071 [00154] [3-[6-amino-5- [3- (dimethylamino) phenyl]-3- pyridyl]phenyl] methanol 2.6979 3.16 382_0135_0291 [00155] 3-[3- (dimethylamino) phenyl]-5-[6-[3- (dimethylamino) propoxy]-3- pyridyl]pyridin- 2-amine 4.66462 3.22 382_0135_0002 [00156] 3-[6-amino-5-[3- (dimethylamino) phenyl]-3- pyridyl] benzamide 3.52109 2.77 382_0135_0347 [00157] 5-(3,4- dimethoxyphen- yl)-3-[3- (dimethylamino) phenyl]pyridin- 2-amine 5.04712 3.61 382_0135_0079 [00158] 4-[2-amino-5-(3- chloro-4-fluoro- phenyl)-3- pyridyl]-2- methoxy-phenol 11.34048 4.10 382_0314_0164 [00159] 5-(4- methoxyphenyl)- 3-(3,4,5- trimethoxyphen- yl)pyridin-2- amine 2.97729 3.18 382_0087_0280 [00160] 4-[2-amino-5-(4- methoxyphenyl)- 3-pyridyl]-2- methoxy-phenol 4.15847 3.20 382_0314_0280 [00161] 5-(3-furyl)-3- (3,4,5- trimethoxyphen- yl)pyridin-2- amine 12.0965 2.48 382_0087_0343 [00162] 5-(2- phenoxyphenyl)- 3-(3,4,5- trimethoxyphen- yl)pyridin-2- amine 9.00592 4.84 382_0087_0063 [00163] 4-[6-amino-5- (3,4,5- trimethoxyphen- yl)-3- pyridyl] benzamide 0.40043 2.19 382_0087_0346 [00164] 4-[2-amino-5-(3- methoxyphenyl)- 3-pyridyl]-2- methoxy-phenol 1.19944 3.20 382_0314_4140 [00165] [4-[2-amino-5- (3,4- dimethoxyphen- yl)-3- pyridyl]phenyl] methanol 5.13242 2.73 382_0285_0079 [00166] 5-[4-(4- methylpiperazin- 1-yl)phenyl]-3- (3,4,5- trimethoxyphen- yl)pyridin-2- amine 0.32234 3.30 382_0087_0218 [00167] 3-(4- fluorophenyl)-N- methyl- imidazo[1,2- b]pyridazin-6- amine 3.25909 2.43 437_0339 [00168] 3-(4- methoxyphenyl)- N-methyl- imidazo[1,2- b]pyridazin-6- amine 4.15763 2.13 437_0280 [00169] 2-[6- (methylamino) imidazo[1,2- b]pyridazin-3- yl]phenol 1.13395 1.98 437_0340 [00170] N-methyl-3-(3- thienyl)imidazo [1,2-b]pyridazin- 6-amine 4.23169 2.07 437_0074 [00171] 3-[6- (methylamino) imidazo[1,2- b]pyridazin-3- yl]phenol 2.17588 1.98 437_0284 [00172] 3-(3,4- dimethoxyphen- yl)-N-methyl- imidazo[1,2- b]pyridazin-6- amine 1.24313 1.97 437_0079 [00173] N,N-dimethyl-3- [6- (methylamino) imidazo[1,2- b]pyridazin-3- yl]benzamide 2.94156 1.59 437_0349 [00174] N-methyl-3-(1- methylpyrazol- 4- yl)imidazo[1,2- b]pyridazin-6- amine 5.63446 0.72 437_7468 [00175] N-[3-[6- (methylamino) imidazo[1,2- b]pyridazin-3- yl]phenyl] acetamide 1.75426 1.53 437_0081 [00176] 3-(6-methoxy-3- pyridyl)-N- methyl- imidazo[1,2- b]pyridazin-6- amine 4.46164 1.51 437_0311 [00177] 6-(1H-indol-5- yl)-N-methyl- pyrazin-2-amine 14.9424 1.74 445_0204 [00178] N-ethyl-2-(3,4,5- trimethoxy- anilino)- 7,8-dihydro- 5H-pyrido[4,3- d]pyrimidine-6- carboxamide 4.24682 1.18 582_9377_5725 [00179] 6-propyl-N- (3,4,5- trimethoxyphen- yl)-7,8-dihydro- 5H-pyrido[4,3- d]pyrimidin-2- amine 14.67829 2.59 582_9377_5632 [00180] [2-[3- (dimethylamino) anilino]-5,7- dihydropyrrolo[3, 4-d]pyrimidin-6- yl]-(2- methoxyphenyl) methanone 10.08397 2.97 585_9372_5053 [00181] N-(2- hydroxyethyl)-4- [3-(4- hydroxyphenyl) imidazo[1,2- a]pyrazin-6- yl+benzamide 0.64093 1.22 388_0080_0328 [00182] 3-[3-(4- hydroxyphenyl) imidazo[1,2- a]pyrazin-6-yl]- N,N-dimethyl- benzamide 0.97398 2.14 388_0080_0349 [00183] 4-[6-[4-(4- isopropyl- piperazin-1- yl)phenyl] imidazo [1,2-a]pyrazin- 3-yl]phenol 0.63733 3.57 388_0080_0182 [00184] 4-[6-(1- benzylpyrazol- 4- yl)imidazo[1,2- a]pyrazin-3- yl]phenol 6.6194 2.99 388_0080_7469 [00185] 4-[3-(2- thienyl)imidazo [1,2-a]pyrazin-6- yl]phenol 6.25235 2.62 388_4147_0080 [00186] 3,6-bis(2- thienyl)imidazo [1,2-a]pyrazine 5.02752 2.70 388_4147_4147 [00187] N-(2- hydroxyethyl)-3- [3-(4- hydroxyphenyl) imidazo[1,2- a]pyrazin-6- yl]benzamide 1.03081 1.22 388_0080_0192 [00188] N-cyclopropyl-4- [3-(4- hydroxyphenyl) imidazo[1,2- a]pyrazin-6- yl]benzamide 1.95812 2.38 388_0080_7489 [00189] 4-[6-[4-(4- methylpiperazin- 1- yl)phenyl] imidazo [1,2-a]pyrazin- 3-yl]phenol 0.67809 2.79 388_0080_0218 [00190] 4-[6-(6-amino-3- pyridyl)imidazo [1,2-a]pyrazin-3- yl]phenol 1.9327 1.39 388_0080_7905 [00191] 5-[3-(2- thienyl)imidazo [1,2-a]pyrazin-6- yl]pyridin-2- amine 8.16191 1.47 388_4147_7905 [00192] 4-[3-(3- acetylphenyl) imidazo[1,2- a]pyrazin-6-yl]- N-(2- dimethylamino- ethyl)benzamide 4.07021 1.79 388_4145_0327 [00193] N-(2- dimethylamino- ethyl)-4-[3-(2- thienyl)imidazo [1,2-a]pyrazin-6- yl]benzamide 8.52139 2.01 388_4147_0327 [00194] 4-[3-(3,5- dimethoxyphen yl)imidazo[1,2- a]pyrazin-6-yl]- N-[3- (dimethylamino) propyl] benzamide 6.69112 1.98 388_7492_0180 [00195] N-(2- dimethylamino- ethyl)-4-[3-(4- pyridyl)imidazo [1,2-a]pyrazin-6- yl]benzamide 6.90909 1.02 388_0069_0327 [00196] 4-[6-[2- (dimethylamino) phenyl]imidazo [1,2-a]pyrazin-3- yl]-2-methoxy- phenol 1.75434 2.79 388_0314_0006 [00197] N-(2- hydroxyethyl)-3- [3-(4-hydroxy-3- methoxy- phenyl)imidazo [1,2-a]pyrazin-6- yl]benzamide 0.8957 1.07 388 _ 0314 _ 0192 [00198] 2-methoxy-4-[6- (3- pyridyl)imidazo [1,2-a]pyrazin-3- yl]phenol 3.06577 1.46 388_0314_0071 [00199] 4-[6-(2- chlorophenyl) imidazo[1,2- a]pyrazin-3-yl]- 2-methoxy- phenol 2.53905 3.28 388_0314_4027 [00200] 4-[6-(3- ethoxyphenyl) imidazo[1,2- a]pyrazin-3-yl]- 2-methoxy- phenol 1.36347 2.88 388_0314_0205 [00201] N-(2- dimethylamino- ethyl)-4-[3-(4- hydroxy-3- methoxy- phenyl)imidazo [1,2-a]pyrazin-6- yl]benzamide 0.44033 1.77 388_0314_0327 [00202] 4-[6-(6-amino-3- pyridyl)imidazo [1,2-a]pyrazin-3- yl]-2-methoxy- phenol 1.41172 1.23 388_0314_7905 [00203] 2-methoxy-4-[6- [6-(4- methylpiperazin- 1-yl)-3- pyridyl]imidazo [1,2-a]pyrazin-3- yl]phenol 1.13372 2.01 388 _0314 _0016 [00204] 2-methoxy-4-[6- (1- methylpyrazol- 4- yl)imidazo[1,2- a]pyrazin-3- yl]phenol 0.74595 1.11 388_0314_8400 [00205] N-[3-[3-(3,4,5- trimethoxyphen- yl)imidazo[1,2- a]pyrazin-6- yl]phenyl]meth- anesulfonamide 2.79564 1.04 388_0087_6488 [00206] N-[3- (dimethylamino) propyl]-4-[3-(4- hydroxy-3- methoxy- phenyl)imidazo [1,2-a]pyrazin-6- yl]benzamide 0.60574 1.83 388_0314_0180 [00207] 2-methoxy-4-[6- [6-(2- morpholinoethyl- amino)-3- pyridyl]imidazo [1,2-a]pyrazin-3- yl]phenol 1.35363 1.33 388 _0314 _0003 [00208] 6-(1- methylpyrazol- 4-yl)-3-(3- thienyl)imidazo [1,2-a]pyrazine 6.37648 1.35 388_0074_8400 [00209] 6-phenyl-3-(3- thienyl)imidazo [1,2-a]pyrazine 3.94995 2.92 388_0074_0061 [00210] [4-[3-(3- thienyl)imidazo [1,2-a]pyrazin-6- yl]phenyl]metha- nol 2.3518 2.16 388_0074_0285 [00211] 4-[3-(4- methoxyphenyl) imidazo[1,2- a]pyrazin-6- yl]phenol 10.45826 2.68 388_0280_0080 [00212] 6-(3-pyridyl)-3- (3- thienyl)imidazo [1,2-a]pyrazine 4.33598 1.70 388_0074_0071 [00213] 3-(4-pyridyl)-6- (2- thienyl)imidazo [1,2-a]pyrazine 5.68757 1.70 388_0069_4147 [00214] 4-[3-(3- thienyl)imidazo [1,2-a]pyrazin-6- yl]phenol 2.70168 2.62 388_0074_0080 [00215] 6-(2-thienyl)-3- (3- thienyl)imidazo [1,2-a ]pyrazine 2.24904 2.70 388_0074_4147 [00216] N-[3-[3-(3- thienyl)imidazo [1,2-a]pyrazin-6- yl]phenyl] acetamide 2.32941 2.16 388_0074_0081 [00217] N-[3-[3-(3- thienyl)imidazo [1,2-a]pyrazin-6- yl]phenyl]meth- anesulfonamide 3.32047 1.30 388_0074_6488 [00218] 6-(2-furyl)-3-(3- thienyl)imidazo [1,2-a]pyrazine 6.25008 1.98 388_0074_0142 [00219] 3-(6- phenylimidazo[1, 2-a]pyrazin-3- yl)phenol 6.54588 2.84 388_0284_0061 [00220] 3-[3-(3- hydroxyphenyl) imidazo[1,2- a]pyrazin-6- yl]benzamide 1.58014 1.69 388_0284_0347 [00221] 4-[6-(3- pyridyl)imidazo [1,2-a]pyrazin-3- yl]phenol 2.72591 1.62 388_0080_0071 [00222] [4-[3-(4- phenoxyphenyl) imidazo[1,2- a]pyrazin-6- yl]phenyl]metha- nol 4.72246 3.88 388_1029_0285 [00223] 4-[6-(4- chlorophenyl) imidazo[1,2- a]pyrazin-3- yl]phenol 6.37838 3.44 388_0080_0160 [00224] 3-[6-(2- thienyl)imidazo [1,2-a]pyrazin-3- yl]phenol 2.78435 2.62 388_0284_4147 [00225] 6-(1- methylpyrazol- 4-yl)-3-(4- phenoxyphenyl) imidazo[1,2- a]pyrazine 1.92958 3.07 388_1029_8400 [00226] 3-[6-(2- furyl)imidazo[1, 2-a]pyrazin-3- yl]phenol 6.11196 1.90 388_0284_0142 [00227] 4-[6-(6- methoxy-3- pyridyl)imidazo 1,2-a]pyrazin-3- yl]phenol 1.97871 2.06 388_0080_0311 [00228] 3-[6-[4- (hydroxymethyl) phenyl]imidazo [1,2-a]pyrazin-3- yl]phenol 3.35687 2.07 388_0284_0285 [00229] 3-[6-(1- methylpyrazol- 4- yl)imidazo[1,2- a]pyrazin-3- yl]phenol 2.78229 1.27 388_0284_8400 [00230] 4-[6-(1- methylpyrazol- 4- yl)imidazo[1,2- a]pyrazin-3- yl]phenol 1.58926 1.27 388_0080_8400 [00231] 6-[6-(4- methylpiperazin- 1-yl)-3-pyridyl]- 3-(4- phenoxyphenyl) imidazo[1,2- a]pyrazine 2.13162 3.97 388_1029_0016 [00232] N-(2- hydroxyethyl)-3- [3-(4- phenoxyphenyl) imidazo[1,2- a ]pyrazin-6- yl]benzamide 1.48118 3.03 388_1029_0192 [00233] N-(2- dimethylamino- ethyl)-4-[3-(4- phenoxyphenyl) imidazo[1,2- a]pyrazin-6- yl]benzamide 0.1649 3.74 388_1029_0327 [00234] N-(2- hydroxyethyl)-4- [3-(4- phenoxyphenyl) imidazo[1,2- a]pyrazin-6- yl]benzamide 0.62307 3.03 388_1029_0328 [00235] 4-[3-(3- chlorophenyl) imidazo[1,2- a]pyrazin-6-yl]- N-[3- (dimethylamino) propyl] benzamide 8.43215 2.90 388_0279_0180 [00236] 5-[3-(4- phenoxyphenyl) imidazo[1,2- a]pyrazin-6- yl]pyridin-2- amine 1.71808 3.19 388_1029_7905 [00237] N-[3- (dimethylamino) propyl]-4-[3-(3- thienyl)imidazo [1,2-a]pyrazin-6- yl]benzamide 3.87213 2.08 388_0074_0180 [00238] 3-(4- methoxyphenyl)- 6-[4-(4- methylpiperazin- 1- yl)phenyl] imidazo [1,2-a]pyrazine 5.25112 2.94 388_0280_0218 [00239] N-(2- hydroxyethyl)-3- [3-(3- thienyl)imidazo 1,2-a]pyrazin-6- yl]benzamide 3.67126 1.31 388_0074_0192 [00240] 6-[6-(4- methylpiperazin- 1-yl)-3-pyridyl]- 3-(3- thienyl)imidazo [1,2-a]pyrazine 7.04574 2.25 388_0074_0016 [00241] 5-[3-(3- thienyl)imidazo [1,2-a]pyrazin-6- yl]pyridin-2- amine 2.45583 1.47 388_0074_7905 [00242] 3,6-bis(3- thienyl)imidazo [1,2-a]pyrazine 8.47406 2.70 388_0074_0074 [00243] N-(2- dimethylamino- ethyl)-4-[3-(3- thienyl)imidazo [1,2-a]pyrazin-6- yl]benzamide 1.89752 2.02 388_0074_0327 [00244] 3-(1- methylpyrazol- 4-yl)-6-(2- phenoxyphenyl) imidazo[1,2- a]pyrazine 1.81873 3.07 388_8400_0063 [00245] 3-[6-[6-(4- methylpiperazin- 1-yl)-3- pyridyl]imidazo [1,2-a]pyrazin-3- yl]phenol 3.14141 2.17 388_0284_0016 [00246] 3-[[5-[3-(1,3- benzodioxol-5- yl)imidazo[1,2- a]pyrazin-6-yl]- 2-pyridyl]oxy]- propan-1-amine 9.85132 2.06 388_0068_0002 [00247] 3-[6-(3- ethoxyphenyl) imidazo[1,2- a]pyrazin-3- yl]phenol 6.6859 3.04 388_0284 _0205 [00248] 3-(1,3- benzodioxol-5- yl)-6-[4-(4- methylpiperazin- 1- yl)phenyl] imidazo [1,2-a]pyrazine 7.93105 2.72 388_0068_0218 [00249] 3-[6-(3- thienyl)imidazo [1,2-a]pyrazin-3- yl]phenol 2.51787 2.62 388_0284_0074 [00250] 3-[6-[4-(4- methylpiperazin- 1- yl)phenyl] imidazo [1,2-a]pyrazin- 3-yl]phenol 1.58793 2.79 388_0284_0218 [00251] 4-[3-(4- chlorophenyl) imidazo[1,2- a]pyrazin-6-yl]- N-[3- (dimethylamino) propyl] benzamide 4.90272 2.90 388_0160_0180 [00252] 4-[3-(1,3- benzodioxol-5- yl)imidazo[1,2- a]pyrazin-6-yl]- N-(2- dimethylamino- ethyl) benzamide 3.79881 1.86 388_0068_0327 [00253] 3-[6-(6-amino-3- pyridyl)imidazo [1,2-a]pyrazin-3- yl]phenol 2.88877 1.39 388_0284_7905 [00254] N-(2- dimethylamino ethyl)-4-[3-(3- hydroxyphenyl) imidazo[1,2- a]pyrazin-6- yl]benzamide 0.81226 1.93 388_0284_0327 [00255] 4-[3-(4- chlorophenyl) imidazo[1,2- a]pyrazin-6-yl]- N-(2- dimethylamino- ethyl) benzamide 4.15862 2.84 388_0160_0327 [00256] 3-[6-[6-(2- morpholinoethyl amino)-3- pyridyl]imidazo [1,2-a]pyrazin-3- yl]phenol 2.93938 1.49 388_0284_0003 [00257] N-[3- (dimethylamino) propyl]-4-[3-(3- hydroxyphenyl) imidazo[1,2- a]pyrazin-6- yl]benzamide 1.61113 1.99 388_0284_0180 [00258] N-(2- hydroxyethyl)-4- [3-(3- hydroxyphenyl) imidazo[1,2- a]pyrazin-6- yl]benzamide 1.72336 1.22 388_0284_0328 [00259] 4-[3-(1,3- benzodioxol-5- yl)imidazo[1,2- a]pyrazin-6-yl]- N-[3- (dimethylamino) propyl] benzamide 6.03233 1.92 388_0068_0180 [00260] 6-[6-(4- methylpiperazin- 1-yl)-3-pyridyl]- 3-phenyl- imidazo[1,2- a]pyrazine 10.85328 2.47 388_0061_0016 [00261] 3-[6-[4-(4- isopropylpiper- azin-1- yl)phenyl] imidazo [1,2-a]pyrazin- 3-yl]phenol 2.61352 357 388_0284_0182 [00262] 5-[3-(1,3- benzodioxol-5- yl)imidazo[1,2- a]pyrazin-6- yl]pyridin-2- amine 10.2391 1.31 388_0068_7905 [00263] 4-[6-[6-[3- (dimethylamino) propoxy]-3- pyridyl]imidazo [1,2-a]pyrazin-3- yl]phenol 1.32178 2.14 388_0080_0002 [00264] 4-[6-[6-(2- morpholinoethyl- amino)-3- pyridyl]imidazo [1,2-a]pyrazin-3- yl]phenol 1.31444 1.49 388_0080_0003 [00265] 4-[6-[6-(4- methylpiperazin- 1-yl)-3- pyridyl]imidazo [1,2-a]pyrazin-3- yl]phenol 2.21078 2.17 388_0080_0016 [00266] 3-[2- (cyclohexyl- amino) imidazo[2,1- b][1,3,4]thia- diazol-5-yl]- N,N- dimethyl- benzamide 0.71795 3.60 699_0052_0349 [00267] N,N-dimethyl-3- [2-[2-(4- sulfamoylphenyl) ethylamino] imidazo[2,1- b][1,3,4]thia- diazol-5- yl]benzamide 0.9091 2.42 699_6182_0349 [00268] 3-[2-[(4- hydroxycyclo- hexyl)amino] imidazo[2,1- b][1,3,4]thia- diazol-5-yl]- N,N- dimethyl- benzamide 0.53282 2.22 699_0240_0349 [00269] 1-[3-[2-[(4- hydroxycyclo- hexyl)amino] imidazo[2,1- b][1,3,4]thia- diazol-5- yl]phenyl] ethanone 0.48712 2.48 699_0240_4145 [00270] 6-(3- chlorophenyl)-3- (3,4- dimethoxyphen- yl)pyrazolo[1,5- a]pyrimidin-7- amine 0.80424 3.50 DT2008- 0028664 [00271] N-[3-[2-(2- furylmethyl- amino) imidazo[2,1- b][1,3,4]thia- diazol-5- yl]phenyl] acetamide 4.56802 2.53 699_0144_0081 [00272] 3-[2- (cyclopropyl- methyl- amino)imidazo [2,1- b][1,3,4]thia- diazol-5-yl]- N,N- dimethyl- benzamide 0.97667 2.59 699_4051_0349 [00273] 3-[2- (isobutylamino) imidazo[2,1- b][1,3,4]thia- diazol-5-yl]- N,N- dimethyl- benzamide 0.28265 3.05 699_0149_0349 [00274] 3-[2-[(4- fluorophenyl) methylamino] imidazo[2,1- b][1,3,4]thia- diazol-5-yl]- N,N- dimethyl- benzamide 2.76099 3.67 699_0224_0349 [00275] N-[3-[2-(2- thienylmethyl- amino)imidazo [2,1- b][1,3,4]thia- diazol-5- yl]phenyl] acetamide 3.92554 3.38 699_0146_0081 [00276] 4-[2-[[5-(1- methylpyrazol- 4- yl)imidazo[2,1- b][1,3,4]thia- diazol-2- yl]amino]ethyl] benzenesulfon- amide 2.26191 1.55 699_6182_7468 [00277] 4-[[5-[3- (dimethylamino) phenyl]imidazo [2,1- b][1,3,4]thia- diazol-2- yl]amino]cyclo- hexanol 5.79421 3.03 699_0240_0135 [00278] N-[3-[2- (isobutylamino) imidazo[2,1- b][1,3,4]thia- diazol-5- yl]phenyl]meth- anesulfonamide 7.06833 2.12 699_0149_6488 [00279] 3-[2-(3- hydroxypropyl amino)imidazo[2, 1- b][1,3,4]thia- diazol-5- yl]benzamide 2.87875 0.73 699_0248_0347 [00280] 4-[2-[(4- hydroxycyclo- hexyl)amino] imidazo[2,1 b][1,3,4]thia- diazol-5-yl] phenol 3.804 2.62 699_0240_0080 [00281] 3-[2-(2- furylmethyl- amino) imidazo[2,1- b][1,3,4]thia- diazol-5- yl]benzamide 1.22619 2.14 699_0144_0347 [00282] 4-[2-[[5-(6- methoxy-3- pyridyl)imidazo [2,1- b][1,3,4]thia- diazol-2- yl]amino]ethyl] benzenesulfon- amide 2.61127 2.35 699_6182_0311 [00283] N,N-dimethyl-3- [2- (tetrahydropyran- 4- ylmethylamino) imidazo[2,1- b][1,3,4]thia- diazol-5- yl]benzamide 2.72692 2.23 699_0243_0349 [00284] N,N-dimethyl-3- [2-(o- tolylmethyl- amino) imidazo[2,1- b][1,3,4]thia- diazol-5- yl]benzamide 3.73043 4.04 699_8074_0349 [00285] N-isobutyl-5-(5- methoxy-3- pyridyl)imidazo [2,1- b][1,3,4]thia- diazol-2-amine 5.16693 2.38 699_0149_0196 [00286] N-(1,3- benzodioxol-5- ylmethyl)-5-(5- methoxy-3- pyridyl)imidazo [2,1- b][1,3,4]thia- diazol-2-amine 0.44781 2.48 699_0236_0196 [00287] N-[4-[3-(4- hydroxy-3- methoxy- phenyl)imidazo [1,2-b]pyridazin- 6- yl]phenyl] acetamide 0.16907 3.03 828_0314_0722 [00288] N-[3-[6-(1,3- benzodioxol-5- yl)imidazo[1,2- b]pyridazin-3- yl]phenyl] acetamide 1.16817 3.11 828_0081_0068 [00289] N-[3-[3-(1,3- benzodioxol-5- yl)imidazo[1,2- b]pyridazin-6- yl]phenyl] acetamide 1.10979 3.11 828_0068_0081 [00290] N-[3-(3- acetylphenyl)-6- [4-(morpholine- 4- carbonyl)phenyl] imidazo[1,2- a]pyridin-8- yl]acetamide 2.02757 1.85 802_4145_0337 [00291] N-[3-[6-[3- (trifluoro- methoxy) phenyl]imidazo [1,2- b]pyridazin-3- yl]phenyl] acetamide 1.5009 4.92 828_0081_0168 [00292] 1-[3-[6-(3,4- dimethoxy- phenyl) imidazo[1,2- b]pyridazin-3- yl]phenyl] ethanone 0.65302 3.50 828_4145_0079 [00293] N-[3-[6-(4- methylsulfonyl- phenyl)imidazo[1, 2-b]pyridazin-3- yl]phenyl] acetamide 1.08226 2.33 828_0081_0174 [00294] N-[3-[3-(3- acetamido- phenyl) imidazo[1,2- b]pyridazin-6- yl]phenyl] acetamide 0.55312 2.73 828_0081_0081 [00295] 3-[2-[(4- methoxyphenyl) methylamino] imidazo[2,1- b][1,3,4]thia- diazol-5-yl]- N,N- dimethyl- benzamide 2.33054 3.37 699_0244_0349 [00296] N-[3-[3-(3- acetylphenyl) imidazo[1,2- b]pyridazin-6- yl]phenyl] acetamide 0.6205 3.05 828_4145_0081 [00297] 4-[3-(3- acetamido- phenyl) imidazo[1,2- b]pyridazin-6- yl]benzamide 0.22155 2.34 828_0081_0346 [00298] N-[4-[3-(3- hydroxyphenyl) imidazo[1,2- b]pyridazin-6- yl]phenyl] acetamide 0.51873 3.19 828_0284_0722 [00299] N-[2-(4- pyridyl)ethyl]-5- (3,4,5- trimethoxyphen- yl)imidazo[2,1- b][1,3,4]thia- diazol-2-amine 1.77014 2.83 699_0039_0087 [00300] N-[3-(4- fluorophenyl)-6- [4-(morpholine- 4- carbonyl)phenyl] imidazo[1,2- a]pyridin-8- yl]formamide 3.59432 2.39 788_0339_0337 [00301] 3-[2- (benzylamino) imidazo[2,1- b][1,3,4]thia- diazol-5-yl]- N,N- dimethyl- benzamide 1.50507 3.53 699_0232_0349 [00302] 5-(6-methoxy-3- pyridyl)-N-(4- pyridylmethyl) imidazo[2,1- b][1,3,4]thia- diazol-2-amine 2.58601 2.23 699_0237_0311 [00303] N-[3-[3-[3- (hydroxymethyl) phenyl]imidazo [1,2-b]pyridazin- 6- yl]phenyl] acetamide 1.63929 2.72 828_0291_0081 [00304] 3-[2-(2- furylmethyl- amino) imidazo[2,1- b][1,3,4]thia- diazol-5-yl]- N,N- dimethyl- benzamide 2.46273 2.59 699_0144_0349 [00305] N-[3-[6-(4- dimethylamino- phenyl)imidazo [1, 2-b]pyridazin-3- yl]phenyl] acetamide 1.09863 3.60 828_0081_0004 [00306] N-[3-(3- acetylphenyl)-6- [4-(morpholine- 4- carbonyl)phenyl] imidazo[1,2- a]pyridin-8- yl]formamide 2.99487 1.80 788_4145_0337 [00307] N-[3-[3-(4- hydroxy-3- methoxy- phenyl)imidazo [1,2-b] pyridazin- 6- yl]phenyl] acetamide 0.10208 3.03 828_0314_0081 [00308] N-[3-[3-[4- (hydroxymethyl) phenyl]imidazo [1,2-b]pyridazin- 6- yl]phenyl]meth- anesulfonamide 0.83024 1.86 828_0285_6488 [00309] 1-[3-[6-(3- hydroxyphenyl) imidazo[1,2- b]pyridazin-3- yl]phenyl] ethanone 0.99396 3.51 828_4145_0284 [00310] [4-[3-[3- (hydroxymethyl) phenyl]imidazo [1,2-b] pyridazin- 6- yl]phenyl] methanol 2.22994 2.72 828_0291_0285 [00311] 4-[3-[3- (hydroxymethyl) phenyl]imidazo [1,2-b] pyridazin- 6-yl]benzamide 1.89185 2.34 828_0291_0346 [00312] N-(2- dimethylamino- ethyl)-3-[6-[4- (hydroxymethyl) phenyl]imidazo [1,2-b]pyridazin- 3-yl]benzamide 1.47637 2.58 828_0176_0285 [00313] 3-[3-(3- hydroxyphenyl) imidazo[1,2- b]pyridazin-6- yl]benzamide 0.31104 2.80 828_0284_0347 [00314] 4-[3-[4- (hydroxymethyl) phenyl]imidazo [1,2-b]pyridazin- 6-yl]-2-methoxy- phenol 0.22297 3.02 828_0285_0314 [00315] 2-(3,4- dimethoxyphen- yl)-6-hydroxy- chromen-4-one 8.95228 2.35 DT2012- 0347380 [00316] [3-[6-(3- pyridyl)imidazo [1,2-b]pyridazin- 3- yl]phenyl]metha- nol 2.03689 2.27 828_0291_0071 [00317] [3-[6-[(4- fluorophenyl) methyl]imidazo [1,2- b]pyridazin-3- yl]phenyl]metha- nol 3.9747 3.56 828_0291_6370 [00318] [3-[6-(3- methoxyphenyl) imidazo[1,2- b]pyridazin-3- yl]phenyl]metha- nol 2.74495 3.33 828_0291_4140 [00319] N-[3-[3-(4- pyridyl)imidazo [1,2-b]pyridazin- 6- yl]phenyl]meth- anesulfonamide 0.29796 1.41 828_0069_6488 [00320] 1-benzyl-N-[4- (4- methylpiperazin- 1-yl)phenyl]-2- (3- pyridyl)pyrrolo [3, 2-c]pyridin-6- amine 13.73604 5.14 809_2675_6001_ 0091 [00321] 2-(1H-pyrazol-4- yl)-N-(2-pyridyl)- 1H-pyrrolo[3,2- c]pyridin-6- amine 7.566 2.14 809_2678_0263_ 0259 [00322] N-(4- methylsulfonyl- phenyl)-2-(1H- pyrazol-4-yl)- 1H-pyrrolo[3,2- c]pyridin-6- amine 4.77594 1.60 809_2678_0263_ 9248 [00323] 1-benzyl-2-(3- pyridyl)-N- pyrimidin-4-yl- pyrrolo[3,2- c]pyridin-6- amine 6.84653 3.86 809_2675_6001_ 6410 [00324] N-(3- methoxyphenyl)- 2-(1H-pyrazol- 4-yl)-1H- pyrrolo[3,2- c]pyridin-6- amine 16.58236 2.60 809_2678_0263_ 0026 [00325] N-(3,4- dimethoxyphen- yl)-2-(1H- pyrazol-4-yl)- 1H-pyrrolo[3,2- c]pyridin-6- amine 12.71137 2.44 809_2678_0263_ 0036 [00326] 1-benzyl-N-[4- (4- methylpiperazin- 1-yl)phenyl]-2- phenyl- pyrrolo[3,2- c]pyridin-6- amine 15.018 6.36 809_9960_6001_ 0091 [00327] 6-(2- methoxyphenyl)- 3-(4- pyridyl)imidazo [1,2-b]pyridazine 0.58491 2.88 828_0069_0083 [00328] 3-[3-(4- pyridyl)imidazo [1,2-b]pyridazin- 6-yl]benzamide 1.2024 1.89 828_0069_0347 [00329] N-[3-(6- phenylimidazo[1, 2-b]pyridazin-3- yl)phenyl] acetamide 0.77278 3.49 828_0081_0061 [00330] N-[3-[6-(3- hydroxyphenyl) imidazo[1,2- b]pyridazin-3- yl]phenyl] acetamide 1.0711 3.19 828_0081_0284 [00331] 3-(3,4- dimethoxyphen- yl)-6-(3- fluorophenyl) imidazo[1,2- b]pyridazine 1.0392 4.08 828_0079_0313 [00332] N-[3-[6-[4- (hydroxymethyl) phenyl]imidazo [1,2-b]pyridazin- 3- yl]phenyl] acetamide 0.49363 2.72 828_0081_0285 [00333] [3-(6- phenylimidazo[1, 2-b]pyridazin-3- yl)phenyl]metha- nol 1.74526 3.49 828_0291_0061 [00334] 6-(3- chlorophenyl)-3- (4- pyridyl)imidazo [1,2-b]pyridazine 0.25819 3.64 828_0069_0279 [00335] 4-[3-(3,4- dimethoxyphen- yl)imidazo[1,2- b]pyridazin-6- yl]-2-methoxy- phenol 0.22231 3.48 828_0079_0314 [00336] N-[3-[6-(2- methoxyphenyl) imidazo[1,2- b]pyridazin-3- yl]phenyl] acetamide 2.85447 3.33 828_0081_0083 [00337] N-[3-[6-[3- (trifluoromethyl) phenyl]imidazo [1,2-b]pyridazin- 3- yl]phenyl] acetamide 1.6027 4.37 828_0081_0312 [00338] [3-[6-(2- methoxyphenyl) imidazo[1,2- b]pyridazin-3- yl]phenyl]metha- nol 1.06972 3.33 828_0291_0083 [00339] 4-[3-[3- (hydroxymethyl) phenyl]imidazo [1,2-b]pyridazin- 6-yl]-2-methoxy- phenol 0.15309 3.02 828_0291_0314 [00340] 3-phenyl-6-(4- pyridyl)imidazo [1,2-b]pyridazine 6.92543 3.04 828_0061_0069 [00341] 3-[3-(4- pyridyl)imidazo [1,2-b]pyridazin- 6-yl]phenol 0.22268 2.73 828_0069_0284 [00342] 3-(3,4- dimethoxyphen- yl)-6-phenyl- imidazo[1,2- b]pyridazine 0.42017 3.94 828_0079_0061 [00343] 3-(3,4- dimethoxyphen- yl)-6-(4- fluorophenyl) imidazo[1,2- b]pyridazine 1.33171 4.08 828_0079_0339 [00344] N-[3-[6-(3,4,5- trimethoxyphen- yl)imidazo[1,2- b]pyridazin-3- yl]phenyl] acetamide 3.13438 3.02 828_0081_0087 [00345] N-[3-[6-(4- hydroxy-3- methoxy- phenyl)imidazo [1,2-b]pyridazin- 3- yl]phenyl] acetamide 0.09296 3.03 828_0081_0314 [00346] 3-phenyl-6-(3- pyridyl)imidazo [1,2-b]pyridazine 3.84274 3.04 828_0061_0071 [00347] [4-[3-(4- pyridyl)imidazo [1,2-b]pyridazin- 6- yl]phenyl]metha- nol 0.2553 2.27 828_0069_0285 [00348] 3-(3,4- dimethoxyphen- yl)-6-(2- methoxyphenyl) imidazo[1,2- b]pyridazine 3.12222 3.78 828_0079_0083 [00349] 3-(3,4- dimethoxyphen- yl)-6-(3- furyl)imidazo[1, 2-b]pyridazine 0.98263 3.08 828_0079_0343 [00350] N-[3-[6-(3- furyl)imidazo[1, 2-b]pyridazin-3- yl]phenyl] acetamide 1.2569 2.63 828_0081_0343 [00351] [3-[6-(3- furyl)imidazo[1, 2-b]pyridazin-3- yl]phenyl] methanol 3.99398 2.63 828_0291_0343 [00352] N,N-dimethyl-4- [3-(4- pyridyl)imidazo [1,2-b]pyridazin- 6-yl]aniline 0.39834 3.14 828_0069_0004 [00353] [3-[6-(4- methylsulfonyl- phenyl)imidazo [1, 2-b]pyridazin-3- yl]phenyl]metha- nol 3.03776 2.33 828_0291_0174 [00354] N-[3-(3- phenylimidazo [1, 2-b]pyridazin-6- yl)phenyl] acetamide 3.66176 3.49 828_0061_0081 [00355] 6-phenyl-3-(4- pyridyl)imidazo [1,2-b]pyridazine 0.22894 3.04 828_0069_0061 [00356] 6-(3- fluorophenyl)-3- (4- pyridyl)imidazo [1,2-b]pyridazine 0.35611 3.18 828_0069_0313 [00357] 3-(3,4- dimethoxyphen- yl)-6-(3- methoxyphenyl) imidazo[1,2- b]pyridazine 0.95169 3.78 828_0079_4140 [00358] N-[3-[6-(5- methoxy-3- pyridyl)imidazo [1,2-b]pyridazin- 3- yl]phenyl] acetamide 0.614 2.12 828_0081_0196 [00359] [3-[6-(5- methoxy-3- pyridyl)imidazo [1,2-b]pyridazin- 3- yl]phenyl] methanol 2.14052 2.11 828_0291_0196 [00360] 6-(1,3- benzodioxol-5- yl)-3-(4- pyridyl)imidazo [1,2-b]pyridazine 0.21745 2.66 828_0069_0068 [00361] 6-(3-furyl)-3-(4- pyridyl)imidazo [1,2-b]pyridazine 1.02049 2.18 828_0069_0343 [00362] N-[3-[6-(3- chlorophenyl) imidazo[1,2- b]pyridazin-3- yl]phenyl] acetamide 0.3705 4.10 828_0081_0279 [00363] N-[3-[6-(3- methoxyphenyl) imidazo[1,2- b]pyridazin-3- yl]phenyl] acetamide 0.40863 3.33 828_0081_4140 [00364] 3-[3-[3- (hydroxymethyl) phenyl]imidazo [1,2-b]pyridazin- 6-yl]phenol 0.95381 3.18 828_0291_0284 [00365] 4-(3- phenylimidazo[1, 2-b]pyridazin-6- yl)benzamide 2.14265 3.10 828_0061_0346 [00366] 3-[3-(1,3- benzodioxol-5- yl)imidazo[1,2- b]pyridazin-6- yl]phenol 0.91497 3.57 828_0068_0284 [00367] 6-phenyl-3-(3- pyridyl)imidazo [1,2-b]pyridazine 1.94131 3.04 828_0071_0061 [00368] 3-(3-pyridyl)-6- (2- thienyl)imidazo [1,2-b]pyridazine 0.34617 2.81 828_0071_4147 [00369] N-[3-[6-(3- acetylphenyl) imidazo[1,2- b]pyridazin-3- yl]phenyl] acetamide 0.46574 3.05 828_0081_4145 [00370] 3-[6-(3- methoxyphenyl) imidazo[1,2- b]pyridazin-3- yl]phenol 1.2357 3.79 828_0284_4140 [00371] 4-[6-(3,4- dimethoxyphen- yl)imidazo[1,2- b]pyridazin-3- yl]-2-methoxy- phenol 0.04451 3.48 828_0314_0079 [00372] 1-[3-[6-(2- methoxyphenyl) imidazo[1,2- b]pyridazin-3- yl]phenyl] ethanone 2.3343 3.65 828_4145_0083 [00373] 1-[3-[6-(1- methylpyrazol- 4- yl)imidazo[1,2- b]pyridazin-3- yl]phenyl] ethanone 0.37322 2.24 828_4145_7468 [00374] N-[3-[3-(2- thienyl)imidazo [1,2-b]pyridazin- 6- yl]phenyl]meth- anesulfonamide 1.20815 2.40 828_4147_6488 [00375] 3-(1,3- benzodioxol-5- yl)-6-(3- pyridyl)imidazo [1,2-b]pyridazine 0.68757 2.66 828_0068_0071 [00376] [4-[3-(3- pyridyl)imidazo [1,2-b]pyridazin- 6- yl]phenyl] methanol 2.9094 2.27 828_0071_0285 [00377] 6-benzyl-3-(3,4- dimethoxyphen- yl)imidazo[1,2- b]pyridazine 0.97448 3.87 828_0079_6001 [00378] 3-[6-[4- (hydroxymethyl) phenyl]imidazo [1,2-b]pyridazin- 3-yl]phenol 0.28545 3.18 828_0284_0285 [00379] [4-[6-(2- methoxyphenyl) imidazo[1,2- b]pyridazin-3- yl]phenyl] methanol 3.90029 3.33 828_0285_0083 [00380] [4-[6-(3- methoxyphenyl) imidazo[1,2- b]pyridazin-3- yl]phenyl] methanol 1.55838 3.33 828_0285_4140 [00381] 2-methoxy-4-[6- (3- methoxyphenyl) imidazo[1,2- b]pyridazin-3- yl]phenol 0.22071 3.63 828_0314_4140 [00382] 1-[3-[6-(3- furyl)imidazo[1, 2-b]pyridazin-3- yl]phenyl] ethanone 3.4398 2.95 828_4145_0343 [00383] 4-[3-(2- thienyl)imidazo [1,2-b]pyridazin- 6-yl]benzamide 0.95101 2.88 828_4147_0346 [00384] 3-[3-(1,3- benzodioxol-5- yl)imidazo[1,2- b]pyridazin-6- yl]-N-(2- hydroxyethyl) benzamide 0.36748 2.26 828_0068_0192 [00385] [3-[3-(1,3- benzodioxol-5- yl)imidazo[1,2- b]pyridazin-6- yl]phenyl] methanol 0.33166 3.11 828_0068_0291 [00386] N-[3-[6-(2- thienyl)imidazo [1,2-b]pyridazin- 3- yl]phenyl] acetamide 0.20995 3.27 828_0081_4147 [00387] 3-(6- phenylimidazo[1, 2-b]pyridazin-3- yl)phenol 0.89352 3.95 828_0284_0061 [00388] 1-[3-[3-(3- hydroxyphenyl) imidazo[1,2- b]pyridazin-6- yl]phenyl]NL ethanone 1.60026 3.51 828_0284_4145 [00389] [4-[6-(3- fluorophenyl) imidazo[1,2- b]pyridazin-3- yl]phenyl] methanol 2.95859 3.63 828_0285_0313 [00390] 1-[3-[3-[3- (hydroxymethyl) phenyl]imidazo [1,2-b]pyridazin- 6- yl]phenyl] ethanone 2.16824 3.04 828_0291_4145 [00391] 1-[3-[6-[3- (dimethylamino) phenyl]imidazo [1,2-b]pyridazin- 3- yl]phenyl] ethanone 0.88623 3.92 828_4145_0135 [00392] 1-[3-[6-(6- amino-3- pyridyl)imidazo [1,2-b]pyridazin- 3- yl]phenyl] ethanone 0.28267 2.36 828_4145_7905 [00393] [4-[3-(2- thienyl)imidazo [1,2-b ]pyridazin- 6- yl]phenyl] methanol 2.35649 3.26 828_4147_0285 [00394] N-[3-[3-(3,4- dimethoxyphen- yl)imidazo[1,2- b]pyridazin-6- yl]phenyl]meth- anesulfonamide 0.70252 2.31 828_0079_6488 [00395] 3-[3-(3- acetylphenyl) imidazo[1,2- b]pyridazin-6- yl]benzamide 0.51895 2.66 828_4145_0347 [00396] N-[3-[3-(3- pyridyl)imidazo [1,2-b]pyridazin- 6- yl]phenyl]meth- anesulfonamide 1.41022 1.41 828_0071_6488 [00397] 3-[6-(4- pyridyl)imidazo [1,2-b]pyridazin- 3-yl]phenol 0.20283 2.73 828_0284_0069 [00398] 3-[6-(5- quinolyl)imidazo [1,2-b]pyridazin- 3-yl]phenol 14.63638 4.11 828_0284_6831 [00399] N-[3-[3-[3- (hydroxymethyl) phenyl]imidazo [1,2-b]pyridazin- 6- yl]phenyl]meth- anesulfonamide 1.15032 1.86 828_0291_6488 [00400] 2-methoxy-4-[6- (2- methoxyphenyl) imidazo[1,2- b]pyridazin-3- yl]phenol 0.95886 3.63 828_0314_0083 [00401] 3-[3-(3- acetylphenyl) imidazo[1,2- b]pyridazin-6- yl]-N-methyl- benzamide 1.71793 2.89 828_4145_7965 [00402] [3-[3-(2- thienyl)imidazo [1,2-b]pyridazin- 6- yl]phenyl]metha- nol 1.68324 3.26 828_4147_0291 [00403] 6-(1- methylpyrazol- 4-yl)-3-(2- thienyl)imidazo [1,2-b]pyridazine 1.3135 2.46 828_4147_7468 [00404] 3-[3-(3,4- dimethoxyphen- yl)imidazo[1,2- b]pyridazin-6- yl]-N-(2- hydroxyethyl) benzamide 0.3666 2.32 828_0079_0192 [00405] 3-(1,3- benzodioxol-5- yl)-6-(1- methylpyrazol- 4- yl)imidazo[1,2- b]pyridazine 0.95557 2.30 828_0068_7468 [00406] 3-(3,4- dimethoxyphen- yl)-6-(1- methylpyrazol- 4- yl)imidazo[1,2- b]pyridazine 0.36693 2.37 828_0079_7468 [00407] 3-[6-(3- fluorophenyl) imidazo[1,2- b]pyridazin-3- yl]phenol 2.26441 4.09 828_0284_0313 [00408] 1-[3-[6-(3- aminophenyl) imidazo[1,2- b]pyridazin-3- yl]phenyl] ethanone 1.12246 2.98 828_4145_0005 [00409] 6-(2- methoxyphenyl)- 3-(3- pyridyl)imidazo [1,2-b]pyridazine 2.3503 2.88 828_0071_0083 [00410] 3-(3,4- dimethoxyphen- yl)-6-(4- pyridyl)imidazo [1,2-b]pyridazine 0.40386 2.72 828_0079_0069 [00411] 3-[6-(3- pyridyl)imidazo [1,2-b]pyridazin- 3-yl]phenol 0.58643 2.73 828_0284_0071 [00412] 3-[6-(1- methylpyrazol- 4- yl)imidazo[1,2- b]pyridazin-3- yl]phenol 0.38762 2.38 828_0284_7468 [00413] [4-[6-(4- fluorophenyl) imidazo[1,2- b]pyridazin-3- yl]phenyl] methanol 2.94383 3.63 828_0285_0339 [00414] 4-[6-(3- hydroxyphenyl) imidazo[1,2- b]pyridazin-3- yl]-2-methoxy- phenol 0.29478 3.49 828_0314_0284 [00415] 6-(3,4- dimethoxyphen- yl)-3-(4- pyridyl)imidazo [1,2-b]pyridazine 0.28231 2.72 828_0069_0079 [00416] 6-(4- fluorophenyl)-3- (3- pyridyl)imidazo [1,2-b]pyridazine 2.77876 3.18 828_0071_0339 [00417] [3-[3-(3- chlorophenyl) imidazo[1,2- b]pyridazin-6- yl]phenyl] methanol 9.81893 4.09 828_0279_0291 [00418] 3-[6-(4- fluorophenyl) imidazo[1,2- b]pyridazin-3- yl]phenol 11.87843 4.09 828_0284_0339 [00419] 3-phenyl-6-(2- thienyl)imidazo [1,2-b]pyridazine 1.9697 4.03 828_0061_4147 [00420] 3-(3,4- dimethoxyphen- yl)-6-(3- pyridyl)imidazo [1,2-b]pyridazine 0.54944 2.72 828_0079_0071 [00421] N-[3-[3-(3- hydroxyphenyl) imidazo[1,2- b]pyridazin-6- yl]phenyl] acetamide 1.64512 3.19 828_0284_0081 [00422] 4-[6-[4- (hydroxymethyl) phenyl]imidazo [1,2-b]pyridazin- 3-yl]-2-methoxy- phenol 0.12455 3.02 828_0314_0285 [00423] 3-[3-(3,4- dimethoxyphen- yl)imidazo[1,2- b]pyridazin-6- yl]-N-methyl- benzamide 3.49397 3.01 828_0079_7965 [00424] N-[3-[3-(4- pyridyl)imidazo [1,2-b]pyridazin- 6- yl]phenyl] acetamide 0.59778 2.27 828_0069_0081 [00425] 6-(3-furyl)-3-(3- pyridyl)imidazo [1,2-b]pyridazine 2.34906 2.18 828_0071_0343 [00426] N-[3-[6-(3,4- dimethoxyphen- yl)imidazo[1,2- b]pyridazin-3- yl]phenyl] acetamide 0.25932 3.18 828_0081_0079 [00427] 3-[6-(3- furyl)imidazo[1, 2-b]pyridazin-3- yl]phenol 1.05684 3.09 828_0284_0343 [00428] 1-[3-[6-(4- pyridyl)imidazo [1,2-b]pyridazin- 3- yl]phenyl] ethanone 0.37149 2.59 828_4145_0069 [00429] 6-(m- tolylmethyl)-3- (4- pyridyl)imidazo [1,2-b]pyridazine 0.97706 3.48 828_0069_6291 [00430] 3-(1,3- benzodioxol-5- yl)-6-(4- fluorophenyl) imidazo[1,2- b]pyridazine 7.60066 4.02 828_0068_0339 [00431] 3,6-bis(3,4- dimethoxyphen- yl)imidazo[1,2- b]pyridazine 0.53841 3.62 828_0079_0079 [00432] 3-[6-(2- methoxyphenyl) imidazo[1,2- b]pyridazin-3- yl]phenol 2.73595 3.79 828_0284_0083 [00433] [4-(6- phenylimidazo[1, 2-b]pyridazin-3- yl)phenyl] methanol 1.45898 3.49 828_0285_0061 [00434] N-[4-[3-[4- (hydroxymethyl) phenyl]imidazo [1,2-b]pyridazin- 6- yl]phenyl] acetamide 21.45348 2.72 828 _0285_0722 [00435] 4-[6-[3- (hydroxymethyl) phenyl]imidazo [1,2-b]pyridazin- 3-yl]-2-methoxy- phenol 0.10235 3.02 828_0314_0291 [00436] 1-[3-[6-[3- (hydroxymethyl) phenyl]imidazo [1,2-b]pyridazin- 3- yl]phenyl] ethanone 0.17883 3.04 828_4145_0291 [00437] 6-(4-pyridyl)-3- (2- thienyl)imidazo [1,2-b]pyridazine 0.49696 2.81 828_4147_0069 [00438] 2-methoxy-4-[3- (2- thienyl)imidazo [1,2-b]pyridazin- 6-yl]phenol 0.69396 3.57 828_4147_0314 [00439] N-(2- hydroxyethyl)-3- (3- phenylimidazo[1, 2-b]pyridazin-6- yl)benzamide 13.8636 2.64 828_0061_0192 [00440] 6-benzyl-3-(4- pyridyl)imidazo [1,2-b]pyridazine 0.6243 2.97 828_0069_6001 [00441] 4-[3-(3- pyridyl)imidazo [1,2-b]pyridazin- 6-yl]benzamide 11.24348 1.89 828_0071_0346 [00442] 1-[3-[6-(3- pyridyl)imidazo [1,2-b]pyridazin- 3- yl]phenyl] ethanone 1.23395 2.59 828_4145_0071 [00443] 1-[3-[6-(3- methoxyphenyl) imidazo[1,2- b]pyridazin-3- yl]phenyl] ethanone 1.78495 3.65 828_4145_4140 [00444] 6-[(4- fluorophenyl) methyl]-3-(4- pyridyl)imidazo [1,2-b] pyridazine 1.44642 3.11 828_0069_6370 [00445] 3-[3-(1,3- benzodioxol-5- yl)imidazo[1,2- b]pyridazin-6- yl]aniline 0.84313 3.05 828_0068_0005 [00446] 3-(1,3- benzodioxol-5- yl)-6-(3- furyl)imidazo[1, 2-b]pyridazine 1.60154 3.02 828_0068_0343 [00447] [4-[6-(3,4- dimethoxyphen- yl)imidazo[1,2- b]pyridazin-3- yl]phenyl] methanol 3.9402 3.17 828_0285_0079 [00448] 3-[3-(1,3- benzodioxol-5- yl)imidazo[1,2- b]pyridazin-6- yl]-N-(2- dimethylamino- ethyl)benzamide 0.39289 2.97 828_0068_0176 [00449] N-[3-[6-(3- chloro-4-fluoro- phenyl)imidazo [1,2-b]pyridazin- 3- yl]phenyl] acetamide 0.52521 4.24 828_0081_0164 [00450] 3-[3-[4- (hydroxymethyl) phenyl]imidazo [1,2-b]pyridazin- 6-yl]phenol 1.13696 3.18 828_0285_0284 [00451] [3-[6-(3,4- dimethoxyphen- yl)imidazo[1,2- b]pyridazin-3- yl]phenyl] methanol 0.74933 6.29 828_0291_0079 [00452] 1-[3-[3-(3- acetylphenyl) imidazo[1,2- b]pyridazin-6- yl]phenyl] ethanone 0.58173 3.37 828_4145_4145 [00453] N-(2- dimethylamino- ethyl)-3-[3-(2- thienyl)imidazo [1,2-b]pyridazin- 6-yl]benzamide 1.1611 3.12 828_4147_0176 [00454] 3-(1,3- benzodioxol-5- yl)-6-phenyl- imidazo[1,2- b]pyridazine 3.08798 3.88 828_0068_0061 [00455] 3-[3-(3- pyridyl)imidazo [1,2-b]pyridazin- 6-yl]phenol 1.81461 2.73 828_0071_0284 [00456] 3-(3,4- dimethoxyphen- yl)-6-(2- thienyl)imidazo [1,2-b]pyridazine 0.21139 3.72 828_0079_4147 [00457] 3-[3-(3- hydroxyphenyl) imidazo[1,2- b]pyridazin-6- yl]phenol 0.98714 3.65 828_0284_0284 [00458] N-[3-[3-[4- (hydroxymethyl) phenyl]imidazo [1,2-b ]pyridazin- 6- yl]phenyl] acetamide 2.2389 2.72 828_0285_0081 [00459] 1-[3-[6-(4- fluorophenyl) imidazo[1,2- b]pyridazin-3- yl]phenyl] ethanone 4.81048 3.95 828_4145_0339 [00460] 3-[3-(3- acetamidophen- yl)imidazo[1,2- b]pyridazin-6- yl]-N-methyl- benzamide 1.3298 2.57 828_0081_7965 [00461] [3-(3- phenylimidazo[1, 2-b]pyridazin-6- yl)phenyl] methanol 1.92857 3.49 828_0061_0291 [00462] 6-(1- methylpyrazol- 4-yl)-3-(4- pyridyl)imidazo [1,2-b] pyridazine 30 1.46 828_0069_7468 [00463] N-(2- dimethylamino- ethyl)-3-[3-[3- (trifluoro- methoxy) phenyl]imidazo [1,2- b]pyridazin-6- yl]benzamide 3.93108 4.78 828_0168_0176 [00464] [4-[3-[4- (hydroxymethyl) phenyl]imidazo [1,2-b]pyridazin- 6- yl]phenyl] methanol 1.03522 2.72 828_0285_0285 [00465] 4-[6-(1,3- benzodioxol-5- yl)imidazo[1,2- b]pyridazin-3- yl]-2-methoxy- phenol 0.1999 3.42 828_0314_0068 [00466] 1-[3-[6-(2- thienyl)imidazo [1,2-b]pyridazin- 3- yl]phenyl] ethanone 0.41575 3.59 828_4145_4147 [00467] 6-(5-methoxy-3- pyridyl)-3-(2- thienyl)imidazo [1,2-b]pyridazine 2.86231 2.66 828_4147_0196 [00468] 3,6-bis(2- thienyl)imidazo [1,2-b] pyridazine 4.89416 3.81 828_4147_4147 [00469] N-(2- dimethylamino- ethyl)-3-[6-(1- methylpyrazol- 4- yl)imidazo[1,2- b]pyridazin-3- yl]benzamide 1.76458 1.77 828_0176_7468 [00470] 3-[6-(1,3- benzodioxol-5- yl)imidazo[1,2- b]pyridazin-3- yl]-N-(2- dimethylamino- ethyl)benzamide 2.01862 2.97 828_0176_0068 [00471] 3-[3-[3-(2- dimethylamino- ethylcarbamoyl) phenyl]imidazo [1, 2-b]pyridazin-6- yl]benzamide 4.14881 2.20 828_0176_0347 [00472] N-(2- hydroxyethyl)-3- [3-(3- hydroxyphenyl) imidazo[1,2- b]pyridazin-6- yl]benzamide 0.35163 2.33 828_0284_0192 [00473] 2-methoxy-4-[6- (3,4,5- trimethoxyphen- yl)imidazo[1,2- b]pyridazin-3- yl]phenol 1.81139 3.32 828_0314_0087 [00474] [3-[3-(3- furyl)imidazo[1, 2-b]pyridazin-6- yl]phenyl] methanol 7.32807 2.63 828_0343_0291 [00475] 4-(6- benzylimidazo[1, 2-b]pyridazin-3- yl)benzamide 0.71127 3.04 828_0346_6001 [00476] 3-[6-(4- acetamidophen- yl)imidazo[1,2- b]pyridazin-3- yl]-N-(2- dimethylamino- ethyl)benzamide 0.98309 2.58 828_0176_0722 [00477] 2-methoxy-4-[6- [3- (trifluoro- methoxy) phenyl]imidazo [1,2- b]pyridazin-3- yl]phenol 0.83451 5.22 828_0314_0168 [00478] N-(2- dimethylamino- ethyl)-3-[6-[3- (hydroxymethyl) phenyl]imidazo [1,2-b]pyridazin- 3-yl]benzamide 0.81608 2.58 828_0176_0291 [00479] 4-[6-[(3,4- difluorophenyl) methyl]imidazo [1,2-b]pyridazin- 3-yl]benzamide 3.07271 3.52 828_0346_6007 [00480] 3-[6-(3- acetamidophen- yl)imidazo[1,2- b]pyridazin-3- yl]-N-(2- dimethylamino- ethyl)benzamide 3.16865 2.58 828_0176_0081 [00481] 2-methoxy-4-[6- [3- (trifluoromethyl) phenyl]imidazo [1,2-b]pyridazin- 3-yl]phenol 1.08271 4.67 828_0314_0312 [00482] 6-benzyl-3-(5- methoxy-3- pyridyl)imidazo [1,2-b]pyridazine 2.67306 2.81 828_0196_6001 [00483] 4-[6-(m- tolylmethyl) imidazo[1,2- b]pyridazin-3- yl]benzamide 3.10262 3.55 828_0346_6291 [00484] N-(2- dimethylamino- ethyl)-3-[6-(2- methoxyphenyl) imidazo[1,2- b]pyridazin-3- yl+benzamide 2.13745 3.19 828_0176_0083 [00485] N-(2- dimethylamino- ethyl)-3-[6-(3- phenoxyphenyl) imidazo[1,2- b]pyridazin-3- yl]benzamide 19.18297 4.85 828_0176_4032 [00486] 3-(6- cyclopropyl- imidazo[1,2- b]pyridazin-3- yl)phenol 1.88565 2.83 828_0284_7494 [00487] 4-[6-(3- fluorophenyl) imidazo[1,2- b]pyridazin-3- yl]-2-methoxy- phenol 0.28065 3.93 828_0314_0313 [00488] 6-[(4- fluorophenyl) methyl]-3-(5- methoxy-3- pyridyl)imidazo [1,2-b]pyridazine 4.41614 2.95 828_0196_6370 [00489] 4-[6-[(4- fluorophenyl) methyl]imidazo [1,2- b]pyridazin-3- yl]benzamide 1.30064 3.18 828_0346_6370 [00490] N-(2- hydroxyethyl)-3- [3-[4- (hydroxymethyl) phenyl]imidazo [1,2-b]pyridazin- 6-yl]benzamide 2.14389 1.87 828_0285_0192 [00491] 3-[3-(4-hydroxy- 3-methoxy- phenyl)imidazo [1,2-b]pyridazin- 6-yl]benzamide 0.22316 2.64 828_0314_0347 [00492] 3-(1- methylpyrazol- 4-yl)-6-(m- tolylmethyl) imidazo[1,2- b]pyridazine 1.79534 3.13 828_7468_6291 [00493] 3-[3-(3- acetylphenyl) imidazo[1,2- b]pyridazin-6- yl]-N-(2- hydroxyethyl) benzamide 0.6293 2.20 828_4145_0192 [00494] [4-(6- benzylimidazo[1, 2-b]pyridazin-3- yl)phenyl] methanol 3.22675 3.42 828_0285_6001 [00495] 4-[6-[(4- fluorophenyl) methyl]imidazo [1,2- b]pyridazin-3- yl]-2-methoxy- phenol 2.08974 3.87 828_0314_6370 [00496] 6-[(4- fluorophenyl) methyl]-3-(1- methylpyrazol- 4- yl)imidazo[1,2- b]pyridazine 1.29697 2.76 828_7468_6370 [00497] N-(2- dimethylamino- ethyl)-3-[6-(4- fluorophenyl) imidazo[1,2- b]pyridazin-3- yl]benzamide 2.23882 3.49 828_0176_0339 [00498] 3-[3-(3- chlorophenyl) imidazo[1,2- b]pyridazin-6- hydroxyethyl) benzamide 30 3.24 828_0279_0192 [00499] 3-[6-(m- tolylmethyl) imidazo[1,2- b]pyridazin-3- yl]benzamide 2.16636 3.55 828_0347_6291 [00500] 1-[3-(6- benzylimidazo[1, 2-b]pyridazin-3- yl)phenyl] ethanone 3.9717 3.74 828_4145_6001 [00501] 5-(6- benzylimidazo[1, 2-b]pyridazin-3- yl)pyridin-2- amine 3.63637 2.73 828_7905_6001 [00502] N-(2- dimethylamino- ethyl)-3-[6-(3- furyl)imidazo[1, 2-b]pyridazin-3- yl]benzamide 3.88391 2.49 828_0176_0343 [00503] 3-[3-[4- (hydroxymethyl) phenyl]imidazo [1,2-b]pyridazin- 6-yl]-N-methyl- benzamide 14.94149 2.56 828_0285_7965 [00504] 4-[4-[3-(2- methoxyphenyl)- 1H- pyrazolo[3,4- b]pyridin-4- yl]phenyl] morpholine 1.38698 3.86 932_2105_0001 [00505] 4-(3-chloro-4- fluoro-phenyl)- 3-(2- methoxyphenyl)- 1H- pyrazolo[3,4- b]pyridine 1.28108 4.72 932_2105_0164 [00506] 3-(2- methoxyphenyl)- 4-(6-methoxy- 3-pyridyl)-1H- pyrazolo[3,4- b]pyridine 2.93037 3.19 932_2105_0311 [00507] 3-(2- methoxyphenyl)- 4-(2- methoxy- pyrimidin- 5-yl)-1H- pyrazolo[3,4- b]pyridine 6.43118 2.57 932_2105_7628 [00508] 4-[3-(3- fluorophenyl)- 1H- pyrazolo[3,4- b]pyridin-4-yl]- N,N-dimethyl- benzamide 3.86464 3.57 932_5640_7464 [00509] N,N-dimethyl-4- [3-(3-thienyl)- 1H- pyrazolo[3,4- b]pyridin-4- yl]benzamide 11.19371 3.20 932_2055_7464 [00510] N-+4-(3- cyclopropyl-1H- pyrazolo[3,4- b]pyridin-4- yl)phenyl] acetamide 8.88989 2.24 932_2070_0722 [00511] 3-[3-(4-pyridyl)- 1H- pyrazolo[3,4- b]pyridin-4- yl]aniline 18.00668 2.08 932_5650_0005 [00512] [4-[3-(3- fluorophenyl)- 1H- pyrazolo[3,4- b+9pyridin-4- yl]phenyl] methanol 3.87681 3.50 932_5640_0285 [00513] 3-(2- methoxyphenyl)- 4-(3-thienyl)- 1H- pyrazolo[3,4- b]pyridine 2.66842 3.75 932_2105_0074 [00514] N-[4-[3-(3,4,5- trimethoxyphen- yl)-1H- pyrazolo[3,4- b]pyridin-4- yl]phenyl] acetamide 2.02053 2.89 932_4516_0722 [00515] 3-(2- methoxyphenyl)- 4-[(E)-styryl]- 1H- pyrazolo[3,4- b]pyridine 1.12832 4.66 932_2105_0170 [00516] 4-(3- fluorophenyl)-3- (2- methoxyphenyl)- 1H- pyrazolo[3,4- b]pyridine 1.35112 4.11 932_2105_0313 [00517] 4-[3-(2- methoxyphenyl)- 1H- pyrazolo[3,4- b]pyridin-4- yl]benzamide 1.47616 2.82 932_2105_0346 [00518] [4-(3-phenyl-1H- pyrazolo[3,4- b]pyridin-4- yl)phenyl] methanol 7.10693 3.36 932_2047_0285 [00519] 3-phenyl-4-(1H- pyrazol-4-yl)- 1H- pyrazolo[3,4- b]pyridine 0.8524 2.43 932_2047_7467 [00520] 4-(4- isopropyl- phenyl)- 3-(3,4,5- trimethophen- yl)-1H- pyrazolo[3,4- b]pyridine 20.88874 4.90 932_4516_0283 [00521] 4-(3- chlorophenyl)-3- cyclopropyl-1H- pyrazolo[3,4- b]pyridine 30 3.61 932_2070_0279 [00522] N-(2- dimethylamino- ethyl)-3-[3-(2- methoxyphenyl)- 1H- pyrazolo[3,4- b]pyridin-4- yl]benzamide 4.85182 3.06 932_2105_0176 [00523] [3-[3-(2- methoxyphenyl)- 1H- pyrazolo[3,4- b]pyridin-4- yl]phenyl] methanol 1.66776 3.20 932_2105_0291 [00524] 4-[3-(3- fluorophenyl)- 1H- pyrazolo[3,4- b]pyridin-4- yl]benzamide 2.04666 3.12 932_5640_0346 [00525] 4-[3-(4- chlorophenyl)- 1H- pyrazolo[3,4- b]pyridin-4- yl]benzamide 5.71214 3.58 932_5666_0346 [00526] 3-[3-(3,4,5- trimethoxyphen- yl)-1H- pyrazolo[3,4- b]pyridin-4- yl]phenol 5.02812 3.35 932_4516_0284 [00527] 1-[3-[3-(4- piperidyl)-1H- pyrazolo[3,4- b]pyridin-4- yl]phenyl] ethanone 19.65771 1.89 932_2802_4145 [00528] N-[4-[3-(3- thienyl)-1H- pyrazolo[3,4- b]pyridin-4- yl]phenyl] acetamide 4.86579 3.14 932_2055_0722 [00529] 2-methoxy-4-[3- (4-piperidyl)- 1H- pyrazolo[3,4- b]pyridin-4- yl]phenol 11.88451 1.87 932_2802_0314 [00530] N-[3-[3-(3,4,5- trimethoxyphen- yl)-1H- pyrazolo[3,4- b]pyridin-4- yl]phenyl]meth- anesulfonamide 12.76436 2.03 932_4516_6488 [00531] 4-(3-furyl)-3-(2- methoxyphenyl)- 1H- pyrazolo[3,4- b]pyridine 4.89672 3.11 932_2105_0343 [00532] 3-[3-(1,3- benzodioxol-5- yl)-1H- pyrazolo[3,4- b]pyridin-4- yl]phenol 6.24902 3.45 932_5654_0284 [00533] 4-(3-furyl)-3-(3- pyridyl)-1H- pyrazolo[3,4- b]pyridine 14.29835 2.05 932_2094_0343 [00534] [4-[3-(3,4,5- trimethoxyphen- yl)-1H- pyrazolo[3,4- b]pyridin-4- yl]phenyl] methanol 5.38048 2.89 932_4516_0285 [00535] 4-(3- methoxyphenyl)- 3-(4-piperidyl)- 1H- pyrazolo[3,4- b]pyridine 17.59629 2.17 932_2802_4140 [00536] 4-[3-(2- methoxyphenyl)- 1H- pyrazolo[3,4- b]pyridin-4- yl]benzonitrile 1.58329 3.82 932_2105_0086 [00537] N,N-dimethyl-4- [3-(3,4,5- trimethoxyphen- yl)-1H- pyrazolo[3,4- b]pyridin-4- yl]benzamide 11.14532 2.95 932_4516_7464 [00538] [4-[3-(1,3- benzodioxol-5- yl)-1H- pyrazolo[3,4- b]pyridin-4- yl]phenyl] methanol 4.64328 2.98 932_5654_0285 [00539] 4-(5-fluoro-2- methoxy- phenyl)-3-(4- piperidyl)-1H- pyrazolo[3,4- b]pyridine 11.69312 2.31 932_2802_8363 [00540] 4-(4- methylsulfonyl- phenyl)-3-(3,4,5- trimethoxyphen- yl)-1H- pyrazolo[3,4- b]pyridine 11.16027 2.49 932_4516_0174 [00541] [4-[3-(3- chlorophenyl)- 1H- pyrazolo[3,4- b]pyridin-4- yl]phenyl] methanol 6.49611 3.96 932_2049_0285 [00542] [3-[3-(1,3- benzodioxol-5- yl)-1H- pyrazolo[3,4- b]pyridin-4- yl]phenyl] methanol 3.09057 2.98 932_5654_0291 [00543] 4-(3-furyl)-3- phenyl-1H- pyrazolo[3,4- b]pyridine 8.62504 3.27 932_2047_0343 [00544] 4-(6-methoxy-3- pyridyl)-3- (3,4,5- trimethoxyphen- yl)-1H- pyrazolo[3,4- b]pyridine 16.92312 2.87 932_4516_0311 [00545] 3-cyclopropyl-4- (2-furyl)-1H- pyrazolo[3,4- b]pyridine 12.61441 2.06 932_2070_0142 [00546] 4-(2-furyl)-3-(2- methoxyphenyl)- 1H- pyrazolo[3,4- b]pyridine 2.27665 3.03 932_2105_0142 [00547] [4-[3-(2- methoxyphenyl)- 1H- pyrazolo[3,4- b]pyridin-4- yl]phenyl] methanol 1.10049 3.20 932_2105_0285 [00548] 1-[3-[3-(2- methoxyphenyl)- 1H- pyrazolo[3,4- b]pyridin-4- yl]phenyl] ethanone 6.60309 3.53 932_2105_4145 [00549] 4-(3-furyl)-3-(4- pyridyl)-1H- pyrazolo[3,4- b]pyridine 20.24336 2.05 932_5650_0343 [00550] 3-[3-(3- fluorophenyl)- 1H- pyrazolo[3,4- b]pyridin-4- yl]aniline 15.07442 3.44 932_5640_0005 [00551] 3-(3-phenyl-1H- pyrazolo[3,4- b]pyridin-4- yl)benzamide 11.71738 2.98 932_2047_0347 [00552] 3-[3-(3,4,5- trimethoxyphen- yl)-1H- pyrazolo[3,4- b]pyridin-4- yl]aniline 14.80741 2.82 932_4516_0005 [00553] 4-(3- fluorophenyl)-3- (3,4,5- trimethoxyphen- yl)-1H- pyrazolo[3,4- b]pyridine 5.22838 3.80 932_4516_0313 [00554] (E)-3-[3-[5-(3- pyridylmethyl- amino)pyrazolo [1,5- a]pyrimidin-3- yl]phenyl]prop- 2-enoic acid 2.27421 3.04 294_4003_0289 [00555] 3-[6-amino-5- (3,4,5- trimethoxyphen- yl)-3- pyridyl] benzamide 0.44196 2.19 382_0087_0347 [00556] 1-[5-[6-amino-5- [3- (dimethylamino) phenyl]-3- pyridyl]-2- thienyl] ethanone 3.41528 3.39 382_0135_0066 [00557] (Z)-5-[6- (methylamino) imidazo[1,2- b]pyridazin-3- yl]pent-4- en-1-ol 31.48029 1.22 437_0299 [00558] 2-methoxy-4-[2- (tetrahydropyran- 4- ylmethylamino) imidazo[2,1- b][1,3,4]thia- diazol-5-yl] phenol 2.16407 2.47 699_0243_0314 [00559] N-[3-[8- acetamido-3- (3,4- dimethoxyphen- yl)imidazo[1,2- a]pyridin-6- yl]phenyl] acetamide 1.59766 2.13 802_0079_0081 [00560] N-[3-(3- acetylphenyl)-6- (3- methoxyphenyl) imidazo[1,2- a]pyridin-8- yl]acetamide 3.05101 2.61 802_4145_4140 [00561] 5-(5-methoxy-3- pyridyl)-N-(4- pyridylmethyl) imidazo[2,1- b][1,3,4]thia- diazol-2-amine 0.93173 1.64 699_0237_0196 [00562] 4-[[5-(3-chloro- 4-fluoro- phenyl)imidazo [2,1- b][1,3,4]thia- diazol-2- yl]amino] cyclohexanol 4.05722 3.67 699_0240_0164 [00563] 4-[2-[[5-(3,4- dimethoxyphen- yl)imidazo[2,1- b][1,3,4]thia- diazol-2- yl]amino]ethyl] benzene- sulfonamide 5.11606 2.81 699_6182_0079 [00564] N-[3-(3- acetylphenyl)-6- (2,4- dimethoxyphen- yl)imidazo[1,2- a]pyridin-8- yl]acetamide 2.50187 2.45 802_4145_4141 [00565] 5-(3,4- dimethoxyphen- yl)-N-[2-(4- pyridyl)ethyl] imidazo[2,1- b][1,3,4]thia- diazol-2-amine 3.1387 2.99 699_0039_0079 [00566] 5-(4-pyridyl)-N- (4- pyridylmethyl) imidazo[2,1- b][1,3,4]thia- diazol-2-amine 2.64747 1.80 699_0237_0069 [00567] 5-(6-methoxy-3- pyridyl)-N-[2-(4- pyridyl)ethyl] imidazo[2,1- b][1,3,4]thia- diazol-2-amine 2.03015 2.52 699_0039_0311 [00568] 4-[2-[[5-(3- pyridyl)imidazo [2,1- b][1,3,4]thia- diazol-2- yl]amino]ethyl] benzene- sulfonamide 1.87926 1.91 699_6182_0071 [00569] 5-(4- morpholinophen- yl)-N-(2- thienylmethyl) imidazo[2,1- b][1,3,4]thia- diazol-2-amine 3.82253 4.03 699_0146_0001 [00570] [4-[2-[(4- methoxyphenyl) methylamino] imidazo[2,1- b][1,3,4]thia- diazol-5- yl]phenyl] methanol 2.8094 3.31 699_0244_0285 [00571] 5-(4- chlorophenyl)- N-(3- pyridylmethyl) imidazo[2,1- b][1,3,4]thia- diazol-2-amine 3.65935 3.62 699_4003_0160 [00572] N-[3-[2-[2-(4- pyridyl)ethyl- amino] imidazo[2,1- b][1,3,4]thia- diazol-5- yl]phenyl] acetamide 1.31627 2.54 699_0039_0081 [00573] N,N-dimethyl-3- [2-[2-(4- pyridyl)ethyl- amino] imidazo[2,1- b][1,3,4]thia- diazol-5- yl]benzamide 0.72142 2.60 699_0039_0349 [00574] 2-methoxy-4-[2- [(4- methoxyphenyl) methylamino] imidazo[2,1- b][1,3,4]thia- diazol-5-yl] phenol 1.77761 3.61 699_0244_0314 [00575] 5-(6-methoxy-3- pyridyl)-N-(3- pyridylmethyl) imidazo[2,1- b][1,3,4]thia- diazol-2-amine 2.93804 2.23 699_4003_0311 [00576] 5-(3-chloro-4- fluoro-phenyl)- N-(2- morpholino- ethyl) imidazo[2,1- b][1,3,4]thia- diazol-2-amine 4.81646 3.05 699_0252_0164 [00577] 5-(4-pyridyl)-N- [2-(4- pyridyl)ethyl] imidazo[2,1- b][1,3,4]thia- diazol-2-amine 2.42663 2.08 699_0039_0069 [00578] 4-[[5-(6- methoxy-3- pyridyl)imidazo [2,1- b][1,3,4]thia- diazol-2- yl]amino] cyclohexanol 1.61261 2.14 699_0240_0311 [00579] 1-[5-[2-(2- morpholinoethyl- amino)imidazo [2,1- b][1,3,4]thia- diazol-5-yl]-2- thienyl] ethanone 3 1.77 699_0252_0066 [00580] N-[3-(3- acetylphenyl)-6- (2- methoxyphenyl) imidazo[1,2- a]pyridin-8- yl]acetamide 1.58352 2.61 802_4145_0083 [00581] N-[3-(3-chloro- 4-fluoro- phenyl)-6-[3- (methanesulfon- amido)phenyl] imidazo[1,2- a]pyridin-8- yl]formamide 2.85911 2.28 788_0164_6488 [00582] 5-(4-pyridyl)-N- (2- thienylmethyl) imidazo[2,1- b][1,3,4]thia- diazol-2-amine 3.61591 2.93 699_0146_0069 [00583] N-[3-[2- (cyclohexyl- amino) imidazo[2,1- b][1,3,4]thia- diazol-5- yl]phenyl]meth- anesulfonamide 4.33348 2.68 699_0052_6488 [00584] 3-[2- (isobutylamino) imidazo[2,1- b][1,3,4]thia- diazol-5- yl]benzamide 1.13221 2.60 699_0149_0347 [00585] 3-[2- (cyclopropyl- methyl- amino)imidazo [2,1- b][1,3,4]thia- diazol-5- yl]benzamide 1.94081 2.14 699_4051_0347 [00586] 4-[[5-(3- fluorophenyl) imidazo[2,1- b][1,3,4]thia- diazol-2- yl]amino]cyclo- hexanol 2.92063 3.06 699_0240_0313 [00587] 4-[[5-(3,4- dimethoxyphen- yl)imidazo[2,1- b][1,3,4]thia- diazol-2- yl]amino]cyclo- hexanol 0.48307 2.60 699_0240_0079 [00588] 5-(3-pyridyl)-N- (2- thienylmethyl) imidazo[2,1- b][1,3,4]thia- diazol-2-amine 1.94173 2.93 699_0146_0071 [00589] 5-(3,4- dimethoxyphen- yl)-N-(4- pyridylmethyl) imidazo[2,1- b][1,3,4]thia- diazol-2-amine 2.1285 2.70 699_0237_0079 [00590] N-[6-(4- aminophenyl)-3- (4- fluorophenyl) imidazo[1,2- a]pyridin-8- yl]acetamide 5.25032 2.53 802_0339_7917 [00591] N-[3-(4- fluorophenyl)-6- (1- methylpyrazol- 4- yl)imidazo[1,2- a]pyridin-8- yl]formamide 8.08703 1.73 788_0339_8400 [00592] 2-amino-1-(3- methoxyphenyl) pyrrolo[3,2- b]quinoxaline-3- carboxamide 1.18486 2.64 DT2012- 0375412 [00593] N-cyclohexyl-5- (3- fluorophenyl) imidazo[2,1- b][1,3,4]thia- diazol-2-amine 4.07753 4.45 699_0052_0313 [00594] N-(2- furylmethyl)-5- (3- pyridyl)imidazo [2,1- b][1,3,4]thia- diazol-2-amine 3.16405 2.07 699_0144_0071 [00595] N-(2- furylmethyl)-5- (1- methylpyrazol- 4- yl)imidazo[2,1- b][1,3,4]thia- diazol-2-amine 5.63578 1.72 699_0144_7468 [00596] 5-(5-methoxy-3- pyridyl)-N-(2- thienylmethyl) imidazo[2,1- b][1,3,4]thia- diazol-2-amine 0.72859 2.77 699_0146_0196 [00597] 5-(3,4- dimethoxyphen- yl)-N-isobutyl- imidazo[2,1- b][1,3,4]thia- diazol-2-amine 2.74508 3.44 699_0149_0079 [00598] 1-[3-[2- (isobutylamino) imidazo[2,1- b][1,3,4]thia- diazol-5- yl]phenyl] ethanone 15.11833 3.31 699_0149_4145 [00599] N-benzyl-5-(3- pyridyl)imidazo 2,1- b][1,3,4]thia- diazol-2-amine 0.8393 3.01 699_0232_0071 [00600] N-benzyl-5-(5- methoxy-3- pyridyl)imidazo [2,1- b][1,3,4]thia- diazol-2-amine 0.34323 2.86 699_0232_0196 [00601] 5-(3-pyridyl)-N- (tetrahydropyran- 4- ylmethyl)imidazo [2,1- b][1,3,4]thia- diazol-2-amine 4.84876 1.71 699_0243_0071 [00602] 5-(5-methoxy-3- pyridyl)-N- (tetrahydropyran- 4- ylmethyl)imidazo [2,1- b][1,3,4]thia- diazol-2-amine 0.38423 1.55 699_0243_0196 [00603] N-[(4- methoxyphenyl) methyl]-5-(5- methoxy-3- pyridyl)imidazo [2,1 b][1,3,4]thia- diazol-2-amine 9.65333 2.70 699_0244_0196 [00604] N-(o- tolylmethyl)-5- (3- pyridyl)imidazo [2,1- b][1,3,4]thia- diazol-2-amine 1.07729 3.53 699_8074_0071 [00605] 1-methyl-N- (4- methylpiperazin- 1-yl)phenyl]-2- [3- (trifluoro- methyl) phenyl]pyrrolo [3, 2-c]pyridin-6- amine 30 5.51 809_2669_5837_ 0091 [00606] 1-methyl-N- pyrimidin-4-yl-2- [3- (trifluoro- methyl) phenyl]pyrrolo [3, 2-c]pyridin-6- amine 16.77669 4.23 809_2669_5837_ 6410 [00607] 2-(3- fluorophenyl)-1- methyl-N-[4-(4- methylpiperazin- 1- yl)phenyl] pyrrolo [3,2-c]pyridin- 6-amine 12.86554 4.78 809_2670_5837_ 0091 [00608] 2-(3- fluorophenyl)-1- methyl-N- pyrimidin-4-yl- pyrrolo[3,2- c]pyridin-6- amine 9.08728 3.49 809_2670_5837_ 6410 [00609] 5-amino-4-(1H- benzimidazol-2- yl)-1-(1,3- benzodioxol-5- yl)-2H-pyrrol-3- one 4.06818 2.64 DT2009- 0160159 [00610] N,N-dimethyl-4- [4-[4-(4- methylpiperazin- 1-yl)anilino]- 1H-pyrrolo[3,2- c]pyridin-2- yl]benzamide 7.04339 3.71 838_2671_0263_ 0091 [00611] 4-[2-(3,5- dimethoxyphen- yl)-1H- pyrrolo[3,2- c]pyridin-4- yl]morpholine 30 2.59 838_2728_0263_ 4009 [00612] N-[4-[[2-(2- methoxyphenyl)- 1H-pyrrolo[3,2- c]pyridin-4- yl]amino] phenyl] acetamide 30 3.54 838_2729_0263_ 0023 [00613] 2-(2- methoxyphenyl)- 1-methyl-N-[3- (trifluoro- methyl) phenyl]pyrrolo [3, 2-c]pyridin-4- amine 30 5.40 838_2729_5837_ 0235 [00614] 8-(2,5- dimethoxyphen- yl)-7-(4- fluorophenyl)-1- methyl-3H- imidazo[1,2- g]purine-2,4- dione [Also listed as: 6-(2,5- dimethoxyphen- yl)-7-(4- fluorophenyl)- 4-methyl- purino[7,8- a]imidazole- 1,3-dione: 18.44433 2.44 DT2012- 0296118 [00615] methyl 2-amino- 1-(3- hydroxphenyl) pyrrolo[3,2- b]quinoxaline-3- carboxylate 2.25787 3.64 DT2012- 0351552

TABLE-US-00004 TABLE 4 Secondary screen- initial candidate compounds re-synthesized and expanded. logP Compound ID. IC50 FYN (con- (prior ID Structure IUPAC name (M) sensus) No. if any) [00616] 5-phenyl-3- (3,4,5- trimethoxy- phenyl)pyridin- 2-amine 1.306193248 3.34 BF000312489 (382_0087_0061) [00617] 5-[4-(4- methylpiper- azin-1- yl)phenyl]- 3-(3,4,5- trimethoxy- phenyl)pyridin- 2-amine 0.232041699 3.30 BF000312520 (382_0087_0218) [00618] 3-[6-amino- 5-(3,4,5- trimethoxy- phenyl)-3- pyridyl]phe- nol 0.52870963 3.04 BF000312527 (382_0087_0284) [00619] 3-[6-amino- 5-(3,4,5- trimethoxy- phenyl)-3- pyridyl]benz- amide 0.4942965 2.19 BF000312539 (382_0087_0347) [00620] 4-[6-amino- 5-(3,4,5- trimethoxy- phenyl)-3- pyridyl]benz- amide 0.4578952 2.19 BF000312540 (382_0087_0346) [00621] 3-[6-amino- 5-(3,4,5- trimethoxy- phenyl)-3- pyridyl]-N- (2- hydroxyethyl) benzamide 1.001189887 1.73 BF000312542 (382_0087_0192) [00622] 5-(4- methylsulfo- nylphenyl)- 3-(3,4,5- trimethoxy- phenyl)pyridin- 2-amine 0.674160478 2.18 BF000312544 [00623] N-[3-[6- amino-5- (3,4,5- trimethoxy- phenyl)-3- pyridyl]phe- nyl]methane- sulfonamide 0.561599306 1.72 BF000312545 (382_0087_6488) [00624] 4-[2-amino- 5-(3,4,5- trimethoxy- phenyl)-3- pyridyl]phe- nol 0.2885 3.04 BF000313556 (382_7249_0087) [00625] 4-[6-amino- 5-(4- hydroxyphe- nyl)-3- pyridyl]benz- amide 1.085653826 2.36 BF000313559 [00626] N-[3-[6- amino-5-(4- hydroxy- phenyl)-3- pyridyl]phe- nyl]acetamide 0.898083782 2.75 BF000313562 (382_7249_0081) [00627] 4-[2-amino- 5-(4- methylsulfo- nylphenyl)- 3- pyridyl]phe- nol 1.551309576 2.35 BF000313563 (382_7249_0174) [00628] N-[3- (dimethyl- amino)propyl]- 4-[3-(4- hydroxyphe- nyl)imidazo [1,2- a]pyrazin-6- yl]benzamide 0.705417706 1.99 BF000333874 [00629] 4-[6-[4-(4- methylpiper- azin-1- yl)phenyl]imi- dazo[1,2- a]pyrazin-3- yl]phenol 0.464568962 2.79 BF000333878 (388_0080_0218) [00630] N-[2- (dimethyl- amino)ethyl]- 4-[3-(4- hydroxyphe- nyl)imidazo[1,2- a]pyrazin-6- yl]benzamide 0.486180008 1.93 BF000333881 [00631] N-(2- hydroxyethyl)- 4-[3-(4- hydroxyphe- nyl)imidazo[1,2- a]pyrazin-6- yl]benzamide 0.739736615 1.22 BF000333882 (388_0080_0328) [00632] N-[3- (dimethyl- amino)propyl]- 4-[3-(4- hydroxy-3- methoxy- phenyl)imi- dazo[1,2- a]pyrazin-6- yl]benzamide 0.647432877 1.83 BF000334019 (388_0314_0180) [00633] N-(2- hydroxyeth- yl)-3-[3-(4- hydroxy-3- methoxy- phenyl)imi- dazo[1,2- a]pyrazin-6- yl]benzamide 1.275657607 1.07 BF000334020 (388_0314_0192) [00634] 4-[2-amino- 5-[4-(4- methylpiper- azin-1- yl)phenyl]- 3- pyridyl]phe- nol 0.520622627 3.47 BF000710044 [00635] 3-[2- (cyclopropyl- methylamino) imidazo[2,1- b][1,3,4]thia- diazol-5-yl]- N,N- dimethyl- benzamide 0.884088514 2.59 BF000714798 (699_4051_0349) [00636] 5-(5- methoxy-3- pyridyl)-N- (2- thienylmeth- yl)imidazo[2,1- b][1,3,4]thia- diazol-2- amine 0.437195357 2.77 BF000714968 (699_0146_0196) [00637] 4-[[5-(3,4- dimethoxy- phenyl)imi- dazo[2,1- b][1,3,4]thia- diazol-2- yl]amino]cy- clohexanol 0.439583985 2.60 BF000717406 (699_0240_0079) [00638] 3-[2-[(4- hydroxycyclo- hexyl)amino] imidazo[2,1- b][1,3,4]thia- diazol-5-yl]- N,N- dimethyl- benzamide 0.288412517 2.22 BF000717418 (699_0240_0349) [00639] 4-[[5-(4- methoxy-3- pyridyl)imi- dazo[2,1- b][1,3,4]thia- diazol-2- yl]amino]cy- clohexanol 0.300821259 1.54 BF000802724 [00640] 2-methoxy- 4-[6- (propylamino) imidazo[1,2- b]pyridazin- 3-yl]phenol 0.081593995 2.71 BF000147080 [00641] 3-(4- pyridyl)-N- (2- thienylmeth- yl)imidazo[1,2- b]pyridazin- 6-amine 0.104821372 2.71 BF000145941 [00642] 2-methoxy- 4-[6- (tetrahydro- pyran-4- ylamino)imi- dazo[1,2- b]pyridazin- 3-yl]phenol 0.112523997 1.79 BF000147168 [00643] 4-[2-amino- 5-(3,4,5- trimethoxy- phenyl)-3- pyridyl]-2- methoxy- phenol 0.115507056 2.88 BF000313035 (382_0314.sub.0087) [00644] 4-[2-amino- 5-[4-(4- methylpiper- azin-1- yl)phenyl]- 3-pyridyl]-2- methoxy- phenol 0.121074357 3.31 BF000313028 [00645] 2-methoxy- 4-[6-(2- thienylmeth- ylamino)imi- dazo[1,2- b]pyridazin- 3-yl]phenol 0.166284575 3.46 BF000145954 [00646] N-[3-[6-(4- hydroxy-3- methoxy- phenyl)imi- dazo[1,2- b]pyridazin- 3-yl]phe- nyl]acetamide 0.166802816 3.03 BF000726183 (828_0081_0314) [00647] 4-[6-(3- hydroxypro- pylamino)imi- dazo[1,2- b]pyridazin- 3-yl]-2- methoxy- phenol 0.205976791 1.20 BF000146250 (229_0248_0314) [00648] 4-[6-amino- 5-(4- hydroxy-3- methoxy- phenyl)-3- pyridyl]benz- amide 0.214088697 2.20 BF000313038 [00649] N-propyl-3- (4- pyridyl)imi- dazo[1,2- b]pyridazin- 6-amine 0.217345163 1.95 BF000147056 [00650] N-[2- (dimethyl- amino)ethyl]- 4-[3-(4- phenoxyphe- nyl)imidazo[1,2- a]pyrazin-6- yl]benzamide 0.22160528 3.74 BF000334031 [00651] 2-methoxy- 4-[6-(2- pyridylmeth- ylamino)imi- dazo[1,2- b]pyridazin- 3-yl]phenol 0.233047949 2.41 BF000817095 [00652] N-[3- (dimethyl- amino)propyl]- 4-[3-(4- phenoxyphe- nyl)imidazo[1,2- a]pyrazin-6- yl]benzamide 0.247391087 3.80 BF000816927 [00653] 3-(4- pyridyl)-N- tetrahydro- pyran-4-yl- imidazo[1,2- b]pyridazin- 6-amine 0.270083246 1.03 BF000817099 [00654] 3-(3,4- dimethoxy- phenyl)-N- propyl- imidazo[1,2- b]pyridazin- 6-amine 0.285138703 2.85 BF000147061 (229_0226_0079) [00655] N-(1,3- benzodioxol- 5- ylmethyl)-3- (4- pyridyl)imi- dazo[1,2- b]pyridazin- 6-amine 0.297126173 2.42 BF000146108 (229_0236_0069) [00656] N-[3-[6-(3,4- dimethoxy- phenyl)imida- zo[1,2- b]pyridazin- 3- yl]phenyl]acet- amide 0.313364743 3.18 BF000726345 (828_0081_0079) [00657] 4-[2-amino- 5-(4- methylsulfo- nylphenyl)- 3-pyridyl]-2- methoxy- phenol 0.315744691 2.19 BF000313040 (382_0314_0174) [00658] N-[2- (dimethyl- amino)ethyl]- 4-[3-(4- hydroxy-3- methoxy- phenyl)imi- dazo[1,2- a]pyrazin-6- yl]benzamide 0.336758519 1.77 BF000334023 [00659] 3-(1,3- benzodioxol- 5-yl)-N-(2- pyridylmeth- yl)imidazo[1,2- b]pyridazin- 6-amine 0.354989794 2.50 BF000146330 (229_4007_0068) [00660] 4-[6-amino- 5-(3,4,5- trimethoxy- phenyl)-3- pyridyl]-N- cyclopropyl- benzamide 0.376810127 2.88 BF000312541 (382_0087_7489) [00661] N-[3-[6- (tetrahydro- pyran-4- ylamino)imi- dazo[1,2- b]pyridazin- 3- yl]phenyl]acet- amide 0.396885185 1.49 BF000146155 (229_0242_0081) [00662] 1-[3-[6- (propylamino) imidazo[1,2- b]pyridazin- 3- yl]phenyl]eth- anone 0.405532058 2.72 BF000147088 (229_0226_4145) [00663] 4-[6-[[(1S)- 1- (hydroxy- methyl)-2- methyl- propyl]amino] imidazo[1,2- b]pyridazin- 3-yl]-2- methoxy- phenol 0.44318569 2.44 BF000146319 [00664] 1-[3-[6-(2- thienylmeth- ylamino)imi- dazo[1,2- b]pyridazin- 3- yl]phenyl]eth- anone 0.450916544 3.48 BF000145962 (229_0146_4145) [00665] N-(2- hydroxyeth- yl)-4-[3-(4- phenoxy- phenyl)imi- dazo[1,2- a]pyrazin-6- yl]benzamide 0.463504693 3.03 BF000334032 (388_1029_0328) [00666] 3-(3,4- dimethoxy- phenyl)-N- tetrahydro- pyran-4-yl- imidazo[1,2- b]pyridazin- 6-amine 0.479948935 1.93 BF000146153 (229_0242_0079) [00667] 3-(3,4- dimethoxy- phenyl)-N-(2- pyridylmeth- yl)imidazo[1,2- b]pyridazin- 6-amine 0.494462769 2.56 BF000147233 [00668] N- tetrahydro- pyran-4-yl-3- (3,4,5- trimethoxy- phenyl)imi- dazo[1,2- b]pyridazin- 6-amine 0.503383229 1.78 BF000147394 (229_0242_0087) [00669] 3-[[3-(4- pyridyl)imi- dazo[1,2- b]pyridazin- 6- yl]amino]pro- pan-1-ol 0.538085737 0.44 BF000722253 [00670] 3-[6- (propylamino) imidazo[1,2- b]pyridazin- 3-yl]phenol 0.59230731 2.86 BF000147075 (229_0226_0284) [00671] 2-methoxy- 4-[6-(1- methyl- pyrazol-4- yl)imidazo[1,2- a]pyrazin-3- yl]phenol 0.624331939 1.11 BF000333452 (388_0314_8400) [00672] (2S)-3- methyl-2- [[3-(4- pyridyl)imi- dazo[1,2- b]pyridazin- 6- yl]amino]bu- tan-1-ol 0.630941398 1.68 BF000817097 [00673] 1-[3-[6-(3- hydroxypro- pylamino)imi- dazo[1,2- b]pyridazin- 3- yl]phenyl]eth- anone 0.64498853 1.21 BF000817098 [00674] 3-[[3-(1,3- benzodioxol- 5- yl)imidazo[1,2- b]pyridazin- 6- yl]amino]pro- pan-1-ol 0.707789559 1.28 BF000146218 (229_0248_0068) [00675] 5-[6-[3- (dimethyl- amino)pro- poxy]- 3-pyridyl]- 3-(3,4,5- trimethoxy- phenyl)pyridin- 2-amine 0.709144298 2.64 BF000312521 (382_0087_0002) [00676] 3-(3,4- dimethoxy- phenyl)-N-(2- thienylmeth- yl)imidazo[1,2- b]pyridazin- 6-amine 0.721406376 3.61 BF000146992 [00677] 3-[[3-(3,4- dimethoxy- phenyl)imi- dazo[1,2- b]pyridazin- 6- yl]amino]pro- pan-1-ol 0.72516936 1.34 BF000146224 [00678] N-[3-[6-(4- pyridyl)imi- dazo[1,2- b]pyridazin- 3- yl]phenyl]acet- amide 0.740677454 2.27 BF000817142 [00679] (2S)-2-[[3- (3,4- dimethoxy- phenyl)imi- dazo[1,2- b]pyridazin- 6-yl]amino]- 3-methyl- butan-1-ol 0.742215008 2.59 BF000147413 (229_0254_0079) [00680] N-[3-[6- [[(1S)-1- (hydroxy- methyl)-2- methyl- propyl]amino] imidazo[1,2- b]pyridazin- 3- yl]phenyl]acet- amide 0.791967537 2.14 BF000146300 (229_0254_0081) [00681] 3-(3- methoxy- phenyl)-N- tetrahydro- pyran-4-yl- imidazo[1,2- b]pyridazin- 6-amine 0.828721524 2.09 BF000146183 (229_0242_4140) [00682] 3-[3-(4- hydroxy- phenyl)imi- dazo[1,2- a]pyrazin-6- yl]-N,N- dimethyl- benzamide 0.870676961 2.14 BF000333343 (388_0080_0349) [00683] 4-[6-(1,3- benzodioxol- 5- ylmethyl- amino)imi- dazo[1,2- b]pyridazin- 3-yl]-2- methoxy- phenol 1.308570599 3.17 BF000146126 [00684] 3-(3- aminophenyl)- N- tetrahydro- pyran-4-yl- imidazo[1,2- b]pyridazin- 6-amine 1.423322773 1.42 BF000146142 (229_0242_0005) [00685] 1-[3-[6-(1,3- benzodioxol- 5- ylmethyl- amino)imi- dazo[1,2- b]pyridazin- 3- yl]phenyl]eth- anone 3.189566346 3.19 BF000147140 [00686] N-(1,3- benzodioxol- 5- ylmethyl)-3- (3,4- dimethoxy- phenyl)imi- dazo[1,2- b]pyridazin- 6-amine 6.216010093 3.32 BF000146114 [00687] 4-[2-amino- 5-(4- piperazin-1- ylphenyl)-3- pyridyl]-2- methoxy- phenol 0.060908784 2.93 BF000707279 [00688] N-benzyl-5- (3- pyridyl)imi- dazo[2,1- b][1,3,4]thia- diazol-2- amine 0.633579663 3.01 BF000714845 (699_0232_0071) [00689] 3-[2- (benzyl- amino)imi- dazo[2,1- b][1,3,4]thia- diazol-5-yl]- N,N- dimethyl- benzamide 1.233285044 3.53 BF000714847 (699_0232_0349) [00690] N-benzyl-5- (5-methoxy- 3- pyridyl)imi- dazo[2,1- b][1,3,4]thia- diazol-2- amine 0.217465905 2.86 BF000714862 (699_0232_0196) [00691] 5-(5- methoxy-3- pyridyl)-N- (tetrahydro- pyran-4- ylmethyl)imi- dazo[2,1- b][1,3,4]thia- diazol-2- amine 0.292588141 1.55 BF000714923 (699_0243_0196) [00692] N-(1,3- benzodioxol- 5- ylmethyl)-5- (5-methoxy- 3- pyridyl)imi- dazo[2,1- b][1,3,4]thia- diazol-2- 0.289073347 2.48 BF000714981 (699_0236_0196) amine [00693] N,N- dimethyl-3- [2- (tetrahydro- pyran-4- ylmethyl- amino)imi- dazo[2,1- b][1,3,4]thia- diazol-5- yl]benzamide 1.363919415 2.23 BF000715802 (699_0243_0349) [00694] 3-[2-(1,3- benzodioxol- 5- ylmethyl- amino)imi- dazo[2,1- b][1,3,4]thia- diazol-5-yl]- N,N- dimethyl- 1.925583132 3.15 BF000717214 benzamide [00695] 2-methoxy- 4-[2- (tetrahydro- pyran-4- ylmethyl- amino)imi- dazo[2,1- b][1,3,4]thia- diazol-5- yl]phenol 0.710456332 2.47 BF000717555 (699_0243_0314) [00696] 3-[3-[3- (hydroxy- methyl)phenyl] imidazo[1,2- b]pyridazin- 6-yl]phenol 1.166257347 3.18 BF000726195 (828_0291_0284) [00697] N-[3-[3-(3- acetamido- phenyl)imi- dazo[1,2- b]pyridazin- 6- yl]phenyl]acet- amide 0.647620035 2.73 BF000726346 (828_0081_0081) [00698] 3-[6-(4- pyridyl)imi- dazo[1,2- b]pyridazin- 3-yl]phenol 0.342140497 2.73 BF000726352 (828_0284_0069) [00699] [3-[6-(4- pyridyl)imi- dazo[1,2- b]pyridazin- 3- yl]phenyl]meth- anol 0.972914631 2.27 BF000726364 [00700] [3-[6-(3,4- dimethoxy- phenyl)imi- dazo[1,2- b]pyridazin- 3- yl]phenyl]meth- anol 0.892824216 3.17 BF000726366 (828_0291_0079) [00701] N-[3-[3-[3- (hydroxy- methyl)phenyl] imidazo[1,2- b]pyridazin- 6- yl]phenyl]acet- amide 1.516622765 2.72 BF000726367 (828_0291_0081) [00702] 4-[6-(3,4- dimethoxy- phenyl)imi- dazo[1,2- b]pyridazin- 3-yl]-2- methoxy- phenol 0.039407867 3.48 BF000726453 (828_0314_0079) [00703] N-[3-[3-(4- hydroxy-3- methoxy- phenyl)imi- dazo[1,2- b]pyridazin- 6- yl]phenyl]acet- amide 0.103548636 3.03 BF000726454 (828_0314_0081) [00704] 1-[3-[6-[3- (hydroxy- methyl)phenyl] imidazo[1,2- b]pyridazin- 3- yl]phenyl]eth- anone 0.290543095 3.04 BF000726471 (828_4145_0291) [00705] 4-[6-[4- (hydroxy- methyl)phenyl] imidazo[1,2- b]pyridazin- 3-yl]-2- methoxy- phenol 0.061804045 3.02 BF000726486 828_0314_0285) [00706] 4-[6-[3- (hydroxy- methyl)phenyl] imidazo[1,2- b]pyridazin- 3-yl]-2- methoxy- phenol 0.062959987 3.02 BF000726487 (828_0314_0291) [00707] 2-methoxy- 4-[6-(4- pyridyl)imi- dazo[1,2- b]pyridazin- 3-yl]phenol 0.079413853 2.57 BF000817169 [00708] 3-(4- pyridyl)-N- (2- pyridylmeth- yl)imidazo[1,2- b]pyridazin- 6-amine 0.170100794 1.66 BF000817170 [00709] 3,5- bis(3,4,5- trimethoxy- phenyl)pyridin- 2-amine 0.08540726 2.87 BF000817175 [00710] 4-[2-amino- 5-[4-(4- isopropylpiper- azin-1- yl)phenyl]-3- pyridyl]-2- methoxy- phenol 0.078146017 4.08 BF000817185 [00711] 4-[3-(4- hydroxy-3- methoxy- phenyl)imi- dazo[1,2- b]pyridazin- 6-yl]-2- methoxy- phenol 0.02944792 3.33 BF000817186 [00712] [3-[3-[3- (hydroxymeth- yl)phenyl]imi- dazo[1,2- b]pyridazin- 6- yl]phenyl]meth- anol 0.828494158 2.72 BF000817188 [00713] 5-(3,4- dimethoxy- phenyl)-N- (tetrahydro- pyran-4- ylmethyl)imi- dazo[2,1- b][1,3,4]thia- diazol-2- amine 1.026007749 2.61 BF000817208 [00714] N-[3-[6-[3- (hydroxy- methyl)phe- nyl]imidazo[1,2- b]pyridazin- 3- yl]phenyl]acet- amide 0.435155145 2.72 BF000817329 [00715] 4-[2-amino- 5-(4- morpholino- phenyl)-3- pyridyl]-2- methoxy- phenol 0.212232208 3.24 BF000817413 [00716] 5-[6-amino- 5-[4-(4- methylpiper- azin-1- yl)phenyl]- 3-pyridyl]-2- methoxy- phenol 9.65 3.31 BF000817418