Imidazol[1,2-α]quinoxalines and derivatives for the treatment of cancers
Imidazo[1,2-a]quinoxaline compounds for the treatment of cancers as well as pharmaceutical compositions that include these compounds and their uses in therapy. The compound of general formula (I):
1. The compound of formula (V):
wherein R 1 , R 2 , and R 3 represent independently an atom of hydrogen, a halogen or a group chosen among hydroxy, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, amino, C 1 -C 4 alkylamino, C 1 -C 4 dialkylamino, cyano, —CF 3 , —(CH 2 ) n NR 4 R 5 , or —NH—(CH 2 ) n NR 4 R 5 radicals,
R′ is selected from methylamino, dimethylamino, ethylamino, diethylamino, aminomethylamine or aminoethylamine group,
n is 1,2,3 or 4,
p is 1,2,3 or 4,
q is 1,2,3,4 or 5,
R 4 and R 5 represent independently an atom of hydrogen or group chosen among the linear or branched C 1 -C 4 alkyl
and/or a physiologically acceptable salt thereof.
2. The compound according to claim 1 wherein R 1 , R 2 and R 3 represent independently an atom of hydrogen, a halogen or a group chosen among the groups methyl, ethyl, propyl, isopropyl, butyl, isobutyl, and tert-butyl.
3. The compound according to claim 1 wherein R 3 is selected among H, Cl, Br, F, hydroxy, methyl, methoxy, ethoxy, —CF 3 , and CN.
4. The compound according to claim 1 wherein R 3 is selected among H, hydroxy, methoxy, ethoxy, Br, CF 3 , and Cl.
5. The compound according to claim 1 wherein q is 1.
6. The compound according to claim 1 wherein R′ is —NH—CH 3 , or —NH—(CH 2 ) 2 —NH 2 .
7. The compound of claim 1 , wherein R 1 is H; R 2 is H, R 3 is —OCH 3 , and R′ is NHCH 3 .
8. The compound of formula (VIII):
wherein R 1 , R 2 , and R 3 represent independently an atom of hydrogen, a halogen or a group chosen among hydroxy, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, amino, C 1 -C 4 alkylamino, C 1 -C 4 dialkylamino, cyano, —CF 3 , —(CH 2 )—NR 4 R 5 , or —NH—(CH 2 ) n NR 4 R 5 radicals,
R′ represents independently an atom of hydrogen, a halogen or a group chosen among C 1 -C 4 alkyl, C 1 -C 4 alkoxy, amino, C 1 -C 4 alkylamino, C 1 -C 4 dialkylamino, cyano, —CF 3 , —(CH 2 ) n NR 4 R 5 , —(CH 2 ) n COR 4 , or —NH—(CH 2 ) n NR 4 R 5 radicals,
n is 0,1,2,3 or 4,
p is 1,2,3, or 4,
q is 1,2,3 or 5,
R 4 and R 5 represent independently an atom of hydrogen or group chosen among the linear or branched C 1 -C 4 alkyl
and/or a physiologically acceptable salt thereof.
9. The compound according to claim 8 of formula (IX):
and/or a physiologically acceptable salt thereof.
10. A compound selected from the group consisting of:
N-methyl-1-phenylimidazo[1,2-a]quinoxalin-4-amine,
N-methyl-1-(2-hydroxyphenyl)imidazo[1,2-a]quinoxalin-4-amine,
N-methyl-1-(3-hydroxyphenyl)imidazo[1,2-a]quinoxalin-4-amine,
N-methyl-1-(4-hydroxyphenyl)imidazo[1,2-a]quinoxalin-4-amine,
N-methyl-1-(2,4-dihydroxyphenyl)imidazo[1,2-a]quinoxalin-4-amine,
N-methyl-1-(2,3-dihydroxyphenyl)imidazo[1,2-a]quinoxalin-4-amine,
N-methyl-1-(2-methoxyphenyl)imidazo[1,2-a]quinoxalin-4-amine,
N-methyl-1-(3-methoxyphenyl)imidazo[1,2-a]quinoxalin-4-amine,
N-methyl-1-(4-methoxyphenyl)imidazo[1,2-a]quinoxalin-4-amine,
N-methyl-1-(2,4-dimethoxyphenyl)imidazo[1,2-a]quinoxalin-4-amine,
N-methyl-1-(2,3-dimethoxyphenyl)imidazo[1,2-a]quinoxalin-4-amine,
N-methyl-1-(3-ethoxyphenyl)imidazo[1,2-a]quinoxalin-4-amine,
N-methyl-1-(4-ethoxyphenyl)imidazo[1,2-a]quinoxalin-4-amine,
N-methyl-1-(3-bromophenyl)imidazo[1,2-a]quinoxalin-4-amine,
N-methyl-1-(4-bromophenyl)imidazo[1,2-a]quinoxalin-4-amine,
N-methyl-1-(3-(trifluoromethyl)phenyl))imidazo[1,2-a]quinoxalin-4-amine,
N-methyl-1-(4-(trifluoromethyl)phenyl))imidazo [1,2-a]quinoxalin-4-amine,
N-methyl-1-(3-chlorophenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-methyl-1-(4-chlorophenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-methyl1-(3-fluorophenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-methyl1-(4-fluorophenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-methyl1-(3-cyanophenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-methyl1-(4-cyanophenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-(2-aminoethyl)-1-(2-hydroxyphenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-(2-aminoethyl)-1-(3-hydroxyphenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-(2-aminoethyl)-1-(4-hydroxyphenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-(2-aminoethyl)-1-(2,4-dihydroxyphenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-(2-aminoethyl)-1-(2,3-dihydroxyphenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-(2-aminoethyl)-1-(2-methoxyphenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-(2-aminoethyl)-1-(3-methoxyphenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-(2-aminoethyl)1-(4-methoxyphenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-(2-aminoethyl)1-(2,4-dimethoxyphenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-(2-aminoethyl)1-(2,3-dimethoxyphenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-(2-aminoethyl)1-(3-ethoxyphenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-(2-aminoethyl)1-(4-ethoxyphenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-(2-aminoethyl)1-(3-bromophenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-(2-aminoethyl)1-(4-bromophenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-(2-aminoethyl)-1-(3-(trifluoromethyl)phenyWimidazo [1,2-a]quinoxalin-4-amine,
N-(2-aminoethyl)-1-(4-(trifluoromethyl)phenyWimidazo [1,2-a]quinoxalin-4-amine,
N-(2-aminoethyl)-1-(3-chlorophenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-(2-aminoethyl)-1-(4-chlorophenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-(2-aminoethyl)-1-(3-fluorophenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-(2-aminoethyl)-1-(4-fluorophenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-(2-aminoethyl)-1-(3-cyanophenyl)imidazo [1,2-a]quinoxalin-4-amine,
N-(2-aminoethyl)-1-(4-cyanophenyl)imidazo [1,2-a]quinoxalin-4-amine,
1-phenylimidazo [1,2-a]quinoxalin-4-amine,
1-(2-hydroxyphenyl)imidazo [1,2-a]quinoxaline,
1-(3-hydroxyphenyl)imidazo [1,2-a]quinoxaline,
1-(4-hydroxyphenyl)imidazo [1,2-a]quinoxaline,
1-(2,4-dihydroxyphenyl)imidazo [1,2-a]quinoxalin-4-amine,
1-(2,3-dihydroxyphenyl)imidazo [1,2-a]quinoxalin-4-amine,
1-(2-methoxyphenyl)imidazo[1,2-a]quinoxalin-4-amine,
1-(3-methoxyphenyl)imidazo[1,2-a]quinoxalin-4-amine,
1-(4-methoxyphenyl)imidazo[1,2-a]quinoxalin-4-amine,
1-(2,4-dimethoxyphenyl)imidazo[1,2-a]quinoxalin-4-amine,
1-(2,3-dimethoxyphenyl)imidazo[1,2-a]quinoxalin-4-amine,
1-(3-ethoxyphenyl)imidazo[1,2-a]quinoxalin-4-amine,
1-(4-ethoxyphenyl)imidazo[1,2-a]quinoxalin-4-amine,
1-(3-bromophenyl)imidazo[1,2-a]quinoxalin-4-amine,
1-(4-bromophenyl)imidazo[1,2-a]quinoxalin-4-amine,
1-(3-(trifluoromethyl)phenyl))imidazo[1,2-a]quinoxalin-4-amine,
1-(4-(trifluoromethyl)phenyl))imidazo[1,2-a]quinoxalin-4-amine,
1-(3-chlorophenyl)imidazo[1,2-a]quinoxalin-4-amine,
1-(4-chlorophenyl)imidazo[1,2-a]quinoxalin-4-amine,
1-(3-fluorophenyl)imidazo[1,2-a]quinoxalin-4-amine,
1-(4-fluorophenyl)imidazo[1,2-a]quinoxalin-4-amine,
1-(3-cyanophenyl)imidazo[1,2-a]quinoxalin-4-amine,
1-(4-cyanophenyl)imidazo[1,2-a]quinoxalin-4-amine,
4-Chloro-1-phenylimidazo[1,2-a]quinoxaline,
4-Chloro-1-(2-hydroxyphenyl)imidazo[1,2-a]quinoxaline,
4-Chloro-1-(3-hydroxyphenyl)imidazo[1,2-a]quinoxaline,
4-Chloro-1-(4-hydroxyphenyl)imidazo[1,2-a]quinoxaline,
4-Chloro-1-(2-methoxyphenyl)imidazo[1,2-a]quinoxaline,
4-Chloro-1-(3-methoxyphenyl)imidazo[1,2-a]quinoxaline,
4-Chloro-1-(4-methoxyphenyl)imidazo[1,2-a]quinoxaline,
4-Chloro-1-(2,4-dimethoxyphenyl)imidazo[1,2-a]quinoxaline,
4-Chloro-1-(2,3-dimethoxyphenyl)imidazo[1,2-a]quinoxaline,
4-methoxy-1-phenylimidazo[1,2-a]quinoxaline,
4-methoxy-1-(2-hydroxyphenyl)imidazo[1,2-a]quinoxaline,
4-methoxy-1-(3-hydroxyphenyl)imidazo[1,2-a]quinoxaline,
4-methoxy-1-(4-hydroxyphenyl)imidazo[1,2-a]quinoxaline,
4-methoxy-1-(2-methoxyphenyl)imidazo[1,2-a]quinoxaline,
4-methoxy-1-(3-methoxyphenyl)imidazo[1,2-a]quinoxaline,
4-methoxy-1-(4-methoxyphenyl)imidazo[1,2-a]quinoxaline,
4-methoxy-1-(2,-dimethoxyphenyl)imidazo[1,2-a]quinoxaline, and
4-methoxy-1-(2,3-dimethoxyphenyl)imidazo[1,2-a]quinoxaline
and physiologically acceptable salts thereof.