MOLECULES THAT BIND TO TDP-43 FOR THE TREATMENT OF AMYOTROPHIC LATERAL SCLEROSIS AND RELATED DISORDERS
Pharmaceutical compositions of the invention comprise TDP-43 binding agents having a disease-modifying action in the treatment of diseases associated with TDP-43 that include ALS, FTLD, CTE, hippocampal sclerosis of aging (CARTS), Alzheimer's disease, and Alzheimer's disease related disorder, and disease that involve excess amounts of TDP-43 in the cytosol.
1 . A compound having formula (I):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug or a complex thereof, wherein:
X 1 is selected from the group consisting of nitrogen and CH;
R 1a is selected from the group consisting of hydrogen, halogen, CF 3 , OCF 3 , C 1-4 linear alkyl, C 3-4 branched alkyl, (C 2-8 dialkylamino)(C 2-4 alkyl), (C 3-6 alkyleneamino)(C 2-4 alkyl), (C 2-8 dialkylamino)(C 2-4 alkoxy), (C 3-6 alkyleneamino)(C 2-4 alkoxy), C 1-4 linear alkoxy, and C 3-4 branched alkoxy;
R 1b is selected from the group consisting of hydrogen, halogen, CF 3 , OCF 3 , C 1-4 linear alkyl, C 3-4 branched alkyl, (C 2-8 dialkylamino)(C 2-4 alkyl), (C 3-6 alkyleneamino)(C 2-4 alkyl), (C 2-8 dialkylamino)(C 2-4 alkoxy), (C 3-6 alkyleneamino)(C 2-4 alkoxy), C 1-4 linear alkoxy, and C 3-4 branched alkoxy;
R 1c is selected from the group consisting of hydrogen, halogen, CF 3 , OCF 3 , C 1-4 linear alkyl, C 3-4 branched alkyl, (C 2-8 dialkylamino)(C 2-4 alkyl), (C 3-6 alkyleneamino)(C 2-4 alkyl), (C 2-8 dialkylamino)(C 2-4 alkoxy), (C 3-6 alkyleneamino)(C 2-4 alkoxy), C 1-4 linear alkoxy, and C 3-4 branched alkoxy;
R 1d is selected from the group consisting of hydrogen, halogen, CF 3 , OCF 3 , C 1-4 linear alkyl, C 3-4 branched alkyl, (C 2-8 dialkylamino)(C 2-4 alkyl), (C 3-6 alkyleneamino)(C 2-4 alkyl), (C 2-8 dialkylamino)(C 2-4 alkoxy), (C 3-6 alkyleneamino)(C 2-4 alkoxy), C 1-4 linear alkoxy, and C 3-4 branched alkoxy;
wherein any two selected from the group consisting of R 1a , R 1b , R 1c , and R 1d are optionally connected to form a ring;
R 2 is selected from the group consisting of —(CH 2 ) n —NR 5 R 6 , —(CH 2 ) n C(O)—NR 5 R 6 ,
n 1 is 1 or 2;
R 4 is hydrogen; CF 3 ; a five-membered monocyclic heteroaryl ring comprising at least one heteroatom selected from the group consisting from O, N, and S that is optionally substituted with up to 2 groups selected from C 1-4 linear alkyl, C 3-4 branched alkyl, C 1-4 linear alkoxy, C 3-4 branched alkoxy, CF 3 , CF 3 O, halogen,
a five-membered monocyclic heteroaryl ring comprising at least one heteroatom selected from the group consisting from O, N, and S;
a phenyl ring that is optionally substituted with up to 2 groups selected from C 1-4 linear alkyl, C 3-4 branched alkyl, C 1-4 linear alkoxy, C 3-4 branched alkoxy, C 3-6 cycloalkyl, C 3-6 cycloalkoxy, CF 3 , CF 3 O, halogen, NR 3a R 3b , SO 2 NR 3a R 3b , NHSO 2 R 3a ,
R 3a is at each occurrence independently selected from the group consisting of C 1-4 linear alkyl and C 3-4 branched alkyl;
R 3b is at each occurrence independently selected from the group consisting of C 1-4 linear alkyl and C 3-4 branched alkyl;
R 5 is selected from the group consisting of hydrogen, C 1-4 linear alkyl, C 3-4 branched alkyl, —CH 2 —(C 1-6 cycloalkyl), C(O)C 1-6 linear alkyl, C(O)C 3-6 branched alkyl, C(O)CH(NH 2 )C 1-6 linear alkyl, C(O)CH(NH 2 )C 3-6 branched alkyl,
R 6 is selected from the group consisting of C 1-4 linear alkyl C 3-4 branched alkyl,
and an optionally substituted benzyl group wherein the optionally substituted benzyl group is substituted with 0 to 2 groups selected from the group consisting of halogen, —CN, —NO 2 , —OH, —NH 2 , C 1-6 alkyl, C 3-7 branched alkyl, C 1-6 linear haloalkyl, C 3-7 branched haloalkyl, C 1-6 linear alkoxy, C 3-7 branched alkoxy, C 1-6 linear haloalkoxy, C 3-7 branched haloalkoxy, C 3-7 cycloalkyl, aryl, heterocycle, and heteroaryl, provided that when R 2 is
R 6 is not hydrogen, C 1-4 linear alkyl, C 3-4 branched alkyl, or benzyl;
n 2 is 1 or 2;
n 3 is 0 or 1;
n 4 is 0 or 1;
n 5 is 0, 1, or 2;
n 6 is 0 or 1;
R 7 is selected from the group consisting of hydrogen and C(O)OR 8 ;
R 8 is selected from the group consisting of C 1-4 linear alkyl and C 3-4 branched alkyl;
X 2 is selected from the group consisting of a single bond, oxygen, CH 2 , CHOH, and NR 9 ;
R 9 is C 1-4 linear alkyl that is optionally substituted with an NH 2 ;
R 10 is selected from the group consisting of OH, OR 11 , NR 12 R 13 , NHSO 2 R 22 , and
R 11 is selected from the group consisting of C 1-4 linear alkyl and C 3-4 branched alkyl;
R 12 is selected from the group consisting of hydrogen, C 1-4 linear alkyl, C 3-4 branched alkyl, C 1-4 linear fluoroalkyl, C(O)R 14 ;
R 13 is selected from the group consisting of hydrogen, C 1-4 linear alkyl, C 3-4 branched alkyl, and heteroaryl;
R 12 and R 13 are optionally taken together with the atoms to which they are connected to form a ring with 3 to 6 atoms;
R 14 is selected from the group consisting of C 1-4 linear alkyl C 3-4 branched alkyl, and
R 15 is selected from the group consisting of C 1-4 linear alkyl and C 3-4 branched alkyl;
R 16 is selected from the group consisting of hydrogen, C 1-4 linear alkyl, C 3-4 branched alkyl, CH 2 —(C 1-6 cycloalkyl), and C(O)R 18 ;
R 7 is selected from the group consisting of hydrogen, benzyl and C(O)R 18 ;
R 8 is selected from the group consisting of C 1-4 linear alkyl and C 3-4 branched alkyl;
R 19 is selected from the group consisting of hydrogen and C(O)R 20 ;
R 20 is selected from the group consisting of C 1-4 linear alkyl and C 3-4 branched alkyl;
R 21 is a benzene ring that is optionally substituted with 0 to 2 groups selected from the group consisting of halogen, —CN, —NO 2 , —OH, —NH 2 , C 1-6 alkyl, C 3-7 branched alkyl, C 1-6 linear haloalkyl, C 3-7 branched haloalkyl, C 1-6 linear alkoxy, C 3-7 branched alkoxy, C 1-6 linear haloalkoxy, C 3-7 branched haloalkoxy, C 3-7 cycloalkyl, aryl, heterocycle, and heteroaryl;
R 22 is selected from the group consisting of C 1-4 linear alkyl, C 3-4 branched alkyl,
n is 2, 3, or 4;
m is 2, 3, or 4;
q is 2, 3, or 4;
y is 2, 3, or 4;
u is 2, 3, or 4;
v is 2, 3, or 4;
w is 2, 3, or 4;
z is 1, 2 or 3;
r is 2, 3, or 4; and
x is 2, 3, or 4.
2 . The compound of claim 1 having formula (II):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complex thereof.
3 . The compound of claim 1 having formula (III):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complex thereof.
4 . The compound of claim 1 having formula (IV):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complex thereof.
5 . The compound of claim 1 having formula (V):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complex thereof.
6 . The compound of claim 1 having formula (VI):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complex thereof.
7 . The compound of claim 1 having formula (VII):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complex thereof.
8 . The compound of claim 1 having formula (VIII):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complex thereof.
9 . The compound of claim 1 having formula (IX):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complex thereof.
10 . The compound of claim 1 having formula (X):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complex thereof.
11 . The compound of claim 1 having formula (XI):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, and a complex thereof.
12 . The compound of claim 1 having formula (XII):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complex thereof.
13 . The compound of claim 1 having formula (XIII):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complex thereof.
14 . The compound of claim 1 having formula (XIV):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrugs, or a complex thereof.
15 . The compound of claim 1 having formula (XV):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complex thereof.
16 . The compound of claim 1 having formula (XVI):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complex thereof.
17 . The compound of claim 1 having formula (XVII):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complex thereof.
18 . The compound of claim 1 having formula (XVIII):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salts, an isotopic analog, a prodrug, or a complex thereof.
19 . The compound of claim 1 having formula (XIX):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complex thereof.
20 . The compound of claim 1 having formula (XX):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complex thereof.
21 . The compound of claim 1 having formula (XXI):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complex thereof.
22 . The compound of claim 1 having formula (XXII):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complexes thereof.
23 . The compound of claim 1 having formula (XXIII):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complex thereof.
24 . The compound of claim 1 having formula (XXIV):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complex thereof.
25 . The compound of claim 1 having formula (XXV):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analogs, a prodrug, or a complex thereof.
26 . The compound of claim 1 having formula (XXVI):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complex thereof.
27 . The compound of claim 1 having formula (XXVII):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complex thereof.
28 . The compound according to claim 1 that is:
N 1 -(3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)-N 1 ,N 3 ,N 3 -trimethyl propane-1,3-diamine;
2-(4-Methoxyphenyl)-N-(3-f{methyl[3-(methylamino)propyl]-amino}propyl)quinolin-4-amine;
N 1 -(3-Aminopropyl)-N 3 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
N 1 -(2-(4-Methoxyphenyl)quinolin-4-yl)-N 3 -(3-(piperidin-1-yl)propyl)propane-1,3-diamine;
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 3 -methyl-N 3 -(3-(piperidin-1-yl)propyl)propane-1,3-diamine;
tert-Butyl N-{3-[(3-{[2-(4-methoxyphenyl)quinolin-4yl]amino}propyl)amino]propyl}carbamate;
N 1 -(3-aminopropyl)-N 3 -(5-fluoro-2-(4-methoxyphenyl)quinolin-4-yl)-N 1 -methylpropane-1,3-diamine:
N-{3-[(3-Aminopropyl)amino]propyl}-2-(4-methoxyphenyl)quinolin-4-amine;
N 1 -(3-Aminopropyl)-N 3 -(6-methoxy-2-(4-methoxyphenyl)quinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
N 1 -(3-Aminopropyl)-N 3 -(2-(2-methyl-4-methoxyphenyl)quinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
N 1 -(3-Aminopropyl)-N 3 -(6,7-dimethoxy-2-(4-methoxyphenyl)quinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
N 1 -(3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)-N 1 ,N 4 -dimethylbutane-1,4-diamine;
N 1 -(2-fluoroethyl)-N 3 -(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)-N 1 ,N 3 -dimethylpropane-1,3-diamine;
3-((3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)amino)-propan-1-ol;
N-(3-(3-methoxypropylamino)propyl)-2-(4-methoxyphenyl)quinolin-4-amine;
N-(3-(2-(4-Methoxyphenyl)quinolin-4-ylamino)propyl)-N-(3-aminopropyl)acetamide;
N 1 -(Cyclopropylmethyl)-N 1 -(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)-N 3 ,N 3 -dimethyl propane-1,3-diamine:
tert-Butyl 3-(((3-(dimethylamino)propyl)(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)amino)methyl)azetidine-1-carboxylate;
tert-Butyl 4-(((3-(dimethylamino)propyl)(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)amino)methyl)piperidine-1-carboxylate:
N 1 -(Azetidin-3-ylmethyl)-N 1 -(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)-N 3 ,N 3 -dimethyl-N 1 -(piperidin-4-ylmethyl)propane-1,3-diamine;
N 1 -(2-(4-Methoxyphenyl)quinolin-4-yl)-N 3 -((1-methyl-1H-imidazol-5-yl)methyl)propane-1,3-diamine;
N-(3-(Hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)propyl)-2-(4-methoxyphenyl)quinolin-4-amine;
N 1 -((6-Aminopyridin-3-yl)methyl)-N 3 -(2-(4-methoxyphenyl)-quinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
1-(Dimethylamino)-3-((3-((2-(4-methoxyphenyl)quinolin-4-yl)-amino)propyl)(methyl)amino)propan-2-ol;
1-(3-((3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)-methylamino)propyl)piperidin-4-ol;
tert-butyl 5-(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)hexahydro-pyrrolo[3,4-c]pyrrole-2(1H)-carboxylate;
N 1 -((6-(dimethylamino)pyridin-3-yl)methyl)-N 3 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 1 -methyl propane-1,3-diamine;
N 1 -(3-aminopropyl)-N 1 -methyl-N 3 -(2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 3 -methyl-N 3 -((1-methylpiperidin-4-yl)methyl)propane-1,3-diamine:
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 3 -methyl-N 3 -(2-(piperidin-2-yl)ethyl)propane-1,3-diamine;
tert-Butyl(2-(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)octahydrocyclopenta[c]pyrrol-4-yl)carbamate:
N 1 -(2-(4-Methoxyphenyl)quinolin-4-yl)-N 3 -(octahydrocyclopenta[c]pyrrol-4-yl)propane-1,3-diamine;
N-(3-(4-Aminohexahydrocyclopenta[c]pyrrol-2(1H)-yl)propyl)-2-(4-methoxyphenyl)quinolin-4-amine;
tert-Butyl 2-(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)hexahydro-1H-pyrrolo[3,4-c]pyridine-5(6H)-carboxylate;
N-(3-(Hexahydro-1H-pyrrolo[3,4-c]pyridin-2(3H)-yl)propyl)-2-(4-methoxyphenyl)quinolin-4-amine;
tert-Butyl 4-((3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)amino)hexahydrocyclopenta[c] pyrrole-2(1H)-carboxylate;
N 1 -((1-(Cyclopropylmethyl)piperidin-4-yl)methyl)-N 3 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 1 -methyl propane-1,3-diamine;
N-(2-(1-(3-Aminopropyl)piperidin-2-yl)ethyl)-2-(4-methoxyphenyl)quinolin-4-amine:
N 1 -(1-(4-Fluorobenzyl)piperidin-4-yl)-N 3 -(2-(4-methoxyphenyl)quinolin-4-yl)propane-1,3-diamine:
tert-Butyl 6-(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)-2,6-diazaspiro[3.4]octane-2-carboxylate;
N-(3-(2,6-Diazaspiro[3.4]octan-6-yl)propyl)-2-(4-methoxyphenyl)quinolin-4-amine:
2-(4-Methoxyphenyl)-N-(3-(4-methyl-1,4-diazepan-1-yl)propyl)quinolin-4-amine:
tert-Butyl 2-(2-((3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)amino)ethyl)piperidine-1-carboxylate;
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 3 -(2-(piperidin-2-yl)ethyl)propane-1,3-diamine;
N-(3-(4-(3-Aminopropyl)piperazin-1-yl)propyl)-2-(4-methoxyphenyl)quinolin-4-amine;
tert-Butyl 4-{[(3-{[2-(4-methoxyphenyl)quinolin-4-yl]amino}propyl)(methyl)amino]methyl}piperidine-1-carboxylate;
N-(3-(N-Methyl-N-((piperidin-4-yl)methyl)amino)propyl)-2-(4-methoxyphenyl)quinolin-4-amine;
N-(3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)-4-(2H-tetrazol-5-yl)benzenesulfonamide;
N 1 -(4-(2H-Tetrazol-5-yl)phenyl)-N 3 -(2-(4-methoxyphenyl)quinolin-4-yl)propane-1,3-diamine;
(1-(3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)piperidin-4-yl)methanol;
1-(Diethylamino)-3-((3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)amino)propan-2-ol;
N 1 -(2-(4-Methoxyphenyl)quinolin-4-yl)-N 3 -((1-methyl-1H-pyrazol-5-yl)methyl)propane-1,3-diamine;
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 3 -(2-(pyridin-2-yl)ethyl)propane-1,3-diamine;
N 1 -(2-(4-Methoxyphenyl)quinolin-4-yl)-N 3 -(4-(piperidin-1-yl)phenyl)propane-1,3-diamine;
N-((1-(3-Aminopropyl)piperidin-3-yl)methyl)-2-(4-methoxyphenyl)quinolin-4-amine;
N-(3-(2-(6-Methoxy-1H-indol-3-yl)ethylamino)propyl)-2-(4-methoxyphenyl)quinolin-4-amine:
tert-Butyl 4-{[({1-[(tert-butoxy)carbonyl]piperidin-4-yl}methyl)(3-{[2-(4-methoxyphenyl)-quinolin-4-yl]amino}propyl)amino]methyl}piperidine-1-carboxylate;
N-(3-(Bis((piperidin-4-yl)methyl)amino)propyl)-2-(4-methoxyphenyl)quinolin-4-amine;
N 1 -(4-Methoxybenzyl)-N 3 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
tert-Butyl(3-((4-((2-(4-methoxyphenyl)quinolin-4-yl)amino)cyclohexyl)amino)propyl)carbamate;
tert-Butyl 4-{[(3-{[2-(4-methoxyphenyl)quinolin-4-yl]amino}propyl)amino]methyl}piperidine-1-carboxylate;
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 3 -(3-(pyridin-4-ylamino)propyl)propane-1,3-diamine;
2-(3-(4-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)piperidin-1-yl)propyl)isoindoline-1,3-dione;
2-(3-(3-(((2-(4-Methoxyphenyl)quinolin-4-yl)amino)methyl)piperidin-1-yl)propyl)isoindoline-1,3-dione;
N-(3-((3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)amino)propyl) methanesulfonamide;
2-(3-(2-(2-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)ethyl)piperidin-1-yl)propyl)isoindoline-1,3-dione;
N-(3-(Hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)propyl)-2-(4-methoxy phenyl)quinolin-4-amine;
2-(4-Methoxyphenyl)-N-(1′-methyl-[1,4′-bipiperidine]-4-yl)quinolin-4-amine;
N 1 -(2-Benzyloctahydrocyclopenta[c]pyrrol-4-yl)-N 3 -(2-(4-methoxyphenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 -((1-(Cyclopropylmethyl)piperidin-4-yl)methyl)-N 3 -(2-(4-methoxyphenyl)quinolin-4-yl)propane-1,3-diamine;
1-(3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)piperidine-4-carboxamide;
2-(4-Methoxyphenyl)-N-(3-(4-methylpiperazin-1-yl)propyl)quinolin-4-amine;
2-(4-Methoxyphenyl)-N-(2-(4-methylpiperazin-1-yl)ethyl)quinolin-4-amine;
2-(4-Methoxyphenyl)-N-(3-morpholinopropyl)quinolin-4-amine;
2-(7-Amino-4-methyl-2-oxo-2H-chromen-3-yl)-N-(3-((3-((2-(4-methoxyphenyl)quinolin-4-yl)amino) propyl)(methyl)amino)propyl)acetamide;
5-(dimethylamino)-N-{3-[(3-{[2-(4-methoxyphenyl)quinolin-4yl]amino}propyl)(methyl)amino]propyl}naphthalene-1-sulfonamide;
cis-N 1 -(6,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)cyclobutane-1,3-diamine;
trans-N 1 -(6,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)cyclobutane-1,3-diamine;
trans-N 1 -(6,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)cyclohexane-1,4-diamine;
N 1 -(6,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
cis-N 1 -(2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)cyclobutane-1,3-diamine;
N 1 -(2-(4-(5,6-dihydropyrrolo[3,4-c]pyrazol-2(4H)-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
cis-N 1 -(6,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)cyclohexane-1,4-diamine;
N 1 -(2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(6,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(3-aminopropyl)-N 1 -methyl-N 3 -(2-(3-(piperazin-1-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(6,7-dimethoxy-2-(4-methoxyphenyl)quinolin-4-yl)cyclohexane-1,4-diamine;
N 1 -(2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)cyclohexane-1,4-diamine;
2-amino-1-(4-(4-(4-((3-(dimethylamino)propyl)amino)quinolin-2-yl)phenyl)piperazin-1-yl)-3-methylbutan-1-one;
2-amino-1-(4-(4-(4-((3-(dimethylamino)propyl)amino)quinolin-2-yl)phenyl)piperazin-1-yl)propan-1-one;
N 1 -(2-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(3-aminopropyl)-N 3 -(6,7-dimethoxy-2-(4-methoxyphenyl)quinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
N 1 -(2-(4-(piperidin-4-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(2-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)quinolin-4-yl)propane-1,3-diamine;
trans-N 1 -(6,7-dimethoxy-2-(4-methoxyphenyl)quinolin-4-yl)cyclobutane-1,3-diamine;
N 1 ,N 1 -dimethyl-N 3 -(2-(3-(piperazin-1-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 ,N 1 -dimethyl-N 3 -(2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(2-(1-(2-(pyrrolidin-1-yl)ethyl)-1H-pyrazol-4-yl)quinolin-4-yl)propane-1,3-diamine;
trans-N 1 -(6,7-dimethoxy-2-(4-methoxyphenyl)quinolin-4-yl)cyclohexane-1,4-diamine;
N-(1-(4-aminocyclohexyl)piperidin-4-yl)-2-(4-methoxyphenyl)quinolin-4-amine;
N 1 -(6-fluoro-2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N-(1-(3-aminopropyl)piperidin-4-yl)-2-(4-methoxyphenyl)quinolin-4-amine;
cis-N1-(6,7-dimethoxy-2-(4-methoxyphenyl)quinolin-4-yl)cyclohexane-1,4-diamine;
2-amino-N-(1-((1-(4-(4-(4-((3-(dimethylamino)propyl)amino)quinolin-2-yl)phenyl)piperazin-1-yl)-3-methyl-1-oxobutan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)-3-methylbutanamide;
N 1 ,N 1 -dimethyl-N 3 -(2-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(6,7-dimethoxy-2-(4-methoxyphenyl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(6,7-dimethoxy-2-(4-methoxyphenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 ,N 1 -dimethyl-N 3 -(2-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
2-amino-N-(1-(4-(4-(4-((3-(dimethylamino)propyl)amino)quinolin-2-yl)phenyl)piperazin-1-yl)-3-methyl-1-oxobutan-2-yl)-3-methylbutanamide;
cis-N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)cyclobutane-1,3-diamine;
N 1 -([2,6′-biquinolin]-4-yl)propane-1,3-diamine;
4-(4-(4-((3-(dimethylamino)propyl)amino)quinolin-2-yl)phenyl)-1-methylpiperazin-2-one;
N 1 -(2-(piperidin-4-yl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(2-(2,3-dihydrobenzofuran-5-yl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(2-(4-(methoxy-d3)phenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 -([2,6′-biquinolin]-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)cyclobutane-1,3-diamine;
N 1 -(2-(1,2,3,6-tetrahydropyridin-4-yl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)cyclohexane-1,4-diamine;
2-(4-methoxyphenyl)-N-(piperidin-4-yl)quinolin-4-amine;
N 1 -(2-(4-(methoxy-d 3 )phenyl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(2-(benzofuran-5-yl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(2-(1-methyl-1H-pyrazol-4-yl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(2-(1-(azetidin-3-yl)-1H-pyrazol-4-yl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(2-(1-cyclopropyl-1H-pyrazol-4-yl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(2-(cyclohex-1-en-1-yl)quinolin-4-yl)propane-1,3-diamine;
(S)-2-amino-N-(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)-N-methylpropanamide;
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 3 ,N 3 -bis(methyl-d3)propane-1,3-diamine;
N 1 -(2-(furan-2-yl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(5-fluoro-2-(4-methoxyphenyl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(2-(1-(2-morpholinoethyl)-1H-pyrazol-4-yl)quinolin-4-yl)propane-1,3-diamine;
3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propan-1-ol;
N 1 -(2-(2-methoxypyrimidin-5-yl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 ,N 1 -dimethyl-N 3 -(2-methylquinolin-4-yl)propane-1,3-diamine;
3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)-N,N-dimethylpropanamide;
N 1 -(2-(6-methoxypyridin-3-yl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(2,2-difluoro-6-(4-methoxyphenyl)-[1,3]dioxolo[4,5-g]quinolin-8-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N-(4,4-difluorocyclohexyl)-2-(4-methoxyphenyl)quinolin-4-amine;
tert-butyl 3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propanoate;
N 1 -(6-methoxy-2-(trifluoromethyl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
2-cyclohexyl-N-(1-isopropylpiperidin-4-yl)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinolin-4-amine;
N 1 -(3-aminopropyl)-N 3 -(6,7-dimethoxyquinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
6-methoxy-N-(1-methylpiperidin-4-yl)-7-(3-(pyrrolidin-1-yl)propoxy)quinolin-4-amine;
N 1 -(6,7-dimethoxyquinolin-4-yl)-N 3 ,N 3 -diethylpropane-1,3-diamine;
6,7-dimethoxy-N-(1′-methyl-[1,4′-bipiperidin]-4-yl)quinolin-4-amine;
N 1 -(3-aminopropyl)-N 3 -(7-chloroquinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
N 1 -(3-aminopropyl)-N 3 -(2-(4-(dimethylamino)phenyl)quinolin-4-yl)-N-methylpropane-1,3-diamine,
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complex thereof.
29 . A composition comprising an effective amount of at least one compound according to claim 1 .
30 . The composition according to claim 29 , further comprising at least one excipient.
31 . The composition according to claim 30 , wherein the at least one compound is at least one selected from the group consisting of:
N 1 -(3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)-N 1 ,N 3 ,N 3 -trimethyl propane-1,3-diamine;
2-(4-Methoxyphenyl)-N-(3-f{methyl[3-(methylamino)propyl]-amino}propyl)quinolin-4-amine;
N 1 -(3-Aminopropyl)-N 3 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
N 1 -(2-(4-Methoxyphenyl)quinolin-4-yl)-N 3 -(3-(piperidin-1-yl)propyl)propane-1,3-diamine;
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 3 -methyl-N 3 -(3-(piperidin-1-yl)propyl)propane-1,3-diamine;
tert-Butyl N-{3-[(3-{[2-(4-methoxyphenyl)quinolin-4yl]amino}propyl)amino]propyl}carbamate;
N 1 -(3-aminopropyl)-N 3 -(5-fluoro-2-(4-methoxyphenyl)quinolin-4-yl)-N 1 -methylpropane-1,3-diamine:
N-{3-[(3-Aminopropyl)amino]propyl}-2-(4-methoxyphenyl)quinolin-4-amine;
N 1 -(3-Aminopropyl)-N 3 -(6-methoxy-2-(4-methoxyphenyl)quinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
N 1 -(3-Aminopropyl)-N 3 -(2-(2-methyl-4-methoxyphenyl)quinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
N 1 -(3-Aminopropyl)-N 3 -(6,7-dimethoxy-2-(4-methoxyphenyl)quinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
N 1 -(3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)-N 1 ,N 4 -dimethylbutane-1,4-diamine;
N 1 -(2-fluoroethyl)-N 3 -(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)-N 1 ,N 3 -dimethylpropane-1,3-diamine;
3-((3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)amino)-propan-1-ol;
N-(3-(3-methoxypropylamino)propyl)-2-(4-methoxyphenyl)quinolin-4-amine;
N-(3-(2-(4-Methoxyphenyl)quinolin-4-ylamino)propyl)-N-(3-aminopropyl)acetamide;
N 1 -(Cyclopropylmethyl)-N 1 -(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)-N 3 ,N 3 -dimethyl propane-1,3-diamine:
tert-Butyl 3-(((3-(dimethylamino)propyl)(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)amino)methyl)azetidine-1-carboxylate;
tert-Butyl 4-(((3-(dimethylamino)propyl)(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)amino)methyl)piperidine-1-carboxylate:
N 1 -(Azetidin-3-ylmethyl)-N 1 -(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)-N 3 ,N 3 -dimethyl-N 1 -(piperidin-4-ylmethyl)propane-1,3-diamine;
N 1 -(2-(4-Methoxyphenyl)quinolin-4-yl)-N 3 -((1-methyl-1H-imidazol-5-yl)methyl)propane-1,3-diamine;
N-(3-(Hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)propyl)-2-(4-methoxyphenyl)quinolin-4-amine;
N 1 -((6-Aminopyridin-3-yl)methyl)-N 3 -(2-(4-methoxyphenyl)-quinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
1-(Dimethylamino)-3-((3-((2-(4-methoxyphenyl)quinolin-4-yl)-amino)propyl)(methyl)amino)propan-2-ol;
1-(3-((3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)-methylamino)propyl)piperidin-4-ol;
tert-butyl 5-(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)hexahydro-pyrrolo[3,4-c]pyrrole-2(1H)-carboxylate;
N 1 -((6-(dimethylamino)pyridin-3-yl)methyl)-N 3 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 1 -methyl propane-1,3-diamine;
N 1 -(3-aminopropyl)-N 1 -methyl-N 3 -(2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 3 -methyl-N 3 -((1-methylpiperidin-4-yl)methyl)propane-1,3-diamine:
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 3 -methyl-N 3 -(2-(piperidin-2-yl)ethyl)propane-1,3-diamine;
tert-Butyl(2-(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)octahydrocyclopenta[c]pyrrol-4-yl)carbamate:
N 1 -(2-(4-Methoxyphenyl)quinolin-4-yl)-N 3 -(octahydrocyclopenta[c]pyrrol-4-yl)propane-1,3-diamine;
N-(3-(4-Aminohexahydrocyclopenta[c]pyrrol-2(1H)-yl)propyl)-2-(4-methoxyphenyl)quinolin-4-amine;
tert-Butyl 2-(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)hexahydro-1H-pyrrolo[3,4-c]pyridine-5(6H)-carboxylate;
N-(3-(Hexahydro-1H-pyrrolo[3,4-c]pyridin-2(3H)-yl)propyl)-2-(4-methoxyphenyl)quinolin-4-amine;
tert-Butyl 4-((3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate;
N 1 -((1-(Cyclopropylmethyl)piperidin-4-yl)methyl)-N 3 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 1 -methyl propane-1,3-diamine;
N-(2-(1-(3-Aminopropyl)piperidin-2-yl)ethyl)-2-(4-methoxyphenyl)quinolin-4-amine:
N 1 -(1-(4-Fluorobenzyl)piperidin-4-yl)-N 3 -(2-(4-methoxyphenyl)quinolin-4-yl)propane-1,3-diamine:
tert-Butyl 6-(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)-2,6-diazaspiro[3.4]octane-2-carboxylate;
N-(3-(2,6-Diazaspiro[3.4]octan-6-yl)propyl)-2-(4-methoxyphenyl)quinolin-4-amine:
2-(4-Methoxyphenyl)-N-(3-(4-methyl-1,4-diazepan-1-yl)propyl)quinolin-4-amine:
tert-Butyl 2-(2-((3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)amino)ethyl)piperidine-1-carboxylate;
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 3 -(2-(piperidin-2-yl)ethyl)propane-1,3-diamine;
N-(3-(4-(3-Aminopropyl)piperazin-1-yl)propyl)-2-(4-methoxyphenyl)quinolin-4-amine;
tert-Butyl 4-{[(3-{[2-(4-methoxyphenyl)quinolin-4-yl]amino}propyl)(methyl)amino]methyl}piperidine-1-carboxylate;
N-(3-(N-Methyl-N-((piperidin-4-yl)methyl)amino)propyl)-2-(4-methoxyphenyl)quinolin-4-amine;
N-(3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)-4-(2H-tetrazol-5-yl)benzenesulfonamide;
N 1 -(4-(2H-Tetrazol-5-yl)phenyl)-N 3 -(2-(4-methoxyphenyl)quinolin-4-yl)propane-1,3-diamine;
(1-(3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)piperidin-4-yl)methanol;
1-(Diethylamino)-3-((3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)amino)propan-2-ol;
N 1 -(2-(4-Methoxyphenyl)quinolin-4-yl)-N 3 -((1-methyl-1H-pyrazol-5-yl)methyl)propane-1,3-diamine;
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 3 -(2-(pyridin-2-yl)ethyl)propane-1,3-diamine;
N 1 -(2-(4-Methoxyphenyl)quinolin-4-yl)-N 3 -(4-(piperidin-1-yl)phenyl)propane-1,3-diamine;
N-((1-(3-Aminopropyl)piperidin-3-yl)methyl)-2-(4-methoxyphenyl)quinolin-4-amine;
N-(3-(2-(6-Methoxy-1H-indol-3-yl)ethylamino)propyl)-2-(4-methoxyphenyl)quinolin-4-amine:
tert-Butyl 4-{[({1-[(tert-butoxy)carbonyl]piperidin-4-yl}methyl)(3-{[2-(4-methoxyphenyl)-quinolin-4-yl]amino}propyl)amino]methyl}piperidine-1-carboxylate;
N-(3-(Bis((piperidin-4-yl)methyl)amino)propyl)-2-(4-methoxyphenyl)quinolin-4-amine;
N 1 -(4-Methoxybenzyl)-N 3 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
tert-Butyl(3-((4-((2-(4-methoxyphenyl)quinolin-4-yl)amino)cyclohexyl)amino)propyl)carbamate;
tert-Butyl 4-{[(3-{[2-(4-methoxyphenyl)quinolin-4-yl]amino}propyl)amino]methyl}piperidine-1-carboxylate;
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 3 -(3-(pyridin-4-ylamino)propyl)propane-1,3-diamine;
2-(3-(4-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)piperidin-1-yl)propyl)isoindoline-1,3-dione;
2-(3-(3-(((2-(4-Methoxyphenyl)quinolin-4-yl)amino)methyl)piperidin-1-yl)propyl)isoindoline-1,3-dione;
N-(3-((3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)amino)propyl) methanesulfonamide;
2-(3-(2-(2-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)ethyl)piperidin-1-yl)propyl)isoindoline-1,3-dione;
N-(3-(Hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)propyl)-2-(4-methoxy phenyl)quinolin-4-amine;
2-(4-Methoxyphenyl)-N-(1′-methyl-[1,4′-bipiperidine]-4-yl)quinolin-4-amine;
N 1 -(2-Benzyloctahydrocyclopenta[c]pyrrol-4-yl)-N 3 -(2-(4-methoxyphenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 -((1-(Cyclopropylmethyl)piperidin-4-yl)methyl)-N 3 -(2-(4-methoxyphenyl)quinolin-4-yl)propane-1,3-diamine;
1-(3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)piperidine-4-carboxamide;
2-(4-Methoxyphenyl)-N-(3-(4-methylpiperazin-1-yl)propyl)quinolin-4-amine;
2-(4-Methoxyphenyl)-N-(2-(4-methylpiperazin-1-yl)ethyl)quinolin-4-amine;
2-(4-Methoxyphenyl)-N-(3-morpholinopropyl)quinolin-4-amine;
2-(7-Amino-4-methyl-2-oxo-2H-chromen-3-yl)-N-(3-((3-((2-(4-methoxyphenyl)quinolin-4-yl)amino) propyl)(methyl)amino)propyl)acetamide;
5-(dimethylamino)-N-{3-[(3-{[2-(4-methoxyphenyl)quinolin-4yl]amino}propyl)(methyl)amino]propyl}naphthalene-1-sulfonamide, cis-N 1 -(6,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)cyclobutane-1,3-diamine;
trans-N 1 -(6,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)cyclobutane-1,3-diamine;
trans-N 1 -(6,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)cyclohexane-1,4-diamine;
N 1 -(6,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
cis-N 1 -(2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)cyclobutane-1,3-diamine;
N 1 -(2-(4-(5,6-dihydropyrrolo[3,4-c]pyrazol-2(4H)-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
cis-N 1 -(6,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)cyclohexane-1,4-diamine;
N 1 -(2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(6,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(3-aminopropyl)-N 1 -methyl-N 3 -(2-(3-(piperazin-1-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(6,7-dimethoxy-2-(4-methoxyphenyl)quinolin-4-yl)cyclohexane-1,4-diamine;
N 1 -(2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)cyclohexane-1,4-diamine;
2-amino-1-(4-(4-(4-((3-(dimethylamino)propyl)amino)quinolin-2-yl)phenyl)piperazin-1-yl)-3-methylbutan-1-one;
2-amino-1-(4-(4-(4-((3-(dimethylamino)propyl)amino)quinolin-2-yl)phenyl)piperazin-1-yl)propan-1-one;
N 1 -(2-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(3-aminopropyl)-N 3 -(6,7-dimethoxy-2-(4-methoxyphenyl)quinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
N 1 -(2-(4-(piperidin-4-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(2-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)quinolin-4-yl)propane-1,3-diamine;
trans-N 1 -(6,7-dimethoxy-2-(4-methoxyphenyl)quinolin-4-yl)cyclobutane-1,3-diamine;
N 1 ,N 1 -dimethyl-N 3 -(2-(3-(piperazin-1-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 ,N 1 -dimethyl-N 3 -(2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(2-(1-(2-(pyrrolidin-1-yl)ethyl)-1H-pyrazol-4-yl)quinolin-4-yl)propane-1,3-diamine;
trans-N 1 -(6,7-dimethoxy-2-(4-methoxyphenyl)quinolin-4-yl)cyclohexane-1,4-diamine;
N-(1-(4-aminocyclohexyl)piperidin-4-yl)-2-(4-methoxyphenyl)quinolin-4-amine;
N 1 -(6-fluoro-2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N-(1-(3-aminopropyl)piperidin-4-yl)-2-(4-methoxyphenyl)quinolin-4-amine;
cis-N 1 -(6,7-dimethoxy-2-(4-methoxyphenyl)quinolin-4-yl)cyclohexane-1,4-diamine;
2-amino-N-(1-((1-(4-(4-(4-((3-(dimethylamino)propyl)amino)quinolin-2-yl)phenyl)piperazin-1-yl)-3-methyl-1-oxobutan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)-3-methylbutanamide;
N 1 ,N 1 -dimethyl-N 3 -(2-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(6,7-dimethoxy-2-(4-methoxyphenyl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(6,7-dimethoxy-2-(4-methoxyphenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 ,N 1 -dimethyl-N 3 -(2-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
2-amino-N-(1-(4-(4-(4-((3-(dimethylamino)propyl)amino)quinolin-2-yl)phenyl)piperazin-1-yl)-3-methyl-1-oxobutan-2-yl)-3-methylbutanamide;
cis-N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)cyclobutane-1,3-diamine;
N 1 -([2,6′-biquinolin]-4-yl)propane-1,3-diamine;
4-(4-(4-((3-(dimethylamino)propyl)amino)quinolin-2-yl)phenyl)-1-methylpiperazin-2-one;
N 1 -(2-(piperidin-4-yl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(2-(2,3-dihydrobenzofuran-5-yl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(2-(4-(methoxy-d3)phenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 -([2,6′-biquinolin]-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)cyclobutane-1,3-diamine;
N 1 -(2-(1,2,3,6-tetrahydropyridin-4-yl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)cyclohexane-1,4-diamine;
2-(4-methoxyphenyl)-N-(piperidin-4-yl)quinolin-4-amine;
N 1 -(2-(4-(methoxy-d3)phenyl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(2-(benzofuran-5-yl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(2-(1-methyl-1H-pyrazol-4-yl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(2-(1-(azetidin-3-yl)-1H-pyrazol-4-yl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(2-(1-cyclopropyl-1H-pyrazol-4-yl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(2-(cyclohex-1-en-1-yl)quinolin-4-yl)propane-1,3-diamine;
(S)-2-amino-N-(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)-N-methylpropanamide;
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 3 ,N 3 -bis(methyl-d3)propane-1,3-diamine;
N 1 -(2-(furan-2-yl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(5-fluoro-2-(4-methoxyphenyl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(2-(1-(2-morpholinoethyl)-1H-pyrazol-4-yl)quinolin-4-yl)propane-1,3-diamine;
3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propan-1-ol;
N 1 -(2-(2-methoxypyrimidin-5-yl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 ,N 1 -dimethyl-N 3 -(2-methylquinolin-4-yl)propane-1,3-diamine;
3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)-N,N-dimethylpropanamide;
N 1 -(2-(6-methoxypyridin-3-yl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(2,2-difluoro-6-(4-methoxyphenyl)-[1,3]dioxolo[4,5-g]quinolin-8-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N-(4,4-difluorocyclohexyl)-2-(4-methoxyphenyl)quinolin-4-amine;
tert-butyl 3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propanoate;
N 1 -(6-methoxy-2-(trifluoromethyl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine,
N 1 -(6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
2-cyclohexyl-N-(1-isopropylpiperidin-4-yl)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinolin-4-amine;
N 1 -(3-aminopropyl)-N 3 -(6,7-dimethoxyquinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
6-methoxy-N-(1-methylpiperidin-4-yl)-7-(3-(pyrrolidin-1-yl)propoxy)quinolin-4-amine;
N 1 -(6,7-dimethoxyquinolin-4-yl)-N 3 ,N 3 -diethylpropane-1,3-diamine;
6,7-dimethoxy-N-(1′-methyl-[1,4′-bipiperidin]-4-yl)quinolin-4-amine;
N 1 -(3-aminopropyl)-N 3 -(7-chloroquinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
N 1 -(3-aminopropyl)-N 3 -(2-(4-(dimethylamino)phenyl)quinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complex thereof.
32 . A method for treating or preventing a disease that involves TDP-43, the method comprising administering to a subject an effective amount of at least one compound having formula (I):
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug or a complex thereof, wherein:
X 1 is selected from the group consisting of nitrogen and CH;
R 1a is selected from the group consisting of hydrogen, halogen, C 1-20 linear alkyl, C 3-20 branched alkyl, C 1-20 linear heteroalkyl, C 3-20 branched heteroalkyl, each of which except hydrogen and halogen are optionally substituted;
R 1b is selected from the group consisting of hydrogen, halogen, C 1-20 linear alkyl, C 3-20 branched alkyl, C 1-20 linear heteroalkyl, C 3-20 branched heteroalkyl, each of which except hydrogen and halogen are optionally substituted;
R 1c is selected from the group consisting of hydrogen, halogen, C 1-20 linear alkyl, C 3-20 branched alkyl, C 1-20 linear heteroalkyl, C 3-20 branched heteroalkyl, each of which except hydrogen and halogen are optionally substituted; and
R 1d is selected from the group consisting of hydrogen, halogen, C 1-20 linear alkyl, C 3-20 branched alkyl, C 1-20 linear heteroalkyl, C 3-20 branched heteroalkyl, each of which except hydrogen and halogen are optionally substituted,
R 2 is a substituted or unsubstituted C 1 -C 20 linear, branched, or cyclic organic group including at least one nitrogen; and
R 4 is a hydrogen, halogen, a hydroxyl group, a cyano group, a nitro group, a substituted or unsubstituted C 0 -C 10 amino group, a substituted or unsubstituted C 1 -C 10 alkyl group, a substituted or unsubstituted C 2 -C 10 alkenyl group, a substituted or unsubstituted C 2 -C 10 alkynyl group, and a substituted or unsubstituted C 1 -C 10 alkoxy group, a substituted or unsubstituted C 3 -C 10 cycloalkyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkyl group, a substituted or unsubstituted C 3 -C 10 cycloalkenyl group, a substituted or unsubstituted C 2 -C 10 heterocycloalkenyl group, a substituted or unsubstituted C 6 -C 20 aryl group, a substituted or unsubstituted C 6 -C 20 aryloxy group, a substituted or unsubstituted C 6 -C 20 arylthio group, a substituted or unsubstituted C 2 -C 20 heteroaryl group, a substituted or unsubstituted C 2 -C 20 heteroaryloxy group, or a substituted or unsubstituted C 2 -C 20 heteroarylthio group,
provided that the following compounds in which each hydrogen is a proton are excluded:
33 . The method of claim 32 , wherein the at least one compound is administered in a composition further comprising at least one excipient.
34 . The method of claim 33 , wherein the diseases that involves TDP-43 is selected from the group consisting of ALS, FTLD, CTE, hippocampal sclerosis of aging (CARTS), Alzheimer's disease, and Alzheimer's disease related disorders.
35 . A method for treating or preventing a disease associated with TDP-43 proteinopathies, the method comprising administering to a subject an effective amount of at least one compound according to claim 1 .
36 . The method of claim 35 , wherein the at least one compound is administered in a composition further comprising at least one excipient.
37 . A method for treating or preventing diseases that involve excess amounts of TDP-43 in the cytosol, the method comprising administering to a subject an effective amount of at least one compound according to claim 1 .
38 . The method of claim 37 , wherein the at least one compound is administered in a composition further comprising at least one excipient.
39 . The method of use of the TDP-43 binders of the present invention as positron emission tomography (PET) imaging agents, wherein the method comprises administering to a subject an effective amount of an isotopically labeled compound according to claim 1 .
40 . The method of use of the TDP-43 binders of the present invention as single-photon emission computed tomography (SPECT) imaging agents, wherein the method comprises administering to a subject an effective amount of an isotopically labeled compound according to claim 1 .
41 . The method of claim 32 , wherein, in formula (I),
R 1a is selected from the group consisting of hydrogen, halogen, C 1-20 linear alkyl, C 3-20 branched alkyl, C 1-20 linear alkoxy, C 3-20 branched alkoxy, C 1-20 linear aminoalkyl, C 3-20 branched aminoalkyl, C 1-20 linear aminoalkoxy, and C 3-20 branched aminoalkoxy, each of which except hydrogen and halogen are optionally substituted;
R 1b is selected from the group consisting of hydrogen, halogen, C 1-20 linear alkyl, C 3-20 branched alkyl, C 1-20 linear alkoxy, C 3-20 branched alkoxy, C 1-20 linear aminoalkyl, C 3-20 branched aminoalkyl, C 1-20 linear aminoalkoxy, and C 3-20 branched aminoalkoxy, each of which except hydrogen and halogen are optionally substituted;
R 1c is selected from the group consisting of hydrogen, halogen, C 1-20 linear alkyl, C 3-20 branched alkyl, C 1-20 linear alkoxy, C 3-20 branched alkoxy, C 1-20 linear aminoalkyl, C 3 -20 branched aminoalkyl, C 1-20 linear aminoalkoxy, and C 3-20 branched aminoalkoxy, each of which except hydrogen and halogen are optionally substituted; and
R 1d is selected from the group consisting of hydrogen, halogen, C 1-20 linear alkyl, C 3-20 branched alkyl, C 1-20 linear alkoxy, C 3-20 branched alkoxy, C 1-20 linear aminoalkyl, C 3 -20 branched aminoalkyl, C 1-20 linear aminoalkoxy, and C 3-20 branched aminoalkoxy, each of which except hydrogen and halogen are optionally substituted.
42 . The method of claim 41 , wherein, in formula (I), at least one selected from the group consisting of R 1a , R 1b , R 1c , and R 1d is a substituted or unsubstituted C 1-20 aminoalkoxy group.
43 . The method of claim 41 , wherein, in formula (I), at least one selected from the group consisting of R 1a , R 1b , R 1c , and R 1d is a substituted or unsubstituted (C 2-8 dialkylamino)(C 2-4 alkoxy) group or a substituted or unsubstituted (C 3-6 alkyleneamino)(C 2-4 alkoxy) group.
44 . The method of claim 32 , wherein the compound is:
N 1 -(3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)-N 1 ,N 3 ,N 3 -trimethyl propane-1,3-diamine;
2-(4-Methoxyphenyl)-N-(3-f{methyl[3-(methylamino)propyl]-amino}propyl)quinolin-4-amine;
N 1 -(3-Aminopropyl)-N 3 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
N 1 -(2-(4-Methoxyphenyl)quinolin-4-yl)-N 3 -(3-(piperidin-yl)propyl)propane-1,3-diamine;
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 3 -methyl-N 3 -(3-(piperidin-1-yl)propyl)propane-1,3-diamine;
tert-Butyl N-{3-[(3-{[2-(4-methoxyphenyl)quinolin-4yl]amino}propyl)amino]propyl}carbamate;
N 1 -(3-aminopropyl)-N 3 -(5-fluoro-2-(4-methoxyphenyl)quinolin-4-yl)-N 1 -methylpropane-1,3-diamine:
N-{3-[(3-Aminopropyl)amino]propyl}-2-(4-methoxyphenyl)quinolin-4-amine;
N 1 -(3-Aminopropyl)-N 3 -(6-methoxy-2-(4-methoxyphenyl)quinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
N 1 -(3-Aminopropyl)-N 3 -(2-(2-methyl-4-methoxyphenyl)quinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
N 1 -(3-Aminopropyl)-N 3 -(6,7-dimethoxy-2-(4-methoxyphenyl)quinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
N 1 -(3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)-N 1 ,N 4 -dimethylbutane-1,4-diamine;
N 1 -(2-fluoroethyl)-N 3 -(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)-N 1 ,N 3 -dimethylpropane-1,3-diamine;
3-((3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)amino)-propan-1-ol;
N-(3-(3-methoxypropylamino)propyl)-2-(4-methoxyphenyl)quinolin-4-amine;
N-(3-(2-(4-Methoxyphenyl)quinolin-4-ylamino)propyl)-N-(3-aminopropyl)acetamide;
N 1 -(Cyclopropylmethyl)-N 1 -(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)-N 3 ,N 3 -dimethyl propane-1,3-diamine:
tert-Butyl 3-(((3-(dimethylamino)propyl)(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)amino)methyl)azetidine-1-carboxylate;
tert-Butyl 4-(((3-(dimethylamino)propyl)(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)amino)methyl)piperidine-1-carboxylate:
N 1 -(Azetidin-3-ylmethyl)-N 1 -(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)-N 3 ,N 3 -dimethyl-N 1 -(piperidin-4-ylmethyl)propane-1,3-diamine;
N 1 -(2-(4-Methoxyphenyl)quinolin-4-yl)-N 3 -((1-methyl-1H-imidazol-5-yl)methyl)propane-1,3-diamine;
N-(3-(Hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)propyl)-2-(4-methoxyphenyl)quinolin-4-amine;
N 1 -((6-Aminopyridin-3-yl)methyl)-N 3 -(2-(4-methoxyphenyl)-quinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
1-(Dimethylamino)-3-((3-((2-(4-methoxyphenyl)quinolin-4-yl)-amino)propyl)(methyl)amino)propan-2-ol;
1-(3-((3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)-methylamino)propyl)piperidin-4-ol;
tert-butyl 5-(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)hexahydro-pyrrolo[3,4-c]pyrrole-2(1H)-carboxylate;
N 1 -((6-(dimethylamino)pyridin-3-yl)methyl)-N 3 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 1 -methyl propane-1,3-diamine;
N 1 -(3-aminopropyl)-N 1 -methyl-N 3 -(2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 3 -methyl-N 3 -((1-methylpiperidin-4-yl)methyl)propane-1,3-diamine:
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 3 -methyl-N 3 -(2-(piperidin-2-yl)ethyl)propane-1,3-diamine;
tert-Butyl(2-(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)octahydrocyclopenta[c]pyrrol-4-yl)carbamate:
N 1 -(2-(4-Methoxyphenyl)quinolin-4-yl)-N 3 -(octahydrocyclopenta[c]pyrrol-4-yl)propane-1,3-diamine;
N-(3-(4-Aminohexahydrocyclopenta[c]pyrrol-2(1H)-yl)propyl)-2-(4-methoxyphenyl)quinolin-4-amine;
tert-Butyl 2-(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)hexahydro-1H-pyrrolo[3,4-c]pyridine-5(6H)-carboxylate;
N-(3-(Hexahydro-1H-pyrrolo[3,4-c]pyridin-2(3H)-yl)propyl)-2-(4-methoxyphenyl)quinolin-4-amine;
tert-Butyl 4-((3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate;
N 1 -((1-(Cyclopropylmethyl)piperidin-4-yl)methyl)-N 3 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 1 -methyl propane-1,3-diamine;
N-(2-(1-(3-Aminopropyl)piperidin-2-yl)ethyl)-2-(4-methoxyphenyl)quinolin-4-amine:
N 1 -(1-(4-Fluorobenzyl)piperidin-4-yl)-N 3 -(2-(4-methoxyphenyl)quinolin-4-yl)propane-1,3-diamine:
tert-Butyl 6-(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)-2,6-diazaspiro[3.4]octane-2-carboxylate;
N-(3-(2,6-Diazaspiro[3.4]octan-6-yl)propyl)-2-(4-methoxyphenyl)quinolin-4-amine:
2-(4-Methoxyphenyl)-N-(3-(4-methyl-1,4-diazepan-1-yl)propyl)quinolin-4-amine:
tert-Butyl 2-(2-((3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)amino)ethyl)piperidine-1-carboxylate;
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 3 -(2-(piperidin-2-yl)ethyl)propane-1,3-diamine;
N-(3-(4-(3-Aminopropyl)piperazin-1-yl)propyl)-2-(4-methoxyphenyl)quinolin-4-amine;
tert-Butyl 4-{[(3-{[2-(4-methoxyphenyl)quinolin-4-yl]amino}propyl)(methyl)amino]methyl}piperidine-1-carboxylate;
N-(3-(N-Methyl-N-((piperidin-4-yl)methyl)amino)propyl)-2-(4-methoxyphenyl)quinolin-4-amine;
N-(3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)-4-(2H-tetrazol-5-yl)benzenesulfonamide;
N 1 -(4-(2H-Tetrazol-5-yl)phenyl)-N 3 -(2-(4-methoxyphenyl)quinolin-4-yl)propane-1,3-diamine;
(1-(3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)piperidin-4-yl)methanol;
1-(Diethylamino)-3-((3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)amino)propan-2-ol;
N 1 -(2-(4-Methoxyphenyl)quinolin-4-yl)-N 3 -((1-methyl-1H-pyrazol-5-yl)methyl)propane-1,3-diamine;
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 3 -(2-(pyridin-2-yl)ethyl)propane-1,3-diamine;
N 1 -(2-(4-Methoxyphenyl)quinolin-4-yl)-N 3 -(4-(piperidin-1-yl)phenyl)propane-1,3-diamine;
N-((1-(3-Aminopropyl)piperidin-3-yl)methyl)-2-(4-methoxyphenyl)quinolin-4-amine;
N-(3-(2-(6-Methoxy-1H-indol-3-yl)ethylamino)propyl)-2-(4-methoxyphenyl)quinolin-4-amine:
tert-Butyl 4-{[({1-[(tert-butoxy)carbonyl]piperidin-4-yl}methyl)(3-{[2-(4-methoxyphenyl)-quinolin-4-yl]amino}propyl)amino]methyl}piperidine-1-carboxylate;
N-(3-(Bis((piperidin-4-yl)methyl)amino)propyl)-2-(4-methoxyphenyl)quinolin-4-amine;
N 1 -(4-Methoxybenzyl)-N 3 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
tert-Butyl(3-((4-((2-(4-methoxyphenyl)quinolin-4-yl)amino)cyclohexyl)amino)propyl)carbamate;
tert-Butyl 4-{[(3-{[2-(4-methoxyphenyl)quinolin-4-yl]amino}propyl)amino]methyl}piperidine-1-carboxylate;
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 3 -(3-(pyridin-4-ylamino)propyl)propane-1,3-diamine;
2-(3-(4-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)piperidin-1-yl)propyl)isoindoline-1,3-dione;
2-(3-(3-(((2-(4-Methoxyphenyl)quinolin-4-yl)amino)methyl)piperidin-1-yl)propyl)isoindoline-1,3-dione;
N-(3-((3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)amino)propyl) methanesulfonamide;
2-(3-(2-(2-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)ethyl)piperidin-1-yl)propyl)isoindoline-1,3-dione;
N-(3-(Hexahydropyrrolo[1,2-a]pyrazin-2(1H)-yl)propyl)-2-(4-methoxy phenyl)quinolin-4-amine;
2-(4-Methoxyphenyl)-N-(1′-methyl-[1,4′-bipiperidine]-4-yl)quinolin-4-amine;
N 1 -(2-Benzyloctahydrocyclopenta[c]pyrrol-4-yl)-N 3 -(2-(4-methoxyphenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 -((1-(Cyclopropylmethyl)piperidin-4-yl)methyl)-N 3 -(2-(4-methoxyphenyl)quinolin-4-yl)propane-1,3-diamine;
1-(3-((2-(4-Methoxyphenyl)quinolin-4-yl)amino)propyl)piperidine-4-carboxamide;
2-(4-Methoxyphenyl)-N-(3-(4-methylpiperazin-1-yl)propyl)quinolin-4-amine;
2-(4-Methoxyphenyl)-N-(2-(4-methylpiperazin-1-yl)ethyl)quinolin-4-amine;
2-(4-Methoxyphenyl)-N-(3-morpholinopropyl)quinolin-4-amine;
2-(7-Amino-4-methyl-2-oxo-2H-chromen-3-yl)-N-(3-((3-((2-(4-methoxyphenyl)quinolin-4-yl)amino) propyl)(methyl)amino)propyl)acetamide;
5-(dimethylamino)-N-{3-[(3-{[2-(4-methoxyphenyl)quinolin-4yl]amino}propyl)(methyl)amino]propyl}naphthalene-1-sulfonamide;
cis-N 1 -(6,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)cyclobutane-1,3-diamine;
trans-N 1 -(6,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)cyclobutane-1,3-diamine;
trans-N 1 -(6,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)cyclohexane-1,4-diamine;
N 1 -(6,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
cis-N 1 -(2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)cyclobutane-1,3-diamine;
N 1 -(2-(4-(5,6-dihydropyrrolo[3,4-c]pyrazol-2(4H)-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
cis-N 1 -(6,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)cyclohexane-1,4-diamine;
N 1 -(2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(6,7-dimethoxy-2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(3-aminopropyl)-N 1 -methyl-N 3 -(2-(3-(piperazin-1-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(6,7-dimethoxy-2-(4-methoxyphenyl)quinolin-4-yl)cyclohexane-1,4-diamine;
N 1 -(2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)cyclohexane-1,4-diamine;
2-amino-1-(4-(4-(4-((3-(dimethylamino)propyl)amino)quinolin-2-yl)phenyl)piperazin-1-yl)-3-methylbutan-1-one;
2-amino-1-(4-(4-(4-((3-(dimethylamino)propyl)amino)quinolin-2-yl)phenyl)piperazin-1-yl)propan-1-one;
N 1 -(2-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(3-aminopropyl)-N 3 -(6,7-dimethoxy-2-(4-methoxyphenyl)quinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
N 1 -(2-(4-(piperidin-4-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(2-(1-(piperidin-4-yl)-1H-pyrazol-4-yl)quinolin-4-yl)propane-1,3-diamine;
trans-N 1 -(6,7-dimethoxy-2-(4-methoxyphenyl)quinolin-4-yl)cyclobutane-1,3-diamine;
N 1 ,N 1 -dimethyl-N 3 -(2-(3-(piperazin-1-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 ,N 1 -dimethyl-N 3 -(2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(2-(1-(2-(pyrrolidin-1-yl)ethyl)-1H-pyrazol-4-yl)quinolin-4-yl)propane-1,3-diamine;
trans-N 1 -(6,7-dimethoxy-2-(4-methoxyphenyl)quinolin-4-yl)cyclohexane-1,4-diamine;
N-(1-(4-aminocyclohexyl)piperidin-4-yl)-2-(4-methoxyphenyl)quinolin-4-amine;
N 1 -(6-fluoro-2-(4-(piperazin-1-yl)phenyl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N-(1-(3-aminopropyl)piperidin-4-yl)-2-(4-methoxyphenyl)quinolin-4-amine;
cis-N 1 -(6,7-dimethoxy-2-(4-methoxyphenyl)quinolin-4-yl)cyclohexane-1,4-diamine;
2-amino-N-(1-((1-(4-(4-(4-((3-(dimethylamino)propyl)amino)quinolin-2-yl)phenyl)piperazin-1-yl)-3-methyl-1-oxobutan-2-yl)amino)-3-methyl-1-oxobutan-2-yl)-3-methylbutanamide;
N 1 ,N 1 -dimethyl-N 3 -(2-(1-(1-methylpiperidin-4-yl)-1H-pyrazol-4-yl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(6,7-dimethoxy-2-(4-methoxyphenyl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(6,7-dimethoxy-2-(4-methoxyphenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 ,N 1 -dimethyl-N 3 -(2-(4-(4-methylpiperazin-1-yl)phenyl)quinolin-4-yl)propane-1,3-diamine;
2-amino-N-(1-(4-(4-(4-((3-(dimethylamino)propyl)amino)quinolin-2-yl)phenyl)piperazin-1-yl)-3-methyl-1-oxobutan-2-yl)-3-methylbutanamide;
cis-N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)cyclobutane-1,3-diamine;
N 1 -([2,6′-biquinolin]-4-yl)propane-1,3-diamine;
4-(4-(4-((3-(dimethylamino)propyl)amino)quinolin-2-yl)phenyl)-1-methylpiperazin-2-one;
N 1 -(2-(piperidin-4-yl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(2-(2,3-dihydrobenzofuran-5-yl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(2-(4-(methoxy-d 3 )phenyl)quinolin-4-yl)propane-1,3-diamine;
N 1 -([2,6′-biquinolin]-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)cyclobutane-1,3-diamine;
N 1 -(2-(1,2,3,6-tetrahydropyridin-4-yl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)cyclohexane-1,4-diamine;
2-(4-methoxyphenyl)-N-(piperidin-4-yl)quinolin-4-amine;
N 1 -(2-(4-(methoxy-d 3 )phenyl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(2-(benzofuran-5-yl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(2-(1-methyl-1H-pyrazol-4-yl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(2-(1-(azetidin-3-yl)-1H-pyrazol-4-yl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(2-(1-cyclopropyl-1H-pyrazol-4-yl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(2-(cyclohex-1-en-1-yl)quinolin-4-yl)propane-1,3-diamine;
(S)-2-amino-N-(3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propyl)-N-methylpropanamide;
N 1 -(2-(4-methoxyphenyl)quinolin-4-yl)-N 3 ,N 3 -bis(methyl-d 3 )propane-1,3-diamine;
N 1 -(2-(furan-2-yl)quinolin-4-yl)propane-1,3-diamine;
N 1 -(5-fluoro-2-(4-methoxyphenyl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(2-(1-(2-morpholinoethyl)-1H-pyrazol-4-yl)quinolin-4-yl)propane-1,3-diamine;
3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propan-1-ol;
N 1 -(2-(2-methoxypyrimidin-5-yl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 ,N 1 -dimethyl-N 3 -(2-methylquinolin-4-yl)propane-1,3-diamine;
3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)-N,N-dimethylpropanamide;
N 1 -(2-(6-methoxypyridin-3-yl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(2,2-difluoro-6-(4-methoxyphenyl)-[1,3]dioxolo[4,5-g]quinolin-8-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N-(4,4-difluorocyclohexyl)-2-(4-methoxyphenyl)quinolin-4-amine;
tert-butyl 3-((2-(4-methoxyphenyl)quinolin-4-yl)amino)propanoate;
N 1 -(6-methoxy-2-(trifluoromethyl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
2-cyclohexyl-N-(1-isopropylpiperidin-4-yl)-6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinolin-4-amine;
N 1 -(3-aminopropyl)-N 3 -(6,7-dimethoxyquinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
6-methoxy-N-(1-methylpiperidin-4-yl)-7-(3-(pyrrolidin-1-yl)propoxy)quinolin-4-amine;
N 1 -(6,7-dimethoxyquinolin-4-yl)-N 3 ,N 3 -diethylpropane-1,3-diamine;
6,7-dimethoxy-N-(1′-methyl-[1,4′-bipiperidin]-4-yl)quinolin-4-amine;
N 1 -(3-aminopropyl)-N 3 -(7-chloroquinolin-4-yl)-N 1 -methylpropane-1,3-diamine;
N 1 -(3-aminopropyl)-N 3 -(2-(4-(dimethylamino)phenyl)quinolin-4-yl)-N-methylpropane-1,3-diamine;
N 1 -(6-methoxy-7-(2-(pyrrolidin-1-yl)ethoxy)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine;
N 1 -(2-(4-(2-(1H-pyrazol-1-yl)ethoxy)phenyl)quinolin-4-yl)-N 3 ,N 3 -dimethylpropane-1,3-diamine,
an enantiomer, a diastereomer, a hydrate, a solvate, a pharmaceutically acceptable salt, an isotopic analog, a prodrug, or a complex thereof.