US2008255120A1PendingUtilityA1
Substituted 2,5-heterocyclic derivatives
Assignee: NOVARTIS VACCINES & DIAGNOSTICPriority: Mar 30, 2004Filed: May 29, 2008Published: Oct 16, 2008
Est. expiryMar 30, 2024(expired)· nominal 20-yr term from priority
A61P 43/00A61P 35/04A61P 35/00A61P 29/00A61P 25/00A61P 13/08A61P 15/00C07D 409/14C07D 417/14C07D 409/04C07D 413/14A61P 17/00C07D 495/04A61P 1/18
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Claims
Abstract
The present invention relates to new substituted five-membered compounds and pharmaceutically acceptable salts, esters or prodrugs thereof, compositions of the new compounds together with pharmaceutically acceptable carriers, and uses of the new compounds. The compounds of the invention have the following general formula:
Claims
exact text as granted — not AI-modified1 . A compound represented by the formula I:
wherein:
ring A is a nitrogen-containing heteroaryl comprising 5 or 6 ring atoms wherein from 1 to 4 ring atoms are nitrogen atoms;
n is an integer selected from zero or one;
R is selected from the group consisting of:
a) hydrogen,
b) hydroxy,
c) alkyl,
d) substituted alkyl,
e) cycloalkyl,
f) substituted cycloalkyl,
g) —SO 2 R 7 where R 7 is C 1 to C 5 alkyl or substituted alkyl,
h) alkoxy,
i) carboxyl,
j) carboxyl ester,
k) nitro,
l) aryl,
m) substituted aryl,
n) heteroaryl,
o) substituted heteroaryl,
p) heterocyclyl,
q) substituted heterocyclyl,
r) acylamino, and
s) acyl;
each R 1 is independently selected from the group consisting of:
a) halo,
b) cyano,
c) nitro,
d) hydroxy,
e) thiol,
f) amino,
g) substituted amino,
h) alkoxy,
i) substituted alkoxy,
j) aryloxy,
k) substituted aryloxy,
l) heteroaryloxy,
m) substituted heteroaryloxy,
n) alkylthio,
o) substituted alkylthio,
p) —C(═O)NR 8 R 8 , wherein each R 8 is independently selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclyl, substituted heterocyclyl, or each R 8 can be optionally joined together with the nitrogen atom pendent thereto to form a heterocyclyl or substituted heterocyclyl,
q) —NHC(═O)—R 9 , wherein R 9 is selected from the group consisting of hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, heterocyclyl, substituted heterocyclyl,
r) aryl or heteroaryl, each of which may be optionally substituted with optionally substituted alkyl or aryl,
s) heterocyclyl, each of which may be optionally substituted with optionally substituted alkyl or aryl, and
t) C 1 to C 5 alkyl optionally substituted with 1 to 3 substituents selected from halo, hydroxy, amino, aryl, C 1 to C 5 alkyl monosubstituted amino, and C 1 to C 5 alkyl disubstituted amino wherein each alkyl group is independent from the other alkyl group;
m is an integer equal to 0, 1 or 2;
R 2 and R 4 are independently selected from the group consisting of:
a) hydrogen,
b) cycloalkyl,
c) substituted cycloalkyl,
d) heterocyclyl,
e) substituted heterocyclyl,
f) aryl,
g) substituted aryl,
h) heteroaryl,
i) substituted heteroaryl,
j) optionally substituted C 1 to C 5 substituted alkyl,
k) optionally substituted C 2 to C 5 alkenyl,
l) optionally substituted C 2 to C 5 alkynyl,
m) optionally substituted C 1 to C 5 alkoxy,
n) hydroxy,
o) amino,
p) C 1 to C 5 alkyl monosubstituted amino, and
q) C 1 to C 5 alkyl disubstituted amino wherein each alkyl group is independent from the other alkyl group,
with the proviso that when one of R 2 or R 4 is cycloalkyl, substituted cycloalkyl, heterocyclyl, substituted heterocyclyl, aryl substituted aryl, heteroaryl, substituted heteroaryl, then the other of R 2 or R 4 is hydrogen;
R 3 is selected from the group consisting of:
a) hydrogen,
b) C 1 to C 5 alkyl, and
c) —C 1 to C 5 alkylene) p -Z optionally substituted on the alkylene chain with 1 to 2 substituents selected from the group consisting of:
i. C 1 to C 5 alkyl optionally substituted with 1 to 3 substituents selected from hydroxy, carboxyl, carboxyl esters, amino, C 1 to C 5 alkyl monosubstituted amino, and C 1 to C 5 alkyl disubstituted amino wherein each alkyl group is independent from the other alkyl group,
ii. C 2 to C 5 alkenyl optionally substituted with 1 to 3 substituents selected from hydroxy, carboxyl, carboxyl esters, amino, C 1 to C 5 alkyl monosubstituted amino, and C 1 to C 5 alkyl disubstituted amino wherein each alkyl group is independent from the other alkyl group with the proviso that said hydroxy substitution is not pendent to a vinyl carbon atom of the substituted alkenyl,
iii. C 2 to C 5 alkynyl optionally substituted with 1 to 3 substituents selected from hydroxy, carboxyl, carboxyl esters, amino, C 1 to C 5 alkyl monosubstituted amino, and C 1 to C 5 alkyl disubstituted amino wherein each alkyl group is independent from the other alkyl group with the proviso that said hydroxyl substitution is not pendent to a acetylene carbon atom of the substituted alkynyl,
iv. C 3 to C 6 cycloalkyl,
v. C 3 to C 6 spirocycloalkyl,
vi. carboxyl,
vii. carboxyl esters,
viii. halo,
ix. hydroxy,
x. C 1 to C 5 alkoxy,
xi. amino,
xii. C 1 to C 5 alkyl monosubstituted amino,
xiii. C 1 to C 5 alkyl disubstituted amino,
xiv. aryl, and
xv. heterocyclyl;
Z is selected from the group consisting of:
a) alkyl,
b) substituted alkyl,
c) alkylamino,
d) alkoxy,
e) substituted alkoxy,
f) cycloalkyl,
g) heterocyclyl,
h) substituted heterocyclyl,
i) aryl,
j) substituted aryl,
k) heteroaryl, and
l) substituted heteroaryl;
p is an integer selected from zero or one;
Q is selected from the group consisting of:
a) —C(X′)NR 6 —,
b) —CH 2 NR 6 —,
c) —NR 6 C(X′)—,
d) —NR 6 C(X′)O—,
e) —NR 6 C(X′)NR 6 —,
f) —OC(X′)NR 6 ,
g) —C(X′)O—,
h) —CR 6 ═CR 6 —,
i) —C≡C—,
j) —S(O) 2 NR 6 —, and
k) —S(O)NR 6 —,
where X′ is selected from the group consisting of oxygen and sulfur and each R 6 is independently selected from the group consisting of hydrogen and C 1 -C 3 alkyl and C 1 -C 3 substituted alkyl,
or R 6 together with Q and the carbon atom attached thereto and together with R 4 and the carbon atom attached thereto join to form a heterocyclyl or substituted heterocyclyl,
with the proviso that when Q is —C(O)NH—, then R 3 is not C 2 alkyl further substituted with at least a —C(O) group at the beta position to the —C(O)NH—,
with the further proviso that when Q is —S(O) 2 NH—, then R 3 is not C 2 alkyl further substituted with at least a —C(O) group;
W is selected from the group consisting of —O—, —S—, —SO—, and —SO 2 —;
with the proviso that when ring A is pyrimidine and Q is —C(O)NR 6 —, then R 4 is not aryl or heteroaryl;
or pharmaceutically acceptable salts, esters or prodrugs thereof.
2 . The compound of claim 1 , wherein ring A is selected from the group consisting of formula IA, IB, IC, ID, IE, and IF:
wherein R, R 1 , R 5 , n and m are as defined above and t is 0 or 1.
3 . The compound of claim 1 , wherein R is selected from the group consisting of hydrogen, alkyl, substituted alkyl, cycloalkyl, substituted cycloalkyl, acylamino, heteroaryl, nitro, aryl —SO 2 R 7 wherein R 7 is hydrogen or methyl, carboxyl ester, and acyl.
4 . The compound of claim 3 , wherein R is selected from the group consisting of:
2-(methylamino)eth-1-yl,
2-(N-methylpiperazin-N′-yl)eth-1-yl,
2-(N-methylpyrrol-2-yl)eth-1-yl,
2-(N-morpholino)eth-1-yl,
2-(piperidin-N-yl)eth-1-yl,
2-(pyridin-2-yl)eth-1-yl,
2-(pyridin-3-yl)eth-1-yl,
2-(pyridin-4-yl)eth-1-yl,
2-(S)-phenylcyclopropyl,
2-aminoeth-1-yl,
2-hydroxyeth-1-yl,
2-phenyleth-1-yl,
2-spirocyclopropyl-2-(4-chlorophenyl)eth-1-yl,
3-(imidazol-N-yl)prop-1-yl,
3-(N-methylpiperazin-N′-yl)prop-1-yl,
3-(N-morpholino)prop-1-yl,
3-aminobut-1-yl,
3-aminoprop-1-yl,
5-carboxy-4-(R,S)-aminopent-1-yl,
aminocarbonyl,
benzyl,
benzylaminocarbonyl,
butyl,
cyclobutyl,
cyclopentyl,
cyclopropyl,
cyclopropylmethyl,
dimethylaminocarbonyl,
ethylaminocarbonyl,
hydrogen,
ethyl,
methyl,
methoxycarbonyl,
methylaminocarbonyl,
methylcarbonyl,
neopentyl,
nitro,
phenyl,
phenylaminocarbonyl,
propyl,
propylaminocarbonyl,
pyridin-2-ylmethyl,
pyridin-3-ylmethyl,
pyridin-4-yl,
pyridin-4-ylmethyl, and
SO 2 CH 3 .
5 . The compound of claim 1 , wherein R 5 is hydrogen or methyl.
6 . The compound of claim 1 , wherein R 1 is selected from the group consisting of hydrogen, C 1-5 alkyl, —C(═O)NR 8 R 8 , and —NHC(═O)—R 9 .
7 . The compound of claim 6 , wherein R 1 is selected from the group consisting of hydrogen, methyl, aminocarbonyl, and methylcarbonylamino.
8 . The compound of claim 1 , wherein R 2 and R 4 are independently selected from the group consisting of hydrogen, hydroxy, amino, C 1 to C 5 alkoxy optionally substituted with aryl or amino.
9 . The compound of claim 8 , wherein R 2 and R 4 are selected from the group consisting of hydrogen, hydroxy, amino, methoxy, benzyloxy, and 2-aminoethoxy.
10 . The compound of claim 1 , wherein R 3 is hydrogen.
11 . The compound of claim 1 , where R 3 is —(C 1 to C 5 alkylene) p -Z wherein p is 0 or 1.
12 . The compound of claim 11 , wherein p is 1 and the alkylene chain is unsubstituted or substituted with a substituent selected from the group consisting of C 1 to C 5 alkyl, C 1 to C 5 alkyl substituted with hydroxy, amino, monosubstituted amino, or disubstituted amino, C 2 to C 5 alkenyl, C 2 to C 5 alkynyl, C 3 to C 6 spirocycloalkyl, carboxyl, carboxyl esters, hydroxy, amino, heterocyclyl and aryl.
13 . The compound of claim 11 , wherein the alkylene chain is unsubstituted or substituted with a substituent selected from the group consisting of:
2-aminoethyl,
2-dimethylaminoethyl, and
2-hydroxyethyl,
2-methylaminoethyl,
3-methylaminopropyl,
amino,
aminomethyl,
carboxyl,
dimethylamino,
dimethylaminomethyl,
ethyl,
methyl,
methylcarboxyl,
morpholino,
hydroxymethyl,
phenyl,
prop-2-enyl,
prop-2-ynyl,
propyl,
spirocyclobutyl, and
spirocyclopropyl.
14 . The compound of claim 11 , wherein Z is selected from the group consisting of cycloalkyl, substituted cycloalkyl, heterocyclyl, substituted heterocyclyl, aryl, substituted aryl, heteroaryl, substituted heteroaryl, alkyl, amino, alkylamino, and dialkylamino.
15 . The compound of claim 1 , wherein R 3 is selected from the group consisting of:
(2-fluoro-4-methoxyphenyl)eth-1-yl,
(2-fluoro-4-methylphenyl)eth-1-yl,
[1-(4-chlorophenyl)cyclobut-1-yl]methyl,
[1-(4-chlorophenyl)cycloprop-1-yl]methyl,
1-(1-aminoethyl)-4-chloro-1H-benzoimidazol-2-yl,
1-(2-aminoethyl)-1H-benzoimidazol-2-yl,
1-(2-aminoethyl)-4-chloro-1H-benzimidazol-2-yl,
1-(2-aminoethyl)-4-methoxy-1H-benzimidazol-2-yl,
1-(2-aminoethyl)-4-phenyl-1H-benzimidazol-2-yl,
1-(2-aminoethyl)-7-chloro-1H-benzimidazol-2-yl,
1-(2-methylpropyl)-4-chloro-1H-benzimidazol-2-yl,
1-(3,3-dimethylbutyl)-4-chloro-1H-benzimidazol-2-yl,
1-(3-aminopropyl)-4-chloro-1H-benzimidazol-2-yl,
1-(4-chlorophenyl)-3-(N-methylamino)prop-1-yl,
1-(4-chlorophenyl)-3-(N,N-dimethylamino)prop-1-yl,
1-(4-chlorophenyl)-3-hydroxyprop-1-yl,
1-(aminomethyl)-2-(2,4-dichlorophenyl)eth-1-yl,
1-(R)-1-(2,4-dichlorobenzyl)-4-(dimethylamino)but-2-yl,
1-(R)-1-(2,4-dichlorobenzyl)-4-(methylamino)but-2-yl,
1-(R)-1-(2,4-dichlorobenzyl)-4-aminobut-2-yl,
1-(R)-2-(2,4-dichlorophenyl)-1-methyleth-1-yl,
1-(R)-4-fluorophenyl)eth-1-yl,
1-(R)-amino-1-(2,4-dichlorobenzyl)eth-1-yl,
1-(R)-aminomethyl-2-(2,4-dichlorophenyl)eth-1-yl,
1-(R)-hydroxymethyl-2-(4-chlorophenyl)eth-1-yl,
1-(R,S)-carboxyl-2-(2,4-dichlorophenyl)eth-1-yl,
1-(R,S)-hydroxymethyl-1-phenylmethyl,
1-(R,S)-hydroxymethyl-2-(2,4-dichlorophenyl)eth-1-yl,
1-(R,S)-hydroxymethyl-2-phenyleth-1-yl,
1-(R,S)-methylcarboxyl-2-(2,4-dichlorophenyl)eth-1-yl,
1-(R,S)-phenyl-2-phenyleth-1-yl,
1-(S)-1-(2,4-dichlorobenzyl)-4-(dimethylamino)but-2-yl,
1-(S)-1-(2,4-dichlorobenzyl)-4-(methylamino)but-2-yl,
1-(S)-1-(2,4-dichlorobenzyl)-4-amino-but-2-yl,
1-(S)-amino-1-(2,4-dichlorobenzyl)eth-1-yl,
1-(S)-aminomethyl-2-(1H-indol-3-yl)eth-1-yl,
1-(S)-aminomethyl-2-(2,4-dichlorophenyl)eth-1-yl,
1-(S)-aminomethyl-2-(indol-3-yl)eth-1-yl,
1-(S)-dimethylamino-2-(2,4-dichlorophenyl)eth-1-yl,
1-(S)-dimethylaminomethyl-2-(2,4-dichlorophenyl)eth-1-yl,
1,2,3,4-tetrahydronaphthalen-1-yl,
1-aminoethyl-4-methoxybenzoimidazol-2-yl,
1-aminomethyl-2-(2,4-dichlorophenyl)eth-1-yl,
1-aminomethyl-2-(4-chlorophenyl)eth-1-yl,
1-aminomethyl-4-chloro-1H-benzimidazole-2-yl,
1-benzylpyrrolidin-3-yl,
1-dimethylamino-3-(2,4-dichlorophenyl)prop-2-yl,
1-ethyl-4-chlorobenzoimidazol-2-yl,
1-hydroxymethyl-2-(2,4-dichlorophenyl)eth-1-yl,
1-hydroxymethyl-2-methylprop-1-yl,
1-isobutyl-4-chlorobenzoimidazol-2-yl,
1-methyl-2-hydroxyeth-1-yl,
1-methyl-4-chlorobenzoimidazol-2-yl,
1-methylbenzoimidazol-2-yl,
1-phenyl-1-(4-chlorophenyl)methyl,
1-phenyl-2-hydroxyeth-1-yl,
2-(2,4-dichlorophenyl)but-1-yl,
2-(2,4-dichlorophenyl)eth-1-yl,
2-(2,4-dichlorophenyl)pent-1-yl,
2-(2,4-dichlorophenyl)pent-4-en-1-yl,
2-(2,4-dichlorophenyl)pent-4-yn-1-yl,
2-(2,4-dichlorophenyl)prop-1-yl,
2-(2,5-dimethoxyphenyl)eth-1-yl,
2-(2,6-dichlorophenyl)eth-1-yl,
2-(2-chlorophenyl)eth-1-yl,
2-(3,4-dichlorophenyl)eth-1-yl,
2-(3,4-dimethoxyphenyl)eth-1-yl,
2-(3-chlorophenyl)eth-1-yl,
2-(3-fluorophenyl)eth-1-yl,
2-(3-methoxyphenyl)eth-1-yl,
2-(4-aminophenyl)eth-1-yl,
2-(4-aminosulfonylphenyl)eth-1-yl,
2-(4-biphenyl)eth-1-yl,
2-(4-bromophenyl)eth-1-yl,
2-(4-chlorophenyl)eth-1-yl,
2-(4-ethoxyphenyl)eth-1-yl,
2-(4-ethylphenyl)eth-1-yl,
2-(4-fluorophenyl)eth-1-yl,
2-(4-methoxyphenyl)eth-1-yl,
2-(4-methylphenyl)eth-1-yl,
2-(4-phenoxyphenyl)eth-1-yl,
2-(N-methylpiperazin-N′-yl)eth-1-yl,
2-(N-methylpyrrol-2-yl)eth-1-yl,
2-(N-morpholino)eth-1-yl,
2-(piperidin-1-yl)eth-1-yl,
2-(piperidin-3-yl)eth-1-yl,
2-(pyridin-2-yl)eth-1-yl,
2-(pyridin-4-yl)eth-1-yl,
2-(R)—(N-morpholino)-2-phenyleth-1-yl,
2-(R)-amino-3-(indol-3-yl)prop-1-yl,
2-(R)-hydroxyindan-1-yl,
2-(R)-methyl-2-phenyleth-1-yl,
2-(R,S)-amino-2-phenyleth-1-yl,
2-(R,S)-hydroxy-2-(4-chlorophenyl)eth-1-yl,
2-(R,S)-methyl-2-phenyleth-1-yl,
2-(S)-amino-3-(indol-3-yl)prop-1-yl,
2-(S)-methyl-2-phenyleth-1-yl,
2-(trifluoromethyl)-4-fluorophenylmethyl,
2,4-dichlorobenzyl,
2,4-dichlorophenylmethyl,
2,2-dimethyl-5-benzyltetrahydropyran-4-yl,
2,2-diphenyleth-1-yl,
2,4-dichlorobenzyl,
2,4-difluorobenzyl,
2,5-difluorobenzyl,
2-aminobenzothiazol-4-yl,
2-aminoeth-1-yl,
2-chlorobenzyl,
2-dimethylaminoeth-1-yl,
2-fluoro-4-chlorobenzyl,
2-fluoro-6-aminobenzyl,
2-methoxybenzyl,
2-methyl-4-chlorophenylmethyl,
2-methylbenzyl,
2-phenethyl,
2-phenylbenzyl,
2-piperidin-N-ylbenzyl,
3-(4-fluorophenyl)prop-1-yl,
3-(pyrrol-N-yl)prop-1-yl,
3,4-dichlorobenzyl,
3,5-dichlorobenzyl,
3,5-difluorobenzyl,
3-amino-1-(4-chlorophenyl)prop-1-yl,
3-bromobenzyl,
3-chlorobenzyl,
3-methoxybenzyl,
4-(2-chlorophenyl)thiazol-2-yl,
4-(3,4-difluorophenyl)thiazol-2-yl,
4-(3-chlorophenyl)thiazol-2-yl,
4-(4-methoxyphenyl)thiazol-2-yl,
4-(aminomethyl)benzothiazol-2-yl,
4-(pyridin-2-yl)thiazol-2-yl,
4-(pyridin-3-yl)thiazol-2-yl,
4-(trifluoromethoxy)-6-(aminomethyl)benzothiazol-2-yl,
4-(trifluoromethyl)-6-(aminomethyl)benzothiazol-2-yl,
4,6-dichlorobenzothiazol-2-yl,
4,6-difluorobenzothiazol-2-yl,
4-amino-2-(4-chlorophenyl)but-1-yl,
4-aminobenzyl,
4-aminosulfonylbenzyl,
4-bromo-6-(aminomethyl)benzothiazol-2-yl,
4-bromo-6-isopropyl-benzothiazol-2-yl,
4-bromobenzothiazol-2-yl,
4-bromobenzyl,
4-chloro-[2-(S)-2-(aminopropanoyl)aminomethyl]benzothiazol-2-yl,
4-chloro-1,3-benzothiazol-2-yl,
4-chloro-5-methylcarboxyl-benzothiazol-2-yl,
4-chloro-6-({[2-(S)-2-amino-3-phenylpropanoyl]amino}methyl)benzothiazol-2-yl,
4-chloro-6-(2-aminoethyl)benzothiazol-2-yl,
4-chloro-6-(2-nitroethyl)benzothiazol-2-yl,
4-chloro-6-(dimethylaminomethyl)benzothiazol-2-yl,
4-chloro-6-(methylaminomethyl)benzothiazol-2-yl,
4-chloro-6-(methylcarbonylaminomethyl)benzothiazol-2-yl,
4-chloro-6-(trifluoromethoxy)benzothiazol-2-yl,
4-chloro-6-(trifluoromethyl)benzothiazol-2-yl,
4-chloro-6-[(2-amino)ethylaminocarbonyl]benzothiazol-2-yl,
4-chloro-6-{[(aminomethylcarbonyl)amino]methyl}benzothiaozl-2-yl,
4-chloro-6-aminomethylbenzothiazol-2-yl,
4-chloro-6-hydroxymethylbenzothiazol-2-yl,
4-chloro-6-methylaminomethylbenzothiazol-2-yl,
4-chloro-6-methylthiazol-2-yl,
4-chloro-6-N-morpholinomethyl-benzothiazol-2-yl,
4-chloro-7-aminomethyl-benzothiazol-2-yl,
4-chloro-7-hydroxymethyl-benzothiazol-2-yl,
4-chlorobenzothiazol-2-yl,
4-chlorobenzoxazol-2-yl,
4-chlorobenzyl,
4-dimethylaminobenzyl,
4-fluorobenzyl,
4-fluorobenzothiazol-2-yl,
4-fluorobenzyl,
4-fluorophenyl,
4-fluorophenylmethyl,
4-hydroxy-2-(4-chlorophenyl)but-1-yl,
4-hydroxybenzothiazol-2-yl,
4-hydroxybenzothiazol-4-yl,
4-methoxy-6-(methylaminomethyl)benzothiazol-1-yl,
4-methoxybenzothiazol-2-yl,
4-methoxythiazol-2-yl,
4-methyl-6-aminomethyl-benzothiazol-2-yl,
4-methylbenzyl,
4-methylthiazol-2-yl,
4-phenylthiazol-2-yl,
5-(2-bromothiophen-5-yl)thiazol-2-yl,
5-(3-bromo-4-methoxyphenyl)thiazol-2-yl,
5-chlorobenzoimidazol-2-yl,
5-chlorobenzothiazol-2-yl,
6-aminomethyl-8-chloroquinolin-2-yl,
6-aminomethyl-benzothiazol-2-yl,
6-chlorobenzothiazol-2-yl,
6-fluorobenzothiazol-2-yl,
7-chlorobenzothiazol-2-yl,
benzoimidazol-2-yl,
benzothiazol-2-yl,
benzothiazol-6-yl,
benzothiophen-2-yl,
benzyl,
indan-1-yl,
naphthalen-1-ylmethyl,
pyridin-2-ylmethyl,
pyridin-3-ylmethyl,
pyridin-4-ylmethyl,
pyrimidin-3-yl,
pyrrolidin-3-yl,
quinolin-2-yl,
quinolin-3-yl,
quinolin-6-yl, and
thiophen-2-ylmethyl.
16 . The compound of claim 1 , wherein Q is selected from the group consisting of —C(O)NH—, —NHC(O)—, —NHC(O)NH—, —NHC(O)O—, —CH 2 NH—, —C(O)N(CH 2 CH 2 NH 2 )—, —C(O)N(CH 3 )—, —SO 2 NH—, —C(O)O—, —CH═CH—, and —C≡C—.
17 . The compound of claim 1 , wherein R 6 together with Q and the carbon atom attached thereto and together with R 4 and the carbon atom attached thereto join to form a substituted heterocyclyl.
18 . The compound of claim 17 , wherein the substituted heterocyclyl is 5,6-dihydropyrimidin-4-one.
19 . The compound of claim 1 , wherein R 6 is hydrogen or C 1-3 alkyl, optionally substituted with amino.
20 . The compound of claim 1 , wherein W is —S—.
21 . A compound selected from the group consisting of:
N-[2-(4-fluorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-(2-phenylethyl)thiophene-2-carboxamide;
N-(4-fluorobenzyl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[2-(4-fluorophenyl)ethyl]-5-{2-[(methylsulfonyl)amino]pyrimidin-4-yl}thiophene-2-carboxamide;
N-[2-(4-chlorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[2-(4-bromophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-{2-[4-(aminosulfonyl)phenyl]ethyl}-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[2-(2-fluorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[2-(2-methoxyphenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[2-(3-fluorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[2-(3-methoxyphenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-[(2S)-2-phenylpropyl]thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[2-(2,6-dichlorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[2-(3,4-dichlorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[3-(4-fluorophenyl)propyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-[2-(ethylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[2-(2,4-dichlorophenyl)ethyl]thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-[2-(neopentylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-[2-(cyclopropylamino)pyrimidin-4-yl]-N-[2-(2,4-dichlorophenyl)ethyl]thiophene-2-carboxamide;
5-[2-(cyclobutylamino)pyrimidin-4-yl]-N-[2-(2,4-dichlorophenyl)ethyl]thiophene-2-carboxamide;
N-(4-chloro-1,3-benzothiazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[4-(aminosulfonyl)benzyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-(thien-2-ylmethyl)thiophene-2-carboxamide;
N-{[1-(4-chlorophenyl)cyclopropyl]methyl}-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-[2-(1-methyl-1H-pyrrol-2-yl)ethyl]thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-{2-[(2-hydroxyethyl)amino]pyrimidin-4-yl}thiophene-2-carboxamide;
N-[2-(4-fluorophenyl)ethyl]-5-[5-methyl-2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[1-(4-fluorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-(2-chlorobenzyl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-(3-chlorobenzyl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-(4-chlorobenzyl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-(2,4-difluorobenzyl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-(2,4-dichlorobenzyl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-(2-morpholin-4-yl-2-phenylethyl)thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-(1-naphthylmethyl)thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-(2-phenylpropyl)thiophene-2-carboxamide;
N-[2-(2-chlorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[2-(3-chlorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[1-(4-chlorobenzyl)-2-hydroxyethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-[(2R)-2-phenylpropyl]thiophene-2-carboxamide;
N-[(2S)-2-amino-2-phenylethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(2-chlorobenzyl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(3-chlorobenzyl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(4-chlorobenzyl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(2,4-difluorobenzyl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(2,5-difluorobenzyl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(3,5-difluorobenzyl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(4-chloro-2-fluorobenzyl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(2,4-dichlorobenzyl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(3,4-dichlorobenzyl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(3,5-dichlorobenzyl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[2-(2-chlorophenyl)ethyl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[2-(3-chlorophenyl)ethyl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[2-(4-chlorophenyl)ethyl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[2-(3,4-dichlorophenyl)ethyl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[2-(2,6-dichlorophenyl)ethyl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[(2R)-2-phenylpropyl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[(2S)-2-phenylpropyl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(2-phenylpropyl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-{[1-(4-chlorophenyl)cyclopropyl]methyl}thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[2-(1-methyl-1H-pyrrol-2-yl)ethyl]thiophene-2-carboxamide;
N-[(1S)-1-(2,4-dichlorobenzyl)-2-hydroxyethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[2-(4-chlorophenyl)-4-hydroxybutyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[(2S)-2-amino-2-phenylethyl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(2-methylbenzyl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(4-methylbenzyl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(2-methoxybenzyl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(3-methoxybenzyl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(3-bromobenzyl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(4-bromobenzyl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(2-hydroxy-1-phenylethyl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[2-(2-fluoro-4-methylphenyl)ethyl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[2-(2-fluoro-4-methoxyphenyl)ethyl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[(2R)-2-(4-chlorophenyl)-2-hydroxyethyl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[2-(2,4-dichlorophenyl)propyl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[2-(2,4-dichlorophenyl)butyl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[2-(2,4-dichlorophenyl)pentyl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[2-(2,4-dichlorophenyl)pent-4-enyl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[2-(2,4-dichlorophenyl)pent-4-ynyl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-1,3-benzothiazol-2-ylthiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(4-chloro-1,3-benzothiazol-2-yl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-{[1-(4-chlorophenyl)cyclobutyl]methyl}thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[(1S)-1-(2,4-dichlorobenzyl)-2-hydroxyethyl]thiophene-2-carboxamide;
methyl 2,4-dichloro-N-({5-[2-(methylamino)pyrimidin-4-yl]thien-2-yl}carbonyl)-L-phenylalaninate;
N-[(1S)-benzyl-2-hydroxyethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[(1S)-2-hydroxy-1-phenylethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[4-amino-2-(4-chlorophenyl)butyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[1-(4-chlorophenyl)-3-hydroxypropyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[1-(2,4-dichlorobenzyl)-2-hydroxyethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[1-(2,4-dichlorobenzyl)-2-hydroxyethyl]thiophene-2-carboxamide;
2,4-dichloro-N-({5-[2-(methylamino)pyrimidin-4-yl]thien-2-yl}carbonyl)-L-phenylalanine;
N-(4-chloro-2-methylbenzyl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(4-chloro-2-methylbenzyl)thiophene-2-carboxamide;
N-[2-amino-1-(4-chlorobenzyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[1-(4-chlorophenyl)-3-(dimethylamino)propyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[1-(4-chlorophenyl)-3-(methylamino)propyl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[1-(4-chlorophenyl)-3-(dimethylamino)propyl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(1,1′-biphenyl-2-ylmethyl)thiophene-2-carboxamide;
N-[3-amino-1-(4-chlorophenyl)propyl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide;
N-[2-amino-1-(2,4-dichlorobenzyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-(4-methyl-1,3-benzothiazol-2-yl)thiophene-2-carboxamide;
N-(4-methoxy-1,3-benzothiazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[2-(4-fluorophenyl)ethyl]thiophene-2-carboxamide;
5-[2-(ethylamino)pyrimidin-4-yl]-N-[2-(4-fluorophenyl)ethyl]thiophene-2-carboxamide;
N-[2-(4-fluorophenyl)ethyl]-N-methyl-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[(1R)-2-(2,4-dichlorophenyl)-1-methylethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[2-amino-1-(2,4-dichlorobenzyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-3-carboxamide;
N-[1-(2-aminoethyl)-1H-benzimidazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[1-(2-aminoethyl)-7-chloro-1H-benzimidazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[(1R)-2-amino-1-(2,4-dichlorobenzyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[(1S)-2-amino-1-(2,4-dichlorobenzyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[(1R)-1-(2,4-dichlorobenzyl)-3-(methylamino)propyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[(1R)-1-(2,4-dichlorobenzyl)-3-(dimethylamino)propyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[(1S)-1-(2,4-dichlorobenzyl)-3-(methylamino)propyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[(1S)-1-(2,4-dichlorobenzyl)-3-(dimethylamino)propyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[(1R)-3-amino-1-(2,4-dichlorobenzyl)propyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[(1S)-3-amino-1-(2,4-dichlorobenzyl)propyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-(2-aminoethyl)-N-(4-chloro-1,3-benzothiazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[1-(2-aminoethyl)-4-chloro-1H-benzimidazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[(1S)-2-amino-1-(2,4-dichlorobenzyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[(1R)-2-amino-1-(2,4-dichlorobenzyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[(1S)-1-(2,4-dichlorobenzyl)-2-(dimethylamino)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[(1S)-1-(2,4-dichlorobenzyl)-2-(dimethylamino)ethyl]thiophene-2-carboxamide;
N-(4-chloro-1,3-benzothiazol-2-yl)-N-methyl-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-(4,6-difluoro-1,3-benzothiazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(4,6-difluoro-1,3-benzothiazol-2-yl)thiophene-2-carboxamide;
N-[1-(3-aminopropyl)-4-chloro-1H-benzimidazol-2-yl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide;
N-[1-(2-aminoethyl)-4-methoxy-1H-benzimidazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[1-(2-aminoethyl)-4-methoxy-1H-benzimidazol-2-yl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-quinolin-2-ylthiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(4-methoxy-1,3-benzothiazol-2-yl)thiophene-2-carboxamide;
3-amino-N-[(1S)-1-(2,4-dichlorobenzyl)-2-(dimethylamino)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[(1S)-1-(2,4-dichlorobenzyl)-2-(dimethylamino)ethyl]-3-methoxy-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(4-methoxy-1,3-benzothiazol-2-yl)thiophene-2-carboxamide;
3-amino-N-(4-chloro-1,3-benzothiazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[1-(hydroxymethyl)-2-methylpropyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-(2-hydroxy-1-methylethyl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[2-(dimethylamino)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-(2-aminoethyl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-pyrrolidin-3-ylthiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-piperidin-3-ylthiophene-2-carboxamide;
N-[(2S)-2-amino-3-(1H-indol-3-yl)propyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[(1S)-2-amino-1-(1H-indol-3-ylmethyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-[4-(methylamino)-1,3,5-triazin-2-yl]thiophene-2-carboxamide;
3-[2-(2,4-dichlorophenyl)ethyl]-6-[2-(methylamino)pyrimidin-4-yl]thieno[3,2-d]pyrimidin-4(3H)-one;
6-(2-aminopyrimidin-4-yl)-3-[2-(2,4-dichlorophenyl)ethyl]thieno[3,2-d]pyrimidin-4(3H)-one;
N-[1-(2-aminoethyl)-4-chloro-1H-benzimidazol-2-yl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide;
N-[1-(3-aminopropyl)-4-chloro-1H-benzimidazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-(4-chloro-1-ethyl-1H-benzimidazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[4-chloro-1-(3,3-dimethylbutyl)-1H-benzimidazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
3-amino-N-[2-(2,4-dichlorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-(4-chloro-1-isobutyl-1H-benzimidazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[1-(2-aminoethyl)-4-ethoxy-1H-benzimidazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[1-(2-aminoethyl)-4-ethoxy-1H-benzimidazol-2-yl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide;
N-[1-(2-aminoethyl)-4-phenyl-1H-benzimidazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[1-(2-aminoethyl)-4-phenyl-1H-benzimidazol-2-yl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(4-hydroxy-1,3-benzothiazol-2-yl)thiophene-2-carboxamide;
N-(2-amino-6-fluorobenzyl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[1-(2,4-dichlorobenzyl)-2-(dimethylamino)ethyl]-3-hydroxy-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[(1S)-2-amino-1-(1H-indol-3-ylmethyl)ethyl]-3-methoxy-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-(1-benzylpyrrolidin-3-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[(1S)-2-amino-1-(2,4-dichlorobenzyl)ethyl]-3-(benzyloxy)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[6-(aminomethyl)-4-chloro-1,3-benzothiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[6-(aminomethyl)-4-chloro-1,3-benzothiazol-2-yl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide;
N-{4-chloro-7-[(methylamino)methyl]-1,3-benzothiazol-2-yl}-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[4-chloro-6-(hydroxymethyl)-1,3-benzothiazol-2-yl]thiophene-2-carboxamide;
N-[4-chloro-7-(hydroxymethyl)-1,3-benzothiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[6-(aminomethyl)-1,3-benzothiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[6-(aminomethyl)-1,3-benzothiazol-2-yl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide;
N-[6-(aminomethyl)-4-methyl-1,3-benzothiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[7-(aminomethyl)-4-chloro-1,3-benzothiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-(4-bromo-1,3-benzothiazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[4-chloro-6-(morpholin-4-ylmethyl)-1,3-benzothiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[4-chloro-6-(morpholin-4-ylmethyl)-1,3-benzothiazol-2-yl]thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-(4-phenyl-1,3-thiazol-2-yl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(4-phenyl-1,3-thiazol-2-yl)thiophene-2-carboxamide;
N-(5-chloro-1,3-benzothiazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[4-(3-chlorophenyl)-1,3-thiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[4-(3,4-difluorophenyl)-1,3-thiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[5-(3-bromo-4-methoxyphenyl)-1,3-thiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(5-chloro-1,3-benzothiazol-2-yl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[4-(3-chlorophenyl)-1,3-thiazol-2-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[4-(3,4-difluorophenyl)-1,3-thiazol-2-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[5-(3-bromo-4-methoxyphenyl)-1,3-thiazol-2-yl]thiophene-2-carboxamide;
N-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]thiophene-2-carboxamide;
N-{4-chloro-6-[(dimethylamino)methyl]-1,3-benzothiazol-2-yl}-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-{4-chloro-6-[(dimethylamino)methyl]-1,3-benzothiazol-2-yl}thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(4-bromo-1,3-benzothiazol-2-yl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(4-fluoro-1,3-benzothiazol-2-yl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(4,6-dichloro-1,3-benzothiazol-2-yl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(7-chloro-1,3-benzothiazol-2-yl)thiophene-2-carboxamide;
N-[6-(2-aminoethyl)-4-chloro-1,3-benzothiazol-2-yl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[4-chloro-6-(2-nitroethyl)-1,3-benzothiazol-2-yl]thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-(4-pyridin-2-yl-1,3-thiazol-2-yl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(4-pyridin-2-yl-1,3-thiazol-2-yl)thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-(4-pyridin-3-yl-1,3-thiazol-2-yl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(4-pyridin-3-yl-1,3-thiazol-2-yl)thiophene-2-carboxamide;
N-[6-(2-aminoethyl)-4-chloro-1,3-benzothiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[4-chloro-6-(2-nitroethyl)-1,3-benzothiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
4-chloro-N-methyl-2-[({5-[2-(methylamino)pyrimidin-4-yl]thien-2-yl}carbonyl)amino]-1,3-benzothiazole-6-carboxamide;
N-(2-aminoethyl)-4-chloro-2-[({5-[2-(methylamino)pyrimidin-4-yl]thien-2-yl}carbonyl)amino]-1,3-benzothiazole-6-carboxamide;
N-(2-aminoethyl)-2-({[5-(2-aminopyrimidin-4-yl)thien-2-yl]carbonyl}amino)-4-chloro-1,3-benzothiazole-6-carboxamide;
N-{4-chloro-6-[(methylamino)methyl]-1,3-benzothiazol-2-yl}-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-{4-chloro-6-[(methylamino)methyl]-1,3-benzothiazol-2-yl}thiophene-2-carboxamide;
methyl 4-chloro-2-[({5-[2-(methylamino)pyrimidin-4-yl]thien-2-yl}carbonyl)amino]-1,3-benzothiazole-5-carboxylate;
methyl 2-({[5-(2-aminopyrimidin-4-yl)thien-2-yl]carbonyl}amino)-4-chloro-1,3-benzothiazole-5-carboxylate;
N-(4-chloro-6-methyl-1,3-benzothiazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(4-chloro-6-methyl-1,3-benzothiazol-2-yl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(4-chloro-1,3-benzoxazol-2-yl)thiophene-2-carboxamide;
N-[6-({[(2S)-2-aminopropanoyl]amino}methyl)-4-chloro-1,3-benzothiazol-2-yl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide;
N-[6-(aminomethyl)-4-bromo-1,3-benzothiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-{4-methoxy-6-[(methylamino)methyl]-1,3-benzothiazol-2-yl}-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-{4-methoxy-6-[(methylamino)methyl]-1,3-benzothiazol-2-yl}thiophene-2-carboxamide;
N-(4-chloro-1,3-benzoxazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[6-({[(2S)-2-amino-3-phenylpropanoyl]amino}methyl)-4-chloro-1,3-benzothiazol-2-yl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide;
N-(6-{[(aminoacetyl)amino]methyl}-4-chloro-1,3-benzothiazol-2-yl)-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide;
N-{6-[(acetylamino)methyl]-4-chloro-1,3-benzothiazol-2-yl}-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide;
N-[6-(aminomethyl)-4-(trifluoromethyl)-1,3-benzothiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[6-(aminomethyl)-4-(trifluoromethyl)-1,3-benzothiazol-2-yl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide;
N-[6-(aminomethyl)-4-(trifluoromethoxy)-1,3-benzothiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[6-(aminomethyl)-4-(trifluoromethoxy)-1,3-benzothiazol-2-yl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide;
N-[4-chloro-6-(trifluoromethyl)-1,3-benzothiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[4-chloro-6-(trifluoromethyl)-1,3-benzothiazol-2-yl]thiophene-2-carboxamide;
N-[4-chloro-6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[4-chloro-6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]thiophene-2-carboxamide;
N-[6-(aminomethyl)-4-bromo-1,3-benzothiazol-2-yl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide;
N-(4-bromo-6-isopropyl-1,3-benzothiazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(4-bromo-6-isopropyl-1,3-benzothiazol-2-yl)thiophene-2-carboxamide;
N-[4-(aminomethyl)-1,3-benzothiazol-2-yl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide;
N-[4-(aminomethyl)-1,3-benzothiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[6-(aminomethyl)-8-chloroquinolin-2-yl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide;
N-[(1S)-2-amino-1-(2,4-dichlorobenzyl)ethyl]-3-methoxy-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-(5-benzyl-2,2-dimethyltetrahydro-2H-pyran-4-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[2-(4-fluorophenyl)ethyl]-5-[5-methyl-2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[2-(4-fluorophenyl)ethyl]-5-[2-(nitroamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-anilinopyrimidin-4-yl)-N-[2-(4-fluorophenyl)ethyl]thiophene-2-carboxamide;
methyl 4-[5-({[2-(4-fluorophenyl)ethyl]amino}carbonyl)thien-2-yl]pyrimidin-2-ylcarbamate;
5-(2-{[(dimethylamino)carbonyl]amino}pyrimidin-4-yl)-N-[2-(4-fluorophenyl)ethyl]thiophene-2-carboxamide;
N-[2-(4-fluorophenyl)ethyl]-5-(2-{[(methylamino)carbonyl]amino}pyrimidin-4-yl)thiophene-2-carboxamide;
5-[2-(acetylamino)pyrimidin-4-yl]-N-[2-(4-fluorophenyl)ethyl]thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-[2-(4-methylphenyl)ethyl]thiophene-2-carboxamide;
N-[2-(4-ethylphenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[2-(4-methoxyphenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[2-(1,1,′-biphenyl-4-yl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[2-(4-ethoxyphenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-[2-(4-phenoxyphenyl)ethyl]thiophene-2-carboxamide;
N-[2-(2,5-dimethoxyphenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[2-(3,4-dimethoxyphenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-[2-(dimethylamino)pyrimidin-4-yl]-N-[2-(4-fluorophenyl)ethyl]thiophene-2-carboxamide;
N-(4-fluorophenyl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-[2-(dimethylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-{2-[(aminocarbonyl)amino]pyrimidin-4-yl}-N-[2-(2,4-dichlorophenyl)ethyl]thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-[2-(propylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-[2-(butylamino)pyrimidin-4-yl]-N-[2-(2,4-dichlorophenyl)ethyl]thiophene-2-carboxamide;
5-{2-[(cyclopropylmethyl)amino]pyrimidin-4-yl}-N-[2-(2,4-dichlorophenyl)ethyl]thiophene-2-carboxamide;
5-[2-(benzylamino)pyrimidin-4-yl]-N-[2-(2,4-dichlorophenyl)ethyl]thiophene-2-carboxamide;
5-[2-(cyclopentylamino)pyrimidin-4-yl]-N-[2-(2,4-dichlorophenyl)ethyl]thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-{2-[(2-morpholin-4-ylethyl)amino]pyrimidin-4-yl}thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-{2-[(3-morpholin-4-ylpropyl)amino]pyrimidin-4-yl}thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-(2-{[3-(4-methylpiperazin-1-yl)propyl]amino}pyrimidin-4-yl)thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-{2-[(2-piperidin-1-ylethyl)amino]pyrimidin-4-yl}thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-{2-[(2-phenylethyl)amino]pyrimidin-4-yl}thiophene-2-carboxamide;
N-1H-benzimidazol-2-yl-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-1,3-benzothiazol-2-yl-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-(6-chloro-1,3-benzothiazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-(6-fluoro-1,3-benzothiazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-1,3-benzothiazol-6-yl-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-quinolin-3-ylthiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-quinolin-6-ylthiophene-2-carboxamide;
N-[5-(5-bromothien-2-yl)-1,3-thiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-(pyridin-2-ylmethyl)thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-(pyridin-3-ylmethyl)thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-(pyridin-4-ylmethyl)thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-(2-pyridin-2-ylethyl)thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-(2-pyridin-4-ylethyl)thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-(2-piperidin-1-ylethyl)thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-[2-(4-methylpiperazin-1-yl)ethyl]thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-(2-morpholin-4-ylethyl)thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-[3-(1H-pyrrol-1-yl)propyl]thiophene-2-carboxamide;
5-{2-[(aminocarbonyl)amino]pyrimidin-4-yl}-N-[2-(4-fluorophenyl)ethyl]thiophene-2-carboxamide;
5-{2-[(2-aminoethyl)amino]pyrimidin-4-yl}-N-[2-(2,4-dichlorophenyl)ethyl]thiophene-2-carboxamide;
5-{2-[(3-aminopropyl)amino]pyrimidin-4-yl}-N-[2-(2,4-dichlorophenyl)ethyl]thiophene-2-carboxamide;
5-{2-[(4-aminobutyl)amino]pyrimidin-4-yl}-N-[2-(2,4-dichlorophenyl)ethyl]thiophene-2-carboxamide;
N˜6˜-{4-[5-({[2-(2,4-dichlorophenyl)ethyl]amino}carbonyl)thien-2-yl]pyrimidin-2-yl}-L-lysine;
N-[2-(2,4-dichlorophenyl)ethyl]-5-[2-(pyridin-4-ylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-(2-{[(2S)-2-phenylcyclopropyl]amino}pyrimidin-4-yl)thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-{2-[(pyridin-2-ylmethyl)amino]pyrimidin-4-yl}thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-{2-[(pyridin-3-ylmethyl)amino]pyrimidin-4-yl}thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-{2-[(pyridin-4-ylmethyl)amino]pyrimidin-4-yl}thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-{2-[(2-pyridin-2-ylethyl)amino]pyrimidin-4-yl}thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-{2-[(2-pyridin-3-ylethyl)amino]pyrimidin-4-yl}thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-{2-[(2-pyridin-4-ylethyl)amino]pyrimidin-4-yl}thiophene-2-carboxamide;
5-[2-({[1-(4-chlorophenyl)cyclopropyl]methyl}amino)pyrimidin-4-yl]-N-[2-(2,4-dichlorophenyl)ethyl]thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-(2-{[2-(1-methyl-1H-pyrrol-2-yl)ethyl]amino}pyrimidin-4-yl)thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-(2-{[2-(4-methylpiperazin-1-yl)ethyl]amino}pyrimidin-4-yl)thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-(2-{[3-(1H-imidazol-1-yl)propyl]amino}pyrimidin-4-yl)thiophene-2-carboxamide;
N-(1,2-diphenylethyl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-(2,2-diphenylethyl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-(2-{[(methylamino)carbonyl]amino}pyrimidin-4-yl)thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-(2-{[(ethylamino)carbonyl]amino}pyrimidin-4-yl)thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-(2-{[(propylamino)carbonyl]amino}pyrimidin-4-yl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(2-pyridin-3-ylethyl)thiophene-2-carboxamide;
5-{2-[(anilinocarbonyl)amino]pyrimidin-4-yl}-N-[2-(2,4-dichlorophenyl)ethyl]thiophene-2-carboxamide;
5-(2-{[(benzylamino)carbonyl]amino}pyrimidin-4-yl)-N-[2-(2,4-dichlorophenyl)ethyl]thiophene-2-carboxamide;
N-(4-aminobenzyl)-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[4-(dimethylamino)benzyl]thiophene-2-carboxamide;
N-[2-(4-aminophenyl)ethyl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-1H-benzimidazol-2-ylthiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(1-methyl-1H-benzimidazol-2-yl)thiophene-2-carboxamide;
N-[(2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-2,3-dihydro-1H-inden-1-yl-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-1,2,3,4-tetrahydronaphthalen-1-ylthiophene-2-carboxamide;
N-[(4-chlorophenyl)(phenyl)methyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[4-fluoro-2-(trifluoromethyl)benzyl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(1H-benzimidazol-2-ylmethyl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(1-benzothien-2-ylmethyl)thiophene-2-carboxamide;
N-(5-chloro-1H-benzimidazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(4-chloro-1-methyl-1H-benzimidazol-2-yl)thiophene-2-carboxamide;
N-(4-chloro-1-methyl-1H-benzimidazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(4-chloro-1-ethyl-1H-benzimidazol-2-yl)thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-[4-chloro-1-(3,3-dimethylbutyl)-1H-benzimidazol-2-yl]thiophene-2-carboxamide;
5-(2-aminopyrimidin-4-yl)-N-(4-chloro-1-isobutyl-1H-benzimidazol-2-yl)thiophene-2-carboxamide;
N-(4-hydroxy-1,3-benzothiazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
5-[2-(methylamino)pyrimidin-4-yl]-N-(2-piperidin-1-ylbenzyl)thiophene-2-carboxamide;
N-(4-chloro-1,3-benzothiazol-2-yl)-3-methoxy-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
N-(4-chloro-1,3-benzothiazol-2-yl)-3-hydroxy-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
3-(2-aminoethoxy)-N-(4-chloro-1,3-benzothiazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide;
3-(4-fluorophenyl)-N-{5-[2-(methylamino)pyrimidin-4-yl]thien-2-yl}propanamide;
3-(2,4-dichlorophenyl)-N-{5-[2-(methylamino)pyrimidin-4-yl]thien-2-yl}propanamide;
N-[5-(2-aminopyrimidin-4-yl)thien-2-yl]-3-(2,4-dichlorophenyl)propanamide;
benzyl 5-[2-(methylamino)pyrimidin-4-yl]thien-2-ylcarbamate;
4-fluorobenzyl 5-[2-(methylamino)pyrimidin-4-yl]thien-2-ylcarbamate;
(2R)-2-amino-3-(1H-indol-3-yl)propyl 5-[2-(methylamino)pyrimidin-4-yl]thien-2-ylcarbamate;
(2S)-2-amino-3-(1H-indol-3-yl)propyl 5-[2-(methylamino)pyrimidin-4-yl]thien-2-ylcarbamate;
N-(4-fluorobenzyl)-N′-{5-[2-(methylamino)pyrimidin-4-yl]thien-2-yl}urea;
N-(2,4-dichlorobenzyl)-N′-{5-[2-(methylamino)pyrimidin-4-yl]thien-2-yl}urea;
4-[5-({[2-(4-fluorophenyl)ethyl]amino}methyl)thien-2-yl]-N-methylpyrimidin-2-amine;
4-[5-({[2-(4-chlorophenyl)ethyl]amino}methyl)thien-2-yl]-N-methylpyrimidin-2-amine;
4-[5-({[2-(2,4-dichlorophenyl)ethyl]amino}methyl)thien-2-yl]-N-methylpyrimidin-2-amine;
4-[5-({[2-(4-chlorophenyl)ethyl]amino}methyl)thien-2-yl]pyrimidin-2-amine;
4-chloro-N-({5-[2-(methylamino)pyrimidin-4-yl]thien-2-yl}methyl)-1,3-benzothiazol-2-amine;
N-{[5-(2-aminopyrimidin-4-yl)thien-2-yl]methyl}-4-chloro-1,3-benzothiazol-2-amine;
N-[2-(4-fluorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-sulfonamide;
N-[2-(4-chlorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-sulfonamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-sulfonamide;
N-(4-fluorobenzyl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-sulfonamide;
N-(2,4-dichlorobenzyl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-sulfonamide;
5-(2-aminopyrimidin-4-yl)-N-[2-(4-fluorophenyl)ethyl]thiophene-2-sulfonamide;
5-(2-aminopyrimidin-4-yl)-N-[2-(2,4-dichlorophenyl)ethyl]thiophene-2-sulfonamide;
5-(2-aminopyrimidin-4-yl)-N-(4-fluorobenzyl)thiophene-2-sulfonamide;
5-(2-aminopyrimidin-4-yl)-N-(2,4-dichlorobenzyl)thiophene-2-sulfonamide;
2-amino-1,3-benzothiazol-4-yl 5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxylate;
2-amino-1,3-benzothiazol-4-yl 5-(2-aminopyrimidin-4-yl)thiophene-2-carboxylate;
4-{5-[(E)-2-(4-chloro-1,3-benzothiazol-2-yl)vinyl]thien-2-yl}pyrimidin-2-amine;
4-{5-[(4-chloro-1,3-benzothiazol-2-yl)ethynyl]thien-2-yl}pyrimidin-2-amine;
N-[2-(4-fluorophenyl)ethyl]-5-[2-(methylamino)pyridin-4-yl]thiophene-2-carboxamide;
N-[2-(2,4-dichlorophenyl)ethyl]-5-[2-(methylamino)pyridin-4-yl]thiophene-2-carboxamide;
N-[2-(4-fluorophenyl)ethyl]-5-(2-{[2-(methylamino)ethyl]amino}pyridin-4-yl)thiophene-2-carboxamide;
5-[2-(acetylamino)pyridin-4-yl]-N-[(1S)-2-amino-1′-(2,4-dichlorobenzyl)ethyl]thiophene-2-carboxamide;
N-[2-(4-fluorophenyl)ethyl]-5-pyridin-4-ylthiophene-2-carboxamide;
4-[5-({[2-(4-fluorophenyl)ethyl]amino}carbonyl)thien-2-yl]pyridine-2-carboxamide;
N-[2-(4-fluorophenyl)ethyl]-5-[6-(methylamino)pyridin-2-yl]thiophene-2-carboxamide;
N-[(1S)-2-amino-1-(2,4-dichlorobenzyl)ethyl]-5-pyridin-4-ylthiophene-2-carboxamide;
N-[2-(4-fluorophenyl)ethyl]-5-(1H-pyrazol-3-yl)thiophene-2-carboxamide;
N-[(1S)-2-amino-1′-(2,4-dichlorobenzyl)ethyl]-5-(1H-pyrazol-4-yl)thiophene-2-carboxamide;
N-[(1S)-2-amino-1-(2,4-dichlorobenzyl)ethyl]-5-(2-amino-1H-imidazol-4-yl)thiophene-2-carboxamide;
5-[2-(acetylamino)-1H-imidazol-4-yl]-N-[(1S)-2-amino-1′-(2,4-dichlorobenzyl)ethyl]thiophene-2-carboxamide; and
N-[2-(2,4-dichlorophenyl)ethyl]-5-pyrimidin-4-ylthiophene-2-carboxamide.
22 . A pharmaceutical composition comprising a compound of claim 1 or a mixture thereof and a pharmaceutically acceptable carrier and/or excipient.
23 . A method for treating a mammalian patient suffering from a disorder mediated, at least in part, by CDC7, PKA and/or Akt, said method comprising administering to a patient suffering from a a disorder mediated, at least in part, by CDC7, PKA and/or Akt, a pharmaceutically effective amount of a composition of claim 22 .
24 . The method of claim 23 , wherein said method further comprises administering additional anticancer agents.
25 . A method for inhibiting PKA in a patient suffering from a disorder mediated, at least in part, by PKA, said method comprising administering to said patient, a pharmaceutically effective amount of a composition of claim 22 .
26 . The method of claim 25 , wherein the disorder is cancer.
27 . A method for inhibiting Akt in a patient suffering from a disorder mediated, at least in part, by Akt, said method comprising administering to said patient, a pharmaceutically effective amount of a composition of claim 22 .
28 . The method of claim 23 , wherein the disorder is cancer.
29 . A method for inhibiting CDC7 in a patient suffering from a disorder mediated, at least in part, by CDC7, said method comprising administering to said patient, a pharmaceutically effective amount of a composition of claim 22 .
30 . The method of claim 29 , wherein the disorder is cancer.Cited by (0)
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