2-aminoimidazole beta-secretase inhibitors for the treatment of alzheimer's disease
View Patent ↗The present invention is directed to 2-aminoimidazole compounds of formula (I) which are inhibitors of the beta-secretase enzyme and that are useful in the treatment of diseases in which the beta-secretase enzyme is involved, such as Alzheimer's disease. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the treatment of such diseases in which the beta-secretase enzyme is involved.
1. A compound of formula (I)
wherein:
R 1 is phenyl which is optionally substituted with one or more groups independent selected from the group consisting of:
(a) halo,
(b) —NO 2 ,
(c) —CN,
(d) —C 1-6 alkyl, and
(h) —O—C 1-6 alkyl;
R 2 is hydrogen;
R 3 is
—(CH 2 ) n -phenyl,
wherein said phenyl moiety is optionally independently substituted with one or more groups independently selected from the group consisting of:
(a) halo,
(b) —OH,
(c) —CN,
(d) —NO 2 ,
(e) —C 1-6 alkyl
(f) —C 2-6 alkenyl
(g) —C 3-6 cycloalkyl,
(h) —O—C 1-6 alkyl,
(i) —O—CH 2 -aryl,
(j) —C 6-10 aryl,
(k) heteroaryl, wherein said heteroaryl is an aromatic cyclic group having 5 to 12 ring atoms, at least one of which is O, N or S,
(l) —NR 6A R 6B ,
(m) —NR 6A C(═O)R 6B ,
(n) a heterocyclic group having 4 to 8 ring atoms, wherein one ring atom is a heteroatom selected from the group consisting of nitrogen, sulfur and oxygen,
(o) —SO 2 C 1-3 alkyl,
(p) —SO 2 NR 6A R 6B , and
(q) —CONR 6A R 6B ,
wherein said alkyl, alkenyl, cycloalkyl, aryl and heteroaryl moiety is optionally substituted with one or more groups independently selected form the group consisting of:
(I) halo,
(II) —C 1-6 alkyl, wherein said alkyl is optionally substituted with one or more fluoro,
(III) —O—C 1-6 alkyl, wherein said alkyl is optionally substituted with one or more fluoro,
(IV) —NHSO 2 R 9 , and
(V) OH;
R 4 is selected from the group consisting of:
(1) hydrogen, and
(2) —C 1-6 alkyl,
wherein said alkyl is optionally substituted with one or more groups independently selected from the group consisting of:
(a) halogen
(b) hydroxyl,
(c) —C 6-10 aryl,
(d) heteroaryl, wherein said heteroaryl is an aromatic cyclic group having 5 to 12 ring atoms, at least one of which is O, N or S,
(e) —OC 1-4 alkyl, and
(f) —C(═O)OR 9 ,
and wherein said alkyl, aryl or heteroaryl is optionally substituted with one or more groups independently selected from the group consisting of:
(I) hydroxy,
(II) fluoro,
(III) —C 1-4 alkyl, optionally substituted by fluoro; and
(IV) —OC 1-4 alkyl;
R 5 is selected from the group consisting of:
(1) hydrogen,
(2) —C 1-6 alkyl, and
(3) a heterocyclic group having 4 to 8 ring atoms, wherein at least one ring atom is a heteroatom selected from the group consisting of nitrogen, sulfur and oxygen,
wherein said alkyl or heterocyclyl is optionally substituted with one or more groups independently selected from the group consisting of:
(a) halogen
(b) hydroxyl,
(c) —C 6-10 aryl,
(d) heteroaryl, wherein said heteroaryl is an aromatic cyclic group having 5 to 12 ring atoms, at least one of which is O, N or S,
(e) a heterocyclic group having 4 to 8 ring atoms, wherein at least one ring atom is a heteroatom selected from the group consisting of nitrogen, sulfur and oxygen,
(f) —OC 1-4 alkyl,
(g) —CN, and
(h) —C(═O)—OR 9 ,
wherein said aryl, heteroaryl or heterocyclic group is optionally substituted with one or more groups independently selected from the group consisting of:
(I) hydroxy,
(II) fluoro,
(III) —C 1-4 alkyl, optionally substituted by fluoro,
(IV) —OC 1-4 alkyl,
(V) —(CH 2 ) n —C 6-10 aryl,
(VI) heteroaryl, and
(VII) —C(═O)OR 9 ;
R 6A and R 6B are independently selected from the group consisting of:
(1) hydrogen,
(2) halogen,
(3) C 1-6 alkyl,
(4) O—C 1-6 alkyl,
(5) —NO 2 ,
(6) cyano
(7) OH
(8) —(CH 2 ) m aryl, and
(9) —NR 7 R 8 , wherein R 7 and R 8 are independently selected from the group consisting of
(I) hydrogen,
(II) —C 1-6 alkyl, and
(III) —C 3-6 cycloalkyl,
or R 7 and R 8 are linked together with the nitrogen to which they are both attached to form a 2-6 membered carbocyclic ring, wherein one or two of the ring carbon atoms is replaced by a nitrogen, oxygen or sulfur,
wherein said R 6A or R 6B alkyl or aryl moiety is optionally substituted with one or more groups independently selected from the group consisting of:
(a) halo,
(b) —C 1-6 alkyl,
(c) —O—C 1-6 alkyl, and
(d) -aryl,
wherein said alkyl or aryl is optionally substituted with one or more halo;
R 9 is selected from the group consisting of:
(1) hydrogen,
(2) C 1-4 alkyl, and
(3) —C 3-8 cycloalkyl,
n is o or 1; and
m is 0, 1, 2 or 3;
provided that when R 2 , R 4 and R 5 are each hydrogen, then R 1 is not 4-methoxyphenyl and R 3 is not (1-methoxy-4-nitrophenyl)methylene;
or a pharmaceutically acceptable salt thereof.
2. A compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 1 is selected from the group consisting of phenyl, 4-methoxyphenyl, 3-methoxyphenyl, 2-methoxyphenyl, 2-bromo-4-methoxyphenyl, 4-chlorophenyl, 3-fluoro-4-methoxyphenyl, 2-nitro-4,5-dimethoxyphenyl and 2-bromo-4,5-dimethoxyphenyl.
3. A compound of claim 1 , or a pharmaceutically acceptable salt thereof, wherein R 3 is benzyl,
and wherein said benzyl moiety is optionally substituted with one or more
(a) halo,
(b) —NO 2 ,
(c) —CN,
(d) —C 1-6 alkyl,
(e) —C 2-6 alkenyl,
(f) —C 3-6 cycloalkyl,
(g) —O—C 1-6 alkyl,
(h) —(C 6-10 ) aryl, or
(i) heteroaryl,
wherein said alkyl, aryl or heteroaryl moiety is optionally substituted with one or more
(I) halo,
(II) —C 1-6 alkyl, wherein said alkyl is optionally substituted with one or more fluoro,
(III) —O—C 1-6 alkyl, wherein said alkyl is optionally substituted with one or more fluoro,
(IV) —NSO 2 R 9 , or OH.
4. A compound of claim 3 , or a pharmaceutically acceptable salt thereof, wherein R 4 is hydrogen.
5. A compound of claim 3 , or a pharmaceutically acceptable salt thereof, wherein R 4 is a C 1-6 alkyl group, which is substituted by one or more
(a) halogen
(b) hydroxyl,
(c) —C 6-10 aryl,
(d) heteroaryl, wherein said heteroaryl is an aromatic cyclic group having 5 to 12 ring atoms, at least one of which is O, N, or S, or
(e) —C(═O)OR 9 ,
and wherein said alkyl, aryl or heteroaryl is optionally substituted with one or more
(I) hydroxy,
(II) fluoro, or
(III) —OC 1-4 alkyl.
6. A compound claim 5 , or a pharmaceutically acceptable salt thereof, wherein R 5 is hydrogen, methyl or ethyl.
7. A compound claim 5 , or a pharmaceutically acceptable salt thereof, wherein R 5 is a substituted C 1-6 alkyl group, which is substituted by one or more
(a) halogen
(b) hydroxyl,
(c) —C 6-10 aryl,
(d) heteroaryl, or
(e) a heterocyclic group having 4 to 8 ring atoms, wherein at least one ring atom is a heteroatom selected from the group consisting of nitrogen, sulfur and oxygen,
wherein said aryl, heteroaryl or heterocyclic group is optionally substituted with one or more
(I) hydroxy,
(II) fluoro, or
(III) —OC 1-4 alkyl.
8. A compound of formula (II):
or a pharmaceutically acceptable salt thereof, wherein R 10 is optionally present at one or more of the ring carbon atoms, and each R 10 is independently selected from the group consisting of
(a) halo,
(b) —OH,
(c) —CN,
(d) —C 1-6 alkyl,
(e) —C 2-6 alkenyl,
(f) —C 3-6 cycloalkyl,
(g) —NO 2 ,
(h) —O—C 1-6 alkyl, and
(i) phenyl;
R 3 is selected from the group consisting of:
—(CH 2 ) n -phenyl,
wherein said phenyl moiety is optionally independently substituted with one or more groups independently selected from the group consisting of:
(a) halo,
(b) —OH,
(c) —CN,
(d) —NO 2 ,
(e) —C 1-6 alkyl
(f) —C 2-6 alkenyl
(g) —C 3-6 cycloalkyl,
(h) —O—C 1-6 alkyl,
(i) —O—CH 2 -aryl,
(j) —C 6-10 aryl,
(k) heteroaryl, wherein said heteroaryl is an aromatic cyclic group having 5 to 12 ring atoms, at least one of which is O, N or S,
(l) —NR 6A R 6B ,
(m) —NR 6A C(═O)R 6B ,
(n) a heterocyclic group having 4 to 8 ring atoms, wherein one ring atom is a heteroatom selected from the group consisting of nitrogen, sulfur and oxygen,
(o) —SO 2 C 1-3 alkyl,
(p) —SO 2 NR 6A R 6B , and
(q) —CONR 6A R 6B ,
wherein said alkyl, alkenyl, cycloalkyl, aryl and heteroaryl moiety is optionally substituted with one or more groups independently selected form the group consisting of:
(I) halo,
(II) —C 1-6 alkyl, wherein said alkyl is optionally substituted with one or more fluoro,
(III) —O—C 1-6 alkyl, wherein said alkyl is optionally substituted with one or more fluoro,
(IV) —NHSO 2 R 9 and
(V) OH;
R 4 is selected from the group consisting of:
(1) hydrogen, and
(2) —C 1-6 alkyl,
wherein said alkyl is optionally substituted with one or more groups independently selected from the group consisting of:
(a) halogen
(b) hydroxyl,
(c) —C 6-10 aryl,
(d) heteroaryl, wherein said heteroaryl is an aromatic cyclic group having 5 to 12 ring atoms, at least one of which is O, N or S,
(e) —OC 1-4 alkyl, and
(f) —C(═O)OR 9 ,
and wherein said alkyl, aryl or heteroaryl is optionally substituted with one or more groups independently selected from the group consisting of:
(I) hydroxy,
(II) fluoro,
(III) —C 1-4 alkyl, optionally substituted by fluoro; and
(IV) —OC 1-4 alkyl;
R 5 is selected from the group consisting of:
(1) hydrogen,
(2) —C 1-6 alkyl, and
(3) a heterocyclic group having 4 to 8 ring atoms, wherein at least one ring atom is a heteroatom selected from the group consisting of nitrogen, sulfur and oxygen,
wherein said alkyl or heterocyclyl is optionally substituted with one or more groups independently selected from the group consisting of:
(a) halogen
(b) hydroxyl,
(c) —C 6-10 aryl,
(d) heteroaryl, wherein said heteroaryl is an aromatic cyclic group having 5 to 12 ring atoms, at least one of which is O, N or S,
(e) a heterocyclic group having 4 to 8 ring atoms, wherein at least one ring atom is a heteroatom selected from the group consisting of nitrogen, sulfur and oxygen,
(f) —OC 1-4 alkyl,
(g) —CN, and
(h) —C(═O)—OR 9 ,
wherein said aryl, heteroaryl or heterocyclic group is optionally substituted with one or more groups independently selected from the group consisting of:
(I) hydroxy,
(II) fluoro,
(III) —C 1-4 alkyl, optionally substituted by fluoro,
(IV) —OC 1-4 alkyl,
(V) —(CH 2 ) n —C 6-10 aryl,
(VI) heteroaryl, and
(VII) —C(═O)OR 9 ;
R 6A and R 6B are independently selected from the group consisting of:
(1) hydrogen,
(2) halogen,
(3) C 1-6 alkyl,
(4) O—C 1-6 alkyl,
(5) —NO 2 ,
(6) cyano
(7) OH
(8) —(CH 2 ) m aryl, and
(9) —NR 7 R 8 , wherein R 7 and R 8 are independently selected from the group consisting of
(I) hydrogen,
(II) —C 1-6 alkyl, and
(III) —C 3-6 cycloalkyl,
or R 7 and R 8 are linked together with the nitrogen to which they are both attached to form a 2-6 membered carbocyclic ring, wherein one or two of the ring carbon atoms is replaced by a nitrogen, oxygen or sulfur,
wherein said R 6A or R 6B alkyl or aryl moiety is optionally substituted with one or more groups independently selected from the group consisting of:
(a) halo,
(b) —C 1-6 alkyl,
(c) —O—C 1-6 alkyl, and
(d) -aryl,
wherein said alkyl or aryl is optionally substituted with one or more halo;
R 9 is selected from the group consisting of:
(1) hydrogen,
(2) C 1-4 alkyl, and
(3) —C 3-8 cycloalkyl,
n is o or 1; and
m is 0, 1, 2 or 3;
provided that when R 4 and R 5 are each hydrogen, then R 10 is not 4-methoxy and R 3 is not (1-methoxy-4-nitrophenyl)methylene;
or a pharmaceutically acceptable salt thereof.
9. A compound of formula (III):
or a pharmaceutically acceptable salt thereof, wherein:
R 10 is optionally present at one or more of the ring carbon atoms, and each R 10 is selected from the group consisting of
(a) halo,
(b) —OH,
(c) —CN,
(d) —C 1-6 alkyl,
(e) —C 2-6 alkenyl,
(f) —C 3-6 cycloalkyl,
(g) —NO 2 ,
(h) 0-O—C 1-6 alkyl, and
(i) phenyl;
R 11 is optionally present at one or more of the ring carbon atoms, and each R 11 is selected from the group consisting of:
(a) halo,
(b) —NO 2 ,
(c) —CN,
(d) —C 1-6 alkyl,
(e) —C 2-6 alkenyl,
(f) —C 3-6 cycloalkyl,
(g) —O—C 1-6 alkyl,
(h) aryl,
(i) heteroaryl,
wherein said alkyl, aryl or heteroaryl moiety is optionally substituted with one or more
(I) halo,
(II) —C 1-6 alkyl, wherein said alkyl is optionally substituted with one or more fluoro,
(III) —O—C 1-6 alkyl, wherein said alkyl is optionally substituted with one or more fluoro,
(IV) —NSO 2 R 9 , or
(V) OH;
R 4 is selected from the group consisting of:
(1) hydrogen, and
(2) —C 1-6 alkyl,
wherein said alkyl is optionally substituted with one or more groups independently selected from the group consisting of:
(a) halogen
(b) hydroxyl,
(c) —C 6-10 aryl,
(d) heteroaryl, wherein said heteroaryl is an aromatic cyclic group having 5 to 12 ring atoms, at least one of which is O, N or S,
(e) —OC 1-4 alkyl, and
(f) —C(═O)OR 9 ,
and wherein said alkyl, aryl or heteroaryl is optionally substituted with one or more groups independently selected from the group consisting of:
(I) hydroxy,
(II) fluoro,
(III) —C 1-4 alkyl, optionally substituted by fluoro; and
(IV) —OC 1-4 alkyl;
R 5 is selected from the group consisting of:
(1) hydrogen,
(2) —C 1-6 alkyl, and
(3) a heterocyclic group having 4 to 8 ring atoms, wherein at least one ring atom is a heteroatom selected from the group consisting of nitrogen, sulfur and oxygen,
wherein said alkyl or heterocyclyl is optionally substituted with one or more groups independently selected from the group consisting of:
(a) halogen
(b) hydroxyl,
(c) —C 6-10 aryl,
(d) heteroaryl, wherein said heteroaryl is an aromatic cyclic group having 5 to 12 ring atoms, at least one of which is O, N or S,
(e) a heterocyclic group having 4 to 8 ring atoms, wherein at least one ring atom is a heteroatom selected from the group consisting of nitrogen, sulfur and oxygen,
(f) —OC 1-4 alkyl,
(g) —CN, and
(h) —C(═O)—OR 9 ,
wherein said alkyl, aryl, heteroaryl or heterocyclic group is optionally substituted with one or more groups independently selected from the group consisting of:
(I) hydroxy,
(II) fluoro,
(III) —C 1-4 alkyl, optionally substituted by fluoro,
(IV) —OC 1-4 alkyl,
(V) —(CH 2 ) n —C 6-10 aryl,
(VI) heteroaryl, and
(VII) —C(═O)OR 9 ;
R 6A and R 6B are independently selected from the group consisting of:
(1) hydrogen,
(2) halogen,
(3) C 1-6 alkyl,
(4) O—C 1-6 alkyl,
(5) —NO 2 ,
(6) cyano
(7) OH
(8) —(CH 2 ) m aryl, and
(9) —NR 7 R 8 , wherein R 7 and R 8 are independently selected from the group consisting of
(I) hydrogen,
(II) —C 1-6 alkyl, and
(III) —C 3-6 cycloalkyl,
or R 7 and R 8 are linked together with the nitrogen to which they are both attached to form a 2-6 membered carbocyclic ring, wherein one or two of the ring carbon atoms is replaced by a nitrogen, oxygen or sulfur,
wherein said R 6A or R 6B alkyl or aryl moiety is optionally substituted with one or more groups independently selected from the group consisting of:
(a) halo,
(b) —C 1-6 alkyl,
(c) —O—C 1-6 alkyl, and
(d) -aryl,
wherein said alkyl or aryl is optionally substituted with one or more halo;
R 9 is selected from the group consisting of:
(1) hydrogen,
(2) C 1-4 alkyl, and
(3) —C 3-8 cycloalkyl,
n is 0 or 1; and
m is 0, 1, 2 or 3;
or a pharmaceutically acceptable salt thereof.
10. A compound which is selected from the group consisting of:
Ex.
No.
Structure
IUPAC Name
1
4-{(1S)-1-(4- methoxylphenyl)-2-[4- (trifluoromethyl)phenyl] ethyl}-1-H-imidazole-2- amine
2
(2-amino-4-{(1S)-1- (4-methoxyphenyl)-2- [4- (trifluoromethyl)phenyl] ethyl}-1H-imidazole- 5-yl)(phenyl)methanol
4
4-{1-(4-methoxyphenyl)- 2-[4-(3- thienyl)phenyl]ethyl}-1- methyl-1H-imidazol-2- amine
7
4-[1-(3-fluoro-4- methoxyphenyl)-2-(2- methoxy-5-nitrophenyl) ethyl]-1H-imidazol-2- amine
8
4-{1-(4-methoxyphenyl)- 2-[4-(trifluoromethyl) phenyl]ethyl}-1H- imidazol-2-amine
9
1-{2-amino-4-[1-(3-fluoro- 4-methoxyphenyl)-2-(2- methoxy-5-nitrophenyl) ethyl]-1H-imidazol-5- yl}propan-1-ol
10
4-[2-(4-chlorophenyl)-1- (4-methoxyphenyl)ethyl]- 1H-imidazol-2-amine
11
4-[2-(2-fluoro-4,5- dimethoxyphenyl)-1-(4- methoxyphenyl)ethyl]-1H- imidazol-2-amine
12
4-[2-(2-amino-1H- imidazol-4-yl)-2-(4- methoxyphenyl)ethyl] benzonitrile
14
4-[2-(2-methoxy-5- nitrophenyl)-1-(4- methoxyphenyl)ethyl]-1H- imidazol-2-amine
15
4-[2-[3-chloro-4- (trifluoromethoxy)phenyl]- 1-(4-methoxyphenyl) ethyl]-1H-imidazol-2- amine
16
4-[2-(2,4-dichloro-5- nitrophenyl)-1-(4- methoxyphenyl)ethyl]-1H- imidazol-2-amine
17
4-[2-(2-fluoro-5- iodophenyl)-1-(4- methoxyphenyl)ethyl]-1H- imidazol-2-amine
19
3-[2-(2-amino-1H- imidazol-4-yl)-2-(4- methoxyphenyl)ethyl]-4- fluorobenzonitrile
20
{2-amino-4-[2-(2- methoxy-5-nitrophenyl)-1- (4-methoxyphenyl)ethyl]- 1H-imidazol-5- yl}(pyridin-4-yl)methanol
22
{2-amino-4-[2-(2- methoxy-5-nitrophenyl)-1- (4-methoxyphenyl)ethyl]- 1H-imidazol-5-yl}(1H- imidazol-2-yl)methanol
23
{2-amino-4-[2-(2- methoxy-5-nitrophenyl)-1- (4-methoxyphenyl)ethyl]- 1H-imidazol-5-yl} (hydroxy)acetic acid
24
{2-amino-4-[2-(2- methoxy-5-nitrophenyl)-1- (4-methoxyphenyl)ethyl]- 1H-imidazol-5- yl}(pyridin-2-yl)methanol
25
4-[2-(4-fluorobiphenyl-3- yl)-1-(4-methoxyphenyl) ethyl]-1H-imidazol-2- amine
26
4-[2-(2-chloro-4- iodophenyl)-1-(4- methoxyphenyl)ethyl]-1H- imidazol-2-amine
27
4-[1-(3-fluoro-4- methoxyphenyl)-2-(2- methoxy-5-nitrophenyl) ethyl]-1H-imidazol-2- amine
28
4-[1-(3-fluoro-4- methoxyphenyl)-2-(2- methoxy-5-nitrophenyl) ethyl]-1H-imidazol-2- amine
29
4-[2-(2-methoxy-5- nitrophenyl)-1-(4- methoxyphenyl)ethyl]-1- methyl-1H-imidazol-2- amine
30
1-ethyl-4-[2-(2-methoxy-5- nitrophenyl)-1-(4- methoxyphenyl)ethyl]-1H- imidazol-2-amine
31
1-isopropyl-4-[2-(2- methoxy-5-nitrophenyl)-1- (4-methoxyphenyl)ethyl]- 1H-imidazol-2-amine
32
4-[2-(2-methoxyphenyl)-1- (4-methoxyphenyl)ethyl]- 1-methyl-1H-imidazol-2- amine
33
4-[1-(4-methoxyphenyl)-2- phenylethyl]-1-methyl-1H- imidazol-2-amine
34
4-[2-[2′-chloro-4′- (trifluoromethyl)biphenyl- 3-yl]-1-(4-methoxyphenyl) ethyl]-1-methyl-1H- imidazol-2-amine
35
4-(1,2-diphenylethyl)-1- methyl-1H-imidazol-2- amine
36
4-[1-(4-methoxyphenyl)-2- (3-nitrophenyl)ethyl]-1- methyl-1H-imidazol-2- amine
37
4-[1-(4-methoxyphenyl)-2- (3-nitrophenyl)ethyl]-1- methyl-1H-imidazol-2- amine
38
4-[2-(3-chlorophenyl)-1- (4-methoxyphenyl)ethyl]- 1-methyl-1H-imidazol-2- amine
39
1-benzyl-4-[1-(4- methoxyphenyl)-2- phenylethyl]-1H-imidazol- 2-amine
40
1-benzyl-4-[2-(2-methoxy- 5-nitrophenyl)-1-(4- methoxyphenyl)ethyl]-1H- imidazol-2-amine
43
N-{3′-[2-(2-amino-1- methyl-1H-imidazol-4-yl)- 2-(4-methoxyphenyl) ethyl]biphenyl-3-yl} methanesulfonamide
44
4-[2-(4-bromophenyl)-1- (4-methoxyphenyl)ethyl]- 1-methyl-1H-imidazol-2- amine
45
4-{1-(4-methoxyphenyl)- 2-[3-(3-thienyl)phenyl] ethyl}-1-methyl-1H- imidazol-2-amine
46
4-[2-[3-(3-furyl)phenyl]-1- (4-methoxyphenyl)ethyl]- 1-methyl-1H-imidazol-2- amine
47
4-{1-(4-methoxyphenyl)- 2-[3-(1-methyl-1H- pyrazol-4-yl)phenyl] ethyl}-I-methyl-1H- imidazol-2-amine
48
4-[2-[3-(3,5- dimethylisoxazol-4- yl)phenyl]-1-(4- methoxyphenyl)ethyl]-1- methyl-1H-imidazol-2- amine
49
5-{3-[2-(2-amino-1- methyl-1H-imidazol-4-yl)- 2-(4-methoxyphenyl) ethyl]phenyl}pyridin-2-ol
50
4-[2-(3-chloro-5- fluorophenyl)-1-(4- methoxyphenyl)ethyl]-1- methyl-1H-imidazol-2- amine
51
4-[2-[5-chloro-2- (trifluoromethyl)phenyl]-1- (4-methoxyphenyl)ethyl]- 1-methyl-1H-imidazol-2- amine
52
4-[2-[4-(3-furyl)phenyl]-1- (4-methoxyphenyl)ethyl]- 1-methyl-1H-imidazol-2- amine
53
4-{1-(4-methoxyphenyl)- 2-[4-(1-methyl-1H- pyrazol-4-yl)phenyl] ethyl}-1-methyl-1H- imidazol-2-amine
54
4-[2-[4-(3,5- dimethylisoxazol-4- yl)phenyl]-1-(4- methoxyphenyl)ethyl]-1- methyl-1H-imidazol-2- amine
55
5-{4-[2-(2-amino-1- methyl-1H-imidazol-4-yl)- 2-(4-methoxyphenyl) ethyl]phenyl}pyridin-2-ol
56
4-[2-(2,5-dichlorophenyl)- 1-(4-methoxyphenyl) ethyl]-1-methyl-1H- imidazol-2-amine
58
4-[2-(3-allylphenyl)-1-(4- methoxyphenyl)ethyl]-1- methyl-1H-imidazol-2- amine
59
4-[1-(4-methoxyphenyl)-2- (3-pent-4-en-1- ylphenyl)ethyl]-1-methyl- 1H-imidazol-2-amine
60
4-[2-(4-allylphenyl)-1-(4- methoxyphenyl)ethyl]-1- methyl-1H-imidazol-2- amine
61
4-[1-(4-methoxyphenyl)-2- (4-pent-4-en-1-ylphenyl) ethyl]-1-methyl-1H- imidazol-2-amine
62
4-[2-(3-cyclopropylphenyl)- 1-(4-methoxyphenyl) ethyl]-1-methyl-1H- imidazol-2-amine
63
4-[2-(4-cyclopropylphenyl)- 1-(4-methoxyphenyl) ethyl]-1-methyl-1H- imidazol-2-amine
66
4-[1-(4-methoxyphenyl)-2- phenylethyl]-1-(2- phenylethyl)-1H-imidazol- 2-amine
67
4-[2-(2-methoxy-5- nitrophenyl)-1-(4- methoxyphenyl)ethyl]-1- (2-phenylethyl)-1H- imidazol-2-amine
68
4-[2-(5-allyl-2- methoxyphenyl)-1-(4- methoxyphenyl)ethyl]-1- methyl-1H-imidazol-2- amine
69
4-{1-(4-methoxyphenyl)- 2-[2-methoxy-5-(3-thienyl) phenyl]ethyl}-1-methyl- 1H-imidazol-2-amine
70
4-[2-[5-(3-furyl)-2- methoxyphenyl]-1-(4- methoxyphenyl)ethyl]-1- methyl-1H-imidazol-2- amine
71
4-[2-[2-methoxy-5-(1- methyl-1H-pyrazol-4- yl)phenyl]-1-(4- methoxyphenyl)ethyl]-1- methyl-1H-imidazol-2- amine
72
4-[2-{2-methoxy-5-[(1E)- pent-1-en-1-yl]phenyl}-1- (4-methoxyphenyl)ethyl]- 1-methyl-1H-imidazol-2- amine
73
4-[2-(5-bromo-2- methoxyphenyl)-1-(4- methoxyphenyl)ethyl]-1- methyl-1H-imidazol-2- amine
74
4-[2-(2,4-dichlorophenyl)- 1-(4-methoxyphenyl) ethyl]-1-methyl-1H- imidazol-2-amine
75
4-[2-(2-chlorophenyl)-1- (4-methoxyphenyl)ethyl]- 1-methyl-1H-imidazol-2- amine
78
3-[2-(2-amino-1-methyl- 1H-imidazol-4-yl)-2-(4- methoxyphenyl)ethyl] benzonitrile
79
4-[2-(4-bromophenyl)-1- (4-methoxyphenyl)ethyl]- 1-(3-phenylpropyl)-1H- imidazol-2-amine
80
3-{2-amino-4-[2-(4- bromophenyl)-1-(4- methoxyphenyl)ethyl]-1H- imidazol-1-yl}propan-1-ol
81
4-[1-(2-bromo-4- methoxyphenyl)-2-(4- bromophenyl)ethyl]-1-(3- phenylpropyl)-1H- imidazol-2-amine
82
4-[2-(4-bromophenyl)-1- (4-methoxyphenyl)ethyl]- 1-[3-(trifluoromethyl) benzyl]-1H-imidazol-2- amine
83
4-[2-(4-bromophenyl)-1- (4-methoxyphenyl)ethyl]- 1-[2-(1,3-dioxolan-2- yl)ethyl]-1H-imidazol-2- amine
84
4-({2-amino-4-[2-(4- bromophenyl)-1-(4- methoxyphenyl)ethyl]-1H- imidazol-1-yl}methyl) phenol
85
1-[(1-benzyl-1H-pyrazol- 4-yl)methyl]-4-[2-(4- bromophenyl)-1-(4- methoxyphenyl)ethyl]-1H- imidazol-2-amine
86
4-[2-(4-bromophenyl)-1- (4-methoxyphenyl)ethyl]- 1-(3-methoxybenzyl)-1H- imidazol-2-amine
87
4-{2-amino-4-[2-(4- bromophenyl)-1-(4- methoxyphenyl)ethyl]-1H- imidazol-1-yl}-3,3- dimethylbutan-1-ol
88
tert-butyl 4-{2-amino-4-[2- (4-bromophenyl)-1-(4- methoxyphenyl)ethyl]-1H- imidazol-1-yl}piperidine- 1-carboxylate
89
4-[2-(4-bromophenyl)-1- (4-methoxyphenyl)ethyl]- 1-(1H-indol-5-ylmethyl)- 1H-imidazol-2-amine
90
4-[2-(4-bromophenyl)-1- (4-methoxyphenyl)ethyl]- 1-(2,2-dimethoxy-2- pyridin-4-ylethyl)-1H- imidazol-2-amine
91
4-[2-(4-bromophenyl)-1- (4-methoxyphenyl)ethyl]- 1-[2-(2-pyridin-4-yl-1H- indol-3-yl)ethyl]-1H- imidazol-2-amine
92
4-[2-(4-bromophenyl)-1- (4-methoxyphenyl)ethyl]- 1-[(1-methyl-2,3-dihydro- 1H-indol-5-yl)methyl]-1H- imidazol-2-amine
95
3-{2-amino-4-[2-(4- bromophenyl)-1-(4- methoxyphenyl)ethyl]-1H- imidazol-1-yl}-2- phenylpropan-1-ol
96
3-{2-amino-4-[1-(2- bromo-4-methoxyphenyl)- 2-(4-bromophenyl)ethyl]- 1H-imidazol-1-yl}propan- 1-ol
97
4-[2-(2,4-dichlorophenyl)- 1-(4-methoxyphenyl) ethyl]-1-(3-phenylpropyl)- 1H-imidazol-2-amine
98
4-[2-(2,4-dichlorophenyl)- 1-(4-methoxyphenyl) ethyl]-1-[3- (trifluoromethyl)benzyl]- 1H-imidazol-2-amine
99
4-[2-(2,4-dichlorophenyl)- 1-(4-methoxyphenyl) ethyl]-1-[2-(1,3-dioxolan- 2-yl)ethyl]-1H-imidazol-2- amine
101
4-[2-(2,4-dichlorophenyl)- 1-(4-methoxyphenyl) ethyl]-1-methyl-1H- imidazol-2-amine
107
4-{1-(4-methoxyphenyl)- 2-[4-(trifluoromethyl) phenyl]ethyl}-1-methyl- 1H-imidazol-2-amine
108
4-[1-(4-methoxyphenyl)-2- (3-pyrimidin-5-ylphenyl) ethyl]-1-methyl-1H- imidazol-2-amine
109
(2-amino-4-{1-(4- methoxyphenyl)-2-[4- (trifluoromethyl)phenyl] ethyl}-1-methyl-1H- imidazol-5-yl)(phenyl) methanol.
11. A pharmaceutical composition comprising a therapeutically effective amount of a compound of any of claims 1 to 10 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.