Quinolinone-pyrazolone M1 receptor positive allosteric modulators

1. A compound of formula (I):

or a pharmaceutically acceptable salt thereof, wherein

R 1A and R 1B are either hydrogen or selected from the group consisting of

(1) halogen,

(2) —C 1-6 alkyl,

(3) —O—C 1-6 alkyl,

(4) —CN;

R 3 is selected from the group consisting of

(1) —C 6-10 aryl,

(2) heteroaryl, wherein the heteroaryl is an aromatic cyclic group, having from five to ten ring atoms, said ring atoms selected from C, O, N, N→O, C(═O) or S, at least one of which is O, N, N→O or S,

(3) a heterocyclic group having 4 to 8 ring atoms selected from C, O, N, N→O, C(═O), SO 2 or S, at least one of which is O, N, N→O, SO 2 or S,

(4) —C 3-8 cycloalkyl,

wherein each aryl, heteroaryl or heterocyclic is substituted with one or more of R 5 group;

R 5 is selected from the group consisting of

(1) halogen,

(2) —C 2-8 alkenyl,

(3) —O—C 1-6 alkyl,

(4) —C(═O)—(O) m —R 7 ,

(5) —NH—C(═O)—R 7 ,

(6) —C 3-8 cycloalkyl,

(7) —S(═O) 2 —R 7 ,

(8) —NH—S(═O) 2 —R 7 ,

(9) —NO 2 ,

(10) —CN;

(11) C 6-10 aryl,

(12) heteroaryl, which is an aromatic cyclic or polycyclic group, having from five to ten ring atoms, said ring atoms selected from C, O, N, N→O, C(═O) or S, at least one of which is O, N, N→O or S,

(13) —NR 9 R 10 ,

(14) —B(OH) 2 ,

wherein said cycloalkyl, aryl or heteroaryl R 5 group is optionally substituted with one or more

(a) halogen,

(b) —C 1-6 alkyl,

(c) —C 3-8 cycloalkyl,

(d) —NR 11 R 12 ,

(e) —O—C 1-6 alkyl,

(f) C 6-10 aryl,

(g) CN,

(h) hydroxyl

(i) —C(═O)—O—R 7 ,

(j) —NH—C(═O)—R 7 ,

(k) —S(═O) 2 —R 7 ,

(l) —NH—S(═O) 2 —R 7 ,

wherein said alkyl or aryl is optionally substituted with one or more

(i) halogen,

(ii) hydroxyl,

(iii) —NR 13 R 14 ;

R 4 is selected from the group consisting of

(1) —C 6-10 aryl,

(2) heteroaryl, which is an aromatic cyclic or polycyclic group, having from five to ten ring atoms, said ring atoms selected from C, O, N, N→O, C(═O) or S, at least one of which is O, N, N→O or S,

(3) a heterocyclic group having 4 to 8 ring atoms selected from C, O, N, N→O, C(═O), SO 2 or S, at least one of which is O, N, N→O, SO 2 or S,

wherein each aryl, heteroaryl or heterocyclic is optionally substituted with one or more R 6 group;

R 6 is selected from the group consisting of

(1) halogen,

(2) —C 1-6 alkyl,

(3) —C 2-8 alkenyl,

(4) —O—C 1-6 alkyl,

(5) hydroxyl,

(6) —C(═O)—(O) m —R 7 ,

(7) —C(═O)—NR 9 R 10 ,

(8) —O—C(═O)—R 7 ,

(9) —NH—C(═O)—R 7 ,

(10) —NH—C(═O)—OR 7 ,

(11) —C 3-8 cycloalkyl,

(12) —S(═O) 2 —R 7 ,

(13) —S(═O) 2 —OR 7 ,

(14) —S(═O) 2 —NR 9 R 10 ,

(15) —NH—S(═O) 2 —R 7 ,

(16) —NO 2 ,

(17) —CN;

(18) —C 6-10 aryl,

(19) —O—C 6-10 aryl,

(20) heteroaryl, which is an aromatic cyclic or polycyclic group, having from five to ten ring atoms, said ring atoms selected from C, O, N, N→O, C(═O) or S, at least one of which is O, N, N→O or S,

(21) —NR 9 R 10 ,

wherein said alkyl, cycloalkyl, aryl or heteroaryl R 5 group is optionally substituted with one or more

(a) halogen,

(b) —C 1-6 alkyl,

(c) —NR 11 R 12 ,

(d) —O—C 1-6 alkyl,

(f) —C 6-10 aryl,

(g) heteroaryl, which is an aromatic cyclic or polycyclic group, having from five to ten ring atoms, said ring atoms selected from C, O, N, N→O, C(═O) or S, at least one of which is O, N, N→O or S,

(h) CN,

(i) hydroxyl

wherein said alkyl, aryl or heteroaryl is optionally substituted with one or more

(i) halogen,

(ii) hydroxyl,

(iii) —NR 13 R 14 ;

R 7 is selected from the group consisting of

(1) hydrogen,

(2) —C 1-6 alkyl;

(3) —C 3-8 cycloalkyl;

(2) —C 2-6 alkenyl;

(3) —C 0-2 alkyl-C 6-10 aryl,

(4) —C 0-2 alkyl-heteroaryl group, wherein the heteroaryl is an aromatic cyclic or polycyclic group, having from five to ten ring atoms, said ring atoms selected from C, O, N, N→O, C(═O) or S, at least one of which is O, N, N→O or S, wherein said alkyl, alkenyl, aryl or heteroaryl R 7 group is optionally substituted with one or more

(a) halogen,

(b) hydroxy,

(c) —O—C 1-6 alkyl,

(d) —C 1-6 alkyl, optionally substituted with halogen;

R 9 and R 10 , or R 11 and R 12 , or R 13 and R 14 are each independently selected from the group consisting of

(1) hydrogen,

(2) —C 1-6 alkyl,

(3) —C 3-8 cycloalkyl, or

(4) —C 6-10 aryl,

wherein said alkyl, cycloalkyl or aryl is optionally substituted with one or more

(a) halogen,

(b) —C 1-6 alkyl,

(c) —C 3-8 cycloalkyl,

(d) —N(—C 1-6 alkyl) 2 ,

(e) —O—C 1-6 alkyl,

(f) —C 6-10 aryl,

(g) heteroaryl, which is an aromatic cyclic or polycyclic cyclic, having from five to ten ring atoms, said ring atoms selected from C, O, N, N→O, C(═O) or S, at least one of which is O, N, N→O or S,

(h) CN,

(i) hydroxyl

(i) —C(═O)—O—R 7 ,

(j) —NH—C(═O)—R 7 ,

(k) —S(═O) 2 —R 7 ,

(l) —NH—S(═O) 2 —R 7 ,

or R 9 and R 10 , or R 11 and R 12 , or R 13 and R 14 are linked together with the nitrogen to which they are both attached to form a 4-8 membered carbocyclic ring, wherein one or two of the ring carbon atoms is replaced by a nitrogen, oxygen or sulfur, and the carbocyclic is optionally substituted with one or more

(a) halogen,

(b) —C 1-6 alkyl,

(c) —O—C 1-6 alkyl, or

(d) —C 6-10 aryl,

m is 0 or 1;

or a pharmaceutically acceptable salt thereof.

2. The compound of claim 1 wherein R 1A and R 1B are both hydrogen.

3. The compound of claim 1 wherein R 3 is selected from the group consisting of

(1) phenyl,

(2) heteroaryl, which is an aromatic cyclic or polycyclic group, having from five to ten ring atoms, said ring atoms selected from C, O, N, N→O, C(═O), SO 2 or S, at least one of which is O, N, N→O, SO 2 or S,

(3) a heterocyclic group having 4 to 8 ring atoms selected from C, O, N, N→O, C(═O), SO 2 or S, at least one of which is O, N, N→O, SO 2 or S,

wherein phenyl, heteroaryl or heterocyclic is optionally substituted with one or more R 5 .

4. The compound of claim 1 wherein R 5 is present at one or more of the ring atoms and is selected from the group consisting of

(1) halogen,

(2) —O—C 1-6 alkyl,

(3) hydroxyl,

(4) —C(═O)—(O) m —R 7 ,

(5) —NH—C(═O)—R 7 ,

(6) —NH—S(═O) 2 —R 7 ,

(7) —NO 2 ,

(8) —CN;

(9) C 6-10 aryl,

(10) heteroaryl, which is an aromatic cyclic or polycyclic group, having from five to ten ring atoms, said ring atoms selected from C, O, N, N→O, C(═O) or S, at least one of which is O, N, N→O or S, and

(11) —NR 9 R 10 ,

wherein said alkyl, cycloalkyl, aryl or heteroaryl R 5 group is optionally substituted with one or more

(d) halogen,

(e) —C 1-6 alkyl,

(f) —C 3-8 cycloalkyl,

(d) —NR 11 R 12 ,

(f) —O—C 1-6 alkyl,

(f) C 6-10 aryl,

(g) CN,

(h) hydroxyl

(i) —C(═O)—O—R 7 ,

(j) —NH—C(═O)—R 7 ,

(k) —S(═O) 2 —R 7 , or

(l) —NH—S(═O) 2 —R 7 ,

wherein said alkyl or aryl is optionally substituted with one or more

(i) halogen,

(ii) hydroxyl, or

(iii) —NR 11 R 12 .

5. The compound of claim 1 wherein R 4 is selected from the group consisting of

(1) phenyl,

(2) heteroaryl, which is an aromatic cyclic or polycyclic group, having from five to ten ring atoms, said ring atoms selected from C, O, N, N→O, C(═O) or S, at least one of which is O, N, N→O or S,

(3) a heterocyclic group having 4 to 8 ring atoms selected from C, O, N, N→O, C(═O), SO 2 or S, at least one of which is O, N, N→O, SO 2 or S,

wherein phenyl, heteroaryl or heterocyclic is optionally substituted with one or more R 6 group.

6. The compound of claim 1 wherein R 3 is phenyl substituted by a heteroaryl, which is an aromatic cyclic or polycyclic group, having from five to ten ring atoms, said ring atoms selected from C, O, N, N→O, C(═O), SO 2 or S, at least one of which is O, N, N→O, SO 2 or S.

7. The compound of claim 1 represented by structural formula (IV):

or pharmaceutically acceptable salt thereof, wherein R 3 , R 1A and R 1B are defined in claim 1 .

8. A compound which is selected from the group consisting of

2-(2-Fluorophenyl)-5-{[4-(methoxy)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(2-Fluorophenyl)-5-(biphenyl-4-ylmethyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

5-(Biphenyl-4-ylmethyl)-2-phenyl-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

5-(Biphenyl-4-ylmethyl)-2-(phenylmethyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

6,9-Difluoro-2-(1-methyl-1H-imidazol-4-yl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

6,9-Difluoro-2-(1-iodophenyl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

6,9-Difluoro-2-[2-(1H-pyrazol-1-yl)phenyl]-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

6,9-Difluoro-2-[2-(hydroxymethyl)phenyl]-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-{2-[(Ethylamino)methyl]phenyl-6,9-difluoro-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

6,9-Difluoro-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2-[3-(trifluoromethyl)pyridin-2-yl]-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

5-[(4-Bromo-2-fluorophenyl)methyl-6,9-difluoro-2-(2-fluorophenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

6,9-Difluoro-2-(2-fluorophenyl)-5-{[2-fluoro-4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

5-[(4-Iodo-2-fluorophenyl)methyl-6,9-difluoro-2-(2-fluorophenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

6,9-Difluoro-2-(2-fluorophenyl)-5-{[2-fluoro-4-(1H-1,2,4-triazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

6,9-Difluoro-5-({2-fluoro-4-[1-(2-methylpropyl)-1H-pyrazol-4-yl]phenyl}methyl)-2-(2-fluorophenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

5-[(5-Bromo-3-fluoropyridin-2-yl)methyl]-6,9-difluoro-2-(2-fluorophenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

6,9-Difluoro-5-{[3-fluoro-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-yl]methyl}-2-(2-fluorophenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

6,9-Difluoro-5-[(5-fluoro-6′-morpholin-4-yl-3,3′-bipyridin-6-yl)methyl]-2-(2-fluorophenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

6,9-Difluoro-2-(2-fluorophenyl)-5-{3-fluoro-5-(1H-pyrazol-1-yl)pyridin-2-yl}methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-Fluorophenyl-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

5-{[4-(3-Methyl-1H-pyrazol-1-yl)phenyl]methyl}-2-phenyl-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(2-Fluorophenyl)-5-(1H-indol-5-ylmethyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(2-Fluorophenyl)-5-[(2-oxo-1-phenylpiperidin-4-yl)methyl]-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

5{[2-Fluoro-4-(1H-indol-5-yl)phenyl]methyl}-2-(2-fluorophenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

5-[(6-Chloropyridin-3-yl)methyl]-2-(2-fluorophenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(2-Fluorophenyl)-5-{[6-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(2-Fluorophenyl)-5-[(2′-methyl-3,3′-bipyridin-6-yl)methyl]-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(2-Fluorophenyl)-5-{[5-(4-methyl-1H-imidazol-1-yl)pyridin-2-yl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

5-Ethyl-2-(2-fluorophenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(2-Fluorophenyl)-5-{[4-(1,3-oxadiazol-2-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(2-Fluorophenyl)-5-{[4-(1-methyl-1H-pyrazol-4-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(2-Fluorophenyl)-5-{[4-(1-methyl-1H-pyrazol-4-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(2,6-Difluorophenyl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(3-Oxo-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-3,5-dihydro-2H-pyrazolo[4,3-c]quinolin-2-yl)benzonitrile;

6-Fluoro-2-(2-fluorophenyl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

6-Fluoro-2-(2-fluoro-3-methylpyridin-4-yl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

9-Fluoro-2-(2-methylphenyl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

9-Bromo-6-fluoro-2-(2-fluorophenyl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(3-Oxo-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-3,5-dihydro-2H-pyrazolo[4,3-c]quinolin-2-yl)benzoic acid;

N-Methyl-2-(3-oxo-5-{[4-(1H-pyrazol-1-yl)phenyl] methyl}- 3,5-dihydro-2H-pyrazolo[4,3-c]quinolin-2-yl)benzamide;

2-(2-Aminophenyl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-[2-(Ethylamino)phenyl]-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

3-Methyl-N-[2-(3-oxo-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-3,5-dihydro-2H-pyrazolo[4,3-c]quinolin-2-yl)phenyl]butanamide;

5-{[4-(1H-Pyrazol-1-yl)phenyl]methyl}-2-[2-(pyrrolodin-1-ylmethyl)phenyl]-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2,5-Bis {[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-[2-(Hydroxymethyl)phenyl]-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

(±)-2-[2-(Hydroxyethyl)phenyl]-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-[2-(1-Hydroxy-1-methylethyl)phenyl]-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

(±)-2-[2-(Hydroxypropyl)phenyl]-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-[2-(2-Hydroxyethyl)phenyl]-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(2-Propanoylphenyl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

Methyl 2-(3-oxo-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-3,5-dihydro-2H-pyrazolo[4,3-c]quinolin-2-yl)benzoate;

2-[2-(Azidomethyl)phenyl]-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-[2-(Aminomethyl)phenyl]-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(2-Fluorophenyl)-5-{[2-fluoro-4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(2-Bromo-6-fluorophenyl)-5-{[2-fluoro-4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

3-Fluoro-2-(3-oxo-5-{[4-(1H-pyrazol-1-yl)phenyl]methy}-3,5-dihydro-2H-pyrazolo[4,3-c]quinolin-2-yl)benzonitrile;

2-(2-Fluoro-6-methylphenyl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(2-Bromo-6-methylphenyl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(2-Bromo-6-methylphenyl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(3-Chloropyridin-4-yl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(4-Methylpyridin-3-yl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

3-(3-Oxo-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-3,5-dihydro-2H-pyrazolo[4,3-c]quinolin-2-yl)pyridine-4-carbonitrile;

2-Piperidin-4-yl-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(1-Acetylpiperidin-4-yl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(3-Chloro-5-methylpyridin-4-yl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(3,5-Dimethylpyridin-4-yl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

4-{[2-(2-Fluorophenyl)-3-oxo-2,3-dihydro-5H-pyrazolo[4,3-c]quinolin-5-yl]methyl}-N-methylpiperidine-1-carboxamide;

2-(2-Fluorophenyl)-5-{[2-(hydroxymethyl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

(3-Oxo-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-3,5-dihydro-2H-pyrazol[4,3-c]quinolin-2-yl)acetic acid;

N,N-Diethyl-2-(3-oxo-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-3,5-dihydro-2H-pyrazol[4,3-c]quinolin-2-yl)acetamide;

6-Bromo-9-fluoro-2-(2-methylphenyl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

9-Fluoro-6-methyl-2-(2-methylphenyl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

9-Fluoro-2-(2-methylphenyl)-3-oxo-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-3,5-dihydro-2H-pyrazolo[4,3-c]quinoline-6-carbonitrile;

5-{[3-Chloro-4-(6-morpholin-4-ylpyridin-3-yl)phenyl]methyl}-2-(2-fluorophenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

(±)-2-[trans-2-(Methyloxy)cyclohexyl]-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

(±)-2-(cis-2-Fluorocyclohexyl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

(±)-2-(Cyclohex-2-en-1-yl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

(±)-2-(3-Oxo-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-3,5-dihydro-2H-pyrazolo[4,3-c]quinolin-2-yl)cyclohexyl acetate;

(±)-2-(2-Oxocyclohexyl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

(±)-2-[trans-2-(Methylamino)cyclohexyl]-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

5-[(4-Iodophenyl)methyl]-9-(methyloxy)-2-(2-methylphenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

9-(Methyloxy)-2-(2-methylphenyl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

9-Hydroxy-2-(2-methylphenyl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(2-Methylphenyl)-3-oxo-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-3,5-dihydro-2H-pyrazolo[4,3-c]quinolin-9-yl trifluoromethanesulfonate;

9-Methyl-2-(2-methylphenyl)-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(2-Methylphenyl)-3-oxo-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-3,5-dihydro-2H-pyrazolo[4,3-c]quinolin-9-yl acetate;

9-Hydroxy-5-[(iodophenyl)methyl]-2-(2-methylphenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

9-Hydroxy-2-(2-methylphenyl)-5-{[4-(6-methylpyridin-3-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

9-(Methyloxy)-2-(2-methylphenyl)-5-{[4-(6-methylpyridin-3-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-[5-(Hydroxymethyl)-1-methyl-1H-imidazol-4-yl]-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-{1-Methyl-5-[(methylamino)methyl]-1H-imidazol-4-yl]-5-{[4-(1H-pyrazol-1-yl)phenyl]methyl}-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

(±)-2-(3-Fluoro-4-methylpyridin-2-yl)-5-trans-2-[(3-fluoro-4-methylpyridin-2-yl)amino]cyclohexy}-9-({[4-(1H-pyrazol-1-yl)phenyl]methyl}amino)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

8-Fluoro-5-{[4-(methyloxy)phenyl]methyl}-2-(2-methylphenyl)-9-({[4-(1H-pyrazol-1-yl)phenyl]methyl}amino)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

(±)-2-(2-Fluorophenyl)-5-{trans-2-[(3-fluoropyridin-2-yl)amino]cyclohexyl}-9-({[4-(1H-pyrazol-1-yl)phenyl]methyl}amino)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

5-[(5-Bromopyridin-2-yl)methyl]-2-(2-methylphenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(2-Methylphenyl)-5-[(5-phenylpyridin-2-yl)methyl]-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(2-Methylphenyl)-5-(pyridin-2-ylmethyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(3,5-Dichloropyridin-4-yl)-5-[(pyridin-2-yl)methyl]-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(2-Methylphenyl)-5-[(5-methylpyridin-2-yl)methyl]-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-(2-Methylphenyl)-5-(4-nitrobenzyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

5-(4-Aminobenzyl)-2-(2-methylphenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

5-[4-(Dimethylamino)benzyl]-2-(2-methylphenyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

N-(4-{[2-(2-Methylphenyl)-3-oxo-2,3-dihydro-5H-pyrazolo[4,3-c]quinolin-5-yl]methyl}phenyl)methanesulfonamide;

2-Allyl-5-[(5-bromopyridin-2-yl)methyl]-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

2-Allyl-5-(4-fluorobenzyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

5-(4-Fluorobenzyl)-2-pyridin-4-yl-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

5-(4-Fluorobenzyl)-2-piperidin-4-yl-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

Methyl 4-[5-(4-fluorobenzyl)-3-oxo-3,5-dihydro-2H-pyrazolo[4,3-c]quinolin-2-yl]piperidine-1-carboxylate;

5-[(4-Fluorophenyl)methyl]-2-(1-methylpiperidin-4-yl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

(±)-5-(4-Fluorobenzyl)-2-[2-(1-hydroxyethyl)phenyl]-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

5-(4-Fluorobenzyl)-2-propyl-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

5-(4-Fluorobenzyl)-2-[2-(hydroxymethyl)phenyl]-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one;

or a pharmaceutically acceptable salt thereof.

9. The compound of claim 1 , wherein the compound of formula (I) is a compound of formula (IA), (IB), (IC), or (ID)

or a pharmaceutically acceptable salt thereof,

wherein R 4 in (IA) is selected from the group consisting of

R 4 in (IB) is selected from the group consisting of:

R 4 in (IC) is selected from the group consisting of

wherein NR 9 R 10 in (ID) is selected from the group consisting of

10. A compound represented by formula (IF), (IG), (IH), (IJ), or (IK)

wherein NR 9 R 10 in (IF) is selected from the group consisting of

R 5 in (IG) is selected from the group consisting of

Q 1 R 3 in (IH) is selected from the group consisting of

Q 1 R 3 in (IJ) is selected from the group consisting of

R 5 in (IK) is selected from the group consisting of

or a pharmaceutically acceptable salt thereof.

11. A compound represented by formula (IL), (IM), (IN), (IO),

wherein R 5 in (IL) is selected from the group consisting of:

R 5 in (IM) is selected from the group consisting of

wherein Q 1 R 3 in (IN) is selected from the group consisting of

wherein R 5 in (IO) is selected from the group consisting of

12. A compound represented by formula (IP), (IQ), (IR), (IS), (IT)

or a pharmaceutically acceptable salt thereof,

wherein R 5 in (IP) is selected from the group consisting of

wherein Q 2 R 4 in (IQ) is selected from the group consisting of

wherein Q 2 R 4 in (IR) is selected from the group consisting of

wherein R 4 in (IS) is selected from the group consisting of

wherein R 4 in (IT) is selected from the group consisting of:

13. The compound of claim 1 , wherein the compound of formula (I) is a compound of formula (IU), (IV), (IW), (IX), or (IY)

or a pharmaceutically acceptable salt thereof,

wherein NR 9 R 10 in (IU) is selected from the group consisting of

wherein NR 9 R 10 in (IV) is selected from the group consisting of:

wherein R 7 in (IW) is selected from the group consisting of

wherein NR 9 R 10 in (IX) is selected from the group consisting of

wherein NR 9 R 10 in (IY) is selected from the group consisting of

14. A compound represented by structural formula (IZ), (IAA), (IBB), or (IDD)

or a pharmaceutically acceptable salt thereof,

wherein R 6 in (IZ) is selected from the group consisting of

wherein R 5 in (IAA) is selected from the group consisting of

wherein Q 1 R 3 in (IBB) is selected from the group consisting of

wherein R 5 in (IDD) is selected from the group consisting of

15. A compound of claim 1 , wherein the compound of formula (I) is a compound of formula (IFF), (IGG), (IHH), (IJJ)

or a pharmaceutically acceptable salt thereof,

wherein R 4 in (IGG) is selected from the group consisting of

wherein R 5 in (IHH) is selected from the group consisting of

and wherein R 5 in (IJJ) is selected from the group consisting of Et, and CN.

16. A compound represented by structural formula (IKK), (ILL), (IMM)

or a pharmaceutically acceptable salt thereof,

wherein NR 9 R 10 in (IKK) is selected from the group consisting of NHSO 2 Ph, NHCOMe, NHCOPh, and N(SO 2 Me) 2 ,

wherein Q 2 R 4 in (ILL) is selected from the group consisting of

wherein R 4 in (IMM) is selected from the group consisting of

17. A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.