WE CLAIM:
1. Novel bicyclic compounds of formula (I)
r^N^o 6 Formula (I)
Hl R7
5 ring A is selected from 6-10 membered aryl, 5-10 membered heteroaryl, 6-10
membered cyclic ring system and 3-10 membered heterocyclyl;
ring B is selected from 6-10 membered aryl, 5-10 membered heteroaryl and 3-10 membered heterocyclyl;
ring C is selected from 6-10 membered aryl, 5-10 membered heteroaryl and io 3-10 membered heterocyclyl;
wherein either of A or B or C is optionally substituted by one or more, identical or different substituents;
1 9
R and R is present or absent and when present is selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, -C(0)alkyl, cycloalkyl, 15 heterocyclyl, aryl, heteroaryl; wherein any of the group is optionally substituted by one or more, identical or different substituents;
R3 is selected from the group consisting of hydrogen, halogen, amino, nitro, alkyl, haloalkyl, alkoxy, hydroxyalkyl, cycloalkyl, heterocyclyl, heteroaryl;
R4 is selected from the group consisting of hydrogen, alkyl, -C(0)-R4a 20 wherein any of the group is optionally substituted by one or more, identical or different substituents;
R4a is selected from the group consisting of hydrogen, alkyl, haloalkyl,
cycloalkyl, heterocyclyl; wherein any of the group is optionally substituted by one
or more, identical or different substituents;
25 R5 and R6 are same or different and each individually is selected from the
group consisting of hydrogen, halogen, amino, nitro, alkyl, haloalkyl, cycloalkyl,
alkoxy, acylamino, alkylamino, dialkylamino, heterocyclyl; wherein any of the group is optionally substituted by one or more, identical or different substituents;
-7
R is selected from the group consisting of hydrogen, alkyl and "n" is 0 to 2.
5 2. The compound of formula (I) according to claim 1, or a pharmaceutically acceptable salt or a stereoisomer thereof, in which the ring A along with the attached ring is specifically represented by
3. The novel bicyclic compounds of formula (I) according to claim 1 wherein the 10 compound is formula (Ia)
R4 R3 N-N
y\ ^Ji JL { C ) Formula (Ia)
R7 R6
or a pharmaceutically acceptable salt or a pharmaceutically acceptable regioisomer thereof: wherein,
x" is selected from O, S or N R', wherein R' is selected from hydrogen, alkyl;
"y" and "z" independently are selected from N, CR", wherein R" is selected from hydrogen, halogen, alkyl; 5 ring C is selected from 6-10 membered aryl, 5-10 membered heteroaryl and
3-10 membered heterocyclyl, optionally substituted by one or more, identical or different substituents;
R3 is selected from the group consisting of hydrogen, halogen, amino, nitro, alkyl, haloalkyl, alkoxy, hydroxyalkyl, cycloalkyl, heterocyclyl, heteroaryl; 10 R4 is selected from the group consisting of hydrogen, alkyl, -C(0)-R4a
wherein any of the group is optionally substituted by one or more, identical or different substituents;
R4a is selected from the group consisting of hydrogen, alkyl, haloalkyl, cycloalkyl, heterocyclyl; wherein any of the group is optionally substituted by one 15 or more, identical or different substituents;
R5 and R6 are same or different and each individually is selected from the group consisting of hydrogen, halogen, amino, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy, acylamino, alkylamino, dialkylamino, heterocyclyl; wherein any of the group is optionally substituted by one or more, identical or different substituents;
-7
20 R is selected from the group consisting of hydrogen, alkyl and
"n" is 0 to 2. 4. The novel bicyclic compounds of formula (I) according to claim 1 wherein the compound is formula (Ib)
ing C is selected from 6-10 membered aryl, 5-10 membered heteroaryl and 3-10 membered heterocyclyl, optionally substituted by one or more, identical or different substituents;
1 9
R and R is present or absent and when present is selected from the group 5 consisting of hydrogen, halogen, alkyl, alkoxy, -C(0)alkyl, cycloalkyl, heterocyclyl, aryl, heteroaryl; wherein any of the group is optionally substituted by one or more, identical or different substituents;
R3 is selected from the group consisting of hydrogen, halogen, amino, nitro, alkyl, haloalkyl, alkoxy, hydroxyalkyl, cycloalkyl, heterocyclyl, heteroaryl; 10 R4 is selected from the group consisting of hydrogen, alkyl, -C(0)-R4a
wherein any of the group is optionally substituted by one or more, identical or different substituents;
R4a is selected from the group consisting of hydrogen, alkyl, haloalkyl, cycloalkyl, heterocyclyl; wherein any of the group is optionally substituted by one 15 or more, identical or different substituents;
R5 and R6 are same or different and each individually is selected from the group consisting of hydrogen, halogen, amino, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy, acylamino, alkylamino, dialkylamino heterocyclyl; wherein any of the group is optionally substituted by one or more, identical or different substituents;
-7
20 R is selected from the group consisting of hydrogen, alkyl and
"n" is 0 to 2. 5. The novel bicyclic compounds of formula (I) according to claim 1 wherein the compound is formula (Ie)
R4 R3 N-N
"d^n^o v_^r5 Formula (Ie)
R7 R6
25 or a pharmaceutically acceptable salt or a pharmaceutically acceptable regioisomer thereof; wherein,
ring C is selected from 6-10 membered aryl, 5-10 membered heteroaryl and 3-10 membered heterocyclyl, optionally substituted by one or more, identical or different substituents;
"A", "B", "C", and "D" independently are selected from O, S, NR', 5 C(R")2, or any of the two A and B or C and D represent CR' form a doublé bond, wherein R' is absent or when present is selected from hydrogen, alkyl and R" is hydrogen, halogen and alkyl;
R3 is selected from the group consisting of hydrogen, halogen, amino, nitro, alkyl, haloalkyl, alkoxy, hydroxyalkyl, cycloalkyl, heterocyclyl, heteroaryl; 10 R4 is selected from the group consisting of hydrogen, alkyl, -C(0)-R4a
wherein any of the group is optionally substituted by one or more, identical or different substituents;
R4a is selected from the group consisting of hydrogen, alkyl, haloalkyl, cycloalkyl, heterocyclyl, wherein any of the group is optionally substituted by one 15 or more, identical or different substituents;
R5 and R6 are same or different and each individually is selected from the group consisting of hydrogen, halogen, amino, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy, acylamino, alkylamino, dialkylamino, heterocyclyl; wherein any of the group is optionally substituted by one or more, identical or different substituents;
-7
20 R is selected from the group consisting of hydrogen, alkyl and
"n" is 0 to 2. 6. The novel bicyclic compounds of formula (I) according to claim 1 wherein the compound is formula (ld)
Rp R4
J/7
"3 in u ^-^R5 Formula (ld)
R7 r6
or a pharmaceutically acceptable salt or a pharmaceutically acceptable regioisomer 25 thereof; wherein,
ring C is selected from 6-10 membered aryl, 5-10 membered heteroaryl and 3-10 membered heterocyclyl, optionally substituted by one or more, identical or different substituents;
1 9
R and R is present or absent and when present is selected from the group 5 consisting of hydrogen, halogen, alkyl, alkoxy, -C(0)alkyl, cycloalkyl, heterocyclyl, aryl, heteroaryl, wherein any of the group is optionally substituted by one or more, identical or different substituents;
R3 is selected from the group consisting of hydrogen, halogen, amino, nitro, alkyl, haloalkyl, hydroxyalkyl, cycloalkyl, heterocyclyl, heteroaryl; 10 R4 is selected from the group consisting of hydrogen, alkyl, -C(0)-R4a
wherein any of the group is optionally substituted by one or more, identical or different substituents;
R4a is selected from the group consisting of hydrogen, alkyl, haloalkyl, cycloalkyl, heterocyclyl, wherein any of the group is optionally substituted by one 15 or more, identical or different substituents;
R5 and R6 are same or different and each individually is selected from the group consisting of hydrogen, halogen, amino, nitro, alkyl, haloalkyl, cycloalkyl, alkoxy, acylamino, alkylamino, dialkylamino, heterocyclyl; wherein any of the group is optionally substituted by one or more, identical or different substituents;
-7
20 R is selected from the group consisting of hydrogen, alkyl and
"n" is 0 to 2.
7. The novel bicyclic compounds of formula (I) according to claims 3-6 wherein the ring C is specifically represented by
O Qt, ö O
H
° vl {/> v_y
8. A novel bicyclic compound selected from the group consisting of
1. 6-Chloro-3-(5-(4-methoxyphenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylquinolin-2(lH)-one
2. 6-Chloro-3-(l-(cyclopropanecarbonyl)-5-(4-methoxyphenyl)-4,5-dihydro-lH-pyrazol-3-yl)-4-methylquinolin-2(lH)-one
3. 6-chloro-3-(5-(4-methoxyphenyl)-l-(tetrahydro-2H-pyran-4-carbonyl)-4,5-dihydro-lH-pyrazol-3-yl)-4-methylquinolin-2(lH)-one
4. 6-chloro-3-(5-(4-methoxyphenyl)-l-(tetrahydrofuran-3-carbonyl)-4,5-dihydro-lH-pyrazol-3-yl)-4-methylquinolin-2(lH)-one
5. 6-Chloro-3-(5-(4-methoxyphenyl)-l-methyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylquinolin-2(lH)-one
6. 6-Chloro-4-methyl-3-(5-(l-methyl-lH-indol-6-yl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)quinolin-2(lH)-one
7. 6-chloro-3-(5-(4-methoxyphenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylquinolin-2(lH)-one
8. N-(4-(3-(6-chloro-4-methyl-2-oxo-l,2-dihydroquinolin-3-yl)-l-propionyl-4,5-dihydro-lH-pyrazol-5-yl)phenyl)propionamide
9. 3-(5-(4-Methoxyphenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methyl-l,5-naphthyridin-2(lH)-one
10. 4-Methyl-3-(5-(l-methyl-lH-indol-5-yl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)quinolin-2(lH)-one
11. 3-(5-(4-Methoxyphenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylquinolin-2( lH)-one
12. 4-Methyl-3-(5-(l-methyl-lH-indol-3-yl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)quinolin-2(lH)-one
13. 3-(5-(4-Methoxyphenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methyl-l,8-naphthyridin-2(lH)-one
14. 6-(5-(4-Methoxyphenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-5-methylpyrido-[2,3-d]pyrimidin-7(8H)-one
15. 6-bromo-3-(5-(4-methoxyphenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylquinolin-2(lH)-one
16. 6-chloro-3-(5-(4-methoxyphenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methyl-l,5-naphthyridin-2(lH)-one
17. 6-Chloro-3-(5-(4-methoxyphenyl)-l-propionyl-lH-pyrazol-3-yl)quinolin-
135
2(lH)-one
18. 6-chloro-3-(5-(4-methoxyphenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-l,4-dimethylquinolin-2(lH)-one
19. 4-(5-(4-methoxyphenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)isoquinolin-3(2H)-one
20. 5-(5-(4-Methoxyphenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno-[2,3-b]pyridin-6(7H)-one
21. 5-(5-(6-methoxypyridin-3-yl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
22. 5-(5-(4-methoxyphenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
23. 6-chloro-4-cyclopropyl-3-(5-(4-methoxyphenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)quinolin-2(lH)-one
24. 6-chloro-4-methyl-3-(5-(l-methyl-lH-indol-3-yl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)quinolin-2(lH)-one
25. 5-(5-(5-methoxypyridin-2-yl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
26. 4-methyl-5-(5-(6-oxo-l,6-dihydropyridin-3-yl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
27. 5-(5-(4-fluorophenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
28. 5-(5-(4-chlorophenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
29. 5-(5-(5-methoxythiophen-2-yl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
30. 5-(5-(2-methoxythiazol-5-yl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
31. 5-(5-(5-bromothiophen-3-yl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
32. 4-methyl-5-(5-phenyl-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
136
33. 4-methyl-5-(l-propionyl-5-(thiophen-3-yl)-4,5-dihydro-lH-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
34. 5-(5-(4-bromothiophen-2-yl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
35. 4-methyl-5-(l-propionyl-5-(pyridin-4-yl)-4,5-dihydro-lH-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
36. 4-methyl-5-(l-propionyl-5-(pyridin-3-yl)-4,5-dihydro-lH-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
37. 4-methyl-5-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
38. 4-methyl-5-(5-(4-(4-methylpiperazin-l-yl)phenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
39. 5-(5-(4-(dimethylamino)phenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
40. 3-chloro-5-(5-(4-methoxyphenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
41. 5-(5-(5-methylthiophen-2-yl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
42. 4-methyl-5-(l-propionyl-5-(4-(trifluoromethyl)phenyl)-4,5-dihydro-lH-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
43. 5-(5-(4-(difluoromethyl)phenyl)- l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
44. 5-(5-(4-ethylphenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
45. 4-methyl-5-(5-(6-methylpyridin-3-yl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
46. 4-methyl-5-(l-propionyl-5-(4-(pyrrolidin-l-yl)phenyl)-4,5-dihydro-lH-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
47. 5-(5-(4-cyclopropylphenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
48. 4-methyl-5-(5-(2-methylthiazol-4-yl)-l-propionyl-4,5-dihydro-lH-
137
pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
49. 5-(5-(4-isopropylphenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
50. 5-(5-(4,6-dimethylpyridin-3-yl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
51. 4-methyl-5-(5-(2-methylpyrimidin-5-yl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
52. 5-(5-(5-chloro-6-methylpyridin-3-yl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
53. 5-(5-(4-methoxy-6-methylpyridin-3-yl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
54. 5-(5-(5,6-dimethylpyridin-3-yl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
55. 5-(5-(5-fluoro-6-methylpyridin-3-yl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
56. 5-(5-(4-chloro-6-methylpyridin-3-yl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
57. 4-methyl-5-(5-(2-methylthiazol-5-yl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
58. 5-(5-cyclohexyl-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
59. 6-chloro-4-methyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl) quinolin- 2( 1H) - one
60. 4-methyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl) quinolin- 2( 1H) - one
61. 6-chloro-4-methyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)-1,5-naphthyridin-2( lH)-one
62. 5-(l-acetyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)-4-methyl-7,7a-dihydrothieno[2,3-b]pyridin-6(7H)-one
63. 5-(l-isobutyryl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)-4-methyl-7,7a-dihydrothieno[2,3-b]pyridin-6(7H)-one
138
64. 4-methyl-5-(5-(p-tolyl)-l-(2,2,2-trifluoroacetyl)-4,5-dihydro-lH-pyrazol-3-yl)-7,7a-dihydrothieno[2,3-b]pyridin-6(7H)-one
65. 5-(5-(2-chloro-4-methylphenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
66. 5-(5-(2-fluoro-4-methylphenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
67. 6-chloro-4-methyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)-1,8-naphthyridin-2( lH)-one
68. 5-(5-(4-(fluoromethyl)phenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
69. 4-methyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)-l,5-naphthyridin-2(lH)-one
70. 2,4-dimethyl-5-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
71. 5-(5-benzyl-1 -propionyl-4,5-dihydro- lH-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
72. 2-chloro-4-methyl-5-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
73. 4-methyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)-l,8-naphthyridin-2(lH)-one
74. 4-methyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)-l,7-naphthyridin-2(lH)-one
75. 4,7-dimethyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl) quinolin- 2( 1H) - one
76. 4,5-dimethyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl) quinolin- 2( 1H) - one
77. 4-methyl-7-morpholino-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)quinolin-2(lH)-one
78. 4,8-dimethyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)-l,7-naphthyridin-2(lH)-one
79. 6-chloro-4-methyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-
139
yl)-1,7-naphthyridin-2( lH)-onev
80. 7-chloro-4-methyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl) quinolin- 2( 1H) - one
81. 4,6-dimethyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)-l,7-naphthyridin-2(lH)-one
82. 4-methyl-7-(4-methylpiperazin-l-yl)-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)quinolin-2(lH)-one
83. 7-fluoro-4-methyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl) quinolin- 2( 1H) - one
84. 4,7-dimethyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)-l,8-naphthyridin-2(lH)-one
85. 4-methyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)-l,6-naphthyridin-2(lH)-one
86. 4-methyl-7-morpholino-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)-l,8-naphthyridin-2(lH)-one
87. 7-(2-methoxyethoxy)-4-methyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)-l,8-naphthyridin-2(lH)-one
or a pharmaceutically acceptable salt thereof or a pharmaceutically acceptable
regioisomer thereof.
9. A novel bicyclic regoisomer compound selected from
(R)-5-(5-(4-methoxyphenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-5 methylthieno[2,3-b]pyridin-6(7H)-one
(S)-5-(5-(4-methoxyphenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-
methylthieno[2,3-b]pyridin-6(7H)-one
(R)-5-(5-(4-chlorophenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-
methylthieno[2,3-b]pyridin-6(7H)-one 10 (S)-5-(5-(4-chlorophenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-
methylthieno[2,3-b]pyridin-6(7H)-one
(R)-4-methyl-5-(l-propionyl-5-(thiophen-3-yl)-4,5-dihydro-lH-pyrazol-3-
yl)thieno[2,3-b]pyridin-6(7H)-one
(S)-4-methyl-5-(l-propionyl-5-(thiophen-3-yl)-4,5-dihydro-lH-pyrazol-3-
yl)thieno[2,3-b]pyridin-6(7H)-one
(R)-4-methyl-5-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)thieno[2,3-b]
(S)-4-methyl-5-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)thieno[2,3-5 b]pyridin-6(7H)-one pyridin-6(7H)-one
(R)-4-methyl-5-(5-(6-methylpyridin-3-yl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-
yl)thieno[2,3-b]pyridin-6(7H)-one
(S)-4-methyl-5-(5-(6-methylpyridin-3-yl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-
yl)thieno[2,3-b]pyridin-6(7H)-one 10 (R)-4-methyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)quinolin-
2(lH)-one
(S)-4-methyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)quinolin-
2(lH)-one
(R)-5-(5-(2-fluoro-4-methylphenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-15 methylthieno[2,3-b]pyridin-6(7H)-one
(S)-5-(5-(2-fluoro-4-methylphenyl)-l-propionyl-4,5-dihydro-lH-pyrazol-3-yl)-4-
methylthieno[2,3-b]pyridin-6(7H)-one
(R)-4-methyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)-l,7-
naphthyridin-2(lH)-one 20 (S)-4-methyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)-l,7-
naphthyridin-2(lH)-one
(R)-4,8-dimethyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)-l,7-
naphthyridin-2(lH)-one
(S)-4,8-dimethyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)-l,7-25 naphthyridin-2(lH)-one
(R)-7-chloro-4-methyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-
yl) quinolin- 2( 1H) - one
(S)-7-chloro-4-methyl-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-
yl) quinolin- 2( 1H) - one 30 (R)-4-methyl-7-(4-methylpiperazin-l-yl)-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-
lH-pyrazol-3-yl)quinolin-2(lH)-one
141
S)-4-methyl-7-(4-methylpiperazin-l-yl)-3-(l-propionyl-5-(p-tolyl)-4,5-dihydro-lH-pyrazol-3-yl)quinolin-2(lH)-one.
10. The pharmaceutical composition, comprising at least one compound according to any one of claims 1 to 9, or a pharmaceutically acceptable salt or a stereoisomer
5 thereof and a pharmaceutically acceptable carrier or excipient.
11. The compound according to any one of claims 1 to 9, or a pharmaceutically acceptable salt or a stereoisomer thereof, for use as a medicament.
12. The method of inhibiting RAD51 protein comprising administering a therapeutically effective amount of a compound according to any one of claims 1 to
io 9.
13. The method as claimed in claim 12 for the treatment of cancer associated with RAD51 protein.