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US 2025/0145601 A1Published application
Novel bicyclic compounds as rad51 inhibitors
AssigneeSatya Therapeutics, Inc.
InventorsSanjita SASMAL, Venkatesham BOORGU, Shankar CHITHALURI
Life of this patent
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Abstract
The present invention relates to novel bicyclic compounds of formula (I) as inhibitors of RAD51 inhibitors, their pharmaceutically acceptable salts, solvates, polymorphs, tautomers, optical and geometric isomers thereof.
Claims20
Novel bicyclic compounds of formula (I)
- 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 3-10 membered heterocyclyl;
- wherein either of A or B or C is optionally substituted by one or more, identical or different substituents;
- R1 and R2 is present or absent and when present is selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, —C(O)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;
- R4 is selected from the group consisting of hydrogen, alkyl, —C(O)—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 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;
- R7 is selected from the group consisting of hydrogen, alkyl and
- “n” is 0 to 2.
11 more elements
A novel bicyclic compound selected from the group consisting of
- 1. 6-Chloro-3-(5-(4-methoxyphenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylquinolin-2(1H)-one
- 2. 6-Chloro-3-(1-(cyclopropanecarbonyl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl)-4-methylquinolin-2(1H)-one
- 3. 6-chloro-3-(5-(4-methoxyphenyl)-1-(tetrahydro-2H-pyran-4-carbonyl)-4,5-dihydro-1H-pyrazol-3-yl)-4-methylquinolin-2(1H)-one
- 4. 6-chloro-3-(5-(4-methoxyphenyl)-1-(tetrahydrofuran-3-carbonyl)-4,5-dihydro-1H-pyrazol-3-yl)-4-methylquinolin-2(1H)-one
- 5. 6-Chloro-3-(5-(4-methoxyphenyl)-1-methyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylquinolin-2(1H)-one
- 6. 6-Chloro-4-methyl-3-(5-(1-methyl-1H-indol-6-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)quinolin-2(1H)-one
- 7. 6-chloro-3-(5-(6-methoxypyridin-3-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylquinolin-2(1H)-one
- 8. N-(4-(3-(6-chloro-4-methyl-2-oxo-1,2-dihydroquinolin-3-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-5-yl)phenyl)propionamide
- 9. 3-(5-(4-Methoxyphenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methyl-1,5-naphthyridin-2(1H)-one
- 10. 4-Methyl-3-(5-(1-methyl-1H-indol-6-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)quinolin-2(1H)-one
- 11. 3-(5-(4-Methoxyphenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylquinolin-2(1H)-one
- 12. 4-Methyl-3-(5-(1-methyl-1H-indol-3-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)quinolin-2(1H)-one
- 13. 3-(5-(4-Methoxyphenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methyl-1,8-naphthyridin-2(1H)-one
- 14. 6-(5-(4-Methoxyphenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-5-methylpyrido-[2,3-d]pyrimidin-7(8H)-one
- 15. 6-bromo-3-(5-(4-methoxyphenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylquinolin-2(1H)-one
- 16. 6-chloro-3-(5-(4-methoxyphenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methyl-1,5-naphthyridin-2(1H)-one
- 17. 6-Chloro-3-(5-(4-methoxyphenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)quinolin-2(1H)-one
- 18. 6-chloro-3-(5-(4-methoxyphenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-1,4-dimethylquinolin-2(1H)-one
- 19. 4-(5-(4-methoxyphenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)isoquinolin-3(2H)-one
- 20. 5-(5-(4-Methoxyphenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno-[2,3-b]pyridin-6(7H)-one
- 21. 5-(5-(6-methoxypyridin-3-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 22. 5-(5-(4-methoxyphenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
- 23. 6-chloro-4-cyclopropyl-3-(5-(4-methoxyphenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)quinolin-2(1H)-one
- 24. 6-chloro-4-methyl-3-(5-(1-methyl-1H-indol-3-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)quinolin-2(1H)-one
- 25. 5-(5-(5-methoxypyridin-2-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 26. 4-methyl-5-(5-(6-oxo-1,6-dihydropyridin-3-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
- 27. 5-(5-(4-fluorophenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 28. 5-(5-(4-chlorophenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 29. 5-(5-(5-methoxythiophen-2-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 30. 5-(5-(2-methoxythiazol-5-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 31. 5-(5-(5-bromothiophen-3-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 32. 4-methyl-5-(5-phenyl-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
- 33. 4-methyl-5-(1-propionyl-5-(thiophen-3-yl)-4,5-dihydro-1H-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
- 34. 5-(5-(4-bromothiophen-2-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 35. 4-methyl-5-(1-propionyl-5-(pyridin-4-yl)-4,5-dihydro-1H-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
- 36. 4-methyl-5-(1-propionyl-5-(pyridin-3-yl)-4,5-dihydro-1H-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
- 37. 4-methyl-5-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
- 38. 4-methyl-5-(5-(4-(4-methylpiperazin-1-yl)phenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
- 39. 5-(5-(4-(dimethylamino)phenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 40. 3-chloro-5-(5-(4-methoxyphenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 41. 5-(5-(5-methylthiophen-2-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 42. 4-methyl-5-(1-propionyl-5-(4-(trifluoromethyl)phenyl)-4,5-dihydro-1H-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
- 43. 5-(5-(4-(difluoromethyl)phenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 44. 5-(5-(4-ethylphenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 45. 4-methyl-5-(5-(6-methylpyridin-3-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
- 46. 4-methyl-5-(1-propionyl-5-(4-(pyrrolidin-1-yl)phenyl)-4,5-dihydro-1H-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
- 47. 5-(5-(4-cyclopropylphenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 48. 4-methyl-5-(5-(2-methylthiazol-4-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
- 49. 5-(5-(4-isopropylphenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 50. 5-(5-(4,6-dimethylpyridin-3-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 51. 4-methyl-5-(5-(2-methylpyrimidin-5-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
- 52. 5-(5-(5-chloro-6-methylpyridin-3-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 53. 5-(5-(4-methoxy-6-methylpyridin-3-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 54. 5-(5-(5,6-dimethylpyridin-3-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 55. 5-(5-(5-fluoro-6-methylpyridin-3-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 56. 5-(5-(4-chloro-6-methylpyridin-3-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 57. 4-methyl-5-(5-(2-methylthiazol-5-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
- 58. 5-(5-cyclohexyl-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 59. 6-chloro-4-methyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)quinolin-2(1H)-one
- 60. 4-methyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)quinolin-2(1H)-one
- 61. 6-chloro-4-methyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)-1,5-naphthyridin-2(1H)-one
- 62. 5-(1-acetyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)-4-methyl-7,7a-dihydrothieno[2,3-b]pyridin-6(7H)-one
- 63. 5-(1-isobutyryl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)-4-methyl-7,7a-dihydrothieno[2,3-b]pyridin-6(7H)-one
- 64. 4-methyl-5-(5-(p-tolyl)-1-(2,2,2-trifluoroacetyl)-4,5-dihydro-1H-pyrazol-3-yl)-7,7a-dihydrothieno[2,3-b]pyridin-6(7H)-one
- 65. 5-(5-(2-chloro-4-methylphenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 66. 5-(5-(2-fluoro-4-methylphenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 67. 6-chloro-4-methyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)-1,8-naphthyridin-2(1H)-one
- 68. 5-(5-(4-(fluoromethyl)phenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 69. 4-methyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)-1,5-naphthyridin-2(1H)-one
- 70. 2,4-dimethyl-5-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
- 71. 5-(5-benzyl-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- 72. 2-chloro-4-methyl-5-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
- 73. 4-methyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)-1,8-naphthyridin-2(1H)-one
- 74. 4-methyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)-1,7-naphthyridin-2(1H)-one
- 75. 4,7-dimethyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)quinolin-2(1H)-one
- 76. 4,5-dimethyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)quinolin-2(1H)-one
- 77. 4-methyl-7-morpholino-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)quinolin-2(1H)-one
- 78. 4,8-dimethyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)-1,7-naphthyridin-2(1H)-one
- 79. 6-chloro-4-methyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)-1,7-naphthyridin-2(1H)-one′
- 80. 7-chloro-4-methyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)quinolin-2(1H)-one
- 81. 4,6-dimethyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)-1,7-naphthyridin-2(1H)-one
- 82. 4-methyl-7-(4-methylpiperazin-1-yl)-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)quinolin-2(1H)-one
- 83. 7-fluoro-4-methyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)quinolin-2(1H)-one
- 84. 4,7-dimethyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)-1,8-naphthyridin-2(1H)-one
- 85. 4-methyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)-1,6-naphthyridin-2(1H)-one
- 86. 4-methyl-7-morpholino-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)-1,8-naphthyridin-2(1H)-one
- 87. 7-(2-methoxyethoxy)-4-methyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)-1,8-naphthyridin-2(1H)-one
- or a pharmaceutically acceptable salt thereof or a pharmaceutically acceptable regioisomer thereof.
85 more elements
A novel bicyclic regioisomer compound selected from
- (R)-5-(5-(4-methoxyphenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- (S)-5-(5-(4-methoxyphenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- (R)-5-(5-(4-chlorophenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- (S)-5-(5-(4-chlorophenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- (R)-4-methyl-5-(1-propionyl-5-(thiophen-3-yl)-4,5-dihydro-1H-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
- (S)-4-methyl-5-(1-propionyl-5-(thiophen-3-yl)-4,5-dihydro-1H-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
- (R)-4-methyl-5-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
- (S)-4-methyl-5-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
- (R)-4-methyl-5-(5-(6-methylpyridin-3-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
- (S)-4-methyl-5-(5-(6-methylpyridin-3-yl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)thieno[2,3-b]pyridin-6(7H)-one
- (R)-4-methyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)quinolin-2(1H)-one
- (S)-4-methyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)quinolin-2(1H)-one
- (R)-5-(5-(2-fluoro-4-methylphenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- (S)-5-(5-(2-fluoro-4-methylphenyl)-1-propionyl-4,5-dihydro-1H-pyrazol-3-yl)-4-methylthieno[2,3-b]pyridin-6(7H)-one
- (R)-4-methyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)-1,7-naphthyridin-2(1H)-one
- (S)-4-methyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)-1,7-naphthyridin-2(1H)-one
- (R)-4,8-dimethyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)-1,7-naphthyridin-2(1H)-one
- (S)-4,8-dimethyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)-1,7-naphthyridin-2(1H)-one
- (R)-7-chloro-4-methyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)quinolin-2(1H)-one
- (S)-7-chloro-4-methyl-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)quinolin-2(1H)-one
- (R)-4-methyl-7-(4-methylpiperazin-1-yl)-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)quinolin-2(1H)-one
- (S)-4-methyl-7-(4-methylpiperazin-1-yl)-3-(1-propionyl-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-3-yl)quinolin-2(1H)-one.
19 more elements
Dependencies are inferred from the claim text.