JP2014533745A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2014533745A5 JP2014533745A5 JP2014544018A JP2014544018A JP2014533745A5 JP 2014533745 A5 JP2014533745 A5 JP 2014533745A5 JP 2014544018 A JP2014544018 A JP 2014544018A JP 2014544018 A JP2014544018 A JP 2014544018A JP 2014533745 A5 JP2014533745 A5 JP 2014533745A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- phenyl
- methyl
- dihydro
- pyrazol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 —C (O) OH Chemical group 0.000 claims description 105
- 125000000217 alkyl group Chemical group 0.000 claims description 103
- 150000003839 salts Chemical class 0.000 claims description 50
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 36
- 125000005843 halogen group Chemical group 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 150000001875 compounds Chemical class 0.000 claims description 34
- 125000000623 heterocyclic group Chemical group 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 9
- 125000002950 monocyclic group Chemical group 0.000 claims description 9
- 102000012199 E3 ubiquitin-protein ligase Mdm2 Human genes 0.000 claims description 8
- 108050002772 E3 ubiquitin-protein ligase Mdm2 Proteins 0.000 claims description 8
- 102000017274 MDM4 Human genes 0.000 claims description 8
- 108050005300 MDM4 Proteins 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 150000001721 carbon Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 6
- 208000035475 disorder Diseases 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 5
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 5
- AYJVXDFOPGRLNI-QHCPKHFHSA-N (4s)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-4-(4-chloro-2-methylphenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2[C@H](C=3C(=CC(Cl)=CC=3)C)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 AYJVXDFOPGRLNI-QHCPKHFHSA-N 0.000 claims description 4
- YDAUQLMQAVQZLU-UHFFFAOYSA-N 4-(4-chloro-3-fluorophenyl)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-2-(2,4-dimethoxypyrimidin-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C=C(F)C(Cl)=CC=3)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 YDAUQLMQAVQZLU-UHFFFAOYSA-N 0.000 claims description 4
- RQRGUXOSYRMAOC-DEOSSOPVSA-N 4-[(4s)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]benzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2[C@H](C=3C=CC(=CC=3)C#N)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 RQRGUXOSYRMAOC-DEOSSOPVSA-N 0.000 claims description 4
- RSRIVJZZBKJDKL-UHFFFAOYSA-N 4-[5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-2-(2,4-dimethoxypyrimidin-5-yl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]-3-fluorobenzonitrile Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C(=CC(=CC=3)C#N)F)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 RSRIVJZZBKJDKL-UHFFFAOYSA-N 0.000 claims description 4
- RQRGUXOSYRMAOC-UHFFFAOYSA-N 4-[5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]benzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(=CC=3)C#N)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 RQRGUXOSYRMAOC-UHFFFAOYSA-N 0.000 claims description 4
- AYJVXDFOPGRLNI-UHFFFAOYSA-N 5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-4-(4-chloro-2-methylphenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 AYJVXDFOPGRLNI-UHFFFAOYSA-N 0.000 claims description 4
- OIFYSZRTTNMVQD-UHFFFAOYSA-N 5-(5-chloro-2-oxo-1h-pyridin-3-yl)-4-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(NC=C(Cl)C=3)=O)C(=O)C2=N1 OIFYSZRTTNMVQD-UHFFFAOYSA-N 0.000 claims description 4
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 claims description 4
- IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- SJSSRJQZFGJFOX-QFIPXVFZSA-N (4s)-5-(5-chloro-2-oxo-1h-pyridin-3-yl)-4-(4-chlorophenyl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2[C@H](C=3C=CC(Cl)=CC=3)N(C=3C(NC=C(Cl)C=3)=O)C(=O)C2=N1 SJSSRJQZFGJFOX-QFIPXVFZSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 claims description 2
- YOXSWOWVTGKRRI-XYXHBKGXSA-N (2s)-2-[[4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]methyl]-n,n-dimethylpyrrolidine-1-carboxamide Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1C[C@@H]1CCCN1C(=O)N(C)C YOXSWOWVTGKRRI-XYXHBKGXSA-N 0.000 claims description 2
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 claims description 2
- SJSSRJQZFGJFOX-JOCHJYFZSA-N (4R)-5-(5-chloro-2-oxo-1H-pyridin-3-yl)-4-(4-chlorophenyl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-3-propan-2-yl-4H-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COc1nc(ncc1-n1nc2C(=O)N([C@@H](c2c1C(C)C)c1ccc(Cl)cc1)c1cc(Cl)c[nH]c1=O)N(C)C SJSSRJQZFGJFOX-JOCHJYFZSA-N 0.000 claims description 2
- ZPZFPPPXKLFRBC-MUUNZHRXSA-N (4r)-4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2[C@@H](C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 ZPZFPPPXKLFRBC-MUUNZHRXSA-N 0.000 claims description 2
- HMHZLUVFZNQBTE-JOCHJYFZSA-N (4r)-5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-(2-hydroxyethyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound N1([C@@H](C2=C(N(N=C2C1=O)CCO)C(C)C)C=1C(=CC(Cl)=CC=1)C)C1=CC=CC(Cl)=C1F HMHZLUVFZNQBTE-JOCHJYFZSA-N 0.000 claims description 2
- AYJVXDFOPGRLNI-HSZRJFAPSA-N (4r)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-4-(4-chloro-2-methylphenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2[C@@H](C=3C(=CC(Cl)=CC=3)C)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 AYJVXDFOPGRLNI-HSZRJFAPSA-N 0.000 claims description 2
- ZPZFPPPXKLFRBC-NDEPHWFRSA-N (4s)-4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2[C@H](C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 ZPZFPPPXKLFRBC-NDEPHWFRSA-N 0.000 claims description 2
- HMHZLUVFZNQBTE-QFIPXVFZSA-N (4s)-5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-(2-hydroxyethyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound N1([C@H](C2=C(N(N=C2C1=O)CCO)C(C)C)C=1C(=CC(Cl)=CC=1)C)C1=CC=CC(Cl)=C1F HMHZLUVFZNQBTE-QFIPXVFZSA-N 0.000 claims description 2
- YBMQYNARIZUNIO-HKBQPEDESA-N (4s)-5-[5-chloro-2-[2-(dimethylamino)ethoxy]phenyl]-4-(4-chloro-2-methylphenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2[C@H](C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)OCCN(C)C)C(=O)C2=N1 YBMQYNARIZUNIO-HKBQPEDESA-N 0.000 claims description 2
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 claims description 2
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 claims description 2
- APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 claims description 2
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 claims description 2
- DZWXCJZDTKKTNU-UHFFFAOYSA-N 2-[(1-acetyl-4-hydroxypiperidin-4-yl)methyl]-4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1CC1(O)CCN(C(C)=O)CC1 DZWXCJZDTKKTNU-UHFFFAOYSA-N 0.000 claims description 2
- QZPHTHGRGSOROE-UHFFFAOYSA-N 2-[(1-acetylpiperidin-4-yl)methyl]-4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1CC1CCN(C(C)=O)CC1 QZPHTHGRGSOROE-UHFFFAOYSA-N 0.000 claims description 2
- YBBQYZSRNHSUCI-UHFFFAOYSA-N 2-[2-(4-acetylpiperazin-1-yl)-2-oxoethyl]-4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1CC(=O)N1CCN(C(C)=O)CC1 YBBQYZSRNHSUCI-UHFFFAOYSA-N 0.000 claims description 2
- IQXKRKFNNIJHKM-UHFFFAOYSA-N 2-[2-[5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]ethyl]isoindole-1,3-dione Chemical compound O=C1C2=NN(CCN3C(C4=CC=CC=C4C3=O)=O)C(C(C)C)=C2C(C=2C(=CC(Cl)=CC=2)C)N1C1=CC=CC(Cl)=C1F IQXKRKFNNIJHKM-UHFFFAOYSA-N 0.000 claims description 2
- YEQFUJXHFVNFLD-UHFFFAOYSA-N 2-[5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]-n-methylacetamide Chemical compound C12=C(C(C)C)N(CC(=O)NC)N=C2C(=O)N(C=2C(=C(Cl)C=CC=2)F)C1C1=CC=C(Cl)C=C1C YEQFUJXHFVNFLD-UHFFFAOYSA-N 0.000 claims description 2
- ZJWOFSLLBIUKPW-UHFFFAOYSA-N 2-[5-(aminomethyl)-2-methoxyphenyl]-4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=C(CN)C=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 ZJWOFSLLBIUKPW-UHFFFAOYSA-N 0.000 claims description 2
- DLKYKILDEXFUBY-UHFFFAOYSA-N 2-[5-(aminomethyl)-2-methoxyphenyl]-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-4-(4-chloro-2-methylphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=C(CN)C=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 DLKYKILDEXFUBY-UHFFFAOYSA-N 0.000 claims description 2
- JZFAHAGJOFEDPR-XYXHBKGXSA-N 2-[[(2s)-1-acetylpyrrolidin-2-yl]methyl]-4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1C[C@@H]1CCCN1C(C)=O JZFAHAGJOFEDPR-XYXHBKGXSA-N 0.000 claims description 2
- KQFUYAPAPGFYMI-UHFFFAOYSA-N 2-[[4-(4-chlorophenyl)-5-(3,4-difluorophenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]methyl]benzonitrile Chemical compound CC(C)C1=C2C(C=3C=CC(Cl)=CC=3)N(C=3C=C(F)C(F)=CC=3)C(=O)C2=NN1CC1=CC=CC=C1C#N KQFUYAPAPGFYMI-UHFFFAOYSA-N 0.000 claims description 2
- AVTJOXSIUYDNFU-UHFFFAOYSA-N 2-benzyl-4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1CC1=CC=CC=C1 AVTJOXSIUYDNFU-UHFFFAOYSA-N 0.000 claims description 2
- WPSSCIDRUBTKAN-UHFFFAOYSA-N 2-benzyl-5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1CC1=CC=CC=C1 WPSSCIDRUBTKAN-UHFFFAOYSA-N 0.000 claims description 2
- 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- ALBXXUZUKJRRRW-UHFFFAOYSA-N 3-(1-aminopropan-2-yl)-5-(3-chloro-2-fluorophenyl)-4-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)CN)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=N1 ALBXXUZUKJRRRW-UHFFFAOYSA-N 0.000 claims description 2
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 claims description 2
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 claims description 2
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 claims description 2
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 claims description 2
- RCVRAHVEDDYMCE-UHFFFAOYSA-N 3-[4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]-4-methoxy-n,n-dimethylbenzamide Chemical compound COC1=CC=C(C(=O)N(C)C)C=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 RCVRAHVEDDYMCE-UHFFFAOYSA-N 0.000 claims description 2
- YVYATCZGDDDVSH-UHFFFAOYSA-N 3-[4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]-4-methoxy-n-(2-pyrrolidin-1-ylethyl)benzamide Chemical compound COC1=CC=C(C(=O)NCCN2CCCC2)C=C1N(C(=C12)C(C)C)N=C1C(=O)N(C=1C(=CC=C(Cl)C=1)C)C2C1=CC=C(Cl)C=C1C YVYATCZGDDDVSH-UHFFFAOYSA-N 0.000 claims description 2
- WKMPZXXAZAQLQZ-UHFFFAOYSA-N 3-[4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]-4-methoxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC=C(OC)C(N2C(=C3C(N(C(=O)C3=N2)C=2C(=CC=C(Cl)C=2)C)C=2C(=CC(Cl)=CC=2)C)C(C)C)=C1 WKMPZXXAZAQLQZ-UHFFFAOYSA-N 0.000 claims description 2
- RUFLPMXZYPSUOV-UHFFFAOYSA-N 3-[5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]benzonitrile Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1C1=CC=CC(C#N)=C1 RUFLPMXZYPSUOV-UHFFFAOYSA-N 0.000 claims description 2
- LFWZYTLMZYUEFQ-UHFFFAOYSA-N 3-[5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]propanenitrile Chemical compound O=C1C2=NN(CCC#N)C(C(C)C)=C2C(C=2C(=CC(Cl)=CC=2)C)N1C1=CC=CC(Cl)=C1F LFWZYTLMZYUEFQ-UHFFFAOYSA-N 0.000 claims description 2
- JGDWYYYDKDRIQZ-UHFFFAOYSA-N 3-[5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-4-(4-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]-4-methoxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC=C(OC)C(N2C(=C3C(N(C(=O)C3=N2)C2=CN(C)C(=O)C(Cl)=C2)C=2C(=CC(Cl)=CC=2)C)C(C)C)=C1 JGDWYYYDKDRIQZ-UHFFFAOYSA-N 0.000 claims description 2
- PMPUDZCQKFOGSX-UHFFFAOYSA-N 3-[5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-4-(4-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]-4-methoxybenzonitrile Chemical compound COC1=CC=C(C#N)C=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 PMPUDZCQKFOGSX-UHFFFAOYSA-N 0.000 claims description 2
- FTDQXIOMMPGVAT-UHFFFAOYSA-N 3-[5-(5-chloro-2-methylphenyl)-4-(4-cyanophenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]-4-methoxybenzonitrile Chemical compound COC1=CC=C(C#N)C=C1N1C(C(C)C)=C2C(C=3C=CC(=CC=3)C#N)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 FTDQXIOMMPGVAT-UHFFFAOYSA-N 0.000 claims description 2
- CRWXYYDAMBWTKL-UHFFFAOYSA-N 3-[5-(5-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4-[4-(trifluoromethyl)phenyl]-4h-pyrrolo[3,4-c]pyrazol-2-yl]-n,4-dimethylbenzamide Chemical compound CNC(=O)C1=CC=C(C)C(N2C(=C3C(N(C(=O)C3=N2)C=2C(=CC=C(Cl)C=2)C)C=2C=CC(=CC=2)C(F)(F)F)C(C)C)=C1 CRWXYYDAMBWTKL-UHFFFAOYSA-N 0.000 claims description 2
- BRWVYJDPNFVUHE-UHFFFAOYSA-N 3-chloro-5-[4-(4-chloro-2-methylphenyl)-2-(2-methoxyphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-5-yl]benzonitrile Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C=C(C=C(Cl)C=3)C#N)C(=O)C2=N1 BRWVYJDPNFVUHE-UHFFFAOYSA-N 0.000 claims description 2
- NFPQHOKNWHJKMC-UHFFFAOYSA-N 3-tert-butyl-5-(3-chloro-2-fluorophenyl)-4-(4-chlorophenyl)-2,4-dihydropyrrolo[3,4-c]pyrazol-6-one Chemical compound C12=C(C(C)(C)C)NN=C2C(=O)N(C=2C(=C(Cl)C=CC=2)F)C1C1=CC=C(Cl)C=C1 NFPQHOKNWHJKMC-UHFFFAOYSA-N 0.000 claims description 2
- KRKJHAZDWLVODZ-UHFFFAOYSA-N 4-(4-chloro-2-fluorophenyl)-5-(5-chloro-1-methyl-2-oxopyridin-3-yl)-2-(2,4-dimethoxypyrimidin-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)F)N(C=3C(N(C)C=C(Cl)C=3)=O)C(=O)C2=N1 KRKJHAZDWLVODZ-UHFFFAOYSA-N 0.000 claims description 2
- RIGFJBPAOUYYDK-UHFFFAOYSA-N 4-(4-chloro-2-fluorophenyl)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-2-(2,4-dimethoxypyrimidin-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)F)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 RIGFJBPAOUYYDK-UHFFFAOYSA-N 0.000 claims description 2
- LQFQEWGXGDBOGP-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(2-chloropyridin-4-yl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C=C(Cl)N=CC=3)C(=O)C2=N1 LQFQEWGXGDBOGP-UHFFFAOYSA-N 0.000 claims description 2
- GNUPSFNBJBWYRB-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-(1-methylpiperidin-4-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1C1CCN(C)CC1 GNUPSFNBJBWYRB-UHFFFAOYSA-N 0.000 claims description 2
- HWOBQJWTOBDSQY-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-(2,3-dihydroxypropyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound O=C1C2=NN(CC(O)CO)C(C(C)C)=C2C(C=2C(=CC(Cl)=CC=2)C)N1C1=CC(Cl)=CC=C1C HWOBQJWTOBDSQY-UHFFFAOYSA-N 0.000 claims description 2
- FMTUQXWHYUZQKX-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 FMTUQXWHYUZQKX-UHFFFAOYSA-N 0.000 claims description 2
- VWMHDGDJQMBFHU-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-(2-methoxyethyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound C12=C(C(C)C)N(CCOC)N=C2C(=O)N(C=2C(=CC=C(Cl)C=2)C)C1C1=CC=C(Cl)C=C1C VWMHDGDJQMBFHU-UHFFFAOYSA-N 0.000 claims description 2
- ZPZFPPPXKLFRBC-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 ZPZFPPPXKLFRBC-UHFFFAOYSA-N 0.000 claims description 2
- MIGFPEUHNSPEGD-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-(4-methoxypyridin-3-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=NC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 MIGFPEUHNSPEGD-UHFFFAOYSA-N 0.000 claims description 2
- MVJPAODGJWVCNG-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-(4-methylpiperazine-1-carbonyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1C(=O)N1CCN(C)CC1 MVJPAODGJWVCNG-UHFFFAOYSA-N 0.000 claims description 2
- BSYBXKOGLZBSHD-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-(oxiran-2-ylmethyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1CC1CO1 BSYBXKOGLZBSHD-UHFFFAOYSA-N 0.000 claims description 2
- KZKVSNXVFALSMC-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-(oxolan-2-ylmethyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1CC1CCCO1 KZKVSNXVFALSMC-UHFFFAOYSA-N 0.000 claims description 2
- IRWCMXNZTJROFT-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-[2-(2-oxopyrrolidin-1-yl)ethyl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1CCN1CCCC1=O IRWCMXNZTJROFT-UHFFFAOYSA-N 0.000 claims description 2
- IIZXQQZRRXYLSE-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-[2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1CC(=O)N1CCC(O)CC1 IIZXQQZRRXYLSE-UHFFFAOYSA-N 0.000 claims description 2
- UNZCOOAPYFTFKR-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-[2-(4-methylpiperazin-1-yl)ethyl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1CCN1CCN(C)CC1 UNZCOOAPYFTFKR-UHFFFAOYSA-N 0.000 claims description 2
- DBEMYIHLOZGDDF-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-[2-oxo-2-(3-oxopiperazin-1-yl)ethyl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1CC(=O)N1CCNC(=O)C1 DBEMYIHLOZGDDF-UHFFFAOYSA-N 0.000 claims description 2
- PSCSHVNMQAGNHC-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-3-propan-2-yl-2-(pyridin-2-ylmethyl)-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1CC1=CC=CC=N1 PSCSHVNMQAGNHC-UHFFFAOYSA-N 0.000 claims description 2
- YDPLGSFJBCHSDW-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-n-methyl-6-oxo-n-phenyl-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazole-2-carboxamide Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1C(=O)N(C)C1=CC=CC=C1 YDPLGSFJBCHSDW-UHFFFAOYSA-N 0.000 claims description 2
- DQKSQGUSULGQMU-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloropyridin-3-yl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C=C(Cl)C=NC=3)C(=O)C2=N1 DQKSQGUSULGQMU-UHFFFAOYSA-N 0.000 claims description 2
- RNZZSMCPSZIPLM-UHFFFAOYSA-N 4-(4-chloro-3-fluorophenyl)-5-(5-chloro-1-methyl-2-oxopyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=C(F)C(Cl)=CC=3)N(C=3C(N(C)C=C(Cl)C=3)=O)C(=O)C2=N1 RNZZSMCPSZIPLM-UHFFFAOYSA-N 0.000 claims description 2
- SPSDWBLEDCVGLA-UHFFFAOYSA-N 4-(4-chloro-3-fluorophenyl)-5-(5-chloro-2-oxo-1h-pyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=C(F)C(Cl)=CC=3)N(C=3C(NC=C(Cl)C=3)=O)C(=O)C2=N1 SPSDWBLEDCVGLA-UHFFFAOYSA-N 0.000 claims description 2
- OZTFXLSOURVIGT-UHFFFAOYSA-N 4-(4-chloro-3-fluorophenyl)-5-(5-chloro-6-oxo-1h-pyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=C(F)C(Cl)=CC=3)N(C=3C=C(Cl)C(=O)NC=3)C(=O)C2=N1 OZTFXLSOURVIGT-UHFFFAOYSA-N 0.000 claims description 2
- BQVXYVMHLPJQST-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-5-(1,5-dimethyl-2-oxopyridin-3-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(N(C)C=C(C)C=3)=O)C(=O)C2=N1 BQVXYVMHLPJQST-UHFFFAOYSA-N 0.000 claims description 2
- IKDAKUWICQIDSR-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-5-(1,5-dimethyl-2-oxopyridin-3-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(N(C)C=C(C)C=3)=O)C(=O)C2=N1 IKDAKUWICQIDSR-UHFFFAOYSA-N 0.000 claims description 2
- RZBALPLOLRLLGL-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-(3,4-difluorophenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C=C(F)C(F)=CC=3)C(=O)C2=N1 RZBALPLOLRLLGL-UHFFFAOYSA-N 0.000 claims description 2
- LXVKCNFEVHJFNO-UHFFFAOYSA-N 4-(4-chlorophenyl)-5-[5-chloro-2-(2h-tetrazol-5-ylmethoxy)phenyl]-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(=CC=C(Cl)C=3)OCC3=NNN=N3)C(=O)C2=N1 LXVKCNFEVHJFNO-UHFFFAOYSA-N 0.000 claims description 2
- RQRGUXOSYRMAOC-XMMPIXPASA-N 4-[(4r)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]benzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2[C@@H](C=3C=CC(=CC=3)C#N)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 RQRGUXOSYRMAOC-XMMPIXPASA-N 0.000 claims description 2
- VFMRTUQQYDQOGC-HSZRJFAPSA-N 4-[(4r)-5-(5-chloro-2-oxo-1h-pyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]benzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2[C@@H](C=3C=CC(=CC=3)C#N)N(C=3C(NC=C(Cl)C=3)=O)C(=O)C2=N1 VFMRTUQQYDQOGC-HSZRJFAPSA-N 0.000 claims description 2
- VFMRTUQQYDQOGC-QHCPKHFHSA-N 4-[(4s)-5-(5-chloro-2-oxo-1h-pyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]benzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2[C@H](C=3C=CC(=CC=3)C#N)N(C=3C(NC=C(Cl)C=3)=O)C(=O)C2=N1 VFMRTUQQYDQOGC-QHCPKHFHSA-N 0.000 claims description 2
- YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 claims description 2
- LXJBEGXWXSMNHG-UHFFFAOYSA-N 4-[4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]-5-methoxypyridine-2-carbonitrile Chemical compound COC1=CN=C(C#N)C=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 LXJBEGXWXSMNHG-UHFFFAOYSA-N 0.000 claims description 2
- VCGVUTSFODIAFH-UHFFFAOYSA-N 4-[5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]-3-methylbenzonitrile Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1C1=CC=C(C#N)C=C1C VCGVUTSFODIAFH-UHFFFAOYSA-N 0.000 claims description 2
- PHONKNJXSTWJFY-UHFFFAOYSA-N 4-[5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]benzamide Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1C1=CC=C(C(N)=O)C=C1 PHONKNJXSTWJFY-UHFFFAOYSA-N 0.000 claims description 2
- ZNNIQRHOWSRDID-UHFFFAOYSA-N 4-[5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]benzonitrile Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1C1=CC=C(C#N)C=C1 ZNNIQRHOWSRDID-UHFFFAOYSA-N 0.000 claims description 2
- UZPGACSHACEKSI-UHFFFAOYSA-N 4-[5-(5-chloro-1-methyl-2-oxopyridin-3-yl)-2-(2,4-dimethoxypyrimidin-5-yl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]-2-fluorobenzonitrile Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C=C(F)C(C#N)=CC=3)N(C=3C(N(C)C=C(Cl)C=3)=O)C(=O)C2=N1 UZPGACSHACEKSI-UHFFFAOYSA-N 0.000 claims description 2
- QCBBDTOZLNYFGQ-UHFFFAOYSA-N 4-[5-(5-chloro-1-methyl-2-oxopyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]-2-fluorobenzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=C(F)C(C#N)=CC=3)N(C=3C(N(C)C=C(Cl)C=3)=O)C(=O)C2=N1 QCBBDTOZLNYFGQ-UHFFFAOYSA-N 0.000 claims description 2
- QFACTYPVKZDPLP-UHFFFAOYSA-N 4-[5-(5-chloro-1-methyl-2-oxopyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]benzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(=CC=3)C#N)N(C=3C(N(C)C=C(Cl)C=3)=O)C(=O)C2=N1 QFACTYPVKZDPLP-UHFFFAOYSA-N 0.000 claims description 2
- IOZOLCKZPLYLKQ-UHFFFAOYSA-N 4-[5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-2-(2,4-dimethoxypyrimidin-5-yl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]benzonitrile Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(=CC=3)C#N)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 IOZOLCKZPLYLKQ-UHFFFAOYSA-N 0.000 claims description 2
- AFQNRQRMSMOQQO-UHFFFAOYSA-N 4-[5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-2-(5-cyano-2-methoxyphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]-3-methylbenzonitrile Chemical compound COC1=CC=C(C#N)C=C1N1C(C(C)C)=C2C(C=3C(=CC(=CC=3)C#N)C)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 AFQNRQRMSMOQQO-UHFFFAOYSA-N 0.000 claims description 2
- OPHHVKUMEIMJFY-UHFFFAOYSA-N 4-[5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]-2-fluorobenzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=C(F)C(C#N)=CC=3)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 OPHHVKUMEIMJFY-UHFFFAOYSA-N 0.000 claims description 2
- HVRFIYKARUWFKC-UHFFFAOYSA-N 4-[5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-4-(4-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]-5-methoxypyridine-2-carbonitrile Chemical compound COC1=CN=C(C#N)C=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 HVRFIYKARUWFKC-UHFFFAOYSA-N 0.000 claims description 2
- UNRJWGHNUAOTHP-UHFFFAOYSA-N 4-[5-(5-chloro-2-methylphenyl)-2-(5-cyano-2-methoxyphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]-3-methylbenzonitrile Chemical compound COC1=CC=C(C#N)C=C1N1C(C(C)C)=C2C(C=3C(=CC(=CC=3)C#N)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 UNRJWGHNUAOTHP-UHFFFAOYSA-N 0.000 claims description 2
- BBYSZUMVPYJQOO-UHFFFAOYSA-N 4-[5-(5-chloro-2-oxo-1h-pyridin-3-yl)-2-(2,4-dimethoxypyrimidin-5-yl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]benzonitrile Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(=CC=3)C#N)N(C=3C(NC=C(Cl)C=3)=O)C(=O)C2=N1 BBYSZUMVPYJQOO-UHFFFAOYSA-N 0.000 claims description 2
- UBDXCWOLGCQOJC-UHFFFAOYSA-N 4-[5-(5-chloro-2-oxo-1h-pyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]-2-fluorobenzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=C(F)C(C#N)=CC=3)N(C=3C(NC=C(Cl)C=3)=O)C(=O)C2=N1 UBDXCWOLGCQOJC-UHFFFAOYSA-N 0.000 claims description 2
- VFMRTUQQYDQOGC-UHFFFAOYSA-N 4-[5-(5-chloro-2-oxo-1h-pyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]benzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(=CC=3)C#N)N(C=3C(NC=C(Cl)C=3)=O)C(=O)C2=N1 VFMRTUQQYDQOGC-UHFFFAOYSA-N 0.000 claims description 2
- FYNWTBPRYFLVCU-UHFFFAOYSA-N 4-[5-(5-chloro-2-oxo-1h-pyridin-3-yl)-2-[4-methoxy-2-(methylamino)pyrimidin-5-yl]-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]benzonitrile Chemical compound COC1=NC(NC)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(=CC=3)C#N)N(C=3C(NC=C(Cl)C=3)=O)C(=O)C2=N1 FYNWTBPRYFLVCU-UHFFFAOYSA-N 0.000 claims description 2
- SAENTOWOUZIBGI-UHFFFAOYSA-N 4-[5-(5-chloro-6-oxo-1h-pyridin-3-yl)-2-(2,4-dimethoxypyrimidin-5-yl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]benzonitrile Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(=CC=3)C#N)N(C=3C=C(Cl)C(=O)NC=3)C(=O)C2=N1 SAENTOWOUZIBGI-UHFFFAOYSA-N 0.000 claims description 2
- NIQDSHQHXGATPM-UHFFFAOYSA-N 4-[5-(5-chloro-6-oxo-1h-pyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]-2-fluorobenzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=C(F)C(C#N)=CC=3)N(C=3C=C(Cl)C(=O)NC=3)C(=O)C2=N1 NIQDSHQHXGATPM-UHFFFAOYSA-N 0.000 claims description 2
- HZMWETDTDRJJRB-UHFFFAOYSA-N 4-[5-(5-chloro-6-oxo-1h-pyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]benzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(=CC=3)C#N)N(C=3C=C(Cl)C(=O)NC=3)C(=O)C2=N1 HZMWETDTDRJJRB-UHFFFAOYSA-N 0.000 claims description 2
- ATMKSZMRLDHODZ-UHFFFAOYSA-N 4-[5-(5-chloro-6-oxo-1h-pyridin-3-yl)-2-[4-methoxy-2-(methylamino)pyrimidin-5-yl]-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]benzonitrile Chemical compound COC1=NC(NC)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(=CC=3)C#N)N(C=3C=C(Cl)C(=O)NC=3)C(=O)C2=N1 ATMKSZMRLDHODZ-UHFFFAOYSA-N 0.000 claims description 2
- CILSJFJSUMUUSU-UHFFFAOYSA-N 4-[[4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]methyl]-4-hydroxy-n-propan-2-ylpiperidine-1-carboxamide Chemical compound C1CN(C(=O)NC(C)C)CCC1(O)CN1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 CILSJFJSUMUUSU-UHFFFAOYSA-N 0.000 claims description 2
- PSBHMQFAIJWIBA-UHFFFAOYSA-N 4-[[4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]methyl]-n-propan-2-ylpiperidine-1-carboxamide Chemical compound C1CN(C(=O)NC(C)C)CCC1CN1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 PSBHMQFAIJWIBA-UHFFFAOYSA-N 0.000 claims description 2
- ZFDXOFADVLDFOH-UHFFFAOYSA-N 4-[[5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]methyl]-1h-quinolin-2-one Chemical compound O=C1C2=NN(CC=3C4=CC=CC=C4NC(=O)C=3)C(C(C)C)=C2C(C=2C(=CC(Cl)=CC=2)C)N1C1=CC=CC(Cl)=C1F ZFDXOFADVLDFOH-UHFFFAOYSA-N 0.000 claims description 2
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 claims description 2
- DDNUWIGTTWWNTD-UHFFFAOYSA-N 5-(2-chloro-5-methoxypyridin-4-yl)-4-(4-chloro-2-methylphenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CN=C(Cl)C=3)OC)C(=O)C2=N1 DDNUWIGTTWWNTD-UHFFFAOYSA-N 0.000 claims description 2
- WOGRNEPYKNYRAY-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(2,4-dichlorophenyl)-2-(2-hydroxyethyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound O=C1C2=NN(CCO)C(C(C)C)=C2C(C=2C(=CC(Cl)=CC=2)Cl)N1C1=CC=CC(Cl)=C1F WOGRNEPYKNYRAY-UHFFFAOYSA-N 0.000 claims description 2
- FOESSPNKSMUVQU-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(3,4-difluorophenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C=C(F)C(F)=CC=3)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=N1 FOESSPNKSMUVQU-UHFFFAOYSA-N 0.000 claims description 2
- QVUQZJZBURHSLW-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(3,4-difluorophenyl)-2-(3-methylbutyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound C12=C(C(C)C)N(CCC(C)C)N=C2C(=O)N(C=2C(=C(Cl)C=CC=2)F)C1C1=CC=C(F)C(F)=C1 QVUQZJZBURHSLW-UHFFFAOYSA-N 0.000 claims description 2
- JFYYWZGFLOOIDT-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-(2,4-difluorophenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1C1=CC=C(F)C=C1F JFYYWZGFLOOIDT-UHFFFAOYSA-N 0.000 claims description 2
- LHXUGFRDBNVUIT-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-(2-chlorophenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1C1=CC=CC=C1Cl LHXUGFRDBNVUIT-UHFFFAOYSA-N 0.000 claims description 2
- GPSWTWVTPSINSB-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-(2-fluorophenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1C1=CC=CC=C1F GPSWTWVTPSINSB-UHFFFAOYSA-N 0.000 claims description 2
- WMPSGRIFZXRFEB-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-(2-hydroxy-2-methylpropyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound O=C1C2=NN(CC(C)(C)O)C(C(C)C)=C2C(C=2C(=CC(Cl)=CC=2)C)N1C1=CC=CC(Cl)=C1F WMPSGRIFZXRFEB-UHFFFAOYSA-N 0.000 claims description 2
- HMHZLUVFZNQBTE-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-(2-hydroxyethyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound O=C1C2=NN(CCO)C(C(C)C)=C2C(C=2C(=CC(Cl)=CC=2)C)N1C1=CC=CC(Cl)=C1F HMHZLUVFZNQBTE-UHFFFAOYSA-N 0.000 claims description 2
- PUYWZQFYSPULBD-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-(2-methoxyethyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound C12=C(C(C)C)N(CCOC)N=C2C(=O)N(C=2C(=C(Cl)C=CC=2)F)C1C1=CC=C(Cl)C=C1C PUYWZQFYSPULBD-UHFFFAOYSA-N 0.000 claims description 2
- UPUQTACBEBMRIU-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=N1 UPUQTACBEBMRIU-UHFFFAOYSA-N 0.000 claims description 2
- BUOAGPCDZLSTGG-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-(2-phenylethyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1CCC1=CC=CC=C1 BUOAGPCDZLSTGG-UHFFFAOYSA-N 0.000 claims description 2
- WHEPFCCOZIXFLC-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-(3-hydroxypropyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound O=C1C2=NN(CCCO)C(C(C)C)=C2C(C=2C(=CC(Cl)=CC=2)C)N1C1=CC=CC(Cl)=C1F WHEPFCCOZIXFLC-UHFFFAOYSA-N 0.000 claims description 2
- AEXRLDGUEODSCQ-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-(3-methylbut-2-enyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound O=C1C2=NN(CC=C(C)C)C(C(C)C)=C2C(C=2C(=CC(Cl)=CC=2)C)N1C1=CC=CC(Cl)=C1F AEXRLDGUEODSCQ-UHFFFAOYSA-N 0.000 claims description 2
- XJYPRHQKEZFLER-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-(3-methylbutyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound C12=C(C(C)C)N(CCC(C)C)N=C2C(=O)N(C=2C(=C(Cl)C=CC=2)F)C1C1=CC=C(Cl)C=C1C XJYPRHQKEZFLER-UHFFFAOYSA-N 0.000 claims description 2
- UVNYTNSLCVSVTL-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-(4-chlorophenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1C1=CC=C(Cl)C=C1 UVNYTNSLCVSVTL-UHFFFAOYSA-N 0.000 claims description 2
- JBEQAJPKJMSHFR-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-(4-hydroxycyclohexyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1C1CCC(O)CC1 JBEQAJPKJMSHFR-UHFFFAOYSA-N 0.000 claims description 2
- OBXCBYXXTYVDSI-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-(cyclohexylmethyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1CC1CCCCC1 OBXCBYXXTYVDSI-UHFFFAOYSA-N 0.000 claims description 2
- NOXKBKWUFKOLHB-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-(oxan-4-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1C1CCOCC1 NOXKBKWUFKOLHB-UHFFFAOYSA-N 0.000 claims description 2
- GKYIFSPUMLSNRN-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-[(2-methyl-1,3-thiazol-4-yl)methyl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1CC1=CSC(C)=N1 GKYIFSPUMLSNRN-UHFFFAOYSA-N 0.000 claims description 2
- DGWXQHKAOFMVFK-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-[2-(1h-imidazol-5-yl)ethyl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1CCC1=CN=CN1 DGWXQHKAOFMVFK-UHFFFAOYSA-N 0.000 claims description 2
- GAIFQWCUGUSUIE-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-[2-(1h-indol-3-yl)ethyl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound O=C1C2=NN(CCC=3C4=CC=CC=C4NC=3)C(C(C)C)=C2C(C=2C(=CC(Cl)=CC=2)C)N1C1=CC=CC(Cl)=C1F GAIFQWCUGUSUIE-UHFFFAOYSA-N 0.000 claims description 2
- PKOHPVVUDUZROD-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-[2-(dimethylamino)ethyl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound O=C1C2=NN(CCN(C)C)C(C(C)C)=C2C(C=2C(=CC(Cl)=CC=2)C)N1C1=CC=CC(Cl)=C1F PKOHPVVUDUZROD-UHFFFAOYSA-N 0.000 claims description 2
- QCXFDHNMOCWGOO-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-cyclopropyl-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1C1CC1 QCXFDHNMOCWGOO-UHFFFAOYSA-N 0.000 claims description 2
- KVQBAECCFMFALF-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-3-cyclobutyl-2-(2-hydroxyethyl)-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC1=CC(Cl)=CC=C1C1C2=C(C3CCC3)N(CCO)N=C2C(=O)N1C1=CC=CC(Cl)=C1F KVQBAECCFMFALF-UHFFFAOYSA-N 0.000 claims description 2
- QRUJCXIVKXOPIJ-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-3-cyclopropyl-2-(2-hydroxyethyl)-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC1=CC(Cl)=CC=C1C1C2=C(C3CC3)N(CCO)N=C2C(=O)N1C1=CC=CC(Cl)=C1F QRUJCXIVKXOPIJ-UHFFFAOYSA-N 0.000 claims description 2
- RSKWVWWNOULHKJ-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-3-cyclopropyl-2-(2-methoxyphenyl)-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C2CC2)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=N1 RSKWVWWNOULHKJ-UHFFFAOYSA-N 0.000 claims description 2
- GUUCXMISBBUFFH-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-3-propan-2-yl-2-(1,3-thiazol-4-ylmethyl)-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1CC1=CSC=N1 GUUCXMISBBUFFH-UHFFFAOYSA-N 0.000 claims description 2
- HWSUWQWVEIWWQQ-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-3-propan-2-yl-2-(2-pyridin-2-ylethyl)-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1CCC1=CC=CC=N1 HWSUWQWVEIWWQQ-UHFFFAOYSA-N 0.000 claims description 2
- OPXLDTUTDCQLID-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-3-propan-2-yl-2-(pyridin-2-ylmethyl)-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1CC1=CC=CC=N1 OPXLDTUTDCQLID-UHFFFAOYSA-N 0.000 claims description 2
- TYWSIURVMYDJIY-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-3-propan-2-yl-2-(pyridin-3-ylmethyl)-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1CC1=CC=CN=C1 TYWSIURVMYDJIY-UHFFFAOYSA-N 0.000 claims description 2
- WZEXNVKJEUXBLY-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-3-propan-2-yl-2-(pyridin-4-ylmethyl)-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1CC1=CC=NC=C1 WZEXNVKJEUXBLY-UHFFFAOYSA-N 0.000 claims description 2
- PKTREAKCQJCNCB-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-3-fluorophenyl)-2-(2-hydroxyethyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound O=C1C2=NN(CCO)C(C(C)C)=C2C(C=2C=C(F)C(Cl)=CC=2)N1C1=CC=CC(Cl)=C1F PKTREAKCQJCNCB-UHFFFAOYSA-N 0.000 claims description 2
- ZYNISQAUMBGSTJ-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chlorophenyl)-2-(1h-imidazol-2-ylmethyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1CC1=NC=CN1 ZYNISQAUMBGSTJ-UHFFFAOYSA-N 0.000 claims description 2
- CJYUPDCUMHCMHU-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-3-[1-(dimethylamino)propan-2-yl]-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)CN(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=N1 CJYUPDCUMHCMHU-UHFFFAOYSA-N 0.000 claims description 2
- FXCJXJZTTZWVDL-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chlorophenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=N1 FXCJXJZTTZWVDL-UHFFFAOYSA-N 0.000 claims description 2
- HDAJQNMJDOETDO-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chlorophenyl)-2-(2-methoxyphenyl)-4-(2-morpholin-4-yl-2-oxoethyl)-3-propan-2-ylpyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(CC(=O)N3CCOCC3)(C=3C=CC(Cl)=CC=3)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=N1 HDAJQNMJDOETDO-UHFFFAOYSA-N 0.000 claims description 2
- URYVVMMWEFMDLZ-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chlorophenyl)-2-(4-methoxypyridin-3-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=NC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=N1 URYVVMMWEFMDLZ-UHFFFAOYSA-N 0.000 claims description 2
- HMYIFNWAXFJNOP-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chlorophenyl)-2-[(2,5-dimethylpyrazol-3-yl)methyl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1CC1=CC(C)=NN1C HMYIFNWAXFJNOP-UHFFFAOYSA-N 0.000 claims description 2
- KAKMQHCSBWFALW-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chlorophenyl)-2-[2-(3-ethyl-2-oxoimidazolidin-1-yl)ethyl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound O=C1N(CC)CCN1CCN1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=N1 KAKMQHCSBWFALW-UHFFFAOYSA-N 0.000 claims description 2
- BBYYJQOKOHLPCF-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chlorophenyl)-3-propan-2-yl-2-(1h-pyrazol-4-yl)-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1C=1C=NNC=1 BBYYJQOKOHLPCF-UHFFFAOYSA-N 0.000 claims description 2
- IDNGXAWKJBFVGN-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chlorophenyl)-3-propan-2-yl-2-(2h-tetrazol-5-ylmethyl)-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1CC=1N=NNN=1 IDNGXAWKJBFVGN-UHFFFAOYSA-N 0.000 claims description 2
- UTRRDMMZSZZPIB-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chlorophenyl)-3-propan-2-yl-2-pyridin-4-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1C1=CC=NC=C1 UTRRDMMZSZZPIB-UHFFFAOYSA-N 0.000 claims description 2
- NTMPRZKGDGPMFD-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-fluorophenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C=CC(F)=CC=3)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=N1 NTMPRZKGDGPMFD-UHFFFAOYSA-N 0.000 claims description 2
- XTRBDZDWKLQSPN-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-fluorophenyl)-2-(3-methylbutyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound C12=C(C(C)C)N(CCC(C)C)N=C2C(=O)N(C=2C(=C(Cl)C=CC=2)F)C1C1=CC=C(F)C=C1 XTRBDZDWKLQSPN-UHFFFAOYSA-N 0.000 claims description 2
- RPKYRYGQCTUGBZ-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-[4-chloro-2-(2-methoxyethoxymethyl)phenyl]-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COCCOCC1=CC(Cl)=CC=C1C1C2=C(C(C)C)N(C=3C(=CC=CC=3)OC)N=C2C(=O)N1C1=CC=CC(Cl)=C1F RPKYRYGQCTUGBZ-UHFFFAOYSA-N 0.000 claims description 2
- KVHUHKCJHOHTMI-UHFFFAOYSA-N 5-(3-chloro-4-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-(2-hydroxyethyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound O=C1C2=NN(CCO)C(C(C)C)=C2C(C=2C(=CC(Cl)=CC=2)C)N1C1=CC=C(F)C(Cl)=C1 KVHUHKCJHOHTMI-UHFFFAOYSA-N 0.000 claims description 2
- DUNHLTCPPXISMB-UHFFFAOYSA-N 5-(3-chloro-4-fluorophenyl)-4-(4-chlorophenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C=C(Cl)C(F)=CC=3)C(=O)C2=N1 DUNHLTCPPXISMB-UHFFFAOYSA-N 0.000 claims description 2
- QWSVSMXQIURNKZ-UHFFFAOYSA-N 5-(3-chloro-4-fluorophenyl)-4-(4-chlorophenyl)-2-(2-methoxyphenyl)-4-methyl-3-propan-2-ylpyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C)(C=3C=CC(Cl)=CC=3)N(C=3C=C(Cl)C(F)=CC=3)C(=O)C2=N1 QWSVSMXQIURNKZ-UHFFFAOYSA-N 0.000 claims description 2
- ILSKQZCULNKRSM-UHFFFAOYSA-N 5-(3-chloro-4-fluorophenyl)-4-(4-chlorophenyl)-4-(2-hydroxy-3-pyrrolidin-1-ylpropyl)-2-(2-methoxyphenyl)-3-propan-2-ylpyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(CC(O)CN3CCCC3)(C=3C=CC(Cl)=CC=3)N(C=3C=C(Cl)C(F)=CC=3)C(=O)C2=N1 ILSKQZCULNKRSM-UHFFFAOYSA-N 0.000 claims description 2
- QVEOEHNRKHXHRY-UHFFFAOYSA-N 5-(3-chloro-4-fluorophenyl)-4-(5-chloropyridin-2-yl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3N=CC(Cl)=CC=3)N(C=3C=C(Cl)C(F)=CC=3)C(=O)C2=N1 QVEOEHNRKHXHRY-UHFFFAOYSA-N 0.000 claims description 2
- IBXWQDNBFLGQOV-UHFFFAOYSA-N 5-(5-chloro-1-ethyl-6-oxopyridin-3-yl)-4-(4-chloro-2-methylphenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound C1=C(Cl)C(=O)N(CC)C=C1N1C(=O)C2=NN(C=3C(=CC=CC=3)OC)C(C(C)C)=C2C1C1=CC=C(Cl)C=C1C IBXWQDNBFLGQOV-UHFFFAOYSA-N 0.000 claims description 2
- FZVOKZVDSZAECZ-UHFFFAOYSA-N 5-(5-chloro-1-ethyl-6-oxopyridin-3-yl)-4-(4-chlorophenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound C1=C(Cl)C(=O)N(CC)C=C1N1C(=O)C2=NN(C=3C(=CC=CC=3)OC)C(C(C)C)=C2C1C1=CC=C(Cl)C=C1 FZVOKZVDSZAECZ-UHFFFAOYSA-N 0.000 claims description 2
- ZUSGXOJEHMHMML-UHFFFAOYSA-N 5-(5-chloro-1-methyl-2-oxopyridin-3-yl)-4-(4-chloro-2-methylphenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(N(C)C=C(Cl)C=3)=O)C(=O)C2=N1 ZUSGXOJEHMHMML-UHFFFAOYSA-N 0.000 claims description 2
- PANLTUPSUITZKH-UHFFFAOYSA-N 5-(5-chloro-1-methyl-2-oxopyridin-3-yl)-4-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(N(C)C=C(Cl)C=3)=O)C(=O)C2=N1 PANLTUPSUITZKH-UHFFFAOYSA-N 0.000 claims description 2
- OWFJNPMLQSQXJK-UHFFFAOYSA-N 5-(5-chloro-1-methyl-2-oxopyridin-3-yl)-4-(4-chlorophenyl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(N(C)C=C(Cl)C=3)=O)C(=O)C2=N1 OWFJNPMLQSQXJK-UHFFFAOYSA-N 0.000 claims description 2
- LJQVUKZVORGQEL-UHFFFAOYSA-N 5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-4-(4-chloro-2-methylphenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 LJQVUKZVORGQEL-UHFFFAOYSA-N 0.000 claims description 2
- RQXAUHYKZHXCFO-UHFFFAOYSA-N 5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-4-(4-chlorophenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 RQXAUHYKZHXCFO-UHFFFAOYSA-N 0.000 claims description 2
- UZHVOERTZALWJN-UHFFFAOYSA-N 5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-4-(4-chlorophenyl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(N(C)C)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 UZHVOERTZALWJN-UHFFFAOYSA-N 0.000 claims description 2
- JFMPRDLNBMLXEF-UHFFFAOYSA-N 5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-4-(4-chlorophenyl)-2-[4-methoxy-2-(methylamino)pyrimidin-5-yl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(NC)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 JFMPRDLNBMLXEF-UHFFFAOYSA-N 0.000 claims description 2
- VJIXYTFQQQTOIG-UHFFFAOYSA-N 5-(5-chloro-2,4-difluorophenyl)-4-(4-chloro-2-methylphenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC(F)=C(Cl)C=3)F)C(=O)C2=N1 VJIXYTFQQQTOIG-UHFFFAOYSA-N 0.000 claims description 2
- LQBNBLSVDLZZMI-UHFFFAOYSA-N 5-(5-chloro-2-methylphenyl)-4-(5-chloropyridin-2-yl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3N=CC(Cl)=CC=3)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 LQBNBLSVDLZZMI-UHFFFAOYSA-N 0.000 claims description 2
- LKJGYPXCEQDHSF-UHFFFAOYSA-N 5-(5-chloro-6-oxo-1h-pyridin-3-yl)-4-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C=C(Cl)C(=O)NC=3)C(=O)C2=N1 LKJGYPXCEQDHSF-UHFFFAOYSA-N 0.000 claims description 2
- YPYQBKQPNRSJLU-UHFFFAOYSA-N 5-[5-chloro-1-(2-hydroxyethyl)-6-oxopyridin-3-yl]-4-(4-chlorophenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C3=CN(CCO)C(=O)C(Cl)=C3)C(=O)C2=N1 YPYQBKQPNRSJLU-UHFFFAOYSA-N 0.000 claims description 2
- IFRLFSYFJZFISV-UHFFFAOYSA-N 5-[5-chloro-1-[2-(dimethylamino)ethyl]-6-oxopyridin-3-yl]-4-(4-chlorophenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C3=CN(CCN(C)C)C(=O)C(Cl)=C3)C(=O)C2=N1 IFRLFSYFJZFISV-UHFFFAOYSA-N 0.000 claims description 2
- YBMQYNARIZUNIO-UHFFFAOYSA-N 5-[5-chloro-2-[2-(dimethylamino)ethoxy]phenyl]-4-(4-chloro-2-methylphenyl)-2-(2-methoxyphenyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)OCCN(C)C)C(=O)C2=N1 YBMQYNARIZUNIO-UHFFFAOYSA-N 0.000 claims description 2
- ZYJZAJSSCZJWTL-UHFFFAOYSA-N 5-[5-chloro-2-[2-(dimethylamino)ethoxy]phenyl]-4-(4-chloro-2-methylphenyl)-2-ethyl-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound C12=C(C(C)C)N(CC)N=C2C(=O)N(C=2C(=CC=C(Cl)C=2)OCCN(C)C)C1C1=CC=C(Cl)C=C1C ZYJZAJSSCZJWTL-UHFFFAOYSA-N 0.000 claims description 2
- KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 claims description 2
- HAOXNUGBZDFVPB-UHFFFAOYSA-N 6-[4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]-1,3-dimethylpyrimidine-2,4-dione Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1C1=CC(=O)N(C)C(=O)N1C HAOXNUGBZDFVPB-UHFFFAOYSA-N 0.000 claims description 2
- VDJFQUDOTQDXAB-UHFFFAOYSA-N 7-[[5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4H-pyrrolo[3,4-c]pyrazol-2-yl]methyl]-5-oxo-4H-pyrazolo[1,5-a]pyrimidine-3-carbonitrile Chemical compound CC(C)c1c2C(N(C(=O)c2nn1Cc1cc(=O)[nH]c2c(cnn12)C#N)c1cccc(Cl)c1F)c1ccc(Cl)cc1C VDJFQUDOTQDXAB-UHFFFAOYSA-N 0.000 claims description 2
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 claims description 2
- GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 claims description 2
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 claims description 2
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- KACZQOKEFKFNDB-UHFFFAOYSA-N ethyl 1h-pyrazole-4-carboxylate Chemical compound CCOC(=O)C=1C=NNC=1 KACZQOKEFKFNDB-UHFFFAOYSA-N 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- UDHRMOWCYWTZJA-LWAJAQLZSA-N methyl (2s)-2-[[4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]methyl]pyrrolidine-1-carboxylate Chemical compound COC(=O)N1CCC[C@H]1CN1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 UDHRMOWCYWTZJA-LWAJAQLZSA-N 0.000 claims description 2
- OATMHJTYDZFHJL-UHFFFAOYSA-N methyl 3-[5-(3-chloro-4-fluorophenyl)-4-(4-chlorophenyl)-2-(2-methoxyphenyl)-6-oxo-3-propan-2-ylpyrrolo[3,4-c]pyrazol-4-yl]propanoate Chemical compound CC(C)C1=C2C(CCC(=O)OC)(C=3C=CC(Cl)=CC=3)N(C=3C=C(Cl)C(F)=CC=3)C(=O)C2=NN1C1=CC=CC=C1OC OATMHJTYDZFHJL-UHFFFAOYSA-N 0.000 claims description 2
- PYHGZMRCOVTXPO-UHFFFAOYSA-N n-[2-[5-(3-chloro-2-fluorophenyl)-4-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-6-oxo-4h-pyrrolo[3,4-c]pyrazol-3-yl]propyl]acetamide Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)CNC(C)=O)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=N1 PYHGZMRCOVTXPO-UHFFFAOYSA-N 0.000 claims description 2
- IMRHOXBGCDZUNF-UHFFFAOYSA-N n-[2-[5-(3-chloro-2-fluorophenyl)-4-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-6-oxo-4h-pyrrolo[3,4-c]pyrazol-3-yl]propyl]formamide Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)CNC=O)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=N1 IMRHOXBGCDZUNF-UHFFFAOYSA-N 0.000 claims description 2
- PAUGXEQSQVHHPG-UHFFFAOYSA-N n-[3-chloro-5-[4-(4-chloro-2-methylphenyl)-2-(2-methoxyphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-5-yl]phenyl]acetamide Chemical compound COC1=CC=CC=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C=C(NC(C)=O)C=C(Cl)C=3)C(=O)C2=N1 PAUGXEQSQVHHPG-UHFFFAOYSA-N 0.000 claims description 2
- WHEWAAXRLULZDS-UHFFFAOYSA-N n-[[3-[4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]-4-methoxyphenyl]methyl]acetamide Chemical compound COC1=CC=C(CNC(C)=O)C=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 WHEWAAXRLULZDS-UHFFFAOYSA-N 0.000 claims description 2
- POEYXKUAFFVQOZ-UHFFFAOYSA-N n-[[3-[4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]-4-methoxyphenyl]methyl]formamide Chemical compound COC1=CC=C(CNC=O)C=C1N1C(C(C)C)=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=N1 POEYXKUAFFVQOZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 claims description 2
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 claims description 2
- ODOZCWBAEOCSHE-UHFFFAOYSA-N tert-butyl 3-[4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-2-yl]pyrrolidine-1-carboxylate Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=CC=C(Cl)C=3)C)C(=O)C2=NN1C1CCN(C(=O)OC(C)(C)C)C1 ODOZCWBAEOCSHE-UHFFFAOYSA-N 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 20
- BIIFEKIGTUMZNZ-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-2-(1-methylpiperidin-4-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)C1=C2C(C=3C(=CC(Cl)=CC=3)C)N(C=3C(=C(Cl)C=CC=3)F)C(=O)C2=NN1C1CCN(C)CC1 BIIFEKIGTUMZNZ-UHFFFAOYSA-N 0.000 claims 1
- FRXDUXKRQHHRRK-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-4-(4-chloro-2-methylphenyl)-3-cyclopropyl-2-(3-methylbutyl)-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound CC(C)CCN1N=C2C(=O)N(C=3C(=C(Cl)C=CC=3)F)C(C=3C(=CC(Cl)=CC=3)C)C2=C1C1CC1 FRXDUXKRQHHRRK-UHFFFAOYSA-N 0.000 claims 1
- FWEMNIDYMWXHEJ-UHFFFAOYSA-N 5-(5-chloro-1-methyl-2-oxopyridin-3-yl)-4-(4-chlorophenyl)-2-[4-methoxy-2-(methylamino)pyrimidin-5-yl]-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(NC)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C=3C(N(C)C=C(Cl)C=3)=O)C(=O)C2=N1 FWEMNIDYMWXHEJ-UHFFFAOYSA-N 0.000 claims 1
- LIFXZKFYYIPQBT-UHFFFAOYSA-N 5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-4-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(Cl)=CC=3)N(C3=CN(C)C(=O)C(Cl)=C3)C(=O)C2=N1 LIFXZKFYYIPQBT-UHFFFAOYSA-N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 description 2
- 208000029742 colonic neoplasm Diseases 0.000 description 2
- GLJMWFSFNGOCDG-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-(2-hydroxyethyl)-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-6-one Chemical compound O=C1C2=NN(CCO)C(C(C)C)=C2C(C=2C(=CC(Cl)=CC=2)C)N1C1=CC(Cl)=CC=C1C GLJMWFSFNGOCDG-UHFFFAOYSA-N 0.000 description 1
- FFDKGWMMRQCCRD-UHFFFAOYSA-N 4-[5-(5-chloro-1-methyl-2-oxopyridin-3-yl)-2-(2,4-dimethoxypyrimidin-5-yl)-6-oxo-3-propan-2-yl-4h-pyrrolo[3,4-c]pyrazol-4-yl]benzonitrile Chemical compound COC1=NC(OC)=NC=C1N1C(C(C)C)=C2C(C=3C=CC(=CC=3)C#N)N(C=3C(N(C)C=C(Cl)C=3)=O)C(=O)C2=N1 FFDKGWMMRQCCRD-UHFFFAOYSA-N 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 208000006332 Choriocarcinoma Diseases 0.000 description 1
- 201000008808 Fibrosarcoma Diseases 0.000 description 1
- 206010023774 Large cell lung cancer Diseases 0.000 description 1
- 206010060862 Prostate cancer Diseases 0.000 description 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 1
- 208000035250 cutaneous malignant susceptibility to 1 melanoma Diseases 0.000 description 1
- 201000009546 lung large cell carcinoma Diseases 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161564591P | 2011-11-29 | 2011-11-29 | |
| US61/564,591 | 2011-11-29 | ||
| PCT/IB2012/056796 WO2013080141A1 (en) | 2011-11-29 | 2012-11-28 | Pyrazolopyrrolidine compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014533745A JP2014533745A (ja) | 2014-12-15 |
| JP2014533745A5 true JP2014533745A5 (enExample) | 2016-01-21 |
| JP5992054B2 JP5992054B2 (ja) | 2016-09-14 |
Family
ID=47428784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014544018A Expired - Fee Related JP5992054B2 (ja) | 2011-11-29 | 2012-11-28 | ピラゾロピロリジン化合物 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US8969341B2 (enExample) |
| EP (1) | EP2785717B1 (enExample) |
| JP (1) | JP5992054B2 (enExample) |
| CN (1) | CN104080787B (enExample) |
| WO (1) | WO2013080141A1 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8440693B2 (en) | 2009-12-22 | 2013-05-14 | Novartis Ag | Substituted isoquinolinones and quinazolinones |
| EP2721007B1 (en) | 2011-06-20 | 2015-04-29 | Novartis AG | Cyclohexyl isoquinolinone compounds |
| JO3357B1 (ar) * | 2012-01-26 | 2019-03-13 | Novartis Ag | مركبات إيميدازوبيروليدينون |
| JP6171003B2 (ja) | 2012-05-24 | 2017-07-26 | ノバルティス アーゲー | ピロロピロリジノン化合物 |
| EP2935263B1 (en) | 2012-12-20 | 2018-12-05 | Merck Sharp & Dohme Corp. | Substituted imidazopyridines as hdm2 inhibitors |
| US9403827B2 (en) | 2013-01-22 | 2016-08-02 | Novartis Ag | Substituted purinone compounds |
| US9556180B2 (en) | 2013-01-22 | 2017-01-31 | Novartis Ag | Pyrazolo[3,4-d]pyrimidinone compounds as inhibitors of the P53/MDM2 interaction |
| CA2913697A1 (en) | 2013-05-27 | 2014-12-04 | Novartis Ag | Imidazopyrrolidinone derivatives and their use in the treatment of disease |
| US8975417B2 (en) | 2013-05-27 | 2015-03-10 | Novartis Ag | Pyrazolopyrrolidine derivatives and their use in the treatment of disease |
| CA2912991A1 (en) * | 2013-05-28 | 2014-12-04 | Novartis Ag | Pyrazolo-pyrrolidin-4-one derivatives and their use in the treatment of disease |
| CA2912986A1 (en) | 2013-05-28 | 2014-12-04 | Novartis Ag | Pyrazolo-pyrrolidin-4-one derivatives as bet inhibitors and their use in the treatment of disease |
| WO2015004610A1 (en) * | 2013-07-11 | 2015-01-15 | Adamed Sp. Z O.O. | 1,5-dihydropyrrol-2-one derivatives as inhibitors of p53-mdm2/mdm4 protein-protein interaction |
| DK3290407T3 (da) | 2013-10-18 | 2020-03-23 | Celgene Quanticel Res Inc | Bromodomæneinhibitorer |
| MX2016006667A (es) * | 2013-11-21 | 2016-07-26 | Novartis Ag | Derivados de pirrolo-pirrolona y su uso como inhibidores. |
| CN105130995B (zh) * | 2015-09-09 | 2017-08-11 | 杭州成邦医药科技有限公司 | 吡咯酮类化合物及其制备方法和应用 |
| CN118436801A (zh) | 2016-05-20 | 2024-08-06 | 豪夫迈·罗氏有限公司 | Protac抗体缀合物及其使用方法 |
| GB201617758D0 (en) * | 2016-10-20 | 2016-12-07 | Almac Discovery Limited | Pharmaceutical compounds |
| BR112020013069A2 (pt) * | 2017-12-29 | 2020-12-01 | Gan & Lee Pharmaceuticals | compostos capazes de serem usados como inibidor de tumor, método de preparação dos mesmos e aplicação dos mesmos |
| EP3511334A1 (en) * | 2018-01-16 | 2019-07-17 | Adamed sp. z o.o. | 1,2,3',5'-tetrahydro-2'h-spiro[indole-3,1'-pyrrolo[3,4-c]pyrrole]-2,3'-dione compounds as therapeutic agents activating tp53 |
| JP7830488B2 (ja) * | 2021-01-21 | 2026-03-16 | ベイジン・ティアンタン・ホスピタル | Ｆｐｒ１のモジュレーター及びそれを使用する方法 |
| WO2022155860A1 (en) * | 2021-01-21 | 2022-07-28 | Biofront Therapeutics (Beijing) Co., Ltd. | Modulators of fpr1 and methods of using the same |
| WO2023056069A1 (en) | 2021-09-30 | 2023-04-06 | Angiex, Inc. | Degrader-antibody conjugates and methods of using same |
| US12251372B2 (en) | 2022-05-25 | 2025-03-18 | Trustees Of Boston University | Antileishmanial compounds, compositions and use thereof |
| WO2024240858A1 (en) | 2023-05-23 | 2024-11-28 | Valerio Therapeutics | Protac molecules directed against dna damage repair system and uses thereof |
Family Cites Families (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR901228A (fr) | 1943-01-16 | 1945-07-20 | Deutsche Edelstahlwerke Ag | Système d'aimant à entrefer annulaire |
| DE1931193A1 (de) | 1968-06-20 | 1970-01-02 | Geigy Ag J R | Verfahren zur Herstellung von neuen Imidazolidinonderivaten |
| GB1524747A (en) | 1976-05-11 | 1978-09-13 | Ici Ltd | Polypeptide |
| ATE28864T1 (de) | 1982-07-23 | 1987-08-15 | Ici Plc | Amide-derivate. |
| GB8327256D0 (en) | 1983-10-12 | 1983-11-16 | Ici Plc | Steroid derivatives |
| US5093330A (en) | 1987-06-15 | 1992-03-03 | Ciba-Geigy Corporation | Staurosporine derivatives substituted at methylamino nitrogen |
| US5010099A (en) | 1989-08-11 | 1991-04-23 | Harbor Branch Oceanographic Institution, Inc. | Discodermolide compounds, compositions containing same and method of preparation and use |
| US5395855A (en) | 1990-05-07 | 1995-03-07 | Ciba-Geigy Corporation | Hydrazones |
| NZ243082A (en) | 1991-06-28 | 1995-02-24 | Ici Plc | 4-anilino-quinazoline derivatives; pharmaceutical compositions, preparatory processes, and use thereof |
| GB9300059D0 (en) | 1992-01-20 | 1993-03-03 | Zeneca Ltd | Quinazoline derivatives |
| TW225528B (enExample) | 1992-04-03 | 1994-06-21 | Ciba Geigy Ag | |
| DK1975181T3 (da) | 1992-10-28 | 2011-06-06 | Genentech Inc | Anvendelse af vaskulære endothelcelle-vækstfaktor-antagonister |
| GB9314893D0 (en) | 1993-07-19 | 1993-09-01 | Zeneca Ltd | Quinazoline derivatives |
| US5508300A (en) | 1994-01-14 | 1996-04-16 | Pfizer Inc. | Dihydro pyrazolopyrroles, compositions and use |
| DE69536015D1 (de) | 1995-03-30 | 2009-12-10 | Pfizer Prod Inc | Chinazolinone Derivate |
| GB9508538D0 (en) | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivatives |
| US5747498A (en) | 1996-05-28 | 1998-05-05 | Pfizer Inc. | Alkynyl and azido-substituted 4-anilinoquinazolines |
| US5843901A (en) | 1995-06-07 | 1998-12-01 | Advanced Research & Technology Institute | LHRH antagonist peptides |
| US5880141A (en) | 1995-06-07 | 1999-03-09 | Sugen, Inc. | Benzylidene-Z-indoline compounds for the treatment of disease |
| EP0836605B1 (en) | 1995-07-06 | 2002-02-06 | Novartis AG | Pyrrolopyrimidines and processes for the preparation thereof |
| US5760041A (en) | 1996-02-05 | 1998-06-02 | American Cyanamid Company | 4-aminoquinazoline EGFR Inhibitors |
| GB9603095D0 (en) | 1996-02-14 | 1996-04-10 | Zeneca Ltd | Quinazoline derivatives |
| JP3370340B2 (ja) | 1996-04-12 | 2003-01-27 | ワーナー―ランバート・コンパニー | チロシンキナーゼの不可逆的阻害剤 |
| EP0907642B1 (en) | 1996-06-24 | 2005-11-02 | Pfizer Inc. | Phenylamino-substituted tricyclic derivatives for treatment of hyperproliferative diseases |
| AU716610B2 (en) | 1996-08-30 | 2000-03-02 | Novartis Ag | Method for producing epothilones, and intermediate products obtained during the production process |
| DE938597T1 (de) | 1996-09-06 | 2000-03-09 | Obducat Ab | Verfahren für das anisotrope ätzen von strukturen in leitende materialien |
| DE19638745C2 (de) | 1996-09-11 | 2001-05-10 | Schering Ag | Monoklonale Antikörper gegen die extrazelluläre Domäne des menschlichen VEGF - Rezeptorproteins (KDR) |
| AU4342997A (en) | 1996-09-13 | 1998-04-02 | Sugen, Inc. | Use of quinazoline derivatives for the manufacture of a medicament in the reatment of hyperproliferative skin disorders |
| EP0837063A1 (en) | 1996-10-17 | 1998-04-22 | Pfizer Inc. | 4-Aminoquinazoline derivatives |
| JP4274583B2 (ja) | 1996-11-18 | 2009-06-10 | ゲゼルシャフト・フュア・ビオテクノロギッシェ・フォルシュンク・ミット・ベシュレンクテル・ハフツング（ゲー・ベー・エフ） | エポチロンｃ，ｄ，ｅ及びｆ、製造と薬剤 |
| US6441186B1 (en) | 1996-12-13 | 2002-08-27 | The Scripps Research Institute | Epothilone analogs |
| CO4950519A1 (es) | 1997-02-13 | 2000-09-01 | Novartis Ag | Ftalazinas, preparaciones farmaceuticas que las comprenden y proceso para su preparacion |
| CO4940418A1 (es) | 1997-07-18 | 2000-07-24 | Novartis Ag | Modificacion de cristal de un derivado de n-fenil-2- pirimidinamina, procesos para su fabricacion y su uso |
| GB9721069D0 (en) | 1997-10-03 | 1997-12-03 | Pharmacia & Upjohn Spa | Polymeric derivatives of camptothecin |
| US6194181B1 (en) | 1998-02-19 | 2001-02-27 | Novartis Ag | Fermentative preparation process for and crystal forms of cytostatics |
| JP2002504540A (ja) | 1998-02-25 | 2002-02-12 | スローン−ケッタリング インスティトゥート フォア キャンサー リサーチ | エポチロンの合成、その中間体およびそのアナログ |
| EP1107964B8 (en) | 1998-08-11 | 2010-04-07 | Novartis AG | Isoquinoline derivatives with angiogenesis inhibiting activity |
| UA71587C2 (uk) | 1998-11-10 | 2004-12-15 | Шерінг Акцієнгезелльшафт | Аміди антранілової кислоти та їхнє застосування як лікарських засобів |
| GB9824579D0 (en) | 1998-11-10 | 1999-01-06 | Novartis Ag | Organic compounds |
| KR100851418B1 (ko) | 1998-11-20 | 2008-08-08 | 코산 바이오사이언시즈, 인코포레이티드 | 에포틸론 및 에포틸론 유도체의 생산을 위한 재조합 방법 및 물질 |
| EP2016953A3 (en) | 1998-12-22 | 2009-04-15 | Genentech, Inc. | Vascular endothelial cell growth factor antagonists and uses thereof |
| JP4673977B2 (ja) | 1999-03-30 | 2011-04-20 | ノバルティス アーゲー | 炎症性疾患治療用フタラジン誘導体 |
| JP4555547B2 (ja) | 2000-08-10 | 2010-10-06 | ファイザー イタリア ソシエタ ア レスポンサビリタ リミタータ | キナーゼ阻害剤としての二環式ピラゾール、それらを製造するための方法およびそれらを含む医薬組成物 |
| PE20020354A1 (es) | 2000-09-01 | 2002-06-12 | Novartis Ag | Compuestos de hidroxamato como inhibidores de histona-desacetilasa (hda) |
| TWI238824B (en) | 2001-05-14 | 2005-09-01 | Novartis Ag | 4-amino-5-phenyl-7-cyclobutyl-pyrrolo[2,3-d]pyrimidine derivatives |
| GB0119249D0 (en) | 2001-08-07 | 2001-10-03 | Novartis Ag | Organic compounds |
| CN100486969C (zh) | 2001-12-18 | 2009-05-13 | 霍夫曼-拉罗奇有限公司 | 顺式-2,4,5-三苯基-咪唑啉及其在肿瘤治疗中的应用 |
| AU2003235504A1 (en) | 2002-05-13 | 2003-11-11 | 3-Dimensional Pharmaceuticals, Inc. | Method for cytoprotection through mdm2 and hdm2 inhibition |
| CA2514733A1 (en) | 2003-02-28 | 2004-09-16 | Transform Pharmaceuticals, Inc. | Pharmaceutical co-crystal compositions of drugs such as carbamazepine, celecoxib, olanzapine, itraconazole, topiramate, modafinil, 5-fluorouracil, hydrochlorothiazide, acetaminophen, aspirin, flurbiprofen, phenytoin and ibuprofen |
| EP1753727B1 (en) | 2004-05-18 | 2008-11-19 | F.Hoffmann-La Roche Ag | Novel cis-imidazolines |
| US20060069085A1 (en) | 2004-09-28 | 2006-03-30 | Rulin Zhao | Preparation of 4,5-dihydro-pyrazolo[3,4-c]pyrid-2-ones |
| US20060160869A1 (en) | 2005-01-05 | 2006-07-20 | Rigel Pharmaceuticals, Inc. | Ubiquitin ligase inhibitors |
| WO2007068637A1 (en) | 2005-12-12 | 2007-06-21 | Nerviano Medical Sciences S.R.L. | Substituted pyrrolo-pyrazole derivatives active as kinase inhibitors |
| WO2007096334A1 (en) | 2006-02-24 | 2007-08-30 | Pfizer Italia Srl | Pyrrolopyrrolones active as kinase inhibitors |
| SI1999114T1 (sl) | 2006-03-22 | 2015-10-30 | F. Hoffmann-La Roche Ag | Pirazoli kot 11-beta-hsd-1 |
| US8367699B2 (en) | 2006-09-15 | 2013-02-05 | Nexuspharma, Inc. | Tetrahydro-isoquinolines |
| EP2103619A4 (en) * | 2006-12-14 | 2011-11-23 | Daiichi Sankyo Co Ltd | IMIDAZOTHIAZOLDERIVATE |
| CN101679246A (zh) | 2007-03-30 | 2010-03-24 | 盐野义制药株式会社 | 新型吡咯啉酮衍生物以及包含其的药物组合物 |
| US8642660B2 (en) | 2007-12-21 | 2014-02-04 | The University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| UY31982A (es) | 2008-07-16 | 2010-02-26 | Boehringer Ingelheim Int | Derivados de 1,2-dihidropiridin-3-carboxamidas n-sustituidas |
| TW201016702A (en) | 2008-09-25 | 2010-05-01 | Shionogi & Co | Novel pyrrolinone derivative and pharmaceutical composition comprising the same |
| US20120208204A1 (en) * | 2009-06-03 | 2012-08-16 | The Brigham And Women's Hospital, Inc. | Compositions and Methods for Inhibiting Tumor Growth |
| US8440693B2 (en) | 2009-12-22 | 2013-05-14 | Novartis Ag | Substituted isoquinolinones and quinazolinones |
| ES2526671T3 (es) | 2010-06-22 | 2015-01-14 | Glaxosmithkline Llc | Compuestos de benzotriazoldiazepina inhibidores de bromodominios |
| US20120065210A1 (en) | 2010-09-15 | 2012-03-15 | Xin-Jie Chu | Substituted hexahydropyrrolo[1,2-c]imidazolones |
| GB201016880D0 (en) | 2010-10-07 | 2010-11-17 | Riotech Pharmaceuticals Ltd | Phosphodiesterase inhibitors |
| EP2705039B1 (en) | 2011-05-04 | 2017-07-26 | Constellation Pharmaceuticals, Inc. | Bromodomain inhibitors and uses thereof |
| US9328117B2 (en) | 2011-06-17 | 2016-05-03 | Constellation Pharmaceuticals, Inc. | Bromodomain inhibitors and uses thereof |
| US8859535B2 (en) | 2011-06-20 | 2014-10-14 | Novartis Ag | Hydroxy substituted isoquinolinone derivatives |
| EP2721007B1 (en) | 2011-06-20 | 2015-04-29 | Novartis AG | Cyclohexyl isoquinolinone compounds |
| WO2013033270A2 (en) | 2011-08-29 | 2013-03-07 | Coferon, Inc. | Bromodomain ligands capable of dimerizing in an aqueous solution, and methods of using same |
| JO3357B1 (ar) | 2012-01-26 | 2019-03-13 | Novartis Ag | مركبات إيميدازوبيروليدينون |
| JP6171003B2 (ja) | 2012-05-24 | 2017-07-26 | ノバルティス アーゲー | ピロロピロリジノン化合物 |
-
2012
- 2012-11-28 US US14/361,068 patent/US8969341B2/en active Active
- 2012-11-28 CN CN201280068311.0A patent/CN104080787B/zh not_active Expired - Fee Related
- 2012-11-28 JP JP2014544018A patent/JP5992054B2/ja not_active Expired - Fee Related
- 2012-11-28 WO PCT/IB2012/056796 patent/WO2013080141A1/en not_active Ceased
- 2012-11-28 EP EP12805775.9A patent/EP2785717B1/en not_active Not-in-force
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104080787B (zh) | 吡唑并吡咯烷化合物 | |
| JP5865519B2 (ja) | イミダゾピロリジノン化合物 | |
| JP2015517566A5 (enExample) | ||
| JP2010539177A5 (enExample) | ||
| US9365576B2 (en) | Pyrrolopyrrolidinone compounds | |
| JP2016172739A5 (enExample) | ||
| US9556180B2 (en) | Pyrazolo[3,4-d]pyrimidinone compounds as inhibitors of the P53/MDM2 interaction | |
| JP2018510183A5 (enExample) | ||
| HRP20200854T1 (hr) | Novi biciklički inhibitori bromodomene | |
| RU2014151004A (ru) | Пирролопиримидоновые и пирролопиридоновые ингибиторы танкиразы | |
| JP2010510319A5 (enExample) | ||
| JP2013523884A5 (enExample) | ||
| JP2012500785A5 (enExample) | ||
| EA034216B1 (ru) | Производные 1-(5-трет-бутил-2-арилпиразол-3-ил)-3-[2-фтор-4-[(3-оксо-4h-пиридо[2,3-b]пиразин-8-ил)окси]фенил]мочевины в качестве ингибиторов raf для лечения рака | |
| JP2013505917A5 (enExample) | ||
| JP2011511034A5 (enExample) | ||
| RU2015108410A (ru) | Соединения диоксин- и оксазин[2,3-d]пиримидина в качестве ингибиторов фосфоинозитид-3-киназы и способы их применения | |
| JP2016525078A5 (enExample) | ||
| JP2006520805A5 (enExample) | ||
| JP2016537384A5 (enExample) | ||
| JP2018512062A5 (enExample) | ||
| WO2014020041A1 (en) | Combinations for the treatment of cancer | |
| JP2018516982A5 (ja) | 免疫療法用組み合わせ組成物 | |
| JP2015512427A5 (enExample) | ||
| JP2016500109A5 (enExample) |