JP2014533745A5 - - Google Patents
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- 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
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- -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
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| US9365576B2 (en) | 2012-05-24 | 2016-06-14 | Novartis Ag | Pyrrolopyrrolidinone compounds |
| RU2690663C2 (ru) | 2012-12-20 | 2019-06-05 | Мерк Шарп И Доум Корп. | Замещенные имидазопиридины в качестве ингибиторов hdm2 |
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| US9556180B2 (en) | 2013-01-22 | 2017-01-31 | Novartis Ag | Pyrazolo[3,4-d]pyrimidinone compounds as inhibitors of the P53/MDM2 interaction |
| US8975417B2 (en) * | 2013-05-27 | 2015-03-10 | Novartis Ag | Pyrazolopyrrolidine derivatives and their use in the treatment of disease |
| CN105209467B (zh) | 2013-05-27 | 2018-06-08 | 诺华股份有限公司 | 咪唑并吡咯烷酮衍生物及其在治疗疾病中的用途 |
| JP2016520118A (ja) * | 2013-05-28 | 2016-07-11 | ノバルティス アーゲー | Ｂｅｔ阻害剤としてのピラゾロ−ピロリジン−４−オン誘導体および疾患の処置におけるその使用 |
| WO2014191911A1 (en) * | 2013-05-28 | 2014-12-04 | Novartis Ag | Pyrazolo-pyrrolidin-4-one derivatives 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 |
| US9034900B2 (en) | 2013-10-18 | 2015-05-19 | Quanticel Pharmaceuticals, Inc. | Bromodomain inhibitors |
| EP3071571A1 (en) * | 2013-11-21 | 2016-09-28 | Novartis AG | Pyrrolopyrrolone derivatives and their use as bet inhibitors |
| 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 |
| JP2019522633A (ja) | 2016-05-20 | 2019-08-15 | ジェネンテック， インコーポレイテッド | Ｐｒｏｔａｃ抗体コンジュゲート及び使用方法 |
| GB201617758D0 (en) * | 2016-10-20 | 2016-12-07 | Almac Discovery Limited | Pharmaceutical compounds |
| KR20200105837A (ko) * | 2017-12-29 | 2020-09-09 | 간 앤 리 파마슈티칼스 | 종양 억제제로 사용될 수 있는 화합물 및 이의 제조방법과 용도 |
| 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 |
| WO2022155859A1 (en) * | 2021-01-21 | 2022-07-28 | Beijing Tiantan Hospital | Modulators of fpr1 and methods of using the same |
| US20240300973A1 (en) * | 2021-01-21 | 2024-09-12 | 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 |
| AU661533B2 (en) | 1992-01-20 | 1995-07-27 | Astrazeneca Ab | Quinazoline derivatives |
| TW225528B (cg-RX-API-DMAC7.html) | 1992-04-03 | 1994-06-21 | Ciba Geigy Ag | |
| WO1994010202A1 (en) | 1992-10-28 | 1994-05-11 | Genentech, Inc. | Vascular endothelial cell growth factor antagonists |
| 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 |
| WO1996030347A1 (en) | 1995-03-30 | 1996-10-03 | Pfizer Inc. | Quinazoline derivatives |
| 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 |
| US5880141A (en) | 1995-06-07 | 1999-03-09 | Sugen, Inc. | Benzylidene-Z-indoline compounds for the treatment of disease |
| US5843901A (en) | 1995-06-07 | 1998-12-01 | Advanced Research & Technology Institute | LHRH antagonist peptides |
| DE69619114T2 (de) | 1995-07-06 | 2002-10-02 | Novartis Ag, Basel | Pyrolopyrimidine und verfahren zu ihrer herstellung |
| 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 |
| ATE213730T1 (de) | 1996-04-12 | 2002-03-15 | Warner Lambert Co | Umkehrbare inhibitoren von tyrosin kinasen |
| CA2258548C (en) | 1996-06-24 | 2005-07-26 | Pfizer Inc. | Phenylamino-substituted tricyclic derivatives for treatment of hyperproliferative diseases |
| NZ334821A (en) | 1996-08-30 | 2000-12-22 | Novartis Ag | Method for producing epothilones |
| ATE247724T1 (de) | 1996-09-06 | 2003-09-15 | 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) |
| CA2265630A1 (en) | 1996-09-13 | 1998-03-19 | Gerald Mcmahon | Use of quinazoline derivatives for the manufacture of a medicament in the treatment of hyperproliferative skin disorders |
| EP0837063A1 (en) | 1996-10-17 | 1998-04-22 | Pfizer Inc. | 4-Aminoquinazoline derivatives |
| PT1367057E (pt) | 1996-11-18 | 2008-12-04 | Biotechnolog Forschung Gmbh | Epotilonas e e f |
| 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 |
| NZ506742A (en) | 1998-02-25 | 2003-09-26 | Sloan Kettering Inst Cancer | Synthesis of desoxyepothilones and hydroxy acid derivative intermediates |
| BR9912938B1 (pt) | 1998-08-11 | 2011-06-28 | derivados de isoquinolina, composição que os compreende, processo para preparação e uso dos mesmos. | |
| 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 |
| NZ511722A (en) | 1998-11-20 | 2004-05-28 | Kosan Biosciences Inc | Recombinant methods and materials for producing epothilone and epothilone derivatives |
| ATE300957T1 (de) | 1998-12-22 | 2005-08-15 | Genentech Inc | Antagonisten von vaskular-endothelialen zellwachstumsfaktoren und ihre anwendung |
| PT1165085E (pt) | 1999-03-30 | 2006-10-31 | Novartis Ag | Derivados de ftalazina para tratar doencas inflamatorias |
| NZ524475A (en) | 2000-08-10 | 2004-11-26 | Pharmacia Italia S | Bicyclo-pyrazoles active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them |
| 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 |
| CA2469187C (en) | 2001-12-18 | 2012-07-17 | F. Hoffmann-La Roche Ag | Cis-2,4,5-triphenyl-imidazolines and their use in the treatment of tumors |
| AU2003235504A1 (en) | 2002-05-13 | 2003-11-11 | 3-Dimensional Pharmaceuticals, Inc. | Method for cytoprotection through mdm2 and hdm2 inhibition |
| JP2007524596A (ja) | 2003-02-28 | 2007-08-30 | トランスフォーム・ファーマシューティカルズ・インコーポレイテッド | 共結晶医薬組成物 |
| CN1953965B (zh) | 2004-05-18 | 2012-07-04 | 霍夫曼-拉罗奇有限公司 | 新型顺式咪唑啉类化合物 |
| US20060069085A1 (en) | 2004-09-28 | 2006-03-30 | Rulin Zhao | Preparation of 4,5-dihydro-pyrazolo[3,4-c]pyrid-2-ones |
| WO2006074262A1 (en) | 2005-01-05 | 2006-07-13 | Rigel Pharmaceuticals, Inc. | Ubiquitin ligase inhibitors |
| CA2631907A1 (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 |
| KR20110007258A (ko) | 2006-03-22 | 2011-01-21 | 에프. 호프만-라 로슈 아게 | 11-베타-ｈｓｄ-1로서의 피라졸 |
| US8367699B2 (en) | 2006-09-15 | 2013-02-05 | Nexuspharma, Inc. | Tetrahydro-isoquinolines |
| JPWO2008072655A1 (ja) * | 2006-12-14 | 2010-04-02 | 第一三共株式会社 | イミダゾチアゾール誘導体 |
| JP5624762B2 (ja) * | 2007-03-30 | 2014-11-12 | 塩野義製薬株式会社 | 新規ピロリノン誘導体およびそれを含有する医薬組成物 |
| CA2709784A1 (en) | 2007-12-21 | 2009-07-09 | 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 |
| JP5637562B2 (ja) | 2008-09-25 | 2014-12-10 | 塩野義製薬株式会社 | 新規ピロリノン誘導体およびそれを含有する医薬組成物 |
| WO2010141738A2 (en) * | 2009-06-03 | 2010-12-09 | President And Fellows Of Harvard College | Compositions and method 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 |
| US9422292B2 (en) | 2011-05-04 | 2016-08-23 | Constellation Pharmaceuticals, Inc. | Bromodomain inhibitors and uses thereof |
| WO2012174487A2 (en) | 2011-06-17 | 2012-12-20 | 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 |
| UY34591A (es) | 2012-01-26 | 2013-09-02 | Novartis Ag | Compuestos de imidazopirrolidinona |
| US9365576B2 (en) | 2012-05-24 | 2016-06-14 | Novartis Ag | Pyrrolopyrrolidinone compounds |
-
2012
- 2012-11-28 WO PCT/IB2012/056796 patent/WO2013080141A1/en not_active Ceased
- 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 EP EP12805775.9A patent/EP2785717B1/en not_active Not-in-force
- 2012-11-28 US US14/361,068 patent/US8969341B2/en active Active