TW201400485A - 吡咯并吡咯啶酮化合物 - Google Patents

Info

Publication number

TW201400485A

TW201400485A TW102118267A TW102118267A TW201400485A TW 201400485 A TW201400485 A TW 201400485A TW 102118267 A TW102118267 A TW 102118267A TW 102118267 A TW102118267 A TW 102118267A TW 201400485 A TW201400485 A TW 201400485A

Authority

TW

Taiwan

Prior art keywords

chloro

phenyl

isopropyl

pyrrolo

dihydro

Prior art date

2012-05-24

Links

• Espacenet
• Global Dossier
• Discuss

• OPYRETPBRCRXQU-UHFFFAOYSA-N 4,6-dihydro-1h-pyrrolo[3,2-b]pyrrol-5-one Chemical class N1C=CC2=C1CC(=O)N2 OPYRETPBRCRXQU-UHFFFAOYSA-N 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 661
• 102000012199 E3 ubiquitin-protein ligase Mdm2 Human genes 0.000 claims abstract description 69
• 108050002772 E3 ubiquitin-protein ligase Mdm2 Proteins 0.000 claims abstract description 69
• 230000000694 effects Effects 0.000 claims abstract description 69
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 48
• 108050005300 MDM4 Proteins 0.000 claims abstract description 47
• 102000017274 MDM4 Human genes 0.000 claims abstract description 47
• 201000010099 disease Diseases 0.000 claims abstract description 42
• 238000011282 treatment Methods 0.000 claims abstract description 39
• 230000001404 mediated effect Effects 0.000 claims abstract description 17
• XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 299
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 143
• -1 Methoxyethyl- Chemical group 0.000 claims description 131
• 150000003839 salts Chemical class 0.000 claims description 112
• 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 106
• 239000000460 chlorine Substances 0.000 claims description 82
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 78
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 62
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 52
• 229910052739 hydrogen Inorganic materials 0.000 claims description 48
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 38
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 37
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 33
• 125000005843 halogen group Chemical group 0.000 claims description 31
• 239000003814 drug Substances 0.000 claims description 27
• 239000008194 pharmaceutical composition Substances 0.000 claims description 21
• 235000019253 formic acid Nutrition 0.000 claims description 19
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 14
• 239000011737 fluorine Substances 0.000 claims description 14
• 229910052731 fluorine Inorganic materials 0.000 claims description 14
• 125000001424 substituent group Chemical group 0.000 claims description 12
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• 238000002560 therapeutic procedure Methods 0.000 claims description 10
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
• 239000001301 oxygen Substances 0.000 claims description 7
• DOYOPBSXEIZLRE-UHFFFAOYSA-N pyrrole-3-carboxylic acid Natural products OC(=O)C=1C=CNC=1 DOYOPBSXEIZLRE-UHFFFAOYSA-N 0.000 claims description 7
• PCYWMDGJYQAMCR-UHFFFAOYSA-N 1h-pyrrole-3-carbonitrile Chemical compound N#CC=1C=CNC=1 PCYWMDGJYQAMCR-UHFFFAOYSA-N 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• SOSFGAIKFDNWDG-UHFFFAOYSA-N 5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-2-(2-methoxyphenyl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=CC=CC=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C(=CC=C(Cl)C=1)C)C2=O SOSFGAIKFDNWDG-UHFFFAOYSA-N 0.000 claims description 5
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
• 125000000217 alkyl group Chemical group 0.000 claims description 4
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 4
• UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
• 125000004432 carbon atom Chemical group C* 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 3
• GOMZDPDQKDZYLD-UHFFFAOYSA-N 2-(2-amino-4-methoxypyrimidin-5-yl)-5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=NC(N)=NC=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C(=CC=C(Cl)C=1)C)C2=O GOMZDPDQKDZYLD-UHFFFAOYSA-N 0.000 claims description 3
• 239000013543 active substance Substances 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
• YZFOGCNKBSEULT-XMMPIXPASA-N (6r)-5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=NC(OC)=NC=C1C(N1C(C)C)=CC2=C1[C@@H](C=1C=CC(Cl)=CC=1)N(C=1C(=CC=C(Cl)C=1)C)C2=O YZFOGCNKBSEULT-XMMPIXPASA-N 0.000 claims description 2
• YZFOGCNKBSEULT-DEOSSOPVSA-N (6s)-5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=NC(OC)=NC=C1C(N1C(C)C)=CC2=C1[C@H](C=1C=CC(Cl)=CC=1)N(C=1C(=CC=C(Cl)C=1)C)C2=O YZFOGCNKBSEULT-DEOSSOPVSA-N 0.000 claims description 2
• 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims description 2
• IRALWLHZVSYHSE-UHFFFAOYSA-N 2-(2-amino-4-methoxypyrimidin-5-yl)-5-(3-chloro-4-fluorophenyl)-6-(4-chlorophenyl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=NC(N)=NC=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C=C(Cl)C(F)=CC=1)C2=O IRALWLHZVSYHSE-UHFFFAOYSA-N 0.000 claims description 2
• HJPAMNFAEFPFAA-UHFFFAOYSA-N 2-(2-amino-4-methoxypyrimidin-5-yl)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-6-(4-chloro-2-methylphenyl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=NC(N)=NC=C1C(N1C(C)C)=CC2=C1C(C=1C(=CC(Cl)=CC=1)C)N(C1=CN(C)C(=O)C(Cl)=C1)C2=O HJPAMNFAEFPFAA-UHFFFAOYSA-N 0.000 claims description 2
• YAORRZXEAIDLOS-UHFFFAOYSA-N 2-(2-amino-4-methoxypyrimidin-5-yl)-5-(5-chloro-2-methoxypyridin-3-yl)-6-(4-chlorophenyl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=NC=C(Cl)C=C1N1C(=O)C(C=C(C=2C(=NC(N)=NC=2)OC)N2C(C)C)=C2C1C1=CC=C(Cl)C=C1 YAORRZXEAIDLOS-UHFFFAOYSA-N 0.000 claims description 2
• LXERHGYQVXUJRQ-UHFFFAOYSA-N 2-(2-amino-4-methoxypyrimidin-5-yl)-6-(4-chlorophenyl)-5-(2,5-dimethylpyrazol-3-yl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=NC(N)=NC=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1N(N=C(C)C=1)C)C2=O LXERHGYQVXUJRQ-UHFFFAOYSA-N 0.000 claims description 2
• AMNGSRKNNMJCAK-UHFFFAOYSA-N 2-(2-amino-4-methoxypyrimidin-5-yl)-6-(4-chlorophenyl)-5-(4-fluoro-2,5-dimethylpyrazol-3-yl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=NC(N)=NC=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1N(N=C(C)C=1F)C)C2=O AMNGSRKNNMJCAK-UHFFFAOYSA-N 0.000 claims description 2
• MUUZZGAMDJCACC-UHFFFAOYSA-N 2-(2-amino-4-methoxypyrimidin-5-yl)-6-(4-chlorophenyl)-5-(oxan-4-yl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=NC(N)=NC=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(Cl)=CC=1)N(C1CCOCC1)C2=O MUUZZGAMDJCACC-UHFFFAOYSA-N 0.000 claims description 2
• RDPVPQKEQQLYDA-UHFFFAOYSA-N 3-[6-(4-chlorophenyl)-5-(oxan-4-yl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxybenzonitrile Chemical compound COC1=CC=C(C#N)C=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(Cl)=CC=1)N(C1CCOCC1)C2=O RDPVPQKEQQLYDA-UHFFFAOYSA-N 0.000 claims description 2
• JIASIEBVVKDQSA-UHFFFAOYSA-N 4-[2-(2,4-dimethoxypyrimidin-5-yl)-5-(oxan-4-yl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-6-yl]benzonitrile Chemical compound COC1=NC(OC)=NC=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(=CC=1)C#N)N(C1CCOCC1)C2=O JIASIEBVVKDQSA-UHFFFAOYSA-N 0.000 claims description 2
• HPUAUMBBZXSYGE-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-6-(4-chloro-2-methylphenyl)-2-(2-methoxyphenyl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=CC=CC=C1C(N1C(C)C)=CC2=C1C(C=1C(=CC(Cl)=CC=1)C)N(C=1C(=C(Cl)C=CC=1)F)C2=O HPUAUMBBZXSYGE-UHFFFAOYSA-N 0.000 claims description 2
• KVFBYPXRLMBHFK-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-6-(4-chloro-2-methylphenyl)-2-(5-fluoro-2-methoxyphenyl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=CC=C(F)C=C1C(N1C(C)C)=CC2=C1C(C=1C(=CC(Cl)=CC=1)C)N(C=1C(=C(Cl)C=CC=1)F)C2=O KVFBYPXRLMBHFK-UHFFFAOYSA-N 0.000 claims description 2
• XFXHIRDFHWUYQO-UHFFFAOYSA-N 5-(3-chloro-2-fluorophenyl)-6-(4-chloro-2-methylphenyl)-2-[5-(hydroxymethyl)-2-methoxyphenyl]-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=CC=C(CO)C=C1C(N1C(C)C)=CC2=C1C(C=1C(=CC(Cl)=CC=1)C)N(C=1C(=C(Cl)C=CC=1)F)C2=O XFXHIRDFHWUYQO-UHFFFAOYSA-N 0.000 claims description 2
• LEBMQPMVEIWNHI-UHFFFAOYSA-N 5-(3-chloro-4-fluorophenyl)-6-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=NC(OC)=NC=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C=C(Cl)C(F)=CC=1)C2=O LEBMQPMVEIWNHI-UHFFFAOYSA-N 0.000 claims description 2
• PHRQUZMQZUQZPF-UHFFFAOYSA-N 5-(3-chloro-4-fluorophenyl)-6-(4-chlorophenyl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=NC(N(C)C)=NC=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C=C(Cl)C(F)=CC=1)C2=O PHRQUZMQZUQZPF-UHFFFAOYSA-N 0.000 claims description 2
• WDEVSGDQMMXJMI-UHFFFAOYSA-N 5-(3-chloro-4-fluorophenyl)-6-(5-chloropyridin-2-yl)-2-(2,4-dimethoxypyrimidin-5-yl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=NC(OC)=NC=C1C(N1C(C)C)=CC2=C1C(C=1N=CC(Cl)=CC=1)N(C=1C=C(Cl)C(F)=CC=1)C2=O WDEVSGDQMMXJMI-UHFFFAOYSA-N 0.000 claims description 2
• MIEMYVCLDZMUGL-UHFFFAOYSA-N 5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-2-(2,4-dimethoxyphenyl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=CC(OC)=CC=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C(=CC=C(Cl)C=1)C)C2=O MIEMYVCLDZMUGL-UHFFFAOYSA-N 0.000 claims description 2
• ZULSNYQIJDALQK-UHFFFAOYSA-N 5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-1-ethyl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound C1=2N(CC)C(C=3C(=NC(OC)=NC=3)OC)=CC=2C(=O)N(C=2C(=CC=C(Cl)C=2)C)C1C1=CC=C(Cl)C=C1 ZULSNYQIJDALQK-UHFFFAOYSA-N 0.000 claims description 2
• YZFOGCNKBSEULT-UHFFFAOYSA-N 5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=NC(OC)=NC=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C(=CC=C(Cl)C=1)C)C2=O YZFOGCNKBSEULT-UHFFFAOYSA-N 0.000 claims description 2
• YYOBZKJTJKLZNG-UHFFFAOYSA-N 5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-2-(2,6-dimethoxypyridin-3-yl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=NC(OC)=CC=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C(=CC=C(Cl)C=1)C)C2=O YYOBZKJTJKLZNG-UHFFFAOYSA-N 0.000 claims description 2
• CQNLQGGJXSRPQH-UHFFFAOYSA-N 5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-2-(2-hydroxyphenyl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound C1=2N(C(C)C)C(C=3C(=CC=CC=3)O)=CC=2C(=O)N(C=2C(=CC=C(Cl)C=2)C)C1C1=CC=C(Cl)C=C1 CQNLQGGJXSRPQH-UHFFFAOYSA-N 0.000 claims description 2
• GSQJRMZJYWCMON-UHFFFAOYSA-N 5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-2-(2-methoxyphenyl)-6-methyl-1-propan-2-ylpyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=CC=CC=C1C(N1C(C)C)=CC2=C1C(C)(C=1C=CC(Cl)=CC=1)N(C=1C(=CC=C(Cl)C=1)C)C2=O GSQJRMZJYWCMON-UHFFFAOYSA-N 0.000 claims description 2
• DYHDRBWGUXTIKZ-UHFFFAOYSA-N 5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-2-(3-methoxypyridin-2-yl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=CC=CN=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C(=CC=C(Cl)C=1)C)C2=O DYHDRBWGUXTIKZ-UHFFFAOYSA-N 0.000 claims description 2
• VWIUKUSNMLAMJQ-UHFFFAOYSA-N 5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-2-(4-methoxypyridin-3-yl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=CC=NC=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C(=CC=C(Cl)C=1)C)C2=O VWIUKUSNMLAMJQ-UHFFFAOYSA-N 0.000 claims description 2
• BGPLNPYJPVUTME-UHFFFAOYSA-N 5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-2-(4-methoxypyrimidin-5-yl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=NC=NC=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C(=CC=C(Cl)C=1)C)C2=O BGPLNPYJPVUTME-UHFFFAOYSA-N 0.000 claims description 2
• QNZXLWQESPUDAO-UHFFFAOYSA-N 5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-2-[2-methoxy-5-(2h-tetrazol-5-yl)phenyl]-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=CC=C(C=2NN=NN=2)C=C1C(N(C=12)C(C)C)=CC=1C(=O)N(C=1C(=CC=C(Cl)C=1)C)C2C1=CC=C(Cl)C=C1 QNZXLWQESPUDAO-UHFFFAOYSA-N 0.000 claims description 2
• MDUZDRLEWCSTAN-UHFFFAOYSA-N 5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-3-fluoro-2-(2-methoxyphenyl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=CC=CC=C1C(N1C(C)C)=C(F)C2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C(=CC=C(Cl)C=1)C)C2=O MDUZDRLEWCSTAN-UHFFFAOYSA-N 0.000 claims description 2
• AIAHKMZLMBDZSR-UHFFFAOYSA-N 5-(5-chloro-2-oxo-1h-pyridin-3-yl)-6-(4-chlorophenyl)-2-[4-methoxy-2-(methylamino)pyrimidin-5-yl]-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=NC(NC)=NC=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C(NC=C(Cl)C=1)=O)C2=O AIAHKMZLMBDZSR-UHFFFAOYSA-N 0.000 claims description 2
• YOVBMDGCLOZVGS-UHFFFAOYSA-N 6-(4-chloro-2-fluorophenyl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-5-(2,5-dimethylpyrazol-3-yl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=NC(N(C)C)=NC=C1C(N1C(C)C)=CC2=C1C(C=1C(=CC(Cl)=CC=1)F)N(C=1N(N=C(C)C=1)C)C2=O YOVBMDGCLOZVGS-UHFFFAOYSA-N 0.000 claims description 2
• OSLNVLCEPCZWRC-UHFFFAOYSA-N 6-(4-chloro-2-methylphenyl)-2-(2-methoxyphenyl)-5-(oxan-4-yl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=CC=CC=C1C(N1C(C)C)=CC2=C1C(C=1C(=CC(Cl)=CC=1)C)N(C1CCOCC1)C2=O OSLNVLCEPCZWRC-UHFFFAOYSA-N 0.000 claims description 2
• BLEVOLXKWGTFKI-UHFFFAOYSA-N 6-(4-chloro-2-methylphenyl)-5-(4-hydroxycyclohexyl)-2-(2-methoxyphenyl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=CC=CC=C1C(N1C(C)C)=CC2=C1C(C=1C(=CC(Cl)=CC=1)C)N(C1CCC(O)CC1)C2=O BLEVOLXKWGTFKI-UHFFFAOYSA-N 0.000 claims description 2
• FKLVAGWTFKZMIT-UHFFFAOYSA-N 6-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-2-(2-methoxyphenyl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=CC=CC=C1C(N1C(C)C)=CC2=C1C(C=1C(=CC(Cl)=CC=1)C)N(C=1C(=CC=C(Cl)C=1)C)C2=O FKLVAGWTFKZMIT-UHFFFAOYSA-N 0.000 claims description 2
• MMDOZNCKVZBKSH-UHFFFAOYSA-N 6-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-5-piperidin-4-yl-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=NC(OC)=NC=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(Cl)=CC=1)N(C1CCNCC1)C2=O MMDOZNCKVZBKSH-UHFFFAOYSA-N 0.000 claims description 2
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