JP2015517566A5 - - Google Patents
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- JP2015517566A5 JP2015517566A5 JP2015513334A JP2015513334A JP2015517566A5 JP 2015517566 A5 JP2015517566 A5 JP 2015517566A5 JP 2015513334 A JP2015513334 A JP 2015513334A JP 2015513334 A JP2015513334 A JP 2015513334A JP 2015517566 A5 JP2015517566 A5 JP 2015517566A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- phenyl
- pyrrol
- isopropyl
- pyrrolo
- 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 methoxyethyl- Chemical group 0.000 claims 103
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 30
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 20
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 14
- 125000005843 halogen group Chemical group 0.000 claims 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 5
- 102000012199 E3 ubiquitin-protein ligase Mdm2 Human genes 0.000 claims 4
- 108050002772 E3 ubiquitin-protein ligase Mdm2 Proteins 0.000 claims 4
- 102000017274 MDM4 Human genes 0.000 claims 4
- 108050005300 MDM4 Proteins 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 230000000694 effects Effects 0.000 claims 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 230000001404 mediated effect Effects 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- INTJZENRAYCATA-UHFFFAOYSA-N pyrrol-3-one Chemical compound O=C1C=CN=C1 INTJZENRAYCATA-UHFFFAOYSA-N 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- FGPTWTSRUGMJDE-QKFKETGDSA-N (6r)-2-(2-amino-4-methoxypyrimidin-5-yl)-5-(3-chloro-4-fluorophenyl)-6-(4-chlorophenyl)-1-[(2r)-1-methoxypropan-2-yl]-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound C1([C@H]2N(C(=O)C=3C=C(N(C2=3)[C@H](C)COC)C=2C(=NC(N)=NC=2)OC)C=2C=C(Cl)C(F)=CC=2)=CC=C(Cl)C=C1 FGPTWTSRUGMJDE-QKFKETGDSA-N 0.000 claims 1
- QCKNGTYKLJBZHR-HSZRJFAPSA-N (6r)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-6-(4-chloro-2-methylphenyl)-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)C)N(C1=CN(C)C(=O)C(Cl)=C1)C2=O QCKNGTYKLJBZHR-HSZRJFAPSA-N 0.000 claims 1
- VTGDOFNBBBIIFU-JOCHJYFZSA-N (6r)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-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(C1=CN(C)C(=O)C(Cl)=C1)C2=O VTGDOFNBBBIIFU-JOCHJYFZSA-N 0.000 claims 1
- VNOJIJITXHFGMF-MUUNZHRXSA-N (6r)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-6-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-6-methyl-1-propan-2-ylpyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=NC(OC)=NC=C1C(N1C(C)C)=CC2=C1[C@@](C)(C=1C=CC(Cl)=CC=1)N(C1=CN(C)C(=O)C(Cl)=C1)C2=O VNOJIJITXHFGMF-MUUNZHRXSA-N 0.000 claims 1
- 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 1
- QLTYTONTIBMGPM-JOCHJYFZSA-N (6r)-5-(5-chloro-6-oxo-1h-pyridin-3-yl)-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=C1[C@@H](C=1C=CC(Cl)=CC=1)N(C=1C=C(Cl)C(=O)NC=1)C2=O QLTYTONTIBMGPM-JOCHJYFZSA-N 0.000 claims 1
- FGPTWTSRUGMJDE-FATZIPQQSA-N (6s)-2-(2-amino-4-methoxypyrimidin-5-yl)-5-(3-chloro-4-fluorophenyl)-6-(4-chlorophenyl)-1-[(2r)-1-methoxypropan-2-yl]-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound C1([C@@H]2N(C(=O)C=3C=C(N(C2=3)[C@H](C)COC)C=2C(=NC(N)=NC=2)OC)C=2C=C(Cl)C(F)=CC=2)=CC=C(Cl)C=C1 FGPTWTSRUGMJDE-FATZIPQQSA-N 0.000 claims 1
- QCKNGTYKLJBZHR-QHCPKHFHSA-N (6s)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-6-(4-chloro-2-methylphenyl)-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)C)N(C1=CN(C)C(=O)C(Cl)=C1)C2=O QCKNGTYKLJBZHR-QHCPKHFHSA-N 0.000 claims 1
- VTGDOFNBBBIIFU-QFIPXVFZSA-N (6s)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-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(C1=CN(C)C(=O)C(Cl)=C1)C2=O VTGDOFNBBBIIFU-QFIPXVFZSA-N 0.000 claims 1
- VNOJIJITXHFGMF-NDEPHWFRSA-N (6s)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-6-(4-chlorophenyl)-2-(2,4-dimethoxypyrimidin-5-yl)-6-methyl-1-propan-2-ylpyrrolo[3,4-b]pyrrol-4-one Chemical compound COC1=NC(OC)=NC=C1C(N1C(C)C)=CC2=C1[C@](C)(C=1C=CC(Cl)=CC=1)N(C1=CN(C)C(=O)C(Cl)=C1)C2=O VNOJIJITXHFGMF-NDEPHWFRSA-N 0.000 claims 1
- 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 1
- QLTYTONTIBMGPM-QFIPXVFZSA-N (6s)-5-(5-chloro-6-oxo-1h-pyridin-3-yl)-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=C1[C@H](C=1C=CC(Cl)=CC=1)N(C=1C=C(Cl)C(=O)NC=1)C2=O QLTYTONTIBMGPM-QFIPXVFZSA-N 0.000 claims 1
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims 1
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims 1
- PCYWMDGJYQAMCR-UHFFFAOYSA-N 1h-pyrrole-3-carbonitrile Chemical compound N#CC=1C=CNC=1 PCYWMDGJYQAMCR-UHFFFAOYSA-N 0.000 claims 1
- FFMAOIYFWDTUHY-UHFFFAOYSA-N 2-(2-amino-4-methoxypyrimidin-5-yl)-5-(5-chloro-1-methyl-2-oxopyridin-3-yl)-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(N(C)C=C(Cl)C=1)=O)C2=O FFMAOIYFWDTUHY-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- XMQRFSWKZVXRFN-UHFFFAOYSA-N 2-(2-amino-4-methoxypyrimidin-5-yl)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-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(C1=CN(C)C(=O)C(Cl)=C1)C2=O XMQRFSWKZVXRFN-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- YMDJIUXSNMFBNK-UHFFFAOYSA-N 2-(2-amino-4-methoxypyrimidin-5-yl)-5-(5-chloro-6-oxo-1h-pyridin-3-yl)-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(=O)NC=1)C2=O YMDJIUXSNMFBNK-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- SMIIJGLUXLTXPE-UHFFFAOYSA-N 2-(2-amino-4-methoxypyrimidin-5-yl)-6-(4-chlorophenyl)-5-(4-methoxycyclohexyl)-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-4-one Chemical compound C1CC(OC)CCC1N1C(=O)C(C=C(C=2C(=NC(N)=NC=2)OC)N2C(C)C)=C2C1C1=CC=C(Cl)C=C1 SMIIJGLUXLTXPE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- AKRDHGGMTLKLII-UHFFFAOYSA-N 2-[2-(2-amino-4-methoxypyrimidin-5-yl)-6-(4-chlorophenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-5-yl]-4-chlorobenzonitrile 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#N)C2=O AKRDHGGMTLKLII-UHFFFAOYSA-N 0.000 claims 1
- NBVBMZRUNBAPLX-GDLZYMKVSA-N 2-[3-[(6r)-5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxyphenyl]acetic acid Chemical compound COC1=CC=C(CC(O)=O)C=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 NBVBMZRUNBAPLX-GDLZYMKVSA-N 0.000 claims 1
- NBVBMZRUNBAPLX-LJAQVGFWSA-N 2-[3-[(6s)-5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxyphenyl]acetic acid Chemical compound COC1=CC=C(CC(O)=O)C=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 NBVBMZRUNBAPLX-LJAQVGFWSA-N 0.000 claims 1
- ZKXXUOFBGYBXBG-UHFFFAOYSA-N 2-[3-[5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-6-(4-chlorophenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxyphenyl]acetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(Cl)=CC=1)N(C1=CN(C)C(=O)C(Cl)=C1)C2=O ZKXXUOFBGYBXBG-UHFFFAOYSA-N 0.000 claims 1
- UWYJVUIKLPQQIR-UHFFFAOYSA-N 2-[3-[5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxyphenyl]-n,n-dimethylacetamide Chemical compound COC1=CC=C(CC(=O)N(C)C)C=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C(=CC=C(Cl)C=1)C)C2=O UWYJVUIKLPQQIR-UHFFFAOYSA-N 0.000 claims 1
- MVNVEOWYICDPQA-UHFFFAOYSA-N 2-[3-[5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxyphenyl]-n-methylacetamide Chemical compound CNC(=O)CC1=CC=C(OC)C(C=2N(C=3C(N(C(=O)C=3C=2)C=2C(=CC=C(Cl)C=2)C)C=2C=CC(Cl)=CC=2)C(C)C)=C1 MVNVEOWYICDPQA-UHFFFAOYSA-N 0.000 claims 1
- WWHWAAJKQGGHIK-UHFFFAOYSA-N 2-[3-[5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxyphenyl]acetamide Chemical compound COC1=CC=C(CC(N)=O)C=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C(=CC=C(Cl)C=1)C)C2=O WWHWAAJKQGGHIK-UHFFFAOYSA-N 0.000 claims 1
- NBVBMZRUNBAPLX-UHFFFAOYSA-N 2-[3-[5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxyphenyl]acetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C(=CC=C(Cl)C=1)C)C2=O NBVBMZRUNBAPLX-UHFFFAOYSA-N 0.000 claims 1
- RUVPTRXOQQUJIP-UHFFFAOYSA-N 2-[4-[5-(3-chloro-2-fluorophenyl)-6-(4-cyanophenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-5-methoxypyridin-2-yl]acetic acid Chemical compound COC1=CN=C(CC(O)=O)C=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(=CC=1)C#N)N(C=1C(=C(Cl)C=CC=1)F)C2=O RUVPTRXOQQUJIP-UHFFFAOYSA-N 0.000 claims 1
- ZVKVJRYUHUKSFD-UHFFFAOYSA-N 2-[5-[5-(3-chloro-2-fluorophenyl)-6-(4-cyanophenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-6-methoxypyridin-3-yl]-n-methylacetamide Chemical compound CNC(=O)CC1=CN=C(OC)C(C=2N(C=3C(N(C(=O)C=3C=2)C=2C(=C(Cl)C=CC=2)F)C=2C=CC(=CC=2)C#N)C(C)C)=C1 ZVKVJRYUHUKSFD-UHFFFAOYSA-N 0.000 claims 1
- CJCXKFFSPDPEDJ-MUUNZHRXSA-N 3-[(6r)-5-(3-chloro-2-fluorophenyl)-6-(4-chloro-2-methylphenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC=C(OC)C(C=2N(C=3[C@H](N(C(=O)C=3C=2)C=2C(=C(Cl)C=CC=2)F)C=2C(=CC(Cl)=CC=2)C)C(C)C)=C1 CJCXKFFSPDPEDJ-MUUNZHRXSA-N 0.000 claims 1
- QIDROMJGYTVCCT-GDLZYMKVSA-N 3-[(6r)-5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxy-n,n-dimethylbenzamide Chemical compound COC1=CC=C(C(=O)N(C)C)C=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 QIDROMJGYTVCCT-GDLZYMKVSA-N 0.000 claims 1
- NZQSMNSXZCVNDS-MUUNZHRXSA-N 3-[(6r)-5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC=C(OC)C(C=2N(C=3[C@H](N(C(=O)C=3C=2)C=2C(=CC=C(Cl)C=2)C)C=2C=CC(Cl)=CC=2)C(C)C)=C1 NZQSMNSXZCVNDS-MUUNZHRXSA-N 0.000 claims 1
- ILWFBBGNMHVGNM-HHHXNRCGSA-N 3-[(6r)-5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=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 ILWFBBGNMHVGNM-HHHXNRCGSA-N 0.000 claims 1
- JQUIAIKLJOCMEX-GDLZYMKVSA-N 3-[(6r)-6-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC=C(OC)C(C=2N(C=3[C@H](N(C(=O)C=3C=2)C=2C(=CC=C(Cl)C=2)C)C=2C(=CC(Cl)=CC=2)C)C(C)C)=C1 JQUIAIKLJOCMEX-GDLZYMKVSA-N 0.000 claims 1
- CJCXKFFSPDPEDJ-NDEPHWFRSA-N 3-[(6s)-5-(3-chloro-2-fluorophenyl)-6-(4-chloro-2-methylphenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC=C(OC)C(C=2N(C=3[C@@H](N(C(=O)C=3C=2)C=2C(=C(Cl)C=CC=2)F)C=2C(=CC(Cl)=CC=2)C)C(C)C)=C1 CJCXKFFSPDPEDJ-NDEPHWFRSA-N 0.000 claims 1
- QIDROMJGYTVCCT-LJAQVGFWSA-N 3-[(6s)-5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxy-n,n-dimethylbenzamide Chemical compound COC1=CC=C(C(=O)N(C)C)C=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 QIDROMJGYTVCCT-LJAQVGFWSA-N 0.000 claims 1
- NZQSMNSXZCVNDS-NDEPHWFRSA-N 3-[(6s)-5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC=C(OC)C(C=2N(C=3[C@@H](N(C(=O)C=3C=2)C=2C(=CC=C(Cl)C=2)C)C=2C=CC(Cl)=CC=2)C(C)C)=C1 NZQSMNSXZCVNDS-NDEPHWFRSA-N 0.000 claims 1
- ILWFBBGNMHVGNM-MHZLTWQESA-N 3-[(6s)-5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=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 ILWFBBGNMHVGNM-MHZLTWQESA-N 0.000 claims 1
- JQUIAIKLJOCMEX-LJAQVGFWSA-N 3-[(6s)-6-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC=C(OC)C(C=2N(C=3[C@@H](N(C(=O)C=3C=2)C=2C(=CC=C(Cl)C=2)C)C=2C(=CC(Cl)=CC=2)C)C(C)C)=C1 JQUIAIKLJOCMEX-LJAQVGFWSA-N 0.000 claims 1
- CJCXKFFSPDPEDJ-UHFFFAOYSA-N 3-[5-(3-chloro-2-fluorophenyl)-6-(4-chloro-2-methylphenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC=C(OC)C(C=2N(C=3C(N(C(=O)C=3C=2)C=2C(=C(Cl)C=CC=2)F)C=2C(=CC(Cl)=CC=2)C)C(C)C)=C1 CJCXKFFSPDPEDJ-UHFFFAOYSA-N 0.000 claims 1
- JVQOZXAGUFLHTP-UHFFFAOYSA-N 3-[5-(3-chloro-4-fluorophenyl)-6-(4-chlorophenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC=C(OC)C(C=2N(C=3C(N(C(=O)C=3C=2)C=2C=C(Cl)C(F)=CC=2)C=2C=CC(Cl)=CC=2)C(C)C)=C1 JVQOZXAGUFLHTP-UHFFFAOYSA-N 0.000 claims 1
- AUCFWTPOSQPMCN-UHFFFAOYSA-N 3-[5-(3-chloro-4-fluorophenyl)-6-(4-chlorophenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C=C(Cl)C(F)=CC=1)C2=O AUCFWTPOSQPMCN-UHFFFAOYSA-N 0.000 claims 1
- LXTGXLSPSBMXFK-UHFFFAOYSA-N 3-[5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-6-(4-chloro-2-methylphenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC=C(OC)C(C=2N(C=3C(N(C(=O)C=3C=2)C2=CN(C)C(=O)C(Cl)=C2)C=2C(=CC(Cl)=CC=2)C)C(C)C)=C1 LXTGXLSPSBMXFK-UHFFFAOYSA-N 0.000 claims 1
- AHKXWUMEVJBCEZ-UHFFFAOYSA-N 3-[5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-6-(4-chlorophenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC=C(OC)C(C=2N(C=3C(N(C(=O)C=3C=2)C2=CN(C)C(=O)C(Cl)=C2)C=2C=CC(Cl)=CC=2)C(C)C)=C1 AHKXWUMEVJBCEZ-UHFFFAOYSA-N 0.000 claims 1
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- QIDROMJGYTVCCT-UHFFFAOYSA-N 3-[5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxy-n,n-dimethylbenzamide Chemical compound COC1=CC=C(C(=O)N(C)C)C=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C(=CC=C(Cl)C=1)C)C2=O QIDROMJGYTVCCT-UHFFFAOYSA-N 0.000 claims 1
- POZXFZSLKQZFDU-UHFFFAOYSA-N 3-[5-(5-chloro-2-methylphenyl)-6-(4-chlorophenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxy-n-(2-methylsulfonylethyl)benzamide Chemical compound COC1=CC=C(C(=O)NCCS(C)(=O)=O)C=C1C(N1C(C)C)=CC2=C1C(C=1C=CC(Cl)=CC=1)N(C=1C(=CC=C(Cl)C=1)C)C2=O POZXFZSLKQZFDU-UHFFFAOYSA-N 0.000 claims 1
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- JQUIAIKLJOCMEX-UHFFFAOYSA-N 3-[6-(4-chloro-2-methylphenyl)-5-(5-chloro-2-methylphenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-2-yl]-4-methoxy-n-methylbenzamide Chemical compound CNC(=O)C1=CC=C(OC)C(C=2N(C=3C(N(C(=O)C=3C=2)C=2C(=CC=C(Cl)C=2)C)C=2C(=CC(Cl)=CC=2)C)C(C)C)=C1 JQUIAIKLJOCMEX-UHFFFAOYSA-N 0.000 claims 1
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- WFWTZNXJCNYUAQ-XMMPIXPASA-N 4-[(6r)-2-[2-(dimethylamino)-4-methoxypyrimidin-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(N(C)C)=NC=C1C(N1C(C)C)=CC2=C1[C@@H](C=1C=CC(=CC=1)C#N)N(C1CCOCC1)C2=O WFWTZNXJCNYUAQ-XMMPIXPASA-N 0.000 claims 1
- HHNKSOUSJFWEBC-RUZDIDTESA-N 4-[(6r)-5-(3-chloro-4-fluorophenyl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-6-yl]benzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1C(N1C(C)C)=CC2=C1[C@@H](C=1C=CC(=CC=1)C#N)N(C=1C=C(Cl)C(F)=CC=1)C2=O HHNKSOUSJFWEBC-RUZDIDTESA-N 0.000 claims 1
- BTRWWPFRLVLFAI-HSZRJFAPSA-N 4-[(6r)-5-(5-chloro-1-methyl-2-oxopyridin-3-yl)-2-(2,4-dimethoxypyrimidin-5-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=C1[C@@H](C=1C=CC(=CC=1)C#N)N(C=1C(N(C)C=C(Cl)C=1)=O)C2=O BTRWWPFRLVLFAI-HSZRJFAPSA-N 0.000 claims 1
- FIXFXNNSCCMJIC-HSZRJFAPSA-N 4-[(6r)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-2-(2,4-dimethoxypyrimidin-5-yl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-6-yl]-2-fluorobenzonitrile Chemical compound COC1=NC(OC)=NC=C1C(N1C(C)C)=CC2=C1[C@@H](C=1C=C(F)C(C#N)=CC=1)N(C1=CN(C)C(=O)C(Cl)=C1)C2=O FIXFXNNSCCMJIC-HSZRJFAPSA-N 0.000 claims 1
- AMVOKCMSEMEARJ-HSZRJFAPSA-N 4-[(6r)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-2-(2,4-dimethoxypyrimidin-5-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=C1[C@@H](C=1C=CC(=CC=1)C#N)N(C1=CN(C)C(=O)C(Cl)=C1)C2=O AMVOKCMSEMEARJ-HSZRJFAPSA-N 0.000 claims 1
- LXWPKTFVYXPXGO-XMMPIXPASA-N 4-[(6r)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-6-yl]benzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1C(N1C(C)C)=CC2=C1[C@@H](C=1C=CC(=CC=1)C#N)N(C1=CN(C)C(=O)C(Cl)=C1)C2=O LXWPKTFVYXPXGO-XMMPIXPASA-N 0.000 claims 1
- RNNIMJVUCFVPIR-QHCPKHFHSA-N 4-[(6s)-2-(2-amino-4-methoxypyrimidin-5-yl)-5-(3-chloro-2-fluorophenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-6-yl]benzonitrile Chemical compound COC1=NC(N)=NC=C1C(N1C(C)C)=CC2=C1[C@H](C=1C=CC(=CC=1)C#N)N(C=1C(=C(Cl)C=CC=1)F)C2=O RNNIMJVUCFVPIR-QHCPKHFHSA-N 0.000 claims 1
- WDNMFYATUPBESP-QHCPKHFHSA-N 4-[(6s)-2-(2-amino-4-methoxypyrimidin-5-yl)-5-(3-chloro-4-fluorophenyl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-6-yl]benzonitrile Chemical compound COC1=NC(N)=NC=C1C(N1C(C)C)=CC2=C1[C@H](C=1C=CC(=CC=1)C#N)N(C=1C=C(Cl)C(F)=CC=1)C2=O WDNMFYATUPBESP-QHCPKHFHSA-N 0.000 claims 1
- WFWTZNXJCNYUAQ-DEOSSOPVSA-N 4-[(6s)-2-[2-(dimethylamino)-4-methoxypyrimidin-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(N(C)C)=NC=C1C(N1C(C)C)=CC2=C1[C@H](C=1C=CC(=CC=1)C#N)N(C1CCOCC1)C2=O WFWTZNXJCNYUAQ-DEOSSOPVSA-N 0.000 claims 1
- HHNKSOUSJFWEBC-VWLOTQADSA-N 4-[(6s)-5-(3-chloro-4-fluorophenyl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-6-yl]benzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1C(N1C(C)C)=CC2=C1[C@H](C=1C=CC(=CC=1)C#N)N(C=1C=C(Cl)C(F)=CC=1)C2=O HHNKSOUSJFWEBC-VWLOTQADSA-N 0.000 claims 1
- BTRWWPFRLVLFAI-QHCPKHFHSA-N 4-[(6s)-5-(5-chloro-1-methyl-2-oxopyridin-3-yl)-2-(2,4-dimethoxypyrimidin-5-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=C1[C@H](C=1C=CC(=CC=1)C#N)N(C=1C(N(C)C=C(Cl)C=1)=O)C2=O BTRWWPFRLVLFAI-QHCPKHFHSA-N 0.000 claims 1
- FIXFXNNSCCMJIC-QHCPKHFHSA-N 4-[(6s)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-2-(2,4-dimethoxypyrimidin-5-yl)-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-6-yl]-2-fluorobenzonitrile Chemical compound COC1=NC(OC)=NC=C1C(N1C(C)C)=CC2=C1[C@H](C=1C=C(F)C(C#N)=CC=1)N(C1=CN(C)C(=O)C(Cl)=C1)C2=O FIXFXNNSCCMJIC-QHCPKHFHSA-N 0.000 claims 1
- LXWPKTFVYXPXGO-DEOSSOPVSA-N 4-[(6s)-5-(5-chloro-1-methyl-6-oxopyridin-3-yl)-2-[2-(dimethylamino)-4-methoxypyrimidin-5-yl]-4-oxo-1-propan-2-yl-6h-pyrrolo[3,4-b]pyrrol-6-yl]benzonitrile Chemical compound COC1=NC(N(C)C)=NC=C1C(N1C(C)C)=CC2=C1[C@H](C=1C=CC(=CC=1)C#N)N(C1=CN(C)C(=O)C(Cl)=C1)C2=O LXWPKTFVYXPXGO-DEOSSOPVSA-N 0.000 claims 1
- SYFLQGBLVFJSKU-UHFFFAOYSA-N 4-[2-(2,4-dimethoxypyrimidin-5-yl)-5-(2,5-dimethylpyrazol-3-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(C=1N(N=C(C)C=1)C)C2=O SYFLQGBLVFJSKU-UHFFFAOYSA-N 0.000 claims 1
- QUNXWDFSYHBUTD-UHFFFAOYSA-N 4-[2-(2,4-dimethoxypyrimidin-5-yl)-5-(4-fluoro-2,5-dimethylpyrazol-3-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(C=1N(N=C(C)C=1F)C)C2=O QUNXWDFSYHBUTD-UHFFFAOYSA-N 0.000 claims 1
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| 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 |
| US9714249B2 (en) | 2013-05-28 | 2017-07-25 | Novartis Ag | Pyrazolo-pyrrolidin-4-one derivatives and their use in the treatment of disease |
| CN105263934B (zh) | 2013-05-28 | 2017-09-08 | 诺华股份有限公司 | 作为bet抑制剂的吡唑并‑吡咯烷‑4‑酮衍生物及其在治疗疾病中的用途 |
| GB201311891D0 (en) | 2013-07-03 | 2013-08-14 | Glaxosmithkline Ip Dev Ltd | Novel compound |
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| CN103724256A (zh) * | 2013-12-13 | 2014-04-16 | 成都丽璟科技有限公司 | 一种合成2-烷氧基-4-取代吡啶类衍生物的方法 |
| US20180228907A1 (en) | 2014-04-14 | 2018-08-16 | Arvinas, Inc. | Cereblon ligands and bifunctional compounds comprising the same |
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| US12312316B2 (en) | 2015-01-20 | 2025-05-27 | Arvinas Operations, Inc. | Compounds and methods for the targeted degradation of androgen receptor |
| EP3302482A4 (en) | 2015-06-05 | 2018-12-19 | Arvinas, Inc. | Tank-binding kinase-1 protacs and associated methods of use |
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| 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 |
| MX2019005007A (es) | 2016-11-01 | 2019-07-18 | Arvinas Inc | Protac dirigidos a la proteína tau y métodos asociados de uso. |
| JP6957620B2 (ja) | 2016-12-01 | 2021-11-02 | アルビナス・オペレーションズ・インコーポレイテッドＡｒｖｉｎａｓ Ｏｐｅｒａｔｉｏｎｓ， Ｉｎｃ． | エストロゲン受容体分解物質としてのテトラヒドロナフタレン誘導体およびテトラヒドロイソキノリン誘導体 |
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