KR102299834B1 - 바이사이클릭 헤테로사이클 화합물 및 치료에서의 그것의 용도 - Google Patents

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Publication number

KR102299834B1

KR102299834B1 KR1020157012696A KR20157012696A KR102299834B1 KR 102299834 B1 KR102299834 B1 KR 102299834B1 KR 1020157012696 A KR1020157012696 A KR 1020157012696A KR 20157012696 A KR20157012696 A KR 20157012696A KR 102299834 B1 KR102299834 B1 KR 102299834B1

Authority

KR

South Korea

Prior art keywords

methyl

dimethyl

pyrrolo

methylpiperazin

oxoethyl

Prior art date

2012-10-19

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.)

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• 229910052739 hydrogen Inorganic materials 0.000 claims description 235
• 239000001257 hydrogen Substances 0.000 claims description 235
• 125000000217 alkyl group Chemical group 0.000 claims description 212
• -1 C=O Inorganic materials 0.000 claims description 168
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 159
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 135
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 126
• 229910052757 nitrogen Inorganic materials 0.000 claims description 118
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• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 94
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• 102000050257 X-Linked Inhibitor of Apoptosis Human genes 0.000 claims description 79
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 73
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 73
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• QPLJYAKLSCXZSF-UHFFFAOYSA-N 2,2,2-trichloroethyl carbamate Chemical compound NC(=O)OCC(Cl)(Cl)Cl QPLJYAKLSCXZSF-UHFFFAOYSA-N 0.000 claims description 5
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• ZZOKVYOCRSMTSS-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl carbamate Chemical compound C1=CC=C2C(COC(=O)N)C3=CC=CC=C3C2=C1 ZZOKVYOCRSMTSS-UHFFFAOYSA-N 0.000 claims description 5
• JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 5
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• 125000000468 ketone group Chemical group 0.000 claims description 5
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• XXFXTBNFFMQVKJ-UHFFFAOYSA-N [diphenyl(trityloxy)methyl]benzene Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)OC(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XXFXTBNFFMQVKJ-UHFFFAOYSA-N 0.000 claims 2
• 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims 2
• 239000007795 chemical reaction product Substances 0.000 claims 2
• 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
• 201000005296 lung carcinoma Diseases 0.000 claims 2
• 125000004385 trihaloalkyl group Chemical group 0.000 claims 2
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• YTVAYXANYPKGTO-TYBLODHISA-N (5s)-1-[[(2r,5r)-1-[2-[6-[(4-fluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-c]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-4,5-dimethylpiperazin-2-one Chemical compound C([C@H](NC[C@@H]1CN2C(CN(C)[C@@H](C)C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=CN=C2CC1=CC=C(F)C=C1 YTVAYXANYPKGTO-TYBLODHISA-N 0.000 claims 1
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• HDZJZLGUWMMRPC-YSZBQJHXSA-N (6s)-4-[[(2r,5r)-1-[2-[3-[(2,4-difluorophenyl)methyl]-7,7-dimethyl-6h-pyrrolo[3,2-c]pyridazin-5-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-6-(methoxymethyl)morpholin-3-one Chemical compound O=C1CO[C@H](COC)CN1C[C@@H]1N(CC(=O)N2C3=CC(CC=4C(=CC(F)=CC=4)F)=NN=C3C(C)(C)C2)C[C@@H](C)NC1 HDZJZLGUWMMRPC-YSZBQJHXSA-N 0.000 claims 1
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• IRKYUHNGGATWEZ-QZTJIDSGSA-N 1-[[(2r,5r)-1-[2-[3-(1,1-difluorobutyl)-7,7-dimethyl-6h-pyrrolo[3,2-c]pyridazin-5-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-4,4-dimethylpyrrolidin-2-one Chemical compound C([C@H]1CN[C@H](C)CN1CC(=O)N1C=2C=C(N=NC=2C(C)(C)C1)C(F)(F)CCC)N1CC(C)(C)CC1=O IRKYUHNGGATWEZ-QZTJIDSGSA-N 0.000 claims 1
• UVWJAYNSPJKAHY-WZONZLPQSA-N 1-[[(2r,5r)-1-[2-[3-[(2,4-difluorophenyl)methyl]-7,7-dimethyl-6h-pyrrolo[3,2-c]pyridazin-5-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-3,4-dimethyl-2h-pyrrol-5-one Chemical compound C([C@H](NC[C@@H]1CN2C(C(C)=C(C)C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NN=C2CC1=CC=C(F)C=C1F UVWJAYNSPJKAHY-WZONZLPQSA-N 0.000 claims 1
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• YQRXDNUWXRGBNN-AUSIDOKSSA-N 1-[[(2r,5r)-1-[2-[3-[(4-fluorophenyl)methyl]-7,7-dimethyl-6h-pyrrolo[3,2-c]pyridazin-5-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-4,4-dimethylpyrrolidin-2-one Chemical compound C([C@H](NC[C@@H]1CN2C(CC(C)(C)C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NN=C2CC1=CC=C(F)C=C1 YQRXDNUWXRGBNN-AUSIDOKSSA-N 0.000 claims 1
• ACQJUZMWNCAIDG-UYAOXDASSA-N 1-[[(2r,5r)-1-[2-[6-(1,1-difluorobutyl)-3,3-dimethyl-2h-pyrrolo[3,2-c]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-3,4-dimethyl-2h-pyrrol-5-one Chemical compound C([C@H]1CN[C@H](C)CN1CC(=O)N1C=2C=C(N=CC=2C(C)(C)C1)C(F)(F)CCC)N1CC(C)=C(C)C1=O ACQJUZMWNCAIDG-UYAOXDASSA-N 0.000 claims 1
• KPIVQOFCCCAEDH-RTBURBONSA-N 1-[[(2r,5r)-1-[2-[6-(1,1-difluorobutyl)-3,3-dimethyl-2h-pyrrolo[3,2-c]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-4,4-dimethylpyrrolidin-2-one Chemical compound C([C@H]1CN[C@H](C)CN1CC(=O)N1C=2C=C(N=CC=2C(C)(C)C1)C(F)(F)CCC)N1CC(C)(C)CC1=O KPIVQOFCCCAEDH-RTBURBONSA-N 0.000 claims 1
• UIPIGZQXCLYXOC-NTKDMRAZSA-N 1-[[(2r,5r)-1-[2-[6-[(2,4-difluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-3,4-dimethyl-2h-pyrrol-5-one Chemical compound C([C@H](NC[C@@H]1CN2C(C(C)=C(C)C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NC=C2CC1=CC=C(F)C=C1F UIPIGZQXCLYXOC-NTKDMRAZSA-N 0.000 claims 1
• XJIWNJOQGDPRQB-AUSIDOKSSA-N 1-[[(2r,5r)-1-[2-[6-[(2,4-difluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-4,4-dimethylpyrrolidin-2-one Chemical compound C([C@H](NC[C@@H]1CN2C(CC(C)(C)C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NC=C2CC1=CC=C(F)C=C1F XJIWNJOQGDPRQB-AUSIDOKSSA-N 0.000 claims 1
• PVTBETDGAWAOFG-NTKDMRAZSA-N 1-[[(2r,5r)-1-[2-[6-[(2,4-difluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-c]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-3,4-dimethyl-2h-pyrrol-5-one Chemical compound C([C@H](NC[C@@H]1CN2C(C(C)=C(C)C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=CN=C2CC1=CC=C(F)C=C1F PVTBETDGAWAOFG-NTKDMRAZSA-N 0.000 claims 1
• OKIPUAJQHGAAIG-AUSIDOKSSA-N 1-[[(2r,5r)-1-[2-[6-[(2,4-difluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-c]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-4,4-dimethylpyrrolidin-2-one Chemical compound C([C@H](NC[C@@H]1CN2C(CC(C)(C)C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=CN=C2CC1=CC=C(F)C=C1F OKIPUAJQHGAAIG-AUSIDOKSSA-N 0.000 claims 1
• OZQNQMWPZQARPO-CJFMBICVSA-N 1-[[(2r,5r)-1-[2-[6-[(4-fluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-3,4-dimethyl-2h-pyrrol-5-one Chemical compound C([C@H](NC[C@@H]1CN2C(C(C)=C(C)C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NC=C2CC1=CC=C(F)C=C1 OZQNQMWPZQARPO-CJFMBICVSA-N 0.000 claims 1
• KAVCEEZPKWOTHJ-VRUSELTQSA-N 1-[[(2r,5r)-1-[2-[6-[(4-fluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-3,4-dimethylpyrrolidin-2-one Chemical compound O=C1C(C)C(C)CN1C[C@@H]1N(CC(=O)N2C3=CC(CC=4C=CC(F)=CC=4)=CN=C3C(C)(C)C2)C[C@@H](C)NC1 KAVCEEZPKWOTHJ-VRUSELTQSA-N 0.000 claims 1
• OZDZHRDZYTTYJK-HYBUGGRVSA-N 1-[[(2r,5r)-1-[2-[6-[(4-fluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-4,4-dimethylpyrrolidin-2-one Chemical compound C([C@H](NC[C@@H]1CN2C(CC(C)(C)C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NC=C2CC1=CC=C(F)C=C1 OZDZHRDZYTTYJK-HYBUGGRVSA-N 0.000 claims 1
• XFLMCOCWXCXNMR-ALRZPZFWSA-N 1-[[(2r,5r)-1-[2-[6-[(4-fluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-4-methylpyrrolidin-2-one Chemical compound O=C1CC(C)CN1C[C@@H]1N(CC(=O)N2C3=CC(CC=4C=CC(F)=CC=4)=CN=C3C(C)(C)C2)C[C@@H](C)NC1 XFLMCOCWXCXNMR-ALRZPZFWSA-N 0.000 claims 1
• BPYIXGGWCSLDPD-XMSQKQJNSA-N 1-[[(2r,5r)-1-[2-[6-[(4-fluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]piperazine-2,5-dione Chemical compound C([C@H](NC[C@@H]1CN2C(CNC(=O)C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NC=C2CC1=CC=C(F)C=C1 BPYIXGGWCSLDPD-XMSQKQJNSA-N 0.000 claims 1
• SQKVRVNPNTVINC-HYBUGGRVSA-N 1-[[(2r,5r)-1-[2-[6-[(4-fluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]piperidin-2-one Chemical compound C([C@H](NC[C@@H]1CN2C(CCCC2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NC=C2CC1=CC=C(F)C=C1 SQKVRVNPNTVINC-HYBUGGRVSA-N 0.000 claims 1
• AUDREFSLNZKLAH-CJFMBICVSA-N 1-[[(2r,5r)-1-[2-[6-[(4-fluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-c]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-3,4-dimethyl-2h-pyrrol-5-one Chemical compound C([C@H](NC[C@@H]1CN2C(C(C)=C(C)C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=CN=C2CC1=CC=C(F)C=C1 AUDREFSLNZKLAH-CJFMBICVSA-N 0.000 claims 1
• JURPFDUMXSSOQU-UYAOXDASSA-N 2-[[(2r,5r)-1-[2-[3-(1,1-difluorobutyl)-7,7-dimethyl-6h-pyrrolo[3,2-c]pyridazin-5-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-3h-isoindol-1-one Chemical compound C1C2=CC=CC=C2C(=O)N1C[C@H]1CN[C@H](C)CN1CC(=O)N1C(C=C(N=N2)C(F)(F)CCC)=C2C(C)(C)C1 JURPFDUMXSSOQU-UYAOXDASSA-N 0.000 claims 1
• RFQWTONABQIWEW-YLJYHZDGSA-N 2-[[(2r,5r)-1-[2-[3-(1,1-difluorobutyl)-7,7-dimethyl-6h-pyrrolo[3,2-c]pyridazin-5-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-6-fluoro-3h-isoindol-1-one Chemical compound C1C2=CC=C(F)C=C2C(=O)N1C[C@H]1CN[C@H](C)CN1CC(=O)N1C(C=C(N=N2)C(F)(F)CCC)=C2C(C)(C)C1 RFQWTONABQIWEW-YLJYHZDGSA-N 0.000 claims 1
• MPWIGZHHNCNVOO-KBMIEXCESA-N 2-[[(2r,5r)-1-[2-[3-[(2,4-difluorophenyl)methyl]-7,7-dimethyl-6h-pyrrolo[3,2-c]pyridazin-5-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-1-oxo-3h-isoindole-5-carbonitrile Chemical compound C([C@H](NC[C@@H]1CN2C(C3=CC=C(C=C3C2)C#N)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NN=C2CC1=CC=C(F)C=C1F MPWIGZHHNCNVOO-KBMIEXCESA-N 0.000 claims 1
• GGSBCIHJHQMJEB-KBMIEXCESA-N 2-[[(2r,5r)-1-[2-[3-[(2,4-difluorophenyl)methyl]-7,7-dimethyl-6h-pyrrolo[3,2-c]pyridazin-5-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-3-oxo-1h-isoindole-5-carbonitrile Chemical compound C([C@H](NC[C@@H]1CN2C(C3=CC(=CC=C3C2)C#N)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NN=C2CC1=CC=C(F)C=C1F GGSBCIHJHQMJEB-KBMIEXCESA-N 0.000 claims 1
• NVKDUOBSCHJBEF-NTKDMRAZSA-N 2-[[(2r,5r)-1-[2-[3-[(2,4-difluorophenyl)methyl]-7,7-dimethyl-6h-pyrrolo[3,2-c]pyridazin-5-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-3h-isoindol-1-one Chemical compound C([C@H](NC[C@@H]1CN2C(C3=CC=CC=C3C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NN=C2CC1=CC=C(F)C=C1F NVKDUOBSCHJBEF-NTKDMRAZSA-N 0.000 claims 1
• DQKBYCWEDPITFE-XMSQKQJNSA-N 2-[[(2r,5r)-1-[2-[3-[(2,4-difluorophenyl)methyl]-7,7-dimethyl-6h-pyrrolo[3,2-c]pyridazin-5-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-4-fluoro-3h-isoindol-1-one Chemical compound C([C@H](NC[C@@H]1CN2C(C3=C(C(=CC=C3)F)C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NN=C2CC1=CC=C(F)C=C1F DQKBYCWEDPITFE-XMSQKQJNSA-N 0.000 claims 1
• KWASCEBFUSALIJ-XMSQKQJNSA-N 2-[[(2r,5r)-1-[2-[3-[(2,4-difluorophenyl)methyl]-7,7-dimethyl-6h-pyrrolo[3,2-c]pyridazin-5-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-4-hydroxy-3h-isoindol-1-one Chemical compound C([C@H](NC[C@@H]1CN2C(C3=C(C(=CC=C3)O)C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NN=C2CC1=CC=C(F)C=C1F KWASCEBFUSALIJ-XMSQKQJNSA-N 0.000 claims 1
• RYWHXXFDHDENSD-HOYKHHGWSA-N 2-[[(2r,5r)-1-[2-[3-[(2,4-difluorophenyl)methyl]-7,7-dimethyl-6h-pyrrolo[3,2-c]pyridazin-5-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-5-fluoro-3h-isoindol-1-one Chemical compound C([C@H](NC[C@@H]1CN2C(C3=CC=C(F)C=C3C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NN=C2CC1=CC=C(F)C=C1F RYWHXXFDHDENSD-HOYKHHGWSA-N 0.000 claims 1
• INFOULWSBBKDHP-WZONZLPQSA-N 2-[[(2r,5r)-1-[2-[3-[(2,4-difluorophenyl)methyl]-7,7-dimethyl-6h-pyrrolo[3,2-c]pyridazin-5-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-5-hydroxy-3h-isoindol-1-one Chemical compound C([C@H](NC[C@@H]1CN2C(C3=CC=C(O)C=C3C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NN=C2CC1=CC=C(F)C=C1F INFOULWSBBKDHP-WZONZLPQSA-N 0.000 claims 1
• ROXCMZCRKWPGCG-HOYKHHGWSA-N 2-[[(2r,5r)-1-[2-[3-[(2,4-difluorophenyl)methyl]-7,7-dimethyl-6h-pyrrolo[3,2-c]pyridazin-5-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-6-fluoro-3h-isoindol-1-one Chemical compound C([C@H](NC[C@@H]1CN2C(C3=CC(F)=CC=C3C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NN=C2CC1=CC=C(F)C=C1F ROXCMZCRKWPGCG-HOYKHHGWSA-N 0.000 claims 1
• XGTYPJLWBJAWIS-WZONZLPQSA-N 2-[[(2r,5r)-1-[2-[3-[(2,4-difluorophenyl)methyl]-7,7-dimethyl-6h-pyrrolo[3,2-c]pyridazin-5-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-6-hydroxy-3h-isoindol-1-one Chemical compound C([C@H](NC[C@@H]1CN2C(C3=CC(O)=CC=C3C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NN=C2CC1=CC=C(F)C=C1F XGTYPJLWBJAWIS-WZONZLPQSA-N 0.000 claims 1
• QHNOWASNJQEWLM-WZONZLPQSA-N 2-[[(2r,5r)-1-[2-[3-[(2,4-difluorophenyl)methyl]-7,7-dimethyl-6h-pyrrolo[3,2-c]pyridazin-5-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-7-fluoro-3h-isoindol-1-one Chemical compound C([C@H](NC[C@@H]1CN2C(C3=C(F)C=CC=C3C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NN=C2CC1=CC=C(F)C=C1F QHNOWASNJQEWLM-WZONZLPQSA-N 0.000 claims 1
• ZJOWQMMGXYFDHJ-CJFMBICVSA-N 2-[[(2r,5r)-1-[2-[3-[(4-fluorophenyl)methyl]-7,7-dimethyl-6h-pyrrolo[3,2-c]pyridazin-5-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-3h-isoindol-1-one Chemical compound C([C@H](NC[C@@H]1CN2C(C3=CC=CC=C3C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NN=C2CC1=CC=C(F)C=C1 ZJOWQMMGXYFDHJ-CJFMBICVSA-N 0.000 claims 1
• HUEUZCKLGGAVOP-UYAOXDASSA-N 2-[[(2r,5r)-1-[2-[6-(1,1-difluorobutyl)-3,3-dimethyl-2h-pyrrolo[3,2-c]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-1h-pyrrolo[3,4-c]pyridin-3-one Chemical compound C1C2=CC=NC=C2C(=O)N1C[C@H]1CN[C@H](C)CN1CC(=O)N1C(C=C(N=C2)C(F)(F)CCC)=C2C(C)(C)C1 HUEUZCKLGGAVOP-UYAOXDASSA-N 0.000 claims 1
• YGBUNJXBNYURQL-TZIWHRDSSA-N 2-[[(2r,5r)-1-[2-[6-(1,1-difluorobutyl)-3,3-dimethyl-2h-pyrrolo[3,2-c]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-3h-isoindol-1-one Chemical compound C1C2=CC=CC=C2C(=O)N1C[C@H]1CN[C@H](C)CN1CC(=O)N1C(C=C(N=C2)C(F)(F)CCC)=C2C(C)(C)C1 YGBUNJXBNYURQL-TZIWHRDSSA-N 0.000 claims 1
• KZJBINMQYZBLTQ-FQRUVTKNSA-N 2-[[(2r,5r)-1-[2-[6-[(2,4-difluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-1-oxo-3h-isoindole-5-carbonitrile Chemical compound C([C@H](NC[C@@H]1CN2C(C3=CC=C(C=C3C2)C#N)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NC=C2CC1=CC=C(F)C=C1F KZJBINMQYZBLTQ-FQRUVTKNSA-N 0.000 claims 1
• RWUGLSQHRDWQKA-FQRUVTKNSA-N 2-[[(2r,5r)-1-[2-[6-[(2,4-difluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-3-oxo-1h-isoindole-5-carbonitrile Chemical compound C([C@H](NC[C@@H]1CN2C(C3=CC(=CC=C3C2)C#N)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NC=C2CC1=CC=C(F)C=C1F RWUGLSQHRDWQKA-FQRUVTKNSA-N 0.000 claims 1
• SZYRJKAUAVQSMJ-CJFMBICVSA-N 2-[[(2r,5r)-1-[2-[6-[(2,4-difluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-3h-isoindol-1-one Chemical compound C([C@H](NC[C@@H]1CN2C(C3=CC=CC=C3C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NC=C2CC1=CC=C(F)C=C1F SZYRJKAUAVQSMJ-CJFMBICVSA-N 0.000 claims 1
• FBCVBPOXQJUCOM-AUSIDOKSSA-N 2-[[(2r,5r)-1-[2-[6-[(2,4-difluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-4-hydroxy-3h-isoindol-1-one Chemical compound C([C@H](NC[C@@H]1CN2C(C3=C(C(=CC=C3)O)C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NC=C2CC1=CC=C(F)C=C1F FBCVBPOXQJUCOM-AUSIDOKSSA-N 0.000 claims 1
• XFZWHYOCJXRJPC-NTKDMRAZSA-N 2-[[(2r,5r)-1-[2-[6-[(2,4-difluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-5-hydroxy-3h-isoindol-1-one Chemical compound C([C@H](NC[C@@H]1CN2C(C3=CC=C(O)C=C3C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NC=C2CC1=CC=C(F)C=C1F XFZWHYOCJXRJPC-NTKDMRAZSA-N 0.000 claims 1
• VNMWZLBKQABREV-NTKDMRAZSA-N 2-[[(2r,5r)-1-[2-[6-[(2,4-difluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-6-hydroxy-3h-isoindol-1-one Chemical compound C([C@H](NC[C@@H]1CN2C(C3=CC(O)=CC=C3C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NC=C2CC1=CC=C(F)C=C1F VNMWZLBKQABREV-NTKDMRAZSA-N 0.000 claims 1
• RHSPNDNLSYKUJO-CJFMBICVSA-N 2-[[(2r,5r)-1-[2-[6-[(2,4-difluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-c]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-3h-isoindol-1-one Chemical compound C([C@H](NC[C@@H]1CN2C(C3=CC=CC=C3C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=CN=C2CC1=CC=C(F)C=C1F RHSPNDNLSYKUJO-CJFMBICVSA-N 0.000 claims 1
• VHLRTLGXLCXZHQ-CJFMBICVSA-N 2-[[(2r,5r)-1-[2-[6-[(4-fluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-1h-pyrrolo[3,4-c]pyridin-3-one Chemical compound C([C@H](NC[C@@H]1CN2C(C3=CN=CC=C3C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NC=C2CC1=CC=C(F)C=C1 VHLRTLGXLCXZHQ-CJFMBICVSA-N 0.000 claims 1
• XYDGOXJJDFKAAT-QFQXNSOFSA-N 2-[[(2r,5r)-1-[2-[6-[(4-fluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-3h-isoindol-1-one Chemical compound C([C@H](NC[C@@H]1CN2C(C3=CC=CC=C3C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NC=C2CC1=CC=C(F)C=C1 XYDGOXJJDFKAAT-QFQXNSOFSA-N 0.000 claims 1
• MURQKJQZUXPUNT-QFQXNSOFSA-N 2-[[(2r,5r)-1-[2-[6-[(4-fluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-5-methoxy-3h-isoindol-1-one Chemical compound C([C@@H](C)NC[C@@H]1CN2C(=O)C3=CC=C(C=C3C2)OC)N1CC(=O)N(C1=C2)CC(C)(C)C1=NC=C2CC1=CC=C(F)C=C1 MURQKJQZUXPUNT-QFQXNSOFSA-N 0.000 claims 1
• LINGVLYPDLNMKZ-QFQXNSOFSA-N 2-[[(2r,5r)-1-[2-[6-[(4-fluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-c]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-3h-isoindol-1-one Chemical compound C([C@H](NC[C@@H]1CN2C(C3=CC=CC=C3C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=CN=C2CC1=CC=C(F)C=C1 LINGVLYPDLNMKZ-QFQXNSOFSA-N 0.000 claims 1
• HIUYIWOWQIJEHS-QFQXNSOFSA-N 2-[[(2r,5r)-1-[2-[6-[(4-fluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-c]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-5-methoxy-3h-isoindol-1-one Chemical compound C([C@@H](C)NC[C@@H]1CN2C(=O)C3=CC=C(C=C3C2)OC)N1CC(=O)N(C1=C2)CC(C)(C)C1=CN=C2CC1=CC=C(F)C=C1 HIUYIWOWQIJEHS-QFQXNSOFSA-N 0.000 claims 1
• WICAOTINHKRDBU-AUSIDOKSSA-N 3-[[(2r,5r)-1-[2-[6-[(4-fluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-5,5-dimethyl-1,3-oxazolidin-2-one Chemical compound C([C@H](NC[C@@H]1CN2C(OC(C)(C)C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NC=C2CC1=CC=C(F)C=C1 WICAOTINHKRDBU-AUSIDOKSSA-N 0.000 claims 1
• UYBUVYYDBONSFM-HYBUGGRVSA-N 4-[[(2r,5r)-1-[2-[6-[(4-fluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-1,4-oxazepan-3-one Chemical compound C([C@H](NC[C@@H]1CN2C(COCCC2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NC=C2CC1=CC=C(F)C=C1 UYBUVYYDBONSFM-HYBUGGRVSA-N 0.000 claims 1
• VXWQCACVEZHNQP-HYBUGGRVSA-N 4-[[(2r,5r)-1-[2-[6-[(4-fluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-1,4-oxazepan-5-one Chemical compound C([C@H](NC[C@@H]1CN2C(CCOCC2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NC=C2CC1=CC=C(F)C=C1 VXWQCACVEZHNQP-HYBUGGRVSA-N 0.000 claims 1
• ISUMZGCKOZIXJV-HYBUGGRVSA-N 4-[[(2r,5r)-1-[2-[6-[(4-fluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-6,6-dimethylmorpholin-3-one Chemical compound C([C@H](NC[C@@H]1CN2C(COC(C)(C)C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NC=C2CC1=CC=C(F)C=C1 ISUMZGCKOZIXJV-HYBUGGRVSA-N 0.000 claims 1
• HOFNRQFANWLTKK-QZTJIDSGSA-N 6-[[(2r,5r)-1-[2-[3-(1,1-difluorobutyl)-7,7-dimethyl-6h-pyrrolo[3,2-c]pyridazin-5-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-7h-pyrrolo[3,4-b]pyridin-5-one Chemical compound C1C2=NC=CC=C2C(=O)N1C[C@H]1CN[C@H](C)CN1CC(=O)N1C(C=C(N=N2)C(F)(F)CCC)=C2C(C)(C)C1 HOFNRQFANWLTKK-QZTJIDSGSA-N 0.000 claims 1
• DHLZEVDCHWUCOP-AUSIDOKSSA-N 6-[[(2r,5r)-1-[2-[6-[(2,4-difluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-c]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-7h-pyrrolo[3,4-b]pyridin-5-one Chemical compound C([C@H](NC[C@@H]1CN2C(C3=CC=CN=C3C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=CN=C2CC1=CC=C(F)C=C1F DHLZEVDCHWUCOP-AUSIDOKSSA-N 0.000 claims 1
• WQQWXIVBXQKIBF-CJFMBICVSA-N 6-[[(2r,5r)-1-[2-[6-[(4-fluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-5h-pyrrolo[3,4-b]pyridin-7-one Chemical compound C([C@H](NC[C@@H]1CN2C(C3=NC=CC=C3C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NC=C2CC1=CC=C(F)C=C1 WQQWXIVBXQKIBF-CJFMBICVSA-N 0.000 claims 1
• IHAZNMDOVWVENX-HYBUGGRVSA-N 6-[[(2r,5r)-1-[2-[6-[(4-fluorophenyl)methyl]-3,3-dimethyl-2h-pyrrolo[3,2-b]pyridin-1-yl]-2-oxoethyl]-5-methylpiperazin-2-yl]methyl]-7h-pyrrolo[3,4-b]pyridin-5-one Chemical compound C([C@H](NC[C@@H]1CN2C(C3=CC=CN=C3C2)=O)C)N1CC(=O)N(C1=C2)CC(C)(C)C1=NC=C2CC1=CC=C(F)C=C1 IHAZNMDOVWVENX-HYBUGGRVSA-N 0.000 claims 1
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