KR102578786B1 - 약학적 화합물 - Google Patents

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Publication number

KR102578786B1

KR102578786B1 KR1020197014352A KR20197014352A KR102578786B1 KR 102578786 B1 KR102578786 B1 KR 102578786B1 KR 1020197014352 A KR1020197014352 A KR 1020197014352A KR 20197014352 A KR20197014352 A KR 20197014352A KR 102578786 B1 KR102578786 B1 KR 102578786B1

Authority

KR

South Korea

Prior art keywords

pyrrolidin

dimethylisoxazol

benzo

imidazol

difluorophenyl

Prior art date

2016-10-18

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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• 150000001875 compounds Chemical class 0.000 title claims abstract description 66
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 57
• 201000011510 cancer Diseases 0.000 claims abstract description 34
• 206010060862 Prostate cancer Diseases 0.000 claims abstract description 18
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims abstract description 18
• 230000000694 effects Effects 0.000 claims abstract description 18
• 150000003839 salts Chemical class 0.000 claims abstract description 16
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 732
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 350
• 238000000034 method Methods 0.000 claims description 278
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 189
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 132
• XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical group O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 75
• -1 isoxazole compound Chemical class 0.000 claims description 70
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 36
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 30
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 20
• 125000000217 alkyl group Chemical group 0.000 claims description 18
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 17
• 125000001072 heteroaryl group Chemical group 0.000 claims description 12
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 11
• 125000003118 aryl group Chemical group 0.000 claims description 11
• YFPCLQKFNXUAAK-UHFFFAOYSA-N cyclopentyl acetate Chemical compound CC(=O)OC1CCCC1 YFPCLQKFNXUAAK-UHFFFAOYSA-N 0.000 claims description 10
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 10
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• 125000004432 carbon atom Chemical group C* 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims description 8
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 7
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 7
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 7
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 230000004777 loss-of-function mutation Effects 0.000 claims description 7
• NXFFJDQHYLNEJK-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1h-cyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)C)=CC(F)=CC=2C=2CCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 NXFFJDQHYLNEJK-UHFFFAOYSA-N 0.000 claims description 6
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 6
• 239000004480 active ingredient Substances 0.000 claims description 6
• 125000000623 heterocyclic group Chemical group 0.000 claims description 6
• 201000005202 lung cancer Diseases 0.000 claims description 6
• 208000020816 lung neoplasm Diseases 0.000 claims description 6
• 206010005003 Bladder cancer Diseases 0.000 claims description 5
• 230000008569 process Effects 0.000 claims description 5
• 229910052721 tungsten Inorganic materials 0.000 claims description 5
• 201000005112 urinary bladder cancer Diseases 0.000 claims description 5
• 229910052727 yttrium Inorganic materials 0.000 claims description 5
• 206010006187 Breast cancer Diseases 0.000 claims description 4
• 208000026310 Breast neoplasm Diseases 0.000 claims description 4
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
• NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 208000032839 leukemia Diseases 0.000 claims description 4
• 238000002560 therapeutic procedure Methods 0.000 claims description 4
• 241001465754 Metazoa Species 0.000 claims description 3
• 102100038895 Myc proto-oncogene protein Human genes 0.000 claims description 3
• 101710135898 Myc proto-oncogene protein Proteins 0.000 claims description 3
• 101710150448 Transcriptional regulator Myc Proteins 0.000 claims description 3
• 230000004913 activation Effects 0.000 claims description 3
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
• IUVCECHSUQJXMM-UHFFFAOYSA-N cyclobutyl acetate Chemical compound CC(=O)OC1CCC1 IUVCECHSUQJXMM-UHFFFAOYSA-N 0.000 claims description 3
• 201000001037 lung lymphoma Diseases 0.000 claims description 3
• ZBIORFWTWOHVLU-ZJSXRUAMSA-N (5R)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]-1-(3-fluorophenyl)pyrrolidin-2-one Chemical compound CC1=NOC(=C1C1=CC2=C(N(C(=N2)[C@H]2CCC(N2C2=CC(=CC=C2)F)=O)[C@H]2CN(CC2)S(=O)(=O)C)C=C1)C ZBIORFWTWOHVLU-ZJSXRUAMSA-N 0.000 claims description 2
• BXMMBJZCICOLJZ-ZJSXRUAMSA-N (5R)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]-1-phenylpyrrolidin-2-one Chemical compound CC1=NOC(=C1C1=CC2=C(N(C(=N2)[C@H]2CCC(N2C2=CC=CC=C2)=O)[C@H]2CN(CC2)S(=O)(=O)C)C=C1)C BXMMBJZCICOLJZ-ZJSXRUAMSA-N 0.000 claims description 2
• STOMFPNBLULCGG-WFCDKWQMSA-N (5S)-1-(3,4-difluorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(2-methyloxan-4-yl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound FC=1C=C(C=CC=1F)N1C(CC[C@H]1C1=NC2=C(N1C1CC(OCC1)C)C=CC(=C2)C=1C(=NOC=1C)C)=O STOMFPNBLULCGG-WFCDKWQMSA-N 0.000 claims description 2
• ULDGTNGEBKCLAO-DVECYGJZSA-N (5S)-1-(3,4-difluorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-(3,3,3-trifluoropropanoyl)pyrrolidin-3-yl]benzimidazol-2-yl]pyrrolidin-2-one Chemical compound FC=1C=C(C=CC=1F)N1C(CC[C@H]1C1=NC2=C(N1[C@H]1CN(CC1)C(CC(F)(F)F)=O)C=CC(=C2)C=1C(=NOC=1C)C)=O ULDGTNGEBKCLAO-DVECYGJZSA-N 0.000 claims description 2
• UTPZDAWGTMIGLA-DEOSSOPVSA-N (5S)-1-(4-chloro-3-fluorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(1,1-dioxothian-4-yl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound ClC1=C(C=C(C=C1)N1C(CC[C@H]1C1=NC2=C(N1C1CCS(CC1)(=O)=O)C=CC(=C2)C=1C(=NOC=1C)C)=O)F UTPZDAWGTMIGLA-DEOSSOPVSA-N 0.000 claims description 2
• PMGUZDKNKIHGQZ-VWLOTQADSA-N (5S)-1-(4-chloro-3-fluorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(1-methylsulfonylpiperidin-4-yl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound ClC1=C(C=C(C=C1)N1C(CC[C@H]1C1=NC2=C(N1C1CCN(CC1)S(=O)(=O)C)C=CC(=C2)C=1C(=NOC=1C)C)=O)F PMGUZDKNKIHGQZ-VWLOTQADSA-N 0.000 claims description 2
• DBPNOZYOMBIZLU-QPPBQGQZSA-N (5S)-1-(4-chlorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]pyrrolidin-2-one Chemical compound ClC1=CC=C(C=C1)N1C(CC[C@H]1C1=NC2=C(N1[C@H]1CN(CC1)S(=O)(=O)C)C=CC(=C2)C=1C(=NOC=1C)C)=O DBPNOZYOMBIZLU-QPPBQGQZSA-N 0.000 claims description 2
• VDOXBIMAXXPWTD-DEOSSOPVSA-N (5S)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(1,1-dioxothian-4-yl)benzimidazol-2-yl]-1-(3-fluorophenyl)pyrrolidin-2-one Chemical compound CC1=NOC(=C1C1=CC2=C(N(C(=N2)[C@@H]2CCC(N2C2=CC(=CC=C2)F)=O)C2CCS(CC2)(=O)=O)C=C1)C VDOXBIMAXXPWTD-DEOSSOPVSA-N 0.000 claims description 2
• FGLKKHAROSYDQM-DEOSSOPVSA-N (5S)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(2-oxaspiro[3.3]heptan-6-yl)benzimidazol-2-yl]-1-(3-fluoro-4-methoxyphenyl)pyrrolidin-2-one Chemical compound CC1=NOC(=C1C1=CC2=C(N(C(=N2)[C@@H]2CCC(N2C2=CC(=C(C=C2)OC)F)=O)C2CC3(COC3)C2)C=C1)C FGLKKHAROSYDQM-DEOSSOPVSA-N 0.000 claims description 2
• RVVRLBMFYANMGW-XXBNENTESA-N (5S)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]-1-(5-fluoropyridin-3-yl)pyrrolidin-2-one Chemical compound CC1=NOC(=C1C1=CC2=C(N(C(=N2)[C@@H]2CCC(N2C=2C=NC=C(C=2)F)=O)[C@H]2CN(CC2)S(=O)(=O)C)C=C1)C RVVRLBMFYANMGW-XXBNENTESA-N 0.000 claims description 2
• FWJIKSRKDGCSJW-MZEQIWSPSA-N [(1R,3R)-3-[2-[(2S)-1-(3-chloro-4-methoxyphenyl)-5-oxopyrrolidin-2-yl]-5-(3,5-dimethyl-1,2-oxazol-4-yl)benzimidazol-1-yl]cyclopentyl] acetate Chemical compound C(C)(=O)O[C@H]1C[C@@H](CC1)N1C(=NC2=C1C=CC(=C2)C=1C(=NOC=1C)C)[C@H]1N(C(CC1)=O)C1=CC(=C(C=C1)OC)Cl FWJIKSRKDGCSJW-MZEQIWSPSA-N 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 201000005787 hematologic cancer Diseases 0.000 claims description 2
• 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims description 2
• GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 claims description 2
• 125000003003 spiro group Chemical group 0.000 claims description 2
• 125000001475 halogen functional group Chemical group 0.000 claims 5
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
• 238000004519 manufacturing process Methods 0.000 claims 2
• ZVOGMGRUBPKDBW-NTKDMRAZSA-N (5R)-1-(3,4-difluorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]pyrrolidin-2-one Chemical compound FC=1C=C(C=CC=1F)N1C(CC[C@@H]1C1=NC2=C(N1[C@H]1CN(CC1)S(=O)(=O)C)C=CC(=C2)C=1C(=NOC=1C)C)=O ZVOGMGRUBPKDBW-NTKDMRAZSA-N 0.000 claims 1
• RPGKLKPABYTBDS-SANMLTNESA-N (5S)-1-(2,3-dihydro-1-benzofuran-5-yl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(1-methylsulfonylpiperidin-4-yl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound Cc1noc(C)c1-c1ccc2n(C3CCN(CC3)S(C)(=O)=O)c(nc2c1)[C@@H]1CCC(=O)N1c1ccc2OCCc2c1 RPGKLKPABYTBDS-SANMLTNESA-N 0.000 claims 1
• DXSLRPZJUKGZFB-RDGATRHJSA-N (5S)-1-(2,3-dihydro-1-benzofuran-5-yl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]pyrrolidin-2-one Chemical compound O1CCC2=C1C=CC(=C2)N1C(CC[C@H]1C1=NC2=C(N1[C@H]1CN(CC1)S(=O)(=O)C)C=CC(=C2)C=1C(=NOC=1C)C)=O DXSLRPZJUKGZFB-RDGATRHJSA-N 0.000 claims 1
• CWDQIHJHVWOKQK-WIIYFNMSSA-N (5S)-1-(3,4-dichlorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(1,1-dioxothian-3-yl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound CC1=C(C(C)=NO1)C1=CC=C2N(C3CCCS(=O)(=O)C3)C(=NC2=C1)[C@@H]1CCC(=O)N1C1=CC(Cl)=C(Cl)C=C1 CWDQIHJHVWOKQK-WIIYFNMSSA-N 0.000 claims 1
• CHPQNARHXRFIQK-DEOSSOPVSA-N (5S)-1-(3,4-dichlorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(1,1-dioxothian-4-yl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound CC1=C(C(C)=NO1)C1=CC=C2N(C3CCS(=O)(=O)CC3)C(=NC2=C1)[C@@H]1CCC(=O)N1C1=CC(Cl)=C(Cl)C=C1 CHPQNARHXRFIQK-DEOSSOPVSA-N 0.000 claims 1
• XYTJGCAPGDACHC-WIIYFNMSSA-N (5S)-1-(3,4-dichlorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(1-methylpyrrolidin-3-yl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound ClC=1C=C(C=CC=1Cl)N1C(CC[C@H]1C1=NC2=C(N1C1CN(CC1)C)C=CC(=C2)C=1C(=NOC=1C)C)=O XYTJGCAPGDACHC-WIIYFNMSSA-N 0.000 claims 1
• LSYSNZWPNDLMJT-VWLOTQADSA-N (5S)-1-(3,4-dichlorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(1-methylsulfonylpiperidin-4-yl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound ClC=1C=C(C=CC=1Cl)N1C(CC[C@H]1C1=NC2=C(N1C1CCN(CC1)S(=O)(=O)C)C=CC(=C2)C=1C(=NOC=1C)C)=O LSYSNZWPNDLMJT-VWLOTQADSA-N 0.000 claims 1
• QQABZVCPNWWMAA-YJLYGGOZSA-N (5S)-1-(3,4-dichlorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(1R,3R)-3-hydroxycyclopentyl]benzimidazol-2-yl]pyrrolidin-2-one Chemical compound ClC=1C=C(C=CC=1Cl)N1C(CC[C@H]1C1=NC2=C(N1[C@H]1C[C@@H](CC1)O)C=CC(=C2)C=1C(=NOC=1C)C)=O QQABZVCPNWWMAA-YJLYGGOZSA-N 0.000 claims 1
• MLORJSBKOXZDCX-DEOSSOPVSA-N (5S)-1-(3,4-difluorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(1,1-dioxothian-4-yl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound CC1=C(C(C)=NO1)C1=CC=C2N(C3CCS(=O)(=O)CC3)C(=NC2=C1)[C@@H]1CCC(=O)N1C1=CC(F)=C(F)C=C1 MLORJSBKOXZDCX-DEOSSOPVSA-N 0.000 claims 1
• BLJLQCZVQABBHU-WIIYFNMSSA-N (5S)-1-(3,4-difluorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(1-methylpyrrolidin-3-yl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound FC=1C=C(C=CC=1F)N1C(CC[C@H]1C1=NC2=C(N1C1CN(CC1)C)C=CC(=C2)C=1C(=NOC=1C)C)=O BLJLQCZVQABBHU-WIIYFNMSSA-N 0.000 claims 1
• MGEBXIDSZOPBPD-QHCPKHFHSA-N (5S)-1-(3,4-difluorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(2-methylpropyl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound FC=1C=C(C=CC=1F)N1C(CC[C@H]1C1=NC2=C(N1CC(C)C)C=CC(=C2)C=1C(=NOC=1C)C)=O MGEBXIDSZOPBPD-QHCPKHFHSA-N 0.000 claims 1
• XDIXTBJESCLKOS-QHCPKHFHSA-N (5S)-1-(3,4-difluorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(3-methoxypropyl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound FC=1C=C(C=CC=1F)N1C(CC[C@H]1C1=NC2=C(N1CCCOC)C=CC(=C2)C=1C(=NOC=1C)C)=O XDIXTBJESCLKOS-QHCPKHFHSA-N 0.000 claims 1
• ROCLLYGGGGTBPI-VWLOTQADSA-N (5S)-1-(3,4-difluorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(pyridin-3-ylmethyl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound FC=1C=C(C=CC=1F)N1C(CC[C@H]1C1=NC2=C(N1CC=1C=NC=CC=1)C=CC(=C2)C=1C(=NOC=1C)C)=O ROCLLYGGGGTBPI-VWLOTQADSA-N 0.000 claims 1
• ZVOGMGRUBPKDBW-DVECYGJZSA-N (5S)-1-(3,4-difluorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]pyrrolidin-2-one Chemical compound FC=1C=C(C=CC=1F)N1C(CC[C@H]1C1=NC2=C(N1[C@H]1CN(CC1)S(=O)(=O)C)C=CC(=C2)C=1C(=NOC=1C)C)=O ZVOGMGRUBPKDBW-DVECYGJZSA-N 0.000 claims 1
• ZVOGMGRUBPKDBW-CYFREDJKSA-N (5S)-1-(3,4-difluorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3S)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]pyrrolidin-2-one Chemical compound FC=1C=C(C=CC=1F)N1C(CC[C@H]1C1=NC2=C(N1[C@@H]1CN(CC1)S(=O)(=O)C)C=CC(=C2)C=1C(=NOC=1C)C)=O ZVOGMGRUBPKDBW-CYFREDJKSA-N 0.000 claims 1
• FBRULYOLFNZEHJ-QFIPXVFZSA-N (5S)-1-(3,4-difluorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-propylbenzimidazol-2-yl]pyrrolidin-2-one Chemical compound FC=1C=C(C=CC=1F)N1C(CC[C@H]1C1=NC2=C(N1CCC)C=CC(=C2)C=1C(=NOC=1C)C)=O FBRULYOLFNZEHJ-QFIPXVFZSA-N 0.000 claims 1
• ZXHMDXFSZLXPMZ-IBGZPJMESA-N (5S)-1-(3,4-difluorophenyl)-5-[6-(3,5-dimethyl-1,2-oxazol-4-yl)-1H-benzimidazol-2-yl]pyrrolidin-2-one Chemical compound FC=1C=C(C=CC=1F)N1C(CC[C@H]1C1=NC2=C(N1)C=CC(=C2)C=1C(=NOC=1C)C)=O ZXHMDXFSZLXPMZ-IBGZPJMESA-N 0.000 claims 1
• CGIWFVPVWSZDBU-DEOSSOPVSA-N (5S)-1-(3,5-dichlorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(1,1-dioxothian-4-yl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound CC1=C(C(C)=NO1)C1=CC=C2N(C3CCS(=O)(=O)CC3)C(=NC2=C1)[C@@H]1CCC(=O)N1C1=CC(Cl)=CC(Cl)=C1 CGIWFVPVWSZDBU-DEOSSOPVSA-N 0.000 claims 1
• JEVJGAISWORGCC-DEOSSOPVSA-N (5S)-1-(3,5-difluorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(1,1-dioxothian-4-yl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound CC1=C(C(C)=NO1)C1=CC=C2N(C3CCS(=O)(=O)CC3)C(=NC2=C1)[C@@H]1CCC(=O)N1C1=CC(F)=CC(F)=C1 JEVJGAISWORGCC-DEOSSOPVSA-N 0.000 claims 1
• QTEKUBLJKFWVBY-YKSBVNFPSA-N (5S)-1-(3,5-difluorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]pyrrolidin-2-one Chemical compound FC=1C=C(C=C(C=1)F)N1C(CC[C@H]1C1=NC2=C(N1[C@H]1CN(CC1)S(=O)(=O)C)C=CC(=C2)C=1C(=NOC=1C)C)=O QTEKUBLJKFWVBY-YKSBVNFPSA-N 0.000 claims 1
• UYKCNNHZSJXEBG-DEOSSOPVSA-N (5S)-1-(3-chloro-4-fluorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(1,1-dioxothian-4-yl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound CC1=C(C(C)=NO1)C1=CC=C2N(C3CCS(=O)(=O)CC3)C(=NC2=C1)[C@@H]1CCC(=O)N1C1=CC(Cl)=C(F)C=C1 UYKCNNHZSJXEBG-DEOSSOPVSA-N 0.000 claims 1
• VUHJNIVODXDQQT-DEOSSOPVSA-N (5S)-1-(3-chloro-4-methoxyphenyl)-5-[1-(4,4-difluorocyclohexyl)-5-(3,5-dimethyl-1,2-oxazol-4-yl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound ClC=1C=C(C=CC=1OC)N1C(CC[C@H]1C1=NC2=C(N1C1CCC(CC1)(F)F)C=CC(=C2)C=1C(=NOC=1C)C)=O VUHJNIVODXDQQT-DEOSSOPVSA-N 0.000 claims 1
• GEJCMSDOFATKMJ-XXBNENTESA-N (5S)-1-(3-chloro-4-methoxyphenyl)-5-[1-[(1R)-3,3-difluorocyclopentyl]-5-(3,5-dimethyl-1,2-oxazol-4-yl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound COc1ccc(cc1Cl)N1[C@@H](CCC1=O)c1nc2cc(ccc2n1[C@@H]1CCC(F)(F)C1)-c1c(C)noc1C GEJCMSDOFATKMJ-XXBNENTESA-N 0.000 claims 1
• VITMRMCYCCOING-QFIPXVFZSA-N (5S)-1-(3-chloro-4-methoxyphenyl)-5-[3-(4,4-difluorocyclohexyl)-6-(3,5-dimethyl-1,2-oxazol-4-yl)imidazo[4,5-b]pyridin-2-yl]pyrrolidin-2-one Chemical compound COc1ccc(cc1Cl)N1[C@@H](CCC1=O)c1nc2cc(cnc2n1C1CCC(F)(F)CC1)-c1c(C)noc1C VITMRMCYCCOING-QFIPXVFZSA-N 0.000 claims 1
• QWCPASKKKFRAJA-JWIMYKKASA-N (5S)-1-(3-chloro-4-methoxyphenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(1,1-dioxothian-3-yl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound ClC=1C=C(C=CC=1OC)N1C(CC[C@H]1C1=NC2=C(N1C1CS(CCC1)(=O)=O)C=CC(=C2)C=1C(=NOC=1C)C)=O QWCPASKKKFRAJA-JWIMYKKASA-N 0.000 claims 1
• NMNIVIDMQQVHLJ-DEOSSOPVSA-N (5S)-1-(3-chloro-4-methoxyphenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(1,1-dioxothian-4-yl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound ClC=1C=C(C=CC=1OC)N1C(CC[C@H]1C1=NC2=C(N1C1CCS(CC1)(=O)=O)C=CC(=C2)C=1C(=NOC=1C)C)=O NMNIVIDMQQVHLJ-DEOSSOPVSA-N 0.000 claims 1
• IIYDGOWPTDNMSD-VWLOTQADSA-N (5S)-1-(3-chloro-4-methoxyphenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(1-methylsulfonylpiperidin-4-yl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound ClC=1C=C(C=CC=1OC)N1C(CC[C@H]1C1=NC2=C(N1C1CCN(CC1)S(=O)(=O)C)C=CC(=C2)C=1C(=NOC=1C)C)=O IIYDGOWPTDNMSD-VWLOTQADSA-N 0.000 claims 1
• OXZXFKZOPIDDAY-MOINULTHSA-N (5S)-1-(3-chloro-4-methoxyphenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(2-methyloxan-4-yl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound ClC=1C=C(C=CC=1OC)N1C(CC[C@H]1C1=NC2=C(N1C1CC(OCC1)C)C=CC(=C2)C=1C(=NOC=1C)C)=O OXZXFKZOPIDDAY-MOINULTHSA-N 0.000 claims 1
• JHTUKUABMVIKOY-DEOSSOPVSA-N (5S)-1-(3-chloro-4-methoxyphenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(2-oxaspiro[3.3]heptan-6-yl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound ClC=1C=C(C=CC=1OC)N1C(CC[C@H]1C1=NC2=C(N1C1CC3(COC3)C1)C=CC(=C2)C=1C(=NOC=1C)C)=O JHTUKUABMVIKOY-DEOSSOPVSA-N 0.000 claims 1
• GYCKOBGJXWOFTR-DEOSSOPVSA-N (5S)-1-(3-chloro-5-fluorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(1,1-dioxothian-4-yl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound CC1=C(C(C)=NO1)C1=CC=C2N(C3CCS(=O)(=O)CC3)C(=NC2=C1)[C@@H]1CCC(=O)N1C1=CC(Cl)=CC(F)=C1 GYCKOBGJXWOFTR-DEOSSOPVSA-N 0.000 claims 1
• KAGQTTDDGFPPSY-VWLOTQADSA-N (5S)-1-(3-chloro-5-methoxyphenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(1,1-dioxothian-4-yl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound ClC=1C=C(C=C(C=1)OC)N1C(CC[C@H]1C1=NC2=C(N1C1CCS(CC1)(=O)=O)C=CC(=C2)C=1C(=NOC=1C)C)=O KAGQTTDDGFPPSY-VWLOTQADSA-N 0.000 claims 1
• YSGAZEMHOQUIJA-WIIYFNMSSA-N (5S)-1-(4-chloro-3-fluorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(1,1-dioxothian-3-yl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound ClC1=C(C=C(C=C1)N1C(CC[C@H]1C1=NC2=C(N1C1CS(CCC1)(=O)=O)C=CC(=C2)C=1C(=NOC=1C)C)=O)F YSGAZEMHOQUIJA-WIIYFNMSSA-N 0.000 claims 1
• OCMWWEDOZWYQGM-JPYJTQIMSA-N (5S)-1-(5-chloro-6-methoxypyridin-3-yl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]pyrrolidin-2-one Chemical compound ClC=1C=C(C=NC=1OC)N1C(CC[C@H]1C1=NC2=C(N1[C@H]1CN(CC1)S(=O)(=O)C)C=CC(=C2)C=1C(=NOC=1C)C)=O OCMWWEDOZWYQGM-JPYJTQIMSA-N 0.000 claims 1
• RYEWWIFCGBHCCF-KOBHVQJXSA-N (5S)-5-[1-(3-aminocyclobutyl)-5-(3,5-dimethyl-1,2-oxazol-4-yl)benzimidazol-2-yl]-1-(3,4-difluorophenyl)pyrrolidin-2-one Chemical compound NC1CC(C1)N1C(=NC2=C1C=CC(=C2)C=1C(=NOC=1C)C)[C@@H]1CCC(N1C1=CC(=C(C=C1)F)F)=O RYEWWIFCGBHCCF-KOBHVQJXSA-N 0.000 claims 1
• LEONGBXKJOYQIY-QHCPKHFHSA-N (5S)-5-[1-(cyclopropylmethyl)-5-(3,5-dimethyl-1,2-oxazol-4-yl)benzimidazol-2-yl]-1-(3,4-difluorophenyl)pyrrolidin-2-one Chemical compound C1(CC1)CN1C(=NC2=C1C=CC(=C2)C=1C(=NOC=1C)C)[C@@H]1CCC(N1C1=CC(=C(C=C1)F)F)=O LEONGBXKJOYQIY-QHCPKHFHSA-N 0.000 claims 1
• OQXAIQCXLLFDQG-JPYJTQIMSA-N (5S)-5-[1-[(1R)-3,3-difluorocyclopentyl]-5-(3,5-dimethyl-1,2-oxazol-4-yl)benzimidazol-2-yl]-1-(3,4-difluorophenyl)pyrrolidin-2-one Chemical compound FC1(C[C@@H](CC1)N1C(=NC2=C1C=CC(=C2)C=1C(=NOC=1C)C)[C@@H]1CCC(N1C1=CC(=C(C=C1)F)F)=O)F OQXAIQCXLLFDQG-JPYJTQIMSA-N 0.000 claims 1
• REIBXPXUCPDXOM-XXBNENTESA-N (5S)-5-[1-[(1R)-3,3-difluorocyclopentyl]-5-(3,5-dimethyl-1,2-oxazol-4-yl)benzimidazol-2-yl]-1-(3-fluoro-4-methoxyphenyl)pyrrolidin-2-one Chemical compound FC1(C[C@@H](CC1)N1C(=NC2=C1C=CC(=C2)C=1C(=NOC=1C)C)[C@@H]1CCC(N1C1=CC(=C(C=C1)OC)F)=O)F REIBXPXUCPDXOM-XXBNENTESA-N 0.000 claims 1
• NHAIOYZVZMAVEK-IBVKSMDESA-N (5S)-5-[1-[(3R)-1-cyclopropylsulfonylpyrrolidin-3-yl]-5-(3,5-dimethyl-1,2-oxazol-4-yl)benzimidazol-2-yl]-1-(3,4-difluorophenyl)pyrrolidin-2-one Chemical compound C1(CC1)S(=O)(=O)N1C[C@@H](CC1)N1C(=NC2=C1C=CC(=C2)C=1C(=NOC=1C)C)[C@@H]1CCC(N1C1=CC(=C(C=C1)F)F)=O NHAIOYZVZMAVEK-IBVKSMDESA-N 0.000 claims 1
• SMXKSNWAZBWQMF-VWLOTQADSA-N (5S)-5-[1-[(4,4-difluorocyclohexyl)methyl]-5-(3,5-dimethyl-1,2-oxazol-4-yl)benzimidazol-2-yl]-1-(3,4-difluorophenyl)pyrrolidin-2-one Chemical compound FC1(CCC(CC1)CN1C(=NC2=C1C=CC(=C2)C=1C(=NOC=1C)C)[C@@H]1CCC(N1C1=CC(=C(C=C1)F)F)=O)F SMXKSNWAZBWQMF-VWLOTQADSA-N 0.000 claims 1
• UOAIQKBWLVTYRU-SANMLTNESA-N (5S)-5-[1-benzyl-5-(3,5-dimethyl-1,2-oxazol-4-yl)benzimidazol-2-yl]-1-(3,4-difluorophenyl)pyrrolidin-2-one Chemical compound C(C1=CC=CC=C1)N1C(=NC2=C1C=CC(=C2)C=1C(=NOC=1C)C)[C@@H]1CCC(N1C1=CC(=C(C=C1)F)F)=O UOAIQKBWLVTYRU-SANMLTNESA-N 0.000 claims 1
• SEQVUOVKZYAMQL-SANMLTNESA-N (5S)-5-[1-benzyl-5-(3,5-dimethyl-1,2-oxazol-4-yl)benzimidazol-2-yl]-1-(3-fluoro-4-methoxyphenyl)pyrrolidin-2-one Chemical compound C(C1=CC=CC=C1)N1C(=NC2=C1C=CC(=C2)C=1C(=NOC=1C)C)[C@@H]1CCC(N1C1=CC(=C(C=C1)OC)F)=O SEQVUOVKZYAMQL-SANMLTNESA-N 0.000 claims 1
• ZEQBWYDMOXWMJJ-QFIPXVFZSA-N (5S)-5-[3-(4,4-difluorocyclohexyl)-6-(3,5-dimethyl-1,2-oxazol-4-yl)imidazo[4,5-b]pyridin-2-yl]-1-(3,4-difluorophenyl)pyrrolidin-2-one Chemical compound Cc1noc(C)c1-c1cnc2n(C3CCC(F)(F)CC3)c(nc2c1)[C@@H]1CCC(=O)N1c1ccc(F)c(F)c1 ZEQBWYDMOXWMJJ-QFIPXVFZSA-N 0.000 claims 1
• RKTXRXVSCGRKQY-QFIPXVFZSA-N (5S)-5-[3-(4,4-difluorocyclohexyl)-6-(3,5-dimethyl-1,2-oxazol-4-yl)imidazo[4,5-b]pyridin-2-yl]-1-(3-fluoro-4-methoxyphenyl)pyrrolidin-2-one Chemical compound COc1ccc(cc1F)N1[C@@H](CCC1=O)c1nc2cc(cnc2n1C1CCC(F)(F)CC1)-c1c(C)noc1C RKTXRXVSCGRKQY-QFIPXVFZSA-N 0.000 claims 1
• DCDQVDSBCQXZSU-QHCPKHFHSA-N (5S)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(1,1-dioxothian-4-yl)benzimidazol-2-yl]-1-(3,4,5-trifluorophenyl)pyrrolidin-2-one Chemical compound CC1=NOC(=C1C1=CC2=C(N(C(=N2)[C@@H]2CCC(N2C2=CC(=C(C(=C2)F)F)F)=O)C2CCS(CC2)(=O)=O)C=C1)C DCDQVDSBCQXZSU-QHCPKHFHSA-N 0.000 claims 1
• KWFZEZDAPAESEU-DEOSSOPVSA-N (5S)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(1,1-dioxothian-4-yl)benzimidazol-2-yl]-1-(3-fluoro-4-methoxyphenyl)pyrrolidin-2-one Chemical compound CC1=NOC(=C1C1=CC2=C(N(C(=N2)[C@@H]2CCC(N2C2=CC(=C(C=C2)OC)F)=O)C2CCS(CC2)(=O)=O)C=C1)C KWFZEZDAPAESEU-DEOSSOPVSA-N 0.000 claims 1
• SUIWGWFEGZXURM-QHCPKHFHSA-N (5S)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(1,1-dioxothian-4-yl)benzimidazol-2-yl]-1-(5-fluoro-6-methoxypyridin-3-yl)pyrrolidin-2-one Chemical compound CC1=NOC(=C1C1=CC2=C(N(C(=N2)[C@@H]2CCC(N2C=2C=NC(=C(C=2)F)OC)=O)C2CCS(CC2)(=O)=O)C=C1)C SUIWGWFEGZXURM-QHCPKHFHSA-N 0.000 claims 1
• LXGVFKUJXLSSIT-MOINULTHSA-N (5S)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(2-methyloxan-4-yl)benzimidazol-2-yl]-1-(3-fluoro-4-methoxyphenyl)pyrrolidin-2-one Chemical compound CC1=NOC(=C1C1=CC2=C(N(C(=N2)[C@@H]2CCC(N2C2=CC(=C(C=C2)OC)F)=O)C2CC(OCC2)C)C=C1)C LXGVFKUJXLSSIT-MOINULTHSA-N 0.000 claims 1
• TVVBEZOVLLEEQW-BWKNWUBXSA-N (5S)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]-1-(2-methylphenyl)pyrrolidin-2-one Chemical compound Cc1noc(C)c1-c1ccc2n([C@@H]3CCN(C3)S(C)(=O)=O)c(nc2c1)[C@@H]1CCC(=O)N1c1ccccc1C TVVBEZOVLLEEQW-BWKNWUBXSA-N 0.000 claims 1
• XUXNRIMMAGAVHN-HXOBKFHXSA-N (5S)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]-1-(3,4,5-trifluorophenyl)pyrrolidin-2-one Chemical compound CC1=NOC(=C1C1=CC2=C(N(C(=N2)[C@@H]2CCC(N2C2=CC(=C(C(=C2)F)F)F)=O)[C@H]2CN(CC2)S(=O)(=O)C)C=C1)C XUXNRIMMAGAVHN-HXOBKFHXSA-N 0.000 claims 1
• DGGIXPDVUABBAR-RLWLMLJZSA-N (5S)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]-1-(3-ethoxy-5-fluorophenyl)pyrrolidin-2-one Chemical compound CCOc1cc(F)cc(c1)N1[C@@H](CCC1=O)c1nc2cc(ccc2n1[C@@H]1CCN(C1)S(C)(=O)=O)-c1c(C)noc1C DGGIXPDVUABBAR-RLWLMLJZSA-N 0.000 claims 1
• UROFXLADVMRGDG-YKSBVNFPSA-N (5S)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]-1-(3-fluoro-4-methoxyphenyl)pyrrolidin-2-one Chemical compound CC1=NOC(=C1C1=CC2=C(N(C(=N2)[C@@H]2CCC(N2C2=CC(=C(C=C2)OC)F)=O)[C@H]2CN(CC2)S(=O)(=O)C)C=C1)C UROFXLADVMRGDG-YKSBVNFPSA-N 0.000 claims 1
• RQNYVPBBMIRSAP-NLFFAJNJSA-N (5S)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]-1-(3-fluoro-5-methoxyphenyl)pyrrolidin-2-one Chemical compound COc1cc(F)cc(c1)N1[C@@H](CCC1=O)c1nc2cc(ccc2n1[C@@H]1CCN(C1)S(C)(=O)=O)-c1c(C)noc1C RQNYVPBBMIRSAP-NLFFAJNJSA-N 0.000 claims 1
• ZBIORFWTWOHVLU-QPPBQGQZSA-N (5S)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]-1-(3-fluorophenyl)pyrrolidin-2-one Chemical compound Cc1noc(C)c1-c1ccc2n([C@@H]3CCN(C3)S(C)(=O)=O)c(nc2c1)[C@@H]1CCC(=O)N1c1cccc(F)c1 ZBIORFWTWOHVLU-QPPBQGQZSA-N 0.000 claims 1
• MITROZSZLRKDRT-BWKNWUBXSA-N (5S)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]-1-(4-methoxyphenyl)pyrrolidin-2-one Chemical compound CC1=NOC(=C1C1=CC2=C(N(C(=N2)[C@@H]2CCC(N2C2=CC=C(C=C2)OC)=O)[C@H]2CN(CC2)S(=O)(=O)C)C=C1)C MITROZSZLRKDRT-BWKNWUBXSA-N 0.000 claims 1
• RJFAOEDALLSLDL-KCWPFWIISA-N (5S)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]-1-(4-propoxyphenyl)pyrrolidin-2-one Chemical compound CC1=NOC(=C1C1=CC2=C(N(C(=N2)[C@@H]2CCC(N2C2=CC=C(C=C2)OCCC)=O)[C@H]2CN(CC2)S(=O)(=O)C)C=C1)C RJFAOEDALLSLDL-KCWPFWIISA-N 0.000 claims 1
• BEVXMMSVWRKZIR-QPPBQGQZSA-N (5S)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]-1-(5-fluoro-2-methylphenyl)pyrrolidin-2-one Chemical compound Cc1noc(C)c1-c1ccc2n([C@@H]3CCN(C3)S(C)(=O)=O)c(nc2c1)[C@@H]1CCC(=O)N1c1cc(F)ccc1C BEVXMMSVWRKZIR-QPPBQGQZSA-N 0.000 claims 1
• UBSUREVLFBGHLE-KNQAVFIVSA-N (5S)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]-1-(6-fluoropyridin-3-yl)pyrrolidin-2-one Chemical compound Cc1noc(C)c1-c1ccc2n([C@@H]3CCN(C3)S(C)(=O)=O)c(nc2c1)[C@@H]1CCC(=O)N1c1ccc(F)nc1 UBSUREVLFBGHLE-KNQAVFIVSA-N 0.000 claims 1
• WUAFPACQBZHXHJ-OFNKIYASSA-N (5S)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]-1-(6-methoxypyridin-3-yl)pyrrolidin-2-one Chemical compound COc1ccc(cn1)N1[C@@H](CCC1=O)c1nc2cc(ccc2n1[C@@H]1CCN(C1)S(C)(=O)=O)-c1c(C)noc1C WUAFPACQBZHXHJ-OFNKIYASSA-N 0.000 claims 1
• QMDOCJCAZXGSJF-YKSBVNFPSA-N (5S)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]-1-[3-(trifluoromethoxy)phenyl]pyrrolidin-2-one Chemical compound CC1=NOC(=C1C1=CC2=C(N(C(=N2)[C@@H]2CCC(N2C2=CC(=CC=C2)OC(F)(F)F)=O)[C@H]2CN(CC2)S(=O)(=O)C)C=C1)C QMDOCJCAZXGSJF-YKSBVNFPSA-N 0.000 claims 1
• PSZXARZIJJBXGH-YKSBVNFPSA-N (5S)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]-1-[4-(trifluoromethoxy)phenyl]pyrrolidin-2-one Chemical compound Cc1noc(C)c1-c1ccc2n([C@@H]3CCN(C3)S(C)(=O)=O)c(nc2c1)[C@@H]1CCC(=O)N1c1ccc(OC(F)(F)F)cc1 PSZXARZIJJBXGH-YKSBVNFPSA-N 0.000 claims 1
• OIJFMBYWYMOYGI-QPPBQGQZSA-N (5S)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]-1-[4-(trifluoromethyl)phenyl]pyrrolidin-2-one Chemical compound Cc1noc(C)c1-c1ccc2n([C@@H]3CCN(C3)S(C)(=O)=O)c(nc2c1)[C@@H]1CCC(=O)N1c1ccc(cc1)C(F)(F)F OIJFMBYWYMOYGI-QPPBQGQZSA-N 0.000 claims 1
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