ES2828504T3 - Compuestos farmacéuticos - Google Patents

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Publication number

ES2828504T3

ES2828504T3 ES17790813T ES17790813T ES2828504T3 ES 2828504 T3 ES2828504 T3 ES 2828504T3 ES 17790813 T ES17790813 T ES 17790813T ES 17790813 T ES17790813 T ES 17790813T ES 2828504 T3 ES2828504 T3 ES 2828504T3

Authority

ES

Spain

Prior art keywords

benzo

pyrrolidin

dimethylisoxazol

imidazol

mmol

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 62
• 150000003839 salts Chemical class 0.000 claims abstract description 17
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 14
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 12
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims abstract description 11
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 8
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 8
• 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
• 125000003003 spiro group Chemical group 0.000 claims abstract description 3
• -1 5- (3,5-dimethylisoxazol-4-yl) -1- (tetrahydro-2H-pyran-4-yl) -1H-benzo [d] imidazol-2-yl Chemical group 0.000 claims description 419
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 330
• 238000000034 method Methods 0.000 claims description 276
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 174
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 132
• 239000002253 acid Substances 0.000 claims description 84
• XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical group O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 57
• 206010028980 Neoplasm Diseases 0.000 claims description 43
• 201000011510 cancer Diseases 0.000 claims description 26
• 230000000694 effects Effects 0.000 claims description 20
• 238000011282 treatment Methods 0.000 claims description 20
• PUPFATUGTIQBQA-UZQPLGKSSA-N fluorophen Chemical compound C([C@@]1(C)C2=CC(O)=CC=C2C[C@H]2[C@@H]1C)CN2CCC1=CC=C(F)C=C1 PUPFATUGTIQBQA-UZQPLGKSSA-N 0.000 claims description 19
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 18
• NYCVCXMSZNOGDH-UHFFFAOYSA-N pyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1CCCC1 NYCVCXMSZNOGDH-UHFFFAOYSA-N 0.000 claims description 18
• 125000000217 alkyl group Chemical group 0.000 claims description 16
• MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 12
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 11
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 11
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 10
• 125000003118 aryl group Chemical group 0.000 claims description 9
• 229910000029 sodium carbonate Inorganic materials 0.000 claims description 9
• 235000017550 sodium carbonate Nutrition 0.000 claims description 9
• 229940124597 therapeutic agent Drugs 0.000 claims description 9
• 230000001225 therapeutic effect Effects 0.000 claims description 9
• 229910052721 tungsten Inorganic materials 0.000 claims description 9
• 230000008569 process Effects 0.000 claims description 8
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 125000004432 carbon atom Chemical group C* 0.000 claims description 7
• 229910052739 hydrogen Inorganic materials 0.000 claims description 7
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 6
• 230000004777 loss-of-function mutation Effects 0.000 claims description 6
• 239000008194 pharmaceutical composition Substances 0.000 claims description 6
• 238000002560 therapeutic procedure Methods 0.000 claims description 6
• 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 claims description 5
• JXEHOLBKBUDBMX-OGDGHAERSA-N (5S)-1-(3,4-difluorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(2-hydroxypropyl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound CC(O)Cn1c(nc2cc(ccc12)-c1c(C)noc1C)[C@@H]1CCC(=O)N1c1ccc(F)c(F)c1 JXEHOLBKBUDBMX-OGDGHAERSA-N 0.000 claims description 4
• 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 description 4
• JWMDDGBGQPDRRZ-VWLOTQADSA-N (5S)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(1-methylsulfonylpiperidin-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)C2CCN(CC2)S(=O)(=O)C)C=C1)C JWMDDGBGQPDRRZ-VWLOTQADSA-N 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• 229910052727 yttrium Inorganic materials 0.000 claims description 4
• 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 description 3
• 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 3
• 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 description 3
• 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 description 3
• 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 description 3
• QFZFAGRBHSCOLG-YKSBVNFPSA-N (5S)-1-(3,5-dichlorophenyl)-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=C(C=1)Cl)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 QFZFAGRBHSCOLG-YKSBVNFPSA-N 0.000 claims description 3
• 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 description 3
• GIXRADJKTSZVTJ-DVECYGJZSA-N (5S)-1-(3-chloro-4-fluorophenyl)-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=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 GIXRADJKTSZVTJ-DVECYGJZSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 3
• OLLNJGACSIZQOK-BWKNWUBXSA-N 3-[(2S)-2-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]-5-oxopyrrolidin-1-yl]-5-fluorobenzonitrile Chemical compound CC1=NOC(=C1C1=CC2=C(N(C(=N2)[C@H]2N(C(CC2)=O)C=2C=C(C#N)C=C(C=2)F)[C@H]2CN(CC2)S(=O)(=O)C)C=C1)C OLLNJGACSIZQOK-BWKNWUBXSA-N 0.000 claims description 3
• BXMMBJZCICOLJZ-CILPGNKCSA-N 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)C2CCC(N2C2=CC=CC=C2)=O)[C@H]2CN(CC2)S(=O)(=O)C)C=C1)C BXMMBJZCICOLJZ-CILPGNKCSA-N 0.000 claims description 3
• 241001465754 Metazoa Species 0.000 claims description 3
• 230000000069 prophylactic effect Effects 0.000 claims description 3
• 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
• 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 description 2
• 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 description 2
• 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 description 2
• KHFVNUDHQRGVGL-YKSBVNFPSA-N (5S)-1-(3-chloro-5-fluorophenyl)-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=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 KHFVNUDHQRGVGL-YKSBVNFPSA-N 0.000 claims description 2
• STKUXGVVJSZLQW-WIIYFNMSSA-N (5S)-1-(4-chloro-3-fluorophenyl)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-(1-methylpyrrolidin-3-yl)benzimidazol-2-yl]pyrrolidin-2-one Chemical compound ClC1=C(C=C(C=C1)N1C(CC[C@H]1C1=NC2=C(N1C1CN(CC1)C)C=CC(=C2)C=1C(=NOC=1C)C)=O)F STKUXGVVJSZLQW-WIIYFNMSSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• BXMMBJZCICOLJZ-QPPBQGQZSA-N (5S)-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 Cc1noc(C)c1-c1ccc2n([C@@H]3CCN(C3)S(C)(=O)=O)c(nc2c1)[C@@H]1CCC(=O)N1c1ccccc1 BXMMBJZCICOLJZ-QPPBQGQZSA-N 0.000 claims description 2
• RAVAVLYPMREPQF-OFNKIYASSA-N (5S)-5-[5-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[(3R)-1-methylsulfonylpyrrolidin-3-yl]benzimidazol-2-yl]-1-pyridin-3-ylpyrrolidin-2-one Chemical compound Cc1noc(C)c1-c1ccc2n([C@@H]3CCN(C3)S(C)(=O)=O)c(nc2c1)[C@@H]1CCC(=O)N1c1cccnc1 RAVAVLYPMREPQF-OFNKIYASSA-N 0.000 claims description 2
• KSVFGSKFUBWSHR-IMMUGOHXSA-N 5-[2-[(2S)-1-(3,4-difluorophenyl)-5-oxopyrrolidin-2-yl]-5-(3,5-dimethyl-1,2-oxazol-4-yl)benzimidazol-1-yl]piperidin-2-one Chemical compound FC=1C=C(C=CC=1F)N1[C@@H](CCC1=O)C1=NC2=C(N1C1CCC(NC1)=O)C=CC(=C2)C=1C(=NOC=1C)C KSVFGSKFUBWSHR-IMMUGOHXSA-N 0.000 claims description 2
• 230000004913 activation Effects 0.000 claims description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
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