JP7281469B2 - Ｃ５ａ受容体調節剤 - Google Patents

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Publication number

JP7281469B2

JP7281469B2 JP2020539784A JP2020539784A JP7281469B2 JP 7281469 B2 JP7281469 B2 JP 7281469B2 JP 2020539784 A JP2020539784 A JP 2020539784A JP 2020539784 A JP2020539784 A JP 2020539784A JP 7281469 B2 JP7281469 B2 JP 7281469B2

Authority

JP

Japan

Prior art keywords

methoxy

dihydro

benzyl

trifluoromethyl

phenyl

Prior art date

2018-01-19

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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• 108010059426 Anaphylatoxin C5a Receptor Proteins 0.000 title description 41
• 102000005590 Anaphylatoxin C5a Receptor Human genes 0.000 title description 41
• 229940075993 receptor modulator Drugs 0.000 title 1
• -1 -tert-butyl 4-[4-methoxy-2-oxo-3-(2-trifluoromethyl-benzyl)-2,3-dihydro-benzimidazol-1-yl]-piperidine-1,3-dicarboxylic acid ester Chemical class 0.000 claims description 543
• 125000000217 alkyl group Chemical group 0.000 claims description 330
• 150000001875 compounds Chemical class 0.000 claims description 229
• 125000001424 substituent group Chemical group 0.000 claims description 149
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 124
• 229910052739 hydrogen Inorganic materials 0.000 claims description 116
• 239000001257 hydrogen Substances 0.000 claims description 116
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 100
• 229910052757 nitrogen Inorganic materials 0.000 claims description 93
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 88
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 87
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 82
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 65
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 55
• 229910052760 oxygen Inorganic materials 0.000 claims description 55
• 239000001301 oxygen Substances 0.000 claims description 55
• 229920006395 saturated elastomer Polymers 0.000 claims description 54
• 238000011282 treatment Methods 0.000 claims description 54
• 125000003545 alkoxy group Chemical group 0.000 claims description 50
• 125000001153 fluoro group Chemical group F* 0.000 claims description 48
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 44
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 42
• 201000010099 disease Diseases 0.000 claims description 41
• 125000005842 heteroatom Chemical group 0.000 claims description 41
• 229910052736 halogen Inorganic materials 0.000 claims description 40
• 208000027866 inflammatory disease Diseases 0.000 claims description 39
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 39
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 37
• 125000002947 alkylene group Chemical group 0.000 claims description 34
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 33
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 32
• 150000003839 salts Chemical class 0.000 claims description 32
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 31
• 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 29
• 125000000623 heterocyclic group Chemical group 0.000 claims description 29
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 27
• 125000004432 carbon atom Chemical group C* 0.000 claims description 25
• 125000001072 heteroaryl group Chemical group 0.000 claims description 25
• 208000035475 disorder Diseases 0.000 claims description 24
• 206010028980 Neoplasm Diseases 0.000 claims description 22
• 230000002265 prevention Effects 0.000 claims description 22
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 19
• 201000011510 cancer Diseases 0.000 claims description 17
• 150000002367 halogens Chemical class 0.000 claims description 17
• 230000009467 reduction Effects 0.000 claims description 17
• 208000023275 Autoimmune disease Diseases 0.000 claims description 16
• 230000000295 complement effect Effects 0.000 claims description 15
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 15
• 206010063837 Reperfusion injury Diseases 0.000 claims description 14
• 239000002253 acid Substances 0.000 claims description 14
• 208000014674 injury Diseases 0.000 claims description 14
• 208000010125 myocardial infarction Diseases 0.000 claims description 14
• 208000019553 vascular disease Diseases 0.000 claims description 14
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 13
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 12
• 206010061218 Inflammation Diseases 0.000 claims description 10
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 10
• 230000004054 inflammatory process Effects 0.000 claims description 10
• 230000001575 pathological effect Effects 0.000 claims description 10
• 208000007536 Thrombosis Diseases 0.000 claims description 9
• 239000003814 drug Substances 0.000 claims description 9
• 210000002889 endothelial cell Anatomy 0.000 claims description 9
• 208000028867 ischemia Diseases 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• 230000006378 damage Effects 0.000 claims description 8
• 208000012947 ischemia reperfusion injury Diseases 0.000 claims description 8
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
• 230000035939 shock Effects 0.000 claims description 8
• 238000002054 transplantation Methods 0.000 claims description 8
• 208000027418 Wounds and injury Diseases 0.000 claims description 7
• 230000002612 cardiopulmonary effect Effects 0.000 claims description 7
• 238000001356 surgical procedure Methods 0.000 claims description 7
• 230000008733 trauma Effects 0.000 claims description 7
• 206010030113 Oedema Diseases 0.000 claims description 6
• 230000004856 capillary permeability Effects 0.000 claims description 6
• 210000004351 coronary vessel Anatomy 0.000 claims description 6
• 230000004064 dysfunction Effects 0.000 claims description 6
• 230000008595 infiltration Effects 0.000 claims description 6
• 238000001764 infiltration Methods 0.000 claims description 6
• 210000000265 leukocyte Anatomy 0.000 claims description 6
• 230000004770 neurodegeneration Effects 0.000 claims description 6
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
• 230000010118 platelet activation Effects 0.000 claims description 6
• 125000004429 atom Chemical group 0.000 claims description 5
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
• 208000010247 contact dermatitis Diseases 0.000 claims description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 5
• 231100000572 poisoning Toxicity 0.000 claims description 4
• 230000000607 poisoning effect Effects 0.000 claims description 4
• 230000000740 bleeding effect Effects 0.000 claims description 3
• GVXWPHZQBXCLRK-QGZVFWFLSA-N (3-methyloxetan-3-yl) (3R)-3-[4-methoxy-2-oxo-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-1-yl]pyrrolidine-1-carboxylate Chemical compound CC1(COC1)OC(=O)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O GVXWPHZQBXCLRK-QGZVFWFLSA-N 0.000 claims description 2
• NNLHLKWMNIVSRZ-UHFFFAOYSA-N 1-(1-benzoylpiperidin-4-yl)-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound C(C1=CC=CC=C1)(=O)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O NNLHLKWMNIVSRZ-UHFFFAOYSA-N 0.000 claims description 2
• WMTXPXSXGWNZRT-HXUWFJFHSA-N 1-[(3R)-1-(2,4-dimethylpyridin-3-yl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound CC1=NC=CC(=C1N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O)C WMTXPXSXGWNZRT-HXUWFJFHSA-N 0.000 claims description 2
• WHZSCGPWIVIGNA-GOSISDBHSA-N 1-[(3R)-1-(2,5-dimethylpyrazol-3-yl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound CN1N=C(C=C1N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O)C WHZSCGPWIVIGNA-GOSISDBHSA-N 0.000 claims description 2
• CNDVWIRTQLQZQI-GOSISDBHSA-N 1-[(3R)-1-(2,6-difluorophenyl)pyrrolidin-3-yl]-4-methoxy-3-[(2-methoxyphenyl)methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)F)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)OC)=O CNDVWIRTQLQZQI-GOSISDBHSA-N 0.000 claims description 2
• VHSLAALSKUTYRD-QGZVFWFLSA-N 1-[(3R)-1-(2,6-difluorophenyl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethoxy)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)F)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)OC(F)(F)F)=O VHSLAALSKUTYRD-QGZVFWFLSA-N 0.000 claims description 2
• ZDIDHWPKMWDFJQ-QGZVFWFLSA-N 1-[(3R)-1-(2,6-difluorophenyl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)F)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O ZDIDHWPKMWDFJQ-QGZVFWFLSA-N 0.000 claims description 2
• QLJFYMMZOFFJMU-MRXNPFEDSA-N 1-[(3R)-1-(2,6-difluorophenyl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]imidazo[4,5-c]pyridin-2-one Chemical compound FC1=C(C(=CC=C1)F)N1C[C@@H](CC1)N1C(N(C=2C(=NC=CC=21)OC)CC1=C(C=CC=C1)C(F)(F)F)=O QLJFYMMZOFFJMU-MRXNPFEDSA-N 0.000 claims description 2
• PBGJNOTZVPGDDI-LJQANCHMSA-N 1-[(3R)-1-(2,6-dimethylphenyl)pyrrolidin-3-yl]-3-[[2-(trifluoromethyl)phenyl]methyl]-5H-imidazo[4,5-c]pyridine-2,4-dione Chemical compound CC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C=2C(NC=CC=21)=O)CC1=C(C=CC=C1)C(F)(F)F)=O PBGJNOTZVPGDDI-LJQANCHMSA-N 0.000 claims description 2
• MWLJKNZXARDTIV-JOCHJYFZSA-N 1-[(3R)-1-(2,6-dimethylphenyl)pyrrolidin-3-yl]-4-(2-hydroxyethoxy)-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound CC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OCCO)CC1=C(C=CC=C1)C(F)(F)F)=O MWLJKNZXARDTIV-JOCHJYFZSA-N 0.000 claims description 2
• ICJOOWLOFNHBJK-OAQYLSRUSA-N 1-[(3R)-1-(2,6-dimethylphenyl)pyrrolidin-3-yl]-4-(2-hydroxyethoxy)-3-[[2-(trifluoromethyl)phenyl]methyl]imidazo[4,5-c]pyridin-2-one Chemical compound CC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C=2C(=NC=CC=21)OCCO)CC1=C(C=CC=C1)C(F)(F)F)=O ICJOOWLOFNHBJK-OAQYLSRUSA-N 0.000 claims description 2
• PNDNPRIAFWXWBN-OAQYLSRUSA-N 1-[(3R)-1-(2,6-dimethylphenyl)pyrrolidin-3-yl]-4-(2-hydroxyethylamino)-3-[[2-(trifluoromethyl)phenyl]methyl]imidazo[4,5-c]pyridin-2-one Chemical compound CC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C=2C(=NC=CC=21)NCCO)CC1=C(C=CC=C1)C(F)(F)F)=O PNDNPRIAFWXWBN-OAQYLSRUSA-N 0.000 claims description 2
• GQFSWGMINJGELO-HXUWFJFHSA-N 1-[(3R)-1-(2,6-dimethylphenyl)pyrrolidin-3-yl]-4-hydroxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound CC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2O)CC1=C(C=CC=C1)C(F)(F)F)=O GQFSWGMINJGELO-HXUWFJFHSA-N 0.000 claims description 2
• LRLKDKOKWUPXFH-JOCHJYFZSA-N 1-[(3R)-1-(2,6-dimethylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[(2-methoxyphenyl)methyl]benzimidazol-2-one Chemical compound CC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)OC)=O LRLKDKOKWUPXFH-JOCHJYFZSA-N 0.000 claims description 2
• VBJWKWDOZPFNEK-OAQYLSRUSA-N 1-[(3R)-1-(2,6-dimethylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[(2-methoxyphenyl)methyl]imidazo[4,5-c]pyridin-2-one Chemical compound CC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C=2C(=NC=CC=21)OC)CC1=C(C=CC=C1)OC)=O VBJWKWDOZPFNEK-OAQYLSRUSA-N 0.000 claims description 2
• FJPDNUMBZULXGX-OAQYLSRUSA-N 1-[(3R)-1-(2,6-dimethylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound CC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O FJPDNUMBZULXGX-OAQYLSRUSA-N 0.000 claims description 2
• KKPWUCRWLSANAS-HXUWFJFHSA-N 1-[(3R)-1-(2,6-dimethylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]imidazo[4,5-c]pyridin-2-one Chemical compound CC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C=2C(=NC=CC=21)OC)CC1=C(C=CC=C1)C(F)(F)F)=O KKPWUCRWLSANAS-HXUWFJFHSA-N 0.000 claims description 2
• YTMQZWZKHZTSIU-LJQANCHMSA-N 1-[(3R)-1-(2-acetyl-6-fluorophenyl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound C(C)(=O)C1=C(C(=CC=C1)F)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O YTMQZWZKHZTSIU-LJQANCHMSA-N 0.000 claims description 2
• ONTUQQPPKSSRDP-QGZVFWFLSA-N 1-[(3R)-1-(2-amino-6-fluorophenyl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound NC1=C(C(=CC=C1)F)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O ONTUQQPPKSSRDP-QGZVFWFLSA-N 0.000 claims description 2
• IBQAGQLUBWNTGX-QGZVFWFLSA-N 1-[(3R)-1-(2-bromo-6-fluorophenyl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound BrC1=C(C(=CC=C1)F)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O IBQAGQLUBWNTGX-QGZVFWFLSA-N 0.000 claims description 2
• OFFKVZBOEOCRIN-GOSISDBHSA-N 1-[(3R)-1-(2-cyano-6-fluorophenyl)pyrrolidin-3-yl]-2-oxo-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazole-4-carboxamide Chemical compound C(#N)C1=C(C(=CC=C1)F)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2C(=O)N)CC1=C(C=CC=C1)C(F)(F)F)=O OFFKVZBOEOCRIN-GOSISDBHSA-N 0.000 claims description 2
• CWDATAHFYIVKFC-HXUWFJFHSA-N 1-[(3R)-1-(2-cyano-6-fluorophenyl)pyrrolidin-3-yl]-N,N-dimethyl-2-oxo-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazole-4-carboxamide Chemical compound CN(C(=O)C1=CC=CC=2N(C(N(C=21)CC1=C(C=CC=C1)C(F)(F)F)=O)[C@H]1CN(CC1)C1=C(C=CC=C1F)C#N)C CWDATAHFYIVKFC-HXUWFJFHSA-N 0.000 claims description 2
• UYWPQTFZUNFHHR-HXUWFJFHSA-N 1-[(3R)-1-(2-cyano-6-fluorophenyl)pyrrolidin-3-yl]-N-(2-hydroxyethyl)-2-oxo-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazole-4-carboxamide Chemical compound OCCNC(=O)C1=CC=CC=2N(C(N(C=21)CC1=C(C=CC=C1)C(F)(F)F)=O)[C@H]1CN(CC1)C1=C(C=CC=C1F)C#N UYWPQTFZUNFHHR-HXUWFJFHSA-N 0.000 claims description 2
• GSKHMNCWGCRAKY-OAQYLSRUSA-N 1-[(3R)-1-(2-cyano-6-fluorophenyl)pyrrolidin-3-yl]-N-(2-methoxyethyl)-2-oxo-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazole-4-carboxamide Chemical compound COCCNC(=O)C1=CC=CC=2N(C(N(C=21)CC1=C(C=CC=C1)C(F)(F)F)=O)[C@H]1CN(CC1)C1=C(C=CC=C1F)C#N GSKHMNCWGCRAKY-OAQYLSRUSA-N 0.000 claims description 2
• CJDFQGLERBZMRH-LJQANCHMSA-N 1-[(3R)-1-(2-cyano-6-fluorophenyl)pyrrolidin-3-yl]-N-methyl-2-oxo-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazole-4-carboxamide Chemical compound CNC(=O)C1=CC=CC=2N(C(N(C=21)CC1=C(C=CC=C1)C(F)(F)F)=O)[C@H]1CN(CC1)C1=C(C=CC=C1F)C#N CJDFQGLERBZMRH-LJQANCHMSA-N 0.000 claims description 2
• LPDGVUUHIDEHFC-GOSISDBHSA-N 1-[(3R)-1-(2-fluoro-4-methylpyridin-3-yl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=NC=CC(=C1N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O)C LPDGVUUHIDEHFC-GOSISDBHSA-N 0.000 claims description 2
• LLFPCAWIFZESTN-QGZVFWFLSA-N 1-[(3R)-1-(2-fluoro-4-methylpyridin-3-yl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]imidazo[4,5-c]pyridin-2-one Chemical compound FC1=NC=CC(=C1N1C[C@@H](CC1)N1C(N(C=2C(=NC=CC=21)OC)CC1=C(C=CC=C1)C(F)(F)F)=O)C LLFPCAWIFZESTN-QGZVFWFLSA-N 0.000 claims description 2
• GLQKFOVCUQCHGM-MRXNPFEDSA-N 1-[(3R)-1-(2-fluoro-6-methoxyphenyl)pyrrolidin-3-yl]-3-[[2-(trifluoromethyl)phenyl]methyl]-5H-imidazo[4,5-c]pyridine-2,4-dione Chemical compound FC1=C(C(=CC=C1)OC)N1C[C@@H](CC1)N1C(N(C=2C(NC=CC=21)=O)CC1=C(C=CC=C1)C(F)(F)F)=O GLQKFOVCUQCHGM-MRXNPFEDSA-N 0.000 claims description 2
• QAPXAULSTPOOOW-GOSISDBHSA-N 1-[(3R)-1-(2-fluoro-6-methoxyphenyl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)OC)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O QAPXAULSTPOOOW-GOSISDBHSA-N 0.000 claims description 2
• GFMRQGKZEDMYTQ-QGZVFWFLSA-N 1-[(3R)-1-(2-fluoro-6-methoxyphenyl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]imidazo[4,5-c]pyridin-2-one Chemical compound FC1=C(C(=CC=C1)OC)N1C[C@@H](CC1)N1C(N(C=2C(=NC=CC=21)OC)CC1=C(C=CC=C1)C(F)(F)F)=O GFMRQGKZEDMYTQ-QGZVFWFLSA-N 0.000 claims description 2
• CQSLUCPOZPEWBG-GOSISDBHSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-3-[(2-methoxyphenyl)methyl]-5H-imidazo[4,5-c]pyridine-2,4-dione Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C=2C(NC=CC=21)=O)CC1=C(C=CC=C1)OC)=O CQSLUCPOZPEWBG-GOSISDBHSA-N 0.000 claims description 2
• FGSJQJOVPVZIQZ-QGZVFWFLSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-3-[[2-(trifluoromethyl)phenyl]methyl]-5H-imidazo[4,5-c]pyridine-2,4-dione Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C=2C(NC=CC=21)=O)CC1=C(C=CC=C1)C(F)(F)F)=O FGSJQJOVPVZIQZ-QGZVFWFLSA-N 0.000 claims description 2
• BSEAAKBARAPNKJ-ZMFCMNQTSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-(1-methylpyrrolidin-3-yl)oxy-3-[[2-(trifluoromethyl)phenyl]methyl]imidazo[4,5-c]pyridin-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C=2C(=NC=CC=21)OC1CN(CC1)C)CC1=C(C=CC=C1)C(F)(F)F)=O BSEAAKBARAPNKJ-ZMFCMNQTSA-N 0.000 claims description 2
• ZVVBSIRWFQCXRV-HXUWFJFHSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-(2-hydroxyethoxy)-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OCCO)CC1=C(C=CC=C1)C(F)(F)F)=O ZVVBSIRWFQCXRV-HXUWFJFHSA-N 0.000 claims description 2
• ALKQCSGIXIWFPG-HXUWFJFHSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-(2-methoxyethylamino)-3-[[2-(trifluoromethyl)phenyl]methyl]imidazo[4,5-c]pyridin-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C=2C(=NC=CC=21)NCCOC)CC1=C(C=CC=C1)C(F)(F)F)=O ALKQCSGIXIWFPG-HXUWFJFHSA-N 0.000 claims description 2
• SYCFLXWNZQQKJD-HSZRJFAPSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-(2-morpholin-4-ylethoxy)-3-[[2-(trifluoromethyl)phenyl]methyl]imidazo[4,5-c]pyridin-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C=2C(=NC=CC=21)OCCN1CCOCC1)CC1=C(C=CC=C1)C(F)(F)F)=O SYCFLXWNZQQKJD-HSZRJFAPSA-N 0.000 claims description 2
• FLIRJABBGRERQI-HXUWFJFHSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-(3-methoxyazetidin-1-yl)-3-[[2-(trifluoromethyl)phenyl]methyl]imidazo[4,5-c]pyridin-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C=2C(=NC=CC=21)N1CC(C1)OC)CC1=C(C=CC=C1)C(F)(F)F)=O FLIRJABBGRERQI-HXUWFJFHSA-N 0.000 claims description 2
• NISUCIVZLXBIHF-JOCHJYFZSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-(4-methylpiperazin-1-yl)-3-[[2-(trifluoromethyl)phenyl]methyl]imidazo[4,5-c]pyridin-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C=2C(=NC=CC=21)N1CCN(CC1)C)CC1=C(C=CC=C1)C(F)(F)F)=O NISUCIVZLXBIHF-JOCHJYFZSA-N 0.000 claims description 2
• MICDUEZYTUTHPM-HXUWFJFHSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-(oxetan-3-yloxy)-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC1COC1)CC1=C(C=CC=C1)C(F)(F)F)=O MICDUEZYTUTHPM-HXUWFJFHSA-N 0.000 claims description 2
• VYNAXEHBRQCGCV-LJQANCHMSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-(oxetan-3-yloxy)-3-[[2-(trifluoromethyl)phenyl]methyl]imidazo[4,5-c]pyridin-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C=2C(=NC=CC=21)OC1COC1)CC1=C(C=CC=C1)C(F)(F)F)=O VYNAXEHBRQCGCV-LJQANCHMSA-N 0.000 claims description 2
• XZMCTUHRHZCWFD-HXUWFJFHSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-[2-hydroxyethyl(methyl)amino]-3-[[2-(trifluoromethyl)phenyl]methyl]imidazo[4,5-c]pyridin-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C=2C(=NC=CC=21)N(C)CCO)CC1=C(C=CC=C1)C(F)(F)F)=O XZMCTUHRHZCWFD-HXUWFJFHSA-N 0.000 claims description 2
• MBELVZIKOBTMBR-GOSISDBHSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-hydroxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2O)CC1=C(C=CC=C1)C(F)(F)F)=O MBELVZIKOBTMBR-GOSISDBHSA-N 0.000 claims description 2
• ZNWBVRUTWMQJPI-HXUWFJFHSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[(2-methoxyphenyl)methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)OC)=O ZNWBVRUTWMQJPI-HXUWFJFHSA-N 0.000 claims description 2
• TULOTFXRBLXXSY-LJQANCHMSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[(2-methoxyphenyl)methyl]imidazo[4,5-c]pyridin-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C=2C(=NC=CC=21)OC)CC1=C(C=CC=C1)OC)=O TULOTFXRBLXXSY-LJQANCHMSA-N 0.000 claims description 2
• YYCYEWVBKICQLJ-JOCHJYFZSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[(2-propan-2-yloxyphenyl)methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)OC(C)C)=O YYCYEWVBKICQLJ-JOCHJYFZSA-N 0.000 claims description 2
• MPLLFJOAEOCVNE-QGZVFWFLSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[(3-methoxypyrazin-2-yl)methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=NC=CN=C1OC)=O MPLLFJOAEOCVNE-QGZVFWFLSA-N 0.000 claims description 2
• RTGYZYOPCIABOF-LJQANCHMSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[(3-propan-2-yloxypyrazin-2-yl)methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=NC=CN=C1OC(C)C)=O RTGYZYOPCIABOF-LJQANCHMSA-N 0.000 claims description 2
• ASIPIPZLUMELEE-HXUWFJFHSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[(3-propan-2-yloxypyridin-2-yl)methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=NC=CC=C1OC(C)C)=O ASIPIPZLUMELEE-HXUWFJFHSA-N 0.000 claims description 2
• KRXYYVFWLBLNHP-LJQANCHMSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[(3-propan-2-ylpyrazin-2-yl)methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=NC=CN=C1C(C)C)=O KRXYYVFWLBLNHP-LJQANCHMSA-N 0.000 claims description 2
• VDRCOOBZXNUMRX-QGZVFWFLSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[(4-methoxypyridazin-3-yl)methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC=1N=NC=CC=1OC)=O VDRCOOBZXNUMRX-QGZVFWFLSA-N 0.000 claims description 2
• HPPJSJXWDHLMOL-GOSISDBHSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[(4-methoxypyrimidin-5-yl)methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC=1C(=NC=NC=1)OC)=O HPPJSJXWDHLMOL-GOSISDBHSA-N 0.000 claims description 2
• SLORHFSJSMTZRQ-GOSISDBHSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[(4-methylpyridazin-3-yl)methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC=1N=NC=CC=1C)=O SLORHFSJSMTZRQ-GOSISDBHSA-N 0.000 claims description 2
• PMDLTIRUWUNLCX-LJQANCHMSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[(4-propan-2-yloxypyridazin-3-yl)methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC=1N=NC=CC=1OC(C)C)=O PMDLTIRUWUNLCX-LJQANCHMSA-N 0.000 claims description 2
• UMVRPDDCSAPJLO-OAQYLSRUSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[(4-propan-2-ylpyridin-3-yl)methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC=1C=NC=CC=1C(C)C)=O UMVRPDDCSAPJLO-OAQYLSRUSA-N 0.000 claims description 2
• POFAVQZECXFKDM-HXUWFJFHSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[(4-propan-2-ylpyrimidin-5-yl)methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC=1C(=NC=NC=1)C(C)C)=O POFAVQZECXFKDM-HXUWFJFHSA-N 0.000 claims description 2
• VHOIUZLBDJQTLJ-MRXNPFEDSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)-1,3-thiazol-4-yl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC=1N=C(SC=1)C(F)(F)F)=O VHOIUZLBDJQTLJ-MRXNPFEDSA-N 0.000 claims description 2
• FPDYDYCMSXAOJC-LJQANCHMSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O FPDYDYCMSXAOJC-LJQANCHMSA-N 0.000 claims description 2
• YHEPMCHOVRHVMG-GOSISDBHSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]imidazo[4,5-c]pyridin-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C=2C(=NC=CC=21)OC)CC1=C(C=CC=C1)C(F)(F)F)=O YHEPMCHOVRHVMG-GOSISDBHSA-N 0.000 claims description 2
• LHNYAMNURQVFPG-GOSISDBHSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)pyridin-3-yl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC=1C(=NC=CC=1)C(F)(F)F)=O LHNYAMNURQVFPG-GOSISDBHSA-N 0.000 claims description 2
• QWOYRMPYMRVXMT-MRXNPFEDSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[[2-methyl-4-(trifluoromethyl)-1,3-thiazol-5-yl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(N=C(S1)C)C(F)(F)F)=O QWOYRMPYMRVXMT-MRXNPFEDSA-N 0.000 claims description 2
• YGNLWVHLPIOUMI-MRXNPFEDSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[[3-(trifluoromethyl)pyrazin-2-yl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=NC=CN=C1C(F)(F)F)=O YGNLWVHLPIOUMI-MRXNPFEDSA-N 0.000 claims description 2
• GBDBRVKXWNDZOV-QGZVFWFLSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[[3-(trifluoromethyl)pyridin-2-yl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=NC=CC=C1C(F)(F)F)=O GBDBRVKXWNDZOV-QGZVFWFLSA-N 0.000 claims description 2
• WROQCFYQVWWVNB-GOSISDBHSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[[4-(trifluoromethyl)pyridin-3-yl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC=1C=NC=CC=1C(F)(F)F)=O WROQCFYQVWWVNB-GOSISDBHSA-N 0.000 claims description 2
• RVDKJVSLHVPRBR-QGZVFWFLSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[[4-(trifluoromethyl)pyrimidin-5-yl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC=1C(=NC=NC=1)C(F)(F)F)=O RVDKJVSLHVPRBR-QGZVFWFLSA-N 0.000 claims description 2
• DOTNDDPUJNDENR-OAQYLSRUSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-morpholin-4-yl-3-[[2-(trifluoromethyl)phenyl]methyl]imidazo[4,5-c]pyridin-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C=2C(=NC=CC=21)N1CCOCC1)CC1=C(C=CC=C1)C(F)(F)F)=O DOTNDDPUJNDENR-OAQYLSRUSA-N 0.000 claims description 2
• QEIFCKRKXIKBQH-OAQYLSRUSA-N 1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-piperidin-4-yloxy-3-[[2-(trifluoromethyl)phenyl]methyl]imidazo[4,5-c]pyridin-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C=2C(=NC=CC=21)OC1CCNCC1)CC1=C(C=CC=C1)C(F)(F)F)=O QEIFCKRKXIKBQH-OAQYLSRUSA-N 0.000 claims description 2
• FJHZQPPEIFMJRQ-OAQYLSRUSA-N 1-[(3R)-1-(2-fluoro-6-morpholin-4-ylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)N1CCOCC1)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O FJHZQPPEIFMJRQ-OAQYLSRUSA-N 0.000 claims description 2
• BDLPMUKTILWFEA-GOSISDBHSA-N 1-[(3R)-1-(2-fluorophenyl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C=CC=C1)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O BDLPMUKTILWFEA-GOSISDBHSA-N 0.000 claims description 2
• FDUHVAKYGPAIKC-GOSISDBHSA-N 1-[(3R)-1-(2-methoxy-6-methylphenyl)pyrrolidin-3-yl]-3-[[2-(trifluoromethyl)phenyl]methyl]-5H-imidazo[4,5-c]pyridine-2,4-dione Chemical compound COC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C=2C(NC=CC=21)=O)CC1=C(C=CC=C1)C(F)(F)F)=O FDUHVAKYGPAIKC-GOSISDBHSA-N 0.000 claims description 2
• PPPNBXQNLIDQKF-OAHLLOKOSA-N 1-[(3R)-1-(3,5-dichloropyridazin-4-yl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound ClC=1N=NC=C(C=1N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O)Cl PPPNBXQNLIDQKF-OAHLLOKOSA-N 0.000 claims description 2
• CWMNGBGMWDBVKD-MRXNPFEDSA-N 1-[(3R)-1-(3,5-difluoropyridin-4-yl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC=1C=NC=C(C=1N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O)F CWMNGBGMWDBVKD-MRXNPFEDSA-N 0.000 claims description 2
• IIRINVBOWKTIET-GOSISDBHSA-N 1-[(3R)-1-(3,5-dimethoxypyridin-4-yl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound COC=1C=NC=C(C=1N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O)OC IIRINVBOWKTIET-GOSISDBHSA-N 0.000 claims description 2
• LBCCBHYVUACJCM-HXUWFJFHSA-N 1-[(3R)-1-(3,5-dimethylpyridin-4-yl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound CC=1C=NC=C(C=1N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O)C LBCCBHYVUACJCM-HXUWFJFHSA-N 0.000 claims description 2
• NAZCBXXWCSIPQZ-OAHLLOKOSA-N 1-[(3R)-1-(4,5-dichloropyridazin-3-yl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound ClC1=C(N=NC=C1Cl)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O NAZCBXXWCSIPQZ-OAHLLOKOSA-N 0.000 claims description 2
• XZUPKPAQKRGKOP-QGZVFWFLSA-N 1-[(3R)-1-(4-chloro-2,5-dimethylpyrazol-3-yl)pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound ClC1=C(N(N=C1C)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O XZUPKPAQKRGKOP-QGZVFWFLSA-N 0.000 claims description 2
• TUCCUUVQADMLEX-JOCHJYFZSA-N 1-[(3R)-1-[2-(azetidin-1-ylmethyl)-6-fluorophenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound N1(CCC1)CC1=C(C(=CC=C1)F)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O TUCCUUVQADMLEX-JOCHJYFZSA-N 0.000 claims description 2
• NWOCUAXZVLVBCI-OAQYLSRUSA-N 1-[(3R)-1-[2-[(dimethylamino)methyl]-6-fluorophenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound CN(C)CC1=C(C(=CC=C1)F)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O NWOCUAXZVLVBCI-OAQYLSRUSA-N 0.000 claims description 2
• QIGCMZKRPKUROK-AREMUKBSSA-N 1-[(3R)-1-[2-[[4-(dimethylamino)piperidin-1-yl]methyl]-6-fluorophenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound CN(C1CCN(CC1)CC1=C(C(=CC=C1)F)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O)C QIGCMZKRPKUROK-AREMUKBSSA-N 0.000 claims description 2
• FSEIEGYDLJMYBS-HSZRJFAPSA-N 1-[(3R)-1-[2-[[bis(2-hydroxyethyl)amino]methyl]-6-fluorophenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound OCCN(CCO)CC1=C(C(=CC=C1)F)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O FSEIEGYDLJMYBS-HSZRJFAPSA-N 0.000 claims description 2
• KJCCTXTXIQYATQ-HSZRJFAPSA-N 1-[(3R)-1-[2-[[ethyl(2-hydroxyethyl)amino]methyl]-6-fluorophenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound C(C)N(CCO)CC1=C(C(=CC=C1)F)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O KJCCTXTXIQYATQ-HSZRJFAPSA-N 0.000 claims description 2
• KNSHOULBAPQHPO-WHCXFUJUSA-N 1-[(3R)-1-[2-fluoro-6-(1-hydroxyethyl)phenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C(C)O)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O KNSHOULBAPQHPO-WHCXFUJUSA-N 0.000 claims description 2
• HKZMCUMMWNVPFO-ROPPNANJSA-N 1-[(3R)-1-[2-fluoro-6-(1-methoxyethyl)phenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C(C)OC)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O HKZMCUMMWNVPFO-ROPPNANJSA-N 0.000 claims description 2
• FIHPOIONABVHRZ-LJQANCHMSA-N 1-[(3R)-1-[2-fluoro-6-(2-hydroxypropan-2-yl)phenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C(C)(C)O)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O FIHPOIONABVHRZ-LJQANCHMSA-N 0.000 claims description 2
• LVJKIPIIHCFUTO-XMMPIXPASA-N 1-[(3R)-1-[2-fluoro-6-(2-morpholin-4-ylethyl)phenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)CCN1CCOCC1)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O LVJKIPIIHCFUTO-XMMPIXPASA-N 0.000 claims description 2
• WWLUKMXYXADZED-RUZDIDTESA-N 1-[(3R)-1-[2-fluoro-6-(3-morpholin-4-ylprop-1-ynyl)phenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C#CCN1CCOCC1)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O WWLUKMXYXADZED-RUZDIDTESA-N 0.000 claims description 2
• ZRYGJJOLFGCASR-RUZDIDTESA-N 1-[(3R)-1-[2-fluoro-6-(3-morpholin-4-ylpropyl)phenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)CCCN1CCOCC1)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O ZRYGJJOLFGCASR-RUZDIDTESA-N 0.000 claims description 2
• IUMLPIUFGQFQMU-LJQANCHMSA-N 1-[(3R)-1-[2-fluoro-6-(hydroxymethyl)phenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)CO)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O IUMLPIUFGQFQMU-LJQANCHMSA-N 0.000 claims description 2
• IWMOTVYUMFFGHG-HXUWFJFHSA-N 1-[(3R)-1-[2-fluoro-6-(methylaminomethyl)phenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)CNC)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O IWMOTVYUMFFGHG-HXUWFJFHSA-N 0.000 claims description 2
• NKTGLPJMFWOSKY-HSZRJFAPSA-N 1-[(3R)-1-[2-fluoro-6-(morpholin-4-ylmethyl)phenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)CN1CCOCC1)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O NKTGLPJMFWOSKY-HSZRJFAPSA-N 0.000 claims description 2
• PVWLKJYTJXICBI-HSZRJFAPSA-N 1-[(3R)-1-[2-fluoro-6-(piperazin-1-ylmethyl)phenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)CN1CCNCC1)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O PVWLKJYTJXICBI-HSZRJFAPSA-N 0.000 claims description 2
• AKBLLIWZSKRKFN-XMMPIXPASA-N 1-[(3R)-1-[2-fluoro-6-(piperidin-1-ylmethyl)phenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)CN1CCCCC1)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O AKBLLIWZSKRKFN-XMMPIXPASA-N 0.000 claims description 2
• FBXHVAOERANLAF-HSZRJFAPSA-N 1-[(3R)-1-[2-fluoro-6-(pyrrolidin-1-ylmethyl)phenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)CN1CCCC1)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O FBXHVAOERANLAF-HSZRJFAPSA-N 0.000 claims description 2
• YKJJEPDQLMXDKD-GWQXNCQPSA-N 1-[(3R)-1-[2-fluoro-6-[(1-methoxypropan-2-ylamino)methyl]phenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)CNC(COC)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O YKJJEPDQLMXDKD-GWQXNCQPSA-N 0.000 claims description 2
• DRGVYWBJZCNZQP-JOCHJYFZSA-N 1-[(3R)-1-[2-fluoro-6-[(3-methoxyazetidin-1-yl)methyl]phenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)CN1CC(C1)OC)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O DRGVYWBJZCNZQP-JOCHJYFZSA-N 0.000 claims description 2
• CGFXJWFZWPDREC-MIHMCVIASA-N 1-[(3R)-1-[2-fluoro-6-[(3-methoxypyrrolidin-1-yl)methyl]phenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)CN1CC(CC1)OC)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O CGFXJWFZWPDREC-MIHMCVIASA-N 0.000 claims description 2
• IYMMTMVOKWCGNE-HSZRJFAPSA-N 1-[(3R)-1-[2-fluoro-6-[(4-hydroxypiperidin-1-yl)methyl]phenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)CN1CCC(CC1)O)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O IYMMTMVOKWCGNE-HSZRJFAPSA-N 0.000 claims description 2
• ASOVDVUJXMSPSV-XMMPIXPASA-N 1-[(3R)-1-[2-fluoro-6-[(4-methoxypiperidin-1-yl)methyl]phenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)CN1CCC(CC1)OC)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O ASOVDVUJXMSPSV-XMMPIXPASA-N 0.000 claims description 2
• LBGJOGAJUJJNDK-XMMPIXPASA-N 1-[(3R)-1-[2-fluoro-6-[(4-methylpiperazin-1-yl)methyl]phenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)CN1CCN(CC1)C)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O LBGJOGAJUJJNDK-XMMPIXPASA-N 0.000 claims description 2
• MCSJYTRSHQSIGY-LWMIZPGFSA-N 1-[(3R)-1-[2-fluoro-6-[1-(3-methoxyazetidin-1-yl)ethyl]phenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C(C)N1CC(C1)OC)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O MCSJYTRSHQSIGY-LWMIZPGFSA-N 0.000 claims description 2
• ARKNOVMEQKFZCQ-JOCHJYFZSA-N 1-[(3R)-1-[2-fluoro-6-[[2-hydroxyethyl(methyl)amino]methyl]phenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)CN(C)CCO)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O ARKNOVMEQKFZCQ-JOCHJYFZSA-N 0.000 claims description 2
• SRBAEXHJZFAUNJ-HSZRJFAPSA-N 1-[(3R)-1-[2-fluoro-6-[[2-methoxyethyl(methyl)amino]methyl]phenyl]pyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)CN(C)CCOC)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O SRBAEXHJZFAUNJ-HSZRJFAPSA-N 0.000 claims description 2
• JRMHIEWGBCRXFQ-HXUWFJFHSA-N 1-[(3R)-1-benzoylpyrrolidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound C(C1=CC=CC=C1)(=O)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O JRMHIEWGBCRXFQ-HXUWFJFHSA-N 0.000 claims description 2
• VEYIPQQSOXBGBD-UHFFFAOYSA-N 1-[1-(2,2-dimethylpropanoyl)piperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound CC(C(=O)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O)(C)C VEYIPQQSOXBGBD-UHFFFAOYSA-N 0.000 claims description 2
• LIALTGBNOCKXOH-UHFFFAOYSA-N 1-[1-(2,4-dimethoxypyridin-3-yl)piperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound COC1=NC=CC(=C1N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O)OC LIALTGBNOCKXOH-UHFFFAOYSA-N 0.000 claims description 2
• HWFCYBMZHQHACT-UHFFFAOYSA-N 1-[1-(2,4-dimethylpyridin-3-yl)piperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound CC1=NC=CC(=C1N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O)C HWFCYBMZHQHACT-UHFFFAOYSA-N 0.000 claims description 2
• SYGMAYQHEYEMQO-UHFFFAOYSA-N 1-[1-(2,6-difluorophenyl)piperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)F)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O SYGMAYQHEYEMQO-UHFFFAOYSA-N 0.000 claims description 2
• LTVDKLKUQWNBNZ-UHFFFAOYSA-N 1-[1-(2,6-difluorophenyl)piperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)pyridin-3-yl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)F)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC=1C(=NC=CC=1)C(F)(F)F)=O LTVDKLKUQWNBNZ-UHFFFAOYSA-N 0.000 claims description 2
• ZUVZOWXYNMYEOY-UHFFFAOYSA-N 1-[1-(2,6-difluorophenyl)piperidin-4-yl]-4-methoxy-3-[[3-(trifluoromethyl)pyridin-2-yl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)F)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=NC=CC=C1C(F)(F)F)=O ZUVZOWXYNMYEOY-UHFFFAOYSA-N 0.000 claims description 2
• KJAPYOHPIDWKGM-UHFFFAOYSA-N 1-[1-(2,6-difluorophenyl)piperidin-4-yl]-4-methoxy-3-[[4-(trifluoromethyl)pyridin-3-yl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)F)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC=1C=NC=CC=1C(F)(F)F)=O KJAPYOHPIDWKGM-UHFFFAOYSA-N 0.000 claims description 2
• VDZBYSIKIKFEOO-UHFFFAOYSA-N 1-[1-(2,6-dimethoxyphenyl)piperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound COC1=C(C(=CC=C1)OC)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O VDZBYSIKIKFEOO-UHFFFAOYSA-N 0.000 claims description 2
• CZPYVUWLPYZJDI-UHFFFAOYSA-N 1-[1-(2,6-dimethylphenyl)azepan-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound CC1=C(C(=CC=C1)C)N1CCC(CCC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O CZPYVUWLPYZJDI-UHFFFAOYSA-N 0.000 claims description 2
• JFWQDDPGBFCJDR-UHFFFAOYSA-N 1-[1-(2,6-dimethylphenyl)piperidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound CC1=C(C(=CC=C1)C)N1CC(CCC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O JFWQDDPGBFCJDR-UHFFFAOYSA-N 0.000 claims description 2
• ONKTXFDNNPZTSN-UHFFFAOYSA-N 1-[1-(2,6-dimethylphenyl)piperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound CC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O ONKTXFDNNPZTSN-UHFFFAOYSA-N 0.000 claims description 2
• USRDFWBYMVDYED-UHFFFAOYSA-N 1-[1-(2,6-dimethylphenyl)piperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)pyridin-3-yl]methyl]benzimidazol-2-one Chemical compound CC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC=1C(=NC=CC=1)C(F)(F)F)=O USRDFWBYMVDYED-UHFFFAOYSA-N 0.000 claims description 2
• JKIXECBJRYSQCL-UHFFFAOYSA-N 1-[1-(2,6-dimethylphenyl)piperidin-4-yl]-4-methoxy-3-[[3-(trifluoromethyl)pyridin-2-yl]methyl]benzimidazol-2-one Chemical compound CC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=NC=CC=C1C(F)(F)F)=O JKIXECBJRYSQCL-UHFFFAOYSA-N 0.000 claims description 2
• SLZMENXXQVJNBD-UHFFFAOYSA-N 1-[1-(2,6-dimethylphenyl)piperidin-4-yl]-4-methoxy-3-[[3-(trifluoromethyl)pyridin-4-yl]methyl]benzimidazol-2-one Chemical compound CC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=NC=C1)C(F)(F)F)=O SLZMENXXQVJNBD-UHFFFAOYSA-N 0.000 claims description 2
• FIDIDNSDCLVWGX-UHFFFAOYSA-N 1-[1-(2,6-dimethylphenyl)piperidin-4-yl]-4-methoxy-3-[[4-(trifluoromethyl)pyridin-3-yl]methyl]benzimidazol-2-one Chemical compound CC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC=1C=NC=CC=1C(F)(F)F)=O FIDIDNSDCLVWGX-UHFFFAOYSA-N 0.000 claims description 2
• PCRHQMJVVFFDLQ-UHFFFAOYSA-N 1-[1-(2-butoxyphenyl)piperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound C(CCC)OC1=C(C=CC=C1)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O PCRHQMJVVFFDLQ-UHFFFAOYSA-N 0.000 claims description 2
• YVBGEFZIKXMMIT-UHFFFAOYSA-N 1-[1-(2-cyclobutyloxyphenyl)piperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound C1(CCC1)OC1=C(C=CC=C1)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O YVBGEFZIKXMMIT-UHFFFAOYSA-N 0.000 claims description 2
• QJCGCMGMYGJGGN-UHFFFAOYSA-N 1-[1-(2-fluoro-4-methylpyridin-3-yl)piperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=NC=CC(=C1N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O)C QJCGCMGMYGJGGN-UHFFFAOYSA-N 0.000 claims description 2
• MSVHPRQRMXOBLN-UHFFFAOYSA-N 1-[1-(2-fluoro-6-methylphenyl)-3,3-dimethylpiperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CC(C(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O)(C)C MSVHPRQRMXOBLN-UHFFFAOYSA-N 0.000 claims description 2
• UPSCLFYTSJSLQW-UHFFFAOYSA-N 1-[1-(2-fluoro-6-methylphenyl)-3-methylpiperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CC(C(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O)C UPSCLFYTSJSLQW-UHFFFAOYSA-N 0.000 claims description 2
• QABSBBUSGBJHJN-UHFFFAOYSA-N 1-[1-(2-fluoro-6-methylphenyl)azepan-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CCC(CCC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O QABSBBUSGBJHJN-UHFFFAOYSA-N 0.000 claims description 2
• DRKQQFAHHCOGHD-UHFFFAOYSA-N 1-[1-(2-fluoro-6-methylphenyl)azetidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CC(C1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O DRKQQFAHHCOGHD-UHFFFAOYSA-N 0.000 claims description 2
• CZOSHXODDGTHAZ-UHFFFAOYSA-N 1-[1-(2-fluoro-6-methylphenyl)piperidin-3-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CC(CCC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O CZOSHXODDGTHAZ-UHFFFAOYSA-N 0.000 claims description 2
• VMYTYHYSLFPLOL-UHFFFAOYSA-N 1-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-4-methoxy-3-[(2-propan-2-yloxyphenyl)methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)OC(C)C)=O VMYTYHYSLFPLOL-UHFFFAOYSA-N 0.000 claims description 2
• VMYSQOAKSQCEDR-UHFFFAOYSA-N 1-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-4-methoxy-3-[(3-methoxypyrazin-2-yl)methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=NC=CN=C1OC)=O VMYSQOAKSQCEDR-UHFFFAOYSA-N 0.000 claims description 2
• KRJLLCGXLGMABS-UHFFFAOYSA-N 1-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-4-methoxy-3-[(3-propan-2-yloxypyrazin-2-yl)methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=NC=CN=C1OC(C)C)=O KRJLLCGXLGMABS-UHFFFAOYSA-N 0.000 claims description 2
• INVHAQRPRJFPJS-UHFFFAOYSA-N 1-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-4-methoxy-3-[(3-propan-2-yloxypyridin-2-yl)methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=NC=CC=C1OC(C)C)=O INVHAQRPRJFPJS-UHFFFAOYSA-N 0.000 claims description 2
• WJSVXVGLNXUZKH-UHFFFAOYSA-N 1-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-4-methoxy-3-[(3-propan-2-ylpyrazin-2-yl)methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=NC=CN=C1C(C)C)=O WJSVXVGLNXUZKH-UHFFFAOYSA-N 0.000 claims description 2
• NEOHSRZZEQBOIV-UHFFFAOYSA-N 1-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-4-methoxy-3-[(4-propan-2-ylpyridin-3-yl)methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC=1C=NC=CC=1C(C)C)=O NEOHSRZZEQBOIV-UHFFFAOYSA-N 0.000 claims description 2
• JUYFGAHFGZYOGZ-UHFFFAOYSA-N 1-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-4-methoxy-3-[(4-propan-2-ylpyrimidin-5-yl)methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC=1C(=NC=NC=1)C(C)C)=O JUYFGAHFGZYOGZ-UHFFFAOYSA-N 0.000 claims description 2
• MJOHFNTUEQJXFN-UHFFFAOYSA-N 1-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-4-methoxy-3-[[2-(oxetan-3-yloxy)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)OC1COC1)=O MJOHFNTUEQJXFN-UHFFFAOYSA-N 0.000 claims description 2
• QSHLKALCDANILB-UHFFFAOYSA-N 1-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O QSHLKALCDANILB-UHFFFAOYSA-N 0.000 claims description 2
• LBFWOSNHOYGSHA-UHFFFAOYSA-N 1-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-4-methoxy-3-[[3-(trifluoromethyl)pyrazin-2-yl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=NC=CN=C1C(F)(F)F)=O LBFWOSNHOYGSHA-UHFFFAOYSA-N 0.000 claims description 2
• JBNYDZDCMFTLAP-UHFFFAOYSA-N 1-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-4-methoxy-3-[[3-(trifluoromethyl)pyridin-2-yl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=NC=CC=C1C(F)(F)F)=O JBNYDZDCMFTLAP-UHFFFAOYSA-N 0.000 claims description 2
• BHXSGUMFXCGGJV-UHFFFAOYSA-N 1-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-4-methyl-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=C1C=CC=C2C)CC1=C(C=CC=C1)C(F)(F)F)=O BHXSGUMFXCGGJV-UHFFFAOYSA-N 0.000 claims description 2
• AZNUAJRLLIELLY-OYKVQYDMSA-N 1-[1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxy-3-[(1S)-1-[2-(trifluoromethyl)phenyl]ethyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CC(CC1)N1C(N(C2=C1C=CC=C2OC)[C@@H](C)C1=C(C=CC=C1)C(F)(F)F)=O AZNUAJRLLIELLY-OYKVQYDMSA-N 0.000 claims description 2
• OKKYURKEXMOFRD-UHFFFAOYSA-N 1-[1-(2-hydroxyphenyl)piperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound OC1=C(C=CC=C1)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O OKKYURKEXMOFRD-UHFFFAOYSA-N 0.000 claims description 2
• KRZZNEGYXOTWAW-UHFFFAOYSA-N 1-[1-(3-fluoropyridin-2-yl)piperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC=1C(=NC=CC=1)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O KRZZNEGYXOTWAW-UHFFFAOYSA-N 0.000 claims description 2
• BYKGZXWYEALQPE-UHFFFAOYSA-N 1-[1-(4,6-dimethoxypyrimidin-5-yl)piperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound COC1=NC=NC(=C1N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O)OC BYKGZXWYEALQPE-UHFFFAOYSA-N 0.000 claims description 2
• CJLUGKXWWKEOQK-UHFFFAOYSA-N 1-[1-(4-chloro-5-cyclopropyl-2-methylpyrazol-3-yl)piperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound ClC1=C(N(N=C1C1CC1)C)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O CJLUGKXWWKEOQK-UHFFFAOYSA-N 0.000 claims description 2
• NDSMRYZKQLCGIY-UHFFFAOYSA-N 1-[1-(4-fluoro-2-methylpyridin-3-yl)piperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=NC=C1)C)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O NDSMRYZKQLCGIY-UHFFFAOYSA-N 0.000 claims description 2
• GFDLNABZRRDEFM-UHFFFAOYSA-N 1-[1-(5-cyclopropyl-2,4-dimethylpyrazol-3-yl)piperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound C1(CC1)C=1C(=C(N(N=1)C)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O)C GFDLNABZRRDEFM-UHFFFAOYSA-N 0.000 claims description 2
• ZSQWIYYPAVEVSV-UHFFFAOYSA-N 1-[1-(5-cyclopropyl-2-methylpyrazol-3-yl)piperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound C1(CC1)C=1C=C(N(N=1)C)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O ZSQWIYYPAVEVSV-UHFFFAOYSA-N 0.000 claims description 2
• CLULPKVKGPKHJH-UHFFFAOYSA-N 1-[1-(cyclopropanecarbonyl)piperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound C1(CC1)C(=O)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O CLULPKVKGPKHJH-UHFFFAOYSA-N 0.000 claims description 2
• DIOFIPDMLZKNCR-UHFFFAOYSA-N 1-[1-[(2,4-dichlorophenyl)methyl]piperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound ClC1=C(CN2CCC(CC2)N2C(N(C3=C2C=CC=C3OC)CC2=C(C=CC=C2)C(F)(F)F)=O)C=CC(=C1)Cl DIOFIPDMLZKNCR-UHFFFAOYSA-N 0.000 claims description 2
• VGUJSYKEQDXFTR-UHFFFAOYSA-N 1-[1-[2-(2-hydroxyethoxy)phenyl]piperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound OCCOC1=C(C=CC=C1)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O VGUJSYKEQDXFTR-UHFFFAOYSA-N 0.000 claims description 2
• XJXLTPKTRNRTRM-UHFFFAOYSA-N 1-[1-[2-(cyclopropylmethoxy)phenyl]piperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound C1(CC1)COC1=C(C=CC=C1)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O XJXLTPKTRNRTRM-UHFFFAOYSA-N 0.000 claims description 2
• JLNSTGNDLGANRI-UHFFFAOYSA-N 1-[2-(2-fluoro-6-methylphenyl)-2-azabicyclo[2.2.1]heptan-5-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C2CC(C(C1)C2)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O JLNSTGNDLGANRI-UHFFFAOYSA-N 0.000 claims description 2
• BJZRMWQZGNKMBK-UHFFFAOYSA-N 1-[3-(2-fluoro-6-methylphenyl)-3-azabicyclo[3.1.1]heptan-6-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CC2C(C(C1)C2)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O BJZRMWQZGNKMBK-UHFFFAOYSA-N 0.000 claims description 2
• WQURVVDILIYWPK-UHFFFAOYSA-N 1-[3-fluoro-1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-4-methoxy-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-2-one Chemical compound FC1CN(CCC1N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O)C1=C(C=CC=C1C)F WQURVVDILIYWPK-UHFFFAOYSA-N 0.000 claims description 2
• AUSZXLHAORIZFA-HXUWFJFHSA-N 2-[3-fluoro-2-[(3R)-3-[4-methoxy-2-oxo-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-1-yl]pyrrolidin-1-yl]phenyl]acetaldehyde Chemical compound FC=1C(=C(C=CC=1)CC=O)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O AUSZXLHAORIZFA-HXUWFJFHSA-N 0.000 claims description 2
• PZYDLPRSMGXITD-HXUWFJFHSA-N 3-[(2,4-difluoro-6-propan-2-yloxyphenyl)methyl]-1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxybenzimidazol-2-one Chemical compound FC1=C(CN2C(N(C3=C2C(=CC=C3)OC)[C@H]2CN(CC2)C2=C(C=CC=C2C)F)=O)C(=CC(=C1)F)OC(C)C PZYDLPRSMGXITD-HXUWFJFHSA-N 0.000 claims description 2
• GSUOKEBLXONVMY-UHFFFAOYSA-N 3-[(2-cyclobutyloxyphenyl)methyl]-1-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-4-methoxybenzimidazol-2-one Chemical compound C1(CCC1)OC1=C(CN2C(N(C3=C2C(=CC=C3)OC)C2CCN(CC2)C2=C(C=CC=C2C)F)=O)C=CC=C1 GSUOKEBLXONVMY-UHFFFAOYSA-N 0.000 claims description 2
• ZHBDOILLVVUNQH-OAQYLSRUSA-N 3-[(2-cyclopropyloxyphenyl)methyl]-1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxybenzimidazol-2-one Chemical compound C1(CC1)OC1=C(CN2C(N(C3=C2C(=CC=C3)OC)[C@H]2CN(CC2)C2=C(C=CC=C2C)F)=O)C=CC=C1 ZHBDOILLVVUNQH-OAQYLSRUSA-N 0.000 claims description 2
• BNJBNQYCFOSZED-UHFFFAOYSA-N 3-[(2-cyclopropyloxyphenyl)methyl]-1-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-4-methoxybenzimidazol-2-one Chemical compound C1(CC1)OC1=C(CN2C(N(C3=C2C(=CC=C3)OC)C2CCN(CC2)C2=C(C=CC=C2C)F)=O)C=CC=C1 BNJBNQYCFOSZED-UHFFFAOYSA-N 0.000 claims description 2
• VCTJRHNVTAAHPE-UHFFFAOYSA-N 3-[(2-cyclopropylphenyl)methyl]-1-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-4-methoxybenzimidazol-2-one Chemical compound C1(CC1)C1=C(CN2C(N(C3=C2C(=CC=C3)OC)C2CCN(CC2)C2=C(C=CC=C2C)F)=O)C=CC=C1 VCTJRHNVTAAHPE-UHFFFAOYSA-N 0.000 claims description 2
• XNQLKFCMDQAIIR-MRXNPFEDSA-N 3-[(3R)-1-(2,6-difluorophenyl)pyrrolidin-3-yl]-7-methoxy-1-[[2-(trifluoromethyl)phenyl]methyl]imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C(=CC=C1)F)N1C[C@@H](CC1)N1C(N(C=2C1=NC=CC=2OC)CC1=C(C=CC=C1)C(F)(F)F)=O XNQLKFCMDQAIIR-MRXNPFEDSA-N 0.000 claims description 2
• RYUSVIGGSDLQJT-HXUWFJFHSA-N 3-[(3R)-1-(2,6-dimethylphenyl)pyrrolidin-3-yl]-7-methoxy-1-[[2-(trifluoromethyl)phenyl]methyl]imidazo[4,5-b]pyridin-2-one Chemical compound CC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C=2C1=NC=CC=2OC)CC1=C(C=CC=C1)C(F)(F)F)=O RYUSVIGGSDLQJT-HXUWFJFHSA-N 0.000 claims description 2
• XUIALUCCXIXWSQ-LJQANCHMSA-N 3-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-7-methoxy-5-methyl-1-[[2-(trifluoromethyl)phenyl]methyl]imidazo[4,5-b]pyridin-2-one Chemical compound FC1=C(C(=CC=C1)C)N1C[C@@H](CC1)N1C(N(C=2C1=NC(=CC=2OC)C)CC1=C(C=CC=C1)C(F)(F)F)=O XUIALUCCXIXWSQ-LJQANCHMSA-N 0.000 claims description 2
• SRNYOVOPKYGODU-MRXNPFEDSA-N 3-[(6-chloro-4-methoxypyridazin-3-yl)methyl]-1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxybenzimidazol-2-one Chemical compound ClC1=CC(=C(N=N1)CN1C(N(C2=C1C(=CC=C2)OC)[C@H]1CN(CC1)C1=C(C=CC=C1C)F)=O)OC SRNYOVOPKYGODU-MRXNPFEDSA-N 0.000 claims description 2
• YQLVJNQVAFRBNJ-GOSISDBHSA-N 3-[(6-chloro-4-propan-2-yloxypyridazin-3-yl)methyl]-1-[(3R)-1-(2-fluoro-6-methylphenyl)pyrrolidin-3-yl]-4-methoxybenzimidazol-2-one Chemical compound ClC1=CC(=C(N=N1)CN1C(N(C2=C1C(=CC=C2)OC)[C@H]1CN(CC1)C1=C(C=CC=C1C)F)=O)OC(C)C YQLVJNQVAFRBNJ-GOSISDBHSA-N 0.000 claims description 2
• NIGDTDUYVSNNSL-UHFFFAOYSA-N 3-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-7-methoxy-1-[[2-(trifluoromethyl)phenyl]methyl]imidazo[4,5-c]pyridin-2-one Chemical compound FC1=C(C(=CC=C1)C)N1CCC(CC1)N1C(N(C2=C1C=NC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O NIGDTDUYVSNNSL-UHFFFAOYSA-N 0.000 claims description 2
• ZOEFQKMYJZQGLE-UHFFFAOYSA-N 3-[4-[4-methoxy-2-oxo-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-1-yl]piperidin-1-yl]-4-methylpyridine-2-carbonitrile Chemical compound COC1=CC=CC=2N(C(N(C=21)CC1=C(C=CC=C1)C(F)(F)F)=O)C1CCN(CC1)C=1C(=NC=CC=1C)C#N ZOEFQKMYJZQGLE-UHFFFAOYSA-N 0.000 claims description 2
• JBMBNBQNKBUXKO-UHFFFAOYSA-N 3-[[2-(cyclopropylmethoxy)phenyl]methyl]-1-[1-(2-fluoro-6-methylphenyl)piperidin-4-yl]-4-methoxybenzimidazol-2-one Chemical compound C1(CC1)COC1=C(CN2C(N(C3=C2C(=CC=C3)OC)C2CCN(CC2)C2=C(C=CC=C2C)F)=O)C=CC=C1 JBMBNBQNKBUXKO-UHFFFAOYSA-N 0.000 claims description 2
• SYLOPJYAJAYFAI-UHFFFAOYSA-N 3-cyclopropyl-5-[4-[4-methoxy-2-oxo-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-1-yl]piperidin-1-yl]-1-methylpyrazole-4-carbaldehyde Chemical compound C1(CC1)C1=NN(C(=C1C=O)N1CCC(CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O)C SYLOPJYAJAYFAI-UHFFFAOYSA-N 0.000 claims description 2
• CUCYRUUZCCGXMB-HXUWFJFHSA-N 3-fluoro-2-[(3R)-3-[4-(hydroxymethyl)-2-oxo-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-1-yl]pyrrolidin-1-yl]benzonitrile Chemical compound FC=1C(=C(C#N)C=CC=1)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2CO)CC1=C(C=CC=C1)C(F)(F)F)=O CUCYRUUZCCGXMB-HXUWFJFHSA-N 0.000 claims description 2
• JUUGEYVHFWLNBX-LJQANCHMSA-N 3-fluoro-2-[(3R)-3-[4-methoxy-2-oxo-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-1-yl]pyrrolidin-1-yl]benzaldehyde Chemical compound FC=1C(=C(C=O)C=CC=1)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O JUUGEYVHFWLNBX-LJQANCHMSA-N 0.000 claims description 2
• WNVFYLOQNWVZIG-LJQANCHMSA-N 3-fluoro-2-[(3R)-3-[4-methoxy-2-oxo-3-[[2-(trifluoromethyl)phenyl]methyl]benzimidazol-1-yl]pyrrolidin-1-yl]benzonitrile Chemical compound FC=1C(=C(C#N)C=CC=1)N1C[C@@H](CC1)N1C(N(C2=C1C=CC=C2OC)CC1=C(C=CC=C1)C(F)(F)F)=O WNVFYLOQNWVZIG-LJQANCHMSA-N 0.000 claims description 2
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