JP2020524719A5

JP2020524719A5 -

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Publication number: JP2020524719A5
Authority: JP; Japan
Prior art keywords: oxo; carboxamide; tetrahydroquinazoline; trifluorobenzyl; dimethyl
Prior art date: 2018-06-21
Legal status : Granted

Application number

JP2020520840A

Other languages

English (en)

Japanese (ja)

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JP7296954B2 (ja

JP2020524719A (ja

Filing date

2018-06-21

Publication date

2021-07-26

2017-06-22 Priority claimed from GB1709959.9A external-priority patent/GB2563642A/en

2018-06-21 Application filed filed Critical

2018-06-21 Priority claimed from PCT/GB2018/051730 external-priority patent/WO2018234808A1/en

2020-08-20 Publication of JP2020524719A publication Critical patent/JP2020524719A/ja

2021-07-26 Publication of JP2020524719A5 publication Critical patent/JP2020524719A5/ja

2023-06-23 Application granted granted Critical

2023-06-23 Publication of JP7296954B2 publication Critical patent/JP7296954B2/ja

Status Active legal-status Critical Current

2038-06-21 Anticipated expiration legal-status Critical

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-1 azido, sulfonyl Chemical group 0.000 claims description 146
150000001875 compounds Chemical class 0.000 claims description 75
125000002950 monocyclic group Chemical group 0.000 claims description 65
125000002619 bicyclic group Chemical group 0.000 claims description 62
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 56
125000000217 alkyl group Chemical group 0.000 claims description 41
229910052736 halogen Inorganic materials 0.000 claims description 34
150000002367 halogens Chemical class 0.000 claims description 34
125000003118 aryl group Chemical group 0.000 claims description 24
150000003839 salts Chemical class 0.000 claims description 20
239000012453 solvate Substances 0.000 claims description 20
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
125000000753 cycloalkyl group Chemical group 0.000 claims description 18
229910052799 carbon Inorganic materials 0.000 claims description 17
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
125000003342 alkenyl group Chemical group 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
125000001072 heteroaryl group Chemical group 0.000 claims description 10
125000000623 heterocyclic group Chemical group 0.000 claims description 10
150000001540 azides Chemical class 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 9
229940124597 therapeutic agent Drugs 0.000 claims description 9
UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims description 8
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 8
125000004104 aryloxy group Chemical group 0.000 claims description 8
ZJXZSIYSNXKHEA-UHFFFAOYSA-N ethyl dihydrogen phosphate Chemical compound CCOP(O)(O)=O ZJXZSIYSNXKHEA-UHFFFAOYSA-N 0.000 claims description 8
MHZDONKZSXBOGL-UHFFFAOYSA-N propyl dihydrogen phosphate Chemical compound CCCOP(O)(O)=O MHZDONKZSXBOGL-UHFFFAOYSA-N 0.000 claims description 8
201000010099 disease Diseases 0.000 claims description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
125000001624 naphthyl group Chemical group 0.000 claims description 7
206010028980 Neoplasm Diseases 0.000 claims description 6
125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
201000011510 cancer Diseases 0.000 claims description 5
239000003112 inhibitor Substances 0.000 claims description 5
125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims description 4
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
125000004175 fluorobenzyl group Chemical group 0.000 claims description 4
HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 4
CAAULPUQFIIOTL-UHFFFAOYSA-N methyl dihydrogen phosphate Chemical compound COP(O)(O)=O CAAULPUQFIIOTL-UHFFFAOYSA-N 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
206010039491 Sarcoma Diseases 0.000 claims description 3
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 3
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
239000002158 endotoxin Substances 0.000 claims description 3
239000003446 ligand Substances 0.000 claims description 3
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
JEXGXMIQQXSICN-ZDUSSCGKSA-N (4S)-1-[(2,3-difluoro-5-methoxyphenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound C1=C2C(N(C(=O)N([C@H]2C)C)CC2=C(F)C(F)=CC(OC)=C2)=CC(=C1)C(=O)NCC1=C(C=C(F)C=C1F)F JEXGXMIQQXSICN-ZDUSSCGKSA-N 0.000 claims description 2
VDALQPBXDJFNMC-LBPRGKRZSA-N (4S)-1-[(2,3-difluoro-6-hydroxyphenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC=C1F)O VDALQPBXDJFNMC-LBPRGKRZSA-N 0.000 claims description 2
BGTUEIQPCOVFSP-ZDUSSCGKSA-N (4S)-1-[(2,3-difluoro-6-methoxyphenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC=C1F)OC BGTUEIQPCOVFSP-ZDUSSCGKSA-N 0.000 claims description 2
PCOAPICEAAGXOI-LBPRGKRZSA-N (4S)-1-[(2,4-difluoro-6-hydroxyphenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC(=C1)F)O PCOAPICEAAGXOI-LBPRGKRZSA-N 0.000 claims description 2
TYWWHARHEICZSL-ZDUSSCGKSA-N (4S)-1-[(2,4-difluoro-6-methoxyphenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC(=C1)F)OC TYWWHARHEICZSL-ZDUSSCGKSA-N 0.000 claims description 2
GKMUPZZKWVZALH-LBPRGKRZSA-N (4S)-1-[(2,6-difluoro-3-hydroxyphenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC=C1O)F GKMUPZZKWVZALH-LBPRGKRZSA-N 0.000 claims description 2
MIQSJBHAXVCIFC-LBPRGKRZSA-N (4S)-1-[(2,6-difluoro-4-hydroxyphenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC(=C1)O)F MIQSJBHAXVCIFC-LBPRGKRZSA-N 0.000 claims description 2
NMFRLKDNNVKXRP-ZDUSSCGKSA-N (4S)-1-[(2,6-difluoro-4-methoxyphenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC(=C1)OC)F NMFRLKDNNVKXRP-ZDUSSCGKSA-N 0.000 claims description 2
VHVNPVYFQANNJC-LBPRGKRZSA-N (4S)-1-[(2-chloro-3,6-difluorophenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC=C1F)F VHVNPVYFQANNJC-LBPRGKRZSA-N 0.000 claims description 2
CLRVRLLTCDBMTG-LBPRGKRZSA-N (4S)-1-[(2-chloro-6-fluoro-3-hydroxyphenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC=C1O)F CLRVRLLTCDBMTG-LBPRGKRZSA-N 0.000 claims description 2
JLQLGPQLESYAOI-ZDUSSCGKSA-N (4S)-1-[(2-chloro-6-fluoro-3-methoxyphenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC=C1OC)F JLQLGPQLESYAOI-ZDUSSCGKSA-N 0.000 claims description 2
JEOFUVXNEUHSKM-LBPRGKRZSA-N (4S)-1-[(2-chloro-6-fluoro-4-hydroxyphenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC(=C1)O)F JEOFUVXNEUHSKM-LBPRGKRZSA-N 0.000 claims description 2
XWICQCKTWFTQQW-ZDUSSCGKSA-N (4S)-1-[(2-chloro-6-fluoro-4-methoxyphenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC(=C1)OC)F XWICQCKTWFTQQW-ZDUSSCGKSA-N 0.000 claims description 2
LZJOJRLKDJTVBT-HNNXBMFYSA-N (4S)-1-[(2-chloro-6-fluorophenyl)methyl]-N-(2-hydroxyethyl)-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)N(CC2=C(C=C(C=C2F)F)F)CCO)C)C)=O)C(=CC=C1)F LZJOJRLKDJTVBT-HNNXBMFYSA-N 0.000 claims description 2
PZVFGWJJMSLXNW-ZDUSSCGKSA-N (4S)-1-[(2-chloro-6-fluorophenyl)methyl]-N-[(2,6-difluoro-4-hydroxyphenyl)methyl]-3,4-dimethyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)O)F)C)C)=O)C(=CC=C1)F PZVFGWJJMSLXNW-ZDUSSCGKSA-N 0.000 claims description 2
ZVABDMCTWJZHMJ-AWEZNQCLSA-N (4S)-1-[(2-chloro-6-fluorophenyl)methyl]-N-[(2,6-difluoro-4-methoxyphenyl)methyl]-3,4-dimethyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)OC)F)C)C)=O)C(=CC=C1)F ZVABDMCTWJZHMJ-AWEZNQCLSA-N 0.000 claims description 2
XYRZRZGDZDDXTJ-AWEZNQCLSA-N (4S)-1-[(2-chloro-6-fluorophenyl)methyl]-N-[(2-fluoro-3-hydroxyphenyl)methyl]-3,4-dimethyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C(=CC=C2)O)F)C)C)=O)C(=CC=C1)F XYRZRZGDZDDXTJ-AWEZNQCLSA-N 0.000 claims description 2
GZSNKVVYQRNSHF-HNNXBMFYSA-N (4S)-1-[(2-chloro-6-fluorophenyl)methyl]-N-[(2-fluoro-3-methoxyphenyl)methyl]-3,4-dimethyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C(=CC=C2)OC)F)C)C)=O)C(=CC=C1)F GZSNKVVYQRNSHF-HNNXBMFYSA-N 0.000 claims description 2
PICCAHDQYHIHRJ-AWEZNQCLSA-N (4S)-1-[(2-chloro-6-fluorophenyl)methyl]-N-[(2-fluoro-6-hydroxyphenyl)methyl]-3,4-dimethyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=CC=C2O)F)C)C)=O)C(=CC=C1)F PICCAHDQYHIHRJ-AWEZNQCLSA-N 0.000 claims description 2
XZGGDMVKSQZERN-HNNXBMFYSA-N (4S)-1-[(2-chloro-6-fluorophenyl)methyl]-N-[(2-fluoro-6-methoxyphenyl)methyl]-3,4-dimethyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=CC=C2OC)F)C)C)=O)C(=CC=C1)F XZGGDMVKSQZERN-HNNXBMFYSA-N 0.000 claims description 2
LENVKOWHQSYQLM-AWEZNQCLSA-N (4S)-1-[(2-chloro-6-fluorophenyl)methyl]-N-[(3-fluoro-5-hydroxyphenyl)methyl]-3,4-dimethyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=CC(=CC(=C2)O)F)C)C)=O)C(=CC=C1)F LENVKOWHQSYQLM-AWEZNQCLSA-N 0.000 claims description 2
DLMRUIXCQMJOSU-HNNXBMFYSA-N (4S)-1-[(2-chloro-6-fluorophenyl)methyl]-N-[(3-fluoro-5-methoxyphenyl)methyl]-3,4-dimethyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=CC(=CC(=C2)OC)F)C)C)=O)C(=CC=C1)F DLMRUIXCQMJOSU-HNNXBMFYSA-N 0.000 claims description 2
GXUCJRLXTPGISZ-AWEZNQCLSA-N (4S)-1-[(2-chloro-6-fluorophenyl)methyl]-N-[(4-fluoro-2-hydroxyphenyl)methyl]-3,4-dimethyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2)F)O)C)C)=O)C(=CC=C1)F GXUCJRLXTPGISZ-AWEZNQCLSA-N 0.000 claims description 2
LGHDMGDLBDKQTD-HNNXBMFYSA-N (4S)-1-[(2-chloro-6-fluorophenyl)methyl]-N-[(4-fluoro-2-methoxyphenyl)methyl]-3,4-dimethyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2)F)OC)C)C)=O)C(=CC=C1)F LGHDMGDLBDKQTD-HNNXBMFYSA-N 0.000 claims description 2
XBHIMYSWNANBFW-INIZCTEOSA-N (4S)-1-[(2-chloro-6-fluorophenyl)methyl]-N-[[2-fluoro-3-(2-hydroxyethoxy)phenyl]methyl]-3,4-dimethyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound O(CCO)C1=CC=CC(CNC(=O)C2=CC=C3C(=C2)N(C(=O)N([C@H]3C)C)CC2=C(Cl)C=CC=C2F)=C1F XBHIMYSWNANBFW-INIZCTEOSA-N 0.000 claims description 2
IQNZMGVIIIOUHG-INIZCTEOSA-N (4S)-1-[(2-chloro-6-fluorophenyl)methyl]-N-[[3-fluoro-5-(2-hydroxyethoxy)phenyl]methyl]-3,4-dimethyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=CC(=CC(=C2)OCCO)F)C)C)=O)C(=CC=C1)F IQNZMGVIIIOUHG-INIZCTEOSA-N 0.000 claims description 2
HMXJMBHQBVUHRO-INIZCTEOSA-N (4S)-1-[(2-chloro-6-fluorophenyl)methyl]-N-[[4-fluoro-2-(2-hydroxyethoxy)phenyl]methyl]-3,4-dimethyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2)F)OCCO)C)C)=O)C(=CC=C1)F HMXJMBHQBVUHRO-INIZCTEOSA-N 0.000 claims description 2
BRCHPQDVICBQGB-LBPRGKRZSA-N (4S)-1-[(2-fluoro-4,5-dihydroxyphenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C=C(C(=C1)O)O BRCHPQDVICBQGB-LBPRGKRZSA-N 0.000 claims description 2
CAAVKYZJGMYRSU-AWEZNQCLSA-N (4S)-1-[(2-fluoro-4,5-dimethoxyphenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound C1=2[C@@H](N(C(=O)N(C=2C=C(C=C1)C(=O)NCC1=C(C=C(F)C=C1F)F)CC1=C(F)C=C(OC)C(OC)=C1)C)C CAAVKYZJGMYRSU-AWEZNQCLSA-N 0.000 claims description 2
VGLYLDSLYPFQDL-LBPRGKRZSA-N (4S)-1-[(3,5-difluoropyridin-4-yl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC=1C=NC=C(C=1CN1C(N([C@H](C2=CC=C(C=C12)C(=O)NCC1=C(C=C(C=C1F)F)F)C)C)=O)F VGLYLDSLYPFQDL-LBPRGKRZSA-N 0.000 claims description 2
MCOHIKIATPNPNR-LBPRGKRZSA-N (4S)-1-[(3-amino-2-chloro-6-fluorophenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound NC=1C(=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC=1)F)Cl MCOHIKIATPNPNR-LBPRGKRZSA-N 0.000 claims description 2
LNXSMRWEUGQQIX-LBPRGKRZSA-N (4S)-1-[(3-carbamoyl-2,6-difluorophenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound C(N)(=O)C=1C(=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC=1)F)F LNXSMRWEUGQQIX-LBPRGKRZSA-N 0.000 claims description 2
IUGFPSJNSCKWKZ-LBPRGKRZSA-N (4S)-1-[(3-carbamoyl-2-chloro-6-fluorophenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound C(N)(=O)C=1C(=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC=1)F)Cl IUGFPSJNSCKWKZ-LBPRGKRZSA-N 0.000 claims description 2
LMLUDKXRQHQKGR-AWEZNQCLSA-N (4S)-1-[(3-fluoro-2-methylpyridin-4-yl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound C1=CC2=C(N(C(=O)N([C@H]2C)C)CC2=C(F)C(C)=NC=C2)C=C1C(=O)NCC1=C(C=C(F)C=C1F)F LMLUDKXRQHQKGR-AWEZNQCLSA-N 0.000 claims description 2
UHIVNWNLUZWZJF-LBPRGKRZSA-N (4S)-1-[(4-amino-2,6-difluorophenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound NC1=CC(=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=C1)F)F UHIVNWNLUZWZJF-LBPRGKRZSA-N 0.000 claims description 2
OCFWSQNCIPXVBU-AWEZNQCLSA-N (4S)-1-[(4-aminophenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound NC1=CC=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C=C1 OCFWSQNCIPXVBU-AWEZNQCLSA-N 0.000 claims description 2
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SRKPSDFAFUFALA-LBPRGKRZSA-N (4S)-1-[(5-chloro-3-fluoro-1-methyl-2-oxopyridin-4-yl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound ClC=1C(=C(C(N(C=1)C)=O)F)CN1C(N([C@H](C2=CC=C(C=C12)C(=O)NCC1=C(C=C(C=C1F)F)F)C)C)=O SRKPSDFAFUFALA-LBPRGKRZSA-N 0.000 claims description 2
HHLPOGQULWXSRS-LBPRGKRZSA-N (4S)-1-[(6-amino-2,3-difluorophenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound NC1=CC=C(C(=C1CN1C(N([C@H](C2=CC=C(C=C12)C(=O)NCC1=C(C=C(C=C1F)F)F)C)C)=O)F)F HHLPOGQULWXSRS-LBPRGKRZSA-N 0.000 claims description 2
GIBBYHYNPJEADH-LBPRGKRZSA-N (4S)-1-[(6-chloro-2,3-difluorophenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound ClC1=CC=C(C(=C1CN1C(N([C@H](C2=CC=C(C=C12)C(=O)NCC1=C(C=C(C=C1F)F)F)C)C)=O)F)F GIBBYHYNPJEADH-LBPRGKRZSA-N 0.000 claims description 2
LBVKBIQNENRKPZ-AWEZNQCLSA-N (4S)-1-[(6-chloro-2-fluoro-3-methylphenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound ClC1=CC=C(C(=C1CN1C(N([C@H](C2=CC=C(C=C12)C(=O)NCC1=C(C=C(C=C1F)F)F)C)C)=O)F)C LBVKBIQNENRKPZ-AWEZNQCLSA-N 0.000 claims description 2
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UFZUUDGROAPMJU-AWEZNQCLSA-N (4S)-1-[[2,3-difluoro-6-(2-hydroxyethoxy)phenyl]methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC=C1F)OCCO UFZUUDGROAPMJU-AWEZNQCLSA-N 0.000 claims description 2
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CSMJIKODJFXJOL-AWEZNQCLSA-N (4S)-1-[[2,6-difluoro-3-(2-hydroxyethylcarbamoyl)phenyl]methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC=C1C(NCCO)=O)F CSMJIKODJFXJOL-AWEZNQCLSA-N 0.000 claims description 2
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HZJAZFFZYCZOMQ-HNNXBMFYSA-N (4S)-1-[[2,6-difluoro-4-(3-hydroxypropoxy)phenyl]methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC(=C1)OCCCO)F HZJAZFFZYCZOMQ-HNNXBMFYSA-N 0.000 claims description 2
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XSJVYVDFNYSYQU-HNNXBMFYSA-N (4S)-1-[[2-chloro-6-fluoro-3-(3-hydroxypropoxy)phenyl]methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC=C1OCCCO)F XSJVYVDFNYSYQU-HNNXBMFYSA-N 0.000 claims description 2
UHQQQEVPDICEBC-HNNXBMFYSA-N (4S)-1-[[2-fluoro-5-(2-hydroxyethoxy)phenyl]methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound C1=C2C(=CC(=C1)C(=O)NCC1=C(C=C(F)C=C1F)F)N(C(=O)N([C@H]2C)C)CC1=C(F)C=CC(OCCO)=C1 UHQQQEVPDICEBC-HNNXBMFYSA-N 0.000 claims description 2
YBCWHNKKCIOEOL-INIZCTEOSA-N (4S)-1-[[2-fluoro-5-(3-hydroxypropoxy)phenyl]methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound C1=2[C@@H](N(C(=O)N(C=2C=C(C=C1)C(=O)NCC1=C(C=C(F)C=C1F)F)CC1=C(F)C=CC(OCCCO)=C1)C)C YBCWHNKKCIOEOL-INIZCTEOSA-N 0.000 claims description 2
OMHSVZMJKNUSOH-RSAXXLAASA-N (4S)-1-[[2-fluoro-6-(2-hydroxyethylamino)phenyl]methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide hydrochloride Chemical compound Cl.FC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC=C1)NCCO OMHSVZMJKNUSOH-RSAXXLAASA-N 0.000 claims description 2
NDNLXNVXVSEJQY-INIZCTEOSA-N (4S)-1-[[2-fluoro-6-(3-hydroxypropylamino)phenyl]methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC1=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC=C1)NCCCO NDNLXNVXVSEJQY-INIZCTEOSA-N 0.000 claims description 2
RFILHPPGQQONRH-MBIQTGHCSA-N (4S)-1-[[4-(2,3-dihydroxypropoxy)-2,6-difluorophenyl]methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound OC(COC1=CC(=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=C1)F)F)CO RFILHPPGQQONRH-MBIQTGHCSA-N 0.000 claims description 2
VFUMVLNABYOPHJ-UQKRIMTDSA-N (4S)-1-[[4-(2-aminoethoxy)-2,6-difluorophenyl]methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide hydrochloride Chemical compound Cl.NCCOC1=CC(=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=C1)F)F VFUMVLNABYOPHJ-UQKRIMTDSA-N 0.000 claims description 2
IMHLDSWIHPQNGM-UQKRIMTDSA-N (4S)-1-[[4-(2-aminoethoxy)-2-chloro-6-fluorophenyl]methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide hydrochloride Chemical compound Cl.NCCOC1=CC(=C(CN2C(N([C@H](C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=C1)F)Cl IMHLDSWIHPQNGM-UQKRIMTDSA-N 0.000 claims description 2
SMWVFTZJSMVCPF-HNNXBMFYSA-N (4S)-1-[[4-(3-aminopropoxy)-2,6-difluorophenyl]methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound C1=2[C@@H](N(C(=O)N(C=2C=C(C=C1)C(=O)NCC1=C(C=C(F)C=C1F)F)CC1=C(F)C=C(OCCCN)C=C1F)C)C SMWVFTZJSMVCPF-HNNXBMFYSA-N 0.000 claims description 2
FLXDGHUSXNLARR-ZDUSSCGKSA-N (4S)-1-[[5-chloro-3-fluoro-1-(2-hydroxyethyl)-2-oxopyridin-4-yl]methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound ClC=1C(=C(C(N(C=1)CCO)=O)F)CN1C(N([C@H](C2=CC=C(C=C12)C(=O)NCC1=C(C=C(C=C1F)F)F)C)C)=O FLXDGHUSXNLARR-ZDUSSCGKSA-N 0.000 claims description 2
AOWYNZHDNGKTPY-LBPRGKRZSA-N (4S)-N,1-bis[(2,6-difluoro-4-hydroxyphenyl)methyl]-3,4-dimethyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound FC1=C(CNC(=O)C2=CC=C3[C@@H](N(C(N(C3=C2)CC2=C(C=C(C=C2F)O)F)=O)C)C)C(=CC(=C1)O)F AOWYNZHDNGKTPY-LBPRGKRZSA-N 0.000 claims description 2
FZKNIXPHFOEFCK-AWEZNQCLSA-N (4S)-N,1-bis[(2,6-difluoro-4-methoxyphenyl)methyl]-3,4-dimethyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound FC1=C(CNC(=O)C2=CC=C3[C@@H](N(C(N(C3=C2)CC2=C(C=C(C=C2F)OC)F)=O)C)C)C(=CC(=C1)OC)F FZKNIXPHFOEFCK-AWEZNQCLSA-N 0.000 claims description 2
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 2
HWDBXBFALMOWDR-UHFFFAOYSA-N 1-(imidazo[1,2-a]pyridin-2-ylmethyl)-3-methyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound C1(F)=CC(F)=C(CNC(=O)C2=CC=C3C(N(C(=O)N(C3)C)CC=3N=C4N(C=3)C=CC=C4)=C2)C(F)=C1 HWDBXBFALMOWDR-UHFFFAOYSA-N 0.000 claims description 2
VUGIXPSCTYBHII-UHFFFAOYSA-N 1-[(1,5-dimethylpyrazol-3-yl)methyl]-3-methyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound C1=C2C(=CC(=C1)C(=O)NCC1=C(C=C(F)C=C1F)F)N(C(=O)N(C2)C)CC=1C=C(C)N(N=1)C VUGIXPSCTYBHII-UHFFFAOYSA-N 0.000 claims description 2
BGTUEIQPCOVFSP-UHFFFAOYSA-N 1-[(2,3-difluoro-6-methoxyphenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC1=C(CN2C(N(C(C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC=C1F)OC BGTUEIQPCOVFSP-UHFFFAOYSA-N 0.000 claims description 2
VJWIZHHUBSSRGW-UHFFFAOYSA-N 1-[(2,4-difluorophenyl)methyl]-3-methyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC1=C(CN2C(N(CC3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)=O)C=CC(=C1)F VJWIZHHUBSSRGW-UHFFFAOYSA-N 0.000 claims description 2
FIXSCOWJAICIJQ-UHFFFAOYSA-N 1-[(2,5-dimethylpyrazol-3-yl)methyl]-N-[(5-fluoro-1-benzofuran-2-yl)methyl]-3,4-dimethyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound C1=CC=2OC(CNC(=O)C3=CC=C4C(=C3)N(C(=O)N(C4C)C)CC=3N(N=C(C=3)C)C)=CC=2C=C1F FIXSCOWJAICIJQ-UHFFFAOYSA-N 0.000 claims description 2
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OEYCOZDVAPBZJG-UHFFFAOYSA-N 1-[(2,6-dimethylphenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound CC1=C(CN2C(N(C(C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC=C1)C OEYCOZDVAPBZJG-UHFFFAOYSA-N 0.000 claims description 2
KJBYJGXYDDWUCW-UHFFFAOYSA-N 1-[(2-amino-6-fluorophenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound NC1=C(CN2C(N(C(C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC=C1)F KJBYJGXYDDWUCW-UHFFFAOYSA-N 0.000 claims description 2
KKZMLJWEZJZQHD-UHFFFAOYSA-N 1-[(2-bromo-6-fluorophenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound C1=2C(N(C(=O)N(C=2C=C(C=C1)C(=O)NCC1=C(C=C(F)C=C1F)F)CC1=C(F)C=CC=C1Br)C)C KKZMLJWEZJZQHD-UHFFFAOYSA-N 0.000 claims description 2
CAHIWBFAWIWVSR-UHFFFAOYSA-N 1-[(2-bromo-6-fluorophenyl)methyl]-3-methyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound BrC1=C(CN2C(N(CC3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)=O)C(=CC=C1)F CAHIWBFAWIWVSR-UHFFFAOYSA-N 0.000 claims description 2
DXUYKOCJEHEVQC-UHFFFAOYSA-N 1-[(2-chloro-4-fluorophenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N(C(C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C=CC(=C1)F DXUYKOCJEHEVQC-UHFFFAOYSA-N 0.000 claims description 2
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NEYRSKXLHZDBRN-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-2-oxo-3-phenylmethoxy-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound C(C1=CC=CC=C1)ON1C(N(C2=CC(=CC=C2C1)C(=O)NCC1=C(C=C(C=C1F)F)F)CC1=C(C=CC=C1F)Cl)=O NEYRSKXLHZDBRN-UHFFFAOYSA-N 0.000 claims description 2
DQAVYPSHLPBIAS-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N(C(C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC=C1)F DQAVYPSHLPBIAS-UHFFFAOYSA-N 0.000 claims description 2
VDRRNPNJRUOZQW-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-3,4-dimethyl-N-[(5-methylfuran-2-yl)methyl]-2-oxo-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N(C(C3=CC=C(C=C23)C(=O)NCC=2OC(=CC=2)C)C)C)=O)C(=CC=C1)F VDRRNPNJRUOZQW-UHFFFAOYSA-N 0.000 claims description 2
MBRVNXPWLUFBNY-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-3-(1-methylimidazol-4-yl)-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N(CC3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C=2N=CN(C=2)C)=O)C(=CC=C1)F MBRVNXPWLUFBNY-UHFFFAOYSA-N 0.000 claims description 2
NXYHMHPTUIHZMZ-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-3-hydroxy-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N(CC3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)O)=O)C(=CC=C1)F NXYHMHPTUIHZMZ-UHFFFAOYSA-N 0.000 claims description 2
SYRMDCOVEKUNBH-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-3-methoxy-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N(CC3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)OC)=O)C(=CC=C1)F SYRMDCOVEKUNBH-UHFFFAOYSA-N 0.000 claims description 2
FSAWXJGTRGIGMK-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-3-methyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N(CC3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)=O)C(=CC=C1)F FSAWXJGTRGIGMK-UHFFFAOYSA-N 0.000 claims description 2
RFVYWWQCTIBZKJ-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-3-methyl-2-oxo-N-[(2-oxo-1,3-dihydroindol-5-yl)methyl]-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N(CC3=CC=C(C=C23)C(=O)NCC=2C=C3CC(NC3=CC=2)=O)C)=O)C(=CC=C1)F RFVYWWQCTIBZKJ-UHFFFAOYSA-N 0.000 claims description 2
JYRPJFMJBYILKQ-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-3-methyl-N-[(1-methylindazol-6-yl)methyl]-2-oxo-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N(CC3=CC=C(C=C23)C(=O)NCC2=CC=C3C=NN(C3=C2)C)C)=O)C(=CC=C1)F JYRPJFMJBYILKQ-UHFFFAOYSA-N 0.000 claims description 2
ZYXUVUCZJPXJMU-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-3-methyl-N-[(5-nitro-1-benzofuran-2-yl)methyl]-2-oxo-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N(CC3=CC=C(C=C23)C(=O)NCC=2OC3=C(C=2)C=C(C=C3)[N+](=O)[O-])C)=O)C(=CC=C1)F ZYXUVUCZJPXJMU-UHFFFAOYSA-N 0.000 claims description 2
JWWCAYDTFKCJFR-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-3-methyl-N-[[3-(1,3-oxazol-2-yl)phenyl]methyl]-2-oxo-4H-quinazoline-7-carboxamide Chemical compound C1(=CC=CC(=C1)CNC(=O)C1=CC=C2C(=C1)N(C(=O)N(C2)C)CC1=C(Cl)C=CC=C1F)C=1OC=CN=1 JWWCAYDTFKCJFR-UHFFFAOYSA-N 0.000 claims description 2
VBQMQTDXZRARSY-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-3-methyl-N-[[3-(1-methylpyrazol-3-yl)phenyl]methyl]-2-oxo-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N(CC3=CC=C(C=C23)C(=O)NCC2=CC(=CC=C2)C2=NN(C=C2)C)C)=O)C(=CC=C1)F VBQMQTDXZRARSY-UHFFFAOYSA-N 0.000 claims description 2
OWPOEPRQRNOVKZ-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-3-methyl-N-[[3-(4-methylpiperazin-1-yl)phenyl]methyl]-2-oxo-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N(CC3=CC=C(C=C23)C(=O)NCC2=CC(=CC=C2)N2CCN(CC2)C)C)=O)C(=CC=C1)F OWPOEPRQRNOVKZ-UHFFFAOYSA-N 0.000 claims description 2
RZGHLOMGHYEPTB-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-4-methyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-3,4-dihydroquinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(NC(C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)=O)C(=CC=C1)F RZGHLOMGHYEPTB-UHFFFAOYSA-N 0.000 claims description 2
CFGLRHWQRBDRGU-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-N-(2,3-dihydro-1,4-benzodioxin-5-ylmethyl)-3-methyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound CN1CC2=CC=C(C=C2N(CC2=C(F)C=CC=C2Cl)C1=O)C(=O)NCC1=C2OCCOC2=CC=C1 CFGLRHWQRBDRGU-UHFFFAOYSA-N 0.000 claims description 2
PFYKEUJWXPCNMX-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-N-[(2,6-difluoro-4-methoxyphenyl)methyl]-3-methyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N(CC3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)OC)F)C)=O)C(=CC=C1)F PFYKEUJWXPCNMX-UHFFFAOYSA-N 0.000 claims description 2
TWOOPICDTBDGNB-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-N-[(2-fluoro-6-methoxyphenyl)methyl]-3-methyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound C1=CC(OC)=C(CNC(=O)C2=CC=C3C(=C2)N(C(=O)N(C3)C)CC2=C(Cl)C=CC=C2F)C(F)=C1 TWOOPICDTBDGNB-UHFFFAOYSA-N 0.000 claims description 2
FAEUVDVTNPCDMZ-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-N-[(2-fluorophenyl)methyl]-3-methyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N(CC3=CC=C(C=C23)C(=O)NCC2=C(C=CC=C2)F)C)=O)C(=CC=C1)F FAEUVDVTNPCDMZ-UHFFFAOYSA-N 0.000 claims description 2
SWYKMUZCBPRNHD-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-N-[(4-fluoro-2-methoxyphenyl)methyl]-3-methyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N(CC3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2)F)OC)C)=O)C(=CC=C1)F SWYKMUZCBPRNHD-UHFFFAOYSA-N 0.000 claims description 2
GMYUKBKCWCXLJA-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-N-[(4-hydroxyphenyl)methyl]-3,4-dimethyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound C1=C2C(=CC(=C1)C(=O)NCC1=CC=C(O)C=C1)N(C(=O)N(C2C)C)CC1=C(Cl)C=CC=C1F GMYUKBKCWCXLJA-UHFFFAOYSA-N 0.000 claims description 2
DKHWBVKNVWYAKR-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-N-[(5-fluoro-1-benzofuran-2-yl)methyl]-3-methyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N(CC3=CC=C(C=C23)C(=O)NCC=2OC3=C(C=2)C=C(C=C3)F)C)=O)C(=CC=C1)F DKHWBVKNVWYAKR-UHFFFAOYSA-N 0.000 claims description 2
UVMWBNHMUOLHPJ-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-N-[(5-hydroxy-1-benzofuran-2-yl)methyl]-3-methyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound OC1=CC=2C=C(CNC(=O)C3=CC=C4C(=C3)N(C(=O)N(C4)C)CC3=C(Cl)C=CC=C3F)OC=2C=C1 UVMWBNHMUOLHPJ-UHFFFAOYSA-N 0.000 claims description 2
OUCWLCOCPCAIRK-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-N-[(6-fluoro-1-benzofuran-2-yl)methyl]-3-methyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N(CC3=CC=C(C=C23)C(=O)NCC=2OC3=C(C=2)C=CC(=C3)F)C)=O)C(=CC=C1)F OUCWLCOCPCAIRK-UHFFFAOYSA-N 0.000 claims description 2
SDXTVEMUPBAMRD-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-N-[(6-methoxy-1-benzofuran-2-yl)methyl]-3-methyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound ClC1=C(CN2C(N(CC3=CC=C(C=C23)C(=O)NCC=2OC3=C(C=2)C=CC(=C3)OC)C)=O)C(=CC=C1)F SDXTVEMUPBAMRD-UHFFFAOYSA-N 0.000 claims description 2
XHBWLUQXEFKHTM-UHFFFAOYSA-N 1-[(2-chloro-6-fluorophenyl)methyl]-N-[(7-methoxy-1-benzofuran-2-yl)methyl]-3-methyl-2-oxo-4H-quinazoline-7-carboxamide Chemical compound C1=CC(=C2C(=C1)C=C(CNC(=O)C1=CC=C3C(=C1)N(C(=O)N(C3)C)CC1=C(Cl)C=CC=C1F)O2)OC XHBWLUQXEFKHTM-UHFFFAOYSA-N 0.000 claims description 2
VBFNBSOREVOUCS-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-3-methyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC1=CC(F)=C(CNC(=O)C2=CC=C3C(N(C(=O)N(C3)C)CC3=C(Cl)C=CC=C3)=C2)C(F)=C1 VBFNBSOREVOUCS-UHFFFAOYSA-N 0.000 claims description 2
BIIQDMNCHVMGKK-UHFFFAOYSA-N 1-[(2-cyano-6-fluorophenyl)methyl]-3-methyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound C(#N)C1=C(CN2C(N(CC3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)=O)C(=CC=C1)F BIIQDMNCHVMGKK-UHFFFAOYSA-N 0.000 claims description 2
LTCUBULSEHZJRP-UHFFFAOYSA-N 1-[(2-fluoro-3-methoxyphenyl)methyl]-3-methyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound C1(F)=CC(F)=C(CNC(=O)C2=CC=C3C(=C2)N(C(=O)N(C3)C)CC2=C(F)C(OC)=CC=C2)C(F)=C1 LTCUBULSEHZJRP-UHFFFAOYSA-N 0.000 claims description 2
VFSAIUARAGGICY-UHFFFAOYSA-N 1-[(2-fluoro-3-methylphenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound C1=C2C(=CC(=C1)C(=O)NCC1=C(C=C(F)C=C1F)F)N(C(=O)N(C2C)C)CC1=C(F)C(C)=CC=C1 VFSAIUARAGGICY-UHFFFAOYSA-N 0.000 claims description 2
UPLXIUZXYQOAHH-UHFFFAOYSA-N 1-[(2-fluoro-3-methylphenyl)methyl]-3-methyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound C1=C2C(=CC(=C1)C(=O)NCC1=C(C=C(F)C=C1F)F)N(C(=O)N(C2)C)CC1=C(F)C(C)=CC=C1 UPLXIUZXYQOAHH-UHFFFAOYSA-N 0.000 claims description 2
BZKIXXSDMRQGDG-UHFFFAOYSA-N 1-[(2-fluoro-4-hydroxyphenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC1=C(CN2C(N(C(C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C=CC(=C1)O BZKIXXSDMRQGDG-UHFFFAOYSA-N 0.000 claims description 2
OHZSTICBKSCTST-UHFFFAOYSA-N 1-[(2-fluoro-4-methoxyphenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC1=C(CN2C(N(C(C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C=CC(=C1)OC OHZSTICBKSCTST-UHFFFAOYSA-N 0.000 claims description 2
AKSZPLYYHVJPLR-UHFFFAOYSA-N 1-[(2-fluoro-6-hydroxyphenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC1=C(CN2C(N(C(C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC=C1)O AKSZPLYYHVJPLR-UHFFFAOYSA-N 0.000 claims description 2
QUYFPSQKTJVKRL-UHFFFAOYSA-N 1-[(2-fluoro-6-methoxyphenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC1=C(CN2C(N(C(C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC=C1)OC QUYFPSQKTJVKRL-UHFFFAOYSA-N 0.000 claims description 2
AAWLPTPUDNLLGW-UHFFFAOYSA-N 1-[(2-fluoro-6-methoxyphenyl)methyl]-3-methyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC1=C(CN2C(N(CC3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)=O)C(=CC=C1)OC AAWLPTPUDNLLGW-UHFFFAOYSA-N 0.000 claims description 2
PXWQSEXCCWQHLM-UHFFFAOYSA-N 1-[(2-fluoro-6-methylphenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC1=C(CN2C(N(C(C3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)C)=O)C(=CC=C1)C PXWQSEXCCWQHLM-UHFFFAOYSA-N 0.000 claims description 2
CMOBWXYXSWASCB-UHFFFAOYSA-N 1-[(2-fluoro-6-methylphenyl)methyl]-3-methyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound C1=C2C(=CC(=C1)C(=O)NCC1=C(C=C(F)C=C1F)F)N(C(=O)N(C2)C)CC1=C(F)C=CC=C1C CMOBWXYXSWASCB-UHFFFAOYSA-N 0.000 claims description 2
HFEJXIDSTXTNKO-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound C1=2C(N(C)C(=O)N(C=2C=C(C=C1)C(=O)NCC1=C(C=C(F)C=C1F)F)CC1=C(F)C=CC=C1)C HFEJXIDSTXTNKO-UHFFFAOYSA-N 0.000 claims description 2
YMVOYDNBWZQKHP-UHFFFAOYSA-N 1-[(2-fluorophenyl)methyl]-3-methyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC1=C(CN2C(N(CC3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)=O)C=CC=C1 YMVOYDNBWZQKHP-UHFFFAOYSA-N 0.000 claims description 2
HMMFKCKIABIXQV-UHFFFAOYSA-N 1-[(3,5-difluorophenyl)methyl]-2-oxo-3-propan-2-yl-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound N1(C(C)C)CC2=C(C=C(C=C2)C(=O)NCC2=C(C=C(F)C=C2F)F)N(C1=O)CC1=CC(F)=CC(F)=C1 HMMFKCKIABIXQV-UHFFFAOYSA-N 0.000 claims description 2
IHEPAXXODXMCCC-UHFFFAOYSA-N 1-[(3,5-difluorophenyl)methyl]-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-3,4-dihydroquinazoline-7-carboxamide Chemical compound FC1=CC(=C(C(F)=C1)CNC(=O)C1=CC=2N(C(=O)NCC=2C=C1)CC1=CC(F)=CC(F)=C1)F IHEPAXXODXMCCC-UHFFFAOYSA-N 0.000 claims description 2
BXJCKZJOTARFNS-UHFFFAOYSA-N 1-[(3,5-difluorophenyl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound C1=C2C(=CC(=C1)C(=O)NCC1=C(C=C(F)C=C1F)F)N(C(=O)N(C2C)C)CC1=CC(F)=CC(F)=C1 BXJCKZJOTARFNS-UHFFFAOYSA-N 0.000 claims description 2
WZVIGTSAYQBAHS-UHFFFAOYSA-N 1-[(3,5-difluorophenyl)methyl]-3-ethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC1=CC(F)=C(CNC(=O)C2=CC=3N(C(=O)N(CC=3C=C2)CC)CC2=CC(F)=CC(F)=C2)C(F)=C1 WZVIGTSAYQBAHS-UHFFFAOYSA-N 0.000 claims description 2
KKBWWFIUBZNSPY-UHFFFAOYSA-N 1-[(3,5-difluorophenyl)methyl]-3-methyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC1=CC(=C(C(F)=C1)CNC(=O)C1=CC=C2C(=C1)N(C(=O)N(C2)C)CC1=CC(F)=CC(F)=C1)F KKBWWFIUBZNSPY-UHFFFAOYSA-N 0.000 claims description 2
DJIGXMAZTGEJQX-UHFFFAOYSA-N 1-[(3,5-difluorophenyl)methyl]-3-methyl-N-[(5-methylfuran-2-yl)methyl]-2-oxo-4H-quinazoline-7-carboxamide Chemical compound C1(=CC=C2C(=C1)N(C(=O)N(C2)C)CC1=CC(=CC(F)=C1)F)C(=O)NCC=1OC(C)=CC=1 DJIGXMAZTGEJQX-UHFFFAOYSA-N 0.000 claims description 2
AGLJUKOHCFGJQG-UHFFFAOYSA-N 1-[(3-carbamoylphenyl)methyl]-3-methyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound C(N)(=O)C=1C=C(CN2C(N(CC3=CC=C(C=C23)C(=O)NCC2=C(C=C(C=C2F)F)F)C)=O)C=CC=1 AGLJUKOHCFGJQG-UHFFFAOYSA-N 0.000 claims description 2
WHQNFYHTPMKJOA-UHFFFAOYSA-N 1-[(3-fluoropyridin-4-yl)methyl]-3,4-dimethyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound FC=1C=NC=CC=1CN1C(N(C(C2=CC=C(C=C12)C(=O)NCC1=C(C=C(C=C1F)F)F)C)C)=O WHQNFYHTPMKJOA-UHFFFAOYSA-N 0.000 claims description 2
MCDUOZJDWARCPY-UHFFFAOYSA-N 1-[(4-bromo-2,5-dimethylpyrazol-3-yl)methyl]-3-methyl-2-oxo-N-[(2,4,6-trifluorophenyl)methyl]-4H-quinazoline-7-carboxamide Chemical compound BrC=1C(=NN(C=1CN1C(N(CC2=CC=C(C=C12)C(=O)NCC1=C(C=C(C=C1F)F)F)C)=O)C)C MCDUOZJDWARCPY-UHFFFAOYSA-N 0.000 claims description 2
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JP2020520840A 2017-06-22 2018-06-21 ヒトｓｔｉｎｇの小分子調節因子 Active JP7296954B2 (ja)