JP2020524719A5 - - Google Patents
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- Publication number
- JP2020524719A5 JP2020524719A5 JP2020520840A JP2020520840A JP2020524719A5 JP 2020524719 A5 JP2020524719 A5 JP 2020524719A5 JP 2020520840 A JP2020520840 A JP 2020520840A JP 2020520840 A JP2020520840 A JP 2020520840A JP 2020524719 A5 JP2020524719 A5 JP 2020524719A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- carboxamide
- tetrahydroquinazoline
- trifluorobenzyl
- dimethyl
- Prior art date
- 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.)
- Granted
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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
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