JPWO2020063676A5 - - Google Patents
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- JPWO2020063676A5 JPWO2020063676A5 JP2021516798A JP2021516798A JPWO2020063676A5 JP WO2020063676 A5 JPWO2020063676 A5 JP WO2020063676A5 JP 2021516798 A JP2021516798 A JP 2021516798A JP 2021516798 A JP2021516798 A JP 2021516798A JP WO2020063676 A5 JPWO2020063676 A5 JP WO2020063676A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- antibody
- cycloalkyl
- alkyl
- ligand
- 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 hydroxy, amino Chemical group 0.000 claims description 208
- 239000003814 drug Substances 0.000 claims description 180
- 229940079593 drug Drugs 0.000 claims description 175
- 150000001875 compounds Chemical class 0.000 claims description 162
- 125000000217 alkyl group Chemical group 0.000 claims description 142
- 150000003839 salts Chemical class 0.000 claims description 111
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 89
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 87
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 82
- 239000012453 solvate Substances 0.000 claims description 71
- 206010028980 Neoplasm Diseases 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 65
- 239000002904 solvent Substances 0.000 claims description 54
- 229910052736 halogen Inorganic materials 0.000 claims description 53
- 150000002367 halogens Chemical class 0.000 claims description 53
- 239000000203 mixture Substances 0.000 claims description 52
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 47
- 229910052799 carbon Inorganic materials 0.000 claims description 45
- 125000001188 haloalkyl group Chemical group 0.000 claims description 43
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 42
- 239000003446 ligand Substances 0.000 claims description 40
- 239000000427 antigen Substances 0.000 claims description 37
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- 102000036639 antigens Human genes 0.000 claims description 37
- 125000003545 alkoxy group Chemical group 0.000 claims description 34
- 239000000126 substance Substances 0.000 claims description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 31
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- 125000004404 heteroalkyl group Chemical group 0.000 claims description 19
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 17
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- 125000004965 chloroalkyl group Chemical group 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
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- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 10
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 8
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- YOHYSYJDKVYCJI-UHFFFAOYSA-N n-[3-[[6-[3-(trifluoromethyl)anilino]pyrimidin-4-yl]amino]phenyl]cyclopropanecarboxamide Chemical compound FC(F)(F)C1=CC=CC(NC=2N=CN=C(NC=3C=C(NC(=O)C4CC4)C=CC=3)C=2)=C1 YOHYSYJDKVYCJI-UHFFFAOYSA-N 0.000 claims description 4
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- 239000004471 Glycine Substances 0.000 claims description 3
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- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 3
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- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 3
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- OBVVKJDJORDBCH-CZDIJEQGSA-N 2-aminoacetic acid (2S)-2-amino-3-phenylpropanoic acid Chemical compound NCC(O)=O.NCC(O)=O.NCC(O)=O.OC(=O)[C@@H](N)CC1=CC=CC=C1 OBVVKJDJORDBCH-CZDIJEQGSA-N 0.000 claims description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 2
- 235000003704 aspartic acid Nutrition 0.000 claims description 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims description 2
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- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 1
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2019
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- 2019-09-25 MX MX2021003382A patent/MX2021003382A/es unknown
- 2019-09-25 CN CN202411019712.8A patent/CN118903456A/zh active Pending
- 2019-09-25 CN CN201980049841.2A patent/CN112512591B/zh active Active
- 2019-09-25 US US17/280,129 patent/US20210353764A1/en active Pending
- 2019-09-25 EP EP19866595.2A patent/EP3858386A4/en active Pending
- 2019-09-25 UA UAA202102037A patent/UA130338C2/uk unknown
- 2019-09-25 CN CN202411019975.9A patent/CN118806924A/zh active Pending
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