JP2019533694A5 - - Google Patents
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- Publication number
- JP2019533694A5 JP2019533694A5 JP2019522859A JP2019522859A JP2019533694A5 JP 2019533694 A5 JP2019533694 A5 JP 2019533694A5 JP 2019522859 A JP2019522859 A JP 2019522859A JP 2019522859 A JP2019522859 A JP 2019522859A JP 2019533694 A5 JP2019533694 A5 JP 2019533694A5
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- oxo
- groups
- dihydro
- triazole
- 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, phenyl Chemical group 0.000 claims 296
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 200
- 150000001875 compounds Chemical class 0.000 claims 57
- 125000001424 substituent group Chemical group 0.000 claims 46
- 125000005843 halogen group Chemical group 0.000 claims 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 44
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 31
- 239000000203 mixture Substances 0.000 claims 31
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 30
- 150000003839 salts Chemical class 0.000 claims 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 28
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 24
- 150000001204 N-oxides Chemical class 0.000 claims 18
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 17
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 17
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 17
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 16
- 125000003118 aryl group Chemical group 0.000 claims 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- 125000001072 heteroaryl group Chemical group 0.000 claims 12
- 238000000034 method Methods 0.000 claims 12
- 125000002950 monocyclic group Chemical group 0.000 claims 12
- 125000004432 carbon atom Chemical group C* 0.000 claims 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 11
- 206010025323 Lymphomas Diseases 0.000 claims 9
- 125000002619 bicyclic group Chemical group 0.000 claims 9
- 208000032839 leukemia Diseases 0.000 claims 9
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims 8
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 229910052757 nitrogen Inorganic materials 0.000 claims 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 8
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical group [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 8
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 7
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 6
- 229910052801 chlorine Inorganic materials 0.000 claims 6
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 4
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 4
- 108010052167 Dihydroorotate Dehydrogenase Proteins 0.000 claims 4
- 102100032823 Dihydroorotate dehydrogenase (quinone), mitochondrial Human genes 0.000 claims 4
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 230000002401 inhibitory effect Effects 0.000 claims 4
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 239000012453 solvate Substances 0.000 claims 4
- 125000003944 tolyl group Chemical group 0.000 claims 4
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 3
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 3
- 208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims 3
- 208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims 3
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 3
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims 3
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 3
- 208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims 3
- 230000001154 acute effect Effects 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 210000004027 cell Anatomy 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 3
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 229910052740 iodine Chemical group 0.000 claims 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 3
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 3
- JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-ethyl Chemical group C[CH]OC JQCSUVJDBHJKNG-UHFFFAOYSA-N 0.000 claims 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 206010052178 Lymphocytic lymphoma Diseases 0.000 claims 2
- 208000025205 Mantle-Cell Lymphoma Diseases 0.000 claims 2
- 208000034578 Multiple myelomas Diseases 0.000 claims 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 210000003719 b-lymphocyte Anatomy 0.000 claims 2
- 230000003833 cell viability Effects 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims 2
- 230000003463 hyperproliferative effect Effects 0.000 claims 2
- 239000011630 iodine Chemical group 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 2
- DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000006413 ring segment Chemical group 0.000 claims 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 210000003491 skin Anatomy 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- 125000006002 1,1-difluoroethyl group Chemical group 0.000 claims 1
- OSCIMHZNLNMRKZ-JTQLQIEISA-N 1-[2-fluoro-4-[(2-fluoro-6-methylphenyl)carbamoyl]-5-[(2S)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-4-methyl-5-oxo-1,2,4-triazole-3-carboxylic acid Chemical compound FC1=C(C=C(C(=C1)C(NC1=C(C=CC=C1C)F)=O)O[C@H](C(F)(F)F)C)N1N=C(N(C1=O)C)C(=O)O OSCIMHZNLNMRKZ-JTQLQIEISA-N 0.000 claims 1
- BSJRKIOZGYTFKG-VIFPVBQESA-N 1-[4-[(2,6-dichlorophenyl)carbamoyl]-2-fluoro-5-[(2S)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-4-ethyl-5-oxo-1,2,4-triazole-3-carboxylic acid Chemical compound ClC1=C(C(=CC=C1)Cl)NC(=O)C1=CC(=C(C=C1O[C@H](C(F)(F)F)C)N1N=C(N(C1=O)CC)C(=O)O)F BSJRKIOZGYTFKG-VIFPVBQESA-N 0.000 claims 1
- APRKSVSZGFCSDA-VIFPVBQESA-N 1-[4-[(2,6-difluorophenyl)carbamoyl]-2-fluoro-5-[(2S)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-4-ethyl-5-oxo-1,2,4-triazole-3-carboxamide Chemical compound FC1=C(C(=CC=C1)F)NC(=O)C1=CC(=C(C=C1O[C@H](C(F)(F)F)C)N1N=C(N(C1=O)CC)C(=O)N)F APRKSVSZGFCSDA-VIFPVBQESA-N 0.000 claims 1
- MUFVKJZGKSKCKV-VIFPVBQESA-N 1-[4-[(2,6-difluorophenyl)carbamoyl]-2-fluoro-5-[(2S)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-4-ethyl-5-oxo-1,2,4-triazole-3-carboxylic acid Chemical compound FC1=C(C(=CC=C1)F)NC(=O)C1=CC(=C(C=C1O[C@H](C(F)(F)F)C)N1N=C(N(C1=O)CC)C(=O)O)F MUFVKJZGKSKCKV-VIFPVBQESA-N 0.000 claims 1
- COZQURSLHGMQIL-QMMMGPOBSA-N 1-[4-[(2,6-difluorophenyl)carbamoyl]-2-fluoro-5-[(2S)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-4-methyl-5-oxo-1,2,4-triazole-3-carboxamide Chemical compound FC1=C(C(=CC=C1)F)NC(=O)C1=CC(=C(C=C1O[C@H](C(F)(F)F)C)N1N=C(N(C1=O)C)C(=O)N)F COZQURSLHGMQIL-QMMMGPOBSA-N 0.000 claims 1
- VTARKQUDMKWXET-QMMMGPOBSA-N 1-[4-[(2,6-difluorophenyl)carbamoyl]-2-fluoro-5-[(2S)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-4-methyl-5-oxo-1,2,4-triazole-3-carboxylic acid Chemical compound FC1=C(C(=CC=C1)F)NC(=O)C1=CC(=C(C=C1O[C@H](C(F)(F)F)C)N1N=C(N(C1=O)C)C(=O)O)F VTARKQUDMKWXET-QMMMGPOBSA-N 0.000 claims 1
- KPZARBZNFZVAET-VIFPVBQESA-N 1-[4-[(2,6-difluorophenyl)carbamoyl]-2-fluoro-5-[(2S)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-N,4-dimethyl-5-oxo-1,2,4-triazole-3-carboxamide Chemical compound FC1=C(C(=CC=C1)F)NC(=O)C1=CC(=C(C=C1O[C@H](C(F)(F)F)C)N1N=C(N(C1=O)C)C(=O)NC)F KPZARBZNFZVAET-VIFPVBQESA-N 0.000 claims 1
- PWJIQVMSPOHPLT-JTQLQIEISA-N 1-[4-[(2,6-difluorophenyl)carbamoyl]-3-[(2S)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-4-ethyl-5-oxo-1,2,4-triazole-3-carboxylic acid Chemical compound FC1=C(C(=CC=C1)F)NC(=O)C1=C(C=C(C=C1)N1N=C(N(C1=O)CC)C(=O)O)O[C@H](C(F)(F)F)C PWJIQVMSPOHPLT-JTQLQIEISA-N 0.000 claims 1
- SLLBQWNAXLRGNN-VIFPVBQESA-N 1-[4-[(2-chloro-6-fluorophenyl)carbamoyl]-2-fluoro-3-[(2S)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-4-ethyl-5-oxo-1,2,4-triazole-3-carboxylic acid Chemical compound ClC1=C(C(=CC=C1)F)NC(=O)C1=C(C(=C(C=C1)N1N=C(N(C1=O)CC)C(=O)O)F)O[C@H](C(F)(F)F)C SLLBQWNAXLRGNN-VIFPVBQESA-N 0.000 claims 1
- ZZXLFVBNZXVAJN-JTQLQIEISA-N 1-[4-[(2-chloro-6-fluorophenyl)carbamoyl]-2-fluoro-5-[(2S)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-4-cyclobutyl-5-oxo-1,2,4-triazole-3-carboxylic acid Chemical compound ClC1=C(C(=CC=C1)F)NC(=O)C1=CC(=C(C=C1O[C@H](C(F)(F)F)C)N1N=C(N(C1=O)C1CCC1)C(=O)O)F ZZXLFVBNZXVAJN-JTQLQIEISA-N 0.000 claims 1
- WVCVFKJSCKNYLE-VIFPVBQESA-N 1-[4-[(2-chloro-6-fluorophenyl)carbamoyl]-2-fluoro-5-[(2S)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-4-cyclopropyl-5-oxo-1,2,4-triazole-3-carboxylic acid Chemical compound ClC1=C(C(=CC=C1)F)NC(=O)C1=CC(=C(C=C1O[C@H](C(F)(F)F)C)N1N=C(N(C1=O)C1CC1)C(=O)O)F WVCVFKJSCKNYLE-VIFPVBQESA-N 0.000 claims 1
- IPTGCOJTXSXNDO-VIFPVBQESA-N 1-[4-[(2-chloro-6-fluorophenyl)carbamoyl]-2-fluoro-5-[(2S)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-4-ethyl-5-oxo-1,2,4-triazole-3-carboxamide Chemical compound ClC1=C(C(=CC=C1)F)NC(=O)C1=CC(=C(C=C1O[C@H](C(F)(F)F)C)N1N=C(N(C1=O)CC)C(=O)N)F IPTGCOJTXSXNDO-VIFPVBQESA-N 0.000 claims 1
- LGTBXNWJLAYAHR-VIFPVBQESA-N 1-[4-[(2-chloro-6-fluorophenyl)carbamoyl]-2-fluoro-5-[(2S)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-4-ethyl-5-oxo-1,2,4-triazole-3-carboxylic acid Chemical compound ClC1=C(C(=CC=C1)F)NC(=O)C1=CC(=C(C=C1O[C@H](C(F)(F)F)C)N1N=C(N(C1=O)CC)C(=O)O)F LGTBXNWJLAYAHR-VIFPVBQESA-N 0.000 claims 1
- BPNKVHXZDJTPOT-QMMMGPOBSA-N 1-[4-[(2-chloro-6-fluorophenyl)carbamoyl]-2-fluoro-5-[(2S)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-4-methyl-5-oxo-1,2,4-triazole-3-carboxylic acid Chemical compound ClC1=C(C(=CC=C1)F)NC(=O)C1=CC(=C(C=C1O[C@H](C(F)(F)F)C)N1N=C(N(C1=O)C)C(=O)O)F BPNKVHXZDJTPOT-QMMMGPOBSA-N 0.000 claims 1
- ZEVXVGJUUYBMBQ-JTQLQIEISA-N 1-[4-[(2-chloro-6-fluorophenyl)carbamoyl]-2-fluoro-5-[(2S)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-5-oxo-4-prop-2-enyl-1,2,4-triazole-3-carboxylic acid Chemical compound ClC1=C(C(=CC=C1)F)NC(=O)C1=CC(=C(C=C1O[C@H](C(F)(F)F)C)N1N=C(N(C1=O)CC=C)C(=O)O)F ZEVXVGJUUYBMBQ-JTQLQIEISA-N 0.000 claims 1
- JVBRDCRTUMDDCU-JTQLQIEISA-N 1-[4-[(2-chloro-6-fluorophenyl)carbamoyl]-2-fluoro-5-[(2S)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-5-oxo-4-propyl-1,2,4-triazole-3-carboxylic acid Chemical compound ClC1=C(C(=CC=C1)F)NC(=O)C1=CC(=C(C=C1O[C@H](C(F)(F)F)C)N1N=C(N(C1=O)CCC)C(=O)O)F JVBRDCRTUMDDCU-JTQLQIEISA-N 0.000 claims 1
- QVYFTZGCYIOCHY-UHFFFAOYSA-N 1-[4-[(2-chloro-6-fluorophenyl)carbamoyl]-3-(1,1-difluoropropan-2-yloxy)phenyl]-4-ethyl-5-oxo-1,2,4-triazole-3-carboxylic acid Chemical compound ClC1=C(C(=CC=C1)F)NC(=O)C1=C(C=C(C=C1)N1N=C(N(C1=O)CC)C(=O)O)OC(C(F)F)C QVYFTZGCYIOCHY-UHFFFAOYSA-N 0.000 claims 1
- HVVAZMYPRRSOSC-JTQLQIEISA-N 1-[4-[(2-chloro-6-fluorophenyl)carbamoyl]-3-[(2S)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-4-ethyl-5-oxo-1,2,4-triazole-3-carboxylic acid Chemical compound ClC1=C(C(=CC=C1)F)NC(=O)C1=C(C=C(C=C1)N1N=C(N(C1=O)CC)C(=O)O)O[C@H](C(F)(F)F)C HVVAZMYPRRSOSC-JTQLQIEISA-N 0.000 claims 1
- JTZZINKWFXPTIR-UHFFFAOYSA-N 1-[4-[(2-chloro-6-fluorophenyl)carbamoyl]-5-(3,3-difluorobutan-2-yloxy)-2-fluorophenyl]-4-ethyl-5-oxo-1,2,4-triazole-3-carboxylic acid Chemical compound ClC1=C(C(=CC=C1)F)NC(=O)C1=CC(=C(C=C1OC(C)C(C)(F)F)N1N=C(N(C1=O)CC)C(=O)O)F JTZZINKWFXPTIR-UHFFFAOYSA-N 0.000 claims 1
- LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 claims 1
- RDEXYUBRYCTEBN-INIZCTEOSA-N 2-[(1S)-1-cyclohexylethoxy]-N-(1,4-dimethylpyrazol-3-yl)-4-(3-ethyl-4-methyl-5-oxo-1,2,4-triazol-1-yl)-5-fluorobenzamide Chemical compound C1(CCCCC1)[C@H](C)OC1=C(C(=O)NC2=NN(C=C2C)C)C=C(C(=C1)N1N=C(N(C1=O)C)CC)F RDEXYUBRYCTEBN-INIZCTEOSA-N 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- NYULXDOWEIURJG-NSHDSACASA-N 4-ethyl-1-[2-fluoro-4-[(2-fluoro-6-methylphenyl)carbamoyl]-5-[(2S)-1,1,1-trifluoropropan-2-yl]oxyphenyl]-5-oxo-1,2,4-triazole-3-carboxylic acid Chemical compound C(C)N1C(=NN(C1=O)C1=C(C=C(C(=C1)O[C@H](C(F)(F)F)C)C(NC1=C(C=CC=C1C)F)=O)F)C(=O)O NYULXDOWEIURJG-NSHDSACASA-N 0.000 claims 1
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| KR102861339B1 (ko) | 2018-02-20 | 2025-09-19 | 르 라보레또레 쎄르비에르 | 삼치환 벤조트리아졸 유도체의 사용 방법 |
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| TW201945346A (zh) | 2018-04-10 | 2019-12-01 | 德商拜耳廠股份有限公司 | 2,4,5-三取代的1,2,4-三唑酮之製備方法 |
| WO2019197269A1 (en) * | 2018-04-11 | 2019-10-17 | Bayer Aktiengesellschaft | Combinations of copanlisib with triazolone derivatives and their use in the treatment of cancer |
| WO2020067412A1 (ja) | 2018-09-28 | 2020-04-02 | 富士フイルム株式会社 | シタラビンを含む抗腫瘍剤、シタラビンと併用される抗腫瘍効果増強剤、抗腫瘍用キット、およびシタラビンと併用される抗腫瘍剤 |
| CR20210394A (es) | 2018-12-21 | 2021-12-13 | Les Laboratoires Servier Sas | Formas de sal y cristalinas de un compuesto orgánico y composiciones farmacéuticas del mismo |
| TW202043208A (zh) * | 2019-01-11 | 2020-12-01 | 美商健生生物科技公司 | 二氫乳清酸脫氫酶抑制劑 |
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| TW202104207A (zh) * | 2019-04-17 | 2021-02-01 | 美商健生生物科技公司 | 二氫乳清酸脫氫酶抑制劑 |
| EP3750892A1 (en) | 2019-06-14 | 2020-12-16 | Yerevan State University | Novel 5-cyclopropyl-furo[3,4-c]pyridine-3,4(1h,5h)-dione 1,1' substituted derivatives and their uses |
| US20220298107A1 (en) * | 2019-08-29 | 2022-09-22 | Janssen Biotech, Inc. | Substituted urea dihydroorotate dehydrogenase inhibitors |
| MX2022004335A (es) * | 2019-10-10 | 2022-07-19 | Janssen Biotech Inc | Biarilos como inhibidores de la dihidroorotato deshidrogenasa. |
| WO2021083182A1 (zh) * | 2019-10-28 | 2021-05-06 | 南京明德新药研发有限公司 | 一种尿酸促排剂及其合成方法和其在医药上的应用 |
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| EP3912627B1 (en) | 2020-05-20 | 2022-09-07 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for the treatment of coronavirus infections |
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| CN111773214B (zh) * | 2020-07-17 | 2021-04-20 | 中国人民解放军军事科学院军事医学研究院 | 2,4,5-三取代的1,2,4-三唑酮在制备抗病毒药物中的用途 |
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| GB2598624A (en) * | 2020-09-07 | 2022-03-09 | Lorico Aurelio | Use of triazole analogues for inhibition of a tripartite VOR protein complex in multicellular organisms |
| WO2022063299A1 (zh) * | 2020-09-28 | 2022-03-31 | 微境生物医药科技(上海)有限公司 | 用作dhodh抑制剂的1,2,4-三唑酮衍生物 |
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| WO2022167402A1 (en) | 2021-02-02 | 2022-08-11 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods of therapy comprising administering a therapeutically effective combination comprising a dhodh inhibitor and an idh inhibitor |
| WO2023280181A1 (zh) * | 2021-07-05 | 2023-01-12 | 微境生物医药科技(上海)有限公司 | 用作dhodh抑制剂的1,2,4-三唑酮衍生物及其制备方法和用途 |
| CN118284603A (zh) * | 2021-11-26 | 2024-07-02 | 南京明德新药研发有限公司 | 三氮唑酮类化合物的晶型及其应用 |
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- 2019-04-26 CL CL2019001160A patent/CL2019001160A1/es unknown
- 2019-04-26 NI NI201900041A patent/NI201900041A/es unknown
- 2019-04-26 CO CONC2019/0004137A patent/CO2019004137A2/es unknown
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2020
- 2020-08-18 US US16/996,721 patent/US11130745B2/en active Active
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2021
- 2021-08-20 US US17/407,951 patent/US11713304B2/en active Active
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2023
- 2023-04-20 US US18/137,281 patent/US12486248B2/en active Active
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