JP2020033357A5 - - Google Patents
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- JP2020033357A5 JP2020033357A5 JP2019184938A JP2019184938A JP2020033357A5 JP 2020033357 A5 JP2020033357 A5 JP 2020033357A5 JP 2019184938 A JP2019184938 A JP 2019184938A JP 2019184938 A JP2019184938 A JP 2019184938A JP 2020033357 A5 JP2020033357 A5 JP 2020033357A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- carboxamide
- alkyl
- pyrazole
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 42
- 125000003118 aryl group Chemical group 0.000 claims 32
- 125000001424 substituent group Chemical group 0.000 claims 30
- 125000001072 heteroaryl group Chemical group 0.000 claims 29
- 125000003545 alkoxy group Chemical group 0.000 claims 28
- 125000005843 halogen group Chemical group 0.000 claims 23
- 150000001875 compounds Chemical class 0.000 claims 21
- 239000000203 mixture Substances 0.000 claims 19
- 150000003839 salts Chemical class 0.000 claims 19
- 239000012453 solvate Substances 0.000 claims 18
- 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 16
- 125000004432 carbon atom Chemical group C* 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 10
- 229910052760 oxygen Inorganic materials 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 10
- 229910052717 sulfur Inorganic materials 0.000 claims 10
- 102000003827 Plasma Kallikrein Human genes 0.000 claims 8
- 108090000113 Plasma Kallikrein Proteins 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 8
- 201000010099 disease Diseases 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 230000000694 effects Effects 0.000 claims 8
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 7
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 7
- -1 benzomorpholinyl Chemical group 0.000 claims 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000001153 fluoro group Chemical group F* 0.000 claims 6
- 125000002950 monocyclic group Chemical group 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 206010012688 Diabetic retinal oedema Diseases 0.000 claims 5
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 5
- 201000011190 diabetic macular edema Diseases 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 239000004215 Carbon black (E152) Substances 0.000 claims 4
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 4
- 125000002619 bicyclic group Chemical group 0.000 claims 4
- 235000010290 biphenyl Nutrition 0.000 claims 4
- 239000004305 biphenyl Substances 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 229930195733 hydrocarbon Natural products 0.000 claims 4
- 150000002430 hydrocarbons Chemical class 0.000 claims 4
- 125000001624 naphthyl group Chemical group 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 206010019860 Hereditary angioedema Diseases 0.000 claims 3
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 2
- 208000031229 Cardiomyopathies Diseases 0.000 claims 2
- 206010008111 Cerebral haemorrhage Diseases 0.000 claims 2
- 208000001953 Hypotension Diseases 0.000 claims 2
- 206010061218 Inflammation Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 206010033645 Pancreatitis Diseases 0.000 claims 2
- 206010051077 Post procedural haemorrhage Diseases 0.000 claims 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 2
- 206010040070 Septic Shock Diseases 0.000 claims 2
- 206010047571 Visual impairment Diseases 0.000 claims 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 2
- 206010003246 arthritis Diseases 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 230000002612 cardiopulmonary effect Effects 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 208000009190 disseminated intravascular coagulation Diseases 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 230000036543 hypotension Effects 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 208000017169 kidney disease Diseases 0.000 claims 2
- 201000001119 neuropathy Diseases 0.000 claims 2
- 230000007823 neuropathy Effects 0.000 claims 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 230000002207 retinal effect Effects 0.000 claims 2
- 230000036303 septic shock Effects 0.000 claims 2
- 238000001356 surgical procedure Methods 0.000 claims 2
- 230000008728 vascular permeability Effects 0.000 claims 2
- 208000029257 vision disease Diseases 0.000 claims 2
- 230000004393 visual impairment Effects 0.000 claims 2
- OMUPFLKDHHROJU-UHFFFAOYSA-N 3-(dimethylamino)-N-[(2-fluoro-3-methoxyphenyl)methyl]-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound CN(C1=NN(C=C1C(=O)NCC1=C(C(=CC=C1)OC)F)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)C OMUPFLKDHHROJU-UHFFFAOYSA-N 0.000 claims 1
- YDHZFMPDUQUAJM-UHFFFAOYSA-N 3-(methoxymethyl)-N-[(3-methoxyphenyl)methyl]-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound COCC1=NN(C=C1C(=O)NCC1=CC(=CC=C1)OC)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O YDHZFMPDUQUAJM-UHFFFAOYSA-N 0.000 claims 1
- FKGBWMYRUOPIHY-UHFFFAOYSA-N 3-(methoxymethyl)-N-[[5-methoxy-2-(trifluoromethyl)phenyl]methyl]-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound COC=1C=CC(=C(C=1)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC)C(F)(F)F FKGBWMYRUOPIHY-UHFFFAOYSA-N 0.000 claims 1
- JJEXYMJFQVLENB-UHFFFAOYSA-N 3-acetamido-N-[(2-fluoro-3-methoxyphenyl)methyl]-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound C(C)(=O)NC1=NN(C=C1C(=O)NCC1=C(C(=CC=C1)OC)F)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O JJEXYMJFQVLENB-UHFFFAOYSA-N 0.000 claims 1
- OOXKEXDZGXUAST-UHFFFAOYSA-N 3-amino-N-[(2-fluoro-3-hydroxyphenyl)methyl]-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound NC1=NN(C=C1C(=O)NCC1=C(C(=CC=C1)O)F)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O OOXKEXDZGXUAST-UHFFFAOYSA-N 0.000 claims 1
- HICYNMRHZGAFMT-UHFFFAOYSA-N 3-amino-N-[(2-fluoro-3-methoxyphenyl)methyl]-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound FC1=C(CNC(=O)C=2C(=NN(C=2)CC2=CC=C(C=C2)CN2C(C=CC=C2)=O)N)C=CC=C1OC HICYNMRHZGAFMT-UHFFFAOYSA-N 0.000 claims 1
- PIQXYEUIEZKEKB-UHFFFAOYSA-N 3-amino-N-[(7-chloro-3,4-dihydro-2H-1,4-benzoxazin-2-yl)methyl]-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound NC1=NN(C=C1C(=O)NCC1OC2=C(NC1)C=CC(=C2)Cl)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O PIQXYEUIEZKEKB-UHFFFAOYSA-N 0.000 claims 1
- BZQHROALKROIIJ-UHFFFAOYSA-N 3-amino-N-[(7-chloro-4-methyl-2,3-dihydro-1,4-benzoxazin-2-yl)methyl]-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound NC1=NN(C=C1C(=O)NCC1OC2=C(N(C1)C)C=CC(=C2)Cl)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O BZQHROALKROIIJ-UHFFFAOYSA-N 0.000 claims 1
- ZRDGSEIHHBOARU-UHFFFAOYSA-N 3-amino-N-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound NC1=NN(C=C1C(=O)NCC1=C(C=CC=C1C(F)(F)F)F)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O ZRDGSEIHHBOARU-UHFFFAOYSA-N 0.000 claims 1
- NFLOZDGNLCLQAJ-UHFFFAOYSA-N 3-cyclopropyl-N-[(2-fluoro-3-methoxyphenyl)methyl]-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound C1(CC1)C1=NN(C=C1C(=O)NCC1=C(C(=CC=C1)OC)F)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O NFLOZDGNLCLQAJ-UHFFFAOYSA-N 0.000 claims 1
- FKXBPOXUNOOPGU-UHFFFAOYSA-N N-[(2,5-difluoro-3-methoxyphenyl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound FC1=C(C=C(C=C1OC)F)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC FKXBPOXUNOOPGU-UHFFFAOYSA-N 0.000 claims 1
- JRSJFSJQRZMHDN-UHFFFAOYSA-N N-[(2,6-difluoro-3-methoxyphenyl)methyl]-1-[[4-[(5-fluoro-2-oxopyridin-1-yl)methyl]phenyl]methyl]-3-(methoxymethyl)pyrazole-4-carboxamide Chemical compound FC1=C(C(=CC=C1OC)F)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC(=C1)F)=O)COC JRSJFSJQRZMHDN-UHFFFAOYSA-N 0.000 claims 1
- PIYDGHWVVUCTNS-UHFFFAOYSA-N N-[(2,6-difluoro-3-methoxyphenyl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound FC1=C(C(=CC=C1OC)F)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC PIYDGHWVVUCTNS-UHFFFAOYSA-N 0.000 claims 1
- BKTJDPOLKWOBHW-UHFFFAOYSA-N N-[(2,6-difluoro-3-methoxyphenyl)methyl]-3-(methoxymethyl)-1-[[4-[(4-methyl-2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound FC1=C(C(=CC=C1OC)F)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=C(C=C1)C)=O)COC BKTJDPOLKWOBHW-UHFFFAOYSA-N 0.000 claims 1
- VTFAEOJNECOMFY-UHFFFAOYSA-N N-[(2-carbamoyl-5-methoxyphenyl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound C(N)(=O)C1=C(C=C(C=C1)OC)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC VTFAEOJNECOMFY-UHFFFAOYSA-N 0.000 claims 1
- PQVWIESRTSEZPB-UHFFFAOYSA-N N-[(2-carbamoyl-6-fluorophenyl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound C(N)(=O)C1=C(C(=CC=C1)F)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC PQVWIESRTSEZPB-UHFFFAOYSA-N 0.000 claims 1
- TVHOOPXMFWZGQK-UHFFFAOYSA-N N-[(2-fluoro-3,6-dimethoxyphenyl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound FC1=C(C(=CC=C1OC)OC)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC TVHOOPXMFWZGQK-UHFFFAOYSA-N 0.000 claims 1
- UZZGYTADFHNIGM-UHFFFAOYSA-N N-[(2-fluoro-3-methoxyphenyl)methyl]-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]-2-(trifluoromethyl)imidazole-4-carboxamide Chemical compound FC1=C(C=CC=C1OC)CNC(=O)C=1N=C(N(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)C(F)(F)F UZZGYTADFHNIGM-UHFFFAOYSA-N 0.000 claims 1
- QZMZZOCEJPCAIJ-UHFFFAOYSA-N N-[(2-fluoro-3-methoxyphenyl)methyl]-1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound FC1=C(C=CC=C1OC)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1N=CC(=C1)C)C(F)(F)F QZMZZOCEJPCAIJ-UHFFFAOYSA-N 0.000 claims 1
- XCBLTBHUJNNESG-UHFFFAOYSA-N N-[(2-fluoro-3-methoxyphenyl)methyl]-2-methyl-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]imidazole-4-carboxamide Chemical compound FC1=C(C=CC=C1OC)CNC(=O)C=1N=C(N(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)C XCBLTBHUJNNESG-UHFFFAOYSA-N 0.000 claims 1
- MLCDWARNPOODOL-UHFFFAOYSA-N N-[(2-fluoro-3-methoxyphenyl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound FC1=C(C=CC=C1OC)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC MLCDWARNPOODOL-UHFFFAOYSA-N 0.000 claims 1
- OAWJOZMRPBQRIM-UHFFFAOYSA-N N-[(2-fluoro-4-methylphenyl)methyl]-1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound FC1=C(C=CC(=C1)C)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1N=CC(=C1)C)C(F)(F)F OAWJOZMRPBQRIM-UHFFFAOYSA-N 0.000 claims 1
- XRBNFAVKAJTXOR-UHFFFAOYSA-N N-[(2-fluoro-4-methylphenyl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound FC1=C(C=CC(=C1)C)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC XRBNFAVKAJTXOR-UHFFFAOYSA-N 0.000 claims 1
- HQJUOFQTROTCAB-UHFFFAOYSA-N N-[(2-fluoro-5-methoxyphenyl)methyl]-1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound FC1=C(C=C(C=C1)OC)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1N=CC(=C1)C)C(F)(F)F HQJUOFQTROTCAB-UHFFFAOYSA-N 0.000 claims 1
- NKTZDNHYVJSOOU-UHFFFAOYSA-N N-[(2-fluoro-5-methoxyphenyl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound FC1=C(C=C(C=C1)OC)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC NKTZDNHYVJSOOU-UHFFFAOYSA-N 0.000 claims 1
- NLVINHRIZCLAQG-UHFFFAOYSA-N N-[(2-fluoro-6-methylphenyl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound FC1=C(C(=CC=C1)C)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC NLVINHRIZCLAQG-UHFFFAOYSA-N 0.000 claims 1
- ZHIGUNZKTJKAFE-UHFFFAOYSA-N N-[(3-chloro-2,6-difluorophenyl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound ClC=1C(=C(C(=CC=1)F)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC)F ZHIGUNZKTJKAFE-UHFFFAOYSA-N 0.000 claims 1
- TVACIVBKATZGQV-UHFFFAOYSA-N N-[(3-ethyl-2-fluorophenyl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound C(C)C=1C(=C(C=CC=1)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC)F TVACIVBKATZGQV-UHFFFAOYSA-N 0.000 claims 1
- SXIKFYGPUGSYOC-UHFFFAOYSA-N N-[(4-chloro-2,6-difluorophenyl)methyl]-1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound ClC1=CC(=C(C(=C1)F)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1N=CC(=C1)C)C(F)(F)F)F SXIKFYGPUGSYOC-UHFFFAOYSA-N 0.000 claims 1
- TZULTWISCDFBIR-UHFFFAOYSA-N N-[(5-chloro-1-benzothiophen-3-yl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound ClC=1C=CC2=C(C(=CS2)CNC(=O)C=2C(=NN(C=2)CC2=CC=C(C=C2)CN2C(C=CC=C2)=O)COC)C=1 TZULTWISCDFBIR-UHFFFAOYSA-N 0.000 claims 1
- AQJYHYPGWCFTGU-UHFFFAOYSA-N N-[(5-chloro-2-cyanophenyl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound ClC=1C=CC(=C(C=1)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC)C#N AQJYHYPGWCFTGU-UHFFFAOYSA-N 0.000 claims 1
- AJVITEJNDAKYPL-UHFFFAOYSA-N N-[(6-chloro-2-fluoro-3-methoxyphenyl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound ClC1=CC=C(C(=C1CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC)F)OC AJVITEJNDAKYPL-UHFFFAOYSA-N 0.000 claims 1
- SPXOTFDBWDBJRN-UHFFFAOYSA-N N-[(6-cyano-2-fluoro-3-methoxyphenyl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound C(#N)C1=CC=C(C(=C1CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC)F)OC SPXOTFDBWDBJRN-UHFFFAOYSA-N 0.000 claims 1
- MKZIFUOKFBQCJL-UHFFFAOYSA-N N-[[2-(difluoromethoxy)-6-fluorophenyl]methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound FC(OC1=C(C(=CC=C1)F)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC)F MKZIFUOKFBQCJL-UHFFFAOYSA-N 0.000 claims 1
- PTXDNBVAMADNIH-UHFFFAOYSA-N N-[[2-(difluoromethyl)-3-methoxyphenyl]methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound FC(C1=C(C=CC=C1OC)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC)F PTXDNBVAMADNIH-UHFFFAOYSA-N 0.000 claims 1
- IBBPTWWPBCQANZ-UHFFFAOYSA-N N-[[2-(difluoromethyl)-5-methoxyphenyl]methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound FC(C1=C(C=C(C=C1)OC)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC)F IBBPTWWPBCQANZ-UHFFFAOYSA-N 0.000 claims 1
- FDDKVGBGYLYHDV-UHFFFAOYSA-N N-[[2-(difluoromethyl)-6-fluoro-3-methoxyphenyl]methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound FC(C1=C(C(=CC=C1OC)F)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC)F FDDKVGBGYLYHDV-UHFFFAOYSA-N 0.000 claims 1
- BZFADXUGNHDNKB-UHFFFAOYSA-N N-[[2-(difluoromethyl)-6-fluorophenyl]methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound FC(C1=C(C(=CC=C1)F)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC)F BZFADXUGNHDNKB-UHFFFAOYSA-N 0.000 claims 1
- GEFVFTYILHWIGO-UHFFFAOYSA-N N-[[2-(difluoromethyl)phenyl]methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound FC(C1=C(C=CC=C1)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC)F GEFVFTYILHWIGO-UHFFFAOYSA-N 0.000 claims 1
- ASCUMAURKSBUPS-UHFFFAOYSA-N N-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound FC1=C(C(=CC=C1)C(F)(F)F)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)C(F)(F)F ASCUMAURKSBUPS-UHFFFAOYSA-N 0.000 claims 1
- MRFKCVIKSCVIEK-UHFFFAOYSA-N N-[[2-fluoro-6-(trifluoromethyl)phenyl]methyl]-1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound FC1=C(C(=CC=C1)C(F)(F)F)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1N=CC(=C1)C)C(F)(F)F MRFKCVIKSCVIEK-UHFFFAOYSA-N 0.000 claims 1
- CMNOMOOEIDZWNA-UHFFFAOYSA-N N-[[3-(difluoromethoxy)-2-fluorophenyl]methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound FC(OC=1C(=C(C=CC=1)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC)F)F CMNOMOOEIDZWNA-UHFFFAOYSA-N 0.000 claims 1
- KVPLENMFVKIMRG-UHFFFAOYSA-N N-[[3-chloro-2-fluoro-6-(trifluoromethyl)phenyl]methyl]-1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound ClC=1C(=C(C(=CC=1)C(F)(F)F)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1N=CC(=C1)C)C(F)(F)F)F KVPLENMFVKIMRG-UHFFFAOYSA-N 0.000 claims 1
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