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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Country Status (42)
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI636047B (zh) | 2013-08-14 | 2018-09-21 | 英商卡爾維斯塔製藥有限公司 | 雜環衍生物 |
| GB201421085D0 (en) | 2014-11-27 | 2015-01-14 | Kalvista Pharmaceuticals Ltd | New enzyme inhibitors |
| GB201421083D0 (en) | 2014-11-27 | 2015-01-14 | Kalvista Pharmaceuticals Ltd | Enzyme inhibitors |
| MY198346A (en) | 2015-10-01 | 2023-08-28 | Biocryst Pharm Inc | Human plasma kallikrein inhibitors |
| IL263235B (en) | 2016-05-31 | 2022-07-01 | Kalvista Pharmaceuticals Ltd | History of pyrazoles as plasma kallikrein inhibitors |
| GB201609519D0 (en) * | 2016-05-31 | 2016-07-13 | Kalvista Pharmaceuticals Ltd | Polymorphs of n-[(2,6-difluoro-3-methoxyphenyl)methyl]-3-(methoxymethyl)-1-({4-[(2-oxopyr idin-1-yl)methyl]phenyl}methyl)pyrazole-4-carboxamide |
| GB201609607D0 (en) * | 2016-06-01 | 2016-07-13 | Kalvista Pharmaceuticals Ltd | Polymorphs of N-(3-Fluoro-4-methoxypyridin-2-yl)methyl)-3-(methoxymethyl)-1-({4-((2-oxopy ridin-1-yl)methyl)phenyl}methyl)pyrazole-4-carboxamide and salts |
| GB201609603D0 (en) | 2016-06-01 | 2016-07-13 | Kalvista Pharmaceuticals Ltd | Polymorphs of N-[(6-cyano-2-fluoro-3-methoxyphenyl)Methyl]-3-(methoxymethyl)-1-({4-[(2-ox opyridin-1-YL)Methyl]phenyl}methyl)pyrazole-4-carboxamide |
| WO2018200674A1 (en) * | 2017-04-26 | 2018-11-01 | Mitobridge, Inc. | Dynamin-1-like protein inhibitors |
| GB201719882D0 (en) * | 2017-11-29 | 2018-01-10 | Kalvista Pharmaceuticals Ltd | Solid forms of a plasma kallikrein inhibitor and salts thereof |
| GB201721515D0 (en) * | 2017-12-21 | 2018-02-07 | Kalvista Pharmaceuticals Ltd | Dosage forms comprising a plasma kallikrein inhibtor |
| GB201719881D0 (en) | 2017-11-29 | 2018-01-10 | Kalvista Pharmaceuticals Ltd | Solid forms of plasma kallikrein inhibitor and salts thereof |
| WO2019106359A1 (en) * | 2017-11-29 | 2019-06-06 | Kalvista Pharmaceuticals Limited | Enzyme inhibitors |
| HUE057912T2 (hu) | 2017-11-29 | 2022-06-28 | Kalvista Pharmaceuticals Ltd | Plazma kallikrein inhibitort tartalmazó dózisformák |
| KR20200143376A (ko) | 2018-03-13 | 2020-12-23 | 샤이어 휴먼 지네틱 테라피즈 인크. | 혈장 칼리크레인 억제제로서의 치환된 이미다조피리딘 및 이의 용도 |
| WO2020113094A1 (en) | 2018-11-30 | 2020-06-04 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| GB201910125D0 (en) * | 2019-07-15 | 2019-08-28 | Kalvista Pharmaceuticals Ltd | Treatments of angioedema |
| GB201910116D0 (en) | 2019-07-15 | 2019-08-28 | Kalvista Pharmaceuticals Ltd | Treatments of hereditary angioedema |
| WO2021028645A1 (en) | 2019-08-09 | 2021-02-18 | Kalvista Pharmaceuticals Limited | Plasma kallikrein inhibitors |
| CN114667289B (zh) | 2019-09-18 | 2025-08-26 | 武田药品工业有限公司 | 杂芳基血浆激肽释放酶抑制剂 |
| EP4031547B1 (en) | 2019-09-18 | 2024-07-17 | Takeda Pharmaceutical Company Limited | Plasma kallikrein inhibitors and uses thereof |
| CN113004286B (zh) * | 2019-12-20 | 2022-08-12 | 成都康弘药业集团股份有限公司 | 作为血浆激肽释放酶抑制剂的三环类化合物及其用途 |
| TW202144331A (zh) * | 2020-02-13 | 2021-12-01 | 德商百靈佳殷格翰國際股份有限公司 | 作為血漿激肽釋放酶抑制劑之雜芳族甲醯胺衍生物 |
| JP7245397B2 (ja) * | 2020-03-04 | 2023-03-23 | メッドシャイン ディスカバリー インコーポレイテッド | 複素環化合物 |
| JP7776453B2 (ja) | 2020-06-16 | 2025-11-26 | メルク・シャープ・アンド・ドーム・エルエルシー | 血漿カリクレイン阻害剤 |
| KR20230038526A (ko) | 2020-07-10 | 2023-03-20 | 머크 샤프 앤드 돔 엘엘씨 | 혈장 칼리크레인 억제제 |
| TW202228686A (zh) | 2020-10-15 | 2022-08-01 | 英商卡爾維斯塔製藥有限公司 | 血管性水腫之治療 |
| US20230381162A1 (en) | 2020-10-23 | 2023-11-30 | Kalvista Pharmaceuticals Limited | Treatments of angioedema |
| JP2024505596A (ja) | 2021-02-09 | 2024-02-06 | カルビスタ・ファーマシューティカルズ・リミテッド | 遺伝性血管性浮腫の治療 |
| WO2023002219A1 (en) | 2021-07-23 | 2023-01-26 | Kalvista Pharmaceuticals Limited | Treatments of hereditary angioedema |
| WO2023185634A1 (zh) * | 2022-03-30 | 2023-10-05 | 南京明德新药研发有限公司 | 作为血浆激肽释放酶抑制剂的杂环类化合物 |
| US20250281397A1 (en) | 2022-04-27 | 2025-09-11 | Kalvista Pharmaceuticals Limited | Formulations of a plasma kallikrein inhibitor |
| JP2025526464A (ja) * | 2022-07-29 | 2025-08-13 | レゾリュート インコーポレイテッド | 血漿カリクレインの阻害剤 |
| WO2024180100A1 (en) | 2023-02-27 | 2024-09-06 | Kalvista Pharmaceuticals Limited | New solid form of a plasma kallikrein inhibitor |
| WO2025001956A1 (zh) | 2023-06-30 | 2025-01-02 | 远森制药（杭州）有限公司 | 杂芳族甲酰胺类化合物及其在医药上的应用 |
| WO2025153806A1 (en) | 2024-01-15 | 2025-07-24 | Kalvista Pharmaceuticals Limited | Methods for determining amidolytic activity |
| WO2025172692A1 (en) | 2024-02-13 | 2025-08-21 | Kalvista Pharmaceuticals Limited | Oral sebetralstat for the treatment of an attack of hereditary angioedema |
| WO2025172693A1 (en) | 2024-02-13 | 2025-08-21 | Kalvista Pharmaceuticals Limited | Oral sebetralstat for the treatment of an attack of hereditary angioedema |
Family Cites Families (98)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5187157A (en) | 1987-06-05 | 1993-02-16 | Du Pont Merck Pharmaceutical Company | Peptide boronic acid inhibitors of trypsin-like proteases |
| GB9019558D0 (en) | 1990-09-07 | 1990-10-24 | Szelke Michael | Enzyme inhibitors |
| SE9301911D0 (sv) | 1993-06-03 | 1993-06-03 | Ab Astra | New peptide derivatives |
| US5589467A (en) | 1993-09-17 | 1996-12-31 | Novo Nordisk A/S | 2,5',N6-trisubstituted adenosine derivatives |
| US5786328A (en) | 1995-06-05 | 1998-07-28 | Genentech, Inc. | Use of kunitz type plasma kallikrein inhibitors |
| US7101878B1 (en) | 1998-08-20 | 2006-09-05 | Agouron Pharmaceuticals, Inc. | Non-peptide GNRH agents, methods and intermediates for their preparation |
| PL215901B1 (pl) * | 1999-04-15 | 2014-02-28 | Bristol Myers Squibb Co | Cykliczny inhibitor bialkowych kinaz tyrozynowych, jego zastosowanie oraz kompozycja farmaceutyczna zawierajaca taki zwiazek |
| EP1441734B1 (en) | 2001-10-26 | 2007-02-28 | Istituto di Richerche di Biologia Molecolare P. Angeletti S.p.A. | Dihydroxypyrimidine carboxamide inhibitors of hiv integrase |
| AU2002363250A1 (en) | 2001-11-01 | 2003-05-12 | Icagen, Inc. | Pyrazole-amides and-sulfonamides |
| GB0205527D0 (en) | 2002-03-08 | 2002-04-24 | Ferring Bv | Inhibitors |
| KR100755577B1 (ko) | 2002-04-26 | 2007-09-12 | 일라이 릴리 앤드 캄파니 | 타키키닌 수용체 길항제로서의 트리아졸 유도체 |
| EP1426364A1 (en) | 2002-12-04 | 2004-06-09 | Aventis Pharma Deutschland GmbH | Imidazole-derivatives as factor Xa inhibitors |
| DE10301300B4 (de) | 2003-01-15 | 2009-07-16 | Curacyte Chemistry Gmbh | Verwendung von acylierten 4-Amidino- und 4-Guanidinobenzylaminen zur Inhibierung von Plasmakallikrein |
| US20040192728A1 (en) | 2003-02-03 | 2004-09-30 | Ellen Codd | Quinoline-derived amide modulators of vanilloid VR1 receptor |
| NZ592039A (en) | 2003-08-27 | 2013-03-28 | Ophthotech Corp | Combination therapy for the treatment of ocular neovascular disorders |
| TW200526588A (en) * | 2003-11-17 | 2005-08-16 | Smithkline Beecham Corp | Chemical compounds |
| GB0403155D0 (en) | 2004-02-12 | 2004-03-17 | Vernalis Res Ltd | Chemical compounds |
| EP1568698A1 (en) | 2004-02-27 | 2005-08-31 | Aventis Pharma Deutschland GmbH | Pyrrole-derivatives as factor Xa inhibitors |
| US7429604B2 (en) | 2004-06-15 | 2008-09-30 | Bristol Myers Squibb Company | Six-membered heterocycles useful as serine protease inhibitors |
| MX2007002214A (es) | 2004-09-03 | 2007-05-07 | Yuhan Corp | Derivados de pirrolo[3,2-c]piridina y procesos para su preparacion. |
| EP2500031A3 (en) | 2005-02-24 | 2012-12-26 | Joslin Diabetes Center, Inc. | Compositions and Methods for Treating Vascular Permeability |
| GB0508472D0 (en) | 2005-04-26 | 2005-06-01 | Glaxo Group Ltd | Compounds |
| KR101142363B1 (ko) | 2005-06-27 | 2012-05-21 | 주식회사유한양행 | 피롤로피리딘 유도체를 포함하는 항암제 조성물 |
| EA200800321A1 (ru) | 2005-07-14 | 2008-06-30 | Такеда Сан Диего, Инк. | Ингибиторы гистондеацетилазы |
| WO2007011328A1 (en) * | 2005-07-14 | 2007-01-25 | Jackson Kenneth A | A method for disabling a hypodermic needle after use |
| US20070254894A1 (en) | 2006-01-10 | 2007-11-01 | Kane John L Jr | Novel small molecules with selective cytotoxicity against human microvascular endothelial cell proliferation |
| GB0606876D0 (en) | 2006-04-05 | 2006-05-17 | Glaxo Group Ltd | Compounds |
| US20070258976A1 (en) | 2006-05-04 | 2007-11-08 | Ward Keith W | Combination Therapy for Diseases Involving Angiogenesis |
| CA2655675A1 (en) | 2006-07-06 | 2008-01-10 | Glaxo Group Limited | Substituted n-phenylmethyl -5-oxo-proline-2-amides as p2x7-receptor antagonists and their methods of use |
| JP5322935B2 (ja) | 2006-07-31 | 2013-10-23 | アクティベサイト ファーマシューティカルズ インコーポレイティッド | 血漿カリクレインの阻害薬 |
| DE102006050672A1 (de) | 2006-10-24 | 2008-04-30 | Curacyte Discovery Gmbh | Hemmstoffe des Plasmins und des Plasmakallikreins |
| KR101578674B1 (ko) | 2006-12-29 | 2015-12-18 | 아비에 도이치란트 게엠베하 운트 콤파니 카게 | 카복스아미드 화합물 및 칼페인 억제제로서의 이의 용도 |
| US20100119512A1 (en) | 2007-01-25 | 2010-05-13 | Joslin Diabetes Center | Methods of diagnosing, treating, and preventing increased vascular permeability |
| AU2008223348A1 (en) | 2007-03-07 | 2008-09-12 | Alantos Pharmaceuticals Holding, Inc. | Metalloprotease inhibitors containing a heterocyclic moiety |
| DK2142516T3 (da) | 2007-03-30 | 2013-04-15 | Sanofi Sa | Pyrimidinhydrazidforbindelser i ders egenskab af pgds-inhibitorer |
| CA2682649A1 (en) | 2007-04-03 | 2008-10-09 | Glaxo Group Limited | Imidazolidine carboxamide derivatives as p2x7 modulators |
| WO2009012998A1 (en) | 2007-07-26 | 2009-01-29 | Syngenta Participations Ag | Novel microbiocides |
| EP2185506A1 (en) | 2007-08-22 | 2010-05-19 | Allergan, Inc. | Pyrrole compounds having sphingosine-1-phosphate receptor agonist or antagonist biological activity |
| CA2709784A1 (en) | 2007-12-21 | 2009-07-09 | University Of Rochester | Method for altering the lifespan of eukaryotic organisms |
| WO2009083553A1 (en) | 2007-12-31 | 2009-07-09 | Rheoscience A/S | Azine compounds as glucokinase activators |
| EP2259679A4 (en) | 2008-01-31 | 2011-09-14 | Joslin Diabetes Ct | METHODS OF TREATING KALLIKREIN RELATED DISORDERS |
| WO2009106980A2 (en) | 2008-02-29 | 2009-09-03 | Pfizer Inc. | Indazole derivatives |
| US8324199B2 (en) | 2008-03-13 | 2012-12-04 | Bristol-Myers Squibb Company | Pyridazine derivatives as factor xia inhibitors |
| CN102149680B (zh) | 2008-07-08 | 2014-12-10 | 第一三共株式会社 | 含氮芳族杂环化合物 |
| US8324385B2 (en) | 2008-10-30 | 2012-12-04 | Madrigal Pharmaceuticals, Inc. | Diacylglycerol acyltransferase inhibitors |
| GB0910003D0 (en) | 2009-06-11 | 2009-07-22 | Univ Leuven Kath | Novel compounds for the treatment of neurodegenerative diseases |
| EP2512466A4 (en) | 2009-12-18 | 2013-07-03 | Activesite Pharmaceuticals Inc | PRODRUGS OF INHIBITORS OF PLASMATIC KALLICREIN |
| JP2011157349A (ja) | 2010-01-07 | 2011-08-18 | Daiichi Sankyo Co Ltd | 含窒素芳香族ヘテロシクリル化合物を含有する医薬組成物 |
| ES2569983T3 (es) | 2010-01-28 | 2016-05-13 | The Medicines Company (Leipzig) Gmbh | Inhibidores de serinproteasa de tipo tripsina y su preparación y uso |
| JP2013121919A (ja) | 2010-03-25 | 2013-06-20 | Astellas Pharma Inc | 血漿カリクレイン阻害剤 |
| EP2590945B1 (en) | 2010-07-07 | 2014-04-30 | The Medicines Company (Leipzig) GmbH | Serine protease inhibitors |
| US20130210809A1 (en) | 2010-07-14 | 2013-08-15 | Christelle Boléa | Novel 2-amino-4-pyrazolyl-thiazole derivatives and their use as allosteric modulators of metabotropic glutamate receptors |
| US9290485B2 (en) * | 2010-08-04 | 2016-03-22 | Novartis Ag | N-((6-amino-pyridin-3-yl)methyl)-heteroaryl-carboxamides |
| EP2458315B1 (de) | 2010-11-25 | 2017-01-04 | Balcke-Dürr GmbH | Regenerativer Wärmetauscher mit zwangsgeführter Rotordichtung |
| WO2012142308A1 (en) | 2011-04-13 | 2012-10-18 | Activesite Pharmaceuticals, Inc. | Prodrugs of inhibitors of plasma kallikrein |
| US9133128B2 (en) | 2011-06-17 | 2015-09-15 | Research Triangle Institute | Pyrazole derivatives as cannabinoid receptor 1 antagonists |
| GB2494851A (en) | 2011-07-07 | 2013-03-27 | Kalvista Pharmaceuticals Ltd | Plasma kallikrein inhibitors |
| WO2013048982A1 (en) | 2011-09-27 | 2013-04-04 | Bristol-Myers Squibb Company | Pyrrolinone carboxamide compounds useful as endothelial lipase inhibitors |
| EP2760828B1 (en) | 2011-09-27 | 2015-10-21 | Bristol-Myers Squibb Company | Pyrrolinone carboxamide compounds useful as endothelial lipase inhibitors |
| US20140378474A1 (en) * | 2012-01-27 | 2014-12-25 | Novartis Ag | 5-membered heteroarylcarboxamide derivatives as plasma kallikrein inhibitors |
| EP2807156A1 (en) | 2012-01-27 | 2014-12-03 | Novartis AG | Aminopyridine derivatives as plasma kallikrein inhibitors |
| NZ628762A (en) | 2012-02-10 | 2016-07-29 | Constellation Pharmaceuticals Inc | Modulators of methyl modifying enzymes, compositions and uses thereof |
| WO2013130603A1 (en) | 2012-02-27 | 2013-09-06 | Board Of Regents, The University Of Texas System | Ganglioside gd2 as a marker and target on cancer stem cells |
| GB201212081D0 (en) | 2012-07-06 | 2012-08-22 | Kalvista Pharmaceuticals Ltd | New polymorph |
| CN104918942A (zh) | 2013-01-08 | 2015-09-16 | 萨维拉制药有限公司 | 嘧啶酮衍生物和它们用于治疗、改善或预防病毒疾病的用途 |
| GB201300304D0 (en) | 2013-01-08 | 2013-02-20 | Kalvista Pharmaceuticals Ltd | Benzylamine derivatives |
| GB2510407A (en) | 2013-02-04 | 2014-08-06 | Kalvista Pharmaceuticals Ltd | Aqueous suspensions of kallikrein inhibitors for parenteral administration |
| WO2014113712A1 (en) | 2013-01-20 | 2014-07-24 | Dyax Corp. | Evaluation and treatment of bradykinin-mediated disorders |
| CN110179795A (zh) | 2013-03-15 | 2019-08-30 | 维颂公司 | 作为丝氨酸蛋白酶抑制剂的多取代芳族化合物的制药用途 |
| MY174018A (en) | 2013-05-23 | 2020-03-04 | Kalvista Pharmaceuticals Ltd | Heterocyclic derivates |
| GB2517908A (en) | 2013-08-14 | 2015-03-11 | Kalvista Pharmaceuticals Ltd | Bicyclic inhibitors |
| CA2920815C (en) | 2013-08-14 | 2021-09-21 | Kalvista Pharmaceuticals Limited | Inhibitors of plasma kallikrein |
| BR112016015449A8 (pt) | 2013-12-30 | 2020-06-09 | Lifesci Pharmaceuticals Inc | compostos inibidores terapêuticos, composição farmacêutica os compreendendo e uso dos mesmos |
| US9611252B2 (en) | 2013-12-30 | 2017-04-04 | Lifesci Pharmaceuticals, Inc. | Therapeutic inhibitory compounds |
| CN106257976B (zh) | 2014-03-07 | 2021-02-02 | 拜奥克里斯特制药公司 | 人类血浆激肽释放酶抑制剂 |
| WO2015171527A1 (en) | 2014-05-05 | 2015-11-12 | Global Blood Therapeutics, Inc. | Pyrazolopyridine pyrazolopyrimidine and related compounds |
| WO2015171526A2 (en) | 2014-05-05 | 2015-11-12 | Global Blood Therapeutics, Inc. | Tricyclic pyrazolopyridine compounds |
| MX381342B (es) | 2014-07-16 | 2025-03-12 | Lifesci Pharmaceuticals Inc | Compuestos terapeuticos inhibidores. |
| US10905683B2 (en) | 2014-08-22 | 2021-02-02 | Biocryst Pharmaceuticals, Inc. | Compositions and uses of amidine derivatives |
| US10189810B2 (en) | 2014-09-17 | 2019-01-29 | Verseon Corporation | Pyrazolyl-substituted pyridone compounds as serine protease inhibitors |
| GB201421088D0 (en) | 2014-11-27 | 2015-01-14 | Kalvista Pharmaceuticals Ltd | New enzyme inhibitors |
| GB201421085D0 (en) | 2014-11-27 | 2015-01-14 | Kalvista Pharmaceuticals Ltd | New enzyme inhibitors |
| GB201421083D0 (en) | 2014-11-27 | 2015-01-14 | Kalvista Pharmaceuticals Ltd | Enzyme inhibitors |
| CN107405333A (zh) | 2015-02-27 | 2017-11-28 | 维颂公司 | 作为丝氨酸蛋白酶抑制剂的被取代的吡唑化合物 |
| WO2017001926A2 (en) | 2015-07-01 | 2017-01-05 | Lifesci Pharmaceuticals, Inc | Therapeutic inhibitory compounds |
| WO2017001936A2 (en) | 2015-07-01 | 2017-01-05 | Lifesci Pharmaceuticals, Inc. | Therapeutic inhibitory compounds |
| JP6855477B2 (ja) | 2015-10-27 | 2021-04-07 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 血漿カリクレイン阻害薬としてのヘテロアリールカルボキサミド誘導体 |
| WO2017072020A1 (en) | 2015-10-27 | 2017-05-04 | Boehringer Ingelheim International Gmbh | Heteroarylcarboxamide derivatives as plasma kallikrein inhibitors |
| GB201609519D0 (en) | 2016-05-31 | 2016-07-13 | Kalvista Pharmaceuticals Ltd | Polymorphs of n-[(2,6-difluoro-3-methoxyphenyl)methyl]-3-(methoxymethyl)-1-({4-[(2-oxopyr idin-1-yl)methyl]phenyl}methyl)pyrazole-4-carboxamide |
| IL263235B (en) | 2016-05-31 | 2022-07-01 | Kalvista Pharmaceuticals Ltd | History of pyrazoles as plasma kallikrein inhibitors |
| GB201609603D0 (en) | 2016-06-01 | 2016-07-13 | Kalvista Pharmaceuticals Ltd | Polymorphs of N-[(6-cyano-2-fluoro-3-methoxyphenyl)Methyl]-3-(methoxymethyl)-1-({4-[(2-ox opyridin-1-YL)Methyl]phenyl}methyl)pyrazole-4-carboxamide |
| GB201609601D0 (en) | 2016-06-01 | 2016-07-13 | Nucana Biomed Ltd | Phosphoramidate compounds |
| GB201609602D0 (en) | 2016-06-01 | 2016-07-13 | Nucuna Biomed Ltd | Chemical compounds |
| GB201609607D0 (en) | 2016-06-01 | 2016-07-13 | Kalvista Pharmaceuticals Ltd | Polymorphs of N-(3-Fluoro-4-methoxypyridin-2-yl)methyl)-3-(methoxymethyl)-1-({4-((2-oxopy ridin-1-yl)methyl)phenyl}methyl)pyrazole-4-carboxamide and salts |
| CN110022875A (zh) | 2016-07-11 | 2019-07-16 | 莱福斯希医药公司 | 治疗性抑制化合物 |
| GB201719882D0 (en) | 2017-11-29 | 2018-01-10 | Kalvista Pharmaceuticals Ltd | Solid forms of a plasma kallikrein inhibitor and salts thereof |
| GB201719881D0 (en) | 2017-11-29 | 2018-01-10 | Kalvista Pharmaceuticals Ltd | Solid forms of plasma kallikrein inhibitor and salts thereof |
| WO2019106359A1 (en) | 2017-11-29 | 2019-06-06 | Kalvista Pharmaceuticals Limited | Enzyme inhibitors |
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