JP2021119196A5 - - Google Patents
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- Publication number
- JP2021119196A5 JP2021119196A5 JP2021080175A JP2021080175A JP2021119196A5 JP 2021119196 A5 JP2021119196 A5 JP 2021119196A5 JP 2021080175 A JP2021080175 A JP 2021080175A JP 2021080175 A JP2021080175 A JP 2021080175A JP 2021119196 A5 JP2021119196 A5 JP 2021119196A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- carboxamide
- pyrazole
- methoxymethyl
- 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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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 417
- -1 3-Fluoro-4-methoxypyridin-2-yl Chemical group 0.000 claims 311
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 220
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 169
- ZVXKYWHJBYIYNI-UHFFFAOYSA-N 1h-pyrazole-4-carboxamide Chemical compound NC(=O)C=1C=NNC=1 ZVXKYWHJBYIYNI-UHFFFAOYSA-N 0.000 claims 144
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 30
- 150000001875 compounds Chemical class 0.000 claims 25
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 25
- 150000003839 salts Chemical class 0.000 claims 25
- 239000012453 solvate Substances 0.000 claims 25
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 20
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 15
- 201000010099 disease Diseases 0.000 claims 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 12
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 10
- 102000003827 Plasma Kallikrein Human genes 0.000 claims 10
- 108090000113 Plasma Kallikrein Proteins 0.000 claims 10
- 230000000694 effects Effects 0.000 claims 10
- RIKMMFOAQPJVMX-UHFFFAOYSA-N fomepizole Chemical compound CC=1C=NNC=1 RIKMMFOAQPJVMX-UHFFFAOYSA-N 0.000 claims 8
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
- LHZHVJWEENFPHR-UHFFFAOYSA-N 3-amino-N-[(3-fluoro-4-methoxypyridin-2-yl)methyl]-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound NC1=NN(C=C1C(=O)NCC1=NC=CC(=C1F)OC)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O LHZHVJWEENFPHR-UHFFFAOYSA-N 0.000 claims 6
- DLOVVYIYYDQZJE-UHFFFAOYSA-N N-[(5-chloro-3-cyanopyridin-2-yl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound ClC=1C=C(C(=NC=1)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC)C#N DLOVVYIYYDQZJE-UHFFFAOYSA-N 0.000 claims 6
- ZGVHOERMFFOQEE-UHFFFAOYSA-N N-[(5-chloro-3-fluoropyridin-2-yl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound ClC=1C=C(C(=NC=1)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC)F ZGVHOERMFFOQEE-UHFFFAOYSA-N 0.000 claims 6
- HHFDDRTYFWHVIW-UHFFFAOYSA-N N-[(6-carbamoyl-2-fluoro-3-methoxyphenyl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound C(N)(=O)C1=CC=C(C(=C1CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC)F)OC HHFDDRTYFWHVIW-UHFFFAOYSA-N 0.000 claims 6
- WONUSGGEAIADDP-UHFFFAOYSA-N N-[(6-cyano-2-fluoro-3-methoxyphenyl)methyl]-1-[[4-[(5-fluoro-2-oxopyridin-1-yl)methyl]phenyl]methyl]-3-(methoxymethyl)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)F)=O)COC)F)OC WONUSGGEAIADDP-UHFFFAOYSA-N 0.000 claims 6
- IYZKNUPIGJTMIO-UHFFFAOYSA-N 3-(methoxymethyl)-N-[(5-methoxy-2-methylphenyl)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 IYZKNUPIGJTMIO-UHFFFAOYSA-N 0.000 claims 5
- LBBWYBIVLDSOSM-UHFFFAOYSA-N N-[(3,5-difluoropyridin-2-yl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound FC=1C(=NC=C(C=1)F)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC LBBWYBIVLDSOSM-UHFFFAOYSA-N 0.000 claims 5
- CXNMCPFLYVYHGI-UHFFFAOYSA-N N-[(3-cyanopyridin-2-yl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound C(#N)C=1C(=NC=CC=1)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC CXNMCPFLYVYHGI-UHFFFAOYSA-N 0.000 claims 5
- GQIPLMKRGZCNHM-UHFFFAOYSA-N N-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound COC1=C(C(=NC=C1C)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC)C GQIPLMKRGZCNHM-UHFFFAOYSA-N 0.000 claims 5
- GLQJORYVDYGMMX-UHFFFAOYSA-N N-[(6-cyano-2-fluoro-3-methoxyphenyl)methyl]-3-(dimethylamino)-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)N(C)C)F)OC GLQJORYVDYGMMX-UHFFFAOYSA-N 0.000 claims 5
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 5
- VBARDULQROXGKU-UHFFFAOYSA-N 3-(dimethylamino)-N-[(3-fluoro-4-methoxypyridin-2-yl)methyl]-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound CN(C1=NN(C=C1C(=O)NCC1=NC=CC(=C1F)OC)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)C VBARDULQROXGKU-UHFFFAOYSA-N 0.000 claims 4
- KIWQUCLXUINFPR-UHFFFAOYSA-N 3-amino-N-[(6-cyano-2-fluoro-3-methoxyphenyl)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#N)OC)F)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O KIWQUCLXUINFPR-UHFFFAOYSA-N 0.000 claims 4
- 206010012688 Diabetic retinal oedema Diseases 0.000 claims 4
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 4
- YBWZNXCRUYMFTB-UHFFFAOYSA-N N-[(2-cyano-3-methoxyphenyl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound C(#N)C1=C(C=CC=C1OC)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC YBWZNXCRUYMFTB-UHFFFAOYSA-N 0.000 claims 4
- MGYKPDJSRMTHTJ-UHFFFAOYSA-N N-[(3-cyano-4-methoxypyridin-2-yl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound C(#N)C=1C(=NC=CC=1OC)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC MGYKPDJSRMTHTJ-UHFFFAOYSA-N 0.000 claims 4
- AXDZSJQRHYIUDG-UHFFFAOYSA-N N-[(5-cyano-2-methoxypyridin-4-yl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound C(#N)C=1C(=CC(=NC=1)OC)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC AXDZSJQRHYIUDG-UHFFFAOYSA-N 0.000 claims 4
- ITJBXHZPNBTJLT-UHFFFAOYSA-N N-[[3-(difluoromethyl)-4-methoxypyridin-2-yl]methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound FC(C=1C(=NC=CC=1OC)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC)F ITJBXHZPNBTJLT-UHFFFAOYSA-N 0.000 claims 4
- 206010030113 Oedema Diseases 0.000 claims 4
- 206010012601 diabetes mellitus Diseases 0.000 claims 4
- 201000011190 diabetic macular edema Diseases 0.000 claims 4
- POFCNULRYFDJGC-UHFFFAOYSA-N N-[(2-cyano-5-methoxyphenyl)methyl]-1-[[4-[(5-fluoro-2-oxopyridin-1-yl)methyl]phenyl]methyl]-3-(methoxymethyl)pyrazole-4-carboxamide Chemical compound C(#N)C1=C(C=C(C=C1)OC)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC(=C1)F)=O)COC POFCNULRYFDJGC-UHFFFAOYSA-N 0.000 claims 3
- HEWVRKZPFMJDLG-UHFFFAOYSA-N N-[(3-cyano-6-methoxypyridin-2-yl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound C(#N)C=1C(=NC(=CC=1)OC)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC HEWVRKZPFMJDLG-UHFFFAOYSA-N 0.000 claims 3
- YUQVECXMJHKKDM-UHFFFAOYSA-N N-[(4-chloro-3-fluoropyridin-2-yl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound ClC1=C(C(=NC=C1)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC)F YUQVECXMJHKKDM-UHFFFAOYSA-N 0.000 claims 3
- CYZQTSMNHNBGJE-UHFFFAOYSA-N N-[(5-chloro-4-methoxypyridin-2-yl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound ClC=1C(=CC(=NC=1)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC)OC CYZQTSMNHNBGJE-UHFFFAOYSA-N 0.000 claims 3
- 230000002207 retinal effect Effects 0.000 claims 3
- 230000008728 vascular permeability Effects 0.000 claims 3
- FLPHKCCGDBZNAY-UHFFFAOYSA-N 3-amino-N-[(2-cyano-5-methoxyphenyl)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)OC)C#N)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O FLPHKCCGDBZNAY-UHFFFAOYSA-N 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
- 206010019860 Hereditary angioedema 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
- 208000021908 Myocardial disease Diseases 0.000 claims 2
- UJZIGMJIMBSAFJ-UHFFFAOYSA-N N-[(2,6-difluoro-3,5-dimethoxyphenyl)methyl]-3-(methoxymethyl)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound FC1=C(C(=C(C=C1OC)OC)F)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)COC UJZIGMJIMBSAFJ-UHFFFAOYSA-N 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
- 230000023555 blood coagulation Effects 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 230000002612 cardiopulmonary effect Effects 0.000 claims 2
- 230000015271 coagulation Effects 0.000 claims 2
- 238000005345 coagulation Methods 0.000 claims 2
- 208000009190 disseminated intravascular coagulation Diseases 0.000 claims 2
- 230000036543 hypotension Effects 0.000 claims 2
- 230000004054 inflammatory process Effects 0.000 claims 2
- 208000020658 intracerebral hemorrhage Diseases 0.000 claims 2
- 208000017169 kidney disease Diseases 0.000 claims 2
- 230000000938 luteal effect Effects 0.000 claims 2
- 230000001404 mediated effect Effects 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
- 230000036303 septic shock Effects 0.000 claims 2
- 230000002792 vascular Effects 0.000 claims 2
- 208000029257 vision disease Diseases 0.000 claims 2
- 230000004393 visual impairment Effects 0.000 claims 2
- LRKPGPJCVAEYLI-UHFFFAOYSA-N 3-amino-N-[[2-(difluoromethyl)-5-methoxyphenyl]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)OC)C(F)F)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O LRKPGPJCVAEYLI-UHFFFAOYSA-N 0.000 claims 1
- JOEWUHMFEBQTSY-UHFFFAOYSA-N 3-amino-N-[[5-methoxy-2-(trifluoromethyl)phenyl]methyl]-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound COc1ccc(c(CNC(=O)c2cn(Cc3ccc(Cn4ccccc4=O)cc3)nc2N)c1)C(F)(F)F JOEWUHMFEBQTSY-UHFFFAOYSA-N 0.000 claims 1
- XXIKICVNFYVRGO-UHFFFAOYSA-N N-[(2,6-difluoro-3-methoxyphenyl)methyl]-3-(dimethylamino)-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)N(C)C XXIKICVNFYVRGO-UHFFFAOYSA-N 0.000 claims 1
- YAEGMEZVGUPMMS-UHFFFAOYSA-N N-[(2-cyano-5-methoxyphenyl)methyl]-3-(dimethylamino)-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound C(#N)C1=C(C=C(C=C1)OC)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)N(C)C YAEGMEZVGUPMMS-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000004644 retinal vein occlusion Diseases 0.000 claims 1
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662343363P | 2016-05-31 | 2016-05-31 | |
| GB1609517.6 | 2016-05-31 | ||
| US62/343,363 | 2016-05-31 | ||
| GBGB1609517.6A GB201609517D0 (en) | 2016-05-31 | 2016-05-31 | Enzyme inhibitors |
| US201762456219P | 2017-02-08 | 2017-02-08 | |
| US62/456,219 | 2017-02-08 | ||
| GB1702044.7 | 2017-02-08 | ||
| GBGB1702044.7A GB201702044D0 (en) | 2017-02-08 | 2017-02-08 | Enzyme inhibitors |
| JP2018560068A JP6884801B2 (ja) | 2016-05-31 | 2017-05-31 | 血漿カリクレインインヒビターとしてのピラゾール誘導体 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018560068A Division JP6884801B2 (ja) | 2016-05-31 | 2017-05-31 | 血漿カリクレインインヒビターとしてのピラゾール誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2021119196A JP2021119196A (ja) | 2021-08-12 |
| JP2021119196A5 true JP2021119196A5 (enExample) | 2021-10-07 |
| JP7109012B2 JP7109012B2 (ja) | 2022-07-29 |
Family
ID=60478506
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018560068A Expired - Fee Related JP6884801B2 (ja) | 2016-05-31 | 2017-05-31 | 血漿カリクレインインヒビターとしてのピラゾール誘導体 |
| JP2021080175A Active JP7109012B2 (ja) | 2016-05-31 | 2021-05-11 | 血漿カリクレインインヒビターとしてのピラゾール誘導体 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018560068A Expired - Fee Related JP6884801B2 (ja) | 2016-05-31 | 2017-05-31 | 血漿カリクレインインヒビターとしてのピラゾール誘導体 |
Country Status (32)
Families Citing this family (28)
| 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 |
| RS60600B1 (sr) | 2016-05-31 | 2020-08-31 | Kalvista Pharmaceuticals Ltd | Derivati pirazola kao inhibitori kalikreina plazme |
| 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 |
| 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 |
| WO2019106359A1 (en) * | 2017-11-29 | 2019-06-06 | Kalvista Pharmaceuticals Limited | Enzyme inhibitors |
| GB201719882D0 (en) * | 2017-11-29 | 2018-01-10 | Kalvista Pharmaceuticals Ltd | Solid forms of a plasma kallikrein inhibitor and salts thereof |
| IL274557B2 (en) | 2017-11-29 | 2024-09-01 | Kalvista Pharmaceuticals Ltd | Dosage forms comprising a plasma kallikrein inhibitor |
| GB201719881D0 (en) * | 2017-11-29 | 2018-01-10 | Kalvista Pharmaceuticals Ltd | Solid forms of plasma kallikrein inhibitor and salts thereof |
| KR20200143376A (ko) | 2018-03-13 | 2020-12-23 | 샤이어 휴먼 지네틱 테라피즈 인크. | 혈장 칼리크레인 억제제로서의 치환된 이미다조피리딘 및 이의 용도 |
| EP3863713B1 (en) | 2018-10-10 | 2023-01-25 | Boehringer Ingelheim International GmbH | Phenyltetrazole derivatives as plasma kallikrein inhibitors |
| EP3886854A4 (en) | 2018-11-30 | 2022-07-06 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| CN114206852A (zh) | 2019-08-09 | 2022-03-18 | 卡尔维斯塔制药有限公司 | 血浆激肽释放酶抑制剂 |
| ES2987744T3 (es) | 2019-09-18 | 2024-11-18 | Takeda Pharmaceuticals Co | Inhibidores de calicreína plasmática y usos de los mismos |
| WO2021055589A1 (en) | 2019-09-18 | 2021-03-25 | Shire Human Genetic Therapies, Inc. | Heteroaryl plasma kallikrein inhibitors |
| TWI873290B (zh) | 2020-02-13 | 2025-02-21 | 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 |
| 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 |
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