JP2016519156A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2016519156A5 JP2016519156A5 JP2016514486A JP2016514486A JP2016519156A5 JP 2016519156 A5 JP2016519156 A5 JP 2016519156A5 JP 2016514486 A JP2016514486 A JP 2016514486A JP 2016514486 A JP2016514486 A JP 2016514486A JP 2016519156 A5 JP2016519156 A5 JP 2016519156A5
- Authority
- JP
- Japan
- Prior art keywords
- ylmethyl
- amino
- amide
- carboxylic acid
- 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
Links
- 125000000217 alkyl group Chemical group 0.000 claims 34
- 125000003545 alkoxy group Chemical group 0.000 claims 25
- 150000001875 compounds Chemical class 0.000 claims 24
- 125000001424 substituent group Chemical group 0.000 claims 16
- 125000001072 heteroaryl group Chemical group 0.000 claims 15
- 125000003118 aryl group Chemical group 0.000 claims 12
- 102000003827 Plasma Kallikrein Human genes 0.000 claims 10
- 108090000113 Plasma Kallikrein Proteins 0.000 claims 10
- 201000010099 disease Diseases 0.000 claims 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 10
- 230000000694 effects Effects 0.000 claims 10
- 125000005843 halogen group Chemical group 0.000 claims 10
- -1 methylenedioxy, ethylenedioxy Chemical group 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 7
- 229910052717 sulfur Inorganic materials 0.000 claims 7
- 206010012688 Diabetic retinal oedema Diseases 0.000 claims 6
- 150000001408 amides Chemical class 0.000 claims 6
- 201000011190 diabetic macular edema Diseases 0.000 claims 6
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000002757 morpholinyl group Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000003386 piperidinyl group Chemical group 0.000 claims 5
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 4
- 206010019860 Hereditary angioedema Diseases 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 150000001491 aromatic compounds Chemical class 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 238000001356 surgical procedure Methods 0.000 claims 3
- 150000005258 1H-pyrrolo(2,3-b)pyridines Chemical class 0.000 claims 2
- QTARJTQMMMFRRC-UHFFFAOYSA-N 5-amino-n-[(1-aminoisoquinolin-6-yl)methyl]-1-[[4-(pyrazol-1-ylmethyl)phenyl]methyl]pyrazole-4-carboxamide Chemical compound NC1=C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)C=NN1CC(C=C1)=CC=C1CN1C=CC=N1 QTARJTQMMMFRRC-UHFFFAOYSA-N 0.000 claims 2
- 125000004070 6 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
- 239000004215 Carbon black (E152) Substances 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
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 2
- 206010040070 Septic Shock 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
- MVXVYAKCVDQRLW-UHFFFAOYSA-N azain Natural products C1=CN=C2NC=CC2=C1 MVXVYAKCVDQRLW-UHFFFAOYSA-N 0.000 claims 2
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 2
- 235000010290 biphenyl Nutrition 0.000 claims 2
- 239000004305 biphenyl Substances 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 230000002612 cardiopulmonary effect Effects 0.000 claims 2
- 230000006735 deficit Effects 0.000 claims 2
- 206010012601 diabetes mellitus Diseases 0.000 claims 2
- 208000009190 disseminated intravascular coagulation Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 150000002430 hydrocarbons Chemical class 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
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 201000001119 neuropathy Diseases 0.000 claims 2
- 230000007823 neuropathy Effects 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims 2
- 230000002207 retinal effect Effects 0.000 claims 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 2
- 230000036303 septic shock Effects 0.000 claims 2
- 230000008728 vascular permeability Effects 0.000 claims 2
- OWQPOVKKUWUEKE-UHFFFAOYSA-N 1,2,3-benzotriazine Chemical class N1=NN=CC2=CC=CC=C21 OWQPOVKKUWUEKE-UHFFFAOYSA-N 0.000 claims 1
- GDAXJBDYNVDMDF-UHFFFAOYSA-N 1,2,4-benzotriazine Chemical compound N1=NC=NC2=CC=CC=C21 GDAXJBDYNVDMDF-UHFFFAOYSA-N 0.000 claims 1
- 150000005057 1,7-naphthyridines Chemical class 0.000 claims 1
- 150000005058 1,8-naphthyridines Chemical class 0.000 claims 1
- VPLIKMCHOHMYFL-UHFFFAOYSA-N 1-[[2-[(4-methylpyrazol-1-yl)methyl]-1,3-thiazol-4-yl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound Cc1cnn(Cc2nc(Cn3cc(C(O)=O)c(n3)C(F)(F)F)cs2)c1 VPLIKMCHOHMYFL-UHFFFAOYSA-N 0.000 claims 1
- UVUGVZJMKMGPPT-UHFFFAOYSA-N 1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound OC(=O)c1cn(Cc2ccc(Cn3ccccc3=O)cc2)nc1C(F)(F)F UVUGVZJMKMGPPT-UHFFFAOYSA-N 0.000 claims 1
- ZNSUFNBJZUAHMQ-UHFFFAOYSA-N 1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]-N-(1H-pyrrolo[2,3-b]pyridin-5-ylmethyl)-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound N1C=CC=2C1=NC=C(C=2)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)C(F)(F)F ZNSUFNBJZUAHMQ-UHFFFAOYSA-N 0.000 claims 1
- CLZJGBDROZBBHL-UHFFFAOYSA-N 1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]-N-(1H-pyrrolo[2,3-b]pyridin-5-ylmethyl)-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound N1C=CC=2C1=NC=C(C=2)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1N=CC(=C1)C)C(F)(F)F CLZJGBDROZBBHL-UHFFFAOYSA-N 0.000 claims 1
- UXSWNBHODCRZQX-UHFFFAOYSA-N 1-[[6-(3,3-difluoropyrrolidin-1-yl)pyridin-3-yl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound OC(=O)c1cn(Cc2ccc(nc2)N2CCC(F)(F)C2)nc1C(F)(F)F UXSWNBHODCRZQX-UHFFFAOYSA-N 0.000 claims 1
- KYEOVWIJJFNXPL-UHFFFAOYSA-N 1-[[6-[3-(hydroxymethyl)pyrrolidin-1-yl]pyridin-3-yl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxylic acid Chemical compound OCC1CCN(C1)c1ccc(Cn2cc(C(O)=O)c(n2)C(F)(F)F)cn1 KYEOVWIJJFNXPL-UHFFFAOYSA-N 0.000 claims 1
- HDIHRESJULZUPH-UHFFFAOYSA-N 1-ethyl-4-methyl-5-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrrole-2-carboxylic acid Chemical compound CCn1c(Cc2ccc(Cn3ccccc3=O)cc2)c(C)cc1C(O)=O HDIHRESJULZUPH-UHFFFAOYSA-N 0.000 claims 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 1
- PWINZESYUZCYRY-UHFFFAOYSA-N 3-amino-n-[(1-aminoisoquinolin-6-yl)methyl]-1-[(6-ethoxypyridin-3-yl)methyl]pyrazole-4-carboxamide Chemical compound C1=NC(OCC)=CC=C1CN1N=C(N)C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C1 PWINZESYUZCYRY-UHFFFAOYSA-N 0.000 claims 1
- HIYGQPZTBFIDNY-UHFFFAOYSA-N 3-amino-n-[(1-aminoisoquinolin-6-yl)methyl]-1-[(6-pyrrolidin-1-ylpyridin-3-yl)methyl]pyrazole-4-carboxamide Chemical compound C1=C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)C(N)=NN1CC(C=N1)=CC=C1N1CCCC1 HIYGQPZTBFIDNY-UHFFFAOYSA-N 0.000 claims 1
- GJNUIQWJKPAZQA-UHFFFAOYSA-N 3-amino-n-[(1-aminoisoquinolin-6-yl)methyl]-1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound C1=C(C)C=NN1CC(C=C1)=CC=C1CN1N=C(N)C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C1 GJNUIQWJKPAZQA-UHFFFAOYSA-N 0.000 claims 1
- KRYGFFGIEKPPMW-UHFFFAOYSA-N 3-cyclopropyl-1-[[6-(3,3-difluoropyrrolidin-1-yl)pyridin-3-yl]methyl]pyrazole-4-carboxylic acid Chemical compound OC(=O)c1cn(Cc2ccc(nc2)N2CCC(F)(F)C2)nc1C1CC1 KRYGFFGIEKPPMW-UHFFFAOYSA-N 0.000 claims 1
- CDDROBVTAJIFPI-UHFFFAOYSA-N 3-cyclopropyl-1-[[6-[2-methoxyethyl(methyl)amino]pyridin-3-yl]methyl]pyrazole-4-carboxylic acid Chemical compound COCCN(C)c1ccc(Cn2cc(C(O)=O)c(n2)C2CC2)cn1 CDDROBVTAJIFPI-UHFFFAOYSA-N 0.000 claims 1
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 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 1
- 208000032843 Hemorrhage Diseases 0.000 claims 1
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims 1
- GOKGDYJODZLJNF-UHFFFAOYSA-N N-(1H-indol-5-ylmethyl)-1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound N1C=CC2=CC(=CC=C12)CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1N=CC(=C1)C)C(F)(F)F GOKGDYJODZLJNF-UHFFFAOYSA-N 0.000 claims 1
- NVEZCZPWINYFRQ-UHFFFAOYSA-N N-(2,3,3a,4,5,6,7,7a-octahydro-1H-indazol-4-ylmethyl)-3-amino-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound Nc1nn(Cc2ccc(Cn3ccccc3=O)cc2)cc1C(=O)NCC1CCCC2NNCC12 NVEZCZPWINYFRQ-UHFFFAOYSA-N 0.000 claims 1
- ZXPGXTZEIVIBIC-UHFFFAOYSA-N N-[(4,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methyl]-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound CC1=C2C(=NC(=C1CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1C(C=CC=C1)=O)C(F)(F)F)C)NC=C2 ZXPGXTZEIVIBIC-UHFFFAOYSA-N 0.000 claims 1
- PYSGSTYUQNZDJG-UHFFFAOYSA-N N-[(4,6-dimethyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methyl]-1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound CC1=C2C(=NC(=C1CNC(=O)C=1C(=NN(C=1)CC1=CC=C(C=C1)CN1N=CC(=C1)C)C(F)(F)F)C)NC=C2 PYSGSTYUQNZDJG-UHFFFAOYSA-N 0.000 claims 1
- 206010051077 Post procedural haemorrhage Diseases 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 208000034158 bleeding Diseases 0.000 claims 1
- 230000000740 bleeding effect Effects 0.000 claims 1
- 125000000259 cinnolinyl group Chemical class N1=NC(=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000002473 indoazoles Chemical class 0.000 claims 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 1
- 150000002475 indoles Chemical class 0.000 claims 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-N iso-quinoline Natural products C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 1
- 150000002537 isoquinolines Chemical class 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- DAOSBZHACYXGLP-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[(2-pyrrolidin-1-ylpyridin-4-yl)methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C=1C=C2C(N)=NC=CC2=CC=1CNC(=O)C(C(=N1)C(F)(F)F)=CN1CC(C=1)=CC=NC=1N1CCCC1 DAOSBZHACYXGLP-UHFFFAOYSA-N 0.000 claims 1
- BGFWCDCOIGUICN-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[(2-pyrrolidin-1-ylpyrimidin-5-yl)methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C=1C=C2C(N)=NC=CC2=CC=1CNC(=O)C(C(=N1)C(F)(F)F)=CN1CC(C=N1)=CN=C1N1CCCC1 BGFWCDCOIGUICN-UHFFFAOYSA-N 0.000 claims 1
- KXNHEPBASBKDTB-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[(5-chloro-6-ethoxypyridin-3-yl)methyl]-3-cyclopropylpyrazole-4-carboxamide Chemical compound C1=C(Cl)C(OCC)=NC=C1CN1N=C(C2CC2)C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C1 KXNHEPBASBKDTB-UHFFFAOYSA-N 0.000 claims 1
- AKRGGXIRZBHZIN-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[(5-chloro-6-pyrrolidin-1-ylpyridin-3-yl)methyl]-3-cyclopropylpyrazole-4-carboxamide Chemical compound C=1C=C2C(N)=NC=CC2=CC=1CNC(=O)C(C(=N1)C2CC2)=CN1CC(C=C1Cl)=CN=C1N1CCCC1 AKRGGXIRZBHZIN-UHFFFAOYSA-N 0.000 claims 1
- XCDBZZWRWFCHFE-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[(5-fluoro-6-pyrrolidin-1-ylpyridin-3-yl)methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C=1C=C2C(N)=NC=CC2=CC=1CNC(=O)C(C(=N1)C(F)(F)F)=CN1CC(C=C1F)=CN=C1N1CCCC1 XCDBZZWRWFCHFE-UHFFFAOYSA-N 0.000 claims 1
- GTQYYNKRYLNCBH-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[(5-pyrrolidin-1-ylpyrazin-2-yl)methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C=1C=C2C(N)=NC=CC2=CC=1CNC(=O)C(C(=N1)C(F)(F)F)=CN1CC(N=C1)=CN=C1N1CCCC1 GTQYYNKRYLNCBH-UHFFFAOYSA-N 0.000 claims 1
- GGVYRGRBULRJBJ-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[(6-ethoxy-5-fluoropyridin-3-yl)methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C1=C(F)C(OCC)=NC=C1CN1N=C(C(F)(F)F)C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C1 GGVYRGRBULRJBJ-UHFFFAOYSA-N 0.000 claims 1
- GKPBRBZRCXWGEQ-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[(6-ethoxypyridin-3-yl)methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C1=NC(OCC)=CC=C1CN1N=C(C(F)(F)F)C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C1 GKPBRBZRCXWGEQ-UHFFFAOYSA-N 0.000 claims 1
- DWFRBDIXHQEHJF-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[(6-propoxypyridin-3-yl)methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C1=NC(OCCC)=CC=C1CN1N=C(C(F)(F)F)C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C1 DWFRBDIXHQEHJF-UHFFFAOYSA-N 0.000 claims 1
- SLRCFYCDNOSNHM-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[(6-pyrrolidin-1-ylpyridin-3-yl)methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C=1C=C2C(N)=NC=CC2=CC=1CNC(=O)C(C(=N1)C(F)(F)F)=CN1CC(C=N1)=CC=C1N1CCCC1 SLRCFYCDNOSNHM-UHFFFAOYSA-N 0.000 claims 1
- NTKGSHJOYRJNMU-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[[2-(pyrazol-1-ylmethyl)-1,3-thiazol-4-yl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C=1C=C2C(N)=NC=CC2=CC=1CNC(=O)C(C(=N1)C(F)(F)F)=CN1CC(N=1)=CSC=1CN1C=CC=N1 NTKGSHJOYRJNMU-UHFFFAOYSA-N 0.000 claims 1
- SCXKYBZCYMWSLK-INIZCTEOSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[[2-[(3s)-3-methylpyrrolidin-1-yl]pyridin-4-yl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C1[C@@H](C)CCN1C1=CC(CN2N=C(C(C(=O)NCC=3C=C4C=CN=C(N)C4=CC=3)=C2)C(F)(F)F)=CC=N1 SCXKYBZCYMWSLK-INIZCTEOSA-N 0.000 claims 1
- VRYHLJFFMXJWLQ-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[[4-(pyrazol-1-ylmethyl)phenyl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C=1C=C2C(N)=NC=CC2=CC=1CNC(=O)C(C(=N1)C(F)(F)F)=CN1CC(C=C1)=CC=C1CN1C=CC=N1 VRYHLJFFMXJWLQ-UHFFFAOYSA-N 0.000 claims 1
- NWLUWTWQKQUQDZ-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[[4-[(4-carbamoylpyrazol-1-yl)methyl]phenyl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C1=C(C(=O)N)C=NN1CC(C=C1)=CC=C1CN1N=C(C(F)(F)F)C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C1 NWLUWTWQKQUQDZ-UHFFFAOYSA-N 0.000 claims 1
- ZSWFNMZXDBXLIE-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[[4-[(4-cyanopyrazol-1-yl)methyl]phenyl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C=1C=C2C(N)=NC=CC2=CC=1CNC(=O)C(C(=N1)C(F)(F)F)=CN1CC(C=C1)=CC=C1CN1C=C(C#N)C=N1 ZSWFNMZXDBXLIE-UHFFFAOYSA-N 0.000 claims 1
- HXLUIKPALDGUQR-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C1=C(C)C=NN1CC(C=C1)=CC=C1CN1N=C(C(F)(F)F)C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C1 HXLUIKPALDGUQR-UHFFFAOYSA-N 0.000 claims 1
- DWHBFTOTOHZYPK-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]-3-morpholin-4-ylpyrazole-4-carboxamide Chemical compound C1=C(C)C=NN1CC(C=C1)=CC=C1CN1N=C(N2CCOCC2)C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C1 DWHBFTOTOHZYPK-UHFFFAOYSA-N 0.000 claims 1
- DCUMHGNRKGNEGD-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]-3-phenylpyrazole-4-carboxamide Chemical compound C1=C(C)C=NN1CC(C=C1)=CC=C1CN1N=C(C=2C=CC=CC=2)C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C1 DCUMHGNRKGNEGD-UHFFFAOYSA-N 0.000 claims 1
- URCKKASOEPCAIT-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]-3-propan-2-ylpyrazole-4-carboxamide Chemical compound C1=C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)C(C(C)C)=NN1CC(C=C1)=CC=C1CN1C=C(C)C=N1 URCKKASOEPCAIT-UHFFFAOYSA-N 0.000 claims 1
- CYHCYCIPTGUNKX-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]-3-thiophen-3-ylpyrazole-4-carboxamide Chemical compound C1=C(C)C=NN1CC(C=C1)=CC=C1CN1N=C(C2=CSC=C2)C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C1 CYHCYCIPTGUNKX-UHFFFAOYSA-N 0.000 claims 1
- LBMILRLEZDRJSC-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[[6-(pyrazol-1-ylmethyl)pyridin-3-yl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C=1C=C2C(N)=NC=CC2=CC=1CNC(=O)C(C(=N1)C(F)(F)F)=CN1CC(C=N1)=CC=C1CN1C=CC=N1 LBMILRLEZDRJSC-UHFFFAOYSA-N 0.000 claims 1
- DSSWHEZOLVGIOD-MRXNPFEDSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[[6-[(2r)-2-methylpyrrolidin-1-yl]pyridin-3-yl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C[C@@H]1CCCN1C(N=C1)=CC=C1CN1N=C(C(F)(F)F)C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C1 DSSWHEZOLVGIOD-MRXNPFEDSA-N 0.000 claims 1
- DSSWHEZOLVGIOD-INIZCTEOSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[[6-[(2s)-2-methylpyrrolidin-1-yl]pyridin-3-yl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C[C@H]1CCCN1C(N=C1)=CC=C1CN1N=C(C(F)(F)F)C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C1 DSSWHEZOLVGIOD-INIZCTEOSA-N 0.000 claims 1
- LQCMCNVSZTUNJE-GOSISDBHSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[[6-[(3r)-3-(hydroxymethyl)pyrrolidin-1-yl]pyridin-3-yl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C=1C=C2C(N)=NC=CC2=CC=1CNC(=O)C(C(=N1)C(F)(F)F)=CN1CC(C=N1)=CC=C1N1CC[C@@H](CO)C1 LQCMCNVSZTUNJE-GOSISDBHSA-N 0.000 claims 1
- HEUBVBUOFPIUJA-GOSISDBHSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[[6-[(3r)-3-fluoropyrrolidin-1-yl]pyridin-3-yl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C=1C=C2C(N)=NC=CC2=CC=1CNC(=O)C(C(=N1)C(F)(F)F)=CN1CC(C=N1)=CC=C1N1CC[C@@H](F)C1 HEUBVBUOFPIUJA-GOSISDBHSA-N 0.000 claims 1
- WETAMWXIAPCHJG-MRXNPFEDSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[[6-[(3r)-3-methylpyrrolidin-1-yl]pyridin-3-yl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C1[C@H](C)CCN1C(N=C1)=CC=C1CN1N=C(C(F)(F)F)C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C1 WETAMWXIAPCHJG-MRXNPFEDSA-N 0.000 claims 1
- HEUBVBUOFPIUJA-SFHVURJKSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[[6-[(3s)-3-fluoropyrrolidin-1-yl]pyridin-3-yl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C=1C=C2C(N)=NC=CC2=CC=1CNC(=O)C(C(=N1)C(F)(F)F)=CN1CC(C=N1)=CC=C1N1CC[C@H](F)C1 HEUBVBUOFPIUJA-SFHVURJKSA-N 0.000 claims 1
- WETAMWXIAPCHJG-INIZCTEOSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-[[6-[(3s)-3-methylpyrrolidin-1-yl]pyridin-3-yl]methyl]-3-(trifluoromethyl)pyrazole-4-carboxamide Chemical compound C1[C@@H](C)CCN1C(N=C1)=CC=C1CN1N=C(C(F)(F)F)C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C1 WETAMWXIAPCHJG-INIZCTEOSA-N 0.000 claims 1
- BMLMQNFIWXYERL-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-1-ethyl-4-methyl-5-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]pyrrole-2-carboxamide Chemical compound CC=1C=C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)N(CC)C=1CC(C=C1)=CC=C1CN1C=C(C)C=N1 BMLMQNFIWXYERL-UHFFFAOYSA-N 0.000 claims 1
- NDPHLXVHICHOPO-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-2,5-dimethyl-1-[(2-phenyl-1,3-thiazol-4-yl)methyl]pyrrole-3-carboxamide Chemical compound CC1=CC(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C(C)N1CC(N=1)=CSC=1C1=CC=CC=C1 NDPHLXVHICHOPO-UHFFFAOYSA-N 0.000 claims 1
- GBMUDCZNXCHCOS-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-2,5-dimethyl-1-[[4-[(2-oxopyridin-1-yl)methyl]phenyl]methyl]pyrrole-3-carboxamide Chemical compound CC1=CC(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C(C)N1CC(C=C1)=CC=C1CN1C=CC=CC1=O GBMUDCZNXCHCOS-UHFFFAOYSA-N 0.000 claims 1
- OUIUBQFLHJFGIC-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-2,5-dimethyl-1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]pyrrole-3-carboxamide Chemical compound C1=C(C)C=NN1CC(C=C1)=CC=C1CN1C(C)=C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)C=C1C OUIUBQFLHJFGIC-UHFFFAOYSA-N 0.000 claims 1
- QRXZKSAIEGYFFV-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-3-(3,5-dimethyl-1,2-oxazol-4-yl)-1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound C1=C(C)C=NN1CC(C=C1)=CC=C1CN1N=C(C2=C(ON=C2C)C)C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C1 QRXZKSAIEGYFFV-UHFFFAOYSA-N 0.000 claims 1
- VOHVWMYNYDPMER-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-3-(difluoromethyl)-1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound C1=C(C)C=NN1CC(C=C1)=CC=C1CN1N=C(C(F)F)C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C1 VOHVWMYNYDPMER-UHFFFAOYSA-N 0.000 claims 1
- VMIWCYSSHRTVOL-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-3-(hydroxymethyl)-1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound C1=C(C)C=NN1CC(C=C1)=CC=C1CN1N=C(CO)C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C1 VMIWCYSSHRTVOL-UHFFFAOYSA-N 0.000 claims 1
- XRSMOUUDULMQKD-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-3-(methoxymethyl)-1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound C1=C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)C(COC)=NN1CC(C=C1)=CC=C1CN1C=C(C)C=N1 XRSMOUUDULMQKD-UHFFFAOYSA-N 0.000 claims 1
- BDJNNTFQHLXNDS-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-3-cyano-1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound C1=C(C)C=NN1CC(C=C1)=CC=C1CN1N=C(C#N)C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C1 BDJNNTFQHLXNDS-UHFFFAOYSA-N 0.000 claims 1
- VUTOLLLOTRHDTA-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-3-cyclobutyl-1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound C1=C(C)C=NN1CC(C=C1)=CC=C1CN1N=C(C2CCC2)C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C1 VUTOLLLOTRHDTA-UHFFFAOYSA-N 0.000 claims 1
- SBMNLZABUQEIIC-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-3-cyclopropyl-1-[(4-methoxy-6-pyrrolidin-1-ylpyridin-3-yl)methyl]pyrazole-4-carboxamide Chemical compound COC1=CC(N2CCCC2)=NC=C1CN(N=1)C=C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)C=1C1CC1 SBMNLZABUQEIIC-UHFFFAOYSA-N 0.000 claims 1
- CUQLASPMTDPMRH-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-3-cyclopropyl-1-[(5-methoxy-6-pyrrolidin-1-ylpyridin-3-yl)methyl]pyrazole-4-carboxamide Chemical compound C=1N=C(N2CCCC2)C(OC)=CC=1CN(N=1)C=C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)C=1C1CC1 CUQLASPMTDPMRH-UHFFFAOYSA-N 0.000 claims 1
- MDTXJNQVRIMIES-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-3-cyclopropyl-1-[(6-phenoxypyridin-3-yl)methyl]pyrazole-4-carboxamide Chemical compound C=1C=C2C(N)=NC=CC2=CC=1CNC(=O)C(C(=N1)C2CC2)=CN1CC(C=N1)=CC=C1OC1=CC=CC=C1 MDTXJNQVRIMIES-UHFFFAOYSA-N 0.000 claims 1
- PMJBHWGXJWWQJR-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-3-cyclopropyl-1-[(6-pyrrolidin-1-ylpyridin-3-yl)methyl]pyrazole-4-carboxamide Chemical compound C=1C=C2C(N)=NC=CC2=CC=1CNC(=O)C(C(=N1)C2CC2)=CN1CC(C=N1)=CC=C1N1CCCC1 PMJBHWGXJWWQJR-UHFFFAOYSA-N 0.000 claims 1
- DYRPOBCRRDNPMT-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-3-cyclopropyl-1-[[4-(triazol-1-ylmethyl)phenyl]methyl]pyrazole-4-carboxamide Chemical compound C=1C=C2C(N)=NC=CC2=CC=1CNC(=O)C(C(=N1)C2CC2)=CN1CC(C=C1)=CC=C1CN1C=CN=N1 DYRPOBCRRDNPMT-UHFFFAOYSA-N 0.000 claims 1
- KEVAPGHQGBLBGH-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-3-cyclopropyl-1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound C1=C(C)C=NN1CC(C=C1)=CC=C1CN1N=C(C2CC2)C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C1 KEVAPGHQGBLBGH-UHFFFAOYSA-N 0.000 claims 1
- MJXNVOXGGURCQI-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-3-cyclopropyl-1-[[6-(diethylamino)-5-fluoropyridin-3-yl]methyl]pyrazole-4-carboxamide Chemical compound C1=C(F)C(N(CC)CC)=NC=C1CN1N=C(C2CC2)C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C1 MJXNVOXGGURCQI-UHFFFAOYSA-N 0.000 claims 1
- PXZBRJHSOLRAIJ-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-3-methyl-1-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]pyrazole-4-carboxamide Chemical compound C1=C(C)C=NN1CC(C=C1)=CC=C1CN1N=C(C)C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)=C1 PXZBRJHSOLRAIJ-UHFFFAOYSA-N 0.000 claims 1
- UAXGFNOVXFRLLA-UHFFFAOYSA-N n-[(1-aminoisoquinolin-6-yl)methyl]-4-methyl-2-[[4-[(4-methylpyrazol-1-yl)methyl]phenyl]methyl]-1,3-thiazole-5-carboxamide Chemical compound C1=C(C)C=NN1CC(C=C1)=CC=C1CC1=NC(C)=C(C(=O)NCC=2C=C3C=CN=C(N)C3=CC=2)S1 UAXGFNOVXFRLLA-UHFFFAOYSA-N 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- 150000003248 quinolines Chemical class 0.000 claims 1
- 150000003252 quinoxalines Chemical class 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361826596P | 2013-05-23 | 2013-05-23 | |
| US61/826,596 | 2013-05-23 | ||
| US201361865756P | 2013-08-14 | 2013-08-14 | |
| US61/865,756 | 2013-08-14 | ||
| PCT/GB2014/051592 WO2014188211A1 (en) | 2013-05-23 | 2014-05-23 | Heterocyclic derivates |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016519156A JP2016519156A (ja) | 2016-06-30 |
| JP2016519156A5 true JP2016519156A5 (enExample) | 2017-06-29 |
| JP6538028B2 JP6538028B2 (ja) | 2019-07-03 |
Family
ID=50841878
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016514486A Expired - Fee Related JP6538028B2 (ja) | 2013-05-23 | 2014-05-23 | 複素環式誘導体 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US9533987B2 (enExample) |
| EP (2) | EP3305778B1 (enExample) |
| JP (1) | JP6538028B2 (enExample) |
| KR (1) | KR102276700B1 (enExample) |
| CN (1) | CN105452240B (enExample) |
| AU (1) | AU2014270152B9 (enExample) |
| BR (1) | BR112015028879B1 (enExample) |
| CA (1) | CA2912285C (enExample) |
| CL (1) | CL2015003442A1 (enExample) |
| ES (2) | ES2626968T3 (enExample) |
| HU (2) | HUE057851T2 (enExample) |
| IL (1) | IL242513A0 (enExample) |
| MX (1) | MX363689B (enExample) |
| MY (1) | MY174018A (enExample) |
| PH (1) | PH12015502549A1 (enExample) |
| PL (2) | PL2999697T3 (enExample) |
| PT (1) | PT3305778T (enExample) |
| RU (1) | RU2712621C2 (enExample) |
| SG (1) | SG11201509303WA (enExample) |
| SI (1) | SI3305778T1 (enExample) |
| WO (1) | WO2014188211A1 (enExample) |
Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX366498B (es) * | 2013-08-14 | 2019-07-11 | Kalvista Pharmaceuticals Ltd | Inhibidores de calicreina plasmatica. |
| 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 |
| US9611252B2 (en) | 2013-12-30 | 2017-04-04 | Lifesci Pharmaceuticals, Inc. | Therapeutic inhibitory compounds |
| KR20160106627A (ko) | 2013-12-30 | 2016-09-12 | 라이프에스씨아이 파마슈티컬스, 인크. | 치료적 억제 화합물 |
| GB201421083D0 (en) * | 2014-11-27 | 2015-01-14 | Kalvista Pharmaceuticals Ltd | Enzyme 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 |
| CN104530013B (zh) * | 2014-12-04 | 2016-06-29 | 中国农业大学 | 基于吲哚环的吡唑酰胺类化合物作为农用杀菌剂的用途 |
| CN104761491B (zh) * | 2015-03-31 | 2018-08-21 | 山东友帮生化科技有限公司 | 2-氨基-3-碘-5-溴吡啶的合成方法 |
| EP3323809A4 (en) * | 2015-06-22 | 2019-01-02 | Sumitomo Dainippon Pharma Co., Ltd. | Bicyclic heterocyclic amide derivative |
| JP6917988B2 (ja) * | 2015-10-27 | 2021-08-11 | 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 |
| US10640486B2 (en) | 2015-10-27 | 2020-05-05 | 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 |
| RU2739447C2 (ru) * | 2016-05-31 | 2020-12-24 | Калвиста Фармасьютикалз Лимитед | Производные пиразола в качестве ингибиторов калликреина |
| 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 |
| WO2018011628A1 (en) | 2016-07-11 | 2018-01-18 | Lifesci Pharmaceuticals, Inc. | Therapeutic inhibitory compounds |
| JP7175914B2 (ja) * | 2017-04-21 | 2022-11-21 | 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剤としてのヘテロアリールカルボキサミド誘導体 |
| 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 |
| JP6828191B2 (ja) | 2018-08-16 | 2021-02-10 | 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剤としての複素芳香族カルボキサミド誘導体 |
| CN112839711A (zh) | 2018-10-10 | 2021-05-25 | 勃林格殷格翰国际有限公司 | 作为血浆激肽释放酶抑制剂的苯基四唑衍生物 |
| AU2019387370A1 (en) | 2018-11-30 | 2021-06-10 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| GB201910116D0 (en) | 2019-07-15 | 2019-08-28 | Kalvista Pharmaceuticals Ltd | Treatments of hereditary angioedema |
| GB201910125D0 (en) | 2019-07-15 | 2019-08-28 | Kalvista Pharmaceuticals Ltd | Treatments of angioedema |
| WO2021028645A1 (en) | 2019-08-09 | 2021-02-18 | Kalvista Pharmaceuticals Limited | Plasma kallikrein inhibitors |
| EP4017850A1 (en) | 2019-08-21 | 2022-06-29 | Kalvista Pharmaceuticals Limited | Enzyme inhibitors |
| GB201918994D0 (en) | 2019-12-20 | 2020-02-05 | Kalvista Pharmaceuticals Ltd | Treatments of diabetic macular edema and impaired visual acuity |
| TW202535863A (zh) | 2020-02-13 | 2025-09-16 | 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 |
| CN115210230A (zh) * | 2020-03-04 | 2022-10-18 | 南京明德新药研发有限公司 | 杂环类化合物 |
| 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 |
| WO2022084693A1 (en) | 2020-10-23 | 2022-04-28 | Kalvista Pharmaceuticals Limited | Treatments of angioedema |
| US20240122909A1 (en) | 2021-02-09 | 2024-04-18 | Kalvista Pharmaceuticals Limited | Treatments of hereditary angioedema |
| 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 |
| PL4288036T3 (pl) | 2022-04-27 | 2024-11-25 | Kalvista Pharmaceuticals Limited | Preparaty inhibitora kalikreiny osoczowej |
| WO2024180100A1 (en) | 2023-02-27 | 2024-09-06 | Kalvista Pharmaceuticals Limited | New solid form of a plasma kallikrein inhibitor |
| 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 (21)
| 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 |
| IL123986A (en) | 1997-04-24 | 2011-10-31 | Organon Nv | Medicinal compounds |
| KR100722344B1 (ko) * | 1999-04-15 | 2007-05-29 | 브리스톨-마이어스스퀴브컴파니 | 환형 단백질 티로신 키나제 억제제 |
| GB0205527D0 (en) | 2002-03-08 | 2002-04-24 | Ferring Bv | Inhibitors |
| CN1934255B (zh) | 2003-08-27 | 2012-07-11 | 奥普索特克公司 | 用于治疗眼新血管疾病的组合治疗 |
| US7429604B2 (en) * | 2004-06-15 | 2008-09-30 | Bristol Myers Squibb Company | Six-membered heterocycles useful as serine protease inhibitors |
| CA2658523C (en) * | 2006-07-31 | 2012-06-12 | Activesite Pharmaceuticals, Inc. | Inhibitors of plasma kallikrein |
| CN101495468A (zh) * | 2006-07-31 | 2009-07-29 | 艾克提弗赛特制药股份有限公司 | 血浆激肽释放酶抑制剂 |
| DE102006050672A1 (de) | 2006-10-24 | 2008-04-30 | Curacyte Discovery Gmbh | Hemmstoffe des Plasmins und des Plasmakallikreins |
| GB0910003D0 (en) | 2009-06-11 | 2009-07-22 | Univ Leuven Kath | Novel compounds for the treatment of neurodegenerative diseases |
| CA2783801A1 (en) * | 2009-12-18 | 2011-06-23 | Activesite Pharmaceuticals, Inc. | Prodrugs of inhibitors of plasma kallikrein |
| JP2013121919A (ja) | 2010-03-25 | 2013-06-20 | Astellas Pharma Inc | 血漿カリクレイン阻害剤 |
| WO2012004678A2 (en) | 2010-07-07 | 2012-01-12 | The Medicines Company (Leipzig) Gmbh | Serine protease inhibitors |
| US9290485B2 (en) * | 2010-08-04 | 2016-03-22 | Novartis Ag | N-((6-amino-pyridin-3-yl)methyl)-heteroaryl-carboxamides |
| EP2697196A1 (en) * | 2011-04-13 | 2014-02-19 | Activesite Pharmaceuticals, Inc. | Prodrugs of inhibitors of plasma kallikrein |
| 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 |
| 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 |
-
2014
- 2014-05-23 RU RU2015154987A patent/RU2712621C2/ru active
- 2014-05-23 BR BR112015028879-0A patent/BR112015028879B1/pt not_active IP Right Cessation
- 2014-05-23 SG SG11201509303WA patent/SG11201509303WA/en unknown
- 2014-05-23 HU HUE17166782A patent/HUE057851T2/hu unknown
- 2014-05-23 AU AU2014270152A patent/AU2014270152B9/en not_active Ceased
- 2014-05-23 JP JP2016514486A patent/JP6538028B2/ja not_active Expired - Fee Related
- 2014-05-23 MY MYPI2015704237A patent/MY174018A/en unknown
- 2014-05-23 KR KR1020157036257A patent/KR102276700B1/ko not_active Expired - Fee Related
- 2014-05-23 PL PL14727034T patent/PL2999697T3/pl unknown
- 2014-05-23 ES ES14727034.2T patent/ES2626968T3/es active Active
- 2014-05-23 MX MX2015016085A patent/MX363689B/es unknown
- 2014-05-23 HU HUE14727034A patent/HUE034829T2/en unknown
- 2014-05-23 WO PCT/GB2014/051592 patent/WO2014188211A1/en not_active Ceased
- 2014-05-23 EP EP17166782.7A patent/EP3305778B1/en active Active
- 2014-05-23 EP EP14727034.2A patent/EP2999697B1/en active Active
- 2014-05-23 SI SI201431947T patent/SI3305778T1/sl unknown
- 2014-05-23 PL PL17166782T patent/PL3305778T3/pl unknown
- 2014-05-23 CA CA2912285A patent/CA2912285C/en active Active
- 2014-05-23 PT PT171667827T patent/PT3305778T/pt unknown
- 2014-05-23 ES ES17166782T patent/ES2909885T3/es active Active
- 2014-05-23 US US14/892,055 patent/US9533987B2/en not_active Expired - Fee Related
- 2014-05-23 CN CN201480037390.8A patent/CN105452240B/zh not_active Expired - Fee Related
-
2015
- 2015-11-06 PH PH12015502549A patent/PH12015502549A1/en unknown
- 2015-11-09 IL IL242513A patent/IL242513A0/en active IP Right Grant
- 2015-11-23 CL CL2015003442A patent/CL2015003442A1/es unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2016519156A5 (enExample) | ||
| RU2015154987A (ru) | Гетероциклические производные | |
| JP2016504378A5 (enExample) | ||
| RU2015133171A (ru) | Бензиламиновые производные | |
| JP2019537571A5 (enExample) | ||
| RU2017122364A (ru) | N-((гет)арилметил)-гетероарил-карбоксамидные соединения в качестве ингибиторов плазменного калликреина | |
| JP2020033357A5 (enExample) | ||
| JP2018515555A5 (enExample) | ||
| RU2018140092A (ru) | Новые пиразолпиримидиновые производные | |
| IL288243B2 (en) | Heteroaryl-substituted pyridines and methods of use | |
| RU2018141881A (ru) | Производные пиразола в качестве ингибиторов калликреина | |
| RU2016108753A (ru) | Ингибиторы ферментов | |
| JP2014531465A5 (enExample) | ||
| IL263511A (en) | 1h-pyrazolo[4,3-b]pyridines as pde1 inhibitors | |
| WO2003051833A2 (en) | Heteroaryl substituted pyrazole modulators of metabotropic glutamate receptor-5 | |
| RU2016133684A (ru) | Бициклические азот-содержащие соединения как агонисты М1 мускариновых рецепторов | |
| RU2015138964A (ru) | Полициклические модуляторы рецептора эстрогена и их применения | |
| AU2014291711A1 (en) | Autotaxin inhibitors comprising a heteroaromatic ring-benzyl-amide-cycle core | |
| AR102852A1 (es) | Inhibidores heterocíclicos de la calicreína plasmática | |
| JP2014511869A5 (enExample) | ||
| HRP20160421T1 (hr) | Derivat azola | |
| JP2019523266A5 (enExample) | ||
| JP2019537603A5 (enExample) | ||
| JP2013536194A5 (enExample) | ||
| JP2017519818A5 (enExample) |