JP2014523897A5 - - Google Patents
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- Publication number
- JP2014523897A5 JP2014523897A5 JP2014517952A JP2014517952A JP2014523897A5 JP 2014523897 A5 JP2014523897 A5 JP 2014523897A5 JP 2014517952 A JP2014517952 A JP 2014517952A JP 2014517952 A JP2014517952 A JP 2014517952A JP 2014523897 A5 JP2014523897 A5 JP 2014523897A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- aminomethyl
- ethoxy
- ethyl
- benzylcarbamoyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 3,4-difluorophenyl Chemical group 0.000 claims 111
- 125000000217 alkyl group Chemical group 0.000 claims 19
- 125000003118 aryl group Chemical group 0.000 claims 14
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 13
- 150000001408 amides Chemical class 0.000 claims 12
- 125000001072 heteroaryl group Chemical group 0.000 claims 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims 8
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 7
- IFLKEBSJTZGCJG-UHFFFAOYSA-N 3-methylthiophene-2-carboxylic acid Chemical compound CC=1C=CSC=1C(O)=O IFLKEBSJTZGCJG-UHFFFAOYSA-N 0.000 claims 6
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 claims 4
- 102000003827 Plasma Kallikrein Human genes 0.000 claims 3
- 108090000113 Plasma Kallikrein Proteins 0.000 claims 3
- 125000002619 bicyclic group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- 125000002950 monocyclic group Chemical group 0.000 claims 3
- 229940080818 propionamide Drugs 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 claims 2
- KDRURSLBLPTKEJ-IOWSJCHKSA-N 3-acetamido-n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=C(NC(C)=O)C=CS1 KDRURSLBLPTKEJ-IOWSJCHKSA-N 0.000 claims 2
- GKOAHNGAVMWGNA-ZWXJPIIXSA-N 3-acetamido-n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-3-(1-benzothiophen-3-yl)-1-oxopropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C2=CC=CC=C2SC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=C(NC(C)=O)C=CS1 GKOAHNGAVMWGNA-ZWXJPIIXSA-N 0.000 claims 2
- HDDOGAGGUYGJLQ-FTJBHMTQSA-N 3-amino-n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-1-oxo-3-(1,3-thiazol-4-yl)propan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]thiophene-2-carboxamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1N=CSC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=C(N)C=CS1 HDDOGAGGUYGJLQ-FTJBHMTQSA-N 0.000 claims 2
- CQSJDKGNONPQOQ-UHFFFAOYSA-N 3-aminothiophene-2-carboxylic acid Chemical compound NC=1C=CSC=1C(O)=O CQSJDKGNONPQOQ-UHFFFAOYSA-N 0.000 claims 2
- BXEAAHIHFFIMIE-UHFFFAOYSA-N 3-chlorothiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC=CC=1Cl BXEAAHIHFFIMIE-UHFFFAOYSA-N 0.000 claims 2
- 206010012688 Diabetic retinal oedema Diseases 0.000 claims 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 2
- 201000011190 diabetic macular edema Diseases 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 2
- NOORMTUTGSQYIZ-AJQTZOPKSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)-3-chlorophenyl]methylamino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]benzamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC=1C=C(Cl)C(CN)=CC=1)NC(=O)C1=CC=CC=C1 NOORMTUTGSQYIZ-AJQTZOPKSA-N 0.000 claims 2
- UXHKCWBMPOSFQY-AJQTZOPKSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)-3-fluorophenyl]methylamino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]benzamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC=1C=C(F)C(CN)=CC=1)NC(=O)C1=CC=CC=C1 UXHKCWBMPOSFQY-AJQTZOPKSA-N 0.000 claims 2
- FLWSQHNEOSDTLW-WUFINQPMSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]-1,2-oxazole-5-carboxamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=CC=NO1 FLWSQHNEOSDTLW-WUFINQPMSA-N 0.000 claims 2
- NXZSBRDPYXWYMY-AJQTZOPKSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]-2,4-dichlorobenzamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=CC=C(Cl)C=C1Cl NXZSBRDPYXWYMY-AJQTZOPKSA-N 0.000 claims 2
- MOIZOCHEDGLANE-AJQTZOPKSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]-3,4-dichlorobenzamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=CC=C(Cl)C(Cl)=C1 MOIZOCHEDGLANE-AJQTZOPKSA-N 0.000 claims 2
- QWEGEWLFUNVAFH-AJQTZOPKSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]-3,4-difluorobenzamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=CC=C(F)C(F)=C1 QWEGEWLFUNVAFH-AJQTZOPKSA-N 0.000 claims 2
- SGUFCVJNEPZKMW-AJQTZOPKSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]-3-chlorobenzamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=CC=CC(Cl)=C1 SGUFCVJNEPZKMW-AJQTZOPKSA-N 0.000 claims 2
- CIHUARIXQZFRDX-XZWHSSHBSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]-3-methyl-1h-pyrrole-2-carboxamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=C(C)C=CN1 CIHUARIXQZFRDX-XZWHSSHBSA-N 0.000 claims 2
- WQZFDLDYUJSANS-AJQTZOPKSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]-4-chlorobenzamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=CC=C(Cl)C=C1 WQZFDLDYUJSANS-AJQTZOPKSA-N 0.000 claims 2
- HAVAYEXOBKJLDE-AJQTZOPKSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]-4-fluorobenzamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=CC=C(F)C=C1 HAVAYEXOBKJLDE-AJQTZOPKSA-N 0.000 claims 2
- HODNEEJOSRVWQT-JHOUSYSJSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]-4-methoxybenzamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=CC=C(OC)C=C1 HODNEEJOSRVWQT-JHOUSYSJSA-N 0.000 claims 2
- PQYXYUJVSKCKFL-JHOUSYSJSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]-4-methylbenzamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=CC=C(C)C=C1 PQYXYUJVSKCKFL-JHOUSYSJSA-N 0.000 claims 2
- UCIXIQRCAGGOJY-AJQTZOPKSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]benzamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=CC=CC=C1 UCIXIQRCAGGOJY-AJQTZOPKSA-N 0.000 claims 2
- ZBMHBTNVTBWRGV-AJQTZOPKSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]cyclohexanecarboxamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1CCCCC1 ZBMHBTNVTBWRGV-AJQTZOPKSA-N 0.000 claims 2
- NBUOOLFOHRYQNL-IOWSJCHKSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]pyridine-3-carboxamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=CC=CN=C1 NBUOOLFOHRYQNL-IOWSJCHKSA-N 0.000 claims 2
- KUPKLNUHJXRSMI-IOWSJCHKSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]pyridine-4-carboxamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=CC=NC=C1 KUPKLNUHJXRSMI-IOWSJCHKSA-N 0.000 claims 2
- GCFLQXXLUPHFNT-XZWHSSHBSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-1-oxo-3-phenylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]thiophene-3-carboxamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=CSC=C1 GCFLQXXLUPHFNT-XZWHSSHBSA-N 0.000 claims 2
- KGASRYBCGZUNAS-ZWXJPIIXSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-1-oxo-3-pyridin-2-ylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]-4-methoxybenzamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1N=CC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=CC=C(OC)C=C1 KGASRYBCGZUNAS-ZWXJPIIXSA-N 0.000 claims 2
- BHVUGAWTPFXTSW-JSOSNVBQSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-1-oxo-3-pyridin-2-ylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]benzamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1N=CC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=CC=CC=C1 BHVUGAWTPFXTSW-JSOSNVBQSA-N 0.000 claims 2
- YYYMEQVUGUUKPY-WUFINQPMSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-1-oxo-3-pyridin-3-ylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]-3-chlorothiophene-2-carboxamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=NC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=C(Cl)C=CS1 YYYMEQVUGUUKPY-WUFINQPMSA-N 0.000 claims 2
- AJYZUIMBRBUFPQ-AJQTZOPKSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-1-oxo-3-pyridin-3-ylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]-4-methoxybenzamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=NC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=CC=C(OC)C=C1 AJYZUIMBRBUFPQ-AJQTZOPKSA-N 0.000 claims 2
- QLQUHMZRFARDGM-AJQTZOPKSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-1-oxo-3-pyridin-3-ylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]-4-methylbenzamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=NC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=CC=C(C)C=C1 QLQUHMZRFARDGM-AJQTZOPKSA-N 0.000 claims 2
- IBCRPNPROJRPGD-IHLOFXLRSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-1-oxo-3-thiophen-2-ylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]benzamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1SC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=CC=CC=C1 IBCRPNPROJRPGD-IHLOFXLRSA-N 0.000 claims 2
- OVUYMWPCQQBURI-AJQTZOPKSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-3-(4-fluorophenyl)-1-oxopropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]benzamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=CC(F)=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=CC=CC=C1 OVUYMWPCQQBURI-AJQTZOPKSA-N 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- QGLIUKRHFCPRGS-WDYNHAJCSA-N (2r)-n-[(2s)-1-[[4-(aminomethyl)-3-fluorophenyl]methylamino]-1-oxo-3-phenylpropan-2-yl]-3-(4-ethoxyphenyl)-n-methyl-2-(propanoylamino)propanamide Chemical compound C1=CC(OCC)=CC=C1C[C@@H](NC(=O)CC)C(=O)N(C)[C@H](C(=O)NCC=1C=C(F)C(CN)=CC=1)CC1=CC=CC=C1 QGLIUKRHFCPRGS-WDYNHAJCSA-N 0.000 claims 1
- YPOGXTFVOIPEHL-WDYNHAJCSA-N (2r)-n-[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-1-oxo-3-phenylpropan-2-yl]-3-(4-ethoxyphenyl)-n-methyl-2-(propanoylamino)propanamide Chemical compound C1=CC(OCC)=CC=C1C[C@@H](NC(=O)CC)C(=O)N(C)[C@H](C(=O)NCC=1C=CC(CN)=CC=1)CC1=CC=CC=C1 YPOGXTFVOIPEHL-WDYNHAJCSA-N 0.000 claims 1
- CNHNTLTXVFZCRI-WUFINQPMSA-N (2r)-n-[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-3-(3,4-dichlorophenyl)-1-oxopropan-2-yl]-3-(4-ethoxyphenyl)-2-(propanoylamino)propanamide Chemical compound C1=CC(OCC)=CC=C1C[C@@H](NC(=O)CC)C(=O)N[C@H](C(=O)NCC=1C=CC(CN)=CC=1)CC1=CC=C(Cl)C(Cl)=C1 CNHNTLTXVFZCRI-WUFINQPMSA-N 0.000 claims 1
- KNHURXIHYWTCFE-OIDHKYIRSA-N (2s)-2-[[(2r)-2-[acetyl-[(2-phenylacetyl)amino]amino]-3-(4-ethoxyphenyl)propanoyl]amino]-n-[[4-(aminomethyl)phenyl]methyl]-3-phenylpropanamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)N(C(C)=O)NC(=O)CC1=CC=CC=C1 KNHURXIHYWTCFE-OIDHKYIRSA-N 0.000 claims 1
- BCVMEJPYJNFSMU-WUFINQPMSA-N (2s)-n-[[4-(aminomethyl)phenyl]methyl]-2-[[(2r)-3-(4-ethoxyphenyl)-2-(propanoylamino)propanoyl]amino]-3-phenylpropanamide Chemical compound C1=CC(OCC)=CC=C1C[C@@H](NC(=O)CC)C(=O)N[C@H](C(=O)NCC=1C=CC(CN)=CC=1)CC1=CC=CC=C1 BCVMEJPYJNFSMU-WUFINQPMSA-N 0.000 claims 1
- PHBWBJVPZUGFDM-ZNZIZOMTSA-N (2s,3s)-2-[[(2r)-2-amino-3-(4-ethoxyphenyl)propanoyl]amino]-n-[[4-(aminomethyl)phenyl]methyl]-3-hydroxy-3-phenylpropanamide Chemical compound C1=CC(OCC)=CC=C1C[C@@H](N)C(=O)N[C@H](C(=O)NCC=1C=CC(CN)=CC=1)[C@@H](O)C1=CC=CC=C1 PHBWBJVPZUGFDM-ZNZIZOMTSA-N 0.000 claims 1
- YXLKCGPSLDBIQH-FGUUHEIUSA-N (2s,3s)-n-[[4-(aminomethyl)phenyl]methyl]-2-[[(2r)-3-(4-ethoxyphenyl)-2-(propanoylamino)propanoyl]amino]-3-hydroxy-3-phenylpropanamide Chemical compound C1=CC(OCC)=CC=C1C[C@@H](NC(=O)CC)C(=O)N[C@H](C(=O)NCC=1C=CC(CN)=CC=1)[C@@H](O)C1=CC=CC=C1 YXLKCGPSLDBIQH-FGUUHEIUSA-N 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- DYSJMQABFPKAQM-UHFFFAOYSA-N 1-benzothiophene-2-carboxylic acid Chemical compound C1=CC=C2SC(C(=O)O)=CC2=C1 DYSJMQABFPKAQM-UHFFFAOYSA-N 0.000 claims 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
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- XRXPBLITZSRMPK-AJQTZOPKSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-3-(4-chlorophenyl)-1-oxopropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]benzamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=CC(Cl)=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=CC=CC=C1 XRXPBLITZSRMPK-AJQTZOPKSA-N 0.000 claims 1
- MNENVOCWAYYIHM-JHOUSYSJSA-N n-[(2r)-1-[[(2s)-1-[[4-(aminomethyl)phenyl]methylamino]-3-(4-methoxyphenyl)-1-oxopropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]benzamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H](CC=1C=CC(OC)=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=CC=CC=C1 MNENVOCWAYYIHM-JHOUSYSJSA-N 0.000 claims 1
- JPIQGCNQXOHJHE-SSBOKUKZSA-N n-[(2r)-1-[[(2s,3r)-1-[[4-(aminomethyl)phenyl]methylamino]-3-hydroxy-1-oxo-3-phenylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]-3-chlorothiophene-2-carboxamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H]([C@H](O)C=1C=CC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=C(Cl)C=CS1 JPIQGCNQXOHJHE-SSBOKUKZSA-N 0.000 claims 1
- BCBPQVFOASQXEY-YKILCQELSA-N n-[(2r)-1-[[(2s,3r)-1-[[4-(aminomethyl)phenyl]methylamino]-3-hydroxy-1-oxo-3-phenylpropan-2-yl]amino]-3-(4-ethoxyphenyl)-1-oxopropan-2-yl]benzamide Chemical compound C1=CC(OCC)=CC=C1C[C@H](C(=O)N[C@@H]([C@H](O)C=1C=CC=CC=1)C(=O)NCC=1C=CC(CN)=CC=1)NC(=O)C1=CC=CC=C1 BCBPQVFOASQXEY-YKILCQELSA-N 0.000 claims 1
- 201000001119 neuropathy Diseases 0.000 claims 1
- 230000007823 neuropathy Effects 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
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- 230000002265 prevention Effects 0.000 claims 1
- 230000002207 retinal effect Effects 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
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| PCT/GB2012/051588 WO2013005045A1 (en) | 2011-07-07 | 2012-07-06 | Benzylamine derivatives as inhibitors of plasma kallikrein |
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Families Citing this family (41)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUE040145T2 (hu) | 2011-10-26 | 2019-02-28 | Allergan Inc | N-karbamid szubsztituált aminosavak amid származékai mint formilpeptidszerû receptor 1 (FPRL1) receptormodulátorok |
| GB201212081D0 (en) * | 2012-07-06 | 2012-08-22 | Kalvista Pharmaceuticals Ltd | New polymorph |
| GB2510407A (en) | 2013-02-04 | 2014-08-06 | Kalvista Pharmaceuticals Ltd | Aqueous suspensions of kallikrein inhibitors for parenteral administration |
| 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 |
| ES2748434T3 (es) * | 2014-01-10 | 2020-03-16 | Univ Cornell | Dipéptidos como inhibidores de inmunoproteasomas humanos |
| US11202817B2 (en) | 2014-08-18 | 2021-12-21 | Cornell University | Dipeptidomimetics as inhibitors of human immunoproteasomes |
| GB201421083D0 (en) | 2014-11-27 | 2015-01-14 | Kalvista Pharmaceuticals Ltd | Enzyme inhibitors |
| GB201421085D0 (en) | 2014-11-27 | 2015-01-14 | Kalvista Pharmaceuticals Ltd | New enzyme inhibitors |
| EP4006012A1 (en) | 2015-10-15 | 2022-06-01 | Cornell University | Proteasome inhibitors and uses thereof |
| ME03794B (me) | 2016-05-31 | 2021-04-20 | 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 |
| GB201713660D0 (en) * | 2017-08-25 | 2017-10-11 | Kalvista Pharmaceuticals Ltd | Pharmaceutical compositions |
| WO2019075252A1 (en) | 2017-10-11 | 2019-04-18 | Cornell University | PEPTIDOMIMETIC INHIBITORS OF PROTEASOME |
| GB201719881D0 (en) | 2017-11-29 | 2018-01-10 | Kalvista Pharmaceuticals Ltd | Solid forms of plasma kallikrein inhibitor and salts thereof |
| PL3716952T3 (pl) | 2017-11-29 | 2022-05-02 | Kalvista Pharmaceuticals Limited | Postacie dawkowania zawierające inhibitor kalikreiny osoczowej |
| CN112135825A (zh) | 2018-03-13 | 2020-12-25 | 夏尔人类遗传性治疗公司 | 血浆激肽释放酶抑制剂及其用途 |
| CN111217670B (zh) * | 2018-11-25 | 2021-04-09 | 中国科学院大连化学物理研究所 | 一种催化还原化合物中羰基为亚甲基的方法 |
| CN113474318A (zh) * | 2019-04-22 | 2021-10-01 | 南京明德新药研发有限公司 | 用作血浆激肽释放酶抑制剂的双环烷类化合物 |
| 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 |
| WO2021032933A1 (en) * | 2019-08-21 | 2021-02-25 | Kalvista Pharmaceuticals Limited | Enzyme inhibitors |
| CN114728962B (zh) | 2019-09-18 | 2025-09-19 | 武田药品工业有限公司 | 血浆激肽释放酶抑制剂及其用途 |
| WO2021055589A1 (en) | 2019-09-18 | 2021-03-25 | Shire Human Genetic Therapies, Inc. | Heteroaryl plasma kallikrein inhibitors |
| GB201918994D0 (en) | 2019-12-20 | 2020-02-05 | Kalvista Pharmaceuticals Ltd | Treatments of diabetic macular edema and impaired visual acuity |
| GB2591730A (en) | 2019-12-09 | 2021-08-11 | Kalvista Pharmaceuticals Ltd | New polymorphs |
| 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 |
| WO2021198534A1 (en) | 2020-04-04 | 2021-10-07 | Oxurion NV | Plasma kallikrein inhibitors for use in the treatment of coronaviral disease |
| 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 |
| JP7787890B2 (ja) | 2020-11-19 | 2025-12-17 | 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 |
| 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 |
| WO2023144030A1 (en) | 2022-01-31 | 2023-08-03 | Oxurion NV | Plasma kallikrein inhibitor therapy for anti-vegf sensitization |
| WO2023148016A1 (en) | 2022-02-04 | 2023-08-10 | Oxurion NV | Biomarker for plasma kallikrein inhibitor therapy response |
| US20250281397A1 (en) | 2022-04-27 | 2025-09-11 | Kalvista Pharmaceuticals Limited | Formulations of a plasma kallikrein inhibitor |
| EP4673437A1 (en) | 2023-02-27 | 2026-01-07 | 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 (22)
| 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 |
| ZA951617B (en) * | 1994-03-04 | 1997-02-27 | Lilly Co Eli | Antithrombotic agents. |
| US5914319A (en) * | 1995-02-27 | 1999-06-22 | Eli Lilly And Company | Antithrombotic agents |
| WO1996031504A1 (en) * | 1995-04-04 | 1996-10-10 | Merck & Co., Inc. | Thrombin inhibitors |
| JP4179878B2 (ja) * | 2001-02-02 | 2008-11-12 | 中外製薬株式会社 | ペプチド誘導体 |
| GB0205527D0 (en) * | 2002-03-08 | 2002-04-24 | Ferring Bv | Inhibitors |
| DE10301300B4 (de) * | 2003-01-15 | 2009-07-16 | Curacyte Chemistry Gmbh | Verwendung von acylierten 4-Amidino- und 4-Guanidinobenzylaminen zur Inhibierung von Plasmakallikrein |
| NZ592039A (en) | 2003-08-27 | 2013-03-28 | Ophthotech Corp | Combination therapy for the treatment of ocular neovascular disorders |
| ES2365815T3 (es) * | 2005-12-14 | 2011-10-11 | Bristol-Myers Squibb Company | Análogos de arilpropionamida, arilacrilamida, arilpropinamida o arilmetilurea como inhibidores del factor xia. |
| EP2051707B1 (en) | 2006-07-31 | 2013-07-17 | Activesite Pharmaceuticals, Inc. | Inhibitors of plasma kallikrein |
| DE102006050672A1 (de) * | 2006-10-24 | 2008-04-30 | Curacyte Discovery Gmbh | Hemmstoffe des Plasmins und des Plasmakallikreins |
| KR20100037600A (ko) * | 2007-06-13 | 2010-04-09 | 브리스톨-마이어스 스큅 컴퍼니 | 응고 인자 억제제로서의 디펩티드 유사체 |
| CN102026996B (zh) | 2008-03-13 | 2015-01-07 | 百时美施贵宝公司 | 作为凝血因子xia抑制剂的哒嗪衍生物 |
| US8609866B2 (en) | 2009-12-18 | 2013-12-17 | Activesite Pharmaceuticals, Inc. | Prodrugs of inhibitors of plasma kallikrein |
| WO2011094496A2 (en) * | 2010-01-28 | 2011-08-04 | The Medicines Company | Trypsin-like serine protease inhibitors, and their preparation and use |
| JP2013121919A (ja) | 2010-03-25 | 2013-06-20 | Astellas Pharma Inc | 血漿カリクレイン阻害剤 |
| ES2483802T3 (es) | 2010-07-07 | 2014-08-07 | The Medicines Company (Leipzig) Gmbh | Inhibidores de serina proteasa |
| 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 |
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- 2012-07-06 KR KR1020147003202A patent/KR101999195B1/ko not_active Expired - Fee Related
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