JP2023040213A5 - - Google Patents
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- Publication number
- JP2023040213A5 JP2023040213A5 JP2023002547A JP2023002547A JP2023040213A5 JP 2023040213 A5 JP2023040213 A5 JP 2023040213A5 JP 2023002547 A JP2023002547 A JP 2023002547A JP 2023002547 A JP2023002547 A JP 2023002547A JP 2023040213 A5 JP2023040213 A5 JP 2023040213A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- amino
- substituted
- thiazole
- carboxamide
- 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 80
- 239000008194 pharmaceutical composition Substances 0.000 claims 22
- 125000001072 heteroaryl group Chemical group 0.000 claims 20
- 125000003118 aryl group Chemical group 0.000 claims 19
- 125000003342 alkenyl group Chemical group 0.000 claims 18
- 125000000304 alkynyl group Chemical group 0.000 claims 18
- 125000004452 carbocyclyl group Chemical group 0.000 claims 17
- 125000000623 heterocyclic group Chemical group 0.000 claims 17
- 125000004404 heteroalkyl group Chemical group 0.000 claims 12
- 125000005842 heteroatom Chemical group 0.000 claims 12
- 206010019860 Hereditary angioedema Diseases 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 150000001875 compounds Chemical class 0.000 claims 6
- 125000006714 (C3-C10) heterocyclyl group Chemical group 0.000 claims 5
- LLPPLVKHKYCFMU-IIDMSEBBSA-N CNC(=O)[C@@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 LLPPLVKHKYCFMU-IIDMSEBBSA-N 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- PQQRHWFRZHFGFM-UHFFFAOYSA-N 1,3-thiazole-4-carboxamide Chemical compound NC(=O)C1=CSC=N1 PQQRHWFRZHFGFM-UHFFFAOYSA-N 0.000 claims 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 4
- 125000002252 acyl group Chemical group 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 3
- 238000011282 treatment Methods 0.000 claims 3
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims 2
- BXOSIXVQJVFKRG-URVUXULASA-N C1=C(C=CC2=CC=CC=C12)C(=O)N1[C@@H](C[C@H](C1)N)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound C1=C(C=CC2=CC=CC=C12)C(=O)N1[C@@H](C[C@H](C1)N)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N BXOSIXVQJVFKRG-URVUXULASA-N 0.000 claims 2
- LSDUXDLFSXDPQA-UZLBHIALSA-N CC1=C(CCNC(=O)C2=CSC(=N2)[C@@H]2C[C@@H](N)CN2C(=O)C2=CN3C=C(Cl)C=CC3=N2)C(C)=NC(N)=C1 Chemical compound CC1=C(CCNC(=O)C2=CSC(=N2)[C@@H]2C[C@@H](N)CN2C(=O)C2=CN3C=C(Cl)C=CC3=N2)C(C)=NC(N)=C1 LSDUXDLFSXDPQA-UZLBHIALSA-N 0.000 claims 2
- BSTKXPMFPPOUDP-HXOBKFHXSA-N CC1=C(CNC(=O)C2=CSC(=N2)[C@@H]2C[C@@H](N)CN2C(=O)C2=CN3C=C(Cl)C=CC3=N2)C(C)=C2C=CN=C(N)C2=C1 Chemical compound CC1=C(CNC(=O)C2=CSC(=N2)[C@@H]2C[C@@H](N)CN2C(=O)C2=CN3C=C(Cl)C=CC3=N2)C(C)=C2C=CN=C(N)C2=C1 BSTKXPMFPPOUDP-HXOBKFHXSA-N 0.000 claims 2
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- BPUYBKGHVHAYKC-GJYPPUQNSA-N CN(C)C(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CN(C)C(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 BPUYBKGHVHAYKC-GJYPPUQNSA-N 0.000 claims 2
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- DCRZJWUVOAVWGB-MMOPVJDHSA-N CNC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 DCRZJWUVOAVWGB-MMOPVJDHSA-N 0.000 claims 2
- IAAFGUQPPVMZNX-MONBJTKQSA-N CNC(=O)[C@H](CC1=CNC2=CC=CC=C12)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@H](CC1=CNC2=CC=CC=C12)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 IAAFGUQPPVMZNX-MONBJTKQSA-N 0.000 claims 2
- YZUIZAHXHMYKIB-XUWXXGDYSA-N CNC(=O)[C@H](CC1=CNC=N1)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@H](CC1=CNC=N1)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 YZUIZAHXHMYKIB-XUWXXGDYSA-N 0.000 claims 2
- VCKGTIQQFDCCCA-WWGRRREGSA-N CNC(=O)[C@H](CCC(N)=O)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@H](CCC(N)=O)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 VCKGTIQQFDCCCA-WWGRRREGSA-N 0.000 claims 2
- IQKGPQDSABYVQE-VKJFTORMSA-N CNC(=O)[C@H](CCCCN)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@H](CCCCN)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 IQKGPQDSABYVQE-VKJFTORMSA-N 0.000 claims 2
- QREFANRJXDCKQV-UWVAXJGDSA-N CNC(=O)[C@H](CCCCNC(C)=O)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@H](CCCCNC(C)=O)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 QREFANRJXDCKQV-UWVAXJGDSA-N 0.000 claims 2
- KOVNKSCBSLWDLG-VKJFTORMSA-N CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(C=CC2=N1)C(F)(F)F Chemical compound CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(C=CC2=N1)C(F)(F)F KOVNKSCBSLWDLG-VKJFTORMSA-N 0.000 claims 2
- LLPPLVKHKYCFMU-VKJFTORMSA-N CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 LLPPLVKHKYCFMU-VKJFTORMSA-N 0.000 claims 2
- RIBQIUQETAVSCK-VKJFTORMSA-N CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(I)C=CC2=N1 Chemical compound CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(I)C=CC2=N1 RIBQIUQETAVSCK-VKJFTORMSA-N 0.000 claims 2
- HZBXWCRJRXMOSH-ALKREAHSSA-N CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(OC)C=CC2=N1 Chemical compound CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(OC)C=CC2=N1 HZBXWCRJRXMOSH-ALKREAHSSA-N 0.000 claims 2
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- ZMMPESRTVFDXKA-UWVAXJGDSA-N CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@H](CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1)NC(C)=O Chemical compound CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@H](CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1)NC(C)=O ZMMPESRTVFDXKA-UWVAXJGDSA-N 0.000 claims 2
- LLPPLVKHKYCFMU-MPGHIAIKSA-N CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@@H]1C[C@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 LLPPLVKHKYCFMU-MPGHIAIKSA-N 0.000 claims 2
- LLPPLVKHKYCFMU-RVKKMQEKSA-N CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@H]1C[C@@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 LLPPLVKHKYCFMU-RVKKMQEKSA-N 0.000 claims 2
- ZMMPESRTVFDXKA-FUHIMQAGSA-N CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@H]1C[C@H](CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1)NC(C)=O Chemical compound CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@H]1C[C@H](CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1)NC(C)=O ZMMPESRTVFDXKA-FUHIMQAGSA-N 0.000 claims 2
- LLPPLVKHKYCFMU-RLFYNMQTSA-N CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@H]1C[C@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 Chemical compound CNC(=O)[C@H](CCCCNC(N)=N)NC(=O)C1=CSC(=N1)[C@H]1C[C@H](N)CN1C(=O)C1=CN2C=C(Cl)C=CC2=N1 LLPPLVKHKYCFMU-RLFYNMQTSA-N 0.000 claims 2
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
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- CBXMSTBUKVKBJV-AOIWGVFYSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CC2=C(S1)C=C(C=C2)C)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CC2=C(S1)C=C(C=C2)C)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N CBXMSTBUKVKBJV-AOIWGVFYSA-N 0.000 claims 2
- UCKDBXMZROGZMA-RYRKJORJSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CC2=C(S1)C=C(C=C2)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CC2=C(S1)C=C(C=C2)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N UCKDBXMZROGZMA-RYRKJORJSA-N 0.000 claims 2
- OZQHKLQLDUISBY-RYRKJORJSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CC2=C(S1)C=CC(=C2)C(F)(F)F)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CC2=C(S1)C=CC(=C2)C(F)(F)F)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N OZQHKLQLDUISBY-RYRKJORJSA-N 0.000 claims 2
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- JZEDSUAQAVMEMU-RYRKJORJSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CC2=C(S1)C=CC(=C2)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CC2=C(S1)C=CC(=C2)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N JZEDSUAQAVMEMU-RYRKJORJSA-N 0.000 claims 2
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- FKQMDAAKAOWPEB-QRWLVFNGSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCC1=C2C=C(Cl)C=CN2C=N1 Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCC1=C2C=C(Cl)C=CN2C=N1 FKQMDAAKAOWPEB-QRWLVFNGSA-N 0.000 claims 2
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- ISBGVOZOKHEQDV-APWZRJJASA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCC1=CC=C(C=C1)C(N)=N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCC1=CC=C(C=C1)C(N)=N ISBGVOZOKHEQDV-APWZRJJASA-N 0.000 claims 2
- SYUKSGXOSHFNNI-UTKZUKDTSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCC1=CC=C2C(N)=NC=CC2=C1 Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCC1=CC=C2C(N)=NC=CC2=C1 SYUKSGXOSHFNNI-UTKZUKDTSA-N 0.000 claims 2
- GPNHMIMNKBPCPE-VLIAUNLRSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCC1=NNC2=C1C=C(Cl)C=C2 Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCC1=NNC2=C1C=C(Cl)C=C2 GPNHMIMNKBPCPE-VLIAUNLRSA-N 0.000 claims 2
- ZVVYLCGUZJCAEU-VLIAUNLRSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCC1=NNC2=C1C=CC(Cl)=C2 Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCC1=NNC2=C1C=CC(Cl)=C2 ZVVYLCGUZJCAEU-VLIAUNLRSA-N 0.000 claims 2
- GFDKMJFZUDZXRK-GCJKJVERSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCCC1=CC=C2C(N)=NC=CC2=C1 Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCCC1=CC=C2C(N)=NC=CC2=C1 GFDKMJFZUDZXRK-GCJKJVERSA-N 0.000 claims 2
- KBCPCNVORWUACK-PBHICJAKSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCCCCCNC(N)=N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)NCCCCCNC(N)=N KBCPCNVORWUACK-PBHICJAKSA-N 0.000 claims 2
- YGODCUSSYXRBRZ-KEYYUXOJSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)N[C@@H](CCCCNC(N)=N)C(N)=O Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=CN2C=C(Cl)C=CC2=N1)C1=NC(=CS1)C(=O)N[C@@H](CCCCNC(N)=N)C(N)=O YGODCUSSYXRBRZ-KEYYUXOJSA-N 0.000 claims 2
- GEJBSTPNTAGZPN-MMOPVJDHSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1=NC2=CC=C(C=C2C=C1)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N GEJBSTPNTAGZPN-MMOPVJDHSA-N 0.000 claims 2
- RAUVCEYTYCBNGN-RYRKJORJSA-N N[C@@H]1C[C@H](N(C1)C(=O)C1CCCCC1)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C1CCCCC1)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N RAUVCEYTYCBNGN-RYRKJORJSA-N 0.000 claims 2
- JBGMLHNBLWKMJG-LMNJBCLMSA-N N[C@@H]1C[C@H](N(C1)C(=O)C=1C=C2C=C(C=NC2=CC=1)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C=1C=C2C=C(C=NC2=CC=1)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N JBGMLHNBLWKMJG-LMNJBCLMSA-N 0.000 claims 2
- PBOYRHRFMVZNFR-KPFFTGBYSA-N N[C@@H]1C[C@H](N(C1)C(=O)C=1C=C2C=CC(=NC2=CC=1)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C=1C=C2C=CC(=NC2=CC=1)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N PBOYRHRFMVZNFR-KPFFTGBYSA-N 0.000 claims 2
- MBWBDEMKWGRUJD-LJHODMEESA-N N[C@@H]1C[C@H](N(C1)C(=O)C=1C=CC2=C(SC=C2Cl)C=1)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C=1C=CC2=C(SC=C2Cl)C=1)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N MBWBDEMKWGRUJD-LJHODMEESA-N 0.000 claims 2
- MLEJYXYWKYQGTH-LMNJBCLMSA-N N[C@@H]1C[C@H](N(C1)C(=O)C=1C=NC2=CC=C(C=C2C=1)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C=1C=NC2=CC=C(C=C2C=1)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N MLEJYXYWKYQGTH-LMNJBCLMSA-N 0.000 claims 2
- OMCCBPSINYKNOP-KEYYUXOJSA-N N[C@@H]1C[C@H](N(C1)C(=O)C=1N=C(N(C=1)C)C)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C=1N=C(N(C=1)C)C)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N OMCCBPSINYKNOP-KEYYUXOJSA-N 0.000 claims 2
- SSTSNQDAUDRZTD-KEYYUXOJSA-N N[C@@H]1C[C@H](N(C1)C(=O)C=1SC2=C(N=1)C=C(C=C2)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(=O)C=1SC2=C(N=1)C=C(C=C2)Cl)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N SSTSNQDAUDRZTD-KEYYUXOJSA-N 0.000 claims 2
- KSHXZRSWQOKILX-IPYPFGDCSA-N N[C@@H]1C[C@H](N(C1)C(C(C)C)=O)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(C(C)C)=O)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N KSHXZRSWQOKILX-IPYPFGDCSA-N 0.000 claims 2
- OCYCSLVKSPDLTL-RYRKJORJSA-N N[C@@H]1C[C@H](N(C1)C(C1=CC=CC=C1)=O)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N Chemical compound N[C@@H]1C[C@H](N(C1)C(C1=CC=CC=C1)=O)C=1SC=C(N=1)C(=O)N[C@H](C(=O)NC)CCCCNC(=N)N OCYCSLVKSPDLTL-RYRKJORJSA-N 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000005549 heteroarylene group Chemical group 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
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| JP2020505842A JP7210540B2 (ja) | 2017-08-04 | 2018-08-03 | 血漿カリクレインの阻害剤およびその使用 |
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| WO2019028362A1 (en) | 2017-08-04 | 2019-02-07 | Dyax Corp. | INHIBITORS OF PLASMATIC KALLIKREIN AND USES THEREOF |
| EP3765459A1 (en) | 2018-03-13 | 2021-01-20 | Shire Human Genetic Therapies, Inc. | Substituted imidazopyridines as inhibitors of plasma kallikrein and uses thereof |
| EP4031245A1 (en) | 2019-09-18 | 2022-07-27 | Takeda Pharmaceutical Company Limited | Heteroaryl plasma kallikrein inhibitors |
| DK4031547T3 (da) | 2019-09-18 | 2024-09-09 | Takeda Pharmaceuticals Co | Plasmakallikreininhibitorer og anvendelser deraf |
| EP4090427A1 (en) | 2020-01-13 | 2022-11-23 | Takeda Pharmaceutical Company Limited | Plasma kallikrein inhibitors and uses thereof for treating pediatric hereditary angioedema attack |
| WO2021198534A1 (en) | 2020-04-04 | 2021-10-07 | Oxurion NV | Plasma kallikrein inhibitors for use in the treatment of coronaviral disease |
| 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 |
| EP4587434A1 (en) * | 2022-09-15 | 2025-07-23 | Takeda Pharmaceutical Company Limited | N-((isoquinolin-6-yl)methyl)-1h-pyrazole-4-carboxamid derivatives as plasma kallikrein inhibitors for the treatment of hereditary angioedema |
| CN116063215A (zh) * | 2023-02-23 | 2023-05-05 | 南京安淮创新药物研究院有限公司 | 一种4-氨基-l-脯氨酸的合成方法 |
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| SK20052000A3 (sk) | 1998-06-30 | 2002-08-06 | Pfizer Products Inc. | Nepeptidové inhibítory VLA-4 dependentnej bunkovej väzby použiteľné pri liečení zápalových, autoimunitných a respiračných chorôb |
| UA96283C2 (uk) * | 2005-12-23 | 2011-10-25 | Зіланд Фарма А/С | Модифіковані міметики лізину |
| US20120009141A1 (en) * | 2008-08-07 | 2012-01-12 | Pharmascience Inc. | Functionalized pyrrolidines and use thereof as iap inhibitors |
| US9079880B2 (en) * | 2010-07-07 | 2015-07-14 | Boehringer Ingelheim International Gmbh | Rho kinase inhibitors |
| US20140378474A1 (en) | 2012-01-27 | 2014-12-25 | Novartis Ag | 5-membered heteroarylcarboxamide derivatives as plasma kallikrein inhibitors |
| JP6092261B2 (ja) * | 2012-02-24 | 2017-03-08 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | 抗ウイルス化合物 |
| GB201209138D0 (en) * | 2012-05-24 | 2012-07-04 | Ono Pharmaceutical Co | Compounds |
| JP6337750B2 (ja) * | 2013-11-22 | 2018-06-06 | 小野薬品工業株式会社 | 化合物 |
| RU2017131562A (ru) | 2015-02-27 | 2019-03-27 | Версеон Корпорейшн | Замещенные пиразольные соединения как ингибиторы сериновых протеаз |
| KR102607829B1 (ko) * | 2015-03-30 | 2023-12-01 | 다케다 파머수티컬 컴패니 리미티드 | 혈장 칼리크레인 저해제 및 유전성 혈관부종 발작을 예방하기 위한 이의 용도 |
| CA2991174A1 (en) * | 2015-07-01 | 2017-01-05 | Lifesci Pharmaceuticals, Inc. | Therapeutic inhibitory compounds |
| DK4019022T3 (en) * | 2015-10-01 | 2024-02-19 | Biocryst Pharm Inc | Human plasma kallikrein inhibitors |
| WO2019028362A1 (en) | 2017-08-04 | 2019-02-07 | Dyax Corp. | INHIBITORS OF PLASMATIC KALLIKREIN AND USES THEREOF |
| EP3765459A1 (en) * | 2018-03-13 | 2021-01-20 | Shire Human Genetic Therapies, Inc. | Substituted imidazopyridines as inhibitors of plasma kallikrein and uses thereof |
| DK4031547T3 (da) * | 2019-09-18 | 2024-09-09 | Takeda Pharmaceuticals Co | Plasmakallikreininhibitorer og anvendelser deraf |
| EP4031245A1 (en) * | 2019-09-18 | 2022-07-27 | Takeda Pharmaceutical Company Limited | Heteroaryl plasma kallikrein inhibitors |
| EP4623913A3 (en) * | 2020-04-17 | 2025-12-24 | Takeda Pharmaceutical Company Limited | Forms and compositions of inhibitors of plasma kallikrein |
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2021
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2023
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2024
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2025
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