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
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- 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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| KR20200143376A (ko) * | 2018-03-13 | 2020-12-23 | 샤이어 휴먼 지네틱 테라피즈 인크. | 혈장 칼리크레인 억제제로서의 치환된 이미다조피리딘 및 이의 용도 |
| CN114667289B (zh) | 2019-09-18 | 2025-08-26 | 武田药品工业有限公司 | 杂芳基血浆激肽释放酶抑制剂 |
| EP4031547B1 (en) * | 2019-09-18 | 2024-07-17 | Takeda Pharmaceutical Company Limited | Plasma kallikrein inhibitors and uses thereof |
| US12528880B2 (en) | 2020-01-13 | 2026-01-20 | 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 |
| JP2025531207A (ja) * | 2022-09-15 | 2025-09-19 | 武田薬品工業株式会社 | 遺伝性血管性浮腫の処置のための血漿カリクレイン阻害剤としてのｎ－（（イソキノリン－６イル）メチル）－１ｈ－ピラゾール－４－カルボキサミド誘導体 |
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| US9079880B2 (en) * | 2010-07-07 | 2015-07-14 | Boehringer Ingelheim International Gmbh | Rho kinase inhibitors |
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| EP2817291A1 (en) * | 2012-02-24 | 2014-12-31 | F. Hoffmann-La Roche AG | Antiviral compounds |
| 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 |
| CN107405333A (zh) * | 2015-02-27 | 2017-11-28 | 维颂公司 | 作为丝氨酸蛋白酶抑制剂的被取代的吡唑化合物 |
| BR112017020864A2 (en) * | 2015-03-30 | 2018-07-10 | Dyax Corp. | plasma kallikrein inhibitors and their uses for the prevention of hereditary angioedema attack |
| WO2017001936A2 (en) | 2015-07-01 | 2017-01-05 | Lifesci Pharmaceuticals, Inc. | Therapeutic inhibitory compounds |
| MY198346A (en) * | 2015-10-01 | 2023-08-28 | Biocryst Pharm Inc | Human plasma kallikrein inhibitors |
| JP7210540B2 (ja) | 2017-08-04 | 2023-01-23 | 武田薬品工業株式会社 | 血漿カリクレインの阻害剤およびその使用 |
| KR20200143376A (ko) * | 2018-03-13 | 2020-12-23 | 샤이어 휴먼 지네틱 테라피즈 인크. | 혈장 칼리크레인 억제제로서의 치환된 이미다조피리딘 및 이의 용도 |
| EP4031547B1 (en) * | 2019-09-18 | 2024-07-17 | Takeda Pharmaceutical Company Limited | Plasma kallikrein inhibitors and uses thereof |
| CN114667289B (zh) * | 2019-09-18 | 2025-08-26 | 武田药品工业有限公司 | 杂芳基血浆激肽释放酶抑制剂 |
| PT4136091T (pt) * | 2020-04-17 | 2025-08-22 | Takeda Pharmaceuticals Co | Formas e composições de inibidores da calicreína plasmática |
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- 2018-08-03 AU AU2018311976A patent/AU2018311976B2/en active Active
- 2018-08-03 EP EP24203482.5A patent/EP4494698A3/en not_active Withdrawn
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- 2018-08-03 WO PCT/US2018/045183 patent/WO2019028362A1/en not_active Ceased
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2021
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2023
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- 2023-12-20 US US18/390,137 patent/US20240199602A1/en active Pending
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2024
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