JP2018507861A5 - - Google Patents
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- JP2018507861A5 JP2018507861A5 JP2017544878A JP2017544878A JP2018507861A5 JP 2018507861 A5 JP2018507861 A5 JP 2018507861A5 JP 2017544878 A JP2017544878 A JP 2017544878A JP 2017544878 A JP2017544878 A JP 2017544878A JP 2018507861 A5 JP2018507861 A5 JP 2018507861A5
- Authority
- JP
- Japan
- Prior art keywords
- optionally substituted
- pharmaceutically acceptable
- acceptable salt
- compound according
- alkyl
- 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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- 150000001875 compounds Chemical class 0.000 claims 42
- 150000003839 salts Chemical class 0.000 claims 41
- -1 nitro, amino Chemical group 0.000 claims 28
- 125000000217 alkyl group Chemical group 0.000 claims 24
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 8
- 150000001412 amines Chemical class 0.000 claims 8
- 125000003107 substituted aryl group Chemical group 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 108010050904 Interferons Proteins 0.000 claims 4
- 102000014150 Interferons Human genes 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical class C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 3
- 239000003443 antiviral agent Substances 0.000 claims 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 150000002460 imidazoles Chemical class 0.000 claims 3
- 229940079322 interferon Drugs 0.000 claims 3
- MTPVBMVUENFFLL-HXUWFJFHSA-N 1-(2-fluorophenyl)-3-[(3s)-2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-3-yl]urea Chemical compound FC1=CC=CC=C1NC(=O)N[C@@H]1C(=O)NC2=CC=CC=C2C(C=2C=CC=CC=2)=N1 MTPVBMVUENFFLL-HXUWFJFHSA-N 0.000 claims 2
- KSHJXDWYTZJUEI-UHFFFAOYSA-N 1-cyclopropyl-3-[[1-(4-hydroxybutyl)benzimidazol-2-yl]methyl]imidazo[4,5-c]pyridin-2-one Chemical compound N=1C2=CC=CC=C2N(CCCCO)C=1CN(C1=O)C2=CN=CC=C2N1C1CC1 KSHJXDWYTZJUEI-UHFFFAOYSA-N 0.000 claims 2
- RDQSNNMSDOHAPG-UHFFFAOYSA-N 2-[[2-[[1-(2-aminoethyl)piperidin-4-yl]amino]-4-methylbenzimidazol-1-yl]methyl]-6-methylpyridin-3-ol Chemical compound CC1=CC=C(O)C(CN2C3=CC=CC(C)=C3N=C2NC2CCN(CCN)CC2)=N1 RDQSNNMSDOHAPG-UHFFFAOYSA-N 0.000 claims 2
- NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 claims 2
- DKORMNNYNRPTBJ-UHFFFAOYSA-N 2-[[6-[[2-(3-hydroxypropyl)-5-methylanilino]methyl]-2-(3-morpholin-4-ylpropylamino)benzimidazol-1-yl]methyl]-6-methylpyridin-3-ol Chemical compound CC1=CC=C(CCCO)C(NCC=2C=C3N(CC=4C(=CC=C(C)N=4)O)C(NCCCN4CCOCC4)=NC3=CC=2)=C1 DKORMNNYNRPTBJ-UHFFFAOYSA-N 0.000 claims 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical class C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 claims 2
- 125000000847 cytosin-1-yl group Chemical group [*]N1C(=O)N=C(N([H])[H])C([H])=C1[H] 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- VHOGYURTWQBHIL-UHFFFAOYSA-N leflunomide Chemical compound O1N=CC(C(=O)NC=2C=CC(=CC=2)C(F)(F)F)=C1C VHOGYURTWQBHIL-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- RTGDFNSFWBGLEC-SYZQJQIISA-N mycophenolate mofetil Chemical compound COC1=C(C)C=2COC(=O)C=2C(O)=C1C\C=C(/C)CCC(=O)OCCN1CCOCC1 RTGDFNSFWBGLEC-SYZQJQIISA-N 0.000 claims 2
- HPNSFSBZBAHARI-RUDMXATFSA-N mycophenolic acid Chemical compound OC1=C(C\C=C(/C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-RUDMXATFSA-N 0.000 claims 2
- XESARGFCSKSFID-FLLFQEBCSA-N pirazofurin Chemical compound OC1=C(C(=O)N)NN=C1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 XESARGFCSKSFID-FLLFQEBCSA-N 0.000 claims 2
- 150000003230 pyrimidines Chemical class 0.000 claims 2
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims 2
- 229940124530 sulfonamide Drugs 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- NHKZSTHOYNWEEZ-AFCXAGJDSA-N taribavirin Chemical compound N1=C(C(=N)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NHKZSTHOYNWEEZ-AFCXAGJDSA-N 0.000 claims 2
- BSDIOOGSAAJMSR-JOCHJYFZSA-N (9br)-9b-(4-chlorophenyl)-1-(4-fluorobenzoyl)-2,3-dihydroimidazo[5,6]pyrrolo[1,2-a]pyridin-5-one Chemical compound C1=CC(F)=CC=C1C(=O)N1[C@@]2(C=3C=CC(Cl)=CC=3)C3=CN=CC=C3C(=O)N2CC1 BSDIOOGSAAJMSR-JOCHJYFZSA-N 0.000 claims 1
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- 108091032973 (ribonucleotides)n+m Proteins 0.000 claims 1
- 102000040650 (ribonucleotides)n+m Human genes 0.000 claims 1
- 150000005071 1,2,4-oxadiazoles Chemical class 0.000 claims 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical class C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 1
- ASILHPOFVOONEE-UHFFFAOYSA-N 1,4-bis(3-methylpyridin-4-yl)-1,4-diazepane Chemical compound CC1=CN=CC=C1N1CCN(C=2C(=CN=CC=2)C)CCC1 ASILHPOFVOONEE-UHFFFAOYSA-N 0.000 claims 1
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 1
- GVVIAZOBDFNZPB-UHFFFAOYSA-N 1h-1-benzazepine-2-carboxamide Chemical compound N1C(C(=O)N)=CC=CC2=CC=CC=C21 GVVIAZOBDFNZPB-UHFFFAOYSA-N 0.000 claims 1
- BLUJRJMLDHEMRX-UHFFFAOYSA-N 2-[[2-hydroxy-5-[(5-methyltetrazol-1-yl)iminomethyl]phenyl]-(4-hydroxyphenyl)methyl]-4-[(5-methyltetrazol-1-yl)iminomethyl]phenol Chemical compound Cc1nnnn1N=Cc1ccc(O)c(c1)C(c1ccc(O)cc1)c1cc(C=Nn2nnnc2C)ccc1O BLUJRJMLDHEMRX-UHFFFAOYSA-N 0.000 claims 1
- BLUJRJMLDHEMRX-BMNRKXRESA-N 2-[[2-hydroxy-5-[(E)-(5-methyltetrazol-1-yl)iminomethyl]phenyl]-(4-hydroxyphenyl)methyl]-4-[(E)-(5-methyltetrazol-1-yl)iminomethyl]phenol Chemical compound Cc1nnnn1\N=C\c2ccc(O)c(c2)C(c3ccc(O)cc3)c4cc(\C=N\n5nnnc5C)ccc4O BLUJRJMLDHEMRX-BMNRKXRESA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- LNZKOJMCKWERFO-UHFFFAOYSA-N 2H-thieno[2,3-d]azepine-2-carboxamide Chemical compound S1C(C=C2C1=CC=NC=C2)C(=O)N LNZKOJMCKWERFO-UHFFFAOYSA-N 0.000 claims 1
- AWSRKKBIPSQHOJ-IBCQBUCCSA-N 4-amino-1-[(2r,3r,4r,5r)-5-(chloromethyl)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](F)[C@H](O)[C@](CO)(CCl)O1 AWSRKKBIPSQHOJ-IBCQBUCCSA-N 0.000 claims 1
- OPRZZDKUMMSNLY-UHFFFAOYSA-N 4-amino-8-[3-[2-(3,4-dimethoxyphenyl)ethylamino]propyl]-6,6-dimethyl-2-(4-methyl-3-nitrophenyl)-3h-imidazo[4,5-h]isoquinoline-7,9-dione Chemical compound C1=C(OC)C(OC)=CC=C1CCNCCCN1C(=O)C(C)(C)C(C=C(N)C2=C3NC(=N2)C=2C=C(C(C)=CC=2)[N+]([O-])=O)=C3C1=O OPRZZDKUMMSNLY-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 1
- 229940127513 Fusion Protein Inhibitors Drugs 0.000 claims 1
- 108091006027 G proteins Proteins 0.000 claims 1
- 102000030782 GTP binding Human genes 0.000 claims 1
- 108091000058 GTP-Binding Proteins 0.000 claims 1
- 101000777301 Homo sapiens Uteroglobin Proteins 0.000 claims 1
- 241000711920 Human orthopneumovirus Species 0.000 claims 1
- 108060003951 Immunoglobulin Proteins 0.000 claims 1
- 101710200424 Inosine-5'-monophosphate dehydrogenase Proteins 0.000 claims 1
- 101710141454 Nucleoprotein Proteins 0.000 claims 1
- YDITYPFXLDVVDY-UHFFFAOYSA-N O=C(NC1CC1)C1=CC2=C(C1)c1ccccc1N(CC2)C(=O)c1ccc(NC(=O)c2ccccc2N2CCCC2)cc1 Chemical compound O=C(NC1CC1)C1=CC2=C(C1)c1ccccc1N(CC2)C(=O)c1ccc(NC(=O)c2ccccc2N2CCCC2)cc1 YDITYPFXLDVVDY-UHFFFAOYSA-N 0.000 claims 1
- 108091034117 Oligonucleotide Proteins 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- XESARGFCSKSFID-UHFFFAOYSA-N Pyrazofurin Natural products OC1=C(C(=O)N)NN=C1C1C(O)C(O)C(CO)O1 XESARGFCSKSFID-UHFFFAOYSA-N 0.000 claims 1
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims 1
- 239000007983 Tris buffer Substances 0.000 claims 1
- QONDPVAVQJCAQR-UHFFFAOYSA-N [difluoromethoxy(trifluoromethoxy)methyl]-methylcyanamide Chemical compound FC(OC(N(C)C#N)OC(F)(F)F)F QONDPVAVQJCAQR-UHFFFAOYSA-N 0.000 claims 1
- WUMYBFXWUJTWTB-UHFFFAOYSA-N [hydroxy(methoxy)phosphoryl] phosphono hydrogen phosphate Chemical compound COP(O)(=O)OP(O)(=O)OP(O)(O)=O WUMYBFXWUJTWTB-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- YUCHAYRHHXJNQK-UHFFFAOYSA-N amitivir Chemical compound N#CNC1=NN=CS1 YUCHAYRHHXJNQK-UHFFFAOYSA-N 0.000 claims 1
- 150000001556 benzimidazoles Chemical class 0.000 claims 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004093 cyano group Chemical group *C#N 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 150000002240 furans Chemical class 0.000 claims 1
- 229940125777 fusion inhibitor Drugs 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 102000055576 human SCGB1A1 Human genes 0.000 claims 1
- 150000005238 imidazo[1,2-a]pyrimidines Chemical class 0.000 claims 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims 1
- 102000018358 immunoglobulin Human genes 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
- 208000015181 infectious disease Diseases 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 229940047124 interferons Drugs 0.000 claims 1
- 150000002545 isoxazoles Chemical class 0.000 claims 1
- 229960000681 leflunomide Drugs 0.000 claims 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims 1
- HPNSFSBZBAHARI-UHFFFAOYSA-N micophenolic acid Natural products OC1=C(CC=C(C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-UHFFFAOYSA-N 0.000 claims 1
- 125000002950 monocyclic group Chemical group 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 229960001521 motavizumab Drugs 0.000 claims 1
- 229960004866 mycophenolate mofetil Drugs 0.000 claims 1
- 229960000951 mycophenolic acid Drugs 0.000 claims 1
- GOFXWTVKPWJNGD-UWJYYQICSA-N n-[2-[(2s)-2-[5-[(3s)-3-aminopyrrolidin-1-yl]-6-methylpyrazolo[1,5-a]pyrimidin-2-yl]piperidine-1-carbonyl]-4-chlorophenyl]methanesulfonamide Chemical compound CC1=CN2N=C([C@H]3N(CCCC3)C(=O)C=3C(=CC=C(Cl)C=3)NS(C)(=O)=O)C=C2N=C1N1CC[C@H](N)C1 GOFXWTVKPWJNGD-UWJYYQICSA-N 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 150000002916 oxazoles Chemical class 0.000 claims 1
- ZYNBKQLXNWLQMM-UHFFFAOYSA-N oxolan-3-yl 2-methylpropanoate Chemical compound CC(C)C(=O)OC1CCOC1 ZYNBKQLXNWLQMM-UHFFFAOYSA-N 0.000 claims 1
- 229960000402 palivizumab Drugs 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical class O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 108090000765 processed proteins & peptides Proteins 0.000 claims 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 229940121649 protein inhibitor Drugs 0.000 claims 1
- 239000012268 protein inhibitor Substances 0.000 claims 1
- 150000003216 pyrazines Chemical class 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 150000003233 pyrroles Chemical class 0.000 claims 1
- 150000004040 pyrrolidinones Chemical class 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 150000007660 quinolones Chemical class 0.000 claims 1
- 230000010076 replication Effects 0.000 claims 1
- 229960000329 ribavirin Drugs 0.000 claims 1
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims 1
- PMAKDNHZVBVWFM-UHFFFAOYSA-N sodium;cyano(1,3,4-thiadiazol-2-yl)azanide Chemical compound [Na+].N#C[N-]C1=NN=CS1 PMAKDNHZVBVWFM-UHFFFAOYSA-N 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- 229950006081 taribavirin Drugs 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- 150000003557 thiazoles Chemical class 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 150000003577 thiophenes Chemical class 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- UNNCHYARSNZOPF-UHFFFAOYSA-L way-154641 Chemical compound [Na+].[Na+].NC(=O)CN(CC(N)=O)S(=O)(=O)C1=CC=CC(NC=2N=C(NC=3C=C(C(C=4C(=CC(NC=5N=C(NC=6C=C(C=CC=6)S(=O)(=O)N(CC(N)=O)CC(N)=O)N=C(NC=6C=C(C=CC=6)S(=O)(=O)N(CC(N)=O)CC(N)=O)N=5)=CC=4)S([O-])(=O)=O)=CC=3)S([O-])(=O)=O)N=C(NC=3C=C(C=CC=3)S(=O)(=O)N(CC(N)=O)CC(N)=O)N=2)=C1 UNNCHYARSNZOPF-UHFFFAOYSA-L 0.000 claims 1
- 0 C*C1CCNCC1 Chemical compound C*C1CCNCC1 0.000 description 3
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562120671P | 2015-02-25 | 2015-02-25 | |
| US62/120,671 | 2015-02-25 | ||
| US201562200483P | 2015-08-03 | 2015-08-03 | |
| US62/200,483 | 2015-08-03 | ||
| PCT/US2016/019393 WO2016138158A1 (en) | 2015-02-25 | 2016-02-24 | Antiviral compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018507861A JP2018507861A (ja) | 2018-03-22 |
| JP2018507861A5 true JP2018507861A5 (OSRAM) | 2019-04-25 |
| JP6716587B2 JP6716587B2 (ja) | 2020-07-01 |
Family
ID=56689780
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017544878A Expired - Fee Related JP6716587B2 (ja) | 2015-02-25 | 2016-02-24 | 抗ウイルス化合物 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US10358453B2 (OSRAM) |
| EP (1) | EP3262048A4 (OSRAM) |
| JP (1) | JP6716587B2 (OSRAM) |
| KR (2) | KR20210028752A (OSRAM) |
| CN (1) | CN107922427B (OSRAM) |
| AU (1) | AU2016222729B2 (OSRAM) |
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2016
- 2016-02-23 MA MA041614A patent/MA41614A/fr unknown
- 2016-02-24 AU AU2016222729A patent/AU2016222729B2/en not_active Ceased
- 2016-02-24 MX MX2017010933A patent/MX385571B/es unknown
- 2016-02-24 JP JP2017544878A patent/JP6716587B2/ja not_active Expired - Fee Related
- 2016-02-24 KR KR1020217006854A patent/KR20210028752A/ko not_active Ceased
- 2016-02-24 UA UAA201709269A patent/UA123393C2/uk unknown
- 2016-02-24 EA EA201791886A patent/EA038732B1/ru unknown
- 2016-02-24 US US15/052,631 patent/US10358453B2/en active Active
- 2016-02-24 CA CA2977150A patent/CA2977150A1/en active Pending
- 2016-02-24 EP EP16756295.8A patent/EP3262048A4/en not_active Withdrawn
- 2016-02-24 BR BR112017018022-7A patent/BR112017018022A2/pt not_active IP Right Cessation
- 2016-02-24 KR KR1020177026450A patent/KR20170122775A/ko not_active Withdrawn
- 2016-02-24 CN CN201680024046.4A patent/CN107922427B/zh active Active
- 2016-02-24 WO PCT/US2016/019393 patent/WO2016138158A1/en not_active Ceased
- 2016-02-25 TW TW105105765A patent/TWI704135B/zh not_active IP Right Cessation
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2017
- 2017-08-15 IL IL254011A patent/IL254011B/en unknown
- 2017-08-24 PH PH12017501534A patent/PH12017501534A1/en unknown
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