EA037868B1 - 2'-замещенные-n6-замещенные пуриновые нуклеотиды для лечения вызванных рнк-вирусом заболеваний - Google Patents

Info

Publication number

EA037868B1

EA037868B1 EA201990628A EA201990628A EA037868B1 EA 037868 B1 EA037868 B1 EA 037868B1 EA 201990628 A EA201990628 A EA 201990628A EA 201990628 A EA201990628 A EA 201990628A EA 037868 B1 EA037868 B1 EA 037868B1

Authority

EA

Eurasian Patent Office

Prior art keywords

formula

hydrogen

virus

compound

methyl

Prior art date

2016-09-07

Links

• Espacenet
• Global Dossier
• Discuss

• 241000700605 Viruses Species 0.000 title claims abstract description 168
• 238000011282 treatment Methods 0.000 title claims abstract description 108
• 239000002213 purine nucleotide Substances 0.000 title description 19
• 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 381
• 150000003839 salts Chemical class 0.000 claims abstract description 130
• 208000001490 Dengue Diseases 0.000 claims abstract description 11
• 206010012310 Dengue fever Diseases 0.000 claims abstract description 11
• 208000025729 dengue disease Diseases 0.000 claims abstract description 11
• 208000003152 Yellow Fever Diseases 0.000 claims abstract description 10
• 241000907316 Zika virus Species 0.000 claims abstract description 8
• 206010014596 Encephalitis Japanese B Diseases 0.000 claims abstract description 5
• 201000005807 Japanese encephalitis Diseases 0.000 claims abstract description 5
• 241000710842 Japanese encephalitis virus Species 0.000 claims abstract description 4
• 201000006449 West Nile encephalitis Diseases 0.000 claims abstract description 4
• 206010057293 West Nile viral infection Diseases 0.000 claims abstract description 4
• 229910052739 hydrogen Inorganic materials 0.000 claims description 413
• 239000001257 hydrogen Substances 0.000 claims description 404
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 220
• 150000002431 hydrogen Chemical class 0.000 claims description 182
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 168
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 115
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 96
• 125000000217 alkyl group Chemical group 0.000 claims description 87
• PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 claims description 80
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 78
• 125000003118 aryl group Chemical group 0.000 claims description 68
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 56
• 241000710815 Dengue virus 2 Species 0.000 claims description 16
• 241000710831 Flavivirus Species 0.000 claims description 11
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 10
• 125000001624 naphthyl group Chemical group 0.000 claims description 9
• 241000725619 Dengue virus Species 0.000 claims description 7
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 3
• 241000710872 Dengue virus 3 Species 0.000 claims description 3
• OIIOPWHTJZYKIL-PMACEKPBSA-N (5S)-5-[[[5-[2-chloro-3-[2-chloro-3-[6-methoxy-5-[[[(2S)-5-oxopyrrolidin-2-yl]methylamino]methyl]pyrazin-2-yl]phenyl]phenyl]-3-methoxypyrazin-2-yl]methylamino]methyl]pyrrolidin-2-one Chemical compound C1(=C(N=C(C2=C(C(C3=CC=CC(=C3Cl)C3=NC(OC)=C(N=C3)CNC[C@H]3NC(=O)CC3)=CC=C2)Cl)C=N1)OC)CNC[C@H]1NC(=O)CC1 OIIOPWHTJZYKIL-PMACEKPBSA-N 0.000 claims 1
• 241000710781 Flaviviridae Species 0.000 abstract description 9
• -1 nucleoside compounds Chemical class 0.000 description 144
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 140
• 208000009341 RNA Virus Infections Diseases 0.000 description 111
• 241001493065 dsRNA viruses Species 0.000 description 104
• 239000000243 solution Substances 0.000 description 97
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 93
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 87
• 229940002612 prodrug Drugs 0.000 description 73
• 239000000651 prodrug Substances 0.000 description 73
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 71
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 68
• 125000001072 heteroaryl group Chemical group 0.000 description 59
• 239000011541 reaction mixture Substances 0.000 description 49
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 49
• 238000005481 NMR spectroscopy Methods 0.000 description 43
• 239000002777 nucleoside Substances 0.000 description 43
• 235000019439 ethyl acetate Nutrition 0.000 description 42
• PTMHPRAIXMAOOB-UHFFFAOYSA-N phosphoramidic acid Chemical compound NP(O)(O)=O PTMHPRAIXMAOOB-UHFFFAOYSA-N 0.000 description 42
• 238000000034 method Methods 0.000 description 41
• 239000000203 mixture Substances 0.000 description 41
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 40
• 238000004440 column chromatography Methods 0.000 description 38
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 34
• 239000007787 solid Substances 0.000 description 34
• 239000000741 silica gel Substances 0.000 description 33
• 229910002027 silica gel Inorganic materials 0.000 description 33
• 239000001226 triphosphate Substances 0.000 description 32
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 31
• 229920006395 saturated elastomer Polymers 0.000 description 31
• 108091032973 (ribonucleotides)n+m Proteins 0.000 description 30
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
• 239000000460 chlorine Substances 0.000 description 30
• 201000010099 disease Diseases 0.000 description 30
• 229910019142 PO4 Inorganic materials 0.000 description 29
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 29
• 235000021317 phosphate Nutrition 0.000 description 29
• 239000010452 phosphate Substances 0.000 description 28
• 235000011178 triphosphate Nutrition 0.000 description 28
• 125000000623 heterocyclic group Chemical group 0.000 description 27
• 239000011734 sodium Substances 0.000 description 27
• 125000000753 cycloalkyl group Chemical group 0.000 description 26
• 239000003814 drug Substances 0.000 description 26
• 208000015181 infectious disease Diseases 0.000 description 26
• UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 26
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 25
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 24
• 239000000047 product Substances 0.000 description 24
• 102000040650 (ribonucleotides)n+m Human genes 0.000 description 23
• 239000001177 diphosphate Substances 0.000 description 22
• XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 22
• 235000011180 diphosphates Nutrition 0.000 description 22
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 22
• 239000012071 phase Substances 0.000 description 22
• 108010081348 HRT1 protein Hairy Proteins 0.000 description 21
• 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 description 21
• JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 20
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
• 230000015572 biosynthetic process Effects 0.000 description 19
• 238000000132 electrospray ionisation Methods 0.000 description 19
• 229940024606 amino acid Drugs 0.000 description 18
• 235000001014 amino acid Nutrition 0.000 description 18
• 150000004712 monophosphates Chemical class 0.000 description 18
• 150000003833 nucleoside derivatives Chemical class 0.000 description 18
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 16
• XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 16
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 16
• 229940079593 drug Drugs 0.000 description 16
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 16
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
• 150000001413 amino acids Chemical class 0.000 description 15
• 239000012267 brine Substances 0.000 description 15
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 14
• 241000710772 Yellow fever virus Species 0.000 description 14
• 125000003342 alkenyl group Chemical group 0.000 description 14
• 239000003795 chemical substances by application Substances 0.000 description 14
• CQRPUKWAZPZXTO-UHFFFAOYSA-M magnesium;2-methylpropane;chloride Chemical compound [Mg+2].[Cl-].C[C-](C)C CQRPUKWAZPZXTO-UHFFFAOYSA-M 0.000 description 14
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 14
• 238000003786 synthesis reaction Methods 0.000 description 14
• 229940051021 yellow-fever virus Drugs 0.000 description 14
• 238000005160 1H NMR spectroscopy Methods 0.000 description 13
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 13
• 241000711557 Hepacivirus Species 0.000 description 13
• 125000003545 alkoxy group Chemical group 0.000 description 13
• 125000004432 carbon atom Chemical group C* 0.000 description 13
• 229910052805 deuterium Inorganic materials 0.000 description 13
• 239000002773 nucleotide Substances 0.000 description 13
• 230000002441 reversible effect Effects 0.000 description 13
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 12
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 12
• 125000000304 alkynyl group Chemical group 0.000 description 12
• 239000002585 base Substances 0.000 description 12
• 229910052794 bromium Inorganic materials 0.000 description 12
• 210000004027 cell Anatomy 0.000 description 12
• 229910052801 chlorine Inorganic materials 0.000 description 12
• 238000001727 in vivo Methods 0.000 description 12
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 12
• 229910052757 nitrogen Inorganic materials 0.000 description 12
• 125000003729 nucleotide group Chemical group 0.000 description 12
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 12
• KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 11
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 11
• 125000002252 acyl group Chemical group 0.000 description 11
• 229910052731 fluorine Inorganic materials 0.000 description 11
• VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 description 11
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 11
• 239000008194 pharmaceutical composition Substances 0.000 description 11
• 125000001424 substituent group Chemical group 0.000 description 11
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 10
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
• DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 10
• 241001465754 Metazoa Species 0.000 description 10
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 10
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
• UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 description 10
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 10
• 239000003937 drug carrier Substances 0.000 description 10
• 230000000694 effects Effects 0.000 description 10
• 150000002243 furanoses Chemical group 0.000 description 10
• 239000010410 layer Substances 0.000 description 10
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 10
• 229910052698 phosphorus Inorganic materials 0.000 description 10
• 241000114864 ssRNA viruses Species 0.000 description 10
• 125000003107 substituted aryl group Chemical group 0.000 description 10
• 230000009385 viral infection Effects 0.000 description 10
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 150000001412 amines Chemical class 0.000 description 9
• 235000019270 ammonium chloride Nutrition 0.000 description 9
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
• 150000008298 phosphoramidates Chemical class 0.000 description 9
• 239000011574 phosphorus Substances 0.000 description 9
• 125000004076 pyridyl group Chemical group 0.000 description 9
• 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 8
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 8
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
• 241000282412 Homo Species 0.000 description 8
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 8
• 125000003275 alpha amino acid group Chemical group 0.000 description 8
• 229910052799 carbon Inorganic materials 0.000 description 8
• 125000001188 haloalkyl group Chemical group 0.000 description 8
• 239000003112 inhibitor Substances 0.000 description 8
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 8
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 8
• RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 8
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 7
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 7
• 206010037660 Pyrexia Diseases 0.000 description 7
• 125000004122 cyclic group Chemical group 0.000 description 7
• 239000011737 fluorine Substances 0.000 description 7
• 238000009472 formulation Methods 0.000 description 7
• 229910052736 halogen Inorganic materials 0.000 description 7
• 150000002367 halogens Chemical class 0.000 description 7
• 125000004433 nitrogen atom Chemical group N* 0.000 description 7
• 239000003960 organic solvent Substances 0.000 description 7
• 229910052760 oxygen Inorganic materials 0.000 description 7
• 238000002360 preparation method Methods 0.000 description 7
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
• 239000007858 starting material Substances 0.000 description 7
• 238000003756 stirring Methods 0.000 description 7
• 238000006467 substitution reaction Methods 0.000 description 7
• 239000000725 suspension Substances 0.000 description 7
• RSPBCKKGNZLEJG-UHFFFAOYSA-N 6-methylpurine-2,6-diamine Chemical class CC1(N)N=C(N)N=C2N=CN=C12 RSPBCKKGNZLEJG-UHFFFAOYSA-N 0.000 description 6
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
• 239000000654 additive Substances 0.000 description 6
• 239000000969 carrier Substances 0.000 description 6
• CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 6
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 6
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 6
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
• 238000001990 intravenous administration Methods 0.000 description 6
• 230000004060 metabolic process Effects 0.000 description 6
• 239000012299 nitrogen atmosphere Substances 0.000 description 6
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 6
• CNNRPFQICPFDPO-UHFFFAOYSA-N octacosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCO CNNRPFQICPFDPO-UHFFFAOYSA-N 0.000 description 6
• 239000012074 organic phase Substances 0.000 description 6
• 125000006239 protecting group Chemical group 0.000 description 6
• 230000002829 reductive effect Effects 0.000 description 6
• REZQBEBOWJAQKS-UHFFFAOYSA-N triacontan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO REZQBEBOWJAQKS-UHFFFAOYSA-N 0.000 description 6
• 230000003612 virological effect Effects 0.000 description 6
• MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 5
• 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 5
• 239000004475 Arginine Substances 0.000 description 5
• DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 5
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 description 5
• 125000004649 C2-C8 alkynyl group Chemical group 0.000 description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
• 241000711573 Coronaviridae Species 0.000 description 5
• LEVWYRKDKASIDU-QWWZWVQMSA-N D-cystine Chemical compound OC(=O)[C@H](N)CSSC[C@@H](N)C(O)=O LEVWYRKDKASIDU-QWWZWVQMSA-N 0.000 description 5
• WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 5
• 239000004471 Glycine Substances 0.000 description 5
• UYTPUPDQBNUYGX-UHFFFAOYSA-N Guanine Natural products O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 5
• XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 5
• ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 5
• QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 5
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 5
• DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 5
• CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 5
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 5
• ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 5
• HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 5
• AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 5
• ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 5
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 5
• FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 5
• COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 5
• AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 5
• QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 5
• OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 5
• KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 5
• ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 5
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 5
• 239000004472 Lysine Substances 0.000 description 5
• ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 5
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
• MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 5
• AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 5
• 239000004473 Threonine Substances 0.000 description 5
• QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 5
• KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 5
• 235000004279 alanine Nutrition 0.000 description 5
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 5
• 239000000427 antigen Substances 0.000 description 5
• 108091007433 antigens Proteins 0.000 description 5
• 102000036639 antigens Human genes 0.000 description 5
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 5
• 235000009697 arginine Nutrition 0.000 description 5
• 235000009582 asparagine Nutrition 0.000 description 5
• 229960001230 asparagine Drugs 0.000 description 5
• 235000003704 aspartic acid Nutrition 0.000 description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
• 229940000635 beta-alanine Drugs 0.000 description 5
• OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 5
• 125000004093 cyano group Chemical group *C#N 0.000 description 5
• 235000018417 cysteine Nutrition 0.000 description 5
• XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 5
• 229960003067 cystine Drugs 0.000 description 5
• 206010014599 encephalitis Diseases 0.000 description 5
• 125000001153 fluoro group Chemical group F* 0.000 description 5
• 235000013922 glutamic acid Nutrition 0.000 description 5
• 239000004220 glutamic acid Substances 0.000 description 5
• ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 5
• HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 5
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
• AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 5
• 229960000310 isoleucine Drugs 0.000 description 5
• 230000000670 limiting effect Effects 0.000 description 5
• 229930182817 methionine Natural products 0.000 description 5
• COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 5
• 230000000069 prophylactic effect Effects 0.000 description 5
• 239000002212 purine nucleoside Substances 0.000 description 5
• 150000003212 purines Chemical class 0.000 description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
• 230000000405 serological effect Effects 0.000 description 5
• 239000002904 solvent Substances 0.000 description 5
• OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 5
• 239000004474 valine Substances 0.000 description 5
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 4
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
• RYYIULNRIVUMTQ-UHFFFAOYSA-N 6-chloroguanine Chemical compound NC1=NC(Cl)=C2N=CNC2=N1 RYYIULNRIVUMTQ-UHFFFAOYSA-N 0.000 description 4
• RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 4
• 241000283690 Bos taurus Species 0.000 description 4
• BGGALFIXXQOTPY-NRFANRHFSA-N C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC Chemical compound C1(=C(C2=C(C=C1)N(C(C#N)=C2)C[C@@H](N1CCN(CC1)S(=O)(=O)C)C)C)CN1CCC(CC1)NC1=NC(=NC2=C1C=C(S2)CC(F)(F)F)NC BGGALFIXXQOTPY-NRFANRHFSA-N 0.000 description 4
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
• 235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
• 241000150452 Orthohantavirus Species 0.000 description 4
• 241000150350 Peribunyaviridae Species 0.000 description 4
• 241000710778 Pestivirus Species 0.000 description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• 240000003768 Solanum lycopersicum Species 0.000 description 4
• 208000036142 Viral infection Diseases 0.000 description 4
• 230000000996 additive effect Effects 0.000 description 4
• 239000002671 adjuvant Substances 0.000 description 4
• 230000000840 anti-viral effect Effects 0.000 description 4
• 239000003443 antiviral agent Substances 0.000 description 4
• IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
• 239000002552 dosage form Substances 0.000 description 4
• 239000003480 eluent Substances 0.000 description 4
• 150000002191 fatty alcohols Chemical class 0.000 description 4
• MDQRDWAGHRLBPA-UHFFFAOYSA-N fluoroamine Chemical compound FN MDQRDWAGHRLBPA-UHFFFAOYSA-N 0.000 description 4
• 238000000338 in vitro Methods 0.000 description 4
• 230000000155 isotopic effect Effects 0.000 description 4
• 210000004185 liver Anatomy 0.000 description 4
• 238000004519 manufacturing process Methods 0.000 description 4
• 238000001819 mass spectrum Methods 0.000 description 4
• QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 4
• 230000004048 modification Effects 0.000 description 4
• 238000012986 modification Methods 0.000 description 4
• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
• 230000017074 necrotic cell death Effects 0.000 description 4
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
• 239000001301 oxygen Substances 0.000 description 4
• 230000036961 partial effect Effects 0.000 description 4
• 239000000843 powder Substances 0.000 description 4
• 230000002265 prevention Effects 0.000 description 4
• 229910052708 sodium Inorganic materials 0.000 description 4
• 229910052717 sulfur Inorganic materials 0.000 description 4
• 239000000829 suppository Substances 0.000 description 4
• 230000008685 targeting Effects 0.000 description 4
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
• 230000001225 therapeutic effect Effects 0.000 description 4
• FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 4
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
• PPDBOQMNKNNODG-NTEUORMPSA-N (5E)-5-(4-chlorobenzylidene)-2,2-dimethyl-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol Chemical compound C1=NC=NN1CC1(O)C(C)(C)CC\C1=C/C1=CC=C(Cl)C=C1 PPDBOQMNKNNODG-NTEUORMPSA-N 0.000 description 3
• ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 3
• JXNPEDYJTDQORS-HZJYTTRNSA-N (9Z,12Z)-octadecadien-1-ol Chemical compound CCCCC\C=C/C\C=C/CCCCCCCCO JXNPEDYJTDQORS-HZJYTTRNSA-N 0.000 description 3
• 229960002666 1-octacosanol Drugs 0.000 description 3
• XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 description 3
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
• 241000710929 Alphavirus Species 0.000 description 3
• 235000017060 Arachis glabrata Nutrition 0.000 description 3
• 244000105624 Arachis hypogaea Species 0.000 description 3
• 235000010777 Arachis hypogaea Nutrition 0.000 description 3
• 235000018262 Arachis monticola Nutrition 0.000 description 3
• 241000712892 Arenaviridae Species 0.000 description 3
• 241000711404 Avian avulavirus 1 Species 0.000 description 3
• 208000000307 Crimean Hemorrhagic Fever Diseases 0.000 description 3
• 201000003075 Crimean-Congo hemorrhagic fever Diseases 0.000 description 3
• 206010012735 Diarrhoea Diseases 0.000 description 3
• 241001493149 Gamboa virus Species 0.000 description 3
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
• 241000711513 Mononegavirales Species 0.000 description 3
• 241000439378 Nyamiviridae Species 0.000 description 3
• 241000922889 Ophioviridae Species 0.000 description 3
• 241000712464 Orthomyxoviridae Species 0.000 description 3
• 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 3
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
• 241000983876 Quadriviridae Species 0.000 description 3
• 241000702247 Reoviridae Species 0.000 description 3
• 241000725643 Respiratory syncytial virus Species 0.000 description 3
• 241000711931 Rhabdoviridae Species 0.000 description 3
• 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 description 3
• 201000003176 Severe Acute Respiratory Syndrome Diseases 0.000 description 3
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
• 241000710924 Togaviridae Species 0.000 description 3
• 241000710886 West Nile virus Species 0.000 description 3
• 238000003556 assay Methods 0.000 description 3
• 210000004369 blood Anatomy 0.000 description 3
• 239000008280 blood Substances 0.000 description 3
• 230000003833 cell viability Effects 0.000 description 3
• 238000006243 chemical reaction Methods 0.000 description 3
• 238000002648 combination therapy Methods 0.000 description 3
• 229940125898 compound 5 Drugs 0.000 description 3
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
• 230000000120 cytopathologic effect Effects 0.000 description 3
• 239000000706 filtrate Substances 0.000 description 3
• 239000012530 fluid Substances 0.000 description 3
• 238000007429 general method Methods 0.000 description 3
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
• 238000007918 intramuscular administration Methods 0.000 description 3
• 229910052740 iodine Inorganic materials 0.000 description 3
• 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
• 210000003734 kidney Anatomy 0.000 description 3
• JXNPEDYJTDQORS-UHFFFAOYSA-N linoleyl alcohol Natural products CCCCCC=CCC=CCCCCCCCCO JXNPEDYJTDQORS-UHFFFAOYSA-N 0.000 description 3
• 150000002632 lipids Chemical class 0.000 description 3
• 229910052744 lithium Inorganic materials 0.000 description 3
• 125000002950 monocyclic group Chemical group 0.000 description 3
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
• 229940055577 oleyl alcohol Drugs 0.000 description 3
• XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 3
• 239000006186 oral dosage form Substances 0.000 description 3
• 125000004430 oxygen atom Chemical group O* 0.000 description 3
• 235000020232 peanut Nutrition 0.000 description 3
• 239000000137 peptide hydrolase inhibitor Substances 0.000 description 3
• 150000003014 phosphoric acid esters Chemical class 0.000 description 3
• 150000003017 phosphorus Chemical class 0.000 description 3
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
• 238000012552 review Methods 0.000 description 3
• 229960000329 ribavirin Drugs 0.000 description 3
• 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 description 3
• 229910052938 sodium sulfate Inorganic materials 0.000 description 3
• 235000011152 sodium sulphate Nutrition 0.000 description 3
• 238000010561 standard procedure Methods 0.000 description 3
• 238000007920 subcutaneous administration Methods 0.000 description 3
• 239000000126 substance Substances 0.000 description 3
• 239000000758 substrate Substances 0.000 description 3
• 239000003826 tablet Substances 0.000 description 3
• 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
• 231100001274 therapeutic index Toxicity 0.000 description 3
• 238000002560 therapeutic procedure Methods 0.000 description 3
• 230000000699 topical effect Effects 0.000 description 3
• 229920002554 vinyl polymer Polymers 0.000 description 3
• GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
• QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
• FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
• 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 2
• JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical compound CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 description 2
• 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 2
• VKKXEIQIGGPMHT-UHFFFAOYSA-N 7h-purine-2,8-diamine Chemical group NC1=NC=C2NC(N)=NC2=N1 VKKXEIQIGGPMHT-UHFFFAOYSA-N 0.000 description 2
• UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
• MSSXOMSJDRHRMC-UHFFFAOYSA-N 9H-purine-2,6-diamine Chemical compound NC1=NC(N)=C2NC=NC2=N1 MSSXOMSJDRHRMC-UHFFFAOYSA-N 0.000 description 2
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
• GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 2
• 229930024421 Adenine Natural products 0.000 description 2
• 241000004176 Alphacoronavirus Species 0.000 description 2
• 241000961634 Alphaflexiviridae Species 0.000 description 2
• 241000520665 Alphatetraviridae Species 0.000 description 2
• 241000025051 Alvernaviridae Species 0.000 description 2
• 241000405487 Amalgaviridae Species 0.000 description 2
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
• 241000256186 Anopheles <genus> Species 0.000 description 2
• 241001493164 Anopheles A virus Species 0.000 description 2
• 241001493162 Anopheles B virus Species 0.000 description 2
• 241000710189 Aphthovirus Species 0.000 description 2
• 241000031976 Aquamavirus Species 0.000 description 2
• 241000233788 Arecaceae Species 0.000 description 2
• 206010003445 Ascites Diseases 0.000 description 2
• CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
• BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 2
• 241001533362 Astroviridae Species 0.000 description 2
• 241001651353 Avihepatovirus Species 0.000 description 2
• NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
• 241001533460 Barnaviridae Species 0.000 description 2
• 241000439483 Benyviridae Species 0.000 description 2
• 241000008904 Betacoronavirus Species 0.000 description 2
• 241000961645 Betaflexiviridae Species 0.000 description 2
• 241000702628 Birnaviridae Species 0.000 description 2
• 241000776207 Bornaviridae Species 0.000 description 2
• 208000014644 Brain disease Diseases 0.000 description 2
• 241001533462 Bromoviridae Species 0.000 description 2
• 241001493154 Bunyamwera virus Species 0.000 description 2
• 241000714198 Caliciviridae Species 0.000 description 2
• 201000009030 Carcinoma Diseases 0.000 description 2
• 241000710190 Cardiovirus Species 0.000 description 2
• 241000520666 Carmotetraviridae Species 0.000 description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• 241001060419 Chrysoviridae Species 0.000 description 2
• 244000241235 Citrullus lanatus Species 0.000 description 2
• 235000012828 Citrullus lanatus var citroides Nutrition 0.000 description 2
• 241000973027 Closteroviridae Species 0.000 description 2
• 206010010071 Coma Diseases 0.000 description 2
• 241001632249 Cosavirus Species 0.000 description 2
• 241000702221 Cystoviridae Species 0.000 description 2
• 241001461743 Deltacoronavirus Species 0.000 description 2
• 241000031978 Dicipivirus Species 0.000 description 2
• 241000615461 Dicistroviridae Species 0.000 description 2
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
• 241001115402 Ebolavirus Species 0.000 description 2
• 208000032274 Encephalopathy Diseases 0.000 description 2
• 241000868840 Endornaviridae Species 0.000 description 2
• 241000709661 Enterovirus Species 0.000 description 2
• 102000004190 Enzymes Human genes 0.000 description 2
• 108090000790 Enzymes Proteins 0.000 description 2
• 241001468007 Erbovirus Species 0.000 description 2
• 208000000624 Esophageal and Gastric Varices Diseases 0.000 description 2
• 208000010201 Exanthema Diseases 0.000 description 2
• 241000711950 Filoviridae Species 0.000 description 2
• 206010054261 Flavivirus infection Diseases 0.000 description 2
• 241000311863 Fusariviridae Species 0.000 description 2
• 241000008920 Gammacoronavirus Species 0.000 description 2
• 241000961639 Gammaflexiviridae Species 0.000 description 2
• 241000893570 Hendra henipavirus Species 0.000 description 2
• 241000709715 Hepatovirus Species 0.000 description 2
• 241001122120 Hepeviridae Species 0.000 description 2
• 241001533448 Hypoviridae Species 0.000 description 2
• 102000014150 Interferons Human genes 0.000 description 2
• 108010050904 Interferons Proteins 0.000 description 2
• 206010023126 Jaundice Diseases 0.000 description 2
• 241001468006 Kobuvirus Species 0.000 description 2
• 150000008575 L-amino acids Chemical class 0.000 description 2
• 241000712902 Lassa mammarenavirus Species 0.000 description 2
• 241000714210 Leviviridae Species 0.000 description 2
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
• 241000253097 Luteoviridae Species 0.000 description 2
• 208000000932 Marburg Virus Disease Diseases 0.000 description 2
• 208000030156 Marburg disease Diseases 0.000 description 2
• 201000011013 Marburg hemorrhagic fever Diseases 0.000 description 2
• 241001661687 Marnaviridae Species 0.000 description 2
• 241000712079 Measles morbillivirus Species 0.000 description 2
• 241000543395 Megabirnaviridae Species 0.000 description 2
• 241000031979 Megrivirus Species 0.000 description 2
• 241001009374 Mesoniviridae Species 0.000 description 2
• 241000711386 Mumps virus Species 0.000 description 2
• LIMFPAAAIVQRRD-BCGVJQADSA-N N-[2-[(3S,4R)-3-fluoro-4-methoxypiperidin-1-yl]pyrimidin-4-yl]-8-[(2R,3S)-2-methyl-3-(methylsulfonylmethyl)azetidin-1-yl]-5-propan-2-ylisoquinolin-3-amine Chemical compound F[C@H]1CN(CC[C@H]1OC)C1=NC=CC(=N1)NC=1N=CC2=C(C=CC(=C2C=1)C(C)C)N1[C@@H]([C@H](C1)CS(=O)(=O)C)C LIMFPAAAIVQRRD-BCGVJQADSA-N 0.000 description 2
• 241001112477 Narnaviridae Species 0.000 description 2
• 241001292005 Nidovirales Species 0.000 description 2
• 241000526636 Nipah henipavirus Species 0.000 description 2
• 241000723741 Nodaviridae Species 0.000 description 2
• 101800001014 Non-structural protein 5A Proteins 0.000 description 2
• 241000713112 Orthobunyavirus Species 0.000 description 2
• 241000150218 Orthonairovirus Species 0.000 description 2
• 241000712894 Orthotospovirus Species 0.000 description 2
• ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
• 241000282579 Pan Species 0.000 description 2
• 241000711504 Paramyxoviridae Species 0.000 description 2
• 241000991583 Parechovirus Species 0.000 description 2
• 241000710936 Partitiviridae Species 0.000 description 2
• 241000520712 Permutotetraviridae Species 0.000 description 2
• 208000004571 Pestivirus Infections Diseases 0.000 description 2
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
• 241000713137 Phlebovirus Species 0.000 description 2
• ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 2
• 241001627241 Picobirnaviridae Species 0.000 description 2
• 241001144416 Picornavirales Species 0.000 description 2
• 241000709664 Picornaviridae Species 0.000 description 2
• 208000005155 Picornaviridae Infections Diseases 0.000 description 2
• 229940123066 Polymerase inhibitor Drugs 0.000 description 2
• 241001533393 Potyviridae Species 0.000 description 2
• YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 2
• 241000720974 Protium Species 0.000 description 2
• 241000711798 Rabies lyssavirus Species 0.000 description 2
• 208000001647 Renal Insufficiency Diseases 0.000 description 2
• 241001534527 Roniviridae Species 0.000 description 2
• 241000710801 Rubivirus Species 0.000 description 2
• 241000315672 SARS coronavirus Species 0.000 description 2
• 241001352312 Salivirus Species 0.000 description 2
• 241000961587 Secoviridae Species 0.000 description 2
• 241001632234 Senecavirus Species 0.000 description 2
• 208000012936 Sheep disease Diseases 0.000 description 2
• 241001493158 Simbu orthobunyavirus Species 0.000 description 2
• 241000710960 Sindbis virus Species 0.000 description 2
• 206010041660 Splenomegaly Diseases 0.000 description 2
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
• 241000249096 Teschovirus Species 0.000 description 2
• 241001493143 Tete orthobunyavirus Species 0.000 description 2
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
• 241000723681 Tomato ringspot virus Species 0.000 description 2
• 241001533336 Tombusviridae Species 0.000 description 2
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
• YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 2
• 241000961632 Tymovirales Species 0.000 description 2
• 241001059845 Tymoviridae Species 0.000 description 2
• ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
• 206010056091 Varices oesophageal Diseases 0.000 description 2
• 241000710959 Venezuelan equine encephalitis virus Species 0.000 description 2
• 241000961586 Virgaviridae Species 0.000 description 2
• 241000710951 Western equine encephalitis virus Species 0.000 description 2
• 229940124928 YF-Vax Drugs 0.000 description 2
• 208000020329 Zika virus infectious disease Diseases 0.000 description 2
• 238000009825 accumulation Methods 0.000 description 2
• 229960001138 acetylsalicylic acid Drugs 0.000 description 2
• 239000002253 acid Substances 0.000 description 2
• DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
• 229960000643 adenine Drugs 0.000 description 2
• 230000029936 alkylation Effects 0.000 description 2
• 238000005804 alkylation reaction Methods 0.000 description 2
• 235000011114 ammonium hydroxide Nutrition 0.000 description 2
• 208000007502 anemia Diseases 0.000 description 2
• 150000001450 anions Chemical class 0.000 description 2
• 230000004596 appetite loss Effects 0.000 description 2
• 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
• 125000003710 aryl alkyl group Chemical group 0.000 description 2
• 125000004429 atom Chemical group 0.000 description 2
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 2
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 2
• 230000009286 beneficial effect Effects 0.000 description 2
• 230000008901 benefit Effects 0.000 description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
• 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 2
• 210000000601 blood cell Anatomy 0.000 description 2
• 230000023555 blood coagulation Effects 0.000 description 2
• 210000004204 blood vessel Anatomy 0.000 description 2
• 238000010504 bond cleavage reaction Methods 0.000 description 2
• 239000002775 capsule Substances 0.000 description 2
• 125000001309 chloro group Chemical group Cl* 0.000 description 2
• 238000011260 co-administration Methods 0.000 description 2
• 229940125773 compound 10 Drugs 0.000 description 2
• 229940125797 compound 12 Drugs 0.000 description 2
• 239000012043 crude product Substances 0.000 description 2
• 125000006165 cyclic alkyl group Chemical group 0.000 description 2
• OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 2
• 230000009615 deamination Effects 0.000 description 2
• 238000006481 deamination reaction Methods 0.000 description 2
• 230000003247 decreasing effect Effects 0.000 description 2
• NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 2
• TXFOLHZMICYNRM-UHFFFAOYSA-N dichlorophosphoryloxybenzene Chemical compound ClP(Cl)(=O)OC1=CC=CC=C1 TXFOLHZMICYNRM-UHFFFAOYSA-N 0.000 description 2
• 239000003085 diluting agent Substances 0.000 description 2
• 238000005516 engineering process Methods 0.000 description 2
• 208000024170 esophageal varices Diseases 0.000 description 2
• 201000010120 esophageal varix Diseases 0.000 description 2
• 150000002148 esters Chemical class 0.000 description 2
• 201000005884 exanthem Diseases 0.000 description 2
• 239000006260 foam Substances 0.000 description 2
• 125000002541 furyl group Chemical group 0.000 description 2
• 210000003494 hepatocyte Anatomy 0.000 description 2
• 125000005842 heteroatom Chemical group 0.000 description 2
• 208000006278 hypochromic anemia Diseases 0.000 description 2
• FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 description 2
• 238000011534 incubation Methods 0.000 description 2
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
• 229940079322 interferon Drugs 0.000 description 2
• 230000005445 isotope effect Effects 0.000 description 2
• ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
• 201000006370 kidney failure Diseases 0.000 description 2
• 239000007788 liquid Substances 0.000 description 2
• DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 2
• 235000021266 loss of appetite Nutrition 0.000 description 2
• 208000019017 loss of appetite Diseases 0.000 description 2
• 230000002503 metabolic effect Effects 0.000 description 2
• 230000037353 metabolic pathway Effects 0.000 description 2
• 229940095102 methyl benzoate Drugs 0.000 description 2
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 2
• 230000035772 mutation Effects 0.000 description 2
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• 230000001338 necrotic effect Effects 0.000 description 2
• 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
• 125000003835 nucleoside group Chemical group 0.000 description 2
• 229940046166 oligodeoxynucleotide Drugs 0.000 description 2
• 239000012044 organic layer Substances 0.000 description 2
• AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 2
• 229960005489 paracetamol Drugs 0.000 description 2
• 230000037361 pathway Effects 0.000 description 2
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
• RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
• UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 2
• 230000026731 phosphorylation Effects 0.000 description 2
• 238000006366 phosphorylation reaction Methods 0.000 description 2
• 208000007232 portal hypertension Diseases 0.000 description 2
• 229910052700 potassium Inorganic materials 0.000 description 2
• 230000002035 prolonged effect Effects 0.000 description 2
• QDQVXVRZVCTVHE-YFKPBYRVSA-N propan-2-yl (2s)-2-aminopropanoate Chemical compound CC(C)OC(=O)[C@H](C)N QDQVXVRZVCTVHE-YFKPBYRVSA-N 0.000 description 2
• 108090000623 proteins and genes Proteins 0.000 description 2
• 238000000746 purification Methods 0.000 description 2
• IGFXRKMLLMBKSA-UHFFFAOYSA-N purine Chemical compound N1=C[N]C2=NC=NC2=C1 IGFXRKMLLMBKSA-UHFFFAOYSA-N 0.000 description 2
• USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 2
• XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
• 206010037844 rash Diseases 0.000 description 2
• 230000001603 reducing effect Effects 0.000 description 2
• 238000010992 reflux Methods 0.000 description 2
• 125000006413 ring segment Chemical group 0.000 description 2
• 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
• 208000037921 secondary disease Diseases 0.000 description 2
• 235000017557 sodium bicarbonate Nutrition 0.000 description 2
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
• 239000011780 sodium chloride Substances 0.000 description 2
• 238000001228 spectrum Methods 0.000 description 2
• 238000010186 staining Methods 0.000 description 2
• 230000000707 stereoselective effect Effects 0.000 description 2
• 239000008223 sterile water Substances 0.000 description 2
• KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
• 239000011593 sulfur Chemical group 0.000 description 2
• 230000003319 supportive effect Effects 0.000 description 2
• 208000024891 symptom Diseases 0.000 description 2
• HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
• RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 2
• 229940124597 therapeutic agent Drugs 0.000 description 2
• XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 description 2
• 150000003573 thiols Chemical class 0.000 description 2
• 206010043554 thrombocytopenia Diseases 0.000 description 2
• RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 2
• 230000001988 toxicity Effects 0.000 description 2
• 231100000419 toxicity Toxicity 0.000 description 2
• 150000003852 triazoles Chemical class 0.000 description 2
• SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 description 2
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
• 125000002264 triphosphate group Chemical group [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 description 2
• 229910052722 tritium Inorganic materials 0.000 description 2
• 241000712461 unidentified influenza virus Species 0.000 description 2
• 229960005486 vaccine Drugs 0.000 description 2
• 230000004580 weight loss Effects 0.000 description 2
• RFUCJKFZFXNIGB-ZBBHRWOZSA-N (1s,2s,3s,4r)-3-[(1s)-1-acetamido-2-ethylbutyl]-4-(diaminomethylideneamino)-2-hydroxycyclopentane-1-carboxylic acid;trihydrate Chemical compound O.O.O.CCC(CC)[C@H](NC(C)=O)[C@@H]1[C@H](O)[C@@H](C(O)=O)C[C@H]1N=C(N)N RFUCJKFZFXNIGB-ZBBHRWOZSA-N 0.000 description 1
• KPARWUJDCIURDN-HUKYDQBMSA-N (2R,3R,4R,5R)-5-[2-amino-6-(dimethylamino)purin-9-yl]-4-fluoro-2-(hydroxymethyl)oxolan-3-ol Chemical compound NC1=NC(=C2N=CN(C2=N1)[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)F)N(C)C KPARWUJDCIURDN-HUKYDQBMSA-N 0.000 description 1
• GZLHGVFMWRCADY-QYYRPYCUSA-N (2r,3r,4r,5r)-5-[2-amino-6-(methylamino)purin-9-yl]-4-fluoro-2-(hydroxymethyl)oxolan-3-ol Chemical compound C1=NC=2C(NC)=NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1F GZLHGVFMWRCADY-QYYRPYCUSA-N 0.000 description 1
• TXWHPSZYRUHEGT-UUOKFMHZSA-N (2r,3r,4s,5r)-2-(2-amino-6-chloropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C12=NC(N)=NC(Cl)=C2N=CN1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O TXWHPSZYRUHEGT-UUOKFMHZSA-N 0.000 description 1
• OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
• 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 description 1
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 description 1
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 description 1
• WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
• FNQJDLTXOVEEFB-UHFFFAOYSA-N 1,2,3-benzothiadiazole Chemical compound C1=CC=C2SN=NC2=C1 FNQJDLTXOVEEFB-UHFFFAOYSA-N 0.000 description 1
• JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
• FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
• BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
• VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
• LDXLEVRZVMQDFN-UHFFFAOYSA-N 1,8-naphthyridine;quinoline Chemical compound N1=CC=CC2=CC=CC=C21.N1=CC=CC2=CC=CN=C21 LDXLEVRZVMQDFN-UHFFFAOYSA-N 0.000 description 1
• UBCHPRBFMUDMNC-UHFFFAOYSA-N 1-(1-adamantyl)ethanamine Chemical compound C1C(C2)CC3CC2CC1(C(N)C)C3 UBCHPRBFMUDMNC-UHFFFAOYSA-N 0.000 description 1
• 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
• WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
• TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
• BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
• AAQTWLBJPNLKHT-UHFFFAOYSA-N 1H-perimidine Chemical compound N1C=NC2=CC=CC3=CC=CC1=C32 AAQTWLBJPNLKHT-UHFFFAOYSA-N 0.000 description 1
• MGAXHFMCFLLMNG-UHFFFAOYSA-N 1h-pyrimidine-6-thione Chemical compound SC1=CC=NC=N1 MGAXHFMCFLLMNG-UHFFFAOYSA-N 0.000 description 1
• HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
• RMFWVOLULURGJI-UHFFFAOYSA-N 2,6-dichloro-7h-purine Chemical compound ClC1=NC(Cl)=C2NC=NC2=N1 RMFWVOLULURGJI-UHFFFAOYSA-N 0.000 description 1
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
• WJSVJNDMOQTICG-UHFFFAOYSA-N 2-amino-1-[(2-methyl-4-methylidene-5-oxooxolan-2-yl)methyl]-7h-purin-6-one Chemical compound NC1=NC=2N=CNC=2C(=O)N1CC1(C)CC(=C)C(=O)O1 WJSVJNDMOQTICG-UHFFFAOYSA-N 0.000 description 1
• ZKKBWNOSVZIFNJ-UHFFFAOYSA-N 2-amino-3,7-dihydropurin-6-one;diphosphono hydrogen phosphate Chemical class O=C1NC(N)=NC2=C1NC=N2.OP(O)(=O)OP(O)(=O)OP(O)(O)=O ZKKBWNOSVZIFNJ-UHFFFAOYSA-N 0.000 description 1
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
• MWBWWFOAEOYUST-UHFFFAOYSA-N 2-aminopurine Chemical group NC1=NC=C2N=CNC2=N1 MWBWWFOAEOYUST-UHFFFAOYSA-N 0.000 description 1
• UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 description 1
• 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
• 125000005916 2-methylpentyl group Chemical group 0.000 description 1
• DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 1
• KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 1
• 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
• LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
• VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
• MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 1
• WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 1
• 125000005917 3-methylpentyl group Chemical group 0.000 description 1
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
• GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 description 1
• CVVBPBHBMYSGCY-UHFFFAOYSA-N 4-chloropurin-2-amine Chemical compound C1=NC(N)=NC2(Cl)N=CN=C21 CVVBPBHBMYSGCY-UHFFFAOYSA-N 0.000 description 1
• CFBVWCHTNQHZLT-UHFFFAOYSA-N 4-methoxy-5-[3-(2-methoxy-4-nitro-5-sulfophenyl)-5-(phenylcarbamoyl)tetrazol-3-ium-2-yl]-2-nitrobenzenesulfonate Chemical compound COC1=CC([N+]([O-])=O)=C(S([O-])(=O)=O)C=C1N1[N+](C=2C(=CC(=C(C=2)S(O)(=O)=O)[N+]([O-])=O)OC)=NC(C(=O)NC=2C=CC=CC=2)=N1 CFBVWCHTNQHZLT-UHFFFAOYSA-N 0.000 description 1
• 101710169336 5'-deoxyadenosine deaminase Proteins 0.000 description 1
• SVXNJCYYMRMXNM-UHFFFAOYSA-N 5-amino-2h-1,2,4-triazin-3-one Chemical compound NC=1C=NNC(=O)N=1 SVXNJCYYMRMXNM-UHFFFAOYSA-N 0.000 description 1
• LRSASMSXMSNRBT-UHFFFAOYSA-N 5-methylcytosine Chemical compound CC1=CNC(=O)N=C1N LRSASMSXMSNRBT-UHFFFAOYSA-N 0.000 description 1
• NOYDQGFVFOQSAJ-UHFFFAOYSA-N 5-nitropyrimidine Chemical compound [O-][N+](=O)C1=CN=CN=C1 NOYDQGFVFOQSAJ-UHFFFAOYSA-N 0.000 description 1
• XZLIYCQRASOFQM-UHFFFAOYSA-N 5h-imidazo[4,5-d]triazine Chemical compound N1=NC=C2NC=NC2=N1 XZLIYCQRASOFQM-UHFFFAOYSA-N 0.000 description 1
• ZKBQDFAWXLTYKS-UHFFFAOYSA-N 6-Chloro-1H-purine Chemical compound ClC1=NC=NC2=C1NC=N2 ZKBQDFAWXLTYKS-UHFFFAOYSA-N 0.000 description 1
• DBCMWACNZJYUHS-UHFFFAOYSA-N 6-ethenyl-7h-purine Chemical compound C=CC1=NC=NC2=C1NC=N2 DBCMWACNZJYUHS-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
• 235000007173 Abies balsamea Nutrition 0.000 description 1
• 241000517645 Abra Species 0.000 description 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
• 239000005964 Acibenzolar-S-methyl Substances 0.000 description 1
• 102000055025 Adenosine deaminases Human genes 0.000 description 1
• 241000713131 Aino virus Species 0.000 description 1
• 241001222053 Akabane virus Species 0.000 description 1
• GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
• 241000436365 Anhembi virus Species 0.000 description 1
• 241000355660 Apeu virus Species 0.000 description 1
• 108091023037 Aptamer Proteins 0.000 description 1
• 208000035143 Bacterial infection Diseases 0.000 description 1
• 239000004857 Balsam Substances 0.000 description 1
• 241001600483 Batai virus Species 0.000 description 1
• 241000710076 Bean common mosaic virus Species 0.000 description 1
• 241001319696 Belmont virus Species 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
• 241000746290 Bimiti virus Species 0.000 description 1
• 241000436368 Birao virus Species 0.000 description 1
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
• 241000436478 Bozo virus Species 0.000 description 1
• 206010048962 Brain oedema Diseases 0.000 description 1
• 240000007124 Brassica oleracea Species 0.000 description 1
• 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
• 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
• 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
• 206010006242 Breast enlargement Diseases 0.000 description 1
• 206010006448 Bronchiolitis Diseases 0.000 description 1
• 241000026568 Buffalo Creek virus Species 0.000 description 1
• 241001493147 Bwamba orthobunyavirus Species 0.000 description 1
• RAXNXVAWPSEVRF-UHFFFAOYSA-N C1(=O)OCOP(O1)(=O)N Chemical class C1(=O)OCOP(O1)(=O)N RAXNXVAWPSEVRF-UHFFFAOYSA-N 0.000 description 1
• 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 description 1
• 241000706143 Cachoeira Porteira virus Species 0.000 description 1
• OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
• 241001493160 California encephalitis virus Species 0.000 description 1
• 241001493150 Capim virus Species 0.000 description 1
• 235000002566 Capsicum Nutrition 0.000 description 1
• 241001441409 Caraparu virus Species 0.000 description 1
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
• 102000053642 Catalytic RNA Human genes 0.000 description 1
• 108090000994 Catalytic RNA Proteins 0.000 description 1
• 208000037404 Central European encephalitis Diseases 0.000 description 1
• 241000375395 Chatanga virus Species 0.000 description 1
• 241001502567 Chikungunya virus Species 0.000 description 1
• 206010008631 Cholera Diseases 0.000 description 1
• 241000251730 Chondrichthyes Species 0.000 description 1
• 101150065749 Churc1 gene Proteins 0.000 description 1
• KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
• 206010010904 Convulsion Diseases 0.000 description 1
• 208000001528 Coronaviridae Infections Diseases 0.000 description 1
• 241001137251 Corvidae Species 0.000 description 1
• HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
• 102000018832 Cytochromes Human genes 0.000 description 1
• 108010052832 Cytochromes Proteins 0.000 description 1
• FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
• 150000008574 D-amino acids Chemical class 0.000 description 1
• 108020004414 DNA Proteins 0.000 description 1
• 241000450599 DNA viruses Species 0.000 description 1
• 208000005156 Dehydration Diseases 0.000 description 1
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
• 241000059498 Douglas virus Species 0.000 description 1
• 101100117236 Drosophila melanogaster speck gene Proteins 0.000 description 1
• 206010059866 Drug resistance Diseases 0.000 description 1
• 241000149824 Dugbe orthonairovirus Species 0.000 description 1
• 241000710945 Eastern equine encephalitis virus Species 0.000 description 1
• 241001589246 Enseada virus Species 0.000 description 1
• 206010066919 Epidemic polyarthritis Diseases 0.000 description 1
• 241000710803 Equine arteritis virus Species 0.000 description 1
• 241000283073 Equus caballus Species 0.000 description 1
• 241001315789 Eretmapodites Species 0.000 description 1
• 241000282326 Felis catus Species 0.000 description 1
• 241000436474 Fort Sherman virus Species 0.000 description 1
• 229940126656 GS-4224 Drugs 0.000 description 1
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
• 241000016006 Groundnut yellow spot orthotospovirus Species 0.000 description 1
• 241001600485 Guaroa virus Species 0.000 description 1
• 241000755301 Gumbo Limbo virus Species 0.000 description 1
• 241000150562 Hantaan orthohantavirus Species 0.000 description 1
• 229940121759 Helicase inhibitor Drugs 0.000 description 1
• 208000032843 Hemorrhage Diseases 0.000 description 1
• 208000005176 Hepatitis C Diseases 0.000 description 1
• 206010019851 Hepatotoxicity Diseases 0.000 description 1
• UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 description 1
• 241000436366 Iaco virus Species 0.000 description 1
• 241000436508 Ilesha virus Species 0.000 description 1
• 244000018716 Impatiens biflora Species 0.000 description 1
• 241000300119 Iquitos virus Species 0.000 description 1
• 241000866035 Iris yellow spot virus Species 0.000 description 1
• 241001494444 Jamestown Canyon virus Species 0.000 description 1
• 241001617355 Jatobal virus Species 0.000 description 1
• 241001481498 Jurona vesiculovirus Species 0.000 description 1
• 241001600488 Kairi virus Species 0.000 description 1
• 241001494421 Keystone virus Species 0.000 description 1
• 241001319704 Kowanyama virus Species 0.000 description 1
• 208000003140 Kyasanur forest disease Diseases 0.000 description 1
• 201000009908 La Crosse encephalitis Diseases 0.000 description 1
• 241000713102 La Crosse virus Species 0.000 description 1
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
• 241000870323 Leanyer virus Species 0.000 description 1
• 241001600482 Lumbo virus Species 0.000 description 1
• 241000701076 Macacine alphaherpesvirus 1 Species 0.000 description 1
• 241000436399 Macaua virus Species 0.000 description 1
• 241000372205 Madre de Dios virus Species 0.000 description 1
• 241000755303 Madrid virus Species 0.000 description 1
• 241001600489 Main Drain virus Species 0.000 description 1
• OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
• 229930195725 Mannitol Natural products 0.000 description 1
• 241001135631 Marituba virus Species 0.000 description 1
• 241000608292 Mayaro virus Species 0.000 description 1
• 201000005505 Measles Diseases 0.000 description 1
• 241001494418 Melao virus Species 0.000 description 1
• 241000030956 Melon yellow spot virus Species 0.000 description 1
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
• 108700011259 MicroRNAs Proteins 0.000 description 1
• 241001371381 Mirim virus Species 0.000 description 1
• 241000143320 Morro Bay virus Species 0.000 description 1
• 201000005805 Murray valley encephalitis Diseases 0.000 description 1
• 208000000112 Myalgia Diseases 0.000 description 1
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
• 229910002651 NO3 Inorganic materials 0.000 description 1
• 241000710765 Negishi virus Species 0.000 description 1
• 241000755161 Nepuyo virus Species 0.000 description 1
• 208000010359 Newcastle Disease Diseases 0.000 description 1
• 241000436367 Ngari virus Species 0.000 description 1
• NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
• 241000411132 Nola virus Species 0.000 description 1
• 241001600486 Northway virus Species 0.000 description 1
• 101710163270 Nuclease Proteins 0.000 description 1
• 241001493141 Nyando virus Species 0.000 description 1
• 241001428748 Ockelbo virus Species 0.000 description 1
• 239000005642 Oleic acid Substances 0.000 description 1
• ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
• 241000250439 Oropouche virus Species 0.000 description 1
• 241000755293 Ossa virus Species 0.000 description 1
• 208000002193 Pain Diseases 0.000 description 1
• 208000002606 Paramyxoviridae Infections Diseases 0.000 description 1
• 241001494479 Pecora Species 0.000 description 1
• 239000006002 Pepper Substances 0.000 description 1
• 108091000080 Phosphotransferase Proteins 0.000 description 1
• 235000016761 Piper aduncum Nutrition 0.000 description 1
• 235000017804 Piper guineense Nutrition 0.000 description 1
• 244000203593 Piper nigrum Species 0.000 description 1
• 235000008184 Piper nigrum Nutrition 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• 241000436422 Potosi virus Species 0.000 description 1
• 241000288906 Primates Species 0.000 description 1
• 102100038239 Protein Churchill Human genes 0.000 description 1
• 241000336513 Pueblo Viejo virus Species 0.000 description 1
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
• 241001521293 Python Species 0.000 description 1
• 101800001554 RNA-directed RNA polymerase Proteins 0.000 description 1
• 241000713124 Rift Valley fever virus Species 0.000 description 1
• 241000907520 Rio Bravo virus Species 0.000 description 1
• 241000710942 Ross River virus Species 0.000 description 1
• 241000425581 Salt ash virus Species 0.000 description 1
• 241000193690 San Angelo virus Species 0.000 description 1
• 241001333897 Sapelovirus Species 0.000 description 1
• 241000660220 Schmallenberg virus Species 0.000 description 1
• 241000710961 Semliki Forest virus Species 0.000 description 1
• 241000059514 Shuni orthobunyavirus Species 0.000 description 1
• BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
• 108020004459 Small interfering RNA Proteins 0.000 description 1
• 241000193685 South River virus Species 0.000 description 1
• 206010041896 St. Louis Encephalitis Diseases 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• 241000282887 Suidae Species 0.000 description 1
• 241000468870 Tahina Species 0.000 description 1
• 241000436397 Taiassui virus Species 0.000 description 1
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
• YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
• 208000004006 Tick-borne encephalitis Diseases 0.000 description 1
• 241001494427 Trivittatus virus Species 0.000 description 1
• 241000706160 Tucunduba virus Species 0.000 description 1
• 241001493078 Turlock orthobunyavirus Species 0.000 description 1
• 206010047700 Vomiting Diseases 0.000 description 1
• 208000001455 Zika Virus Infection Diseases 0.000 description 1
• 208000035332 Zika virus disease Diseases 0.000 description 1
• 241000015558 Zucchini lethal chlorosis orthotospovirus Species 0.000 description 1
• DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
• CGTWCAVZZBLHQH-UHFFFAOYSA-N [cyano-(3-phenoxyphenyl)methyl] 2,2-dichloro-1-(4-ethoxyphenyl)cyclopropane-1-carboxylate Chemical compound C1=CC(OCC)=CC=C1C1(C(=O)OC(C#N)C=2C=C(OC=3C=CC=CC=3)C=CC=2)C(Cl)(Cl)C1 CGTWCAVZZBLHQH-UHFFFAOYSA-N 0.000 description 1
• 210000001015 abdomen Anatomy 0.000 description 1
• 210000000683 abdominal cavity Anatomy 0.000 description 1
• 238000010521 absorption reaction Methods 0.000 description 1
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
• 150000007513 acids Chemical class 0.000 description 1
• 239000013543 active substance Substances 0.000 description 1
• 125000004442 acylamino group Chemical group 0.000 description 1
• 230000010933 acylation Effects 0.000 description 1
• 238000005917 acylation reaction Methods 0.000 description 1
• 239000000443 aerosol Substances 0.000 description 1
• 150000001298 alcohols Chemical class 0.000 description 1
• 229910052783 alkali metal Inorganic materials 0.000 description 1
• 150000001340 alkali metals Chemical class 0.000 description 1
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
• 150000001342 alkaline earth metals Chemical class 0.000 description 1
• 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
• 125000000266 alpha-aminoacyl group Chemical group 0.000 description 1
• DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
• 229960003805 amantadine Drugs 0.000 description 1
• 150000001408 amides Chemical class 0.000 description 1
• 125000000539 amino acid group Chemical group 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• 239000000908 ammonium hydroxide Substances 0.000 description 1
• 229940035676 analgesics Drugs 0.000 description 1
• 239000000730 antalgic agent Substances 0.000 description 1
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
• 239000003242 anti bacterial agent Substances 0.000 description 1
• 230000000692 anti-sense effect Effects 0.000 description 1
• 229940088710 antibiotic agent Drugs 0.000 description 1
• 230000005875 antibody response Effects 0.000 description 1
• 229940121357 antivirals Drugs 0.000 description 1
• 238000013459 approach Methods 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
• 229940072107 ascorbate Drugs 0.000 description 1
• 235000010323 ascorbic acid Nutrition 0.000 description 1
• 239000011668 ascorbic acid Substances 0.000 description 1
• CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical class N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
• 208000022362 bacterial infectious disease Diseases 0.000 description 1
• 150000007514 bases Chemical class 0.000 description 1
• RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
• 229940050390 benzoate Drugs 0.000 description 1
• WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
• 239000011230 binding agent Substances 0.000 description 1
• 239000012867 bioactive agent Substances 0.000 description 1
• 230000004071 biological effect Effects 0.000 description 1
• 230000000740 bleeding effect Effects 0.000 description 1
• 208000006752 brain edema Diseases 0.000 description 1
• 210000000481 breast Anatomy 0.000 description 1
• 125000001246 bromo group Chemical group Br* 0.000 description 1
• 244000309464 bull Species 0.000 description 1
• 239000011575 calcium Substances 0.000 description 1
• 229910052791 calcium Inorganic materials 0.000 description 1
• 125000004452 carbocyclyl group Chemical group 0.000 description 1
• 229910002091 carbon monoxide Inorganic materials 0.000 description 1
• 150000005323 carbonate salts Chemical class 0.000 description 1
• 150000001735 carboxylic acids Chemical class 0.000 description 1
• 230000015556 catabolic process Effects 0.000 description 1
• 238000004113 cell culture Methods 0.000 description 1
• 241000902900 cellular organisms Species 0.000 description 1
• 238000012512 characterization method Methods 0.000 description 1
• 238000002512 chemotherapy Methods 0.000 description 1
• DDYAZDRFUVZBMM-UHFFFAOYSA-N chloro-[chloro-di(propan-2-yl)silyl]oxy-di(propan-2-yl)silane Chemical compound CC(C)[Si](Cl)(C(C)C)O[Si](Cl)(C(C)C)C(C)C DDYAZDRFUVZBMM-UHFFFAOYSA-N 0.000 description 1
• WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
• 239000003086 colorant Substances 0.000 description 1
• 239000012230 colorless oil Substances 0.000 description 1
• 229940125904 compound 1 Drugs 0.000 description 1
• 229940126214 compound 3 Drugs 0.000 description 1
• 230000008878 coupling Effects 0.000 description 1
• 238000010168 coupling process Methods 0.000 description 1
• 238000005859 coupling reaction Methods 0.000 description 1
• 125000001485 cycloalkadienyl group Chemical group 0.000 description 1
• 125000000392 cycloalkenyl group Chemical group 0.000 description 1
• 229940104302 cytosine Drugs 0.000 description 1
• 238000006731 degradation reaction Methods 0.000 description 1
• 230000018044 dehydration Effects 0.000 description 1
• 238000006297 dehydration reaction Methods 0.000 description 1
• 238000013461 design Methods 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• 239000008121 dextrose Substances 0.000 description 1
• 235000014113 dietary fatty acids Nutrition 0.000 description 1
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
• XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
• IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
• 239000007884 disintegrant Substances 0.000 description 1
• 208000035475 disorder Diseases 0.000 description 1
• 239000006185 dispersion Substances 0.000 description 1
• 238000002651 drug therapy Methods 0.000 description 1
• 201000002491 encephalomyelitis Diseases 0.000 description 1
• 239000002702 enteric coating Substances 0.000 description 1
• 238000009505 enteric coating Methods 0.000 description 1
• 230000032050 esterification Effects 0.000 description 1
• 238000005886 esterification reaction Methods 0.000 description 1
• 235000019197 fats Nutrition 0.000 description 1
• 229930195729 fatty acid Natural products 0.000 description 1
• 239000000194 fatty acid Substances 0.000 description 1
• 150000004665 fatty acids Chemical class 0.000 description 1
• 230000002349 favourable effect Effects 0.000 description 1
• 230000012953 feeding on blood of other organism Effects 0.000 description 1
• JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
• 238000001914 filtration Methods 0.000 description 1
• 239000000796 flavoring agent Substances 0.000 description 1
• 235000019634 flavors Nutrition 0.000 description 1
• XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 description 1
• 229960004413 flucytosine Drugs 0.000 description 1
• 238000002637 fluid replacement therapy Methods 0.000 description 1
• 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 1
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
• 239000012634 fragment Substances 0.000 description 1
• 239000012458 free base Substances 0.000 description 1
• 125000000524 functional group Chemical group 0.000 description 1
• JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
• YRTCKZIKGWZNCU-UHFFFAOYSA-N furo[3,2-b]pyridine Chemical compound C1=CC=C2OC=CC2=N1 YRTCKZIKGWZNCU-UHFFFAOYSA-N 0.000 description 1
• JUQAECQBUNODQP-UHFFFAOYSA-N furo[3,2-d]pyrimidine Chemical compound C1=NC=C2OC=CC2=N1 JUQAECQBUNODQP-UHFFFAOYSA-N 0.000 description 1
• 150000002334 glycols Chemical class 0.000 description 1
• 239000003979 granulating agent Substances 0.000 description 1
• 125000005843 halogen group Chemical group 0.000 description 1
• 230000002440 hepatic effect Effects 0.000 description 1
• 230000007686 hepatotoxicity Effects 0.000 description 1
• 231100000304 hepatotoxicity Toxicity 0.000 description 1
• 150000002391 heterocyclic compounds Chemical class 0.000 description 1
• 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 229950007035 homocamfin Drugs 0.000 description 1
• 125000002632 imidazolidinyl group Chemical group 0.000 description 1
• 125000002636 imidazolinyl group Chemical group 0.000 description 1
• 125000006302 indol-3-yl methyl group Chemical group [H]N1C([H])=C(C2=C([H])C([H])=C([H])C([H])=C12)C([H])([H])* 0.000 description 1
• HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 1
• 230000036512 infertility Effects 0.000 description 1
• 206010022000 influenza Diseases 0.000 description 1
• 208000037797 influenza A Diseases 0.000 description 1
• 208000037798 influenza B Diseases 0.000 description 1
• 239000004615 ingredient Substances 0.000 description 1
• 230000002401 inhibitory effect Effects 0.000 description 1
• 230000005764 inhibitory process Effects 0.000 description 1
• 238000002347 injection Methods 0.000 description 1
• 239000007924 injection Substances 0.000 description 1
• 239000011630 iodine Chemical group 0.000 description 1
• 125000002346 iodo group Chemical group I* 0.000 description 1
• QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
• ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• 239000002502 liposome Substances 0.000 description 1
• 239000000314 lubricant Substances 0.000 description 1
• QUXHCILOWRXCEO-UHFFFAOYSA-M magnesium;butane;chloride Chemical compound [Mg+2].[Cl-].CCC[CH2-] QUXHCILOWRXCEO-UHFFFAOYSA-M 0.000 description 1
• 239000000594 mannitol Substances 0.000 description 1
• 235000010355 mannitol Nutrition 0.000 description 1
• 238000002483 medication Methods 0.000 description 1
• 229940126601 medicinal product Drugs 0.000 description 1
• 201000011475 meningoencephalitis Diseases 0.000 description 1
• LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 1
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
• QTFKTBRIGWJQQL-UHFFFAOYSA-N meturedepa Chemical compound C1C(C)(C)N1P(=O)(NC(=O)OCC)N1CC1(C)C QTFKTBRIGWJQQL-UHFFFAOYSA-N 0.000 description 1
• 229950009847 meturedepa Drugs 0.000 description 1
• 239000002679 microRNA Substances 0.000 description 1
• 230000003278 mimic effect Effects 0.000 description 1
• 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
• 125000001620 monocyclic carbocycle group Chemical group 0.000 description 1
• 125000002757 morpholinyl group Chemical group 0.000 description 1
• 208000013465 muscle pain Diseases 0.000 description 1
• YCWKZLXTHMGYAO-UHFFFAOYSA-N n-methylcyclopropanamine;hydrochloride Chemical compound Cl.CNC1CC1 YCWKZLXTHMGYAO-UHFFFAOYSA-N 0.000 description 1
• 239000007922 nasal spray Substances 0.000 description 1
• IQZPDFORWZTSKT-UHFFFAOYSA-N nitrosulphonic acid Chemical compound OS(=O)(=O)[N+]([O-])=O IQZPDFORWZTSKT-UHFFFAOYSA-N 0.000 description 1
• 239000003921 oil Substances 0.000 description 1
• ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
• 230000003287 optical effect Effects 0.000 description 1
• 239000007935 oral tablet Substances 0.000 description 1
• 150000007524 organic acids Chemical class 0.000 description 1
• 239000003791 organic solvent mixture Substances 0.000 description 1
• 229960003752 oseltamivir Drugs 0.000 description 1
• NENPYTRHICXVCS-YNEHKIRRSA-N oseltamivir acid Chemical compound CCC(CC)O[C@@H]1C=C(C(O)=O)C[C@H](N)[C@H]1NC(C)=O NENPYTRHICXVCS-YNEHKIRRSA-N 0.000 description 1
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
• KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
• 230000006320 pegylation Effects 0.000 description 1
• 239000003961 penetration enhancing agent Substances 0.000 description 1
• 230000035699 permeability Effects 0.000 description 1
• 208000025858 pestivirus infectious disease Diseases 0.000 description 1
• 239000003208 petroleum Substances 0.000 description 1
• 230000003285 pharmacodynamic effect Effects 0.000 description 1
• 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
• 229950000688 phenothiazine Drugs 0.000 description 1
• 238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 1
• LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 1
• 102000020233 phosphotransferase Human genes 0.000 description 1
• XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
• 239000006187 pill Substances 0.000 description 1
• 125000004193 piperazinyl group Chemical group 0.000 description 1
• 125000003386 piperidinyl group Chemical group 0.000 description 1
• 239000011591 potassium Substances 0.000 description 1
• CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
• 230000003389 potentiating effect Effects 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• 230000003449 preventive effect Effects 0.000 description 1
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
• 102000004169 proteins and genes Human genes 0.000 description 1
• CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 1
• OUFHXMSGJIYFPW-UHFFFAOYSA-N pyrazino[2,3-c]pyridazine Chemical compound N1=NC=CC2=NC=CN=C21 OUFHXMSGJIYFPW-UHFFFAOYSA-N 0.000 description 1
• 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
• FVLAYJRLBLHIPV-UHFFFAOYSA-N pyrimidin-5-amine Chemical compound NC1=CN=CN=C1 FVLAYJRLBLHIPV-UHFFFAOYSA-N 0.000 description 1
• HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
• 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
• 125000000168 pyrrolyl group Chemical group 0.000 description 1
• 238000005173 quadrupole mass spectroscopy Methods 0.000 description 1
• JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
• 150000003254 radicals Chemical class 0.000 description 1
• 229940118771 rapivab Drugs 0.000 description 1
• 230000009467 reduction Effects 0.000 description 1
• 230000010076 replication Effects 0.000 description 1
• 238000011160 research Methods 0.000 description 1
• 230000029058 respiratory gaseous exchange Effects 0.000 description 1
• 108091092562 ribozyme Proteins 0.000 description 1
• 229960000888 rimantadine Drugs 0.000 description 1
• 229920002477 rna polymer Polymers 0.000 description 1
• 201000005404 rubella Diseases 0.000 description 1
• 229930195734 saturated hydrocarbon Natural products 0.000 description 1
• 230000009291 secondary effect Effects 0.000 description 1
• 229910052709 silver Inorganic materials 0.000 description 1
• 239000004332 silver Substances 0.000 description 1
• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
• AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
• 235000019345 sodium thiosulphate Nutrition 0.000 description 1
• 239000002594 sorbent Substances 0.000 description 1
• 241000894007 species Species 0.000 description 1
• WWUZIQQURGPMPG-KRWOKUGFSA-N sphingosine Chemical compound CCCCCCCCCCCCC\C=C\[C@@H](O)[C@@H](N)CO WWUZIQQURGPMPG-KRWOKUGFSA-N 0.000 description 1
• 125000003003 spiro group Chemical group 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
• 229940086735 succinate Drugs 0.000 description 1
• KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
• 229960002317 succinimide Drugs 0.000 description 1
• 150000003871 sulfonates Chemical class 0.000 description 1
• 125000004434 sulfur atom Chemical group 0.000 description 1
• 239000000375 suspending agent Substances 0.000 description 1
• 238000013268 sustained release Methods 0.000 description 1
• 239000012730 sustained-release form Substances 0.000 description 1
• 229940095064 tartrate Drugs 0.000 description 1
• 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 238000012360 testing method Methods 0.000 description 1
• 150000003536 tetrazoles Chemical class 0.000 description 1
• VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
• RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 description 1
• 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
• 229930192474 thiophene Natural products 0.000 description 1
• 229940113082 thymine Drugs 0.000 description 1
• 210000001519 tissue Anatomy 0.000 description 1
• JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
• 238000011269 treatment regimen Methods 0.000 description 1
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical compound C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
• 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 229940035893 uracil Drugs 0.000 description 1
• 210000003462 vein Anatomy 0.000 description 1
• 230000029812 viral genome replication Effects 0.000 description 1
• 208000016261 weight loss Diseases 0.000 description 1
• 229960001515 yellow fever vaccine Drugs 0.000 description 1
• AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical compound N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 description 1