EA007867B1 - Композиции для лечения флавивирусных и пестивирусных инфекций и способы их применения - Google Patents
Композиции для лечения флавивирусных и пестивирусных инфекций и способы их применения Download PDFInfo
- Publication number
- EA007867B1 EA007867B1 EA200201262A EA200201262A EA007867B1 EA 007867 B1 EA007867 B1 EA 007867B1 EA 200201262 A EA200201262 A EA 200201262A EA 200201262 A EA200201262 A EA 200201262A EA 007867 B1 EA007867 B1 EA 007867B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- alkyl
- pharmaceutically acceptable
- compound
- pharmaceutical composition
- pestivirus
- Prior art date
Links
- 241000710778 Pestivirus Species 0.000 title claims abstract description 72
- 241000710831 Flavivirus Species 0.000 title claims abstract description 55
- 238000000034 method Methods 0.000 title abstract description 57
- 239000000203 mixture Substances 0.000 title abstract description 19
- 229940002612 prodrug Drugs 0.000 claims abstract description 153
- 239000000651 prodrug Substances 0.000 claims abstract description 153
- 150000003839 salts Chemical class 0.000 claims abstract description 127
- 239000002777 nucleoside Substances 0.000 claims abstract description 91
- 150000003833 nucleoside derivatives Chemical class 0.000 claims abstract description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 586
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 252
- 150000001875 compounds Chemical class 0.000 claims description 246
- 125000002252 acyl group Chemical group 0.000 claims description 234
- 229910019142 PO4 Inorganic materials 0.000 claims description 191
- 239000010452 phosphate Substances 0.000 claims description 190
- -1 6-azacytosine Chemical compound 0.000 claims description 166
- 229910052739 hydrogen Inorganic materials 0.000 claims description 161
- 239000001257 hydrogen Substances 0.000 claims description 149
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 110
- 125000003342 alkenyl group Chemical group 0.000 claims description 91
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 85
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 82
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 82
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 82
- 229910052794 bromium Inorganic materials 0.000 claims description 82
- 239000000460 chlorine Substances 0.000 claims description 82
- 229910052801 chlorine Inorganic materials 0.000 claims description 82
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 81
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 79
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 72
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims description 72
- 125000000304 alkynyl group Chemical group 0.000 claims description 67
- 125000003118 aryl group Chemical group 0.000 claims description 63
- IGFXRKMLLMBKSA-UHFFFAOYSA-N purine Chemical compound N1=C[N]C2=NC=NC2=C1 IGFXRKMLLMBKSA-UHFFFAOYSA-N 0.000 claims description 63
- 150000002632 lipids Chemical group 0.000 claims description 61
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
- 125000001424 substituent group Chemical group 0.000 claims description 58
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 56
- 239000008194 pharmaceutical composition Substances 0.000 claims description 56
- 235000012000 cholesterol Nutrition 0.000 claims description 55
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 55
- 229920002554 vinyl polymer Polymers 0.000 claims description 55
- 229940024606 amino acid Drugs 0.000 claims description 54
- 150000001413 amino acids Chemical class 0.000 claims description 54
- 150000001720 carbohydrates Chemical class 0.000 claims description 54
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 54
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 53
- 150000003459 sulfonic acid esters Chemical class 0.000 claims description 53
- 229930024421 Adenine Natural products 0.000 claims description 40
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 40
- 229960000643 adenine Drugs 0.000 claims description 40
- 229940104302 cytosine Drugs 0.000 claims description 36
- 239000003937 drug carrier Substances 0.000 claims description 35
- 239000003795 chemical substances by application Substances 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
- 150000002148 esters Chemical class 0.000 claims description 28
- 230000003441 anti-flavivirus Effects 0.000 claims description 25
- 125000001246 bromo group Chemical group Br* 0.000 claims description 25
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 25
- 208000015181 infectious disease Diseases 0.000 claims description 25
- 125000002346 iodo group Chemical group I* 0.000 claims description 25
- 208000005176 Hepatitis C Diseases 0.000 claims description 23
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 23
- 239000003085 diluting agent Substances 0.000 claims description 23
- 239000003814 drug Substances 0.000 claims description 23
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 20
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 19
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 16
- RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical compound CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims description 16
- 125000003729 nucleotide group Chemical group 0.000 claims description 15
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 230000000840 anti-viral effect Effects 0.000 claims description 11
- 239000002552 dosage form Substances 0.000 claims description 11
- 239000002773 nucleotide Substances 0.000 claims description 11
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 10
- FDGQSTZJBFJUBT-UHFFFAOYSA-N hypoxanthine Chemical compound O=C1NC=NC2=C1NC=N2 FDGQSTZJBFJUBT-UHFFFAOYSA-N 0.000 claims description 10
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 10
- 229960000329 ribavirin Drugs 0.000 claims description 10
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 8
- 229940113082 thymine Drugs 0.000 claims description 8
- 229940035893 uracil Drugs 0.000 claims description 8
- 102000014150 Interferons Human genes 0.000 claims description 7
- 108010050904 Interferons Proteins 0.000 claims description 7
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 229940079322 interferon Drugs 0.000 claims description 7
- 150000003548 thiazolidines Chemical class 0.000 claims description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 239000002775 capsule Substances 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- UGQMRVRMYYASKQ-UHFFFAOYSA-N Hypoxanthine nucleoside Natural products OC1C(O)C(CO)OC1N1C(NC=NC2=O)=C2N=C1 UGQMRVRMYYASKQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims description 3
- LRSASMSXMSNRBT-UHFFFAOYSA-N 5-methylcytosine Chemical compound CC1=CNC(=O)N=C1N LRSASMSXMSNRBT-UHFFFAOYSA-N 0.000 claims description 3
- ZKBQDFAWXLTYKS-UHFFFAOYSA-N 6-Chloro-1H-purine Chemical compound ClC1=NC=NC2=C1NC=N2 ZKBQDFAWXLTYKS-UHFFFAOYSA-N 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 238000001990 intravenous administration Methods 0.000 claims description 3
- 238000007920 subcutaneous administration Methods 0.000 claims description 3
- MSSXOMSJDRHRMC-UHFFFAOYSA-N 9H-purine-2,6-diamine Chemical compound NC1=NC(N)=C2NC=NC2=N1 MSSXOMSJDRHRMC-UHFFFAOYSA-N 0.000 claims description 2
- 208000036142 Viral infection Diseases 0.000 claims 24
- 230000009385 viral infection Effects 0.000 claims 24
- 230000002155 anti-virotic effect Effects 0.000 claims 5
- 229940121759 Helicase inhibitor Drugs 0.000 claims 4
- 229940123066 Polymerase inhibitor Drugs 0.000 claims 4
- 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 claims 2
- BOEYJNQMEZILNE-UHFFFAOYSA-N 5-nitropyrimidine Chemical compound [O-][N+](=O)C1=CN=C=N[CH]1 BOEYJNQMEZILNE-UHFFFAOYSA-N 0.000 claims 2
- 229940124158 Protease/peptidase inhibitor Drugs 0.000 claims 2
- XRECTZIEBJDKEO-UHFFFAOYSA-N flucytosine Chemical compound NC1=NC(=O)NC=C1F XRECTZIEBJDKEO-UHFFFAOYSA-N 0.000 claims 2
- 229960004413 flucytosine Drugs 0.000 claims 2
- 208000006454 hepatitis Diseases 0.000 claims 2
- 231100000283 hepatitis Toxicity 0.000 claims 2
- MRWXACSTFXYYMV-FDDDBJFASA-N nebularine Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC=C2N=C1 MRWXACSTFXYYMV-FDDDBJFASA-N 0.000 claims 2
- 239000002212 purine nucleoside Substances 0.000 claims 2
- 239000002718 pyrimidine nucleoside Substances 0.000 claims 2
- NMUSYJAQQFHJEW-UHFFFAOYSA-N 5-Azacytidine Natural products O=C1N=C(N)N=CN1C1C(O)C(O)C(CO)O1 NMUSYJAQQFHJEW-UHFFFAOYSA-N 0.000 claims 1
- NMUSYJAQQFHJEW-KVTDHHQDSA-N 5-azacytidine Chemical compound O=C1N=C(N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NMUSYJAQQFHJEW-KVTDHHQDSA-N 0.000 claims 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 229960002756 azacitidine Drugs 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- FVLAYJRLBLHIPV-UHFFFAOYSA-N pyrimidin-5-amine Chemical compound NC1=CN=CN=C1 FVLAYJRLBLHIPV-UHFFFAOYSA-N 0.000 claims 1
- 235000021317 phosphate Nutrition 0.000 description 185
- 150000004712 monophosphates Chemical class 0.000 description 146
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 138
- 239000001226 triphosphate Substances 0.000 description 136
- 235000011178 triphosphate Nutrition 0.000 description 136
- 239000002585 base Substances 0.000 description 129
- 239000001177 diphosphate Substances 0.000 description 127
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 127
- 235000011180 diphosphates Nutrition 0.000 description 127
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 80
- 150000002431 hydrogen Chemical class 0.000 description 62
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 58
- 239000011737 fluorine Substances 0.000 description 58
- 229910052731 fluorine Inorganic materials 0.000 description 58
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 54
- 125000005140 aralkylsulfonyl group Chemical group 0.000 description 53
- 235000014633 carbohydrates Nutrition 0.000 description 52
- 150000003904 phospholipids Chemical class 0.000 description 51
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 43
- 125000003282 alkyl amino group Chemical group 0.000 description 42
- 125000003835 nucleoside group Chemical group 0.000 description 34
- 235000000346 sugar Nutrition 0.000 description 34
- 229910004013 NO 2 Inorganic materials 0.000 description 29
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 28
- 241000700605 Viruses Species 0.000 description 26
- DEMJYWYZJFNNNB-UHFFFAOYSA-N OP(O)(O)=O.OP(O)(O)=O.OP(O)(O)=O Chemical compound OP(O)(O)=O.OP(O)(O)=O.OP(O)(O)=O DEMJYWYZJFNNNB-UHFFFAOYSA-N 0.000 description 24
- 239000002342 ribonucleoside Substances 0.000 description 21
- 230000000694 effects Effects 0.000 description 20
- NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 description 18
- 239000003112 inhibitor Substances 0.000 description 17
- CSSIWXFUZVBFND-UHFFFAOYSA-N OP(O)(=O)OP(=O)(O)O.OP(O)(=O)OP(=O)(O)O.OP(O)(=O)OP(=O)(O)O Chemical compound OP(O)(=O)OP(=O)(O)O.OP(O)(=O)OP(=O)(O)O.OP(O)(=O)OP(=O)(O)O CSSIWXFUZVBFND-UHFFFAOYSA-N 0.000 description 16
- WYVPBFVWZCTMPP-UHFFFAOYSA-N OP(O)(=O)OP(=O)(O)OP(=O)(O)O.OP(O)(=O)OP(=O)(O)OP(=O)(O)O.OP(O)(=O)OP(=O)(O)OP(=O)(O)O Chemical compound OP(O)(=O)OP(=O)(O)OP(=O)(O)O.OP(O)(=O)OP(=O)(O)OP(=O)(O)O.OP(O)(=O)OP(=O)(O)OP(=O)(O)O WYVPBFVWZCTMPP-UHFFFAOYSA-N 0.000 description 16
- 229910052700 potassium Inorganic materials 0.000 description 14
- 125000006239 protecting group Chemical group 0.000 description 13
- 239000000126 substance Substances 0.000 description 12
- MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical group CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 10
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- 229940079593 drug Drugs 0.000 description 9
- 238000011084 recovery Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 8
- DDIYWLKNBSUXJC-UHFFFAOYSA-N cyclopropyl phosphono hydrogen phosphate Chemical compound C1CC1OP(=O)(O)OP(=O)(O)O DDIYWLKNBSUXJC-UHFFFAOYSA-N 0.000 description 8
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 8
- 239000007800 oxidant agent Substances 0.000 description 8
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
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- 229910052799 carbon Inorganic materials 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 239000003638 chemical reducing agent Substances 0.000 description 7
- ZWBMVHLPYUKGKY-UHFFFAOYSA-N cyclopropyl [hydroxy(phosphonooxy)phosphoryl] hydrogen phosphate Chemical compound C1CC1OP(=O)(O)OP(=O)(O)OP(=O)(O)O ZWBMVHLPYUKGKY-UHFFFAOYSA-N 0.000 description 7
- UXBXOCZWFRBBBW-UHFFFAOYSA-N cyclopropyl dihydrogen phosphate Chemical compound OP(O)(=O)OC1CC1 UXBXOCZWFRBBBW-UHFFFAOYSA-N 0.000 description 7
- 238000007429 general method Methods 0.000 description 7
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- CZPRKINNVBONSF-UHFFFAOYSA-M zinc;dioxido(oxo)phosphanium Chemical compound [Zn+2].[O-][P+]([O-])=O CZPRKINNVBONSF-UHFFFAOYSA-M 0.000 description 6
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- 239000004480 active ingredient Substances 0.000 description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 5
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- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 5
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- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 5
- 238000010561 standard procedure Methods 0.000 description 5
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- JWDLEVZYUTZUBA-UHFFFAOYSA-N 2-amino-3,7-dihydropurin-6-one;phosphono dihydrogen phosphate Chemical compound OP(O)(=O)OP(O)(O)=O.O=C1NC(N)=NC2=C1NC=N2 JWDLEVZYUTZUBA-UHFFFAOYSA-N 0.000 description 4
- BALXSYQWXWVVJJ-UHFFFAOYSA-N 2-amino-3,7-dihydropurin-6-one;phosphoric acid Chemical compound OP(O)(O)=O.O=C1NC(N)=NC2=C1NC=N2 BALXSYQWXWVVJJ-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
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| US20767400P | 2000-05-26 | 2000-05-26 | |
| US28327601P | 2001-04-11 | 2001-04-11 | |
| PCT/US2001/016687 WO2001092282A2 (en) | 2000-05-26 | 2001-05-23 | Methods and compositions for treating flaviviruses and pestiviruses |
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| EA200601591A EA200601591A1 (ru) | 2000-05-26 | 2001-05-23 | Применение рибонуклеозидных соединений для лечения флавивирусных и пестивирусных инфекций |
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| DE69929060T2 (de) * | 1998-08-10 | 2006-08-31 | Idenix (Cayman) Ltd. | Beta-l-2'-deoxynukleoside für die behandlung von hepatitis b virus |
| US20020056123A1 (en) * | 2000-03-09 | 2002-05-09 | Gad Liwerant | Sharing a streaming video |
| MY164523A (en) * | 2000-05-23 | 2017-12-29 | Univ Degli Studi Cagliari | Methods and compositions for treating hepatitis c virus |
| EA007867B1 (ru) * | 2000-05-26 | 2007-02-27 | Айденикс (Кайман) Лимитед | Композиции для лечения флавивирусных и пестивирусных инфекций и способы их применения |
| ES2402597T3 (es) * | 2000-10-18 | 2013-05-07 | Gilead Pharmasset Llc | Nucleósidos modificados para el tratamiento de infecciones víricas y proliferación celular anormal |
| US7105499B2 (en) | 2001-01-22 | 2006-09-12 | Merck & Co., Inc. | Nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase |
| US8481712B2 (en) | 2001-01-22 | 2013-07-09 | Merck Sharp & Dohme Corp. | Nucleoside derivatives as inhibitors of RNA-dependent RNA viral polymerase |
| SI1355916T1 (sl) * | 2001-01-22 | 2007-04-30 | Merck & Co Inc | Nukleozidni derivati kot inhibitorji RNA-odvisne RNA virusne polimeraze |
| GB0114286D0 (en) * | 2001-06-12 | 2001-08-01 | Hoffmann La Roche | Nucleoside Derivatives |
| US6949522B2 (en) | 2001-06-22 | 2005-09-27 | Pharmasset, Inc. | β-2′- or 3′-halonucleosides |
| US20040006002A1 (en) * | 2001-09-28 | 2004-01-08 | Jean-Pierre Sommadossi | Methods and compositions for treating flaviviruses and pestiviruses using 4'-modified nucleoside |
| JP2005504087A (ja) | 2001-09-28 | 2005-02-10 | イデニクス（ケイマン）リミテツド | ４’が修飾されたヌクレオシドを使用するｃ型肝炎ウイルス治療のための方法および組成物 |
| WO2003051898A1 (en) * | 2001-12-17 | 2003-06-26 | Ribapharm Inc. | Unusual nucleoside libraries, compounds, and preferred uses as antiviral and anticancer agents |
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| US7217815B2 (en) | 2002-01-17 | 2007-05-15 | Valeant Pharmaceuticals North America | 2-beta -modified-6-substituted adenosine analogs and their use as antiviral agents |
| US7323453B2 (en) | 2002-02-13 | 2008-01-29 | Merck & Co., Inc. | Methods of inhibiting orthopoxvirus replication with nucleoside compounds |
| US7247621B2 (en) * | 2002-04-30 | 2007-07-24 | Valeant Research & Development | Antiviral phosphonate compounds and methods therefor |
| MXPA04010983A (es) * | 2002-05-06 | 2005-02-14 | Genelabs Tech Inc | Derivados de nucleosidos para tratar infecciones por el virus de la hepatitis c. |
| AU2003269892A1 (en) * | 2002-06-27 | 2004-01-19 | Isis Pharmaceuticals, Inc. | Nucleoside derivatives as inhibitors of rna-dependent rna viral polymerase |
| JP5087211B2 (ja) | 2002-06-28 | 2012-12-05 | イデニクス（ケイマン）リミテツド | フラビウィルス感染治療のための２′および３′−ヌクレオシドプロドラッグ |
| MXPA04012802A (es) * | 2002-06-28 | 2005-04-19 | Idenix Cayman Ltd | Ester 2'-c-metil-3'-o-l-valina de ribofuranosil-citidina para el tratamiento de infecciones por flaviviridae. |
| EP2799442A1 (en) * | 2002-06-28 | 2014-11-05 | IDENIX Pharmaceuticals, Inc. | Modified 2' and 3' -nucleoside prodrugs for treating flaviridae infections |
| US7608600B2 (en) * | 2002-06-28 | 2009-10-27 | Idenix Pharmaceuticals, Inc. | Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections |
| CN101172993A (zh) * | 2002-06-28 | 2008-05-07 | 埃迪尼克斯(开曼)有限公司 | 用于治疗黄病毒感染的2′－c－甲基－3′－o－l－缬氨酸酯核糖呋喃基胞苷 |
| RU2366661C2 (ru) * | 2002-06-28 | 2009-09-10 | Айденикс (Кайман) Лимитед | Пролекарства модифицированных 2'- и 3'-нуклеозидов для лечения инфекций flaviviridae |
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