JP4514242B2 - 抗ウイルスピリミジンヌクレオシド類似体 - Google Patents
抗ウイルスピリミジンヌクレオシド類似体 Download PDFInfo
- Publication number
- JP4514242B2 JP4514242B2 JP54673298A JP54673298A JP4514242B2 JP 4514242 B2 JP4514242 B2 JP 4514242B2 JP 54673298 A JP54673298 A JP 54673298A JP 54673298 A JP54673298 A JP 54673298A JP 4514242 B2 JP4514242 B2 JP 4514242B2
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- Japan
- Prior art keywords
- alkyl
- group
- halogens
- methanol
- mmol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 230000000840 anti-viral effect Effects 0.000 title abstract description 20
- 229940127073 nucleoside analogue Drugs 0.000 title description 2
- 239000002718 pyrimidine nucleoside Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 46
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 241000701085 Human alphaherpesvirus 3 Species 0.000 claims abstract description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 26
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 13
- 241000701022 Cytomegalovirus Species 0.000 claims abstract description 11
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims abstract description 3
- 239000003443 antiviral agent Substances 0.000 claims description 7
- 241000700605 Viruses Species 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 23
- 150000002367 halogens Chemical class 0.000 abstract description 23
- 125000003118 aryl group Chemical group 0.000 abstract description 15
- -1 arythiol Chemical group 0.000 abstract description 12
- 230000003389 potentiating effect Effects 0.000 abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 7
- 125000002877 alkyl aryl group Chemical group 0.000 abstract description 6
- 229940002612 prodrug Drugs 0.000 abstract description 6
- 239000000651 prodrug Substances 0.000 abstract description 6
- 125000004104 aryloxy group Chemical group 0.000 abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 abstract description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 3
- 125000003282 alkyl amino group Chemical group 0.000 abstract description 2
- 150000001356 alkyl thiols Chemical class 0.000 abstract description 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 2
- 125000004663 dialkyl amino group Chemical group 0.000 abstract description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 2
- 150000003573 thiols Chemical class 0.000 abstract description 2
- 150000002431 hydrogen Chemical class 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 102
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 47
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- 239000000047 product Substances 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 26
- 239000002904 solvent Substances 0.000 description 22
- 239000003480 eluent Substances 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 19
- 239000007787 solid Substances 0.000 description 17
- 235000019439 ethyl acetate Nutrition 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000012043 crude product Substances 0.000 description 15
- 239000000243 solution Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 10
- 238000001819 mass spectrum Methods 0.000 description 10
- 239000012299 nitrogen atmosphere Substances 0.000 description 10
- 238000010898 silica gel chromatography Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 9
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- 239000002777 nucleoside Substances 0.000 description 8
- 238000007821 culture assay Methods 0.000 description 7
- 238000000338 in vitro Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- 208000036142 Viral infection Diseases 0.000 description 6
- 229960004150 aciclovir Drugs 0.000 description 6
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 229940087646 methanolamine Drugs 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 230000002265 prevention Effects 0.000 description 6
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 230000009385 viral infection Effects 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 150000001345 alkine derivatives Chemical group 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Natural products O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 239000006071 cream Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 150000003833 nucleoside derivatives Chemical class 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 238000001665 trituration Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 229920001429 chelating resin Polymers 0.000 description 3
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002773 nucleotide Substances 0.000 description 3
- 125000003729 nucleotide group Chemical group 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- MXQACMJEKYMFOM-UHFFFAOYSA-N 1,7-dihydropyrrolo[2,3-d]pyrimidin-2-one Chemical compound N1C(=O)N=C2NC=CC2=C1 MXQACMJEKYMFOM-UHFFFAOYSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- MXHRCPNRJAMMIM-SHYZEUOFSA-N 2'-deoxyuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 MXHRCPNRJAMMIM-SHYZEUOFSA-N 0.000 description 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- CXQLEVUWAFTOOE-GVDBMIGSSA-N 5-dec-1-ynyl-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C#CCCCCCCCC)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 CXQLEVUWAFTOOE-GVDBMIGSSA-N 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 239000001177 diphosphate Substances 0.000 description 2
- 235000011180 diphosphates Nutrition 0.000 description 2
- XQRLCLUYWUNEEH-UHFFFAOYSA-L diphosphonate(2-) Chemical compound [O-]P(=O)OP([O-])=O XQRLCLUYWUNEEH-UHFFFAOYSA-L 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000001605 fetal effect Effects 0.000 description 2
- 210000002950 fibroblast Anatomy 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
- 230000007886 mutagenicity Effects 0.000 description 2
- 231100000299 mutagenicity Toxicity 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 150000003014 phosphoric acid esters Chemical class 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
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- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 239000005450 thionucleoside Substances 0.000 description 2
- 239000001226 triphosphate Substances 0.000 description 2
- 235000011178 triphosphate Nutrition 0.000 description 2
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 2
- 229940035893 uracil Drugs 0.000 description 2
- PDWIQYODPROSQH-VPENINKCSA-N (2r,4s,5r)-5-(hydroxymethyl)oxolane-2,4-diol Chemical compound OC[C@H]1O[C@@H](O)C[C@@H]1O PDWIQYODPROSQH-VPENINKCSA-N 0.000 description 1
- LPBFZPLRLJQKHY-RCCFBDPRSA-N 1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(11-hydroxyundec-1-ynyl)pyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C#CCCCCCCCCCO)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 LPBFZPLRLJQKHY-RCCFBDPRSA-N 0.000 description 1
- MTJSWISCRCFSQT-QJPTWQEYSA-N 1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(5-hydroxypent-1-ynyl)pyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C#CCCCO)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 MTJSWISCRCFSQT-QJPTWQEYSA-N 0.000 description 1
- WRZPEEWYUHHKPC-PWRODBHTSA-N 1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-tetradec-1-ynylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C#CCCCCCCCCCCCC)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 WRZPEEWYUHHKPC-PWRODBHTSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- GAUSMJHDHCSZOX-UHFFFAOYSA-N 2,2,2-trifluoro-n-prop-2-ynylacetamide Chemical compound FC(F)(F)C(=O)NCC#C GAUSMJHDHCSZOX-UHFFFAOYSA-N 0.000 description 1
- QEQSBBLXFXHATM-UHFFFAOYSA-N 2-(3,3-dihydroxypropylamino)-1,7-dihydropurin-6-one Chemical compound N1C(NCCC(O)O)=NC(=O)C2=C1N=CN2 QEQSBBLXFXHATM-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- BZSHBOXLWHVZER-YNEHKIRRSA-N 5-(6-hydroxyhex-1-ynyl)-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C#CCCCCO)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 BZSHBOXLWHVZER-YNEHKIRRSA-N 0.000 description 1
- PGRIBSVBDKBPAD-IPMKNSEASA-N 5-dodec-1-ynyl-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C#CCCCCCCCCCC)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 PGRIBSVBDKBPAD-IPMKNSEASA-N 0.000 description 1
- CDEURGJCGCHYFH-DJLDLDEBSA-N 5-ethynyl-2'-deoxyuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(C#C)=C1 CDEURGJCGCHYFH-DJLDLDEBSA-N 0.000 description 1
- FJZHJDDOSWANSO-BFHYXJOUSA-N 5-hept-1-ynyl-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C#CCCCCC)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 FJZHJDDOSWANSO-BFHYXJOUSA-N 0.000 description 1
- NWZZMQOOZLSLRJ-YNEHKIRRSA-N 5-hex-1-ynyl-1-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C#CCCCC)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 NWZZMQOOZLSLRJ-YNEHKIRRSA-N 0.000 description 1
- GMVPRGQOIOIIMI-DODZYUBVSA-N 7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]heptanoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DODZYUBVSA-N 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
- 241000416162 Astragalus gummifer Species 0.000 description 1
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- 201000006082 Chickenpox Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 239000003298 DNA probe Substances 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 1
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 208000007514 Herpes zoster Diseases 0.000 description 1
- 241000700588 Human alphaherpesvirus 1 Species 0.000 description 1
- 241000701074 Human alphaherpesvirus 2 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
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical group S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 206010046980 Varicella Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
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- 235000010443 alginic acid Nutrition 0.000 description 1
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- 150000004781 alginic acids Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 150000001504 aryl thiols Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- ILLHQJIJCRNRCJ-UHFFFAOYSA-N dec-1-yne Chemical compound CCCCCCCCC#C ILLHQJIJCRNRCJ-UHFFFAOYSA-N 0.000 description 1
- MXHRCPNRJAMMIM-UHFFFAOYSA-N desoxyuridine Natural products C1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 MXHRCPNRJAMMIM-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical class OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
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- 229940074045 glyceryl distearate Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 125000003835 nucleoside group Chemical group 0.000 description 1
- GYCKQBWUSACYIF-UHFFFAOYSA-N o-hydroxybenzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 1
- UMIPWJGWASORKV-UHFFFAOYSA-N oct-1-yne Chemical compound CCCCCCC#C UMIPWJGWASORKV-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000005440 p-toluyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C(*)=O)C([H])([H])[H] 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000008300 phosphoramidites Chemical class 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910001467 sodium calcium phosphate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 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
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 230000007923 virulence factor Effects 0.000 description 1
- 239000000304 virulence factor Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Virology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9708611.0 | 1997-04-28 | ||
| GBGB9708611.0A GB9708611D0 (en) | 1997-04-28 | 1997-04-28 | Chemical compounds |
| PCT/GB1998/001222 WO1998049177A1 (en) | 1997-04-28 | 1998-04-27 | Anti-viral pyrimidine nucleoside analogues |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001522369A JP2001522369A (ja) | 2001-11-13 |
| JP2001522369A5 JP2001522369A5 (enExample) | 2005-09-08 |
| JP4514242B2 true JP4514242B2 (ja) | 2010-07-28 |
Family
ID=10811493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP54673298A Expired - Lifetime JP4514242B2 (ja) | 1997-04-28 | 1998-04-27 | 抗ウイルスピリミジンヌクレオシド類似体 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6573247B1 (enExample) |
| EP (1) | EP0980377B1 (enExample) |
| JP (1) | JP4514242B2 (enExample) |
| AT (1) | ATE221543T1 (enExample) |
| AU (1) | AU737902B2 (enExample) |
| CA (1) | CA2288147C (enExample) |
| DE (1) | DE69806919T2 (enExample) |
| DK (1) | DK0980377T3 (enExample) |
| ES (1) | ES2181208T3 (enExample) |
| GB (1) | GB9708611D0 (enExample) |
| NZ (1) | NZ500881A (enExample) |
| PT (1) | PT980377E (enExample) |
| WO (1) | WO1998049177A1 (enExample) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9708611D0 (en) * | 1997-04-28 | 1997-06-18 | Univ Cardiff | Chemical compounds |
| GB9716231D0 (en) | 1997-07-31 | 1997-10-08 | Amersham Int Ltd | Base analogues |
| CN1307421C (zh) | 1997-08-08 | 2007-03-28 | 塞米得肿瘤学美国公司 | 克服生物及化学治疗抗性的方法与组合物 |
| CN1192102C (zh) | 1998-01-23 | 2005-03-09 | 新生物生物公司 | 酶催化的治疗剂 |
| US7462605B2 (en) | 1998-01-23 | 2008-12-09 | Celmed Oncology (Usa), Inc. | Phosphoramidate compounds and methods of use |
| US6683061B1 (en) | 1999-07-22 | 2004-01-27 | Newbiotics, Inc. | Enzyme catalyzed therapeutic activation |
| AU774492B2 (en) | 1999-07-22 | 2004-07-01 | Celmed Oncology (Usa) Inc. | Methods for treating therapy-resistant tumors |
| GB0009486D0 (en) | 2000-04-17 | 2000-06-07 | Univ Cardiff | Chemical compounds |
| GB0011203D0 (en) * | 2000-05-09 | 2000-06-28 | Univ Cardiff | Chemical compounds |
| WO2003077215A2 (en) * | 2002-03-08 | 2003-09-18 | Glen Research Corporation | Fluorescent nitrogenous base and nucleosides incorporating same |
| WO2004046331A2 (en) | 2002-11-15 | 2004-06-03 | Idenix (Cayman) Limited | 2’-branched nucleosides and flaviviridae mutation |
| GB0609178D0 (en) | 2006-05-09 | 2006-06-21 | Univ Cardiff | Novel compounds |
| US7951789B2 (en) | 2006-12-28 | 2011-05-31 | Idenix Pharmaceuticals, Inc. | Compounds and pharmaceutical compositions for the treatment of viral infections |
| NZ599289A (en) | 2009-10-16 | 2014-11-28 | Melinta Therapeutics Inc | Antimicrobial compounds and methods of making and using the same |
| KR20190044136A (ko) | 2009-10-16 | 2019-04-29 | 멜린타 서브시디어리 코프. | 항미생물성 화합물 및 이의 제조 방법 및 사용 방법 |
| CN102725274A (zh) | 2009-10-16 | 2012-10-10 | Rib-X制药公司 | 抗微生物化合物和其制备和使用方法 |
| GB201016855D0 (en) * | 2010-10-06 | 2010-11-17 | Nucana Biomed Ltd | Chemical compounds |
| US9243025B2 (en) | 2011-03-31 | 2016-01-26 | Idenix Pharmaceuticals, Llc | Compounds and pharmaceutical compositions for the treatment of viral infections |
| EA201391536A1 (ru) | 2011-04-15 | 2014-08-29 | Мелинта Терапьютикс, Инк. | Противомикробные соединения и способы их получения и применения |
| GB201111779D0 (en) | 2011-07-08 | 2011-08-24 | Univ Cardiff | Chemical compounds |
| AR088441A1 (es) | 2011-09-12 | 2014-06-11 | Idenix Pharmaceuticals Inc | Compuestos de carboniloximetilfosforamidato sustituido y composiciones farmaceuticas para el tratamiento de infecciones virales |
| WO2013056046A1 (en) | 2011-10-14 | 2013-04-18 | Idenix Pharmaceuticals, Inc. | Substituted 3',5'-cyclic phosphates of purine nucleotide compounds and pharmaceutical compositions for the treatment of viral infections |
| WO2013177188A1 (en) | 2012-05-22 | 2013-11-28 | Idenix Pharmaceuticals, Inc. | 3',5'-cyclic phosphoramidate prodrugs for hcv infection |
| US9296778B2 (en) | 2012-05-22 | 2016-03-29 | Idenix Pharmaceuticals, Inc. | 3′,5′-cyclic phosphate prodrugs for HCV infection |
| JP6165848B2 (ja) | 2012-05-22 | 2017-07-19 | イデニク ファーマシューティカルズ エルエルシー | 肝疾患のためのｄ−アミノ酸化合物 |
| HUE029038T2 (en) | 2012-05-25 | 2017-01-30 | Janssen Sciences Ireland Uc | Uracil spirooxetan nucleosides |
| EP2900682A1 (en) | 2012-09-27 | 2015-08-05 | IDENIX Pharmaceuticals, Inc. | Esters and malonates of sate prodrugs |
| NZ706985A (en) | 2012-10-08 | 2018-08-31 | Centre Nat Rech Scient | 2’-chloro nucleoside analogs for hcv infection |
| EP2909222B1 (en) | 2012-10-22 | 2021-05-26 | Idenix Pharmaceuticals LLC | 2',4'-bridged nucleosides for hcv infection |
| EP2935304A1 (en) | 2012-12-19 | 2015-10-28 | IDENIX Pharmaceuticals, Inc. | 4'-fluoro nucleosides for the treatment of hcv |
| EP2970358B1 (en) | 2013-03-04 | 2021-06-30 | Idenix Pharmaceuticals LLC | 3'-deoxy nucleosides for the treatment of hcv |
| WO2014137930A1 (en) | 2013-03-04 | 2014-09-12 | Idenix Pharmaceuticals, Inc. | Thiophosphate nucleosides for the treatment of hcv |
| US20140271547A1 (en) | 2013-03-13 | 2014-09-18 | Idenix Pharmaceuticals, Inc. | Amino acid phosphoramidate pronucleotides of 2'-cyano, azido and amino nucleosides for the treatment of hcv |
| WO2014165542A1 (en) | 2013-04-01 | 2014-10-09 | Idenix Pharmaceuticals, Inc. | 2',4'-fluoro nucleosides for the treatment of hcv |
| WO2014197578A1 (en) | 2013-06-05 | 2014-12-11 | Idenix Pharmaceuticals, Inc. | 1',4'-thio nucleosides for the treatment of hcv |
| EP3027636B1 (en) | 2013-08-01 | 2022-01-05 | Idenix Pharmaceuticals LLC | D-amino acid phosphoramidate pronucleotides of halogeno pyrimidine compounds for liver disease |
| EP3038623A4 (en) | 2013-09-09 | 2017-04-19 | Melinta Therapeutics, Inc. | Antimicrobial compounds and methods of making and using the same |
| SG10201801956SA (en) | 2013-09-09 | 2018-04-27 | Melinta Therapeutics Inc | Antimicrobial compounds and methods of making and using the same |
| EP3131914B1 (en) | 2014-04-16 | 2023-05-10 | Idenix Pharmaceuticals LLC | 3'-substituted methyl or alkynyl nucleosides for the treatment of hcv |
| JP2018507881A (ja) | 2015-03-11 | 2018-03-22 | メリンタ セラピューティクス，インコーポレイテッド | 抗微生物化合物ならびにこれらを作製および使用する方法 |
| CA3023317A1 (en) | 2016-05-06 | 2017-11-09 | Melinta Therapeutics, Inc. | Antimicrobials and methods of making and using same |
| US20220396830A1 (en) * | 2021-05-13 | 2022-12-15 | Promega Corporation | Bioluminescent detection of dna synthesis |
| WO2024044375A2 (en) * | 2022-08-26 | 2024-02-29 | Regents Of The University Of Minnesota | Antiviral compounds |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62255499A (ja) * | 1986-04-28 | 1987-11-07 | Teijin Ltd | 螢光性ヌクレオシド又はヌクレオチド |
| US5047519A (en) * | 1986-07-02 | 1991-09-10 | E. I. Du Pont De Nemours And Company | Alkynylamino-nucleotides |
| GB9109186D0 (en) * | 1991-04-29 | 1991-06-19 | Wellcome Found | Preparation of thionucleosides |
| YU43193A (sh) * | 1992-06-22 | 1997-01-08 | Eli Lilly And Company | 2'-deoksi-2',2'-difluoro(4-supstituisani)pirimidinski nukleozidi antivirusnog i antikancerogenog dejstva i međuproizvodi |
| JPH06192285A (ja) * | 1992-12-25 | 1994-07-12 | Yamasa Shoyu Co Ltd | １−（β−Ｄ−エリスロ−ペントフラン−２−ウロシル）ピリミジン誘導体の製造法 |
| DE4321978A1 (de) * | 1993-07-01 | 1995-01-12 | Boehringer Mannheim Gmbh | Liponucleotide von Desoxynucleosiden, deren Herstellung sowie deren Verwendung als antivirale Arzneimittel |
| GB9505025D0 (en) * | 1995-03-13 | 1995-05-03 | Medical Res Council | Chemical compounds |
| GB9708611D0 (en) * | 1997-04-28 | 1997-06-18 | Univ Cardiff | Chemical compounds |
| GB9716231D0 (en) * | 1997-07-31 | 1997-10-08 | Amersham Int Ltd | Base analogues |
| AU774492B2 (en) * | 1999-07-22 | 2004-07-01 | Celmed Oncology (Usa) Inc. | Methods for treating therapy-resistant tumors |
| HK1053126A1 (zh) * | 1999-07-22 | 2003-10-10 | 新生物生物公司 | 酶催化的治疗活化 |
| MXPA02000761A (es) * | 1999-07-22 | 2002-08-12 | Newbiotics Inc | Agentes terapeuticos anti-infecciosos catalizados por enzima. |
-
1997
- 1997-04-28 GB GBGB9708611.0A patent/GB9708611D0/en active Pending
-
1998
- 1998-04-27 ES ES98919313T patent/ES2181208T3/es not_active Expired - Lifetime
- 1998-04-27 EP EP98919313A patent/EP0980377B1/en not_active Expired - Lifetime
- 1998-04-27 PT PT98919313T patent/PT980377E/pt unknown
- 1998-04-27 CA CA002288147A patent/CA2288147C/en not_active Expired - Lifetime
- 1998-04-27 AT AT98919313T patent/ATE221543T1/de active
- 1998-04-27 DK DK98919313T patent/DK0980377T3/da active
- 1998-04-27 DE DE69806919T patent/DE69806919T2/de not_active Expired - Lifetime
- 1998-04-27 AU AU72193/98A patent/AU737902B2/en not_active Expired
- 1998-04-27 US US09/403,853 patent/US6573247B1/en not_active Expired - Lifetime
- 1998-04-27 NZ NZ500881A patent/NZ500881A/en not_active IP Right Cessation
- 1998-04-27 JP JP54673298A patent/JP4514242B2/ja not_active Expired - Lifetime
- 1998-04-27 WO PCT/GB1998/001222 patent/WO1998049177A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| ATE221543T1 (de) | 2002-08-15 |
| DE69806919T2 (de) | 2003-02-27 |
| AU737902B2 (en) | 2001-09-06 |
| GB9708611D0 (en) | 1997-06-18 |
| AU7219398A (en) | 1998-11-24 |
| NZ500881A (en) | 2001-11-30 |
| WO1998049177A1 (en) | 1998-11-05 |
| DE69806919D1 (de) | 2002-09-05 |
| CA2288147C (en) | 2008-03-11 |
| DK0980377T3 (da) | 2002-11-18 |
| ES2181208T3 (es) | 2003-02-16 |
| US6573247B1 (en) | 2003-06-03 |
| WO1998049177A8 (en) | 2000-01-13 |
| EP0980377B1 (en) | 2002-07-31 |
| PT980377E (pt) | 2002-12-31 |
| EP0980377A1 (en) | 2000-02-23 |
| JP2001522369A (ja) | 2001-11-13 |
| CA2288147A1 (en) | 1998-11-05 |
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