DE69806919T2 - Antivirale pyrimidin-nukleosid-analogen - Google Patents
Antivirale pyrimidin-nukleosid-analogenInfo
- Publication number
- DE69806919T2 DE69806919T2 DE69806919T DE69806919T DE69806919T2 DE 69806919 T2 DE69806919 T2 DE 69806919T2 DE 69806919 T DE69806919 T DE 69806919T DE 69806919 T DE69806919 T DE 69806919T DE 69806919 T2 DE69806919 T2 DE 69806919T2
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- group
- halogens
- compound according
- aryl
- 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
Links
- 230000000840 anti-viral effect Effects 0.000 title abstract description 20
- 239000002718 pyrimidine nucleoside Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 49
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 31
- 150000002367 halogens Chemical class 0.000 claims abstract description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
- 241000701085 Human alphaherpesvirus 3 Species 0.000 claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 claims abstract description 18
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 17
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
- 241000701022 Cytomegalovirus Species 0.000 claims abstract description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 7
- 229940002612 prodrug Drugs 0.000 claims abstract description 7
- 239000000651 prodrug Substances 0.000 claims abstract description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 4
- 150000001356 alkyl thiols Chemical class 0.000 claims abstract description 4
- -1 arythiol Chemical group 0.000 claims abstract description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims abstract description 3
- 150000003573 thiols Chemical class 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract 5
- 238000011282 treatment Methods 0.000 claims description 11
- 208000036142 Viral infection Diseases 0.000 claims description 9
- 230000009385 viral infection Effects 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 239000002777 nucleoside Substances 0.000 claims description 8
- 238000011321 prophylaxis Methods 0.000 claims description 8
- 150000001345 alkine derivatives Chemical group 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 150000001504 aryl thiols Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 230000003389 potentiating effect Effects 0.000 abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 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
- 239000002904 solvent Substances 0.000 description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 18
- 239000007787 solid Substances 0.000 description 17
- 239000012043 crude product Substances 0.000 description 16
- 235000019439 ethyl acetate Nutrition 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 14
- 239000003480 eluent Substances 0.000 description 14
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000001819 mass spectrum Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000012299 nitrogen atmosphere Substances 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 8
- 238000000338 in vitro Methods 0.000 description 8
- 241000700605 Viruses Species 0.000 description 7
- 229940087646 methanolamine Drugs 0.000 description 7
- 201000006082 Chickenpox Diseases 0.000 description 6
- 208000007514 Herpes zoster Diseases 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- 206010046980 Varicella 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
- 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
- 125000001424 substituent group Chemical group 0.000 description 6
- 229910019142 PO4 Inorganic materials 0.000 description 5
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 230000008878 coupling Effects 0.000 description 5
- 238000010168 coupling process Methods 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 235000021317 phosphate Nutrition 0.000 description 5
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000001665 trituration Methods 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229940127073 nucleoside analogue Drugs 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
- 230000037396 body weight Effects 0.000 description 3
- 229920001429 chelating resin Polymers 0.000 description 3
- 239000001177 diphosphate Substances 0.000 description 3
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical class [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 3
- 235000011180 diphosphates Nutrition 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000001226 triphosphate Substances 0.000 description 3
- 235000011178 triphosphate Nutrition 0.000 description 3
- 125000002264 triphosphate group Chemical class [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-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
- VQCQTJWSCCBUFL-UHFFFAOYSA-N 5-iodo-1-methylpyrimidine-2,4-dione Chemical compound CN1C=C(I)C(=O)NC1=O VQCQTJWSCCBUFL-UHFFFAOYSA-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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 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
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000007884 disintegrant Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 210000002950 fibroblast Anatomy 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
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- 238000010438 heat treatment Methods 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
- 125000003835 nucleoside group Chemical group 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
- 150000003254 radicals Chemical group 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
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- 239000007858 starting material Substances 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
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- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 239000005450 thionucleoside Substances 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
- IVWWFWFVSWOTLP-YVZVNANGSA-N (3'as,4r,7'as)-2,2,2',2'-tetramethylspiro[1,3-dioxolane-4,6'-4,7a-dihydro-3ah-[1,3]dioxolo[4,5-c]pyran]-7'-one Chemical compound C([C@@H]1OC(O[C@@H]1C1=O)(C)C)O[C@]21COC(C)(C)O2 IVWWFWFVSWOTLP-YVZVNANGSA-N 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 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
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- MXHRCPNRJAMMIM-SHYZEUOFSA-N 2'-deoxyuridine Chemical class C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C=C1 MXHRCPNRJAMMIM-SHYZEUOFSA-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
- KSNXJLQDQOIRIP-UHFFFAOYSA-N 5-iodouracil Chemical class IC1=CNC(=O)NC1=O KSNXJLQDQOIRIP-UHFFFAOYSA-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
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- 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
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- 235000019759 Maize starch Nutrition 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
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- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008365 aqueous carrier Substances 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
- 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
- 229910000389 calcium phosphate Inorganic materials 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
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
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- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
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- 230000005494 condensation Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- ILLHQJIJCRNRCJ-UHFFFAOYSA-N dec-1-yne Chemical compound CCCCCCCCC#C ILLHQJIJCRNRCJ-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 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
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 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
- 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
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- UHUSDOQQWJGJQS-UHFFFAOYSA-N glycerol 1,2-dioctadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCCCCCCCCCCC UHUSDOQQWJGJQS-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 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
- 239000003701 inert diluent Substances 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
- 239000010410 layer 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
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- OSSQSXOTMIGBCF-UHFFFAOYSA-N non-1-yne Chemical compound CCCCCCCC#C OSSQSXOTMIGBCF-UHFFFAOYSA-N 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
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide 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
- 239000012044 organic layer 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 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
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 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
- 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
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 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
- 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)
- Virology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 (2)
| Publication Number | Publication Date |
|---|---|
| DE69806919D1 DE69806919D1 (de) | 2002-09-05 |
| DE69806919T2 true DE69806919T2 (de) | 2003-02-27 |
Family
ID=10811493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69806919T Expired - Lifetime DE69806919T2 (de) | 1997-04-28 | 1998-04-27 | Antivirale pyrimidin-nukleosid-analogen |
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 |
| DE69840216D1 (de) | 1997-08-08 | 2008-12-24 | Celmed Oncology Usa Inc | Verfahren und Zubereitungen um Resistenz gegen biologische oder chemische Therapien zu Überwinden |
| US7462605B2 (en) | 1998-01-23 | 2008-12-09 | Celmed Oncology (Usa), Inc. | Phosphoramidate compounds and methods of use |
| ES2172303T3 (es) | 1998-01-23 | 2002-09-16 | Newbiotics Inc | Agentes terapeuticos obtenidos por catalisis enzimatica. |
| IL147749A0 (en) | 1999-07-22 | 2002-08-14 | Newbiotics Inc | Methods for treating therapy-resistant tumors |
| US6683061B1 (en) | 1999-07-22 | 2004-01-27 | Newbiotics, Inc. | Enzyme catalyzed therapeutic activation |
| GB0009486D0 (en) * | 2000-04-17 | 2000-06-07 | Univ Cardiff | Chemical compounds |
| GB0011203D0 (en) * | 2000-05-09 | 2000-06-28 | Univ Cardiff | Chemical compounds |
| US7144995B2 (en) | 2002-03-08 | 2006-12-05 | Glen Research Corporation | Fluorescent nitrogenous base and nucleosides incorporating same |
| PT1576138T (pt) | 2002-11-15 | 2017-05-03 | Idenix Pharmaceuticals Llc | 2'-metil-nucleósidos em combinação com interferão e mutação de flaviviridae |
| GB0609178D0 (en) | 2006-05-09 | 2006-06-21 | Univ Cardiff | Novel compounds |
| US20080261913A1 (en) | 2006-12-28 | 2008-10-23 | Idenix Pharmaceuticals, Inc. | Compounds and pharmaceutical compositions for the treatment of liver disorders |
| NZ599290A (en) | 2009-10-16 | 2014-10-31 | Melinta Therapeutics Inc | Antimicrobial compounds and methods of making and using the same |
| EA201270568A1 (ru) | 2009-10-16 | 2012-11-30 | Риб-Экс Фармасьютикалз, Инк. | Антимикробные композиции и способы их получения и применения |
| NZ599291A (en) | 2009-10-16 | 2014-06-27 | Melinta Therapeutics Inc | Antimicrobial compounds and methods of making and using the same |
| GB201016855D0 (en) * | 2010-10-06 | 2010-11-17 | Nucana Biomed Ltd | Chemical compounds |
| EP2691409B1 (en) | 2011-03-31 | 2018-02-21 | Idenix Pharmaceuticals LLC. | Compounds and pharmaceutical compositions for the treatment of viral infections |
| MY173518A (en) | 2011-04-15 | 2020-01-30 | Melinta Therapeutics Inc | Antimicrobial compounds and methods of making and using the same |
| 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 |
| EP2768838A1 (en) | 2011-10-14 | 2014-08-27 | IDENIX Pharmaceuticals, Inc. | Substituted 3',5'-cyclic phosphates of purine nucleotide compounds and pharmaceutical compositions for the treatment of viral infections |
| BR112014029115A8 (pt) | 2012-05-22 | 2018-04-03 | Idenix Pharmaceuticals Inc | Composto, composição farmacêutica, e, uso de um composto ou composição |
| EP2852604B1 (en) | 2012-05-22 | 2017-04-12 | Idenix Pharmaceuticals LLC | 3',5'-cyclic phosphoramidate prodrugs for hcv infection |
| EP2852605B1 (en) | 2012-05-22 | 2018-01-31 | Idenix Pharmaceuticals LLC | 3',5'-cyclic phosphate prodrugs for hcv infection |
| ES2597757T3 (es) | 2012-05-25 | 2017-01-20 | Janssen Sciences Ireland Uc | Nucleósidos de uracilespirooxetano |
| US9192621B2 (en) | 2012-09-27 | 2015-11-24 | Idenix Pharmaceuticals Llc | Esters and malonates of SATE prodrugs |
| BR112015007698A2 (pt) | 2012-10-08 | 2017-08-22 | Idenix Pharmaceuticals Inc Centre National De La Recherche Scientifique E Univ Montpellier 2 Science | Composto, composição farmacêutica, e, uso de um composto |
| EP2909222B1 (en) | 2012-10-22 | 2021-05-26 | Idenix Pharmaceuticals LLC | 2',4'-bridged nucleosides for hcv infection |
| WO2014099941A1 (en) | 2012-12-19 | 2014-06-26 | Idenix Pharmaceuticals, Inc. | 4'-fluoro nucleosides for the treatment of hcv |
| WO2014137930A1 (en) | 2013-03-04 | 2014-09-12 | Idenix Pharmaceuticals, Inc. | Thiophosphate nucleosides for the treatment of hcv |
| WO2014137926A1 (en) | 2013-03-04 | 2014-09-12 | Idenix Pharmaceuticals, Inc. | 3'-deoxy nucleosides for the treatment of hcv |
| EP2970357B1 (en) | 2013-03-13 | 2025-01-01 | Idenix Pharmaceuticals LLC | Amino acid phosphoramidate pronucleotides of 2'-cyano, azido and amino nucleosides for the treatment of hcv |
| EP2981542B1 (en) | 2013-04-01 | 2021-09-15 | Idenix Pharmaceuticals LLC | 2',4'-fluoro nucleosides for the treatment of hcv |
| US10005779B2 (en) | 2013-06-05 | 2018-06-26 | Idenix Pharmaceuticals Llc | 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 |
| SG10201801956SA (en) | 2013-09-09 | 2018-04-27 | Melinta Therapeutics Inc | Antimicrobial compounds and methods of making and using the same |
| EP3038623A4 (en) | 2013-09-09 | 2017-04-19 | Melinta Therapeutics, Inc. | Antimicrobial compounds and methods of making and using the same |
| WO2015161137A1 (en) | 2014-04-16 | 2015-10-22 | Idenix Pharmaceuticals, Inc. | 3'-substituted methyl or alkynyl nucleosides for the treatment of hcv |
| BR112017019349A2 (pt) | 2015-03-11 | 2018-06-05 | Melinta Therapeutics Inc | compostos antimicrobianos e métodos de fabricação e uso dos mesmos |
| US11098047B2 (en) | 2016-05-06 | 2021-08-24 | BioVersys AG | 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 |
| WO2001007454A1 (en) * | 1999-07-22 | 2001-02-01 | Newbiotics, Inc. | Enzyme catalyzed therapeutic activation |
| IL147749A0 (en) * | 1999-07-22 | 2002-08-14 | Newbiotics Inc | Methods for treating therapy-resistant tumors |
| EP1202749A2 (en) * | 1999-07-22 | 2002-05-08 | Newbiotics, Inc. | Enzyme catalyzed anti-infective therapeutic agents |
-
1997
- 1997-04-28 GB GBGB9708611.0A patent/GB9708611D0/en active Pending
-
1998
- 1998-04-27 JP JP54673298A patent/JP4514242B2/ja not_active Expired - Lifetime
- 1998-04-27 DK DK98919313T patent/DK0980377T3/da active
- 1998-04-27 AU AU72193/98A patent/AU737902B2/en not_active Expired
- 1998-04-27 WO PCT/GB1998/001222 patent/WO1998049177A1/en not_active Ceased
- 1998-04-27 NZ NZ500881A patent/NZ500881A/en not_active IP Right Cessation
- 1998-04-27 PT PT98919313T patent/PT980377E/pt unknown
- 1998-04-27 CA CA002288147A patent/CA2288147C/en not_active Expired - Lifetime
- 1998-04-27 EP EP98919313A patent/EP0980377B1/en not_active Expired - Lifetime
- 1998-04-27 ES ES98919313T patent/ES2181208T3/es not_active Expired - Lifetime
- 1998-04-27 DE DE69806919T patent/DE69806919T2/de not_active Expired - Lifetime
- 1998-04-27 US US09/403,853 patent/US6573247B1/en not_active Expired - Lifetime
- 1998-04-27 AT AT98919313T patent/ATE221543T1/de active
Also Published As
| Publication number | Publication date |
|---|---|
| WO1998049177A8 (en) | 2000-01-13 |
| EP0980377A1 (en) | 2000-02-23 |
| CA2288147A1 (en) | 1998-11-05 |
| CA2288147C (en) | 2008-03-11 |
| AU737902B2 (en) | 2001-09-06 |
| JP2001522369A (ja) | 2001-11-13 |
| PT980377E (pt) | 2002-12-31 |
| JP4514242B2 (ja) | 2010-07-28 |
| ES2181208T3 (es) | 2003-02-16 |
| EP0980377B1 (en) | 2002-07-31 |
| ATE221543T1 (de) | 2002-08-15 |
| DE69806919D1 (de) | 2002-09-05 |
| WO1998049177A1 (en) | 1998-11-05 |
| DK0980377T3 (da) | 2002-11-18 |
| AU7219398A (en) | 1998-11-24 |
| NZ500881A (en) | 2001-11-30 |
| US6573247B1 (en) | 2003-06-03 |
| GB9708611D0 (en) | 1997-06-18 |
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