AU2002365234B2 - N4-acylcytosine nucleosides for treatment of viral infections - Google Patents
N4-acylcytosine nucleosides for treatment of viral infections Download PDFInfo
- Publication number
- AU2002365234B2 AU2002365234B2 AU2002365234A AU2002365234A AU2002365234B2 AU 2002365234 B2 AU2002365234 B2 AU 2002365234B2 AU 2002365234 A AU2002365234 A AU 2002365234A AU 2002365234 A AU2002365234 A AU 2002365234A AU 2002365234 B2 AU2002365234 B2 AU 2002365234B2
- Authority
- AU
- Australia
- Prior art keywords
- hydrogen
- fluorine
- pharmaceutically acceptable
- dideoxy
- active compound
- 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.)
- Ceased
Links
- 238000011282 treatment Methods 0.000 title claims description 24
- 239000002777 nucleoside Substances 0.000 title description 29
- 125000003835 nucleoside group Chemical group 0.000 title description 7
- 208000036142 Viral infection Diseases 0.000 title description 3
- 230000009385 viral infection Effects 0.000 title description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 940
- 229910052731 fluorine Inorganic materials 0.000 claims description 620
- 150000001875 compounds Chemical class 0.000 claims description 415
- 229940002612 prodrug Drugs 0.000 claims description 360
- 239000000651 prodrug Substances 0.000 claims description 360
- 150000003839 salts Chemical class 0.000 claims description 349
- 125000000217 alkyl group Chemical group 0.000 claims description 96
- 125000003118 aryl group Chemical group 0.000 claims description 57
- -1 sulfonate ester Chemical group 0.000 claims description 55
- 125000000304 alkynyl group Chemical group 0.000 claims description 52
- 229910052736 halogen Inorganic materials 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 46
- 229910052794 bromium Inorganic materials 0.000 claims description 45
- 229910052801 chlorine Inorganic materials 0.000 claims description 42
- 125000003342 alkenyl group Chemical group 0.000 claims description 39
- 229910019142 PO4 Inorganic materials 0.000 claims description 36
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical group [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 36
- 239000010452 phosphate Substances 0.000 claims description 36
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 32
- 125000001188 haloalkyl group Chemical group 0.000 claims description 31
- 125000005843 halogen group Chemical group 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 30
- 125000004001 thioalkyl group Chemical group 0.000 claims description 27
- 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 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 208000015181 infectious disease Diseases 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 15
- 125000002252 acyl group Chemical group 0.000 claims description 13
- 238000001727 in vivo Methods 0.000 claims description 13
- 150000001413 amino acids Chemical class 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
- 235000012000 cholesterol Nutrition 0.000 claims description 12
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 12
- 150000002632 lipids Chemical class 0.000 claims description 12
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 12
- UHDGCWIWMRVCDJ-UHFFFAOYSA-N 1-beta-D-Xylofuranosyl-NH-Cytosine Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(CO)O1 UHDGCWIWMRVCDJ-UHFFFAOYSA-N 0.000 claims description 7
- UHDGCWIWMRVCDJ-PSQAKQOGSA-N Cytidine Natural products O=C1N=C(N)C=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-PSQAKQOGSA-N 0.000 claims description 7
- UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- YBJUNIVCKRWVAA-FPVIDPCTSA-N 6-amino-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(4-fluorobenzoyl)-1H-pyrimidin-2-one Chemical compound C1=CC(N)(C(=O)C=2C=CC(F)=CC=2)NC(=O)N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YBJUNIVCKRWVAA-FPVIDPCTSA-N 0.000 claims description 3
- YSLHKCWTZCBOCO-FPVIDPCTSA-N 6-amino-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(4-nitrobenzoyl)-1H-pyrimidin-2-one Chemical compound C1=CC(N)(C(=O)C=2C=CC(=CC=2)[N+]([O-])=O)NC(=O)N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YSLHKCWTZCBOCO-FPVIDPCTSA-N 0.000 claims description 2
- NOIZCHKDVXBABB-DBMQZSJKSA-N 6-amino-6-(4-tert-butylbenzoyl)-5-fluoro-3-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrimidin-2-one Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)C1(N)C(F)=CN([C@@H]2O[C@H](CO)CC2)C(=O)N1 NOIZCHKDVXBABB-DBMQZSJKSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- XDFKGNSHGAWJKK-PWUXRVMCSA-N 6-amino-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(4-methylbenzoyl)-1H-pyrimidin-2-one Chemical compound C1=CC(C)=CC=C1C(=O)C1(N)C=CN([C@H]2[C@@H]([C@H](O)[C@@H](CO)O2)O)C(=O)N1 XDFKGNSHGAWJKK-PWUXRVMCSA-N 0.000 claims 2
- XPZKEBBLAZUJAS-OBNKUBODSA-N 6-amino-5-fluoro-3-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-6-(4-iodobenzoyl)-1H-pyrimidin-2-one Chemical compound IC1=CC=C(C(=O)C2(NC(N([C@H]3CC[C@@H](CO)O3)C=C2F)=O)N)C=C1 XPZKEBBLAZUJAS-OBNKUBODSA-N 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- XMNMKEYOIYJGRD-FPVIDPCTSA-N 6-amino-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(3-fluorobenzoyl)-1H-pyrimidin-2-one Chemical compound C1=CC(N)(C(=O)C=2C=C(F)C=CC=2)NC(=O)N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O XMNMKEYOIYJGRD-FPVIDPCTSA-N 0.000 claims 1
- WLVNAHXIMSQHMW-OCDMVOQQSA-N 6-amino-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(4-ethylbenzoyl)-5-fluoro-1H-pyrimidin-2-one Chemical compound C(C)C1=CC=C(C(=O)C2(NC(N([C@H]3[C@H](O)[C@H](O)[C@@H](CO)O3)C=C2F)=O)N)C=C1 WLVNAHXIMSQHMW-OCDMVOQQSA-N 0.000 claims 1
- TXJDZHCOMITEDO-USNNFTJFSA-N 6-amino-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(4-propylbenzoyl)-1H-pyrimidin-2-one Chemical compound C1=CC(CCC)=CC=C1C(=O)C1(N)C=CN([C@H]2[C@@H]([C@H](O)[C@@H](CO)O2)O)C(=O)N1 TXJDZHCOMITEDO-USNNFTJFSA-N 0.000 claims 1
- HXXNIIFACRGMJY-PNXMHIEFSA-N 6-amino-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(thiophene-2-carbonyl)-1H-pyrimidin-2-one Chemical compound C1=CC(N)(C(=O)C=2SC=CC=2)NC(=O)N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O HXXNIIFACRGMJY-PNXMHIEFSA-N 0.000 claims 1
- DJVMNMGZLLNCOX-OBNKUBODSA-N 6-amino-5-fluoro-6-(4-fluorobenzoyl)-3-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrimidin-2-one Chemical compound C1=C(F)C(N)(C(=O)C=2C=CC(F)=CC=2)NC(=O)N1[C@H]1CC[C@@H](CO)O1 DJVMNMGZLLNCOX-OBNKUBODSA-N 0.000 claims 1
- ORAFXVZDHPCYMY-QQDBQQHDSA-N 6-amino-6-(1-benzothiophene-2-carbonyl)-5-fluoro-3-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrimidin-2-one Chemical compound C1=C(F)C(N)(C(=O)C=2SC3=CC=CC=C3C=2)NC(=O)N1[C@H]1CC[C@@H](CO)O1 ORAFXVZDHPCYMY-QQDBQQHDSA-N 0.000 claims 1
- DMEDABDOQFXXBC-OBNKUBODSA-N 6-amino-6-(3-chlorobenzoyl)-5-fluoro-3-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrimidin-2-one Chemical compound C1=C(F)C(N)(C(=O)C=2C=C(Cl)C=CC=2)NC(=O)N1[C@H]1CC[C@@H](CO)O1 DMEDABDOQFXXBC-OBNKUBODSA-N 0.000 claims 1
- VCLLXLWPTDLADT-OBNKUBODSA-N 6-amino-6-(4-chlorobenzoyl)-5-fluoro-3-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-1H-pyrimidin-2-one Chemical compound C1=C(F)C(N)(C(=O)C=2C=CC(Cl)=CC=2)NC(=O)N1[C@@H]1O[C@H](CO)C=C1 VCLLXLWPTDLADT-OBNKUBODSA-N 0.000 claims 1
- QFZSFOGFWZZUNY-OBNKUBODSA-N 6-amino-6-(4-chlorobenzoyl)-5-fluoro-3-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrimidin-2-one Chemical compound ClC1=CC=C(C(=O)C2(NC(N([C@H]3CC[C@@H](CO)O3)C=C2F)=O)N)C=C1 QFZSFOGFWZZUNY-OBNKUBODSA-N 0.000 claims 1
- VIVHUVPGOGXJLT-POXCNRTASA-N 6-amino-6-(4-ethylbenzoyl)-5-fluoro-3-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-1H-pyrimidin-2-one Chemical compound C1=CC(CC)=CC=C1C(=O)C1(N)C(F)=CN([C@H]2C=C[C@@H](CO)O2)C(=O)N1 VIVHUVPGOGXJLT-POXCNRTASA-N 0.000 claims 1
- GYKMBBKSGZJFDI-POXCNRTASA-N 6-amino-6-(4-ethylbenzoyl)-5-fluoro-3-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrimidin-2-one Chemical compound C1=CC(CC)=CC=C1C(=O)C1(N)C(F)=CN([C@@H]2O[C@H](CO)CC2)C(=O)N1 GYKMBBKSGZJFDI-POXCNRTASA-N 0.000 claims 1
- AMHSVLOKQVVFRS-OBNKUBODSA-N 6-amino-6-(cyclohexanecarbonyl)-5-fluoro-3-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrimidin-2-one Chemical compound C1(CCCCC1)C(=O)C1(NC(N([C@H]2CC[C@@H](CO)O2)C=C1F)=O)N AMHSVLOKQVVFRS-OBNKUBODSA-N 0.000 claims 1
- 239000002259 anti human immunodeficiency virus agent Substances 0.000 claims 1
- 229940124411 anti-hiv antiviral agent Drugs 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000000232 haloalkynyl group Chemical group 0.000 claims 1
- 125000004401 m-toluyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C(*)=O 0.000 claims 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 description 936
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 919
- 239000011737 fluorine Substances 0.000 description 615
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 393
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 307
- 125000001153 fluoro group Chemical group F* 0.000 description 222
- 229910052792 caesium Inorganic materials 0.000 description 49
- 235000021317 phosphate Nutrition 0.000 description 34
- 241000700721 Hepatitis B virus Species 0.000 description 33
- 241000725303 Human immunodeficiency virus Species 0.000 description 23
- 239000000203 mixture Substances 0.000 description 23
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 20
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 13
- 239000001226 triphosphate Substances 0.000 description 13
- 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 12
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical class NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 125000001544 thienyl group Chemical group 0.000 description 12
- 235000011178 triphosphate Nutrition 0.000 description 12
- 229940024606 amino acid Drugs 0.000 description 11
- 235000001014 amino acid Nutrition 0.000 description 11
- 125000005140 aralkylsulfonyl group Chemical group 0.000 description 11
- 229940104302 cytosine Drugs 0.000 description 11
- 239000001177 diphosphate Substances 0.000 description 11
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 11
- 235000011180 diphosphates Nutrition 0.000 description 11
- 150000002431 hydrogen Chemical class 0.000 description 11
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 11
- 150000004712 monophosphates Chemical class 0.000 description 11
- 150000003904 phospholipids Chemical class 0.000 description 11
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 11
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 10
- 150000003833 nucleoside derivatives Chemical class 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 208000031886 HIV Infections Diseases 0.000 description 7
- 208000037357 HIV infectious disease Diseases 0.000 description 7
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 7
- 208000030507 AIDS Diseases 0.000 description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000002541 furyl group Chemical group 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 6
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 125000001624 naphthyl group Chemical group 0.000 description 6
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- CFJYNSNXFXLKNS-UHFFFAOYSA-N p-menthane Chemical compound CC(C)C1CCC(C)CC1 CFJYNSNXFXLKNS-UHFFFAOYSA-N 0.000 description 6
- 230000002265 prevention Effects 0.000 description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 125000003396 thiol group Chemical class [H]S* 0.000 description 5
- 230000005526 G1 to G0 transition Effects 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
- 125000001769 aryl amino group Chemical group 0.000 description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- CRSOQBOWXPBRES-UHFFFAOYSA-N neopentane Chemical compound CC(C)(C)C CRSOQBOWXPBRES-UHFFFAOYSA-N 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 229940124597 therapeutic agent Drugs 0.000 description 4
- WGECXQBGLLYSFP-UHFFFAOYSA-N (+-)-2,3-dimethyl-pentane Natural products CCC(C)C(C)C WGECXQBGLLYSFP-UHFFFAOYSA-N 0.000 description 3
- XSSYCIGJYCVRRK-RQJHMYQMSA-N (-)-carbovir Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1C[C@H](CO)C=C1 XSSYCIGJYCVRRK-RQJHMYQMSA-N 0.000 description 3
- BZHMBWZPUJHVEE-UHFFFAOYSA-N 2,4-dimethylpentane Chemical compound CC(C)CC(C)C BZHMBWZPUJHVEE-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- BXZVVICBKDXVGW-NKWVEPMBSA-N Didanosine Chemical compound O1[C@H](CO)CC[C@@H]1N1C(NC=NC2=O)=C2N=C1 BXZVVICBKDXVGW-NKWVEPMBSA-N 0.000 description 3
- 108010050904 Interferons Proteins 0.000 description 3
- 102000014150 Interferons Human genes 0.000 description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 3
- 125000003368 amide group Chemical group 0.000 description 3
- 230000000840 anti-viral effect Effects 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- BFAKENXZKHGIGE-UHFFFAOYSA-N bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene Chemical compound FC1=C(C(=C(C(=C1F)I)F)F)N=NC1=C(C(=C(C(=C1F)F)I)F)F BFAKENXZKHGIGE-UHFFFAOYSA-N 0.000 description 3
- BEWYHVAWEKZDPP-UHFFFAOYSA-N bornane Chemical compound C1CC2(C)CCC1C2(C)C BEWYHVAWEKZDPP-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- QHMGJGNTMQDRQA-UHFFFAOYSA-N dotriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC QHMGJGNTMQDRQA-UHFFFAOYSA-N 0.000 description 3
- 230000002255 enzymatic effect Effects 0.000 description 3
- 208000006454 hepatitis Diseases 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- PLZDDPSCZHRBOY-UHFFFAOYSA-N inaktives 3-Methyl-nonan Natural products CCCCCCC(C)CC PLZDDPSCZHRBOY-UHFFFAOYSA-N 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 229940079322 interferon Drugs 0.000 description 3
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 230000010076 replication Effects 0.000 description 3
- 230000003612 virological effect Effects 0.000 description 3
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 3
- 229960002555 zidovudine Drugs 0.000 description 3
- MEBONNVPKOBPEA-UHFFFAOYSA-N 1,1,2-trimethylcyclohexane Chemical compound CC1CCCCC1(C)C MEBONNVPKOBPEA-UHFFFAOYSA-N 0.000 description 2
- WINCSBAYCULVDU-UHFFFAOYSA-N 1,1,2-trimethylcyclopentane Chemical compound CC1CCCC1(C)C WINCSBAYCULVDU-UHFFFAOYSA-N 0.000 description 2
- OBKHYUIZSOIEPG-UHFFFAOYSA-N 1,1,3-trimethylcyclopentane Chemical compound CC1CCC(C)(C)C1 OBKHYUIZSOIEPG-UHFFFAOYSA-N 0.000 description 2
- QEGNUYASOUJEHD-UHFFFAOYSA-N 1,1-dimethylcyclohexane Chemical compound CC1(C)CCCCC1 QEGNUYASOUJEHD-UHFFFAOYSA-N 0.000 description 2
- QWHNJUXXYKPLQM-UHFFFAOYSA-N 1,1-dimethylcyclopentane Chemical compound CC1(C)CCCC1 QWHNJUXXYKPLQM-UHFFFAOYSA-N 0.000 description 2
- XAZKFISIRYLAEE-UHFFFAOYSA-N 1,3-dimethylcyclopentane Chemical compound CC1CCC(C)C1 XAZKFISIRYLAEE-UHFFFAOYSA-N 0.000 description 2
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 2
- CXOWYJMDMMMMJO-UHFFFAOYSA-N 2,2-dimethylpentane Chemical compound CCCC(C)(C)C CXOWYJMDMMMMJO-UHFFFAOYSA-N 0.000 description 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 2
- WBRFDUJXCLCKPX-UHFFFAOYSA-N 2,3-dimethylheptane Chemical compound CCCCC(C)C(C)C WBRFDUJXCLCKPX-UHFFFAOYSA-N 0.000 description 2
- ZALHPSXXQIPKTQ-UHFFFAOYSA-N 2,6-dimethyloctane Chemical compound CCC(C)CCCC(C)C ZALHPSXXQIPKTQ-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Chemical compound CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 2
- SGVYKUFIHHTIFL-UHFFFAOYSA-N 2-methylnonane Chemical compound CCCCCCCC(C)C SGVYKUFIHHTIFL-UHFFFAOYSA-N 0.000 description 2
- AEXMKKGTQYQZCS-UHFFFAOYSA-N 3,3-dimethylpentane Chemical compound CCC(C)(C)CC AEXMKKGTQYQZCS-UHFFFAOYSA-N 0.000 description 2
- DUPUVYJQZSLSJB-UHFFFAOYSA-N 3-ethyl-2-methylpentane Chemical compound CCC(CC)C(C)C DUPUVYJQZSLSJB-UHFFFAOYSA-N 0.000 description 2
- SFRKSDZMZHIISH-UHFFFAOYSA-N 3-ethylhexane Chemical compound CCCC(CC)CC SFRKSDZMZHIISH-UHFFFAOYSA-N 0.000 description 2
- AORMDLNPRGXHHL-UHFFFAOYSA-N 3-ethylpentane Chemical compound CCC(CC)CC AORMDLNPRGXHHL-UHFFFAOYSA-N 0.000 description 2
- SEEOMASXHIJCDV-UHFFFAOYSA-N 3-methyloctane Chemical compound CCCCCC(C)CC SEEOMASXHIJCDV-UHFFFAOYSA-N 0.000 description 2
- PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 description 2
- DOGIHOCMZJUJNR-UHFFFAOYSA-N 4-methyloctane Chemical compound CCCCC(C)CCC DOGIHOCMZJUJNR-UHFFFAOYSA-N 0.000 description 2
- SFLGIMGLWCVAHP-UHFFFAOYSA-N 5h-oxathiole Chemical compound C1OSC=C1 SFLGIMGLWCVAHP-UHFFFAOYSA-N 0.000 description 2
- JGKIMJMEFCPMHB-FPVIDPCTSA-N 6-amino-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(4-iodobenzoyl)-1H-pyrimidin-2-one Chemical compound C1=CC(N)(C(=O)C=2C=CC(I)=CC=2)NC(=O)N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O JGKIMJMEFCPMHB-FPVIDPCTSA-N 0.000 description 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- 206010008909 Chronic Hepatitis Diseases 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- IFTRQJLVEBNKJK-UHFFFAOYSA-N Ethylcyclopentane Chemical compound CCC1CCCC1 IFTRQJLVEBNKJK-UHFFFAOYSA-N 0.000 description 2
- 206010016654 Fibrosis Diseases 0.000 description 2
- 206010019759 Hepatitis chronic persistent Diseases 0.000 description 2
- GWESVXSMPKAFAS-UHFFFAOYSA-N Isopropylcyclohexane Chemical compound CC(C)C1CCCCC1 GWESVXSMPKAFAS-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 208000037581 Persistent Infection Diseases 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- XNKLLVCARDGLGL-JGVFFNPUSA-N Stavudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1C=C[C@@H](CO)O1 XNKLLVCARDGLGL-JGVFFNPUSA-N 0.000 description 2
- 241000700605 Viruses Species 0.000 description 2
- 229960004150 aciclovir Drugs 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 2
- 238000011914 asymmetric synthesis Methods 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 229930006742 bornane Natural products 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 125000002837 carbocyclic group Chemical group 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000001684 chronic effect Effects 0.000 description 2
- 230000007882 cirrhosis Effects 0.000 description 2
- 208000019425 cirrhosis of liver Diseases 0.000 description 2
- KVZJLSYJROEPSQ-UHFFFAOYSA-N cis-DMCH Natural products CC1CCCCC1C KVZJLSYJROEPSQ-UHFFFAOYSA-N 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- HINAOCRDJFBYGD-UHFFFAOYSA-N fenchane Chemical compound C1CC2C(C)(C)CC1(C)C2 HINAOCRDJFBYGD-UHFFFAOYSA-N 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- FNAZRRHPUDJQCJ-UHFFFAOYSA-N henicosane Chemical compound CCCCCCCCCCCCCCCCCCCCC FNAZRRHPUDJQCJ-UHFFFAOYSA-N 0.000 description 2
- GNECQVKDNNGLCG-UHFFFAOYSA-N henicosylcyclopentane Chemical compound CCCCCCCCCCCCCCCCCCCCCC1CCCC1 GNECQVKDNNGLCG-UHFFFAOYSA-N 0.000 description 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 2
- BJQWYEJQWHSSCJ-UHFFFAOYSA-N heptacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCC BJQWYEJQWHSSCJ-UHFFFAOYSA-N 0.000 description 2
- NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- PXEZIKSRSYGOED-UHFFFAOYSA-N heptatriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC PXEZIKSRSYGOED-UHFFFAOYSA-N 0.000 description 2
- HMSWAIKSFDFLKN-UHFFFAOYSA-N hexacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC HMSWAIKSFDFLKN-UHFFFAOYSA-N 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- YDLYQMBWCWFRAI-UHFFFAOYSA-N hexatriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC YDLYQMBWCWFRAI-UHFFFAOYSA-N 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 235000013847 iso-butane Nutrition 0.000 description 2
- ZUBZATZOEPUUQF-UHFFFAOYSA-N isononane Chemical compound CCCCCCC(C)C ZUBZATZOEPUUQF-UHFFFAOYSA-N 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 230000008384 membrane barrier Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 2
- BDJAEZRIGNCQBZ-UHFFFAOYSA-N methylcyclobutane Chemical compound CC1CCC1 BDJAEZRIGNCQBZ-UHFFFAOYSA-N 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- LBQAJLBSGOBDQF-UHFFFAOYSA-N nitro azanylidynemethanesulfonate Chemical compound [O-][N+](=O)OS(=O)(=O)C#N LBQAJLBSGOBDQF-UHFFFAOYSA-N 0.000 description 2
- IGGUPRCHHJZPBS-UHFFFAOYSA-N nonacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCC IGGUPRCHHJZPBS-UHFFFAOYSA-N 0.000 description 2
- LQERIDTXQFOHKA-UHFFFAOYSA-N nonadecane Chemical compound CCCCCCCCCCCCCCCCCCC LQERIDTXQFOHKA-UHFFFAOYSA-N 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- SNXOSZZZNFRFNZ-UHFFFAOYSA-N nonatriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC SNXOSZZZNFRFNZ-UHFFFAOYSA-N 0.000 description 2
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 2
- 229940127073 nucleoside analogue Drugs 0.000 description 2
- ZYURHZPYMFLWSH-UHFFFAOYSA-N octacosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC ZYURHZPYMFLWSH-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- BVKCQBBZBGYNOP-UHFFFAOYSA-N octatriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC BVKCQBBZBGYNOP-UHFFFAOYSA-N 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- VHQQPFLOGSTQPC-UHFFFAOYSA-N pentatriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC VHQQPFLOGSTQPC-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 2
- 125000005499 phosphonyl group Chemical group 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 description 2
- TVSBRLGQVHJIKT-UHFFFAOYSA-N propan-2-ylcyclopentane Chemical compound CC(C)C1CCCC1 TVSBRLGQVHJIKT-UHFFFAOYSA-N 0.000 description 2
- DEDZSLCZHWTGOR-UHFFFAOYSA-N propylcyclohexane Chemical compound CCCC1CCCCC1 DEDZSLCZHWTGOR-UHFFFAOYSA-N 0.000 description 2
- KDIAMAVWIJYWHN-UHFFFAOYSA-N propylcyclopentane Chemical compound CCCC1CCCC1 KDIAMAVWIJYWHN-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- KUPLEGDPSCCPJI-UHFFFAOYSA-N tetracontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC KUPLEGDPSCCPJI-UHFFFAOYSA-N 0.000 description 2
- POOSGDOYLQNASK-UHFFFAOYSA-N tetracosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC POOSGDOYLQNASK-UHFFFAOYSA-N 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
- BGXXXYLRPIRDHJ-UHFFFAOYSA-N tetraethylmethane Chemical compound CCC(CC)(CC)CC BGXXXYLRPIRDHJ-UHFFFAOYSA-N 0.000 description 2
- GWVDBZWVFGFBCN-UHFFFAOYSA-N tetratriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC GWVDBZWVFGFBCN-UHFFFAOYSA-N 0.000 description 2
- 150000007970 thio esters Chemical class 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- JXTPJDDICSTXJX-UHFFFAOYSA-N triacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC JXTPJDDICSTXJX-UHFFFAOYSA-N 0.000 description 2
- FIGVVZUWCLSUEI-UHFFFAOYSA-N tricosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCC FIGVVZUWCLSUEI-UHFFFAOYSA-N 0.000 description 2
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 2
- ZISSAWUMDACLOM-UHFFFAOYSA-N triptane Chemical compound CC(C)C(C)(C)C ZISSAWUMDACLOM-UHFFFAOYSA-N 0.000 description 2
- 230000005748 tumor development Effects 0.000 description 2
- VKJLDXGFBJBTRQ-RFZPGFLSSA-N (1r,2r)-1,2-dimethylcyclopropane Chemical compound C[C@@H]1C[C@H]1C VKJLDXGFBJBTRQ-RFZPGFLSSA-N 0.000 description 1
- VCJPCEVERINRSG-YIZRAAEISA-N (1r,2s,4s)-1,2,4-trimethylcyclohexane Chemical compound C[C@H]1CC[C@@H](C)[C@@H](C)C1 VCJPCEVERINRSG-YIZRAAEISA-N 0.000 description 1
- DQTVJLHNWPRPPH-JVHMLUBASA-N (1r,3s)-1,2,3-trimethylcyclohexane Chemical compound C[C@H]1CCC[C@@H](C)C1C DQTVJLHNWPRPPH-JVHMLUBASA-N 0.000 description 1
- XAZKFISIRYLAEE-KNVOCYPGSA-N (1r,3s)-1,3-dimethylcyclopentane Chemical compound C[C@H]1CC[C@@H](C)C1 XAZKFISIRYLAEE-KNVOCYPGSA-N 0.000 description 1
- PNUFYSGVPVMNRN-IEESLHIDSA-N (1s,2r)-1,2,4-trimethylcyclopentane Chemical compound CC1C[C@H](C)[C@H](C)C1 PNUFYSGVPVMNRN-IEESLHIDSA-N 0.000 description 1
- VKJLDXGFBJBTRQ-SYDPRGILSA-N (1s,2r)-1,2-dimethylcyclopropane Chemical compound C[C@H]1C[C@H]1C VKJLDXGFBJBTRQ-SYDPRGILSA-N 0.000 description 1
- PQXAPVOKLYINEI-SFYZADRCSA-N (1s,3r)-1-ethyl-3-methylcyclopentane Chemical compound CC[C@H]1CC[C@@H](C)C1 PQXAPVOKLYINEI-SFYZADRCSA-N 0.000 description 1
- QVADRSWDTZDDGR-VKHMYHEASA-N (S)-alpha-hydroxyglutaric acid-gamma-lactone Chemical compound OC(=O)[C@@H]1CCC(=O)O1 QVADRSWDTZDDGR-VKHMYHEASA-N 0.000 description 1
- BXIIJPAVISPOGI-UHFFFAOYSA-N 1,1,2-trimethylcyclopropane Chemical compound CC1CC1(C)C BXIIJPAVISPOGI-UHFFFAOYSA-N 0.000 description 1
- WOJSMJIXPQLESQ-UHFFFAOYSA-N 1,1,3,5-tetramethylcyclohexane Chemical compound CC1CC(C)CC(C)(C)C1 WOJSMJIXPQLESQ-UHFFFAOYSA-N 0.000 description 1
- GQJXBLQVJKRGPQ-UHFFFAOYSA-N 1,1,4-trimethylcycloheptane Chemical compound CC1CCCC(C)(C)CC1 GQJXBLQVJKRGPQ-UHFFFAOYSA-N 0.000 description 1
- PBIJFSCPEFQXBB-UHFFFAOYSA-N 1,1-dimethylcyclopropane Chemical compound CC1(C)CC1 PBIJFSCPEFQXBB-UHFFFAOYSA-N 0.000 description 1
- PSGQRAAEZLHVDT-UHFFFAOYSA-N 1,2,3-trimethylcyclopropane Chemical compound CC1C(C)C1C PSGQRAAEZLHVDT-UHFFFAOYSA-N 0.000 description 1
- ODNRTOSCFYDTKF-UHFFFAOYSA-N 1,3,5-trimethylcyclohexane Chemical compound CC1CC(C)CC(C)C1 ODNRTOSCFYDTKF-UHFFFAOYSA-N 0.000 description 1
- CUJPFPXNDSIBPG-UHFFFAOYSA-N 1,3-propanediyl Chemical group [CH2]C[CH2] CUJPFPXNDSIBPG-UHFFFAOYSA-N 0.000 description 1
- OMIVCRYZSXDGAB-UHFFFAOYSA-N 1,4-butanediyl Chemical group [CH2]CC[CH2] OMIVCRYZSXDGAB-UHFFFAOYSA-N 0.000 description 1
- XKKCQTLDIPIRQD-JGVFFNPUSA-N 1-[(2r,5s)-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)CC1 XKKCQTLDIPIRQD-JGVFFNPUSA-N 0.000 description 1
- SSOKTUYAEOXEPO-UHFFFAOYSA-N 1-methyl-1-propylcyclohexane Chemical compound CCCC1(C)CCCCC1 SSOKTUYAEOXEPO-UHFFFAOYSA-N 0.000 description 1
- UMWPTXOKSJXVDS-UHFFFAOYSA-N 1-methyl-2-propan-2-ylcyclohexane Chemical compound CC(C)C1CCCCC1C UMWPTXOKSJXVDS-UHFFFAOYSA-N 0.000 description 1
- QUKOJKFJIHSBKV-UHFFFAOYSA-N 2,2,3,3-tetramethylpentane Chemical compound CCC(C)(C)C(C)(C)C QUKOJKFJIHSBKV-UHFFFAOYSA-N 0.000 description 1
- OWFKEHICSVOVAC-UHFFFAOYSA-N 2,2,3,4,4-pentamethylpentane Chemical compound CC(C)(C)C(C)C(C)(C)C OWFKEHICSVOVAC-UHFFFAOYSA-N 0.000 description 1
- VZFMYOCAEQDWDY-UHFFFAOYSA-N 2,2,3,4-tetramethylpentane Chemical compound CC(C)C(C)C(C)(C)C VZFMYOCAEQDWDY-UHFFFAOYSA-N 0.000 description 1
- XTDQDBVBDLYELW-UHFFFAOYSA-N 2,2,3-trimethylpentane Chemical compound CCC(C)C(C)(C)C XTDQDBVBDLYELW-UHFFFAOYSA-N 0.000 description 1
- GUMULFRCHLJNDY-UHFFFAOYSA-N 2,2,4,4-tetramethylpentane Chemical compound CC(C)(C)CC(C)(C)C GUMULFRCHLJNDY-UHFFFAOYSA-N 0.000 description 1
- GPBUTTSWJNPYJL-UHFFFAOYSA-N 2,2-dimethyloctane Chemical compound CCCCCCC(C)(C)C GPBUTTSWJNPYJL-UHFFFAOYSA-N 0.000 description 1
- JLCYYQOQSAMWTA-UHFFFAOYSA-N 2,3,3,4-tetramethylpentane Chemical compound CC(C)C(C)(C)C(C)C JLCYYQOQSAMWTA-UHFFFAOYSA-N 0.000 description 1
- OKVWYBALHQFVFP-UHFFFAOYSA-N 2,3,3-trimethylpentane Chemical compound CCC(C)(C)C(C)C OKVWYBALHQFVFP-UHFFFAOYSA-N 0.000 description 1
- XDRDDPSGUQMOBO-UHFFFAOYSA-N 2,3,4,4-tetramethylhexane Chemical compound CCC(C)(C)C(C)C(C)C XDRDDPSGUQMOBO-UHFFFAOYSA-N 0.000 description 1
- RLPGDEORIPLBNF-UHFFFAOYSA-N 2,3,4-trimethylpentane Chemical compound CC(C)C(C)C(C)C RLPGDEORIPLBNF-UHFFFAOYSA-N 0.000 description 1
- YPMNDMUOGQJCLW-UHFFFAOYSA-N 2,3-dimethyloctane Chemical compound CCCCCC(C)C(C)C YPMNDMUOGQJCLW-UHFFFAOYSA-N 0.000 description 1
- QALGVLROELGEEM-UHFFFAOYSA-N 2,4,4-trimethylheptane Chemical compound CCCC(C)(C)CC(C)C QALGVLROELGEEM-UHFFFAOYSA-N 0.000 description 1
- IXAVTTRPEXFVSX-UHFFFAOYSA-N 2,4-dimethyloctane Chemical compound CCCCC(C)CC(C)C IXAVTTRPEXFVSX-UHFFFAOYSA-N 0.000 description 1
- FZYYPNOHKXTKLI-NTSWFWBYSA-N 2-amino-9-[(2r,5s)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-3h-purin-6-one Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](CO)C=C1 FZYYPNOHKXTKLI-NTSWFWBYSA-N 0.000 description 1
- QQCWGAMGBCGAQJ-UHFFFAOYSA-N 3,4-dimethyloctane Chemical compound CCCCC(C)C(C)CC QQCWGAMGBCGAQJ-UHFFFAOYSA-N 0.000 description 1
- VRHRGVJOUHJULC-UHFFFAOYSA-N 3,5-dimethyloctane Chemical compound CCCC(C)CC(C)CC VRHRGVJOUHJULC-UHFFFAOYSA-N 0.000 description 1
- JEEQUUSFXYRPRK-UHFFFAOYSA-N 3,6-dimethyloctane Chemical compound CCC(C)CCC(C)CC JEEQUUSFXYRPRK-UHFFFAOYSA-N 0.000 description 1
- UVBCRFAFWVSXOL-JGVFFNPUSA-N 3-azido-1-[(2r,5s)-5-(hydroxymethyl)oxolan-2-yl]-5-methylpyrimidine-2,4-dione Chemical compound O=C1N(N=[N+]=[N-])C(=O)C(C)=CN1[C@@H]1O[C@H](CO)CC1 UVBCRFAFWVSXOL-JGVFFNPUSA-N 0.000 description 1
- AJDIFHIHSYVDGP-UHFFFAOYSA-N 3-ethyl-2,2,3-trimethylpentane Chemical compound CCC(C)(CC)C(C)(C)C AJDIFHIHSYVDGP-UHFFFAOYSA-N 0.000 description 1
- PJIFKODHGMUPFH-UHFFFAOYSA-N 3-ethyl-2,3-dimethylhexane Chemical compound CCCC(C)(CC)C(C)C PJIFKODHGMUPFH-UHFFFAOYSA-N 0.000 description 1
- MMASVVOQIKCFJZ-UHFFFAOYSA-N 3-ethyl-2,3-dimethylpentane Chemical compound CCC(C)(CC)C(C)C MMASVVOQIKCFJZ-UHFFFAOYSA-N 0.000 description 1
- VLHAGZNBWKUMRW-UHFFFAOYSA-N 3-ethyl-2,4-dimethylpentane Chemical compound CCC(C(C)C)C(C)C VLHAGZNBWKUMRW-UHFFFAOYSA-N 0.000 description 1
- NKMJCVVUYDKHAV-UHFFFAOYSA-N 3-ethyl-2-methylheptane Chemical compound CCCCC(CC)C(C)C NKMJCVVUYDKHAV-UHFFFAOYSA-N 0.000 description 1
- MVLOWDRGPHBNNF-UHFFFAOYSA-N 3-ethyl-2-methylhexane Chemical compound CCCC(CC)C(C)C MVLOWDRGPHBNNF-UHFFFAOYSA-N 0.000 description 1
- ZGJCTUKRTSBTIQ-UHFFFAOYSA-N 3-ethyl-3,4-dimethylhexane Chemical compound CCC(C)C(C)(CC)CC ZGJCTUKRTSBTIQ-UHFFFAOYSA-N 0.000 description 1
- CYWROHZCELEGSE-UHFFFAOYSA-N 3-ethyl-3-methylhexane Chemical compound CCCC(C)(CC)CC CYWROHZCELEGSE-UHFFFAOYSA-N 0.000 description 1
- GIEZWIDCIFCQPS-UHFFFAOYSA-N 3-ethyl-3-methylpentane Chemical compound CCC(C)(CC)CC GIEZWIDCIFCQPS-UHFFFAOYSA-N 0.000 description 1
- OKCRKWVABWILDR-UHFFFAOYSA-N 3-ethyl-4-methylhexane Chemical compound CCC(C)C(CC)CC OKCRKWVABWILDR-UHFFFAOYSA-N 0.000 description 1
- OEYGTUAKNZFCDJ-UHFFFAOYSA-N 3-ethyloctane Chemical compound CCCCCC(CC)CC OEYGTUAKNZFCDJ-UHFFFAOYSA-N 0.000 description 1
- ZGFNWCSPWANUIS-VSBTWAGUSA-N 3-fluoro-N-[1-[(2S,3R,4S,5R)-2-fluoro-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide Chemical compound F[C@@]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C(=O)N=C(NC(C2=CC(=CC=C2)F)=O)C=C1 ZGFNWCSPWANUIS-VSBTWAGUSA-N 0.000 description 1
- ZMEDGZAGMLTROM-UHFFFAOYSA-N 4,4-dimethyloctane Chemical compound CCCCC(C)(C)CCC ZMEDGZAGMLTROM-UHFFFAOYSA-N 0.000 description 1
- WREGKURFCTUGRC-UHFFFAOYSA-N 4-Amino-1-[5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1C1OC(CO)CC1 WREGKURFCTUGRC-UHFFFAOYSA-N 0.000 description 1
- IALRSQMWHFKJJA-UHFFFAOYSA-N 4-Methylnonane Natural products CCCCCC(C)CCC IALRSQMWHFKJJA-UHFFFAOYSA-N 0.000 description 1
- SZSDUEDWZYYMTK-HOPMXRPOSA-N 4-amino-1-[(2S,3R,4S,5R)-2-(4-ethylbenzoyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoropyrimidin-2-one Chemical compound C(C)C1=CC=C(C(=O)[C@@]2([C@H](O)[C@H](O)[C@@H](CO)O2)N2C(=O)N=C(N)C(=C2)F)C=C1 SZSDUEDWZYYMTK-HOPMXRPOSA-N 0.000 description 1
- OOBICGOWICFMIX-POYBYMJQSA-N 4-amino-1-[(2r,5s)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1[C@H]1C=C[C@@H](CO)O1 OOBICGOWICFMIX-POYBYMJQSA-N 0.000 description 1
- OEPQUYSQHIUHDR-HCWSKCQFSA-N 4-amino-1-[(2s,3r,4s,5r)-2-fluoro-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1[C@@]1(F)[C@H](O)[C@H](O)[C@@H](CO)O1 OEPQUYSQHIUHDR-HCWSKCQFSA-N 0.000 description 1
- JTEGQNOMFQHVDC-RQJHMYQMSA-N 4-amino-1-[(2s,5r)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)SC1 JTEGQNOMFQHVDC-RQJHMYQMSA-N 0.000 description 1
- DUMNJQREQSPHHQ-HHQFNNIRSA-N 4-amino-1-[(2s,5r)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one;2-phosphonoacetic acid Chemical compound OC(=O)CP(O)(O)=O.O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)SC1 DUMNJQREQSPHHQ-HHQFNNIRSA-N 0.000 description 1
- XXXIWLRSPLBZOD-ZBEGNZNMSA-N 4-amino-1-[(2s,5s)-2-benzoyl-5-(hydroxymethyl)oxolan-2-yl]-5-fluoropyrimidin-2-one Chemical compound C1=C(F)C(N)=NC(=O)N1[C@]1(C(=O)C=2C=CC=CC=2)O[C@H](CO)CC1 XXXIWLRSPLBZOD-ZBEGNZNMSA-N 0.000 description 1
- HSBKFSPNDWWPSL-CAHLUQPWSA-N 4-amino-5-fluoro-1-[(2r,5s)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one Chemical compound C1=C(F)C(N)=NC(=O)N1[C@H]1C=C[C@@H](CO)O1 HSBKFSPNDWWPSL-CAHLUQPWSA-N 0.000 description 1
- QHLDBFLIDFTHQI-UHFFFAOYSA-N 4-ethyl-2,2-dimethylhexane Chemical compound CCC(CC)CC(C)(C)C QHLDBFLIDFTHQI-UHFFFAOYSA-N 0.000 description 1
- SIKFMUYSQCEQOO-UHFFFAOYSA-N 4-ethyl-2,4-dimethylhexane Chemical compound CCC(C)(CC)CC(C)C SIKFMUYSQCEQOO-UHFFFAOYSA-N 0.000 description 1
- KYCZJIBOPKRSOV-UHFFFAOYSA-N 4-ethyl-2-methylhexane Chemical compound CCC(CC)CC(C)C KYCZJIBOPKRSOV-UHFFFAOYSA-N 0.000 description 1
- ZRTXVJYJVBTXHE-UHFFFAOYSA-N 4-ethyl-3,3-dimethylhexane Chemical compound CCC(CC)C(C)(C)CC ZRTXVJYJVBTXHE-UHFFFAOYSA-N 0.000 description 1
- MPYQJQDSICRCJJ-UHFFFAOYSA-N 4-ethyl-4-methylheptane Chemical compound CCCC(C)(CC)CCC MPYQJQDSICRCJJ-UHFFFAOYSA-N 0.000 description 1
- NRJUFUBKIFIKFI-UHFFFAOYSA-N 4-ethyloctane Chemical compound CCCCC(CC)CCC NRJUFUBKIFIKFI-UHFFFAOYSA-N 0.000 description 1
- ABYGSZMCWVXFCQ-UHFFFAOYSA-N 4-propylheptane Chemical compound CCCC(CCC)CCC ABYGSZMCWVXFCQ-UHFFFAOYSA-N 0.000 description 1
- NDIVKJFUWNXJJN-FPVIDPCTSA-N 6-amino-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(3-nitrobenzoyl)-1H-pyrimidin-2-one Chemical compound C1=CC(N)(C(=O)C=2C=C(C=CC=2)[N+]([O-])=O)NC(=O)N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NDIVKJFUWNXJJN-FPVIDPCTSA-N 0.000 description 1
- BSSDTTPDXHUFRY-OBNKUBODSA-N 6-amino-6-(3-bromobenzoyl)-5-fluoro-3-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrimidin-2-one Chemical compound C1=C(F)C(N)(C(=O)C=2C=C(Br)C=CC=2)NC(=O)N1[C@H]1CC[C@@H](CO)O1 BSSDTTPDXHUFRY-OBNKUBODSA-N 0.000 description 1
- ZZOWHGNRJBACEC-OBNKUBODSA-N 6-amino-6-(4-bromobenzoyl)-5-fluoro-3-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrimidin-2-one Chemical compound C1=C(F)C(N)(C(=O)C=2C=CC(Br)=CC=2)NC(=O)N1[C@H]1CC[C@@H](CO)O1 ZZOWHGNRJBACEC-OBNKUBODSA-N 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- HEZMQKDNJZOBEM-NOFOHJPNSA-N C1CCC[C@@H]2CCCC[C@H]21.C1CCC[C@@H]2CCCC[C@H]21 Chemical compound C1CCC[C@@H]2CCCC[C@H]21.C1CCC[C@@H]2CCCC[C@H]21 HEZMQKDNJZOBEM-NOFOHJPNSA-N 0.000 description 1
- 208000010667 Carcinoma of liver and intrahepatic biliary tract Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- KUMXLFIBWFCMOJ-UHFFFAOYSA-N Dimethyl-aethyl-propyl-methan Natural products CCCC(C)(C)CC KUMXLFIBWFCMOJ-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 229940124602 FDA-approved drug Drugs 0.000 description 1
- UYTPUPDQBNUYGX-UHFFFAOYSA-N Guanine Natural products O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 1
- 206010073069 Hepatic cancer Diseases 0.000 description 1
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
- 101900297506 Human immunodeficiency virus type 1 group M subtype B Reverse transcriptase/ribonuclease H Proteins 0.000 description 1
- 102100034343 Integrase Human genes 0.000 description 1
- XETQTCAMTVHYPO-UHFFFAOYSA-N Isocamphan von ungewisser Konfiguration Natural products C1CC2C(C)(C)C(C)C1C2 XETQTCAMTVHYPO-UHFFFAOYSA-N 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 206010023126 Jaundice Diseases 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- 208000001940 Massive Hepatic Necrosis Diseases 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- IALRSQMWHFKJJA-JTQLQIEISA-N Nonane, 4-methyl- Chemical compound CCCCC[C@@H](C)CCC IALRSQMWHFKJJA-JTQLQIEISA-N 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- 102000001253 Protein Kinase Human genes 0.000 description 1
- 108010092799 RNA-directed DNA polymerase Proteins 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 108020005202 Viral DNA Proteins 0.000 description 1
- 229960004748 abacavir Drugs 0.000 description 1
- MCGSCOLBFJQGHM-SCZZXKLOSA-N abacavir Chemical compound C=12N=CN([C@H]3C=C[C@@H](CO)C3)C2=NC(N)=NC=1NC1CC1 MCGSCOLBFJQGHM-SCZZXKLOSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 231100000354 acute hepatitis Toxicity 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 238000012925 biological evaluation Methods 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- ZAGHKONXGGSVDV-UHFFFAOYSA-N butylcyclopentane Chemical compound CCCCC1CCCC1 ZAGHKONXGGSVDV-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 125000005518 carboxamido group Chemical group 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- 238000004296 chiral HPLC Methods 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 208000037976 chronic inflammation Diseases 0.000 description 1
- 230000006020 chronic inflammation Effects 0.000 description 1
- KVZJLSYJROEPSQ-OCAPTIKFSA-N cis-1,2-dimethylcyclohexane Chemical compound C[C@H]1CCCC[C@H]1C KVZJLSYJROEPSQ-OCAPTIKFSA-N 0.000 description 1
- PQXAPVOKLYINEI-UHFFFAOYSA-N cis-1-Methyl-3-ethyl-cyclopentan Natural products CCC1CCC(C)C1 PQXAPVOKLYINEI-UHFFFAOYSA-N 0.000 description 1
- NNBZCPXTIHJBJL-AOOOYVTPSA-N cis-decalin Chemical compound C1CCC[C@H]2CCCC[C@H]21 NNBZCPXTIHJBJL-AOOOYVTPSA-N 0.000 description 1
- GBBJCSTXCAQSSJ-XQXXSGGOSA-N clevudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1[C@H](F)[C@@H](O)[C@H](CO)O1 GBBJCSTXCAQSSJ-XQXXSGGOSA-N 0.000 description 1
- 230000001010 compromised effect Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- LMGZGXSXHCMSAA-UHFFFAOYSA-N cyclodecane Chemical compound C1CCCCCCCCC1 LMGZGXSXHCMSAA-UHFFFAOYSA-N 0.000 description 1
- JJWIOXUMXIOXQN-UHFFFAOYSA-N cyclohexadecane Chemical compound C1CCCCCCCCCCCCCCC1 JJWIOXUMXIOXQN-UHFFFAOYSA-N 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 1
- GPTJTTCOVDDHER-UHFFFAOYSA-N cyclononane Chemical compound C1CCCCCCCC1 GPTJTTCOVDDHER-UHFFFAOYSA-N 0.000 description 1
- SRONXYPFSAKOGH-UHFFFAOYSA-N cyclopentadecane Chemical compound C1CCCCCCCCCCCCCC1 SRONXYPFSAKOGH-UHFFFAOYSA-N 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- UCGNTQHMZUJDJR-UHFFFAOYSA-N docosylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCCCCCC1CCCCC1 UCGNTQHMZUJDJR-UHFFFAOYSA-N 0.000 description 1
- DHSBZVCYIOGRQS-UHFFFAOYSA-N docosylcyclopentane Chemical compound CCCCCCCCCCCCCCCCCCCCCCC1CCCC1 DHSBZVCYIOGRQS-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- UFGYKQGTOYNLLD-UHFFFAOYSA-N dodecylcyclopentane Chemical compound CCCCCCCCCCCCC1CCCC1 UFGYKQGTOYNLLD-UHFFFAOYSA-N 0.000 description 1
- CNMRBOKAAZWYBQ-UHFFFAOYSA-N dotriacontylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCCC1 CNMRBOKAAZWYBQ-UHFFFAOYSA-N 0.000 description 1
- DMSJNAIKBCWKTA-UHFFFAOYSA-N dotriacontylcyclopentane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCC1 DMSJNAIKBCWKTA-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000003821 enantio-separation Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- NEZRFXZYPAIZAD-UHFFFAOYSA-N ethylcyclobutane Chemical compound CCC1CCC1 NEZRFXZYPAIZAD-UHFFFAOYSA-N 0.000 description 1
- FOTXAJDDGPYIFU-UHFFFAOYSA-N ethylcyclopropane Chemical compound CCC1CC1 FOTXAJDDGPYIFU-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229930006738 fenchane Natural products 0.000 description 1
- 229960004413 flucytosine Drugs 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- IVSXFFJGASXYCL-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=NC=N[C]21 IVSXFFJGASXYCL-UHFFFAOYSA-N 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- FXKJJAAVRNCTIT-UHFFFAOYSA-N henicosylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCCCCC1CCCCC1 FXKJJAAVRNCTIT-UHFFFAOYSA-N 0.000 description 1
- CJVRVCCEILWVOL-UHFFFAOYSA-N hentriacontylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCCC1 CJVRVCCEILWVOL-UHFFFAOYSA-N 0.000 description 1
- RCNBICDSOBNGRO-UHFFFAOYSA-N hentriacontylcyclopentane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCC1 RCNBICDSOBNGRO-UHFFFAOYSA-N 0.000 description 1
- 231100000234 hepatic damage Toxicity 0.000 description 1
- 208000002672 hepatitis B Diseases 0.000 description 1
- 231100000844 hepatocellular carcinoma Toxicity 0.000 description 1
- OJQBAJIDUKKNJG-UHFFFAOYSA-N heptacosylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCCC1 OJQBAJIDUKKNJG-UHFFFAOYSA-N 0.000 description 1
- GXBBDUZLKYHFHZ-UHFFFAOYSA-N heptacosylcyclopentane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCC1 GXBBDUZLKYHFHZ-UHFFFAOYSA-N 0.000 description 1
- VLHZQNGNJQYAIZ-UHFFFAOYSA-N heptadecylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCC1CCCCC1 VLHZQNGNJQYAIZ-UHFFFAOYSA-N 0.000 description 1
- SSQOCAUNFVDULL-UHFFFAOYSA-N heptadecylcyclopentane Chemical compound CCCCCCCCCCCCCCCCCC1CCCC1 SSQOCAUNFVDULL-UHFFFAOYSA-N 0.000 description 1
- YCOZIPAWZNQLMR-UHFFFAOYSA-N heptane - octane Natural products CCCCCCCCCCCCCCC YCOZIPAWZNQLMR-UHFFFAOYSA-N 0.000 description 1
- BOFNAOHMSHEKQL-UHFFFAOYSA-N heptylcyclopentane Chemical compound CCCCCCCC1CCCC1 BOFNAOHMSHEKQL-UHFFFAOYSA-N 0.000 description 1
- IAAZRRNEHQJEJS-UHFFFAOYSA-N hexacosylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCCC1 IAAZRRNEHQJEJS-UHFFFAOYSA-N 0.000 description 1
- VQSWPSXXWBSRQN-UHFFFAOYSA-N hexacosylcyclopentane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCC1 VQSWPSXXWBSRQN-UHFFFAOYSA-N 0.000 description 1
- NRHBFNBZAZZTAU-UHFFFAOYSA-N hexadecylcyclohexane Chemical compound CCCCCCCCCCCCCCCCC1CCCCC1 NRHBFNBZAZZTAU-UHFFFAOYSA-N 0.000 description 1
- OVSLZZWDHQVSFR-UHFFFAOYSA-N hexatriacontylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCCC1 OVSLZZWDHQVSFR-UHFFFAOYSA-N 0.000 description 1
- XMXSTJPMDVDRRH-UHFFFAOYSA-N hexatriacontylcyclopentane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCC1 XMXSTJPMDVDRRH-UHFFFAOYSA-N 0.000 description 1
- LKHGKBBAJAFMSQ-UHFFFAOYSA-N hexylcyclopentane Chemical compound CCCCCCC1CCCC1 LKHGKBBAJAFMSQ-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 description 1
- 229960001627 lamivudine Drugs 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 201000007270 liver cancer Diseases 0.000 description 1
- 201000002250 liver carcinoma Diseases 0.000 description 1
- 230000008818 liver damage Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- YGZQYMMFALYKCO-GXTWGEPZSA-N n-[1-[(2r,5s)-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]benzamide Chemical compound O1[C@H](CO)CC[C@@H]1N1C(=O)N=C(NC(=O)C=2C=CC=CC=2)C=C1 YGZQYMMFALYKCO-GXTWGEPZSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229940094933 n-dodecane Drugs 0.000 description 1
- HOWGUJZVBDQJKV-UHFFFAOYSA-N n-propyl-nonadecane Natural products CCCCCCCCCCCCCCCCCCCCCC HOWGUJZVBDQJKV-UHFFFAOYSA-N 0.000 description 1
- MMENDLLEZBPHSR-UHFFFAOYSA-N nonacosylcyclopentane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCC1 MMENDLLEZBPHSR-UHFFFAOYSA-N 0.000 description 1
- YVTPTBVYGTYTKP-UHFFFAOYSA-N nonadecylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCCC1CCCCC1 YVTPTBVYGTYTKP-UHFFFAOYSA-N 0.000 description 1
- DNSPFUFOXYIYCY-UHFFFAOYSA-N nonadecylcyclopentane Chemical compound CCCCCCCCCCCCCCCCCCCC1CCCC1 DNSPFUFOXYIYCY-UHFFFAOYSA-N 0.000 description 1
- CLMFECCMAVQYQA-UHFFFAOYSA-N nonylcyclohexane Chemical compound CCCCCCCCCC1CCCCC1 CLMFECCMAVQYQA-UHFFFAOYSA-N 0.000 description 1
- QUXXWIDLWMFSTJ-UHFFFAOYSA-N octacosylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCCC1 QUXXWIDLWMFSTJ-UHFFFAOYSA-N 0.000 description 1
- QBXAVSNMLFNZOR-UHFFFAOYSA-N octacosylcyclopentane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCC1 QBXAVSNMLFNZOR-UHFFFAOYSA-N 0.000 description 1
- MWWVNZNVTGBKQO-UHFFFAOYSA-N octadecylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCC1CCCCC1 MWWVNZNVTGBKQO-UHFFFAOYSA-N 0.000 description 1
- BMGGVLNZZWZSDT-UHFFFAOYSA-N octadecylcyclopentane Chemical compound CCCCCCCCCCCCCCCCCCC1CCCC1 BMGGVLNZZWZSDT-UHFFFAOYSA-N 0.000 description 1
- FBXWCEKQCVOOLT-UHFFFAOYSA-N octylcyclohexane Chemical compound CCCCCCCCC1CCCCC1 FBXWCEKQCVOOLT-UHFFFAOYSA-N 0.000 description 1
- HARXDULSBROLME-UHFFFAOYSA-N octylcyclopentane Chemical compound CCCCCCCCC1CCCC1 HARXDULSBROLME-UHFFFAOYSA-N 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229930004008 p-menthane Natural products 0.000 description 1
- JZIWECMAEHNDRL-UHFFFAOYSA-N pentacosylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC1CCCCC1 JZIWECMAEHNDRL-UHFFFAOYSA-N 0.000 description 1
- KPZXPRZDTHVHLX-UHFFFAOYSA-N pentacosylcyclopentane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC1CCCC1 KPZXPRZDTHVHLX-UHFFFAOYSA-N 0.000 description 1
- ZNUABQHWFGTOCO-UHFFFAOYSA-N pentadecylcyclohexane Chemical compound CCCCCCCCCCCCCCCC1CCCCC1 ZNUABQHWFGTOCO-UHFFFAOYSA-N 0.000 description 1
- WTFOZIBFLJCOHA-UHFFFAOYSA-N pentatriacontylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCCC1 WTFOZIBFLJCOHA-UHFFFAOYSA-N 0.000 description 1
- IVYUBHPJNFFACJ-UHFFFAOYSA-N pentatriacontylcyclopentane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCC1 IVYUBHPJNFFACJ-UHFFFAOYSA-N 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- DGZUEIPKRRSMGK-UHFFFAOYSA-N quadricyclane Chemical compound C1C2C3C2C2C3C12 DGZUEIPKRRSMGK-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- WJXREUZUPGMAII-UHFFFAOYSA-N sulfurazidic acid Chemical compound OS(=O)(=O)N=[N+]=[N-] WJXREUZUPGMAII-UHFFFAOYSA-N 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- WMFMOFURZNHHDD-UHFFFAOYSA-N tetracosylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCC1CCCCC1 WMFMOFURZNHHDD-UHFFFAOYSA-N 0.000 description 1
- HCYULJKBGLUBDO-UHFFFAOYSA-N tetracosylcyclopentane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCC1CCCC1 HCYULJKBGLUBDO-UHFFFAOYSA-N 0.000 description 1
- NQAVPKIJZCHUNS-UHFFFAOYSA-N tetradecylcyclohexane Chemical compound CCCCCCCCCCCCCCC1CCCCC1 NQAVPKIJZCHUNS-UHFFFAOYSA-N 0.000 description 1
- MJWRHKSSZBHAEW-UHFFFAOYSA-N tetradecylcyclopentane Chemical compound CCCCCCCCCCCCCCC1CCCC1 MJWRHKSSZBHAEW-UHFFFAOYSA-N 0.000 description 1
- IQNOOEILKDDPAZ-UHFFFAOYSA-N tetratriacontylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCCC1 IQNOOEILKDDPAZ-UHFFFAOYSA-N 0.000 description 1
- ZTKZBMRGTUDQQJ-UHFFFAOYSA-N tetratriacontylcyclopentane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCC1 ZTKZBMRGTUDQQJ-UHFFFAOYSA-N 0.000 description 1
- KVZJLSYJROEPSQ-HTQZYQBOSA-N trans-1,2-dimethylcyclohexane Chemical compound C[C@@H]1CCCC[C@H]1C KVZJLSYJROEPSQ-HTQZYQBOSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- OLTHARGIAFTREU-UHFFFAOYSA-N triacontane Natural products CCCCCCCCCCCCCCCCCCCCC(C)CCCCCCCC OLTHARGIAFTREU-UHFFFAOYSA-N 0.000 description 1
- HLUVZZITVLCHHG-UHFFFAOYSA-N triacontylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCCC1 HLUVZZITVLCHHG-UHFFFAOYSA-N 0.000 description 1
- LUTRXSGNOWYTNZ-UHFFFAOYSA-N tricosylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC1CCCCC1 LUTRXSGNOWYTNZ-UHFFFAOYSA-N 0.000 description 1
- MVLKTFOLEWGUOV-UHFFFAOYSA-N tricosylcyclopentane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC1CCCC1 MVLKTFOLEWGUOV-UHFFFAOYSA-N 0.000 description 1
- DKRUJKKWJGNYQN-UHFFFAOYSA-N tridecylcyclohexane Chemical compound CCCCCCCCCCCCCC1CCCCC1 DKRUJKKWJGNYQN-UHFFFAOYSA-N 0.000 description 1
- 125000002264 triphosphate group Chemical class [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 description 1
- SUJUOAZFECLBOA-UHFFFAOYSA-N tritriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC SUJUOAZFECLBOA-UHFFFAOYSA-N 0.000 description 1
- JKDDSQDZJYBASB-UHFFFAOYSA-N tritriacontylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCCC1 JKDDSQDZJYBASB-UHFFFAOYSA-N 0.000 description 1
- WORVRGQZSXETON-UHFFFAOYSA-N tritriacontylcyclopentane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCC1 WORVRGQZSXETON-UHFFFAOYSA-N 0.000 description 1
- MFAFEMCKJDFCCE-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC.CCCCCCCCCCC MFAFEMCKJDFCCE-UHFFFAOYSA-N 0.000 description 1
- UIKNJDHXJRISIU-UHFFFAOYSA-N undecylcyclohexane Chemical compound C(CCCCCCCCCC)C1CCCCC1.C(CCCCCCCCCC)C1CCCCC1 UIKNJDHXJRISIU-UHFFFAOYSA-N 0.000 description 1
- 229960000523 zalcitabine Drugs 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- 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
- A61P31/14—Antivirals for RNA viruses
-
- 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
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
-
- 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
- C07H19/16—Purine radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Virology (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Public Health (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)
- Biotechnology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34155501P | 2001-12-14 | 2001-12-14 | |
| US60/341,555 | 2001-12-14 | ||
| PCT/US2002/040081 WO2003063771A2 (en) | 2001-12-14 | 2002-12-13 | N4-acylcytosine nucleosides for treatment of viral iinfections |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2002365234A1 AU2002365234A1 (en) | 2003-09-18 |
| AU2002365234B2 true AU2002365234B2 (en) | 2009-01-29 |
Family
ID=23338072
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2002365234A Ceased AU2002365234B2 (en) | 2001-12-14 | 2002-12-13 | N4-acylcytosine nucleosides for treatment of viral infections |
| AU2002364730A Abandoned AU2002364730A1 (en) | 2001-12-14 | 2002-12-16 | N4-acylcytosine-1,3-dioxolane nucleosides for treatment of viral infections |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2002364730A Abandoned AU2002364730A1 (en) | 2001-12-14 | 2002-12-16 | N4-acylcytosine-1,3-dioxolane nucleosides for treatment of viral infections |
Country Status (10)
| Country | Link |
|---|---|
| US (6) | US7105527B2 (https=) |
| EP (1) | EP1569652A4 (https=) |
| JP (1) | JP2005519916A (https=) |
| KR (1) | KR100978904B1 (https=) |
| CN (1) | CN100560073C (https=) |
| AU (2) | AU2002365234B2 (https=) |
| BR (1) | BR0214944A (https=) |
| CA (1) | CA2470255C (https=) |
| MX (1) | MXPA04005779A (https=) |
| WO (2) | WO2003063771A2 (https=) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6790228B2 (en) * | 1999-12-23 | 2004-09-14 | Advanced Cardiovascular Systems, Inc. | Coating for implantable devices and a method of forming the same |
| EP1964569A3 (en) | 2000-04-13 | 2009-07-22 | Pharmasset, Inc. | 3'-or 2'-hydroxymethyl substituted nucleoside derivatives for treatment of viral infections |
| MY164523A (en) * | 2000-05-23 | 2017-12-29 | Univ Degli Studi Cagliari | Methods and compositions for treating hepatitis c virus |
| KR20080021797A (ko) | 2000-05-26 | 2008-03-07 | 이데닉스(케이만)리미티드 | 플라비바이러스 및 페스티바이러스의 치료방법 및 조성물 |
| EP1569652A4 (en) * | 2001-12-14 | 2008-07-02 | Pharmasset Inc | NUCLEOSIDES N SP 4 / SP-ACYLCYTOSINES FOR THE TREATMENT OF VIRAL INFECTIONS |
| US7608600B2 (en) | 2002-06-28 | 2009-10-27 | Idenix Pharmaceuticals, Inc. | Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections |
| NZ537662A (en) | 2002-06-28 | 2007-10-26 | Idenix Cayman Ltd | 2'-C-methyl-3'-O-L-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections |
| PL374781A1 (en) * | 2002-06-28 | 2005-10-31 | Idenix (Cayman) Limited | 2'-c-methyl-3'-o-l-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections |
| JP2006507235A (ja) | 2002-08-01 | 2006-03-02 | フアーマセツト・インコーポレイテツド | フラビウイルス科ウイルス感染治療のためのビシクロ［４．２．１］ノナン系を有する化合物 |
| HUE033832T2 (en) * | 2002-11-15 | 2018-01-29 | Idenix Pharmaceuticals Llc | 2'-methyl nucleosides in combination with interferon and Flaviviridae mutation |
| RU2005121904A (ru) | 2002-12-12 | 2006-01-20 | Айденикс (Кайман) Лимитед (Ky) | Способ получения 2`-разветвленных нуклеозидов |
| CA2425031A1 (en) * | 2003-04-01 | 2004-10-01 | Smithkline Beecham Corporation | Pharmaceutical compositions |
| EP2345657A1 (en) * | 2003-05-30 | 2011-07-20 | Pharmasset, Inc. | Modified fluorinated nucleoside analogues |
| WO2005097618A2 (en) * | 2004-04-01 | 2005-10-20 | Achillion Pharmaceuticals, Inc. | Low dose therapy for treating viral infections |
| CN101023094B (zh) * | 2004-07-21 | 2011-05-18 | 法莫赛特股份有限公司 | 烷基取代的2-脱氧-2-氟代-d-呋喃核糖基嘧啶和嘌呤及其衍生物的制备 |
| AU2005285045B2 (en) | 2004-09-14 | 2011-10-13 | Gilead Sciences, Inc. | Preparation of 2'fluoro-2'- alkyl- substituted or other optionally substituted ribofuranosyl pyrimidines and purines and their derivatives |
| WO2006044968A2 (en) * | 2004-10-19 | 2006-04-27 | Achillion Pharmaceuticals, Inc. | Combination therapy for treating viral infections |
| US7968703B2 (en) * | 2005-03-07 | 2011-06-28 | Shire Canada Inc. | Process and methods for the preparation of optically active cis-2-hydroxymethyl-4- (cytosin-1'-yl)-1,3-oxathiolane or pharmaceutically acceptable salts thereof |
| EP1976382B1 (en) * | 2005-12-23 | 2013-04-24 | IDENIX Pharmaceuticals, Inc. | Process for preparing a synthetic intermediate for preparation of branched nucleosides |
| GB0623493D0 (en) | 2006-11-24 | 2007-01-03 | Univ Cardiff | Chemical compounds |
| US7964580B2 (en) | 2007-03-30 | 2011-06-21 | Pharmasset, Inc. | Nucleoside phosphoramidate prodrugs |
| US8173621B2 (en) | 2008-06-11 | 2012-05-08 | Gilead Pharmasset Llc | Nucleoside cyclicphosphates |
| SG194404A1 (en) | 2008-12-23 | 2013-11-29 | Gilead Pharmasset Llc | Synthesis of purine nucleosides |
| KR20110098849A (ko) | 2008-12-23 | 2011-09-01 | 파마셋 인코포레이티드 | 뉴클레오시드 유사체 |
| PT2376088T (pt) | 2008-12-23 | 2017-05-02 | Gilead Pharmasset Llc | Fosforamidatos de nucleósidos de 2-amino-purina 6-osubstituída |
| TWI598358B (zh) | 2009-05-20 | 2017-09-11 | 基利法瑪席特有限責任公司 | 核苷磷醯胺 |
| US8618076B2 (en) | 2009-05-20 | 2013-12-31 | Gilead Pharmasset Llc | Nucleoside phosphoramidates |
| PT2609923T (pt) | 2010-03-31 | 2017-08-30 | Gilead Pharmasset Llc | Processo para a cristalização de 2-(((s)- (perfluorofenoxi)(fenoxi)fosforil)amino)propanoato de (s)-isopropilo |
| PL3290428T3 (pl) | 2010-03-31 | 2022-02-07 | Gilead Pharmasset Llc | Tabletka zawierająca krystaliczny (S)-2-(((S)-(((2R,3R,4R,5R)-5-(2,4-diokso-3,4-dihydropirymidyn-1(2H)-ylo)-4-fluoro-3-hydroksy-4-metylotetrahydrofuran-2-ylo)metoksy)(fenoksy)fosforylo)amino)propanian izopropylu |
| AU2011336632B2 (en) | 2010-11-30 | 2015-09-03 | Gilead Pharmasset Llc | Compounds |
| PL2709613T5 (pl) | 2011-09-16 | 2020-12-14 | Gilead Pharmasset Llc | Metody leczenia hcv |
| US8889159B2 (en) | 2011-11-29 | 2014-11-18 | Gilead Pharmasset Llc | Compositions and methods for treating hepatitis C virus |
| CN103242400B (zh) * | 2012-02-08 | 2016-06-08 | 河南师范大学 | 具有抗hiv活性的5-取代嘧啶核苷-噻唑啉酮杂化体及其制备方法 |
| PT2950786T (pt) | 2013-01-31 | 2020-03-03 | Gilead Pharmasset Llc | Formulação de combinação de dois compostos antivirais |
| EA201690473A1 (ru) | 2013-08-27 | 2017-03-31 | ГАЙЛИД ФАРМАССЕТ ЭлЭлСи | Комбинированный состав двух противовирусных соединений |
| CA3182565A1 (en) | 2015-03-06 | 2016-09-15 | Atea Pharmaceuticals, Inc. | .beta.-d-2'-deoxy-2'-.alpha.-fluoro-2'-.beta.-c-substituted-2-modified-n6-substituted purine nucleotides for hcv treatment |
| US10711029B2 (en) | 2016-07-14 | 2020-07-14 | Atea Pharmaceuticals, Inc. | Beta-d-2′-deoxy-2′-alpha-fluoro-2′-beta-c-substituted-4′fluoro-n6-substituted-6-amino-2-substituted purine nucleotides for the treatment of hepatitis c virus infection |
| DK3512863T3 (da) | 2016-09-07 | 2022-03-07 | Atea Pharmaceuticals Inc | 2¿-substituerede-N6-substituerede purinnukleotider til behandling af RNA-virus |
| CN115477679A (zh) | 2017-02-01 | 2022-12-16 | 阿堤亚制药公司 | 用于治疗丙型肝炎病毒的核苷酸半硫酸盐 |
| EP3773753A4 (en) | 2018-04-10 | 2021-12-22 | ATEA Pharmaceuticals, Inc. | TREATMENT OF PATIENTS INFECTED WITH THE HEPATITIS C VIRUS WITH CIRRHOSIS |
| US10874687B1 (en) | 2020-02-27 | 2020-12-29 | Atea Pharmaceuticals, Inc. | Highly active compounds against COVID-19 |
| KR20240022574A (ko) | 2021-06-17 | 2024-02-20 | 아테아 파마슈티컬즈, 인크. | 유리한 항-hcv 조합 요법 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0311100A2 (de) * | 1987-10-09 | 1989-04-12 | F. Hoffmann-La Roche Ag | Neue Dideoxycytidin-Derivate, ihre Herstellung und Verwendung für Pharmazeutika |
| WO1999026958A1 (en) * | 1997-11-25 | 1999-06-03 | Protarga, Inc. | Nucleoside analog compositions and uses thereof |
| WO1999043691A1 (en) * | 1998-02-25 | 1999-09-02 | Emory University | 2'-fluoronucleosides |
| AU2002228749B2 (en) * | 2000-10-18 | 2008-04-24 | Pharmasset Inc | Modified nucleosides for treatment of viral infections and abnormal cellular proliferation |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US13660A (en) * | 1855-10-09 | Improvements | ||
| US3309359A (en) * | 1965-10-22 | 1967-03-14 | Hoffmann La Roche | N-mono-acyl-5-fluorocytosine derivatives and process |
| NL8202626A (nl) | 1982-06-29 | 1984-01-16 | Stichting Rega V Z W | Derivaten van 9-(2-hydroxyethoxymethyl)guanine. |
| US4522811A (en) * | 1982-07-08 | 1985-06-11 | Syntex (U.S.A.) Inc. | Serial injection of muramyldipeptides and liposomes enhances the anti-infective activity of muramyldipeptides |
| GB8719367D0 (en) * | 1987-08-15 | 1987-09-23 | Wellcome Found | Therapeutic compounds |
| US6350753B1 (en) * | 1988-04-11 | 2002-02-26 | Biochem Pharma Inc. | 2-Substituted-4-substituted-1,3-dioxolanes and use thereof |
| NL8901258A (nl) | 1989-05-19 | 1990-12-17 | Stichting Rega V Z W | 5-halogeno-2',3'-dideoxycytidinederivaten in geneesmiddelen voor het behandelen van retrovirus-infecties. |
| DD293498A5 (de) | 1989-07-20 | 1991-09-05 | Zi Fuer Molekularbiologie Der Adw,De | Verfahren zur herstellung eines mittels fuer die behandlung oder prophylaxe von hepatits-infektionen bei mensch und tier |
| JPH05310777A (ja) | 1992-05-14 | 1993-11-22 | Yoshitomi Pharmaceut Ind Ltd | ２’−デオキシ−２’−メチリデンシチジン化合物 |
| TW254946B (https=) * | 1992-12-18 | 1995-08-21 | Hoffmann La Roche | |
| TW374087B (en) * | 1993-05-25 | 1999-11-11 | Univ Yale | L-2',3'-dideoxy nucleotide analogs as anti-hepatitis B(HBV) and anti-HIV agents |
| TW530047B (en) | 1994-06-08 | 2003-05-01 | Pfizer | Corticotropin releasing factor antagonists |
| US5703058A (en) * | 1995-01-27 | 1997-12-30 | Emory University | Compositions containing 5-fluoro-2',3'-didehydro-2',3'-dideoxycytidine or a mono-, di-, or triphosphate thereof and a second antiviral agent |
| GB9525606D0 (en) | 1995-12-14 | 1996-02-14 | Iaf Biochem Int | Method and compositions for the synthesis of dioxolane nucleosides with - configuration |
| AU4988697A (en) * | 1996-10-24 | 1998-05-15 | Vion Pharmaceuticals, Inc. | Monophosphate prodrugs of beta-l-fd4c and beta-l-fddc as potent antiviral agents |
| AU1201502A (en) * | 2000-10-13 | 2002-04-22 | Shire Biochem Inc | Dioxolane analogs for improved inter-cellular delivery |
| EP1569652A4 (en) * | 2001-12-14 | 2008-07-02 | Pharmasset Inc | NUCLEOSIDES N SP 4 / SP-ACYLCYTOSINES FOR THE TREATMENT OF VIRAL INFECTIONS |
-
2002
- 2002-12-13 EP EP02804833A patent/EP1569652A4/en not_active Withdrawn
- 2002-12-13 WO PCT/US2002/040081 patent/WO2003063771A2/en not_active Ceased
- 2002-12-13 KR KR1020047009263A patent/KR100978904B1/ko not_active Expired - Fee Related
- 2002-12-13 CA CA2470255A patent/CA2470255C/en not_active Expired - Fee Related
- 2002-12-13 BR BR0214944-3A patent/BR0214944A/pt not_active Application Discontinuation
- 2002-12-13 MX MXPA04005779A patent/MXPA04005779A/es active IP Right Grant
- 2002-12-13 CN CNB028278402A patent/CN100560073C/zh not_active Expired - Fee Related
- 2002-12-13 AU AU2002365234A patent/AU2002365234B2/en not_active Ceased
- 2002-12-13 JP JP2003563467A patent/JP2005519916A/ja active Pending
- 2002-12-13 US US10/318,511 patent/US7105527B2/en not_active Expired - Fee Related
- 2002-12-16 AU AU2002364730A patent/AU2002364730A1/en not_active Abandoned
- 2002-12-16 US US10/320,350 patent/US6908924B2/en not_active Ceased
- 2002-12-16 WO PCT/US2002/040090 patent/WO2003051306A2/en not_active Ceased
-
2006
- 2006-07-31 US US11/461,338 patent/US20070078080A1/en not_active Abandoned
-
2007
- 2007-06-21 US US11/821,076 patent/USRE42015E1/en not_active Expired - Fee Related
-
2008
- 2008-01-04 US US11/969,427 patent/US8114997B2/en not_active Expired - Fee Related
-
2012
- 2012-02-13 US US13/371,654 patent/US20120202766A1/en not_active Abandoned
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0311100A2 (de) * | 1987-10-09 | 1989-04-12 | F. Hoffmann-La Roche Ag | Neue Dideoxycytidin-Derivate, ihre Herstellung und Verwendung für Pharmazeutika |
| WO1999026958A1 (en) * | 1997-11-25 | 1999-06-03 | Protarga, Inc. | Nucleoside analog compositions and uses thereof |
| WO1999043691A1 (en) * | 1998-02-25 | 1999-09-02 | Emory University | 2'-fluoronucleosides |
| AU2002228749B2 (en) * | 2000-10-18 | 2008-04-24 | Pharmasset Inc | Modified nucleosides for treatment of viral infections and abnormal cellular proliferation |
Non-Patent Citations (2)
| Title |
|---|
| Lee et al. J. Med. Chem. 1999 42, 1320-1328 * |
| Zhang et al. J. Org. Chem. 2000, 65, 7075-7082 * |
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA04005779A (es) | 2005-05-16 |
| WO2003051306A2 (en) | 2003-06-26 |
| EP1569652A4 (en) | 2008-07-02 |
| CA2470255A1 (en) | 2003-08-07 |
| WO2003063771A3 (en) | 2005-07-07 |
| US20070078080A1 (en) | 2007-04-05 |
| US8114997B2 (en) | 2012-02-14 |
| USRE42015E1 (en) | 2010-12-28 |
| BR0214944A (pt) | 2005-06-07 |
| WO2003051306A3 (en) | 2003-12-18 |
| US20030176319A1 (en) | 2003-09-18 |
| CN1617726A (zh) | 2005-05-18 |
| CA2470255C (en) | 2012-01-17 |
| WO2003063771A2 (en) | 2003-08-07 |
| US6908924B2 (en) | 2005-06-21 |
| JP2005519916A (ja) | 2005-07-07 |
| EP1569652A2 (en) | 2005-09-07 |
| US20040214844A1 (en) | 2004-10-28 |
| US7105527B2 (en) | 2006-09-12 |
| AU2002364730A8 (en) | 2003-06-30 |
| KR100978904B1 (ko) | 2010-08-31 |
| AU2002364730A1 (en) | 2003-06-30 |
| US20120202766A1 (en) | 2012-08-09 |
| CN100560073C (zh) | 2009-11-18 |
| US20090176730A1 (en) | 2009-07-09 |
| KR20040094398A (ko) | 2004-11-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2002365234B2 (en) | N4-acylcytosine nucleosides for treatment of viral infections | |
| AU2002365234A1 (en) | N4-acylcytosine nucleosides for treatment of viral infections | |
| EP1058686B1 (en) | 2'-fluoronucleosides | |
| JP6553551B2 (ja) | Ｂ型肝炎抗ウイルス剤 | |
| AU693079B2 (en) | Enantiomerically pure beta -D-dioxolane nucleosides with selective anti-hepatitis B virus activity | |
| US5990093A (en) | Treating HBV with phospholipid prodrugs of β-L-2',3'-dideoxyadenosine 5'-monophosphate | |
| EP2710023A2 (en) | Purine monophosphate prodrugs for treatment of viral infections | |
| CA2685748A1 (en) | Azido purine nucleosides for treatment of viral infections | |
| JP2003176296A (ja) | 単環式ヌクレオシド、その類似体および使用 | |
| WO2012121939A2 (en) | Aminopyrazine compounds | |
| TW201538517A (zh) | 作為流感病毒ｒｎａ複製之抑制劑之經４’－二氟甲基取代之核苷衍生物 | |
| EP3523292B1 (en) | Heteroaryl compounds and their use as mer inhibitors | |
| WO2010068708A2 (en) | 3'-azido purine nucleotide prodrugs for treatment of viral infections | |
| EA036892B1 (ru) | Макрогетероциклические нуклеозидные производные и их аналоги, получение и применение | |
| CN101479289A (zh) | 治疗化合物 | |
| JP2022531899A (ja) | Ｓｔｉｎｇモジュレータとしての修飾環状ジヌクレオシド化合物 | |
| BR112016008934B1 (pt) | Pró-fármaco mútuo compreendendo ácidos graxos de cadeia curta e zebularina ou 1- ciano-citarabina para tratamento de câncer, e uso do referido pró-fármaco | |
| JP2024515786A (ja) | プリンヌクレオシド、それらの中間体、およびそれらの調製方法 | |
| HK40012561B (en) | Heteroaryl compounds and their use as mer inhibitors |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| TC | Change of applicant's name (sec. 104) |
Owner name: PHARMASSET INC Free format text: FORMER NAME: PHARMASSET LTD. |
|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |