JP2010515760A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2010515760A5 JP2010515760A5 JP2009545720A JP2009545720A JP2010515760A5 JP 2010515760 A5 JP2010515760 A5 JP 2010515760A5 JP 2009545720 A JP2009545720 A JP 2009545720A JP 2009545720 A JP2009545720 A JP 2009545720A JP 2010515760 A5 JP2010515760 A5 JP 2010515760A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- aryl
- compound according
- alkenyl
- 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.)
- Pending
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 112
- 150000001875 compounds Chemical class 0.000 claims description 105
- -1 NH 2 Chemical group 0.000 claims description 72
- 125000003118 aryl group Chemical group 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 37
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 125000003342 alkenyl group Chemical group 0.000 claims description 26
- 125000000304 alkynyl group Chemical group 0.000 claims description 24
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 125000003107 substituted aryl group Chemical group 0.000 claims description 22
- 229940002612 prodrug Drugs 0.000 claims description 21
- 239000000651 prodrug Substances 0.000 claims description 21
- 229910052731 fluorine Inorganic materials 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 19
- 241001465754 Metazoa Species 0.000 claims description 16
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000002252 acyl group Chemical group 0.000 claims description 14
- 125000000539 amino acid group Chemical group 0.000 claims description 14
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
- 239000001177 diphosphate Substances 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 239000001226 triphosphate Substances 0.000 claims description 10
- 102000006992 Interferon-alpha Human genes 0.000 claims description 9
- 108010047761 Interferon-alpha Proteins 0.000 claims description 9
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 8
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 8
- 208000036142 Viral infection Diseases 0.000 claims description 8
- 125000004423 acyloxy group Chemical group 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 125000002264 triphosphate group Chemical group [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 claims description 8
- 230000009385 viral infection Effects 0.000 claims description 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 6
- 150000001413 amino acids Chemical class 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 235000011180 diphosphates Nutrition 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 6
- 229960000329 ribavirin Drugs 0.000 claims description 6
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 6
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
- 229940124683 HCV polymerase inhibitor Drugs 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 239000002246 antineoplastic agent Substances 0.000 claims description 4
- 239000003443 antiviral agent Substances 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 201000011510 cancer Diseases 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- ISQVBYGGNVVVHB-UHFFFAOYSA-N cyclopentylmethanol Chemical compound OCC1CCCC1 ISQVBYGGNVVVHB-UHFFFAOYSA-N 0.000 claims description 3
- 150000004712 monophosphates Chemical group 0.000 claims description 3
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- OSBKZZCHLHZCDB-PBXRRBTRSA-N (2r,3r,4r)-2,3,4,5-tetrahydroxy-2-methylpentanal Chemical compound O=C[C@@](O)(C)[C@H](O)[C@H](O)CO OSBKZZCHLHZCDB-PBXRRBTRSA-N 0.000 claims description 2
- KDKMTIRSYIHSTB-MROZADKFSA-N (2r,3r,4r)-2,3,4,5-tetrahydroxypentanethial Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)C=S KDKMTIRSYIHSTB-MROZADKFSA-N 0.000 claims description 2
- NJYXSKVOTDPOAT-LMVFSUKVSA-N (2r,3r,4r)-2-fluoro-3,4,5-trihydroxypentanal Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](F)C=O NJYXSKVOTDPOAT-LMVFSUKVSA-N 0.000 claims description 2
- SQXRWAVEVYDDBF-LMVFSUKVSA-N (2r,3r,4r)-2-fluoro-3,4,5-trihydroxypentanethial Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](F)C=S SQXRWAVEVYDDBF-LMVFSUKVSA-N 0.000 claims description 2
- NJYXSKVOTDPOAT-WDCZJNDASA-N (2s,3r,4r)-2-fluoro-3,4,5-trihydroxypentanal Chemical compound OC[C@@H](O)[C@@H](O)[C@H](F)C=O NJYXSKVOTDPOAT-WDCZJNDASA-N 0.000 claims description 2
- SQXRWAVEVYDDBF-WDCZJNDASA-N (2s,3r,4r)-2-fluoro-3,4,5-trihydroxypentanethial Chemical compound OC[C@@H](O)[C@@H](O)[C@H](F)C=S SQXRWAVEVYDDBF-WDCZJNDASA-N 0.000 claims description 2
- ANFWGLPWDSXJEH-CRCLSJGQSA-N (3s,4r)-3,4,5-trihydroxypentanethial Chemical compound OC[C@@H](O)[C@@H](O)CC=S ANFWGLPWDSXJEH-CRCLSJGQSA-N 0.000 claims description 2
- JBFNVLCLNHQXCH-CRCLSJGQSA-N (3s,4r)-3-fluoro-4,5-dihydroxypentanethial Chemical compound OC[C@@H](O)[C@@H](F)CC=S JBFNVLCLNHQXCH-CRCLSJGQSA-N 0.000 claims description 2
- LFRDGHVRPSURMV-YFKPBYRVSA-N (4s)-4,5-dihydroxypentanal Chemical compound OC[C@@H](O)CCC=O LFRDGHVRPSURMV-YFKPBYRVSA-N 0.000 claims description 2
- XFBDCPQESJYXPC-YFKPBYRVSA-N (4s)-4,5-dihydroxypentanethial Chemical compound OC[C@@H](O)CCC=S XFBDCPQESJYXPC-YFKPBYRVSA-N 0.000 claims description 2
- LPXOUBDTZSHIOQ-UHFFFAOYSA-N 1,2,4-triazine-5-carbonitrile Chemical compound N#CC1=CN=NC=N1 LPXOUBDTZSHIOQ-UHFFFAOYSA-N 0.000 claims description 2
- IJIHMDVMMUTJEJ-UHFFFAOYSA-N 1,2,4-triazine-5-carboxamide Chemical compound NC(=O)C1=CN=NC=N1 IJIHMDVMMUTJEJ-UHFFFAOYSA-N 0.000 claims description 2
- GERSIKCSWYDFSJ-UHFFFAOYSA-N 1,2,4-triazine-5-carboxylic acid Chemical compound OC(=O)C1=CN=NC=N1 GERSIKCSWYDFSJ-UHFFFAOYSA-N 0.000 claims description 2
- IWUCXVSUMQZMFG-RGDLXGNYSA-N 1-[(2s,3s,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide Chemical compound N1=C(C(=O)N)N=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 IWUCXVSUMQZMFG-RGDLXGNYSA-N 0.000 claims description 2
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical compound O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 claims description 2
- UADBLZFWTJHOJC-UHFFFAOYSA-N 2-(hydroxymethyl)cyclopentan-1-ol Chemical compound OCC1CCCC1O UADBLZFWTJHOJC-UHFFFAOYSA-N 0.000 claims description 2
- VQKBTEBRZHBIGE-BYPYZUCNSA-N 2-[(1s)-1,2-dihydroxyethyl]sulfanylacetaldehyde Chemical compound OC[C@@H](O)SCC=O VQKBTEBRZHBIGE-BYPYZUCNSA-N 0.000 claims description 2
- ASJSAQIRZKANQN-CRCLSJGQSA-N 2-deoxy-D-ribose Chemical compound OC[C@@H](O)[C@@H](O)CC=O ASJSAQIRZKANQN-CRCLSJGQSA-N 0.000 claims description 2
- NGWKEVMCTIVMBA-UHFFFAOYSA-N 2-fluoro-4-(hydroxymethyl)pyrrolidin-3-ol Chemical compound OCC1CNC(F)C1O NGWKEVMCTIVMBA-UHFFFAOYSA-N 0.000 claims description 2
- DITIGNGDSVRJFX-UHFFFAOYSA-N 3-(hydroxymethyl)-4-methylidenecyclopentane-1,2-diol Chemical compound OCC1C(O)C(O)CC1=C DITIGNGDSVRJFX-UHFFFAOYSA-N 0.000 claims description 2
- DWROYQTVCUQGJR-UHFFFAOYSA-N 3-(hydroxymethyl)cyclopent-3-ene-1,2-diol Chemical compound OCC1=CCC(O)C1O DWROYQTVCUQGJR-UHFFFAOYSA-N 0.000 claims description 2
- BSQXZHMREYHKOM-UHFFFAOYSA-N 4-(hydroxymethyl)pyrrolidin-3-ol Chemical compound OCC1CNCC1O BSQXZHMREYHKOM-UHFFFAOYSA-N 0.000 claims description 2
- UKDQIWLEEJYIDQ-UHFFFAOYSA-N 4-(hydroxymethyl)pyrrolidine-2,3-diol Chemical compound OCC1CNC(O)C1O UKDQIWLEEJYIDQ-UHFFFAOYSA-N 0.000 claims description 2
- AAJXJLYUWKMQNO-UHFFFAOYSA-N 4-chloro-2-(1,2-oxazol-5-yl)phenol Chemical compound OC1=CC=C(Cl)C=C1C1=CC=NO1 AAJXJLYUWKMQNO-UHFFFAOYSA-N 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 claims description 2
- 102000016928 DNA-directed DNA polymerase Human genes 0.000 claims description 2
- 108010014303 DNA-directed DNA polymerase Proteins 0.000 claims description 2
- 241001115402 Ebolavirus Species 0.000 claims description 2
- 241001466953 Echovirus Species 0.000 claims description 2
- 241000709661 Enterovirus Species 0.000 claims description 2
- 241000991587 Enterovirus C Species 0.000 claims description 2
- 208000005176 Hepatitis C Diseases 0.000 claims description 2
- 241000725303 Human immunodeficiency virus Species 0.000 claims description 2
- 229940121740 Inosine monophosphate dehydrogenase inhibitor Drugs 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 2
- 101710118046 RNA-directed RNA polymerase Proteins 0.000 claims description 2
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 claims description 2
- 229940122055 Serine protease inhibitor Drugs 0.000 claims description 2
- 101710102218 Serine protease inhibitor Proteins 0.000 claims description 2
- 108010078233 Thymalfasin Proteins 0.000 claims description 2
- 102400000800 Thymosin alpha-1 Human genes 0.000 claims description 2
- 241000700647 Variola virus Species 0.000 claims description 2
- 241000700605 Viruses Species 0.000 claims description 2
- 241000710886 West Nile virus Species 0.000 claims description 2
- GAADRFVRUBFCML-UHFFFAOYSA-N [2-(hydroxymethyl)cyclobutyl]methanol Chemical compound OCC1CCC1CO GAADRFVRUBFCML-UHFFFAOYSA-N 0.000 claims description 2
- WUMYBFXWUJTWTB-UHFFFAOYSA-N [hydroxy(methoxy)phosphoryl] phosphono hydrogen phosphate Chemical compound COP(O)(=O)OP(O)(=O)OP(O)(O)=O WUMYBFXWUJTWTB-UHFFFAOYSA-N 0.000 claims description 2
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 claims description 2
- 230000001093 anti-cancer Effects 0.000 claims description 2
- 230000000340 anti-metabolite Effects 0.000 claims description 2
- 229940100197 antimetabolite Drugs 0.000 claims description 2
- 239000002256 antimetabolite Substances 0.000 claims description 2
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- LMYOLOWXQDLHKQ-UHFFFAOYSA-N cyclopent-2-en-1-ylmethanol Chemical compound OCC1CCC=C1 LMYOLOWXQDLHKQ-UHFFFAOYSA-N 0.000 claims description 2
- RGAPPBGFFPGONM-CRCLSJGQSA-N diazonio-[(2s,3s)-1,2-dihydroxy-5-sulfanylidenepentan-3-yl]azanide Chemical compound OC[C@@H](O)[C@H](CC=S)N=[N+]=[N-] RGAPPBGFFPGONM-CRCLSJGQSA-N 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 208000002672 hepatitis B Diseases 0.000 claims description 2
- 229940125697 hormonal agent Drugs 0.000 claims description 2
- 238000000338 in vitro Methods 0.000 claims description 2
- 238000001727 in vivo Methods 0.000 claims description 2
- 239000002348 inosinate dehydrogenase inhibitor Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
- DZONTPIFZFRSGP-UHFFFAOYSA-N methyl triazine-5-carboxylate Chemical compound COC(=O)C1=CN=NN=C1 DZONTPIFZFRSGP-UHFFFAOYSA-N 0.000 claims description 2
- 229930014626 natural product Natural products 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000002777 nucleoside Substances 0.000 claims description 2
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- QOTUIIJRVXKSJU-UHFFFAOYSA-N pyrrolidin-3-ylmethanol Chemical compound OCC1CCNC1 QOTUIIJRVXKSJU-UHFFFAOYSA-N 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 239000003001 serine protease inhibitor Substances 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- NHKZSTHOYNWEEZ-AFCXAGJDSA-N taribavirin Chemical compound N1=C(C(=N)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 NHKZSTHOYNWEEZ-AFCXAGJDSA-N 0.000 claims description 2
- 229950006081 taribavirin Drugs 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 2
- NZVYCXVTEHPMHE-ZSUJOUNUSA-N thymalfasin Chemical compound CC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(N)=O)C(O)=O NZVYCXVTEHPMHE-ZSUJOUNUSA-N 0.000 claims description 2
- 229960004231 thymalfasin Drugs 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 230000003612 virological effect Effects 0.000 claims description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 5
- 235000011178 triphosphate Nutrition 0.000 claims 5
- MJMJUKHABPJQGX-CRCLSJGQSA-N (3s,4r)-3-fluoro-4,5-dihydroxypentanal Chemical compound OC[C@@H](O)[C@@H](F)CC=O MJMJUKHABPJQGX-CRCLSJGQSA-N 0.000 claims 1
- OIEIKVCEXBMETK-BYPYZUCNSA-N 2-[(1s)-1,2-dihydroxyethoxy]acetaldehyde Chemical compound OC[C@@H](O)OCC=O OIEIKVCEXBMETK-BYPYZUCNSA-N 0.000 claims 1
- WQSIEHZPHQVPFS-UHFFFAOYSA-N 3-fluoro-4-(hydroxymethyl)pyrrolidin-2-ol Chemical compound OCC1CNC(O)C1F WQSIEHZPHQVPFS-UHFFFAOYSA-N 0.000 claims 1
- 102000004163 DNA-directed RNA polymerases Human genes 0.000 claims 1
- 108090000626 DNA-directed RNA polymerases Proteins 0.000 claims 1
- 241000701076 Macacine alphaherpesvirus 1 Species 0.000 claims 1
- 230000001548 androgenic effect Effects 0.000 claims 1
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 1
- 238000000034 method Methods 0.000 description 14
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 8
- 0 CCCC(C(CC)(CC1)N)=C=CC(CO*C)C1O Chemical compound CCCC(C(CC)(CC1)N)=C=CC(CO*C)C1O 0.000 description 2
- BPZTVHFVZNQDRE-HCWXCVPCSA-N C[C@@H]1S[C@H](CO)C[C@H]1O Chemical compound C[C@@H]1S[C@H](CO)C[C@H]1O BPZTVHFVZNQDRE-HCWXCVPCSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- SZYJWAORZUSFHW-NTSWFWBYSA-N C=C1S[C@H](CO)C[C@@]1(C(F)(F)F)O Chemical compound C=C1S[C@H](CO)C[C@@]1(C(F)(F)F)O SZYJWAORZUSFHW-NTSWFWBYSA-N 0.000 description 1
- ODXHHVUBNLIWGL-BPDFOOOXSA-N CC([C@]1(C)F)S[C@H](CO)[C@H]1O Chemical compound CC([C@]1(C)F)S[C@H](CO)[C@H]1O ODXHHVUBNLIWGL-BPDFOOOXSA-N 0.000 description 1
- NBIAJCFWHPLRMX-BGPJRJDNSA-N C[C@@H]([C@@H]1O)S[C@H](CO)[C@H]1O Chemical compound C[C@@H]([C@@H]1O)S[C@H](CO)[C@H]1O NBIAJCFWHPLRMX-BGPJRJDNSA-N 0.000 description 1
- AOOQTVGJBDRQBU-WDSKDSINSA-N C[C@@H]1S[C@H](CO)CC1 Chemical compound C[C@@H]1S[C@H](CO)CC1 AOOQTVGJBDRQBU-WDSKDSINSA-N 0.000 description 1
- AHYCTNVIMLVRSL-UHFFFAOYSA-N OCC1CC(O)N(F)C1 Chemical compound OCC1CC(O)N(F)C1 AHYCTNVIMLVRSL-UHFFFAOYSA-N 0.000 description 1
- USYKCURAQZSEQC-MOJAZDJTSA-N OC[C@H]([C@H]1O)S[C@@H](C2)[C@]12F Chemical compound OC[C@H]([C@H]1O)S[C@@H](C2)[C@]12F USYKCURAQZSEQC-MOJAZDJTSA-N 0.000 description 1
- UPJFKPIKYKGMAS-RMILHFBTSA-N OC[C@H]1S[C@@H](C2)C2[C@@H]1O Chemical compound OC[C@H]1S[C@@H](C2)C2[C@@H]1O UPJFKPIKYKGMAS-RMILHFBTSA-N 0.000 description 1
- 108020000999 Viral RNA Proteins 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88027807P | 2007-01-12 | 2007-01-12 | |
| PCT/US2008/050929 WO2008089105A2 (en) | 2007-01-12 | 2008-01-11 | Antiviral nucleoside analogs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010515760A JP2010515760A (ja) | 2010-05-13 |
| JP2010515760A5 true JP2010515760A5 (en:Method) | 2012-03-01 |
Family
ID=39471795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009545720A Pending JP2010515760A (ja) | 2007-01-12 | 2008-01-11 | 抗ウイルス性ヌクレオシド類似体 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US8440813B2 (en:Method) |
| EP (2) | EP2535345A1 (en:Method) |
| JP (1) | JP2010515760A (en:Method) |
| CN (1) | CN101611046A (en:Method) |
| AU (1) | AU2008206406A1 (en:Method) |
| CA (1) | CA2674589A1 (en:Method) |
| CY (1) | CY1113282T1 (en:Method) |
| DK (1) | DK2114980T3 (en:Method) |
| ES (1) | ES2390188T3 (en:Method) |
| HR (1) | HRP20120758T1 (en:Method) |
| IL (1) | IL199664A0 (en:Method) |
| MX (1) | MX2009007333A (en:Method) |
| NZ (2) | NZ598927A (en:Method) |
| PH (1) | PH12012502284A1 (en:Method) |
| PL (1) | PL2114980T3 (en:Method) |
| PT (1) | PT2114980E (en:Method) |
| SG (1) | SG177974A1 (en:Method) |
| SI (1) | SI2114980T1 (en:Method) |
| WO (1) | WO2008089105A2 (en:Method) |
Families Citing this family (97)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8124759B2 (en) * | 2007-05-09 | 2012-02-28 | Abbott Laboratories | Inhibitors of protein kinases |
| PL2155758T3 (pl) | 2007-05-10 | 2013-06-28 | Biocryst Pharm Inc | Pochodne tetrahydrofuro[3,4-d]dioksolanu przeznaczone do stosowania w leczeniu infekcji wirusowych i raka |
| TW200942243A (en) | 2008-03-05 | 2009-10-16 | Biocryst Pharm Inc | Antiviral therapeutic agents |
| US20090247750A1 (en) * | 2008-03-28 | 2009-10-01 | Biocryst Pharmaceuticals, Inc. | Process for preparing nucleoside analogs |
| SI2268642T1 (sl) | 2008-04-23 | 2015-05-29 | Gilead Sciences, Inc. | 1'-substituirani karba-nukleozidni analogi za antivirusno zdravljenje |
| WO2010002877A2 (en) | 2008-07-03 | 2010-01-07 | Biota Scientific Management | Bycyclic nucleosides and nucleotides as therapeutic agents |
| PL2396340T3 (pl) | 2009-02-10 | 2014-05-30 | Gilead Sciences Inc | Analogi karba-nukleozydu do terapii przeciwwirusowych |
| ME02656B (me) * | 2009-09-21 | 2017-06-20 | Gilead Sciences Inc | 2' -fluoro supstituisani karba-nukleozidni analozi za antiviralno lečenje |
| WO2011035250A1 (en) * | 2009-09-21 | 2011-03-24 | Gilead Sciences, Inc. | Processes and intermediates for the preparation of 1'-substituted carba-nucleoside analogs |
| US7973013B2 (en) | 2009-09-21 | 2011-07-05 | Gilead Sciences, Inc. | 2'-fluoro substituted carba-nucleoside analogs for antiviral treatment |
| US8455451B2 (en) | 2009-09-21 | 2013-06-04 | Gilead Sciences, Inc. | 2'-fluoro substituted carba-nucleoside analogs for antiviral treatment |
| EP2552922A1 (en) | 2010-03-31 | 2013-02-06 | Bristol-Myers Squibb Company | Substituted pyrrolotriazines as protein kinase inhibitors |
| TW201201815A (en) | 2010-05-28 | 2012-01-16 | Gilead Sciences Inc | 1'-substituted-carba-nucleoside prodrugs for antiviral treatment |
| US9090642B2 (en) | 2010-07-19 | 2015-07-28 | Gilead Sciences, Inc. | Methods for the preparation of diasteromerically pure phosphoramidate prodrugs |
| JP5969471B2 (ja) | 2010-07-22 | 2016-08-17 | ギリード・サイエンシズ・インコーポレーテッド | パラミクソウイルス科ウイルス感染症を治療するための方法及び化合物 |
| TW201305185A (zh) * | 2010-09-13 | 2013-02-01 | Gilead Sciences Inc | 用於抗病毒治療之２’－氟取代之碳－核苷類似物 |
| PH12013500311B1 (en) | 2010-09-20 | 2017-11-08 | Gilead Sciences Inc | 2' -fluoro substituted carba-nucleoside analogs for antiviral treatment |
| ES2701020T3 (es) | 2010-09-22 | 2019-02-20 | Alios Biopharma Inc | Nucleósidos azido y análogos nucleotídicos |
| WO2012088266A2 (en) | 2010-12-22 | 2012-06-28 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of fgfr3 |
| ES2744587T3 (es) | 2011-04-13 | 2020-02-25 | Gilead Sciences Inc | Análogos de N-nucleósido de pirimidina 1-sustituidos para un tratamiento antiviral |
| KR20140036269A (ko) | 2011-07-01 | 2014-03-25 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | Alk1 억제제로서의 히드록시메틸아릴-치환된 피롤로트리아진 |
| US9403863B2 (en) | 2011-09-12 | 2016-08-02 | Idenix Pharmaceuticals Llc | Substituted carbonyloxymethylphosphoramidate compounds and pharmaceutical compositions for the treatment of viral infections |
| CA2752008A1 (en) | 2011-09-13 | 2013-03-13 | Universite De Montreal | Combination therapy using ribavirin as elf4e inhibitor |
| UA117095C2 (uk) | 2011-12-22 | 2018-06-25 | Аліос Біофарма, Інк. | Нуклеозидна сполука або її фармацевтично прийнятна сіль |
| EP3210993B1 (en) * | 2012-03-13 | 2018-12-12 | Gilead Sciences, Inc. | 2'- substituted carba-nucleoside analogs for antiviral treatment |
| US9441007B2 (en) | 2012-03-21 | 2016-09-13 | Alios Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| USRE48171E1 (en) | 2012-03-21 | 2020-08-25 | Janssen Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| AR090699A1 (es) | 2012-04-18 | 2014-12-03 | Biocryst Pharm Inc | Compuestos inhibidores de la actividad de la arn polimerasa viral |
| SI2861595T1 (sl) | 2012-06-13 | 2017-04-26 | Incyte Holdings Corporation | Substituirane triciklične spojine kot inhibitorji fgfr |
| US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
| MX2015005949A (es) * | 2012-11-16 | 2015-09-08 | Biocryst Pharm Inc | Nucleosidos que contienen aza-azucar antiviral. |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| ES2657451T3 (es) | 2013-04-19 | 2018-03-05 | Incyte Holdings Corporation | Heterocíclicos bicíclicos como inhibidores del FGFR |
| KR102314960B1 (ko) | 2013-10-11 | 2021-10-19 | 얀센 바이오파마, 인코퍼레이트. | 치환된 뉴클레오사이드, 뉴클레오타이드 및 이의 유사체 |
| UA119050C2 (uk) * | 2013-11-11 | 2019-04-25 | Ґілеад Саєнсиз, Інк. | ПІРОЛО[1.2-f][1.2.4]ТРИАЗИНИ, ЯКІ ВИКОРИСТОВУЮТЬСЯ ДЛЯ ЛІКУВАННЯ РЕСПІРАТОРНО-СИНЦИТІАЛЬНИХ ВІРУСНИХ ІНФЕКЦІЙ |
| WO2015143712A1 (en) | 2014-03-28 | 2015-10-01 | Merck Sharp & Dohme Corp. | 4'-substituted nucleoside reverse transcriptase inhibitors |
| TWI678369B (zh) | 2014-07-28 | 2019-12-01 | 美商基利科學股份有限公司 | 用於治療呼吸道合胞病毒感染之噻吩並［３,２-ｄ］嘧啶、呋喃並［３,２-ｄ］嘧啶及吡咯並［３,２-ｄ］嘧啶化合物類 |
| TWI673283B (zh) | 2014-08-21 | 2019-10-01 | 美商基利科學股份有限公司 | ２’－氯胺基嘧啶酮及嘧啶二酮核苷類 |
| ES2749679T3 (es) | 2014-10-22 | 2020-03-23 | Bristol Myers Squibb Co | Compuestos de pirrolotriazina amina sustituidos como inhibidores de PI3k |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| US10214537B2 (en) | 2014-10-22 | 2019-02-26 | Bristol-Myers Squibb Company | Bicyclic heteroaryl amine compounds |
| TWI740546B (zh) * | 2014-10-29 | 2021-09-21 | 美商基利科學股份有限公司 | 製備核糖苷的方法 |
| WO2016134294A1 (en) | 2015-02-20 | 2016-08-25 | Incyte Corporation | Bicyclic heterocycles as fgfr4 inhibitors |
| CA2976790C (en) | 2015-02-20 | 2024-02-27 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| AU2016229966B2 (en) | 2015-03-06 | 2018-09-27 | Atea Pharmaceuticals, Inc. | Beta-D-2'-deoxy-2'alpha-fluoro-2'-beta-C-substituted-2-modified-N6-substituted purine nucleotides for HCV treatment |
| CN104876935B (zh) * | 2015-05-18 | 2017-04-19 | 南方医科大学 | 2‑氨基吡咯并[1,2‑f][1,2,4]三嗪类化合物、合成方法及应用 |
| CN114366745A (zh) | 2015-09-16 | 2022-04-19 | 吉利德科学公司 | 治疗沙粒病毒科和冠状病毒科病毒感染的方法 |
| US10953029B2 (en) | 2015-09-23 | 2021-03-23 | Merck Sharp & Dohme Corp. | 4′-Substituted nucleoside reverse transcriptase inhibitors and preparations thereof |
| CN109071467B (zh) | 2016-03-09 | 2023-04-04 | 艾丽奥斯生物制药有限公司 | 无环抗病毒药 |
| EP3426287A4 (en) | 2016-03-09 | 2020-03-11 | Los Angeles Biomedical Research Institute at Harbor-UCLA Medical Center | Methods and kits for use in preventing and treating vulvovaginal candidiasis |
| LT3436461T (lt) | 2016-03-28 | 2024-03-12 | Incyte Corporation | Pirolotriazino junginiai kaip tam inhibitoriai |
| WO2018013937A1 (en) | 2016-07-14 | 2018-01-18 | 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 |
| ES2907874T3 (es) | 2016-09-07 | 2022-04-26 | Atea Pharmaceuticals Inc | Nucleótidos de purina 2'-sustituidos-N6-sustituidos para el tratamiento de virus de ARN |
| EP3538108A4 (en) * | 2016-11-10 | 2020-06-17 | Oyagen, Inc. | METHODS OF TREATING AND INHIBITING EBOLA VIRUS INFECTION |
| JP7066728B2 (ja) | 2017-02-01 | 2022-05-13 | アテア ファーマシューティカルズ， インコーポレイテッド | Ｃ型肝炎ウイルスの治療のためのヌクレオチドヘミ硫酸塩 |
| KR102460968B1 (ko) | 2017-03-14 | 2022-11-01 | 길리애드 사이언시즈, 인코포레이티드 | 고양이 코로나바이러스 감염의 치료 방법 |
| CN110636884B (zh) | 2017-05-01 | 2022-10-04 | 吉利德科学公司 | 新结晶形式 |
| CN107056775A (zh) * | 2017-05-24 | 2017-08-18 | 佛山科学技术学院 | 丙型肝炎病毒ns5b聚合酶抑制剂 |
| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
| TW201919648A (zh) | 2017-07-11 | 2019-06-01 | 美商基利科學股份有限公司 | 用於治療病毒感染之含rna聚合酶抑制劑與環糊精的組合物 |
| US11040975B2 (en) | 2017-12-08 | 2021-06-22 | Merck Sharp & Dohme Corp. | Carbocyclic nucleoside reverse transcriptase inhibitors |
| WO2019200005A1 (en) | 2018-04-10 | 2019-10-17 | Atea Pharmaceuticals, Inc. | Treatment of hcv infected patients with cirrhosis |
| KR20210018265A (ko) | 2018-05-04 | 2021-02-17 | 인사이트 코포레이션 | Fgfr 억제제의 고체 형태 및 이의 제조 방법 |
| MX2020011639A (es) | 2018-05-04 | 2021-02-15 | Incyte Corp | Sales de un inhibidor de receptores de factor de crecimiento de fibroblastos (fgfr). |
| KR20210102364A (ko) | 2018-12-12 | 2021-08-19 | 얀센 바이오파마, 인코퍼레이트. | 항바이러스제로서의 사이클로펜틸 뉴클레오시드 유사체 |
| WO2020185532A1 (en) | 2019-03-08 | 2020-09-17 | Incyte Corporation | Methods of treating cancer with an fgfr inhibitor |
| US11591329B2 (en) | 2019-07-09 | 2023-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| WO2021067374A1 (en) | 2019-10-01 | 2021-04-08 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| JP7675711B2 (ja) | 2019-10-14 | 2025-05-13 | インサイト・コーポレイション | Ｆｇｆｒ阻害剤としての二環式複素環 |
| WO2021076728A1 (en) | 2019-10-16 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| CR20220285A (es) | 2019-12-04 | 2022-10-27 | Incyte Corp | Derivados de un inhibidor de fgfr |
| WO2021113479A1 (en) | 2019-12-04 | 2021-06-10 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| WO2021146424A1 (en) | 2020-01-15 | 2021-07-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| TWI789695B (zh) | 2020-01-27 | 2023-01-11 | 美商基利科學股份有限公司 | 治療sars cov-2感染之方法 |
| US11738025B2 (en) | 2020-02-04 | 2023-08-29 | Oyagen, Inc. | Method for treating coronavirus infections |
| CN113214262B (zh) * | 2020-02-05 | 2023-07-07 | 华创合成制药股份有限公司 | 一种含有胍基的化合物及其制备方法和用途 |
| TWI874791B (zh) | 2020-02-18 | 2025-03-01 | 美商基利科學股份有限公司 | 抗病毒化合物 |
| CN115135383B (zh) | 2020-02-18 | 2024-06-11 | 吉利德科学公司 | 抗病毒化合物 |
| TWI883391B (zh) | 2020-02-18 | 2025-05-11 | 美商基利科學股份有限公司 | 抗病毒化合物 |
| TWI791193B (zh) | 2020-02-18 | 2023-02-01 | 美商基利科學股份有限公司 | 抗病毒化合物 |
| US10874687B1 (en) | 2020-02-27 | 2020-12-29 | Atea Pharmaceuticals, Inc. | Highly active compounds against COVID-19 |
| JP7554841B2 (ja) | 2020-03-12 | 2024-09-20 | ギリアード サイエンシーズ， インコーポレイテッド | １’－シアノヌクレオシドを調製する方法 |
| KR102906891B1 (ko) | 2020-04-06 | 2026-01-05 | 길리애드 사이언시즈, 인코포레이티드 | 1'-시아노 치환된 카르바뉴클레오시드 유사체의 흡입 제형 |
| KR20230018473A (ko) | 2020-05-29 | 2023-02-07 | 길리애드 사이언시즈, 인코포레이티드 | 렘데시비르 치료 방법 |
| JP2023531524A (ja) | 2020-06-24 | 2023-07-24 | ギリアード サイエンシーズ， インコーポレイテッド | １’－シアノヌクレオシド類似体及びその使用 |
| EP4183792A4 (en) * | 2020-07-14 | 2024-03-20 | Sichuan University | NITROGEN-CONTAINING 3-DESOXY-2-KETONE ACID DERIVATIVE, PRODUCTION PROCESS THEREOF AND USE THEREOF |
| AU2021331214B2 (en) | 2020-08-27 | 2024-01-04 | Gilead Sciences, Inc. | Compounds and methods for treatment of viral infections |
| JP2024513575A (ja) | 2021-04-12 | 2024-03-26 | インサイト・コーポレイション | Ｆｇｆｒ阻害剤及びネクチン－４標的化剤を含む併用療法 |
| CA3216162A1 (en) | 2021-04-16 | 2022-10-20 | Gilead Sciences, Inc. | Methods of preparing carbanucleosides using amides |
| EP4352060A1 (en) | 2021-06-09 | 2024-04-17 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| AR126102A1 (es) | 2021-06-09 | 2023-09-13 | Incyte Corp | Heterociclos tricíclicos como inhibidores de fgfr |
| JP2024525164A (ja) | 2021-06-17 | 2024-07-10 | アテア ファーマシューティカルズ， インコーポレイテッド | 有利な抗ｈｃｖ併用療法 |
| CA3228162A1 (en) | 2021-08-18 | 2023-02-23 | Gilead Sciences, Inc. | Phospholipid compounds and methods of making and using the same |
| MX2024002116A (es) | 2021-08-20 | 2024-03-06 | Shionogi & Co | Derivados de nucleosido y profarmacos de los mismos que tienen accion inhibidora del crecimiento viral. |
| KR20240154647A (ko) | 2022-03-02 | 2024-10-25 | 길리애드 사이언시즈, 인코포레이티드 | 바이러스성 감염 치료를 위한 화합물 및 방법 |
| US12357577B1 (en) | 2024-02-02 | 2025-07-15 | Gilead Sciences, Inc. | Pharmaceutical formulations and uses thereof |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU771776B2 (en) | 1999-01-13 | 2004-04-01 | Genentech Inc. | Serine protease inhibitors |
| IL153020A0 (en) * | 2000-05-26 | 2003-06-24 | Idenix Cayman Ltd | Methods and compositions for treating flaviviruses and pestiviruses |
| WO2003062255A2 (en) * | 2002-01-17 | 2003-07-31 | Ribapharm Inc. | Sugar modified nucleosides as viral replication inhibitors |
| US7429565B2 (en) | 2003-04-25 | 2008-09-30 | Gilead Sciences, Inc. | Antiviral phosphonate analogs |
| US20050182252A1 (en) | 2004-02-13 | 2005-08-18 | Reddy K. R. | Novel 2'-C-methyl nucleoside derivatives |
| EP1814561A4 (en) | 2004-10-29 | 2012-12-19 | Biocryst Pharm Inc | THEROPUTICAL FUROPYRIMIDINES AND THIENOPYRIMIDINES |
| TW200942243A (en) * | 2008-03-05 | 2009-10-16 | Biocryst Pharm Inc | Antiviral therapeutic agents |
| WO2010002877A2 (en) * | 2008-07-03 | 2010-01-07 | Biota Scientific Management | Bycyclic nucleosides and nucleotides as therapeutic agents |
-
2008
- 2008-01-11 WO PCT/US2008/050929 patent/WO2008089105A2/en not_active Ceased
- 2008-01-11 PL PL08727625T patent/PL2114980T3/pl unknown
- 2008-01-11 US US12/522,892 patent/US8440813B2/en active Active
- 2008-01-11 NZ NZ598927A patent/NZ598927A/xx not_active IP Right Cessation
- 2008-01-11 MX MX2009007333A patent/MX2009007333A/es active IP Right Grant
- 2008-01-11 SI SI200830771T patent/SI2114980T1/sl unknown
- 2008-01-11 ES ES08727625T patent/ES2390188T3/es active Active
- 2008-01-11 EP EP12168831A patent/EP2535345A1/en not_active Withdrawn
- 2008-01-11 PT PT08727625T patent/PT2114980E/pt unknown
- 2008-01-11 SG SG2012002614A patent/SG177974A1/en unknown
- 2008-01-11 CA CA002674589A patent/CA2674589A1/en not_active Abandoned
- 2008-01-11 EP EP08727625A patent/EP2114980B1/en not_active Not-in-force
- 2008-01-11 DK DK08727625.9T patent/DK2114980T3/da active
- 2008-01-11 AU AU2008206406A patent/AU2008206406A1/en not_active Abandoned
- 2008-01-11 NZ NZ578556A patent/NZ578556A/en not_active IP Right Cessation
- 2008-01-11 JP JP2009545720A patent/JP2010515760A/ja active Pending
- 2008-01-11 HR HRP20120758AT patent/HRP20120758T1/hr unknown
- 2008-01-11 CN CNA2008800038586A patent/CN101611046A/zh active Pending
-
2009
- 2009-07-02 IL IL199664A patent/IL199664A0/en unknown
-
2012
- 2012-09-25 CY CY20121100876T patent/CY1113282T1/el unknown
- 2012-11-20 PH PH12012502284A patent/PH12012502284A1/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010515760A5 (en:Method) | ||
| JP2011525171A5 (en:Method) | ||
| ES2392948T3 (es) | Intermedio para inhibidores nucleosídicos de VHC | |
| KR101765997B1 (ko) | Hcv rna 복제 억제제로서의 2',4'-다이플루오로-2'-메틸 치환된 뉴클레오시드 유도체 | |
| ES2907874T3 (es) | Nucleótidos de purina 2'-sustituidos-N6-sustituidos para el tratamiento de virus de ARN | |
| JP6776273B2 (ja) | ＨＣＶ治療に対するβ−Ｄ−２’−デオキシ−２’−α−フルオロ−２’−β−Ｃ−置換−２−修飾−Ｎ６−置換プリンヌクレオチド | |
| KR20230170015A (ko) | 항바이러스제로서의 뉴클레오시드 및 뉴클레오티드 유사체 | |
| AU2014265293B2 (en) | 4'-Fluoro-2'-methyl substituted nucleoside derivatives | |
| JP2016503800A5 (en:Method) | ||
| JP2013523765A5 (en:Method) | ||
| US20070042988A1 (en) | Antiviral phosphoramidates | |
| JP2010526834A5 (en:Method) | ||
| JP2019524795A (ja) | 置換ヌクレオシド、ヌクレオチド、及びそのアナログ | |
| JP2012519691A5 (en:Method) | ||
| JP2009510075A (ja) | 抗ウイルス剤としての修飾４’−ヌクレオシド | |
| CA2632626C (en) | Ester prodrugs of 2'-fluoro-2'-alkyl-2'-deoxycytidines and their use in the treatment of hcv infection | |
| JP2013056886A5 (en:Method) | ||
| JP2008510748A (ja) | 抗ウイルス４’−アジド−ヌクレオシド | |
| WO2009099596A4 (en) | Macrocyclic serine protease inhibitors | |
| ZA200400925B (en) | Novel virus proliferation inhibition/virucidal method and novel pyradine nucleotide/pyradine nucleoside analogue | |
| JP7151956B2 (ja) | ヌクレオシドホスフェート化合物並びに当該ヌクレオシドホスフェート化合物の調製方法及び使用 | |
| JP2014532716A5 (en:Method) | ||
| JP6671355B2 (ja) | 呼吸器多核体ウイルスのｒｎａ複製の阻害剤としての４’‐ビニル置換ヌクレオシド誘導体 | |
| RU2012129657A (ru) | Гетероциклические противовирусные соединения | |
| ES2338642T3 (es) | Terapia de combinacion para tratar virus de la hepatitis b. |