JP2011525171A5 - - Google Patents
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- JP2011525171A5 JP2011525171A5 JP2010549889A JP2010549889A JP2011525171A5 JP 2011525171 A5 JP2011525171 A5 JP 2011525171A5 JP 2010549889 A JP2010549889 A JP 2010549889A JP 2010549889 A JP2010549889 A JP 2010549889A JP 2011525171 A5 JP2011525171 A5 JP 2011525171A5
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- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- aryl
- compound
- compound according
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims description 155
- 125000000217 alkyl group Chemical group 0.000 claims description 154
- 239000000651 prodrug Substances 0.000 claims description 63
- 229940002612 prodrug Drugs 0.000 claims description 63
- 229910052760 oxygen Inorganic materials 0.000 claims description 62
- 150000003839 salts Chemical class 0.000 claims description 59
- 125000003118 aryl group Chemical group 0.000 claims description 52
- -1 amino, substituted amino Chemical group 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 38
- 229910052717 sulfur Inorganic materials 0.000 claims description 36
- 229910052731 fluorine Inorganic materials 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 32
- 125000003342 alkenyl group Chemical group 0.000 claims description 28
- 125000000304 alkynyl group Chemical group 0.000 claims description 28
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 28
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 28
- 125000002252 acyl group Chemical group 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 241001465754 Metazoa Species 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000003107 substituted aryl group Chemical group 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 229910052740 iodine Inorganic materials 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 12
- 125000000539 amino acid group Chemical group 0.000 claims description 12
- 239000001177 diphosphate Substances 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
- 102000006992 Interferon-alpha Human genes 0.000 claims description 10
- 108010047761 Interferon-alpha Proteins 0.000 claims description 10
- 208000036142 Viral infection Diseases 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 150000004712 monophosphates Chemical class 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 239000001226 triphosphate Substances 0.000 claims description 10
- 230000009385 viral infection Effects 0.000 claims description 10
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 8
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 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
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 150000001413 amino acids Chemical class 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 8
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-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
- 125000000464 thioxo group Chemical group S=* 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
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 235000011180 diphosphates Nutrition 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 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
- 125000004429 atom Chemical group 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical group OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 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
- 239000003814 drug Substances 0.000 claims description 5
- 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 4
- 229940124683 HCV polymerase inhibitor Drugs 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
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 239000002777 nucleoside Substances 0.000 claims description 4
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 4
- 239000000137 peptide hydrolase inhibitor Substances 0.000 claims description 4
- 230000000069 prophylactic effect Effects 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- ISQVBYGGNVVVHB-UHFFFAOYSA-N cyclopentylmethanol Chemical compound OCC1CCCC1 ISQVBYGGNVVVHB-UHFFFAOYSA-N 0.000 claims description 3
- 230000002401 inhibitory effect Effects 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
- 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
- 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
- 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
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000001960 7 membered carbocyclic group Chemical group 0.000 claims description 2
- 125000003627 8 membered carbocyclic group Chemical group 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
- 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 group [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
- 108020000999 Viral RNA Proteins 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
- 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
- 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
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 208000002672 hepatitis B Diseases 0.000 claims description 2
- 229940125697 hormonal agent Drugs 0.000 claims description 2
- 239000002348 inosinate dehydrogenase inhibitor Substances 0.000 claims description 2
- 238000013160 medical therapy Methods 0.000 claims description 2
- 229930014626 natural product Natural products 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
- 125000005346 substituted cycloalkyl 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
- 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
- 230000003612 virological effect Effects 0.000 claims description 2
- 235000011178 triphosphate Nutrition 0.000 claims 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 4
- 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
- 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 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
- 241000991587 Enterovirus C Species 0.000 claims 1
- 208000006454 hepatitis Diseases 0.000 claims 1
- 231100000283 hepatitis Toxicity 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 238000000034 method Methods 0.000 description 15
- 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 CP(*C1)(OC2=C1CCC(*)=CC2)=O Chemical compound CP(*C1)(OC2=C1CCC(*)=CC2)=O 0.000 description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- RPKSKPXUWAPKLX-SSDOTTSWSA-N C[C@H](CCC1)C1=[IH]1CC1 Chemical compound C[C@H](CCC1)C1=[IH]1CC1 RPKSKPXUWAPKLX-SSDOTTSWSA-N 0.000 description 1
- 208000005176 Hepatitis C Diseases 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
- 208000000474 Poliomyelitis Diseases 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3405308P | 2008-03-05 | 2008-03-05 | |
| US61/034,053 | 2008-03-05 | ||
| US7937008P | 2008-07-09 | 2008-07-09 | |
| US61/079,370 | 2008-07-09 | ||
| PCT/US2009/036213 WO2009111653A2 (en) | 2008-03-05 | 2009-03-05 | Antiviral therapeutic agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011525171A JP2011525171A (ja) | 2011-09-15 |
| JP2011525171A5 true JP2011525171A5 (enExample) | 2013-03-14 |
Family
ID=41054287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010549889A Withdrawn JP2011525171A (ja) | 2008-03-05 | 2009-03-05 | 抗ウイルス性治療用薬剤 |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US7994139B2 (enExample) |
| EP (1) | EP2265275A2 (enExample) |
| JP (1) | JP2011525171A (enExample) |
| KR (1) | KR20100137494A (enExample) |
| CN (1) | CN102834513A (enExample) |
| AR (1) | AR071745A1 (enExample) |
| AU (1) | AU2009221770A1 (enExample) |
| BR (1) | BRPI0910388A2 (enExample) |
| CA (1) | CA2717173A1 (enExample) |
| EA (1) | EA201070988A1 (enExample) |
| IL (1) | IL207826A0 (enExample) |
| MX (1) | MX2010009646A (enExample) |
| NZ (1) | NZ588179A (enExample) |
| PE (1) | PE20091727A1 (enExample) |
| TW (1) | TW200942243A (enExample) |
| WO (1) | WO2009111653A2 (enExample) |
Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG177974A1 (en) * | 2007-01-12 | 2012-02-28 | Biocryst Pharm Inc | Antiviral nucleoside analogs |
| WO2008141079A1 (en) | 2007-05-10 | 2008-11-20 | Biocryst Pharmaceuticals, Inc. | Tetrahydrofuro [3 4-d] dioxolane compounds for use in the treatment of viral infections and cancer |
| US20090247750A1 (en) * | 2008-03-28 | 2009-10-01 | Biocryst Pharmaceuticals, Inc. | Process for preparing nucleoside analogs |
| AU2009240630B2 (en) | 2008-04-23 | 2013-07-18 | Gilead Sciences, Inc. | Carba-nucleoside analogs for antiviral treatment |
| EP2313102A2 (en) | 2008-07-03 | 2011-04-27 | Biota Scientific Management | Bycyclic nucleosides and nucleotides as therapeutic agents |
| TWI483950B (zh) | 2009-09-21 | 2015-05-11 | Gilead Sciences Inc | 用於製備１’－取代碳核苷類似物之方法及中間物 |
| TW201201815A (en) | 2010-05-28 | 2012-01-16 | Gilead Sciences Inc | 1'-substituted-carba-nucleoside prodrugs for antiviral treatment |
| WO2012012465A1 (en) | 2010-07-19 | 2012-01-26 | Clarke, Michael, O'neil Hanrahan | Methods for the preparation of diasteromerically pure phosphoramidate prodrugs |
| PH12013500035A1 (en) | 2010-07-22 | 2013-03-11 | Gilead Sciences Inc | Methods and compounds for treating paramyxoviridae virus infections |
| EP2898885B1 (en) | 2010-10-15 | 2017-11-22 | Biocryst Pharmaceuticals, Inc. | Pyrrolopyrimidine derivatives for use in the treatment of viral infections |
| WO2013033093A1 (en) * | 2011-08-29 | 2013-03-07 | Biocryst Pharmaceuticals, Inc. | Heterocyclic compounds as janus kinase inhibitors |
| AR090699A1 (es) | 2012-04-18 | 2014-12-03 | Biocryst Pharm Inc | Compuestos inhibidores de la actividad de la arn polimerasa viral |
| US8906929B2 (en) * | 2012-08-16 | 2014-12-09 | Bristol-Myers Squibb Company | Inhibitors of human immunodeficiency virus replication |
| CN105008369B (zh) * | 2013-03-14 | 2017-07-11 | 百时美施贵宝公司 | 人类免疫缺陷病毒复制抑制剂 |
| CN104946646B (zh) * | 2014-03-25 | 2020-03-31 | 中国医学科学院基础医学研究所 | 用于预防和/或治疗埃博拉病毒性出血热的小核酸分子、dna分子、蛋白及应用 |
| 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 |
| GEAP202215528A (en) | 2015-03-06 | 2022-11-10 | Atea Pharmaceuticals Inc | B-D-2'-DEOXY-2'a-FLUORO-2'-B-C-SUBSTITUTED-2-MODIFIED-N6-SUBSTITUTED PURINE NUCLEOTIDES FOR HCV TREATMENT |
| SG10202109869XA (en) | 2015-09-16 | 2021-10-28 | Gilead Sciences Inc | Methods for treating arenaviridae and coronaviridae virus infections |
| EP3222292A1 (en) | 2016-03-03 | 2017-09-27 | Heidelberg Pharma GmbH | Amanitin conjugates |
| US10512649B2 (en) | 2016-03-06 | 2019-12-24 | Biocryst Pharmaceuticals, Inc. | Methods and compositions for treatment of zika virus infection |
| LU100724B1 (en) | 2016-07-14 | 2018-07-31 | 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 |
| BR112019004297A2 (pt) | 2016-09-07 | 2019-05-28 | Atea Pharmaceuticals Inc | método, uso de uma quantidade eficaz de um composto, composto, e, composição farmacêutica. |
| SG11201906163TA (en) | 2017-02-01 | 2019-08-27 | Atea Pharmaceuticals Inc | Nucleotide hemi-sulfate salt for the treatment of hepatitis c virus |
| CN110869028B (zh) | 2017-03-14 | 2023-01-20 | 吉利德科学公司 | 治疗猫冠状病毒感染的方法 |
| ES2938859T3 (es) | 2017-05-01 | 2023-04-17 | Gilead Sciences Inc | Una forma cristalina de (S)-2-etilbutilo 2-(((S)-(((2R,3S,4R,5R)-5-(4-aminopirrolo[2,1-f][1,2,4]triazin-7-il)-5-ciano-3,4-dihidroxitetrahidrofuran-2-il)metoxi)(fenoxi)fosforil)amino)propanoato |
| WO2019014247A1 (en) | 2017-07-11 | 2019-01-17 | Gilead Sciences, Inc. | COMPOSITIONS COMPRISING POLYMERASE RNA INHIBITOR AND CYCLODEXTRIN FOR THE TREATMENT OF VIRAL INFECTIONS |
| EP3773753A4 (en) | 2018-04-10 | 2021-12-22 | ATEA Pharmaceuticals, Inc. | TREATMENT OF PATIENTS INFECTED WITH THE HEPATITIS C VIRUS WITH CIRRHOSIS |
| WO2020151682A1 (zh) * | 2019-01-23 | 2020-07-30 | 成都先导药物开发股份有限公司 | 一种大环类免疫调节剂 |
| CN118662520A (zh) | 2020-01-27 | 2024-09-20 | 吉利德科学公司 | 用于治疗SARS CoV-2感染的方法 |
| EP4106876B1 (en) | 2020-02-18 | 2025-09-17 | Gilead Sciences, Inc. | Antiviral compounds |
| 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 |
| TWI794742B (zh) | 2020-02-18 | 2023-03-01 | 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 |
| US11613553B2 (en) | 2020-03-12 | 2023-03-28 | Gilead Sciences, Inc. | Methods of preparing 1′-cyano nucleosides |
| EP4132651B1 (en) | 2020-04-06 | 2026-03-18 | Gilead Sciences, Inc. | Inhalation formulations of 1'-cyano substituted carbanucleoside analogs |
| ES3041698T3 (en) | 2020-05-29 | 2025-11-13 | Gilead Sciences Inc | Remdesivir for the treatment of viral infections |
| EP4172160A2 (en) | 2020-06-24 | 2023-05-03 | Gilead Sciences, Inc. | 1'-cyano nucleoside analogs and uses thereof |
| HUE067491T2 (hu) | 2020-08-27 | 2024-10-28 | Gilead Sciences Inc | Vegyületek és eljárások vírusfertõzések kezelésére |
| KR102923359B1 (ko) | 2021-04-16 | 2026-02-05 | 길리애드 사이언시즈, 인코포레이티드 | 아미드를 사용한 카르바뉴클레오시드를 제조하는 방법 |
| 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 |
| EP4387977A1 (en) | 2021-08-18 | 2024-06-26 | Gilead Sciences, Inc. | Phospholipid compounds and methods of making and using the same |
| AU2023227794A1 (en) | 2022-03-02 | 2024-10-17 | Gilead Sciences, Inc. | Compounds and methods for treatment of viral infections |
| US12357577B1 (en) | 2024-02-02 | 2025-07-15 | Gilead Sciences, Inc. | Pharmaceutical formulations and uses thereof |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6472393B1 (en) | 1999-01-13 | 2002-10-29 | Genentech, Inc. | Serine protease inhibitors |
| JP2002279640A (ja) | 2001-03-21 | 2002-09-27 | Ricoh Co Ltd | ウォブル検出回路とその装置 |
| CA2523083C (en) | 2003-04-25 | 2014-07-08 | Gilead Sciences, Inc. | Antiviral phosphonate analogs |
| WO2005021568A2 (en) * | 2003-08-27 | 2005-03-10 | Biota, Inc. | Novel tricyclic nucleosides or nucleotides as therapeutic agents |
| US20050182252A1 (en) | 2004-02-13 | 2005-08-18 | Reddy K. R. | Novel 2'-C-methyl nucleoside derivatives |
| KR20070100237A (ko) | 2004-10-29 | 2007-10-10 | 바이오크리스트 파마수티컬즈, 인코퍼레이티드 | 치료용 푸로피리미딘 및 티에노피리미딘 |
| CA2597683A1 (en) | 2005-02-28 | 2006-09-08 | Genelabs Technologies, Inc. | Tricyclic-nucleoside prodrugs for treating viral infections |
| US7842672B2 (en) * | 2006-07-07 | 2010-11-30 | Gilead Sciences, Inc. | Phosphonate inhibitors of HCV |
| SG177974A1 (en) | 2007-01-12 | 2012-02-28 | Biocryst Pharm Inc | Antiviral nucleoside analogs |
| WO2008141079A1 (en) | 2007-05-10 | 2008-11-20 | Biocryst Pharmaceuticals, Inc. | Tetrahydrofuro [3 4-d] dioxolane compounds for use in the treatment of viral infections and cancer |
-
2009
- 2009-03-04 TW TW098107018A patent/TW200942243A/zh unknown
- 2009-03-05 US US12/398,866 patent/US7994139B2/en not_active Expired - Fee Related
- 2009-03-05 AR ARP090100788A patent/AR071745A1/es not_active Application Discontinuation
- 2009-03-05 PE PE2009000334A patent/PE20091727A1/es not_active Application Discontinuation
- 2009-03-05 KR KR1020107022136A patent/KR20100137494A/ko not_active Withdrawn
- 2009-03-05 WO PCT/US2009/036213 patent/WO2009111653A2/en not_active Ceased
- 2009-03-05 JP JP2010549889A patent/JP2011525171A/ja not_active Withdrawn
- 2009-03-05 MX MX2010009646A patent/MX2010009646A/es not_active Application Discontinuation
- 2009-03-05 CA CA2717173A patent/CA2717173A1/en not_active Abandoned
- 2009-03-05 EP EP09716971A patent/EP2265275A2/en not_active Withdrawn
- 2009-03-05 CN CN2009801168793A patent/CN102834513A/zh active Pending
- 2009-03-05 EA EA201070988A patent/EA201070988A1/ru unknown
- 2009-03-05 BR BRPI0910388A patent/BRPI0910388A2/pt not_active IP Right Cessation
- 2009-03-05 AU AU2009221770A patent/AU2009221770A1/en not_active Abandoned
- 2009-03-05 NZ NZ588179A patent/NZ588179A/xx not_active IP Right Cessation
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2010
- 2010-08-26 IL IL207826A patent/IL207826A0/en unknown
-
2011
- 2011-07-12 US US13/181,078 patent/US20120142617A1/en not_active Abandoned
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