TW200425898A - Method and compositions for treating flaviviruses and pestiviruses - Google Patents
Method and compositions for treating flaviviruses and pestiviruses Download PDFInfo
- Publication number
- TW200425898A TW200425898A TW093123890A TW93123890A TW200425898A TW 200425898 A TW200425898 A TW 200425898A TW 093123890 A TW093123890 A TW 093123890A TW 93123890 A TW93123890 A TW 93123890A TW 200425898 A TW200425898 A TW 200425898A
- Authority
- TW
- Taiwan
- Prior art keywords
- alkyl
- fluorenyl
- group
- monophosphate
- pharmaceutically acceptable
- Prior art date
Links
- 241000710831 Flavivirus Species 0.000 title claims abstract description 88
- 241000710778 Pestivirus Species 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims abstract description 26
- 239000000203 mixture Substances 0.000 title claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 153
- 229940002612 prodrug Drugs 0.000 claims abstract description 151
- 239000000651 prodrug Substances 0.000 claims abstract description 151
- 238000011282 treatment Methods 0.000 claims abstract description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 616
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 261
- 229910052799 carbon Inorganic materials 0.000 claims description 250
- 150000001875 compounds Chemical class 0.000 claims description 236
- 229910019142 PO4 Inorganic materials 0.000 claims description 223
- 235000021317 phosphate Nutrition 0.000 claims description 223
- 239000010452 phosphate Substances 0.000 claims description 220
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 219
- 229910052739 hydrogen Inorganic materials 0.000 claims description 201
- 239000001257 hydrogen Substances 0.000 claims description 201
- -1 sulfanylsulfonyl Chemical group 0.000 claims description 191
- 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 170
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 142
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 142
- 229910052794 bromium Inorganic materials 0.000 claims description 142
- 150000002431 hydrogen Chemical group 0.000 claims description 120
- 125000003342 alkenyl group Chemical group 0.000 claims description 112
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 106
- 239000011737 fluorine Substances 0.000 claims description 106
- 229910052731 fluorine Inorganic materials 0.000 claims description 106
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- 125000003118 aryl group Chemical group 0.000 claims description 97
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 96
- 239000000460 chlorine Substances 0.000 claims description 96
- 229910052801 chlorine Inorganic materials 0.000 claims description 96
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 93
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 93
- 125000000304 alkynyl group Chemical group 0.000 claims description 92
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- 238000001727 in vivo Methods 0.000 claims description 85
- 239000002243 precursor Substances 0.000 claims description 84
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 82
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 79
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 78
- 125000001424 substituent group Chemical group 0.000 claims description 77
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 75
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- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 74
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- 150000001413 amino acids Chemical class 0.000 claims description 71
- 238000012360 testing method Methods 0.000 claims description 69
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- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 claims description 63
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- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 52
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 42
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- 206010054261 Flavivirus infection Diseases 0.000 claims description 30
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 30
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
- 208000004571 Pestivirus Infections Diseases 0.000 claims description 28
- IGFXRKMLLMBKSA-UHFFFAOYSA-N purine Chemical compound N1=C[N]C2=NC=NC2=C1 IGFXRKMLLMBKSA-UHFFFAOYSA-N 0.000 claims description 28
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- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 26
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims description 25
- 230000000087 stabilizing effect Effects 0.000 claims description 25
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 23
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- 229910052740 iodine Inorganic materials 0.000 claims description 22
- 239000011630 iodine Substances 0.000 claims description 22
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 17
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- 238000004519 manufacturing process Methods 0.000 claims description 15
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- 229910052702 rhenium Inorganic materials 0.000 claims description 14
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 claims description 14
- 239000004575 stone Substances 0.000 claims description 13
- 125000005496 phosphonium group Chemical group 0.000 claims description 11
- 150000003254 radicals Chemical class 0.000 claims description 11
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 10
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Classifications
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- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
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- 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
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- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
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| AU2001245575A1 (en) * | 2000-03-09 | 2001-09-17 | Videoshare, Inc. | Sharing a streaming video |
| MY164523A (en) * | 2000-05-23 | 2017-12-29 | Univ Degli Studi Cagliari | Methods and compositions for treating hepatitis c virus |
| YU92202A (sh) | 2000-05-26 | 2006-01-16 | Idenix (Cayman) Limited | Metode i smeše za lečenje flavi virusa i pesti virusa |
| CA2426187C (en) * | 2000-10-18 | 2011-08-16 | Pharmasset Limited | Modified nucleosides for the treatment of viral infections and abnormal cellular proliferation |
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| CN1267446C (zh) | 2001-01-22 | 2006-08-02 | 默克公司 | 作为依赖于rna的rna病毒聚合酶的抑制剂的核苷衍生物 |
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| US20070032448A1 (en) * | 2002-01-17 | 2007-02-08 | Zhi Hong | Sugar modified nucleosides as viral replication inhibitors |
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| US20040063658A1 (en) * | 2002-05-06 | 2004-04-01 | Roberts Christopher Don | Nucleoside derivatives for treating hepatitis C virus infection |
| CA2488484A1 (en) * | 2002-06-27 | 2004-01-08 | Merck & Co., Inc. | Nucleoside derivatives as inhibitors of rna-dependent rna viral polymerase |
| 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 |
| KR20050055630A (ko) * | 2002-06-28 | 2005-06-13 | 이데닉스 (케이만) 리미티드 | 플라비비리다에 감염 치료를 위한 1'-, 2'- 및 3'-변형된뉴클레오시드 유도체 |
| RU2005102096A (ru) * | 2002-06-28 | 2005-11-20 | Айденикс (Кайман) Лимитед (Ky) | 2'и 3'-нуклеозидные пролекарства для лечения инфекций, вызываемых flaviviridae |
| AU2003248748A1 (en) | 2002-06-28 | 2004-01-19 | Idenix (Cayman) Limited | 2'-c-methyl-3'-o-l-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections |
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