MXPA04005779A - Nucleosidos de n4-acilcitosina para el tratamiento de infecciones virales. - Google Patents
Nucleosidos de n4-acilcitosina para el tratamiento de infecciones virales.Info
- Publication number
- MXPA04005779A MXPA04005779A MXPA04005779A MXPA04005779A MXPA04005779A MX PA04005779 A MXPA04005779 A MX PA04005779A MX PA04005779 A MXPA04005779 A MX PA04005779A MX PA04005779 A MXPA04005779 A MX PA04005779A MX PA04005779 A MXPA04005779 A MX PA04005779A
- Authority
- MX
- Mexico
- Prior art keywords
- hydrogen
- fluorine
- dideoxy
- pharmaceutically acceptable
- prodrugs
- Prior art date
Links
- 229940002612 prodrug Drugs 0.000 claims abstract description 355
- 239000000651 prodrug Substances 0.000 claims abstract description 355
- 150000003839 salts Chemical class 0.000 claims abstract description 330
- 238000000034 method Methods 0.000 claims abstract description 45
- 208000015181 infectious disease Diseases 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 880
- 239000001257 hydrogen Substances 0.000 claims description 880
- 229910052731 fluorine Inorganic materials 0.000 claims description 620
- 150000001875 compounds Chemical class 0.000 claims description 399
- 125000000217 alkyl group Chemical group 0.000 claims description 95
- -1 sulfonate ester Chemical class 0.000 claims description 81
- 125000000304 alkynyl group Chemical group 0.000 claims description 74
- 125000003118 aryl group Chemical group 0.000 claims description 71
- 125000003342 alkenyl group Chemical group 0.000 claims description 70
- 125000001188 haloalkyl group Chemical group 0.000 claims description 50
- 229910052794 bromium Inorganic materials 0.000 claims description 45
- 229910052801 chlorine Inorganic materials 0.000 claims description 45
- 229910052740 iodine Inorganic materials 0.000 claims description 45
- 229910052736 halogen Inorganic materials 0.000 claims description 44
- 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 42
- 150000002431 hydrogen Chemical group 0.000 claims description 41
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 37
- 125000004001 thioalkyl group Chemical group 0.000 claims description 37
- 238000011282 treatment Methods 0.000 claims description 35
- 229910019142 PO4 Inorganic materials 0.000 claims description 34
- 239000010452 phosphate Substances 0.000 claims description 34
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical group [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 33
- 125000005843 halogen group Chemical group 0.000 claims description 30
- 150000002367 halogens Chemical group 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 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 22
- 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 19
- 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 18
- 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 18
- 238000001727 in vivo Methods 0.000 claims description 13
- 150000001413 amino acids Chemical class 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
- 235000012000 cholesterol Nutrition 0.000 claims description 11
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 11
- 150000002632 lipids Chemical class 0.000 claims description 11
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 11
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims description 2
- 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 description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000002672 4-bromobenzoyl group Chemical group BrC1=CC=C(C(=O)*)C=C1 0.000 claims 2
- 239000002259 anti human immunodeficiency virus agent Substances 0.000 claims 2
- 229940124411 anti-hiv antiviral agent Drugs 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- QBEIABZPRBJOFU-CAHLUQPWSA-N 4-amino-5-fluoro-1-[(2r,5s)-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one Chemical group C1=C(F)C(N)=NC(=O)N1[C@@H]1O[C@H](CO)CC1 QBEIABZPRBJOFU-CAHLUQPWSA-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
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 claims 1
- 241000700721 Hepatitis B virus Species 0.000 abstract description 33
- 241000725303 Human immunodeficiency virus Species 0.000 abstract description 24
- 239000000203 mixture Substances 0.000 abstract description 23
- 241000282414 Homo sapiens Species 0.000 abstract description 9
- 208000036142 Viral infection Diseases 0.000 abstract description 4
- 241001465754 Metazoa Species 0.000 abstract description 3
- 230000009385 viral infection Effects 0.000 abstract description 3
- 239000011737 fluorine Substances 0.000 description 576
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 560
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 299
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 290
- 125000001153 fluoro group Chemical group F* 0.000 description 285
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 278
- 239000000460 chlorine Substances 0.000 description 50
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 40
- 235000021317 phosphate Nutrition 0.000 description 31
- 239000002777 nucleoside Substances 0.000 description 29
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 15
- 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 13
- 238000003786 synthesis reaction Methods 0.000 description 12
- 125000001544 thienyl group Chemical group 0.000 description 12
- 239000001226 triphosphate Substances 0.000 description 12
- 235000001014 amino acid Nutrition 0.000 description 11
- 235000011178 triphosphate Nutrition 0.000 description 11
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Natural products NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 10
- 229940104302 cytosine Drugs 0.000 description 10
- 239000001177 diphosphate Substances 0.000 description 10
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 10
- 235000011180 diphosphates Nutrition 0.000 description 10
- 150000004712 monophosphates Chemical class 0.000 description 10
- 125000003835 nucleoside group Chemical group 0.000 description 10
- 230000002265 prevention Effects 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 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 9
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical group OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 8
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 8
- 150000003833 nucleoside derivatives Chemical class 0.000 description 8
- 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
- 125000001624 naphthyl group Chemical group 0.000 description 7
- 208000030507 AIDS Diseases 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000005140 aralkylsulfonyl group Chemical group 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
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- 238000006243 chemical reaction Methods 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
- 125000002541 furyl group Chemical group 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
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- 229910052792 caesium Inorganic materials 0.000 description 5
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 5
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- 150000003904 phospholipids Chemical class 0.000 description 5
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- 230000005526 G1 to G0 transition Effects 0.000 description 4
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- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 4
- 125000003282 alkyl amino group Chemical group 0.000 description 4
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- 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
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- WJXREUZUPGMAII-UHFFFAOYSA-N sulfurazidic acid Chemical compound OS(=O)(=O)N=[N+]=[N-] WJXREUZUPGMAII-UHFFFAOYSA-N 0.000 description 1
- BZWKPZBXAMTXNQ-UHFFFAOYSA-N sulfurocyanidic acid Chemical compound OS(=O)(=O)C#N BZWKPZBXAMTXNQ-UHFFFAOYSA-N 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
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- HLUVZZITVLCHHG-UHFFFAOYSA-N triacontylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCCC1 HLUVZZITVLCHHG-UHFFFAOYSA-N 0.000 description 1
- NJQPETPMXWCDOA-UHFFFAOYSA-N triacontylcyclopentane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCC1 NJQPETPMXWCDOA-UHFFFAOYSA-N 0.000 description 1
- MVLKTFOLEWGUOV-UHFFFAOYSA-N tricosylcyclopentane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC1CCCC1 MVLKTFOLEWGUOV-UHFFFAOYSA-N 0.000 description 1
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- WORVRGQZSXETON-UHFFFAOYSA-N tritriacontylcyclopentane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCC1 WORVRGQZSXETON-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
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- A—HUMAN NECESSITIES
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- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
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- A—HUMAN NECESSITIES
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- 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)
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- Engineering & Computer Science (AREA)
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- Oncology (AREA)
- Communicable Diseases (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)
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| US34155501P | 2001-12-14 | 2001-12-14 | |
| PCT/US2002/040081 WO2003063771A2 (en) | 2001-12-14 | 2002-12-13 | N4-acylcytosine nucleosides for treatment of viral iinfections |
Publications (1)
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| MXPA04005779A true MXPA04005779A (es) | 2005-05-16 |
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| EP (1) | EP1569652A4 (enExample) |
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| KR (1) | KR100978904B1 (enExample) |
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| CA (1) | CA2470255C (enExample) |
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| US6790228B2 (en) * | 1999-12-23 | 2004-09-14 | Advanced Cardiovascular Systems, Inc. | Coating for implantable devices and a method of forming the same |
| JP2003532643A (ja) | 2000-04-13 | 2003-11-05 | フアーマセツト・リミテツド | 肝炎ウイルス感染症を治療するための３’−または２’−ヒドロキシメチル置換ヌクレオシド誘導体 |
| MY164523A (en) | 2000-05-23 | 2017-12-29 | Univ Degli Studi Cagliari | Methods and compositions for treating hepatitis c virus |
| PL359169A1 (en) | 2000-05-26 | 2004-08-23 | Idenix (Cayman) Limited | Methods and compositions for treating flaviviruses and pestiviruses |
| BR0214944A (pt) * | 2001-12-14 | 2005-06-07 | Pharmasset Ltd | Nucleosìdeos de n4-acilcitosina para o tratamento de infecções virais |
| US7608600B2 (en) | 2002-06-28 | 2009-10-27 | Idenix Pharmaceuticals, Inc. | Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections |
| CN101172993A (zh) | 2002-06-28 | 2008-05-07 | 埃迪尼克斯(开曼)有限公司 | 用于治疗黄病毒感染的2′－c－甲基－3′－o－l－缬氨酸酯核糖呋喃基胞苷 |
| KR20050035194A (ko) * | 2002-06-28 | 2005-04-15 | 이데닉스 (케이만) 리미티드 | 플라비비리다에 감염 치료용 2'-ｃ-메틸-3'-ｏ-ｌ-발린에스테르 리보푸라노실 사이티딘 |
| EP1545545A4 (en) | 2002-08-01 | 2008-09-03 | Pharmasset Inc | COMPOUNDS WITH THE BICYCLO 4.2.1 NONAN SYSTEM FOR THE TREATMENT OF FLAVIVIRIDAE / I INFECTIONS |
| AU2003298658A1 (en) | 2002-11-15 | 2004-06-15 | Idenix (Cayman) Limited | 2'-branched nucleosides and flaviviridae mutation |
| US7598373B2 (en) | 2002-12-12 | 2009-10-06 | Idenix Pharmaceuticals, Inc. | Process for the production of 2-C-methyl-D-ribonolactone |
| CA2425031A1 (en) * | 2003-04-01 | 2004-10-01 | Smithkline Beecham Corporation | Pharmaceutical compositions |
| RU2358979C2 (ru) | 2003-05-30 | 2009-06-20 | Фармассет, Инк. | Модифицированные фторированные аналоги нуклеозида |
| US7741334B2 (en) * | 2004-04-01 | 2010-06-22 | 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 |
| ES2725457T3 (es) | 2004-09-14 | 2019-09-24 | Gilead Pharmasset Llc | Preparación de ribofuranosil pirimidinas y purinas 2'fluoro-2'-alquil-sustituidas u otras opcionalmente sustituidas y sus derivados |
| EP1802315A2 (en) * | 2004-10-19 | 2007-07-04 | 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 |
| US7781576B2 (en) * | 2005-12-23 | 2010-08-24 | 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 |
| AR074897A1 (es) | 2008-12-23 | 2011-02-23 | Pharmasset Inc | Fosforamidatos de nucleosidos |
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| CL2009002206A1 (es) | 2008-12-23 | 2011-08-26 | Gilead Pharmasset Llc | Compuestos derivados de pirrolo -(2-3-d]-pirimidin-7(6h)-tetrahidrofuran-2-il fosfonamidato, composicion farmaceutica; y su uso en el tratamiento de enfermedades virales. |
| US8618076B2 (en) | 2009-05-20 | 2013-12-31 | Gilead Pharmasset Llc | Nucleoside phosphoramidates |
| TWI576352B (zh) | 2009-05-20 | 2017-04-01 | 基利法瑪席特有限責任公司 | 核苷磷醯胺 |
| AP2012006535A0 (en) | 2010-03-31 | 2012-10-31 | Gilead Pharmasset Llc | Stereoselective synthesis of phosphorous containing actives |
| 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 |
| ES2716158T3 (es) | 2010-11-30 | 2019-06-10 | Gilead Pharmasset Llc | 2'-spiro-nucleótidos para el tratamiento de hepatitis C |
| HRP20180237T4 (hr) | 2011-09-16 | 2020-12-11 | Gilead Pharmasset Llc | Metode za liječenje hcv-a |
| 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 |
| EP2950786B1 (en) | 2013-01-31 | 2019-11-27 | Gilead Pharmasset LLC | Combination formulation of two antiviral compounds |
| EA201690473A1 (ru) | 2013-08-27 | 2017-03-31 | ГАЙЛИД ФАРМАССЕТ ЭлЭлСи | Комбинированный состав двух противовирусных соединений |
| FI3265102T3 (fi) | 2015-03-06 | 2025-10-31 | Atea Pharmaceuticals Inc | Beta-d-2'-deoksi-2'-alfa-fluori-2'-beta-c-substituoituja-2-modifioituja-n6-substituoituja puriininukleotideja hcv-hoitoa varten |
| 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 |
| PT3512863T (pt) | 2016-09-07 | 2022-03-09 | Atea Pharmaceuticals Inc | Nucleótidos de purina 2'-substituídos-n6-substituídos para tratamento de vírus de rna |
| 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 |
| CN112351799A (zh) | 2018-04-10 | 2021-02-09 | 阿堤亚制药公司 | 具有硬化的hcv感染患者的治疗 |
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| WO1998017281A1 (en) * | 1996-10-24 | 1998-04-30 | Vion Pharmaceuticals, Inc. | MONOPHOSPHATE PRODRUGS OF β-L-FD4C AND β-L-FddC AS POTENT ANTIVIRAL AGENTS |
| WO1999026958A1 (en) * | 1997-11-25 | 1999-06-03 | Protarga, Inc. | Nucleoside analog compositions and uses thereof |
| EA200700564A1 (ru) * | 1998-02-25 | 2007-08-31 | Эмори Юниверсити | 2`-фторнуклеозиды |
| CN100376570C (zh) * | 2000-10-13 | 2008-03-26 | 希拉生物化学股份有限公司 | 改善胞间传输的二氧戊环类似物 |
| KR20090089922A (ko) * | 2000-10-18 | 2009-08-24 | 파마셋 인코포레이티드 | 바이러스 감염 및 비정상적인 세포 증식의 치료를 위한 변형된 뉴클레오시드 |
| BR0214944A (pt) * | 2001-12-14 | 2005-06-07 | Pharmasset Ltd | Nucleosìdeos de n4-acilcitosina para o tratamento de infecções virais |
-
2002
- 2002-12-13 BR BR0214944-3A patent/BR0214944A/pt not_active Application Discontinuation
- 2002-12-13 KR KR1020047009263A patent/KR100978904B1/ko not_active Expired - Fee Related
- 2002-12-13 EP EP02804833A patent/EP1569652A4/en not_active Withdrawn
- 2002-12-13 CN CNB028278402A patent/CN100560073C/zh not_active Expired - Fee Related
- 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
- 2002-12-13 AU AU2002365234A patent/AU2002365234B2/en not_active Ceased
- 2002-12-13 WO PCT/US2002/040081 patent/WO2003063771A2/en not_active Ceased
- 2002-12-13 CA CA2470255A patent/CA2470255C/en not_active Expired - Fee Related
- 2002-12-13 MX MXPA04005779A patent/MXPA04005779A/es active IP Right Grant
- 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
- 2002-12-16 AU AU2002364730A patent/AU2002364730A1/en not_active Abandoned
-
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
Also Published As
| Publication number | Publication date |
|---|---|
| US7105527B2 (en) | 2006-09-12 |
| WO2003051306A3 (en) | 2003-12-18 |
| US6908924B2 (en) | 2005-06-21 |
| US20030176319A1 (en) | 2003-09-18 |
| WO2003063771A2 (en) | 2003-08-07 |
| US20040214844A1 (en) | 2004-10-28 |
| WO2003051306A2 (en) | 2003-06-26 |
| KR20040094398A (ko) | 2004-11-09 |
| CA2470255A1 (en) | 2003-08-07 |
| US20120202766A1 (en) | 2012-08-09 |
| USRE42015E1 (en) | 2010-12-28 |
| AU2002364730A1 (en) | 2003-06-30 |
| CN1617726A (zh) | 2005-05-18 |
| CA2470255C (en) | 2012-01-17 |
| CN100560073C (zh) | 2009-11-18 |
| WO2003063771A3 (en) | 2005-07-07 |
| EP1569652A4 (en) | 2008-07-02 |
| AU2002364730A8 (en) | 2003-06-30 |
| JP2005519916A (ja) | 2005-07-07 |
| EP1569652A2 (en) | 2005-09-07 |
| US20090176730A1 (en) | 2009-07-09 |
| US8114997B2 (en) | 2012-02-14 |
| AU2002365234B2 (en) | 2009-01-29 |
| US20070078080A1 (en) | 2007-04-05 |
| KR100978904B1 (ko) | 2010-08-31 |
| BR0214944A (pt) | 2005-06-07 |
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