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
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- 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
- MJWRHKSSZBHAEW-UHFFFAOYSA-N tetradecylcyclopentane Chemical compound CCCCCCCCCCCCCCC1CCCC1 MJWRHKSSZBHAEW-UHFFFAOYSA-N 0.000 description 1
- IQNOOEILKDDPAZ-UHFFFAOYSA-N tetratriacontylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCCC1 IQNOOEILKDDPAZ-UHFFFAOYSA-N 0.000 description 1
- ZTKZBMRGTUDQQJ-UHFFFAOYSA-N tetratriacontylcyclopentane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCC1 ZTKZBMRGTUDQQJ-UHFFFAOYSA-N 0.000 description 1
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- OLTHARGIAFTREU-UHFFFAOYSA-N triacontane Natural products CCCCCCCCCCCCCCCCCCCCC(C)CCCCCCCC OLTHARGIAFTREU-UHFFFAOYSA-N 0.000 description 1
- HLUVZZITVLCHHG-UHFFFAOYSA-N triacontylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCCC1 HLUVZZITVLCHHG-UHFFFAOYSA-N 0.000 description 1
- 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
- DKRUJKKWJGNYQN-UHFFFAOYSA-N tridecylcyclohexane Chemical compound CCCCCCCCCCCCCC1CCCCC1 DKRUJKKWJGNYQN-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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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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- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
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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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- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Virology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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)
| Publication Number | Publication Date |
|---|---|
| MXPA04005779A true MXPA04005779A (es) | 2005-05-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA04005779A MXPA04005779A (es) | 2001-12-14 | 2002-12-13 | Nucleosidos de n4-acilcitosina para el tratamiento de infecciones virales. |
Country Status (10)
| Country | Link |
|---|---|
| US (6) | US7105527B2 (https=) |
| EP (1) | EP1569652A4 (https=) |
| JP (1) | JP2005519916A (https=) |
| KR (1) | KR100978904B1 (https=) |
| CN (1) | CN100560073C (https=) |
| AU (2) | AU2002365234B2 (https=) |
| BR (1) | BR0214944A (https=) |
| CA (1) | CA2470255C (https=) |
| MX (1) | MXPA04005779A (https=) |
| WO (2) | WO2003063771A2 (https=) |
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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 |
| EP1964569A3 (en) | 2000-04-13 | 2009-07-22 | Pharmasset, Inc. | 3'-or 2'-hydroxymethyl substituted nucleoside derivatives for treatment of viral infections |
| MY164523A (en) | 2000-05-23 | 2017-12-29 | Univ Degli Studi Cagliari | Methods and compositions for treating hepatitis c virus |
| EP1736478B1 (en) | 2000-05-26 | 2015-07-22 | IDENIX Pharmaceuticals, Inc. | Methods and compositions for treating flaviviruses and pestiviruses |
| AU2002365234B2 (en) * | 2001-12-14 | 2009-01-29 | Pharmasset Inc | N4-acylcytosine nucleosides for treatment of viral infections |
| NZ537662A (en) | 2002-06-28 | 2007-10-26 | Idenix Cayman Ltd | 2'-C-methyl-3'-O-L-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections |
| CN1678326A (zh) * | 2002-06-28 | 2005-10-05 | 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 |
| US7608600B2 (en) | 2002-06-28 | 2009-10-27 | Idenix Pharmaceuticals, Inc. | Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections |
| WO2004013300A2 (en) | 2002-08-01 | 2004-02-12 | Pharmasset Inc. | Compounds with the bicyclo[4.2.1]nonane system for the treatment of flaviviridae infections |
| LT1576138T (lt) | 2002-11-15 | 2017-06-26 | Idenix Pharmaceuticals Llc | 2`-šakoti nukleozidai derinyje su interferonu ir flaviviridae mutacija |
| AU2003300901A1 (en) | 2002-12-12 | 2004-06-30 | Idenix (Cayman) Limited | Process for the production of 2'-branched nucleosides |
| CA2425031A1 (en) * | 2003-04-01 | 2004-10-01 | Smithkline Beecham Corporation | Pharmaceutical compositions |
| HUE029877T2 (en) * | 2003-05-30 | 2017-04-28 | Gilead Pharmasset Llc | Modified fluorinated nucleoside analogues |
| 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 |
| US8492539B2 (en) | 2004-09-14 | 2013-07-23 | Gilead Pharmasset Llc | Preparation of 2′-fluoro-2′-alkyl-substituted or other optionally substituted ribofuranosyl pyrimidines and purines and their derivatives |
| CA2584670A1 (en) * | 2004-10-19 | 2006-04-27 | Achillion Pharmaceuticals, Inc. | Combination therapy for treating viral infections |
| US7968703B2 (en) * | 2005-03-07 | 2011-06-28 | Shire Canada Inc. | Process and methods for the preparation of optically active cis-2-hydroxymethyl-4- (cytosin-1'-yl)-1,3-oxathiolane or pharmaceutically acceptable salts thereof |
| ES2422290T3 (es) * | 2005-12-23 | 2013-09-10 | Idenix Pharmaceuticals Inc | Procedimiento para preparar un producto intermedio sintético para la preparación de nucleósidos ramificados |
| 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 |
| PA8855601A1 (es) | 2008-12-23 | 2010-07-27 | Forformidatos de nucleósidos | |
| AU2009329872B2 (en) | 2008-12-23 | 2016-07-07 | Gilead Pharmasset Llc | Synthesis of purine nucleosides |
| NZ593649A (en) | 2008-12-23 | 2013-11-29 | Gilead Pharmasset Llc | Nucleoside analogs |
| TWI583692B (zh) | 2009-05-20 | 2017-05-21 | 基利法瑪席特有限責任公司 | 核苷磷醯胺 |
| US8618076B2 (en) | 2009-05-20 | 2013-12-31 | Gilead Pharmasset Llc | Nucleoside phosphoramidates |
| SG184324A1 (en) | 2010-03-31 | 2012-11-29 | Gilead Pharmasset Llc | Nucleoside phosphoramidates |
| US8563530B2 (en) | 2010-03-31 | 2013-10-22 | Gilead Pharmassel LLC | Purine nucleoside phosphoramidate |
| CA2818853A1 (en) | 2010-11-30 | 2012-06-07 | Gilead Pharmasset Llc | 2'-spirocyclo-nucleosides for use in therapy of hcv or dengue virus |
| EP2709613B2 (en) | 2011-09-16 | 2020-08-12 | Gilead Pharmasset LLC | Methods for treating hcv |
| US8889159B2 (en) | 2011-11-29 | 2014-11-18 | Gilead Pharmasset Llc | Compositions and methods for treating hepatitis C virus |
| CN103242400B (zh) * | 2012-02-08 | 2016-06-08 | 河南师范大学 | 具有抗hiv活性的5-取代嘧啶核苷-噻唑啉酮杂化体及其制备方法 |
| EP2950786B1 (en) | 2013-01-31 | 2019-11-27 | Gilead Pharmasset LLC | Combination formulation of two antiviral compounds |
| PT3038601T (pt) | 2013-08-27 | 2020-06-30 | Gilead Pharmasset Llc | Formulação combinada de dois compostos antivirais |
| CA3182565A1 (en) | 2015-03-06 | 2016-09-15 | Atea Pharmaceuticals, Inc. | .beta.-d-2'-deoxy-2'-.alpha.-fluoro-2'-.beta.-c-substituted-2-modified-n6-substituted purine nucleotides for hcv treatment |
| 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 |
| WO2018048937A1 (en) | 2016-09-07 | 2018-03-15 | Atea Pharmaceuticals, Inc. | 2'-substituted-n6-substituted purine nucleotides for rna virus treatment |
| IL288737B (en) | 2017-02-01 | 2022-09-01 | Atea Pharmaceuticals Inc | Hemisulfate nucleotide salt for treatment of hepatitis c virus |
| EP3773753A4 (en) | 2018-04-10 | 2021-12-22 | ATEA Pharmaceuticals, Inc. | TREATMENT OF PATIENTS INFECTED WITH THE HEPATITIS C VIRUS WITH CIRRHOSIS |
| US10874687B1 (en) | 2020-02-27 | 2020-12-29 | Atea Pharmaceuticals, Inc. | Highly active compounds against COVID-19 |
| IL308921A (en) | 2021-06-17 | 2024-01-01 | Atea Pharmaceuticals Inc | Combination anti-HCV therapy is beneficial |
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| US13660A (en) * | 1855-10-09 | Improvements | ||
| US3309359A (en) * | 1965-10-22 | 1967-03-14 | Hoffmann La Roche | N-mono-acyl-5-fluorocytosine derivatives and process |
| NL8202626A (nl) | 1982-06-29 | 1984-01-16 | Stichting Rega V Z W | Derivaten van 9-(2-hydroxyethoxymethyl)guanine. |
| US4522811A (en) * | 1982-07-08 | 1985-06-11 | Syntex (U.S.A.) Inc. | Serial injection of muramyldipeptides and liposomes enhances the anti-infective activity of muramyldipeptides |
| GB8719367D0 (en) * | 1987-08-15 | 1987-09-23 | Wellcome Found | Therapeutic compounds |
| ZA886890B (en) * | 1987-10-09 | 1989-05-30 | Hoffmann La Roche | Novel dideoxycytidine derivatives |
| US6350753B1 (en) * | 1988-04-11 | 2002-02-26 | Biochem Pharma Inc. | 2-Substituted-4-substituted-1,3-dioxolanes and use thereof |
| NL8901258A (nl) | 1989-05-19 | 1990-12-17 | Stichting Rega V Z W | 5-halogeno-2',3'-dideoxycytidinederivaten in geneesmiddelen voor het behandelen van retrovirus-infecties. |
| DD293498A5 (de) | 1989-07-20 | 1991-09-05 | Zi Fuer Molekularbiologie Der Adw,De | Verfahren zur herstellung eines mittels fuer die behandlung oder prophylaxe von hepatits-infektionen bei mensch und tier |
| JPH05310777A (ja) | 1992-05-14 | 1993-11-22 | Yoshitomi Pharmaceut Ind Ltd | ２’−デオキシ−２’−メチリデンシチジン化合物 |
| TW254946B (https=) * | 1992-12-18 | 1995-08-21 | Hoffmann La Roche | |
| TW374087B (en) * | 1993-05-25 | 1999-11-11 | Univ Yale | L-2',3'-dideoxy nucleotide analogs as anti-hepatitis B(HBV) and anti-HIV agents |
| TW530047B (en) | 1994-06-08 | 2003-05-01 | Pfizer | Corticotropin releasing factor antagonists |
| US5703058A (en) * | 1995-01-27 | 1997-12-30 | Emory University | Compositions containing 5-fluoro-2',3'-didehydro-2',3'-dideoxycytidine or a mono-, di-, or triphosphate thereof and a second antiviral agent |
| GB9525606D0 (en) | 1995-12-14 | 1996-02-14 | Iaf Biochem Int | Method and compositions for the synthesis of dioxolane nucleosides with - configuration |
| AU4988697A (en) * | 1996-10-24 | 1998-05-15 | Vion Pharmaceuticals, Inc. | Monophosphate prodrugs of beta-l-fd4c and beta-l-fddc as potent antiviral agents |
| EP1042341A1 (en) * | 1997-11-25 | 2000-10-11 | Protarga Inc. | Nucleoside analog compositions and uses thereof |
| WO1999043691A1 (en) * | 1998-02-25 | 1999-09-02 | Emory University | 2'-fluoronucleosides |
| AU2002212015B2 (en) * | 2000-10-13 | 2007-01-25 | Shire Canada Inc. | Dioxolane analogs for improved inter-cellular delivery |
| WO2002032920A2 (en) * | 2000-10-18 | 2002-04-25 | Pharmasset Limited | Modified nucleosides for treatment of viral infections and abnormal cellular proliferation |
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- 2002-12-16 WO PCT/US2002/040090 patent/WO2003051306A2/en not_active Ceased
- 2002-12-16 US US10/320,350 patent/US6908924B2/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 |
|---|---|
| CN1617726A (zh) | 2005-05-18 |
| CA2470255A1 (en) | 2003-08-07 |
| WO2003051306A3 (en) | 2003-12-18 |
| WO2003063771A2 (en) | 2003-08-07 |
| KR20040094398A (ko) | 2004-11-09 |
| EP1569652A2 (en) | 2005-09-07 |
| KR100978904B1 (ko) | 2010-08-31 |
| AU2002365234B2 (en) | 2009-01-29 |
| JP2005519916A (ja) | 2005-07-07 |
| US8114997B2 (en) | 2012-02-14 |
| US20120202766A1 (en) | 2012-08-09 |
| WO2003051306A2 (en) | 2003-06-26 |
| BR0214944A (pt) | 2005-06-07 |
| US20070078080A1 (en) | 2007-04-05 |
| CA2470255C (en) | 2012-01-17 |
| US20030176319A1 (en) | 2003-09-18 |
| AU2002364730A1 (en) | 2003-06-30 |
| US7105527B2 (en) | 2006-09-12 |
| AU2002364730A8 (en) | 2003-06-30 |
| EP1569652A4 (en) | 2008-07-02 |
| CN100560073C (zh) | 2009-11-18 |
| USRE42015E1 (en) | 2010-12-28 |
| US20040214844A1 (en) | 2004-10-28 |
| US6908924B2 (en) | 2005-06-21 |
| US20090176730A1 (en) | 2009-07-09 |
| WO2003063771A3 (en) | 2005-07-07 |
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