AU2002365234B2 - N4-acylcytosine nucleosides for treatment of viral infections - Google Patents
N4-acylcytosine nucleosides for treatment of viral infections Download PDFInfo
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- AU2002365234B2 AU2002365234B2 AU2002365234A AU2002365234A AU2002365234B2 AU 2002365234 B2 AU2002365234 B2 AU 2002365234B2 AU 2002365234 A AU2002365234 A AU 2002365234A AU 2002365234 A AU2002365234 A AU 2002365234A AU 2002365234 B2 AU2002365234 B2 AU 2002365234B2
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- Australia
- Prior art keywords
- hydrogen
- fluorine
- pharmaceutically acceptable
- dideoxy
- active compound
- 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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- 238000011282 treatment Methods 0.000 title claims description 24
- 239000002777 nucleoside Substances 0.000 title description 29
- 125000003835 nucleoside group Chemical group 0.000 title description 7
- 208000036142 Viral infection Diseases 0.000 title description 3
- 230000009385 viral infection Effects 0.000 title description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 940
- 229910052731 fluorine Inorganic materials 0.000 claims description 620
- 150000001875 compounds Chemical class 0.000 claims description 415
- 229940002612 prodrug Drugs 0.000 claims description 360
- 239000000651 prodrug Substances 0.000 claims description 360
- 150000003839 salts Chemical class 0.000 claims description 349
- 125000000217 alkyl group Chemical group 0.000 claims description 96
- 125000003118 aryl group Chemical group 0.000 claims description 57
- -1 sulfonate ester Chemical group 0.000 claims description 55
- 125000000304 alkynyl group Chemical group 0.000 claims description 52
- 229910052736 halogen Inorganic materials 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 46
- 229910052794 bromium Inorganic materials 0.000 claims description 45
- 229910052801 chlorine Inorganic materials 0.000 claims description 42
- 125000003342 alkenyl group Chemical group 0.000 claims description 39
- 229910019142 PO4 Inorganic materials 0.000 claims description 36
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical group [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 36
- 239000010452 phosphate Substances 0.000 claims description 36
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 33
- 229910052799 carbon Inorganic materials 0.000 claims description 32
- 125000001188 haloalkyl group Chemical group 0.000 claims description 31
- 125000005843 halogen group Chemical group 0.000 claims description 31
- 150000002367 halogens Chemical class 0.000 claims description 30
- 125000004001 thioalkyl group Chemical group 0.000 claims description 27
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 208000015181 infectious disease Diseases 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 15
- 125000002252 acyl group Chemical group 0.000 claims description 13
- 238000001727 in vivo Methods 0.000 claims description 13
- 150000001413 amino acids Chemical class 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 12
- 235000012000 cholesterol Nutrition 0.000 claims description 12
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 12
- 150000002632 lipids Chemical class 0.000 claims description 12
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 12
- 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 7
- 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 7
- 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 7
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- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
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- YSLHKCWTZCBOCO-FPVIDPCTSA-N 6-amino-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(4-nitrobenzoyl)-1H-pyrimidin-2-one Chemical compound C1=CC(N)(C(=O)C=2C=CC(=CC=2)[N+]([O-])=O)NC(=O)N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YSLHKCWTZCBOCO-FPVIDPCTSA-N 0.000 claims description 2
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- 238000004519 manufacturing process Methods 0.000 claims 2
- XMNMKEYOIYJGRD-FPVIDPCTSA-N 6-amino-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(3-fluorobenzoyl)-1H-pyrimidin-2-one Chemical compound C1=CC(N)(C(=O)C=2C=C(F)C=CC=2)NC(=O)N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O XMNMKEYOIYJGRD-FPVIDPCTSA-N 0.000 claims 1
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- TXJDZHCOMITEDO-USNNFTJFSA-N 6-amino-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(4-propylbenzoyl)-1H-pyrimidin-2-one Chemical compound C1=CC(CCC)=CC=C1C(=O)C1(N)C=CN([C@H]2[C@@H]([C@H](O)[C@@H](CO)O2)O)C(=O)N1 TXJDZHCOMITEDO-USNNFTJFSA-N 0.000 claims 1
- HXXNIIFACRGMJY-PNXMHIEFSA-N 6-amino-3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(thiophene-2-carbonyl)-1H-pyrimidin-2-one Chemical compound C1=CC(N)(C(=O)C=2SC=CC=2)NC(=O)N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O HXXNIIFACRGMJY-PNXMHIEFSA-N 0.000 claims 1
- DJVMNMGZLLNCOX-OBNKUBODSA-N 6-amino-5-fluoro-6-(4-fluorobenzoyl)-3-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrimidin-2-one Chemical compound C1=C(F)C(N)(C(=O)C=2C=CC(F)=CC=2)NC(=O)N1[C@H]1CC[C@@H](CO)O1 DJVMNMGZLLNCOX-OBNKUBODSA-N 0.000 claims 1
- ORAFXVZDHPCYMY-QQDBQQHDSA-N 6-amino-6-(1-benzothiophene-2-carbonyl)-5-fluoro-3-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrimidin-2-one Chemical compound C1=C(F)C(N)(C(=O)C=2SC3=CC=CC=C3C=2)NC(=O)N1[C@H]1CC[C@@H](CO)O1 ORAFXVZDHPCYMY-QQDBQQHDSA-N 0.000 claims 1
- DMEDABDOQFXXBC-OBNKUBODSA-N 6-amino-6-(3-chlorobenzoyl)-5-fluoro-3-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrimidin-2-one Chemical compound C1=C(F)C(N)(C(=O)C=2C=C(Cl)C=CC=2)NC(=O)N1[C@H]1CC[C@@H](CO)O1 DMEDABDOQFXXBC-OBNKUBODSA-N 0.000 claims 1
- VCLLXLWPTDLADT-OBNKUBODSA-N 6-amino-6-(4-chlorobenzoyl)-5-fluoro-3-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-1H-pyrimidin-2-one Chemical compound C1=C(F)C(N)(C(=O)C=2C=CC(Cl)=CC=2)NC(=O)N1[C@@H]1O[C@H](CO)C=C1 VCLLXLWPTDLADT-OBNKUBODSA-N 0.000 claims 1
- QFZSFOGFWZZUNY-OBNKUBODSA-N 6-amino-6-(4-chlorobenzoyl)-5-fluoro-3-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrimidin-2-one Chemical compound ClC1=CC=C(C(=O)C2(NC(N([C@H]3CC[C@@H](CO)O3)C=C2F)=O)N)C=C1 QFZSFOGFWZZUNY-OBNKUBODSA-N 0.000 claims 1
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- AMHSVLOKQVVFRS-OBNKUBODSA-N 6-amino-6-(cyclohexanecarbonyl)-5-fluoro-3-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]-1H-pyrimidin-2-one Chemical compound C1(CCCCC1)C(=O)C1(NC(N([C@H]2CC[C@@H](CO)O2)C=C1F)=O)N AMHSVLOKQVVFRS-OBNKUBODSA-N 0.000 claims 1
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- 125000000232 haloalkynyl group Chemical group 0.000 claims 1
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- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
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- 229930004008 p-menthane Natural products 0.000 description 1
- JZIWECMAEHNDRL-UHFFFAOYSA-N pentacosylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC1CCCCC1 JZIWECMAEHNDRL-UHFFFAOYSA-N 0.000 description 1
- KPZXPRZDTHVHLX-UHFFFAOYSA-N pentacosylcyclopentane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCC1CCCC1 KPZXPRZDTHVHLX-UHFFFAOYSA-N 0.000 description 1
- ZNUABQHWFGTOCO-UHFFFAOYSA-N pentadecylcyclohexane Chemical compound CCCCCCCCCCCCCCCC1CCCCC1 ZNUABQHWFGTOCO-UHFFFAOYSA-N 0.000 description 1
- WTFOZIBFLJCOHA-UHFFFAOYSA-N pentatriacontylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCCC1 WTFOZIBFLJCOHA-UHFFFAOYSA-N 0.000 description 1
- IVYUBHPJNFFACJ-UHFFFAOYSA-N pentatriacontylcyclopentane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCC1 IVYUBHPJNFFACJ-UHFFFAOYSA-N 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
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- 239000000047 product Substances 0.000 description 1
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- 239000001294 propane Substances 0.000 description 1
- 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
- 150000003254 radicals Chemical class 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- WJXREUZUPGMAII-UHFFFAOYSA-N sulfurazidic acid Chemical compound OS(=O)(=O)N=[N+]=[N-] WJXREUZUPGMAII-UHFFFAOYSA-N 0.000 description 1
- 208000011580 syndromic disease Diseases 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
- KVZJLSYJROEPSQ-HTQZYQBOSA-N trans-1,2-dimethylcyclohexane Chemical compound C[C@@H]1CCCC[C@H]1C KVZJLSYJROEPSQ-HTQZYQBOSA-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
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- LUTRXSGNOWYTNZ-UHFFFAOYSA-N tricosylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC1CCCCC1 LUTRXSGNOWYTNZ-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
- 125000002264 triphosphate group Chemical class [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 description 1
- SUJUOAZFECLBOA-UHFFFAOYSA-N tritriacontane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC SUJUOAZFECLBOA-UHFFFAOYSA-N 0.000 description 1
- JKDDSQDZJYBASB-UHFFFAOYSA-N tritriacontylcyclohexane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC1CCCCC1 JKDDSQDZJYBASB-UHFFFAOYSA-N 0.000 description 1
- 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
- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A61P31/14—Antivirals for RNA viruses
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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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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
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- A—HUMAN NECESSITIES
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- 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
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- 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)
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| US34155501P | 2001-12-14 | 2001-12-14 | |
| US60/341,555 | 2001-12-14 | ||
| PCT/US2002/040081 WO2003063771A2 (en) | 2001-12-14 | 2002-12-13 | N4-acylcytosine nucleosides for treatment of viral iinfections |
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| AU2002365234A1 AU2002365234A1 (en) | 2003-09-18 |
| AU2002365234B2 true AU2002365234B2 (en) | 2009-01-29 |
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| AU2002364730A Abandoned AU2002364730A1 (en) | 2001-12-14 | 2002-12-16 | N4-acylcytosine-1,3-dioxolane nucleosides for treatment of viral infections |
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| JP (1) | JP2005519916A (https=) |
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| 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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| 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 |
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-
2002
- 2002-12-13 AU AU2002365234A patent/AU2002365234B2/en not_active Ceased
- 2002-12-13 KR KR1020047009263A patent/KR100978904B1/ko 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 CN CNB028278402A patent/CN100560073C/zh not_active Expired - Fee Related
- 2002-12-13 BR BR0214944-3A patent/BR0214944A/pt not_active Application Discontinuation
- 2002-12-13 WO PCT/US2002/040081 patent/WO2003063771A2/en not_active Ceased
- 2002-12-13 MX MXPA04005779A patent/MXPA04005779A/es active IP Right Grant
- 2002-12-13 EP EP02804833A patent/EP1569652A4/en not_active Withdrawn
- 2002-12-13 CA CA2470255A patent/CA2470255C/en not_active Expired - Fee Related
- 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
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2006
- 2006-07-31 US US11/461,338 patent/US20070078080A1/en not_active Abandoned
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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
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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 |
| 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 |
| MXPA04005779A (es) | 2005-05-16 |
| WO2003063771A3 (en) | 2005-07-07 |
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