CA2352229C - Glyceryl nucleotides, method for the production thereof and their use - Google Patents
Glyceryl nucleotides, method for the production thereof and their use Download PDFInfo
- Publication number
- CA2352229C CA2352229C CA002352229A CA2352229A CA2352229C CA 2352229 C CA2352229 C CA 2352229C CA 002352229 A CA002352229 A CA 002352229A CA 2352229 A CA2352229 A CA 2352229A CA 2352229 C CA2352229 C CA 2352229C
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- CA
- Canada
- Prior art keywords
- radicals
- hydrogen
- group
- hydroxyl
- radical
- Prior art date
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- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 title claims abstract description 28
- 238000000034 method Methods 0.000 title claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- -1 mercepto Chemical group 0.000 claims abstract description 135
- 150000001875 compounds Chemical class 0.000 claims abstract description 103
- 150000003254 radicals Chemical class 0.000 claims abstract description 82
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 61
- 125000003835 nucleoside group Chemical group 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 15
- 125000002252 acyl group Chemical group 0.000 claims abstract description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 12
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 11
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 9
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000005035 acylthio group Chemical group 0.000 claims abstract description 8
- 125000005108 alkenylthio group Chemical group 0.000 claims abstract description 8
- 150000005840 aryl radicals Chemical class 0.000 claims abstract description 8
- 125000005110 aryl thio group Chemical group 0.000 claims abstract description 8
- 201000011510 cancer Diseases 0.000 claims abstract description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 57
- 239000001257 hydrogen Substances 0.000 claims description 57
- 150000003833 nucleoside derivatives Chemical class 0.000 claims description 34
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 239000002777 nucleoside Substances 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 239000002502 liposome Substances 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical group OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 claims description 15
- 239000011737 fluorine Chemical group 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 15
- 229910052698 phosphorus Inorganic materials 0.000 claims description 15
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 15
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000004429 atom Chemical group 0.000 claims description 10
- 125000004437 phosphorous atom Chemical group 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 125000003277 amino group Chemical class 0.000 claims description 8
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000011574 phosphorus Substances 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- YEENKMKEGPBVHG-UHFFFAOYSA-N 1,3-diphosphoglycerol Chemical group OP(=O)(O)OCC(O)COP(O)(O)=O YEENKMKEGPBVHG-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 239000002105 nanoparticle Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- RDAIEEVTJKDDQZ-UHFFFAOYSA-N 2,3-dihydroxypropyl phosphono hydrogen phosphate Chemical group OCC(O)COP(O)(=O)OP(O)(O)=O RDAIEEVTJKDDQZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000002103 4,4'-dimethoxytriphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)(C1=C([H])C([H])=C(OC([H])([H])[H])C([H])=C1[H])C1=C([H])C([H])=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- XEHVFKKSDRMODV-UHFFFAOYSA-N ethynyl Chemical group C#[C] XEHVFKKSDRMODV-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 2
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims description 2
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims 1
- 125000000837 carbohydrate group Chemical group 0.000 claims 1
- 208000035473 Communicable disease Diseases 0.000 abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 129
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 64
- 239000000243 solution Substances 0.000 description 39
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 30
- 239000006188 syrup Substances 0.000 description 28
- 235000020357 syrup Nutrition 0.000 description 28
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 229910052740 iodine Inorganic materials 0.000 description 20
- 239000000741 silica gel Substances 0.000 description 20
- 229910002027 silica gel Inorganic materials 0.000 description 20
- 210000004027 cell Anatomy 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 14
- 239000011630 iodine Substances 0.000 description 14
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical compound OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 description 11
- 238000002560 therapeutic procedure Methods 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 238000009833 condensation Methods 0.000 description 9
- 230000005494 condensation Effects 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 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 description 8
- 238000000338 in vitro Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- 239000012467 final product Substances 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 7
- 238000001819 mass spectrum Methods 0.000 description 7
- 239000000546 pharmaceutical excipient Substances 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
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- 229960005102 foscarnet Drugs 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 6
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- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 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
-
- 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
-
- 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
-
- 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
- A61P31/18—Antivirals for RNA viruses for HIV
-
- 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
- A61P31/20—Antivirals for DNA viruses
-
- 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
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
-
- 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
- C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
- C07H19/207—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids the phosphoric or polyphosphoric acids being esterified by a further hydroxylic compound, e.g. flavine adenine dinucleotide or nicotinamide-adenine dinucleotide
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Virology (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Oncology (AREA)
- Genetics & Genomics (AREA)
- Communicable Diseases (AREA)
- Hematology (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19855963A DE19855963A1 (de) | 1998-12-04 | 1998-12-04 | Amphiphile Glycerylnucleotide, Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE19855963.1 | 1998-12-04 | ||
| PCT/EP1999/009461 WO2000034298A1 (de) | 1998-12-04 | 1999-12-03 | Glycerylnucleotide, verfahren zu ihrer herstellung und ihre verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2352229A1 CA2352229A1 (en) | 2000-06-15 |
| CA2352229C true CA2352229C (en) | 2009-06-09 |
Family
ID=7889957
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002352229A Expired - Fee Related CA2352229C (en) | 1998-12-04 | 1999-12-03 | Glyceryl nucleotides, method for the production thereof and their use |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6787525B1 (enExample) |
| EP (1) | EP1135401B1 (enExample) |
| JP (1) | JP4879398B2 (enExample) |
| AT (1) | ATE243220T1 (enExample) |
| AU (1) | AU1558800A (enExample) |
| CA (1) | CA2352229C (enExample) |
| DE (2) | DE19855963A1 (enExample) |
| DK (1) | DK1135401T3 (enExample) |
| ES (1) | ES2201805T3 (enExample) |
| WO (1) | WO2000034298A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10228059B4 (de) * | 2002-06-19 | 2005-12-29 | Eberhard-Karls-Universität Tübingen | Verwendung von amphiphilen Nucleosid-Phosphonoameisensäure-Derivaten zur Behandlung von viralen Infektionskrankheiten |
| US7593913B2 (en) * | 2006-01-11 | 2009-09-22 | Siemens Medical Solutions Usa, Inc. | Systems and method for integrative medical decision support |
| CA2812962C (en) | 2010-09-22 | 2020-03-31 | Alios Biopharma, Inc. | Azido nucleosides and nucleotide analogs |
| EP2794627B1 (en) | 2011-12-22 | 2018-09-26 | Alios Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| US9441007B2 (en) | 2012-03-21 | 2016-09-13 | Alios Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| USRE48171E1 (en) | 2012-03-21 | 2020-08-25 | Janssen Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| HUE029038T2 (en) | 2012-05-25 | 2017-01-30 | Janssen Sciences Ireland Uc | Uracil spirooxetan nucleosides |
| EP2935303B1 (en) | 2012-12-21 | 2021-02-17 | Janssen BioPharma, Inc. | 4'-fluoro-nucleosides, 4'-fluoro-nucleotides and analogs thereof for the treatment of hcv |
| AU2014331863C1 (en) | 2013-10-11 | 2019-05-16 | Alios Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03236396A (ja) * | 1990-02-10 | 1991-10-22 | Tosoh Corp | 修飾オリゴデオキシヌクレオチド及びそれを含むｄｎａ |
| JPH0421694A (ja) * | 1990-05-16 | 1992-01-24 | Asahi Chem Ind Co Ltd | 新規なヌクレオシド―リン脂質複合体 |
| DE69119074T2 (de) * | 1990-06-15 | 1996-12-12 | University Of North Carolina At Chapel Hill, Chapel Hill, N.C. | Kovalente-ther lipidnukleosid-konjugate |
| CA2129986C (en) | 1992-02-13 | 2003-12-09 | Albert Reto Schwendener | Amphiphile nucleosidphosphatanaloga |
| DE4418690A1 (de) * | 1994-05-28 | 1996-01-11 | Boehringer Mannheim Gmbh | Neue Lipidester von Nucleosid-Monophosphaten und deren Verwendung als immunsuppressive Arzneimittel |
| DE69535758D1 (de) * | 1994-08-29 | 2008-07-03 | Univ Wake Forest | Lipid-analoge zur behandlung von viralen infektionen |
| AU3120797A (en) | 1996-05-08 | 1998-07-31 | Weider Nutrition Group, Inc. | Structured glycerols and structured phosphatides |
| US6686462B2 (en) * | 1997-02-28 | 2004-02-03 | The Regents Of The University Of California | Antiviral compounds and methods of administration |
-
1998
- 1998-12-04 DE DE19855963A patent/DE19855963A1/de not_active Withdrawn
-
1999
- 1999-12-03 DE DE59906041T patent/DE59906041D1/de not_active Expired - Lifetime
- 1999-12-03 AT AT99958161T patent/ATE243220T1/de not_active IP Right Cessation
- 1999-12-03 AU AU15588/00A patent/AU1558800A/en not_active Abandoned
- 1999-12-03 DK DK99958161T patent/DK1135401T3/da active
- 1999-12-03 EP EP99958161A patent/EP1135401B1/de not_active Expired - Lifetime
- 1999-12-03 WO PCT/EP1999/009461 patent/WO2000034298A1/de not_active Ceased
- 1999-12-03 JP JP2000586741A patent/JP4879398B2/ja not_active Expired - Fee Related
- 1999-12-03 CA CA002352229A patent/CA2352229C/en not_active Expired - Fee Related
- 1999-12-03 US US09/856,165 patent/US6787525B1/en not_active Expired - Fee Related
- 1999-12-03 ES ES99958161T patent/ES2201805T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| AU1558800A (en) | 2000-06-26 |
| JP4879398B2 (ja) | 2012-02-22 |
| ATE243220T1 (de) | 2003-07-15 |
| DE59906041D1 (de) | 2003-07-24 |
| CA2352229A1 (en) | 2000-06-15 |
| JP2002531573A (ja) | 2002-09-24 |
| US6787525B1 (en) | 2004-09-07 |
| EP1135401B1 (de) | 2003-06-18 |
| WO2000034298A1 (de) | 2000-06-15 |
| DE19855963A1 (de) | 2000-06-08 |
| DK1135401T3 (da) | 2003-10-06 |
| EP1135401A1 (de) | 2001-09-26 |
| ES2201805T3 (es) | 2004-03-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20141203 |