NO319321B1 - Neuraminsyreforbindelser, preparat inneholdende disse forbindelser samt anvendelse derav. - Google Patents
Neuraminsyreforbindelser, preparat inneholdende disse forbindelser samt anvendelse derav. Download PDFInfo
- Publication number
- NO319321B1 NO319321B1 NO19990672A NO990672A NO319321B1 NO 319321 B1 NO319321 B1 NO 319321B1 NO 19990672 A NO19990672 A NO 19990672A NO 990672 A NO990672 A NO 990672A NO 319321 B1 NO319321 B1 NO 319321B1
- Authority
- NO
- Norway
- Prior art keywords
- compound
- group
- pharmacologically acceptable
- acid
- acceptable salt
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 340
- 238000002360 preparation method Methods 0.000 title claims description 8
- -1 neuraminic acid compound Chemical class 0.000 claims abstract description 198
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 38
- 150000003839 salts Chemical class 0.000 claims abstract description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 34
- 125000005843 halogen group Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- 239000002253 acid Substances 0.000 claims description 39
- 125000002252 acyl group Chemical group 0.000 claims description 35
- 125000001931 aliphatic group Chemical group 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 208000036142 Viral infection Diseases 0.000 claims description 8
- 230000009385 viral infection Effects 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000000400 lauroyl 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])[H] 0.000 claims description 6
- 125000001419 myristoyl 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])[H] 0.000 claims description 6
- 125000002801 octanoyl group Chemical group C(CCCCCCC)(=O)* 0.000 claims description 6
- 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 6
- 125000003696 stearoyl 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])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000003074 decanoyl group Chemical group [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(*)=O 0.000 claims description 5
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
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- 108010006232 Neuraminidase Proteins 0.000 abstract description 16
- 150000002148 esters Chemical group 0.000 abstract description 15
- 230000002401 inhibitory effect Effects 0.000 abstract description 15
- CERZMXAJYMMUDR-UHFFFAOYSA-N neuraminic acid Natural products NC1C(O)CC(O)(C(O)=O)OC1C(O)C(O)CO CERZMXAJYMMUDR-UHFFFAOYSA-N 0.000 abstract description 13
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 132
- 238000006243 chemical reaction Methods 0.000 description 118
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 105
- 238000000034 method Methods 0.000 description 105
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 20
- 229940126062 Compound A Drugs 0.000 description 19
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- 238000005481 NMR spectroscopy Methods 0.000 description 19
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- 125000000755 henicosyl 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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 1
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000008011 inorganic excipient Substances 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229940046892 lead acetate Drugs 0.000 description 1
- 125000002463 lignoceryl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 229940031703 low substituted hydroxypropyl cellulose Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Chemical class 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229940037627 magnesium lauryl sulfate Drugs 0.000 description 1
- HBNDBUATLJAUQM-UHFFFAOYSA-L magnesium;dodecyl sulfate Chemical compound [Mg+2].CCCCCCCCCCCCOS([O-])(=O)=O.CCCCCCCCCCCCOS([O-])(=O)=O HBNDBUATLJAUQM-UHFFFAOYSA-L 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- ZUSSTQCWRDLYJA-UHFFFAOYSA-N n-hydroxy-5-norbornene-2,3-dicarboximide Chemical compound C1=CC2CC1C1C2C(=O)N(O)C1=O ZUSSTQCWRDLYJA-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000008012 organic excipient Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- REJGOFYVRVIODZ-UHFFFAOYSA-N phosphanium;chloride Chemical class P.Cl REJGOFYVRVIODZ-UHFFFAOYSA-N 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 235000019423 pullulan Nutrition 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- NGHMEZWZOZEZOH-UHFFFAOYSA-N silicic acid;hydrate Chemical compound O.O[Si](O)(O)O NGHMEZWZOZEZOH-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 235000019385 spermaceti wax Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- QQWYQAQQADNEIC-UHFFFAOYSA-N tert-butyl [[cyano(phenyl)methylidene]amino] carbonate Chemical compound CC(C)(C)OC(=O)ON=C(C#N)C1=CC=CC=C1 QQWYQAQQADNEIC-UHFFFAOYSA-N 0.000 description 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
- 125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- STYLPRGRDWXUBE-UHFFFAOYSA-N tert-butylsilyl trifluoromethanesulfonate Chemical compound CC(C)(C)[SiH2]OS(=O)(=O)C(F)(F)F STYLPRGRDWXUBE-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 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
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002469 tricosyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- 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
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Pulmonology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Pyrane Compounds (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21345696 | 1996-08-13 | ||
| PCT/JP1997/002810 WO1998006712A1 (en) | 1996-08-13 | 1997-08-12 | Neuraminic acid compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO990672D0 NO990672D0 (no) | 1999-02-12 |
| NO990672L NO990672L (no) | 1999-04-13 |
| NO319321B1 true NO319321B1 (no) | 2005-07-11 |
Family
ID=16639524
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19990672A NO319321B1 (no) | 1996-08-13 | 1999-02-12 | Neuraminsyreforbindelser, preparat inneholdende disse forbindelser samt anvendelse derav. |
Country Status (17)
| Country | Link |
|---|---|
| EP (1) | EP0934939B1 (cs) |
| KR (1) | KR100526666B1 (cs) |
| CN (1) | CN1126752C (cs) |
| AT (1) | ATE239006T1 (cs) |
| AU (1) | AU723994B2 (cs) |
| CA (1) | CA2263336C (cs) |
| CZ (1) | CZ293041B6 (cs) |
| DE (1) | DE69721553T2 (cs) |
| DK (1) | DK0934939T3 (cs) |
| ES (1) | ES2198002T3 (cs) |
| HU (1) | HU226130B1 (cs) |
| IL (1) | IL128358A (cs) |
| NO (1) | NO319321B1 (cs) |
| NZ (1) | NZ334101A (cs) |
| PT (1) | PT934939E (cs) |
| RU (1) | RU2169145C2 (cs) |
| WO (1) | WO1998006712A1 (cs) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6518305B1 (en) | 1998-04-23 | 2003-02-11 | Abbott Laboratories | Five-membered carbocyclic and heterocyclic inhibitors of neuraminidases |
| US6593314B1 (en) | 1999-10-19 | 2003-07-15 | Abbott Laboratories | Neuraminidase inhibitors |
| AU2001252578A1 (en) * | 2000-04-25 | 2001-11-07 | Sankyo Company Limited | Preventives for influenza |
| AUPR001000A0 (en) | 2000-09-08 | 2000-10-05 | Biota Scientific Management Pty Ltd | Novel chemical compounds and their use |
| WO2002076980A1 (en) * | 2001-03-27 | 2002-10-03 | Sankyo Company, Limited | Sialic acid derivatives |
| WO2002092555A1 (en) * | 2001-05-11 | 2002-11-21 | Sankyo Company, Limited | Sialic acid derivatives |
| WO2003022841A1 (en) * | 2001-09-07 | 2003-03-20 | Biota Scientific Management Pty Ltd | Intermediates for preparing neuraminidase inhibitor conjugates |
| RU2237470C1 (ru) * | 2003-01-27 | 2004-10-10 | Купсин Евгений Вениаминович | Комбинированный препарат для устранения симптомов простудных заболеваний и гриппа (варианты) |
| TWI549956B (zh) * | 2007-04-11 | 2016-09-21 | 第一三共股份有限公司 | 神經胺酸衍生物及其製造方法 |
| CN102532080A (zh) * | 2010-12-29 | 2012-07-04 | 中国科学院上海药物研究所 | 新型唾液酸衍生物及其制备方法,包含该衍生物的药物组合物,以及其用途 |
| WO2012114350A1 (en) * | 2011-02-24 | 2012-08-30 | Cadila Healthcare Limited | Process for the preparation of zanamivir |
| RU2520836C1 (ru) * | 2013-02-27 | 2014-06-27 | Александр Васильевич Иващенко | (3r,4r,5s)-4-амино-5-(2,2-дифторацетиламино)-3-(1-этилпропокси)-циклогекс-1-енкарбоновая кислота и ее эфиры, способ их получения и применения |
| CN117243852A (zh) * | 2023-11-01 | 2023-12-19 | 华熙生物科技股份有限公司 | 一种皮肤外用组合物及其用途 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2000786C1 (ru) * | 1989-07-25 | 1993-10-15 | Научно-исследовательский институт экспериментальной медицины РАМН | Противовирусное средство при гриппозной инфекции |
| CZ288492B6 (en) * | 1990-04-24 | 2001-06-13 | Biota Scient Management | Derivatives of alpha-D-neuraminic acid, process of their preparation, their use and pharmaceutical preparations based thereon |
| RU2032683C1 (ru) * | 1991-07-02 | 1995-04-10 | Андрейчиков Юрий Сергеевич | 2-метил-5-метокси-3-метоксалилацетобензофуран, проявляющий противовирусную активность в отношении вируса гриппа типа а и в |
| AU659501B2 (en) * | 1991-10-23 | 1995-05-18 | Biota Scientific Management Pty Ltd | Antiviral 4-substituted-2-deoxy-2,3-didehydro-derivatives of alpha-D-neuraminic acid |
| RU2030412C1 (ru) * | 1992-03-04 | 1995-03-10 | Иркутский институт органической химии СО РАН | Способ получения 2-формил-2,5- дибутилтио-2,3- дигидро-4h-пирана |
| AUPM354694A0 (en) * | 1994-01-27 | 1994-02-17 | Biota Scientific Management Pty Ltd | Chemical compounds |
-
1997
- 1997-08-12 CA CA002263336A patent/CA2263336C/en not_active Expired - Fee Related
- 1997-08-12 WO PCT/JP1997/002810 patent/WO1998006712A1/ja not_active Ceased
- 1997-08-12 AU AU37858/97A patent/AU723994B2/en not_active Ceased
- 1997-08-12 HU HU9903632A patent/HU226130B1/hu not_active IP Right Cessation
- 1997-08-12 RU RU99105348/04A patent/RU2169145C2/ru not_active IP Right Cessation
- 1997-08-12 DK DK97934769T patent/DK0934939T3/da active
- 1997-08-12 DE DE69721553T patent/DE69721553T2/de not_active Expired - Lifetime
- 1997-08-12 NZ NZ334101A patent/NZ334101A/en not_active IP Right Cessation
- 1997-08-12 CN CN97198571A patent/CN1126752C/zh not_active Expired - Fee Related
- 1997-08-12 AT AT97934769T patent/ATE239006T1/de active
- 1997-08-12 ES ES97934769T patent/ES2198002T3/es not_active Expired - Lifetime
- 1997-08-12 IL IL12835897A patent/IL128358A/xx not_active IP Right Cessation
- 1997-08-12 CZ CZ1999365A patent/CZ293041B6/cs not_active IP Right Cessation
- 1997-08-12 PT PT97934769T patent/PT934939E/pt unknown
- 1997-08-12 EP EP97934769A patent/EP0934939B1/en not_active Expired - Lifetime
- 1997-08-12 KR KR10-1999-7001217A patent/KR100526666B1/ko not_active Expired - Fee Related
-
1999
- 1999-02-12 NO NO19990672A patent/NO319321B1/no not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CZ36599A3 (cs) | 1999-06-16 |
| CA2263336A1 (en) | 1998-02-19 |
| ATE239006T1 (de) | 2003-05-15 |
| ES2198002T3 (es) | 2004-01-16 |
| WO1998006712A1 (en) | 1998-02-19 |
| KR100526666B1 (ko) | 2005-11-08 |
| EP0934939B1 (en) | 2003-05-02 |
| RU2169145C2 (ru) | 2001-06-20 |
| CA2263336C (en) | 2007-03-13 |
| AU723994B2 (en) | 2000-09-07 |
| HUP9903632A2 (hu) | 2001-08-28 |
| IL128358A0 (en) | 2000-01-31 |
| HK1022687A1 (en) | 2000-08-18 |
| DE69721553T2 (de) | 2004-07-22 |
| EP0934939A1 (en) | 1999-08-11 |
| PT934939E (pt) | 2003-07-31 |
| CN1232461A (zh) | 1999-10-20 |
| IL128358A (en) | 2003-04-10 |
| KR20000029971A (ko) | 2000-05-25 |
| HUP9903632A3 (en) | 2002-04-29 |
| NZ334101A (en) | 2001-07-27 |
| DE69721553D1 (de) | 2003-06-05 |
| AU3785897A (en) | 1998-03-06 |
| CN1126752C (zh) | 2003-11-05 |
| NO990672L (no) | 1999-04-13 |
| HU226130B1 (en) | 2008-05-28 |
| EP0934939A4 (cs) | 1999-09-15 |
| DK0934939T3 (da) | 2003-07-21 |
| CZ293041B6 (cs) | 2004-01-14 |
| NO990672D0 (no) | 1999-02-12 |
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