AU2003210125B2 - Use of polysaccharide derivatives as anti-infective substances - Google Patents
Use of polysaccharide derivatives as anti-infective substances Download PDFInfo
- Publication number
- AU2003210125B2 AU2003210125B2 AU2003210125A AU2003210125A AU2003210125B2 AU 2003210125 B2 AU2003210125 B2 AU 2003210125B2 AU 2003210125 A AU2003210125 A AU 2003210125A AU 2003210125 A AU2003210125 A AU 2003210125A AU 2003210125 B2 AU2003210125 B2 AU 2003210125B2
- Authority
- AU
- Australia
- Prior art keywords
- starch
- sub
- benzyl
- alkyl
- quab
- 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.)
- Ceased
Links
- 150000004676 glycans Chemical class 0.000 title claims abstract description 46
- 229920001282 polysaccharide Polymers 0.000 title claims abstract description 43
- 239000005017 polysaccharide Substances 0.000 title claims abstract description 43
- 239000000126 substance Substances 0.000 title description 14
- 230000002924 anti-infective effect Effects 0.000 title description 7
- 229920002472 Starch Polymers 0.000 claims abstract description 33
- 235000019698 starch Nutrition 0.000 claims abstract description 24
- 238000006467 substitution reaction Methods 0.000 claims abstract description 21
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 18
- 239000008107 starch Substances 0.000 claims abstract description 18
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 8
- 208000035473 Communicable disease Diseases 0.000 claims abstract description 6
- 150000001450 anions Chemical group 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 229920002261 Corn starch Polymers 0.000 claims description 10
- 239000008120 corn starch Substances 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 229940100445 wheat starch Drugs 0.000 claims description 9
- 125000005647 linker group Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 229920001592 potato starch Polymers 0.000 claims description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 150000004804 polysaccharides Polymers 0.000 claims description 4
- -1 rice starch Polymers 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 3
- 241000196324 Embryophyta Species 0.000 claims description 2
- 229940099112 cornstarch Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229940116317 potato starch Drugs 0.000 claims description 2
- 229940100486 rice starch Drugs 0.000 claims description 2
- 229940032147 starch Drugs 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 7
- 230000002401 inhibitory effect Effects 0.000 abstract description 7
- 238000000034 method Methods 0.000 abstract description 6
- 239000000203 mixture Substances 0.000 abstract description 6
- 208000015181 infectious disease Diseases 0.000 abstract description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract description 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 3
- 125000004663 dialkyl amino group Chemical group 0.000 abstract description 3
- 229910052736 halogen Inorganic materials 0.000 abstract description 3
- 150000002367 halogens Chemical class 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract description 2
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 abstract 1
- CSPHGSFZFWKVDL-UHFFFAOYSA-M (3-chloro-2-hydroxypropyl)-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)CCl CSPHGSFZFWKVDL-UHFFFAOYSA-M 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 150000001875 compounds Chemical class 0.000 description 19
- 239000003153 chemical reaction reagent Substances 0.000 description 14
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- 239000000243 solution Substances 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 230000000840 anti-viral effect Effects 0.000 description 6
- 125000002091 cationic group Chemical group 0.000 description 6
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- 235000002595 Solanum tuberosum Nutrition 0.000 description 5
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- 230000000694 effects Effects 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
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- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- 241001529453 unidentified herpesvirus Species 0.000 description 3
- 229920000945 Amylopectin Polymers 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229920001661 Chitosan Polymers 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000295644 Staphylococcaceae Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical group [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 241000209140 Triticum Species 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
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- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 229960004150 aciclovir Drugs 0.000 description 2
- MKUXAQIIEYXACX-UHFFFAOYSA-N aciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(COCCO)C=N2 MKUXAQIIEYXACX-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000002777 nucleoside Substances 0.000 description 2
- 150000003833 nucleoside derivatives Chemical class 0.000 description 2
- 239000002773 nucleotide Substances 0.000 description 2
- 125000003729 nucleotide group Chemical group 0.000 description 2
- ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical compound OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229920001059 synthetic polymer Polymers 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- 230000009385 viral infection Effects 0.000 description 2
- HEEACTTWORLLPM-UHFFFAOYSA-N 2-(1h-imidazol-5-yl)ethanol Chemical compound OCCC1=CNC=N1 HEEACTTWORLLPM-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000867607 Chlorocebus sabaeus Species 0.000 description 1
- VWFCHDSQECPREK-LURJTMIESA-N Cidofovir Chemical compound NC=1C=CN(C[C@@H](CO)OCP(O)(O)=O)C(=O)N=1 VWFCHDSQECPREK-LURJTMIESA-N 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- 102000016928 DNA-directed DNA polymerase Human genes 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229920002097 Lichenin Polymers 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- 241000187644 Mycobacterium vaccae Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- JNTOCHDNEULJHD-UHFFFAOYSA-N Penciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(CCC(CO)CO)C=N2 JNTOCHDNEULJHD-UHFFFAOYSA-N 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 229920000289 Polyquaternium Polymers 0.000 description 1
- 229920001218 Pullulan Polymers 0.000 description 1
- 239000004373 Pullulan Substances 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- GCQYYIHYQMVWLT-HQNLTJAPSA-N Sorivudine Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(\C=C\Br)=C1 GCQYYIHYQMVWLT-HQNLTJAPSA-N 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 108020005202 Viral DNA Proteins 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 238000009635 antibiotic susceptibility testing Methods 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000000035 biogenic effect Effects 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
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- 239000006227 byproduct Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229920006319 cationized starch Polymers 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
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- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical group [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
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- IRSCQMHQWWYFCW-UHFFFAOYSA-N ganciclovir Chemical compound O=C1NC(N)=NC2=C1N=CN2COC(CO)CO IRSCQMHQWWYFCW-UHFFFAOYSA-N 0.000 description 1
- 229960002963 ganciclovir Drugs 0.000 description 1
- 238000010559 graft polymerization reaction Methods 0.000 description 1
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- 210000003734 kidney Anatomy 0.000 description 1
- TWNIBLMWSKIRAT-VFUOTHLCSA-N levoglucosan Chemical group O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O2 TWNIBLMWSKIRAT-VFUOTHLCSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
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- 244000005700 microbiome Species 0.000 description 1
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- 231100000219 mutagenic Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
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- 231100000956 nontoxicity Toxicity 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 230000002246 oncogenic effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 229960001179 penciclovir Drugs 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003138 primary alcohols Chemical group 0.000 description 1
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- 235000019423 pullulan Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
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- 238000003756 stirring Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
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- 231100000378 teratogenic Toxicity 0.000 description 1
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- 231100000419 toxicity Toxicity 0.000 description 1
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- 230000007704 transition Effects 0.000 description 1
- PUVAFTRIIUSGLK-UHFFFAOYSA-M trimethyl(oxiran-2-ylmethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1CO1 PUVAFTRIIUSGLK-UHFFFAOYSA-M 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
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- LTVDFSLWFKLJDQ-UHFFFAOYSA-N α-tocopherolquinone Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)(O)CCC1=C(C)C(=O)C(C)=C(C)C1=O LTVDFSLWFKLJDQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/716—Glucans
- A61K31/717—Celluloses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/716—Glucans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/716—Glucans
- A61K31/718—Starch or degraded starch, e.g. amylose, amylopectin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/716—Glucans
- A61K31/719—Pullulans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/716—Glucans
- A61K31/721—Dextrans
-
- 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
-
- 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
- A61P31/04—Antibacterial agents
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10200717.9 | 2002-01-10 | ||
| DE10200717A DE10200717A1 (de) | 2002-01-10 | 2002-01-10 | Verwendung von Polysaccharid-Derivaten als antiinfektive Substanzen |
| PCT/DE2003/000095 WO2003057227A1 (de) | 2002-01-10 | 2003-01-10 | Verwendung von polysaccharid-derivaten als antiinfektive substanzen |
Publications (2)
| Publication Number | Publication Date |
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| AU2003210125A1 AU2003210125A1 (en) | 2003-07-24 |
| AU2003210125B2 true AU2003210125B2 (en) | 2008-01-24 |
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Family Applications (1)
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|---|---|---|---|
| AU2003210125A Ceased AU2003210125B2 (en) | 2002-01-10 | 2003-01-10 | Use of polysaccharide derivatives as anti-infective substances |
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|---|---|
| US (1) | US7297687B2 (enExample) |
| EP (1) | EP1465640B8 (enExample) |
| JP (1) | JP4452777B2 (enExample) |
| KR (1) | KR100913301B1 (enExample) |
| CN (1) | CN1615141B (enExample) |
| AT (1) | ATE408411T1 (enExample) |
| AU (1) | AU2003210125B2 (enExample) |
| BR (1) | BRPI0306851A8 (enExample) |
| CA (1) | CA2472586C (enExample) |
| DE (2) | DE10200717A1 (enExample) |
| ES (1) | ES2314205T3 (enExample) |
| MX (1) | MXPA04006673A (enExample) |
| NO (1) | NO20043265L (enExample) |
| PL (1) | PL206600B1 (enExample) |
| RU (1) | RU2332221C2 (enExample) |
| WO (1) | WO2003057227A1 (enExample) |
| ZA (1) | ZA200405400B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004110193A1 (en) * | 2003-06-13 | 2004-12-23 | Wadstroem Torkel | Product for absorption purposes |
| CN100469707C (zh) * | 2005-03-11 | 2009-03-18 | 中国石化北京燕化石油化工股份有限公司 | 一种高浊高铁循环冷却水的处理方法 |
| KR101278106B1 (ko) * | 2011-03-03 | 2013-06-24 | 이원실 | 이온성 액체를 이용한 셀룰로오스계 고분자 항균제의 제조방법 |
| EP2822384A1 (de) | 2012-03-09 | 2015-01-14 | Friedrich-Schiller-Universität Jena | Di- und multifunktional amin-modifizierte oligo- und polysaccharidderivate als antiinfektive substanzen und deren verwendung |
| US20170360040A1 (en) * | 2014-12-02 | 2017-12-21 | B.G. Negev Technologies And Applications Ltd., At Ben-Gurion University | Modified polysaccharides for use as anti-microbial agents |
| FR3064473B1 (fr) * | 2017-04-03 | 2021-02-12 | Basf Beauty Care Solutions France Sas | Ingredient protecteur de l'equilibre de la flore microbienne cutanee et/ou mucosale |
| CN112423771B (zh) * | 2018-07-20 | 2023-05-09 | 株式会社资生堂 | 病毒灭活剂 |
| CN115260320B (zh) * | 2021-04-30 | 2023-05-05 | 中国科学院化学研究所 | 离子型多糖衍生物用作防冰涂层材料的应用 |
| KR102559540B1 (ko) | 2022-09-19 | 2023-07-25 | 문건희 | 토류벽시스템용 토류벽체 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JPH0457969A (ja) * | 1990-06-27 | 1992-02-25 | Unitika Ltd | 抗菌性布帛の製造方法 |
| WO2000026447A1 (en) * | 1998-10-29 | 2000-05-11 | Ciba Specialty Chemicals Holding Inc. | Incorporation of organic anti-microbials into fibres during a fibre spinning process |
| US6306835B1 (en) * | 1997-09-23 | 2001-10-23 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Biocidal chitosan derivatives |
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| JPS60203265A (ja) * | 1984-03-28 | 1985-10-14 | ダイセル化学工業株式会社 | 抗血液凝固性高分子材料 |
| DE3711680A1 (de) * | 1987-04-07 | 1988-10-27 | Hoechst Ag | Waessrige biozide kationische kunststoffdispersionen und deren verwendung als fungizide, bakterizide und algizide ausruestungsmittel |
| DE3720555A1 (de) * | 1987-06-22 | 1989-01-05 | Henkel Kgaa | Verwendung von unloeslichen, polyfunktionellen quartaeren ammoniumverbindungen zur adsorptiven bindung von mikroorganismen |
| IT1231168B (it) * | 1989-07-21 | 1991-11-22 | Texcontor Ets | Copolimeri saccaridici aventi attivita' antibatterica. |
| US5731259A (en) | 1991-05-03 | 1998-03-24 | Societa Consortile Ricerche Angelini S.P.A. | Cationic polysaccharides |
| IT1249309B (it) * | 1991-05-03 | 1995-02-22 | Faricerca Spa | Polisaccaridi di tipo cationico |
| GB2262531B (en) * | 1991-12-17 | 1995-12-06 | Erba Carlo Spa | Antiviral sulphated polysaccharides |
| JPH05295002A (ja) * | 1992-04-23 | 1993-11-09 | Nichiden Kagaku Kk | 抗菌性澱粉、水溶性多糖類及びその製造方法 |
| ZA947572B (en) * | 1993-09-29 | 1995-09-28 | Hampton Roads Medical College | Contraceptive compositions |
| RU2098114C1 (ru) * | 1995-02-03 | 1997-12-10 | Музыка Владислав Иванович | Препарат, воздействующий на функциональную активность клеток эукариот и прокариот |
| JPH10155898A (ja) * | 1996-11-26 | 1998-06-16 | Toyobo Co Ltd | 抗菌性付与抗血栓性材料 |
| US6096291A (en) | 1996-12-27 | 2000-08-01 | Biovector Therapeutics, S.A. | Mucosal administration of substances to mammals |
| CA2268464A1 (en) * | 1998-04-09 | 1999-10-09 | National Starch And Chemical Investment Holding Corporation | Nonionically derivatized starches and their use in non-aerosol, low voc hair cosmetic compositions |
-
2002
- 2002-01-10 DE DE10200717A patent/DE10200717A1/de not_active Withdrawn
-
2003
- 2003-01-10 MX MXPA04006673A patent/MXPA04006673A/es active IP Right Grant
- 2003-01-10 WO PCT/DE2003/000095 patent/WO2003057227A1/de not_active Ceased
- 2003-01-10 CA CA2472586A patent/CA2472586C/en not_active Expired - Fee Related
- 2003-01-10 DE DE50310510T patent/DE50310510D1/de not_active Expired - Lifetime
- 2003-01-10 KR KR1020047010731A patent/KR100913301B1/ko not_active Expired - Fee Related
- 2003-01-10 AU AU2003210125A patent/AU2003210125B2/en not_active Ceased
- 2003-01-10 RU RU2004124389/15A patent/RU2332221C2/ru not_active IP Right Cessation
- 2003-01-10 EP EP03729214A patent/EP1465640B8/de not_active Expired - Lifetime
- 2003-01-10 PL PL370887A patent/PL206600B1/pl not_active IP Right Cessation
- 2003-01-10 AT AT03729214T patent/ATE408411T1/de not_active IP Right Cessation
- 2003-01-10 JP JP2003557585A patent/JP4452777B2/ja not_active Expired - Fee Related
- 2003-01-10 ES ES03729214T patent/ES2314205T3/es not_active Expired - Lifetime
- 2003-01-10 BR BRPI0306851A patent/BRPI0306851A8/pt not_active IP Right Cessation
- 2003-01-10 US US10/500,807 patent/US7297687B2/en not_active Expired - Fee Related
- 2003-01-10 CN CN038021072A patent/CN1615141B/zh not_active Expired - Fee Related
-
2004
- 2004-07-07 ZA ZA2004/05400A patent/ZA200405400B/en unknown
- 2004-08-04 NO NO20043265A patent/NO20043265L/no not_active Application Discontinuation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0457969A (ja) * | 1990-06-27 | 1992-02-25 | Unitika Ltd | 抗菌性布帛の製造方法 |
| US6306835B1 (en) * | 1997-09-23 | 2001-10-23 | Board Of Supervisors Of Louisiana State University And Agricultural And Mechanical College | Biocidal chitosan derivatives |
| WO2000026447A1 (en) * | 1998-10-29 | 2000-05-11 | Ciba Specialty Chemicals Holding Inc. | Incorporation of organic anti-microbials into fibres during a fibre spinning process |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1615141A (zh) | 2005-05-11 |
| JP2005519057A (ja) | 2005-06-30 |
| CA2472586C (en) | 2011-03-15 |
| EP1465640A1 (de) | 2004-10-13 |
| JP4452777B2 (ja) | 2010-04-21 |
| US20050054609A1 (en) | 2005-03-10 |
| BRPI0306851A8 (pt) | 2017-04-25 |
| EP1465640B1 (de) | 2008-09-17 |
| RU2332221C2 (ru) | 2008-08-27 |
| WO2003057227A1 (de) | 2003-07-17 |
| CA2472586A1 (en) | 2003-07-17 |
| BRPI0306851A2 (pt) | 2016-11-16 |
| ZA200405400B (en) | 2005-11-30 |
| AU2003210125A1 (en) | 2003-07-24 |
| KR20040079415A (ko) | 2004-09-14 |
| NO20043265L (no) | 2004-08-04 |
| MXPA04006673A (es) | 2004-11-10 |
| DE10200717A1 (de) | 2003-07-31 |
| EP1465640B8 (de) | 2009-04-01 |
| PL206600B1 (pl) | 2010-08-31 |
| PL370887A1 (en) | 2005-05-30 |
| ES2314205T3 (es) | 2009-03-16 |
| KR100913301B1 (ko) | 2009-08-26 |
| ATE408411T1 (de) | 2008-10-15 |
| US7297687B2 (en) | 2007-11-20 |
| DE50310510D1 (de) | 2008-10-30 |
| RU2004124389A (ru) | 2005-05-10 |
| CN1615141B (zh) | 2013-08-14 |
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Owner name: DOW GLOBAL TECHNOLOGIES INC. Free format text: FORMER OWNER WAS: DOW WOLFF CELLULOSICS GMBH |
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| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |