CA2711663C - Liquid antiseptic compositions containing iodine and a sugar and/or sugar alcohol - Google Patents
Liquid antiseptic compositions containing iodine and a sugar and/or sugar alcohol Download PDFInfo
- Publication number
- CA2711663C CA2711663C CA2711663A CA2711663A CA2711663C CA 2711663 C CA2711663 C CA 2711663C CA 2711663 A CA2711663 A CA 2711663A CA 2711663 A CA2711663 A CA 2711663A CA 2711663 C CA2711663 C CA 2711663C
- Authority
- CA
- Canada
- Prior art keywords
- tissue
- composition
- antiseptic composition
- tissue antiseptic
- viscosity
- 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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- 239000000203 mixture Substances 0.000 title claims abstract description 328
- 239000011630 iodine Substances 0.000 title claims abstract description 67
- 229910052740 iodine Inorganic materials 0.000 title claims abstract description 67
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 230000002421 anti-septic effect Effects 0.000 title claims description 138
- 150000005846 sugar alcohols Chemical class 0.000 title claims description 43
- 239000007788 liquid Substances 0.000 title claims description 25
- 210000001519 tissue Anatomy 0.000 claims description 145
- 239000004094 surface-active agent Substances 0.000 claims description 78
- 150000002772 monosaccharides Chemical class 0.000 claims description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 47
- 239000002562 thickening agent Substances 0.000 claims description 46
- 239000004599 antimicrobial Substances 0.000 claims description 39
- 210000004400 mucous membrane Anatomy 0.000 claims description 28
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 25
- 230000000845 anti-microbial effect Effects 0.000 claims description 25
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 25
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 24
- 239000000811 xylitol Substances 0.000 claims description 24
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 24
- 235000010447 xylitol Nutrition 0.000 claims description 24
- 229960002675 xylitol Drugs 0.000 claims description 24
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 21
- 239000002888 zwitterionic surfactant Substances 0.000 claims description 20
- 239000003945 anionic surfactant Substances 0.000 claims description 19
- 239000002736 nonionic surfactant Substances 0.000 claims description 14
- 229940061720 alpha hydroxy acid Drugs 0.000 claims description 12
- 150000001280 alpha hydroxy acids Chemical class 0.000 claims description 12
- 239000007853 buffer solution Substances 0.000 claims description 11
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 11
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 10
- 229930195725 Mannitol Natural products 0.000 claims description 10
- 239000000594 mannitol Substances 0.000 claims description 10
- 235000010355 mannitol Nutrition 0.000 claims description 10
- 230000000249 desinfective effect Effects 0.000 claims description 6
- 239000003906 humectant Substances 0.000 claims description 6
- 150000002632 lipids Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000005259 measurement Methods 0.000 claims description 3
- 230000003260 anti-sepsis Effects 0.000 abstract description 5
- 229920000642 polymer Polymers 0.000 description 104
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 65
- -1 dextrose Chemical class 0.000 description 45
- 238000000034 method Methods 0.000 description 38
- CPKVUHPKYQGHMW-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one;molecular iodine Chemical compound II.C=CN1CCCC1=O CPKVUHPKYQGHMW-UHFFFAOYSA-N 0.000 description 37
- 239000000243 solution Substances 0.000 description 37
- 239000003981 vehicle Substances 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- 238000012360 testing method Methods 0.000 description 21
- 125000002091 cationic group Chemical group 0.000 description 20
- 229920000153 Povidone-iodine Polymers 0.000 description 18
- 229960001621 povidone-iodine Drugs 0.000 description 18
- 125000000217 alkyl group Chemical group 0.000 description 17
- 239000000178 monomer Substances 0.000 description 17
- 210000003708 urethra Anatomy 0.000 description 17
- 229910019142 PO4 Inorganic materials 0.000 description 16
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 16
- 125000003277 amino group Chemical group 0.000 description 15
- 235000021317 phosphate Nutrition 0.000 description 15
- 241000894006 Bacteria Species 0.000 description 14
- 238000009472 formulation Methods 0.000 description 14
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 14
- 239000000126 substance Substances 0.000 description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 13
- 206010052428 Wound Diseases 0.000 description 13
- 230000002209 hydrophobic effect Effects 0.000 description 13
- 229920001223 polyethylene glycol Polymers 0.000 description 13
- 239000004820 Pressure-sensitive adhesive Substances 0.000 description 12
- 208000027418 Wounds and injury Diseases 0.000 description 12
- 229920001577 copolymer Polymers 0.000 description 12
- 230000009467 reduction Effects 0.000 description 12
- JKXYOQDLERSFPT-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-octadecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO JKXYOQDLERSFPT-UHFFFAOYSA-N 0.000 description 10
- 239000002202 Polyethylene glycol Substances 0.000 description 10
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 10
- 229940064804 betadine Drugs 0.000 description 10
- 239000000872 buffer Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000008367 deionised water Substances 0.000 description 9
- 229910021641 deionized water Inorganic materials 0.000 description 9
- 239000001630 malic acid Substances 0.000 description 9
- 235000011090 malic acid Nutrition 0.000 description 9
- 210000001331 nose Anatomy 0.000 description 9
- 150000003904 phospholipids Chemical class 0.000 description 9
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 229940064004 antiseptic throat preparations Drugs 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 8
- 150000001261 hydroxy acids Chemical class 0.000 description 8
- 239000004310 lactic acid Substances 0.000 description 8
- 235000014655 lactic acid Nutrition 0.000 description 8
- 239000010452 phosphate Substances 0.000 description 8
- 238000005096 rolling process Methods 0.000 description 8
- 238000005070 sampling Methods 0.000 description 8
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 229920002472 Starch Polymers 0.000 description 7
- 230000001580 bacterial effect Effects 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 229920006317 cationic polymer Polymers 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 229940035535 iodophors Drugs 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 230000000813 microbial effect Effects 0.000 description 7
- 125000000913 palmityl 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])[H] 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 241000894007 species Species 0.000 description 7
- 239000008107 starch Substances 0.000 description 7
- 235000019698 starch Nutrition 0.000 description 7
- 230000008719 thickening Effects 0.000 description 7
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 6
- 238000003556 assay Methods 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 6
- BXWNKGSJHAJOGX-UHFFFAOYSA-N n-hexadecyl alcohol Natural products CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 229920001983 poloxamer Polymers 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229920001817 Agar Polymers 0.000 description 5
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 5
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 239000004098 Tetracycline Substances 0.000 description 5
- 239000008272 agar Substances 0.000 description 5
- 125000000129 anionic group Chemical group 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 229960000541 cetyl alcohol Drugs 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 230000002147 killing effect Effects 0.000 description 5
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 5
- 229920001282 polysaccharide Polymers 0.000 description 5
- 239000005017 polysaccharide Substances 0.000 description 5
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 5
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 5
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 244000005714 skin microbiome Species 0.000 description 5
- 239000000600 sorbitol Substances 0.000 description 5
- 235000010356 sorbitol Nutrition 0.000 description 5
- 150000003871 sulfonates Chemical class 0.000 description 5
- 238000001356 surgical procedure Methods 0.000 description 5
- 229960002180 tetracycline Drugs 0.000 description 5
- 229930101283 tetracycline Natural products 0.000 description 5
- 235000019364 tetracycline Nutrition 0.000 description 5
- 150000003522 tetracyclines Chemical class 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- VAZJLPXFVQHDFB-UHFFFAOYSA-N 1-(diaminomethylidene)-2-hexylguanidine Polymers CCCCCCN=C(N)N=C(N)N VAZJLPXFVQHDFB-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 4
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 206010034133 Pathogen resistance Diseases 0.000 description 4
- 229920002413 Polyhexanide Polymers 0.000 description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 235000010419 agar Nutrition 0.000 description 4
- 125000003172 aldehyde group Chemical group 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 239000002537 cosmetic Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000003205 fragrance Substances 0.000 description 4
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229920001519 homopolymer Polymers 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 4
- 230000000415 inactivating effect Effects 0.000 description 4
- 210000003928 nasal cavity Anatomy 0.000 description 4
- 230000037311 normal skin Effects 0.000 description 4
- 229920001515 polyalkylene glycol Polymers 0.000 description 4
- 229920001451 polypropylene glycol Polymers 0.000 description 4
- 150000004804 polysaccharides Chemical class 0.000 description 4
- 229920002635 polyurethane Polymers 0.000 description 4
- 239000004814 polyurethane Substances 0.000 description 4
- 150000003138 primary alcohols Chemical class 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 125000004434 sulfur atom Chemical group 0.000 description 4
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 4
- 150000003512 tertiary amines Chemical group 0.000 description 4
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 4
- 239000001993 wax Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- 244000303965 Cyamopsis psoralioides Species 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 3
- 239000004386 Erythritol Substances 0.000 description 3
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- 229920002907 Guar gum Polymers 0.000 description 3
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 229920002125 Sokalan® Polymers 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 150000008051 alkyl sulfates Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 229920001400 block copolymer Polymers 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 235000015165 citric acid Nutrition 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 3
- 235000019414 erythritol Nutrition 0.000 description 3
- 229940009714 erythritol Drugs 0.000 description 3
- 239000012847 fine chemical Substances 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- 235000010417 guar gum Nutrition 0.000 description 3
- 239000000665 guar gum Substances 0.000 description 3
- 229960002154 guar gum Drugs 0.000 description 3
- 239000002054 inoculum Substances 0.000 description 3
- 235000010445 lecithin Nutrition 0.000 description 3
- 239000000787 lecithin Substances 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 210000000214 mouth Anatomy 0.000 description 3
- 229920001206 natural gum Polymers 0.000 description 3
- 229920005615 natural polymer Polymers 0.000 description 3
- 230000003472 neutralizing effect Effects 0.000 description 3
- 231100000344 non-irritating Toxicity 0.000 description 3
- 229920002401 polyacrylamide Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 230000002035 prolonged effect Effects 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- 238000011084 recovery Methods 0.000 description 3
- 230000002441 reversible effect Effects 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- WRTMQOHKMFDUKX-UHFFFAOYSA-N triiodide Chemical compound I[I-]I WRTMQOHKMFDUKX-UHFFFAOYSA-N 0.000 description 3
- 210000001215 vagina Anatomy 0.000 description 3
- 238000009736 wetting Methods 0.000 description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 2
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 2
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- IBBQVGDGTMTZRA-UHFFFAOYSA-N sodium;2-sulfobenzene-1,3-dicarboxylic acid Chemical compound [Na].OC(=O)C1=CC=CC(C(O)=O)=C1S(O)(=O)=O IBBQVGDGTMTZRA-UHFFFAOYSA-N 0.000 description 1
- WGRULTCAYDOGQK-UHFFFAOYSA-M sodium;sodium;hydroxide Chemical compound [OH-].[Na].[Na+] WGRULTCAYDOGQK-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229920003179 starch-based polymer Polymers 0.000 description 1
- 239000004628 starch-based polymer Substances 0.000 description 1
- 229940098760 steareth-2 Drugs 0.000 description 1
- 229940100459 steareth-20 Drugs 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 229940117986 sulfobetaine Drugs 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 239000012085 test solution Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- RRHXZLALVWBDKH-UHFFFAOYSA-M trimethyl-[2-(2-methylprop-2-enoyloxy)ethyl]azanium;chloride Chemical compound [Cl-].CC(=C)C(=O)OCC[N+](C)(C)C RRHXZLALVWBDKH-UHFFFAOYSA-M 0.000 description 1
- 239000006150 trypticase soy agar Substances 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
- A61K31/047—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates having two or more hydroxy groups, e.g. sorbitol
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/18—Iodine; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
- A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0043—Nose
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- 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
- A61P31/02—Local antiseptics
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Dermatology (AREA)
- Inorganic Chemistry (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Otolaryngology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1810907P | 2007-12-31 | 2007-12-31 | |
| US61/018,109 | 2007-12-31 | ||
| PCT/US2008/088428 WO2009088826A1 (en) | 2007-12-31 | 2008-12-29 | Liquid antiseptic compositions containing iodine and a sugar and/or sugar alcohol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2711663A1 CA2711663A1 (en) | 2009-07-16 |
| CA2711663C true CA2711663C (en) | 2017-01-10 |
Family
ID=40430202
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2711663A Active CA2711663C (en) | 2007-12-31 | 2008-12-29 | Liquid antiseptic compositions containing iodine and a sugar and/or sugar alcohol |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US10052384B2 (enExample) |
| EP (1) | EP2249805B1 (enExample) |
| JP (3) | JP6117460B2 (enExample) |
| CN (1) | CN101951887B (enExample) |
| AU (1) | AU2008346755B2 (enExample) |
| BR (1) | BRPI0819566A2 (enExample) |
| CA (1) | CA2711663C (enExample) |
| WO (1) | WO2009088826A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007031756A1 (en) * | 2005-09-16 | 2007-03-22 | Reckitt Benckiser Inc | Foaming topical compositions |
| US8808722B2 (en) | 2010-06-29 | 2014-08-19 | 3M Innovative Properties Company | Stable antiseptic compositions and methods |
| CN103006464A (zh) * | 2011-09-20 | 2013-04-03 | 天津博克尼科技发展有限公司 | 一种含碘的免水消毒洗手液 |
| CN109908170A (zh) * | 2019-04-16 | 2019-06-21 | 山东名德医疗科技有限公司 | 一种新型怡尔碘皮肤黏膜消毒液及其制备方法 |
| WO2022077100A1 (en) * | 2020-10-13 | 2022-04-21 | Goodman Janice | Iodine and polyol composition, method, and use |
| WO2022172807A1 (ja) * | 2021-02-12 | 2022-08-18 | 一丸ファルコス株式会社 | 口腔ケア用組成物 |
| FR3122572A1 (fr) * | 2021-05-07 | 2022-11-11 | Nadine GRISLAIN | Composition pharmaceutique bioadhésive comprenant du PVPI |
| KR20240044421A (ko) * | 2021-08-06 | 2024-04-04 | 가부시기가이샤오오쓰까세이야꾸고오죠오 | 소독용 조성물 |
| WO2023042226A1 (en) * | 2021-09-17 | 2023-03-23 | Kejriwal Anil | Molecular iodine and butylene glycol based formulation and its application in scalp care |
| WO2023084536A1 (en) * | 2021-11-09 | 2023-05-19 | Kejriwal Anil | Molecular iodine and butylene glycol based formulation and its application in acne care |
| WO2023084537A1 (en) * | 2021-11-09 | 2023-05-19 | Kejriwal Anil | Molecular iodine and alcohol based formulation and its application in air sanitization/disinfection |
| EP4642430A1 (en) | 2022-12-28 | 2025-11-05 | Solventum Intellectual Properties Company | Antiseptic compositions and methods |
Family Cites Families (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3728449A (en) * | 1972-05-01 | 1973-04-17 | West Laboratories Inc | Germicidal iodine compositions for application to skin tissue including teats of milk animals |
| US4401651A (en) | 1979-04-18 | 1983-08-30 | Knutson Richard A | Wound-healing compositions containing povidone-iodine |
| US4597975A (en) | 1981-11-06 | 1986-07-01 | Woodward Fred E | Iodine surface active compositions |
| GB8520664D0 (en) | 1985-08-17 | 1985-09-25 | Euro Celtique Sa | Suppository |
| CA1287584C (en) | 1986-09-02 | 1991-08-13 | Seiichi Komori | Wound-healing preparations |
| WO1988004168A1 (en) * | 1986-12-08 | 1988-06-16 | Arseco, Inc. | A storage stable topical composition |
| AU618517B2 (en) | 1986-12-23 | 1992-01-02 | Eugene J. Van Scott | Additives enhancing topical actions of therapeutic agents |
| CA1273576A (en) | 1987-09-16 | 1990-09-04 | Patrick A. Beauchamp | Topical treatment for diseased skin disorders |
| JP3055796B2 (ja) | 1990-11-19 | 2000-06-26 | 善蔵 田村 | 殺菌消毒剤組成物 |
| US5663208A (en) | 1991-03-01 | 1997-09-02 | Warner-Lambert Company | Antifungal wound healing compositions and methods for preparing and using same |
| GB9306296D0 (en) * | 1993-03-26 | 1993-05-19 | Diversey Corp | Improved iodophors,production and use thereof |
| JP3108262B2 (ja) * | 1993-12-22 | 2000-11-13 | 明治製菓株式会社 | 研磨剤を含有しない口腔用半練状製剤 |
| JP4169804B2 (ja) * | 1994-06-10 | 2008-10-22 | 小林製薬株式会社 | 香料を配合したヨウ素製剤 |
| WO1997000667A1 (en) | 1995-06-22 | 1997-01-09 | Minnesota Mining And Manufacturing Company | Stable hydroalcoholic compositions |
| US5643608A (en) | 1996-03-01 | 1997-07-01 | West Agro, Inc. | Low pH germicidal iodine compositions having enhanced stability |
| FR2747938B1 (fr) * | 1996-04-24 | 1998-10-02 | Naphtachimie Sa | Procede et dispositif de traitement thermique de produits circulant dans un conduit |
| US7060253B1 (en) | 1996-09-20 | 2006-06-13 | Mundschenk David D | Topical formulations and delivery systems |
| US5908619A (en) | 1997-01-09 | 1999-06-01 | Minnesota Mining And Manufacturing Company | Hydroalcoholic compositions thickened using surfactant/polymer complexes |
| US6582711B1 (en) | 1997-01-09 | 2003-06-24 | 3M Innovative Properties Company | Hydroalcoholic compositions thickened using polymers |
| US5897872A (en) | 1997-11-12 | 1999-04-27 | Picciano; Dante J. | Iodine-containing nasal moisturizing saline solution |
| US6635676B2 (en) | 1999-04-28 | 2003-10-21 | Regents Of The University Of Michigan | Non-toxic antimicrobial compositions and methods of use |
| US6559189B2 (en) | 1999-04-28 | 2003-05-06 | Regents Of The University Of Michigan | Non-toxic antimicrobial compositions and methods of use |
| RU2220710C2 (ru) | 1999-11-01 | 2004-01-10 | Комаров Виталий Петрович | Состав для промывания носовой полости |
| PL363113A1 (en) | 2000-03-27 | 2004-11-15 | Schott Glas | New cosmetic, personal care, cleaning agent, and nutritional supplement compositions comprising bioactive glass and methods of making and using the same |
| US6582676B2 (en) * | 2000-08-14 | 2003-06-24 | The University Of British Columbia | Hydrogen generation from water split reaction |
| US6521243B2 (en) * | 2000-12-22 | 2003-02-18 | Pharma C And D, Limited | Ionic chitosan -iodine complexes: antiseptic hydrogels and wound healing promoters |
| US20020098154A1 (en) | 2001-01-20 | 2002-07-25 | Dyer Gordon Wayne | Methods and apparatus for medicating the nasal sinuses |
| WO2002094179A2 (en) | 2001-05-23 | 2002-11-28 | J.B. Chemicals & Pharmaceuticals Ltd. | Novel topical microbicidal compositions |
| CN1323584A (zh) | 2001-05-30 | 2001-11-28 | 陈民桂 | 治疗眼耳鼻喉外用药液 |
| US6846846B2 (en) | 2001-10-23 | 2005-01-25 | The Trustees Of Columbia University In The City Of New York | Gentle-acting skin disinfectants |
| US6838078B2 (en) | 2002-01-16 | 2005-01-04 | 3M Innovative Properties Company | Film-forming compositions and methods |
| US7147873B2 (en) | 2002-01-16 | 2006-12-12 | 3M Innovative Properties Company | Antiseptic compositions and methods |
| US6696041B2 (en) | 2002-03-20 | 2004-02-24 | Richard L. Hansen | Treatment of colds, flu like infections and other general nasal based infections with a solution containing iodine and other broad spectrum microbicides and a method for its use |
| BRPI0414193A (pt) * | 2003-09-09 | 2006-10-31 | 3M Innovative Properties Co | composição antimicrobiana, kit antimicrobiano e métodos de usar a composição e de aplicar uma composição antimicrobiana a um substrato |
| US20050058673A1 (en) | 2003-09-09 | 2005-03-17 | 3M Innovative Properties Company | Antimicrobial compositions and methods |
| DE10360847A1 (de) | 2003-12-20 | 2005-07-28 | Cord Contract Research And Development Gmbh | Medizinisches Gleitgel |
| US20050191270A1 (en) | 2004-02-27 | 2005-09-01 | Hydromer, Inc. | Anti-infectious hydrogel compositions |
| US20060051384A1 (en) | 2004-09-07 | 2006-03-09 | 3M Innovative Properties Company | Antiseptic compositions and methods of use |
| US8198326B2 (en) | 2004-09-07 | 2012-06-12 | 3M Innovative Properties Company | Phenolic antiseptic compositions and methods of use |
| US20070048345A1 (en) * | 2005-08-31 | 2007-03-01 | Kimberly-Clark Worldwide, Inc. | Antimicrobial composition |
-
2008
- 2008-12-29 BR BRPI0819566 patent/BRPI0819566A2/pt not_active Application Discontinuation
- 2008-12-29 AU AU2008346755A patent/AU2008346755B2/en not_active Ceased
- 2008-12-29 US US12/345,085 patent/US10052384B2/en active Active
- 2008-12-29 JP JP2010541510A patent/JP6117460B2/ja active Active
- 2008-12-29 CA CA2711663A patent/CA2711663C/en active Active
- 2008-12-29 CN CN200880127411XA patent/CN101951887B/zh active Active
- 2008-12-29 EP EP08870511.6A patent/EP2249805B1/en active Active
- 2008-12-29 WO PCT/US2008/088428 patent/WO2009088826A1/en not_active Ceased
-
2014
- 2014-12-05 JP JP2014246711A patent/JP6268082B2/ja active Active
-
2016
- 2016-10-28 JP JP2016212021A patent/JP6254243B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| AU2008346755B2 (en) | 2012-09-27 |
| EP2249805A1 (en) | 2010-11-17 |
| US20090169647A1 (en) | 2009-07-02 |
| WO2009088826A1 (en) | 2009-07-16 |
| JP6268082B2 (ja) | 2018-01-24 |
| AU2008346755A1 (en) | 2009-07-16 |
| CN101951887B (zh) | 2013-03-13 |
| CA2711663A1 (en) | 2009-07-16 |
| BRPI0819566A2 (pt) | 2015-05-05 |
| JP2011507976A (ja) | 2011-03-10 |
| CN101951887A (zh) | 2011-01-19 |
| EP2249805B1 (en) | 2014-11-05 |
| US10052384B2 (en) | 2018-08-21 |
| JP6254243B2 (ja) | 2017-12-27 |
| JP2017039770A (ja) | 2017-02-23 |
| JP6117460B2 (ja) | 2017-04-19 |
| JP2015057429A (ja) | 2015-03-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20131230 |