CA1099728A - Process for the peparation of iodophor compounds and methods for stabilizing iodophor pharmaceutical compositions containing same - Google Patents
Process for the peparation of iodophor compounds and methods for stabilizing iodophor pharmaceutical compositions containing sameInfo
- Publication number
- CA1099728A CA1099728A CA300,344A CA300344A CA1099728A CA 1099728 A CA1099728 A CA 1099728A CA 300344 A CA300344 A CA 300344A CA 1099728 A CA1099728 A CA 1099728A
- Authority
- CA
- Canada
- Prior art keywords
- ions
- iodide
- iodine
- iodophor
- ion
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 83
- 238000000034 method Methods 0.000 title claims abstract description 46
- 230000008569 process Effects 0.000 title abstract description 9
- 239000008194 pharmaceutical composition Substances 0.000 title description 2
- 230000000087 stabilizing effect Effects 0.000 title description 2
- 239000011630 iodine Substances 0.000 claims abstract description 118
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 118
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 109
- -1 persulfate ions Chemical class 0.000 claims abstract description 58
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 claims abstract description 57
- 229940006461 iodide ion Drugs 0.000 claims abstract description 51
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000003599 detergent Chemical class 0.000 claims abstract description 32
- 150000002500 ions Chemical class 0.000 claims abstract description 26
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims abstract description 21
- 229920000036 polyvinylpyrrolidone Polymers 0.000 claims abstract description 20
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims abstract description 17
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000000129 anionic group Chemical class 0.000 claims abstract description 16
- 125000002091 cationic group Chemical class 0.000 claims abstract description 13
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims abstract description 11
- SXDBWCPKPHAZSM-UHFFFAOYSA-M bromate Inorganic materials [O-]Br(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-M 0.000 claims abstract description 10
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000011109 contamination Methods 0.000 claims abstract description 7
- 229910001919 chlorite Inorganic materials 0.000 claims abstract 5
- 229910052619 chlorite group Inorganic materials 0.000 claims abstract 5
- 239000000203 mixture Substances 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 230000002070 germicidal effect Effects 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 12
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 12
- 150000004694 iodide salts Chemical class 0.000 claims description 9
- 239000004094 surface-active agent Substances 0.000 claims description 8
- JLKDVMWYMMLWTI-UHFFFAOYSA-M potassium iodate Chemical group [K+].[O-]I(=O)=O JLKDVMWYMMLWTI-UHFFFAOYSA-M 0.000 claims description 7
- 239000001230 potassium iodate Substances 0.000 claims description 7
- 235000006666 potassium iodate Nutrition 0.000 claims description 7
- 229940093930 potassium iodate Drugs 0.000 claims description 7
- 239000003381 stabilizer Substances 0.000 claims description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 5
- 230000001590 oxidative effect Effects 0.000 claims description 5
- HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 claims description 4
- UNMYWSMUMWPJLR-UHFFFAOYSA-L Calcium iodide Chemical compound [Ca+2].[I-].[I-] UNMYWSMUMWPJLR-UHFFFAOYSA-L 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 2
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 claims description 2
- 229940046413 calcium iodide Drugs 0.000 claims description 2
- 229910001640 calcium iodide Inorganic materials 0.000 claims description 2
- 150000002462 imidazolines Chemical class 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 2
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 claims 5
- 229940107816 ammonium iodide Drugs 0.000 claims 5
- 229910002651 NO3 Inorganic materials 0.000 claims 4
- 230000009972 noncorrosive effect Effects 0.000 claims 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical group [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims 1
- 239000007859 condensation product Substances 0.000 claims 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims 1
- ICIWUVCWSCSTAQ-UHFFFAOYSA-M iodate Chemical compound [O-]I(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-M 0.000 abstract description 26
- 238000004519 manufacturing process Methods 0.000 abstract description 20
- 238000002360 preparation method Methods 0.000 abstract description 20
- 239000002552 dosage form Substances 0.000 abstract description 10
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical class C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 abstract description 9
- 229940069328 povidone Drugs 0.000 abstract description 9
- 239000004480 active ingredient Substances 0.000 abstract description 6
- 239000000356 contaminant Substances 0.000 abstract description 6
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 abstract 1
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- CPKVUHPKYQGHMW-UHFFFAOYSA-N 1-ethenylpyrrolidin-2-one;molecular iodine Chemical compound II.C=CN1CCCC1=O CPKVUHPKYQGHMW-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- 229920000153 Povidone-iodine Polymers 0.000 description 23
- 229960001621 povidone-iodine Drugs 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- 229940005633 iodate ion Drugs 0.000 description 17
- 239000002904 solvent Substances 0.000 description 11
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 10
- 239000002253 acid Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 229940035535 iodophors Drugs 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 6
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 230000032683 aging Effects 0.000 description 5
- 230000000845 anti-microbial effect Effects 0.000 description 5
- QBWCMBCROVPCKQ-UHFFFAOYSA-M chlorite Chemical compound [O-]Cl=O QBWCMBCROVPCKQ-UHFFFAOYSA-M 0.000 description 5
- 229940005993 chlorite ion Drugs 0.000 description 5
- 150000002894 organic compounds Chemical class 0.000 description 5
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 5
- 239000002798 polar solvent Substances 0.000 description 5
- 229920001983 poloxamer Polymers 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 230000001473 noxious effect Effects 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 229940104261 taurate Drugs 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000002736 nonionic surfactant Substances 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 229910001961 silver nitrate Inorganic materials 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 3
- 238000004448 titration Methods 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 241000212342 Sium Species 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000005529 alkyleneoxy group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000000502 dialysis Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- ICIWUVCWSCSTAQ-UHFFFAOYSA-N iodic acid Chemical class OI(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 150000001455 metallic ions Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229940127557 pharmaceutical product Drugs 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 150000003077 polyols Chemical class 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 231100000563 toxic property Toxicity 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- KCBAMQOKOLXLOX-BSZYMOERSA-N CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O Chemical compound CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O KCBAMQOKOLXLOX-BSZYMOERSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000905957 Channa melasoma Species 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 101001126084 Homo sapiens Piwi-like protein 2 Proteins 0.000 description 1
- 241000575946 Ione Species 0.000 description 1
- LTXREWYXXSTFRX-QGZVFWFLSA-N Linagliptin Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=CC4=C(C)N=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 LTXREWYXXSTFRX-QGZVFWFLSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000353097 Molva molva Species 0.000 description 1
- 101100345589 Mus musculus Mical1 gene Proteins 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 102100029365 Piwi-like protein 2 Human genes 0.000 description 1
- 241001208007 Procas Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 206010052428 Wound Diseases 0.000 description 1
- GYMWQLRSSDFGEQ-ADRAWKNSSA-N [(3e,8r,9s,10r,13s,14s,17r)-13-ethyl-17-ethynyl-3-hydroxyimino-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate;(8r,9s,13s,14s,17r)-17-ethynyl-13-methyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17-diol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1.O/N=C/1CC[C@@H]2[C@H]3CC[C@](CC)([C@](CC4)(OC(C)=O)C#C)[C@@H]4[C@@H]3CCC2=C\1 GYMWQLRSSDFGEQ-ADRAWKNSSA-N 0.000 description 1
- YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 description 1
- ORKACOJUXFAAGG-UHFFFAOYSA-N [I].C(CCCCCCCCCCCCCCCCC)N Chemical compound [I].C(CCCCCCCCCCCCCCCCC)N ORKACOJUXFAAGG-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- MWOBKFYERIDQSZ-UHFFFAOYSA-N benzene;sodium Chemical compound [Na].C1=CC=CC=C1 MWOBKFYERIDQSZ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- DHEIAYDROZXXGS-UHFFFAOYSA-N ethanol;iodine Chemical compound [I].CCO DHEIAYDROZXXGS-UHFFFAOYSA-N 0.000 description 1
- NNYBQONXHNTVIJ-UHFFFAOYSA-N etodolac Chemical compound C1COC(CC)(CC(O)=O)C2=C1C(C=CC=C1CC)=C1N2 NNYBQONXHNTVIJ-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000727 fraction Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 159000000011 group IA salts Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910001505 inorganic iodide Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940063718 lodine Drugs 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 229940051866 mouthwash Drugs 0.000 description 1
- YAQZXMVNFHVFHT-UHFFFAOYSA-N n-(6-aminohexyl)-5-iodonaphthalene-1-sulfonamide Chemical compound C1=CC=C2C(S(=O)(=O)NCCCCCCN)=CC=CC2=C1I YAQZXMVNFHVFHT-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229940005654 nitrite ion Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229940090890 povidone-iodine douche Drugs 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000011012 sanitization Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- PWWJJDVDTKXWOF-UHFFFAOYSA-M sodium;2-[hexadecanoyl(methyl)amino]ethanesulfonate Chemical compound [Na+].CCCCCCCCCCCCCCCC(=O)N(C)CCS([O-])(=O)=O PWWJJDVDTKXWOF-UHFFFAOYSA-M 0.000 description 1
- IZWPGJFSBABFGL-GMFCBQQYSA-M sodium;2-[methyl-[(z)-octadec-9-enoyl]amino]ethanesulfonate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC(=O)N(C)CCS([O-])(=O)=O IZWPGJFSBABFGL-GMFCBQQYSA-M 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 230000003330 sporicidal effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000008791 toxic response Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- 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
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
- A01N59/12—Iodine, e.g. iodophors; 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/56—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
- A61K47/58—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Inorganic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Wood Science & Technology (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/797,094 US4113857A (en) | 1977-05-16 | 1977-05-16 | Process for the preparation of iodophor compounds and methods for stabilizing iodophor pharmaceutical compositions containing the same |
| US797,094 | 1977-05-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1099728A true CA1099728A (en) | 1981-04-21 |
Family
ID=25169886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA300,344A Expired CA1099728A (en) | 1977-05-16 | 1978-04-03 | Process for the peparation of iodophor compounds and methods for stabilizing iodophor pharmaceutical compositions containing same |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4113857A (OSRAM) |
| JP (1) | JPS53148540A (OSRAM) |
| AT (1) | AT362082B (OSRAM) |
| AU (1) | AU519505B2 (OSRAM) |
| BE (1) | BE866395A (OSRAM) |
| CA (1) | CA1099728A (OSRAM) |
| CH (1) | CH639278A5 (OSRAM) |
| DE (1) | DE2821199A1 (OSRAM) |
| DK (1) | DK156983C (OSRAM) |
| ES (1) | ES469385A1 (OSRAM) |
| FI (1) | FI61609C (OSRAM) |
| FR (1) | FR2390963A1 (OSRAM) |
| GB (1) | GB1580596A (OSRAM) |
| IL (1) | IL54419A (OSRAM) |
| IN (1) | IN148864B (OSRAM) |
| NL (1) | NL185705C (OSRAM) |
| NO (1) | NO153833C (OSRAM) |
| NZ (1) | NZ187097A (OSRAM) |
| PT (1) | PT67861B (OSRAM) |
| SE (1) | SE443700B (OSRAM) |
| ZA (1) | ZA782026B (OSRAM) |
Families Citing this family (67)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7902893L (sv) * | 1979-04-02 | 1980-10-03 | Astra Chem Prod Ab | Desinfektionsmedel |
| US4323557A (en) * | 1979-07-31 | 1982-04-06 | Minnesota Mining & Manufacturing Company | Pressure-sensitive adhesive containing iodine |
| US4310509A (en) * | 1979-07-31 | 1982-01-12 | Minnesota Mining And Manufacturing Company | Pressure-sensitive adhesive having a broad spectrum antimicrobial therein |
| US4271149A (en) * | 1979-09-21 | 1981-06-02 | West Agro-Chemical, Inc. | Germicidal iodine compositions with enhanced iodine stability |
| US4481167A (en) * | 1980-04-11 | 1984-11-06 | The Dow Chemical Company | Sanitizing complexes of polyoxazolines or polyoxazines and polyhalide anions |
| EP0094219A1 (en) * | 1982-05-07 | 1983-11-16 | Diversey Corporation | Germicidal iodine compositions |
| ZA833754B (en) * | 1982-05-25 | 1984-02-29 | Edward Sturdy Wilson | Iodophors |
| US4521403A (en) * | 1983-01-20 | 1985-06-04 | Simon Gilbert I | Chemotherapeutic method for treating periodontal disease |
| DE3313655C2 (de) * | 1983-03-02 | 1995-03-23 | Euro Celtique Sa | Pharmazeutisches Jodophor-Präparat |
| NO168565C (no) * | 1983-03-02 | 1992-03-11 | Euro Celtique Sa | Fremgangsmaate for fremstilling av standardiserte jodoforpreparater |
| US4792445A (en) * | 1983-11-04 | 1988-12-20 | Mario Flores Rivera | Highly stable free iodine iodophor compositions, process for preparing same and process for using same |
| US4567036A (en) * | 1983-12-30 | 1986-01-28 | Simon Gilbert I | Chemotherapeutic method for treating periodontal disease, and composition therefore |
| US4575491A (en) * | 1984-05-31 | 1986-03-11 | Euroceltique, S.A. | Method of controlling and determining germicidal activity |
| US4946673A (en) * | 1984-05-31 | 1990-08-07 | Euroceltique, S.A. | Iodine-containing germicidal preparations and method of controlling germicidal activity |
| US4997625A (en) * | 1985-08-07 | 1991-03-05 | Simon Gilbert I | Chemical sterilization |
| US4923677A (en) * | 1985-08-07 | 1990-05-08 | Roy T. Witkin | Chemical sterilization |
| US4684519A (en) * | 1986-04-09 | 1987-08-04 | Gaf Corporation | Method of preparing a polyvinylpyrrolidone-halogen complex of improved stability |
| US4842858A (en) * | 1987-03-03 | 1989-06-27 | Gaf Corporation | Polymeric halophors |
| US4830851A (en) * | 1987-03-03 | 1989-05-16 | Gaf Corporation | Polymeric halophors |
| ATE198400T1 (de) * | 1987-07-01 | 2001-01-15 | Novapharm Res Pty Ltd | Biozide zusammensetzung |
| US5409697A (en) * | 1987-07-01 | 1995-04-25 | Novapharm Research Pty. Ltd. | Biocidal composition |
| US5066497A (en) * | 1988-07-28 | 1991-11-19 | Albert L. Jacobs, Jr. | Antimicrobial veterinary compositions and methods |
| US4935248A (en) * | 1988-07-28 | 1990-06-19 | Albert L. Jacobs | Antimicrobial veterinary compositions and methods |
| US4904480A (en) * | 1988-09-19 | 1990-02-27 | Becton, Dickinson And Company | Radiation compatible iodine formulation |
| US4996048A (en) * | 1988-11-30 | 1991-02-26 | Euroceltique, S.A. | Stabilizing packaged iodophor and minimizing leaching of iodine through packaging |
| US4865752A (en) * | 1988-12-05 | 1989-09-12 | Jacobs Albert L | Separation and filtration membranes and their regeneration |
| US4978527A (en) * | 1989-04-10 | 1990-12-18 | Minnesota Mining And Manufacturing Company | Film-forming emulsion containing iodine and methods of use |
| IE63315B1 (en) * | 1989-04-24 | 1995-04-05 | Becton Dickinson Co | Radiation sterilizable antimicrobial ointment and process to manufacture |
| US5232692A (en) * | 1989-04-28 | 1993-08-03 | Research And Education Institute, Inc. | Povidone-iodine neonatal ophthalmic antimicrobial prophylactic agent |
| GB9006346D0 (en) * | 1990-03-21 | 1990-05-16 | Euro Celtique Sa | Pharmaceutical composition |
| US5019380A (en) * | 1990-04-27 | 1991-05-28 | Bausch & Lomb Incorporated | Novel antimicrobial compositions and process for preparing the same |
| US5261353A (en) * | 1990-11-05 | 1993-11-16 | Stevenson Dale V | Udder care plus indicator |
| US5116623A (en) * | 1991-01-22 | 1992-05-26 | Becton, Dickinson And Company | Periodate iodophor composition with increased stability |
| US5229027A (en) * | 1991-03-20 | 1993-07-20 | Colgate-Palmolive Company | Aqueous liquid automatic dishwashing detergent composition comprising hypochlorite bleach and an iodate or iodide hypochlorite bleach stabilizer |
| US5130124A (en) * | 1991-05-01 | 1992-07-14 | Isp Investments Inc. | Stabilized, aqueous, film-forming antimicrobial compositions of hydrogen peroxide |
| US5180061A (en) * | 1991-09-09 | 1993-01-19 | Becton, Dickinson And Company | Stable iodophor in polyurethane foam |
| US5152987A (en) * | 1991-10-08 | 1992-10-06 | Isp Investments Inc. | Process for preparing water-insoluble PVP-iodine product |
| WO1993006837A1 (en) * | 1991-10-08 | 1993-04-15 | Isp Investments Inc. | Process for preparing pvp-iodine product |
| EP0565288B1 (en) * | 1992-03-27 | 2001-01-03 | Unilever N.V. | Production of iodophors |
| US5616348A (en) * | 1992-09-18 | 1997-04-01 | West Agro, Inc. | Germicidal detergent-iodine compositions including polyvinyl pyrrolidone and compatible nonionic surfactant complexors |
| GB9306296D0 (en) * | 1993-03-26 | 1993-05-19 | Diversey Corp | Improved iodophors,production and use thereof |
| US5863556A (en) * | 1993-08-20 | 1999-01-26 | Euro-Celtique, S.A. | Preparations for the external application of antiseptic agents and/or agents promoting the healing of wounds |
| JP3005484U (ja) * | 1994-06-21 | 1994-12-20 | 昌弘 米田 | 紙製包装用箱 |
| WO1997034476A1 (en) * | 1996-03-22 | 1997-09-25 | Viatro, Corp. | Medical waste solidifier and microbicidal composition |
| US6203484B1 (en) | 1997-03-24 | 2001-03-20 | Basf Corporation | Methods for disinfecting wastes |
| DE29923766U1 (de) * | 1998-05-27 | 2001-06-07 | Euroceltique S.A., Luxemburg/Luxembourg | Wirkstoffapplikationssystem umfassend einen hochverdichteten festen Arzneimittelvorrat |
| US6231830B1 (en) * | 1999-03-04 | 2001-05-15 | George Madray | Method of making molecular chlorine dioxide |
| US6534075B1 (en) | 1999-03-26 | 2003-03-18 | Ecolab Inc. | Antimicrobial and antiviral compositions and treatments for food surfaces |
| US6436445B1 (en) * | 1999-03-26 | 2002-08-20 | Ecolab Inc. | Antimicrobial and antiviral compositions containing an oxidizing species |
| HU229598B1 (en) | 1999-05-27 | 2014-02-28 | Euro Celtique Sa | Preparations for the application of anti-inflammatory agents |
| US7297344B1 (en) | 1999-05-27 | 2007-11-20 | Euro-Celtique, S.A. | Preparations for the promotion of wound healing in the upper respiratory tract and/or ear |
| US7300667B1 (en) | 1999-05-27 | 2007-11-27 | Euro-Celtique, S.A. | Preparations for the application of anti-inflammatory, especially antiseptic agents and/or agents promoting the healing of wounds, to the lower respiratory tract |
| AU4957199A (en) * | 1999-06-21 | 2001-01-09 | Symbollon Corporation | Iodine germicides that continuously generate free molecular iodine |
| US6855328B2 (en) * | 2002-03-28 | 2005-02-15 | Ecolab Inc. | Antimicrobial and antiviral compositions containing an oxidizing species |
| WO2004101432A2 (en) * | 2003-05-12 | 2004-11-25 | Johnsondiversey, Inc. | Preparation of and dispensing chlorine dioxide |
| ES2292874T3 (es) * | 2003-05-19 | 2008-03-16 | Euro-Celtique S.A. | Composiciones liposomales secas de pvp-yodo. |
| JP2006206480A (ja) * | 2005-01-27 | 2006-08-10 | Nippo Kagaku Kk | 水性組成物 |
| US20090003931A1 (en) * | 2007-06-28 | 2009-01-01 | Off The Wall Products, Llc | Control barrier with light assembly |
| JPWO2012153741A1 (ja) * | 2011-05-10 | 2014-07-31 | 株式会社ネオス | ヨウ素−β−シクロデキストリン包接化合物溶液 |
| TW201325601A (zh) | 2011-09-16 | 2013-07-01 | Foresight Biotherapeutics Inc | 安定之普維酮－碘組成物 |
| WO2015080984A1 (en) | 2013-11-27 | 2015-06-04 | BioPharmX, Inc. | Solid oral dosage form for breast symptoms |
| CN104069070A (zh) * | 2014-06-27 | 2014-10-01 | 深圳市格易通消毒药械科技有限公司 | 一种具有高效杀菌消毒作用的聚维酮碘粉剂及其制备方法 |
| WO2016175727A1 (en) * | 2015-04-27 | 2016-11-03 | Aydin Kimya Sanayi Ve Ticaret Anonim Sirketi | Production method of iodophor based antimicrobial hydrogel |
| CN115316399A (zh) * | 2018-04-03 | 2022-11-11 | 本部三庆株式会社 | 干燥固体以及由其制造的液体氯氧化物 |
| IL275909B (en) * | 2020-03-23 | 2021-05-31 | Iocure Inc | An iodine preparation for the treatment of pathogens in the respiratory system |
| CN111632192B (zh) * | 2020-06-19 | 2021-09-24 | 浙江大学 | 兼具抗菌、促成骨分化及矿化的载碘钛合金植入物及其制备方法 |
| CN114208820B (zh) * | 2021-11-24 | 2022-10-21 | 佛山市正典生物技术有限公司 | 一种含有砜和/或亚砜的含碘消毒剂及其制备方法和用途 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3028300A (en) * | 1960-09-13 | 1962-04-03 | West Laboratories Inc | Germicidal compositions and methods for preparing the same |
| US3039916A (en) * | 1961-03-27 | 1962-06-19 | West Laboratories Inc | Anionic iodine complexes |
| US3367877A (en) * | 1965-02-03 | 1968-02-06 | West Laboratories Inc | Detergent-hydriodic acid compositions |
| US3966090A (en) * | 1969-02-17 | 1976-06-29 | Dart Industries Inc. | Package for dispensing an antiseptic composition |
| US3644650A (en) * | 1969-06-26 | 1972-02-22 | Chemed Corp | Solutions of germicidal iodine complexes |
| DE2438594A1 (de) * | 1974-08-10 | 1976-02-26 | Basf Ag | Desinfektionsmittel |
| DE2537303C3 (de) * | 1975-06-02 | 1980-03-13 | Flow Pharmaceuticals, Inc., Palo Alto, Calif. (V.St.A.) | Sterile wäßrige Lösung für die Abgabe oder Verteilung von verfügbarem Jod und deren Verwendung |
| DE2540170C3 (de) * | 1975-09-10 | 1979-01-18 | Basf Ag, 6700 Ludwigshafen | Verwendung von in organischer Lösung hergestelltem Polyvinylpyrrolidon zur Herstellung von stabilen wäßrigen PoIyvinylpyrrolidon-Jod-Lösungen |
| SE410271B (sv) * | 1976-04-28 | 1979-10-08 | Landstingens Inkopscentral | Protes for amputerade underben med ingaende mellanlegg |
-
1977
- 1977-05-16 US US05/797,094 patent/US4113857A/en not_active Expired - Lifetime
-
1978
- 1978-03-29 NO NO781082A patent/NO153833C/no unknown
- 1978-03-30 DK DK140778A patent/DK156983C/da not_active IP Right Cessation
- 1978-03-30 FI FI780963A patent/FI61609C/fi not_active IP Right Cessation
- 1978-04-03 PT PT67861A patent/PT67861B/pt unknown
- 1978-04-03 CA CA300,344A patent/CA1099728A/en not_active Expired
- 1978-04-03 IL IL54419A patent/IL54419A/xx unknown
- 1978-04-06 SE SE7803912A patent/SE443700B/sv not_active IP Right Cessation
- 1978-04-10 ZA ZA00782026A patent/ZA782026B/xx unknown
- 1978-04-10 NL NLAANVRAGE7803770,A patent/NL185705C/xx not_active IP Right Cessation
- 1978-04-10 AU AU34918/78A patent/AU519505B2/en not_active Expired
- 1978-04-13 IN IN411/CAL/78A patent/IN148864B/en unknown
- 1978-04-14 CH CH403178A patent/CH639278A5/de not_active IP Right Cessation
- 1978-04-18 GB GB15162/78A patent/GB1580596A/en not_active Expired
- 1978-04-26 BE BE187119A patent/BE866395A/xx not_active IP Right Cessation
- 1978-04-27 NZ NZ187097A patent/NZ187097A/xx unknown
- 1978-04-28 JP JP5016578A patent/JPS53148540A/ja active Granted
- 1978-05-03 ES ES469385A patent/ES469385A1/es not_active Expired
- 1978-05-12 FR FR7814266A patent/FR2390963A1/fr active Granted
- 1978-05-12 AT AT347678A patent/AT362082B/de not_active IP Right Cessation
- 1978-05-13 DE DE19782821199 patent/DE2821199A1/de active Granted
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1099728A (en) | Process for the peparation of iodophor compounds and methods for stabilizing iodophor pharmaceutical compositions containing same | |
| US4829129A (en) | Reaction product of polymer with chlorine dioxide | |
| EP0487066B1 (en) | Disinfectant composition | |
| KR970007930B1 (ko) | 유기 안정제 | |
| US5204060A (en) | Method for disinfection | |
| US3689660A (en) | Stable liquid antimicrobial composition | |
| CA1334162C (en) | Biocidal composition | |
| KR20010023072A (ko) | 요오드프로피닐 화합물과 포름알데히드 도너의 안정화된 혼합물 | |
| US5409697A (en) | Biocidal composition | |
| US5019380A (en) | Novel antimicrobial compositions and process for preparing the same | |
| US4719106A (en) | Iodophor composition with immediate and long action microbicidal action | |
| KR20070039404A (ko) | 표면을 살균하거나 소독하는 방법 | |
| US4297232A (en) | Glycol-iodine composition and method of preparation | |
| US6534076B1 (en) | Stabilized isothiazolone compositions and methods of stabilization of isothiazolone | |
| RU2022564C1 (ru) | Средство для дезинфекции | |
| EP0799570A1 (en) | Preparation and uses of microbicidal formulations | |
| US2552490A (en) | Active chlorine-containing composition | |
| US3130123A (en) | Process for preparing methyl and ethyl mercury hydroxyquinolinates and products obtained thereby | |
| JP2661745B2 (ja) | 工業用殺菌剤及び殺菌方法 | |
| EP0037866B1 (en) | Glycol-iodine composition and method of preparation | |
| HU200958B (en) | Fungicidal agent for protecting new-cut timber from becoming blue and mould-fungus infection | |
| RU2163143C2 (ru) | Средство для дезинфекции | |
| DE19537534A1 (de) | Alkylamino-bis-methylensulfon-pyrrolidinium-sulfomethyl-betaine, Verfahren zur Herstellung und ihre Verwendung | |
| EP0298065A2 (en) | Prophylactic agent for controlling venereal diseases | |
| CS277380B6 (sk) | Povrchovo aktivně amínoxidové dezlnficienciá |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |