CN102309473A - 含有季铵化合物及精油和/或精油成分的协同组合的抗微生物组合物 - Google Patents
含有季铵化合物及精油和/或精油成分的协同组合的抗微生物组合物 Download PDFInfo
- Publication number
- CN102309473A CN102309473A CN2011102381998A CN201110238199A CN102309473A CN 102309473 A CN102309473 A CN 102309473A CN 2011102381998 A CN2011102381998 A CN 2011102381998A CN 201110238199 A CN201110238199 A CN 201110238199A CN 102309473 A CN102309473 A CN 102309473A
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- China
- Prior art keywords
- zinc
- compositions
- concentration
- quaternary ammonium
- oil
- 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.)
- Pending
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- 230000000845 anti-microbial effect Effects 0.000 title claims abstract description 49
- 150000003856 quaternary ammonium compounds Chemical class 0.000 title claims abstract description 26
- 239000000341 volatile oil Substances 0.000 title claims abstract description 17
- 239000000470 constituent Substances 0.000 title abstract 3
- 239000011885 synergistic combination Substances 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims abstract description 63
- 230000002195 synergetic effect Effects 0.000 claims abstract description 9
- CRDAMVZIKSXKFV-FBXUGWQNSA-N (2-cis,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C/CO CRDAMVZIKSXKFV-FBXUGWQNSA-N 0.000 claims description 37
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 claims description 37
- 229940043259 farnesol Drugs 0.000 claims description 37
- 229930002886 farnesol Natural products 0.000 claims description 37
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 claims description 37
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 claims description 35
- 229960003260 chlorhexidine Drugs 0.000 claims description 35
- -1 acetaminol Chemical compound 0.000 claims description 31
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 claims description 28
- 229960001950 benzethonium chloride Drugs 0.000 claims description 24
- 229960000686 benzalkonium chloride Drugs 0.000 claims description 22
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 150000003751 zinc Chemical class 0.000 claims description 15
- 239000011701 zinc Substances 0.000 claims description 14
- 229910052725 zinc Inorganic materials 0.000 claims description 13
- VAZJLPXFVQHDFB-UHFFFAOYSA-N 1-(diaminomethylidene)-2-hexylguanidine Polymers CCCCCCN=C(N)N=C(N)N VAZJLPXFVQHDFB-UHFFFAOYSA-N 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 229920002413 Polyhexanide Polymers 0.000 claims description 12
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 10
- 229940123208 Biguanide Drugs 0.000 claims description 8
- 239000002562 thickening agent Substances 0.000 claims description 7
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 claims description 6
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 claims description 6
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 claims description 6
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 claims description 6
- RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 claims description 6
- WHMDKBIGKVEYHS-IYEMJOQQSA-L Zinc gluconate Chemical compound [Zn+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O WHMDKBIGKVEYHS-IYEMJOQQSA-L 0.000 claims description 6
- CANRESZKMUPMAE-UHFFFAOYSA-L Zinc lactate Chemical compound [Zn+2].CC(O)C([O-])=O.CC(O)C([O-])=O CANRESZKMUPMAE-UHFFFAOYSA-L 0.000 claims description 6
- 229940043350 citral Drugs 0.000 claims description 6
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 claims description 6
- 239000000174 gluconic acid Substances 0.000 claims description 6
- 235000012208 gluconic acid Nutrition 0.000 claims description 6
- 229930007744 linalool Natural products 0.000 claims description 6
- 239000011670 zinc gluconate Substances 0.000 claims description 6
- 235000011478 zinc gluconate Nutrition 0.000 claims description 6
- 229960000306 zinc gluconate Drugs 0.000 claims description 6
- 239000011576 zinc lactate Substances 0.000 claims description 6
- 235000000193 zinc lactate Nutrition 0.000 claims description 6
- 229940050168 zinc lactate Drugs 0.000 claims description 6
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 5
- 239000003974 emollient agent Substances 0.000 claims description 5
- 239000004246 zinc acetate Substances 0.000 claims description 5
- 235000013904 zinc acetate Nutrition 0.000 claims description 5
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 claims description 4
- 239000003349 gelling agent Substances 0.000 claims description 4
- ORMHZBNNECIKOH-UHFFFAOYSA-N 4-(4-hydroxy-4-methylpentyl)cyclohex-3-ene-1-carbaldehyde Chemical compound CC(C)(O)CCCC1=CCC(C=O)CC1 ORMHZBNNECIKOH-UHFFFAOYSA-N 0.000 claims description 3
- WEEGYLXZBRQIMU-UHFFFAOYSA-N Eucalyptol Chemical compound C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 claims description 3
- 229960005233 cineole Drugs 0.000 claims description 3
- 230000002829 reductive effect Effects 0.000 claims description 3
- 230000000638 stimulation Effects 0.000 claims description 3
- WGIWBXUNRXCYRA-UHFFFAOYSA-H trizinc;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O WGIWBXUNRXCYRA-UHFFFAOYSA-H 0.000 claims description 3
- 239000011746 zinc citrate Substances 0.000 claims description 3
- 235000006076 zinc citrate Nutrition 0.000 claims description 3
- 229940068475 zinc citrate Drugs 0.000 claims description 3
- VGTSYTYRRZZILH-UHFFFAOYSA-N 2,3-dihydroxypropanoic acid;zinc Chemical compound [Zn].OCC(O)C(O)=O VGTSYTYRRZZILH-UHFFFAOYSA-N 0.000 claims description 2
- 239000005792 Geraniol Substances 0.000 claims description 2
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims description 2
- BJIOGJUNALELMI-ONEGZZNKSA-N Isoeugenol Natural products COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 claims description 2
- YMCOHQVWOBMDCZ-UHFFFAOYSA-L Zinc undecylenate Chemical compound [Zn+2].[O-]C(=O)CCCCCCCCC=C.[O-]C(=O)CCCCCCCCC=C YMCOHQVWOBMDCZ-UHFFFAOYSA-L 0.000 claims description 2
- HMKKIXGYKWDQSV-KAMYIIQDSA-N alpha-Amylcinnamaldehyde Chemical compound CCCCC\C(C=O)=C\C1=CC=CC=C1 HMKKIXGYKWDQSV-KAMYIIQDSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- BJIOGJUNALELMI-ARJAWSKDSA-N cis-isoeugenol Chemical compound COC1=CC(\C=C/C)=CC=C1O BJIOGJUNALELMI-ARJAWSKDSA-N 0.000 claims description 2
- MFGZXPGKKJMZIY-UHFFFAOYSA-N ethyl 5-amino-1-(4-sulfamoylphenyl)pyrazole-4-carboxylate Chemical compound NC1=C(C(=O)OCC)C=NN1C1=CC=C(S(N)(=O)=O)C=C1 MFGZXPGKKJMZIY-UHFFFAOYSA-N 0.000 claims description 2
- 229940113087 geraniol Drugs 0.000 claims description 2
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 claims description 2
- 230000001524 infective effect Effects 0.000 claims description 2
- 230000001717 pathogenic effect Effects 0.000 claims description 2
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 claims description 2
- SRWMQSFFRFWREA-UHFFFAOYSA-M zinc formate Chemical compound [Zn+2].[O-]C=O SRWMQSFFRFWREA-UHFFFAOYSA-M 0.000 claims description 2
- 239000011787 zinc oxide Substances 0.000 claims description 2
- VRGNUPCISFMPEM-ZVGUSBNCSA-L zinc;(2r,3r)-2,3-dihydroxybutanedioate Chemical compound [Zn+2].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O VRGNUPCISFMPEM-ZVGUSBNCSA-L 0.000 claims description 2
- XDWXRAYGALQIFG-UHFFFAOYSA-L zinc;propanoate Chemical compound [Zn+2].CCC([O-])=O.CCC([O-])=O XDWXRAYGALQIFG-UHFFFAOYSA-L 0.000 claims description 2
- SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 claims 1
- OWNADIPBYYPFRQ-UHFFFAOYSA-N OC(C1=CC=CC=N1)=O.OC(C1=CC=CC=N1)=O.[SeH2] Chemical compound OC(C1=CC=CC=N1)=O.OC(C1=CC=CC=N1)=O.[SeH2] OWNADIPBYYPFRQ-UHFFFAOYSA-N 0.000 claims 1
- 229940101267 panthenol Drugs 0.000 claims 1
- 235000020957 pantothenol Nutrition 0.000 claims 1
- 239000011619 pantothenol Substances 0.000 claims 1
- 229960000314 zinc acetate Drugs 0.000 claims 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 claims 1
- 239000000499 gel Substances 0.000 abstract description 24
- 239000006210 lotion Substances 0.000 abstract description 15
- 239000000344 soap Substances 0.000 abstract description 4
- 239000006071 cream Substances 0.000 abstract 1
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- 239000003921 oil Substances 0.000 description 47
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- 239000000463 material Substances 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 17
- 230000000694 effects Effects 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000002585 base Substances 0.000 description 15
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- 241000191967 Staphylococcus aureus Species 0.000 description 11
- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 150000001298 alcohols Chemical class 0.000 description 10
- 238000005660 chlorination reaction Methods 0.000 description 10
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 239000006072 paste Substances 0.000 description 9
- 235000002639 sodium chloride Nutrition 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 6
- 239000004599 antimicrobial Substances 0.000 description 5
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Abstract
本发明涉及含有季铵化合物及精油和/或精油成分的协同组合的抗微生物组合物,它显示出增强的抗微生物效果。可将这种组合包含在洗剂、凝胶、乳膏、肥皂等中,施用于皮肤或粘膜。本发明基于,或至少部分基于发现了用精油或其单个成分和低浓度的季铵化合物的组合产生协同抗微生物效果。
Description
本发明专利申请是国际申请号为PCT/US2004/022505、国际申请日为2004年7月15日、进入中国国家阶段的申请号为200480020534.5、发明名称为“含有季铵化合物及精油和/或精油成分的协同组合的抗微生物组合物”的发明专利申请的分案申请。
相关申请的交叉参考
本申请要求分别于2003年7月17日和2003年12月18日提交的美国临时申请序列号60/488,349和60/530,864的权益,各自以整体纳入本文作为参考。
技术领域
本发明涉及含有季铵化合物及精油和/或单个精油成分的组合的组合物,以及使用此种组合物的方法。它基于,或至少部分基于发现了该组合物显示出协同增效的抗微生物效果。
背景技术
精油是从植物或动物来源得到的挥发油,由几种成分,例如单萜和倍半萜烃类,单萜和倍半萜醇、酯、醚、醛、酮、氧化物等的复杂混合物组成。这些精油及其分离成分常常用作香料和香精,并广泛用于治愈伤口的民间医药。
科学研究证实了精油的有益效果。人们发现桉树精油“具有中枢和外周止痛效果以及依赖或不依赖于嗜中性粒细胞的消炎活性”(Silva等,2003,J.Ethnopharmacol.89(2-3);277-283),在来自薰衣草的精油中观察到类似活性(Hajhashemi等,2003,J.Ethnopharmacol.89(1):67-71)。有证据证明,精油具有抗菌(Bezic等,2003,Phytother.Res.17(9):1037-1040;Goren等,2003,Z.Naturforsch.58(9-10):687-690;de Abreu Gonzaga等,2003,Planta Med.69(8):773-775;Valero和Salmera,2003,Int.J.Food Microbiol.85(1-2):73-81)和抗真菌(Paranagama等,2003,Lett.Appl.Microbiol.37(1):86-90:Shin,2003,Arch.Pharm.Res.26(5):389-393;Velluti等,2003,Int.J.Food Microbiol.89:145-154)活性。也观察到了精油的抗病毒活性,包括对1型和2型单纯疱疹病毒的直接抗病毒效果(Garcia等,Phytother.Res.17(9):1073-1075;Minami等,2003,Microbial Immunol.47(a):681-684;Schuhmacher等,2003,Phytomedicine10:504-510)。
季铵化合物(″QAC″)是其中有机自由基取代了天然铵阳离子的所有四个氢的一组铵盐。它们含有与四个有机自由基连接的一个中心氮原子和一个酸自由基。QAC趋于分布在两相界面上(液相-液相或固相-液相),在这两个不同相之间引入连续性。已知QAC具有强大的抗微生物活性,能够破坏细菌的细胞活动。QAC已用作杀菌剂、消毒剂、防腐剂、抗微生物剂等。
Johnson等(美国6,319,958和美国20020165130)涉及采用倍半萜化合物促进对外源性抗微生物化合物的摄取。类似地,一篇相关论文揭示了采用倍半萜化合物,如橙花叔醇、法尼醇、没药醇和阿普利酮(apritone)提高细菌穿透性和对外源性抗微生物化合物的易感性,表明倍半萜化合物具有非特异性和普遍的效果(Brehm-Stecher等2003,《抗微生物剂和化疗》(Antimicrobial Agents andChemotherapy),47(10):3357-3360)。具体说,Brehm-Stecher等报道,橙花叔醇、法尼醇、没药醇和阿普利酮提高了金黄色葡萄球菌对抗生素红霉素、庆大霉素、万古霉素、环丙沙星(ciproflaxin)、氯林可霉素和四环素的易感性。此外,Brehm-St echer等没有公开将QAC用作抗微生物剂。
在各种专业和非专业应用领域中,一直需要一种无刺激性、安全和有效的菌组合物。
发明内容
本发明涉及含有季铵化合物及精油和/或单个精油成分的组合的抗微生物组合物。可将这种组合包含于洗剂、凝胶、乳膏、肥皂等中,施用于皮肤或粘膜。本发明基于,或至少部分基于观察到用精油和/或单个精油成分及低浓度的季铵化合物组合获得了协同抗微生物效果。
具体实施方式
本发明涉及组合物及其使用方法,其中通过包括协同量的季铵化合物及精油和/或一种或多种单个精油成分提高了凝胶、乳膏、软膏、洗剂或肥皂的抗微生物活性。本发明制剂包含协同有效量的至少一种季铵化合物及至少一种精油和/或单个精油成分。
本发明所用术语“协同”和“协同有效”指施用两种或多种物质产生的生物学效果大于单独施用这些物质产生的生物学效果之和。
适用于本发明的季铵化合物的例子包括但不限于:苯扎氯铵(″BZK″)、苯索氯铵(″BZT″),其它苯扎卤铵(benzalkonium halides)或苯索卤铵(benzethoniumhalides),包括但不限于:苯扎溴铵、苯扎氟铵、苯索溴铵、苯索氟铵、氯化十六烷基吡啶、氯化烷基酰氨基丙烷鎓(alkylamidopropalkonium chloride)、氯化二十二烷基鎓(behenalkonium chloride),甲基硫酸二十二烷基鎓(behentrimoniummethosulphate),二十二烷基酰氨基丙基乙基二鎓(behenamidopropylethyldimonium ethosulphate),氯化十八烷基鎓(stearalkoniumchloride),氯化十八烯基鎓(olealkonium chloride),氯化十六烷基鎓(cetrimoniumchloride),地喹氯铵,硫酸N-十四烷基-N-甲基-吗啉蓊甲酯,聚二氯[N-[3-(二甲基胺基)丙基]-N’-[3-(乙烯基氧乙烯二甲基胺)丙基]脲],α-4-[1-三(2-羟乙基)氯化铵-2-丁烯基]-ω-三(2-羟乙基)氯化铵,聚[氧乙烯(二甲基亚胺基)乙烯(二甲基亚胺基)-二氯乙烯]。
季铵化合物的浓度可以在约0.01%和0.5%之间;优选的季铵化合物是浓度在0.05%和0.3%之间,更优选在0.1%和0.2%之间的苯索氯铵或苯扎氯铵。除非特别说明,这些百分数和本文中的其它百分数是质量/质量百分数。
本文所述的精油(″EO″)是获自植物或动物来源的挥发油,或其合成等价物,由几种成分,如单萜和倍半萜烃类,单萜和倍半萜醇、酯、醚、醛、酮、氧化物等的复杂混合物组成。EO的例子包括但不限于:佛手柑油、香鼠尾草油、依兰油、橙花油、檀木油、蓝丹油、姜油、薄荷油、薰衣草油、茉莉油、老鹳草油波旁、薄荷油、丁香油、广藿香油、迷迭香油、玫瑰木油、檀木油、茶树油、香草油、柠檬草油、香柏油、香胶树油、红橘油、扁柏油、亥巴油(Hiba oil)、银杏油(ginko oil)、桉叶油、柠檬油、橙油和甜橙油。
精油的单个成分(″IC″)可以是从(天然)油中分离的,或完全或部分合成的,包括但不限于:1-香茅醇、α-戊基肉桂醛、新铃兰醛(lyral)、香叶醇、法尼醇、羟基香茅醛、异丁子香酚、丁子香酚、桉树脑、里哪醇、柠檬醛、麝香草酚、柠檬烯和薄荷醇。
IC的其它例子包括倍半萜化合物,它们可以是精油中的活性化合物。从3个5-碳异戊二烯单元通过生物合成形成含有15个碳的倍半萜化合物。倍半萜化合物包括但不限于:法尼醇、橙花叔醇、没药醇、阿普利酮、母菊兰烯、檀香脑、姜醇、胡萝卜醇和石竹素(caryophyllen)。
本发明包括一种或多种EO的混合物、一种或多种IC的混合物以及一种或多种EO和一种或多种IC的混合物。
EO和IC的浓度可以在0.01%和10%之间;优选在0.05%和1.0%之间或在0.05%和0.5%之间,更优选在0.2%和0.5%之间。在优选实施方式中,EO是柠檬油和/或IC是法尼醇。
在某些具体的非限制性实施方式中,本发明提供了制剂,包括但不限于凝胶、乳膏、洗剂或软膏,它还包含一定量的锌,使其能够抑制该制剂的施用对皮肤或粘膜的刺激。可通过加入锌来抵消精油的刺激效果。在局部用药组合物中使用锌是本领域公知的,公开于以下专利:美国专利号5,708,023、5,965,610、5,985,918和6,037,386。
在本发明优选实施方式中,采用了低浓度的两种或多种水溶性锌盐。术语“低浓度”指以重量比计(w/w),游离锌离子(Zn2+)在凝胶或乳膏中所占百分数小于0.5%。适用于这些组合物的锌盐包括乙酸锌(在水中的摩尔溶解度为1.64摩尔/升)、丁酸锌(在水中的摩尔溶解度为0.4摩尔/升)、柠檬酸锌(在水中的摩尔溶解度为<0.1摩尔/升)、葡糖酸锌(在水中的摩尔溶解度为0.28摩尔/升)、甘油酸锌(水溶性中等)、乙醇酸锌(水溶性中等)、甲酸锌(在水中的摩尔溶解度为0.33摩尔/升)、乳酸锌(在水中的摩尔溶解度为0.17摩尔/升)、吡啶甲酸(picolinate)锌(水溶性中等)、丙酸锌(在水中的摩尔溶解度为1.51摩尔/升)、水杨酸锌(水溶性低)、酒石酸锌(水溶性中等)和十一碳烯酸锌(水溶性中等)。在尤其优选的实施方式中,锌盐包含有效量的两种或多种下述锌盐的组合:乙酸锌(0.05-2.0%)、柠檬酸锌(0.05-2.0%)、葡糖酸锌(0.05-2.0%)和乳酸锌(0.05-2.0%)。在优选实施方式中,锌盐是0.2-0.6%葡糖酸锌、0.1-0.3%乙酸锌和0.1-0.3%乳酸锌。在尤其优选的实施方式中,锌盐是0.3%葡糖酸锌、0.1%乙酸锌和0.1%乳酸锌,或0.2%乳酸锌和0.2%葡糖酸锌。国际专利申请号PCT/US03/03896,2003年8月14日公开为WO 03/066001中描述了可含有本发明的协同组合的其它组合物,以整体纳入本文作为参考。
可将本发明的凝胶、软膏、洗剂或乳膏局部施用于皮肤或身体的各种粘膜,包括但不限于口腔、鼻腔、阴道或直肠腔粘膜。
在优选实施方式中,凝胶、洗剂、软膏或乳膏可含有水、胶凝剂、增稠剂、亲水或疏水聚合物、乳化剂、润肤剂和/或醇如乙醇的混合物。在优选实施方式中,本文要求保护的组合物含有10-90w/w%的醇、15-70w/w%的水、0.05-3.0w/w%的增稠剂和/或胶凝剂,以及0.1-3.0w/w%的润肤剂。
在优选实施方式中,如果存在增稠剂,它不是聚丙烯酸基增稠剂,例如但不限于:卡波姆、聚羰乙烯或Ultrez,因为发现聚丙烯酸基增稠剂与季铵化合物不相容。虽然不希望受限于任何具体理论,但相信这种增稠剂的阴离子基团可与季铵化合物的阳离子基团可能发生相互作用。优选地,如果采用胶凝剂,它不是阴离子物质,而最好是非离子或阳离子物质。
本发明组合物还可任选地包括一种或多种附加抗微生物剂,例如但不限于:抗病毒药、抗菌药或抗真菌物质。抗微生物剂也包括具有杀病毒或抑病毒,杀菌或抑菌,或者杀真菌或抑真菌性质的任何组合的物质。抗微生物剂是本领域普通技术人员熟知的。抗微生物剂的例子包括但不限于:碘消灵、碘酒、苯甲酸、脱氢乙酸、丙酸、山梨酸、羟苯甲酸甲酯、羟苯甲酸乙酯、羟苯甲酸丙酯、羟苯甲酸丁酯、溴棕三甲铵、氯己定(游离碱和/或盐)、其它双胍如聚亚己基缩二胍(PHMB)和葡糖酸氯己定(CHG)、氯甲酚(chloroeresol)、氯二甲酚(chlorxylenol)、苯甲醇、溴硝丙二醇、氯丁醇、乙醇、苯氧乙醇、苯基乙醇、2,4-二氯苯甲醇、硫柳汞、氯林可霉素、红霉素、过氧化苯甲酰、莫匹罗星、枯草杆菌素、多粘菌素B、新霉素、三氯生、对氯间二甲苯、磷酸胆碱钙、咪康唑、氟康唑、伊康唑(itriconazole)、酮康唑,及其药学上可接受的盐。可在参考文献,如Goodman和Gilman的《治疗学的药理学基础》(The Pharmacological Basis of Therapeutics)(Goodman Gilman A,Rall TW,Nies AS,Taylor P,编(Pergamon Press;Elmsford,N.Y.:1990))中找到用于本发明的抗微生物剂的这些和其它例子,将其内容纳入本文作为参考。
在一个实施方式中,本发明组合物含有选自二葡糖酸氯己定(CHG)和聚亚己基缩二胍(PHMB)的双胍化合物。该双胍化合物的优选浓度为0.1-2.0w/w%。
药学上可接受的氯己定盐是本领域普通技术人员熟知的,包括但不限于:棕榈酸氯己定、二氨基苯膦酸氯己定、二葡糖酸氯己定(″CHG″)、二乙酸氯己定、二盐酸氯己定、二氯氯己定、二氢碘氯己定、二高氯酸氯己定、二硝酸氯己定、硫酸氯己定、亚硫酸氯己定、硫代硫酸氯己定、磷酸氯己定二酸、二氟磷酸氯己定、二甲酸氯己定、二丙酸氯己定、二碘代丁酸氯己定、二正戊酸氯己定、二己酸氯己定、丙二酸氯己定、琥珀酸氯己定、苹果酸氯己定、酒石酸氯己定、二单乙醇酸氯己定、单二乙醇酸氯己定、乳酸氯己定、二-α-羟基异丁酸氯己定、二葡糖酸氯己定、二异硫代硫酸氯己定、二苯甲酸氯己定、二肉桂酸氯己定、二扁桃酸氯己定、二间苯二酸氯己定、二-2-羟基萘酸氯己定和双羟萘酸氯己定。
在本发明组合物的配制中,认为制剂还可包含不具有上述成分的活性的成分,它们在制剂中起辅助作用,与所述组合物作为整体使用。这种成分的例子是生物应用制剂的生产领域的普通技术人员熟知的。这些成分的例子包括(例如)以下物质:粘合剂、润肤剂、防腐剂(如羟苯甲酸甲酯)、润滑剂、着色剂、香料等。因此,当所考虑的表面是皮肤时,本发明组合物可含有加入已知洗剂或药剂的成分,它们对皮肤而言是生理可接受的,且不含会逆转或阻碍刺激物灭活剂的作用的成分。
在本发明的某些非限制性实施方式中,可将该组合物加入预先存在的制剂中,只要这些制剂中的成分不防止或阻碍要求保护的组合物的活性。在优选实施方式中,可将要求保护的组合物加入市售的乳膏、软膏、凝胶或洗剂中。市售润滑剂的例子包括但不限于:以商品名″KY JELLY″、″ASTROGLIDE″和″PREVACARE″出售的润滑剂。市售洗剂的例子包括但不限于:以商品名″SOFT-SENSE″、″LOTION SOFT″、″CUREL″和″KERI″出售的洗剂。已知SOFT-SENSE(Johnson&Son,Inc.,Racine,Wis.)含有纯化水、甘油USP、氯化二硬酯酰二鎓、凡士林USP、棕榈酸异丙酯、1-十六醇、乙酸生育基(tocopheryl)酯(维生素E USP)、二甲基硅油、二氧化钛USP、羟苯甲酸甲酯、羟苯甲酸丙酯、氯化钠和香料。LOTION SOFT(Calgon Vestal,St.Louise,Mo.)是一种非离子保湿洗剂,已知含有黏多糖。已知CUREL(Bausch&Lomb Incorporated,Rochester,N.Y.)含有去离子水、甘油、季铵-5、凡士林、棕榈酸异丙酯、1-十六烷醇、二甲基硅油、氯化钠、香料、羟苯甲酸甲酯和羟苯甲酸丙酯。
要求保护的组合物可用于防汗剂、须后洗剂、水醇性皮肤消毒剂和治疗性乳膏等。
本发明的某些优选实施方式包含(举例但不作为限制)以下物质的一种或多种:醇(10-90w/w%),可以包括乙醇、正丙醇和异丙醇的一种或多种;一种或多种抗刺激量的锌化合物;一种或多种羟乙基纤维素与三甲基铵取代的环氧化物(聚季铵盐),例如U-care聚合物如Ucare JR125、JR 400、JR 30M、LR 400、LR30M或Ucare聚合物LK发生反应生成的聚季铵盐;羟丙基甲基纤维素如甲基纤维素A、E、K和40系列产品如甲基纤维素K4MS、甲基纤维素K100、甲基纤维素40-202、甲基纤维素K15MS等;一种或多种季铵化合物如BZK或BZT;十六烷基三甲基氯化铵(″CTAC″);十六烷基三甲基溴化铵(″CTAB″);氯化十八烯基鎓;氯化十八烷基鎓;Incroquat BA
85(氯化巴西棕榈酰氨基丙基鎓);甲基硫酸二(二十二烷基二鎓);Incroquat BES-35S(乙基硫酸二十二烷基酰氨基丙基乙基二鎓和十八烷醇);Incroquat B-65C(氯化二十二烷基鎓和十六烷醇);Incroquat Behenyl TMS(甲基硫酸二十二烷基三鎓和十六烯醇);以及一种或多种润肤剂,如Procetyl 10聚丙二醇-10十六烷基醚、Procetyl50聚丙二醇-50十六烷基醚、Promyristyl PM-3聚丙二醇-3十四烷基醚、聚丙二醇-3苯甲醚十四烷酸酯(Crodamol STS of Croda)、PEG 20杏树甘油酯、ProbutylDB-10、Glucam P20、Glucam E-10、Glucam P-10、Glucam E-20、Glucam P-20二硬脂酸酯、甘油、丙二醇、乙酸十四烷酯和乙酰化的羊毛脂醇(Acetulan)、羟化牛奶甘油酯(Cremerol HMG);硅酮液如Dow Corning硅酮液245、244、246、344、345、556;精油如柠檬油、香茅油、檀木油、柠檬草油、广藿香油、丁香油、百里香油、老鹳草油、罗勒油;精油的单个成分、如法尼醇、香茅醇、里哪醇、丁子香酚、柠檬醛、麝香草酚、桉树脑、薄荷醇;以及双胍如葡糖酸氯己定或聚亚己基缩二胍。
本发明提供了用上述组合物获得抗微生物效果的方法,该方法包括将有效量的组合物施用于表面。抗微生物效果明显降低了被一种或多种致病性传染物感染或现有感染继续发展的风险。不需将感染风险降低至零,但优选降低至少10%、20%、30%、40%、50%、60%、70%、80%或90%。可提供保护的抗传染物的例子包括但不限于:葡萄球菌属种如金黄色葡萄球菌和表皮葡萄球菌,链球菌属种如肺炎链球菌,肠球菌属种,沙门氏菌属种如伤寒沙门氏菌,埃希氏菌属种如大肠埃希氏菌,弧菌属种,奈瑟氏球菌属如脑膜炎奈瑟氏球菌和淋病奈瑟氏球菌,人类免疫缺陷病毒(HIV),人乳头瘤病毒(HPV),单纯疱疹病毒(HSV),沙眼衣原体,阴道滴虫和白念珠菌。
在本发明的一个实施方式中,本发明组合物不含抗生素,包括但不限于:四环素、氨苄青霉素、利福平、万古霉素、两性霉素B、制霉菌素和枯草杆菌素。
以下是含有和不含锌盐的本发明制剂的具体的非限制性例子。
不含锌盐的制剂
一般配方
具体配方
(A)醇类手术用手制剂-1
(B)醇类手术用手制剂-2
(C)醇类手术用手制剂-3
(D)术前皮肤消毒剂-1
含有锌盐的制剂
一般配方
具体配方
(E)醇类手消毒剂-1
(F)醇类手消毒剂-2
(G)醇类手术用手制剂-1
(H)醇类手术用手制剂-2
(I)醇类手术用手制剂-3
(J)醇类手术用手制剂-3
(K)抗刺激手术用手制剂-4
(L)抗刺激手术用手制剂-5
(M)含锌凝胶的醇类手术用手制剂-5
对于戴乳胶手套而对乳胶过敏的人而言,使用以下制剂是有利的。
(N)醇基抗刺激手术用制剂
(O)局部乳膏-1
(P)局部乳膏-2
(Q)局部乳膏-3
(R)局部乳膏-4
(S)术前皮肤消毒剂-1
(T)术前皮肤消毒剂-2
(U)术前皮肤消毒剂-3
(V)术前皮肤消毒剂-4
(W)锌凝胶洗手液#1
(X)锌凝胶洗手液#2
(Y)用于下层乳胶手套的锌凝胶乳膏/洗剂
(Z)抗刺激消毒肥皂
实施例
6.1.实施例1
在存在或不存在EO和IC,存在或不存在抗微生物化合物,如苯扎氯铵(BZK),葡糖酸氯己定(CHG)、2-巯基吡啶氧化锌(ZP)和三氯生(TC)的情况下制备用作抗刺激药的含锌盐局部制剂。评价了以下EO和IC:代表精油的柠檬油、代表萜烯醇的法尼醇和里哪醇以及代表醛类的柠檬醛。然后评价所得制剂的抗微生物活性。
6.1.1.方法
制备醇基锌凝胶
按以下方法制备醇基凝胶,将抗微生物剂、EO和/或IC加入下述基料中:
基料#1
在血清存在下评价快速抗微生物活性。
为测定可能被含有细菌的血液或其它蛋白质液体污染的抗菌组合物在皮肤上的效力,在血清存在下评价抗微生物活性,如下所述。简要说,将0.5毫升108CFU金黄色葡萄球菌/毫升加入无菌培养管中的成年牛血清中并混合。将0.5毫升测试制剂加入各管并涡旋搅拌。15秒后,用药物灭活培养基(LTSB)将它进一步稀释到1∶100,将0.5毫升铺于TSA平板上。在37℃孵育该板24小时,测定培养物的每毫升菌落数。
6.1.2.结果
据观察,当与BZK组合时,法尼醇、里哪醇、柠檬醛和柠檬油显示出协同的抗微生物效果。当法尼醇与其它抗微生物化合物、CHG、ZP或TC组合时,没有观察到这种协同作用。参见以下表1。
表1.
EO和IC成分与抗微生物剂的协同效果
受试生物体:金黄色葡萄球菌
注:BZK:苯扎氯铵(0.12%);PHMB:盐酸聚亚己基缩二胍(0.15%);CHG:葡糖酸氯己定(0.05%);TC:三氯生(0.3%);ZP:2-巯基吡啶氧化锌(0.5%);F:法尼醇(0.3%);LO:柠檬油(0.3%);LI:里哪醇;(0.3%);CI:柠檬醛(0.3%)。
从表1中可以看出,在所用的这些抗微生物化合物中,只有季铵化合物苯扎氯铵与EO和IC结合后,显示出明显的协同活性。
6.2.实施例2
本实施例显示了含有季铵化合物苯索氯铵(BZT)和法尼醇的组合物在锌盐存在下的抗微生物活性。如实施例1所述评价抗微生物活性。
将法尼醇和BZT以表2所示的比例掺入基料#1(含有锌盐)和下述基料#2(不含锌盐)中。
基料#2(不含锌盐)
表2
测试生物体:金黄色葡萄球菌
结果证明,在存在或不存在锌盐的情况下,BZT和法尼醇都有协同抗微生物效果。
6.3.实施例3
用实施例1所述的相同方法评价了将不同比例的法尼醇和季铵化合物掺入基料#2中的抗微生物效果。结果见表3。
表3
测试生物体:金黄色葡萄球菌
凝胶基中的组(w/w%) | cfu/毫升 | log10降低 |
对照凝胶 | 1.4×107 | 0.0 |
BZT(0.18%)(防腐剂水平) | 3.3×105 | 1.6 |
BZT(0.12%) | 4.7×105 | 1.5 |
BZT(0.06%) | 5.7×105 | 1.4 |
BZK(0.12%)(防腐剂水平) | 5.4×105 | 1.4 |
BZK(0.06%) | 1.8×106 | 0.9 |
法尼醇(0.5%) | 4.5×105 | 1.5 |
法尼醇(0.3%) | 4.6×105 | 1.5 |
BZT(0.18%)+法尼醇(0.5%) | 6.7×101 | 5.3 |
BZT(0.18%)+法尼醇(0.3%) | 6.7×101 | 5.3 |
BZT(0.12%)+法尼醇(0.3%) | 1.0×102 | 5.1 |
BZT(0.06%)+法尼醇(0.3%) | 1.0×102 | 5.1 |
BZK(0.12%)+法尼醇(0.5%) | 2.0×102 | 4.8 |
BZK(0.12%)+法尼醇(0.3%) | 3.7×103 | 3.6 |
BZK(0.06%)+法尼醇(0.3%) | 7.9×103 | 3.2 |
结果证明,当在对金黄色葡萄球菌进行的基于血清的快速测定中与法尼醇组合使用时,季铵化合物BZK和BZT都有协同抗微生物活性。
6.4.实施例4
用实施例1所述的相同测定方法评价了在存在或不存在季铵化合物BZK和BZT的情况下,掺入基料#2中的各种EO和IC的抗微生物效果。所用各种试剂的量见表4。除金黄色葡萄球菌外,也用大肠埃希氏菌进行了快速测定。结果见表4。
表4
注:BZK:苯扎氯铵(0.12w/w%:防腐剂水平);BZT:苯索氯铵(0.18w/w%:防腐剂水平);所有其它EO/IC(0.5w/w%)。
这些结果证明,当各种精油与季铵化合物组合使用时,在基于血清的快速测定中对金黄色葡萄球菌具有快速的协同抗微生物活性。具体说,广藿香油、罗勒油、桉叶油、百里香油、丁香油、老鹳草油和香茅油显示出显著的抗微生物效果。
6.5.实施例5
用实施例1所述的相同测定方法评价了在法尼醇和季铵化合物的组合中加入各种双胍抗微生物化合物,将其掺入基料#2的效果。结果见表5。
表5
PHMB似乎提高了BZT和法尼醇的组合的活性。
6.6.实施例6
该实施例证明了含有法尼醇与各种抗微生物剂组合的凝胶的抗微生物活性。选择抗微生物剂的浓度,使这些成分达到留在皮肤上的护肤制剂中允许的水平。用实施例1所述的方法测定抗微生物活性。数据见表6。
表6
测试生物体:金黄色葡萄球菌
(a)对照基料实验的菌落数是3.4×107cfu/毫升。
(b)作为对照,凝胶基料与表6中所示凝胶相同,但不含任何抗微生物剂。
结果显示,法尼醇提高抗微生物剂活性的能力因化合物而不同。法尼醇与季铵化合物苯扎氯铵(BZT)和苯索氯铵(BZK)具有协同作用。在双胍类抗微生物化合物中,它提高了盐酸聚亚己基缩二胍(PHMB)的活性,但未提高葡糖酸氯己定(CHG)的活性。法尼醇与三氯生也没有任何协同作用,也不提高三氯生的作用。因此,法尼醇的协同作用或提高抗微生物剂/防腐剂的活性的能力对所讨论抗微生物剂具有特异性。
用与上述表6相同的法尼醇浓度(0.3w/w%,即1.35mM每100克凝胶)进行了类似研究,将各种抗微生物剂以相同摩尔浓度加入凝胶(0.06mM每100克凝胶)中。数据见下表7。
表7
测试生物体:金黄色葡萄球菌
(a)对照基料实验的菌落数是6.4×107cfu/毫升。
(b)作为对照,使用凝胶基料与表7中所示凝胶相同,但不含任何防腐剂/抗微生物剂。
(c)由于三氯生即使在1.04mM浓度下也无效,所以没有用0.06mM浓度进行实验。
与表6所示结果类似,法尼醇对各种抗微生物剂的抗微生物活性的提高效果不同。法尼醇似乎与BZT,而非三氯生具有协同的抗微生物活性。PHMB似乎提高了法尼醇的活性。法尼醇发挥协同作用的机制或提高抗微生物剂的活性的机制因化合物而不同,但对于相同化合物是相同的,与浓度无关(无论化合物的浓度是以w/w%计还是以摩尔分数计)。
本说明书引用了各种参考文献、专利、刊物、产品说明书等,将这些公开以整体纳入本文作为参考。
Claims (12)
1.一种局部使用的抗微生物组合物,所述组合物含有:
(a)季铵化合物;和
(b)单个精油成分;
其中所述季铵化合物和所述单个精油成分以显示协同抗微生物活性的量存在,其中所述单个精油成分的浓度是0.05-1.0%w/w。
2.如权利要求1所述的组合物,其特征在于,所述季铵化合物的浓度是0.01-0.5%w/w。
3.如权利要求1所述的组合物,其特征在于,所述季铵化合物选自苯扎氯铵和苯索氯铵。
4.如权利要求1所述的组合物,其特征在于,所述单个精油成分选自1-香茅醇、α-戊基肉桂醛、新铃兰醛、香叶醇、法尼醇、羟基香茅醛、异丁子香酚、丁子香酚、桉树脑、里哪醇和柠檬醛。
5.如权利要求4所述的组合物,其特征在于,所述单个精油成分为法尼醇。
6.如权利要求1所述的组合物,其特征在于,所述组合物还包含能够降低刺激的量的两种或多种锌盐。
7.如权利要求6所述的组合物,其特征在于,所述两种或多种锌盐选自乙酸锌、柠檬酸锌、葡糖酸锌、甘油酸锌、乙醇酸锌、甲酸锌、乳酸锌、吡啶甲酸锌、丙酸锌、水杨酸锌、酒石酸锌、十一碳烯酸锌、氧化锌和硬脂酸锌。
8.如权利要求6所述的组合物,其特征在于,所述两种或多种锌盐各自的浓度为0.1-0.5重量%。
9.如权利要求1所述的组合物,其特征在于,所述组合物还包含泛酰醇,其浓度为0.5%-2%w/w。
10.如权利要求1所述的组合物,其特征在于,所述组合物还包含选自葡糖酸氯己定和聚亚己基缩二胍的双胍化合物,其中所述双胍化合物的浓度为0.1-2.0%w/w。
11.如权利要求1所述的组合物,其特征在于,所述组合物还包含浓度为10-90%w/w的醇、浓度为15-70%w/w的水、浓度为0.05-3.0%w/w的增稠剂和/或胶凝剂,以及浓度为0.1-3.0%w/w的润肤剂。
12.一种在对象的表面上产生抗微生物效果的方法,所述方法包括将有效量的权利要求1-11中任一项所述组合物施用于该表面,其中,所述表面是皮肤,所述抗微生物效果是被一种或多种致病性传染物感染的风险降低。
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- 2004-07-15 CN CN2011102381998A patent/CN102309473A/zh active Pending
- 2004-07-15 AU AU2004258899A patent/AU2004258899B2/en not_active Ceased
- 2004-07-15 CN CN2011102382242A patent/CN102319409A/zh active Pending
- 2004-07-15 WO PCT/US2004/022505 patent/WO2005009352A2/en active Application Filing
- 2004-07-15 BR BRPI0412675-0A patent/BRPI0412675A/pt not_active IP Right Cessation
- 2004-07-15 JP JP2006520288A patent/JP2007534620A/ja active Pending
- 2004-07-15 MX MXPA06000543A patent/MXPA06000543A/es active IP Right Grant
- 2004-07-15 CA CA2532730A patent/CA2532730C/en not_active Expired - Fee Related
- 2004-07-15 US US10/891,624 patent/US7871649B2/en not_active Expired - Fee Related
- 2004-07-15 EP EP04778149A patent/EP1651176A4/en not_active Withdrawn
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-
2010
- 2010-11-29 US US12/955,432 patent/US9421263B2/en not_active Expired - Fee Related
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Also Published As
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AU2004258899B2 (en) | 2009-09-03 |
EP1651176A4 (en) | 2008-05-07 |
JP2012107027A (ja) | 2012-06-07 |
CN102319409A (zh) | 2012-01-18 |
CN101217870B (zh) | 2011-10-12 |
CN101217870A (zh) | 2008-07-09 |
WO2005009352A3 (en) | 2007-11-29 |
US9421263B2 (en) | 2016-08-23 |
CA2532730A1 (en) | 2005-02-03 |
EP1651176A2 (en) | 2006-05-03 |
US20050019431A1 (en) | 2005-01-27 |
CA2532730C (en) | 2013-02-26 |
JP2007534620A (ja) | 2007-11-29 |
BRPI0412675A (pt) | 2006-10-03 |
US7871649B2 (en) | 2011-01-18 |
WO2005009352A2 (en) | 2005-02-03 |
AU2004258899A1 (en) | 2005-02-03 |
US20110070316A1 (en) | 2011-03-24 |
MXPA06000543A (es) | 2006-03-30 |
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