CN103501779A - 含水性贴附剂 - Google Patents
含水性贴附剂 Download PDFInfo
- Publication number
- CN103501779A CN103501779A CN201280006051.4A CN201280006051A CN103501779A CN 103501779 A CN103501779 A CN 103501779A CN 201280006051 A CN201280006051 A CN 201280006051A CN 103501779 A CN103501779 A CN 103501779A
- Authority
- CN
- China
- Prior art keywords
- general formula
- water
- nonionic surfactant
- property
- effective ingredient
- 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.)
- Granted
Links
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- 230000001070 adhesive effect Effects 0.000 title claims abstract description 79
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- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 32
- 239000002736 nonionic surfactant Substances 0.000 claims abstract description 30
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- 229960002373 loxoprofen Drugs 0.000 claims abstract description 12
- BAZQYVYVKYOAGO-UHFFFAOYSA-M loxoprofen sodium hydrate Chemical compound O.O.[Na+].C1=CC(C(C([O-])=O)C)=CC=C1CC1C(=O)CCC1 BAZQYVYVKYOAGO-UHFFFAOYSA-M 0.000 claims abstract description 12
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Abstract
本发明的目的在于提供一种含水性贴附剂,其中洛索洛芬等具有规定的环状酮结构的有效成分的稳定性优异。在具有支持体和位于上述支持体上的粘合剂层的含水性贴附剂中,粘合剂层含有有效成分、非离子型表面活性剂和水,所述有效成分包含具有规定的环状酮结构的化合物、其药理学上允许的盐或溶剂化物。非离子型表面活性剂优选具有6.0以上、且9.5以下的HLB值,优选为环氧乙烷加成型、且环氧乙烷加成摩尔数为5摩尔以下。
Description
技术领域
本发明涉及一种含水性贴附剂。
背景技术
近年来,为了进行透皮给予来代替药物的口服给予、通过注射的静脉给予等,正积极地开发贴附剂,该贴附剂中,在粘合剂中配合了有效成分的粘合剂层位于支持体上。因为贴附剂在从贴附于皮肤上开始到剥离为止的期间、能在长时间内使大致一定量的有效成分透皮吸收,所以是有用的。
另一方面,贴附剂的粘合剂层中,除含有有效成分之外,还含有以粘合剂为代表的多种成分,由此,贴附剂中的有效成分易于经时劣化,提高其稳定性是重要的。
贴附剂包括含有水的含水性贴附剂(巴布剂)、及非水性贴附剂(贴片剂、膏药剂等)这两种类型。其中,对于非水性贴附剂,暗示了通过使用2-巯基苯并咪唑等抗氧化剂,可以提高有效成分的稳定性(专利文献1)。
专利文献1:日本特开平11-79980号公报
发明内容
但是,对于含水性贴附剂,由于在粘合剂层中还含有水,所以一般认为从与非水性贴附剂不同的观点考虑必须提高有效成分的稳定性。另外,有效成分的分解根据该有效成分的不同而不同,因此,提高稳定性所必需的对策也必须根据有效成分的不同而进行研究。
本发明是鉴于以上情况而完成的,本发明的目的在于提供一种含水性贴附剂,其中,洛索洛芬(loxoprofen)等具有规定的环状酮结构的有效成分(药物)的稳定性优异。
本发明人等发现:具有规定的环状酮结构的有效成分在水性环境中的反应性(分解性)被非离子型表面活性剂抑制,从而完成了本发明。具体而言,本发明提供以下方案。
(1)一种含水性贴附剂,具有支持体、和位于上述支持体上的粘合剂层,
上述粘合剂层含有有效成分、非离子型表面活性剂和水,所述有效成分包含通式1所示的化合物、其药理学上允许的盐或溶剂化物,
······通式1
式中,n为0、1或2,R为有机基团。
(2)如(1)所述的含水性贴附剂,其中,上述化合物为洛索洛芬。
(3)如(1)或(2)所述的含水性贴附剂,其中,上述非离子型表面活性剂具有6.0以上、且9.5以下的HLB值。
(4)如(1)至(3)中任一项所述的含水性贴附剂,其中,上述非离子型表面活性剂为环氧乙烷加成型,且环氧乙烷加成摩尔数为5摩尔以下。
(5)如(4)所述的含水性贴附剂,其中,上述非离子型表面活性剂为选自聚氧乙烯氢化蓖麻油(环氧乙烷加成摩尔数为5摩尔)、及聚氧乙烯十二烷基醚(环氧乙烷加成摩尔数为2摩尔)中的1种以上。
(6)一种方法,所述方法针对具有支持体和位于上述支持体上的粘合剂层的含水性贴附剂,通过在上述粘合剂层中配合包含通式1所示的化合物、其药理学上允许的盐或溶剂化物的有效成分、水以及非离子型表面活性剂,由此抑制上述化合物变为通式2或通式3所示的化合物,
······通式1
······通式2
······通式3
通式1~3中,n为0、1或2,R为有机基团。
(7)一种含有非离子型表面活性剂的制剂,对于具有支持体和位于上述支持体上的粘合剂层的含水性贴附剂,所述制剂与有效成分(包含通式1所示的化合物、其药理学上允许的盐或溶剂化物)和水一同配合在上述粘合剂层中,用于抑制上述化合物变为通式2或通式3所示的化合物。
根据本发明,具有规定的环状酮结构的有效成分在水性环境中的反应性被非离子型表面活性剂抑制,因此可以提高含水性贴附剂中的洛索洛芬等具有规定的环状酮结构的有效成分的稳定性。
具体实施方式
以下对本发明的实施方式进行说明,但不限定本发明的主旨。
本发明的贴附剂具有支持体和位于上述支持体上的粘合剂层,上述粘合剂层至少含有下述有效成分、非离子型表面活性剂和水,所述有效成分包含通式1所示的化合物、其药理学上允许的盐或溶剂化物。
[粘合剂层]
非离子型表面活性剂以往作为水性贴附剂中的表面活性剂使用,但没有想到其作为药物稳定剂是有用的。本发明人惊奇地发现:非离子型表面活性剂在水性贴附剂中抑制具有规定的环状酮结构的有效成分的反应性(分解性)。具体而言,下述非离子型表面活性剂在水性贴附剂中抑制通式1所示的化合物变化为通式2或3所示的化合物,所述非离子型表面活性剂的HLB值为6.0以上、且9.5以下,及/或为环氧乙烷加成型,环氧乙烷加成摩尔数为5摩尔以下。需要说明的是,该反应与有效成分的酯化(特别是与薄荷醇等生成酯体)完全不同(详情参见Journal of Chromatography A、2008年、1208、p.164-174)。
从通式1到通式2的变化通过酮的碳与其α位的碳之间的键开裂而产生,从通式1到通式3的变化通过α位的碳发生羟基化而产生。一般认为对于上述所有反应来说,环式结构的碳数及R不起作用,所以n可以为0、1、或2中的任一个,R可以为任意有机基团。需要说明的是,本发明中的有效成分的稳定性,是指由通式1的化合物生成的通式2及3的化合物的总和降低,优选是指通式2及3的化合物两者的生成量降低,但只要至少一者的生成量降低即可。
因此,通式1所示的化合物没有特别限定,可以为洛索洛芬等。另外,药理学上允许的盐为上述化合物及/或其溶剂化物的盐,没有特别限定,可以为钠盐、钾盐等碱金属盐;钙盐、镁盐等碱土金属盐等中的1种或2种以上。另外,溶剂化物为上述化合物及/或其药理学上允许的盐的溶剂化物,没有特别限定,通常为水合物。需要说明的是,有效成分(药物)可以以盐、游离体、溶剂化物(例如水合物)、非溶剂化物(例如非水合物)等任意形态配合。
具体而言,洛索洛芬通常以下述化学式1所示的钠盐·二水合物的形态配合,没有特别限定,也可以以其他盐、游离体、非水合物中的任一种形态配合。
····化学式1
非离子型表面活性剂在水性环境中抑制以下化学式2或3所示的化合物的生成。
····化学式2
····化学式3
HLB值为6.0以上、且9.5以下的非离子型表面活性剂没有特别限定,可以为下述非离子型表面活性剂中的1种或2种以上:硬脂酸甘油酯(含有20%的单甘油酯、HLB值7.0)、单硬脂酸聚甘油酯(HLB值9.0)、三硬脂酸聚甘油酯(HLB值9.5)、三硬脂酸十甘油酯(HLB值7.5)、三油酸聚甘油酯(HLB值7.0)、单硬脂酸聚氧乙烯甘油酯(环氧乙烷加成摩尔数5、HLB值9.5)、椰子油脂肪酸失水山梨醇酯(HLB值8.6)、单棕榈酸失水山梨醇酯(HLB值6.7)、聚氧乙烯失水山梨醇单硬脂酸酯(环氧乙烷加成摩尔数6、HLB值9.5)、聚氧乙烯山梨醇四油酸酯(环氧乙烷加成摩尔数6、HLB值8.5)、聚氧乙烯氢化蓖麻油(环氧乙烷加成摩尔数5。HLB值6.0)、聚氧乙烯氢化蓖麻油(环氧乙烷加成摩尔数10、HLB值6.5)、聚氧乙烯植物甾醇(环氧乙烷加成摩尔数5、HLB值9.5)、聚氧乙烯十二烷基醚(环氧乙烷加成摩尔数2、HLB值9.5)、聚氧乙烯硬脂基醚(环氧乙烷加成摩尔数2、HLB值8.0)、聚氧乙烯十二烷基醚(环氧乙烷加成摩尔数4、HLB值9.0)、聚氧乙烯油基醚(环氧乙烷加成摩尔数2、HLB值7.5)、聚氧乙烯山嵛基醚(环氧乙烷加成摩尔数5、HLB值7.0)、聚氧乙烯聚氧丙烯十六烷基醚(环氧乙烷加成摩尔数1、环氧丙烷加成摩尔数4、HLB值9.5)、聚氧乙烯聚氧丙烯十六烷基醚(环氧乙烷加成摩尔数1、环氧丙烷加成摩尔数8、HLB值9.5)、聚乙二醇单油酸酯(环氧乙烷加成摩尔数6、HLB值8.5)等。另外,优选为环氧乙烷加成型、且环氧乙烷加成摩尔数为5摩尔以下,具体而言,优选聚氧乙烯氢化蓖麻油(环氧乙烷加成摩尔数为5摩尔)、及聚氧乙烯十二烷基醚(环氧乙烷加成摩尔数为2摩尔)中的1种或2种。
非离子型表面活性剂的配合量没有特别限定,相对于有效成分的配合量,优选为10~500质量%。非离子型表面活性剂的配合量通常可以从相对于粘合剂层为3.0质量%以下的范围内选择。
由于利用非离子型表面活性剂,有效成分的稳定性显著提高,所以对于以稳定性为目的的其他成分,可以减少配合量,或也可以不配合。具体而言,在粘合剂层中可以配合选自亚硫酸盐、亚硫酸氢盐、及焦亚硫酸盐中的1种以上,相对于有效成分的配合,其配合量可以为1质量%以下。
亚硫酸盐可以为亚硫酸氢钠盐、亚硫酸氢钾盐等碱金属盐,钙盐、钡盐等碱土金属盐等,亚硫酸氢盐可以为钠盐、钾盐等碱金属盐、铵盐等,焦亚硫酸盐可以为钠盐、钾盐等碱金属盐等、具体而言,可以为亚硫酸钠、亚硫酸氢钠、焦亚硫酸钠。
本发明的含水性贴附剂中的粘合剂层含有水。水的配合量没有特别限定,相对于粘合剂层,可以为30~70质量%左右。
除上述成分之外,根据需要,粘合剂层可以含有聚丙烯酸及/或其盐等赋形剂、表面活性剂、交联剂、交联控制剂、增粘剂、保湿剂、药物的助溶剂、pH调节剂、清凉化剂、水溶性高分子化合物、无机粉体、抗氧化剂、防腐剂、色素等任意成分。
作为聚丙烯酸及/或其盐,可以举出聚丙烯酸、聚丙烯酸钠、聚丙烯酸部分中和物“NP-800(商品名)”及“NP-700(商品名)”(昭和电工社制)等,可以含有单独1种或含有2种以上的组合。
除了非离子型表面活性剂之外,还可以配合一般的表面活性剂。作为上述表面活性剂,可以添加例如二辛基磺基琥珀酸钠、烷基硫酸盐、2-乙基己基烷基硫酸酯钠盐、正十二烷基苯磺酸钠等阴离子表面活性剂;十六烷基三甲基氯化铵、十八烷基二甲基苄基氯化铵、聚氧乙烯十二烷基单甲基氯化铵等阳离子表面活性剂。
作为交联剂,可以举出多价金属盐,其中,优选铝化合物。作为铝化合物,可以举出二羟基氨基乙酸铝、氢氧化铝这样的氢氧化物,或氯化铝、硫酸铝、乙酸铝、硬脂酸铝这样的无机酸或有机酸的盐,铝矾(ammonium alum)这样的复盐,铝酸钠这样的铝酸盐,无机性铝配盐及有机性铝螯合化物等。上述铝化合物可以为水溶性,也可以为难溶性。
另外,作为交联剂可以使用氢氧化铝凝胶,上述情况下,优选pH为4.5以上、且6.0以下。pH超过6.0时,氢氧化铝凝胶的铝难于溶出,粘合剂的交联反应不充分、保型性易恶化。但相对于此,使用二羟基氨基乙酸铝时,粘合剂层的pH可以超过6.0。
需要说明的是,pH可以使用pH调节剂进行设定,作为上述pH调节剂,可以举出酒石酸、磷酸、苹果酸、柠檬酸、盐酸、氢氧化钠、三乙醇胺、二乙醇胺、二异丙醇胺等,它们可以单独含有1种或含有2种以上的组合,优选酒石酸。
作为增粘剂,可以举出甲基丙烯酸·丙烯酸正丁酯共聚物、丙烯酸甲酯·丙烯酸2-乙基己基酯共聚物、聚丁烯、酯胶、萜烯树脂、脂环族饱和烃树脂等。相对于粘合剂层,其配合量可以为1质量%以上、30质量%以下,优选为2质量%以上、10质量%以下。
作为交联控制剂,可以举出乙二胺四乙酸钠(EDTA钠)、柠檬酸等,它们可以单独含有1种或含有2种以上的组合,优选乙二胺四乙酸钠。
作为保湿剂,可以举出浓甘油、山梨糖醇、乙二醇、丙二醇、聚乙二醇、聚丙二醇、液体石蜡、1,3-丙二醇、1,3-丁二醇、麦芽糖醇、木糖醇等多元醇等,它们可以单独含有1种或含有2种以上的组合,其中,优选浓甘油。需要说明的是,甘油的配合量可考虑制造成本或产生渗出的容易性等而适当设定。
作为药物的助溶剂,可以举出克罗米通(Crotamiton)、N-甲基-2-吡咯烷酮等吡咯烷酮衍生物、薄荷油、1,3-丁二醇等,它们可以单独含有1种或组合含有2种以上。
作为清凉化剂,除樟脑、百里酚之外,还可以举出1-薄荷醇、dl-薄荷醇、2-甲基-3-(1-基氧基)-1,2-丙二醇、3-1-薄荷氧基-1,2-丙二醇、5-甲基-2-(1-甲基乙基)-环己基-2-羟基丙酯等薄荷醇衍生物等,它们可以单独含有1种或组合含有2种以上。
作为水溶性高分子化合物,可以举出明胶、琼脂、聚乙烯醇、聚乙烯吡咯烷酮、碳酸亚丙酯、羧甲基纤维素、羧甲基纤维素钠、羟丙基纤维素、羟丙甲基纤维素、羟乙基纤维素、甲基纤维素、藻酸钠、马来酸酐共聚物、角叉菜胶等,它们可以单独含有1种或组合含有2种以上。
作为无机粉体,可以举出例如高岭土、氧化锌、氧化钛、硅酸酐等,它们可以单独含有1种或组合含有2种以上。
作为抗氧化剂,可以举出生育酚乙酸酯、抗坏血酸及/或其衍生物、亚硫酸钠、二丁基羟基甲苯等,它们可以单独含有1种或组合含有2种以上。
作为防腐剂,可以举出对羟基苯甲酸甲酯、对羟基苯甲酸丁酯、对羟基苯甲酸丙酯、百里酚等,它们可以单独含有1种或组合含有2种以上。
作为色素,对其种类没有特别限定,可以举出法定色素手册中记载的色素,它们可以单独使用1种或组合使用2种以上。
[支持体]
支持体可以由目前已知的贴附剂中使用的织物、无纺布、编织布等布帛、树脂膜、纸及它们的层合体构成。支持体的材质可以为选自聚丙烯、聚乙烯、聚丁烯、聚对苯二甲酸乙二醇酯、人造丝、棉、聚氨酯中的1种或2种以上,没有特别限定,但优选为聚对苯二甲酸乙二醇酯。从成本的方面考虑,优选使用由下述无纺布构成的支持体,所述无纺布由聚对苯二甲酸乙二醇酯形成。另外,使用树脂膜时,可以使用通过印刷或精炼白色、肉色等的涂料进行了着色、或写入了文字等的支持体,为了提高粘合剂的粘合性,也可以使用经过了聚氨酯处理、或消光处理等的支持体。
[剥离衬垫]
本发明的贴附剂也可以进一步具有被覆粘合剂层的剥离衬垫。作为上述剥离衬垫,优选聚对苯二甲酸乙二醇酯、聚丙烯等的树脂膜,也可以使用经过硅等的剥离处理、实行了压花加工的剥离衬垫。另外,也可以使用印刷或精炼了白色等的涂料的材料作为剥离衬垫。
(制备方法)
本发明的贴附剂可以通过现有方法制备,可以如下进行制备,即,将上述必需成分及根据需要的上述任意成分适当配合,利用公知的方法进行捏合直至均匀,在剥离衬垫上延展,使贴附剂单位面积中的粘合剂质量为0.03~0.15g/cm2后,在该粘合剂层的表面上进一步层合支持体,然后,裁切成100mm×140mm的矩形状。另外,也可以如下进行制备,即,事先在支持体上使粘合剂延展,之后将剥离衬垫层合于其上。
以下给出实施例及比较例,具体地说明本发明,但本发明不限定于实施例。
实施例
[试验例1]
将表1所示的各成分经一定时间搅拌并混合后,在剥离衬垫上均匀地延展,使每1片贴附剂(140mm×100mm)中的粘合剂质量为约10g。之后,将聚对苯二甲酸乙二醇酯制无纺布贴合于粘合剂层的表面,由此制备贴附剂。
[表1]
表1中的表面活性剂如表2所示,由此制备贴附剂。将各贴附剂在40℃或60℃下放置后,切出表面积为10cm2的断片,精密称量其质量。之后,将剥离衬垫膜剥离,放入50mL的沉淀管中,向其中添加甲醇,振荡30分钟,提取药物。将提取液进行高速离心分离,将经过过滤处理的液体作为试样溶液,利用HPLC,测定化学式1~3、洛索洛芬的甘油酯(称作“GE”)、薄荷醇酯(称作“ME”)的质量。其结果示于表3。
[表2]
[表3]
(将开始时的洛索洛芬钠的量设为100时的相对质量)
如表2及3所示,全部实施例中特别是化学式3的生成被抑制,其中,在实施例8~13中,进一步地,化学式2及3两者的生成被抑制。由此,可知非离子型表面活性剂抑制水性环境中的化学式3的生成,具有6.0以上、且9.5以下的HLB值的环氧乙烷加成型、且环氧乙烷加成摩尔数为5摩尔以下的非表面活性剂进一步抑制化学式2及3两者的生成。另一方面,确认了洛索洛芬的酯体的生成量在各贴附剂之间没有显著差异。由此,可知非离子型表面活性剂特异性地抑制水性中由化学式1变化为化学式2及3。
在40℃及60℃下,将实施例8及市售品(Loxonin(注册商标)巴布剂100mg:配合聚山梨酸酯80作为表面活性剂)的贴附剂放置1~6个月,利用色差(ΔE)评价粘合剂层(药剂面)从刚刚制作贴附剂后开始有何种程度的着色。其结果示于表4。色差(ΔE)如下得到,即,通过色彩色差计(X-Rite Inc.制、Model SP64)测定粘合剂层表面的色度,利用下述式子算出刚刚制作贴附剂后与在40℃及60℃下放置1~6个月后的期间内的色度差。即,将白-黑的程度用L-级表示、红-绿的程度用a-级表示、蓝-黄的程度用b-级表示时,色差以各级之差的二次方之和的平方根、ΔE(=((Δa)2+(Δb)2+(ΔL)2)1/2)表示。
[表4]
如表4所示,确认了对于经时的粘合剂层着色,与市售品相比在实施例8中被抑制。
Claims (7)
2.如权利要求1所述的含水性贴附剂,其中,所述化合物为洛索洛芬。
3.如权利要求1或2所述的含水性贴附剂,其中,所述非离子型表面活性剂具有6.0以上、且9.5以下的HLB值。
4.如权利要求1至3中任一项所述的含水性贴附剂,其中,所述非离子型表面活性剂为环氧乙烷加成型,且环氧乙烷加成摩尔数为5摩尔以下。
5.如权利要求4所述的含水性贴附剂,其中,所述非离子型表面活性剂为选自聚氧乙烯氢化蓖麻油、及聚氧乙烯十二烷基醚中的1种以上,聚氧乙烯氢化蓖麻油的环氧乙烷加成摩尔数为5摩尔,聚氧乙烯十二烷基醚的环氧乙烷加成摩尔数为2摩尔。
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CN107106511A (zh) * | 2014-12-22 | 2017-08-29 | 久光制药株式会社 | 泥罨剂 |
CN114007594A (zh) * | 2019-06-24 | 2022-02-01 | 帝国制药株式会社 | 水性贴剂 |
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CN105473132B (zh) * | 2013-08-23 | 2019-01-29 | 久光制药株式会社 | 泥罨剂及其制造方法 |
EP3263097B1 (en) | 2015-02-24 | 2021-08-25 | Hisamitsu Pharmaceutical Co., Inc. | Adhesive skin poultice |
JP6613878B2 (ja) * | 2015-12-25 | 2019-12-04 | ライオン株式会社 | 口腔用ポリマーゲル製剤 |
JP6594937B2 (ja) * | 2016-09-05 | 2019-10-23 | 久光製薬株式会社 | シート状パック剤及びその製造方法 |
KR102000435B1 (ko) * | 2018-01-18 | 2019-07-16 | 대화제약 주식회사 | 하이드로겔 패치 형태의 경피투여용 약학 조성물 |
JP2019206497A (ja) | 2018-05-30 | 2019-12-05 | 小林製薬株式会社 | 外用医薬組成物 |
JP7257410B2 (ja) * | 2018-09-26 | 2023-04-13 | ニチバン株式会社 | 含水系貼付剤 |
WO2020166665A1 (ja) | 2019-02-14 | 2020-08-20 | 久光製薬株式会社 | パップ剤 |
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- 2012-01-30 TW TW101102865A patent/TW201236701A/zh unknown
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Patent Citations (5)
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US5891920A (en) * | 1994-10-05 | 1999-04-06 | Hisamitsu Pharmaceutical Co., Inc. | Medicinal adjuvants consisting of N-subsitituted-o-toluidine derivatives, and percutaneously absorbable preparations comprising the adjuvants |
JPH08165251A (ja) * | 1994-12-12 | 1996-06-25 | Hisamitsu Pharmaceut Co Inc | 溶解剤および該溶解剤を含有する外用製剤 |
WO2009031318A1 (ja) * | 2007-09-05 | 2009-03-12 | Kowa Co., Ltd. | 鎮痛・抗炎症剤含有外用剤 |
CN101896175A (zh) * | 2007-12-12 | 2010-11-24 | 帝国制药株式会社 | 含有环氧洛芬的水性贴剂 |
WO2010103845A1 (ja) * | 2009-03-11 | 2010-09-16 | 興和株式会社 | 鎮痛・抗炎症剤含有外用剤 |
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CN107106511A (zh) * | 2014-12-22 | 2017-08-29 | 久光制药株式会社 | 泥罨剂 |
CN107106511B (zh) * | 2014-12-22 | 2020-12-08 | 久光制药株式会社 | 泥罨剂 |
CN114007594A (zh) * | 2019-06-24 | 2022-02-01 | 帝国制药株式会社 | 水性贴剂 |
Also Published As
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JPWO2012102242A1 (ja) | 2014-06-30 |
JP2014156497A (ja) | 2014-08-28 |
TW201236701A (en) | 2012-09-16 |
JP2014156498A (ja) | 2014-08-28 |
JP5781097B2 (ja) | 2015-09-16 |
JP2014156499A (ja) | 2014-08-28 |
KR20140035879A (ko) | 2014-03-24 |
JP5702489B2 (ja) | 2015-04-15 |
JP5981488B2 (ja) | 2016-08-31 |
WO2012102242A1 (ja) | 2012-08-02 |
CN103501779B (zh) | 2016-08-10 |
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