CN105979926A - 作为渗透增强剂的辛酰丙氨酸乙酯 - Google Patents
作为渗透增强剂的辛酰丙氨酸乙酯 Download PDFInfo
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- CN105979926A CN105979926A CN201580008368.5A CN201580008368A CN105979926A CN 105979926 A CN105979926 A CN 105979926A CN 201580008368 A CN201580008368 A CN 201580008368A CN 105979926 A CN105979926 A CN 105979926A
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- Prior art keywords
- acid
- agent
- decoyl
- vitamin
- ethyl ester
- Prior art date
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Abstract
本发明涉及渗透增强剂,特别是在化妆品或其他局部组合物中将辛酰丙氨酸乙酯用作渗透增强剂,和包含该渗透增强剂与活性成分,特别是UV‑过滤剂、防痤疮活性物、抗衰老活性物、消炎剂、头发调节剂、防汗剂或除臭剂、增白剂、自晒黑剂和/或维生素组合的化妆品组合物。
Description
1.发明领域
本发明涉及辛酰丙氨酸乙酯作为渗透增强剂在化妆品或其他局部组合物中的用途,和包含辛酰丙氨酸乙酯与活性成分,特别是对皮肤有利的那些,如UV-过滤剂、防痤疮活性物、抗衰老活性物、消炎剂、头发调节剂、防汗剂或除臭剂、增白剂、自晒黑剂和维生素的组合的化妆品组合物。
2.现有技术描述
对于皮肤吸收促进剂(也称为渗透增强剂),在其开始用于化妆品组合物之前,经皮给药治疗体系是第一应用领域。药物活性物通过皮肤的递送是令人高度关注的,因为它能够全身性给药而避免肝首过机制。然而,皮肤阻隔性能阻碍大多数分子通过皮肤。渗透增强剂可用于促进关注物质的吸收。已研究了不同化学基团的渗透增强活性,并且已识别很多作用方式和相互作用的位点。在作用机制中,渗透增强作用通过以下方式实现:1)使溶剂性能适合于关注的物质以改进至皮肤的分配,2)与细胞间的脂质基质相互作用,从而改变阻隔结构,3)修饰细胞间蛋白以提高渗透性,和/或4)在皮肤中产生蓄积作用。
所述并且在药物组合物中使用的第一皮肤渗透增强剂中的一种为二甲亚砜(DMSO),一种属于亚砜类的通用溶剂。
特别设计为皮肤渗透增强剂的第一物质为氮酮月桂氮酮,一种非常亲油的物质,其通过与角质层中的脂质相互作用而改进渗透性。
吡咯烷酮类如N-甲基-2-吡咯烷酮(NMP)已用于消炎药物的皮肤吸收,但具有阻碍其使用的毒理学问题。
还已描述萜烯类如薄荷醇的使用,其中气味可使该应用具有挑战性。薄荷醇不仅通过与这些活性物形成共溶体系而提高渗透药物的溶解性,还通过借助其与脂质域的相互作用改变角质层的阻隔性能而提高渗透性。
脂肪酸,主要是不饱和脂肪酸(油酸),已成功用作增强剂。由于它们非常亲油,因此它们使角质层的脂质域改性,而醇类如乙醇或月桂醇溶解并提取角质层的脂质且与脂质双层相互作用,使得它们主要改进亲水性分子的渗透性。
近年来,将越来越多的活性成分用于化妆品中。由于局部施用途径,渗透增强剂还可用于个人护理应用。在化妆品领域中施用渗透增强剂的主要焦点不是全身性递送物质,而是提高活性物至皮肤的渗透,以增强化妆品的功效。通常将渗透增强剂如溶剂体系(例如丙二醇)用于化妆品组合物中,其通过提高药物分配或试剂促进角质层水和而起作用。
通常化妆品产品需要具有良好的皮肤相容性,并且成分应具有良好的毒理学特性。
很多研究已显示氨基酸酯是具有低毒性和非常好的生物相容性的有效渗透增强剂。
欧洲专利申请EP 0 552 505 A1公开了用于药物活性物质的皮肤吸收促进剂,其包含具有式:R1NH-R3–COOR2的氨基酸衍生物,其中R1为氢原子、具有1-20个碳原子的酰基或具有1-20个碳原子的烃基,R2为氢原子或具有1-20个碳原子的烃基,以及R3为-CHR4或苄基,R4为氢原子、甲基、异丙基、2-甲基丙基或1-甲基丙基。所提出的选自吲哚美辛、酮洛芬、***龙和吲哚洛尔的药物活性物质的吸收促进剂的最有效的候选为N-正十二烷酰基甘氨酸的酯。还已测试十二烷酰基氨基酸如丙氨酸、缬氨酸、亮氨酸和异亮氨酸的乙酯。
N-月桂酰基异丙基肌氨酸酯为化妆品领域中很多专利申请的主题:
其为如国际专利族WO 2003/039448所概述的选择的候选以用于溶解很多在用聚合物增稠的化妆品和皮肤用组合物中的脂相的组分和活性物。所述聚合物具有100000道尔顿以下的平均分子量,优选1000-30000,其包含a)具有带有至少一个杂原子的重复烃单元的聚合物主链,和b)任选地至少一个脂肪侧链和/或至少一个脂肪端链,其任选官能化,具有12-120个碳原子,键合于所述单元,脂肪链占杂原子单元和脂肪链的总数的40-98%。这些组合物也可包含UV-过滤剂。
欧洲申请EP 1277462 A1的主题为意欲用于人工晒黑皮肤的化妆品或皮肤用组合物,其包含至少一种自晒黑剂和至少一种N-酰基氨基酸酯。已显示N-酰基氨基酸酯的加入改进了自晒黑剂在用于人工晒黑皮肤的组合物中的着色和稳定性。选择N-月桂酰基肌氨酸异丙基酯与自晒黑剂组合。
包含至少一种1,3,5-三嗪衍生物和至少一种N-酰基氨基酸酯的组合物及其在或用于制造用于保护皮肤、嘴唇或覆盖物以防紫外线辐射的化妆品组合物中的用途公开在欧洲申请EP 1 269 980 A1中。选择与1,3,5-三嗪衍生物组合的N-酰基氨基酸酯为N-月桂酰基肌氨酸异丙基酯,其改进了组合物的防晒因子。
US申请US 2005/0065251 A1的发明涉及由聚酰胺构成的化妆品组合物,其特征在于其包含至少有机UV过滤剂,和至少氨基酸N-酰化的酯,并且涉及其在或用于制备用于保护皮肤、嘴唇或皮肤附属物以防紫外线辐射的组合物中的用途。优选的氨基酸N-酰化的酯再次为N-月桂酰基肌氨酸异丙基酯。
N-月桂酰基肌氨酸异丙基酯的使用具有一些限制。其为具有蜡状质地的半固体,其难以并入皮肤组合物,因为其熔点在室温以上。该熔点也阻止物质在皮肤上熔融。
本发明的目的是提供与其他化妆品添加剂具有良好的耐受性和改进的相容性的用于局部组合物的有效渗透增强剂,其可容易地并入化妆品组合物。所述渗透增强剂也可提供良好的感官特性。
3.发明描述
本发明涉及辛酰丙氨酸乙酯在化妆品和其他局部或口服组合物中作为渗透增强剂的用途。就本发明而言,渗透也可包括透过和吸收。
本发明的一个实施方案涉及包含辛酰丙氨酸乙酯作为渗透增强剂的化妆品组合物。这些组合物包含辛酰丙氨酸酯与活性物的组合,优选与UV-过滤剂、防痤疮活性物、抗衰老活性物、消炎剂、头发调节剂、防汗剂或除臭剂、增白剂、自晒黑剂和维生素的组合。
令人惊奇的是,发现包含辛酰丙氨酸乙酯的组合物提供非常好的感官特性,同时赋予皮肤润湿的感觉而不是令人不愉快的粘性。辛酰丙氨酸乙酯也比其他N-辛基氨基酸酯更促进活性物的皮肤渗透,尤其是亲水性活性物的渗透。
化妆品组合物基于总组合物可包含0.1-90重量%辛酰丙氨酸乙酯,通常基于总组合物可包含1-30重量%,优选2-10重量%,更优选2-5重量%。
结果是与熟知和确定的参照如DMI和乙基二甘醇相比,辛酰丙氨酸乙酯具有与角质层相距更小的汉森溶解度参数(HSP),这说明作为皮肤渗透增强剂的良好潜力。汉森溶解度参数为良好分配至角质层的关键指标,条件为分子在RT下为液体且具有足够小的分子体积。
对于包含活性物的化妆品组合物而言,加入作为渗透增强剂的辛酰丙氨酸乙酯具有很多优点。因为靶向作用快速实现和/或所需组织(层)更加有效地定向和/或可使用更低浓度的活性成分,尤其可改进包含具有不利的相容性性能的活性物的配制剂的皮肤相容性。
渗透增强剂本身与DMI相比以更小程度渗透通过皮肤,并且因此较不可能全身可得到。此外,辛酰丙氨酸乙酯可在皮肤中代谢,从而有助于改进毒理学特性。
此外,察觉到辛酰丙氨酸乙酯具有与其他柔润剂相近的润湿作用,察觉到其比其他柔润剂更快地吸收,从而其在局部组合物中的施用导致令人愉快的感官特性。
辛酰丙氨酸乙酯为无气味的液体物质,并且因此非常易于并入化妆品和局部组合物。得到的配制剂具有非常好的物理化学稳定性。作为极性柔润剂,其具有有益增溶性能并且可改进活性物在组织上的分散和分布。
活性化合物
本发明配制剂包含辛酰丙氨酸酯与化妆品可接受的活性化合物的组合。
根据本发明,活性化合物(一种或多种化合物)可有利地选自UV-过滤剂、防痤疮活性物、抗衰老活性物、消炎剂、头发生长调节剂、对头发或毛囊起作用的试剂、防汗剂或除臭剂、增白剂、自晒黑剂、多肽、寡肽、蛋白质、乙酰水杨酸、阿托品、甘菊环,氢化可的松及其衍生物,例如氢化可的松17-戊酸酯,维生素,尤其是B和D系列,特别是维生素B1、维生素B12、维生素D,维生素A及其衍生物,例如棕榈酸视黄酯,维生素E或其衍生物,例如生育酚乙酸酯,维生素C及其衍生物,例如抗坏血酸基葡糖苷,以及还有烟酰胺、泛醇、红没药醇、表面麻醉剂(polydocanol),不饱和脂肪酸,例如必需脂肪酸(常称作维生素F),尤其是γ-亚麻酸、油酸、二十碳五烯酸、二十二碳六烯酸及其衍生物,氯霉素、咖啡因、***素、百里酚、樟脑、角鲨烯,植物和动物来源的提取物或其他产品,例如月见草油、琉璃苣油或角豆油、鱼油、鳕鱼肝油,以及还有神经酰胺和神经酰胺类化合物、乳香提取物、绿茶提取物、荷花提取物、甘草提取物、金缕梅、去屑活性化合物(例如二硫化硒、1-氧-2-巯基吡啶锌、吡罗克酮、醇胺、氯咪巴唑、羟甲辛吡酮(octopirox)、表面麻醉剂及其组合),以及络合的活性化合物,例如γ-米谷酚和钙盐如泛酸钙、氯化钙和乙酸钙的那些。
活性化合物也可选自NO合成酶抑制剂,尤其是如果本发明组合物用于处理和预防皮肤内因和/或外因衰老的症状以及用于处理和预防紫外辐射对皮肤和毛发的有害作用。优选的NO合成酶抑制剂为硝基精氨酸。
此外,活性化合物还有利地选自:儿茶酚和儿茶酚的胆汁酸酯以及含有儿茶酚或儿茶酚的胆汁酸酯的植物或植物部分如山茶科(Theacease)植物家族的叶子,尤其是山茶属植物(绿茶)的叶子的含水或有机提取物。儿茶酚是一组如下化合物,其被认为是氢化黄酮或花色素且为“儿茶酚”衍生物(儿茶酚、3,3',4',5,7-黄烷五醇、2-(3,4-二羟基苯基)苯并二氢吡喃-3,5,7-三醇)。就本发明而言,表儿茶酚((2R,3R)-3,3',4',5,7-黄烷五醇)也是一种有利的活性化合物。
优选的活性化合物还有选自如下的多酚或儿茶酚:(-)-儿茶酚、(+)-儿茶酚、(-)-儿茶酚没食子酸酯、(-)-没食子儿茶酚没食子酸酯、(+)-表儿茶酚、(-)-表儿茶酚、(-)-表儿茶酚没食子酸酯、(-)-表没食子儿茶酚或(-)-表没食子儿茶酚没食子酸酯。
就本发明而言,黄酮和它的衍生物(经常也一起统称作“黄酮”)也是有利的活性化合物。其它有利的活性化合物是葡萄糖四羟基齐墩果烯酸酯(sericoside)、吡哆醇、维生素K、生物素和芳香物质。
优选活性化合物(一种或多种化合物)可非常有利地选自如下亲水性活性化合物:α-羟基酸,如乳酸或水杨酸或其盐,例如乳酸Na、乳酸Ca、TEA乳酸盐、脲、尿囊素、丝氨酸、山梨糖醇、甘油、奶蛋白、泛醇或壳聚糖。
最优选地,活性化合物选自UV-过滤剂、防痤疮活性物、抗衰老活性物、消炎剂、头发生长调节剂、对头发或毛囊起作用的试剂、防汗剂或除臭剂、增白剂、自晒黑剂和维生素。
a)UV-过滤剂
据研究所选渗透增强剂明显改进UV-过滤剂的增溶,并因此大大提高本发明化妆品组合物的UV保护性能。
辛酰丙氨酸乙酯具有令人关注的UV过滤剂增溶性能。已知的UV-过滤剂如乙基己基三嗪酮(Uvinul T150),与在己二酸二丁基酯中16重量%相比,在其他典型使用的溶剂中更好地增溶,例如23重量%,从而提高在溶剂中可得到的浓度。这可又对于设计具有改进的感官特性的配制剂是有益的。也可实现更均匀的分布和更好地渗透至角质层的上层。
此外,是颜料并在物理上起作用的UV过滤剂的UV保护作用也通过加入辛酰丙氨酸乙酯而改进。由于增强剂的优异铺展性能,这些种类的UV过滤剂在化妆品组合物和施用后在皮肤上具有改进的均匀分布。
因此,活性化合物(一种或多种化合物)还可非常有利地选自光过滤剂活性化合物。
合适的光过滤活性化合物为吸收在UV-B和/或UV-A范围的紫外线的物质。这些应理解为能够吸收紫外线并以长波辐射形式,如热量再次释放所吸收的能量的有机物质。有机物质可以是油溶性或水溶性的。合适的UV过滤剂例如为2,4,6-三芳基-1,3,5-三嗪,其中芳基在每种情况下可以带有至少一个取代基,其优选选自羟基,烷氧基,尤其是甲氧基,烷氧基羰基,尤其是甲氧基羰基和乙氧基羰基。此外合适的是对氨基苯甲酸酯,肉桂酸酯,二苯甲酮,樟脑衍生物和遮蔽紫外线的颜料如二氧化钛、滑石和氧化锌。特别优选基于二氧化钛的颜料。
可使用的油溶性UV-B过滤剂例如为如下物质:
3-亚苄基樟脑及其衍生物,如3-(4-甲基亚苄基)樟脑;4-氨基苯甲酸衍生物,优选4-(二甲氨基)苯甲酸2-乙基己酯、4-(二甲氨基)苯甲酸2-辛酯和4-(二甲氨基)苯甲酸戊酯;肉桂酸酯,优选4-甲氧基肉桂酸2-乙基己基酯、4-甲氧基肉桂酸丙基酯、4-甲氧基肉桂酸异戊基酯、4-甲氧基肉桂酸异戊基酯和2-氰基-3-苯基-肉桂酸2-乙基己基酯(2-氰基-3,3-二苯基丙烯酸-2-乙基己酯);水杨酸酯,优选水杨酸2-乙基己基酯、水杨酸4-异丙基苄基酯和5-甲基-2-(1-甲基乙基)环己醇2-氨基苯甲酸酯(salicylic acid homomenthylester);二苯甲酮衍生物,优选2-羟基-4-甲氧基二苯甲酮、2-羟基-4-甲氧基-4'-甲基二苯甲酮和2,2'-二羟基-4-甲氧基二苯甲酮;苄基丙二酸的酯,优选4-甲氧基苄基丙二酸二(2-乙基己基)酯;三嗪衍生物,如2,4,6-三苯胺基(对羰基-2'-乙基-1'-己基氧基)]-1,3,5-三嗪(辛基三嗪酮)和二辛基丁酰胺三嗪酮;丙烷-1,3-二酮,如1-(4-叔丁基苯基)-3-(4'-甲氧基苯基)丙烷-1,3-二酮。
可能的水溶性物质为:
·2-苯基苯并咪唑-5-磺酸及其碱金属盐、碱土金属盐、铵盐、烷基铵盐、链烷醇铵盐和葡糖铵(glucammonium)盐;
·二苯甲酮的磺酸衍生物,优选2-羟基-4-甲氧基二苯甲酮-5-磺酸及其盐;
·3-亚苯基樟脑的磺酸衍生物如4-(2-氧代-3-亚冰片基甲基)苯磺酸和2-甲基-5-(2-氧代-3-亚冰片基)磺酸及其盐。
特别优选使用肉桂酸酯,优选4-甲氧基肉桂酸2-乙基己基酯、4-甲氧基肉桂酸异戊基酯和2-氰基-3-苯基-肉桂酸2-乙基己基酯(2-氰基-3,3-二苯基丙烯酸-2-乙基己酯)。
此外,优选使用二苯甲酮衍生物,尤其是2-羟基-4-甲氧基二苯甲酮、2-羟基-4-甲氧基-4'-甲基二苯甲酮和2,2'-二羟基-4-甲氧基二苯甲酮,以及使用丙烷-1,3-二酮,如1-(4-叔丁基苯基)-3-(4'-甲氧基苯基)丙烷-1,3-二酮。
可能的典型UV-A过滤剂为:
·苯甲酰基甲烷衍生物,如1-(4'-叔丁基苯基)-3-(4'-甲氧基苯基)-丙烷-1,3-二酮、4-叔丁基-4'-甲氧基二苯甲酰基甲烷或1-苯基-3-(4'-异丙基苯基)-丙烷-1,3-二酮;
·二苯甲酮的氨基-羟基取代的衍生物,如N,N-二乙基氨基-羟基苯甲酰基-正己基-苯甲酸酯。
UV-A和UV-B过滤剂当然也可以混合物使用。
其他合适的UV过滤剂物质在下表中提及。
除上述两组主要防晒物质外,还可使用抗氧化剂类型的次要防晒剂,其阻断在UV辐射穿入皮肤时引发的光化学和细胞反应链。典型实例为UV引发的超氧化物歧化酶、过氧化氢酶、生育酚(维生素E)和抗坏血酸(维生素C)中的功能和/或结构改变。
另一组合适的活性物为消炎物质,其对由UV光损伤的皮肤具有有益作用。这类物质例如但不限于为红没药醇、植醇和植烷三醇和乙酰水杨酸。
所提及的可用于本发明组合物的活性化合物和活性化合物组合的列表当然不意欲限制。活性化合物可单独或彼此以任何所需组合使用。
在本发明组合物中的这类活性物(一种或多种化合物)的量基于组合物的总重量优选为0.001-30重量%,特别优选0.05-20重量%,特别是1-10重量%。
b)自晒黑剂和增白剂
此外,辛酰丙氨酸乙酯改进自晒黑剂的均匀性。由于加入渗透增强剂,自晒黑剂和增白剂可更加均匀地施用并导致均匀的皮肤晒黑或皮肤增白效果。
合适的自晒黑剂为吡唑啉-4,5-二酮衍生物、戊二醛、四氧嘧啶、茚三酮、4,4-二羟基吡唑啉-5-二酮和二羟基丙酮。优选与渗透增强剂一起使用的自晒黑剂为二羟基丙酮(DHA)。自晒黑剂的量基于化妆品组合物总重量为0.05-10重量百分数,优选0.1-5重量百分数。
通常,增白剂需要穿过皮肤以展现它们的功能,很多包含防止黑色素形成并因此必须对皮肤的黑色素细胞起作用的酪氨酸抑制剂。增白剂的实例为:熊果苷、阿魏酸、曲酸、香豆酸、植物提取物和抗坏血酸(维生素C)。
c)防痤疮活性物
防痤疮活性物如消炎剂、抗生素、类维生素A、抗菌和角质层分离剂通常引起不希望的副作用。因此,有利地是在皮肤上层、皮肤的皮脂腺细胞和/或毛孔中改进的渗透和分布,可减少这些活性物的剂量。
与渗透增强剂组合使用的防痤疮活性物选自α-羟基酸(AHA)(包括乙醇酸和乳酸)、β-羟基酸如水杨酸;过氧化苯甲酰;羟基喹啉;硫磺;抗生素如四环素、dapzone、多西环素、二甲胺四环素、红霉素、克林霉素;壬二酸;类维生素A;异维A酸;维生素A-衍生的局部类维生素A,其包括维A酸、异维A酸、莫维A胺、阿达帕林和他扎罗汀;烟酰胺、尿囊素和植物提取物。
d)抗衰老活性物
很多用作防痤疮活性物的角质层分离剂也称为抗衰老活性物。尤其是α-和β-羟基酸和类维生素A和视黄酸。
另一类抗衰老活性物包含维生素、蛋白质水解产物、多肽和改性多肽、β-葡聚糖和植物提取物。
e)维生素
根据本发明优选使用的维生素B组的维生素、维生素原或维生素前体,或其衍生物或2-呋喃酮的衍生物尤其包括:
维生素B1,俗名硫胺素,化学名3-[(4'-氨基-2'-甲基-5'-嘧啶基)甲基]-5-(2-羟乙基)-4-甲基噻唑氯化物。
维生素B2,俗名核黄素,化学名7,8-二甲基-10-(1-D-核糖基)-苯并[g]喋啶-2,4(3H,10H)-二酮。核黄素例如在乳清中以游离形式存在,且其它核黄素衍生物可从细菌和酵母中分离。根据本发明同样合适的核黄素立体异构体为可从鱼肉或肝脏分中分离且具有D-***糖基而不是D-核糖基的来苏黄素。
维生素B3。该名称通常用于化合物烟酸和烟酰胺。根据本发明优选烟酰胺。
维生素B5(泛酸和泛醇)。优选使用泛醇。根据本发明可使用的泛醇衍生物尤其为泛醇的酯和醚以及阳离子衍生泛醇。在本发明的另一优选实施方案中,除泛酸或泛醇外,也可使用2-呋喃酮的衍生物。特别优选的衍生物为市售物质二氢-3-羟基-4,4-二甲基-2(3H)-呋喃酮(Merck),其俗名为泛酰内酯,4-羟甲基丁内酯(Merck);3,3-二甲基-2-羟基丁内酯(Aldrich)和2,5-二氢-5-甲氧基-2-呋喃酮(Merck),其中明确包括所有立体异构体。
这些化合物有利地赋予本发明医学化妆品以补水和皮肤光滑性能。
维生素B6,其不应理解为同一物质,而是已知俗名为吡哆素、吡哆胺和吡哆醇的5-羟甲基-2-甲基吡啶-3-醇的衍生物。
维生素B7(生物素)也称为维生素H或“皮肤维生素”。生物素是(3aS,4S,6aR)-2-氧代六氢噻吩并[3,4-d]咪唑-4-戊酸。
根据本发明,特别优选的维生素为泛醇、泛酰内酯、烟酰胺和生物素。
f)头发调节剂
头发调节剂包括:
-诱导新头发周期生长,提高生长速率,或提高毛干的宽度的头发生长刺激剂;
-对头发起作用,如提高头发体积、头发光泽和头发强度和头发厚度的试剂;
-对毛囊起作用的试剂和
-头发生长抑制剂。
为了成为有效的头发调节剂,通常必须经表皮和透过毛囊渗透,直到毛囊根部,以使得渗透增强剂的加入直接提高头发调节剂的效用。
大多数头发调节剂为防止和减缓头发损失的头发生长刺激活性物。利用头发生长刺激活性物的药物处理通常涉及包括但不限制于米诺地尔、非那雄胺、度他雄胺、比卡鲁胺、氟他胺、***衍生物或孕烷衍生物的药物的使用。
其他用于化妆品组合物中的头发生长刺激剂为锌和锌盐、不饱和脂肪酸、原花青素低聚物、γ-亚麻酸、生物素、胎盘提取物、泛酸及其衍生物、***素如比马***素、甲基酰胺基二氢诺尔阿尔法***素(noralfaprosta)和/或他氟***素;镁、尿囊素、茶碱和植物提取物(包括但不限制于大麦、葡萄籽、苹果籽、锯棕榈、熊果、绿茶、蜂胶、刺五加根、松树皮的提取物)。
已知嘌呤和嘌呤衍生物减少头发损失。
已知的例如用于治疗头发的头皮循环促进剂包括但不限制于乙酰胆碱衍生物,烟酸衍生物,来自胡椒、人参、当药的植物提取物。
对毛囊起作用的合适试剂为牛磺酸和牛磺酸衍生物或L-肉碱或L-肉碱衍生物。
头发生长抑制剂主要用于化妆原因。它们包括但不限制于烟酰胺、噻唑烷酮衍生物、蛋白激酶C抑制剂、鸟氨酸脱羧基酶抑制剂、三羟基嘌呤的盐;大豆蛋白水解产物、脲、水杨酸、柳树提取物、金缕梅提取物、山金车提取物、金丝桃提取物、白柳提取物和作为(BASF BeautyCare Solutions)销售的薄荷醇的组合。
g)除臭或防汗剂
化妆品除臭剂抵消、掩饰或除去身体气味。由于皮肤细菌对顶泌汗液的作用并形成具有令人不愉悦的气味的降解产物而产生身体气味。因此,除臭剂包含充当抗微生物剂、气味吸收剂和/或酶抑制剂的活性成分。
合适的抗微生物剂一般为所有对***有效的物质,例如4-羟基苯甲酸及其盐和酯、N-(4-氯苯基)-N’-(3,4-二氯苯基)脲、2,4,4’-三氯-2’-羟基二苯基醚(三氯生)、4-氯-3,5-二甲基苯酚、2,2’-亚甲基双(6-溴-4-氯苯酚)、3-甲基-4-(1-甲基乙基)苯酚、2-苄基-4-氯苯酚、3-(4-氯苯氧基)-1,2-丙二醇、3-碘-2-丙基丁基氨基甲酸酯、氯己定、3,4,4’-三氯对称二苯脲(TTC)、抗菌芳香剂、百里香酚、百里香油、丁子香酚、丁子香油、薄荷醇、薄荷油、金合欢醇、苯氧基乙醇、甘油单癸酸酯、甘油单辛酸酯、甘油单月桂酸酯(GML)、双甘油单癸酸酯(DMC)、水杨酸N-烷基酰胺,例如N-辛基水杨酰胺或N-癸基水杨酰胺。
合适的酶抑制剂为例如酯酶抑制剂。这些优选为三烷基柠檬酸酯如三甲基柠檬酸酯、三丙基柠檬酸酯、三异丙基柠檬酸酯、三丁基柠檬酸酯,特别是三乙基柠檬酸酯(CAT)。这些物质抑制酶活性,从而减少气味的形成。其他适合酯酶抑制剂的物质为甾醇硫酸酯或磷酸酯,例如羊毛甾醇、胆甾醇、菜油甾醇、豆甾醇和谷甾醇的硫酸酯或磷酸酯,二羧酸及其酯,例如戊二酸、单乙基戊二酸酯、二乙基戊二酸酯、己二酸、单乙基己二酸酯、二乙基己二酸酯、丙二酸和二乙基丙二酸酯,羟基羧酸及其酯,例如柠檬酸、苹果酸、酒石酸或二乙基酒石酸酯,以及甘氨酸锌。
合适的气味吸收剂为能够吸收并基本保留形成气味的化合物的物质。它们降低单个组分的分压,因此也减少它们的扩散速率。重要的是,在该方法中,香气必须没有减少地保留。气味吸收剂对细菌无效。它们例如包含,作为主要组分的蓖麻油酸的复合锌盐或本领域技术人员作为“固香剂”已知的特殊中和大部分气味的芳香剂,例如岩蔷薇或苏合香或某些松香酸衍生物的提取物。气味遮蔽剂为芳香剂或芳香油,除了其作为气味遮蔽剂的功能之外,还给予除臭剂其各自的香调。可提及的芳香油例如为天然和合成的芳香剂的混合物。天然芳香剂为来自花、茎和叶、果实、果皮、根、木、香草和草、针状物和枝、树脂和香脂的提取物。动物原料也是合适的,例如麝猫香和海狸香。典型的合成芳香剂化合物为酯类、醚类、醛类、酮类、醇类和烃类产品。酯类芳香剂化合物例如为乙酸苄酯、乙酸对叔丁基环己基酯、乙酸芳樟酯、乙酸苯乙基酯、苯甲酸芳樟酯、甲酸苄酯、环己基丙酸烯丙基酯、丙酸苏合香酯和水杨酸苄酯。醚类例如包括苄基乙基醚,且醛类例如包括具有8-18个碳原子的线性链烷醛、柠檬醛、香茅醛、香茅氧基乙醛、仙客来醛、羟基香茅醛、铃兰醛和波洁红醛(bourgenonal),酮类例如包括紫罗兰酮和甲基柏木酮,醇类包括茴香脑、香茅醇、丁子香酚、异丁子香酚、香叶醇、芳樟醇、苯乙醇和松油醇,以及烃类主要包括萜类和香脂。然而,优选使用一起产生令人愉快的香调的不同芳香剂的混合物。大部分用作芳香组分的相对低挥发性的精油也适合作为芳香油,例如鼠尾草油、春黄菊油、丁子香油、蜂花油、薄荷油、肉桂叶油、椴树花油、刺柏油、岩兰油、乳香油、格蓬油、岩蔷薇油和杂薰衣草油。优选单独或混合使用如下物质:香柠檬油、二氢月桂烯醇、铃兰醛、新铃兰醛(lyral)、香茅醇、苯乙醇、己基肉桂醛、香叶醇、苄基丙酮、仙客来醛、芳樟醇、乙氧基甲氧基环十一烷(boisambrene forte)、龙涎呋喃(ambroxan)、吲哚、二氢茉莉酮酸甲酯(hedione)、檀香(sandelice)、柠檬油、橘子油、橙油、烯丙基戊基甘醇酸酯、女贞醛(cyclovertal)、杂熏衣草油、香紫苏油、突厥酮、波旁香叶油、水杨酸环己酯、龙涎香(iso-E-super)、Fixolide NP、橡苔(evernyl)、异甲基紫罗兰酮(iraldein gamma)、苯乙酸、乙酸香叶酯、乙酸苄酯、氧化玫瑰、多米亚(romillat)、依罗酯(irotyl)和2-叔丁基环己基乙基碳酸酯(floramat)。
防汗剂
防汗剂通过影响外泌汗腺的活性,从而中和腋下湿润和身体气味而减少汗液的形成。含水或无水的防汗剂配制剂通常包含收敛性的活性成分。
收敛性防汗剂活性成分主要为铝、锆或锌的盐。这些合适的防汗的活性成分为,例如氯化铝、水合氯化铝、水合二氯化铝(aluminiumdichlorohydrate)、倍半羟基氯化铝及其例如与1,2-丙二醇的复合物化合物、尿囊素羟基铝(aluminium hydroxyallantoinate)、酒石酸氯化铝、三氯羟铝锆、四氯羟铝锆、五氯羟铝锆及其例如与氨基酸如甘氨酸的复合物化合物。化妆品和/或药物组合物
本发明渗透增强剂用于化妆品或其他局部组合物,优选乳液型组合物,最优选辛酰丙氨酸乙酯在W/O型乳液中作为渗透增强剂使用。这些化妆品或其他局部组合物包含渗透增强剂与至少一种与其不同并选自化妆品活性化合物、乳化剂、表面活性剂、防腐剂、芳香油、增稠剂、头发聚合物、头发和皮肤调节剂、接枝聚合物、水溶性或水分散性含聚硅氧烷聚合物、凝胶剂、护理剂、着色剂、调色剂、染料、颜料、用于赋予稠度的试剂、润湿剂、再加油剂(re-oiling)、胶原、蛋白水解产物、脂质、抗氧化剂、消泡剂、抗静电物、柔润剂和软化剂的组分的组合。
抗氧化剂有利地选自氨基酸(如甘氨酸、组氨酸、酪氨酸、色氨酸)及其衍生物,咪唑(如尿刊酸)及其衍生物,肽如D,L-肌肽、D-肌肽、L-肌肽及其衍生物(如鹅肌肽),类胡萝卜素,胡萝卜素(如β-胡萝卜素、番茄红素)及其衍生物,绿原酸及其衍生物,硫辛酸及其衍生物(如二氢硫辛酸),金硫葡糖(aurothioglucose),丙硫氧嘧啶和其它硫醇(如硫氧还蛋白(thiorodoxin)、谷胱甘肽、半胱氨酸、胱氨酸、胱胺及其糖基、N-乙酰基、甲基、乙基、丙基、戊基、丁基和月桂基、棕榈酰基、油基、γ-亚油酸基、胆甾烯基和甘油基酯)及其盐,硫代二丙酸二月桂酯,硫代二丙酸二硬脂基酯,硫代二丙酸及其衍生物(酯、醚、肽、类脂、核苷酸、核苷及盐),以及非常低耐受剂量(如pmol至μmol/kg)的磺酰亚胺化合物(如丁硫堇磺酰亚胺,高半胱氨酸磺酰亚胺,丁硫堇砜,五-、六-、七硫堇磺酰亚胺),以及(金属)螯合剂(如α-羟基脂肪酸、棕榈酸、肌醇六磷酸、乳铁蛋白),α-羟基酸(如柠檬酸、乳酸、苹果酸),腐殖酸,胆汁酸、胆汁萃取物,胆红素,胆绿素,EDTA及其衍生物,不饱和脂肪酸及其衍生物(如γ-亚麻酸、亚油酸、油酸),叶酸及其衍生物,泛醌和泛醌醇及其衍生物,维生素C及衍生物(如抗坏血酸钠、棕榈酸抗坏血酸酯、抗坏血酸磷酸镁,乙酸抗坏血酸酯),生育酚及衍生物(如维生素E乙酸酯,生育酚三烯醇),维生素A及衍生物(维生素A棕榈酸酯),以及苯偶姻树脂的松柏基苯甲酸酯,芸香亭酸及其衍生物,α-糖基芸香苷,阿魏酸,亚糠基葡萄糖醇,肌肽,丁羟基甲苯,丁羟基茴香醚,去甲二氢愈创木树酯酸,去甲二氢愈创木酸,三羟基丙基苯基酮,尿酸及其衍生物,甘露糖及其衍生物,锌及其衍生物(如ZnO、ZnSO4),硒及其衍生物(如硒代甲硫氨酸),均二苯代乙烯及其衍生物(如均二苯代乙烯氧化物,反式均二苯代乙烯氧化物)。
辛酰丙氨酸乙酯的制备方法
辛酰丙氨酸乙酯(KE 4610)的制备为两步法:
步骤1:在水溶液中根据Schotten-Baumann方法用辛酰氯酰化丙氨酸。
在15℃下在4-5h的时间内将120kg(0.74kmol)辛酰氯加入66kg(0.74kmol)丙氨酸在100kg水和30kg乙醇中的剧烈搅拌的水溶液。通过持续加入20%NaOH(约140kg)而使pH值保持在11-12。温度不应超过25℃,pH值不应低于10.5。在完成辛酰氯的加料后,反应混合物在20-25℃和最小为9的pH下后反应约2h。
该混合物在搅拌下加热至70℃并保持1h,然后通过加入约80kg30%HCl水溶液而调整到pH为1.8-2.3。在停止搅拌器后,体系开始分离成盐水溶液和有机层,其包含85-90%辛酰丙氨酸、辛酸(水解产物)、乙醇和一些水。除去水相并在步骤2中进一步处理有机相(约205kg)。
步骤2:酯化和纯化
通过利用蒸馏除去水/乙醇,加入新鲜乙醇直到达到所需酯化程度(至少80-90%)(其可由GC-分析或通过测定剩余酸值控制)而使有机层经受酯化。然后使酯化混合物经受分馏。在至多105℃的温度和<1毫巴下除去低沸物水、乙醇和辛酸,最后产物可在137-140℃下在<1毫巴下蒸馏。为了得到高纯度的酯,通过加入部分量的苏打或NaOH而在蒸馏之前将混合物调整到pH=7,以使挥发性酸转化成不可蒸馏的盐。优选产物在蒸馏后具有<1的酸值。
渗透增强剂的功效与制备方法无关,使得技术人员已知的辛酰丙氨酸乙酯的其他制备方法是可能且合适的。
4.实施例
4.1直接施用于皮肤的增强剂的渗透研究(预孵化)
本研究的目标是测定三种测试物质(一种为最接近现有技术渗透增强剂)在化妆品配制剂中充当皮肤渗透增强剂的效力:
·二甲基异山梨糖醇(DMI),熟知的渗透增强剂-用于化妆品中
·渗透增强剂1(PE1)-辛酰丙氨酸乙酯
·渗透增强剂2(PE2)-最接近现有技术分子十二烷酰基丙氨酸乙酯
测试由渗透测试中专用的独立测试机构进行。配制剂1(W/O配制剂)为所用的配制剂且不包含渗透增强剂。将皮肤用所选的渗透增强剂(DMI、PE1和PE2)预孵化并在30min的孵化时间后由皮肤表面除去配制剂,并且施用掺有放射性标记的3H-咖啡因或3H-维生素E乙酸酯的配制剂1。
表1:实验装置:
研究了三种渗透增强剂对皮肤吸收并入w/o配制剂中的咖啡因和维生素E乙酸酯(分别是代表性的亲水性和亲油性化妆品活性物)的速率的影响。放射性标记的咖啡因和维生素E乙酸酯作为标记物使用。利用经切皮(dermatomized)的人体皮肤(厚度约500μm)进行体外皮肤渗透研究,时间为24h,重复三次。在四个采样时间(1、3、6和24h)对受体分隔区进行取样以筛选渗透促进作用。
测试化合物3H-咖啡因和3H-维生素E乙酸酯的经皮吸收通过测量受体介质中放射性标记的物质的量监测。测试化合物利用液体闪烁计数定量。在开始体外渗透实验前,证明对于两种同位素闪烁计数的线性度。
测试方法描述
材料与方法
表2:将配制剂1用作W/O配制剂(配制剂1):
根据欧盟委员会的SCCP指南,由外科手术切除的人体皮肤为适合模拟体内条件下化合物至和跨过人体皮肤的穿透和渗透过程的体外试验体系。
对于渗透研究,使用切皮成500±100μm厚度的一个供体的人体皮肤(女性腹部皮肤),并且测试进行三次。整个厚度的皮肤由皮肤活检制备并在-20℃下储存。根据OECD指南,在-20℃下储存至多466天的皮肤不会改变其渗透性。在融化之后立即使用该皮肤。避免重复冻融循环。
配制剂1(不含有渗透增强剂)掺有放射性标记的3H-咖啡因(比活:60Ci/mmol)和3H-维生素E乙酸酯(比活:50Ci/mmol)并作为对照直接施用到皮肤。放射性标记的试样制备如下:使配制剂1掺有放射性标记的3H-咖啡因或3H-维生素E乙酸酯,其分别导致2960000cpm/50μl或1264557cpm/50μl。将三种不同渗透增强剂(DMI、PE1和PE2)中的一种在施用放射性掺入的W/O配制剂之前施用到皮肤上。
Krebs Ringer缓冲液(KRB,pH=7.4)根据内标操作程序制备。对于3H-咖啡因,KRB用作受体介质。对于3H-维生素E乙酸酯,补充有2%牛血清白蛋白(BSA)的KRB用作受体介质。3H-咖啡因和3H-维生素E乙酸酯的溶液用于验证检测方法并用于评估线性度。
输送研究
在人体皮肤上,以测试和参照项的四倍测定进行渗透研究。对于输送研究,将经切皮的皮肤切有24mm直径的孔,并且对于每一试样在五个点上测量皮肤的厚度。随后,使皮肤片固定在圆柱形玻璃Franz池上,其可作为扩散室使用。下部(受体)室具有约12ml的体积,而上部(供体)室的体积可以变化。***皮肤,其中皮层面向下方,使得皮肤的角质层在最上方。
在施用配制剂之前,将渗透增强剂施用到并铺展在皮肤上(每个20μl)。使用该方法以避免由于渗透增强剂与化妆品组合物中的组分可能的相互作用而产生的作用。
将在室温下为固体的PE2(C12),在水浴(在35-40℃下)中温和熔化并作为液体施用。在孵化30min后,用棉球将液体渗透增强剂温和移除。在皮肤上固化的PE2的情况下,用钳子将固体膜移除。其后,将50μl的配制剂施用在皮肤表面。使受体介质在32℃下恒温并在400rpm的速率下连续搅拌。皮肤的扩散面积约为1.8cm2。在24小时的时间内监测通过皮肤至受体介质的渗透。在1、3、6和24小时之后的4个不同时间点,通过取出200μl的试样而对受体介质进行取样。在取出该体积的试样后,将受体介质利用预温热的KRB/KRB+2%BSA再次填充。考虑到通过取样引入稀释,对受体室中的活性成分浓度进行校正。将取出的试样与210μl或500μl的闪烁液在200rpm下混合至少1小时并且利用闪烁计数测量放射性。
以释放至受体介质的活性物[cpm cm-2]相对于时间绘图给出结果。通过线性回归,在未知的试样中活性成分的量利用相应校准计算。
结果
渗透性研究的结果总结于下表中。
表3:具有标准差(n=3)的24小时后3H-咖啡因的平均累积的输送、渗透系数和增强比的值。
使用PE1检测到最强的渗透增强作用。该配制剂的输送为不含有任何渗透增强剂的对照的约5倍高,并且明显高于DMI或PE2。
表4:具有标准差(n=3)的渗透性研究的24小时时3H-维生素E乙酸酯的平均累积的输送、渗透系数和增强比的值。
对于维生素E乙酸酯,可检测到更缓慢的输送。原因可能是该亲油性物质由配制剂的不足释放和/或结合到皮肤内的亲油结构。施用的渗透增强剂DMI和PE1在24h检测时间内仅显示轻微的渗透增强作用。然而PE2减少了维生素E乙酸酯的输送并实际上充当阻滞剂。与现有技术分子PE2(十二烷基丙氨酸乙酯)相比,PE1(辛酰丙氨酸乙酯)提高了1.5倍的渗透作用。
结论
对于并入w/o配制剂的亲水性物质咖啡因,最有效的渗透增强剂为PE1。DMI提高咖啡因输送约两倍,PE2提高咖啡因输送约3倍。
所使用的渗透增强剂没有显著提高并入相同w/o配制剂中的亲油性维生素E乙酸酯的输送。然而,辛酰丙氨酸乙酯作为渗透增强剂的使用与DMI或十二烷酰基丙氨酸乙酯相比仍然是有利的,因为其没有对亲油性分子维生素E乙酸酯的渗透显示阻滞作用。
4.2并入W/O配制剂(并入)的增强剂的渗透研究
当并入化妆品配制剂且不直接施用到皮肤时,所述研究使用三种充当皮肤渗透增强剂的测试物质在相似实验装置中部分重复:
·二甲基异山梨糖醇(DMI),熟知的渗透增强剂-用于化妆品中
·渗透增强剂1(PE1)-辛酰丙氨酸乙酯
·渗透增强剂2(PE2)-现有技术渗透增强剂Transcutol(Gattefossee),二甘醇单***
配制剂1(W/O配制剂)充当基础配制剂并充当不含有任何渗透增强剂的参照。这次,皮肤不用所选渗透增强剂(DMI、PE1和DGME)预孵化,而是将5%的各渗透增强剂并入配制剂1,并且使得到的配制剂再次掺入放射性标记的3H-咖啡因或3H-维生素E乙酸酯。
表5:包含渗透增强剂的W/O配制剂的组合物:
结果:
渗透性研究的结果总结于表6中。
表6:具有标准差(n=4)的渗透性研究24小时时3H-咖啡因的平均累积输送、渗透系数和增强比的值。
从不含和含有渗透增强剂的w/o配制剂中渗透
结论:
同样,如果将渗透增强剂并入W/O配制剂,则对于亲水性标记物化合物咖啡因,最有效的渗透增强剂为PE1。DMI导致略微降低的咖啡因输送,而DGME与不含任何增强剂的参照配制剂相比略微提高了输送。
Claims (15)
1.化妆品组合物,包含辛酰丙氨酸乙酯作为渗透增强剂。
2.根据权利要求1的化妆品组合物,其特征在于其基于总组合物包含0.1-90重量%辛酰丙氨酸乙酯。
3.根据权利要求1或2的化妆品组合物,其特征在于其为乳液组合物。
4.化妆品组合物,包含辛酰丙氨酸乙酯和至少一种活性剂。
5.根据权利要求4的化妆品组合物,其特征在于活性剂选自UV-过滤剂、防痤疮活性物、抗衰老活性物、消炎剂、头发生长调节剂、对头发或毛囊起作用的试剂、防汗剂或除臭剂、增白剂、自晒黑剂、多肽、寡肽、蛋白质、乙酰水杨酸、阿托品、甘菊环,氢化可的松及其衍生物,例如氢化可的松17-戊酸酯,维生素,尤其是B和D系列,特别是维生素B1、维生素B12、维生素D,维生素A及其衍生物,例如棕榈酸视黄酯,维生素E或其衍生物,例如生育酚乙酸酯,维生素C及其衍生物,例如抗坏血酸基葡糖苷,以及还有烟酰胺、泛醇、红没药醇表面麻醉剂,不饱和脂肪酸,例如必需脂肪酸(常称作维生素F),尤其是γ-亚麻酸、油酸、二十碳五烯酸、二十二碳六烯酸及其衍生物,氯霉素、咖啡因、***素、百里酚、樟脑、角鲨烯,植物和动物来源的提取物或其他产品,例如月见草油、琉璃苣油或角豆油、鱼油、鳕鱼肝油,以及还有神经酰胺和神经酰胺类化合物、乳香提取物、绿茶提取物、荷花提取物、甘草提取物、金缕梅、去屑活性化合物(例如二硫化硒、1-氧-2-巯基吡啶锌、吡罗克酮、醇胺、氯咪巴唑、羟甲辛吡酮、表面麻醉剂及其组合),以及络合的活性化合物,例如γ-米谷酚和钙盐如泛酸钙、氯化钙和乙酸钙的那些,NO合成酶抑制剂如硝基精氨酸;儿茶酚和儿茶酚的胆汁酸酯,包含儿茶酚或儿茶酚的胆汁酸酯的植物或植物部分的提取物,山茶科植物家族的叶子;多酚;黄酮及其衍生物;葡萄糖四羟基齐墩果烯酸酯、吡哆醇、维生素K、生物素和芳香物质;α-羟基酸如乳酸或水杨酸或其盐如乳酸Na、乳酸Ca或TEA乳酸盐;脲;尿囊素;丝氨酸;山梨糖醇;牛奶蛋白和泛醇。
6.根据权利要求4的化妆品组合物,其特征在于活性剂选自UV-过滤剂、防痤疮活性物、抗衰老活性物、消炎剂、头发调节剂、防汗剂或除臭剂、增白剂、自晒黑剂和维生素。
7.化妆品组合物,包含辛酰丙氨酸乙酯和至少一种UV-过滤剂。
8.化妆品组合物,包含辛酰丙氨酸乙酯和至少一种自晒黑剂或至少一种增白剂。
9.化妆品组合物,包含辛酰丙氨酸乙酯和至少一种防汗剂和/或除臭剂。
10.化妆品组合物,包含辛酰丙氨酸乙酯和至少一种防痤疮活性物和/或至少一种消炎活性物。
11.化妆品组合物,包含辛酰丙氨酸乙酯和至少一种抗衰老活性物。
12.化妆品组合物,包含辛酰丙氨酸乙酯和维生素。
13.化妆品组合物,包含辛酰丙氨酸乙酯和至少一种头发调节活性物。
14.辛酰丙氨酸乙酯作为药物和化妆品活性物质用渗透增强剂的用途。
15.通过局部施用包含辛酰丙氨酸乙酯的组合物而增强药物和化妆品活性物质的皮肤渗透的方法。
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