CN114096227B - 包含5-苄氨基水杨酸衍生物的化妆品组合物及其局部使用方法 - Google Patents
包含5-苄氨基水杨酸衍生物的化妆品组合物及其局部使用方法 Download PDFInfo
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- CN114096227B CN114096227B CN202080049650.9A CN202080049650A CN114096227B CN 114096227 B CN114096227 B CN 114096227B CN 202080049650 A CN202080049650 A CN 202080049650A CN 114096227 B CN114096227 B CN 114096227B
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/74—Biological properties of particular ingredients
- A61K2800/78—Enzyme modulators, e.g. Enzyme agonists
- A61K2800/782—Enzyme inhibitors; Enzyme antagonists
Abstract
本发明涉及包含化学式I所示的5‑苄氨基水杨酸化合物或其美容学上可接受的盐;以及适合局部施用的美容学上可接受的赋形剂的组合物。包含化学式I所示的5‑苄氨基水杨酸化合物或其美容学上可接受的盐可用于通过对皮肤的抗氧化、抗炎及美白作用来减少或改善人体皮肤老化。
Description
技术领域
本发明涉及用于抗炎、抗氧化、皮肤美白及抗老化的化妆品组合物,其包含5-苄氨基水杨酸衍生物或其美容学上可接受的盐。
本发明涉及包含5-苄氨基水杨酸衍生物或其美容学上可接受的盐;以及将适合局部施用的美容学上可接受的赋形剂的化妆品组合物应用于皮肤,以预防和减少作为皮肤老化和皮肤损伤的主要风险因素的氧化应激及炎症。
本发明涉及包含5-苄氨基水杨酸衍生物或其美容学上可接受的盐;以及将适合局部施用的美容学上可接受的赋形剂的化妆品组合物应用于皮肤,以改善包括皮肤粗糙、皱纹、色素沉着及干燥的皮肤老化现象。
背景技术
皮肤老化及损伤是由内源性(遗传、细胞代谢、激素及新陈代谢)和外源性(光照、污染、电离、辐射、化学物质及毒素)因素的复合作用引起的,并通过皮肤组织中的各种信号转导通路进行。这些因素不仅会影响皮肤的外观,还会引起各皮肤层中积累的结构和生理变化以及退行性变化,从而导致皮肤老化和损伤。随着皮肤老化,出现的主要特征有皱纹、粗糙、干燥和色素沉着病变等。
由活性氧(reactive oxygen species,ROS)诱导的氧化应激在内源性和外源性皮肤老化及损伤过程中起着重要作用。内源性老化是随着年龄的增长皮肤细胞活性逐渐降低而发生的,这是由皮肤细胞的新陈代谢过程中过量产生的活性氧等引起的。外源性老化是由紫外线(UV)引起的光老化、公害、微生物等外部环境因素引起的。众所周知,皮肤老化及损伤尤其是由紫外线被皮肤吸收时出现的活性氧产生的二次反应诱导的。另外,活性氧通过基质金属蛋白酶(matrix metalloproteases,MMPs)减少作为结缔组织成分的胶原蛋白合成并通过攻击皮肤纤维加速老化。
抗氧化剂长期以来被用于抗老化化妆品中。目前,作为抗氧化成分,市面上287种产品中86%使用生育酚及其衍生物,30%使用维生素C衍生物。即,有限地使用特定抗氧化剂作为抗氧化剂成分,因此需要开发具有经证实的抗氧化作用和稳定性的新型抗氧化剂。稳定性比α-生育酚高的α-生育酚乙酸酯(维生素E醋酸酯)曾被用作化妆品成分,但发现它会引起皮肤过敏或皮疹,对皮肤的效果也尚不清楚。维生素C(抗坏血酸盐)的抗老化效果已得到充分证明,但由于其皮肤渗透性低以及稳定性低,因此难以用作化妆品成分。维生素C衍生物已被开发并用作化妆品成分,但很少有结果表明它们被皮肤组织吸收并显示出效果。因此,发现具有稳定性和安全性的抗氧化剂对于延缓皮肤老化和维持细胞正常功能非常重要。因此,为了延缓皮肤老化和维持正常的细胞功能,开发具有稳定性和安全性的抗氧化物质尤为重要。
前列腺素E2(PGE2)是一种炎症介质,在与内源性和外源性老化因素相关的皮肤损伤中起重要作用。环氧化酶-2(cyclooxygenase-2,COX-2)是PGE2合成所需的一种酶,在成纤维细胞(fibroblast)和角质细胞(keratinocyte)中的表达随着内源性和外源性老化而增加。对于培养的成纤维细胞,用PGE2处理可使前胶原的量减少60%,而用COX-2抑制剂处理可使PGE2减少并使前胶原的量增加至两倍。另外,PGE2刺激黑素细胞树突(melanocytedendrite),该黑素细胞树突参与黑素体(melanosome)从皮肤到角质细胞的转移,因此抑制COX-2可以在紫外线刺激的角质细胞中防止色素沉着(pigmentation)。
据报道,代表性COX-2抑制剂水杨酸(salicylate)及其衍生物,如丁基辛醇水杨酸酯(Butyloctyl Salicylate)、辛酰水杨酸(Capryloyl Salicylic Acid)、异鲸蜡醇水杨酸酯(Isocetyl Salicylate)、水杨酸镁(Magnesium Salicylate)、水杨酸钠(SodiumSalicylate)、TEA-水杨酸酯(TEA-Salicylate),十三烷醇水杨酸酯(TridecylSalicylate)、水杨酸戊酯(Amyl Salicylate)、水杨酸己酯(Hexyl Salicylate)、异十三烷醇水杨酸酯(Isotridecyl Salicylate)等,在特定浓度下可安全用于化妆品中。然而,有报道称,当局部使用这些COX-2抑制剂时,会引起诸如皮肤干燥、红斑、刺激、感觉异常、瘙痒和肠胃失调等副作用,因此限制了作为化妆品成分的应用。
发明内容
技术问题
微粒体前列腺素E合酶-1(Microsomal prostaglandin E synthase-1,mPGES-1)是直接参与从PGH2(Prostaglandin H2)生成PGE2的最终步骤的酶,据报道,与现有的COX-2抑制剂不同,其抑制剂不会引起胃肠道和心血管损伤等副作用。mPGES-1的表达在70%的紫外线刺激皮肤组织和老年皮肤中有所增加。因此,能够预料到通过局部抑制皮肤组织中mPGES-1的活性,可以安全地得到抗炎和抗老化效果。
由此,本发明人试图利用具有抗氧化作用和mPGES-1抑制作用的化合物来制备可以安全地用于人体皮肤并且对皮肤具有抗老化作用的化妆品组合物。
本发明的目的在于提供一种能够减轻由老化、各种压力或公害等引起的皮肤刺激,并对皮肤具有抗氧化、抗炎、美白和抗老化作用的物质。
本发明的另一目的在于提供一种可以通过使用去除自由基和抑制微粒体mPGES-1活性的有效成分来提高皱纹改善和美白效果以及改善皮肤问题的化妆品组合物。
本发明旨在提供一种用于预防和减少人体皮肤老化过程中发生的氧化应激及炎症的化妆品组合物。
另外,本发明旨在提供一种用于预防和减轻人体皮肤老化的化妆品使用方法。
技术方案
本发明提供用于抗炎、抗氧化、皮肤美白及抗老化的化妆品组合物,其包含如下化学式I所示的5-苄氨基水杨酸衍生物或其美容学上可接受的盐。
[化学式I]
其中,
X为CO、SO2或(CH2)n,
R1为氢或C1-C6烷基,
R2为氢或C1-C6烷基,
R3为氢或C1-C5酰基,
R4为苯基、苯氧基、C6-C10芳基或C5-C10杂芳基,上述芳基或杂芳基可以被选自硝基(nitro)、卤素(halogen)、C1-C6烷基、C1-C6卤代烷基、C1-C5烷氧基以及C1-C5卤代烷氧基中的一个或多个取代基所取代,
n为1至5的整数。
本发明提供用于减少人体皮肤老化过程中发生的氧化应激及炎症的化妆品组合物,其包含上述化学式I所示的5-苄氨基水杨酸衍生物或其美容学上可接受的盐。
本发明提供用于改善人体皮肤老化的化妆品组合物的用途,该化妆品组合物包含上述化学式I所示的5-苄氨基水杨酸衍生物或其美容学上可接受的盐。
发明的效果
在本发明中,包含如下化学式I所示的5-苄氨基水杨酸衍生物或其美容学上可接受的盐具有减少人体皮肤老化过程中发生的氧化应激及炎症的效果。
当局部使用本发明的组合物时,具有皮肤组织的抗炎和抗氧化效果、美白效果以及减少皱纹等的老化改善效果。
附图说明
图1是用低温扫描电子显微镜(Cryo-SEM)确认纳米乳化组合物的颗粒的结果。
图2是用电泳光散射法(Electrophoretic light scattering,ELS)测量纳米乳化组合物的尺寸的结果。
图3是在临床上确认皮肤亮度改善效果的结果。
图4是在临床上确认皮肤黑色素改善效果的结果。
具体实施方式
本发明提供用于抗炎、抗氧化、皮肤美白及抗老化的化妆品组合物,其包含如下化学式I所示的5-苄氨基水杨酸衍生物或其美容学上可接受的盐。
[化学式I]
其中,
X为CO、SO2或(CH2)n,
R1为氢或C1-C6烷基,
R2为氢或C1-C6烷基,
R3为氢或C1-C5酰基,
R4为苯基、苯氧基、C6-C10芳基或C5-C10杂芳基,上述芳基或杂芳基可以被选自硝基(nitro)、卤素(halogen)、C1-C6烷基、C1-C6卤代烷基、C1-C5烷氧基以及C1-C5卤代烷氧基中的一个或多个取代基所取代,
n为1至5的整数。
本发明提供用于减少人体皮肤老化过程中发生的氧化应激及炎症的化妆品组合物,其包含上述化学式I所示的5-苄氨基水杨酸衍生物或其美容学上可接受的盐。
本发明人利用具有抗氧化作用和mPGES-1抑制作用的5-苄氨基水杨酸衍生物来制备可以安全地用于人体皮肤的化妆品组合物,并验证5-苄氨基水杨酸衍生物对人体皮肤是否具有抗老化效果,从而完成了本发明。
本发明的组合物由上述化学式I所示的5-苄氨基水杨酸衍生物或其美容学上可接受的盐组成。
在一实施方式中,上述化学式I所示的化合物中的X可以为(CH2)n。
在一实施方式中,上述化学式I所示的化合物中的R4可以为被选自未取代苯基或硝基(nitro)、卤素(halogen)、C1-C6烷基、C1-C6卤代烷基、C1-C5烷氧基以及C1-C5卤代烷氧基中的一个或多个取代基所取代的苯基。
在一实施方式中,上述化学式I所示的化合物中的R4可以为被选自硝基、卤素、C1-C6烷基、C1-C6卤代烷基、C1-C5烷氧基以及C1-C5卤代烷氧基中的一个或多个取代基所取代的C6-C10芳基。
作为5-苄氨基水杨酸衍生物的优选例,例如但不限于:2-羟基-5-苯乙基氨基苯甲酸(化合物1)、2-羟基-5-[2-(4-三氟甲基-苯基)-乙氨基]-苯甲酸(化合物2)、2-羟基-5-[2-(3-三氟甲基-苯基)-乙氨基]-苯甲酸(化合物3)、5-[2-(3,5-双-三氟甲基-苯基)-乙氨基]-2-羟基-苯甲酸(化合物4)、2-羟基-5-[2-(2-硝基-苯基)-乙氨基]-苯甲酸(化合物5)、5-[2-(4-氯-苯基)-乙氨基]-2-羟基-苯甲酸(化合物6)、5-[2-(3,4-二氟-苯基)-乙氨基]-2-羟基-苯甲酸(化合物7)、5-[2-(3,4-二氯-苯基)-乙氨基]-2-羟基-苯甲酸(化合物8)、5-[2-(4-氟-2-三氟甲基-苯基)-乙氨基]-2-羟基-苯甲酸(化合物9)、5-[2-(2-氟-4-三氟甲基-苯基)-乙氨基]-2-羟基-苯甲酸(化合物10)、2-羟基-5-[2-(4-甲氧基-苯基)-乙氨基]-苯甲酸(化合物11)、2-羟基-5-)-2-邻甲苯基-乙氨基)-苯甲酸(化合物12)、2-羟基-5-(3-苯基-丙氨基)-苯甲酸(化合物13)、2-羟基-5-[3-(4-三氟甲基-苯基)-丙氨基]-苯甲酸(化合物14)、5-[3-(4-氟-苯基)-丙氨基]-2-羟基-苯甲酸(化合物16)、2-羟基-5-(3-对甲苯基-丙氨基)-苯甲酸(化合物17)、2-乙酰氧基-5-[2-(4-三氟甲基-苯基)-乙氨基]-苯甲酸(化合物18)、5-[2-(2-氯-苯基)-乙氨基]-2-羟基-苯甲酸(化合物19)、5-苄氨基水杨酸(化合物20)、5-(4-硝基苄基)氨基水杨酸(化合物21)、5-(4-氯苄基)氨基水杨酸(化合物22)、5-(4-三氟甲基苄基)氨基水杨酸(化合物23)、5-(4-氟苄基)氨基水杨酸(化合物24)、5-(4-甲氧基苄基)氨基水杨酸(化合物25)、5-(4-五氟苄基)氨基水杨酸(化合物26)、5-(4-硝基苄基)氨基-2-羟乙基苯甲酸酯(化合物27)、5-(4-硝基苄基)-N-乙酰氨基-2-羟乙基苯甲酸酯(化合物28)、5-(4-硝基苄基)-N-乙酰氨基-2-羟乙基苯甲酸酯(化合物29)、5-(4-硝基苄基)氨基水杨酸(化合物30)、5-(4-硝基苯磺酰基)氨基水杨酸(化合物31)、5-[2-(4-硝基苯基)-乙基]氨基水杨酸(化合物32)以及5-[3-(4-硝基-苯基)-正丙基]氨基水杨酸(化合物33)。
在特定的优选实施方式中,化学式I所示的化合物为2-羟基-5-[2-(4-三氟甲基苯基)乙氨基]苯甲酸(TFM,化合物2)或其美容学上可接受的盐。
在一具体例中,上述化学式I所示的化合物可以为如下化学式II所示的化合物。
[化学式II]
本发明的5-苄氨基水杨酸衍生物或其美容学上可接受的盐可以通过各种公知方法制备,包括美国专利No.6573402中记载的反应式。
下面所描述的术语的定义可适用于术语本身的使用或与其他术语的组合。
“烷基”(包括卤代烷基的‘烷基’)或“烷烃”是完全饱和的直链或支链非芳香烃。典型地,直链或支链烷基具有1个至约20个碳原子,优选1个至约10个碳原子,除非另有定义。C1-C6直链或支链烷基也称为“低级烷基”。在一实施方式中,烷基是C1-C6烷基,更优选C1-C3烷基。更具体地,优选的烷基包括但不限于甲基、乙基、丙基、异丙基、丁基、仲丁基以及叔丁基。
另外,在整篇说明书、实施例和权利要求书中所使用的术语“烷基”(或“低级烷基”)旨在包括“未取代的烷基”和“取代的烷基”,“取代的烷基”具有烷基残基烃主链的一个或多个碳上的氢被取代的取代基。除非另有说明,否则这些取代基是卤素、羟基、羰基(羧基、烷氧基羰基、甲酰基或如烷基C(0)的酰基)、硫代羰基(例如,硫酯、硫代乙酸酯或硫代甲酸酯)、烷氧基、磷酰基、磷酸盐(phosphate)、膦酸盐(phosphonate)、次膦酸盐(phosphinate)、氨基、酰胺基、脒、亚胺、氰基、硝基、叠氮基、甲硅烷基醚、巯基、烷硫基、硫酸盐、磺酸盐、氨磺酰基、磺氨基、磺酰基、杂环基、芳烷基(aralkyl)或芳族或杂芳族残基。
本领域技术人员应理解,在合适的情况下,烃链中取代的残基其本身可以具有取代基。例如,取代的烷基可以包括醚、烷基硫醇、羰基(包括酮,醛,羧酸盐及酯)、-CF3、-CN、氨基、叠氮基、亚氨基、酰胺基、磷酰基(包括膦酸盐及次膦酸盐)、磺酰基(包括硫酸盐、磺酰氨基、氨磺酰基及磺酸盐)或甲硅烷基的取代和未取代形式作为取代基。作为一例,取代的烷基如下所述。环烷基可以进一步被烷基、烯基、烷氧基、烷硫基、氨基烷基、羰基-取代的烷基、-CF3以及-CN等取代。
当与诸如酰基、酰氧基、烷基、烯基、炔基或烷氧基等化学残基一起使用时,术语“Cx-Cy”意在包括在链中含有x个至y个碳的基团。例如,术语“Cx-Cy烷基”是指取代或未取代的饱和烃基,并且指在包括卤代烷基如三氟甲基、2,2,2-三氟乙基的链中含有x个至y个碳的直链烷基及支链烷基。对于C0烷基,基团在末端位置时代表氢,在内部时代表键。术语“C2烯基”及“C2-炔基”其长度和加增的取代基与以上记载的烷基相似,但分别表示含有一个或多个双键或三键的取代或未取代的不饱和脂肪族基团。
当与诸如酰基、酰氧基、烷基、烯基、炔基或烷氧基等化学残基一起使用时,“低级”意在包括在取代基中具有10个以下的非-氢原子的基团。优选为6个以下。例如,“低级烷基”是指含有10个以下,优选含有6个以下碳原子的烷基。在特定实施方式中,如本文所定义的酰基、酰氧基、烷基、烯基、炔基或烷氧基的取代基是低级酰基、低级酰氧基、低级烷基、低级烯基、低级炔基或低级烷氧基,无论它们是单独存在还是与其他取代基如羟烷基和芳烷基(在这种情况下,在计数烷基取代基中的碳原子时,不计数芳基中的原子)一起存在。
术语“烷酰基”或“酰基”是指HC(O)或烃基-C(O)-,优选地,烃基-C(0)-表示由烷基-C(0)-表示的基团。优选地,烷酰基是C2-C10烷酰基,更优选是C3-C6烷酰基。更具体地,优选的烷酰基包括但不限于乙酰基、丙酰基和环己烷羰基。
术语“烷氧基”(包括卤代烷氧基的‘烷氧基’)是指连接有氧的烷基,优选低级烷基。在一具体例中,优选地,烷氧基是C1-C5烷氧基,更优选是C1-C3烷氧基。更具体地,优选的烷氧基包括但不限于甲氧基、乙氧基及丙氧基。
术语“胺”及“氨基”是指本领域公知的未取代和取代的胺及其盐。例如,包括如下化学式III或化学式IV所示的胺基。
[化学式III]
-N(R5)2
[化学式IV]
-N(R5)3 +
R5独立地表示氢或烃基(hydrocarbyl group),或者两个R5与其所连接的N原子一起形成环结构中具有4个至8个原子的杂环。
如本文所用的术语“芳基”包括取代或未取代的芳族基团,其中环的每个原子是碳。优选地,该环是6元至10元环,更优选地是6元环。
如本文所用的术语“杂芳基”包括在环中包含一个或多个选自N、O和S的杂原子的取代或未取代的杂芳族基团。优选地,该环是5元至10元环。
术语“芳基”或“杂芳基”包括多环系统,其中两个以上碳在相邻的环上具有共同的两个以上环。此时,环中一个以上是芳族,其他环可以不是芳族,例如,环烷基、环烯基、芳基、杂芳基和/或杂环基。
本发明的芳基或杂芳基的例子可以包括:苯、萘、菲、苯酚、苯胺等。芳基的示例性取代基包括例如卤素、卤代烷基如三氟甲基、羟基、羰基(羧基、烷氧基羰基、甲酰基或酰基如烷基C(0))、烷氧基、磷酰基、膦酸酯基、次膦酸酯基、氨基、脒基、亚胺基、氰基、硝基、叠氮基、甲硅烷基醚、巯基、烷硫基、硫酸盐、磺酸盐、氨磺酰基、磺酰氨基、磺酰基、杂环基、芳烷基、芳族残基或杂芳族残基。
如本文所用的术语“卤代”及“卤素”是指卤素,包括氯、氟、溴及碘。
术语“取代的”是指具有取代主链的一个或多个碳原子上的氢的取代基。应当理解,“取代”或“取代的”包括这样的默认条件,即这种取代取决于取代的原子及取代基的允许的原子价,并且该取代例如产生不会自发发生的稳定的化合物。如本文所用的术语“取代的”旨在包括有机化合物的所有可接受的取代基。在广泛的方面,可接受的取代基包括有机化合物的非环状和环状、支链和直链、碳环和杂环、芳族和非芳族取代基。对于合适的有机化合物,可接受的取代基可以是一个或多个,在两个以上的情况下,它们可以相同或不同。出于本发明的目的,杂原子例如氮是氢取代基和/或满足杂原子的原子价的本文所述的任何取代基,例如卤素、卤代烷基、羟基、羰基(羧基、烷氧基羰基、甲酰基或酰基)、硫代羰基(硫酯、硫代乙酸酯)、膦酸酯、次膦酸酯、氨基、酰氨基、脒、亚胺、氰基、硝基、叠氮基、巯基、烷硫基、硫酸盐、磺酸盐、氨磺酰基、磺酰氨基、磺酰基、杂环基、芳烷基,或者芳族或杂芳族残基。本领域技术人员应理解,在合适的情况下,取代基其本身可以被取代。除非特别说明为“未取代”,否则本文提及的化学残基应理解为包括取代的变体。例如,“芳基”或残基默认包括取代和未取代的变体。
如本文所用的术语“美容学上可接受的盐”是指由酸或碱形成的无毒或几乎无毒的盐。当本发明的化合物为酸性时,本发明的化合物的碱加成盐可以通过将化合物的游离碱与足量的优选碱和合适的惰性溶剂反应来制备。美容学上可接受的碱加成盐包括但不限于由钠、钾、钙、铵、镁或有机氨基制备的盐。
当本发明的化合物为碱性时,化合物的游离碱可以与足量的优选酸和合适的惰性溶剂反应以制备化合物的酸加成盐。美容学上可接受的酸加成盐包括丙酸、异丁酸、草酸、苹果酸、丙二酸、苯甲酸、琥珀酸、辛二酸、富马酸、扁桃酸、邻苯二甲酸、苯磺酸、对甲苯磺酸、柠檬酸、酒石酸、甲磺酸、盐酸、溴酸(bromic acid)、硝酸、碳酸(carbonic acid)、一氢碳酸、磷酸、一氢磷酸、硫酸、一氢硫酸、碘化氢或亚磷酸(phosphorous acid)的盐。另外,本发明的美容学上可接受的盐包括但不限于氨基酸的盐,例如藻酸盐(arginate),以及有机酸的类似物,例如葡萄糖醛酸(gluculonic)或半乳糖醛酸(galacturonic)。
例如,作为本发明的优选一例的2-羟基-5-[2-(4-三氟甲基苯基)-乙氨基]-苯甲酸(化合物2)的美容学上可接受的盐通过以下反应方法制备,但本发明的范围不限于此。
<反应式1>
在上述反应式中,M是美容学上可接受的金属或碱性有机化合物,例如二乙胺、锂、钠或钾。
更具体地,二乙胺盐可以通过将化合物溶解于醇中,滴加二乙胺,搅拌混合物,真空蒸馏,加入醚使残留物结晶来制备。碱金属盐可以通过在溶剂如醇、丙酮或乙腈中用无机试剂如氢氧化锂、氢氧化钠或氢氧化钾制备优选盐,然后冷冻干燥来制备。另外,锂盐可以用乙酸锂制备,钠盐可以用2-乙基己烷钠或乙酸钠制备,钾盐可以用乙酸钾制备。
本发明的一些化合物可以是水合形式,也可以以溶剂化或非溶剂化形式存在。本发明的一些化合物以结晶形式或无定形形式存,并且以任何物理形式包括在本发明的范围内。另外,本发明的一些化合物可能含有一个或多个不对称碳原子或双键,因此以两种以上异构体形式存在,例如外消旋体、对映异构体、非对映异构体、几何异构体等。本发明包括这些化合物的单独异构体。
<组合物>
本发明还提供一种组合物,其可以包含上述化学式I所示的5-苄氨基水杨酸衍生物或其美容学上可接受的盐以及美容学上可接受的赋形剂或添加剂。上述化学式I所示的5-苄氨基水杨酸衍生物或其美容学上可接受的盐可以单独给药。在一具体例中,包含上述化学式I所示的化合物的组合物可包含适当的赋形剂、稀释剂等。
对于上述赋形剂或添加剂,只要是本领域化妆品组合物制备中使用的赋形剂或添加剂均可使用,优选地,可以举例例如神经酰胺、非离子表面活性剂、高级醇、胆固醇、酯油、丙二醇、β-谷甾醇以及植物油等。
在一具体例中,相对于组合物的总重量,本发明的化妆品组合物包含0.001重量百分比至1重量百分比,优选0.01重量百分比至0.1重量百分比,更优选0.02重量百分比至0.1重量百分比的化学式I所示的化合物或其美容学上可接受的盐,基于组合物的总重量。当以这种方式包含时,可以得到抗氧化、增强皮肤舒缓、抗炎、美白或改善皱纹的效果。
在一具体例中,为了提高皮肤吸收率并得到对皮肤的高效果,本发明的化妆品组合物可以以乳化成纳米尺寸的方式含有5-苄氨基水杨酸衍生物或其美容学上可接受的盐的纳米乳化化妆品组合物。
上述纳米乳化化妆品组合物在包含5-苄氨基水杨酸衍生物的基础上还包含甘油、三乙醇胺、乙二胺四乙酸三钠、二丙二醇、氢化卵磷脂、维生素、肽等作为水相成分,可以包含植物角鲨烷、苯基聚三甲基硅氧烷、环戊硅氧烷、辛酸十六烷基酯、绣线菊籽油、聚二甲基硅氧烷、生育酚乙酸酯、蜂蜡等作为油相成分。
上述纳米乳化化妆品组合物可以包含0.02~0.1重量百分比的化学式I所示的化合物、卵磷脂、30~60重量百分比的甘油、5~20重量百分比的聚甘油-10油酸酯、1~5重量百分比的1,2-己二醇、1~10重量百分比的氢化卵磷脂。
本发明的纳米乳化组合物的制备方法的描述如下,但不限于此。
在本发明中,为了使上述化学式I所示的化合物作为美容产品商品化,以最终化妆品组合物为基准,将含有0.02-0.1重量百分比的上述化学式I所示的化合物水溶液以及作为乳化剂的2-10重量百分比的氢化卵磷脂和5-15重量百分比的聚甘油的水相成分混合物在单独溶解槽中制备。此后,将化学式I所示的化合物的水溶液加入到含有卵磷脂和聚甘油的水相成分混合物中,并用均质混合机或桨叶式混合机预混合以获得初级预乳化组合物。将预乳化组合物置于微流化器中并在1000bar下二次乳化3次以制备含有化学式I所示的化合物的纳米乳化化妆品组合物。
本发明中用作乳化剂的卵磷脂(lecithin)是一种称为磷脂酰胆碱(phosphatidylcholine)的物质,是构成动物细胞膜系统的主要磷脂成分之一,其结构为甘油的一侧结合有亲水性成分如磷酸和胆碱等,另一侧结合有疏水性酰基,因此是具有表面活性的物质。此类卵磷脂与皮肤的脂质成分相似,具有高亲肤性,因此在化妆品透皮吸收过程中可以促进角质层的皮肤渗透性。
本发明的纳米乳化化妆品组合物构成平均粒径为100-150nM的细而均匀的颗粒。因此,当制备包含本发明的纳米乳化化妆品组合物的化妆品时,可以提供剂型品质优异、有效成分的透皮吸收率及皱纹改善和美白效果显著提高的化妆品。
包含化学式II所示的化合物的纳米乳化化妆品组合物使用甘油、聚甘油-10油酸酯、1,2-己二醇、氢化卵磷脂作为水相成分。
<功能性化妆品>
本发明提供包含上述组合物的功能性化妆品。本发明的化妆品可以商品化为美容产品并局部用于皮肤上。本发明的美容产品可以是用于面部或身体的浓缩精华、面膜、面霜、精华、护肤膏(balm)或凝胶的形式。
本发明的功能性化妆品可以用于抗氧化、增强皮肤舒缓、抗炎、美白或改善皱纹。为了上述效果,本发明的功能性化妆品可以包含0.0001重量百分比至0.1重量百分比的上述化学式I所示的化合物作为有效成分。
为了改善皱纹,本发明的化妆品可以在包含上述化学式I所示的5-苄氨基水杨酸衍生物或其美容学上可接受的盐的基础上还包含选自视黄醇、棕榈酸视黄酯、腺苷以及聚乙氧基化视黄酰胺中的至少一种。
为了美白,本发明的化妆品可以包含选自构树提取物、熊果苷、乙基抗坏血酸醚、油溶性甘草提取物、抗坏血酸葡萄糖苷、抗坏血酸磷酸镁、烟酰胺、α-红没药醇以及抗坏血酸四异棕榈酸酯中的至少一种。
本发明的化妆品可以以膏、凝胶、面霜、乳液、粉、固体皂、液体皂、洗发水、护发素、溶液、悬浮液、乳浊液、矿物化妆品、粉末香水、含表面活性剂或无表面活性剂的洁面乳、油、粉状粉底、乳液粉底、染发剂、蜡、柔肤水、滋养水、滋养霜、按摩霜、精华液、洁面霜、洁面泡沫、面膜、底霜、眼霜、香薰、软膏、洁面水、蜡粉底、喷雾中的任一种形式使用。
本发明还提供5-苄氨基水杨酸衍生物或其美容学上可接受的盐用于预防和减少人体皮肤老化过程中的氧化应激及炎症的用途。即,提供用于改善人体皮肤老化的化妆品组合物或包含上述组合物化妆品,其包含上述化学式I所示的5-苄氨基水杨酸衍生物或其美容学上可接受的盐。更具体地,包含5-苄氨基水杨酸衍生物或其美容学上可接受的盐的化妆品组合物或化妆品可以用于改善人体皮肤老化,包括皮肤纹理、皱纹、着色及干燥。
在一具体例中,本发明的组合物用于制备改善人体皮肤老化过程的化妆品。在一具体例中,本发明的组合物用于制备通过对氧化应激及炎症的药理抑制改善皮肤老化过程的化妆品。在一具体例中,本发明的组合物用于制备通过抑制氧化应激及前列腺素E2合成来改善皮肤老化过程的化妆品。在一具体例中,本发明的组合物用于制备通过抑制氧化应激及微粒体前列腺素E合酶-1来改善皮肤的化妆品。
在下文中,将详细说明实施例以使本领域技术人员能够理解本发明。然而,以下实施例是以说明为目的而提供的,并非旨在限制本发明的范围。总之,在不脱离本发明的精神和范围或牺牲所有物质优势的情况下,可以进行各种改变是显而易见的。
<实施例>
实施例1:对人体皮肤的安全性评价
通过对33人志愿者的贴片测试评价化合物2的安全性。此时,将用包含0.0544mg/ml的化合物2的组合物处理过的贴片贴在试验部位24小时后,取下贴片并标记该部位。1小时后,判断并记录反应性,24小时后,评价反应性和皮肤刺激指数,结果见表2和表3。皮肤反应程度的判断标准如下表1所示。
表1
符号 | 等级(Grade) | 判断标准 |
+ | 1 | 轻微红斑 |
++ | 2 | 红斑 |
+++ | 3 | 严重红斑伴有水肿 |
++++ | 4 | 严重红斑伴有水肿和小水疱 |
皮肤反应性是通过将33名受试者的评价值的平均值乘以25得到的,并将该值除以评价次数得到皮肤刺激指数。
参照皮肤刺激指数表(表1)判断试验物质的皮肤刺激程度。
表2
皮肤刺激指数 | 分类 |
0.00-0.25 | 非(无)刺激性 |
0.26-1.00 | 轻度刺激性 |
1.01-2.50 | 中度刺激性 |
2.51-4.00 | 重度刺激性 |
表3
参见上述表3,在使用化合物2期间,没有任何特别的皮肤不良反应的报告,皮肤科医生在医学检查中也未发现任何异常。
实施例2:制备纳米乳化组合物
为了提高化合物2的透皮吸收率,以最终化妆品组合物为基准,将0.05重量百分比的化合物、50重量百分比的甘油、10.00重量百分比的聚甘油-10油酸酯、2.00重量百分比的1,2-己二醇、5.00重量百分比的氢化卵磷脂以及水用均质混合机预混合,获得初级预乳化组合物,将其置于微流化器中并在1000bar下二次乳化3次,制备得到由平均粒径为100-150nM的细而均匀的颗粒构成的纳米乳化组合物。
通过低温扫描显微镜确认脂质体的形成,并利用电泳光散射法(Electrophoreticlight scattering,ELS)测量纳米乳化组合物的尺寸。结果分别如图1和图2所示。
实施例3:制备试验产品及对照产品
作为试验产品,制备包含0.064重量百分比的实施例2的纳米乳化组合物(化合物2为0.0032重量百分比)、30重量百分比的甘油、28.5重量百分比的蜗牛分泌物滤液、5.0重量百分比的丁二醇、3.0重量百分比的异戊二醇以及纯净水的浓缩精华。
作为对照产品,制备包含除本发明的纳米乳化组合物之外的其余成分的产品。
实施例4:临床上对皱纹和美白的改善效果
为了确认含有化合物2的浓缩精华的皱纹和美白效果,对22名30~55岁的健康韩国女性(以下简称“受试者”)进行测试。对上述受试者,每天早晚两次取适量的含有化合物2的浓缩精华(试验产品)沿皮肤纹理从脸部内侧包括眼周的皱纹向外侧涂抹并使皮肤吸收,连续涂抹2个月。
皱纹程度及着色程度的测定部位为受试者的眼周部位和脸颊部位,将面部的左右两侧分别指定为特定区域,在面部的一半涂抹试验产品,在另一半涂抹对照产品。为了测定皱纹及着色程度,让受试者在室温为20~25℃、湿度为40~60%的恒温恒湿条件的候诊室休息30分钟,使皮肤表面温度和湿度适应测定空间的环境,同时在休息期间限制水分的摄入。为了客观测定,由一名研究人员进行测定,并在使用产品前(访问1)、使用产品4周后(访问2)和8周后(访问3)对同一部位进行测定。
(1)皱纹改善效果
为了测定各受试者的皱纹改善效果,对应用试验产品和对照产品的部位制作使用产品前、使用4周后和8周后的皮肤仿品(replica),并利用能见度仪SV700(VisiometerSV700)(Courage_Khazaka electronic GmbH,Germany)和实施透明度轮廓分析(transparancy profilometry analysis)进行分析,皱纹参数使用R1、R2、R3、R4及R5(R1:皮肤粗糙度(Skin roughness),R2:最大粗糙度(Maximum roughness),R3:平均粗糙度(Average roughness),R4:平滑深度(Smoothness depth),R5:算术平均粗糙度(Arithmetic average roughness))。结果示于下表4和表5中。
表4
表5
在使用试验产品(含有化合物2的浓缩精华)的实施例中,皮肤皱纹参数R1、R2、R3以及R5显示出显著且明显的降低,R4显示出降低趋势,由此确认皮肤皱纹改善效果非常优异。
(2)美白效果
用光谱仪CM700-d(Spectrometer CM700-d)(Konica Minolta,Japan)3次测定皮肤亮度,然后取平均值作为皮肤亮度评价数据,用测定变量中的L*值评价皮肤亮度,用皮肤黑色素和血红素测试仪MX18(Mexameter MX18)(courage+Khazaka electronic Gmbh,Germany)测定皮肤黑色素。Mexameter是一种窄带反射分光光度计(Narrow-bandreflectance spectro-photometer),从探头(probe)发出568nm(绿色)、660nm(红色)、880nm(红外)的光来测定皮肤反射的光,单位为M.I(黑色素指数(Melanin Index))。结果示于图3和图4中。
在使用试验产品(含有化合物2的浓缩精华)的实施例中,表示皮肤亮度的L*值明显增加,M.I值降低,由此确认对皮肤美白的效果非常优异。
以下,示出在身体或脸部皮肤上局部使用的剂型化的本发明的化妆品的非限制性制备例。
制备例1:纳米乳化组合物
纳米乳化组合物的成分见表6。
表6
成分 |
化合物2 |
氢化卵磷脂(Hydrogenated Lecithin) |
水(Water) |
甘油(Glycerin) |
聚甘油-10油酸酯(Polyglyceryl-10Oleate) |
1,2-己二醇(1,2-Hexanediol) |
三氟甲基苯乙基美沙拉秦(Trifluoromethyl Phenethyl Mesalazine) |
制备例2:制备浓缩精华
用如下表7所示的成分制备浓缩精华。
表7
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制备例3:制备爽肤水
用如下表8所示的成分制备爽肤水。
表8
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制备例4:制备乳液
用如下表9所示的成分制备乳液。
表9
成分 |
化合物2 |
丁二醇 |
甘油 |
1,2-己二醇 |
甲基葡糖醇聚醚-20(Methylgluceth-20) |
三氟甲基苯乙基美沙拉秦 |
氢化卵磷脂 |
聚甘油-10油酸酯 |
透明质酸钠 |
积雪草(Centella Asiatica) |
甜菜碱 |
甘油聚醚-26 |
水解霍霍巴酯(Hydrolyzed Jojoba Esters) |
尿囊素 |
黄原胶(Xanthan Gum) |
丙烯酸酯/C10-30烷基丙烯酸酯交联聚合物 |
丙二醇(Propanediol) |
聚甘油-10月桂酸酯(Plyglyceryl-10Laurate) |
氨丁三醇(Tromethamine) |
乳香油(Boswellia Carterii Oil) |
水 |
制备例5:制备面膜片
用如下表10所示的成分制备面膜片。
表10
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产业上的可利用性
本发明的包含5-苄氨基水杨酸衍生物或其美容学上可接受的盐的用于抗炎、抗氧化、皮肤美白及抗老化的化妆品组合物可以用于化妆品的制备。
Claims (5)
1.一种用于抗炎、抗氧化、皮肤美白及抗老化的化妆品组合物,其包含2-羟基-5-[2-(4-三氟甲基-苯基)-乙氨基]-苯甲酸,其特征在于,
化妆品组合物为纳米乳化化妆品组合物,所述纳米乳化化妆品组合物包含0.02~0.1重量百分比的2-羟基-5-[2-(4-三氟甲基-苯基)-乙氨基]-苯甲酸、卵磷脂、30~60重量百分比的甘油、5~20重量百分比的聚甘油-10油酸酯、1~5重量百分比的1,2-己二醇和1~10重量百分比的氢化卵磷脂。
2.一种功能性化妆品,其特征在于,包含权利要求1的化妆品组合物。
3.根据权利要求2所述的化妆品,其特征在于,为了改善皱纹,包含选自视黄醇、棕榈酸视黄酯、腺苷以及聚乙氧基化视黄酰胺中的至少一种。
4.根据权利要求2所述的化妆品,其特征在于,为了美白,包含选自构树提取物、熊果苷、乙基抗坏血酸醚、油溶性甘草提取物、抗坏血酸葡萄糖苷、抗坏血酸磷酸镁、烟酰胺、α-红没药醇以及抗坏血酸四异棕榈酸酯中的至少一种。
5.根据权利要求2所述的化妆品,其特征在于,上述功能性化妆品以凝胶、固体皂、液体皂、洗发水、护发素、悬浮液、乳浊液、矿物化妆品、粉末香水、含表面活性剂或无表面活性剂的洁面乳、油、粉状粉底、乳液粉底、染发剂、柔肤水、滋养水、滋养霜、按摩霜、精华液、洁面霜、洁面泡沫、面膜、底霜、眼霜、香薰、软膏、洁面水、蜡粉底、喷雾中的一种形式使用。
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JP2004137212A (ja) * | 2002-10-18 | 2004-05-13 | Noevir Co Ltd | 水性スティック状化粧料 |
CN102316863A (zh) * | 2009-02-09 | 2012-01-11 | 纽若泰克制药株式会社 | 5-苄基氨基水杨酸衍生物或其盐的医药用途 |
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US3632760A (en) * | 1969-06-25 | 1972-01-04 | Merck & Co Inc | Treatment of inflammation |
JP2004137212A (ja) * | 2002-10-18 | 2004-05-13 | Noevir Co Ltd | 水性スティック状化粧料 |
CN102316863A (zh) * | 2009-02-09 | 2012-01-11 | 纽若泰克制药株式会社 | 5-苄基氨基水杨酸衍生物或其盐的医药用途 |
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