CN101683310A - 作为化妆品和药物活性化合物的邻氨基苯甲酰胺及其衍生物 - Google Patents
作为化妆品和药物活性化合物的邻氨基苯甲酰胺及其衍生物 Download PDFInfo
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- CN101683310A CN101683310A CN200910173877A CN200910173877A CN101683310A CN 101683310 A CN101683310 A CN 101683310A CN 200910173877 A CN200910173877 A CN 200910173877A CN 200910173877 A CN200910173877 A CN 200910173877A CN 101683310 A CN101683310 A CN 101683310A
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- acid
- chemical compound
- polyethylene glycol
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- acyloxy
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Abstract
本发明涉及作为化妆品和药物活性化合物的邻氨基苯甲酰胺及其衍生物。公开了通式1的特定化合物(以及相应的混合物)的用途,尤其是作为用于抑制由P物质诱导的来自肥大细胞的组胺释放的化妆品试剂的用途。
Description
[1]本申请是2003年11月20日提交的申请号为200380104016.7(PCT/EP2003/012990)之申请的分案申请。
[2]本发明涉及通式1的化合物或者两种或多种不同的通式1化合物的混合物的特定用途。
本发明还涉及迄今未知的通式1的被选化合物。
本发明的第一方面涉及通式1的化合物或者通式1的两种或多种不同化合物的混合物用作抑制由P物质诱导的、来自肥大细胞的组胺释放的化妆品制剂或者用作制备抑制由P物质诱导的、来自肥大细胞的组胺释放的药物。
本文中,下述内容适用于通式1的化合物和所述混合物中的通式1的任一种化合物:
m=0,1,2或3,
p=0,1或2,
n=0,1或2,
附带条件是当n=1或2时,p+m>0,
其中,当n=1或2时,在每种情况下都成对的R1和R2在每种情况下都表示H或者共同表示另一个化学键(例如在肉桂酸的衍生物中);
其中,当m=1,2或3时,其它独立的每个X表示OH、烷氧基或酰氧基,
其中,当p=1或2时,其它独立的每个Y表示OH、烷氧基或酰氧基,
附带条件是当p+m>0时,X或Y至少有一次选自OH和酰氧基;
R3=H或者烷基(尤其是-CH3,以及具有2-30个碳原子的直链或支化烷基链)。
本文中,R3=H也适合于相应的药学上可接受的物质组(原文如此),。
本文中,通式1的化合物可以是任意的异构体或异构体混合物的形式,例如对于n=1且R1,R2=其他化学键时,其为顺式或反式异构体的形式。
对于X或Y=酰氧基,优选地:酰基=CO-R,其中R=-CH3,或者具有2-30个碳原子的直链或者支化烷基自由基。
由于在相应的刺激之后,肥大细胞释放的介质例如组胺,在很大程度上导致例如发痒(痒症)、疼痛或者变红反应的症状,因此肥大细胞在过敏和发炎过程中发挥重要作用。大量研究已经能够表明由皮肤中的神经末梢释放的神经肽P物质会引起肥大细胞的脱粒。因此,P物质被认为是周围神经系统和症状例如发炎过程,发痒和疼痛的最重要的联系纽带之一。
在药物和化妆品工业中,日益需要组胺释放抑制剂。高浓度组胺的非控制释放伴随着例如发痒、疼痛或者变红反应的症状。尤其对于荨麻疹(风疹),已经确定了组胺释放和严重发痒之间的明确相关性。术语荨麻疹历史上来源于皮肤在接触大荨麻(拉丁名称:Urtica dioica L.)之后所观察到的症状(发痒、灼烧感和伤痕的扩展)。在这一特殊的情况中,其中起作用的是已经含在大荨麻中且储存在其特殊的分泌器官中并且在接触皮肤之后通过所谓的螫毛被注射到皮肤中的组胺,所述螫毛具有注射针的形式。结果是变红、发痒和伤痕的扩展。
各种形式的荨麻疹的一个共同特征是特殊类型的细胞即所谓肥大细胞的活化。肥大细胞还可以被称作人体的“消防队”或者“边境警察”。尤其常常发现肥大细胞位于人体与环境直接接触的部位,即皮肤,以及肠胃道和呼吸道的粘膜中。由各种介质导致的肥大细胞的活化(免疫球蛋白例如1gE或者神经肽例如P物质)可以伴随有严重的发炎反应、发痒和直至过敏性休克的严重过敏反应。为此,肥大细胞产生多种产物,包括组胺。这些产物由储存血管中的细胞即所谓的颗粒细胞所存储,并且一旦活化就被大量地释放到皮肤中。相反,——在此组胺具有特别重要的作用——这导致血管在相关皮肤位置变成“泄漏的”并且血液组分(主要是流体)渗入组织。结果产生伤痕。而且,发生血管扩张(血管舒张)。因此,血液更大程度地充满相关皮肤区域,导致变红。对于发痒的产生解释如下:一方面,从肥大细胞中释放组胺直接导致发痒。另一方面,组胺和其他肥大细胞产物刺激皮肤中的神经纤维。这种刺激此时导致神经纤维释放引起发痒的物质(所谓的神经肽)。反过来,这些神经肽(例如P物质)是良好的肥大细胞激活剂,从而肥大细胞刺激神经导致神经刺激肥大细胞。在皮肤和粘膜中,肥大细胞优选位于血管和神经直接相邻的位置。因而,难怪“相邻”肥大细胞、血管和神经纤维之间的联系能够非常好地发挥作用。
部分归因于肥大细胞释放高浓度组胺的发痒,能够引起各种疾病。这些疾病主要包括过敏性皮肤反应(食物过敏、化学物质)、痒症(风疹)、与植物(例如大荨麻)接触、昆虫叮咬、牛皮癣、感染和轻微烧伤、损伤愈合、肉体刺激,例如热或机械摩擦和镍过敏。
令人惊喜地是,在申请人进行的广泛研究中,已经发现上述通式1的化合物和两种或多种不同的通式1化合物的混合物非常适合用来抑制由P物质诱导的、来自肥大细胞的组胺释放。后面以实施例和表格的形式总结了所选研究结果。
在可根据本发明使用的通式1的化合物中,特定的分组和单个物质尤其适合用来抑制由P物质诱导的、来自肥大细胞的组胺释放。这些优选的分组和单个物质可见于从属权利要求、后面的实施例和相关表格。
根据本发明的第二方面,已经惊喜地发现通式1的化合物或两种或多种不同的通式1化合物的混合物不仅可用于抑制由P物质诱导的、来自肥大细胞的组胺释放,而且更一般地可用于治疗或预防发痒(痒症)、皮肤变红、伤痕扩展和/或过敏性皮肤反应(以及适用于制备相应的药物)。
通常,上述适合根据本发明用来抑制由P物质诱导的、来自肥大细胞的组胺释放的通式1化合物确实还可以用于治疗或预防发痒(痒症)、皮肤变红、伤痕扩展和/或过敏性皮肤反应的更一般的目的。
但是,同样在此范围内,优选的通式1的特定化合物可见于从属权利要求、实施例和相关表格。
本文中,指出了发痒不仅与上述机理有关,还与干性皮肤、老年性皮肤、受机械或化学刺激的皮肤,或者受日光刺激的皮肤有关。而且,心理因素例如焦虑或者紧张会引起发痒。对皮肤造成严重刺激的肥皂、清洁剂和溶剂会导致水合脂膜(hydrolipid film)被破坏并且结果导致发痒反应。发痒还会在创伤或烧伤(例如在刮伤或者晒伤后)愈合过程中发生,以至于这里使用预防或者缓解发痒的化妆品配方也能够有助于保护皮肤的最佳生理条件。而且,存在大量可用在老化皮肤上的化妆品。虽然没有详细阐述发痒和变红反应的基本生化过程,但是发现在这里组胺也具有重要作用。
因此容易理解在药物和化妆品工业中,对于发现抑制从肥大细胞释放组胺和/或能够用于治疗或预防发痒、皮肤变红、伤痕扩展或过敏性皮肤反应的活性化合物相当关注。
根据本发明的通式1的化合物或两种或多种不同的通式1化合物的混合物可以为植物提取物的组分的形式,如果需要可对该植物提取物进行后处理。特别地,如果需要已经进行后处理的植物提取物可以是来自燕麦类属、石竹类属、蝇子草类属或者女娄菜类属的植物的提取物,特别是燕麦提取物或康乃馨提取物。
如果对植物提取物进行了后处理,则优选保证相比于未经后处理的提取物,一种或多种通式1的化合物的比例相对于其他被提取组分的比例增加。
虽然不是在所有情况下均需要进行分离与纯化,但在某些情况下使用经分离和纯化的通式1的化合物或经分离和纯化的两种或多种不同的通式1化合物的混合物对于所述指定用途是有利的。来自植物提取物的通式1化合物或者相应混合物的分离和纯化被认为是后处理,其中通式1的化合物的比例相对于其他被提取组分的比例增加。
最后,根据另一方面,本发明还涉及可用于指定目的且迄今未知的选定的通式1的化合物。根据本发明的这些新型化合物可见于所附表格。
关于现有技术,给出以下内容:
其中,下述治疗措施已知用于缓解略微明显的发痒:含有大豆油(Balneumhermal)、液体石蜡(oleatum fat)或者γ-亚麻酸(linola fat油浴)的药用油浴、护肤霜(洗剂形式的水/油乳液),例如Bepanthenol Roche Lotion F或Eucerin cum aqua、含有杏仁或荷荷芭油的护肤油,以及含有保湿因子例如尿素或水杨酸的制剂。对于非常明显的皮疹/伤痕,例如使用含有类固醇的外用试剂。
具有缓解发痒的活性的活性化合物包括例如chromogycate二钠、戊脉安、酮替芬或曲尼司特,所述活性是基于有目的地抑制介质诱导的、来自肥大细胞的组胺释放。已知商品名为曲尼司特(Tranilast)的物质是N-(3,4-二甲氧基-肉桂酰基)邻氨基苯甲酸,它是一种出现在中国药用植物南天竹(Nandina domestica)中的天然邻氨基苯甲酰胺,但是它并没有落入通式1的范围内。
在多份专利和出版物中报道了在过敏反应例如支气管哮喘、过敏性鼻炎、过敏性结膜炎、食物过敏、荨麻疹或者异位性皮肤炎中使用曲尼司特的可能性(DE 2402398;EP 0074725;US 4070484;H.Shioda等人,Allergy 34,213-119(1979);M.Kojima等人,Oyo Yakuri 28(4),623-628(1984),Azuma等人,Br.J.Pharmacol.第58卷,第483-488页,(1976);Koda等人,Int.Archs.Allergy appl.Immun.第77卷,第244-245页,(1985);Komatsu等人,Japan J.ofPharmacol.第46卷,第43-51页,(1988);Hachisuka等人,Arch.Dermatol.Res.第280卷,第158-162页,(1988))。
如Komatsu等人所报道的,曲尼司特抑制抗原(DNP蛔虫;具有2,4-二硝基苯基-专一性的1gE抗体)诱导的、来自肥大细胞的、浓度为10-3-10-5M的组胺释放。在浓度约为10-4M时能够实现50%的组胺释放抑制率。另一方面,该公开中没有描述其他邻氨基苯甲酰胺对抑制来自肥大细胞的组胺释放的影响。
Hachisuka等人(Arch.Dermatol.Res.第280卷,第158-162页,(1988))研究了各种活性化合物对抑制P物质诱导的、来自肥大细胞的组胺释放的影响。这里,对比了chromogycate二钠(原文如此)、酮替芬和曲尼司特的活性。仅在约为10-3M的相对高浓度下,能够实现对P物质诱导的组胺释放的50%的抑制率。对于分子量为327的曲尼司特,10-3M对应于327μg/ml或327ppm的浓度。一种已知的抗过敏试剂DSCG(chromogycate二钠)的值位于同等的浓度范围(在10-3M下41%的抑制率)。在该研究工作范围内,对其他邻氨基苯甲酰胺没有更详细地研究。
Kojima Masami等人(Oyo Yakuri 28(4),623-628(1984)描述了其他邻氨基苯甲酰胺,例如在4-位去甲基化的曲尼司特(N-(3-甲氧基,(原文如此)4-羟基肉桂酰基)邻氨基苯甲酸)的抗过敏作用,但是据称该物质仅具有等同于曲尼司特的抑制效果。
在US 4,070,484中,描述了以200mg/kg的剂量口服单取代的N-(4-羟基肉桂酰基)邻氨基苯甲酸,实现了对鼠肥大细胞的抗原诱导破坏的36.7%的抑制率,与其对比,在相同的实验条件下,相应的(二甲基化)曲尼司特(N-(3,4-二甲氧基肉桂酰基)邻氨基苯甲酸)显示了更高的抑制率,即46.1%。该文件中没有提供与由P物质诱导的、来自肥大细胞的组胺释放抑制明确相关的对比数值。
邻氨基苯甲酰胺被描述为特定植物例如燕麦(Avena sativa)或者康乃馨(Dianthussp.)的组分。燕麦的燕麦蒽酰胺(avenanthramides)是由非取代或取代的邻氨基苯甲酸的部分结构和非取代或取代的肉桂酸的部分结构组成的酰胺,而另一方面,康乃馨种属中的酰胺基本上由邻氨基苯甲酸的部分结构和苯甲酸的部分结构组成。植物生理研究表明所谓燕麦的燕麦蒽酰胺和所谓康乃馨中的dianthramides都起到植物抗毒素的作用并且由于部分防御机理由微生物感染后的植物形成。
在民间医药中长久以来就已知使用燕麦提取物来缓解发痒,并且在下述文献中提及:Hagers Handbuch der Pharmazeutischen Praxis,第4卷,由K.Keller、H.Rimpler、G.Schneider发表,Springer Verlag,Berlin,1992,第437-446页;US FederalRegister October 3/1989;54,190 proposed rules,pp 40808-40811;Bundesanzeiger No.193,15.10.1987。在更近期的出版物中已经描述了使用富含邻氨基苯甲酰胺的特定酵母提取物级分来缓解发痒和皮肤变红(J.Vollhardt等人,Proceedings of the XXIst IFSCCIntemational Congress,Berlin,Sept.11-14,2000,395页;Verlag für Chemische Industrie,H.Ziolkowsky GmbH Augsburg Germany)。但是,该出版物没有报道来自含有超过30种物质的所谓燕麦的燕麦蒽酰胺中的哪种邻氨基苯甲酰胺或者哪些邻氨基苯甲酰胺参与了变红反应和发痒的缓解。
本发明基于广泛研究,尤其基于以下方面:
-对于具有缓解变红和发痒作用的邻氨基苯甲酰胺的鉴定的结构/活性考虑。
-制备具有高浓度特异性的、高效的邻氨基苯甲酰胺的植物提取物,特别是制备特定的燕麦和康乃馨提取物级分以及特别是由燕麦和/或康乃馨制备纯化分离的活性化合物。
-合成具有缓解发痒作用的邻氨基苯甲酰胺。
所述研究的目的是能够以优选高纯形式获得特殊活性的化合物,以使其可以用在不含任何毒理学上或者皮肤病学上关键的辅助组分(合成副产物或植物提取的辅助组分)的药物或化妆品中。
一般来说,应当牢记在化妆品和/或药物产品中使用的物质应当是:
-毒理学上可接受的,
-皮肤对其有良好耐受性的,
-稳定的(尤其在常规化妆品和/或药物配方中),
-优选无嗅的,以及
-能够廉价生产的(即使用标准工艺和/或从标准前体开始)处于与活性相关的浓度范围内。
根据本发明的用途和本发明化合物的优选实施方案可见于下面的实施例和相关表格:
1.合成通式1的邻氨基苯甲酰胺
实施例1
合成在核内非取代或取代的肉桂酰邻氨基苯甲酸衍生物,以N-(4-羟基肉桂酰基)邻氨基苯甲酸(燕麦蒽酰胺D,10;参见表1a)为例
燕麦蒽酰胺D(10)
将15g(91mmol)4-羟基肉桂酸、50ml乙酸酐和0.5ml嘧啶在室温下搅拌20小时。将该混合物倒入冰水中,分离出沉淀的4-乙酰氧基肉桂酸并干燥(18g)。最初加入15g(77mmol)4-乙酰氧基肉桂酸并滴加15g(100mmol)亚硫酰氯。然后在回流下搅拌该混合物1小时,通过蒸馏分离出过量的亚硫酰氯,并将50ml甲苯加入该酰氯中。加入7g(51mmol)邻氨基苯甲酸在70ml嘧啶中形成的溶液并在90℃下搅拌该反应混合物2小时。冷却后,将反应混合物倒入冰水中并用乙酸乙酯萃取,有机相水洗直至中性,真空下除去溶剂。将300g 10%的氢氧化钠溶液加入残余物中,在回流下搅拌该混合物1-2小时。冷却后,用浓盐酸酸化该混合物,并用乙酸乙酯萃取,有机相水洗直至中性,真空下除去溶剂。通过伴随加热反复在乙醇中溶解并加入水来冷却和沉淀从而重结晶粗产物(23g),进一步使用RP-18中压色谱仪(柱:YMC ODS-AQ,洗脱液:甲醇/水50∶50+0.5ml乙酸/l,λ280nm)来纯化(产量:1.1g 10,纯度:95%)。
光谱数据:1H-MNR(300MHz,D6丙酮):8.91(1H,dd,J=1.2和8.5Hz),8.14(1H,dd,J=1.7和8.1Hz),7.67(1H,d,J=15.4Hz),7.61(1H,m),7.60(2H,d,J=8.7Hz),7.16(1H,m),6.92(2H,d,J=8.7Hz),6.64(1H,d,J=15.4Hz)。-13C-NMR(75.5MHz,D6丙酮):170.5(s),165.3(s),160.2(s),143.3(s),142.7(d),135.2(d),132.2(d),130.8(2C,d),127.3(s),123.0(d),120.9(d),119.8(d),116.6(2C,d),115.8(s)。
实施例2
核内非取代或取代肉桂酰邻氨基苯甲酸衍生物的催化加氢产生相应的二氢化合物(8,表1a),以N-(4-羟基肉桂酰基)邻氨基苯甲酸(燕麦蒽酰胺D,10)为例。
二氢燕麦蒽酰胺D(8)
将140mg N-(4-羟基肉桂酰基)邻氨基苯甲酸(燕麦蒽酰胺D,10)溶解在20ml乙醇中,在钯(5%在活性碳上)的存在下用氢气使其定量氢化。
光谱数据:1H-MNR(300MHz,D6丙酮):8.68(1H,dd,J=0.8和8.4Hz),8.08(1H,dd,J=1.5和7.8Hz),7.59(1H,m),7.15(1H,m),7.12(2H,d,J=8.5Hz),6.77(2H,d,J=8.5Hz),2.95(2H,t,J=7.6Hz),2.75(2H,t,J=7.6Hz)。
2.从植物中萃取邻氨基苯甲酰胺级分
实施例3
从培养的燕麦(Avena sativa)中萃取含邻氨基苯甲酰胺的提取物
将143kg乙醇/水7∶3(m/m)加入9kg培养的燕麦中,在室温下浸泡该混合物3天。过滤后,真空下将该提取物浓缩至水相(17.4kg,固含量:2.5%,在干提取物中燕麦蒽酰胺A、B和C的总和:0.093%)。
通过使用Amberlite XAD-16(270g)搅拌来按份(2kg)萃取该水溶液。吸附剂树脂经玻璃料分离,水洗并用甲醇/水1∶1(V/V)洗脱。真空下将合并的洗出液脱溶剂。干提取物:8.5g,燕麦蒽酰胺A、B和C的总和:1.2%。
将该干提取物溶解在乙醇/水1∶1(V∶V)中,通过用乙醇/水1∶1(V∶V)稀释调节至燕麦蒽酰胺A、B和C的总含量为500ppm。
3.对于用通式1的邻氨基苯甲酰胺来抑制由P物质诱导的、来自肥大细胞的组胺释放的活性研究
3.1.合成的邻氨基苯甲酰胺
试验制剂
储备溶液:燕麦蒽酰胺2-19(结构式:见表1a)和dianthramides 20-29(结构式:见表1b);浓度:1%的乙醇溶液;使用前在4℃下贮存。
试剂
P物质:BACHEM。
试验设计:
通过采用甲泛葡胺离心来分离来自鼠的腹膜组织的肥大细胞,并用P物质(10μm)刺激。氯化钙用作阳性对照组。
样品制备:试验和参照物质:
对应于分别为0.5;0.05和0.005%(V/V)的乙醇浓度,用缓冲介质稀释合成方法制备的通式2-29的燕麦蒽酰胺和dianthramides(参见表1a/1b)至最终浓度(0.5;5和50ppm,见表1a/1b)。同样用缓冲介质稀释用作阳性对照组的氯化钙,使得溶液的浓度为10-8-10-2M。
培养方案:
试验体系:在P物质和参比物(CaCl2)或者特定的待试验样品的存在下培养最终试验溶液2分钟(培养温度:37℃)。在不存在P物质和参比或样品物质的情况下培养的细胞用作空白。
细胞溶菌作用后组胺总含量的测定:
首先通过离心将反应溶液脱除细胞组分。然后将存在于上层清液中的组胺转化成带有OPT的衍生物,并且通过光度法(荧光仪Cytofluor 2350)测定溶液的荧光性。
结果:
氯化钙依浓度抑制P物质诱导的、来自肥大细胞的组胺释放。使用浓度为639μM的氯化钙能够实现50%的抑制率。这对应于预期值并因此验证了基本试验设计。
表1a/1b中给出了各种燕麦蒽酰胺和dianthramides的值,基于由P物质刺激的细胞的组胺含量以%抑制率表示。
3.2.直接对比来自燕麦籽的邻氨基苯甲酰胺级分和由相同质量比的合成方法制备的燕麦邻氨基苯甲酰胺组成的重构产物
试验制剂
储备溶液:GS-101100-A和GS-101100-B(样品组成:见表2;燕麦蒽酰胺A、B和C在甘油中的总浓度:500ppm;使用前在4℃下贮存)。
试剂
P物质:BACHEM。
试验设计:
通过采用甲泛葡胺离心来分离来自鼠的腹膜组织的肥大细胞,并用P物质(10μm)刺激。氯化钙用作阳性对照组。
样品制备:试验和参照物质:
相应于分别为0.1;1和10%(V/V)的乙醇浓度,用缓冲介质稀释GS-101100-A和GS-101100-B样品至最终浓度(0.5;5和50ppm,见表2)。同样用缓冲介质稀释用作阳性对照组的氯化钙,使得溶液的浓度为10-5-(原文如此)10-2M。
培养方案:
试验体系:在P物质和参比物(CaCl2)或者特定的待试验样品的存在下培养最终试验溶液2分钟(培养温度:37℃)。在不存在P物质和参比或样品物质的情况下培养的细胞用作空白。
细胞溶菌作用后组胺总含量的测定:
首先通过离心将反应溶液脱除细胞组分。然后将存在于上层清液中的组胺转化成带有OPT的衍生物,并且通过光度法(荧光仪Cytofluor 2350)测定溶液的荧光性。
结果:
氯化钙依浓度抑制P物质诱导的、来自肥大细胞的组胺释放。在该试验组中,使用浓度为432μM的氯化钙能够实现50%的抑制率。这对应于预期值并因此验证了基本试验设计。
表2中以%抑制率表示给出了各种燕麦蒽酰胺的值,所述抑制率是基于在未加入抑制剂的情况下由P物质刺激的细胞的组胺含量。
4.结果和结构/活性考虑
4.1.合成的邻氨基苯甲酰胺
对具有肉桂酸的部分结构和二羟基肉桂酸的部分结构(燕麦蒽酰胺)的选定的高纯邻氨基苯甲酰胺的试验结果表明,取决于取代样品,活性有显著差异。使用在肉桂酸/二羟基肉桂酸部分的3-和4-位上具有邻羟基的通式2和3的物质实现了最高的活性,即完全抑制组胺的释放(参见表1a)。另一方面,在此,邻氨基苯甲酸部分中的其他羟基不会导致活性额外增加。物质2(对于0.5、5和50ppm的活性物质浓度,分别为7%、80%和108%,参见表1a)和物质3(对于0.5、5和50ppm的活性物质浓度,分别为11%、62%和106%,参见表1a)的基本相同的抑制数据表明了这一点。因此,使用5ppm的剂量已经能够实现对组胺释放的抑制率大于50%,同时,另一方面,在相同的试验条件下,甚至以50ppm的最高剂量,曲尼司特(物质15,表1a)仅能够实现21%的组胺释放抑制率。
对于在肉桂酸/二氢肉桂酸部分只具有一个游离羟基的邻氨基苯甲酰胺,也能观察到明显大于曲尼司特的活性,特别是当该游离羟基排布在肉桂酸/二氢肉桂酸部分组分的4-位上(表1a:物质4-10)时。在此,对于50ppm的剂量,抑制组胺释放的百分率为37-49%。同样,在邻氨基苯甲酸部分的额外取代不会导致活性有任何显著的增加。因此,同样在仅具有肉桂酸/二氢肉桂酸部分中的一个游离羟基的一组邻氨基苯甲酰胺中,直接与曲尼司特对比,其具有明显更高的活性。
对于在邻氨基苯甲酸残基中只具有一个游离羟基的邻氨基苯甲酰胺,也能观察到大于曲尼司特的活性,特别是当该游离羟基位于邻氨基苯甲酸残基的4-位上(表1:物质11-13)时。这里,在剂量为50ppm时,抑制组胺释放的百分率为30-36%。
物质2-13是通式1的化合物的优选小组的说明性代表物质,对于这些物质:
n=1且
另外:
m=1,2或3,
附带条件是X至少一次选自OH或(原文如此)酰氧基(Oacyl)。
和/或
p=1或2,
附带条件是Y至少一次选自OH和酰氧基(Oacyl)。
物质14-19还包括曲尼司特(物质15),对比于上述物质,它们在组胺释放方面不再发挥令人满意的抑制效果。
曲尼司特的较低活性与Hachisuka等人的研究是一致的(Arch Dermatol Res第280卷,第158-162页;1988)。这些作者们仅在浓度为327ppm时能够实现50%的组胺释放抑制率。很明显,肉桂酸部分或者二氢肉桂酸部分中邻羟基的烷基化伴随着活性的显著下降。
在具有苯甲酸部分结构的化合物(dianthramides)中的相应的结构/活性考虑导致可比较的结果。这里,在苯甲酸残基的3-和4-位上具有两个邻羟基的化合物(参见表1b;尤其参见物质20)具有最高的活性。在其分子的苯甲酸部分具有至少一个游离羟基的dianthramides也表现出尽管略低但仍然良好的活性。
表1b中列出的化合物20-29是通式1的化合物的优选小组的说明性代表物质,对于这些物质,n=0。
4.2.源自植物的邻氨基苯甲酸级分
除了用合成方法制备的燕麦蒽酰胺和dianthramides以外,还就用于抑制有P物质诱导的、来自肥大细胞的组胺释放的适宜性研究了各种植物提取物。表2通过实例给出了具有完全相等的质量比的燕麦提取物(参见表2:样品GS10100-A,将燕麦蒽酰胺3、4和5的总量调整为500ppm的燕麦提取物;结构式:也参见表1a;)和含有合成的燕麦蒽酰胺3、4和5的总量为500ppm的合成重构产物(样品GA10100-B,也参见表1a)的直接对比结果。
所述两种样品的直接对比结果证明,对于由P物质诱导的、来自肥大细胞的组胺释放的抑制主要是由含在燕麦提取物中的燕麦蒽酰胺3、4和5导致的(参见表1a)。
该发现表明,通常,除了根据本发明的合成化合物以外,由其制备的含有标准量的这些物质的植物提取物和级分也能优选用作由P物质诱导的、来自肥大细胞的组胺释放的抑制剂,并且因此能够预防发炎、变红和发痒反应和/或用于缓解这些症状。
5.所选的用作组胺释放抑制剂的已知和迄今未知的物质的综述:
在表3和4中,通过实例列出了优选用作组胺释放抑制剂的一方面迄今未知的物质和另一方面已知的物质。物质2-29已经列于表1a和1b中;物质30-80未在这些表中列出。
表3和4中给出的物质都是酸;但是,应该指出也可以同样的方式使用相应的酯(其中R3=烷基而不是R3=H)和相应的药学上可接受的盐。
6.试验结果总结以及补充评论
令人惊喜地是,所做试验表明,本发明的通式1的化合物以明显低于曲尼司特的使用浓度抑制由P物质诱导的、来自肥大细胞的组胺释放,因此,由于更低的治疗使用浓度和与其相关的更低的毒性危险可能性,通式1的化合物优选用作活性化合物。根据本发明可以使用的化合物和混合物可以是高纯合成产物、来自植物提取物例如燕麦(Avena sative)或者康乃馨种属(Dianthus spec.)的纯化分离产物,或者来自植物例如燕麦(Avena sative)或康乃馨(Dianthus spec.)的特定提取物级分,其含有本发明的化合物,优选以高浓度使用这些物质。
也可优选使用在肉桂酸/二氢肉桂酸部分或者在苯甲酸部分的羟基被烷基化的化合物(前体)(X或Y=Oacyl,其中acyl=CO-R,其中R=-CH3,或者具有2-30个碳原子的直链或支化烷基)代替试验化合物。而且,还可以优选使用在邻氨基苯甲酸部分的羟基被烷基化的前体(其中R=-CH3,或者链长为C2-30的直链或支化烷基)。一旦局部使用,相应的通式1的酰化或者烷基化的化合物非常好地渗入到深层皮肤。在此,它们被存在于人体和动物皮肤中的非特异性酯酶内源性地裂解,以至于实际的有效成分仅在作用部位释放。
取决于物质,根据本发明可以使用的通式1的化合物的使用浓度为0.0001-10%(m/m),优选0.001-1%(m/m),所述浓度基于待用的化妆品或药物最终产品的总质量。
根据本发明所使用的组胺释放抑制剂,尤其是燕麦蒽酰胺和dianthramide类型的组胺释放抑制剂易于加入常规的化妆品或皮肤病/角膜病配方例如喷雾、烟雾、面霜、香波、软膏、酊剂、乳液、指甲护理产品(例如指甲油、指甲油清洗剂、指甲香脂)等中。本文中,在某些情况下是有利的,还能够组合本发明的组胺释放抑制剂与其他活性化合物,例如和其他的,甚至任选协同增效的组胺释放抑制剂,或者和抗发炎物质和/或缓解发痒和变红的物质,其作用基于不同的作用原理,例如抑制发炎介质(尤其是白三烯、前列腺素或细胞因子(原文如此))的释放。本文中,含有根据本发明的组胺释放抑制剂的化妆品和/或皮肤病/角膜病的配方可以另有常规组成,并且用于在皮肤病或角膜病治疗方面治疗皮肤和/或毛发或者在护理美容方面的治疗。但是它们还可以用在装饰性美容的化妆品中。
含有本发明的组胺释放抑制剂的化妆品配方还可以包含其他抗发炎的活性化合物或者具有缓解变红和发痒作用的活性化合物。本文中,适用于或者常规用于美容和/或皮肤病应用的所有抗发炎活性化合物和缓解变红和发痒的活性化合物都可以使用。有利地是所用的抗发炎活性化合物和缓解变红和发痒的活性化合物是甾族的皮质甾类抗发炎物质,例如氢化可的松、地塞米松、地塞米松磷酸酯、甲基脱氢皮质(甾)醇或可的松,能够通过加入其他甾类抗发炎试剂来扩展该列表。也可以使用非甾类抗发炎试剂。在此可通过举例方式提及的有:昔康,例如吡罗昔康或替诺昔康;水杨酸盐,例如阿司匹林、舒林酸、solprin或芬度柳;乙酸衍生物,例如双氯芬酸、芬氯酸、吲哚美辛、舒林酸、托美汀或clindanac;芬那酸(Fenamate)类,例如美非那、甲氯芬那、氟芬那、尼氟灭;丙酸衍生物,例如布洛芬、萘普生、苯恶洛芬;或者吡唑,例如保泰松、羟基保泰松、febrazone或阿扎丙宗。或者,也可以使用天然的抗发炎物质和缓解变红和/或发痒的物质。可以使用植物提取物、特殊的高活性植物提取物级分和从植物提取物分离出来的高纯活性物质。特别优选来自甘菊、真芦荟、没药种、茜草、柳树、柳草的提取物、级分和活性物质以及纯物质例如尤其是没药醇、芹菜素-7-葡糖苷、乳香酸、植物甾醇、甘草甜素、甘草黄酮或licochalkon A。含有组胺释放抑制剂的配方还可以含有两种或多种抗发炎活性化合物的混合物。
含有根据本发明的组胺释放抑制剂的化妆品配方还含有用于防腐的活性化合物,能够使用适用于或常规用于美容和/或皮肤病应用的所有防腐剂。有利的是选择以下防腐剂:例如尤其是苯甲酸及其酯和盐、丙酸及其盐、水杨酸及其盐、2,4-己酸(山梨酸)及其盐、甲醛和多聚甲醛、2-羟基二苯醚及其盐、2-锌硫化嘧啶-N-氧化物、无机硫化物和二硫化物、碘酸钠、三氯叔丁醇、4-羟基苯甲酸及其盐和酯、无水乙酸(原文如此)、甲酸、1,6-双(4-脒-2-溴苯氧基)-n-己烷及其盐、乙基汞-(II)-巯基苯甲酸的钠盐、苯基汞及其盐、10-十一碳烯酸及其盐、5-氨基-1,3-双(2-乙基己基)-5-甲基六氢化嘧啶、5-溴-5-硝基-1,3-二恶烷、2-溴-2-硝基-1,3-丙二醇、2,4-二氯苄醇、N-(4-氯代苯基)-N’-(3,4-二氯苯基)脲、4-氯-m-甲酚、2,4,4’-三氯-2’-羟基-二苯醚、4-氯-3,5-二甲基苯酚、1,1’-亚甲基-二(3-(1-羟甲基-2,4-二氧咪唑啉啶(dioximidazolidin)-5-基)脲)、聚-(六亚甲基缩二胍)氢氯化物、2-苯氧基乙醇、六亚甲基四胺、1-(3-氯丙烯)-3,5,7-三氮杂-1-氮阳离子-金刚烷氯化物、1(4-氯代-苯氧基)-1(1H-咪唑-1-基)-3,3-二甲基-2-丁酮、1,3-双-(羟甲基)-5,5-二甲基-2,4-咪唑啉啶二酮、苄醇、吡啶酮氨基乙醇盐、1,2-二溴-2,4-二氰丁烷、2,2’-亚甲基-双(6-溴-4-氯-苯酚)、溴氯苯、5-氯-2-甲基-3(2H)-异噻唑啉酮和2-甲基-3(2H)异噻唑啉酮(原文如此)与氯化镁和硝酸镁的混合物、2-苄基-4-氯苯酚、2-氯-乙酰胺、氯乙酰胺、氯乙酰胺乙酸酯、氯乙酰胺葡糖酸盐、葡糖酸盐氢氯化物、1-苯氧基-异丙醇、溴化和氯化-N-烷基(C12-C22)三甲胺、4,4-二甲基-1,3-恶唑烷、N-羟甲基-N-(1,3-二(羟甲基)-2,5-二羰基-二氧咪唑啉啶(dioximidazolidin)-4-基)-N’-羟甲基脲、1,6-双(4-脒基-苯氧基)-n-己烷及其盐、戊二醛5-乙基-1-氮杂脱氧胞苷-3,7-二氧-二环(3.3.0)辛烷、3-(4-氯代苯氧基)-1,2-丙二醇、季铵盐、氯化烷基-(C8-C18)-二甲基苯胺、溴化烷基-(C8-C18)-二甲基苯胺、糖酸烷基-(C8-C18)-二甲基苯甲胺、苄基半缩醛、3-碘代-2-丙炔基氨基甲酸丁酯、羟甲基氨基乙酸钠或者羟甲基氨基乙酸钠(原文如此)。
其他抗菌或抗真菌活性物质也可以特别有利地用在含有本发明组胺释放抑制剂的化妆品配方中,可以使用适用于或者常规用于美容和/或皮肤病应用的所有抗菌或抗真菌活性物质。除了大量的常规抗生素以外,尤其是与化妆品相关的产物,例如三氯生、climbazol、辛氧基甘油、羟甲辛吡酮(octopirox)(1-羟基-4-甲基-6-(2,4,4-三甲基戊基)-2(1H)-吡啶酮,2-氨基乙醇)、甲壳素、法呢醇、甘油单月桂酸酯,尤其是用于治疗狐臭、脚臭或者头皮屑的物质的组合在这里是有利的。
另外,本发明的组胺释放抑制剂的协同混合物也可以特别有利地与用于控制体味的抑制排汗的活性化合物(抗排汗)联用联用。所使用的抑制排汗的活性化合物特别是铝盐,例如氯化铝、氢氯酸铝、硝酸盐、硫酸盐、乙酸盐等。但是,另外,使用锌、镁和锆化合物也是有利的。实质上,铝盐和——在略低的程度上——铝/锆盐的组合已经证明它们用在美容和皮肤病的抗排汗中的价值。皮肤对其有更好的耐受性但不是非常有效的部分中和的羟基氯化铝也值得提及。除了铝盐,也可以使用其他物质,例如a)蛋白沉淀的物质,例如尤其是甲醛、戊二醛、天然和合成的鞣剂和三氯乙酸,它们导致汗腺表面封闭,b)通过堵塞外围神经通路来关闭汗腺的交感神经供应的局部麻醉剂(尤其是例如利多卡因、丙胺卡因或者这些物质的混合物的稀溶液),c)X、A或Y类沸石,其除了减少汗液分泌以外,还用作不良气味的吸附剂,以及d)肉毒毒素(细菌Chlostridium botulinum的毒素),其还用在多汗、病态增加的汗液分泌中,其作用是基于不可逆地阻断汗液分泌相关的传递物质乙酰胆碱的释放。
与(金属)螯合剂联用联用在含有本发明的组胺释放抑制剂的化妆品配方中是有利的,可以使用适用于或者常规用于美容和/或皮肤病应用的所有金属螯合剂。优选使用的(金属)螯合剂尤其是α-羟基脂肪酸、肌醇六磷酸、乳铁传递蛋白、a-羟基酸,例如尤其是柠檬酸、酒石酸和苹果酸以及腐殖酸、胆汁酸、胆汁提取物、胆红素、胆绿素或EDTA、EGTA及其衍生物。
为了使用,以对于化妆品和皮肤病产品的常规方式将含有根据本发明的组胺释放抑制剂的配方足量涂覆在皮肤和/或毛发上。本文中,含有根据本发明的混合物且还用作遮光剂的化妆品和皮肤病配方提供了特殊的优点。有利的是这些配方含有至少一种UVA过滤物和/或至少一种UVB过滤物和/或至少一种无机颜料。本文中,所述配方可以具有各种形式,例如这种类型的配方常规使用的形式。因此,它们可以是例如溶液、油包水(W/O)型或水包油(O/W)型乳液,或者例如水包油包水(W/O/W)型复合乳液、凝胶、水分散液、杆状固体或者还可以是气溶胶。
如所提及的,为了获得保护毛发和/或皮肤不受整个范围的紫外辐射的化妆品配方,含有根据本发明的组胺释放抑制剂的配方可以有利地与在UVB范围内吸收UV辐射的物质联用联用,过滤物质的总量为例如0.01%(m/m)-40%(m/m),优选0.1%-10%(m/m),特别是1.0-5.0%(m/m),以配方的总重量计。它们还可以用作毛发的遮光剂。如果本发明的配方含有UVB过滤物质,这些配方可以是油溶性的或水溶性的。有利的油溶性UVB过滤物是例如:3-亚苄基樟脑衍生物、优选3-(4-甲基亚苄基)樟脑、3-亚苄基樟脑;4-氨基苯甲酸衍生物,优选4-(二甲基-氨基)苯甲酸2-乙基己酯、4-(二甲基氨基)苯甲酸戊酯;肉桂酸酯,优选4-甲氧基肉桂酸2-乙基己酯、4-甲氧基-肉桂酸异戊酯;水杨酸酯,优选水杨酸-2-乙基己酯、水杨酸-4-异丙基苄酯、水杨酸同孟酯;苯甲酮衍生物,优选2-羟基-4-甲氧基苯甲酮、2-羟基-4-甲氧基-4’-甲基苯甲酮、2,2’-二羟基-4-甲氧基-苯甲酮;亚苄基丙二酸酯,优选4-甲氧基亚苄基丙二酸二(2-乙基己基)酯、2,4,6-三苯胺基-(p-碳-2’-乙基-1’-己氧基)-1,3,5-三嗪。有利的水溶性UVB过滤物是例如2-苯基苯并咪唑-5-磺酸盐,例如其钠盐、钾盐或三乙醇胺盐,以及磺酸本身;苯甲酮的磺酸衍生物,优选2-羟基-4-甲氧基苯甲酮-5-磺酸及其盐;3-亚苄基樟脑的磺酸衍生物,例如4-(2-氧-3-亚冰片基甲基)苯磺酸、2-甲基-5-(2-氧-3-亚冰片基-甲基)磺酸及其盐,以及1,4-二(2-氧-10-磺基-3-亚冰片基甲基)苯及其盐(相应的10-硫酸根合化合物,例如相应的钠盐、钾盐或三乙醇胺盐),以及苯-1,4-二(2-氧-3-亚冰片基甲基)-10-磺酸(原文如此)。
上述列出的可以与根据本发明的组胺释放抑制剂联用的UVB过滤物当然不应当被理解为限制性的。使用UVA过滤物也是有利的,例如常含在化妆品配方中的过滤物。这些物质优选是二苯甲酰甲烷的衍生物,尤其是1-(4’-三-丁基苯基)-3-(4’-甲氧基-苯基)-丙烷-1,3-二酮和1-苯基-3-(4’-异丙基苯基)丙烷-1,3-二酮。可使用的量为用于UVB组合的量。
在化妆品配方中,根据本发明的组胺释放抑制剂可以有利联用,例如在这些配方中通常与下述物质联用:例如抗氧剂、香油、防起泡剂、具有着色作用的颜料、增稠剂、表面活性物质、乳化剂、增塑物质、湿润和/或保湿物质、脂肪、油、蜡或其他常用的化妆品配方组分,例如醇、多元醇、聚合物、泡沫稳定剂、电解质、有机溶剂或硅氧烷衍生物。根据本发明,适用于或者常规用于美容和/或皮肤病应用的所有可想到的抗氧剂、香油、防起泡试剂、具有着色作用的颜料、增稠剂、表面活性物质、乳化剂、增塑物质、湿润和/或保湿物质、脂肪、油、蜡、醇、多元醇、聚合物、泡沫稳定剂、电解质、有机溶剂或硅氧烷衍生物都可以用在这里。
在含有根据本发明的组胺释放抑制剂的、用于皮肤的局部预防或美容治疗的配方中含有高含量的治疗物质通常是有利的。根据一个优选实施方案,所述组合物含有一种或多种动物和/或植物的治疗脂肪和油,例如橄榄油、向日葵油、纯化大豆油、棕榈油、芝麻油、油菜籽油、杏仁油、琉璃苣油、月见草油、椰子油、牛油树脂、荷荷芭油、鲸油、牛脂、牛蹄油和猪油,以及任选的其他治疗组分,例如具有8-30个碳原子的脂肪醇。这里使用的脂肪醇可以是饱和或不饱和以及直链或支化的。例如,可以使用癸醇、癸烯醇、辛醇、八烯醇、十二醇、十二烯醇、辛二烯醇、癸二烯醇、十二二烯醇、油醇、蓖麻(原文如此)醇、芥子醇、十八烷醇、异十八烷醇、十六醇、月桂醇、十四烷醇、花生醇、辛醇、癸醇、亚油醇、山萮醇,及其格尔伯特醇,其中可以由其他化学结构上相关的醇来扩展该列表。所述脂肪醇优选来自天然脂肪酸,并且通常由相应的脂肪酸的酯通过还原制备。此外,可以使用由天然产生的脂肪和饱和油通过还原形成的脂肪醇级分,例如牛油、花生油、菜籽油、棉籽油、大豆油、向日葵油、棕榈核油、亚麻子油、玉米油、蓖麻油、油菜籽油、芝麻油、可可油和可可脂。
此外,优选与本发明的组胺释放抑制剂联用的治疗物质还包括
-神经酰胺,神经酰胺应理解为N-酰基鞘氨醇(鞘氨醇的脂肪酰胺)或者该脂质的合成类似物(所谓的假神经酰胺),其明显提高角质层的保水能力,
-磷脂,例如大豆卵磷脂、鸡蛋卵磷脂和脑磷脂,
-凡士林、石蜡和硅油;硅油包括,尤其是二烷基和烷芳基硅氧烷,例如二甲基聚硅氧烷和甲基苯基聚硅氧烷,及其烷氧基化和季铵盐化衍生物。
有利的是还可以将动物和/或植物水解蛋白加入含有根据本发明的组胺释放抑制剂的配方中。在此,尤其是弹性蛋白、胶原质、角蛋白、乳蛋白、大豆蛋白、燕麦蛋白、豌豆蛋白、杏仁蛋白和小麦蛋白级分或者相应的水解蛋白,及其与脂肪酸的缩合产物,以及季铵盐化水解蛋白是有利的,优选使用植物水解蛋白。
至于含有根据本发明的组胺释放抑制剂的美容或皮肤病配方是溶液或乳液的情况,使用的溶剂可以是:
-水或水溶液;
-脂肪油、脂肪、蜡和其他天然和合成的脂肪物质,优选脂肪酸与具有低碳数的醇例如异丙醇、丙二醇或者丙三醇的酯,或者脂肪醇与具有低碳数的烷酸或与脂肪酸的酯;
-醇、二醇或者具有低碳数的多元醇,及其酯,优选乙醇、异丙醇、丙二醇、丙三醇、乙二醇、乙二醇单乙基或单丁基醚、丙二醇单甲基、单乙基或单丁基醚、二乙二醇单甲基或单乙基醚和类似物。
尤其是可以使用上述溶剂的混合物。对于醇溶剂,水可以作为另一组分。
含有根据本发明的组胺释放抑制剂的化妆品配方还可以含有抗氧剂,可以使用适用于或常规用于美容和/或皮肤病应用的所有抗氧剂。有利的是所述抗氧剂选自:氨基酸(例如甘氨酸、组胺酸、酪氨酸、色氨酸)及其衍生物;咪唑(例如尿刊酸)及其衍生物;肽例如D,L-肌肽、D-肌肽、L-肌肽及其衍生物(例如鹅肌肽);类胡萝卜素、胡萝卜素(α-胡萝卜素、β-胡萝卜素、番茄红素)及其衍生物;硫辛酸及其衍生物(例如二氢硫辛酸);金硫葡糖、丙硫氧嘧啶和其他硫醇(例如硫氧环蛋白、谷胱甘肽、半胱氨酸、胱氨酸、胱氨及其糖基、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-亚油基、胆甾烯基以及甘油酯)及其盐;硫代二丙酸二月桂酯、硫代二丙酸二硬脂酸酯、硫代二丙酸及其衍生物(酯、醚、肽、脂质、核苷酸、核苷和盐);非常低的容许剂量的硫氧胺化合物(例如丁基硫堇硫氧胺、高半胱氨酸硫氧胺、丁硫氨酸砜、戊-、己-、更-硫堇硫氧胺);(金属)螯合剂例如α-羟基脂肪酸、棕榈酸、肌醇六磷酸、铁乳蛋白、α-羟基酸(例如柠檬酸、酒石酸、苹果酸)、腐殖酸、胆汁酸、胆汁提取物、胆红素、胆绿素、EDTA、EGTA及其衍生物;不饱和脂肪酸及其衍生物(例如γ-亚麻酸、亚油酸、油酸);叶酸及其衍生物;泛醌、辅酵素及其衍生物;维生素C及其衍生物(例如棕榈酸抗坏血酸酯、棕榈酸抗坏血酸镁、乙酸抗坏血酸酯)、生育酚及其衍生物(例如乙酸维生素E酯);维生素A及其衍生物(棕榈酸维生素A酯);安息香树脂的松柏苯甲酸脂、芸香亭酸及其衍生物;阿魏酸(ferulic acid)及其衍生物;丁羟基甲苯、丁羟基苯甲醚、去甲二氢guaiacic酸(nordihydroguaiacic acid)、去甲二氢愈创木酸、三羟基苯丁酮、尿酸及其衍生物;甘露糖及其衍生物;锌及其衍生物(例如ZnO、ZnSO4(原文如此));硒及其衍生物(例如甲硫氨酸硒);芪及其衍生物(例如氧化芪、反式-氧化芪);以及根据本发明适用的所述活性化合物的衍生物(盐、酯、醚、糖、核苷酸、核苷、肽和脂质)。
含有根据本发明的组胺释放抑制剂的化妆品配方还可以含有维生素和维生素前体,可以使用适用于或者常规用于美容和/或皮肤病应用的所有维生素和维生素前体。这里尤其应当提到维生素和维生素前体例如生育酚、维生素A、烟酸、尼克酰胺(nicotinomide)、B群的其他维生素,尤其是生物素和维生素C。此外,在这组泛醇及其衍生物,特别是泛醇的酯和醚,以及阳离子方法得到的泛醇的衍生物中,例如三乙酸泛醇酯、泛醇、其单乙醚和单乙酸酯,以及阳离子泛醇衍生物是优选使用的。
含有根据本发明的组胺释放抑制剂的化妆品配方还可以含有具有美白祛斑作用的活性化合物。本文中,根据本发明,适用于或者常规用于美容和/或皮肤病应用的所有美白祛斑活性化合物都可以使用。在此范围内,有利的美白祛斑活性化合物是曲酸、氢醌、熊果素、抗坏血酸、磷酸抗坏血酸镁、甘草根提取物及其组分、甘草黄酮或licochalkonA、或尤其是含有美白祛斑的芪衍生物的酸模属和副枝(Ramulus)种属的提取物、松木种属(Pinus)的提取物或者葡萄种属的提取物。
含有根据本发明的组胺释放抑制剂的化妆品配方还可以含有具有皮肤褐变作用的活性化合物。在此范围内上,适用于或者常规用于美容和/或皮肤病应用的所有皮肤褐变活性化合物都可以使用。在此提及二羟丙酮(DHA;1,3-二羟基-2-丙酮)作为实例。DHA可以具有单体或二聚体的形式,在晶体形式中二聚体的比例占主导地位。
含有根据本发明的组胺释放抑制剂的化妆品配方还可以含有单-、二-和寡聚糖,例如葡萄糖、半乳糖、果糖、甘露糖、果糖(原文如此)和乳糖。
含有根据本发明的组胺释放抑制剂的化妆品配方还可以含有植物提取物,其通常通过提取整棵植物来制备,但是在个别情况下也可单一地从植物的花和/或叶、木头、树皮和根中制得。针对根据本发明使用的植物提取物,特别参考在Industrieverbandund Waschmittel e.V.(IKW)出版的Leitfaden zur Inhaltsstoffdeklarationkosmetischer Mittel(Guide to the Declaration of Constituents of Cosmetic Agents)的第3版第44页开始的表格中列出的提取物。来自芦荟、金缕梅、海藻、槲树皮、柳草、大荨麻、野芝麻、蛇麻草、甘菊、芪草、山金车花、金盏草、牛蒡根、马尾草、山楂、菩提花、杏仁、松针、七叶树、檀香木、杜松、椰子、芒果、杏、橙、柠檬、酸橙、柚子、苹果、绿茶、柚子籽、小麦、燕麦、大麦、鼠尾草、百里香、罗勒、迷迭香、桦树、锦葵、苦藻(bitter-crass)、柳树皮、芒柄花、款冬、木槿、人参和姜根的提取物是特别有利的。在这些提取物中,来自真芦荟、甘菊、海藻、迷迭香、金盏草、人参、黄瓜、鼠尾草、大荨麻、菩提花、山金车花和金缕梅是特别优选的。还可以使用两种或多种植物提取物的混合物。用于制备上述植物提取物的萃取试剂可以是,除了其他还有,水、醇及其混合物。在这些醇中,低级醇例如乙醇和异丙醇,多元醇例如乙二醇、丙二醇和丁二醇是这里优选的,尤其是都用作单一的萃取剂以及作为与水的混合物。根据本发明,所述植物提取物可以纯态或者以稀释形式使用。
含有根据本发明的组胺释放抑制剂的化妆品配方还可以含有阴离子、阳离子、非离子和/或两性表面活性剂,尤其是如果将结晶或微晶固体例如无机微细颜料加入本发明配方中时。表面活性剂是能够溶解于水中的有机、非极性物质的两性物质。本文中,表面活性剂分子的亲水部分通常是极性官能团,例如-COO-、-OSO3 2-、-SO3 -,而憎水部分通常是非极性的碳水化合物基团。通常根据分子的亲水部分的性质和电荷对表面活性剂进行分类。这里将其分为四组:
-阴离子表面活性剂,
-阳离子表面活性剂,
-两性离子表面活性剂,
-非离子表面活性剂。
阴离子表面活性剂通常含有羧酸盐、硫酸盐或磺酸盐基团作为官能团。在水溶液中,它们在酸性或中性介质中形成带负电荷的有机离子。实质上,阳离子表面活性剂的唯一特征是存在季胺基团。在水溶液中,它们在酸性或中性介质中形成带正电荷的有机离子。两性离子表面活性剂通式含有阴离子和阳离子基团,并且因此依赖于pH值,在水溶液中具有类似阴离子或阳离子表面活性剂的性质。在强酸性介质中它们具有正电荷,在碱性介质中,它们具有负电荷。另一方面在中性pH范围内,它们是两性离子。聚醚链是典型的非离子表面活性剂。非离子表面活性剂在水性介质中不形成离子。
A.阴离子表面活性剂
可有利地使用的阴离子表面活性剂是酰基氨基酸(及其盐),例如
-酰基谷氨酸盐,例如酰基谷氨酸钠、二-TEA-棕榈酰基-天冬氨酸盐和辛基/癸酸甘油酯谷氨酸钠,
-酰基肽,例如棕榈酰基-水解乳蛋白、酰基水解大豆蛋白钠和酰基水解角原蛋白钠/钾,
-肌氨酸盐,例如十四酰肌氨酸盐、TEA月桂酰肌氨酸盐、月桂酰肌氨酸钠,和椰油基肌氨酸钠,
-牛磺酸盐,例如月桂酰牛磺酸钠和甲基椰油基牛磺酸钠,
-酰基乳酸盐、月桂酰乳酸盐、己酸基乳酸盐,
-丙氨酸盐,
羧酸及其衍生物,例如
-例如,月桂酸、硬脂酸铝、链烷醇酸镁和十一烯酸锌,
-酯-羧酸,例如硬脂酰乳酸钙、laureth-6柠檬酸盐和PEG-4月桂酰胺羧酸钠,
-醚-羧酸,例如laureth-13羧酸钠和PEG-6椰子酰胺羧酸钠,磷酸酯和盐,例如DEA-oleth-10磷酸盐和二(laureth)-4磷酸盐,磺酸及其盐,例如
-酰基磺酸盐,例如椰油基-磺酸钠/铵,
-磺酸烷基月桂酯,
-磺酸烷基酯,例如椰子单甘酯硫酸钠、C12-14烯烃-磺酸钠、月桂醇磺基-乙酸钠和PEG-3椰子酰胺硫酸镁,
-磺基琥珀酸盐,例如二辛基磺基琥珀酸钠、laureth-磺基琥珀酸二钠、月桂基-磺基琥珀酸二钠和十一烯酸单乙醇酰胺磺基琥珀酸二钠
以及
硫酸盐,例如
-烷基醚硫酸盐,例如钠盐、铵盐、镁盐、MIPA、TIPA laureth硫酸盐、myreth硫酸钠和C12-13 pareth硫酸钠,
-烷基硫酸盐,例如钠盐、铵盐和TEA月桂基硫酸盐。
B.阳离子表面活性剂
可有利地使用的阳离子表面活性剂是
-烷基胺,
-烷基咪唑,
-乙氧基胺和
-季(铵)盐表面活性剂。
RNH2CH2CH2COO-(在pH=7时)
RNHCH2CH2COO-B+(在pH=12时)B+=任意的阳离子,例如Na+
-酯季铵盐
季铵盐表面活性剂含有至少一个通过共价键连接在4烷基或芳基上的N原子。这导致不管pH值如何都产生正电荷。烷基甜菜碱、烷基氨基丙基甜菜碱和烷基氨基丙基羟基硫烷是有利的。此外,优选所用的阳离子表面活性剂选自以下物质:季铵盐化合物,特别是苄基三烷基氯化或溴化铵,例如苄基二甲基硬脂酰基氯化铵,以及烷基三烷基-铵盐,例如十六烷基三甲基氯化或溴化铵、二烷基二甲基氯化或溴化铵、烷基氨基乙基-三甲基硫化铵醚、烷基吡啶盐,例如月桂基-或十六烷基氯化嘧啶、咪唑衍生物和阳离子性质的化合物,例如铵氧化物,例如烷基二甲基氧化铵或三级氨基乙基二甲基氧化铵。使用十六烷基甲基铵盐是特别有利的。
C.两性离子表面活性剂
可有利地使用的两性离子表面活性剂是
-酰基-/二烷基乙二胺,例如酰基两性乙酸钠、酰基两性二丙酸二钠、烷基两性二乙酸二钠、酰基两性羟基丙基磺酸钠、酰基两性二乙酸二钠和酰基两性丙酸钠,
-N-烷基氨基酸,例如氨基丙基烷基甘氨酸、烷基-氨基丙酸、烷基亚氨基二丙酸钠和月桂两性羧基甘氨酸钠。
D.非离子表面活性剂
可有利地使用的非离子表面活性剂是
-醇,
-链烷醇酰胺,例如椰子酰胺MEA/DEA/MIPA,
-铵氧化物,例如椰子酰基丙基氧化铵,
-酯,由羧酸与环氧乙烷、丙三醇、失水山梨糖醇或其他醇酯化形成,
-醚,例如乙氧基/丙氧基化醇、乙氧基/丙氧基化酯、乙氧基/丙氧基化甘油酯、乙氧基/丙氧基化胆固醇、乙氧基/丙氧基化三甘油酯、乙氧基/丙氧基化羊毛脂、乙氧基/丙氧基化聚硅氧烷、丙氧基化POE醚和烷基聚糖苷,例如月桂基糖苷、癸基糖苷和椰子糖苷。
-蔗糖酯和醚
-聚甘油酯、二甘油酯、单甘油酯
-甲基葡萄糖酯,羟基酸酯
使用阴离子和/或两性离子表面活性剂与一种或多种非离子表面活性剂的组合也是有利的。以配方的总重量计,表面活性物质可以1-98%(m/m)的浓度存在于含有本发明的组胺释放抑制剂的配方中。
含有根据本发明的组胺释放抑制剂的化妆品或皮肤病配方还可以为乳液形式。
油相可以有利地选自下组物质:
-矿物质油,矿物质蜡
-脂肪油、脂肪、蜡和其他天然和合成的脂肪物质,优选脂肪酸与具有低碳数的醇例如异丙醇、丙二醇或甘油的酯,或者脂肪醇与具有低碳数的烷酸或者与脂肪酸的酯;
-安息香烷基酯;
-硅油,例如二甲基聚硅氧烷、二乙基聚硅氧烷、二苯基聚硅氧烷及其混合形式。
有利的是在芳族羧酸与具有3-30个碳原子链长的饱和和/或不饱和、支化和/或直链醇的酯中,可以使用具有3-30个碳原子链长的饱和和/或不饱和、支化和/或直链烷羧酸与具有3-30个碳原子链长的饱和和/或不饱和、支化和/或直链醇的酯。优选的酯油是十四烷酸异丙酯、棕榈酸异丙酯、硬脂酸异丙酯、油酸异丙酯、硬脂酸正丁酯、月桂酸正己酯、油酸正癸酯、硬脂酸异辛酯、硬脂酸异壬酯、异壬酸异壬酯、棕榈酸2-乙基己酯、月桂酸2-乙基己酯、硬脂酸2-己基癸酯、棕榈酸2-辛基十二烷酯、油酸油酯、芥子酸油酯、油酸芥子酯、芥子酸芥子酯,以及这些酯的合成的、半合成的和天然混合物,例如荷荷芭油。
此外,有利的是油相可以选自包括以下物质的组:支化和直链碳水化合物和蜡、硅油、二烷基醚、包括饱和或不饱和的支化或直链醇的组,以及脂肪酸甘油三酸酯,特别是链长为8-24个碳原子,尤其是12-18个碳原子的饱和或不饱和的支化或直链烷羧酸的三甘油酯。脂肪酸三甘油酯可以有利地例如选自包括以下物质的组:合成的、半合成的和天然油,例如橄榄油、向日葵油、大豆油、花生油、油菜籽油、杏仁油、棕榈油、椰子油、棕榈核油等。也可以有利地使用这些油和蜡组分的任意混合物。在某些情况下,使用蜡例如棕榈酸十六烷酯作为油相的唯一脂质组分也是有利的;有利的是所述油相选自异硬脂酸2-乙基己酯、辛基十二烷醇、异壬酸异十三烷酯、异十二烷、椰子酸2-乙基己酯、苯甲酸C12-15-烷基酯、辛-癸酸三甘油酯和二辛酰醚。苯甲酸C12-15-烷基酯和异硬脂酸2-乙基己酯和混合物、苯甲酸C12-15-烷酯和异壬酸异十三酯的混合物以及异硬脂酸2-乙基己酯、苯甲酸C12-15-烷酯和异壬酸异十三酯的混合物是特别有利的。可以有利地使用碳水化合物石蜡油、角鲨烷和角鲨烯。有利的是油相还可以含有环状或线性硅油或者全部由这些油组成,但是优选使用除了硅油以外的额外的其他油相组分。环甲基硅酮(例如十甲基环戊硅氧烷)可有利地用作硅油。但是,还可以有利地使用其他硅油,例如十一甲基环三硅氧烷、聚二甲基硅氧烷和聚(甲基-苯基硅氧烷)。此外,环甲基硅酮和异壬酸异十三酯的混合物以及环甲基硅酮和异硬脂酸2-乙基己酯的混合物是特别有利的。
含有根据本发明的组胺释放抑制剂且具有乳液形式的配方的水相可以含有:醇、二醇或具有低碳数的多元醇及其醚,优选乙醇、异丙醇、丙二醇、丙三醇、乙二醇、乙二醇单乙醚或单丁醚、丙二醇单甲醚或单乙醚或单丁醚、二乙二醇单甲醚或单乙醚及类似产物,以及具有低碳数的醇,例如乙醇、异丙醇、1,2-丙二醇、丙三醇,以及特别地,一种或多种增稠剂,所述增稠剂有利地选自包括以下物质的组:二氧化硅、硅酸铝、多糖及其衍生物,例如透明质酸、黄原胶、羟丙基-甲基纤维素,特别有利的是选自聚丙烯酸酯,优选来自包括所谓的卡波姆(carbopol)的聚丙烯酸酯,例如980、981、1382、2984、5984类型的卡波姆,在每种情况下都是它们自身或者它们的组合。
含有根据本发明的组胺释放抑制剂且具有乳液形式的配方有利地含有一种或多种乳化剂。O/W乳化剂可以例如有利地选自包括聚乙氧基化、聚丙氧基化或聚乙氧基化和聚丙氧基化产物,例如:
-脂肪醇乙氧基化物
-乙氧基化羊毛蜡醇
-通式为R-O-(-CH2-CH2-O-)n-R’的聚乙二醇醚
-通式为R-COO-(-CH2-CH2-O-)n-H的脂肪酸乙氧基化物
-通式为R-COO-(-CH2-CH2-O-)n-R’的醚化脂肪酸乙氧基化物
-通式为R-COO-(-CH2-CH2-O-)n-C(O)-R’的酯化脂肪酸乙氧基化物
-聚乙二醇甘油脂肪酸酯
-乙氧基化失水山梨糖醇酯
-胆固醇乙氧基化物
-乙氧基化三甘油酯
-通式为R-COO-(-CH2-CH2-O-)n-OOH的烷基醚羧酸,n表示(原文如此)5-30的数字
-聚氧乙烯山梨醇脂肪酸酯
-通式为R-O-(-CH2-CH2-O-)n-SO3-H的烷基醚硫酸盐
-通式为R-O-(-CH2-CH(CH3)-O-)n-H的脂肪醇丙氧基化物
-通式为R-O-(-CH2-CH(CH3)-O-)n-R’的聚丙二醇醚
-丙氧基化羊毛蜡醇
-酯化脂肪酸丙氧基化物R-COO-(-CH2-CH(CH3)-O-)n-R’
-通式为R-COO-(-CH2-CH(CH3)-O-)n-C(O)-R’的酯化脂肪酸丙氧基化物
-通式为R-COO-(-CH2-CH(CH3)-O-)n-H的脂肪酸丙氧基化物
-聚丙二醇甘油脂肪酸酯
-丙氧基化失水山梨糖醇酯
-胆固醇丙氧基化物
-丙氧基化三甘油酯
-通式为R-O-(-CH2-CH(CH3)-O-)n-CH2-COOH的烷基醚羧酸
-烷基醚硫酸盐和所述硫酸盐所基于的、通式为R-O-(-CH2-CH(CH3)-O-)n-SO3-H的酸
-通式为R-O-Xn-Ym-H的脂肪醇乙氧基化物/丙氧基化物
-通式为R-O-Xn-Ym-R’的聚丙二醇醚
-通式为R-COO-Xn-Ym-R’的酯化脂肪酸丙氧基化物
-通式为R-COO-Xn-Ym-H的脂肪酸乙氧基化物/丙氧基化物。
根据本发明,所用的聚乙氧基化、聚丙氧基化或聚乙氧基化和聚丙氧基化W/O乳化剂特别有利地选自包括具有11-18,特别有利地具有14.5-15.5的HLB值的物质,O/W乳化剂最好含有不饱和R和/或R’基团。如果O/W乳化剂含有不饱和R和/或R’基团,或者如果存在异烷基衍生物,则这些乳化剂的优选HLB值也可以更低或者更高。
脂肪醇乙氧基化物选自包括乙氧基化硬脂醇、十六烷醇、十六烷硬脂醇(棕榈醇)是有利的。下述物质是特别优选的:
聚乙二醇(13)硬脂醚(Steareth-13),
聚乙二醇(14)硬脂醚(Steareth-14),
聚乙二醇(15)硬脂醚(Steareth-15),
聚乙二醇(16)硬脂醚(Steareth-16),
聚乙二醇(17)硬脂醚(Steareth-17),
聚乙二醇(18)硬脂醚(Steareth-18),
聚乙二醇(19)硬脂醚(Steareth-19),
聚乙二醇(20)硬脂醚(Steareth-20),
聚乙二醇(12)异硬脂醚(Isosteareth-12),
聚乙二醇(13)异硬脂醚(Isosteareth-13),
聚乙二醇(14)异硬脂醚(Isosteareth-14),
聚乙二醇(15)异硬脂醚(Isosteareth-15),
聚乙二醇(16)异硬脂醚(Isosteareth-16),
聚乙二醇(17)异硬脂醚(Isosteareth-17),
聚乙二醇(18)异硬脂醚(Isosteareth-18),
聚乙二醇(19)异硬脂醚(Isosteareth-19),
聚乙二醇(20)异硬脂醚(Isosteareth-20),
聚乙二醇(13)十六烷基醚(Ceteth-13),
聚乙二醇(14)十六烷基醚(Ceteth-14),
聚乙二醇(15)十六烷基醚(Ceteth-15),
聚乙二醇(16)十六烷基醚(Ceteth-16),
聚乙二醇(17)十六烷基醚(Ceteth-17),
聚乙二醇(18)十六烷基醚(Ceteth-18),
聚乙二醇(19)十六烷基醚(Ceteth-19),
聚乙二醇(20)十六烷基醚(Ceteth-20),
聚乙二醇(13)异十六烷基醚(Isoceteth-13),
聚乙二醇(14)异十六烷基醚(Isoceteth-14),
聚乙二醇(15)异十六烷基醚(Isoceteth-15),
聚乙二醇(16)异十六烷基醚(Isoceteth-16),
聚乙二醇(17)异十六烷基醚(Isoceteth-17),
聚乙二醇(18)异十六烷基醚(Isoceteth-18),
聚乙二醇(19)异十六烷基醚(Isoceteth-19),
聚乙二醇(20)异十六烷基醚(Isoceteth-20),
聚乙二醇(12)油基醚(Oleth-12),
聚乙二醇(13)油基醚(Oleth-13),
聚乙二醇(14)油基醚(Oleth-14),
聚乙二醇(15)油基醚(Oleth-15),
聚乙二醇(12)月桂基醚(Laureth-12),
聚乙二醇(12)异月桂基醚(Isolaureth-12),
聚乙二醇(13)十六烷基硬脂醚(Ceteareth-13),
聚乙二醇(14)十六烷基硬脂醚(Ceteareth-14),
聚乙二醇(15)十六烷基硬脂醚(Ceteareth-15),
聚乙二醇(16)十六烷基硬脂醚(Ceteareth-16),
聚乙二醇(17)十六烷基硬脂醚(Ceteareth-17),
聚乙二醇(18)十六烷基硬脂醚(Ceteareth-18),
聚乙二醇(19)十六烷基硬脂醚(Ceteareth-19),
聚乙二醇(20)十六烷基硬脂醚(Ceteareth-20)。
此外,脂肪酸乙氧基化物选自下组是有利的:
聚乙二醇(20)硬脂酸盐,
聚乙二醇(21)硬脂酸盐,
聚乙二醇(22)硬脂酸盐,
聚乙二醇(23)硬脂酸盐,
聚乙二醇(24)硬脂酸盐,
聚乙二醇(25)硬脂酸盐,
聚乙二醇(12)异硬脂酸盐,
聚乙二醇(13)异硬脂酸盐,
聚乙二醇(14)异硬脂酸盐,
聚乙二醇(15)异硬脂酸盐,
聚乙二醇(16)异硬脂酸盐,
聚乙二醇(17)异硬脂酸盐,
聚乙二醇(18)异硬脂酸盐,
聚乙二醇(19)异硬脂酸盐,
聚乙二醇(20)异硬脂酸盐,
聚乙二醇(21)异硬脂酸盐,
聚乙二醇(22)异硬脂酸盐,
聚乙二醇(23)异硬脂酸盐,
聚乙二醇(24)异硬脂酸盐,
聚乙二醇(25)异硬脂酸盐,
聚乙二醇(12)油酸盐,
聚乙二醇(13)油酸盐,
聚乙二醇(14)油酸盐,
聚乙二醇(15)油酸盐,
聚乙二醇(16)油酸盐,
聚乙二醇(17)油酸盐,
聚乙二醇(18)油酸盐,
聚乙二醇(19)油酸盐,
聚乙二醇(20)油酸盐。
有利的是laureth-11-羧酸钠可以用作乙氧基化烷基醚羧酸或其盐。有利的是laureth1-4硫酸钠可以用作烷基醚硫酸盐。有利的是聚乙二醇(30)胆固醇醚可以用作乙氧基化胆固醇衍生物。聚乙二醇(25)大豆甾醇也证明是可用的。
有利的是聚乙二醇(60)月见草三甘油酯可以用作乙氧基化三甘油酯。
此外,有利的是聚乙二醇甘油脂肪酸酯选自包括:
聚乙二醇(20)月桂酸甘油酯,
聚乙二醇(21)月桂酸甘油酯,
聚乙二醇(22)月桂酸甘油酯,
聚乙二醇(23)月桂酸甘油酯,
聚乙二醇(6)癸酸/正亮氨酸甘油酯,
聚乙二醇(20)油酸甘油酯,
聚乙二醇(20)异硬脂酸甘油酯,
聚乙二醇(18)油酸/椰子酸甘油酯。
而且,有利的是失水山梨糖醇酯选自包括:
聚乙二醇(20)失水山梨糖醇单月桂酸酯,
聚乙二醇(20)失水山梨糖醇单硬脂酸酯,
聚乙二醇(20)失水山梨糖醇单异硬脂酸酯,
聚乙二醇(20)失水山梨糖醇单棕榈酸酯,
聚乙二醇(20)失水山梨糖醇单油酸酯。
以下物质可以用作有利的W/O乳化剂:具有8-30个碳原子的脂肪醇、具有8-24个,特别是12-18个碳原子链长的饱和和/或不饱和的支化和/或直链烷羧酸的单甘油酯、具有8-24个,特别是12-18个碳原子链长的饱和和/或不饱和的支化和/或直链烷羧酸的二甘油酯、具有8-24个,特别是12-18个碳原子链长的饱和和/或不饱和的支化和/或直链醇的单甘油酯、具有8-24个,特别是12-18个碳原子链长的饱和和/或不饱和的支化和/或直链醇的二甘油酯、具有8-24个,特别是12-18个碳原子链长的饱和和/或不饱和的支化和/或直链烷羧酸的丙二醇酯、具有8-24个,特别是12-18个碳原子链长的饱和和/或不饱和的支化和/或直链烷羧酸的失水山梨糖醇酯。
特别有利的W/O乳化剂是甘油单硬脂酸酯、甘油单异硬脂酸酯、甘油单十四烷酸酯、甘油单油酸酯、二甘油单硬脂酸酯、二甘油单异硬脂酸酯、丙二醇单硬脂酸酯、丙二醇单异硬脂酸酯、丙二醇单十四烷酸酯、丙二醇单月桂酸酯、失水山梨糖醇单异硬脂酸酯、失水山梨糖醇单月桂酸酯、失水山梨糖醇单十四烷酸酯、失水山梨糖醇单异油酸酯、蔗糖二硬脂酸酯、十四烷醇、十八烷醇、二十烷醇、山萮醇、异山萮醇、沙油醇、鲛肝醇、聚乙二醇(2)硬脂醚(Steareth-2)、甘油单月桂酸酯、甘油单正亮氨酸酯、甘油单辛酸酯。
根据本发明的通式1的物质还可以用作香料组合物(芳香组合物)的组分,并且由于其特异活性,用作由P物质诱导的、来自肥大细胞的组胺释放的抑制剂,能够例如赋予最终香料制品以抗过敏或缓解发痒的作用。特别优选的芳香组合物包含(a)具有感官作用的量的香料,(b)具有例如抗过敏或缓解发痒作用的量的一种或多种通式1的化合物,以及(c)任选一种或多种赋形剂和/或添加剂。由于香料在最终化妆品中的比例通常在约1%(m/m)左右,因此含有根据本发明的通式1的化合物的香料优选由约0.1-10%(m/m)的一种或多种通式1的化合物组成。仅具有弱的内在气味或者甚至是完全无嗅的通式1的物质被证明是特别有利的;由于这一特性决定了它们尤其是在芳香组合物中用作由P物质诱导的、来自肥大细胞的组胺释放的抑制剂。
本发明的优选实施方案和其他方面可见所附权利要求。
表1a
%抑制率
表3 表3续
表3续:
表4:
Claims (9)
4.根据权利要求3的用途,其中:
m+p≥2
附带条件是取代基X和Y中的至少两种选自OH和酰氧基。
5.根据权利要求1-4中任一项的用途,其中通式1的化合物或者两种或多种不同的通式1化合物的混合物为植物提取物组分的形式,任选地对该植物提取物进行后处理。
6.根据权利要求5的用途,其中所述任选进行后处理的植物提取物是来自燕麦属、石竹属、蝇子草属或者女娄菜属植物的提取物。
7.根据权利要求5或6的用途,其中对所述植物提取物进行后处理,使得与未经后处理的提取物相比,至少一种通式1的化合物的比例相对于其他被提取的化合物的比例增加。
8.根据权利要求1-4中任一项的用途,其中使用经分离和纯化的通式1的化合物或者经分离和纯化的两种或多种不同的通式1化合物的混合物。
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US (2) | US8203016B2 (zh) |
EP (1) | EP1567143B1 (zh) |
JP (2) | JP2006514931A (zh) |
KR (1) | KR20050085127A (zh) |
CN (2) | CN100548289C (zh) |
AU (1) | AU2003288126A1 (zh) |
BR (1) | BRPI0307117B8 (zh) |
DE (1) | DE10254872A1 (zh) |
WO (1) | WO2004047833A2 (zh) |
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WO2024028511A1 (en) | 2022-08-05 | 2024-02-08 | Symrise Ag | Composition with improved water resistance |
WO2024028512A1 (en) | 2022-08-05 | 2024-02-08 | Symrise Ag | Compositions comprising an antimicrobial boosting agent |
WO2024028514A1 (en) | 2022-08-05 | 2024-02-08 | Symrise Ag | Composition with improved spf and uva photoprotection |
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JPS5126839B1 (zh) | 1970-01-16 | 1976-08-09 | ||
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JPS5838444A (ja) | 1981-08-29 | 1983-03-05 | Shimadzu Corp | クロマトグラフ質量分析計 |
JPS5838244A (ja) | 1981-09-01 | 1983-03-05 | Kissei Pharmaceut Co Ltd | 核置換シンナモイルアントラニル酸塩およびその製造方法 |
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JPS60116657A (ja) * | 1983-11-30 | 1985-06-24 | Ono Pharmaceut Co Ltd | アニリン誘導体 |
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JPH07116029B2 (ja) | 1989-04-04 | 1995-12-13 | キッセイ薬品工業株式会社 | トラニラスト水溶液製剤 |
CA2017287A1 (en) * | 1989-05-23 | 1990-11-23 | Shunji Naruto | Substituted phenol derivatives and their use |
JPH08143525A (ja) * | 1994-11-21 | 1996-06-04 | Banyu Pharmaceut Co Ltd | ヒドロキシ安息香酸アミド誘導体を有効成分とする骨疾患の予防・治療剤 |
FR2737408B1 (fr) | 1995-07-31 | 1997-09-05 | Oreal | Utilisation d'un antagoniste de bradykinine dans une composition cosmetique, pharmaceutique ou dermatologique et composition obtenue |
JP3621483B2 (ja) * | 1995-12-01 | 2005-02-16 | 花王株式会社 | ヒスタミン遊離抑制剤 |
AU724646B2 (en) | 1996-03-15 | 2000-09-28 | Eli Lilly And Company | Method of treating common cold or allergic rhinitis |
WO2000067626A2 (en) | 1999-05-06 | 2000-11-16 | Ceapro Inc. | Oat extracts: refining, compositions and methods of use |
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ES2462925T3 (es) * | 2006-06-14 | 2014-05-26 | Symrise Ag | Compuestos con efecto antimicrobiano para el tratamiento de fetidez oral |
-
2002
- 2002-11-25 DE DE10254872A patent/DE10254872A1/de not_active Withdrawn
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2003
- 2003-11-20 JP JP2004554400A patent/JP2006514931A/ja active Pending
- 2003-11-20 CN CNB2003801040167A patent/CN100548289C/zh not_active Expired - Lifetime
- 2003-11-20 CN CN200910173877XA patent/CN101683310B/zh not_active Expired - Lifetime
- 2003-11-20 US US10/535,985 patent/US8203016B2/en active Active
- 2003-11-20 KR KR1020057009267A patent/KR20050085127A/ko active Search and Examination
- 2003-11-20 BR BRPI0307117A patent/BRPI0307117B8/pt active IP Right Grant
- 2003-11-20 EP EP03780002.6A patent/EP1567143B1/de not_active Expired - Lifetime
- 2003-11-20 WO PCT/EP2003/012990 patent/WO2004047833A2/de active Application Filing
- 2003-11-20 AU AU2003288126A patent/AU2003288126A1/en not_active Abandoned
-
2010
- 2010-08-05 JP JP2010176413A patent/JP5467014B2/ja not_active Expired - Lifetime
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- 2012-06-15 US US13/524,374 patent/US8409552B2/en not_active Expired - Lifetime
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
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CN105078821A (zh) * | 2015-08-14 | 2015-11-25 | 台山美环健芦荟制品有限公司 | 一种含芦荟鲜汁的抗刺激抗过敏产品及其制备方法 |
CN107625680A (zh) * | 2017-09-26 | 2018-01-26 | 杭州梵琳科技有限公司 | 舒敏水剂及其制备方法 |
CN107625680B (zh) * | 2017-09-26 | 2020-07-10 | 杭州梵琳科技有限公司 | 舒敏水剂及其制备方法 |
CN115243664A (zh) * | 2020-03-06 | 2022-10-25 | 西姆莱斯股份公司 | 提高皮肤渗透性的包含燕麦蒽酰胺的组合物 |
CN115279333A (zh) * | 2020-03-06 | 2022-11-01 | 西姆莱斯股份公司 | 包含燕麦蒽酰胺和β-葡聚糖的组合物或燕麦提取物 |
Also Published As
Publication number | Publication date |
---|---|
US8203016B2 (en) | 2012-06-19 |
US20060089413A1 (en) | 2006-04-27 |
WO2004047833A3 (de) | 2005-01-13 |
CN100548289C (zh) | 2009-10-14 |
EP1567143A2 (de) | 2005-08-31 |
EP1567143B1 (de) | 2013-08-14 |
US20120315233A1 (en) | 2012-12-13 |
CN101683310B (zh) | 2012-12-12 |
CN1713904A (zh) | 2005-12-28 |
BR0307117A (pt) | 2004-12-28 |
BRPI0307117B8 (pt) | 2021-05-25 |
BRPI0307117B1 (pt) | 2017-07-18 |
US8409552B2 (en) | 2013-04-02 |
DE10254872A1 (de) | 2004-06-03 |
JP2010248268A (ja) | 2010-11-04 |
WO2004047833A2 (de) | 2004-06-10 |
JP2006514931A (ja) | 2006-05-18 |
JP5467014B2 (ja) | 2014-04-09 |
AU2003288126A1 (en) | 2004-06-18 |
KR20050085127A (ko) | 2005-08-29 |
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