CN101528758B - [(4-氧代-4h-苯并吡喃-3-基)羟甲基]-或[(4-氧代-4h-苯并吡喃-3-基)甲基]膦酸衍生物 - Google Patents
[(4-氧代-4h-苯并吡喃-3-基)羟甲基]-或[(4-氧代-4h-苯并吡喃-3-基)甲基]膦酸衍生物 Download PDFInfo
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- CN101528758B CN101528758B CN2007800402648A CN200780040264A CN101528758B CN 101528758 B CN101528758 B CN 101528758B CN 2007800402648 A CN2007800402648 A CN 2007800402648A CN 200780040264 A CN200780040264 A CN 200780040264A CN 101528758 B CN101528758 B CN 101528758B
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- 208000024891 symptom Diseases 0.000 description 1
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- 238000007910 systemic administration Methods 0.000 description 1
- 229940104261 taurate Drugs 0.000 description 1
- BORJONZPSTVSFP-UHFFFAOYSA-N tetradecyl 2-hydroxypropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)O BORJONZPSTVSFP-UHFFFAOYSA-N 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 210000004906 toe nail Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000015193 tomato juice Nutrition 0.000 description 1
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- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical class OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- HTJNEBVCZXHBNJ-XCTPRCOBSA-H trimagnesium;(2r)-2-[(1s)-1,2-dihydroxyethyl]-3,4-dihydroxy-2h-furan-5-one;diphosphate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.OC[C@H](O)[C@H]1OC(=O)C(O)=C1O HTJNEBVCZXHBNJ-XCTPRCOBSA-H 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
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- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
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- 239000011710 vitamin D Substances 0.000 description 1
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- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
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Abstract
本发明涉及通式(I)的化合物或其盐,其中R1-R3各自彼此独立地表示H、羟基或含1-8个C原子的烷氧基,R4表示含1-4个C原子的烷基、H、羟基或含1-8个C原子的烷氧基,R5表示H或羟基,和R6表示H或含1-18个C原子的烷基,但是其中所有R1-R4不能同时等于H,还涉及它们的组合物以及它们的制备和用途。
Description
本发明涉及[(4-氧代-4H-苯并吡喃-3-基)羟甲基]-或[(4-氧代-4H-苯并吡喃-3-基)甲基]膦酸,其衍生物和/或其盐,包含这些化合物的组合物和混合物和它们的制备和用途。
根据本发明的化合物的应用领域是例如,化妆品。护理化妆品的目的在于无论将其施用在哪里均可以获得皮肤年轻的印象。原则上,存在各种实现该目的的方式。例如,可以通过敷粉或霜弥补已有皮肤损害,诸如不规则的色素沉着或皱纹。另一种途径是防止皮肤受到导致皮肤永久性损害和由此老化的环境影响。因此这种理念是以预防性方式干预并且因此延缓老化过程。这种情况的一个实例为已经提及的UV过滤剂,由于在某些波长范围吸收,它预防或至少减轻皮肤损害。而就UV过滤剂而言,损害情况,即UV辐射被皮肤屏蔽,另一种途径包括尝试巩固皮肤对损害的天然防御机制或修复机制。最后,另一种途径包括补偿皮肤随年龄增长对有害影响的防御功能的减弱,这通过外部提供能够替代这种减弱的防御或修复功能的物质。例如,皮肤具有清除由外部和内部应激因素产生的自由基的能力。这种能力随年龄的增长而减弱,从而使老化过程随年龄增长而加速。
在现代社会中,皮肤的某种程度的晒黑认为是有吸引力的并且认为是活力和动感的表现。除了太阳对皮肤的这种所需作用之外,还发生许多不希望的副作用,例如晒斑或皮肤过早老化和起皱。280-400nm的波长范围在此具有特别的重要性。这种范围涵盖了波长在280和320nm之间的UV-B射线,它们在太阳红斑的形成方面扮演关键角色,以及波长在320和400nm之间的UV-A射线,它们晒黑皮肤,而且使皮肤老化,帮助触发红斑反应或能加剧某些人中的这种反应乃至触发光毒或光过敏和刺激性反应。
皮肤损害不仅由日光引起,而且由其它外部影响,例如冷或热引起。另外,皮肤经历自然老化,随之皱纹形成,皮肤弹性降低。
然而,在化妆品制备中的另一困难是期望结合到化妆品组合物中的活性化合物通常不稳定并且可能在所述组合物中被破坏。该破坏可能例如由于与大气氧反应或吸收UV射线而引起。这样破坏的分子可能例如因它们的结构改变而改变颜色和/或损失活性。
解决所述问题的一种已知的方式是向组合物添加抗氧化剂。
根据CDChemie Lexikon[CD Rompp′s Lexicon of Chemistry]-1.0版,Stuttgart/New York:Georg Thieme Verlag 1995,抗氧化剂是抑制或防止由于氧气作用,尤其氧化过程而引起待保护的物质不希望的改变的化合物。应用领域是,例如,在塑料和橡胶中防老化;在脂肪中防酸败,在油、家畜饲料、车用汽油和喷气燃料中防结胶,在变速器和涡轮机油中防淤渣生成,在香料中防气味损害。作为抗氧化剂有效的化合物尤其是,酚类、氢醌类、焦儿茶酚类和芳族胺类(它们中每一种被空间位阻基团取代),和它们的金属络合物。根据抗氧化剂的作用通常在于它们充当在氧化期间产生的自由基的自由基清除剂。
因此仍存在对皮肤耐受并且还适合用于皮肤护理组合物并且可以按适合的方式结合到化妆品组合物中的抗氧化剂的需求。
本发明目的因此是提供应用于化妆品组合物中时可以赋予体细胞抗氧化应激的保护作用和/或对抗皮肤老化的化合物。
已经令人惊奇地发现,[(4-氧代-4H-苯并吡喃-3-基)羟甲基]-或[(4-氧代-4H-苯并吡喃-3-基)甲基]膦酸,其衍生物或其盐妇产适合作为人类皮肤的抗氧化剂。
至今,未取代的色酮-3-甲烷膦酸和其甲基、乙基、异丙基和正丁基酯是已知的。然而,Kostka等人,Phosphorus,Sulfur and Silicon and theRelated Elements(1991),57(3-4),279-85仅仅描述了这些化合物的合成。
本发明因此首先涉及式I化合物或其盐:
其中
R1-R3各自彼此独立地表示H、羟基或含1-8个C原子的烷氧基,
R4表示含1-4个C原子的烷基、H、羟基或含1-8个C原子的烷氧基,
R5表示H或羟基,和
R6表示H或含1-18个C原子的烷基,
但是其中所有R1-R4不能同时等于H。
在式I中,含1-8个C原子的烷氧基表示例如,甲氧基、乙氧基、丙氧基、丁氧基、戊氧基、己氧基、庚氧基或辛氧基,其中在每种情况下还可以经由氧键接所述烷基的异构化代表物。
在式I中,含1-18个C原子的烷基表示例如,甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、正C5H11至正C18H37,和它们的异构化形式。含1-5个C原子的烷基是例如,甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基或正戊基。
R1-R3优选各自彼此独立地是H、羟基、甲氧基或乙氧基,尤其优选H或羟基。
R4优选是H、甲基、乙基或羟基,尤其优选甲基或羟基。
R1非常尤其优选是H。
R2和R3各自彼此独立地非常尤其优选是羟基。
R5非常尤其优选是羟基。
R6尤其优选是H或含1-5个C原子的烷基,非常尤其优选H或甲基。
本发明此外涉及包含至少一种式I化合物的组合物,这相当于根据本发明的化合物的优选用途。
所述盐优选是具有不阻碍式I化合物结合到组合物中的平衡离子的那些。例如,优选它们是碱金属、碱土金属或铵盐。根据本发明尤其优选所述盐是钠、钾、镁或铵盐,例如三乙醇铵盐。
特别地,根据本发明的化合物或组合物的优点是抗氧化作用和皮肤的良好耐受性。待根据本发明采用的化合物的特别作用性能具有特别的优点,这经由该化合物在组合物中的稳定性和在皮肤中或上的抗氧化作用表现出来。
由于这些性能,本发明涉及如上所指出的式I化合物用作抗氧化剂或用于制备组合物,尤其是具有抗氧化性能的组合物,或用于制备可以赋予体细胞抗氧化应激保护作用和/或可以对抗皮肤老化或可以帮助降低皮肤老化影响的组合物的用途。
所述组合物在此通常是指可局部施用的组合物,例如化妆品、药物或皮肤病制剂,或食品或食品增补剂。在这种情况下,所述组合物包含化妆品、药物或皮肤病学上或对于食品适合的赋形剂和,取决于所需性能分布,任选的其它合适成分。
局部组合物优选用作化妆品或皮肤病组合物。
对于本发明而言,术语组合物或制剂作为同义词使用。
根据本发明,式I化合物通常以0.01wt%-20wt%,优选0.1wt%-10wt%,尤其优选1wt%-8wt%的量使用。本领域技术人员根据组合物的预计作用相应地选择用量是绝对没有困难的。
为了式I化合物能够尤其充分地显示它们作为皮肤自由基清除剂的积极作用,可优选允许式I化合物渗入较深皮层。为此可有若干可能性,例如也可在组合物中提供能够经由外皮层输送式I化合物的相应输送剂,例如脂质体。最后,式I化合物的全身输送也是可以的。那么,例如以适合于口服的方式设计所述组合物。
一般而言,式I的物质充当自由基清除剂。这类自由基不但通过日光产生,而且在各种条件下形成。实例是缺氧,它阻滞细胞色素氧化酶上游的电子流动并引起超氧化物自由基负离子的形成;炎症,它尤其与白血球的膜NADPH氧化酶引起的超氧化物阴离子形成相关,而且与羟基自由基及其它通常涉及吞噬作用现象的反应性物质的形成(经由在铁(II)离子存在下的歧化)有关;以及类脂自氧化,它一般由羟基自由基引发并且产生油脂烷氧基自由基和氢过氧化物。
认为优选的式I化合物还充当酶抑制剂。它们据认为抑制组氨酸脱羧酶、蛋白质激酶、弹性蛋白酶、醛糖还原酶和透明质酸酶,并因此使得血管鞘的基本物质的完好性得以保持。另外,它们据认为非特异地抑制儿茶酚O-甲基转移酶,使可得的儿茶酚胺的量提高和因此脉管强度提高。另外,它们抑制AMP磷酸二酯酶,给予这些物质抑制凝血细胞聚集的潜能。
由于这些性能,根据本发明的化合物或组合物一般适合于免疫保护和适合于保护DNA和RNA。特别地,组合物适合于保护DNA和RNA以免受氧化性攻击,免受自由基影响和免受由于辐射,尤其是UV辐射所造成的损害。根据本发明的组合物的另一优点是细胞保护,尤其是保护朗氏细胞(Langerhans cell)免受由上述影响所造成的损害。所有这些用途或式I化合物用于制备可相应使用的组合物的用途也明确是本发明的主题。
特别地,根据本发明的优选组合物还适合于治疗与影响分化和细胞增殖的角质化缺陷有关的皮肤病,尤其用于治疗普通痤疮、黑头痤疮、多形痤疮、玫瑰痤疮、结节性痤疮、聚会性痤疮、年龄导致的痤疮、作为副作用出现的痤疮如日光痤疮、药物导致的痤疮或职业痤疮;用于治疗角质化的其它缺陷,尤其是鳞癣、鱼鳞癣型态、Darier病、掌跖角化病、粘膜白斑病、粘膜白斑型态、皮肤和粘膜(口腔)疱疹(苔藓病);用于治疗与角质化缺陷有关且具有炎症和/或免疫变应性组分的其它皮肤疾病,尤其是影响皮肤、粘膜和手指和脚趾甲的所有形式的牛皮癣,和牛皮癣风湿病和皮肤特应性如湿疹,或呼吸特应性,或牙龈肥厚;该化合物此外可用于与角质化缺陷无关的一些炎症;用于治疗可能是病毒来源的所有良性或恶性真皮或表皮赘疣,如寻常疣、扁平疣、疣状表皮发育不良、口腔乳头状瘤、佛罗里达乳头状瘤,以及可能由UV辐射引起的赘疣,尤其是嗜碱细胞上皮瘤和脊细胞上皮瘤;用于治疗其它皮肤病如大疱性皮炎和影响胶原的疾病;用于治疗某些眼睛疾病,尤其是角膜疾病;用于克服或抗击光引起的与老化有关的皮肤老化;用于减少色素沉着和光化角化病;以及用于治疗与正常老化或光引起的老化有关的所有疾病;用于预防或愈合由局部或全身施用皮质类固醇所引起的表皮和/或真皮的萎缩和所有其它类型的皮肤萎缩的创伤/伤痕;用于预防或治疗伤口愈合的缺陷;用于预防或消除由妊娠所引起的拉伸印记或促进伤口愈合;用于抗击皮脂产生的缺陷,例如痤疮或简单皮脂溢中的hyperseborrhoea;用于抗击或预防类似癌症的状态或致癌前的状态,尤其是早幼粒细胞白血病;用于治疗炎症性疾病,例如关节炎;用于治疗皮肤或身体其它区域的所有病毒引起的疾病;用于预防或治疗秃发,用于治疗皮肤病或具有免疫组分的身体其它区域的疾病;用于治疗心血管疾病,例如动脉硬化或高血压,和非胰岛素依赖性糖尿病;用于治疗由UV辐射所引起的皮肤问题。
式I化合物的抗氧化作用可以例如利用2,2-二苯基-1-苦基偕腙肼(DPPH)试验证实。2,2-二苯基-1-苦基偕腙肼是在溶解状态下稳定的自由基。不成对电子导致在515nm处的强吸收谱带;该溶液具有深紫色。在自由基清除剂存在下,电子配对,吸收消失,并且考虑吸收的电子,脱色化学计量地进行。在光度计中测量吸光率。如下测定待试验的物质的抗自由基性能:测量所使用的2,2-二苯基-1-苦基偕腙肼的50%已经与自由基清除剂反应时的浓度。这一浓度表示为EC50,即应该认为是在给定测量条件下该物质的性能的值。将研究的物质与标准物(例如生育酚)对比。EC50值在此是相应化合物清除自由基的能力的量度。EC50值越低,清除自由基的能力越高。抗氧化剂作用的另一重要方面是达到这种EC50值的时间。这种时间(以分钟为单位)给出TEC50值,该值允许得出关于这些抗氧化剂清除自由基的速率的结论。对于本发明而言,在小于60分钟内达到这一值的抗氧化剂认为是快速的,仅在超过120分钟之后达到该EC50值的那些认为具有延时作用。
抗自由基效率(AE)(在C.Sanchez-Moreno,J.A.Larrauri和F.Saura-Calixto在J.Sci.Food Agric.1998,76(2),270-276中进行了描述)由上述量根据以下关系式给出:
低AE(×10-3)在至多大约10的范围中,中等AE在10-20的范围中,高AE根据本发明具有大于20的值。
根据本发明可能尤其优选的是将快速作用抗氧化剂与具有缓慢或延时作用的那些组合。快速作用抗氧化剂与延时抗氧化剂的典型的重量百分率之比为10∶1-1∶10,优选10∶1-1∶1,对于皮肤保护组合物,尤其优选5∶1-2∶1的范围内。然而,在根据本发明同样优选的其它组合物中,出于作用优化目的,提供比快速作用抗氧化剂更多的延时抗氧化剂可能是有利的。典型的组合物则显示快速作用抗氧化剂与延时抗氧化剂的重量百分率之比在1∶1-1∶10,优选1∶2-1∶8的范围内。
如果组合物包含一种或多种另外的抗氧化剂,则可以进一步改善抗氧化应激或抗自由基影响的保护作用,本领域技术人员适当地选择快速作用抗氧化剂或延时抗氧化剂是绝对没有困难的。
在本发明的一个优选的实施方案中,所述组合物因此是一种用于对抗氧化应激而保护体细胞,尤其是用于降低皮肤老化的组合物,其特征在于,除了所述一种或多种式I化合物之外,它还包含一种或多种另外抗氧化剂。
存在很多从专业文献中已知的经证实可用作抗氧化剂的物质,例如氨基酸(例如甘氨酸、组氨酸、酪氨酸、色氨酸)和其衍生物,咪唑(例如尿刊酸)和其衍生物,肽如D,L-肌肽、D-肌肽、L-肌肽和其衍生物(例如鹅肌肽),类胡萝卜素,胡萝卜素(例如α-胡萝卜素、β-胡萝卜素、番茄红素)和其衍生物,绿原酸和其衍生物,硫辛酸和其衍生物(例如二氢硫辛酸),金硫葡糖,丙硫氧嘧啶和其它硫醇(例如硫氧还蛋白、谷胱甘肽、半胱氨酸、胱氨酸、胱胺,和其葡糖基、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、胆甾醇基和甘油基酯)和其盐,硫代二丙酸二月桂基酯,硫代二丙酸二硬脂基酯,硫代二丙酸和其衍生物(酯、醚、肽、类脂、核苷酸、核苷和盐)和非常低耐受剂量(例如pmol至μmol/kg)的亚硫酰亚胺(sulfoximine)化合物(例如丁硫堇亚硫酰亚胺,高半胱氨酸亚硫酰亚胺,丁硫堇砜,戊-、己-和庚硫堇亚硫酰亚胺),以及(金属)螯合剂(例如α-羟基脂肪酸、棕榈酸、植酸、乳铁蛋白),α-羟基酸(例如柠檬酸、乳酸、苹果酸),腐殖酸,胆汁酸,胆汁提取物,胆红素,胆绿素,EDTA,EGTA,和其衍生物,不饱和脂肪酸和其衍生物,维生素C和衍生物(例如抗坏血酸棕榈酸酯、抗坏血酸磷酸镁、抗坏血酸乙酸酯),生育酚和衍生物(例如维生素E乙酸酯),维生素A和衍生物(例如维生素A棕榈酸酯)和苯偶姻树脂的苯甲酸松柏基酯,芸香亭酸和其衍生物,α-葡糖基芸香苷,阿魏酸,糠叉葡萄糖醇,肌肽,丁基羟基甲苯,丁基羟基茴香醚,去甲二氢愈创木酸,三羟基丙基苯基酮,栎精,尿酸和其衍生物,甘露糖和其衍生物,锌和其衍生物(例如ZnO、ZnSO4),硒和其衍生物(例如硒代蛋氨酸),二苯乙烯和其衍生物(例如氧化二苯乙烯、反式-氧化二苯乙烯)。
适合的抗氧化剂还有通式A或B的化合物
其中
R1可以选自基团-C(O)CH3、-CO2R3、-C(O)NH2和-C(O)N(R4)2,
X表示O或NH,
R2表示含1-30个C原子的线性或支化烷基,
R3表示含1-20个C原子的线性或支化烷基,
R4,在每种情况下,彼此独立地表示H或含1-8个C原子的线性或支化烷基,
R5表示含1-8个C原子的线性或支化烷基或含1-8个C原子的线性或支化烷氧基,和
R6表示含1-8个C原子的线性或支化烷基,优选2-(4-羟基-3,5-二甲氧基苄叉基)丙二酸和/或2-(4-羟基-3,5-二甲氧基苄基)丙二酸,尤其优选2-(4-羟基-3,5-二甲氧基苄叉基)丙二酸双(2-乙基己基)酯(例如ST液体)和/或2-(4-羟基-3,5-二甲氧基苄基)丙二酸双(2-乙基己基)酯(例如RonaAP)。
抗氧化剂的混合物同样适合用于根据本发明的化妆品组合物。已知的且市售的混合物是,例如,包含作为活性化合物的卵磷脂,L-(+)-抗坏血酸棕榈酸酯和柠檬酸(例如AP),天然生育酚,L-(+)-抗坏血酸棕榈酸酯,L-(+)-抗坏血酸和柠檬酸(例如K LIQUID),天然来源的生育酚提取物,L-(+)-抗坏血酸棕榈酸酯,L-(+)-抗坏血酸和柠檬酸(例如L LIQUID),DL-α-生育酚,L-(+)-抗坏血酸棕榈酸酯,柠檬酸和卵磷脂(例如LM)或丁基羟基甲苯(BHT),L-(+)-抗坏血酸棕榈酸酯和柠檬酸(例如2004)的那些混合物。这种类型的抗氧化剂与式I化合物在这样的组合物中通常以1000∶1至1∶1000,优选100∶1至1∶100的重量百分率之比使用。
根据本发明的组合物可包含维生素作为另外的成分。根据本发明的化妆品组合物优选包含选自以下的维生素和维生素衍生物:维生素A、维生素A丙酸酯、维生素A棕榈酸酯、维生素A乙酸酯、视黄醇、维生素B、氯化硫胺素盐酸盐(维生素B1)、核黄素(维生素B2)、烟酰胺、维生素C(抗坏血酸)、维生素D、麦角钙化醇(维生素D2)、维生素E、DL-α-生育酚、生育酚E乙酸酯、生育酚琥珀酸氢酯、维生素K1、七叶苷(维生素P活性化合物)、硫胺素(维生素B1)、烟酸(烟碱酸)、吡哆醇、吡哆醛、吡多胺(维生素B6)、泛酸、生物素、叶酸和钴胺(维生素B12)、尤其优选维生素A棕榈酸酯、维生素C和其衍生物、DL-α-生育酚、生育酚E乙酸酯、烟酸、泛酸和生物素。维生素通常在此与式I化合物以1000∶1至1∶1000,优选100∶1至1∶100的重量百分率之比使用。
根据本发明尤其优选的组合物除了式I化合物之外还包含纯UV过滤剂。
当与式I化合物组合使用二(苯甲酰基)甲烷衍生物(它们尤其优选作为UV-A过滤剂)时,产生附加的优点:UV-敏感的二(苯甲酰基)甲烷衍生物还由于式I化合物的存在而被稳定化。本发明因此还涉及式I化合物用于使组合物中的二(苯甲酰基)甲烷衍生物稳定的用途。
原则上,所有的UV过滤剂都适合与根据本发明的式I化合物组合。尤其优选生理学可接受性已被证实的UV过滤剂。对于UVA和UVB过滤剂都存在许多从专业文献中已知的经证实物质,例如:
苄叉樟脑衍生物如3-(4′-甲基苄叉)-dl-樟脑(例如6300),3-苄叉樟脑(例如SD),N-{(2和4)-[(2-氧代冰片-3-叉基)甲基]-苄基}丙烯酰胺的聚合物(例如SW),N,N,N-三甲基-4-(2-氧代冰片-3-叉基甲基)苯铵硫酸甲酯盐(例如SK)或(2-氧代冰片-3-叉基)甲苯-4-磺酸(例如SL),
苯基苯并咪唑磺酸类,如2-苯基苯并咪唑-5-磺酸和其钾、钠和三乙醇胺盐(例如232),2,2-(1,4-亚苯基)双苯并咪唑-4,6-二磺酸和其盐(例如AP)或2,2-(1,4-亚苯基)双苯并咪唑-6-磺酸;
和其它物质,如
以上列举的化合物应该仅认为是实例。当然也可使用其它UV过滤剂。
通常以0.5-10wt%,优选1-8wt%的量将这些有机UV过滤剂结合到化妆品制剂中。
其它适合的有机UV过滤剂是,例如,
-2-(2H-苯并三唑-2-基)-4-甲基-6-(2-甲基-3-(1,3,3,3-四甲基-1-(三甲基甲硅烷基氧基)二硅氧烷基)丙基)苯酚(例如),
-α-(三甲基甲硅烷基)-ω-[三甲基甲硅烷基)氧基]聚[氧基(二甲基[和约6%甲基[2-[对-[2,2-双(乙氧基羰基]乙烯基]苯氧基]-1-亚甲基乙基]和约1.5%甲基[3-[对-[2,2-双(乙氧基羰基)乙烯基])苯氧基)丙烯基)和0.1至0.4%(甲基氢]亚甲硅烷基]](n≈60)(CAS号207 574-74-1),
-2,2′-亚甲基双(6-(2H-苯并三唑-2-基)-4-(1,1,3,3-四甲基丁基)苯酚)(CAS号103 597-45-1),
-2,2′-(1,4-亚苯基)双(1H-苯并咪唑-4,6-二磺酸,单钠盐)(CAS号180898-37-7),
-2,4-双{[4-(2-乙基己基氧基)-2-羟基]苯基}-6-(4-甲氧基苯基)-1,3,5-三嗪(CAS号103 597-45-,187 393-00-6),
通常以0.5-20wt%,优选1-15wt%的量将有机UV过滤剂结合到化妆品制剂中。
可想到的无机UV过滤剂是选自以下的那些:二氧化钛,例如,涂覆的二氧化钛(例如T-2000、T-AQUA),锌氧化物(例如),铁氧化物或铈氧化物。这些无机UV过滤剂一般以0.5-20wt%,优选2-10wt%的量结合到化妆品品组合物中。
具有UV-过滤性能的优选化合物是3-(4′-甲基苄叉)-dl-樟脑、1-(4-叔丁基苯基)-3-(4-甲氧基苯基)丙烷-1,3-二酮、4-异丙基二(苯甲酰基)甲烷、2-羟基-4-甲氧基二苯甲酮、甲氧基肉桂酸辛基酯、水杨酸3,3,5-三甲基环己基酯、4-(二甲基氨基)苯甲酸2-乙基己基酯、2-氰基-3,3-二苯基丙烯酸2-乙基己基酯、2-苯基苯并咪唑-5-磺酸和其钾、钠和三乙醇胺盐。
一种或多种式I化合物与其它UV过滤剂的组合能够优化对抗UV辐射的损害作用的保护作用。
优化的组合物可包含,例如,有机UV过滤剂4′-甲氧基-6-羟基黄酮与1-(4-叔丁基苯基)-3-(4-甲氧基苯基)丙烷-1,3-二酮和3-(4′-甲基苄叉)-dl-樟脑的组合。这种组合产生宽带保护,这可通过加入无机UV过滤剂,如二氧化钛微粒补充。
所有所述UV过滤剂也可以以包囊形式使用。尤其有利的是采用包囊形式的有机UV过滤剂。详细地,产生以下优点:
-胶囊壁的亲水性可独立于UV过滤剂的溶解性而被调节。因此,例如,还可将疏水性UV过滤剂引入纯含水的组合物中。另外,在施用包含疏水性UV过滤剂的组合物时经常被视为令人不愉快的油状印象得到抑制。
-某些UV过滤剂,尤其是二(苯甲酰基)甲烷衍生物,在化妆品品组合物中仅显示降低的光稳定性。通过将损害这些过滤剂的光稳定性的这些过滤剂或化合物,例如,肉桂酸衍生物包囊,使得整个组合物的光稳定性可得到提高。
-有机UV过滤剂的皮肤渗透和与此相关的在直接施用到人类皮肤上时的刺激可能性在文献中被一再讨论。通过在此提出的对相应物质的包囊抑制这种作用。
-一般地,通过对各个UV过滤剂或其它成分的包囊使得可以避免由各组合物成分彼此间的相互作用所引起的组成问题,如结晶过程、沉淀和附聚物形成,因为这种相互作用得到抑制。
因此根据本发明优选的是一种或多种上述UV过滤剂呈包囊形式。在此有利的是,胶囊小到以致它们不能用肉眼观察到。为了实现上述效果,另外必需使胶囊足够稳定且被包囊的活性化合物(UV过滤剂)仅低程度地释放到环境中或完全不释放。
合适的胶囊可具有无机或有机聚合物构成的壁。例如,US 6,242,099 B1描述了具有由壳多糖、壳多糖衍生物或多羟基化多元胺构成的壁的合适的胶囊的制备。根据本发明尤其优选使用的胶囊具有可通过,例如描述于申请WO 00/09652、WO 00/72806和WO 00/71084中的溶胶-凝胶方法而得到的壁。在此同样优选其壁由硅胶(二氧化硅;未限定的硅氧化物氢氧化物)构成的胶囊。本领域技术人员,例如从所引用的专利申请中得知相应胶囊的制备,这些专利申请的内容也明确属于本申请的主题。
所述胶囊在根据本发明的组合物中的优选存在量确保所包囊的UV过滤剂以上述量存在于所述组合物中。
根据本发明的组合物还可包含其它的常规皮肤保护或皮肤护理活性化合物。这些化合物原则上可以是本领域技术人员已知的任何活性化合物。
尤其优选的活性化合物是嘧啶羧酸类和/或芳基肟类。
嘧啶羧酸类存在于适盐微生物中并且在这些生物体的渗透调节中发挥作用(E.A.Galinski等人,Eur.J.Bio-chem.,149(1985)135-139页)。在嘧啶羧酸中,在此尤其应该提及依克多因(ectoine)((S)-1,4,5,6-四氢-2-甲基-4-嘧啶甲酸)和羟基依克多因((S,S)-1,4,5,6-四氢-5-羟基-2-甲基-4-嘧啶甲酸)和其衍生物。这些化合物使在水溶液和有机溶剂中的酶和其它生物分子稳定化。另外,它们尤其使酶针对变性条件例如盐、极端pH值、表面活性剂、脲、氯化胍和其它化合物而稳定化。
依克多因和依克多因衍生物,如羟基依克多因可有利地用于药剂中。特别地,羟基依克多因可用于制备用于治疗皮肤疾病的药剂。羟基依克多因和其它依克多因衍生物的其它应用领域通常是在其中例如使用海藻糖作为添加剂的领域中。因此,依克多因衍生物,例如羟基依克多因可用作干酵母和细菌细胞中的保护剂。药物产品,如非糖基化的、药物活性肽和蛋白质,例如t-PA也可用依克多因或其衍生物保护。
在化妆品应用中,尤其应该提及依克多因和依克多因衍生物用于护理老化、干性或刺激性皮肤的用途。因此,欧洲专利申请EP-A-0 671 161尤其描述了将依克多因和羟基依克多因用于化妆品组合物,如粉剂,皂,含表面活性剂的清洁产品,唇膏,胭脂,化妆品,护理霜和防晒制剂中。
这里优选使用下式C的嘧啶甲酸:
其中R1是基团H或C1-8-烷基,R2是基团H或C1-4-烷基,R3、R4、R5和R6各自彼此独立地是选自基团H、OH、NH2和C1-4-烷基的基团。优选使用其中R2是甲基或乙基和R1或R5和R6是H的嘧啶甲酸。尤其优选使用嘧啶甲酸依克多因((S)-1,4,5,6-四氢-2-甲基-4-嘧啶甲酸)和羟基依克多因((S,S)-1,4,5,6-四氢-5-羟基-2-甲基-4-嘧啶甲酸)。根据本发明的组合物优选包含至多15wt%的量的这种类型的嘧啶甲酸。嘧啶甲酸在此优选以相对式I化合物为100∶1至1∶100的重量百分率之比使用,其中重量百分率之比1∶10至10∶1是尤其优选的。
在芳基肟类中,优选使用也称作HMLO、LPO或F5的2-羟基-5-甲基-月桂苯酮肟。其在化妆品剂中使用的适用性例如在DE-A-41 16 123中进行了公开。包含2-羟基-5-甲基月桂苯酮肟的组合物因此适用于治疗伴随炎症的皮肤疾病。已知的是,这种类型的组合物可例如,用于治疗牛皮癣,各种不同形式的湿疹,刺激性和毒性皮炎,UV皮炎和其它的皮肤和外皮附件的过敏性和/或炎症性疾病。除了式I化合物外,还包含芳基肟,优选2-羟基-5-甲基月桂苯酮肟的根据本发明的组合物具有令人惊奇的抗炎症适应性。所述组合物在此优选包含0.01-10wt%的芳基肟,其中尤其优选所述组合物包含0.05-5wt%芳基肟。
可以用于所述组合物的所有化合物或组分是已知且可商购的或可以通过已知的方法合成。
所述一种或多种式I化合物可以以常规方式结合到化妆品或皮肤病组合物中。合适的组合物是用于外部使用的那些,例如呈霜、洗剂、凝胶形式或作为可被喷雾到皮肤上的溶液。适合于内用的是例如胶囊、包衣片剂、粉末、片剂溶液或溶液之类的施用形式。
可以提及的根据本发明的组合物的应用形式的实例是:溶液、悬浮液、乳液、PIT乳液、糊剂、软膏、凝胶、霜、洗剂、粉剂、皂、含表面活性剂的清洁制剂、油、气溶胶和喷剂。其它应用形式的实例是棒,香波和淋浴用组合物。任何所需常规赋形剂,助剂和任选的其它活性化合物可加入所述组合物中。
优选的助剂源自防腐剂、稳定剂、增溶剂、着色剂、气味改进剂。
软膏、糊剂、霜和凝胶可包含常规赋形剂,例如动物和植物脂肪、蜡、石蜡、淀粉、黄蓍胶、纤维素衍生物、聚乙二醇、硅酮、膨润土、硅石、滑石和氧化锌或这些物质的混合物。
粉剂和喷剂可包含常规赋形剂,例如乳糖、滑石、硅石、氢氧化铝、硅酸钙和聚酰胺粉末或这些物质的混合物。喷剂可另外包含常规推进剂,例如氟氯烃、丙烷/丁烷或二甲基醚。
溶液和乳液可包含常规赋形剂,如溶剂,增溶剂和乳化剂,例如水、乙醇、异丙醇、碳酸乙酯、乙酸乙酯、苯甲醇、苯甲酸苄酯、丙二醇、1,3-丁二醇、油、尤其是棉籽油、花生油、玉米胚油、橄榄油、蓖麻油和芝麻油、甘油脂肪酸酯、聚乙二醇和脱水山梨糖醇的脂肪酸酯或这些物质的混合物。
悬浮液可包含常规赋形剂,如液体稀释剂,例如水,乙醇或丙二醇,悬浮介质,例如乙氧基化异硬脂醇,聚氧乙烯山梨糖醇酯和聚氧乙烯脱水山梨糖醇酯,微晶纤维素,偏铝酸(Aluminum metahydroxide),膨润土,琼脂和黄蓍胶或这些物质的混合物。
皂可包含常规赋形剂,如脂肪酸的碱金属盐,脂肪酸单酯的盐,脂肪酸蛋白水解产物,异硫代硫酸盐,羊毛脂,脂肪醇,植物油,植物提取物,甘油,糖或这些物质的混合物。
含表面活性剂的清洁产品可包含常规赋形剂,如脂肪醇硫酸酯的盐、脂肪醇醚硫酸盐、磺基琥珀酸单酯、脂肪酸蛋白水解产物、异硫代硫酸盐、咪唑啉鎓衍生物、牛磺酸甲酯、肌氨酸盐、脂肪酸酰胺醚硫酸盐、烷基酰氨基甜菜碱、脂肪醇、脂肪酸甘油酯、脂肪酸二乙醇酰胺、植物和合成油、羊毛脂衍生物、乙氧基化甘油脂肪酸酯或这些物质的混合物。
面部和身体用油可包含常规赋形剂,如合成油,如脂肪酸酯,脂肪醇,硅油,天然油,如植物油和油状植物提取物,石蜡油,羊毛脂油或这些物质的混合物。
其它的典型化妆品应用形式还有唇膏,唇护理棒,睫毛膏,眼线笔,眼影,胭脂,化妆粉,化妆乳和化妆蜡,和防晒剂,晒前用和晒后用制剂。
根据本发明的优选组合物形式尤其包括乳液。
根据本发明的乳液是有利的并且包含,例如,所述脂肪,油,蜡和其它类脂,以及水和乳化剂,如常用于这类组合物的那些。
脂相可有利地选自以下物质组:
-矿物油,矿物蜡;
-油,如癸酸或辛酸的甘油三酯,另外,天然油例如,蓖麻油;
-脂肪,蜡和其它天然和合成脂肪物质,优选由脂肪酸与具有低碳数的醇,例如与异丙醇,丙二醇或甘油形成的酯,或由脂肪醇与具有低碳数的链烷酸或与脂肪酸形成的酯;
-硅油,如二甲基聚硅氧烷,二乙基聚硅氧烷,二苯基聚硅氧烷和其混合形式。
就本发明而言,乳液,油凝胶或水分散体或脂分散体的油相有利地选自由链长为3至30个C原子的饱和和/或不饱和,支化和/或未支化的链烷羧酸和链长为3至30个C原子的饱和和/或不饱和,支化和/或未支化的醇形成的酯,或选自由芳族羧酸和链长为3至30个C原子的饱和和/或不饱和,支化和/或未支化的醇形成的酯。这种类型的酯油可因而有利地选自肉豆蔻酸异丙酯、棕榈酸异丙基酯、硬脂酸异丙基酯、油酸异丙基酯、硬脂酸正丁基酯、月桂酸正己基酯、油酸正癸基酯、硬脂酸异辛基酯、硬脂酸异壬基酯、异壬酸异壬基酯、棕榈酸2-乙基己基酯、月桂酸2-乙基己基酯、硬脂酸2-己基癸基酯、棕榈酸2-辛基十二烷基酯、油酸油基酯、芥酸油基酯、油酸瓢儿菜基酯、芥酸瓢儿菜基酯和这类酯的合成、半合成和天然混合物,例如霍霍巴油。
油相可另外有利地选自支化和未支化的烃和烃蜡,硅油,二烷基醚,或选自饱和或不饱和,支化或未支化的醇,和脂肪酸三甘油酯,特别是链长为8-24,尤其是12-18个C原子的饱和和/或不饱和,支化和/或未支化的链烷羧酸的三甘油酯。脂肪酸三甘油酯可有利地例如,选自合成、半合成和天然油,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、棕榈仁油和类似物。
这种类型的油和蜡组分的任何所需混合物也可有利地用于本发明目的。使用蜡,例如棕榈酸鲸蜡基酯作为油相的唯一类脂组分也可能是有利的。
油相有利地选自异硬脂酸2-乙基己基酯、辛基十二烷醇、异壬酸异十三烷基酯、异二十烷、椰油酸2-乙基己基酯、苯甲酸C12-15-烷基酯、辛酸/癸酸甘油三酯、二辛基醚。
尤其有利的是苯甲酸C12-15-烷基酯和异硬脂酸2-乙基己基酯的混合物,苯甲酸C12-15-烷基酯和异壬酸异十三烷基酯的混合物,以及苯甲酸C12-15-烷基酯、异硬脂酸2-乙基己基酯和异壬酸异十三烷基酯的混合物。
在所述烃中,石蜡油,角鲨烷和角鲨烯可有利地用于本发明目的。
另外,油相还可以有利地具有一定含量的环状或线性硅油或完全由这类油组成,但优选除了所述硅油外还使用附加含量的其它油相组分。
待根据本发明使用的硅油有利地是环二甲基硅酮(八甲基环四硅氧烷)。然而,使用其它硅油,例如六甲基环三硅氧烷,聚二甲基硅氧烷,聚(甲基苯基硅氧烷)对本发明目的也是有利的。
还尤其有利的是环二甲基硅酮和异壬酸异十三烷基酯的混合物,和环二甲基硅酮和异硬脂酸2-乙基己基酯的混合物。
根据本发明的组合物的水相任选有利地包含具有低碳数的醇,二醇或多元醇和它们的醚,优选乙醇、异丙醇、丙二醇、甘油、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、二甘醇单甲基或单乙基醚和类似产品,另外,具有低碳数的醇,例如乙醇、异丙醇、1,2-丙二醇、甘油,尤其是一种或多种增稠剂,所述增稠剂可有利地选自二氧化硅、硅酸铝、多糖或其衍生物,例如透明质酸、黄原胶、羟基丙基甲基纤维素、尤其有利地选自聚丙烯酸酯,优选选自所谓卡波普(Carbopols)的聚丙烯酸酯,例如卡波普等级980,981,1382,2984、5984,在每种情况下单独或组合使用。
尤其使用上述溶剂的混合物。在醇属溶剂的情况下,水可以是另一成分。
根据本发明的乳液是有利的,并且包含,例如,所述脂肪,油,蜡和其它类脂,以及水和乳化剂,如常用于这类制剂的那些。
在一个优选实施方案中,根据本发明的组合物包含亲水性表面活性剂。
亲水性表面活性剂优选选自烷基葡糖苷、酰基乳酸盐/酯、甜菜碱和椰油两性乙酸盐。
烷基葡糖苷自身有利地选自由以下结构式表征的烷基葡糖苷:
其中R是含4至24个碳原子的支化或未支化烷基基团,和其中DP表示至多2的平均葡糖基化度。
值DP表示根据本发明使用的烷基葡糖苷的糖苷化度并且定义为
其中p1、p2、p3…pi表示单倍,二倍,三倍...i-倍葡糖基化产物的以重量百分比计的比例。根据本发明有利的产物是葡糖基化度为1-2,尤其有利地为1.1至1.5,非常尤其有利地为1.2-1.4,尤其是1.3的那些。
值DP考虑了以下情况,烷基葡糖苷由于其制备原因而一般为单和低聚葡糖苷的混合物形式。按照本发明,通常为约40-70wt%的相对高含量的单葡糖苷是有利的。
根据本发明特别有利的烷基葡糖苷选自辛基吡喃葡糖苷、壬基吡喃葡糖苷、癸基吡喃葡糖苷、十一烷基吡喃葡糖苷、十二烷基吡喃葡糖苷、十四烷基吡喃葡糖苷和十六烷基吡喃葡糖苷。
酰基乳酸盐自身有利地选自由以下结构式表征的物质:
其中R1是含1至30个碳原子的支化或未支化烷基基团,M+选自碱金属离子和被一个或多个烷基和/或一个或多个羟基烷基基团取代的铵离子或对应于一半当量的碱土金属离子。
甜菜碱有利地选自由以下结构式表征的物质:
其中R2是含1至30个碳原子的支化或未支化烷基基团。
R2尤其有利地是含6至12个碳原子的支化或未支化烷基基团。
根据本发明的组合物有利地特征在于亲水性表面活性剂以浓度0.01-20wt%,优选0.05-10wt%,尤其优选0.1-5wt%存在,在每种情况下基于组合物的总重。
为了使用,将根据本发明的化妆品和皮肤病组合物按照对于化妆品而言的常规方式以足够量施用到皮肤和/或毛发上。
根据本发明的化妆品和皮肤病组合物可以各种不同的形式存在。因此,它们可以是例如,溶液,无水组合物,油包水(W/O)型或水包油(O/W)型乳液或微乳液,多重乳液,例如水包油包水(W/O/W)型多重乳液,凝胶,固体棒,软膏或气溶胶。还有利的是将依克多因以包囊形式施用,例如在胶原基质和其它常规包囊材料中,例如作为纤维素包囊形式,在明胶,蜡基质中或脂质体包囊。特别地,如描述于DE-A 43 08 282中的蜡基质已被证实有利。优选乳液。O/W乳液是尤其优选的。乳液,W/O乳液和O/W乳液可按照常规方式得到。
可以使用的乳化剂是,例如,已知的W/O和O/W乳化剂。有利地在根据本发明的优选的O/W乳液中使用其它的常规共乳化剂。
根据本发明有利的共乳化剂是,例如,O/W乳化剂,主要来自HLB值为11-16的物质,非常尤其有利地HLB值为14.5-15.5的物质,只要O/W乳化剂具有饱和基团R和R′。如果O/W乳化剂具有不饱和基团R和/或R′或在异烷基衍生物情况下,则这些乳化剂的优选的HLB值也可更低或更高。
有利的是选择脂肪醇乙氧基化物,其选自乙氧基化硬脂醇、鲸蜡醇、鲸蜡基硬脂醇(十六/十八烷醇)。尤其优选以下:聚乙二醇(13)硬脂基醚(硬脂基聚氧乙烯醚-13)、聚乙二醇(14)硬脂基醚(硬脂基聚氧乙烯醚-14)、聚乙二醇(15)硬脂基醚(硬脂基聚氧乙烯醚-15)、聚乙二醇(16)硬脂基醚(硬脂基聚氧乙烯醚-16)、聚乙二醇(17)硬脂基醚(硬脂基聚氧乙烯醚-17)、聚乙二醇(18)硬脂基醚(硬脂基聚氧乙烯醚-18)、聚乙二醇(19)硬脂基醚(硬脂基聚氧乙烯醚-19)、聚乙二醇(20)硬脂基醚(硬脂基聚氧乙烯醚-20)、聚乙二醇(12)异硬脂基醚(异硬脂基聚氧乙烯醚-12)、聚乙二醇(13)异硬脂基醚(异硬脂基聚氧乙烯醚-13)、聚乙二醇(14)异硬脂基醚(异硬脂基聚氧乙烯醚-14)、聚乙二醇(15)异硬脂基醚(异硬脂基聚氧乙烯醚-15)、聚乙二醇(16)异硬脂基醚(异硬脂基聚氧乙烯醚-16)、聚乙二醇(17)异硬脂基醚(异硬脂基聚氧乙烯醚-17)、聚乙二醇(18)异硬脂基醚(异硬脂基聚氧乙烯醚-18)、聚乙二醇(19)异硬脂基醚(异硬脂基聚氧乙烯醚-19)、聚乙二醇(20)异硬脂基醚(异硬脂基聚氧乙烯醚-20)、聚乙二醇(13)鲸蜡基醚(十六烷基聚氧乙烯醚-13)、聚乙二醇(14)鲸蜡基醚(十六烷基聚氧乙烯醚-14)、聚乙二醇(15)鲸蜡基醚(十六烷基聚氧乙烯醚-15)、聚乙二醇(16)鲸蜡基醚(十六烷基聚氧乙烯醚-16)、聚乙二醇(17)鲸蜡基醚(十六烷基聚氧乙烯醚-17)、聚乙二醇(18)鲸蜡基醚(十六烷基聚氧乙烯醚-18)、聚乙二醇(19)鲸蜡基醚(十六烷基聚氧乙烯醚-19)、聚乙二醇(20)鲸蜡基醚(十六烷基聚氧乙烯醚-20)、聚乙二醇(13)异鲸蜡基醚(异十六烷基聚氧乙烯醚-13)、聚乙二醇(14)异鲸蜡基醚(异十六烷基聚氧乙烯醚-14)、聚乙二醇(15)异鲸蜡基醚(异十六烷基聚氧乙烯醚-15)、聚乙二醇(16)异鲸蜡基醚(异十六烷基聚氧乙烯醚-16)、聚乙二醇(17)异鲸蜡基醚(异十六烷基聚氧乙烯醚-17)、聚乙二醇(18)异鲸蜡基醚(异十六烷基聚氧乙烯醚-18)、聚乙二醇(19)异鲸蜡基醚(异十六烷基聚氧乙烯醚-19)、聚乙二醇(20)异鲸蜡基醚(异十六烷基聚氧乙烯醚-20)、聚乙二醇(12)油基醚(油基聚氧乙烯醚-12)、聚乙二醇(13)油基醚(油基聚氧乙烯醚-13)、聚乙二醇(14)油基醚(油基聚氧乙烯醚-14)、聚乙二醇(15)油基醚(油基聚氧乙烯醚-15)、聚乙二醇(12)月桂基醚(月桂基聚氧乙烯醚-12)、聚乙二醇(12)异月桂基醚(异月桂基聚氧乙烯醚-12)、聚乙二醇(13)鲸蜡基硬脂基醚(十六烷基十八烷基聚氧乙烯醚-13)、聚乙二醇(14)鲸蜡基硬脂基醚(十六烷基十八烷基聚氧乙烯醚-14)、聚乙二醇(15)鲸蜡基硬脂基醚(十六烷基十八烷基聚氧乙烯醚-15)、聚乙二醇(16)鲸蜡基硬脂基醚(十六烷基十八烷基聚氧乙烯醚-16)、聚乙二醇(17)鲸蜡基硬脂基醚(十六烷基十八烷基聚氧乙烯醚-17)、聚乙二醇(18)鲸蜡基硬脂基醚(十六烷基十八烷基聚氧乙烯醚-18)、聚乙二醇(19)鲸蜡基硬脂基醚(十六烷基十八烷基聚氧乙烯醚-19)、聚乙二醇(20)鲸蜡基硬脂基醚(十六烷基十八烷基聚氧乙烯醚-20)。
从下组选择脂肪酸乙氧基化物也是有利的:
聚乙二醇(20)硬脂酸酯、聚乙二醇(21)硬脂酸酯、聚乙二醇(22)硬脂酸酯、聚乙二醇(23)硬脂酸酯、聚乙二醇(24)硬脂酸酯、聚乙二醇(25)硬脂酸酯、聚乙二醇(12)异硬脂酸酯、聚乙二醇(13)异硬脂酸酯、聚乙二醇(14)异硬脂酸酯、聚乙二醇(15)异硬脂酸酯、聚乙二醇(16)异硬脂酸酯、聚乙二醇(17)异硬脂酸酯、聚乙二醇(18)异硬脂酸酯、聚乙二醇(19)异硬脂酸酯、聚乙二醇(20)异硬脂酸酯、聚乙二醇(21)异硬脂酸酯、聚乙二醇(22)异硬脂酸酯、聚乙二醇(23)异硬脂酸酯、聚乙二醇(24)异硬脂酸酯、聚乙二醇(25)异硬脂酸酯、聚乙二醇(12)油酸酯、聚乙二醇(13)油酸酯、聚乙二醇(14)油酸酯、聚乙二醇(15)油酸酯、聚乙二醇(16)油酸酯、聚乙二醇(17)油酸酯、聚乙二醇(18)油酸酯、聚乙二醇(19)油酸酯、聚乙二醇(20)油酸酯。
可有利地使用的乙氧基化烷基醚羧酸或其盐是月桂基聚氧乙烯醚-11羧酸钠。可有利地使用的烷基醚硫酸盐是月桂基聚氧乙烯醚-14硫酸钠。可有利地使用的乙氧基化胆甾醇衍生物是聚乙二醇(30)胆甾醇基醚。聚乙二醇(25)大豆甾醇也被证实是成功的。可有利地使用的乙氧基化甘油三酯是聚乙二醇(60)月见草甘油酯。
另外有利的是从以下选择聚乙二醇甘油脂肪酸酯:聚乙二醇(20)甘油基月桂酸酯,聚乙二醇(21)甘油基月桂酸酯,聚乙二醇(22)甘油基月桂酸酯,聚乙二醇(23)甘油基月桂酸酯,聚乙二醇(6)甘油基癸酸酯/辛酸酯,聚乙二醇(20)甘油基油酸酯,聚乙二醇(20)甘油基异硬脂酸酯,聚乙二醇(18)甘油基油酸酯/椰油酸酯。
同样可有利地从以下选择脱水山梨糖醇酯:聚乙二醇(20)脱水山梨糖醇单月桂酸酯,聚乙二醇(20)脱水山梨糖醇单硬脂酸酯,聚乙二醇(20)脱水山梨糖醇单异硬脂酸酯,聚乙二醇(20)脱水山梨糖醇单棕榈酸酯,聚乙二醇(20)脱水山梨糖醇单油酸酯。
任选的,但根据本发明可能有利的W/O乳化剂是以下乳化剂:
含8至30个碳原子的脂肪醇,链长为8至24个碳原子,尤其是12-18个碳原子的饱和和/或不饱和,支化和/或未支化链烷羧酸的单甘油酯,链长为8至24个碳原子,尤其是12-18个碳原子的饱和和/或不饱和,支化和/或未支化链烷羧酸的二甘油酯,链长为8至24个碳原子,尤其是12-18个碳原子的饱和和/或不饱和,支化和/或未支化醇的单甘油醚,链长为8至24个碳原子,尤其是12-18个碳原子的饱和和/或不饱和,支化和/或未支化醇的二甘油醚,链长为8至24个碳原子,尤其是12-18个碳原子的饱和和/或不饱和,支化和/或未支化链烷羧酸的丙二醇酯,和链长为8-24个碳原子,尤其是12-18个碳原子的饱和和/或不饱和,支化和/或未支化链烷羧酸的脱水山梨糖醇酯。
尤其有利的W/O乳化剂是单硬脂酸甘油酯、单异硬脂酸甘油酯、单肉豆蔻酸甘油酯、单油酸甘油酯、单硬脂酸二甘油酯、单异硬脂酸二甘油酯、丙二醇单硬脂酸酯、丙二醇单异硬脂酸酯、丙二醇单辛酸酯、丙二醇单月桂酸酯、脱水山梨糖醇单异硬脂酸酯、脱水山梨糖醇单月桂酸酯、脱水山梨糖醇单辛酸酯、脱水山梨糖醇单异油酸酯、蔗糖二硬脂酸酯、鲸蜡醇、硬脂醇、花生醇、山萮醇、异山嵛醇、鲨油醇、鲛肝醇、聚乙二醇(2)硬脂基醚(硬脂基聚氧乙烯醚-2)、单月桂酸甘油酯、单癸酸甘油酯、单辛酸甘油酯或PEG 30二聚羟基硬脂酸酯。
根据本发明的优选的组合物特别适用于针对老化过程和针对氧化应激,即针对例如由日光照射、热或其它影响产生的自由基引起的损害而保护人类皮肤。在这方面,它们以常用于该用途的各种施用形式存在。例如,它们可尤其是作为洗剂或乳液的形式,如霜或乳剂(O/W、W/O、O/W/O、W/O/W)的形式、油-醇、油-水或水-醇凝胶或溶液的形式,固体棒的形式存在或可被配制为气溶胶形式。
组合物可包含常用于这类组合物中的化妆品助剂,例如,增稠剂、软化剂、润湿剂、表面活性剂、乳化剂、防腐剂、消泡剂、香料、蜡、羊毛脂、推进剂、将组合物自身或皮肤着色的染料和/或颜料和通常用于化妆品中的其它成分。
所使用的染料优选是在Cosmetics Regulation,Annex 3中作为positivelist列出的许可染料。
所使用的防腐剂优选是在Cosmetics Regulation,Annex 6中作为positive list列出的许可防腐剂,或还有抗菌颜料,例如,WO 2004/0092283或WO 2004/091567中描述的那些。
适合的防腐剂因此还有对羟基苯甲酸的烷基酯,乙内酰脲衍生物,丙酸盐或许多铵化合物。
非常尤其优选的防腐剂是对羟基苯甲酸甲酯、对羟苯甲酸丙酯、咪唑烷基脲、脱羟基乙酸钠或苄醇。防腐剂以0.5-2wt%的量使用。
通常将润肤剂或软化剂引入化妆品组合物。它们优选以0.5-50wt%,优选5-30wt%使用,基于整个组合物。一般而言,软化剂可以按类别分类,例如可有酯类,脂肪酸类或脂肪醇类,多元醇类,烃类和含至少一个酰胺结构单元的油类。
特别地,代表性的含至少一个酰胺结构单元的油连同它们的合成在EP1044676和EP 0928608中进行了描述。尤其优选指出的化合物是N-月桂酰基肌氨酸异丙酯,它可从Ajinomoto以产品名称Eldew SL-205商购。
所述酯中,可以选择一酯或二酯。在这一方面,实例是己二酸二丁酯,癸二酸二乙酯,diisopropyl dimerate或琥珀酸二辛酯。支化脂肪酸酯是例如,肉豆蔻酸2-乙基己酯、硬脂酸异丙酯或棕榈酸异十八烷基酯。三元酸酯是例如,三亚油酸三异丙酯或柠檬酸三月桂酯。直链脂肪酸酯是例如,棕榈酸月桂酯、乳酸肉豆蔻酯、芥酸油基酯或油酸硬脂基酯。优选的酯是椰油基-辛酸酯/癸酸酯(=INCI名称,它们是由椰子脂肪醇与饱和中链脂肪酸制成的酯),丙二醇肉豆蔻基醚乙酸酯,己二酸二异丙酯或辛酸鲸蜡基酯。
适合的脂肪醇和酸是含10-20个C原子的化合物。尤其优选的化合物是鲸蜡基、肉豆蔻基、棕榈基或硬脂醇或酸。
适合的多元醇是线性或带支链烷基多羟基化合物,例如丙二醇、山梨糖醇或甘油。然而,还可能使用聚合物多元醇,例如聚丙二醇或聚乙二醇。丁二醇和丙二醇也是尤其适合的用于提高渗透能力的化合物。
作为软化剂的烃的实例是通常含12-30个C原子的化合物。具体实例是苯甲酸芳烷基酯、苯甲酸烷基酯、矿物油、凡士林、角鲨烯或异链烷烃。
其它润肤剂或疏水试剂优选是苯甲酸C12-C15烷基酯、己二酸二辛酯、硬脂酸辛酯、辛基十二烷醇、月桂酸己酯、新戊酸辛基十二烷基酯、环二甲基硅酮、二辛酸醚、二甲聚硅氧烷、苯基三甲聚硅氧烷、肉豆蔻酸异丙酯、辛酸/癸酸甘油酯、丙二醇二辛酸酯/二癸酸酯或油酸癸基酯。
在本发明意义上的化妆品组合物的功能成分的另一种类是增稠剂。增稠剂通常以0.1-20wt%,优选0.5-10wt%的量使用,基于总量。这些化合物的实例是交联的聚丙烯酸酯材料,可从B.F.Goodrich Company以商品名Carbopol商购。还可能使用增稠剂例如黄原胶、角叉菜胶、明胶、刺槐树胶、果胶或卡罗布豆粉。
在某些情况下,化合物既是增稠剂又是软化剂。它们的实例是硅酮胶(动态粘度>10厘沱),酯,例如甘油硬脂酸酯,或纤维素衍生物例如羟丙基纤维素。
所使用的分散剂或增溶剂可以是油,蜡或其它类脂,低级一元醇或低级多元醇或它们的混合物。尤其优选的一元醇或多元醇包括乙醇、异丙醇、丙二醇、甘油和山梨糖醇。
本发明的一个优选实施方案是乳液,其以保护性霜或乳剂形式存在,并除了式I化合物外,还包含,例如,脂肪醇,脂肪酸,脂肪酸酯,尤其是脂肪酸的甘油三酯,羊毛脂,天然和合成油或蜡和在水存在下的乳化剂。
其它优选的实施方案是基于天然或合成油和蜡,羊毛脂,脂肪酸酯,尤其是脂肪酸的三甘油酯的油状洗剂,或基于低级醇例如乙醇,或二醇例如丙二醇,和/或多元醇例如甘油,和油,蜡和脂肪酸酯例如脂肪酸的三甘油酯的油醇类洗剂。
根据本发明的组合物还可以呈醇凝胶形式,其包含一种或多种低级醇或多元醇,如乙醇、丙二醇或甘油,和增稠剂如硅藻土。油醇凝胶还包含天然或合成油或蜡。
固体棒由天然或合成的蜡和油、脂肪醇、脂肪酸、脂肪酸酯、羊毛脂和其它类脂组成。
如果组合物配制为气溶胶,则一般使用常规推进剂,如烷烃、氟代烷烃和氯氟烷烃。
化妆品组合物还可用于抗光化学损害而保护毛发,这样防止颜色变化,漂白或机械性质的损害。在这种情况下,合适的配方是冲洗掉型洗发剂,洗剂,凝胶或乳液的形式,所述组合物在洗发之前或之后,在染色或漂白之前或之后或在持久烫发之前或之后施用。也可选择用于定型或处理头发的洗剂或凝胶的形式,用于刷或吹卷发的洗剂或凝胶的形式,用于头发的发蜡,持久烫发组合物,头发的染色剂或漂白剂的形式的组合物。除了式I化合物外,组合物还可包含用于这类组合物中的各种助剂,如表面活性剂,增稠剂,聚合物,软化剂,防腐剂,泡沫稳定剂,电解质,有机溶剂,硅酮衍生物,油,蜡,防油脂剂,将组合物自身或头发着色的染料和/或颜料,或常用于头发护理的其它成分。
如上所述,所述组合物可以包括或包含,基本构成自或构成自所述必要或任选的成分。可以用于所述组合物的所有化合物或组分是已知且可商购的或可以通过已知的方法合成。
本发明另外涉及用于制备组合物的方法,其特征在于将至少一种含上述基团的式I化合物与化妆品、药物或皮肤病学上或对于食品而言适合的赋形剂混合,并涉及式I化合物用于制备组合物,尤其是具有抗氧化性能的组合物的用途。
根据本发明的组合物可利用本领域技术人员熟知的技术而制备。
混合可引起式I化合物溶解,乳化或分散在赋形剂中。
本发明还涉及式I化合物的制备方法,其中R6彼此独立地表示含1-18个C原子的烷基,优选含1-5个C原子的烷基,尤其优选甲基,R5=OH,其特征在于使式II的化合物
其中R1-R4可以具有上述含义之一,
与选自POCl3,光气或三氟磺酸酐的试剂和芳烷基-、二芳基-或二烷基甲酰胺反应而获得式III的中间体
其中R1-R4可以具有上述含义之一,
并随后使它与膦酸二烷基酯反应。
膦酸二烷基酯的烷基形成R6。
获得上述式III的中间体的反应亦称Vilsmeier反应。
芳烷基-、二芳基-或二烷基甲酰胺的实例是N-苯基-N-甲基甲酰胺、N,N-二苯基甲酰胺、N,N-二甲基甲酰胺、N,N-二乙基甲酰胺、N,N-二丁基甲酰胺。还可能使用N,N-甲酰基哌啶代替甲酰胺。
Vilsmeier反应优选在POCl3和二甲基甲酰胺存在下进行。
Vilsmeier反应优选在惰性气体条件下进行。POCl3或选自所述组的另一种试剂有利地在温度<5℃下引入。实际的反应温度在-50至75℃,优选-20至30℃。反应尤其优选在室温下进行。
式III的中间体与膦酸二烷基酯的反应优选在惰性气体条件下且在20-100℃,优选25-85℃之间的反应温度下进行。使用的催化剂可以是例如,亚磷酸三烷基酯、CsF、KF、DBU(二氮杂双环十一碳-7-烯)、钠、甲醇钠、三乙胺或还有NaOH,但是其中在使用NaOH的情况下要求进一步的相转移催化剂。优选使用亚磷酸三烷基酯。
亚磷酸三烷基酯的烷基优选相同于所述膦酸二烷基酯的烷基并且代表式I化合物中的具有相关公开含义的R6。
酯水解(例如通过与盐酸反应)获得其中R6在每种情况下表示H的式I化合物。
在随后的还原步骤中,例如通过使用氢碘酸在红磷存在下还原,可以获得其中R5表示H的式I化合物。
例如,还原在乙酸中在10-150℃,优选20-125℃的温度下,尤其优选在100-120℃下进行。
例如,通过添加碱或碱土金属氢氧化物、碳酸盐或碳酸氢盐在极性溶剂,例如乙醇、甲醇或异丙醇中进行到式I的膦酸的盐的转化。
指出的式II的化合物和合成中的其它反应物可商购或可通过本领域技术人员从文献熟知的合成得到。适合的反应条件的选择是合成领域技术人员已知的标准技术。
还注意到,式I化合物可对所述组合物具有稳定作用。当用于相应的产品中时,这些产品因此也保持较长时间稳定且不改变其外观。特别地,成分,如维生素的功效甚至在延长时间内应用或延长时间储存的情况下也得到保持。在用于针对UV射线的影响而保护皮肤的组合物的情况下,这些化妆品尤其特别有利,因为这些化妆品经受尤其高的由UV辐射引起的应激。
式I化合物的这种积极效果使得它非常适用于化妆品或药物组合物中。
式I化合物的性能对用于食品或用作食品增补剂或用作功能食品同样应该视为积极的。关于食品给出的其它解释也相应地适用于食品增补剂和功能食品。
可按照本发明用一种或多种式I化合物强化的食品包括适合被动物进食或被人进食的所有物质,例如维生素和其维生素原、脂肪、矿物质或氨基酸。(食品可以是固体,也可是液体,即以饮料形式存在)。本发明因此还涉及式I化合物用作人类或动物营养品的食品添加剂的用途,以及涉及是食品或食品增补剂并且包含相应赋形剂的组合物。
可按照本发明用一种或多种式I化合物强化的食品还有,例如,源自单一天然来源的食品,例如,糖,单一植物物种的不加甜味的汁、蜜液或酱泥,例如,不加甜味的苹果汁(例如还有不同种类的苹果汁的混合物),葡萄柚汁,橙汁,苹果原浆果片,杏泥,番茄汁,番茄酱,番茄泥等。食品的其它实例是源自单一植物物种的谷物或谷类和由这类植物物种制成的材料,例如,谷类糖浆,黑麦粉,小麦粉或燕麦麸。这类食品的混合物也适用于按照本发明用一种或多种式I化合物强化,例如多重维生素制剂,矿物质混合物或加甜味果汁。可以提及的食品的其它实例是食品制剂,例如加工谷物,饼干,混合饮料,尤其为儿童制成的食品,如酸奶,疗养食品,低热值食品或动物饲料。
可按照本发明用一种或多种式I化合物强化的食品因此包括碳水化合物、类脂、蛋白质、无机元素、微量元素、维生素、水或植物和动物的活性代谢物的所有可食用的组合。
可按照本发明用一种或多种式I化合物强化的食品优选口服施用,例如为膳食、丸剂、片剂、胶囊、粉末、糖浆、溶液或悬浮剂的形式。
用一种或多种式I化合物强化的根据本发明的食品可利用本领域技术人员熟知的技术制备。
由于它们作为抗氧化剂或自由基清除剂的作用,式I化合物还适合作为药剂成分,其中它们支持或替代清除身体内自由基的自然机制。式I化合物在一些情况下可以与自由基清除剂,例如维生素C在它们的作用方面进行比较。式I化合物可以用于,例如,预防性治疗皮肤的炎症和过敏并且在某些情况下用于预防某些类型的癌症。式I化合物尤其是适合于制备治疗炎症、过敏和刺激,尤其是皮肤的那些症状的药剂。此外可能制备充当静脉补药,提高血液毛细管强度的试剂,cuperose抑制剂,化学、物理或光化红斑的抑制剂,敏感皮肤治疗剂,解充血剂,脱水剂,减肥剂,抗皱纹剂,细胞外基质的合成组分的刺激剂,改进皮肤弹性的增强剂和抗老化剂的药剂。另外,在这方面优选的式I化合物显示抗过敏和消炎和抗刺激作用。它们因此适合于制备治疗炎症或过敏性反应的药剂。
将在下面参考实施例更详细地阐明本发明。本发明可以在整个要求的范围内实施并且不局限于在此给出的实施例。
实施例
实施例1:[(7,8-二羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸的制备
程序:
第一步:
将10g(59.5mmol)2,3,4-三羟基苯乙酮溶于最初在-50℃(干冰/乙醇)下引入的120ml N,N-二甲基甲酰胺,随后缓慢地经大约30分钟逐滴添加21.8ml(237.9mmol)磷酰氯。
随后在-20℃下搅拌该透明溶液30min.,移除冷浴,并在室温下继续搅拌过夜。将完整的反应溶液倒入大约200ml冰/水中,并在抽吸下过滤所得悬浮液并用水冲洗。在真空干燥箱中在45℃和200毫巴下将所获得的固体干燥过夜。
1H NMR(500MHz)in DMSOδ(ppm):.7.0(d,1H),7.5(d,1H),8.8(s,1H),10.1(s,1H),10.6(bs,OH).
13C NMR(75MHz)in DMSOδ(ppm):114.8,115.5,117.7,119,133.6,146.3,151.3,162.3,174.5,188.6.
ESI-MS(m/z):206.
第二步:
在氩气下在RT(RT=室温)下将4.3g(20.858mmol)7,8-二羟基-4-氧代-4H-1-苯并吡喃-3-甲醛悬浮在19ml膦酸二甲酯中,然后添加几滴亚磷酸三甲基酯。然后在85℃下搅拌该悬浮液1.5h,在RT下继续搅拌过夜。
对于后处理,将反应溶液添加到200ml二氯甲烷中并在RT下搅拌1h。该膦酸酯作为固体沉淀。
1H NMR(250MHz)in DMSOδ(ppm):.3.6(d,3H),3.7(d,3H),5.25(bd,1H),6.2(bs,OH),6.95(d,1H),7.45(d,1H),8.25(d,1H),9.45(bs,OH),10.53(bs,OH).
13C NMR(63MHz)in DMSOδ(ppm):53(d),53.4(d),54.8,58.1,60.8,114.4,115.4,116.5,120.6,133.0,146.6,150.3,155.2,174.1.
31P NMR(100MHz)in DMSOδ(ppm):25.3.
第三步:
将5.2g(16.44mmol)[(7,8-二羟基-4-氧代-4H-1-苯并吡喃-3-基)羟甲基]膦酸二甲酯悬浮在40ml 2N盐酸中并加热到沸点。在完全水解之后,将反应溶液冷却到RT,在这期间膦酸作为固体沉淀。在过滤之后,用少量水洗涤产物并干燥。
1H NMR(250MHz)in DMSOδ(ppm):.5.0(d,1H),6.9(d,1H),7.4(d,1H),8.2(d,1H),9.4(bs,OH),10.25(bs,OH).
13C NMR(63MHz)in DMSOδ(ppm):59.1,61.8,114.2,115.4,116.8,121.9,132.9,146.5,150.0,154.7.
31P NMR(100MHz)in DMSOδ(ppm):18.8.
ESI-MS(m/z):288.
实施例2:
与实施例1类似地使以下物质反应:
a)2,4-二羟基-3-甲基苯乙酮与磷酰氯,随后与膦酸二甲酯在二甲基甲酰胺中反应,获得[(7-羟基-8-甲基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸二甲酯。
1H NMR(300MHz)in DMSOδ(ppm):2.25(s,3H),3.66(d,3H),3.74(d,3H),5.27(d,1H),7.03(d,1H),7.81(d,1H),8.3(d,1H).
酯水解产生[(7-羟基-8-甲基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸。
1H NMR(300MHz)in DMSOδ(ppm):2.21(s,3H),5.0(d,1H),6.98(d,1H),7.76(d,1H),8.23(d,1H).
b)2,4-二羟基苯乙酮与磷酰氯,随后与膦酸二甲酯在二甲基甲酰胺中反应,获得[(7-羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸二甲酯。
1H NMR(500MHz)in DMSOδ(ppm):3.63(d,3H),3.72(d,3H),5.24(d,1H),6.87(d,1H),6.95(dd,1H),7.93(d,1H),8.21(d,1H).
酯水解产生[(7-羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸。
1H NMR(300MHz)in DMSOδ(ppm):5.18(d,1H),6.9(d,1H),6.97(dd,1H),7.97(d,1H),8.21(d,1H).
c)2,4-二羟基苯乙酮与磷酰氯,随后与膦酸二乙酯在二甲基甲酰胺中反应,获得[(7-羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸二乙酯。
d)2,5-二羟基苯乙酮与磷酰氯,随后与膦酸二甲酯在二甲基甲酰胺中反应,获得[(6-羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸二甲酯。
1H NMR(300MHz)in DMSOδ(ppm):.3.62(d,3H),3.71(d,3H),5.75(d,1H),7.23(dd,1H),7.35(d,1H),7.49(d,1H),8.27(d,1H).
酯水解产生[(6-羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸。
1H NMR(300MHz)in DMSOδ(ppm):5.2(d,1H),7.22(dd,1H),7.33(d,1H),7.51(d,1H),8.24(d,1H).
e)2-羟基-5-甲氧基苯乙酮与磷酰氯,随后与膦酸二甲酯在二甲基甲酰胺中反应,获得[(6-甲氧基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸二甲酯。
1H NMR(300MHz)in DMSOδ(ppm):3.62(d,3H),3.71(d,3H),3.83(s,3H),5.28(d,1H),7.35(dd,1H),7.44(d,1H),7.54(d,1H),8.29(d,1H).
酯水解产生[(6-甲氧基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸。
1H NMR(300MHz)in DMSOδ(ppm):3.84(s,3H),5.1(d,1H),7.36(dd,1H),7.44(d,1H),7.56(d,1H),8.26(d,1H).
f)2,5-二羟基苯乙酮与磷酰氯,随后与膦酸二丁酯在二甲基甲酰胺中反应,获得[(6-羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸二丁酯。
g)2,3,4-三羟基苯乙酮与磷酰氯,随后与膦酸二(十二烷基)酯在二甲基甲酰胺中反应,获得[(7,8-二羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸二(十二烷基)酯。
酯水解产生[(7,8-二羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸。
h)2,3,4-三羟基苯乙酮与磷酰氯,随后与膦酸二(十八烷基)酯在二甲基甲酰胺中反应,获得[(7,8-二羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸二(十八烷基)酯。
实施例3:
将根据实施例2d)制备的[(6-羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸溶于乙醇,随后添加1M KOH溶液直到固体沉淀,获得[(6-羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸的钾盐。
实施例4:[(6-羟基-4-氧代-4H-苯并吡喃-3-基)甲基]膦酸的制备
将[(6-羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸(10mmol)(根据实施例2d)制备),氢碘酸(57%)(38mmol)和红磷(20mmol)添加到乙酸(100ml)中。在110-115℃下加热该混合物直到反应完成。随后过滤该热反应混合物,并用10ml热乙酸洗涤残余物两次。通过添加Na2SO3水溶液将该滤液脱色。固体在6-10℃的温度下沉淀。在过滤之后,用少量冷水洗涤该固体并干燥,获得[(6-羟基-4-氧代-4H-苯并吡喃-3-基)甲基]膦酸。
1H NMR(300MHz)in DMSOδ(ppm):.2.9(d,2H),7.25(dd,1H),7.38(d,1H),7.5(d,1H),8.2(d,1H).
31P NMR(100MHz)in DMSOδ(ppm):16.8.
MS(m/z):222(M+).
实施例5:根据实施例1制备的[(7,8-二羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸的抗氧化性能。
a)抗氧化功效的测定基础是所谓的DPPH试验,如以下文献中所述:Bünger等人[Buenger,J.Ackermann,H.,Jentzsch,A.,Mehling,A.,Pfizner,I.,Reiffen,K.-A.,Schroeder,K.-R.和Wollenweber U.,An interlaboratorycomparison of methods used to assess antioxidant potentials,int.J.Cosm.Sci.,28(2006)1-12]。在DPPH试验中测定[(7,8-二羟基-4-氧代-4H-苯并吡喃-3-基)羟基甲基]膦酸的抗氧化功效。EC50值是0.24μmol/l并反映出优异的自由基清除剂性能。
b)抗氧化功效的测定基础还有所谓的TEAC试验(trolox等效抗氧化活性试验),如以下文献中所述:Buenger等人[Buenger,J.,Ackermann,H.,Jentzsch,A.,Mehling,A.,Pfizner,I.,Reiffen,K.-A.,Schroeder,K.-R.和Wollenweber U.,An interlaboratory comparison of methods used to assessantioxidant potentials,Int.J.Cosm.Sci.,28(2006),1-12]。
ABTS[2,2′-连氮基双(3-乙基苯并噻唑啉-6-磺酸)]通过产生在734nm处吸收的稳定的自由基阳离子与过氧化二硫酸钾反应。所测量的抗氧化剂减少自由基阳离子并因此使在734nm处的吸收能力减弱。在6分钟的固定时间跨度之后测量吸收率。所测量的物质的抗氧化潜能表示为与trolox相比的活性。所测量的物质在测量期间可以溶于水或乙醇中。
与trolox的1.0相比,所测得的值是0.93,即根据本发明的化合物显示高的抗氧化潜能。
实施例6:组合物
包含根据实施例1或2的化合物的化妆品组合物的示例性配方在下面给出。此外,指出了可商购化合物的INCI名称。
UV-Pearl,OMC代表具有以下INCI名称的组合物:水(EU:Aqua)、甲氧基肉桂酸乙基己酯、硅石、PVP、氯苯甘醚(Chlorphenesin)、BHT;这种组合物可从Merck KGaA,Darmstadt以品名UV PearlTMOMC商购。表中指出的其它UV-Pearls各自具有类似组成,只是OMC已经被指出的UV过滤剂替代。
表1W/O乳液(数据以wt%为单位)
1-1 | 1-2 | 1-3 | 1-4 | 1-5 | 1-6 | 1-7 | 1-8 | 1-9 | 1-10 | |
二氧化钛 | 2 | 5 | 3 | |||||||
[(7,8-二羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸 | 5 | 3 | 2 | 1 | 2 | 1 | 1 | |||
[(6-羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸 | 1 | 2 | 1 | |||||||
氧化锌 | 5 | 2 | ||||||||
UV-Pearl,OMC | 30 | 15 | 15 | 15 | 15 | 15 | 15 | 15 | 15 | 15 |
聚甘油基-3-Dimerate | 3 | 3 | 3 | 3 | 3 | 3 | 3 | 3 | 3 | 3 |
白蜂蜡 | 0.3 | 0.3 | 0.3 | 0.3 | 0.3 | 0.3 | 0.3 | 0.3 | 0.3 | 0.3 |
氢化蓖麻油 | 0.2 | 0.2 | 0.2 | 0.2 | 0.2 | 0.2 | 0.2 | 0.2 | 0.2 | 0.2 |
液体石蜡 | 7 | 7 | 7 | 7 | 7 | 7 | 7 | 7 | 7 | 7 |
辛酸/癸酸甘油三酯 | 7 | 7 | 7 | 7 | 7 | 7 | 7 | 7 | 7 | 7 |
月桂酸己基酯 | 4 | 4 | 4 | 4 | 4 | 4 | 4 | 4 | 4 | 4 |
PVP/二十碳烯共聚物 | 2 | 2 | 2 | 2 | 2 | 2 | 2 | 2 | 2 | 2 |
丙二醇 | 4 | 4 | 4 | 4 | 4 | 4 | 4 | 4 | 4 | 4 |
硫酸镁 | 0.6 | 0.6 | 0.6 | 0.6 | 0.6 | 0.6 | 0.6 | 0.6 | 0.6 | 0.6 |
生育酚 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 |
乙酸生育酚酯 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 |
环二甲基硅酮 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 |
对羟基苯甲酸丙酯 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 |
对羟基苯甲酸甲酯 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 |
水 | 至100 | 至100 | 至100 | 至100 | 至100 | 至100 | 至100 | 至100 | 至100 | 至100 |
表1(续)
1-11 | 1-12 | 1-13 | 1-14 | 1-15 | 1-16 | 1-17 | 1-18 | |
二氧化钛 | 3 | 2 | 3 | 2 | 5 | |||
丙二酸苄叉酯聚硅氧烷 | 1 | 0.5 | ||||||
亚甲基双苯并三唑基四甲基丁基苯酚 | 1 | 1 | 0.5 | |||||
[(7,8-二羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸 | 5 | 3 | 2 | 5 | 1 | 3 | 7 | 2 |
聚甘油基-3-Dimerate | 3 | 3 | 3 | 3 | ||||
白蜂蜡 | 0.3 | 0.3 | 0.3 | 0.3 | 2 | 2 | 2 | 2 |
氢化蓖麻油 | 0.2 | 0.2 | 0.2 | 0.2 | ||||
液体石蜡 | 7 | 7 | 7 | 7 | ||||
辛酸/癸酸甘油三酯 | 7 | 7 | 7 | 7 | ||||
月桂酸己基酯 | 4 | 4 | 4 | 4 | ||||
PVP/二十碳烯共聚物 | 2 | 2 | 2 | 2 | ||||
丙二醇 | 4 | 4 | 4 | 4 | ||||
硫酸镁 | 0.6 | 0.6 | 0.6 | 0.6 | ||||
生育酚 | 0.5 | 0.5 | 0.5 | 0.5 | ||||
乙酸生育酚酯 | 0.5 | 0.5 | 0.5 | 0.5 | 1 | 1 | 1 | 1 |
环二甲基硅酮 | 0.5 | 0.5 | 0.5 | 0.5 | ||||
对羟基苯甲酸丙酯 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 |
对羟基苯甲酸甲酯 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 |
二椰油基季戊四醇基柠檬酸酯(和)脱水山梨糖醇倍半油酸酯(和)白蜂蜡(和)硬脂酸铝 | 6 | 6 | 6 | 6 | ||||
PEG-7氢化蓖麻油 | 1 | 1 | 1 | 1 | ||||
硬脂酸锌 | 2 | 2 | 2 | 2 | ||||
芥酸油基酯 | 6 | 6 | 6 | 6 | ||||
油酸癸基酯 | 6 | 6 | 6 | 6 | ||||
二甲聚硅氧烷 | 5 | 5 | 5 | 5 | ||||
氨丁三醇(Tromethamine) | 1 | 1 | 1 | 1 | ||||
甘油 | 5 | 5 | 5 | 5 | ||||
尿囊素 | 0.2 | 0.2 | 0.2 | 0.2 | ||||
水 | 至100 | 至100 | 至100 | 至100 | 至100 | 至100 | 至100 | 至100 |
表2:O/W乳液,数据以wt%为单位
2-1 | 2-2 | 2-3 | 2-4 | 2-5 | 2-6 | 2-7 | 2-8 | 2-9 | 2-10 | |
二氧化钛 | 2 | 5 | 3 | |||||||
亚甲基双苯并三唑基四甲基丁基苯酚 | 1 | 2 | 1 | |||||||
[(7,8-二羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸二甲酯 | 1 | 3 | 3 | 2 | 5 | 5 | 3 | 1 | ||
[(7,8-二羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 |
[(6-羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸 | 1 | 5 | 4 | 6 | 7 | 2 | 1 | |||
4-甲基苄叉樟脑 | 2 | 3 | 4 | 3 | 2 | |||||
BMDBM | 1 | 3 | 3 | 3 | 3 | 3 | 3 |
硬脂醇(和)硬脂基聚氧乙烯醚-7(和)硬脂基聚氧乙烯醚-10 | 3 | 3 | 3 | 3 | 3 | 3 | 3 | 3 | 3 | 3 |
硬脂酸甘油基酯(和)十六烷基聚氧乙烯醚-20 | 3 | 3 | 3 | 3 | 3 | 3 | 3 | 3 | 3 | 3 |
硬脂酸甘油基酯 | 3 | 3 | 3 | 3 | 3 | 3 | 3 | 3 | 3 | 3 |
微蜡 | 1 | 1 | 1 | 1 | 1 | 1 | 1 | 1 | 1 | 1 |
辛酸十六/十八烷基酯 | 11.5 | 11.5 | 11.5 | 11.5 | 11.5 | 11.5 | 11.5 | 11.5 | 11.5 | 11.5 |
辛酸/癸酸甘油三酯 | 6 | 6 | 6 | 6 | 6 | 6 | 6 | 6 | 6 | 6 |
油酸油基酯 | 6 | 6 | 6 | 6 | 6 | 6 | 6 | 6 | 6 | 6 |
丙二醇 | 4 | 4 | 4 | 4 | 4 | 4 | 4 | 4 | 4 | 4 |
硬脂酸甘油基酯SE | ||||||||||
硬脂酸 | ||||||||||
牛油果(Persea Gratissima) | ||||||||||
对羟基苯甲酸丙酯 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 |
对羟基苯甲酸甲酯 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 |
氨丁三醇 | 1.8 | |||||||||
甘油 | ||||||||||
水 | 至100 | 至100 | 至100 | 至100 | 至100 | 至100 | 至100 | 至100 | 至100 | 至100 |
2-11 | 2-12 | 2-13 | 2-14 | 2-15 | 2-16 | 2-17 | 2-18 | |
二氧化钛 | 3 | 2 | 2 | 5 | ||||
丙二酸苄叉酯聚硅氧烷 | 1 | 0.5 | ||||||
亚甲基双苯并三唑基四甲基丁基苯酚 | 1 | 1 | 0.5 | |||||
[(7,8-二羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸二甲酯 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 |
氧化锌 | 2 | |||||||
UV-Pearl,OMC | 15 | 15 | 15 | 30 | 30 | 30 | 15 | 15 |
4-甲基苄叉樟脑 | 3 | |||||||
BMDBM | 1 | |||||||
苯基苯并咪唑磺酸 | 4 |
硬脂醇(和)硬脂基聚氧乙烯醚-7(和)硬脂基聚氧乙烯醚-10 | 3 | 3 | 3 | 3 | ||||
硬脂酸甘油基酯(和)十六烷基聚氧乙烯醚-20 | 3 | 3 | 3 | 3 | ||||
硬脂酸甘油基酯 | 3 | 3 | 3 | 3 | ||||
微蜡 | 1 | 1 | 1 | 1 | ||||
辛酸十六/十八烷基酯 | 11.5 | 11.5 | 11.5 | 11.5 | ||||
辛酸/癸酸甘油三酯 | 6 | 6 | 6 | 6 | 14 | 14 | 14 | 14 |
油酸油基酯 | 6 | 6 | 6 | 6 | ||||
丙二醇 | 4 | 4 | 4 | 4 | ||||
硬脂酸甘油基酯SE | 6 | 6 | 6 | 6 | ||||
硬脂酸 | 2 | 2 | 2 | 2 | ||||
牛油果(Persea Gratissima) | 8 | 8 | 8 | 8 | ||||
对羟基苯甲酸丙酯 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 |
对羟基苯甲酸甲酯 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 |
氨丁三醇 | 1.8 | |||||||
甘油 | 3 | 3 | 3 | 3 | ||||
水 | 至100 | 至100 | 至100 | 至100 | 至100 | 至100 | 至100 | 至100 |
表3:凝胶,数据以wt%为单位
3-1 | 3-2 | 3-3 | 3-4 | 3-5 | 3-6 | 3-7 | 3-8 | 3-9 | 3-10 | |
a=含水凝胶 | ||||||||||
二氧化钛 | 2 | 5 | 3 | |||||||
[(6-羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸 | 1 | 2 | 1 | 1 | ||||||
[(6-羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸,钾盐 | 1 | 3 | 2 | 5 | 5 | 2 | ||||
[(7,8-二羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 |
[(7,8-二羟基-4-氧代-4H-苯并吡喃-3-基)羟甲基]膦酸,钾盐 | 1 | 5 | 4 | 6 | 7 | 2 | 1 |
丙二酸苄叉酯聚硅氧烷 | 1 | 1 | 2 | 1 | 1 | |||||
亚甲基双苯并三唑基四甲基丁基苯酚 | 1 | 1 | 2 | 1 | ||||||
氧化锌 | 2 | 5 | 2 | |||||||
UV-Pearl,甲氧基肉桂酸乙基己基酯 | 30 | 15 | 15 | 15 | 15 | 15 | 15 | 15 | 15 | 15 |
4-甲基苄叉樟脑 | 2 | |||||||||
丁基甲氧基二(苯甲酰基)甲烷 | 1 | |||||||||
苯基苯并咪唑磺酸 | 4 | |||||||||
扁桃(Prunus Dulcis) | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 5 |
乙酸生育酚酯 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 | 0.5 |
辛酸/癸酸甘油三酯 | 3 | 3 | 3 | 3 | 3 | 3 | 3 | 3 | 3 | 3 |
辛基十二烷醇 | 2 | 2 | 2 | 2 | 2 | 2 | 2 | 2 | 2 | 2 |
油酸癸基酯 | 2 | 2 | 2 | 2 | 2 | 2 | 2 | 2 | 2 | 2 |
PEG-8(和)生育酚(和)抗坏血酸棕榈酸酯(和)抗坏血酸(和)柠檬酸 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 |
山梨糖醇 | 4 | 4 | 4 | 4 | 4 | 4 | 4 | 4 | 4 | 4 |
聚丙烯酰胺(和)C13-14异链烷烃(和)月桂基聚氧乙烯醚-7 | 3 | 3 | 3 | 3 | 3 | 3 | 3 | 3 | 3 | 3 |
对羟基苯甲酸丙酯 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 | 0.05 |
对羟基苯甲酸甲酯 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 | 0.15 |
氨丁三醇 | 1.8 | |||||||||
水 | 至100 | 至100 | 至100 | 至100 | 至100 | 至100 | 至100 | 至100 | 至100 | 至100 |
Claims (24)
2.根据权利要求1的化合物,其特征在于取代基R5表示羟基。
3.制备根据权利要求1或2的式I化合物的方法,其中R6彼此独立地表示含1-18个C原子的烷基和R5=OH,其特征在于,
使式II的化合物
其中R1-R4具有上述含义之一,
与选自POCl3、光气或三氟磺酸酐的试剂和芳烷基-、二芳基-或二烷基甲酰胺反应以获得式III的中间体,
其中R1-R4具有根据权利要求1的含义之一,
并随后使其与膦酸二烷基酯反应。
4.制备根据权利要求1的式I化合物的方法,其中R5表示羟基,R6表示H,其特征在于在根据权利要求3的方法之后进行酯水解。
5.制备根据权利要求1的式I化合物的盐方法,其中R5表示羟基,R6表示H,其特征在于在根据权利要求3的方法之后进行酯水解,并将所获得的化合物转化成它们的盐。
6.制备式权利要求1的I化合物的方法,其中R5表示H,R6表示H,其特征在于在根据权利要求4的方法之后进行还原。
7.制备式权利要求1的I化合物的盐的方法,其中R5表示H,R6表示H,其特征在于在根据权利要求5的方法之后进行还原。
8.包含至少一种根据权利要求1或2的式I化合物的组合物。
9.根据权利要求8的组合物,其特征在于所述组合物以0.01wt%-20wt%的量包含至少一种式I化合物。
10.根据权利要求8的组合物,其特征在于所述组合物以0.1wt%-10wt%的量包含至少一种式I化合物。
11.根据权利要求8-10中任一项的组合物,其特征在于它包含一种或多种另外的抗氧化剂和/或维生素。
12.根据权利要求8-10中任一项的组合物,其中所述组合物包含一种或多种UV过滤剂。
13.根据权利要求11的组合物,其中所述组合物包含一种或多种UV过滤剂。
14.根据权利要求8-10中任一项的组合物,其特征在于所述组合物是食品或食品增补剂并且包含适合于食品的赋形剂和任选的其它食品增补剂。
15.根据权利要求11的组合物,其特征在于所述组合物是食品或食品增补剂并且包含适合于食品的赋形剂和任选的其它食品增补剂。
16.根据权利要求8-10中任一项的组合物,其特征在于所述组合物包含适合于药物、皮肤病或化妆品应用的赋形剂。
17.根据权利要求11的组合物,其特征在于所述组合物包含适合于药物、皮肤病或化妆品应用的赋形剂。
18.根据权利要求12的组合物,其特征在于所述组合物包含适合于药物、皮肤病或化妆品应用的赋形剂。
19.根据权利要求13的组合物,其特征在于所述组合物包含适合于药物、皮肤病或化妆品应用的赋形剂。
20.制备根据权利要求8-19中任一项的组合物的方法,其特征在于将至少一种式I化合物与药物、化妆品或皮肤病上适合的或适合于食品的赋形剂混合。
21.根据权利要求1或2的式I化合物在制备具有抗氧化性能的组合物中的用途。
22.根据权利要求1或2的式I化合物在制备组合物中的用途,所述组合物能够对体细胞施加对抗氧化应激的保护作用和/或能够对抗皮肤老化或可以帮助降低皮肤老化的影响。
23.根据权利要求1或2的式I化合物作为抗氧化剂的非诊断和治疗用途。
24.根据权利要求1或2的式I化合物作为人类或动物营养的食品添加剂的非诊断和治疗用途。
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PCT/EP2007/008589 WO2008052631A1 (de) | 2006-10-28 | 2007-10-04 | [(4-oxo-4h-chromen-3-yl)-hydroxymethyl]- oder [(4-oxo-4h-chromen-3-yl)-methyl]-phosphonsäurederivate |
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US3251664A (en) * | 1960-08-04 | 1966-05-17 | Petrolite Corp | Fuel compositions containing branched polyalkylenepolyamines and derivatives thereof |
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