CN107920978A - 改善的内酰胺溶解度 - Google Patents
改善的内酰胺溶解度 Download PDFInfo
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4913—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having five membered rings, e.g. pyrrolidone carboxylic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
Abstract
包含内酰胺和乳酸烷基酯的组合物。所述组合物适合用作抗微生物、抗生物膜和抑菌组合物。
Description
本申请要求于2015年8月20日提交的EP 15181856.4的优先权,其出于所有目的通过引用并入本文。
技术领域
本发明涉及包含内酰胺和乳酸烷基或烯基酯的组合物。所述组合物适合用作抗微生物、抗生物膜和抑菌组合物。
背景技术
WO 2007/085042和WO 2004/016588公开了用于抗微生物益处的内酰胺和关于其合成的步骤。WO2014/118240公开了包含内酰胺和助水溶物的抗微生物组合物。
然而,这些内酰胺的使用受到相对低的溶解度的限制,特别是在水性的或基本上水性的组合物中。
发明内容
本发明涉及内酰胺和乳酸烷基或烯基酯的组合。已经显示该组合改善内酰胺溶解度。这在水性的或基本上水性的组合物中尤其明显。
更具体地,本发明涉及如WO 2007/085042和WO 2004/016588所述的内酰胺与乳酸烷基或烯基酯的组合。WO 2007/085042和WO2004/016588的内容,特别是其中明确说明的内酰胺结构,通过引用并入本文。
例如,在第一方面,本发明涉及组合物,其包含内酰胺和乳酸烷基或烯基酯,其中所述内酰胺是具有式(I)或(II)的内酰胺:
(I)或(II)
其中:
R1和R2各自独立地选自氢、卤素、烷基、环烷基、烷氧基、氧代烷基、烯基、杂环基、杂芳基、芳基和芳烷基;和
R3选自氢、羟基、烷基、环烷基、烷氧基、氧代烷基、烯基、杂环基、杂芳基、环烷基、芳基、芳烷基和–C(O)CR6=CH2;
R4和R5独立地选自氢、芳基、杂环基、杂芳基和芳烷基;和
R6选自氢和甲基;和
R7选自氢和–C(O)CR6=CH2;和
优选地,R4和R5中的至少一个是氢。
应理解的是,在适当的情况下,基团可以任选地被取代。任选的取代基可以包括卤素、C1-4烷基、C1-4卤代烷基(例如CF3)和C1-4烷氧基。
烷基可以例如是C1-12烷基,例如C1-6烷基。芳基可以例如是C6-10芳基,例如苯基。
优选地,R1和R2中的至少一个选自杂环基、杂芳基、芳基和芳烷基。
优选地,R1是氢。优选地,R3是氢。优选地,R4是氢。优选地,R5是氢。优选地,R6是氢。优选地,R7是氢。优选地,R2是芳基或芳烷基。更优选地,R2是苯基或取代的苯基,例如单取代的苯基。取代可以是邻位、间位或对位。优选地,其是对位。优选的取代基包括卤素和甲基。例如但不限于,R2可以选自苯基、4-氟苯基、4-氯苯基、4-溴苯基和4-甲基苯基。
因此,在第一方面,本发明可以提供组合物,其包含内酰胺和乳酸烷基或烯基酯,其中所述内酰胺是具有式Ia或式IIa的内酰胺:
其中R是H、卤素(优选F、Cl或Br)或C1-4烷基(优选甲基)。
在一些实施方式中,内酰胺是具有式Ia的内酰胺。在一些实施方式中,内酰胺是具有式IIa的内酰胺。
优选的内酰胺可以包括:
4-(4-氯苯基)-5-亚甲基-吡咯-2-酮(Ref.488);
5-亚甲基-4-(对甲苯基)吡咯-2-酮(Ref.491);
4-苯基-5-羟基-5-甲基-1H-吡咯-2-酮(Ref.131);
4-(4-氟苯基)-5-羟基-5-甲基-1H-吡咯-2-酮(Ref.258);
4-(4-溴苯基)-5-羟基-5-甲基-1H-吡咯-2-酮(Ref.316)。
组合物可以是水性的或非水性的。
优选地,组合物是水性的或基本上水性的。例如,组合物可以是至少40重量%的水,至少50重量%的水,至少60重量%的水,至少70重量%的水。
如本文所用,在水性的和基本上水性的之间做出区分。应理解,基本上水性的组合物在性质上可以不是完全水性的。例如,它们可以是两相的,或者含有非水性材料在水性溶液中的乳液。
优选地,组合物是水性的。
组合物可以是但不限于个人护理组合物、家庭护理组合物、药物组合物或工业组合物(例如抗生物膜涂料或漆,例如用于海上环境)中的任一种。组合物也可以是农业化学品。组合物可以适合用作抗微生物、抗生物膜和抑菌组合物。本文提供了这样的组合物的非限制性实例。组合物也可以用作添加剂组合物;换句话说,组合物可以与另外的成分(例如赋形剂)组合以形成如上所述的组合物。
优选地,组合物是水性家庭护理组合物或水性个人护理组合物(例如,皮肤清洁组合物)。
合适地,乳酸烷基或烯基酯是乳酸C2-20烷基或烯基酯,例如乳酸C2-15烷基或烯基酯。例如,乳酸烷基或烯基酯可以是乳酸C12-15烷基酯。烷基和烯基链可以包括衍生自脂肪酸(包括棕榈油酸,油酸,月桂酸,肉豆蔻酸,棕榈酸和硬脂酸)的那些。在一些情况下,组合物包含如所述的乳酸烷基酯。
如本文所用,烷基和烯基是指直链和支链基团两者。在一些情况下,基团是直链。在一些情况下,基团是支链。在就链长给出碳原子范围的情况下,应理解,可以存在链长的混合物,尽管在一些情况下,乳酸烷基或烯基酯是指具有限定的烷基或烯基基团的单一化合物。
乳酸酯的量可以是组合物的至少0.01重量%,例如组合物的至少0.1重量%,组合物的至少0.5重量%,组合物的至少1重量%,或更高。
优选的乳酸烷基酯是乳酸乙酯。这甚至在低浓度下也改善溶解度,且被归类为“绿色溶剂”。其是环境友好的,并且其生产原料可以从生物质通过发酵产生。
在水性组合物中,乳酸乙酯的量可以是组合物的至多10重量%。例如,它可以是至多7重量%,至多5重量%,至多3重量%,或甚至低至至多1重量%。
在非水性组合物中,乳酸乙酯的量可以更高,例如至多50重量%,例如至多25重量%。自然地,也可以使用适用于水性组合物的较低量。
乳酸烷基或烯基酯也可以是较长链的乳酸酯。例如,乳酸酯可以是乳酸C12-15烷基或烯基酯,例如如在Dow 中使用的。应理解,上述量可以类似地应用。
优选地,组合物含有0.000001至50重量%的内酰胺,更优选0.001至50重量%,甚至更优选0.01至5重量%,最优选0.01至2重量%。
应理解,关于第一方面描述的选项和优选项在可能的情况下同样适用于其他方面,反之亦然。
具体实施方式
内酰胺可以使用在WO 2007/085042和WO 2004/016588中所述的方法获得,其全部内容通过引用并入本文。
组合物
本文所述的组合物可以是具有抗微生物活性的组合物。在一些情况下,组合物是抗菌的。它们可以具有杀菌和/或抑菌活性。发明人已经观察到期望的抑菌活性。因此,在一些情况下,组合物是抑菌组合物。
组合物还可以预防和/或抑制生物膜的形成。当微生物粘附到表面时,形成生物膜。可以形成生物膜细胞外聚合物质。生物膜(也被称为粘泥(slime))在工业环境中带来问题;例如它们可以形成在装置的管道中,或工业和农业结构中、太阳能电池板上、以及船体和其他船舶结构上。生物膜也可以在家庭环境中造成问题。例如,生物膜可以在家用电器例如洗衣机中形成。生物膜也存在于个人护理中,例如它们可以形成在牙齿表面上。
适用于任何和所有这些应用的组合物都在本发明的范围内。在一些情况下,组合物是漆或其他涂料。在这样的情况下,组合物还可以包含粘结剂,任选地颜料和任选地一种或多种常规添加剂(例如,以改变表面张力、改善流动性、改善成品外观、增加湿边、改善颜料稳定性等——这样的添加剂是本领域已知的)。组合物可以包含水性溶剂或有机溶剂以适应目的。
组合物还可以用于医疗应用,例如用于涂覆包括医疗装置的设备。
在一些情况下,组合物是药物组合物。换句话说,组合物可以包含如本文所述的内酰胺和药学上可接受的赋形剂。组合物可适用于局部使用(例如它可以是霜剂或洗剂),它可适用于眼部使用(例如它可以用作药物滴眼剂),它可适用于耳朵使用(例如它可以用作滴耳剂),它可适用作漱口剂,或它可适用于口服施用。
在一些情况下,组合物是适用于家庭(通常被称为家庭护理组合物)或机构的组合物。家庭护理组合物包括但不限于清洁产品、洗衣洗涤剂和织物调理剂。在一些情况下,组合物是家庭护理组合物,例如洗衣液。因此组合物可以包含洗涤表面活性剂和助洗剂。组合物可以是织物调理剂(也被称为织物柔顺剂)并且可以包含抗静电剂。组合物也可以是家庭清洁产品。
在一些情况下,组合物是个人护理组合物。例如,组合物可以旨在用于皮肤上(例如霜剂、清洁剂或精华液(serum))。例如,组合物可用于痤疮的预防和治疗。例如,组合物可以包含聚二甲基硅氧烷、凡士林、保湿剂(例如透明质酸或甘油)和神经酰胺中的一种或多种。在一些情况下,组合物是包含洗涤剂的个人护理组合物,例如,组合物可以是洗脸或沐浴凝胶或洗发香波。组合物可以是除香波以外的毛发处理组合物。组合物可以是除臭组合物(例如,除臭粉末、糊剂或液体)。组合物可以是口腔护理组合物(例如牙膏或漱口水),并且可以包含例如氟化物和/或调味剂。
在一些情况下,组合物是隐形眼镜清洁液。
组合物可以是适用于农业的组合物,例如作为土壤添加剂(固体或液体)。
组合物可以是适用于玻璃或透镜的处理或制造的组合物,例如作为用于太阳能电池板的添加剂/处理剂。
实施例
以下实施例使用但不限于4-(4-氯苯基)-5-亚甲基-吡咯-2-酮和乳酸乙酯。
将过量的固体内酰胺(约3mg)置于配有0.45μm尼龙过滤器的 MiniUniprep样品小瓶中。加入水或水+乳酸乙酯(500μL),摇晃混合物并短暂地轻敲以开始分散固体,然后使用配有小瓶支架的平板摇床摇动混合物48小时(见下图)。48小时后,通过将具有整体式过滤器的柱塞在小瓶上向下按压,从系统中除去固体(见下图)。这除去固体并在内室内提供过滤溶液,然后使其准备用于分析。
使用HPLC分析定量溶解在溶液中的内酰胺的水平。在配有Thermo Gold C18柱(15×2.1×3μm)的Agilent系列HPLC上分析样品,用60/40的甲醇/水(+0.1%甲酸)等度洗脱,流速为0.4mL/min,在285nm处使用DAD检测器。4-(4-氯苯基)-5-亚甲基-吡咯-2-酮具有约2.8分钟的保留时间。
测量溶液中的内酰胺的绝对水平,并报告为相对于单独的水的内酰胺溶解度的增加。结果如下所示。
应理解,除非另有明确规定,否则所有的优选项是可以组合的。
Claims (7)
1.一种组合物,其包含内酰胺和乳酸烷基或烯基酯,其中所述内酰胺是具有式Ia或式IIa的内酰胺:
其中R是H、卤素或C1-4烷基。
2.权利要求1所述的组合物,其中R是H、F、Cl、Br或Me。
3.前述权利要求中任一项所述的组合物,其中所述内酰胺选自:
4.前述权利要求中任一项所述的组合物,其中所述乳酸烷基酯是乳酸乙酯。
5.权利要求4的组合物,其中所述组合物是水性组合物。
6.权利要求4或权利要求5所述的组合物,其中乳酸乙酯的量是所述组合物的0.01至10重量%。
7.权利要求1至3中任一项所述的组合物,其中所述乳酸烷基酯是乳酸C12-15烷基酯。
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