WO2014198602A1 - New succinate derivatives - Google Patents
New succinate derivatives Download PDFInfo
- Publication number
- WO2014198602A1 WO2014198602A1 PCT/EP2014/061561 EP2014061561W WO2014198602A1 WO 2014198602 A1 WO2014198602 A1 WO 2014198602A1 EP 2014061561 W EP2014061561 W EP 2014061561W WO 2014198602 A1 WO2014198602 A1 WO 2014198602A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- acid
- formula
- skin
- compounds
- trimethylcyclohexyl
- Prior art date
Links
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- 239000004172 quinoline yellow Substances 0.000 description 1
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 230000035322 succinylation Effects 0.000 description 1
- 238000010613 succinylation reaction Methods 0.000 description 1
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- 229960000894 sulindac Drugs 0.000 description 1
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- HBPNTDBLHQHPLH-UHFFFAOYSA-N tetradecyl 16-methylheptadecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC(C)C HBPNTDBLHQHPLH-UHFFFAOYSA-N 0.000 description 1
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- DZKXJUASMGQEMA-UHFFFAOYSA-N tetradecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC DZKXJUASMGQEMA-UHFFFAOYSA-N 0.000 description 1
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- UPSPUYADGBWSHF-UHFFFAOYSA-N tolmetin Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=C(CC(O)=O)N1C UPSPUYADGBWSHF-UHFFFAOYSA-N 0.000 description 1
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- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
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- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
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- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- OEIXGLMQZVLOQX-UHFFFAOYSA-N trimethyl-[3-(prop-2-enoylamino)propyl]azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CCCNC(=O)C=C OEIXGLMQZVLOQX-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 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
- FQAZRHVERGEKOS-UHFFFAOYSA-N tripropan-2-yl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CC(C)OC(=O)CC(O)(C(=O)OC(C)C)CC(=O)OC(C)C FQAZRHVERGEKOS-UHFFFAOYSA-N 0.000 description 1
- ODHUFJLMXDXVRC-UHFFFAOYSA-N tripropyl 2-hydroxypropane-1,2,3-tricarboxylate Chemical compound CCCOC(=O)CC(O)(C(=O)OCCC)CC(=O)OCCC ODHUFJLMXDXVRC-UHFFFAOYSA-N 0.000 description 1
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- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
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- 150000003751 zinc Chemical class 0.000 description 1
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- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 1
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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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
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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
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
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- A—HUMAN NECESSITIES
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
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- 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
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- 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
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- A—HUMAN NECESSITIES
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- A61Q19/007—Preparations for dry skin
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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
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
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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
- A61Q19/04—Preparations for care of the skin for chemically tanning the skin
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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
- A61Q19/08—Anti-ageing preparations
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
- C07C235/74—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of a saturated carbon skeleton
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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
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/48—Thickener, Thickening system
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- A—HUMAN NECESSITIES
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- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
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- A61K2800/524—Preservatives
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- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/59—Mixtures
- A61K2800/591—Mixtures of compounds not provided for by any of the codes A61K2800/592 - A61K2800/596
Definitions
- the invention relates generally to new succinate derivatives. Moreover, the invention relates to the use of one or more succinate derivatives in cosmetic or pharmaceutical compo- sitions, which are preferably dermatological compositions and are preferably used topically.
- Cellular ageing can be subdivided into two different processes. One is intrinsic ageing, caused by factors derived from inside the cells. The second is extrinsic ageing, caused by factors from the cells environment.
- the process of ageing leads to a plethora of cellular, metabolic and tissue-derived changes. Among these a re - a decline in metabolic activity, a lower rate of cell division, a reduced DNA repair capacity, an accumulation of oxidized bio- molecules (DNA, proteins, carbohydrates and lipids), an accumulation of misfolded proteins, cellular stiffening of vessel walls and an impaired peripheral blood circulation. All these as- pects are closely interlinked with each other.
- the epidermis In premature skin aging one can observe changes within all the dermal layers: In the upper skin layer, the epidermis, one can usually observe a influence on the epidermal thickness. The epidermis becomes thinner with aging. This is caused by a reduced mitotic activity of keratinocytes within the stratum basale; the consequence is a reduced water-binding capacity, a lowered elasticity, a compromised barrier function and wrinkle formation. I n the dermis, the amount of fibroblast decreases and their activity falls. The consequence is a reduced production of tropocollagen, hyaluronic acid and elastin that leads to a loss of elasticity, reduced sebum production and reduced perspiration.
- UVB irradiation is a key factor during extrinsic skin aging and it alters cutaneous structure and function. Repeated exposure to UV radiation from the sun causes premature aging of skin. Under conditions of increased formation of oxidative stress as associated e.g. with UV irradiation, free radicals are formed, that cause damages to the cell contents and induced apoptosis, and aging. In particular, sunbathing and the visit of solarium amplify aging and support the formation of age spots, which result in additional premature skin ageing. To combat wrinkles, which are visible signs of skin ageing, a lot of anti-ageing cosmetic products have been developed yet, which promote the reduction of wrinkles. Quite a series of facial products with various substances, e.g. vitamin C, vitamin E, Q.10, lipoic acid, collagen and hyaluronic acid (HA) have been developed with the promise to be "wrinkles killer".
- various substances e.g. vitamin C, vitamin E, Q.10, lipoic acid
- ROS Reactive oxygen species
- the proteasome degrades damaged, misfolded, oxidized or unnecessary proteins. It is involved in turn over regulation of proteins, cell cycle control, gene expression, (oxidative) stress, im mune response and carcinogenesis.
- the proteasomal main function is the cell clearance of abnormal, denatured or in general damaged and unwanted proteins as well as for the regulated degradation of short-lived proteins. The efficacy of the degradation process is of enormous importance for the cellular homeostasis.
- the 20S proteasome is a cylin- dric structure, with a molecular weight of 700 kDa.
- the outer rings are made of 7 different [alpha]-subunits.
- the other 2 rings build the middle structure of the 20S proteasome and consist of 7 diverse [beta]-subunits.
- the outer [alpha]-rings control the access of 20S-proteasome substrates into the inner proteolytic chamber.
- This proteolytic activity could be divided into three different parts: 1. Peptidyl-glutamyl-peptide-hydrolysing activity (caspase like activity); 2. Trypsin like activity a nd 3. Chymotrypsin like activity.
- proteolytic action results in the generation of oligopeptides, generally with a length of 8-10 amino acids.
- polyubiquitination is not necessary to degrade proteins.
- the 20S proteasome is ATP-independent.
- proteasome In the skin the proteasome has an important role in ageing/photo-ageing. Following UV en- ergy absorption there are different changes in the skin, including production of free radicals, modified proteins and 4-hydroxy-2-nonenal (HNE). These products affect the gene expression in skin cells and lead to an increase of matrix metalloproteinases (M M Ps) and a decrease of their inhibitors (TIM Ps) which results in a reduction of collagen and therefore in wrinkle formation. A drastic decline in proteasome activity and a simultaneous accumula- tion of modified and ubiquitinated proteins after UV irradiation in human keratinocytes has been reported.
- M M Ps matrix metalloproteinases
- TIM Ps inhibitors
- proteasome activity Today it is proven that there is a decline of proteasome activity and expression in human keratinocytes and fibroblasts during ageing. It is evident that this down regulation of proteasome activity is a result of protein aggregation. I n a circuit, shrinking of proteasome activity leads to new protein aggregates and non degraded polyubiquitinated pro- teins, which in turn affect the proteasome again. Based on these findings, skin ageing is linked to proteasome dysfunction and preservation of "normal" proteasome function allays skin ageing. SDS and some fatty acids have been reported to stimulate proteasome activities in the test tube by favoring the open confirmation of the proteasome.
- proteasome activity WO 02/080876
- Palmitoyl Isoleucin Besides the stimulation of proteasome activity by stimulation of one or more of the enzymatic activities, the upregulation of the proteasomal proteins itself is a potent method to induce the proteasomal degradation. This is of special interest regarding the fact that not only proteasomal activity declines in elderly people but also the expression of proteasomal subunits.
- proteasome Maintenance of cellular homeostasis influences the rate of ageing and is determined by several factors, including efficient proteolysis of damaged proteins. Protein degradation is predominantly catalyzed by the proteasome. Specifically, the proteasome is responsible for cell clearance of abnormal, denatured or in general damaged proteins as well as for the reg- ulated degradation of short-lived proteins. As the proteasome has an impaired function during ageing, actives that restore its function are needed. Furthermore, UV irradiation impairs proteasomal function, thereby enhancing the cellular deposition of toxic proteins. I mportantly, centenarians show a very high activity of the proteasome and are a good example of healthy ageing.
- proteasome activators enhance the survival of Huntington's disease neuronal model cells and the development of Alzheimer's disease and Parkinson's disease is partly based on an inefficient proteasomal clearance.
- the most important intrinsic ROS source is the mitochondrion. This is a cellular organelle with the function to generate ATP, the driving force for nearly every biological function in the cellular metabolism.
- the mitochondrial electron transport chain does not work with 100% efficiency, thus generating misdirected electrons. These electrons finally lead to the generation of superoxides and therewith oxidative stress.
- the strongest intracellular radical scavenging mechanism is the glutathione system. It combines enzymes like catalase and superoxide dismutase (SOD) that can dissipate free radicals. Even small doses of UV or other ROS generating circumstances can override these protective systems.
- SOD superoxide dismutase
- extrinsic antioxidants becomes important.
- One is the supply with chemical antioxidants. Molecules, those are capable of detoxifying ROS.
- a second strategy is to supply substances, which are able to induce intrinsic cellular antioxidative systems like Hemoxidase 1 (HOI). WHITENING
- skin-lightening agents are used: if for some reason the melanin-forming melanocytes in human skin are not evenly distributed, pigment spots occur which are either lighter or darker than the surrounding skin area. To balance out this pigment spots, skin lightening agents are sold which at least partially help. Aside from many peple want to lighten their skin colour or to prevent skin pigmentation -so therefore the need is big of safe effective skin and hair lightening agents.
- the therapeutic treatment of melanin-induced pigmentation disorders such as hyperpigmentations is one area of application (e.g. scar hyperpigmentations, post-traumatic drug-induced hyperpigmentations, post-inflammatory hyperpigmentations induced by phototoxic reactions, ephelides).
- I ncreasing in Skin pigmentation, caused by UV Light can be avoided by using UV-absorbing substances.
- the UV absorbers do not bring about a true lightening. Therefore, object of the present invention was to provide compositions comprising active compounds, which have positive benefits to human skin cell, and thereby provide moisturizing and/or anti-ageing effects.
- the object was to provide active compounds which are capable to promote cell repair and regeneration, and thus prolong the health of cell life span of a cell in nucleus and cytoplasm in eukaryotes.
- the active compounds to be specified should be toxicologically safe, effective already at relatively low concentrations, well tolerated by the skin, stable (in particular in normal cosmetic and/or pharmaceutical formulations), and easy to formulate and economical to produce. Description of the invention
- the subject of the invention relates to a compound of formula (I):
- Ri, R'i, R 2 , R' 2 , R3, R'3, R 4 R' 4 , R5, R'5, R6, R7 are independently of one another and denote hydrogen, hydroxyl, Ci to C 6 -alkyl group or R 6 and R 7 form together a C5-C6 ring system, and
- n 0, 1, 2, 3, or 4.
- Cito C 6 -alkyl group represents alkyl moieties, which maybe branched or linear, and which maybe saturated or unsaturated.
- Preferred alkyl moieties maybe selectd from the group consisting of methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert. -butyl, n- pentyl, 2-methylbutyl, neopentyl, hexyl, methylpentyl, dimethylbutyl, especially preferred are methyl, ethyl and iso-propyl.
- R 6 and R 7 form together a C5-C6 ring system
- R 6 and R 7 and the nitrogen atom may form together a saturated or unsaturated ring, which are preferably not further substituted, preferred is that R 6 and R 7 and the nitrogen atom together form a six ring system, that is preferably a saturated hexyl ring system.
- R 6 , R 7 of formula (I) are independently of one another and denote hydrogen, methyl, ethyl, isopropyl or R 6 and R 7 form together with the nitrogen of formula (I) a C6-ring system, which is preferably a saturated hexyl ring system.
- R 6 , R 7 of formula (II) are independently of one another and denote hydrogen, methyl, ethyl, isopropyl or R 6 and R 7 form together with the nitrogen of formula (II) a C6-ring system, which is preferably a saturated hexyl ring system.
- the compounds of formula (I) and (I I) are selected from the group of following compounds:
- compounds of formula (I), respectively formula (I I) have the ability to prolong health span of a cell. Especially, cellular repair mechanism in human skin can be activated, antioxidative effects can be obeserved and apoptosis can be reduced. It has been proved to be particularly advantageous to use a mixture of two compounds of formula (I), e.g. preferred are herewith a combination of tra/is-3,3,5-trimethylcyclohexyl 4- (dimethylamino)-4-oxobutanoate (S7a) and c/ ' s-3,3,5-trimethylcyclohexyl 4-(dimethylamino)- 4-oxobutanoate (S7b).
- trans:cis 1:200 to 200:1.
- trans : cis from 1:60 to 50:1, more preferably 1: 50 to 1: 5, most preferably, 1:13 to 1:4.
- the effects are also clearly positive when one of the enantiomeric forms is used alone.
- a preferred embodiment is ⁇ , ⁇ -Dimethyl-succinamic acid 3,3,5-trimethylcyclohexyl ester (S7), which is selected from the enantomeric form of
- Another preferred embodiment is ⁇ , ⁇ -Dimethyl-succinamic acid 3,3,5-trimethyl-cyclohexyl ester (S7), which is selected from the enantomeric form of
- an enantiomeric mixture of 3,3,5-trimethylcyclohexyl) 3-(dimethylamino)- 3-oxo-propanoate (S9) comprises of
- trans : cis from 1:200 to 200:1.
- the ratio from trans : cis is from 1:60 to 50:1, more preferably 1: 50 to 1: 5, most preferably, 1:13 to 1:4.
- the enantiomeric forms alone e.g. S7a' or S7a" or S7b' or S7b" are advantageous, for that the single enantiomeric forms already have the ability to prolong health span of a cell, especially, cellular repair mechanism in human skin can be activated, antioxidative effects can be obeserved and apoptosis can be reduced.
- an object of the invention is one or more compounds of formula (I), respectively formula (I I) for use in the treatment of cellular ageing and cell life span.
- a further object of the invention is one or more compounds of formula (I), respectively formula (II) for use in the treatment of free-radical activity, in the form that the renewal and differentiation of keratinocytes is regulated, the functional condition of the skin is improved ot is kept in good functional condition, for for skin protection or treating dry skin.
- a concentration of from about 0.001 to 15 %, preferred 0.1 to 2 %, and most preferred 0.01 to 5.0 % by weight of the compound of formula (I), respectively formula (I I) in a pharmaceu- tical or cosmetic composition is preferred, in case of more than two compounds of formula
- one or more compounds of formula (I), respectively formula (I I) can be used for activation and/ or reactivation and/or protection of proteasome in nucleus and cytoplasm in eukaryotes.
- one or more compounds of formula (I), respectively formula (II) means that a mixture of two or more kind of compound of formula (I), respectively formula (II) maybe also possible used.
- proteasome has an impaired function as already described above, during aging it is im- portant to protect, activat or reactivate proteasome, thus positively contributing to affect the anti-ageing.
- a further object of the invention is the use, especially the cosmetically use of one or more compounds of formula (I), respectively formula (I I) is especially for the treatment of cellular ageing and prolongation of cell life span, which is preferably in the form of anti-aging, delay- ing aging, toning, moisturizing and/or whitening.
- the one or more compounds of formula (I) is used for activation and/ or reactivation and/or protection of proteasome in nucleus and cytoplasm in eukaryotes.
- the one or more compounds of formula (I), respectively formula (I I) are used as active substances in the preparation of a cosmetical or pharmaceu- tical composition, which are preferably dermatological compositions, preferably for topical use on the skin.
- active substances means that compounds according to formula (I), respectively formula (II) show in an effective amount effects and benefits to the skin that contributes to skin health care, e.g. ageing, antioxidative effects, depigmentation, whitening.
- the one or more compounds of formula (I), respectively formula (II) have an anti-free-radical activity, thus when these active substances are formulated in cosmetic or pharmaceutical compositions, the compositions regulating the renewal and differentiation of the keratinocytes, for improving the functional condition of the skin or keeping them in a good functional condition, for skin protection or treating dry skin. Therefore, in another preferred embodiment the one or more used compounds of formula (I), respectively formula (II) have an anti-free-radical activity, thus regulating the renewal and differentiation of the keratinocytes, for improving the functional condition of the skin or keeping them in a good functional condition, for skin protection or treating dry skin.
- the one or more compounds of formula (I), respectively formula (II) is ⁇ , ⁇ -Dimethyl-succinamic acid 3,3,5-trimethyl-cyclohexyl ester (S7), wherein all enantiomeric and diastereomeic forms are incorporated herewith.
- the used one or more compounds of formula (I), respectively formula (II) is tra/is-3,3,5-trimethylcyclohexyl 4-(dimethylamino)-4- oxobutanoate (s7a),
- ratio of trans is about 1:200 to 200:1.
- the present invention also refers to a non-therapeutic (rather cosmetic) method for activation and/ or reactivation and/ or ptotection of proteasome in nucleus and cytoplasmin eukaryotes, wherein one or more compounds of formula (I)
- Ri, R'i, R 2 , R' 2 , R3, R'3, R 4 R' 4 , R5, R'5, R6, R7 are independently of one another and denote hydrogen, hydroxyl, Ci to C 6 -alkyl group or R 6 and R 7 form together a C5-C6 ring system, and
- n 0, 1, 2, 3, or 4
- formula (I) is administered to human tissue or skin.
- the compound of formula (I) is simplified to formula (II), in the case that R'i, R' 3 and R' 5 denote hydrogen thus formula (I) can be represent as follows:
- the present invention refers to a method for affecting a skin care treatment, comprising topically applying to the skin a skin care efficient amount of one or more of a compound of formula (I), respectively formula (I I).
- Skin care treatment is preferably, for whitening or for reducing signs of aging.
- the present invention refers to a method for the treatment of the epidermis of human beings suffering from the signs of aging, suffering from dry skin and for the prevention of maladies associated with free radical formation on skin, comprising topically administering an effective amount of one or more compounds of formula (I), respectively formula (II) to the epidermis.
- compositions may be prepared using a pharmacological concentration of the active compounds or its salts disclosed in the present invention. It is not intended that the present invention be limited by the particular nature of the therapeutic preparation, so long as the preparation comprises the active agent or its salts.
- These therapeutic preparations can be administered to mammals for veterinary use, such as with domestic animals, and clinical use in humans in a manner similar to other therapeutic agents.
- the dosage required for therapeutic efficacy will vary according to the type of use and mode of administration, as well as the particularized requirements of individual hosts. A person having ordinary skill in this art would readily be able to determine, without undue experimentation, the appropriate dosages and routes of administration of ascorbic acid of the present invention.
- a further object of the invention is one or more compounds of formula (I), respectively formula (I I) as a medicament.
- the one or more compounds of formula (I), respectively formula (I I) is for use in the treatment of cellular ageing and cell life span, the treatment of free- radical activity, in the form that the renewal and differentiation of keratinocytes is regulat- ed, the functional condition of the skin is improved ot is kept in good functional condition, for for skin protection or treating dry skin.
- a preferred embodiment of the present invention relates to pharmaceutical compositions, comprising
- Ri, R'i, R 2 , R' 2 , R3, R'3, R 4 R' 4 , R5, R'5, R6, R7 are independently of one another and denote hydrogen, hydroxyl, Ci to C 6 -alkyl group or R 6 and R 7 form together a C5-C6 ring system, and
- n 0, 1, 2, 3, or 4
- the compounds of formula (I), respectively formula (I I) can easily be incorporated in the given concentrations in common cosmetic compositions such as pump sprays, aerosol sprays, creams, ointments, tinctures, lotions and the like without having an odorous, colouring or sensating effect. I n this case, it is also possible and in many cases advantageous to combine the compounds of formula (I), respectively formula (II) with further active ingredients.
- Another object of the invention is the cosmetical use of one or more compounds of formula (I), respectively formula (I I) for the treatment of anti-aging, delaying aging, toning, moisturizing and/or whitening.
- the cosmetical use of one or more compounds of formula (I), respectively formula (I I) is preferably for activation and/ or reactivation and/or protection of proteasome in nucleus and cytoplasm in eukaryotes.
- Another pre- ferred embodiment is the use of one or more compounds of formula (I), respectively formula (I I), wherein the one or more compounds of formula (I) or (II) have an anti-free-radical activity, thus regulating the renewal and differentiation of the keratinocytes, for improving the functional condition of the skin or keeping them in a good functional condition, for skin protection or treating dry skin.
- compositions according to the present invention can be produced by conventional processes known per se, such that one or more compounds of formula (I), respectively formula (I I) are incorporated into products particularly for topical application which can have a conventional composition and which in addition to the effects mentioned hereinbefore or hereinafter can also be used for the treatment, care and cleansing of the skin or hair.
- a preferred embodiment of the present invention relates to cosmetic compositions, com- prising
- Ri, R'i, R 2 , R' 2 , R3, R'3, R 4 R' 4 , R5, R'5, R6, R7 are independently of one another and denote hydrogen, hydroxyl, Ci to C 6 -alkyl group or R 6 and R 7 form together a C5-C6 ring system, and
- n 0, 1, 2, 3, or 4
- the cosmetic or pharmaceutical acceptable carriers are, preferably, selected from the group consisting of water, alcohols containing 2 to 6 carbon atoms, polyols containing 1 to 10 carbon atoms and 2 to 4 hydroxyl groups and oil bodies. Particularly preferably are, besides water, ethanol, isopropyl alcohol, ethylene glycol, propylene glycol, glycerol, trime- thylolpropane, pentaerythritol and esters of linear or branched, saturated, and, particularly, unsaturated fatty acids containing 6 to 22, and, preferably, 8 to 18 carbon atoms with alco- hols containing 1 to 6 carbon atoms.
- the cosmetic or pharmaceutical compositions according to the invention may contain components (a) and (b) in the weight ratio of from 0.1:99 to 99.9:1, preferably, of from 10:90 to 90:10, more preferably of from 25 :75 to 75 :25, and most preferably of from 40:60 to 60:40.
- Components (a+b) and (c) may be contained in the weight ratio of from 0.01:99.9 to 2:98, preferably of from 0.5:99.5 to 1.5 : 98.5, and specifically of about 1:99.
- compositions according to the invention preferably comprise as active substance of compound (I) and respectively formula (II):
- trans-3,3,5-trimethylcyclohexyl 4-(dimethylamino)-4-oxobutanoate (s7a) may be preferably both Enantiomer (IS ⁇ ffj-S ⁇ -trimethylcyclohexyl] 4-(dimethylamino)-4-oxo- 4-(dimethylamino)-4-oxo-butanoate:
- Vll lb and the c/ ' s-3,3,5-trimethylcyclohexyl 4-(dimethylamino)-4-oxobutanoate (s7b) is may be preferably both Enantiomer (lR,5R)-3,3,5-tr methy ⁇ cyc ⁇ ohexy ⁇ ] 4-(dimethylamino)-4-oxo- butanoat and/or (IS ⁇ Sj-S ⁇ -trimethylcyclohexyl] 4-(dimethylamino)-4-oxo-butanoate:
- the pharmaceutical or cosmetic composition comprises one or more compounds of formula (I), respectively formula (I I), wherein the compounds of formula (I), respectively formula (I I) is selected from the group of consisting of coumpounds SI, S2, S6, S7, S8, S9, S10 and wherein the compounds are selected individual, such that each enantiomeric form of SI, S2, S6, S7, S8, S9, S10 as described above can be selected solely.
- a cosmetic or pharamaceutical composition which comprises one or more compounds of formula (I), respectively formula (II) selected from S7a' and/or 7a" and/or S7b' and/or S7b".
- the cosmetic or pharmaceutical compositions according to the invention may comprsises further additives which are selected from the group consisting of surfactants, oil bodies, emulsifiers, superfatting agents, pearlising waxes, consistency factors, polymers, silicone compounds, waxes, stabilizers, antidandruff agents, film formers, swelling agents, hy- drotropes, preservatives, solubilizers, complexing agents, reducing agents, alkalising agents, perfume oils, dyes, thickeners, fats, lecithins, phospholipids, UV protection factors, moisturizers, biogenic agents, antioxidants, deodorants, a ntiperspirants, insect repellants, self- tanning agents, tyrosine inhibitors (depigmenting agents), and the like as additional auxiliaries and additives.
- surfactants oil bodies, emulsifiers, superfatting agents, pearlising waxes, consistency factors, polymers, silicone compounds, waxes, stabilizers, antidand
- additives are selected from the group consisting of
- UV-filters UV-absorbers
- glycosaminoglycans (b5) glycosaminoglycans (GAGs) and further substances stimulating the synthesis of gly- cosaminoglycans;
- a cosmetic composition preferably a topical preparation according to the invention containing
- anti-ageing or biogenic agents are, for example antioxidants, primary or second dary sun protection factors, matrix-metalloproteinase inhibitors (M M PI), skin moisturizing agents, glycosaminglycan stimulators, anti-inflammatory agents and TRPVl antagonists.
- M M PI matrix-metalloproteinase inhibitors
- Antioxidants amino acids (preferably glycine, histidine, tyrosine, tryptophane) and derivatives thereof, imidazoles (preferably urocanic acid) and derivatives thereof, peptides, preferably D,L-carnosine, D-carnosine, L-carnosine and derivatives thereof (preferably anserine), carnitine, creatine, matrikine peptides (preferably lysyl- threonyl-threonyl-lysyl-serine) and palmitoylated pentapeptides, carotenoids, carotenes (preferably alpha-carotene, beta-carotene, lycopene) and derivatives thereof, lipoic acid and derivatives thereof (preferably dihydrolipoic acid), aurothioglucose, propyl thiouracil and other thiols (preferably thioredoxine, glutathione, cysteine, cystine, cystamine and
- chelators preferably alpha-hydroxy fatty acids, palmitic acid, phytic acid, lactoferrin, alpha-hydroxy acids (preferably citric acid, lactic acid, malic acid), humic acid, bile acid, bile extracts, tannins, bilirubin, biliverdin, EDTA, EGTA and derivatives thereof), unsaturated fatty acids and derivatives thereof (preferably gamma-linolenic acid, linoleic acid, oleic acid), folic acid and derivatives thereof, ubiquinone and derivatives thereof, ubiquinol and derivatives thereof, vitamin C and derivatives (preferably ascorbyl palmitate, Mg ascorbyl phosphate, ascorbyl acetate, ascorbyl glucoside), tocopherols and derivatives (preferably vitamin E acetate), vitamin A and derivatives (vitamin A palmitate) and coniferyl benzoate of benzoic resin,
- metal chelators preferably alpha-hydroxy fatty
- antioxidants are selected from the group consisting of vitamin A and derivatives, vitamin C and derivatives, tocopherol and derivatives, preferably tocopheryl acetate, and ubiquinone.
- Primary sun protection factors in the context of the invention are, for example, organic substances (light filters) which are liquid or crystalline at room temperature and which are capable of absorbing ultraviolet radiation and of releasing the energy absorbed in the form of longer-wave radiation, for example heat.
- formulations according to the invention advantageously contain at least one UV-A filter and/or at least one UV-B filter and/or a broadband filter and/or at least one inorganic pigment.
- Formulations according to the invention preferably contain at least one UV-B filter or a broadband filter, more particularly preferably at least one UV-A filter and at least one UV-B filter.
- Preferred cosmetic compositions preferably topical formulations according to the present invention comprise one, two, three or more sun protection factors selected from the group consisting of 4-aminobenzoic acid and derivatives, salicylic acid derivatives, benzophenone derivatives, dibenzoylmethane derivatives, diphenyl acrylates, 3-imidazol-4-yl acrylic acid and esters thereof, benzofuran derivatives, benzylidene malonate derivatives, polymeric UV absorbers containing one or more organosilicon radicals, cinnamic acid derivatives, camphor derivatives, trianilino-s-triazine derivatives, 2-hydroxyphenylbenzotriazole derivatives, phenylbenzimidazole sulfonic acid derivatives and salts thereof, anthranilic acid menthyl esters, benzotriazole deriva- tivesand indole derivatives.
- sun protection factors selected from the group consisting of 4-aminobenzoic acid and derivatives, sal
- UV filters cited below which can be used within the context of the present invention are preferred but naturally are not limiting.
- UV filters which are preferably used are selected from the group consisting of p-aminobenzoic acid
- Broadband filters which are preferably combined with one or more compounds of formula (I) in a preparation according to the present invention are selected from the group consisting of
- UV-A filters filters which are preferably combined with one or more compounds of formula (I) in a preparation according to the present invention are selected from the group consisting of
- UV filters which are more preferably combined with one or more compounds of formula (I) in a preparation according to the present invention are selected from the group consisting of
- these preparations contain at least one UVA filter and/or at least one UVB filter and/or at least one inorganic pigment.
- the preparations may be present here in various forms such as are conventionally used for sun protection preparations. Thus, they may be in form of a solution, an emulsion of the water-in-oil type (W/O) or of the oil-in-water type (O/W) or a multiple emulsion, for example of the water-in-oil-in-water type (W/O/W), a gel, a hydrodispersion, a solid stick or else an aerosol.
- a formulation according to the invention contains a total amount of sunscreen agents, i.e. in particular UV filters and/or inorganic pigments (UV filtering pigments) so that the formulation according to the invention has a light protection factor of greater than or equal to 2 (preferably greater than or equal to 5).
- sunscreen agents i.e. in particular UV filters and/or inorganic pigments (UV filtering pigments) so that the formulation according to the invention has a light protection factor of greater than or equal to 2 (preferably greater than or equal to 5).
- UV filters and/or inorganic pigments UV filtering pigments
- Secondary sun protection factors of the antioxidant type interrupt the photochemical reaction chain which is initiated when UV rays penetrate into the skin.
- Typical examples are amino acids (for example glycine, histidine, tyrosine, tryptophane) and derivatives thereof, imidazoles (for example urocanic acid) and derivatives thereof, peptides, such as D,L-carnosine, D-carnosine, L-carnosine and derivatives thereof (for example anserine), carotinoids, carotenes (for example alpha-carotene, beta-carotene, lycopene) and derivatives thereof, chlorogenic acid and derivatives thereof, liponic acid and derivatives thereof (for example dihydroliponic acid), aurothioglucose, propylthiouracil and other thiols (for example thioredoxine, glutathione, cysteine, cystine, cystamine and
- Advantageous inorganic secondary light protection pigments are finely dispersed metal oxides and metal salts which are also mentioned in WO 2005 123101 Al.
- the total quantity of inorganic pigments, in particular hydrophobic inorganic micro-pigments in the finished cosmetic preparation according to the present invention is advantageously from 0.1 to 30% by weight, preferably 0.5 to 10.0% by weight, in each case based on the total weight of the preparation.
- particulate UV filters or inorganic pigments which can optionally be hydrophobed, can be used, such as the oxides of titanium (Ti0 2 ), zinc (ZnO), iron (Fe 2 0 3 ), zirconium (Zr0 2 ), silicon (Si0 2 ), manganese (e.g. MnO), aluminium (Al 2 0 3 ), cerium (e.g. Ce 2 0 3 ) and/or mixtures thereof.
- Matrix-Metalloproteinase inhibitors comprise ma- trix-metalloproteinase inhibitors, especially those inhibiting matrix-metalloproteinases enzymatically cleaving collagen, selected from the group consisting of: ursolic acid, retinyl palmitate, propyl gallate, precocenes, 6-hydroxy-7-methoxy-2,2-dimethyl- l(2H)-benzopyran, 3,4-dihydro-6-hydroxy-7-methoxy-2,2-dimethyl-l(2H)-benzopyran, benzamidine hydrochloride, the cysteine proteinase inhibitors N-ethylmalemide and epsilon-amino-n-caproic acid of the serinprotease inhibitors: phenylmethylsufonyl- fluoride, collhibin (company Pentapharm; INCI : hydrolysed rice protein), oenotherol (company Soliance; INCI
- SymMatrix (company Sym- rise, INCI: Maltodextrin, Rubus Fruticosus (Blackberry) Leaf Extract).
- Preferred actives of are selected from the group consisting of retinyl palmitate, ursolic acid, extracts from the leaves of the Rosaceae family, sub-family Rosoideae, genistein and daidzein.
- Skin-moisturizing agents are selected from the group consisting of alkane diols or alkane triols comprising 3 to 12 carbon atoms, preferably C 3 -Ci 0 -alkane diols and C 3 -Ci 0 -alkane triols. More preferably the skin moisturiz- ing agents are selected from the group consisting of: glycerol, 1,2-propylene glycol, 1,2-butylene glycol, 1,3-butylene glycol, 1,2-penta nediol, 1,2-hexanediol, 1,2- octanediol and 1,2-decanediol.
- compositions comprise substances stimu- lating the synthesis of glycosaminoglycans selected from the group consisting of hyaluronic acid and derivatives or salts, Subliskin (Sederma, INCI : Sinorhizobium Meliloti Ferment Filtrate, Cetyl Hydroxyethylcellulose, Lecithin), Hyalufix (BASF, INCI : Water, Butylene Glycol, Alpinia galanga leaf extract, Xanthan Gum, Caprylic/Capric Triglyceride), Stimulhyal (Soliance, I NCI : Calcium ketogluconate), Syn-Glycan (DSM, INCI : Tetradecyl Aminobutyroylvalylaminobutyric Urea Trifluoroacetate, Glycerin, Magnesium chloride), Kalpariane (Biotech Marine), DC Upregulex (Distinctive Cosmetic Ingredient
- Dragosantol and Dragosantol 100 from Sym- rise, oat glucan, Echinacea purpurea extract and soy protein hydrolysate are selected from the group consisting of hya luronic acid and derivatives or salts, retinol and derivatives, (-)-alpha-bisabolol or synthetic alpha-bisabolol such as e.g.
- compositions may also contain anti-inflammatory and/or redness and/or itch ameliorating ingredients, in particular steroidal substances of the corticosteroid type selected from the group consisting of hydrocortisone, dexamethasone, dexamethasone phosphate, methyl prednisolone or cortisone, are advantageously used as anti-inflammatory active ingredients or active ingredients to relieve reddening and itching, the list of which can be extended by the addition of other steroidal anti-inflammatories. Non-steroidal anti-inflammatories can also be used.
- oxicams such as piroxicam or tenoxicam
- salicylates such as aspirin, disalcid, solprin or fendosal
- acetic acid derivatives such as diclofenac, fenclofenac, indomethacin, sulindac, tolmetin or clindanac
- fenamates such as mefenamic, meclofenamic, flufenamic or niflumic
- propionic acid derivatives such as ibuprofen, naproxen, benoxaprofen or pyrazoles such as phenylbutazone, oxyphenylbutazone, febrazone or azapropazone.
- Anthranilic acid derivatives in particular avenanthramides described in WO 2004047833 Al, are preferred anti-itch ingredients in a composition according to the present invention.
- TRPV1 antagonists Suitable compounds which reduce the hypersensitivity of skin nerves based on their action as TRPV1 antagonists, encompass e.g. trans-4-tert-butyl cyclohexanol as described in WO 2009 087242 Al, or indirect modulators of TRPV1 by an activation of the ⁇ -receptor, e.g. acetyl tetrapeptide-15, are preferred.
- the total amount thereof preferably is in the range of from 0.1 to 3 % b.w., based on the total weight of the preparation.
- the total amount thereof preferably is in the range of from 0.1 to 2 % b.w., based on the total weight of the preparation.
- the total amount thereof preferably is in the range of from 0.01 to 3 % b.w., based on the total weight of the preparation.
- the total amount thereof preferably is in the range of from 0.001 to 0.1 % b.w., based on the total weight of the preparation.
- the total amount thereof preferably is in the range of from 0.01 to 3 % b.w., based on the total weight of the preparation.
- the total amount thereof preferably is in the range of from 0.01 to 1 % b.w., based on the total weight of the preparation.
- the total amount thereof preferably is in the range of from 0.01 to 0.5 % b.w., based on the total weight of the preparation.
- the total amount thereof preferably is in the range of from 0.01 to 1 % b.w., based on the total weight of the preparation.
- Echinacea purpurea extract is used as component (b5) or as constituent of component (b5)
- the total amount thereof preferably is in the range of from 0.1 to 0.6 % b.w., based on the total weight of the preparation.
- Alpinia galanga leaf extract is used as component (b5) or as constituent of component (b5)
- the total amount thereof preferably is in the range of from 0.1 to 5 % b.w., based on the total weight of the preparation.
- the total amount thereof preferably is in the range of from 0.1 to 5 % b.w., based on the total weight of the preparation.
- Tetradecyl Aminobutyroylvalylaminobutyric Urea Trifluoroacetate is used as component (b5) or as constituent of component (b5), the total amount thereof preferably is in the range of from 0.1 to 3 % b.w., based on the total weight of the preparation.
- the total amount thereof preferably is in the range of from 1 to 3 % b.w., based on the total weight of the preparation.
- the total amount thereof preferably is in the range of from 0.01 to 1 % b.w., based on the total weight of the preparation.
- the total amount thereof preferably is in the range of from 0.01 to 3 % b.w., based on the total weight of the preparation.
- the total amount thereof preferably is in the range of from 0.01 to 2 % b.w., based on the total weight of the preparation.
- a cosmetic composition preferably a topical preparation according to the invention containing
- proteasom can be significantly degraded by free radicals.
- the combination of one or more compounds of formula (I), respectively formula (I I) and one or more antioxidants of component (bl) is particularly beneficial because antioxidants additionally protect proteasom from reactive oxygen species.
- the combination of one or more compounds of formula (I), respectively formula (I I) and one or more sun protection factors of component (b2) is particularly beneficial because UV light is one major source for reactive oxygen species.
- collagen fragments in the dermis resulting from UVB-induced collagen degradation and strongly reduced proteasom in human skin are therefore cosmetic, dermato- logical and/or pharmaceutical preparations according to the invention which additionally include one or more UV filters (UV absorbers) and which thus act as compositions with pro- teasom stimulating activity and additionally as a sunscreen, overall resulting in a higher, improved proteasom level.
- UV filters UV absorbers
- the combination of one or more compounds of formula (I), respectively formula (II) and one or more agents selected from the group consisting of matrix-metalloproteinase (MMP) inhibitor (b3) is particularly beneficial resulting in an overall higher, improved proteasom level.
- MMP matrix-metalloproteinase
- the combination of one or more compounds of formula (I), respectively formula (II) and one or more skin moisturizing agents (b4) is particularly beneficial because skin moisturizing agents additionally improve the moisture status of the skin.
- the combination of one or more compounds of formula (I) and one or more agents selected from the group consisting of glycosaminoglycans (GAGs) and further substances stimulating the synthesis of glycosaminoglycans (b5) is particularly beneficial resulting in an overall higher, improved GAG level.
- the total quantity of antioxidants of component (bl) is in the range of from about 0.001 to about 10 % b.w. preferably in the range of from about 0.01 to about 5 % b.w., more preferably in the range of from about 0.05 to about 3 % b.w. and/or
- the total quantity of sun protection factors (UV filters and/or absorbers) of component (b2) is in the range of from about 0.01 to about 40 % b.w., preferably in the range of from about 0.1 to about 30 % by weight, more preferably in the range of from about 0.2 to about 20 % by weight, even more preferably in the range of from about 0.5 to about 15 % by weight, in particular in the range of from about 1.0 to about 10 % by weight, and/or
- the total quantity of matrix-metalloproteinase (MMP) inhibitors of component (b3) is in the range of from about 0.01 to about 5 % b.w. preferably in the range of from about 0.01 to about 3 % b.w. more preferably in the range of from about 0.05 to about 2 % b.w. and/or
- the total quantity of skin moisturizing agents of component (b4) is in the range of from about 0.1 to about 30 % b.w, preferably in the range of from about 0.25 to about 20 % b.w. more preferably in the range of from about 0.5 to about 10 % b.w., even more preferably in the range of from about 1 to about 5 % b.w. and/or
- • the total quantity of glycosaminoglycans and substances stimulating the synthesis of glycosaminoglycans of component (b5) is in the range of from about 0.01 to about 10 % b.w. preferably in the range of from about 0.05 to about 5 % b.w., more preferably in the range of from about 0.1 to about 3 % b.w.,
- the total quantity of anti-inflammatory agents of component (b6) is in the range of from about 0.01 to about 10 % b.w. preferably in the range of from about 0.05 to about 5 % b.w., more preferably in the range of from about 0.1 to about 3 % b.w.
- the total quantity of TRVP1 antagonists of component (b5) is in the range of from about 0.001 to about 5 % b.w. preferably in the range of from about 0.01 to about 3 % b.w., more preferably in the range of from about 0.05 to about 2 % b.w.
- anionic and/or amphoteric or zwitterionic surfactants are soaps, alkyl benzenesulfonates, al- kanesulfonates, olefin sulfonates, alkylether sulfonates, glycerol ether sulfonates, methyl ester sulfonates, sulfofatty acids, alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, fatty acid ether sulfates, hydroxy mixed ether sulfates, monoglyceride (ether) sulfates, fatty acid amide (ether) sulfates, mono- and dialkyl sulfosuccinates, mono- and dialkyl sulfosuccinamates, sulfotriglycerides, amide soaps, ether
- anionic surfactants contain polyglycol ether chains, they may have a conventional homolog distribution although they preferably have a narrow-range homolog distribution.
- Typical examples of amphoteric or zwitterionic surfac- tants are alkylbetaines, alkylamidobetaines, aminopropionates, aminoglycinates, imidazolin- ium betaines and sulfobetaines.
- the surfactants mentioned are all known compounds. Information on their structure and production can be found in relevant synoptic works, cf. for example J. Falbe (ed.) # "Surfactants in Consumer Products", Springer Verlag, Berlin, 1987, pages 54 to 124 or J.
- the percentage content of surfactants in the preparations may be from 0.1 to 10% by weight and is preferably from 0.5 to 5% by weight, based on the preparation.
- Suitable oil bodies which form constituents of the O/W emulsions, are, for example, Guer- bet alcohols based on fatty alcohols having 6 to 18, preferably 8 to 10, carbon atoms, esters of I inear C6-C 22 -fatty acids with linear or branched C6-C 2 2-fatty alcohols or esters of branched C 6 -C 13-carboxylic acids with linear or branched C 6 -C 22 -fatty alcohols, such as, for example, myristyl myristate, myristyl palmitate, myristyl stearate, myristyl isostearate, myristyl ole- ate, myristyl behenate, myristyl erucate, cetyl myristate, cetyl palmitate, cetyl stearate, ce- tyl isostearate, cetyl oleate, cetyl behenate, cetyl erucate, stearyl
- esters of linear C 6 -C 22 - fatty acids with branched alcohols in particular 2-ethylhexanol
- esters of Ci 8 -C 38 - alkylhy- droxy carboxylic acids with linear or branched C 6 -C 22 -fatty alcohols in particular Dioctyl Malate
- esters of linear and/or branched fatty acids with polyhydric alcohols such as, for example, propylene glycol, dimerdiol or trimertriol
- Guerbet alcohols triglycerides based on C 6 -Ci 0 -fatty acids, liquid mono-/di-/ti"iglyceride mixtures based on C 6 -Ci 8 -fatty acids
- esters of C 6 - C 22 -fatty alcohols and/or Guerbet alcohols with aromatic carboxylic acids in particular benzoic acid
- esters of C 2 - Ci 2 -dicarboxylic acids in particular 2-eth
- Fin- solv ® TN linear or branched, symmetrical or asymmetrical dialkyl ethers having 6 to 22 carbon atoms per alkyl group, such as, for example, dicaprylyl ether (Cetiol ® OE), ring-opening products of epoxidized fatty acid esters with polyols, silicone oils (cyclomethicones, silicone methicone grades, etc.) and/or aliphatic or naphthenic hydrocarbons, such as, for example, squalane, squalene or dialkylcyclohexanes.
- dicaprylyl ether Cetiol ® OE
- silicone oils cyclomethicones, silicone methicone grades, etc.
- aliphatic or naphthenic hydrocarbons such as, for example, squalane, squalene or dialkylcyclohexanes.
- surfactants may also be added to the preparations as emulsifiers, including for exam- pie:
- polyol esters and, in particular, polyglycerol esters such as, for example, polyglycerol polyricinoleate, polyglycerol poly-12-hydroxystearate or polyglycerol dimerate isos- tearate. Mixtures of compounds from several of these classes are also suitable;
- the addition products of ethylene oxide and/or propylene oxide onto fatty alcohols, fatty acids, alkylphenols, glycerol mono- and diesters and sorbitan mono- and diesters of fatty acids or onto castor oil are known commercially available products. They are homologue mixtures of which the average degree of alkoxylation corresponds to the ratio between the quantities of ethylene oxide and/or propylene oxide and substrate with which the addition reaction is carried out. C12/18 fatty acid monoesters and diesters of addition products of ethylene oxide onto glycerol are known as lipid layer enhancers for cosmetic formulations.
- the preferred emulsifiers are described in more detail as follows:
- Partial glycerides Typical examples of suitable partial glycerides are hydroxystearic acid monoglyceride, hydroxystearic acid diglyceride, isostearic acid monoglyceride, isostearic acid diglyceride, oleic acid monoglyceride, oleic acid diglyceride, ricinoleic acid monoglyceride, ricinoleic acid diglyceride, linoleic acid monoglyceride, linoleic acid diglyceride, linolenic acid monoglyceride, linolenic acid diglyceride, erucic acid monoglyceride, erucic acid diglyceride, tartaric acid monoglyceride, tartaric acid diglyceride, citric acid monoglyceride, citric acid diglyceride, malic acid monoglyceride, malic acid diglyceride and technical mixtures thereof which may still contain small quantities of triglyceride from the
- Sorbitan esters are sorbitan monoisostearate, sorbitan ses- quiisostearate, sorbitan diisostearate, sorbitan triisostearate, sorbitan monooleate, sorbitan sesquioleate, sorbitan dioleate, sorbitan trioleate, sorbitan monoerucate, sorbitan sesquierucate, sorbitan dierucate, sorbitan trierucate, sorbitan monoricino- leate, sorbitan sesquiricinoleate, sorbitan diricinoleate, sorbitan triricinoleate, sorbitan monohydroxystearate, sorbitan sesquihydroxystearate, sorbitan dihydroxystea- rate, sorbitan trihydroxystearate, sorbitan monotartrate, sorbitan sesquitartrate, sorbitan ditartrate, sorbitan tritartrate, sorbitan
- Polyglycerol esters are Polyglyceryl-
- polystyrene resin examples include the mono-, di- and triesters of trimethylol propane or pen- taerythritol with lauric acid, cocofatty acid, tallow fatty acid, palmitic acid, stearic acid, oleic acid, behenic acid and the like optionally reacted with 1 to 30 mol ethylene oxide.
- Anionic emulsifiers are aliphatic C12-22 fatty acids, such as palmitic acid, stearic acid or behenic acid for example, and C12-22 dicarboxylic acids, such as azelaic acid or sebacic acid for example.
- Amphoteric emulsifiers are amphboteric or zwitterionic surfactants.
- Zwitterionic surfactants are surface-active compounds which contain at least one quaternary ammonium group and at least one carboxylate and one sulfonate group in the molecule.
- Particularly suitable zwitterionic surfactants are the so-called betaines, such as the N-alkyl-N,N-dimethyl ammonium glycinates, for example cocoalkyl dimethyl ammonium glycinate, N-acylaminopropyl-N,N-dimethyl ammonium glycinates, for example cocoacylaminopropyl dimethyl ammonium glycinate, and 2-alkyl-3-carboxymethyl-3-hydroxyethyl imidazolines containing 8 to 18 carbon atoms in the alkyl or acyl group and cocoacylaminoethyl hydroxyethyl car- boxymethyl glycinate.
- betaines such as the N-alkyl-N,N-dimethyl ammonium glycinates, for example cocoalkyl dimethyl ammonium glycinate, N-acylaminopropyl-N,N-dimethyl ammonium glycinates, for example cocoacy
- Ampholytic surfactants are also suitable emulsifiers.
- Ampholytic surfactants are surface-active compounds which, in addition to a C 8 /i 8 alkyl or acyl group, contain at least one free amino group and at least one -COOH- or -SO3H- group in the molecule and which are capable of forming inner salts.
- ampholytic surfactants are N-alkyl glycines, N-alkyl propionic acids, N-alkylaminobutyric acids, N-alkyliminodipropionic acids, N- hydroxyethyl-N-alkylamidopropyl glycines, N-alkyl taurines, N-alkyl sarcosines, 2- alkylaminopropionic acids and alkylaminoacetic acids containing around 8 to 18 carbon atoms in the alkyl group.
- Particularly preferred ampholytic surfactants are N- cocoalkylaminopropionate, cocoacylaminoethyl aminopropionate and C12/18 acyl sar- cosine.
- Superfatting agents may be selected from such substances as, for example, lanolin and lecithin and also polyethoxylated or acylated lanolin and lecithin derivatives, polyol fatty acid esters, monoglycerides and fatty acid alkanolamides, the fatty acid alkanolamides also serving as foam stabilizers.
- the consistency factors mainly used are fatty alcohols or hydroxyfatty alcohols containing 12 to 22 and preferably 16 to 18 carbon atoms and also partial glycerides, fatty acids or hydroxyfatty acids. A combination of these substances with alkyl oligoglucosides and/or fatty acid N-methyl glucamides of the same chain length and/or polyglycerol poly-12- hydroxystea rates is preferably used. 5. Thickening agents and rheology additives
- Suitable thickeners are polymeric thickeners, such as Aerosil ® types (hydrophilic silicas), polysaccharides, more especially xanthan gum, guar-gua r, agar-agar, alginates and tyloses, car- boxymethyl cellulose and hydroxyethyl cellulose, also relatively high molecular weight poly- ethylene glycol monoesters and diesters of fatty acids, polyacrylates (for example Carbo- pols ® [Goodrich] or Synthalens ® [Sigma]), polyacrylamides, polyvinyl alcohol and polyvinyl pyrrolidone, surfactants such as, for example, ethoxylated fatty acid glycerides, esters of fatty acids with polyols, for example pentaerythritol or trimethylol propane, narrow-range fatty alcohol ethoxylates and electrolytes, such as sodium chloride and ammonium chloride.
- Aerosil ® types
- Suitable cationic polymers are, for example, cationic cellulose derivatives such as, for example, the quaternized hydroxyethyl cellulose obtainable from Amerchol under the name of Polymer JR 400 ® , cationic starch, copolymers of dia llyl ammonium salts and acrylamides, quaternized vinyl pyrrolidone/vinyl imidazole polymers such as, for example, Luviquat ® (BASF), condensation products of polyglycols and amines, quaternized collagen polypeptides such as, for example, Lauryldimonium Hydroxypropyl Hydrolyzed Collagen (Lamequat ® L, Grunau), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers such as, for example, amodimethicone, copolymers of adipic acid and dimethylaminohy- droxypropyl diethylenetriamine (Cartaretine , Sandoz
- Suitable anionic, zwitterionic, amphoteric and nonionic polymers are, for example, vinyl ace- tate/crotonic acid copolymers, vinyl pyrrolidone/vinyl acrylate copolymers, vinyl acetate/butyl maleate/isobornyl acrylate copolymers, methyl vinylether/maleic anhydride copolymers and esters thereof, uncrosslinked and polyol-crosslinked polyacrylic acids, acrylamidopropyl trimethylammonium chloride/acrylate copolymers, octylacryl- amide/methyl methacrylate/tert.-butylaminoethyl methacrylate/2-hydroxypropyl methacry- late copolymers, polyvinyl pyrrolidone, vinyl pyrrolidone/vinyl acetate copolymers, vinyl pyrrolidone/dimethylaminoethyl methacrylate/vinyl caprolactam
- Suitable pearlising waxes are, for example, alkylene glycol esters, especially ethylene glycol distearate; fatty acid alkanolamides, especially cocofatty acid diethanolamide; partial glycerides, especially stearic acid monoglyceride; esters of polybasic, optionally hydroxy- substituted carboxylic acids with fatty alcohols containing 6 to 22 carbon atoms, especially long-chain esters of tartaric acid; fatty compounds, such as for example fatty alcohols, fatty ketones, fatty aldehydes, fatty ethers and fatty carbonates which contain in all at least 24 carbon atoms, especially laurone and distearylether; fatty acids, such as stearic acid, hy- droxystearic acid or behenic acid, ring opening products of olefin epoxides containing 12 to 22 carbon atoms with fatty alcohols containing 12 to 22 carbon atoms and/or polyols containing 2 to 15 carbon
- Suitable silicone compounds are, for example, dimethyl polysiloxanes, methylphenyl pol- ysiloxanes, cyclic silicones and amino-, fatty acid-, alcohol-, polyether-, epoxy-, fluorine-, glycoside- and/or alkyl-modified silicone compounds which may be both liquid and resin-like at room temperature.
- Other suitable silicone compounds are simethicones which are mixtures of dimethicones with an average chain length of 200 to 300 dimethylsiloxane units and hydrogenated silicates.
- waxes may also be present in the preparations, more especially natural waxes such as, for example, candelilla wax, carnauba wax, Japan wax, espartograss wax, cork wax, guaruma wax, rice oil wax, sugar cane wax, ouricury wax, montan wax, bees- wax, shellac wax, spermaceti, lanolin (wool wax), uropygial fat, ceresine, ozocerite (earth wax), petrolatum, paraffin waxes and microwaxes; chemically modified waxes (hard waxes) such as, for example, montan ester waxes, sasol waxes, hydrogenated jojoba waxes and synthetic waxes such as, for example, polyalkylene waxes and polyethylene glycol waxes.
- natural waxes such as, for example, candelilla wax, carnauba wax, Japan wax, espartograss wax, cork wax, guaruma
- Metal salts of fatty acids such as, for example, magnesium, aluminium and/or zinc stearate or ricinoleate may be used as stabilizers.
- compositions may also contain one or more substances with a physiological cooling effect (cooling agents), which are preferably selected here from the following list: menthol and menthol derivatives (for example L-menthol, D-menthol, racemic menthol, isomenthol, neoisomenthol, neomenthol) menthylethers (for example (l-menthoxy)-l,2-propandiol, (I- menthoxy)-2-methyl-l,2-propandiol, l-menthyl-methylether), menthylesters (for example menthylformiate, menthylacetate, menthylisobutyrate, menthyllactates, L-menthyl-L- lactate, L-menthyl-D-lactate, menthyl-(2-methoxy)acetate, menthyl-(2-methoxyethoxy- )acetate, menthylpyroglutamate), menthylcarbonates (for example menth
- Suitable anti-microbial agents are, in principle, a ll substances effective against Gram- positive bacteria, such as, for example, 4- hydroxybenzoic acid and its salts and esters, N-(4- chlorophenyl)-N'-(3,4- dichlorophenyl)urea, 2,4,4'-trichloro-2'-hydroxy-diphenyl ether (triclosan), 4-chloro-3,5-dimethyl-phenol, 2,2'-methylenebis(6-bromo-4- chlorophenol), 3- methyl-4-(l-methylethyl)phenol, 2-benzyl-4-chloro-phenol, 3-(4-chlorophenoxy)-l,2- propanediol, 3-iodo-2-propynyl butylcarbamate, chlorhexidine, 3,4,4'-trichlorocarbanilide (TTC), antibacterial fragrances, thymol, thyme oil, eugenol, oil of cloves, menthol, mint
- Suitable enzyme inhibitors are, for example, esterase inhibitors. These are preferably trialkyl citrates, such as trimethyl citrate, tripropyl citrate, triisopropyl citrate, tributyl citrate and, in particular, triethyl citrate (Hydagen CAT).
- the substances inhibit enzyme activity, thereby reducing the formation of odour.
- esterase inhibitors are sterol sulfates or phosphates, such as, for example, lanosterol, cholesterol, campesterol, stigmasterol and sitosterol sulfate or phosphate, dicarboxylic acids and esters thereof, such as, for example, glutaric acid, monoethyl glutarate, diethyl glutarate, adipic acid, monoethyl adipate, diethyl adipate, malonic acid and diethyl malonate, hydroxycarboxylic acids and esters thereof, such as, for example, citric acid, malic acid, tartaric acid or diethyl tartrate, and zinc glycinate.
- sterol sulfates or phosphates such as, for example, lanosterol, cholesterol, campesterol, stigmasterol and sitosterol sulfate or phosphate
- dicarboxylic acids and esters thereof such as, for example, glutaric acid, monoethy
- Suitable odour absorbers are substances which are a ble to absorb and largely retain odour- forming compounds. They lower the partial pressure of the individual components, thus also reducing their rate of diffusion. It is important that perfumes must remain unimpaired in this process. Odour absorbers are not effective against bacteria. They comprise, for exam ple, as main constituent, a complex zinc salt of ricinoleic acid or specific, largely odour- neutral fragrances which are known to the person skilled in the art as "fixatives", such as, for exam ple, extracts of labdanum or styrax or certain abietic acid derivatives.
- the odour masking agents are fragrances or perfume oils, which, in addition to their function as odour masking agents, give the deodorants their respective fragrance note.
- Perfume oils which may be mentioned are, for exam ple, mixtures of natural and synthetic fragrances. Natural fragrances are extracts from flowers, stems and leaves, fruits, fruit peels, roots, woods, herbs and grasses, needles and branches, and resins and balsams. Also suitable are animal products, such as, for example, civet and castoreum .
- Typical synthetic fragrance compounds are products of the ester, ether, aldehyde, ketone, alcohol, and hydrocarbon type.
- Fragrance compounds of the ester type are, for example, benzyl acetate, p-tert-butylcyclohexyl acetate, linalyl acetate, phenylethyl acetate, lina lyl benzoate, benzyl formate, allyl cyclohex- ylpropionate, styrallyl propionate and benzyl salicylate.
- the ethers include, for example, benzyl ethyl ether
- the aldehydes include, for example, the linear alkanals having 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamen aldehyde, hy- droxycitronellal, lilial and bourgeonal
- the ketones include, for example, the ionones and methyl cedryl ketone
- the alcohols include anethole, citronellol, eugenol, isoeugenol, gera- niol, linaool, phenylethyl alcohol and terpineol
- a nd the hydrocarbons include mainly the terpenes and balsams.
- fragrance oils which are mostly used as aroma components, are also suitable as perfume oils, e.g. sage oil, camomile oil, oil of cloves, melissa oil, mint oil, cinnamon leaf oil, linden flower oil, juni- perberry oil, vetiver oil, olibanum oil, galbanum oil, labdanum oil and lavandin oil.
- Suitable astringent antiperspirant active ingredients are primarily salts of aluminium, zirco- nium or of zinc.
- Such suitable antihydrotic active ingredients are, for example, aluminium chloride, aluminium chlorohydrate, aluminium dichlorohydrate, aluminium sesquichlorohy- drate and complex compounds thereof, e.g. with 1,2- propylene glycol, aluminium hydroxy- allantoinate, aluminium chloride tartrate, aluminium zirconium trichlorohydrate, aluminium zirconium tetrachlorohydrate, aluminium zirconium pentachlorohydrate and complex com- pounds thereof, e.g. with amino acids, such as glycine.
- Standard film formers are, for example, chitosan, microcrystalline chitosan, quaternized chitosan, polyvinyl pyrrolidone, vinyl pyrrolidone/vinyl acetate copolymers, polymers of the acrylic acid series, quaternary cellulose derivatives, collagen, hyaluronic acid and salts thereof and similar compounds.
- Suitable antidandruff agents are Pirocton Olamin (l-hydroxy-4-methyl-6-(2,4,4-trimethyl- pentyl)-2-(lH)-pyridinone monoethanolamine salt), Baypival (Climbazole), Ketoconazol ® (4- acetyl-l- ⁇ 4-[2-(2,4-dichlorophenyl) r-2-(lH-imidazol-l-ylmethyl)-l,3-dioxylan-c-4-ylmethoxy- phenylj-piperazine, ketoconazole, elubiol, selenium disulfide, colloidal sulfur, sulfur poly- ethylene glycol sorbitan monooleate, sulfur ricinol polyethoxylate, sulfur tar distillate, salicylic acid (or in combination with hexachlorophene), undecylenic acid, monoethanolamide sulfosuccinate Na salt, Lamepon U D (protein/undec
- Preferred cosmetics carrier materials are solid or liquid at 25°C and 1013 mbar (including highly viscous substances) as for example glycerol, 1,2-propylene glycol, 1,2-butylene glycol, 1,3-propylene glycol, 1,3-butylene glycol, ethanol, water and mixtures of two or more of said liquid carrier materials with water.
- these preparations according to the invention may be produced using preservatives or solubilizers.
- Other preferred liquid carrier substances which may be a component of a preparation according to the invention are selected from the group consisting of oils such as vegetable oil, neutral oil and mineral oil.
- Preferred solid carrier materials which may be a component of a preparation according to the invention are hydrocolloids, such as starches, degraded starches, chemically or physically modified starches, dextrins, (powdery) maltodextrins (preferably with a dextrose equivalent value of 5 to 25, preferably of 10 - 20), lactose, silicon dioxide, glucose, modified celluloses, gum arabic, ghatti gum, traganth, karaya, carrageenan, pullulan, curdlan, xanthan gum, gellan gum, guar flour, carob bean flour, alginates, agar, pectin and inulin and mixtures of two or more of these solids, in particular maltodextrins (preferably with a dextrose equivalent value of 15 - 20), lactose, silicon dioxide and/or glucose.
- hydrocolloids such as starches, degraded starches, chemically or physically modified starches, dextrins, (p
- hydrotropes for example ethanol, isopropyl alcohol or polyols
- Suitable polyols preferably contain 2 to 15 carbon atoms and at least two hydroxyl groups.
- the polyols may contain other functional groups, more especial- ly amino groups, or may be modified with nitrogen. Typical examples are
- alkylene glycols such as, for example, ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, hexylene glycol and polyethylene glycols with an average molecular weight of 100 to 1000 Dalton;
- methylol compounds such as, in particular, trimethylol ethane, trimethylol propane, trimethylol butane, pentaerythritol and dipentaerythritol;
- lower alkyl glucosides particularly those containing 1 to 8 carbon atoms in the alkyl group, for example methyl and butyl glucoside;
- sugar alcohols containing 5 to 12 carbon atoms for example sorbitol or mannitol
- sugars containing 5 to 12 carbon atoms for example glucose or sucrose
- dialcoholamines such as diethanolamine or 2-aminopropane-l,3-diol. 16.
- Suitable preservatives are, for exam ple, phenoxyethanol, formaldehyde solution, parabens, pentanediol or sorbic acid and the other classes of compounds listed in Appendix 6, Parts A and B of the Kosmetikverowski ("Cosmetics Directive").
- Suitable perfume oils are mixtures of natural and synthetic perfumes.
- Natural perfumes include the extracts of blossoms (lily, lavender, rose, jasmine, neroli, ylang-ylang), stems and leaves (geranium, patchouli, petitgrain), fruits (a nise, coriander, caraway, juniper), fruit peel (bergamot, lemon, orange), roots (nutmeg, angelica, celery, cardamom, costus, iris, calmus), woods (pinewood, sandalwood, guaiac wood, cedarwood, rosewood), herbs and grasses (tarragon, lemon grass, sage, thyme), needles and branches (spruce, fir, pine, dwarf pine), resins and balsams (galbanum, elemi, benzoin, myrrh, olibanum, opoponax).
- Typical synthetic perfume compounds are products of the ester, ether, aldehyde, ketone, alcohol and hydrocarbon type.
- perfume compounds of the ester type are benzyl acetate, phenoxyethyl isobu- tyrate, p-tert.
- butyl cyclohexylacetate linalyl acetate, dimethyl benzyl carbinyl acetate, phenyl ethyl acetate, linalyl benzoate, benzyl formate, ethylmethyl phenyl glycinate, allyl cyclo- hexyl propionate, styrallyl propionate and benzyl salicylate.
- Ethers include, for example, benzyl ethyl ether while aldehydes include, for exa mple, the linear alkanals containing 8 to 18 carbon atoms, citral, citronellal, citronellyloxyacetaldehyde, cyclamen aldehyde, hydroxy- citronellal, lilial and bourgeonal.
- suitable ketones are the ionones, ⁇ - isomethylionone and methyl cedryl ketone.
- Suitable alcohols are anethol, citronellol, euge- nol, isoeugenol, geraniol, linalool, phenylethyl alcohol and terpineol.
- the hydrocarbons mainly include the terpenes and balsams. However, it is preferred to use mixtures of different perfume com pounds which, together, produce an agreeable perfume.
- Other suitable perfume oils are essential oils of relatively low volatility which are mostly used as aroma components. Examples are sage oil, camomile oil, clove oil, melissa oil, mint oil, cinnamon leaf oil, lime-blossom oil, juniper berry oil, vetiver oil, olibanum oil, galbanum oil, ladanum oil and lavendin oil.
- bergamot oil dihydromyrcenol, lilial, lyral, citronellol, phenylethyl alcohol, hex- ylcinnamaldehyde, geraniol, benzyl acetone, cyclamen aldehyde, linalool, Boisambrene Forte, Ambroxan, indole, hedione, sandelice, citrus oil, mandarin oil, orange oil, allylamyl glycolate, cyclovertal, lavendin oil, clary oil, damascone, geranium oil bourbon, cyclohexyl salicylate, Vertofix Coeur, Iso-E-Super, Fixolide N P, evernyl, iraldein gamma, phenylacetic acid, geranyl acetate, benzyl acetate, rose oxide,
- Suitable dyes are any of the substances suitable and approved for cosmetic purposes as listed, for example, in the publication "Kosmetician mistakestoff” of the Farbstoff- kom mission der Deutschen Anlagenstician, Verlag Chemie, Weinheim, 1984, pages 81 to 106.
- Examples include cochineal red A (C.I . 16255), patent blue V (C.I . 42051), indigotin (C.I. 73015), chlorophyllin (C.I . 75810), quinoline yellow (C.I . 47005), titanium dioxide (C.I . 77891), indanthrene blue RS (C.I. 69800) and madder lake (C.I . 58000).
- Luminol may also be present as a luminescent dye.
- Advantageous coloured pigments are for example titanium dioxide, mica, iron oxides (e.g. Fe 2 0 3 Fe 3 0 4 , FeO(OH)) and/or tin oxide.
- Advantageous dyes are for example carmine, Berlin blue, chromium oxide green, ultramarine blue and/or manganese violet.
- compositions according to the present inventions are selected from the group of products for treatment, protecting, care and cleansing of the skin and/or hair or as a makeup product, preferably as a leave-on product (meaning that the one or more compounds of formula (I) stay on the skin and/or hair for a longer period of time, compared to rinse-off products, so that the moisturizing and/or anti-ageing and/or wound healing promoting action thereof is more pronounced).
- the formulations according to the invention are preferably in the form of an emulsion, e.g. W/O (water-in-oil), O/W (oil-in-water), W/O/W (water-in-oil-in-water), 0/W/O (oil-in-water- in-oil) emulsion, PIT emulsion, Pickering emulsion, emulsion with a low oil content, micro- or nanoemulsion, a solution, e.g.
- a gel including hydrogel, hydrodispersion gel, oleogel
- spray e.g. pump spray or spray with propellant
- a foam or an impregnating solution for cosmetic wipes e.g. soap, synthetic detergent, liquid washing, shower and bath preparation, bath product (capsule, oil, tablet, salt, bath salt, soap, etc.), effervescent preparation, a skin care product such as e.g.
- an emulsion as described above, ointment, paste, gel (as described above), oil, balsam, serum, powder (e.g. face powder, body powder), a mask, a pencil, stick, roll-on, pump, aerosol (foaming, non-foaming or post- foaming), a deodorant and/or antiperspirant, mouthwash and mouth rinse, a foot care product (including keratolytic, deodorant), an insect repellent, a sunscreen, aftersun preparation, a shaving product, aftershave balm, pre- and aftershave lotion, a depilatory agent, a hair care product such as e.g.
- shampoo including 2-in-l shampoo, anti-dandruff shampoo, baby shampoo, shampoo for dry scalps, concentrated shampoo
- conditioner hair tonic, hair water, hair rinse, styling creme, pomade, perm and setting lotion
- hair spray e.g. gel or wax
- hair smoothing agent detangling agent, relaxer
- hair dye such as e.g. temporary direct-dyeing hair dye, semi-permanent hair dye, permanent hair dye, hair conditioner, hair mousse, eye care product, make-up, make-up remover or baby product.
- the formulations according to the invention are particularly preferably in the form of an emulsion, in particular in the form of a W/O, O/W, W/O/W, 0/W/O emulsion, PIT emulsion, Pickering emulsion, emulsion with a low oil content, micro- or nanoemulsion, a gel (including hydrogel, hydrodispersion gel, oleogel), a solution e.g. in oil (fatty oils or fatty acid esters, in particular C 6 -C 32 fatty acid C 2 -C 30 esters)) or silicone oil, or a spray (e.g. pump spray or spray with propellant).
- a gel including hydrogel, hydrodispersion gel, oleogel
- a solution e.g. in oil (fatty oils or fatty acid esters, in particular C 6 -C 32 fatty acid C 2 -C 30 esters)) or silicone oil
- a spray e.g. pump spray or spray with propellant.
- Auxiliary substances and additives can be included in quantities of 5 to 99 % b.w., preferably 10 to 80 % b.w., based on the total weight of the formulation.
- the amounts of cosmetic or dermatological auxiliary agents and additives and perfume to be used in each case can easily be determined by the person skilled in the art by simple trial and error, depending on the nature of the particular product.
- the preparations can also contain water in a quantity of up to 99 % b.w., preferably 5 to 80 % b.w., based on the total weight of the preparation. It should be noted that the information on additives and their ranges for cosmetic compositions are also valid for pharmaceutical or dermatalogical formulations.
- compositions may also be administered orally, preferably in the form of a capsule.
- the compositions are typically encapsulated by means of a solid covering material, which is preferably selected from starches, degraded or chemically or physically modified starches (in particular dextrins and maltodextrins), gelatins, gum arabic, agar-agar, ghatti gum, gellan gum, modified and non-modified celluloses, pullulan, curdlan, carrageenans, alginic acid, alginates, pectin, inulin, xanthan gum and mixtures of two or more of said substances.
- a solid covering material which is preferably selected from starches, degraded or chemically or physically modified starches (in particular dextrins and maltodextrins), gelatins, gum arabic, agar-agar, ghatti gum, gellan gum, modified and non-modified celluloses, pullulan, curdlan, carrageenans, al
- the solid covering material is preferably selected from gelatin (preferred are pork, beef, chicken and/or fish gelatins and mixtures thereof, preferably comprising at least one gelatin with a bloom value of greater than or equal to 200, preferably with a bloom value of greater than or equal to 240), maltodextrin (preferably obtained from maize (corn), wheat, tapioca or potato, preferred maltodextrins have a DE value of 10 - 20), modified cellulose (for exam ple cellulose ether), alginates (for example Na-alginate), carrageenan (beta-, iota-, lamb- da- and/or kappa carrageenan), gum arabic, curdlan and/or agar-agar.
- gelatin preferred are pork, beef, chicken and/or fish gelatins and mixtures thereof, preferably comprising at least one gelatin with a bloom value of greater than or equal to 200, preferably with a bloom value of greater than or equal to 240
- Gelatin is preferably used, in particular, because of its good availability in different bloom values.
- Particularly preferred, especially for oral use are seamless gelatin or alginate capsules, the covering of which dissolves very rapidly in the mouth or bursts when chewing. Production may take place, for example, as described in EP 0389700 Al, US 4,251,195, US 6,214,376, WO 2003 055587 or WO 2004 050069 Al.
- microcapsules are understood to be spherical aggregates with a diameter of about 0.1 to about 5 mm which contain at least one solid or liquid core surrounded by at least one continuous membrane. More precisely, they are finely dispersed liquid or solid phases coated with film-forming polymers, in the production of which the polymers are deposited onto the material to be encapsulated after emulsification and coacervation or interfacial polymerization. I n another process, liquid active principles are absorbed in a matrix (“microsponge”) and, as microparticles, may be additionally coated with film-forming polymers.
- microsponge a matrix
- microscopically small capsules also known as nanocapsules
- multiple-core aggregates also known as microspheres, which contain two or more cores distributed in the continuous membrane material.
- single-core or multiple-core microcapsules may be surrounded by an additional second, third etc. membrane.
- the membrane may consist of natural, semisynthetic or synthetic materials.
- Natural membrane materials are, for example, gum arabic, agar agar, agarose, maltodextrins, alginic acid and salts thereof, for example sodium or calcium alginate, fats and fatty acids, cetyl alcohol, collagen, chitosan, lecithins, gelatin, albumin, shellac, polysaccharides, such as starch or dextran, polypeptides, protein hydrolyzates, sucrose and waxes.
- Semisynthetic membrane materials are inter alia chemically modified celluloses, more particularly cellulose esters and ethers, for example cellulose acetate, ethyl cellulose, hydroxy- propyl cellulose, hydroxypropyl methyl cellulose and carboxymethyl cellulose, and starch derivatives, more particularly starch ethers and esters.
- Synthetic membrane materials are, for example, polymers, such as polyacrylates, polyamides, polyvinyl alcohol or polyvinyl pyr- rolidone.
- microcapsules examples are the following commercial products (the membrane material is shown in brackets) Hallcrest Microcapsules (gelatin, gum arabic), Coletica Thalas- pheres (maritime collagen), Lipotec Millicapseln (alginic acid, agar agar), Induchem Unispheres (lactose, microcrystalline cellulose, hydroxypropylmethyl cellulose), Unicetin C30 (lactose, microcrystalline cellulose, hydroxypropylmethyl cellulose), Kobo Glycospheres (modified starch, fatty acid esters, phospholipids), Softspheres (modified agar agar) and Kuhs Probiol Nanospheres (phospholipids).
- the active principles are released from the microcapsules by mechanical, thermal, chemical or enzymatic destruction of the membrane, normally during the use of the preparations containing the microcapsules.
- a shell is obtained by coazervation, precipitation or polycondensation of anionic and cationic polymers has been quite suitable for the formation of stable capsules.
- a preferred process for the encapsulation of active principles according to the present invention is characterised in that it comprises the steps of
- anionic and cationic polymers in steps (a) and (c) can be exchanged.
- Gel formers are substances which are capable of forming gels in aqueous solution at temperatures above 40° C.
- Typical examples of such gel formers are heteropolysaccharides and proteins.
- Preferred thermogelling heteropolysaccharides are agaroses which may be present in the form of the agar agar obtainable from red algae, even together with up to 30% by weight of non-gel-forming agaropectins.
- the principal constituent of agaroses are linear polysaccharides of Galactose and 3,6-anhydro-L-galactose with alternate 1,3- and 1,4-glycosidic bonds.
- the heteropolysaccharides preferably have a molecular weight of 110,000 to 160,000 and are both odourless and tasteless. Suitable alternatives are pectins, xanthans (including xanthan gum) and mixtures thereof. Other preferred types are those which in 1% by weight aqueous solution still form gels that do not melt below 80° C. and solidify again above 40° C. Examples from the group of thermogelling proteins are the various gelatines.
- alginic acid is a mixture of carboxyl-containing polysaccharides with the following idealized monomer unit:
- the average molecular weight of the alginic acid or the alginates is in the range from 150,000 to 250,000.
- Salts of alginic acid and complete and partial neutralization products thereof are understood
- the alkali metal salts preferably sodium alginate ("algin") and the ammonium and alkaline earth metal salts.
- Mixed alginates for example sodium/magnesium or sodium/calcium alginates, are particularly preferred.
- carboxymethyl celluloses and anionic chitosan derivatives for example the carboxylation and above all succinylation products are also suitable for this purpose.
- Chitosans are biopolymers which belong to the group of hydrocol- loids. Chemically, they are partly de-acetylated chitins differing in their molecular weights which contain the following - idealized - monomer unit:
- chitosans are cationic biopolymers under these conditions.
- the positively charged chitosans are capable of interacting with oppositely charged surfaces and are therefore used in cosmetic hair-care and body-care products and pharmaceutical preparations.
- a 1 to 10 and preferably 2 to 5% by weight aqueous solution of the gel former, preferably agar agar, is normally prepared and heated under reflux.
- a second aqueous solution containing the cationic polymer, preferably chitosan, in quantities of 0.1 to 2 and preferably 0.25 to 0.5% by weight and the active principle in quantities of 0.1 to 25 and preferably 0.25 to 10% by weight is added in the boiling heat, preferably at 80 to 100 ° C; this mixture is called the matrix.
- the charging of the microcapsules with active principles may also comprise 0.1 to 25% by weight, based on the weight of the capsules.
- water-insoluble constituents for example inorganic pigments
- inorganic pigments may also be added at this stage to adjust viscosity, generally in the form of aqueous or aqueous/alcoholic dispersions.
- emulsifiers and/or solubilisers to the matrix.
- the matrix After its preparation from gel former, cationic polymer and active principle, the matrix optionally is very finely dispersed in an oil phase with intensive shearing in order to produce small particles in the subsequent encapsulation process. It has proved to be particularly advantageous in this regard to heat the matrix to temperatures in the range from 40 to 60° C while the oil phase is cooled to 10 to 20° C.
- the actual encapsulation i.e. formation of the membrane by contacting the cationic polymer in the matrix with the anionic polymers, takes place in the third step.
- the result- ing aqueous preparations generally have a microcapsule content of 1 to 10% by weight.
- the solution of the polymers can be of advantage for the solution of the polymers to contain other ingredients, for example emulsifiers or preservatives.
- microcapsules with a mean diameter of preferably 1 to 3 mm are obtained. It is advisable to sieve the capsules to ensure a uniform size distribution.
- the microcapsules thus obtained may have any shape with- in production-related limits, but are preferably substantially spherical.
- compositions of the present invention are preferably dermatological compositions, which are preferably administered topically to the skin. Therefore, an object of the invention is a method for cosmetically affecting a skin care treatment comprising topically applying to the skin a skin care efficient amount of one or more of a compound of formula (I), respectively formula (I I).
- Another object of the invention is a method for the cosmetically treatment of the epidermis of human beings suffering from the signs of aging, suffering from dry skin and for the prevention of free radical formation on skin, comprising topically administering an effective amount of one or more compounds of formula (I) ), respectively formula (I I) to the epider- mis.
- the present invention also refers to a process for preparing a cream, especially intended for topically treatment of skin to reduce signs of aging, reduce dry skin and maladies associated with free radical formation on skin, comprising blending one or more compounds of formula (I), respectively formula (II) with a cream base.
- cream base means a basic formulation com prising ingredients, which are mentioned above, thus the formulation, can be used as cream or lotion or ointment.
- a process is preferred for the cosmetical or dermatological treatment of the skin, comprising applying a cosmetic or pharmaceutical composition of the present invention to the skin.
- the filtrate comprising the intermediate can be used for the next step.
- a) 426g (3,00 Mol) of Homomenthol is added to the above-mentioned filtrate, the temperature is raised to 60°C and under stirring and a vacuum of lOOmbar the Ethyl acetate is distilled off the reaction mixture.
- 56g of Sulfuric acid are added at a tempera- ture of 50°C within 20minutes, stirring is continued for 6h.
- 500g of Toluene are added to the reaction mixture and after cooling to 5-10°C the dosage of 500g of iced water follows.
- NHDF (normal human dermal fibroblasts) cells are disseminated in a 96-well microtiter plate in a concentration of 1x105 cells/well (DMEM, 10% FCS). After cultivation for 24 h at 37°C and 5% C02 in DMEM medium, enriched with 10% FCS, various concentrations of the test substances and are added and incubated for a further 72 h. The maximum concentration of the test substances used corresponds from 0.3 times of the IC20 value of the cytotoxicity assay.
- the 20S Proteasome Assay (AAT Bioquest, Inc.) is performed according to the manu- facturer's protocol.
- the AmpliteTM Flourometric 20S Proteasome Assay Kit is a homogenous fluorescent assay that measures the chymotrypsin-like protease activity associated with the proteasome complex.
- This kit uses LLVY_R110 as a flourogenic indicator for proteasome activity. Cleavage of LLVY-R110 by proteasome generates the strongly green fluorescent R110 that is monitored fluorometrically. The fluorescence of the blank wells with growth medium was subtracted from the value for those wells with the cells. The results of the cells with treatment with different substances were compared with untreated cells.
- HHFSC Human Hair Follicle Stem Cells
- HHFSC Human Hair Follicle Stem Cells isolated from hair follicle bulge (Celprogen) were cultivated in culture ware pre-coated with Human Hair Follicle Stem Cell Extra-cellular Matrix (Celprogen). The cells were incubated 2 h prior to and 16 h after UVB irradiation with test com pounds. Cells were irradiated with 25 mJ/cm 2 UVB in the presence of buffer solution. Apoptosis induction was evaluated by caspase 3/7 protein expression (Caspase-Glo 3/7, Promega) and quantified by chemiluminescence measurement.
- Results are mean values from 2 independent experiments with quadruple determinations each.
- RFU DAPI Relative fluorescence units (Ex 380/20, Em 440/40) of the wells with test substance, DAPI and DCF treatment, with cells
- RFU DCF Relative fluorescence units (Ex 485/20, Em 528/20) of the wells with test substance, DAPI and DCF treatment, with cells
- RFU control Relative fluorescence units of the wells without test substance, DAPI and DCF treatment, with cells (The control was calculated like the other samples.)
- RFU BLANK Relative fluorescence units of the wells without test substance, without DAPI and DCF treatment but with cells
- NHDF normal human dermal fibroblast cells
- the maximum concentration of the test substances used corresponds to 0.2 times the value of the IC20 of the cytotoxicity assay.
- the protein amount was determined using the Biorad BCA assay. All samples were adjusted to the same protein level before application on a fast Criterion Gel (Biorad) to perform electrophoresis for 20 minutes at 300 V. Thereafter the proteins were transferred to a PVDF membrane on a semi-dry blotter (30 minutes, 25 V). The blotted membrane is blocked for 4 hours in a 5% milk powder solution in TBST at 4°C. After washing, the membrane is incubated with the first antibody solution HO-1 from abeam (1:500 in 1% milk powder in TBST) over night.
- NHDF normal human dermal fibroblasts
- DMEM fully enriched medium
- FCS fully enriched medium
- Various concen- trations of the test substances and TGF-betal as internal standard are added and incubated for 72 h.
- the maximum concentration of the test substances used corresponds to 0.2 times the value of the IC20 of the cytotoxicity assay.
- B16V mouse melanoma cells are disseminated in a 96-well micro-titre plate in a concentration of 7.5 x 10 3 cells/well. After cultivation for 24 h at 37°C and 5% C02 in RPM I medium, enriched with 10% foetal calf serum, various concentrations of the test substances and 0.6 mM tyrosine and 10 nM -MSH (-melanocyte stimulating hormone) are added and incubated for a further 96 h. The maximum concentration of the test substances used corresponds to 0.1 times the value of the IC 2 o value of the cytotoxicity assay. Only tyrosine and -MSH are added to the controls.
- Atest compound absorption of the wells with test substance and with cells
- the IC 50 for each test compound is calculated. This is the concentration of a test compound at which pigmentation is inhibited by 50%.
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Abstract
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Priority Applications (3)
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EP14727834.5A EP3008038B1 (en) | 2013-06-09 | 2014-06-04 | New succinate derivatives |
US14/896,824 US9820923B2 (en) | 2013-06-09 | 2014-06-04 | Succinate derivatives |
BR112015030331-5A BR112015030331B1 (en) | 2013-06-09 | 2014-06-04 | SUCCINATE DERIVATIVES, THEIR USES, COSMETIC OR PHARMACEUTICAL COMPOSITION, COSMETIC METHODS, AND PROCESS TO PREPARE A CREAM |
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EP13171161.6A EP2810934A1 (en) | 2013-06-09 | 2013-06-09 | New succinate derivatives |
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WO2018171917A1 (en) | 2017-03-21 | 2018-09-27 | Symrise Ag | 2,3,6-trimethylcyclohexanol as a scenting and/or flavoring agent |
CN109311804A (en) * | 2016-06-08 | 2019-02-05 | 高级醇工业株式会社 | Cosmetic base and cosmetics comprising amide alcohol ester |
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DE102016225735A1 (en) | 2016-12-21 | 2018-06-21 | Henkel Ag & Co. Kgaa | Cosmetic agents against body odor with improved long-term effect |
US20220313586A1 (en) * | 2021-03-31 | 2022-10-06 | L'oreal | Cosmetic composition with glaucine, retinol and peptides to combat skin aging |
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2013
- 2013-06-09 EP EP13171161.6A patent/EP2810934A1/en not_active Withdrawn
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- 2014-06-04 BR BR112015030331-5A patent/BR112015030331B1/en active IP Right Grant
- 2014-06-04 EP EP14727834.5A patent/EP3008038B1/en active Active
- 2014-06-04 US US14/896,824 patent/US9820923B2/en active Active
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EP2810934A1 (en) | 2014-12-10 |
EP3008038B1 (en) | 2018-04-04 |
EP3008038A1 (en) | 2016-04-20 |
US20160128923A1 (en) | 2016-05-12 |
BR112015030331A8 (en) | 2019-12-24 |
BR112015030331A2 (en) | 2017-07-25 |
BR112015030331B1 (en) | 2020-09-29 |
US9820923B2 (en) | 2017-11-21 |
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