HK1111351B - Cosmetic compositions comprising specific cyclohexanmono-, -di-or-triols or cyclohexyl methan-or-ethan-or-propoanols - Google Patents

Description

Cosmetic composition comprising a specific cyclohexanmono-, di-or-triol or cyclohexylmethyl-or-ethyl-or-propanol

Technical Field

The present invention relates to topical cosmetic compositions and methods for improving skin morphology, including reducing redness, inflammation, irritation, and skin aging, as well as skin imperfections associated with skin disorders, and for maintaining healthy skin and hair.

Background

The day-to-day abrasion of the skin results in a number of conditions which are unpleasant, uncomfortable and unsightly, including redness of the skin and various skin symptoms associated with skin disorders such as inflammation, irritation and skin aging. The present invention provides cosmetic compositions and methods that can be used to alleviate these symptoms, promote appeal and/or improve skin morphology. In addition, the present invention also includes therapeutic cosmetic compositions and methods that can be used to maintain healthy skin and hair, as well as reduce hair follicle stimulation and hair loss.

It has been disclosed that organic alcohols, glycols and polyols can be used topically to treat a variety of dermatological conditions.

U.S. patent No. 6,290,937 to Brown, published at 18.9.2001 and withdrawn from the publication by the patent office, describes a series of pharmaceutical compositions which are said to enhance the melanin content in mammalian melanocytes and which are also useful for treating skin proliferative disorders, such as acne vulgaris. The disclosed compositions may utilize C₃-C₅₀Glycols as pharmaceutically active agents; 1, 2-cis-and 1, 2-trans-cyclohexanediols are particularly disclosed as active ingredients. Furthermore, 1, 2-cis-cyclopentanediol is a preferred active compound. Since this patent has been withdrawn from disclosure, it cannot constitute a priority.

U.S.6,184,422 to Barbier et al, published 2/6/2001, discloses a group of unsaturated long chains of cyclohexanediols (e.g., C)₁₂) And (3) derivatives. It is taught that these substances can be used topically for the treatment of hyperproliferative diseases and sebaceous gland diseases, such as acne. Related U.S.5,969,190 is also seen.

U.S.5,886,233 to Steinmeyer et al, published 3, 23, 1999, describes cyclohexanone derivatives useful in the synthesis of vitamin D compounds. These compounds are said to be useful in the treatment of skin, for example in the treatment of acne.

U.S.6,277,837 to DeLuca, Jr et al, published on 8/21 of 2001, describes a group of compounds including cyclohexanediol moieties associated with vitamin D, which compositions are taught to be useful in the treatment of cell proliferative disorders, such as psoriasis. Related U.S.6,127,559; 5,945,410; 5,936,133, respectively; and 5,843,928.

U.S.5,641,809 to Hagen et al, published 24.6.1997, describes a skin treatment composition comprising lanolin and esters of lanolin acids. This patent teaches that lanolin includes C₉-C₂₂As one component.

U.S.6,723,755 to Chomczynski, published on 20.4.2004, relates to the use of cyclohexanol-derived materials in the treatment of rosacea, acne vulgaris and inflammatory conditions. The U.S. and PCT family of patents disclosed in this publication are published as patent applications at 12 months 2003.

Other cyclohexane derivatives, inositol, containing 6 hydroxyl groups, have been used in pharmaceutical and cosmetic applications. This particular compound is involved in The maintenance of The skin (see Daniel BMowrey, The Scientific differentiation of Herbal Medicine, pp.247-251, 1986). For example, in U.S.4,803,069 to kekekesis, published 2/7/1989, inositol is used as an added component in the treatment of acne along with plant extracts and erythromycin. In this patent, it is taught that inositol provides a normal effect to the skin when used with other components.

U.S. Pat. No. 5,116,605 to Alt, published 3/26 1992, describes the use of inositol as a solubilizing and/or dispersing agent in compositions for alleviating male sexual deterioration.

U.S.5,962,517 to Murad, published 5.10.1999, describes the use of inositol as an added component given orally in the treatment of acne using zinc compounds and vitamin a.

U.S.6,645,510 to Coury et al, published 11/2003, describes an emulsion-based skin product that may include inositol as a healing agent.

Brief description of the invention

The present invention relates to a method for improving skin morphology by treating skin redness and various skin conditions associated with skin disorders including inflammation, irritation, and skin aging in humans comprising topically applying to a human in need thereof a safe and effective amount (e.g., from about 0.001 to about 10 mg/cm) at the site of said condition²) Having the formulaA compound of the formula (I) is,

wherein R is¹Is selected from-OH and C₁-C₃Alkyl OH (alkanol), and R²，R³，R⁴，R⁵And R⁶Each independently selected from-H, -OH, C₁-C₆Alkyl and C₃-C₆A cycloalkyl group; wherein the total number of-OH groups in the compound is no more than 5.

Particularly preferred compounds are cyclohexanol, cyclohexanediols (including 1, 2-cyclohexanediol, 1, 3-cyclohexanediol, and 1, 4-cyclohexanediol), cyclohexanetriol (including 1, 2, 3-cyclohexanetriol and 1, 3, 5-cyclohexanetriol), and mixtures of these. The active substance may be applied together with a cosmetic carrier.

The present invention also includes methods of maintaining healthy hair and reducing hair loss in humans comprising administering to the scalp of a patient in need of treatment a safe and effective amount of an active compound as defined above.

Finally, the present invention includes topically applied cosmetic compositions comprising from about 0.001% to about 10% of an active compound as defined above, and a cosmetically acceptable topical carrier. The cosmetic composition may, for example, be a gel, cream, paste, solid, tonic, soap, body hygiene liquid, face pack gel or shampoo.

All percentages and ratios given herein are by weight unless specifically stated otherwise.

All patents and other publications cited in this application are incorporated herein by reference.

Detailed Description

The term "safe and effective amount" as used herein is intended to define the amount of active or cosmetic composition containing the active that is used to provide effective treatment of the condition being treated, such as skin redness, skin inflammation, skin irritation, and skin aging, or for the purpose of maintaining the skin and hair, without providing the user with a significant risk of side effects associated with the use of any active.

The present invention provides a composition and method for improving skin morphology by reducing skin redness and symptoms associated with skin inflammation, irritation, and skin aging. This object is achieved by means of a topically applied active substance having the formula:

in the formula, R¹Is selected from-OH and C₁-C₃Alkyl OH (C)₁-C₃Alkanol), and R²，R³，R⁴，R⁵And R⁶Each independently selected from-H, -OH, C₁-C₆Alkyl and C₃-C₆A cycloalkyl group. The total number of-OH groups in the compound should not exceed 5. In the formula, R is preferred²，R³，R⁴，R⁵And R⁶Selected from-H and-OH, further, the molecule as a whole contains no more than 3 hydroxyl groups. Preferred compounds for use in the present invention are selected from the group consisting of cyclohexanol, 2-cyclohexylethanol, cyclohexylmethanol, 3-cyclohexyl-1-propanol, 1, 4-cyclohexanediol, 1, 3-cyclohexanediol, 1, 2-cyclohexanediol, 4-cyclohexylcyclo-hexanol, 4-methylcyclohexanol, 1, 2, 3-cyclohexanetriol, 1, 3, 5-cyclohexanetriol, and 1, 4, 5-cyclohexanetriol. Mixtures of these materials may also be used. Cis and trans isomers (or mixtures) of these actives may also be used herein. Isomers (structural and stereochemistry), phospho-and phosphatidyl-derivatives and metabolites of these active compounds are also included within the definition of compounds.

Relevant substances which have been tested and found to be unusable in the present invention include cyclohexane, cyclohexene, cyclohexyl acetate, cyclohexyl chloride, 4-cyclohexyl-1-butanol, cyclohexylcarboxylic acid, 1-methylcyclohexanol, and menthol. In fact, menthol not only does not provide a benefit for use in the present invention, but it also irritates (and thus reddens) the skin to which it is applied. Other materials that cannot be added to the present invention include 1, 2-cyclopentanediol (cis and trans isomers), 5-norbornene-2, 2-dimethanol, and (1R, 2R, 3S, 5S- (-) -pinanediol.

Particularly preferred compounds for use in the present invention include 1, 2-cyclohexanediol, 1, 3-cyclohexanediol, 1, 4-cyclohexanediol, 1, 3, 5-cyclohexanetriol and 1, 2, 3-cyclohexanetriol, and mixtures of these. Cis and trans isomers of these substances, as well as optical isomers of these substances, are also active in the present invention.

The active substance is topically applied to the skin at the site to be treated (e.g., the site that is to be tested for redness of the skin or symptoms associated with skin disease). The active substance is topically applied to the skin in an amount of about 0.001 to about 10mg/cm²Preferably from about 0.1 to about 1mg/cm²More preferably from about 0.1 to about 0.5mg/cm²But this may vary depending on the formulation, the person and the nature of the particular skin condition being treated. The present invention can provide a means for the user to improve skin morphology by reducing skin spots and blemishes, soothing and improving irritated and inflamed skin, reducing redness, swelling, and skin scarring, maintaining skin texture, removing clogged and inflamed pores, maintaining healthy skin appearance, and maintaining healthy hair and reducing hair loss.

The active substance may be applied in combination with a cosmetic topical carrier. Topical cosmetic carriers are well known in the art and are described in Harichian et al U S6,696,069, 696,069, published 24/2004, Makimoto et al U S6,692,754, 692,754, published 9/12/2003, U S6,660,283, published 9/12/2003, and Harichian et al U S6,623,778, published 23/9/2003, all of which are incorporated herein by reference.

When used with a topical cosmetic carrier, the active is included in the topical cosmetic composition with the topical cosmetic carrier. In the topical cosmetic compositions, the active material is generally present in an amount of from about 0.001% to about 10% of the composition, preferably from about 0.1% to about 10% of the composition, more preferably from about 1% to about 5% of the composition, and most preferably about 1% of the composition, with the balance of the composition generally being achieved by including a topical cosmetic carrier. Other suitable cosmetic or therapeutic actives, for example, skin and/or hair care agents, preservatives, anti-inflammatory agents, depigmenting agents, allergy inhibitors, antipruritics, anti-wrinkle agents, anti-hair loss agents, herbal extracts, natural product agents, hair growth agents, sunscreens, or cosmetic agents may be included in the compositions of the present invention. Topical cosmetic carriers are a substance or mixture of substances that are compatible with the active (and supplemental active, if included), are non-irritating when applied to the skin, provide a cosmetic benefit, and can aid in the penetration of the active into the skin.

The carrier may comprise a single component or a combination of two or more components. Preferred cosmetic carriers comprise one or more ingredients selected from the group consisting of water, alcohol, aloe vera gel, allantoin, glycerin, vitamin a and E oils, mineral oil, propylene glycol, polypropylene glycol-2-myristate propionate, dimethyl isosorbide, and combinations thereof. Particularly preferred carriers include glycerol, propylene glycol, dimethyl isosorbide, water and mixtures of these.

The topical cosmetic carrier may comprise one or more ingredients selected from emollients, propellants, solvents, humectants, thickeners, powders, and fragrances in addition to, or in the alternative to, the preferred topical cosmetic carrier ingredients listed above. Those skilled in the art will be able to select and optimize carrier ingredients for use in the topical cosmetic compositions used in the present invention without undue experimentation.

If a softener is included in the carrier, it is typically present at a level of about 5% to about 95% of the total carrier. Suitable emollients include stearyl alcohol, glyceryl monoricinoleate, glyceryl monostearate, propane-1, 2-diol, butane-1, 3-diol, mink oil, cetyl alcohol, isopropyl isostearate, stearic acid, isobutyl palmitate, isocetyl stearate, oleyl alcohol, isopropyl laurate, hexyl laurate, decyl oleate, octadecan-2-ol, isocetyl alcohol, cetyl palmitate, di-n-butyl sebacate, isopropyl myristate, isopropyl palmitate, isopropyl stearate, butyl stearate, polyethylene glycol, triethylene glycol, lanolin, sesame oil, coconut oil, peanut oil, castor oil, acetylated lanolin alcohols, petrolatum, mineral oil, butyl myristate, isostearic acid, palmitic acid, isopropyl linoleate, lauryl lactate, myristyl myristate, Polydimethylsiloxanes, and mixtures of these. Preferred softeners include stearyl alcohol and dimethicone.

If a solvent is used, it typically comprises from about 5% to about 95% of the total vehicle. Suitable propellants include propane, butane, isobutane, dimethyl ether, carbon dioxide, nitrous oxide, nitrogen, and mixtures of these.

If a solvent is used, it typically comprises from about 5% to about 95% of the total vehicle. Suitable solvents include, for example, water, ethanol, methylene chloride, isopropanol, castor oil, ethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol monoethyl ether, dimethyl sulfoxide, dimethylformamide, tetrahydrofuran, glycols, including propylene glycol, and mixtures of these materials. Preferred solvents include ethanol, water, glycols, and mixtures thereof.

If a humectant is used, it typically comprises from about 5% to about 95% of the carrier. Suitable humectants include, for example, glycerin, sorbitol, sodium 2-pyrrolidone-5-carboxylate, soluble collagen, dibutyl phthalate, gelatin, panthenol, and mixtures of these materials. The preferred humectant is glycerin.

If a thickening agent is used in the topical carrier, it typically comprises from about 0.1% to about 95% of the carrier composition. One example of such materials is carbomer-based materials, including crosslinked acrylic polymers, which are commercially available from Spectrum Quality Products, Gardena, California as emulsifying stabilizers and viscosity modifiers in cosmetic compositions. The carrier composition may also include powders for the purpose of providing different desired rheological properties to the final composition. Typically, these powder materials are used at relatively low levels, generally from about 0% to about 25% of the topical carrier. Exemplary powders include chalk, talc, diatomaceous earth, kaolin, starch, gums, colloidal silica, sodium polyacrylate, tetraalkyl ammonium montmorillonite, trialkyl aryl montmorillonite, chemically modified magnesium aluminum silicate, organo-modified montmorillonite clay, hydrated aluminum silicate, fumed silica, carboxyvinyl polymer, sodium carboxymethyl cellulose, ethylene glycol monostearate, and mixtures of these materials. If included in the topical carrier, the fragrance typically comprises from about 0.001% to about 0.5% of the carrier. If the cosmetic composition to be formulated is a pigmented cosmetic product, it may also include colorants (dyes, pigments) at levels determined in the art.

Waxes may also be included in the topical carrier, primarily to take advantage of their ability to provide the carrier with the desired rheological properties, such as viscosity, examples of suitable waxes include animal waxes, vegetable waxes, paraffin waxes, different fractions of natural waxes, synthetic waxes, petroleum waxes, ethylene polymers, hydrocarbon types such as Fischer-Tropsch waxes, silicone waxes and mixtures of these materials having melting points between about 40 ℃ and 100 ℃.

Techniques for formulating topical carriers, and components comprising such carriers, which can be used in the present invention are described in the following references: modern pharmaceuticals, chapters 9 and 10, Banker & Rhodes, eds (1979); lieberman et al, Pharmaceutical Dosage Forms (1981); and Ansel, Introduction to Pharmaceutical Dosage Forms, 2 nd edition (1976); international Cosmetic Ingredient Dictionary, 10 th edition, (2004), Cosmetic, Toiletry, and Fragrance Association, all of which are incorporated herein by reference. Topical cosmetic compositions that can be topically applied to the skin can be in any form, including solutions, oils, creams, ointments, gels, lotions, sprays, skin patches, and the like.

The active substances used in the present invention may be supplemented with cosmetic and/or pharmaceutical actives and herbal extracts known in the art to provide further benefits to the user. These cosmetic and pharmaceutical compounds may include, for example, vitamins, steroids, non-steroidal anti-inflammatory compounds, retinoids, antibiotics and other antibacterial agents, antifungal agents, antioxidants, herbal extracts, and natural product extracts. Examples of specific substances include vitamin C, vitamin K, vitamin B, benzoyl peroxide, lycopene, inositol, erythromycin, minoxidil, zinc oxide, retinol, panthenol, retinoic acid, keratin, hydrolyzed wheat protein, green tea extract, garlic extract, and mixtures thereof. These compounds have different effects on the skin and/or hair. However, none of them is intended to completely replace the active compounds of the present invention. Substances administered orally or as part of a composition of the invention may be administered orally as part of a single composition or as a supplement to a composition/method of the invention to provide an enhancing or supplementing effect to an active compound of the invention. Oral supplements in the present invention may be taken once daily or 1 time every 2-3 days. A particularly safe and useful oral supplement in the present invention is a treated tomato product selected from the group consisting of tomato juice, homogenate, condensate, paste, extract product, and mixtures thereof. For example, a topically applied supplement of the present invention may comprise a once daily oral dose of 200ml of tomato juice. The effect of the tomato product may be further enhanced with vitamins or other cosmetic or pharmaceutical supplements that are beneficial in the treatment of the present invention. Tomato products extracted with water retain their activity in the present invention. This indicates that their active ingredients are water insoluble.

The present invention also relates to a method for maintaining healthy hair and reducing hair loss in humans comprising topically applying to the scalp of a patient in need of treatment a safe and effective amount of a compound selected from the group consisting of active substances having the general formula described above. Generally, the amount of active employed is from about 0.001 to about 10mg/cm²Preferably from about 0.1 to about 0.5mg/cm². The active may be used in combination with a topical cosmetic carrier such as those described above; shampoos, hair conditioners, hair sprays and hair foams are particularly suitable vehicles. Stereoisomers and optical isomers of the active substance may be used.

The present invention also relates to topical cosmetic compositions which may be used in the methods of treatment defined herein. These compositions comprise: from about 0.001% to about 10%, preferably from about 0.5% to about 10%, more preferably from about 1% to about 5%, most preferably about 1% of an active having the formula:

wherein R is¹Is selected from-OH and C₁-C₃Alkyl OH (alkanol), and R²，R³，R⁴，R⁵And R⁶Each independently selected from-H, -OH, C₁-C₆Alkyl and C₃-C₆A cycloalkyl group; provided that the total number of-OH groups in the active material does not exceed 5; as defined above, the balancing substance of the composition is a topical cosmetic carrier.

Preferred actives include cyclohexanol, 2-cyclohexylethanol, cyclohexylmethanol, 3-cyclohexyl-1-propanol, 1, 4-cyclohexanediol, 1, 3-cyclohexanediol, 1, 2-cyclohexanediol, 4-cyclohexylcyclohexanol, 4-methylcyclohexanol, 1, 2, 3-cyclohexanetriol, 1, 3, 5-cyclohexanetriol, and 1, 4, 5-cyclohexanetriol, and mixtures thereof. Cis and trans isomers and optical isomers of these substances may be used. Particularly preferred materials include 1, 2-cyclohexanediol, 1, 3-cyclohexanediol, 1, 4-cyclohexanediol, 1, 2, 3-cyclohexanetriol, 1, 3, 5-cyclohexanetriol, and mixtures thereof.

The compositions of the present invention may be formulated in any conventional manner, including, for example, gels, creams, pastes, solids, tonics, soaps, body hygiene lotions, face-wrap gels, or shampoos.

Example 1

The cosmetic compositions of the present invention having the compositions listed in the following table were prepared as follows: carbomer 940, 5 g; 1, 4-cyclohexanediol, 10 g; and glycerol, 3g mixed with 982g water. The resulting gel was adjusted to pH 7.0 with sodium hydroxide to further thicken the gel. 2-3 times per day at a dose of 1cm²Applying about 0.01ml aliquots of the composition to the facial skin provides improvement in skin morphology and reduces skin irritation and skin inflammation symptoms.

Components % by weight

Carbomer 940(Spectrum Quality Products, Inc) 0.5

Glycerol 0.3

1, 4-cyclohexanediol (cis/trans) 1.0

Sodium hydroxide is sufficient to condition the composition

To pH 7.0

Water balance

Carbomer may be substituted in whole or in part with carbopol 940(Noveon, inc., Cleveland, Ohio).

Example 2

The cosmetic composition of the present invention was prepared by mixing the following ingredients with 981g of water:

carbomer 9405 g

10g of 1, 2, 3-cyclohexanetriol (cis/trans)

Glycerol 1g

Inositol 2g

Methylparaben (methylparaben) 1g

The resulting gel was adjusted to pH 7.0 with sodium hydroxide to further thicken the gel. Manually applying aliquots of the formulation to the skin of the face and neck 2-3 times daily provides the benefits as described herein.

Example 3

The cosmetic composition of the present invention was prepared by mixing the following ingredients with 984g of water:

carbomer 9405 g

10g of 1, 4-cyclohexanediol (trans)

Propylene glycol 2001 g

The resulting gel was adjusted to pH 7.0 with sodium hydroxide to further thicken the gel. Manually applying aliquots of the gel to facial skin 2-3 times daily provides the benefits as described herein.

Example 4

The cosmetic composition of the present invention was prepared by mixing the following ingredients with 985.2g of water:

carbomer 9405 g

4g of 1, 3-cyclohexanediol (cis/trans)

4g of 1, 4-cyclohexanediol (cis/trans)

Glycerol 1g

Aloe extract (powder, Spectrum Quality Products) 0.5g

Garlic extract (powder, Spectrum Quality Products) 0.3g

The resulting gel was adjusted to pH 7.0 with sodium hydroxide to further thicken the gel. Manually applying aliquots of the gel to the facial and forearm skin 1-3 times daily provides the benefits as described herein.

Example 5

The cosmetic composition of the present invention was prepared by dissolving the following ingredients in 998g of water:

0.5g of 1, 4-cyclohexanediol (cis/trans)

0.5g of 1, 2, 3-cyclohexanetriol (cis/trans)

Glycerol 1g

A10 ml aliquot of the solution was poured into a 15ml dropper bottle and the solution applied to the patient's scalp 1 time a day. Hair follicle stimulation and hair loss are reduced.

Claims (14)

1. Use of a compound in racemic form selected from the group consisting of cyclohexanol, 2-cyclohexylethanol, cyclohexylmethanol, 3-cyclohexyl-1-propanol, 1, 4-cyclohexanediol, 1, 3-cyclohexanediol, 1, 2-cyclohexanediol, 4-cyclohexylcyclo-hexanol, 4-methylcyclohexanol, 1, 2, 3-cyclohexanetriol, 1, 3, 5-cyclohexanetriol, 1, 4, 5-cyclohexanetriol, and mixtures thereof, for the preparation of a cosmetic product for alleviating the symptoms of aging of the human skin.

2. Use according to claim 1, wherein the compound is used for the preparation of a cosmetic for relieving and ameliorating irritated and inflamed skin to improve skin morphology.

3. Use according to claim 1, wherein the amount is from 0.001 to about 10mg/cm²In an amount to apply the compound to the skin.

4. Use according to claim 3, wherein the compound is applied to the skin in a topical cosmetic carrier.

5. Use according to claim 1, wherein the compound is used for the preparation of a cosmetic product for maintaining healthy hair and reducing hair loss for improving skin morphology.

6. Use according to claim 3, wherein the compound is selected from the group consisting of 1, 2-cyclohexanediol, 1, 3-cyclohexanediol, 1, 4-cyclohexanediol, 1, 2, 3-cyclohexanetriol, 1, 3, 5-cyclohexanetriol, and mixtures thereof.

7. Use according to claim 3, wherein the compound is selected from the group consisting of 1, 2-cyclohexanediols, 1, 3-cyclohexanediols and mixtures thereof.

8. Use according to claim 4, wherein the cosmetic carrier comprises a substance selected from the group consisting of propylene glycol, glycerol, water, dimethyl isosorbide, and mixtures thereof.

9. Use according to claim 6, wherein the cosmetic carrier comprises a substance selected from the group consisting of propylene glycol, glycerol, water, dimethyl isosorbide, and mixtures thereof.

10. Use according to claim 4, wherein the carrier is formulated in a composition selected from the group consisting of a solution, a suspension, a gel, a paste, a solid and a soap.

11. Use according to claim 4, wherein the compound for topical application is supplemented by a medically active oral supplement.

12. Use according to claim 11, wherein the oral supplement is a tomato product selected from the group consisting of juices, homogenates, condensates, pastes, extracts, and mixtures thereof.

13. Use according to claim 15, wherein the compound is applied to the scalp in a topical cosmetic carrier.

14. Use according to claim 5, wherein the compound is formulated in a composition selected from the group consisting of lotions, shampoos, hair conditioners, hair sprays and hair foams.