HK1181669B - Composition, method and kit for enhancing hair - Google Patents

Abstract

A composition comprising a compound of the formula (I) wherein the dashed bonds represent a single or double bond; R and R' are individually selected from the group consisting of hydrogen, a C1-C6 straight or branched chain alkyl that may be substituted; X is selected from the group consisting of a halide, a halide containing group or a hydrogen; y is 0 or 1, x is 0 or 1 and x and y are not both 1 or not both 0; or a salt thereof. Compositions for topical application and methods of topical application of a composition to modify hair are also described wherein the modification includes increased curl of hair on a subject or hair that is not biologically attached to or is not naturally a part of a subject (e.g., hair of a wig or extension) ("non-natural hair"). In another embodiment, the modification includes increased curl of the hair together with conditioning hair and/or cosmetically improving the appearance or beauty of the hair (e.g., increased look and feel of softness and silkiness). Thus, the compositions described may be applied to existing hair on the scalp or eyelashes or non-natural hair to increase the curl and/or the look and feel of the hair. In one embodiment, a composition includes an effective amount of a compound (molecule) represented by the following formula (II) wherein the dashed bonds represent a single or double bond and when a bond in either chain is a double bond, cis or trans configuration is contemplated; wherein A and B are individually selected from a hydrogen atom, a hydroxyl group (-OH) and a halogen atom (e.g., a fluorine atom), with the proviso that when one of A and B is a hydroxyl group, the other of A and B is a hydrogen atom and when one of A and B is a halogen atom, the other of A and B is a halogen atom or a hydrogen atom; wherein Z is a cycloalkyl moiety having from three to seven carbon atoms, an aryl moiety including from four to ten carbon atoms or a heteroaryl moiety including three to nine carbon atoms and at least one heteroatom selected from nitrogen, oxygen and sulfur; and wherein X1 and X2 are individually selected from a hydrogen atom, a C1-C6 straight or branched chain that may be substituted, (III) and (IV), and R5 is an alkyl moiety having from one to six carbon atoms; wherein R1 and R2 are individually selected from an oxo group (=O), a hydroxyl group (-OH) or an ester group (-O(CO)R6), and R6 is a saturated or unsaturated acyclic hydrocarbon group having from 1 to about 20 carbon atoms, and -(CH2)mR7 wherein m is 0 or an integer of from 1 to 10, and R7 is cycloalkyl group, having from three to seven carbon atoms, or an aryl or heteroaryl group, as defined above; wherein y is 0 or 1, x is 0 or 1 and x and y are not both 1, or a salt thereof.

Description

Compositions, methods and kits for enhancing hair

Technical Field

The present invention relates to compositions, methods and kits for strengthening human hair, including eyelashes.

Background

Certain therapeutic agents are known to induce hair growth. One example is minoxidil (minoxidil), 6- (1-piperidinyl) -2, 4-pyrimidinediamine 3-oxide (U.S. Pat. Nos. 3,382,247 and 3,644,363). Minoxidil was originally prepared and sold for use as an antihypertensive drug. It is observed that, in connection with the use of minoxidil for this latter purpose, the use of minoxidil also produces an increase in hair growth and thickness, as reported in U.S. Pat. Nos. 4,139,619 and 4,968,812. Now, minoxidil is marketed by Pfizer under the trademark RogaineAre marketed for the treatment of hair loss on the scalp of males (male alopecia areata) and on the scalp of females. Another example is finasteride (Propecia)) From Merck&Co, marketed. Finasteride was originally developed for benign prostatic hypertrophy and was found to be effective in treating male alopecia areata, as reported in U.S. patent No. 4,968,812.

Upjohn Company identified prostaglandin F2 α analogs, commonly known as latanoprost (latanoprost), and its chemical name is isopropyl- (Z) -7- [ (1R, 2R, 3R, 5S) -3, 5-dihydroxy-2- [ (3R) -3-hydroxy-5-phenylpentyl ] p]Cyclopentyl group]-5-heptenoic acid ester. Latanoprost from Pharmacia&Upjohn (now part of Pfizer) under the trademark XalaranAre marketed for the reduction of elevated intraocular pressure in glaucoma and ocular hypertension patients. In the form of 0.005% (50. mu.g/mL) latanoprost eye drops and applied directly to the eye via a dropper. A drop generally contains about1.5 μ g of latanoprost.

In its use for reducing intraocular pressure, latanoprost has been reported to cause increased pigmentation and growth of eyelashes in some patients. It is pointed out in us patent No. 6,262,105 that the use of latanoprost results in increased length of eyelashes, increased number of eyelashes along the normal eyelash line, increased thickness and gloss of eyelashes, additional eyelash-like end hair in the transition area adjacent to the normal eyelash growing area, increased eyelash-like end hair in the middle and outer canthus area, increased pigmentation of eyelashes, increased number of hairs on the skin adjacent to the eyelid, increased length and increased gloss and thickness, and increased vertical angle of eyelashes and eyelash-like end hair.

Alcon, Inc ("Alcon") introduced a prostaglandin F2 α analog, commonly known as Travoprost (Travoprost), whose chemical name is isopropyl (Z) -7- [ (1R, 2R, 3R, 5S) -3, 5-dihydroxy-2- [ (1E, 3R) -3-hydroxy-4- [ (α, α, α -trifluoro-m-tolyl) oxy ] -1-butenyl ] cyclopentyl ] -5-heptenoate, for the treatment of glaucoma. Alcon also seeks travoprost patent protection for growing hair in U.S. patent application No. 2003/0199590.

Allergan, Inc. ("Allergan") introduced Bimatoprost (Bimatoprost), which is chemically known as cyclopentane N-ethyl heptanamide-5-cis-2- (3 α -hydroxy-5-phenyl-1-trans-pentenyl) -3, 5-dihydroxy, [1 α,2 α,3 α,5 α ], for the treatment of glaucoma. U.S. patent No. 7,351,404 is directed to the use of this and similar molecules for growing hair, including eyelashes. Allergan distinguishes bimatoprost molecules from other prostaglandins based on whether bimatoprost is a prostamide.

U.S. patent nos. 5,886,035 and 5,985,920 describe fluorine-containing prostaglandin derivatives useful as preventive or therapeutic agents for ocular diseases such as glaucoma or elevated intraocular pressure.

Brief description of the drawings

Figure 1 shows a process scheme from a Corey acetate derivative to a difluoro compound comprising an ethyl amide.

Detailed Description

Compositions for topical application, methods of topically applying compositions to enhance hair, and kits are described. Enhancing hair as described herein includes stimulating or promoting the growth of existing hair (including stimulating or promoting the rate at which hair roots or cells in hair follicles associated with actual hair formation are hair growth or accelerate hair growth). In this sense, hair growth includes an increase in length and/or an increase in hair diameter. Enhancing hair also includes stimulating or promoting new hair growth (e.g., at the site of a dormant hair follicle). Enhancing hair also includes conditioning hair and/or cosmetically enhancing the appearance or aesthetics of hair such that the hair (treated with the compound or composition comprising the compound) appears or feels longer, denser, and/or fuller. Enhancing hair also includes blackening hair by stimulating melanocytes or similar cells that produce dark pigmented melanin. The location of the hair includes the scalp (e.g., scalp hair), the eyelids (e.g., eyelashes), and the eyebrows (e.g., eyebrows), as well as any other portion of the human skin where hair is present or may be desired to be present.

In one embodiment, the composition comprises an effective hair enhancing amount of a compound represented by the following structural formula:

wherein the dotted bond represents a single or double bond, which may be in either the cis or trans configuration; r and R' are independently selected from hydrogen or C₁-C₆Straight or branched chain alkyl (e.g., methyl, ethyl, isopropyl), which may be substituted (e.g., with another substituent (e.g., serinamide, -CH (CH)₂OH)₂) By substitution of one or more of the bonds to carbon atoms of alkyl groupsA plurality of hydrogen atoms); x is halogen (e.g. F, Cl, Br, I), halogen-containing group (e.g. CF)₃) Or hydrogen; y is 0 and x is 1, or y is 1 and x is 0. The molecule can be characterized as difluoroprostaglandin or prostanoid because its backbone is similar to that of prostaglandin.

The difluoro compound may be in the form of a free form of the molecule (molecule) or an acceptable salt thereof (compound). An acceptable salt is a dermatologically acceptable salt or a pharmaceutically acceptable salt. Examples of salts are molecular hydrohalic salts, such as hydrochloride salts. In one embodiment, the resulting salt compound will have protons from hydrohalides bonded to the nitrogen of the molecule and balanced by the charge of the halides. Throughout this specification, unless otherwise indicated, reference to a compound includes a molecule or compound.

In another embodiment, the compound has the following structural formula:

wherein R, R', X, y and x are as defined above, or an acceptable salt thereof.

In a particular embodiment, the compound is one of the following molecules or a salt thereof:

in one embodiment, one or more compounds as described above are mixed with a dermatologically compatible vehicle or carrier to form a composition. Suitable vehicles include, for example, aqueous solutions, such as physiological saline, oils (e.g., castor oil), solutions, foams, creams or ointments. In addition, suitable vehicles may contain dermatologically compatible preservatives such as benzalkonium chloride, surfactants such as polysorbate 80, liposomes or polymers such as methylcellulose, polyvinyl alcohol, polyvinylpyrrolidone, and hyaluronic acid; these can be used to increase viscosity. Antimicrobial agents such as phenoxyethanol, chlorphenesin, and/or parabens may also be added.

In one embodiment, a dermatological composition for enhancing the topical treatment of hair is also disclosed, comprising an effective hair-enhancing amount of one or more compounds as defined above and a dermatologically compatible carrier. An effective amount of the active compound can be determined by one of ordinary skill in the art, but will vary depending on the compound employed, the frequency of administration, and the result desired. The amount of the one or more compounds is generally from about 0.0000001% to about 10% by weight of the dermatological composition, preferably from about 0.0001% to about 10% by weight of the total dermatological composition.

In another embodiment, a composition may comprise the difluoroprostaglandin or prostaglandin like compound or compound in combination with other hair treatment adjuncts such as antioxidants (e.g., vitamin E), vasodilators (e.g., minoxidil), antimicrobial agents (e.g., benzoyl peroxide), or anti-inflammatory agents (e.g., hydrocortisone, cyclooxygenase inhibitors, lipoxygenase inhibitors).

The composition may be applied topically, e.g., to human skin, i.e., the surface of the skin, an area where hair enhancement is desired, such as directly to the skin in an existing hair or area where hair enhancement is desired, as opposed to indirectly (such as to the surface of the eye). Such locations may include the scalp, eyelash area or eyelids or eyebrows of a male or female. Applying a compound or composition to the base of one or more hairs (e.g., without actually contacting the skin) can create a capillary action in which the compound or composition is drawn along the length of the one or more hairs toward the hair follicle. It may be desirable to repeat administration over a sustained period of time (e.g., daily administration over several weeks or longer (e.g., one month to several months)).

Where hair is not present, the composition may be applied directly to the skin where hair growth is desired. This may include, for example, the scalp where the density of existing hair has been reduced by alopecia or other mechanisms (e.g., hair loss as a side effect of chemotherapy). In certain cultures of asia, the absence of pubic hairs is considered bad luck and may be a serious problem, especially for women. This problem can be solved by applying the composition to the vaginal area. In one embodiment, repeated daily topical application of the composition to an area of skin where hair growth is desired may continue until hair growth is achieved and may continue periodically (daily, weekly) to maintain that growth. In one embodiment, such topical application to the skin may, for example, utilize a delivery vehicle comprising the composition, which is a foam or cream.

To enhance eyelashes, a composition comprising at least one difluoroprostaglandin or prostanoid-like compound as described above may be applied to the skin adjacent to or at the base of the eyelids where hair grows from the hair follicle (e.g., along the eyelash line). Alternatively or additionally, the composition may be applied to the eyelashes themselves. Repeated application of the composition to the eyelashes or to an area of eyelid skin associated with the eyelashes (e.g., the base of the eyelid containing the hair follicle in which the eyelashes grow) for several consecutive days, weeks, or months (e.g., six months, regularly daily application) will condition and cosmetically enhance the existing eyelashes, thereby making the eyelashes appear longer, denser, and/or fuller. Such application will also stimulate or promote eyelash growth.

In another embodiment, a kit is disclosed. The kit may include in a container a composition of at least one difluoroprostaglandin or prostanoid-like compound as described above in a dermatologically compatible vehicle or carrier. The container includes an amount of the composition for repeated administration over a period of time, such as a composition sufficient for daily administration over a period of 3-6 months. The container may also include an applicator, such as a mascara brush, eyeliner brush, or other implement for applying the composition to the skin. In the case of a composition in the form of a foam, the container may be pressurized and include a nozzle to dispense the desired amount onto the user's hand.

Example 1: synthesis of 3, 3-difluoro-4-phenoxybut-1-enyl-3, 5-dihydroxycyclopentyl-hept-5-enoic acid

Starting from the Corey acetate derivative, the omega chain backbone, such as dimethyl-2-oxo-3-phenoxy-propyl phosphonate, is added by an exchange reaction. The oxo group at the 2-position is retained in the formed intermediate and then reduced with a fluorine compound to produce a difluoro precursor. Subsequently, the α chain was added to another site of the Corey ester acetate derivative, thereby obtaining 3, 3-difluoro-4-phenoxybut-1-enyl-3, 5-dihydroxycyclopentyl-hept-5-enoic acid.

Example 2: synthesis of methyl 3, 3-difluoro-4-phenoxybut-1-enyl-3, 5-dihydroxycyclopentyl-hept-5-enoate Become into

To 3, 3-difluoro-4-phenoxybut-1-enyl-3, 5-dihydroxycyclopentyl-hept-5-enoic acid methyl iodide in Tetrahydrofuran (THF) solution was added to form 3, 3-difluoro-4-phenoxybut-1-enyl-3, 5-dihydroxycyclopentyl-hept-5-enoic acid methyl ester.

Example 3: 3, 3-difluoro-4-phenoxybut-1-enyl-3, 5-dihydroxycyclopentyl-N-ethylhept-5-enamide Of (2)Become into

To 3, 3-difluoro-4-phenoxybut-1-enyl-3, 5-dihydroxycyclopentyl-hept-5-enoic acid methyl ester was added ethylamine in water to form 3, 3-difluoro-4-phenoxybut-1-enyl-3, 5-dihydroxycyclopentyl-N-ethylhept-5-enamide.

Figure 1 shows the process flow from the acetic acid Corney ester derivative to the acid, to the ester and then to the ethylamide (compound 3). U.S. patent No. 5,886,035 also describes methods of making difluoro-prostaglandin derivatives, but does not describe the use of such derivatives in hair (eyelash) growth.

The following example provides representative composition 3 comprising a difluoro compound such as compound 3:

example 4: composition for eyelashes

Composition (I)	Percentage of
		1. Water (of water)	97.791
2. Sodium chloride	0.877
		3. Panthenol	0.020
4. Citric acid	0.030
		5. Phenoxyethanol	0.300
6. Chlorophytin ether	0.300
		7. Disodium hydrogen phosphate	0.142
8. Difluoro compounds	0.024
		9. Alcohol(s)	0.216
10. Cellulose gum	0.300

Example 5: composition for eyelashes

Composition (I)	Percentage of
		USP Water	94.519
2. Sodium chloride	0.077
		3. Phosphoric acid	0.03

4. Phenoxyethanol	0.3
		5. Chlorophytin ether	0.3
6. Disodium hydrogen phosphate	0.142
		7. Cellulose gum	0.36
8. Biotin	0.5
		9. Glycerol	0.6
10. Extract of Swertia Japonica (Swertia Japonica)	0.045
		11. Saw Palmetto (Saw palm etto) extract	0.064
12. Tea (Camellia Sinensis) leaf extract	0.054
		13. Ginseng (Panax Ginseng)	0.075
14. Octapeptide-2	0.93
		15. Biotin acyl tripeptide-1	0.93
16. Wheat protein	0.25
		17. Marigold (Calendala)	0.8
18. Difluoro compounds	0.024

Example 6: composition for eyelashes

Composition (I)	Percentage of
		USP Water	96.031
2. Rosemary (Rosemary) plant extract (actiphyte)	0.025
		3. Phosphoric acid	0.001
4. Phenoxyethanol	0.3
		5. Chlorophytin ether	0.3
6. Disodium hydrogen phosphate	0.985
		7. Cellulose gum	0.36
8. Biotin	0.24
		9. Panthenol	0.25
10. Plant extract of Nettle (Nettle)	0.1

11. Plant extract of Horsetail (Horsetail)	0.098
		12. Plant extract of Psoralea Seed (Psoralea Seed)	0.015
13. Mulberry Root (Mulberry Root) extract	0.07
		14. Plant extract of Japanese green tea	0.25
15. Glycerol	0.6
		16. Difluoro compounds	0.024

Example 7: composition for scalp

Composition (I)	Percentage of
		1. Water (W)	95.00000
2. Acrylate copolymer	1.50000
		3. Glycerol	1.00000
4. Phenoxyethanol	0.80000
		5. Sodium cocoyl glutamate	0.35000
6. Chlorophytin ether	0.30000
		7. Polysorbate ester	0.25000
8. Difluoro compounds	0.02400
		EDTA disodium salt	0.10000
10. Perfume	0.09610
		11. Aminomethyl propanol	0.09000
12. Ginseng root extract	0.08000
		13. Panthenol	0.08000
14. Ginkgo biloba (Ginko Bilola) leaf extract	0.05000
		15. Biotin	0.05000
16. Serenoa Serrulate (Serenoa Serrulate) fruit extract	0.00640
		17. Swertia japonica Makino extract	0.00450
18. Hydrolyzed wheat protein	0.00300
		19. Ethanol	0.21600

Example 8:comparison of 3, 3-difluoro-4-phenoxybut-1-enyl-3, 5-dihydroxycyclopentyl-N-ethylhept-5-enamide (Compound (3)) with 16-phenoxy PGF_2αExperiment of activity of ethylamide (the molecules differ by substituents on the C15 atom, the latter having hydrogen atoms and hydroxyl (-OH) groups attached to C15, respectively).

The results of the experiments show that there are significant differences in the extent to which each of these molecules stimulates or promotes eyelash growth. Specifically, compound (3) allowed significant eyelash growth in independent tests with daily application of concentrations of 0.025%, 0.010% and 0.003% for as little as 10-14 days. Growth was dramatic (described as "burst") with daily administration of a concentration of 0.025%. Another molecule (16-phenoxy)PGF_2αEthylamide) at concentrations of 0.025%, 0.010% and 0.003% for several weeks or more, eyelash growth was also insignificant. 16-phenoxy PGF, even after up to 12 weeks of application, in terms of density (number of new eyelashes), thickness and length_2αThe final effect of the ethylamide application is significantly lower than the effect of the compound (3) application. Analysis of the effect of the application of the compound (3) molecule shows that the application of the compound (3) molecule appears to stimulate the resting eyelash follicles to begin to produce new eyelashes and to cause the existing eyelashes to grow at a faster rate.

The test results lead to the following conclusions: the difluoro atom at C15 significantly and uniquely enhances the ability to strengthen hair, including stimulating or stimulating hair. Without wishing to be bound by theory, it is believed that this phenomenon is due to unique biochemical pathways and mechanisms of action, and that this pathway leads to abnormally strong stimulation of hair follicles.

Presumably, compared to PGF having a hydroxyl group at C15_2αAmide molecules there is a different and novel set of molecular receptor sites for difluoroprostaglandin amide molecules having 2 fluorine atoms at the C15 position.

In another embodiment, compositions for topical application and methods of topically applying compositions to modify hair are described, wherein the modification comprises increasing the curl of the subject's hair or hair that is not biologically attached to the subject or is not a natural part of the subject (i.e., a wig or extension) ("non-natural hair"). In another embodiment, the alteration comprises increasing the frizz of the hair while conditioning the hair and/or cosmetically enhancing the appearance or aesthetics of the hair (e.g., increasing the soft and silky look and feel). Thus, the described compositions may be applied to existing hair of the scalp or eyelashes or unnatural hair to increase the curl, size (volume), and/or look and feel of the hair. In one embodiment, the composition comprises an effective amount of a compound represented by the following structural formula:

wherein the dotted bonds represent single or double bonds, and when the bond in either chain is a double bond, either the cis or trans configuration is envisaged;

wherein A and B are independently selected from a hydrogen atom, a hydroxyl group (-OH), and a halogen atom (e.g., fluorine atom), with the proviso that when one of A and B is a hydroxyl group, the other of A and B is a hydrogen atom, and when one of A and B is a halogen atom, the other of A and B is a halogen atom or a hydrogen atom;

wherein Z is a cycloalkyl moiety having 3 to 7 carbon atoms, an aryl moiety comprising 4 to 10 carbon atoms or a heteroaryl moiety comprising 3 to 9 carbon atoms and at least one heteroatom selected from nitrogen, oxygen and sulfur; and

wherein X₁And X₂Independently selected from hydrogen atoms, optionally substituted C₁-C₆Straight or branched chain alkyl (e.g., methyl, ethyl, propyl) (e.g., serinamide, -CH (CH)₂OH)₂)、And is

R⁵Is an alkyl moiety having from 1 to 6 carbon atoms;

wherein R is₁And R₂Independently selected from oxo (═ O), hydroxy (-OH) or ester (-O (CO) R₆) And R is₆Is a saturated or unsaturated acyclic hydrocarbyl group having from 1 to about 20 carbon atoms, and- (CH)₂)_mR₇Wherein m is 0 or an integer of 1 to 10, and R₇Is cycloalkyl having 3 to 7 carbon atoms or aryl or heteroaryl as defined above;

wherein y is 0 or 1, x is 0 or 1, and x and y are not simultaneously 1.

The compounds may be combined in free form (molecules) or in an acceptable salt thereof (compounds) such as a cationic or anionic salt formed on the nitrogen atom of the molecule, with a carrier suitable for topical application to mammalian skin. Unless otherwise specified, reference to a compound includes a molecule or compound.

In one embodiment, the compound may be represented by the following structural formula:

wherein, A, B, X₁、X₂X and Y are as defined above, and Y is selected from alkyl, halogen atoms (e.g., fluorine, chlorine), nitro, amino, thiol, hydroxyl, alkoxy, alkylcarboxy, halogen-substituted alkyl (wherein the alkyl includes from 1-6 carbon atoms), and n is 0 or an integer from 1 to 3; or an acceptable salt thereof.

In another embodiment, the compound has the following structural formula:

wherein, A, B, X₁、X₂X, Y and Y are as defined above; or an acceptable salt thereof.

In a particular embodiment, the compound is selected from any of the above compounds (1) - (5) or a molecule having any of the following structural formulae or a salt thereof:

compounds (6) - (9) can be prepared using techniques known in the art, including, for example, the techniques described in U.S. patent nos. 5,001,153, 5,422,368, 5,510,383, and 5,607,978.

In one embodiment, one or more of the compounds described above, including compounds (1) - (9), are mixed with a dermatologically compatible vehicle or carrier. Suitable vehicles include, for example, aqueous solutions (e.g., physiological saline), oils (e.g., castor oil), aqueous solutions, aqueous/alcoholic solutions, or ointments. In addition, suitable vehicles may contain dermatologically compatible preservatives (e.g., benzalkonium chloride), surfactants (e.g., polysorbate 80), liposomes or polymers (e.g., methylcellulose, polyvinyl alcohol, polyvinylpyrrolidone, and hyaluronic acid); these can be used to increase viscosity.

In one embodiment, also disclosed are dermatological compositions for topical treatment to induce or stimulate existing hair alteration (including frizz increase) comprising one or more compounds as defined above and a dermatologically compatible carrier in an amount effective to alter hair, wherein the alteration includes hair frizz increase or frizz increase. An effective amount of a compound can be determined by one of ordinary skill in the art, but will vary depending on the compound employed, the frequency of administration, and the result desired. The compound is typically present in an amount of from about 0.0000001% to about 50% by weight of the dermatological composition, preferably from about 0.001% to about 50% by weight of the total dermatological composition, and more preferably from about 0.1% to 30% by weight of the composition. In another embodiment, the composition may comprise the compound or one or more compounds in combination with other hair treatment adjuncts such as antioxidants (e.g. vitamin E), vasodilators (e.g. minoxidil), antibacterial agents (e.g. benzoyl peroxide) or anti-inflammatory agents (e.g. hydrocortisone, cyclooxygenase inhibitors, lipoxygenase inhibitors).

The composition can be topically applied to existing hair and remain on the hair. Such locations may include scalp or eyelash areas of a male or female. Repeated administration over a sustained period of time (e.g., daily administration over several weeks or longer (e.g., one month to several months)) may be desirable. The composition may benefit persons who naturally have straight hair to aid in such hair curling. Demonstration of the effectiveness of the composition of compound (3) (dechlorinated-dihydroxy-difluoro-ethyl chloroprostate (ethylcloprostate)) or compound (8) (trifluoromethyl dechlorinated ethyl chloroprost amide (prostenolamide)) when applied to hair of a generally straight asian person demonstrates a profound frizzing effect.

In one embodiment, the composition is suitable for modifying eyelashes. To alter eyelashes, the subject will be provided with the composition and instructions (e.g., by instructions on or with a kit that includes the composition and instructions). The subject will be instructed to apply the composition to the eyelashes. In addition to altering the eyelashes (e.g., increasing curl and/or look and feel), it is anticipated that application to the hair follicle will increase the thickness (e.g., diameter) of the hair follicle.

In one embodiment, the composition may be topically applied to the hair on the scalp. For example, a subject interested in establishing curl in a portion of the subject's hair or in enhancing natural curl will be directed (e.g., by instructions on or with the kit) to apply the composition topically to the desired portion of hair and to leave the composition on the hair. To increase or maintain the curl for a period of time (e.g., days, weeks), the subject will be instructed to repeat the administration for a period of days to weeks.

In another embodiment, the above-described application can be used to alter non-natural hair (e.g., hair that is not bioattached to the subject or is not a natural part of the subject). Examples of such hair include, but are not limited to, wigs and extensions.

In another embodiment, a kit is disclosed. The kit may include in a container a composition of at least one compound of structural formula III or IV as described above in a dermatologically compatible vehicle or carrier. The container includes an amount of the composition for repeated administration over a period of time, such as a composition sufficient for daily administration over a period of 6 months. The container may also include an applicator, such as a mascara brush or other implement for applying the composition to the skin. In the case of a composition in the form of a foam, the container may be pressurized and include a nozzle to dispense the desired amount onto the user's hand.

Example 9

The following examples use trifluoromethyl dechlorinated ethyl prostate alcohol amide (TDP) as compound. TDP has the following structural formula:

a TDP solution was prepared containing 97.6% water, 0.24% TDP and 2.16% ethanol. A sample of human hair from a subject was treated with water alone while the other samples were treated with a TDP solution. The treatment involved immersing the dry hair sample in a solution of water and TDP for one minute. Unexpectedly, a clear increase in curl occurred in each hair sample when treated with the TDP solution. Hair treated with water alone did not show similar frizz. The results are shown in FIG. 1. Furthermore, the hair treated with the TDP solution had a clear and perceptible increase in the appearance and feel of softness and silkiness compared to hair treated with water alone.

In the foregoing detailed description, reference has been made to specific embodiments thereof. It will, however, be evident that various modifications and changes may be made thereto without departing from the broader spirit and scope of the following claims. The specification and drawings are, accordingly, to be regarded in an illustrative rather than a restrictive sense.

Claims (7)

1. A method of enhancing hair comprising

Applying directly to hair an effective hair-curling amount of a composition comprising a compound of the formula:

wherein the dotted bond represents a single or double bond;

wherein A and B are independently selected from a hydrogen atom, a hydroxyl group (-OH), and a halogen atom, with the proviso that when one of A and B is a hydroxyl group, the other of A and B is a hydrogen atom, and when one of A and B is a halogen atom, the other of A and B is a halogen atom;

wherein Z is an aryl moiety comprising 4 to 10 carbon atoms; and

wherein X₁And X₂Independently selected from a hydrogen atom or C which may be substituted₁-C₆Straight or branched chain;

wherein R is₁And R₂Each is a hydroxyl group; and

wherein y is 0 or 1, x is 0 or 1, and x and y are not simultaneously 1.

2. The method of claim 1, wherein the hair comprises eyelashes.

3. The method of claim 1, wherein each of a and B is a fluorine atom.

4. The method of claim 3, wherein y is 0 and x is 1.

5. The method of claim 1, wherein y is 0 and x is 1.

6. The method of claim 1, wherein Z is substituted with trifluoromethyl.

7. The method of claim 1, wherein one of a and B is a hydrogen atom and the other of a and B is a hydroxyl group.