US20100021412A1 - Reduction of hair growth - Google Patents
Reduction of hair growth Download PDFInfo
- Publication number
- US20100021412A1 US20100021412A1 US12/572,564 US57256409A US2010021412A1 US 20100021412 A1 US20100021412 A1 US 20100021412A1 US 57256409 A US57256409 A US 57256409A US 2010021412 A1 US2010021412 A1 US 2010021412A1
- Authority
- US
- United States
- Prior art keywords
- agonist
- acid
- skin
- hair growth
- area
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
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Classifications
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- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
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- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
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- A61K2800/70—Biological properties of the composition as a whole
Definitions
- the invention relates to reducing hair growth in mammals, particularly for cosmetic purposes.
- a main function of mammalian hair is to provide environmental protection. However, that function has largely been lost in humans, in whom hair is kept or removed from various parts of the body essentially for cosmetic reasons. For example, it is generally preferred to have hair on the scalp but not on the face.
- the rate and character of hair growth can be altered by applying to the skin inhibitors of certain enzymes.
- These inhibitors include inhibitors of 5-alpha reductase, ornithine decarboxylase, S-adenosylmethionine decarboxylase, gamma-glutamyl transpeptidase, and transglutaminase. See, for example, Breuer et al., U.S. Pat. No. 4,885,289; Shander, U.S. Pat. No. 4,720,489; Ahluwalia, U.S. Pat. No. 5,095,007; Ahluwalia et al., U.S. Pat. No. 5,096,911; and Shander et al., U.S. Pat. No. 5,132,293.
- Farnesoid X receptor forms a heterodimer with the retinoid X receptor (RXR) and binds to an inverted hexanucleotides repeat spaced by one nucleotide in the promoters of its target genes.
- Farnesoid X receptor is activated through interaction with ligands such as farnesoids and bile acids.
- coactivators DRIP205/TRAP220, SRC-1 and PGC-1alpha
- SRC-1 and PGC-1alpha that bridge between the ligand-activated farnesoid X receptors and the basal transcription machinery, and/or influence the chromatin structure, can enhance the transcriptional activity of farnesoid X receptor.
- Farnesoid X receptor helps maintain bile acid homeostasis by modulating the expression of genes involved in the synthesis and transport of bile acid.
- Bile acids are the end product of cholesterol catabolism. Synthesis of bile acid is the predominant mechanisms for the excretion of excess cholesterol. Most bile acids in human are chenodeoxycholic acid, cholic acid, deoxycholic acid, ursodeoxycholic acid and lithocholic acid. While the level of bile acids is increased, farnesoid X receptor is activated and upregulates the expression of the bile salt export pump that is responsible for bile acid excretion.
- bile acid-activated farnesoid X receptor represses the transcription of cholesterol 7alpha-hydroxylase (CYP7A1), which the rate-limiting enzyme in the bile acid biosynthesis pathway.
- CYP7A1 cholesterol 7alpha-hydroxylase
- the invention provides a method (typically a cosmetic method) of reducing unwanted mammalian (preferably human) hair growth by applying to the skin an agonist of farnesoid X receptor in an amount effective to reduce hair growth.
- the agonist interacts strongly with the farnesoid X receptor.
- the unwanted hair growth may be undesirable from a cosmetic standpoint.
- the invention provides a method of reducing unwanted mammalian hair growth by applying to the skin a compound selected from the group consisting of bile acids, analogs of bile acids, and derivatives of bile acids.
- the invention provides a method of reducing unwanted mammalian hair growth by applying to the skin a compound selected from the group consisting of farnesoids, analogs of farnesoids, and derivatives of farnesoids.
- the invention provides a method of reducing unwanted mammalian hair growth by applying to the skin a compound that increases the formation of FXR-RXR heterodimer, the expression of farnesoid X receptor, or promotes coactivator recruitment and interaction with FXR-RXR heterodimer.
- the invention provides a method of providing a benefit to exfoliated skin by applying any of the above agonists/compounds.
- the agonist/compound will be included in a topical composition along with a dermatologically or cosmetically acceptable vehicle.
- the present invention also relates to topical compositions comprising a dermatologically or cosmetically acceptable vehicle and an agonist of farnesoid X receptor.
- the present invention further relates to topical compositions comprising a dermatologically or cosmetically acceptable vehicle and (a) a compound selected from the group consisting of bile acids, analogs or derivatives of bile acids; (b) a compound selected from the group consisting of farnesoids, analogs or derivatives of farnesoids; and/or (c) a compound that increases the formation of FXR-RXR heterodimer, the expression of farnesoid X receptor, or promotes coactivator recruitment and interaction with FXR-RXR heterodimer.
- the present invention relates to the use of an agonist of farnesoid X receptor for the manufacture of a therapeutic topical composition for reducing hair growth.
- the present invention relates to the use of a compound for the manufacture of a therapeutic topical composition for reducing hair growth, wherein the compound is (a) a compound that selected from the group consisting of bile acids, analogs or derivatives of bile acids; (b) a compound selected from the group consisting of farnesoids, analogs or derivatives of farnesoids; and/or (c) a compound that increases the formation of FXR-RXR heterodimer, the expression of farnesoid X receptor, or promotes coactivator recruitment and interaction with FXR-RXR heterodimer.
- the agonist/compound is not a carbomate or ester of ⁇ -difluoromethylornithine.
- Carbamates, esters, and other conjugates of ⁇ -difluoromethylornithine are described in U.S. Ser. No. 10/397,132, which was filed on Mar. 26, 2003, is owned by the same owner as the present application, and is hereby incorporated herein by reference.
- Antist of farnesoid X receptor means a compound that activates farnesoid X receptor.
- An agonist that “interacts strongly” with the farnesoid X receptor is one that binds the receptor with such affinity that it elicits a response that is at least approximately comparable to (in magnitude) to that elicited by farnesoids.
- Specific compounds include both the compound itself and pharmacologically acceptable salts of the compound.
- An example of a preferred composition includes at least one agonist of farnesoid X receptor in a cosmetically and/or dermatologically acceptable vehicle.
- the composition may be a solid, semi-solid, or liquid.
- the composition may be, for example, a cosmetic and dermatologic product in the form of an, for example, ointment, lotion, foam, cream, gel, or solution.
- the composition may also be in the form of a shaving preparation, an aftershave or an antiperspirant.
- the vehicle itself can be inert or it can possess cosmetic, physiological and/or pharmaceutical benefits of its own.
- Examples of agonists of farnesoid X receptor include bile acids, farnesoids, their analogs and derivatives, and other compounds.
- agonists of farnesoid X receptor are disclosed in WO2004007521, WO03015771, WO2004048349, WO03076418, WO2004046162, WO03060078, WO02072598, WO03080803, WO2003086303, WO 2004046068, U.S. Pat. 20030187042, U.S. Pat. 0040176426, U.S. Pat. 20040180942, U.S. Pat. No. 6,452,032, U.S. Pat. 2003203939, U.S. Pat. 2005004165, J. med. Chem. (2000), 43(6), 2971-2974, Mol. Gen. Met.
- Farnesoid X receptor agonists Farnesoid X receptor agonists
- Farnesol Farnesal Farnesyl acetate Farnesoic acid Methyl farnesyl ether Methyl farnesoate Ethyl farnesyl ether Ethyl farnesoate 7-Methyl-9-(3,3-dimethyloxivanyl)-3-methyl-2,6-nonadienoic acid methyl ester (also known as Juvenile hormone III)
- Lithocholic acid Cholic acid
- Ursodeoxycholic acid 6-alpha-Ethyl chenodeoxycholic acid Benzenesulfonamide, N-(2,2,2-trifluoroethyl)-N-[4-[2,2,2-trifluoro-1- hydroxy-1-(trifluoromethyl)ethyl]phenyl]-(also known as T0901317)
- the composition may include more than one agonist of farnesoid X receptor.
- the composition may include one or more other types of hair growth reducing agents, such as those described in U.S. Pat. No. 4,885,289; U.S. Pat. No. 4,720,489; U.S. Pat. No. 5,132,293; U.S. Pat. No. 5,096,911; U.S. Pat. No. 5,095,007; U.S. Pat. No. 5,143,925; U.S. Pat. No. 5,328,686; U.S. Pat. No. 5,440,090; U.S. Pat. No. 5,364,885; U.S. Pat. No. 5,411,991; U.S. Pat. No.
- the concentration of the agonist in the composition may be varied over a wide range up to a saturated solution, preferably from 0.1% to 30% by weight or even more; the reduction of hair growth increases as the amount of agonist applied increases per unit area of skin.
- the maximum amount effectively applied is limited only by the rate at which the agonist penetrates the skin.
- the effective amounts may range, for example, from 10 to 3000 micrograms or more per square centimeter of skin.
- the vehicle can be inert or can possess cosmetic, physiological and/or pharmaceutical benefits of its own.
- Vehicles can be formulated with liquid or solid emollients, solvents, thickeners, humectants and/or powders.
- Emollients include stearyl alcohol, mink oil, cetyl alcohol, oleyl alcohol, isopropyl laurate, polyethylene glycol, petroleum jelly, palmitic acid, oleic acid, and myristyl myristate.
- Solvents include ethyl alcohol, isopropanol, acetone, diethylene glycol, ethylene glycol, dimethyl sulfoxide, and dimethyl formamide.
- the composition optionally can include components that enhance the penetration of the agonist into the skin and/or to the site of action.
- penetration enhancers include urea, polyoxyethylene ethers (e.g., Brij-30 and Laureth-4), 3-hydroxy-3,7,11-trimethyl-1,6,10-dodecatriene, terpenes, cis-fatty acids (e.g., oleic acid, palmitoleic acid), acetone, laurocapram, dimethylsulfoxide, 2-pyrrolidone, oleyl alcohol, glyceryl-3-stearate, propan-2-ol, myristic acid isopropyl ester, cholesterol, and propylene glycol.
- a penetration enhancer can be added, for example, at concentrations of 0.1% to 20% or 0.5% to 5% by weight.
- the composition also can be formulated to provide a reservoir within or on the surface of the skin to provide for a continual slow release of the agonist.
- the composition also may be formulated to evaporate slowly from the skin, allowing the agonist extra time to penetrate the skin.
- a topical cream composition containing an agonist of farnesoid X receptor may be prepared by mixing together water and all water soluble components in a mixing vessel-A.
- the pH is adjusted in a desired range from about 3.5 to 8.0.
- the vessel temperature may be raised to up to 45° C. The selection of pH and temperature will depend on the stability of the agonist.
- the oil soluble components, except for the preservative and fragrance components, are mixed together in another container (B) and heated to up to 70° C. to melt and mix the components.
- the heated contents of vessel B are poured into the water phase (container A) with brisk stirring. Mixing is continued for about 20 minutes.
- the preservative components are added at temperature of about 40° C.
- the fragrance components are added at about 25° C.-30° C. while the contents are still being mixed and the viscosity has not yet built up to the desired range. If it is desired to increase the viscosity of the resulting emulsion, shear can be applied using a conventional homogenizer, for example a Silverson L4R homogenizer with a square hole high sheer screen.
- the topical composition can be fabricated by including the agonist in the water phase during formulation preparation or can be added after the formulation (vehicle) preparation has been completed. The agonist can also be added during any step of the vehicle preparation.
- the components of come cream formulations are described in the examples below.
- a hydroalcoholic formulation containing an agonist of farnesoid X receptor is prepared by mixing the formulation components in a mixing vessel.
- the pH of the formulation is adjusted to a desired value in the range of 3.5-8.0.
- the pH adjustment can also be made to cause complete dissolution of the formulation ingredients.
- heating can be applied to up to 45° C., or even up to 70° C. depending on the stability of the agonist to achieve dissolution of the formulation ingredients.
- the components of two hydroalcoholic formulations are listed below.
- the composition should be applied topically to a selected area of the body from which it is desired to reduce hair growth.
- the composition can be applied to the face, particularly to the beard area of the face, i.e., the cheek, neck, upper lip, and chin.
- the composition also may be used as an adjunct to other methods of hair removal including shaving, waxing, mechanical epilation, chemical depilation, electrolysis and laser-assisted hair removal. Other actions that make their concept appearance are concurrent skin benefits in addition to hair reduction.
- the composition can also be applied to the legs, arms, torso or armpits.
- the composition is suitable, for example, for reducing the growth of unwanted hair in women.
- the composition should be applied once or twice a day, or even more frequently, to achieve a perceived reduction in hair growth. Perception of reduced hair growth could occur as early as 24 hours or 48 hours (for instance, between normal shaving intervals) following use or could take up to, for example, three months. Reduction in hair growth is demonstrated when, for example, the rate of hair growth is slowed, the need for removal is reduced, the subject perceives less hair on the treated site, or quantitatively, when the weight of hair removed (i.e., hair mass) is reduced.
- Human hair follicles in growth phase were isolated from face-lift tissue (obtained from plastic surgeons) under dissecting scope using a scalpel and watchmakers forceps. The skin was sliced into thin strips exposing 2-3 rows of follicles that could readily be dissected. Follicles were placed into 0.5 ml William's E medium (Life Technologies, Gaithersburg, Md.) supplemented with 2 mM L-glutamine, 10 ⁇ g/ml insulin, 10 ng/ml hydrocortisone, 100 units of penicillin, 0.1 mg/ml streptomycin and 0.25 ⁇ g/ml amphotericin B.
- the follicles were incubated in 24-well plates (1 follicle/well) at 37° C. in an atmosphere of 5% CO 2 and 95% air. Compounds are dissolved into dimethyl sulfoxide as 100-fold stock solution.
- the control hair follicles were treated with dimethyl sulfoxide without prostaglandin.
- the follicles were photographed in the 24-well plates under the dissecting scope at a power of 10 ⁇ .
- image recordings were made on day 0 (day follicles were placed in culture), and again on day 7.
- the length of hair follicle was assessed using an image analysis software system. The growth of hair fiber was calculated by the subtracting the follicle length on day 0 from that determined on day 7.
- the agonists of farnesoid X receptor demonstrated a significant reduction of human hair follicle growth. All of the six agonists of farnesoid X receptor tested significantly reduced hair growth. The results are provided in Table II. The hair growth inhibition profile by the agonists of farnesoid X receptor was found to be dose-dependent. The results are provided in Table III.
Abstract
Mammalian hair growth is reduced by applying an agonist of farnesoid X receptor.
Description
- This application is a continuation of U.S. patent application Ser. No. 11/141,798, filed May 31, 2005, which is incorporated herein by reference in its entirety.
- The invention relates to reducing hair growth in mammals, particularly for cosmetic purposes.
- A main function of mammalian hair is to provide environmental protection. However, that function has largely been lost in humans, in whom hair is kept or removed from various parts of the body essentially for cosmetic reasons. For example, it is generally preferred to have hair on the scalp but not on the face.
- Various procedures have been employed to remove unwanted hair, including shaving, electrolysis, depilatory creams or lotions, waxing, plucking, and therapeutic antiandrogens. These conventional procedures generally have drawbacks associated with them. Shaving, for instance, can cause nicks and cuts, and can leave a perception of an increase in the rate of hair regrowth. Shaving also can leave an undesirable stubble. Electrolysis, on the other hand, can keep a treated area free of hair for prolonged periods of time, but can be expensive, painful, and sometimes leaves scarring. Depilatory creams, though very effective, typically are not recommended for frequent use due to their high irritancy potential. Waxing and plucking can cause pain, discomfort, and poor removal of short hair. Finally, antiandrogens—which have been used to treat female hirsutism—can have unwanted side effects.
- It has previously been disclosed that the rate and character of hair growth can be altered by applying to the skin inhibitors of certain enzymes. These inhibitors include inhibitors of 5-alpha reductase, ornithine decarboxylase, S-adenosylmethionine decarboxylase, gamma-glutamyl transpeptidase, and transglutaminase. See, for example, Breuer et al., U.S. Pat. No. 4,885,289; Shander, U.S. Pat. No. 4,720,489; Ahluwalia, U.S. Pat. No. 5,095,007; Ahluwalia et al., U.S. Pat. No. 5,096,911; and Shander et al., U.S. Pat. No. 5,132,293.
- Farnesoid X receptor (also known as “FXR”, “RIP14”, “bile acid receptor”, “BAR”, “HRR1” and “NR1H4”) is a member of the family of ligand-activated transcription factors that bind to specific cis-acting regulatory elements in the promoters of their target genes and modulate gene expression in response to ligands. Some of these receptors bind to their target genes as dimers consisting of two molecules of the same receptor homodimers), while others bind to as dimers consisting of one molecule each of two different receptors (heterodimers). Farnesoid X receptor forms a heterodimer with the retinoid X receptor (RXR) and binds to an inverted hexanucleotides repeat spaced by one nucleotide in the promoters of its target genes. Farnesoid X receptor is activated through interaction with ligands such as farnesoids and bile acids. In addition, coactivators (DRIP205/TRAP220, SRC-1 and PGC-1alpha) that bridge between the ligand-activated farnesoid X receptors and the basal transcription machinery, and/or influence the chromatin structure, can enhance the transcriptional activity of farnesoid X receptor.
- Farnesoid X receptor helps maintain bile acid homeostasis by modulating the expression of genes involved in the synthesis and transport of bile acid. Bile acids are the end product of cholesterol catabolism. Synthesis of bile acid is the predominant mechanisms for the excretion of excess cholesterol. Most bile acids in human are chenodeoxycholic acid, cholic acid, deoxycholic acid, ursodeoxycholic acid and lithocholic acid. While the level of bile acids is increased, farnesoid X receptor is activated and upregulates the expression of the bile salt export pump that is responsible for bile acid excretion. In addition to bile acid excretion, bile acid-activated farnesoid X receptor represses the transcription of cholesterol 7alpha-hydroxylase (CYP7A1), which the rate-limiting enzyme in the bile acid biosynthesis pathway.
- In one aspect, the invention provides a method (typically a cosmetic method) of reducing unwanted mammalian (preferably human) hair growth by applying to the skin an agonist of farnesoid X receptor in an amount effective to reduce hair growth. Preferably, the agonist interacts strongly with the farnesoid X receptor. The unwanted hair growth may be undesirable from a cosmetic standpoint.
- In another aspect, the invention provides a method of reducing unwanted mammalian hair growth by applying to the skin a compound selected from the group consisting of bile acids, analogs of bile acids, and derivatives of bile acids.
- In another aspect, the invention provides a method of reducing unwanted mammalian hair growth by applying to the skin a compound selected from the group consisting of farnesoids, analogs of farnesoids, and derivatives of farnesoids.
- In a another aspect, the invention provides a method of reducing unwanted mammalian hair growth by applying to the skin a compound that increases the formation of FXR-RXR heterodimer, the expression of farnesoid X receptor, or promotes coactivator recruitment and interaction with FXR-RXR heterodimer.
- In a further aspect, the invention provides a method of providing a benefit to exfoliated skin by applying any of the above agonists/compounds.
- Typically, in practicing the aforementioned methods, the agonist/compound will be included in a topical composition along with a dermatologically or cosmetically acceptable vehicle. Accordingly, the present invention also relates to topical compositions comprising a dermatologically or cosmetically acceptable vehicle and an agonist of farnesoid X receptor. The present invention further relates to topical compositions comprising a dermatologically or cosmetically acceptable vehicle and (a) a compound selected from the group consisting of bile acids, analogs or derivatives of bile acids; (b) a compound selected from the group consisting of farnesoids, analogs or derivatives of farnesoids; and/or (c) a compound that increases the formation of FXR-RXR heterodimer, the expression of farnesoid X receptor, or promotes coactivator recruitment and interaction with FXR-RXR heterodimer.
- In addition, the present invention relates to the use of an agonist of farnesoid X receptor for the manufacture of a therapeutic topical composition for reducing hair growth. Further, the present invention relates to the use of a compound for the manufacture of a therapeutic topical composition for reducing hair growth, wherein the compound is (a) a compound that selected from the group consisting of bile acids, analogs or derivatives of bile acids; (b) a compound selected from the group consisting of farnesoids, analogs or derivatives of farnesoids; and/or (c) a compound that increases the formation of FXR-RXR heterodimer, the expression of farnesoid X receptor, or promotes coactivator recruitment and interaction with FXR-RXR heterodimer.
- In some embodiments, the agonist/compound is not a carbomate or ester of α-difluoromethylornithine. Carbamates, esters, and other conjugates of α-difluoromethylornithine are described in U.S. Ser. No. 10/397,132, which was filed on Mar. 26, 2003, is owned by the same owner as the present application, and is hereby incorporated herein by reference.
- “Agonist of farnesoid X receptor”, as used herein, means a compound that activates farnesoid X receptor.
- An agonist that “interacts strongly” with the farnesoid X receptor is one that binds the receptor with such affinity that it elicits a response that is at least approximately comparable to (in magnitude) to that elicited by farnesoids.
- Specific compounds include both the compound itself and pharmacologically acceptable salts of the compound.
- Other features and advantages of the invention may be apparent from the detailed description and from the claims.
- An example of a preferred composition includes at least one agonist of farnesoid X receptor in a cosmetically and/or dermatologically acceptable vehicle. The composition may be a solid, semi-solid, or liquid. The composition may be, for example, a cosmetic and dermatologic product in the form of an, for example, ointment, lotion, foam, cream, gel, or solution. The composition may also be in the form of a shaving preparation, an aftershave or an antiperspirant. The vehicle itself can be inert or it can possess cosmetic, physiological and/or pharmaceutical benefits of its own.
- Examples of agonists of farnesoid X receptor include bile acids, farnesoids, their analogs and derivatives, and other compounds.
- Derivatives and analogs of bile acids are known. For example, J. Med. Chem. (2004), 47, 4559-4569 describes bile acid derivatives. J. Biol. Chem. (2004), 279(10), 8856-8861. describes various bile acids. Derivatives and analogs of farnesoids are known. For example, U.S. Pat. No. 6,187,814 describes farnesoid derivatives. Other examples of agonists of farnesoid X receptor are disclosed in WO2004007521, WO03015771, WO2004048349, WO03076418, WO2004046162, WO03060078, WO02072598, WO03080803, WO2003086303, WO 2004046068, U.S. Pat. 20030187042, U.S. Pat. 0040176426, U.S. Pat. 20040180942, U.S. Pat. No. 6,452,032, U.S. Pat. 2003203939, U.S. Pat. 2005004165, J. med. Chem. (2000), 43(6), 2971-2974, Mol. Gen. Met. (2004), 83, 184-187, Drugs for the future 91999), 24(4), 431-438, Current Pharmaceutical Design (2001), 7, 231-259. Examples of coactivators involved in FXR-RCR hetrodimer are disclosed in Genes & Dev. (2004), 18, 157-169 and J. Biol. Chem. (2004), 279(35), 36184-36191. All of these references are incorporated by reference.
- Specific examples of agonists of farnesoid X receptor are provided in Tables I.
-
TABLE I Examples of Farnesoid X receptor agonists Farnesol Farnesal Farnesyl acetate Farnesoic acid Methyl farnesyl ether Methyl farnesoate Ethyl farnesyl ether Ethyl farnesoate 7-Methyl-9-(3,3-dimethyloxivanyl)-3-methyl-2,6-nonadienoic acid methyl ester (also known as Juvenile hormone III) Lithocholic acid Cholic acid Deoxycholic acid Chenodeoxycholic acid Ursodeoxycholic acid 6-alpha-Ethyl chenodeoxycholic acid Benzenesulfonamide, N-(2,2,2-trifluoroethyl)-N-[4-[2,2,2-trifluoro-1- hydroxy-1-(trifluoromethyl)ethyl]phenyl]-(also known as T0901317) Benzoic acid, 3-[2-[2-chloro-4-[[3-(2,6-dichlorophenyl)-5-(1-methylethyl)- 4-isoxazolyl]methoxy]phenyl]ethenyl]-(also known as GW4064) Phosphonic acid, [[3,5-bis(1,1-dimethylethyl)-4- hydroxyphenyl]ethenylidene]bis-,tetraethyl ester (also known as SR-12813) Phosphonic acid, [2-[3,5-bis(1,1-dimethylethyl)-4- hydroxyphenyl]ethylidene]bis-,tetrakis(1-methylethyl) ester (also known as SR-45023A or apomine) Phosphonic acid, [2-[3,5-bis(1,1-dimethylethyl)-4- hydroxyphenyl]ethylidene]bis-,tetraethyl ester (also known as SR-9213) Phosphonic acid, [[3,5-bis(1,1-dimethylethyl)-4- hydroxyphenyl]ethenylidene]bis-,tetrakis(1-methylethyl) ester (also known as SR-12823i) 7-Methyl-9-(3,3-dimethyloxivanyl)-3-methyl-2,6-nonadienoic acid ethyl ester 3α,7α-dihydroxy-6α-ethyl-5p-cholan-24-oic acid 3α,7α-dihydroxy-6α-propyl-5p-cholan-24-oic acid 3α,7α-dihydroxy-6α-allyl-5p-cholan-24-oic acid - The composition may include more than one agonist of farnesoid X receptor. In addition, the composition may include one or more other types of hair growth reducing agents, such as those described in U.S. Pat. No. 4,885,289; U.S. Pat. No. 4,720,489; U.S. Pat. No. 5,132,293; U.S. Pat. No. 5,096,911; U.S. Pat. No. 5,095,007; U.S. Pat. No. 5,143,925; U.S. Pat. No. 5,328,686; U.S. Pat. No. 5,440,090; U.S. Pat. No. 5,364,885; U.S. Pat. No. 5,411,991; U.S. Pat. No. 5,648,394; U.S. Pat. No. 5,468,476; U.S. Pat. No. 5,475,763; U.S. Pat. No. 5,554,608; U.S. Pat. No. 5,674,477; U.S. Pat. No. 5,728,736; U.S. Pat. No. 5,652,273; WO 94/27586; WO 94/27563; and WO 98/03149, all of which are incorporated herein by reference.
- The concentration of the agonist in the composition may be varied over a wide range up to a saturated solution, preferably from 0.1% to 30% by weight or even more; the reduction of hair growth increases as the amount of agonist applied increases per unit area of skin. The maximum amount effectively applied is limited only by the rate at which the agonist penetrates the skin. The effective amounts may range, for example, from 10 to 3000 micrograms or more per square centimeter of skin.
- The vehicle can be inert or can possess cosmetic, physiological and/or pharmaceutical benefits of its own. Vehicles can be formulated with liquid or solid emollients, solvents, thickeners, humectants and/or powders. Emollients include stearyl alcohol, mink oil, cetyl alcohol, oleyl alcohol, isopropyl laurate, polyethylene glycol, petroleum jelly, palmitic acid, oleic acid, and myristyl myristate. Solvents include ethyl alcohol, isopropanol, acetone, diethylene glycol, ethylene glycol, dimethyl sulfoxide, and dimethyl formamide.
- The composition optionally can include components that enhance the penetration of the agonist into the skin and/or to the site of action. Examples of penetration enhancers include urea, polyoxyethylene ethers (e.g., Brij-30 and Laureth-4), 3-hydroxy-3,7,11-trimethyl-1,6,10-dodecatriene, terpenes, cis-fatty acids (e.g., oleic acid, palmitoleic acid), acetone, laurocapram, dimethylsulfoxide, 2-pyrrolidone, oleyl alcohol, glyceryl-3-stearate, propan-2-ol, myristic acid isopropyl ester, cholesterol, and propylene glycol. A penetration enhancer can be added, for example, at concentrations of 0.1% to 20% or 0.5% to 5% by weight.
- The composition also can be formulated to provide a reservoir within or on the surface of the skin to provide for a continual slow release of the agonist. The composition also may be formulated to evaporate slowly from the skin, allowing the agonist extra time to penetrate the skin.
- A topical cream composition containing an agonist of farnesoid X receptor may be prepared by mixing together water and all water soluble components in a mixing vessel-A. The pH is adjusted in a desired range from about 3.5 to 8.0. In order to achieve complete dissolution of ingredients the vessel temperature may be raised to up to 45° C. The selection of pH and temperature will depend on the stability of the agonist. The oil soluble components, except for the preservative and fragrance components, are mixed together in another container (B) and heated to up to 70° C. to melt and mix the components. The heated contents of vessel B are poured into the water phase (container A) with brisk stirring. Mixing is continued for about 20 minutes. The preservative components are added at temperature of about 40° C. Stirring is continued until the temperature reaches about 25° C. to yield a soft cream with a viscosity of 8,000-12,000 cps, or a desired viscosity. The fragrance components are added at about 25° C.-30° C. while the contents are still being mixed and the viscosity has not yet built up to the desired range. If it is desired to increase the viscosity of the resulting emulsion, shear can be applied using a conventional homogenizer, for example a Silverson L4R homogenizer with a square hole high sheer screen. The topical composition can be fabricated by including the agonist in the water phase during formulation preparation or can be added after the formulation (vehicle) preparation has been completed. The agonist can also be added during any step of the vehicle preparation. The components of come cream formulations are described in the examples below.
-
-
INCI Name W/w (%) DI Water 61.00-75.00 Agonist of farnesoid X receptor 1.00-15.00 Mineral oil 1.90 Glyceryl stearate 3.60 PEG 100 stearate 3.48 Cetearyl alcohol 2.59 Ceteareth-20 2.13 Dimethicone, 100 ct 0.48 Lipidure PMBa 3.00 Advanced moisture complexb 5.00 Stearyl alcohol 1.42 Preservative, fragrance and color pigment qs Total 100.00 apolyquartinium-51 (Collaborative Labs, NY); bglycerin and water and sodium PCA and urea and trehalose and polyqauternium-51 and sodium hyaluronate (Collaborative Labs, NY) -
-
INCI Name w/w (%) Agonist of farnesoid X receptor 0.5-15.00 Glycerol (glycerin) 0-5 Isoceteth-20 3-7 Glyceryl isostearate 1.5-5 Dicaprylyl ether 3-15 Glyceryl triacetate (triacetin) 0.5-10 Preservative, fragrance and color pigment q.s. Water q.s. to 100.00 -
-
INCI Name w/w (%) Agonist of farnesoid X receptor 0.5-15.00 Glycerol (glycerin) 0-5 Isoceteth-20 3-7 Glyceryl isostearate 1.5-5 Dicaprylyl ether 3-15 1-dodecyl-2-pyrrolidanone 0.5-10% Preservative, fragrance and color q.s. Water to 100.00 -
-
INCI Name w/w (%) Water 70 Glyceryl stearate 4 PEG-100 4 Cetearyl alcohol 3 Ceteareth-20 2.5 Mineral oil 2 Stearyl alcohol 2 Dimethicone 0.5 Preservatives 0.43 1-Dodecyl-2-pyrrolidanone 1-10 Total 100.00
An agonist of farnesoid X receptor is added to the example 4 formulation and mixed until solubilized. -
-
INCI Name w/w (%) Water 70-80 Glyceryl stearate 4 PEG-100 4 Cetearyl alcohol 3 Ceteareth-20 2.5 Mineral oil 2 Stearyl alcohol 2 Dimethicone 0.5 Preservatives 0.43 Monocaprylate/Caprate (Estol 3601, Uniquema, NJ) 1-10 Total 100.00
An agonist of farnesoid X receptor is added to the example 5 formulation and mixed until solubilized. -
-
INCI Name w/w (%) Water 70-80 Glyceryl stearate 4 PEG-100 4 Cetearyl alcohol 3 Ceteareth-20 2.5 Mineral oil 2 Stearyl alcohol 2 Dimethicone 0.5 Preservatives 0.43 cis Fatty acids 1-10 Total 100.00
An agonist of farnesoid X receptor is added to the example 6 formulation and mixed until solubilized. -
-
INCI Name w/w (%) Water 70-80% Glyceryl stearate 4 PEG-100 4 Cetearyl alcohol 3 Ceteareth-20 2.5 Mineral oil 2 Stearyl alcohol 2 Dimethicone 0.5 Preservatives 0.43 Terpene(s) 1-10 Total 100.00
An agonist of farnesoid X receptor is added to the example 7 formulation and mixed until solubilized. -
-
INCI Name w/w (%) Water 70-80% Glyceryl stearate 4 PEG-100 4 Cetearyl alcohol 3 Ceteareth-20 2.5 Mineral oil 2 Stearyl alcohol 2 Dimethicone 0.5 Preservatives 0.43 Polyoxyethylene sorbitans (tween) 1-10 Total 100.00
An agonist of farnesoid X receptor is added to the example 8 formulation and mixed until solubilized. - A hydroalcoholic formulation containing an agonist of farnesoid X receptor is prepared by mixing the formulation components in a mixing vessel. The pH of the formulation is adjusted to a desired value in the range of 3.5-8.0. The pH adjustment can also be made to cause complete dissolution of the formulation ingredients. In addition, heating can be applied to up to 45° C., or even up to 70° C. depending on the stability of the agonist to achieve dissolution of the formulation ingredients. The components of two hydroalcoholic formulations are listed below.
-
-
INCI Name w/w (%) Water 48.00-62.50 An agonist of farnesoid X receptor 0.5-15.00 Ethanol 16.00 Propylene glycol 5.00 Dipropylene glycol 5.00 Benzyl alcohol 400 Propylene carbonate 2.00 Captex-300a 5.00 Total 100.00 acaprylic/capric triglyceride (Abitec Corp., OH). -
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INCI Name w/w (%) Water 53.00-67.9 An agonist of farnesoid X receptor 0.1-15.00 Ethanol 16.00 Propylene glycol 5.00 Dipropylene glycol dimethyl ether 5.00 Benzyl alcohol 4.00 Propylene carbonate 2.00 Total 100.00 -
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INCI Name w/w (%) Ethanol (alcohol) 80 Water 17.5 Propylene glycol dipelargonate 2.0 Propylene glycol 0.5 Total 100.00
An agonist of farnesoid X receptor is added to the example 11 formulation and mixed until solubilized. - The composition should be applied topically to a selected area of the body from which it is desired to reduce hair growth. For example, the composition can be applied to the face, particularly to the beard area of the face, i.e., the cheek, neck, upper lip, and chin. The composition also may be used as an adjunct to other methods of hair removal including shaving, waxing, mechanical epilation, chemical depilation, electrolysis and laser-assisted hair removal. Other actions that make their concept appearance are concurrent skin benefits in addition to hair reduction.
- The composition can also be applied to the legs, arms, torso or armpits. The composition is suitable, for example, for reducing the growth of unwanted hair in women. In humans, the composition should be applied once or twice a day, or even more frequently, to achieve a perceived reduction in hair growth. Perception of reduced hair growth could occur as early as 24 hours or 48 hours (for instance, between normal shaving intervals) following use or could take up to, for example, three months. Reduction in hair growth is demonstrated when, for example, the rate of hair growth is slowed, the need for removal is reduced, the subject perceives less hair on the treated site, or quantitatively, when the weight of hair removed (i.e., hair mass) is reduced.
- Human Hair Follicle Growth Assay:
- Human hair follicles in growth phase (anagen) were isolated from face-lift tissue (obtained from plastic surgeons) under dissecting scope using a scalpel and watchmakers forceps. The skin was sliced into thin strips exposing 2-3 rows of follicles that could readily be dissected. Follicles were placed into 0.5 ml William's E medium (Life Technologies, Gaithersburg, Md.) supplemented with 2 mM L-glutamine, 10 μg/ml insulin, 10 ng/ml hydrocortisone, 100 units of penicillin, 0.1 mg/ml streptomycin and 0.25 μg/ml amphotericin B. The follicles were incubated in 24-well plates (1 follicle/well) at 37° C. in an atmosphere of 5% CO2 and 95% air. Compounds are dissolved into dimethyl sulfoxide as 100-fold stock solution. The control hair follicles were treated with dimethyl sulfoxide without prostaglandin. The follicles were photographed in the 24-well plates under the dissecting scope at a power of 10×. Typically, image recordings were made on day 0 (day follicles were placed in culture), and again on day 7. The length of hair follicle was assessed using an image analysis software system. The growth of hair fiber was calculated by the subtracting the follicle length on day 0 from that determined on day 7.
- Hamster Hair Mass Assay:
- Hamster hair mass was determined using a method similar to that described in previous patent (US2004/0198821).
- The agonists of farnesoid X receptor demonstrated a significant reduction of human hair follicle growth. All of the six agonists of farnesoid X receptor tested significantly reduced hair growth. The results are provided in Table II. The hair growth inhibition profile by the agonists of farnesoid X receptor was found to be dose-dependent. The results are provided in Table III.
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TABLE II Inhibition of human hair follicle growth by the agonists of farnestoid X receptor. Dose Hair follicle length increase (mm) FXR agonists (μM) Treated Control % Inhibition Deoxycholic acid 100 0.06 ± 0.05 1.07 ± 0.14 94.3 ± 4.7 Ursodeoxycholic 200 0.20 ± 0.11 1.07 ± 0.14 81.3 ± 10.3 acid Chenodeoxycholic 100 0.05 ± 0.06 1.07 ± 0.14 95.3 ± 5.6 acid Lithocholic acid 50 0.02 ± 0.02 1.07 ± 0.14 98.1 ± 1.9 Farnesol 100 0.04 ± 0.07 0.87 ± 0.23 95.4 ± 8.0 Juvenile 100 0.21 ± 0.15 0.87 ± 0.23 75.9 ± 17.2 hormone III -
TABLE III Dose-dependent reduction of human hair follicle growth by the agonists of farnestoid X receptor. Dose Growth of follicle (mm) FXR agonists (μM) Treated Control % Reduction Deoxycholic acid 10 1.20 ± 0.49 1.76 ± 0.36 31.8 ± 18.1 50 0.54 ± 0.34 1.76 ± 0.36 69.3 ± 13.6 100 0.54 ± 0.34 1.76 ± 0.36 69.3 ± 13.6 Ursodeoxycholic acid 50 1.12 ± 0.24 1.76 ± 0.36 36.3 ± 13.6 100 0.86 ± 0.20 1.76 ± 0.36 51.1 ± 11.4 150 0.61 ± 0.20 1.76 ± 0.36 65.3 ± 11.4 Chenodeoxycholic 5 1.53 ± 0.29 1.55 ± 0.02 1.3 ± 18.7 acid 25 0.79 ± 0.27 1.55 ± 0.02 49.0 ± 17.4 50 0.13 ± 0.10 1.55 ± 0.02 91.6 ± 6.5 Lithocholic acid 2 0.82 ± 0.14 1.24 ± 0.23 33.9 ± 11.3 10 0.44 ± 0.16 1.24 ± 0.23 64.5 ± 12.9 20 0.03 ± 0.06 1.24 ± 0.23 97.6 ± 4.8 - Furthermore, the agonists of farnestoid X receptor were tested in the hamster hair mass assay. The agonists reduced hair mass in vivo as shown in Table IV.
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TABLE IV Reduction of hamster hair mass by the agonists of farnestoid X receptor. Dose Hair mass (mg) FXR agonists (w/v) Vehicle* Treated Control % Inhibition Lithocholic acid 4% ethanol 1.01 ± 0.12 1.96 ± 0.19 46.4 ± 6.0 Chenodeoxycholic acid 5% ethanol 0.54 ± 0.08 2.28 ± 0.19 76.4 ± 2.6 Deoxycholic acid 5% ethanol 0.92 ± 0.14 2.66 ± 0.28 63.6 ± 6.0 Ursodeoxycholic acid 5% ethanol 1.02 ± 0.16 2.43 ± 0.31 56.8 ± 3.8 *The vehicle contains 90% ethanol and 10% propylene glycol. - Accordingly, other embodiments are within the scope of the following claims.
Claims (49)
1. A method of reducing mammalian hair growth which comprises
selecting an area of skin from which reduced hair growth is desired; and
applying to said area of skin a dermatologically acceptable composition comprising an agonist of farnesoid X receptor in an amount effective to reduce hair growth,
wherein said agonist is not a carbamate or ester of α-difluoromethylornithine and farnesol.
2. The method of claim 1 , wherein said agonist is a bile acid.
3. The method of claim 1 , wherein said agonist is an analog of a bile acid.
4. The method of claim 1 , wherein said agonist is a derivative of a bile acid.
5. The method of claim 1 , wherein said agonist interacts strongly with the farnesoid X receptor.
6. The method of claim 1 , wherein said agonist is lithocholic acid.
7. The method of claim 1 , wherein said agonist is cholic acid.
8. The method of claim 1 , wherein said agonist is deoxycholic acid.
9. The method of claim 1 , wherein said agonist is chenodeoxycholic acid.
10. The method of claim 1 , wherein said agonist is ursodeoxycholic acid.
11. The method of claim 1 , wherein said agonist is 6-alpha-ethyl chenodeoxycholic acid.
12. The method of claim 1 , wherein said agonist is a farnesoid.
13. The method of claim 1 , wherein said agonist is an analog of a farnesoid.
14. The method of claim 1 , wherein said agonist is a derivative of a farnesoid.
15. The method of claim 1 , wherein said agonist is farnesol.
16. The method of claim 1 , wherein said agonist is farnesal.
17. The method of claim 1 , wherein said agonist is farnesyl acetate.
18. The method of claim 1 , wherein said agonist is farnesoic acid
19. The method of claim 1 , wherein said agonist is methyl farnesyl ether.
20. The method of claim 1 , wherein said agonist is methyl farnesoate.
21. The method of claim 1 , wherein said agonist is ethyl farnesyl ether.
22. The method of claim 1 , wherein said agonist is ethyl farnesoate.
23. The method of claim 1 , wherein said agonist is 7-methyl-9-(3,3-dimethyloxivanyl)-3-methyl-2,6-nonadienoic acid methyl ester (juvenile hormone III).
24. The method of claim 1 , wherein said agonist is 7-methyl-9-(3,3-dimethyloxivanyl)-3-methyl-2,6-nonadienoic acid ethyl ester.
25. The method of claim 1 , wherein said agonist is 3alpha,7alpha-dihydroxy-6alpha-ethyl-5p-cholan-24-oic acid.
26. The method of claim 1 , wherein said agonist is 3alpha,7alpha-dihydroxy-6alpha-propyl-5p-cholan-24-oic acid.
27. The method of claim 1 , wherein said agonist is 3alpha,7alpha-dihydroxy-6alpha-allyl-5p-cholan-24-oic acid.
28. The method of claim 1 , wherein said agonist is benzenesulfonamide, N-(2,2,2-trifluoroethyl)-N-[4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]-.
29. The method of claim 1 , wherein said agonist is benzoic acid, 3-[2-[2-chloro-4-[[3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methoxy]phenyl]ethenyl]-.
30. The method of claim 1 , wherein said agonist is phosphonic acid, [[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]ethenylidene]bis-, tetraethyl ester.
31. The method of claim 1 , wherein said agonist is phosphonic acid, [2-[3,5-bis(1-dimethylethyl)-4-hydroxyphenyl]ethylidene]bis-, tetrakis(1-methylethyl) ester.
32. The method of claim 1 , wherein said agonist is phosphonic acid, [2-[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]ethylidene]bis-, tetraethyl ester.
33. The method of claim 1 , wherein said agonist is phosphonic acid, [[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]ethenylidene]bis-, tetrakis(1-methylethyl) ester.
34. The method of claim 1 , wherein the concentration of said agonist in said composition is between 0.1% and 30%.
35. The method of claim 1 , wherein the composition provides a reduction in hair growth of at least 30% when tested in the Human Hair Follicle assay.
36. The method of claim 1 , wherein the agonist is applied to the skin in an amount of from 10 to 3000 micrograms of said agonist per square centimeter of skin.
37. The method of claim 1 , wherein said area of skin is on the face of a human.
38. The method of claim 37 , wherein the composition is applied to the area of skin in conjunction with shaving.
39. The method of claim 1 , wherein said area of skin is on a leg of the human.
40. The method of claim 1 , wherein said area of skin is on an arm of the human.
41. The method of claim 1 , wherein said area of skin is in an armpit of the human.
42. The method of claim 1 , wherein said area of skin is on the torso of the human.
43. The method of claim 1 , wherein said hair growth comprises androgen stimulated hair growth.
44. The method of claim 1 , wherein the composition further includes a second component that also causes a reduction in hair growth.
45. A method of reducing mammalian hair growth, which comprises
selecting an area of skin including hair follicles from which reduced hair growth is desired; and
applying to the area of skin a dermatologically acceptable composition comprising a compound selected from the group consisting of bile acids, bile acid analogues, and bile acid derivatives in an amount effective to reduce hair growth.
46. A method of reducing mammalian hair growth, which comprises
selecting an area of skin including hair follicles from which reduced hair growth is desired; and
applying to the area of skin, in an amount effective to reduce hair growth, a dermatogically acceptable composition comprising a compound, other than a carbamate or ester of α-difluoromethylomithine and farnesol, selected from the group consisting of compounds that increase the formation of FXR-RXR heterodimer, compounds that promote coactivator recruitment and interaction with FXR-RXR, and compounds that increase the expression of farnesoid X receptor.
47. A method of reducing mammalian hair growth, which comprises
selecting an area of skin from which reduced hair growth is desired; and
applying to the area of skin a dermatologically acceptable composition comprising a compound selected from the group consisting of farsenoids, analogues of farsenoids, and derivatives of farsenoids in an amount effective to reduce hair growth.
48. A method of treating an area of exfoliated skin, comprising applying an agonist of farnesoid X receptor to the area of exfoliated skin.
49. The method of claim 48 , wherein the area of exfoliated skin has been shaved prior to application of the agonist of farnesoid X receptor.
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US11077123B2 (en) * | 2016-02-29 | 2021-08-03 | Tel Hashomer Medical Research Infrastructure And Services Ltd. | Use of bile acids and bile salts as anti bacterial agents for inhibition of bacterial conjugation and horizontal gene transfer |
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Citations (77)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3426137A (en) * | 1965-12-23 | 1969-02-04 | Olin Mathieson | Hair growth inhibiting by aminobenzophenones |
US3878239A (en) * | 1972-05-09 | 1975-04-15 | Ono Pharmaceutical Co | Prostaglandin D compounds production |
US4039669A (en) * | 1975-08-01 | 1977-08-02 | Sterling Drug Inc. | Composition for topical application and use thereof |
US4139638A (en) * | 1976-09-23 | 1979-02-13 | Schering Corporation | Methods for the treatment of hirsutism |
US4161540A (en) * | 1966-08-22 | 1979-07-17 | Schering Corporation | Antiandrogenic agents and methods for the treatment of androgen dependent disease states |
US4185099A (en) * | 1977-01-04 | 1980-01-22 | Also Laboratori S.a.S. di Dr.P. Sorbini & C | Hair and scalp treatment with compositions containing chenodeoxycholic or ursodeoxycholic acid |
US4191775A (en) * | 1977-12-15 | 1980-03-04 | Imperial Chemical Industries Limited | Amide derivatives |
US4201873A (en) * | 1975-09-17 | 1980-05-06 | The Upjohn Company | 9-Deoxy-9,10-didehydro-PGD2 analogs |
US4203924A (en) * | 1976-01-08 | 1980-05-20 | The Upjohn Company | 2-Decarboxy-2-hydroxymethyl-deoxy-9,10-didehydro-PGD2 analogs |
US4269831A (en) * | 1979-05-09 | 1981-05-26 | Sterling Drug Inc. | Topical dermatological method of use of an androstenopyrazole |
US4370315A (en) * | 1977-02-22 | 1983-01-25 | Sederma | Post-depilatory composition reducing progressively the growth of body hair |
US4508714A (en) * | 1983-11-14 | 1985-04-02 | Tihomir Cecic | Organic scalp lotion |
US4517175A (en) * | 1982-06-07 | 1985-05-14 | Kao Corporation | Hair cosmetics |
US4562204A (en) * | 1982-06-30 | 1985-12-31 | Ono Pharmaceutical Co., Ltd. | Trans-Δ2 -prostaglandin D derivatives, process for their preparation and compositions containing them |
US4720489A (en) * | 1984-10-15 | 1988-01-19 | Douglas Shander | Hair growth modification with ornithine decarboxylase inhibitors |
US4885289A (en) * | 1983-12-12 | 1989-12-05 | Breuer Miklos M | Alteration of character of male beard growth |
US4935231A (en) * | 1985-08-28 | 1990-06-19 | Repligen Corporation | Use of thioredoxin, thioredoxin-derived, or thioredoxin-like dithiol peptides in hair care preparations |
US5095007A (en) * | 1990-10-24 | 1992-03-10 | Ahluwalia Gurpreet S | Alteration of rate and character of hair growth |
US5096911A (en) * | 1990-06-25 | 1992-03-17 | Ahluwalia Gurpreet S | Alteration of rate and character of hair growth |
US5132293A (en) * | 1990-08-14 | 1992-07-21 | Douglas Shander | Enzymic alteration of hair growth |
US5143925A (en) * | 1990-12-20 | 1992-09-01 | Douglas Shander | Alteration of rate and character of hair growth |
US5183817A (en) * | 1981-02-17 | 1993-02-02 | Bazzano Gail S | Combinations of retinoids and minoxidil-type compounds for hair growth |
US5189212A (en) * | 1990-09-07 | 1993-02-23 | University Of Georgia Research Foundation, Inc. | Triarylethylene carboxylic acids with estrogenic activity |
US5271942A (en) * | 1990-12-05 | 1993-12-21 | Ulrich Heverhagen | Agent for reducing the growth of or removing the hair on the human body |
US5300284A (en) * | 1991-09-04 | 1994-04-05 | Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. | Glycosaminoglycanase inhibitor andethane diol composition for maintenance of hair growth |
US5328686A (en) * | 1991-10-30 | 1994-07-12 | Douglas Shander | Treatment of acne or of pseudofolliculitis barbae |
US5362748A (en) * | 1993-09-15 | 1994-11-08 | The Procter & Gamble Company | Methods of using diethyldithiocarbamic acid for the prevention of hair growth |
US5364885A (en) * | 1992-11-13 | 1994-11-15 | Ahluwalia Gurpreet S | Reduction of hair growth |
US5411991A (en) * | 1992-12-22 | 1995-05-02 | Shander; Douglas | Method of reducing hair growth employing sulfhydryl active compounds |
US5444090A (en) * | 1991-11-05 | 1995-08-22 | Ahluwalia; Gurpreet S. | Method of reducing the rate of hair growth |
US5455234A (en) * | 1994-03-16 | 1995-10-03 | Ahluwalia; Gurpreet S. | Inhibition of hair growth |
US5468476A (en) * | 1994-03-16 | 1995-11-21 | Ahluwalia; Gurpreet S. | Reduction of hair growth |
US5474763A (en) * | 1994-03-11 | 1995-12-12 | Shander; Douglas | Reduction of hair growth |
US5554608A (en) * | 1994-09-28 | 1996-09-10 | Ahluwalia; Gurpreet S. | Inhibition of hair growth |
US5645825A (en) * | 1995-06-07 | 1997-07-08 | The Procter & Gamble Company | Depilatory compositions comprising sulfhydryl compounds |
US5648394A (en) * | 1993-05-27 | 1997-07-15 | Boxall; Brian Alfred | Topical composition for inhibiting hair growth |
US5652273A (en) * | 1995-11-30 | 1997-07-29 | Henry; James | Reduction of hair growth |
US5674477A (en) * | 1995-02-28 | 1997-10-07 | Ahluwalia; Gurpreet S. | Reduction of hair growth |
US5700835A (en) * | 1995-12-22 | 1997-12-23 | Alcon Laboratories, Inc. | 3-Oxa-D-prostaglandins for lowering IOP |
US5728736A (en) * | 1995-11-29 | 1998-03-17 | Shander; Douglas | Reduction of hair growth |
US5824694A (en) * | 1994-06-22 | 1998-10-20 | Bethesda Pharmaceuticals, Inc. | Thiazolidine derivatives for the treatment of psoriasis |
US5840752A (en) * | 1996-11-21 | 1998-11-24 | Henry; James P. | Reduction of hair growth |
US5866595A (en) * | 1991-09-26 | 1999-02-02 | The Regents Of The University Of California | Calcium antagonists for treatment of vascular restenosis |
US5908867A (en) * | 1996-07-18 | 1999-06-01 | Henry; James P. | Reduction of hair growth |
US5939458A (en) * | 1997-09-22 | 1999-08-17 | Henry; James P. | Reduction of hair growth |
US5958946A (en) * | 1998-01-20 | 1999-09-28 | Styczynski; Peter | Modulation of hair growth |
US5962466A (en) * | 1996-12-13 | 1999-10-05 | Styczynski; Peter | Reduction of hair growth using inhibitors of matrix metalloproteinases |
US5972944A (en) * | 1993-09-15 | 1999-10-26 | Warner-Lambert Company | Use of thiazolidinedione derivatives in the treatment of anovulation, hyperandrogenism and hirsutism |
US6020006A (en) * | 1998-10-27 | 2000-02-01 | The Gillette Company | Reduction of hair growth |
US6037326A (en) * | 1996-12-31 | 2000-03-14 | Styczynski; Peter | Reduction of hair growth |
US6060471A (en) * | 1998-01-21 | 2000-05-09 | Styczynski; Peter | Reduction of hair growth |
US6060515A (en) * | 1997-01-24 | 2000-05-09 | The Regents Of The University Of California | Treatment of skin conditions by use of PPARα activators |
US6071955A (en) * | 1999-02-25 | 2000-06-06 | The Regents Of The University Of California | FXR, PPARA and LXRA activators to treat acne/acneiform conditions |
US6093748A (en) * | 1995-02-28 | 2000-07-25 | Ahluwalia; Gurpreet S. | Inhibition of hair growth |
US6121269A (en) * | 1999-02-22 | 2000-09-19 | Henry; James P. | Reduction of hair growth |
US6187814B1 (en) * | 1997-01-24 | 2001-02-13 | The Regents Of The University Of California | Treatment of skin conditions with FXR activators |
US6235737B1 (en) * | 2000-01-25 | 2001-05-22 | Peter Styczynski | Reduction of hair growth |
US6239170B1 (en) * | 1993-05-28 | 2001-05-29 | Gurpreet S. Ahluwalia | Inhibition of hair growth |
US6248751B1 (en) * | 1993-05-28 | 2001-06-19 | Gurpreet S. Ahluwalia | Inhibition of hair growth |
US6284234B1 (en) * | 1998-08-04 | 2001-09-04 | Johnson & Johnson Consumer Companies, Inc. | Topical delivery systems for active agents |
US6299865B1 (en) * | 2000-05-02 | 2001-10-09 | Peter Styczynski | Reduction of hair growth |
US20020019338A1 (en) * | 2000-08-01 | 2002-02-14 | Hebert Rolland F. | Water-soluble salts of 2-difluoromethyl-2,5-diaminopentanoic acid (DFMO) |
US6369098B1 (en) * | 1999-10-05 | 2002-04-09 | Bethesda Pharmaceuticals, Inc. | Dithiolane derivatives |
US20020044953A1 (en) * | 2000-07-28 | 2002-04-18 | Michelet Jean Francois | Use of non-prostanoic agonists of prostaglandin EP-2 and/or EP-4 receptors as cosmetic agents for attenuating, reducing or stopping the loss of head hair and other hairs |
US20020045659A1 (en) * | 2000-07-28 | 2002-04-18 | Michelet Jean Francois | Use, in cosmetic preparations, of prostaglandin EP-3 receptor agonists to attenuate, reduce or stop the growth of head hair and other hairs |
US20020052414A1 (en) * | 2000-07-28 | 2002-05-02 | Bruno Bernard | Use, in cosmetic preparations, of prostaglandin EP-2 and/or EP-4 receptor antagonists to attenuate, reduce or stop the growth of head hair and other hairs |
US20020052416A1 (en) * | 2000-07-28 | 2002-05-02 | Michelet Jean Francois | Use of prostaglandin EP-3 receptor antagonists as cosmetic agents for attenuating, reducing or stopping the loss of head hair and other hairs |
US6414017B2 (en) * | 1993-05-28 | 2002-07-02 | The Gillette Company | Inhibition of hair growth |
US6452032B1 (en) * | 1999-06-11 | 2002-09-17 | Allergan Sales, Llc | Organosilyl compounds having nuclear hormone receptor modulating activity |
US20030012755A1 (en) * | 2001-06-27 | 2003-01-16 | Peter Styczynski | Reduction of hair growth |
US6613780B2 (en) * | 1997-06-27 | 2003-09-02 | Kaneka Corporation | Heat shock factor activity inhibitor |
US20030187042A1 (en) * | 2001-08-13 | 2003-10-02 | Ulrike Bauer | NR1H4 nuclear receptor binding compounds |
US6743419B1 (en) * | 1992-12-22 | 2004-06-01 | The Gillette Company | Method of reducing hair growth employing sulfhydryl active compounds |
US6743822B2 (en) * | 2001-08-10 | 2004-06-01 | The Gillette Company | Reduction of hair growth |
US20040176426A1 (en) * | 2000-09-05 | 2004-09-09 | Tularik, Inc. | FXR modulators |
US20040180942A1 (en) * | 2001-12-21 | 2004-09-16 | X-Ceptor Therapeutics, Inc. | Heterocyclic modulators of nuclear receptors |
US20040192778A1 (en) * | 2003-03-26 | 2004-09-30 | Anwar Jardien | Reduction of hair growth |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US530284A (en) * | 1894-12-04 | Heinrich muller | ||
GB1458349A (en) | 1972-12-05 | 1976-12-15 | Sykora F | Composition for and a process therewith of treating the hair and/or scalps of animals |
GB9118866D0 (en) | 1991-09-04 | 1991-10-23 | Unilever Plc | Cosmetic composition |
IT1258069B (en) * | 1992-04-10 | 1996-02-20 | COMPOSITION FOR TOPICAL USE WITH STIMULUS ACTIVITY FOR GROWTH, REGENERATION, PREVENTION OF ENRIGEMENT AND NATURAL REPIGMENTATION OF HAIR | |
AU3931093A (en) | 1993-03-19 | 1994-10-11 | Handelman, Joseph H. | Topical composition for inhibiting hair growth |
WO1998002134A1 (en) | 1996-07-12 | 1998-01-22 | Johnson & Johnson Consumer Products, Inc. | Methods for altering hair growth and hair pigmentation by apoptosis in the follicular papillae and compositions therefor |
AU3982601A (en) | 2000-02-23 | 2001-09-03 | Orentreich Foundation For The | Methods and compositions for the treatment of alopecia and other disorders of the pilosebaceous apparatus |
DK1392714T3 (en) | 2001-03-12 | 2006-01-09 | Intercept Pharmaceuticals Inc | Steroids as Agonists for FXR |
JP2005501229A (en) | 2001-06-26 | 2005-01-13 | アナダーム リサーチ コーポレイション | Mammalian hair growth mediated by FKBP51 / 52 and CYP40 |
US20030036561A1 (en) * | 2001-08-10 | 2003-02-20 | Peter Styczynski | Reduction of hair growth |
AU2003228283A1 (en) | 2002-03-07 | 2003-09-22 | X-Ceptor Therapeutics, Inc. | Quinazolinone modulators of nuclear receptors |
WO2003080803A2 (en) | 2002-03-21 | 2003-10-02 | Smithkline Beecham Corporation | Methods of using farnesoid x receptor (fxr) agonists |
ITMI20021532A1 (en) | 2002-07-12 | 2004-01-12 | Roberto Pellicciari | CHEMICAL COMPOUNDS |
EP1583509B1 (en) * | 2002-09-09 | 2014-05-07 | Nestec S.A. | Orally administrable composition for improving hair and coat quality |
WO2004046162A2 (en) | 2002-11-14 | 2004-06-03 | The Scripps Research Institute | Non-steroidal fxr agonists |
EP1562915A1 (en) | 2002-11-22 | 2005-08-17 | SmithKline Beecham Corporation | Farnesoid x receptor agonists |
JP3913718B2 (en) * | 2003-06-27 | 2007-05-09 | 花王株式会社 | Hair growth inhibiting skin external preparation |
-
2005
- 2005-05-31 US US11/141,798 patent/US7618956B2/en not_active Expired - Fee Related
-
2006
- 2006-05-15 CA CA2729431A patent/CA2729431A1/en not_active Abandoned
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- 2006-05-15 EP EP06759810A patent/EP1888176A2/en not_active Withdrawn
- 2006-05-15 CA CA2729438A patent/CA2729438A1/en not_active Abandoned
- 2006-05-15 CA CA2729440A patent/CA2729440A1/en not_active Abandoned
- 2006-05-15 BR BRPI0611490-3A patent/BRPI0611490A2/en not_active IP Right Cessation
- 2006-05-15 WO PCT/US2006/018663 patent/WO2006130330A2/en active Application Filing
- 2006-05-15 KR KR1020077027693A patent/KR20080010444A/en not_active Application Discontinuation
- 2006-05-15 CA CA2729437A patent/CA2729437A1/en not_active Abandoned
- 2006-05-15 CN CNA2006800188989A patent/CN101184532A/en active Pending
- 2006-05-15 AU AU2006252877A patent/AU2006252877B2/en not_active Ceased
- 2006-05-15 MX MX2007015060A patent/MX2007015060A/en active IP Right Grant
- 2006-05-15 CA CA002608053A patent/CA2608053A1/en not_active Abandoned
-
2009
- 2009-10-02 US US12/572,564 patent/US20100021412A1/en not_active Abandoned
Patent Citations (81)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3426137A (en) * | 1965-12-23 | 1969-02-04 | Olin Mathieson | Hair growth inhibiting by aminobenzophenones |
US4161540A (en) * | 1966-08-22 | 1979-07-17 | Schering Corporation | Antiandrogenic agents and methods for the treatment of androgen dependent disease states |
US3878239A (en) * | 1972-05-09 | 1975-04-15 | Ono Pharmaceutical Co | Prostaglandin D compounds production |
US4039669A (en) * | 1975-08-01 | 1977-08-02 | Sterling Drug Inc. | Composition for topical application and use thereof |
US4201873A (en) * | 1975-09-17 | 1980-05-06 | The Upjohn Company | 9-Deoxy-9,10-didehydro-PGD2 analogs |
US4203924A (en) * | 1976-01-08 | 1980-05-20 | The Upjohn Company | 2-Decarboxy-2-hydroxymethyl-deoxy-9,10-didehydro-PGD2 analogs |
US4139638A (en) * | 1976-09-23 | 1979-02-13 | Schering Corporation | Methods for the treatment of hirsutism |
US4185099A (en) * | 1977-01-04 | 1980-01-22 | Also Laboratori S.a.S. di Dr.P. Sorbini & C | Hair and scalp treatment with compositions containing chenodeoxycholic or ursodeoxycholic acid |
US4370315A (en) * | 1977-02-22 | 1983-01-25 | Sederma | Post-depilatory composition reducing progressively the growth of body hair |
US4191775A (en) * | 1977-12-15 | 1980-03-04 | Imperial Chemical Industries Limited | Amide derivatives |
US4269831A (en) * | 1979-05-09 | 1981-05-26 | Sterling Drug Inc. | Topical dermatological method of use of an androstenopyrazole |
US5183817A (en) * | 1981-02-17 | 1993-02-02 | Bazzano Gail S | Combinations of retinoids and minoxidil-type compounds for hair growth |
US4517175A (en) * | 1982-06-07 | 1985-05-14 | Kao Corporation | Hair cosmetics |
US4562204A (en) * | 1982-06-30 | 1985-12-31 | Ono Pharmaceutical Co., Ltd. | Trans-Δ2 -prostaglandin D derivatives, process for their preparation and compositions containing them |
US4508714A (en) * | 1983-11-14 | 1985-04-02 | Tihomir Cecic | Organic scalp lotion |
US4885289A (en) * | 1983-12-12 | 1989-12-05 | Breuer Miklos M | Alteration of character of male beard growth |
US4720489A (en) * | 1984-10-15 | 1988-01-19 | Douglas Shander | Hair growth modification with ornithine decarboxylase inhibitors |
US4935231A (en) * | 1985-08-28 | 1990-06-19 | Repligen Corporation | Use of thioredoxin, thioredoxin-derived, or thioredoxin-like dithiol peptides in hair care preparations |
US5096911A (en) * | 1990-06-25 | 1992-03-17 | Ahluwalia Gurpreet S | Alteration of rate and character of hair growth |
US5132293A (en) * | 1990-08-14 | 1992-07-21 | Douglas Shander | Enzymic alteration of hair growth |
US5189212A (en) * | 1990-09-07 | 1993-02-23 | University Of Georgia Research Foundation, Inc. | Triarylethylene carboxylic acids with estrogenic activity |
US5095007A (en) * | 1990-10-24 | 1992-03-10 | Ahluwalia Gurpreet S | Alteration of rate and character of hair growth |
US5271942A (en) * | 1990-12-05 | 1993-12-21 | Ulrich Heverhagen | Agent for reducing the growth of or removing the hair on the human body |
US5143925A (en) * | 1990-12-20 | 1992-09-01 | Douglas Shander | Alteration of rate and character of hair growth |
US5300284A (en) * | 1991-09-04 | 1994-04-05 | Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. | Glycosaminoglycanase inhibitor andethane diol composition for maintenance of hair growth |
US5866595A (en) * | 1991-09-26 | 1999-02-02 | The Regents Of The University Of California | Calcium antagonists for treatment of vascular restenosis |
US5328686A (en) * | 1991-10-30 | 1994-07-12 | Douglas Shander | Treatment of acne or of pseudofolliculitis barbae |
US5444090A (en) * | 1991-11-05 | 1995-08-22 | Ahluwalia; Gurpreet S. | Method of reducing the rate of hair growth |
US5364885A (en) * | 1992-11-13 | 1994-11-15 | Ahluwalia Gurpreet S | Reduction of hair growth |
US6743419B1 (en) * | 1992-12-22 | 2004-06-01 | The Gillette Company | Method of reducing hair growth employing sulfhydryl active compounds |
US5411991A (en) * | 1992-12-22 | 1995-05-02 | Shander; Douglas | Method of reducing hair growth employing sulfhydryl active compounds |
US5648394A (en) * | 1993-05-27 | 1997-07-15 | Boxall; Brian Alfred | Topical composition for inhibiting hair growth |
US6248751B1 (en) * | 1993-05-28 | 2001-06-19 | Gurpreet S. Ahluwalia | Inhibition of hair growth |
US6239170B1 (en) * | 1993-05-28 | 2001-05-29 | Gurpreet S. Ahluwalia | Inhibition of hair growth |
US6414017B2 (en) * | 1993-05-28 | 2002-07-02 | The Gillette Company | Inhibition of hair growth |
US5972944A (en) * | 1993-09-15 | 1999-10-26 | Warner-Lambert Company | Use of thiazolidinedione derivatives in the treatment of anovulation, hyperandrogenism and hirsutism |
US5362748A (en) * | 1993-09-15 | 1994-11-08 | The Procter & Gamble Company | Methods of using diethyldithiocarbamic acid for the prevention of hair growth |
US5474763A (en) * | 1994-03-11 | 1995-12-12 | Shander; Douglas | Reduction of hair growth |
US5468476A (en) * | 1994-03-16 | 1995-11-21 | Ahluwalia; Gurpreet S. | Reduction of hair growth |
US5455234A (en) * | 1994-03-16 | 1995-10-03 | Ahluwalia; Gurpreet S. | Inhibition of hair growth |
US5824694A (en) * | 1994-06-22 | 1998-10-20 | Bethesda Pharmaceuticals, Inc. | Thiazolidine derivatives for the treatment of psoriasis |
US5554608A (en) * | 1994-09-28 | 1996-09-10 | Ahluwalia; Gurpreet S. | Inhibition of hair growth |
US5674477A (en) * | 1995-02-28 | 1997-10-07 | Ahluwalia; Gurpreet S. | Reduction of hair growth |
US6093748A (en) * | 1995-02-28 | 2000-07-25 | Ahluwalia; Gurpreet S. | Inhibition of hair growth |
US5776442A (en) * | 1995-02-28 | 1998-07-07 | Ahluwalia; Gurpreet S. | Reduction of hair growth |
US5645825A (en) * | 1995-06-07 | 1997-07-08 | The Procter & Gamble Company | Depilatory compositions comprising sulfhydryl compounds |
US5728736A (en) * | 1995-11-29 | 1998-03-17 | Shander; Douglas | Reduction of hair growth |
US5824665A (en) * | 1995-11-30 | 1998-10-20 | Henry; James | Reduction of hair growth |
US5652273A (en) * | 1995-11-30 | 1997-07-29 | Henry; James | Reduction of hair growth |
US6218435B1 (en) * | 1995-11-30 | 2001-04-17 | James Henry | Reduction of hair growth |
US5700835A (en) * | 1995-12-22 | 1997-12-23 | Alcon Laboratories, Inc. | 3-Oxa-D-prostaglandins for lowering IOP |
US5908867A (en) * | 1996-07-18 | 1999-06-01 | Henry; James P. | Reduction of hair growth |
US5840752A (en) * | 1996-11-21 | 1998-11-24 | Henry; James P. | Reduction of hair growth |
US5962466A (en) * | 1996-12-13 | 1999-10-05 | Styczynski; Peter | Reduction of hair growth using inhibitors of matrix metalloproteinases |
US6037326A (en) * | 1996-12-31 | 2000-03-14 | Styczynski; Peter | Reduction of hair growth |
US6187814B1 (en) * | 1997-01-24 | 2001-02-13 | The Regents Of The University Of California | Treatment of skin conditions with FXR activators |
US6060515A (en) * | 1997-01-24 | 2000-05-09 | The Regents Of The University Of California | Treatment of skin conditions by use of PPARα activators |
US6613780B2 (en) * | 1997-06-27 | 2003-09-02 | Kaneka Corporation | Heat shock factor activity inhibitor |
US5939458A (en) * | 1997-09-22 | 1999-08-17 | Henry; James P. | Reduction of hair growth |
US5958946A (en) * | 1998-01-20 | 1999-09-28 | Styczynski; Peter | Modulation of hair growth |
US6060471A (en) * | 1998-01-21 | 2000-05-09 | Styczynski; Peter | Reduction of hair growth |
US6284234B1 (en) * | 1998-08-04 | 2001-09-04 | Johnson & Johnson Consumer Companies, Inc. | Topical delivery systems for active agents |
US6419913B1 (en) * | 1998-08-04 | 2002-07-16 | Johnson & Johnson Consumer Companies, Inc. | Topical delivery systems for active agents |
US6020006A (en) * | 1998-10-27 | 2000-02-01 | The Gillette Company | Reduction of hair growth |
US6121269A (en) * | 1999-02-22 | 2000-09-19 | Henry; James P. | Reduction of hair growth |
US6071955A (en) * | 1999-02-25 | 2000-06-06 | The Regents Of The University Of California | FXR, PPARA and LXRA activators to treat acne/acneiform conditions |
US6452032B1 (en) * | 1999-06-11 | 2002-09-17 | Allergan Sales, Llc | Organosilyl compounds having nuclear hormone receptor modulating activity |
US6369098B1 (en) * | 1999-10-05 | 2002-04-09 | Bethesda Pharmaceuticals, Inc. | Dithiolane derivatives |
US6235737B1 (en) * | 2000-01-25 | 2001-05-22 | Peter Styczynski | Reduction of hair growth |
US6299865B1 (en) * | 2000-05-02 | 2001-10-09 | Peter Styczynski | Reduction of hair growth |
US20020052416A1 (en) * | 2000-07-28 | 2002-05-02 | Michelet Jean Francois | Use of prostaglandin EP-3 receptor antagonists as cosmetic agents for attenuating, reducing or stopping the loss of head hair and other hairs |
US20020052414A1 (en) * | 2000-07-28 | 2002-05-02 | Bruno Bernard | Use, in cosmetic preparations, of prostaglandin EP-2 and/or EP-4 receptor antagonists to attenuate, reduce or stop the growth of head hair and other hairs |
US20020045659A1 (en) * | 2000-07-28 | 2002-04-18 | Michelet Jean Francois | Use, in cosmetic preparations, of prostaglandin EP-3 receptor agonists to attenuate, reduce or stop the growth of head hair and other hairs |
US20020044953A1 (en) * | 2000-07-28 | 2002-04-18 | Michelet Jean Francois | Use of non-prostanoic agonists of prostaglandin EP-2 and/or EP-4 receptors as cosmetic agents for attenuating, reducing or stopping the loss of head hair and other hairs |
US20020019338A1 (en) * | 2000-08-01 | 2002-02-14 | Hebert Rolland F. | Water-soluble salts of 2-difluoromethyl-2,5-diaminopentanoic acid (DFMO) |
US20040176426A1 (en) * | 2000-09-05 | 2004-09-09 | Tularik, Inc. | FXR modulators |
US20030012755A1 (en) * | 2001-06-27 | 2003-01-16 | Peter Styczynski | Reduction of hair growth |
US6743822B2 (en) * | 2001-08-10 | 2004-06-01 | The Gillette Company | Reduction of hair growth |
US20030187042A1 (en) * | 2001-08-13 | 2003-10-02 | Ulrike Bauer | NR1H4 nuclear receptor binding compounds |
US20040180942A1 (en) * | 2001-12-21 | 2004-09-16 | X-Ceptor Therapeutics, Inc. | Heterocyclic modulators of nuclear receptors |
US20040192778A1 (en) * | 2003-03-26 | 2004-09-30 | Anwar Jardien | Reduction of hair growth |
Also Published As
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WO2006130330A3 (en) | 2007-03-22 |
CA2729431A1 (en) | 2006-12-07 |
CA2729438A1 (en) | 2006-12-07 |
BRPI0611490A2 (en) | 2010-09-08 |
CA2608053A1 (en) | 2006-12-07 |
AU2006252877A1 (en) | 2006-12-07 |
US7618956B2 (en) | 2009-11-17 |
EP1888176A2 (en) | 2008-02-20 |
CA2729440A1 (en) | 2006-12-07 |
MX2007015060A (en) | 2008-01-28 |
WO2006130330A2 (en) | 2006-12-07 |
US20060269496A1 (en) | 2006-11-30 |
JP4801150B2 (en) | 2011-10-26 |
AU2006252877B2 (en) | 2011-05-26 |
KR20080010444A (en) | 2008-01-30 |
JP2008542372A (en) | 2008-11-27 |
CA2729437A1 (en) | 2006-12-07 |
CN101184532A (en) | 2008-05-21 |
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