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US3689668A - Method of alleviating wrinkles on skin - Google Patents

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US3689668A
US3689668A US3689668DA US3689668A US 3689668 A US3689668 A US 3689668A US 3689668D A US3689668D A US 3689668DA US 3689668 A US3689668 A US 3689668A
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arginine
di
diethylaminoethanol
para
method
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Emile Leon Piette
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Emile Leon Piette
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    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/96Cosmetics or similar toilet preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/98Cosmetics or similar toilet preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution of animal origin
    • A61K8/981Cosmetics or similar toilet preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution of animal origin of mammals or bird
    • A61K8/982Reproductive organs; Embryos, Eggs
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES
    • A61K8/00Cosmetics or similar toilet preparations
    • A61K8/18Cosmetics or similar toilet preparations characterised by the composition
    • A61K8/30Cosmetics or similar toilet preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toilet preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/44Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILET PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/08Anti-ageing preparations

Abstract

Cosmetic compositions containing an amine, such as the diaspartate of arginine para-aminobenzoyl-diethylaminoethanol, and a method for the substantial reduction of folds and wrinkles in the skin are disclosed. The cosmetic compositions are useful in that they have a hydrating effect on the human skin such that the complexion and brightness thereof can be substantially improved, whereas the folds and wrinkles of the skin can be substantially reduced.

Description

United States Paten Piette Sept. 5, 1972 [54] METHOD OF ALLEVIATING WRINKLES ON SKIN [72] Inventor: Emile Leon Piette, 40, Avenue Moliere, Brussels 18, Belgium 1968, abandoned.

[30] Foreign Application Priority Data Oct. 18, 1967 Belgium ..49740 [52] US. Cl. ..424/319, 424/105, 424/329 [51] Int. Cl. ..A6lk 7/00 [58] Field of Search ..424/319 [56] References Cited FOREIGN PATENTS OR APPLICATIONS 640,462 3/ 1964 Belgium OTHER PUBLICATIONS Chemical Abstracts, Vol. 63, p. 13415 (b), 1965.

Primary Examiner-Albert T. Meyers" Assistant Examiner -Doris J. Funderburk Attorney-Sughrue, Mion, Zinn & Macpeak [57] ABSTRACT Cosmetic compositions containing an amine, such as the di-aspartate of arginine para-aminobenzoyldiethylaminoethanol, and a method for the substantial reduction of folds and wrinkles in the skin are disclosed. The cosmetic compositions are useful in that they have a hydrating effect on the human skin such that the complexion and brightness thereof can be substantially improved, whereas the folds and wrinkles of the skin can be substantially reduced.

13 Claims, No Drawings METHOD OF ALLEVIATING WRINKLES ON SKIN When each R represents a methylene group Cl-l and m is 2, the compound of the general formu- CROSS'REFERENCE To RELATED la l is the tri-aspartate of di-L-arginine para- APPLICATIONS aminobenzoyl-diethylaminoethanol.

This application is a continuation of my co-pending 5 When each R represents an ethylene group -(CH application, Ser, No. 736,032, filed June 1 l, 1968 now and m is 2, the compound of the general formula I is abandoned. the tri-glutatmate of di-L-arginine para-aminobenzoyldiethylaminoethanole BACKGROUND OF THE INVENTION The compounds of the general formula I are crystal- 1, Fi ld f h I ti lizable and have similar physico-chemical and biologi- This invention relates to cosmetic compositions ha cal properties. They can be used in their dextrogyre ing such a hydrating effect on the human skin that the gy e o ace c o s a d also as complexion and brightness thereof can be substantially acid addition Salts, Such as the hydroehloridesimproved, whereas the folds and wrinkles of the skin The compounds of the general formula I m y be can be substantially reduced by applying the cosmetic prepared by reaction of one or two moles of arginine compositions to the human skin. glutamate or aspartate with one mole of para- 2. Description of the Prior Art aminobenzoyl-diethylamino-ethanol in a solvent, such The appearance of the skin depends from the comas distilled water, at the reflux boiling temperature of plexion, brightness, ruggedness (folds and wrinkles) the reaction medium. After evaporation under reduced and wear thereof. As is known, the relief of the skin pressure, the product is crystallized at a temperature of may be influenced by hydrating cosmetic compositions less than 0 C or is dried in a drying closet. Crystalline n g. as aetive ingredients, gly or Combmed, pure products, which are clearly distinguished from Various Products Such as extracts y tisues mere mixtures of the starting reactants, are thus obplacenta), animal Serums or plasmas, amniotic fluid, mi d i h i ld f98 t 99%, Plant eXtraetS, leeithines, amino-alcohols, Such as The preparation of the compounds of formula I is choline and the Sa ts a derivatives thereof, and the described with more details in the following examples. like.

This invention relates to cosmetic compositions hav- EXAMPLE 1 ing a significant hydrating activity when topically applied to human skin, due to the presence in the To 46.82 grams of dry (l) arginine di-( l+) glutacosmetic compositions of amine compounds as defined mate dissolved in 500 millilitres of fresh distilled water, hereafter which have a hydrating activity which was h d at 80 C, 2353 grams f i b lunknown heretofore and which have not been used in diethylaminoethanol are added, while stirring.

- cosmetology until now- The e amine comp n m y The mixture is maintained at the boiling temperature also be added to known hydrating cosmetic composi- C) under d d r ss re and is then conliOnS, in which hey increase surprisingly the hydrating centrated, by distillation of the aqueous solvent, until activity of the known hydrating ihgfedlehtsan opalescent product is obtained. The product is then crystallized at a temperature of less than 0 C and dried SUMMARY OF THE INVENTION during 24 hours at 45 C in a drying closet.

The invention concerns a method for substantially Yi ld; 98 t 99%. About 69 grams of crystalline direducing the folds and wrinkles in skin by topically ap- (1+) glutamate of (l) arginine para- P y hydrating Cosmetic compositions Containing, as aminobenzoyl-diethylaminoethanol are thus obactive ingredient, at least one amine compound, which 45 mi d may be represented by the following general formula: Melting P i t; 172 173 C NH C2115 o I 0OOH-HzN-il-NH-(CHz)sCHNHzCOOH COOH-lh-(CHQPOil-Q-Nflt 1 (52115 [en-N112 ()HNH2 A 9 a *B s9, 1 (I) in which R represents an alkylene group -(Cll..),, EXAMPLEZ where n l or 2, and m represents 1 or 2.

To a solution of 50.45 grams of the DETAILED DESCRIPTION OF THE INVENTION monohydrochloride of l) arginine di-( 1+) glutamate When each R in the above described formula dissolved in 450 millilitres of fresh distilled water, represents a methylene group (-Cl-l and m is l, heated at 80 C, 23.63 grams of para-aminobenzoylthe compound of the general formula I is the diaspardiethylaminoethanol are added, while stirring the reactate of arginine para-aminobenzoyltion medium. By treating this medium as described in diethylaminoethanol. Example 1. 72.5 grams of crystalline di-( 1+) glutamate When each R represents an ethylene group (Cl-l of l) arginine para-aminobenzoyland m is l, the compound of the general formula I is diethylaminoethanol are obtained. This compound the di-glutamate of arginine para-aminobenzoylstarts melting at 159 C with decomposition and melts diethylaminoethanol. until ll 72 C.

EXAMPLE 3 EXAMPLE 4 To a boiling solution of 44 grams of dry (1) arginine di-(l-) aspartate in 500 millilitres of fresh distilled water, 23.63 grams of para-aminobenzoyldiethylaminoethanol are added while stirring. The reaction mixture is then treated as described in Example l. About 66 grams of crystalline di-( l--) aspartate of l) arginine diethylaminoethanol are obtained.

Melting point: l44l48 C.

EXAMPLE 5 To a boiling solution of 47.65 grams of the monohydrochloride of l) arginine de (l)aspartate in 500 milliliters of fresh distilled water, 23.63 grams of para-aminobenzoyl-diethylaminoethanol are added while stirring. The reaction mixture is then treated as described in Example 1. About 70 grams of the crystalline monohydrochloride of di( 1) aspartate of l)arginine paraaminobenzoyl-diethylaminoethanol are obtained. This compound starts melting at 152 C (with decomposition).

EXAMPLE 6 100 milliliters of a 1N solution of hydrochloric acid are added to 44 grams of (l) arginine di (l) aspartate. The obtained solution is heated to boiling tem-- perature and 400 milliliters of fresh distilled water are added thereto. While maintaining the temperature at 85 C and while stirring the mixture, 23.63 grams of para-aminobenzoyldiethylaminoethanol are added. The reaction mixture is then treated as described in Example l. About 70 grams of crystalline monohydrochloride of di(1) asparate of l)arginine para-aminobenzoyl-diethylaminoethanol are obtained.

EXAMPLE 7 The tri-glutamate of di-arginine para-aminobenzoyldiethylaminoethanol (M.P.: 235-238 C) and the hydrochloride thereof are prepared by the procedure described in Examples 1, 2 and 3, except that two moles of di-arginine glutamate per mole of paraaminobenzoyl-diethylaminoethanol are used.

EXAMPLE 8 The tri-aspartate of di-arginine para-aminobenzoyldiethylaminoethanol (M.P.: 205208 C) and the hydrochloride thereof are prepared by the procedure described in Examples 4, 5 and 6, except that two moles of di-arginine aspartate per mole of parapara-aminobenzoylaminobenzoyl-diethylaminoethano1 are used. 1

The compounds of the general formula 1 and the hydrochlorides thereof are soluble in water. All that is necessary is to apply topically the compounds of the general formula I in an effective amount of the compound sufficient to alleviate the folds and wrinkles of the skin.

The hydrating cosmetic compositions for external use according to this invention, which contain, as active ingredients, at least one compound of formula 1, may take various forms and may be used on the human skin. Said compositions may take the form of fatty or non fatty creams, milky suspensions or emulsions of the water-in-oil or oil-in-water types, lotions, gels or jellies, colloidal or non colloidal aqueous or oily solutions, pastes, soaps, aerosols, soluble tablets (to be dissolved in a fluid, such as water) or sticks.

The amount of active ingredient contained in the hydrating cosmetic compositions according to the invention applied to the skin may vary between wide limits, depending from the formulating and from the frequency of use of said compositions. Generally, said compositions contain from 0.1% to 2%, by weight of the composition of active ingredient of the formula 1.

The hydrating cosmetic compositions used in the method according to the invention may contain not only one or more active ingredients of the formula 1 but also conventional vehicles or carriers, such as solvents, fats, oils and mineral waxes, fatty acids and derivatives thereof, alcohols and derivatives thereof, glycols and derivatives thereof, glycerol and derivatives thereof, sorbitol and derivatives thereof, surface-active agents of the anionic, cationic or non ionic type, emulsifying agents, preserving agents, perfumes, etc.

A few examples of hydrating cosmetic agents used in the method according to this invention are given hereafter. These examples are only illustrative and must not be considered as limiting the scope of the invention. In said examples, the percentages are by weight.

EXAMPLE 1 Hydrating Milk Mono and diglycerides of fatty acids 5 to 6% (palmitic and stearic acids) Condensate of polyglycol and saturated 2.5 to 3% fatty alcohol ethers with polyoxyethylene lsopropyleneglycol 5 to 15% Perhydrosqualene 5 to 15% Amniotic fluid 2 to 10% Tri-aspartate of di-arginine-paraaminobenzoyl diethylaminoethanol 0.5 to 1% Distilled water q.s.ad.

EXAMPLE ll Hydrating Milk High fatty alcohols (such as cetyl, stearyl, myristyl alcohols) 5 to 6% Condensate of polyglycol and saturated fatty alcohol ethers with polyoxyethylene 2.5 to 3% lsopropyleneglycol 5 to 15% Perhydrosqualene 5 to 15% Amniotic fluid 2 to 10% Tri-aspartate of di-arginine-paraaminobenzoyl-diethylaminoethanol 0.5 to 1% Distilled water q.s.ad. 100% EXAMPLE III Hydrating Milk Mono and diglycerides of palmitic and stearic acids to 6% Condensate of polyglycol and saturated fatty alcohol ethers with polyoxyethylene 2.5 to 3% Glycerol 5 to 15% Ester of stearic acid and octyldodecanol 5 to 15% Amniotic fluid 2 to Fri-glutamate of di-arginine paraaminobenzoyl diethylaminoethanol 0.5 to 1% Distilled water q.s.ad. 100% EXAMPLE IV Cream of the Oil-in-Water Type Liquid paraffin 40 to 60% White wax 5 to 10% Solid paraffin 2 to 8% Borax 0.1 to 0.5% Di-aspartate of arginine para-aminobenzoyl diethylaminoethanol 0.5 to 1% Distilled water q.s.ad. 100% EXAMPLE V Cream of the Water-in-Oil Type Liquid paraffin 30 to 50% Ozokerite 3 to 8% Solid paraffin l to 3% Lanoline 1.5 to 4% Mono-diglycerides of fat-forming fatty acids with not more than l/l00 of 1% butylated anisole, l/lOO of 1% butylated hydroxy toluene, and H100 of 1% citric acid in propylene glycol added as a preservative (Arlacel l86-Atlas Chemical Industries-Wilmington, Delaware, U.S.A.) l to 2% Polysorbate 80, an ester of sorbitan etherified with polyethylene glycol (Tween 80 Atlas Chemical Industries) 0.1 to 0.3% Di-glutamate of arginine paraaminobenzoyl-diethylaminoethanol 0.5 to 1% Water q.s.ad. 100% EXAMPLE VI Hydrating Lotion Triethanolamine lauryl sulfate 1 to 5% lsopropanol 40 to 60% Cetiol V (decylic ester of oleic acid- Dehydag Deutsche Hydrierwerke, Dusseldorf, Germany) 2 to 6% Triglutamate of di-arginine para-aminobenzoyl diethylaminoethanol 0.5 to 1% Water q.s.ad. 100% EXAMPLE VII Cream of the Water-in-Oil Type Amphoccrine K (Dehydag), a mixture of fatty alcohols and waxy esters of animal origin 40 to 60% Placenta extract 5 to Tri-aspartate of di-arginine paraaminobenzoyl diethylaminoethanol 0.5 to 1% Water q.s.ad. 100% EXAMPLE VIII Hydrating Aerosol The cream of the oil-in-water of Example IV and 8% by weight of a mixture of 40% dichlorodifluoromethane and 60% dichlorotetrafluoromethane are introduced into an aerosol container.

To the formulations described in Examples I to VIII,

like), dyes or pigments (such as zinc oxide, titanium oxide, ochre and the like), as well as preserving or antioxidizing agents (such as butylhydroxy toluene, butylhydroxy ariisole, sorbic acid, methyl para-hydroxybenzoate, and the like) may be added in suitable amounts, as well known in cosmetology.

Tests have been made in vivo with the hydrating cosmetic compositions according to the invention. These tests have clearly shown that said compositions have remarkable hydrating properties when topically applied to the skin.

These tests have shown the hydrating properties of the compounds of formula I as well as the synergistic effect of these compounds on already known hydrating products (such as amniotic fluid, placenta extract and the like), when they are used jointly with these known products.

The tests have been made by applying on the human face (forehead and cheeks) masks for taking impressions of the relief of the skin before and after treatment by means of various hydrating compositions. For taking such impressions, compositions of the Laboratory of Dr. Renaux (Paris, France) containing rubber or plastic materials, which cure in contact with the skin, have been used. The masks obtained after curing or hardening on the face of the rubber or plastic-based compositions and after removing the hardened layers from the face may be used for determining objectively the effectiveness of the hydrating compositions acco rding to the invention for reducing or alleviating the skin wrinkles, manly by hydrating the skin. The effect of reducing or alleviating the skin wrinkles is determined by counting with an approximation of il% the impressions of the wrinkles on surfaces of an area of 3cm ofthe masks.

The count of impressions on the masks taken before the treatment by means of hydrating compositions is used as base for the subsequent counts. A value of is given to the number of wrinkle impressions counted on the mask taken before the treatment by means of the hydrating compositions.

As control, a hydrating cream containing only water as the hydrating ingredient has been used.

Said control cream had the following composition.

Formulation A Monoand di-glycerides of palmitic and stearic acids 6% Condensate of polyglycol and saturated fatty alcohols with polyoxyethylene 3% Ester of stearic acid and diethyldodecanol 10% Preserving agent and perfume q.s.

Water q.s.ad. 100% For one series of tests, 1% of tri-aspartate of arginine para-aminobenzoyl-diethylaminoethanol (Formulation B) was added to said base or control cream.

For another series of tests, 20% of amniotic fluid, 10% of human placenta extract and 0.1% of choline chloride (Formulation C) was added to the control cream, these three known products being commonly used in hydrating creams of good quality.

For still another series of tests, 20% of amniotic fluid, 10% of human placenta extract, 0.1% of choline chloride and 1% of tri-aspartate of arginine paraaminobenzoyl-diethylaminoethanol (Formulation D) were added to the control cream.

Finally, for the last series of tests, a cream (Formulation E) similar to Formulation D was used, except that it contained 10% in place of 20% of amniotic fluid,

.in place of of placenta extract and 0.05% in place of 0.1% of choline chloride (i.e., 50% less of these active ingredients than in Formulation D), the proportion of tri-aspartate of arginine paraaminobenzoyldiethylaminoethanol remaining identical 1%).

The various tests were each made on fifteen 40 to 50 years old patients before and after daily treatments, in the evening, with the various creams (Formulations A to E) during 30 days, on the forehead or on the cheeks, of the patients.

The control cream A and the creams B to E were applied respectively on the lefthand part of the forehead or the lefthand cheek and on the righthand part of the forehead or righthand check.

a. First series of tests An impression of the face skin of patients was taken by means of a mask and the number of impressed wrinkles was counted. A value of 100% was given to the average of the total number of impressed wrinkles.

The patients were then treated, during 30 days, by means of the control cream (Formulation A) and by means of the cream (Formulation B) according to the invention.

After said treatment, a new impression of the'face of the 15 patients was taken and the number of remaining wrinkle impressions was counted. By taking the average number of remaining wrinkle impressions, the percentage of the remaining wrinkles was determined in comparison with the percentage 100%) determined before the treatment.

The following results were obtained:

TABLE 1 Treated Before After Treatment Skin Treatment Part Formula- Formulation A tion B Forehead 100% 90%(:1%) 49%(:1%) Cheeks 100% 45%(:1%)

cream A.

diethylaminoethanol to cream C, the anti-wrinkle effect of cream C is surprisingly increased of 18% and 19%, whereas the known active ingredients (amniotic fluid, placenta extract and choline chloride) have themselves, at the indicated doses, an anti-wrinkle effect which is substantially equivalent to that of the triaspartate of arginine para-aminobenzoyl diethylaminoethanol, as shown by a comparison of the results obtained with cream B (Table l) and cream C (Table 11) c. Third series of tests The procedure was the same as in the first series of tests, except that creams D and E were used and that the results were compared to those obtained with con-- trol cream A.

These results are given in the following table:

tri-aspartate of arginine para-aminobenzoyl diethylaminoethanol on conventional ingredients (amniotic fluid, placenta extract and choline chloride), since the results obtained when the percentage of these three known active ingredients is reduced by 50% and when the percentage (1%) of the above tri-aspartate is maintained are nearly the same and even slightly better than the. results obtained with a twofold percentage of these three active ingredients.

Tests made with hydrating compositions containing other compounds of the formula I have given similar results.

What is claimed is:

l. A method of temporarily alleviating wrinkles on human skin, which comprises topically applying to said skin a wrinkle alleviating effective amount of at least one compound of the formula:

in which R represents an alkylene group (Cl-l wherein n=1 or 2, and m represents 1 or 2, or the acid addition salt thereof.

2. The method of claim 1 wherein the compound is the di-aspartate of arginine para-aminobenzoyldiethylaminoethanol.

3. The method of claim 1 wherein the compound is an acid addition salt of the di-aspartate of arginine para-aminobenzoyl-diethylaminoethanol.

4. The method of claim 1 wherein the compound is the hydrochloride of di-aspartate of arginine paraaminobenzoyl-diethylaminoethanol. v

5. The method of claim 1 wherein the compound is the di-glutamate of arginine para-aminobenzoyldiethylaminoethanol.

6. The method of claim 1 wherein the compound is the hydrochloride of di-glutamate of arginine paraaminobenzoyl-diethylaminoethanol.

7. The method of claim 1 wherein the compound is the tri-aspartate of di-L-arginine para-aminobenzoyldiethylaminoethanol.

8. The method of claim 1 wherein the compound is an acid addition salt of the tri-aspartate of di-L-arginine para-aminobenzoyl-diethylaminoethanol.

9. The method of claim 1 wherein the compound is the hydrochloride of tri-aspartate of di-L-arginine paraaminobenzoyl-diethylaminoethanol.

10. The method of claim 1 wherein the compound is the tri-glutamate of di-L-arginine-para-aminobenzoyldiethylaminoethanol.

11. The method of claim 1 wherein the compound is an acid addition salt of the tri-glutamate of di-L-arginine-para-aminobenzoyl-diethylaminoethanol.

12. The method of claim 1 wherein the ingredient is the hydrochloride of the tri-glutamate of di-L-argininepara-aminobenzoyl-diethylaminoethanol.

13. The method of claim 1 wherein the compound is contained in a cosmetically acceptable inert carrier at a level of from 0.1% to about 2% by weight of the composition. I I

Claims (12)

  1. 2. The method of claim 1 wherein the compound is the di-aspartate of arginine para-aminobenzoyl-diethylaminoethanol.
  2. 3. The method of claim 1 wherein the compound is an acid addition salt of the di-aspartate of arginine para-aminobenzoyl-diethylaminoethanol.
  3. 4. The method of claim 1 wherein the compound is the hydrochloride of di-aspartate of arginine para-aminobenzoyl-diethylaminoethanol.
  4. 5. The method of claim 1 wherein the compound is the di-glutamate of arginine para-aminobenzoyl-diethylaminoethanol.
  5. 6. The method of claim 1 wherein the compound is the hydrochloride of di-glutamate of arginine para-aminobenzoyl-diethylaminoethanol.
  6. 7. The method of claim 1 wherein the compound is the tri-aspartate of di-L-arginine para-aminobenzoyl-diethylaminoethanol.
  7. 8. The method of claim 1 wherein the compound is an acid addition salt of the tri-aspartate of di-L-arginine para-aminobenzoyl-diethylaminoethanol.
  8. 9. The method of claim 1 wherein the compound is the hydrochloride of tri-aspartate of di-L-arginine para-aminobenzoyl-diethylaminoethanol.
  9. 10. The method of claim 1 wherein the compound is the tri-glutamate of di-L-arginine-para-aminobenzoyl-diethylaminoethanol.
  10. 11. The method of claim 1 wherein the compound is an acid addition salt of the tri-glutamate of di-L-arginine-para-aminobenzoyl-diethylaminoethanol.
  11. 12. The method of claim 1 wherein the ingredient is the hydrochloride of the tri-glutamate of di-L-arginine-para-aminobenzoyl-diethylaminoethanol.
  12. 13. The method of claim 1 wherein the compound is contained in a cosmetically acceptable inert carrier at a level of from 0.1% to about 2% by weight of the composition.
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Cited By (16)

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US5385938A (en) * 1986-12-23 1995-01-31 Yu; Ruey J. Method of using glycolic acid for treating wrinkles
US5389677A (en) * 1986-12-23 1995-02-14 Tristrata Inc Method of treating wrinkles using glycalic acid
US5554597A (en) * 1986-12-23 1996-09-10 Tristrata Inc Compositions comprising 2-hydroxycarboxylic acids and related compounds, and methods for alleviating signs of dermatological aging
US5665776A (en) * 1986-12-23 1997-09-09 Tristrata Technology, Inc. Additives enhancing topical actions of therapeutic agents
US5686489A (en) * 1986-12-23 1997-11-11 Tristrata Technology, Inc. Alpha hydroxyacid esters for skin aging
US5834510A (en) * 1986-12-23 1998-11-10 Tristrata Technology, Inc. Compositions comprising 2-hydroxycarboxylic acids and related compounds, and methods for alleviating signs of dermatological aging
US5886041A (en) * 1989-08-15 1999-03-23 Tristrata Technology, Inc. Amphoteric compositions and polymeric forms of alpha hydroxyacids, and their therapeutic use
US5942250A (en) * 1986-12-23 1999-08-24 Tristrata Technology, Inc. Compositions and methods for enhancing the topical effects of sunscreen agents
US6191167B1 (en) 1997-12-29 2001-02-20 Tristrata Technology, Inc. Pharmaceutical compositions containing hydroxycarboxylic acid and/or ketocarboxylic acids and methods of using the same
US6335023B1 (en) 1999-06-30 2002-01-01 Ruey J. Yu Oligosaccharide aldonic acids and their topical use
US6384079B1 (en) 1986-12-23 2002-05-07 Tristrata Technology, Incorporated Compositions comprising 2-hydroxycarboxylic acids and related compounds, and methods for alleviating signs of dermatological aging
US6688311B2 (en) * 2002-03-14 2004-02-10 Allergan, Inc. Method for determining effect of a clostridial toxin upon a muscle
US20040180854A1 (en) * 2001-11-13 2004-09-16 Yu Ruey J. Oligosaccharide aldonic acids and their topical use
US20070134158A1 (en) * 2002-03-14 2007-06-14 Allergan, Inc. Method for comparing multiple botulinum neurotoxins
US8013017B2 (en) 2001-05-31 2011-09-06 Upsher-Smith Laboratories, Inc. Dermatological compositions and methods
US20170157015A1 (en) * 2014-06-18 2017-06-08 Medicell Technologies, Llc Stem cell stimulating compositions and methods

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Patent Citations (1)

* Cited by examiner, † Cited by third party
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BE640462A (en) * 1963-11-27 1964-03-16

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Chemical Abstracts, Vol. 63, p. 13415 (b), 1965. *

Cited By (84)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5385938A (en) * 1986-12-23 1995-01-31 Yu; Ruey J. Method of using glycolic acid for treating wrinkles
US5389677A (en) * 1986-12-23 1995-02-14 Tristrata Inc Method of treating wrinkles using glycalic acid
US5422370A (en) * 1986-12-23 1995-06-06 Tristrata Inc Method of using 2-hydroxypropanoic acid (lactic acid) for the treatment of wrinkles
US5470880A (en) * 1986-12-23 1995-11-28 Tristrata Inc Method of using citric acid for the treatment of wrinkles
US5550158A (en) * 1986-12-23 1996-08-27 Tristrata, Inc. Method of treating wrinkles using glucoheptonic acid
US5550154A (en) * 1986-12-23 1996-08-27 Tristrata, Inc. Method of treating wrinkles using glucuronic acid or glucuronolactone
US5554654A (en) * 1986-12-23 1996-09-10 Tristrata Inc Method for enhancing the therapeutic effect of an anti-acne agent
US5554597A (en) * 1986-12-23 1996-09-10 Tristrata Inc Compositions comprising 2-hydroxycarboxylic acids and related compounds, and methods for alleviating signs of dermatological aging
US5554651A (en) * 1986-12-23 1996-09-10 Tristrata, Inc. Method of treating wrinkles using citramalic acid
US5554652A (en) * 1986-12-23 1996-09-10 Tristrata Inc Method of treating wrinkles using alpha hydroxyacids, alpha ketoacids and a sunscreen agent
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