WO1996029080B1 - Poly(hydroxy acid)/polymer conjugates for skin applications - Google Patents
Poly(hydroxy acid)/polymer conjugates for skin applicationsInfo
- Publication number
- WO1996029080B1 WO1996029080B1 PCT/US1996/003177 US9603177W WO9629080B1 WO 1996029080 B1 WO1996029080 B1 WO 1996029080B1 US 9603177 W US9603177 W US 9603177W WO 9629080 B1 WO9629080 B1 WO 9629080B1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- hydroxy acid
- groups
- group
- skin
- Prior art date
Links
- 229920000642 polymer Polymers 0.000 title claims abstract 9
- 210000003491 Skin Anatomy 0.000 title claims abstract 7
- -1 Poly(hydroxy acid) Polymers 0.000 title claims abstract 4
- 239000000203 mixture Substances 0.000 claims abstract 23
- 239000002537 cosmetic Substances 0.000 claims abstract 3
- 125000000524 functional group Chemical group 0.000 claims abstract 2
- 230000000699 topical Effects 0.000 claims abstract 2
- 150000001261 hydroxy acids Chemical class 0.000 claims 8
- 229920001577 copolymer Polymers 0.000 claims 7
- 239000000969 carrier Substances 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 239000000499 gel Substances 0.000 claims 2
- 230000000475 sunscreen Effects 0.000 claims 2
- 239000000516 sunscreening agent Substances 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- CWSZBVAUYPTXTG-UHFFFAOYSA-N 5-[6-[[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxymethyl]-3,4-dihydroxy-5-[4-hydroxy-3-(2-hydroxyethoxy)-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxyoxan-2-yl]oxy-6-(hydroxymethyl)-2-methyloxane-3,4-diol Chemical compound O1C(CO)C(OC)C(O)C(O)C1OCC1C(OC2C(C(O)C(OC)C(CO)O2)OCCO)C(O)C(O)C(OC2C(OC(C)C(O)C2O)CO)O1 CWSZBVAUYPTXTG-UHFFFAOYSA-N 0.000 claims 1
- 229940035676 ANALGESICS Drugs 0.000 claims 1
- 229940035674 ANESTHETICS Drugs 0.000 claims 1
- 229940064005 Antibiotic throat preparations Drugs 0.000 claims 1
- 229940083879 Antibiotics FOR TREATMENT OF HEMORRHOIDS AND ANAL FISSURES FOR TOPICAL USE Drugs 0.000 claims 1
- 229940042052 Antibiotics for systemic use Drugs 0.000 claims 1
- 229940042786 Antitubercular Antibiotics Drugs 0.000 claims 1
- 208000002399 Aphthous Stomatitis Diseases 0.000 claims 1
- 206010012444 Dermatitis diaper Diseases 0.000 claims 1
- 229920002307 Dextran Polymers 0.000 claims 1
- 208000003105 Diaper Rash Diseases 0.000 claims 1
- 229940093922 Gynecological Antibiotics Drugs 0.000 claims 1
- 241000238631 Hexapoda Species 0.000 claims 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 claims 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Natural products OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 239000004372 Polyvinyl alcohol Substances 0.000 claims 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims 1
- 229920002472 Starch Polymers 0.000 claims 1
- 229940024982 Topical Antifungal Antibiotics Drugs 0.000 claims 1
- 229940029983 VITAMINS Drugs 0.000 claims 1
- 229940021016 Vitamin IV solution additives Drugs 0.000 claims 1
- 208000000260 Warts Diseases 0.000 claims 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims 1
- 239000000443 aerosol Substances 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 230000003444 anaesthetic Effects 0.000 claims 1
- 230000000202 analgesic Effects 0.000 claims 1
- 239000000730 antalgic agent Substances 0.000 claims 1
- 239000003242 anti bacterial agent Substances 0.000 claims 1
- 230000000843 anti-fungal Effects 0.000 claims 1
- 230000000845 anti-microbial Effects 0.000 claims 1
- 230000001166 anti-perspirant Effects 0.000 claims 1
- 230000001139 anti-pruritic Effects 0.000 claims 1
- 229940121375 antifungals Drugs 0.000 claims 1
- 239000004599 antimicrobial Substances 0.000 claims 1
- 239000003213 antiperspirant Substances 0.000 claims 1
- 239000003908 antipruritic agent Substances 0.000 claims 1
- 230000003115 biocidal Effects 0.000 claims 1
- 229920001400 block copolymer Polymers 0.000 claims 1
- 229920005605 branched copolymer Polymers 0.000 claims 1
- 150000001720 carbohydrates Chemical class 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- 239000006071 cream Substances 0.000 claims 1
- 150000001991 dicarboxylic acids Chemical class 0.000 claims 1
- 239000000975 dye Substances 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000000816 ethylene group Chemical class [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 239000006260 foam Substances 0.000 claims 1
- 239000003205 fragrance Substances 0.000 claims 1
- 239000003193 general anesthetic agent Substances 0.000 claims 1
- 229920002674 hyaluronan Polymers 0.000 claims 1
- 229960003160 hyaluronic acid Drugs 0.000 claims 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 claims 1
- 239000000077 insect repellent Substances 0.000 claims 1
- 229940079866 intestinal antibiotics Drugs 0.000 claims 1
- 239000006210 lotion Substances 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000002773 nucleotide Substances 0.000 claims 1
- 125000003729 nucleotide group Chemical group 0.000 claims 1
- 239000002674 ointment Substances 0.000 claims 1
- 229940005935 ophthalmologic Antibiotics Drugs 0.000 claims 1
- 150000002917 oxazolidines Chemical class 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims 1
- 229920001888 polyacrylic acid Polymers 0.000 claims 1
- 239000004584 polyacrylic acid Substances 0.000 claims 1
- 229920002451 polyvinyl alcohol Polymers 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 150000004040 pyrrolidinones Chemical class 0.000 claims 1
- 150000004508 retinoic acid derivatives Chemical class 0.000 claims 1
- 201000010153 skin papilloma Diseases 0.000 claims 1
- MAKUBRYLFHZREJ-JWBQXVCJSA-M sodium;(2S,3S,4R,5R,6R)-3-[(2S,3R,5S,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5,6-trihydroxyoxane-2-carboxylate Chemical compound [Na+].CC(=O)N[C@@H]1C[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](C([O-])=O)O[C@@H](O)[C@H](O)[C@H]1O MAKUBRYLFHZREJ-JWBQXVCJSA-M 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 239000007921 spray Substances 0.000 claims 1
- 235000019698 starch Nutrition 0.000 claims 1
- 239000008107 starch Substances 0.000 claims 1
- 230000001225 therapeutic Effects 0.000 claims 1
- 239000011732 tocopherol Substances 0.000 claims 1
- 125000002640 tocopherol group Chemical group 0.000 claims 1
- 229930003799 tocopherols Natural products 0.000 claims 1
- 235000019149 tocopherols Nutrition 0.000 claims 1
- 150000003628 tricarboxylic acids Chemical class 0.000 claims 1
- XTXRWKRVRITETP-UHFFFAOYSA-N vinyl acetate Chemical class CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 239000011782 vitamin Substances 0.000 claims 1
- 235000013343 vitamin Nutrition 0.000 claims 1
- 229930003231 vitamins Natural products 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000003241 dermatological agent Substances 0.000 abstract 1
Abstract
A method for alleviating the symptoms of a cosmetic or dermatologic skin condition is described. An effective amount of a poly(hydroxy acid)/polymer conjugate in a pharmaceutically or cosmetically acceptable vehicle is provided. Topical compositions of the conjugates with another cosmetic or dermatological agent, and compounds of the conjugates having attached physiologically active functional groups, are also provided.
Claims
1. A composition for treatment of the skin, comprising an effective amount of a composition comprising one or more hydroxy acid copolymers in combination with a suitable carrier for topical application to skin in need of treatment, wherein the hydroxy acid copolymer comprises polymerized hydroxy acids having cosmetic or therapeutic activity covalently joined to a polymer backbone, the hydroxy acid copolymer having the formula PaHb, wherein P is a polymer backbone block consisting predominantly of non-hydroxy acid subunits, H is a polymer block consisting predominantly of hydroxy acid subunits, a is the number of P blocks, b is the number of H blocks, a and b are integers of at least one, and the copolymer is either a linear, brush or branched copolymer.
2. The composition of claim 1 wherein the sum of a and b is less than about 100.
3. The composition of claim 1 wherein the linkages between the hydroxy acid subunits and the polymer backbone are degradable under the conditions present on the skin in the carrier.
4. The composition of claim 1 wherein the hydroxy acid subunits have a molecular weight of 600 or less.
5. The composition of claim 1 wherein the hydroxy acid is selected from the group consisting of glycolic, lactic, hydroxybutyric, hydroxypentanoic, hydroxy hexanoic, carbonic, glyceric and salicylic.
6. The composition of claim 1 wherein the number of hydroxy acid subunits in the hydroxy acid blocks is between one and 100.
7. The composition of claim 1 wherein the backbone polymer comprises subunits selected from the group consisting of alkylene oxides, (meth)acrylates, ethylenes, vinyl alcohols, vinyl acetates, pyrrolidones, oxazolidines, saccharides, amino acids, nucleotides, and phenols.
8. The composition of claim 1 where the backbone polymer is selected from me group consisting of polyalkylene oxide, polyvinyl alcohol, dextran, starch, hyaluronic acid, hydroxyethylcellulose, and polyacrylic acid.
9. The composition of claiml wherein the backbone polymer blocks have a molecular weight between 200 and 100,000.
10. The composition of claim 10 wherein the copolymer further comprises covalently attached groups which are biologically functional on the skin.
11. The composition of claim 41 wherein the biologically functional groups are selected from the group consisting of sunscreens, vitamins, tocopherols, retinoic acid derivatives, fragrances, antimicrobials, wart removers, bleaches, and dyes.
12. The composition of claim 1 wherein the copolymer further comprises groups capable of being polymerized to crosslink the block copolymers.
13. The composition of claim 1 wherein the polymerizable groups are ethylenically unsamrated.
14. The composition of claim 13 wherein the groups are selected from the group consisting of unsamrated monocarboxylic groups, unsamrated dicarboxylic acids, unsamrated tricarboxylic acids, allyl groups, vinyl groups, and ester, ether, and amides containing 12 or fewer carbons.
15. The composition of claim 1 wherein the composition further comprises materials selected from the group consisting of antibiotics, antifungals, pediculicides, antiperspirants, antipruritics, analgesics, anesthetics, blister treatments, canker sore treatments, insect bite treatments, diaper rash treatments, insect repellents, and sunscreens.
16. The composition of claim 1 wherein the carrier is selected from the group consisting of powders, solutions, gels, creams, ointments, sticks, emulsions, foams, aerosols, sprays, and lotions.
17. The composition of claim 1 wherein the composition is substantially anhydrous.
18. The composition of claim 12, wherein the polymerizable hydroxyacid copolymers are polymerized on the skin to form a gel coating.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8528448A JPH11502228A (en) | 1995-03-09 | 1996-03-08 | Poly (hydroxy acid) / polymer conjugates for application to the skin |
| EP96910388A EP0814815A4 (en) | 1995-03-09 | 1996-03-08 | Poly(hydroxy acid)/polymer conjugates for skin applications |
| CA002214884A CA2214884C (en) | 1995-03-09 | 1996-03-08 | Poly(hydroxy acid)/polymer conjugates for skin applications |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/401,931 US5618850A (en) | 1995-03-09 | 1995-03-09 | Hydroxy-acid cosmetics |
| US401,931 | 1995-03-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO1996029080A1 WO1996029080A1 (en) | 1996-09-26 |
| WO1996029080B1 true WO1996029080B1 (en) | 1996-11-21 |
Family
ID=23589844
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1996/003177 WO1996029080A1 (en) | 1995-03-09 | 1996-03-08 | Poly(hydroxy acid)/polymer conjugates for skin applications |
Country Status (5)
| Country | Link |
|---|---|
| US (3) | US5618850A (en) |
| EP (1) | EP0814815A4 (en) |
| JP (1) | JPH11502228A (en) |
| CA (1) | CA2214884C (en) |
| WO (1) | WO1996029080A1 (en) |
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