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(12) Patent Application Publication (10) Pub. No.: US 2008/0025929 A1 Burton Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2008/0025929 A1 Burton Et Al US 20080025929A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2008/0025929 A1 Burton et al. (43) Pub. Date: Jan. 31, 2008 (54) TOPCAL FORMULATIONS FOR THE Related U.S. Application Data TREATMENT OF SIKIN CONDITIONS (60) Provisional application No. 60/546,043, filed on Feb. (75) Inventors: Graham W. Burton, Ottawa (CA); 19, 2004. Janusz Daroszweski, Ottawa (CA) Correspondence Address: Publication Classification CLARK & ELBNG LLP 101 FEDERAL STREET (51) Int. Cl. A6IR 8/00 (2006.01) BOSTON, MA 02110 A6IP 7/8 (2006.01) (73) Assignee: Chemaphor, Inc., Ottawa (CA) (21) Appl. No.: 10/589,700 (52) U.S. Cl. ......................................................... 424/59 (22) PCT Fed: Feb. 17, 2005 (57) ABSTRACT (86) PCT No.: PCT/BOS/O1369 The invention features compositions for topical administra tion of an oxidatively transformed carotenoid or 2-methyl S 371 (c)(1), 6-oxo-2,4-heptadienal and methods of treating skin condi (2), (4) Date: Aug. 10, 2007 tions therewith. US 2008/0025929 A1 Jan. 31, 2008 TOPCAL FORMULATIONS FOR THE acid esters, polyethylene glycol alkyl ethers, Sugar esters, TREATMENT OF SIKIN CONDITIONS polyethylene glycol alkyl phenols, polyoxyethylene-polyox ypropylene block copolymers, Sorbitan fatty acid esters, BACKGROUND OF THE INVENTION lower alcohol fatty acid esters, ionic Surfactants, tocopherol esters, and sterol esters. 0001. The invention relates to the formulation of caro 0010. In yet another embodiment of the above aspects, tenoid oxidation products and their use in the treatment of the composition further includes a UV light blocker, a skin conditions. corticosteroid, an antihistamine, a retinoid, 5-fluorouracil, 0002 Carotenoids are naturally occurring substances epinephrine, anthralin, calcipotriene, methotrexate, maspro which contain extensively conjugated polyene chains, which col, trimethaxate gluconate, cyclosporin, paclitaxel, 5-amino give rise to their many varied and brilliant colors. Caro levulinic acid, bergasol, benzoporphyrin, hydroxy acid, ret tenoids are reactive towards molecular oxygen (O). For inoic acid, diphency prone, aldara, imiquimod, gamma-lino example, beta-carotene has been shown to have antioxidant lenic acid, chloroxine, coal tar, ketoconazole, pyrithione, properties at the low oxygen pressures found in tissues and salicylic acid, Zinc salts, selenium sulfide, piroctone ola pro-oxidant properties at higher pressures (Burton and mine, sulphur, or mixtures thereof. Exemplary UV light Ingold, Science, 224:569 (1984)). The oxidation of caro blockers include those selected from amino benzoic acids, tenoids with molecular oxygen has been shown to produce benzophenones, camphors, cinnamates, dibenzoyl meth a mixture of polymeric material and many low molecular anes, salicylates, metal oxides, and mixtures thereof. Exem weight products, including 2-methyl-6-oxo-2,4-heptadienal plary antihistamines include mepyramine, diphenhy (U.S. Pat. No. 5,475,006 and PCT Publication No. dramine, and antazoline. Exemplary corticosteroids include 96/05160). alclometasone dipropionate, amcinonide, betamethasone 0003) A variety of biological activities have been attrib dipropionate, betamethasone Valerate, clobetasol propi uted to carotenoids. For example, carotenoids have been onate, desonide, desoximetaSone, dexamethasone, diflo shown to retard the development of some experimentally rasone diacetate, flucinolone acetonide, flumethasone, fluo induced animal tumors (N. I. Krinsky, Annu. Rev. Nutr., 13, cinonide, flurandrenolide, halcinonide, halobetasol 561-587 (1993); Matthews-Roth, Curr. Top. Nutr. Dis., propionate, hydrocortisone butyrate, hydrocortisone Valer 22:17-38 (1989)). Furthermore, epidemiological evidence ate, methylprednisolone, mometasone furoate, prednisolone, indicates that carotenoid intake correlates inversely with the and triamcinolone acetonide. incidence of some types of cancer (Peto et al. Nature, 0011. In still another embodiment of the above aspects, 290:201-208 (1981)). Beta-carotene and phytoene have been the composition is formulated as a cream, lotion, spray, used in combination with UV light therapy to treat psoriasis Stick, ointment, soap, body wash, shampoo, or mask. (U.S. Pat. No. 4,642.318). 0012. In a third aspect, the invention features a method of 0004. In contrast, little is known about the biological treating a skin condition in a mammal by applying oxida activity of the oxidation products of carotenoids or their use tively transformed carotenoid to the skin of the mammal in for the treatment of skin conditions. an amount Sufficient to treat the skin condition. 0005. There is a need for new compositions and methods 0013. In a fourth aspect, the invention features a method for the treatment of skin conditions, such as photoaging, of treating a skin condition in a mammal by applying dandruff, psoriasis, eczema, keloids, keratosis, and warts, 2-methyl-6-oxo-2,4-heptadienal to the skin of the mammal among others. in an amount Sufficient to treat the skin condition. 0014. In one embodiment of the above methods, the skin SUMMARY OF THE INVENTION condition is dandruff. For the treatment of dandruff, the 0006. In a first aspect, the invention features a composi method can also include the administration of chloroxine, tion formulated for topical administration including from coal tar, ketoconazole, pyrithione, Salicylic acid, Zinc salts, 0.0001% to 5% (w/w) oxidatively transformed carotenoid. Selenium sulfide, piroctone olamine, Sulphur, or combina 0007. In a second aspect, the invention features a com tion thereof to the mammal. position formulated for topical administration including 0015. In another embodiment of the above methods, the from 0.0001% to 5% (w/w) 2-methyl-6-oxo-2,4-heptadi skin condition is psoriasis. For the treatment of psoriasis, the enal. method can also include the administration of a corticoster 0008. In one embodiment of the above aspects, the com oid, 5-fluorouracil, epinephrine, anthralin, calcipotriene, position further includes an antioxidant. The antioxidant can methotrexate, masprocol, trimethaxate gluconate, retinoids, be selected from thiols, sulphoximines, metal chelators, fatty cyclosporin, paclitaxel, 5-amino levulinic acid, bergasol, acids, vitamins, phenols, stilbenes, uric acid, mannose, sele benzoporphyrin, or combination thereof to the mammal. nium and propyl gallate. Desirably, the antioxidant is vita 0016. In yet another embodiment of the above methods, min E. the skin condition is photoaging. For the treatment of 0009. In another embodiment of the above aspects, the photoaging, the method can also include the administration composition further includes one or more solubilizing of a UV light blocker, hydroxy acid, retinoic acid, gamma excipients wherein the class of excipient is selected from the linolenic acid, or combination thereof to the mammal. group consisting of polyethoxylated fatty acids, PEG-fatty 0017. In still another embodiment of the above methods, acid diesters, PEG-fatty acid mono-ester and di-ester mix the skin condition is eczema. For the treatment of eczema, tures, polyethylene glycol glycerol fatty acid esters, alcohol the method can also include the administration of an anti oil transesterification products, polyglycerized fatty acids, histamine, corticosteroid, or combination thereof to the propylene glycol fatty acid esters, mixtures of propylene mammal. Corticosteroids useful for the treatment of eczema glycol esters-glycerol esters, mono- and diglycerides, sterol using the methods described herein include alclometasone and sterol derivatives, polyethylene glycol sorbitan fatty dipropionate, amcinonide, betamethasone dipropionate, US 2008/0025929 A1 Jan. 31, 2008 betamethasone Valerate, clobetasol propionate, desonide, carboxylic carotenoids, Such as apocarotenoic acid, B-apo desoximetasone, dexamethasone, diflorasone diacetate, flu 8-carotenoic acid, azafrin, bixin, carboxylcarotenes, croce cinolone acetonide, flumethasone, fluocinonide, flurandre tin, diapocarotenoicacid, neurosporaxanthin, norbixin, and nolide, halcinonide, halobetasol propionate, hydrocortisone lycopenoicacid. butyrate, hydrocortisone Valerate, methylprednisolone, 0025. As used herein “oxidatively transformed caro mometasone furoate, prednisolone, and triamcinolone tenoid refers to a carotenoid which has been reacted with up acetonide. Antihistamines useful for the treatment of eczema to 6 to 8 molar equivalents of oxygen resulting in a mixture using the methods described herein include mepyramine, of very low molecular weight oxidative cleavage products diphenhydramine, and antazoline. and a large proportion of oligomers and polymers. The 0.018. In still another embodiment of the above methods, resulting reaction produces a mixture that includes molecu the skin condition is selected from warts, keloids, and lar species having molecular weights ranging from about keratosis. 100 to 8,000 Daltons. The polymeric material is believed to 0019. In a fifth aspect, the invention features a container beformed by the many possible chemical recombinations of including a composition of the invention and packaged the various oxidative fragments that are formed. Methods of under an atmosphere purged of oxygen gas. making the oxidatively transformed carotenoid are 0020. In a sixth aspect, the invention features a compo described in U.S. Pat. No. 5,475,006 and U.S. Ser. No. sition comprising from 0.001% to 3% by weight antioxidant 08/527,039, filed Sep. 12, 1995, each of which are incor and oxidatively transformed
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