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III III USOO5520905A United States Patent (19) 11 Patent Number: 5,520,905 Uhlmann Et Al

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III III USOO5520905A United States Patent (19) 11 Patent Number: 5,520,905 Uhlmann Et Al III III USOO5520905A United States Patent (19) 11 Patent Number: 5,520,905 Uhlmann et al. 45 Date of Patent: May 28, 1996 54 COSMETIC OR DERMATOLOGICAL 56) References Cited PREPARATION COMPRISING DELTA-AMNOLEVULINIC ACID CONTENT U.S. PATENT DOCUMENTS ASAN ACTIVE INGREDIENT 4,568,665 2/1986 Mitchell ...................................... 54/9 5,211,938 5/1993 Kennedy et al. ........................ 424/7. (75) Inventors: Beate Uhlmann, Tobias Mann, both of Hamburg; Heinrich Gers-Barlag, FOREIGN PATENT DOCUMENTS Kummerfeld, Gerhard Sauermann, 202778 11/1986 European Pat. Off.. Wiemersdorf, all of Germany 2728242 1/1979 Germany. 9/01727 2/1991 WIPO 73) Assignee: Beiersdorf Aktiengesellschaft, Hamburg, Germany 92fO9635 6/1994 WIPO. Primary Examiner—C. Warren Ivy 21 Appl. No.: 260,843 Assistant Examiner-Evelyn Huang Attorney, Agent, or Firm-Sprung Horn Kramer & Woods 22 Filed: Jun. 16, 1994 (30) Foreign Application Priority Data 57 ABSTRACT Jun. 24, 1993 DE Germany .......................... 432O 871. A cosmetic or dermatological preparation comprising 8-ami nolevulinic acid as an active ingredient. (51) Int. Cl. ................. A61K 7/42 (52) U.S. Cl. ................................ 424/59; 424/60; 514/561 58) Field of Search ......................... 424/59, 60, 514/561 20 Claims, No Drawings 5,520,905 2 COSMETIC ORDERMATOLOGICAL difficult to incorporate them satisfactorily into such formu PREPARATION COMPRSNG lations. DELTA-AMNOLEVULNCACD CONTENT It has already been suggested that Vitamin E, a substance ASAN ACTIVE INGREDIENT known to have an anti-oxidant action, should be used in light-protection formulations, but here too, the results have been far less satisfactory than expected. DESCRIPTION An object of the present invention is therefore to provide The invention in question concerns cosmetic and derma cosmetic and dermatological substances and preparations tological preparations. The invention mainly concerns containing active substances which would guarantee reliable preparations which alleviate the adverse effects caused by 10 protection from ultra-violet radiation and/or prevent the exposure to light, particularly exposure to ultra-violet light adverse effects caused by exposure to UV, alleviate existing and preparations which forestall such damage i.e. act as a damage or cure it completely. preventative against such damage when applied before In particular it is an object of the present invention to exposure to light, particularly exposure to ultra-violet light. provide cosmetic and dermatological substances and prepa The harmful effects of the Sun's ultra-violet radiation on 15 rations containing active substances which would counteract the skin is generally well-known. While rays with a wave the aging of the skin which is caused or exacerbated by length of less than 290 nm (the so-called UVC range) are exposure to UV. absorbed by the ozone layer in the earth's atmosphere, rays Finally it is an object of the present invention to provide in the range between 290 nm and 320 nm, the so-called UVB cosmetic and dermatological substances and preparations range, cause erythema, a simple sun-burn or even light to 20 containing active substances which would counteract acne severe burning. aestivalis. The erythema effect is at a maximum with sunlight in a A person skilled in the art could not predict-and this is the premise for the solution to these problems-that cos narrower range around 308 nm. metic ordermatological preparations comprising 8-aminole A number of compounds are known to protect against 25 UVB radiation. These are derivatives of 3-benzylidene cam vulinic acid as an active ingredient would remedy the phor, 4-aminobenzoic acid, cinnamic acid, salicylic acid, problems with the current state of the art. benzophenon and 2-phenylbenzimidazol. 8-aminolevulinic acid (also called 6-ALA, 5-amino-4- Filter substances for radiation in the range between 320 oxopentanoic acid, 8-amino-Y-keto-valeric acid) has the nm and approx. 400 nm, the co-called UVA range, are also 30 following structure: important as this radiation can also cause adverse effects. UVA radiation damages the elastic and collagenic fibres of the connective tissue which causes premature aging of the HOOC-CH2-CH-C-CH-NH2 skin and has been found to cause a number of photo-toxic and photo-allergenic reactions. Furthermore, the damaging 35 8-aminolevulinic acid is an intermediate product of the effect of UVB radiation can be exacerbated by UVA radia biosynthesis of porphyrin and is formed during the citric tion. acid cycle. Certain derivatives of dibenzoylmethane are predomi Heretofore, it was not known how to incorporate 8-ami nantly used to protect against rays in the UVA range. nolevulinic acid into cosmetic or dermatological formula However, UV radiation can also cause photo-chemical reac 40 tions. tions where the photo-chemical reaction products attack the B. Ortel, A. Tanew and H. Honigsmann (J. Photochem. skin's metabolism. Photobiol. B: Biol., 17 (1993), pp. 273-278) explain that Photo-chemical reaction products of this type are gener administering 8-aminolevulinic acid externally to tumour ally radical compounds, e.g. hydroxy radicals. Undefined cells induces the biosynthesis of porphyrins. The increased radical photo products, which occur in the skin itself may 45 photosensitivity caused by the increase in porphyrin con also cause uncontrolled reactions on account of their high centration facilitates the killing of these tumour cells by reactivity. Furthermore, UV radiation can also cause the means of radiation with light of the appropriate wave-length. appearance of singlet oxygen, a non-radical activated State However, a person skilled in the art and with knowledge of the oxygen molecule, in addition to short-lived epoxides of this document could not have arrived at the invention etc. For example, compared with the triplet oxygen gener 50 being submitted in this case. ally present (radical ground state), singlet oxygen is char Particularly valuable preparations are also obtained by acterised by an increase in reactivity, although activated, combining 8-aminolevulinic acid with antioxidants. reactive (radical) triplet states of the oxygen molecule also The antioxidants according to the invention may usefully eXSt. be selected from the standard group of cosmetic and der 55 matological antioxidants, particularly the group consisting Antioxidants and/or radical inhibitors can be incorporated of tocopherols and their derivatives, particularly O-toco into cosmetic and/or dermatological formulations to prevent pherol and/or O-tocopheryl esters, especially O-tocophery these reactions. lacetate, in addition to sesame oil, bile acid derivatives such It is known that certain types of photodermatosis can be as methyl, ethyl, propyl, amyl, butyl and lauric gallate, the triggered by certain emulsifiers and also by various types of 60 coniferylbenzoate of benzoin, nordihydroguaiacinic acid, fat with simultaneous exposure to sunlight. These types of nordihydroguaiaretic acid, butylhydroxyanisole, butylhy photodermatosis are called acne aestivalis. droxytoluol, ascorbic acid, citric acid, phosphoric acid, The compounds used as light protection agents in cos lecithin, trihydroxybutyrophenon, carotenes, vitamin A and metic and dermatological light protection formulations, its derivatives, particularly retinylpalmitate, ascorbic acid, some of which are mentioned above, are notable for their 65 ascorbylpalmitate, dilaurylthiodipropionate, distearylthio satisfactory light protection properties. However, a disad dipropionate, monoisopropylcitrate, thiodipropionic acid vantage of these products is that sometimes it has been and EDTA and EDTA derivatives. 5,520,905 3 4 It is preferable to select the antioxidants according to the 8-aminolevulinic acid as an active ingredient and/or the invention from the group of tocopherols and their deriva combinations according to the invention which consist of tives. 8-aminolevulinic acids and at least one other substance Tocopherols, also called vitamin E, are derived from the selected from the antioxidant group, particularly tocopherols parent substance tocol ((2-methyl-2-(4,8,12-trimethyltride 5 and tocopherylester, cyl)-chroman-Ö-ol) and have the following structures: would have sufficient stability for the application R KO CH2 N / N / N ( H2 CH: ths CH3 C. C C yetH2 yetCH etectCH2 CH yetCH2 yetCH R /N C / N O /|\ CH2 CH2 CH2 CH2 CH2 CH2 CH3 CH3 R" Here K represents either H or an acyl group independently would lead to skin-compatible products of one another, R, R and R" mean H or a methyl group, e.g.: 20 would not attack the skin's own microorganism flora Ra Ras R"; K= H : Tocol would counteract light-induced aging of the skin R = R = R" = Methyl, K = H : O-tocopherol would counteract acne aestivalis. R=R"s Methyl, R's K = H : B-tocopherol acetate In particular, no one could have predicted that 8-aminole R = R = R" = methyl, Kc -C-CH3: o-Tocopherolacetate vulinic acid and/or cosmetic or dermatological preparations O 25 comprising 8-aminolevulinic acid as an active ingredient and/or the combinations according to the invention which and other variations. In these esters, K represents the acyl consist of 8-aminolevulinic acids and at least one other group as follows: substance selected from the antioxidant group, particularly tocopherols and tocopherylester, would be notable for a 30 marked delayed action. Furthermore, the 8-aminolevulinic acid and/or cosmetic or dermatological preparations comprising 6-aminolevulinic whereby
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