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Novel resorcinol derivatives for skinRelated Patent Categories: Drug, Bio-affecting And Body Treating Compositions, Bleach For Live Hair Or Skin (e.g., Peroxides, Etc.)Novel resorcinol derivatives for skin description/claimsThe Patent Description & Claims data below is from USPTO Patent Application 20060210498, Novel resorcinol derivatives for skin. Brief Patent Description - Full Patent Description - Patent Application Claims
FIELD OF THE INVENTION [0001] The invention relates to 4-substituted cyclo-alkyl methyl resorcinol derivatives, cosmetic compositions containing same, and cosmetic methods of using and making same. More specifically, the present invention relates to 4-substituted cyclo-alkyl methyl resorcinol derivatives as skin lightening actives, cosmetic compositions and methods of using same for skin lightening. BACKGROUND OF THE INVENTION [0002] Many people are concerned with the degree of pigmentation of their skin. For example, people with age spots or freckles may wish such pigmented spots to be less pronounced. Others may wish to reduce the skin darkening caused by exposure to sunlight or to lighten their natural skin color. To meet this need, many attempts have been made to develop products that reduce the pigment production in the melanocytes. However, the substances identified thus far tend to have either low efficacy or undesirable side effects, such as, for example, toxicity or skin irritation. Therefore, there is a continuing need for new skin lightening agents, with improved overall effectiveness, as well as agents that lend themselves to ease of processing in their manufacture. [0003] Resorcinol derivatives are generally known compounds and can be readily obtained, for example, by a method wherein a saturated carboxylic acid and resorcinol are condensed in the presence of zinc chloride and the resultant condensate is reduced with zinc amalgam/hydrochloric acid (Lille. J. Bitter, L A. Peiner. V, Tr. Nauch-Issled. Inst. slantsev 1969, No. 18, 127), or by a method wherein resorcinol and a corresponding alkyl alcohol are reacted in the presence of an alumina catalyst at a high temperature of from 200 to 400.degree. C. (British Patent No. 1,581,428). [0004] Resorcinol derivatives have cosmetic skin and hair benefits. Certain resorcinol derivatives, particularly 4-substituted resorcinol derivatives, are useful in cosmetic compositions for skin lightening benefits. Resorcinol derivatives are described in many publications, including U.S. Pat. No. 4,959,393; Hu et al., U.S. Pat. No. 6,132,740; Bradley, et al., U.S. Pat. No. 6,504,037; and Japanese published patent applications JP 2001-010925 and JP2000-327557. Skin lightening compounds that may be derived from coumarin are disclosed in U.S. Patent Publication No. 2004/0042983. Some of these compounds can be difficult to formulate and/or irritating to the skin. [0005] Applicants have now discovered new compounds that which deliver skin lightening benefits. The general chemical formulas and structures of these compounds are discussed in more detail herein below. Especially, 4-substituted cycloalkyl methyl resorcinol derivatives, have been found to be effective and possibly less irritating to the skin and are relatively simple to manufacture. SUMMARY OF THE INVENTION [0006] Applicants have now discovered new 4-substituted resorcinol derivatives that have skin lightening activity. Accordingly, the present invention provides novel compounds of general formula I, of which compound of general formula B is an example, cosmetic compositions and methods comprising same, particularly for skin lightening, as well as a process for producing the inventive compounds: Wherein X.sub.1 and/or X.sub.2 represents hydrogen (H), linear or branched, saturated or unsaturated C.sub.1-C.sub.12 alkyl, alkenyl, acyl groups. Preferably, X.sub.1 and/or X.sub.2 represents hydrogen (H); linear or branched, saturated or unsaturated C.sub.1-C.sub.12 alkyl or acyl groups. More preferably, X.sub.1 and/or X.sub.2 represents hydrogen. R.sub.1 represents hydrogen (H), linear or branched, cyclic or acyclic, saturated or unsaturated C.sub.1-C.sub.12 alkyl, alkenyl, cycloalkyl, or cycloalkenyl group. Preferably, R.sub.1 represents hydrogen (H) or C.sub.1 alkyl group (i.e, methyl group). More preferably, R.sub.1 represents hydrogen. n represents 0, 1. When n 0, the ring is a cyclopentyl with or without one heteroatom from O, N or S and/or with or without one double bond. When n=1, the ring is a cyclohexyl with or without one heteroatom from O, N or S and/or with or without one double bond. m=1, 2, 3, 4, 5, 6 (i.e, an integer between 1 and 6). [0007] Preferred compounds include: n=0, m=1, R.sub.1=H, alkyl, and/or alkenyl; anywhere in the ring. n=1, m=1, R.sub.1=H, alkyl, and/or alkenyl; anywhere in the ring. n=0, m=2-5, R.sub.1=H, alkyl, and/or alkenyl; any substitution pattern anywhere in the ring. n=1, m=2-6, R.sub.1.dbd.H, alkyl and/or alkenyl; any substitution pattern anywhere in the ring. [0008] Cosmetic compositions according to the present invention include: [0009] a. about 0.0001 wt. % to about 50 wt. % of a 4-substituted resorcinol derivative of the general formula B; and [0010] b. a cosmetically acceptable vehicle. [0011] The inventive compounds and compositions may be applied to the skin as part of inventive cosmetic method for skin lightening. [0012] In another aspect, the present invention relates to a process for synthesizing the novel resorcinol compounds of general formula 1, 11 and/or B1, having the following general reaction scheme: Wherein a, b, c, d represent reaction steps, reagents and conditions: [0013] (a) cycloalkylcarbonyl chloride, ZnCl.sub.2, organic solvent (e.g. dichloromethane); (b) acetic anhydride, triethylamine; (c) hydrogen, catalyst (e.g. Pd/C), acid (e.g. acetic); (d) aqueous acid hydrolysis (e.g. 3M HCl:methanol). DETAILED DESCRIPTION OF THE INVENTION [0014] The invention is concerned with new 4-substituted resorcinol derivatives for cosmetically lightening skin color, cosmetic compositions and methods emplying same, and a process for producing same. [0015] As used herein, the term "cosmetic composition" is intended to describe compositions for topical application to human skin, including leave-on and wash-off products. [0016] The term "skin" as used herein includes the skin on the face, neck, chest, back, arms, axillae, hands, legs, and scalp. [0017] Except in the examples, or where otherwise explicitly indicated, all numbers in this description indicating amounts of material or conditions of reaction, physical properties of materials and/or use are to be understood as modified by the word "about". All amounts are by weight of the composition, unless otherwise specified. Continue reading about Novel resorcinol derivatives for skin... 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