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(19) United States (12) Patent Application Publication (10) Pub US 20140212362A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2014/0212362 A1 Pippin (43) Pub. Date: J 11]. 31, 2014 (54) COMPOSITION AND METHOD FOR (60) Provisional application No. 61/540,953, ?led on Sep. TREATMENT OF SYMPTOMS ASSOCIATED 29, 2011. WITH VARIOUS SKIN CONDITIONS _ _ _ _ Publication Classi?cation (71) Applicant: THERACEUTIX, LLC, Exton, PA A61KIIlt. 31/4164 (2006.01) (72) Inventor: Douglas A. Pippin, Chester Springs, PA A61K 45/06 (200601) (Us) C 07D 233/64 (2006.01) (52) US. Cl. - _ CPC ........ .. A61K31/4164 (2013.01); C07D 233/64 (73) Ass1gnee. LEISERACEUTIX, LLC, Exton, PA (201301); A61K 45/06 (201301) USPC ............................ .. 424/59; 514/400; 514/171 (21) Appl. No.: 14/230,494 (57) ABSTRACT Compositions containing imidazole-based compounds, and (22) Filed; Mar, 31, 2014 optionally, colloidal oatmeal, for the treatment, prevention, and management of symptoms, conditions, diseases, and dis Related US. Application Data orders of the skin. Also, methods for the' treatment, preven tion, and management of symptoms, condltlons, d1seases, and (63) Continuation of application No. PCT/US2012/ disorders of the skin using compositions containing imida 057431, ?led on Sep. 27, 2012. zole-based compounds, and optionally, colloidal oatmeal. US 2014/0212362 A1 Jul. 31, 2014 COMPOSITION AND METHOD FOR [0011] Another aspect of the invention relates to a method TREATMENT OF SYMPTOMS ASSOCIATED of suppressing a dermatologic immune response in a patient WITH VARIOUS SKIN CONDITIONS in need thereof, comprising topically administering an effec tive composition comprising the imidazole compound con CROSS-REFERENCE TO RELATED tained in a dermatologically acceptable carrier. APPLICATIONS [0012] Another aspect of the invention relates to a compo [0001] This application is a continuation claiming bene?t sition comprising an imidazole compound of the formula: under 35 U.S.C. §§120 and 365(c) of PCT International Application No. PCT/US2012/057431, ?led Sep. 27, 2012, and claiming bene?t under 35 U.S.C. §119(e) of US. Provi R7 R8 sional Application No. 61/540,953, ?led Sep. 29, 2011. The HO disclosures of PCT International Application No. PCT/ R9 US2012/057431 and US. Provisional Application No. 61/540,953 are incorporated herein by reference in their — R6 entirety. HN / N FIELD OF THE INVENTION [0002] This invention relates to compositions containing R1 0 imidazole-based compounds, and optionally, colloidal oat meal, and to methods of their use for the treatment, preven tion, and management of symptoms, conditions, diseases, and wherein: disorders of the skin. [0013] R1 is hydrogen, alkyl or aryl; [0014] R6 is OR10 or OC(O)R10; SUMMARY OF THE INVENTION [0015] R7 is ORll or OC(O)R11; [0003] One aspect of the invention relates to a method of [0016] R8 is OR12 or OC(O)R12; and treating, managing, or preventing a dermatological or skin [0017] R9 is hydrogen, CHzOR13 or CHZOC(O)R13; and condition, which comprises topically administering to a sub each of R10, R11, R12 and R13 is independently hydrogen or ject in need thereof a therapeutically or prophylactically lower alkyl, effective composition comprising an imidazole compound of and pharmaceutically, dermatologically, or cosmetically the formula: acceptable salts thereof. [0018] Another aspect of the invention relates to composi tions containing combinations of imidazole-based com R7 R8 pounds and, optionally, colloidal oatmeal, and to methods of HO their use for the treatment, prevention, and management of in?ammatory or immune-mediated symptoms, conditions, R9 diseases, and disorders of the skin. — R6 [0019] Another aspect of the invention relates to combina tions of imidazole-based compounds and, optionally, colloi HN / N dal oatmeal, and to methods of their use for the treatment, prevention, and management of various skin symptoms, con ditions, diseases, and disorders. R1 0 [0020] Another aspect of the invention relates to combina tions of imidazole-based compounds and colloidal oatmeal wherein: and to methods of their use for the treatment, prevention, and [0004] R1 is hydrogen, alkyl or aryl; management of atopic dermatitis, seborrheic dermatitis, con [0005] R6 is ORlo or OC(O)R10; tact dermatitis, cutaneous sarcoidosis, drug induced photo [0006] R7 is ORll or OC(O)R11; sensitivity, ?xed drug eruptions, id reactions, bullous skin [0007] R8 is ORl2 or OC(O)R12; and diseases, discoid lupus erythematosus, subacute cutaneous [0008] R9 is hydrogen, CHzOR13 or CHZOC(O)R13; and lupus, alopecia areata, sea bathers eruptions, psoriasis, each of R10, R11, R12 and R13 is independently hydrogen or dyshidrotic eczema, and pompholyx. lower alkyl, [0021] Another aspect of the invention relates to composi and pharmaceutically, dermatologically, or cosmetically tions and methods for treating in?ammatory and/or immune acceptable salts thereof. mediated dermatoses with imidazole-based compounds and [0009] Another aspect of the invention relates to a method combinations of imidazole-based compounds and colloidal of caring for skin, which comprises topically administering to oatmeal. the skin of a subj ect in need thereof a composition comprising [0022] Another aspect of the invention relates to care, the imidazole compound in an amount and for a time suf? supplement, and pharmaceutical compositions containing cient to effect a change in the skin. imidazole-based compounds, colloidal oatmeal, and other [0010] Another aspect of the invention relates to a method ingredients used to treat disorders of the skin, as well as to of delivering or depositing a bene?t agent onto skin, which compositions suitable for use in personal care applications, comprises topically administering to the skin of a subject a and in particular skin care compositions, which effectively composition comprising the imidazole compound contained deliver and/ or deposit various bene?t agents into and onto the in a dennatologically acceptable carrier. skin. US 2014/0212362 A1 Jul. 31, 2014 [0023] Another aspect of the invention relates to composi which reduces the severity of the disease or disorder, or tions and methods for treating contact dermatitis. retards or slows the progression of the disease or disorder. [0024] These and further aspects of the claimed invention [0031] Unless otherwise indicated, the term “include” has will now be explained in more detail. the same meaning as “include, but are not limited to,” and the term “includes” has the same meaning as “includes, but is not DETAILED DESCRIPTION OF THE INVENTION limited to.” Similarly, the term “such as” has the same mean ing as the term “such as, but not limited to.” De?nitions [0032] Unless otherwise indicated, one or more adjectives [0025] Unless otherwise indicated, the term “alkyl” means immediately preceding a series of nouns is to be construed as a straight chain, branched and/ or cyclic (“cycloalkyl”) hydro applying to each of the nouns. For example, the phrase carbon having from 1 to 20 (e.g., l to 10 or 1 to 4) carbon “optionally substituted A, B, or C” has the same meaning as atoms. Alkyl moieties having from 1 to 4 carbons are referred “optionally substituted A, optionally substituted B, or option to as “lower alkyl.” Examples of alkyl groups include, but are ally substituted C.” not limited to, methyl, ethyl, propyl, isopropyl, n-butyl, t-bu [0033] It should be noted that a chemical moiety that forms tyl, isobutyl, pentyl, hexyl, isohexyl, heptyl, 4,4-dimethyl part of a larger compound may be described herein using a pentyl, octyl, 2,2,4-trimethylpentyl, nonyl, decyl, undecyl name commonly accorded it when it exists as a single mol and dodecyl. Cycloalkyl moieties may be monocyclic or mul ecule or a name commonly accorded its radical. ticyclic, and examples include cyclopropyl, cyclobutyl, [0034] It should also be noted that if the stereochemistry of cyclopentyl, cyclohexyl, and adamantyl. Additional a structure or a portion of a structure is not indicated with, for examples of alkyl moieties have linear, branched and/or example, bold or dashed lines, the structure or the portion of cyclic portions (e. g., l-ethyl-4-methyl-cyclohexyl). The term the structure is to be interpreted as encompassing all stereoi “alkyl” includes saturated hydrocarbons as well as alkenyl somers of it. Moreover, any atom shown in a drawing with and alkynyl moieties. unsatis?ed valences is assumed to be attached to enough [0026] Unless otherwise indicated, the terms “manage,” hydrogen atoms to satisfy the valences. “managing” and “management” encompass preventing the [0035] As used herein, the term “bene?t agent” includes recurrence of the speci?ed disease or disorder in a patient who any active ingredient that is to be delivered into and/or onto has already suffered from the disease or disorder, and/or the skin at a desired location, such as a cosmetic, care or lengthening the time that a patient who has suffered from the pharmaceutical agent, and that is capable of providing a cos disease or disorder remains in remission. The terms encom metic, care, or therapeutic effect. pass modulating the threshold, development and/or duration [0036] By “cosmetic agent,” it is meant any ingredient that of the disease or disorder, or changing the way that a patient is appropriate for cosmetically treating, providing nutrients responds to the disease or disorder. to, and/or conditioning the hair, nail, and/or skin via topical [0027] Unless otherwise indicated, the terms “prevent,” application. “preventing” and “prevention” contemplate an action that [0037] By “pharmaceutical agent,” it is mean any drug that occurs before a patient begins to suffer from the speci?ed is either hydrophobic or hydrophilic in nature and appropriate disease or disorder, which inhibits or reduces the severity of for topical use. the disease or disorder. In other words, the terms encompass [0038] As used herein “medicament agents” include those prophylaxis. agents capable of promoting recovery from injury and illness.
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