Cytoprotective compounds, pharmaceutical and cosmetic formulations, and methods

Abstract

Cytoprotective compounds, many of which are phenolic derivatives characterized by a substituted phenol having certain conjugated bonds, are useful in the treatment of certain ischemic or inflammatory conditions, including but not limited to stroke, myocardial infarction, congestive heart failure, and skin disorders characterized by inflammation or oxidative damage. They are also useful in the manufacture of pharmaceutical and cosmetic formulations for the treatment of such conditions.

1 - 10 . (canceled)  
     
     
         111 . A compound of formula A  
       
         
           
           
               
               
           
         
         or formula B  
         
           
             
             
                 
                 
             
           
         
         mixtures and pharmaceutically acceptable salts thereof.  
       
     
     
         112 . The compound of  claim 111 , where the compound is of formula A:  
       
         
           
           
               
               
           
         
         and pharmaceutically acceptable salts thereof.  
       
     
     
         113 . The compound of  claim 111 , where the compound is of formula B:  
       
         
           
           
               
               
           
         
         and pharmaceutically acceptable salts thereof.  
       
     
     
         114 . A skin care composition comprising a therapeutically effective amount of one or more compounds of  claim 111  and a pharmaceutically or cosmetically acceptable carrier or excipient.  
     
     
         115 . The skin care composition of  claim 114 , formulated for topical administration to the skin of a mammalian subject.  
     
     
         116 . The skin care composition of  claim 115 , wherein said composition is included in a topical cosmetic formulation.  
     
     
         117 . The skin care composition of  claim 115 , wherein said composition is included in a topical pharmaceutical formulation.  
     
     
         118 . The skin care composition of  claim 114 , wherein the composition is formulated for transdermal administration to a mammalian subject.  
     
     
         119 . The skin care composition of  claim 115 , wherein the composition is formulated for oral administration to a mammalian subject.  
     
     
         120 . A method of regulating skin condition wherein the skin condition is characterized by oxidative stress comprising administering to a subject suffering from a skin condition a composition of  claim 114 .  
     
     
         121 . The method of  claim 120 , wherein the skin condition is selected from the group consisting of dermatitis, contact dermatitis, acne, pimples, blackheads, oiliness, facial shine, foundation breakthrough, excessive sebum production, visible and/or tactile discontinuities, psoriasis, and combinations thereof.  
     
     
         122 . The method of  claim 121 , wherein the skin condition is acne, pimples, blackheads, oiliness, facial shine, foundation breakthrough, and excessive sebum production.  
     
     
         123 . The method of  claim 122 , wherein the skin condition is acne.  
     
     
         124 . The method of  claim 121 , wherein the skin condition is psoriasis.  
     
     
         125 . A method of regulating and/or preventing signs of skin aging comprising administering to a subject suffering from skin aging a composition of  claim 114 .  
     
     
         126 . The method as in  claim 120  or  125 , wherein the signs of skin aging and/or the skin condition are selected from the group consisting of the development of textural discontinuities, wrinkles, fine superficial wrinkles, coarse deep wrinkles, skin lines, facial frown lines, expression lines, rhytides, dermatoheliosis, photodamage, premature skin aging, crevices, bumps, pits, large pores, orange-peel skin appearance, dryness, scaliness, flakiness, blemishes, acne, pimples, breakouts, excess skin oil problems, over production of sebum, oiliness, facial shine, foundation breakthrough, abnormal desquamation, abnormal epidermal differentiation, abnormal skin turnover, keratoses, hyperkeratinization; inadequate skin moisturization, environmental dryness, loss of skin elasticity, elastosis, sagging, puffiness in the eye area and jowls, loss of skin firmness, loss of skin tightness, loss of skin recoil from deformation, non-melanin skin discoloration, undereye circles, blotching, rosacea, sallowness, discoloration caused by telangiectasia or spider vessels, melanin-related hyperpigmented skin regions, age spots, liver spots, brown spots, freckles, post-inflammatory hyperpigmentation, inflammation due to acne lesion, in-grown hair, insect/spider bite or sting, scratch, cut, wound, and/or abrasion, atrophy, collagen breakdown and structural alterations or abnormalities, changes in the stratum corneum, dermis, epidermis, the skin vascular system such as telangiectasia or spider vessels; tissue responses to insult from itch or pruritus; and alterations to underlying tissues such as subcutaneous fat, cellulite, muscles, trabeculae, and septae, and combinations thereof.  
     
     
         127 . A method of regulating and/or preventing signs of skin damage due to extrinsic factors comprising administering to a subject suffering from skin damage a composition of  claim 114 .  
     
     
         128 . The method as in  claim 127 , wherein the extrinsic factors are selected from exposure to UV radiation, smoke, ozone, pollutants, stress and/or fatigue, sunlight, wearing diapers and combinations thereof.  
     
     
         129 . The method as in  claim 128 , wherein exposure to the extrinsic factors lead to diaper rash, erythema, UV radiation damage, sunburn, photoaging, contact dermatitis, and combinations thereof.  
     
     
         130 . The method as in  claim 129 , wherein the exposure leads to erythma.  
     
     
         131 . The method as in  claim 129 , wherein the exposure leads to diaper rash.  
     
     
         132 . A product comprising instructions directing a user to apply a skin care composition comprising a skin care composition of  claim 114 .  
     
     
         133 . A method of promoting a product by directing a user to apply a skin care composition comprising a skin care composition of  claim 114 .  
     
     
         134 . Use of a composition comprising a skin care composition of  claim 114  in the manufacture of a cosmetic for treating a mammalian subject of a dermatologic condition.  
     
     
         135 . A pharmaceutical composition comprising a therapeutically effective amount of a compound of  claim 111  further comprising a pharmaceutically acceptable carrier or excipient.  
     
     
         136 . A method for regulating and/or reducing the symptoms associated with inflammatory disorders and/or autoimmune disorders comprising administration to a subject in need of such treatment a composition of  claim 135 .  
     
     
         137 . The method of  claim 136  wherein the disorder is selected from the group consisting of diabetes, renal disease, pre-menstrual syndrome, asthma, rheumatoid arthritis, osteoarthritis, muscle fatigue, irritable bowel syndrome, inflammatory bowel disease and intermittent claudication.