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KR-20260065802-A - esters of triparotene

KR20260065802AKR 20260065802 AKR20260065802 AKR 20260065802AKR-20260065802-A

Abstract

A topical, local skin care composition is described that contains a specific tryphalotene fatty acid ester and one or more of these compounds. In some embodiments, upon hydrolysis in the skin, the shorter-chain tryphalotene fatty acid ester releases short-chain fatty acids, such as octanoic acid and lauric acid, which are known to contribute to improved penetration in local skin delivery. A method of applying the topical composition topically to the skin of a subject to inhibit or reduce signs of photoaging or acne is also described.

Inventors

  • 윈 다니엘

Assignees

  • 액테라 인그리디언츠 인코포레이티드

Dates

Publication Date
20260511
Application Date
20240829
Priority Date
20230901

Claims (16)

  1. As a compound of chemical formula I, Chemical Formula I A compound, wherein R1 is an unsubstituted hydrocarbyl having 7 to 17 carbon atoms.
  2. A compound according to claim 1, wherein R1 is a saturated or unsaturated, linear or branched, aliphatic hydrocarbyl group.
  3. A compound according to claim 1, wherein R1 is an unsubstituted linear or branched alkyl or alkenyl.
  4. A compound according to claim 1, wherein R1 is a C7 , C11 , or C15 alkyl.
  5. A compound according to claim 1, wherein R1 is a C17 alkenyl.
  6. In claim 1, the compound is selected from the group consisting of the following: Chemical formula II (3''-(tert-butyl)-4'-(2-(octanoyloxy)ethoxy)-4''-(pyrrolidin-1-yl)-[1,1':3',1''-terphenyl]-4-carboxylic acid), Chemical formula III (3''-(tert-butyl)-4'-(2-(dodecanoyloxy)ethoxy)-4''-(pyrrolidine-1-yl)-[1,1':3',1''-terphenyl]-4-carboxylic acid), Chemical formula IV (3''-(tert-butyl)-4'-(2-(palmitoyloxy)ethoxy)-4''-(pyrrolidin-1-yl)-[1,1':3',1''-terphenyl]-4-carboxylic acid), and Chemical formula V (3''-(tert-butyl)-4'-(2-(oleoyloxy)ethoxy)-4''-(pyrrolidin-1-yl)-[1,1':3',1''-terphenyl]-4-carboxylic acid).
  7. A topical skin care composition comprising a compound of any one of claims 1 to 6 in a cosmetically acceptable lipophilic carrier, wherein said compound is at least partially soluble in the cosmetically acceptable lipophilic carrier.
  8. A composition according to claim 7, wherein the cosmetically acceptable lipophilic carrier is selected from the group consisting of softening esters, triglycerides, vegetable oils, polyesters, polyol esters, wax esters, gerbet esters, fatty alcohols, fatty acid ethers, vegetable waxes, hydrocarbon fluids, petroleum jelly, alkanes, isoalkanes, silicones, squalanes, and combinations thereof.
  9. A composition according to claim 7, wherein the cosmetically acceptable lipophilic carrier comprises an ester.
  10. A composition according to claim 7, wherein the compound is soluble in a cosmetically acceptable lipophilic carrier in a minimum amount of about 1 weight percent.
  11. A composition according to claim 7, wherein the weight ratio of the compound to the cosmetically acceptable lipophilic carrier is at least 1:99.
  12. A composition according to claim 7, wherein the weight ratio of the compound to the cosmetically acceptable lipophilic carrier is about 1:9 to about 3:7.
  13. In claim 7, the composition comprises an oil phase containing a compound and an aqueous phase containing water in the lipophilic carrier.
  14. A composition according to claim 13, in the form of a water-in-oil emulsion, an oil-in-water emulsion, or a suspension of oil droplets in an aqueous matrix, such as a gel.
  15. A composition according to claim 7, wherein the composition further comprises at least one component selected from the group consisting of ascorbic acid and its derivatives, ferulic acid, azelaic acid, kojic acid, mandelic acid, alpha-hydroxy acid, beta-hydroxy acid, lipohydroxy acid, bakuchiol, fruit acid, polysaccharide, hyaluronic acid, moisturizer, gluconolactone, heparan sulfate, arbutin, niacinamide, resveratrol, hydroquinone, exfoliant, keratolytic agent, plant extract, marine extract, fermentation extract, isoflavone, bisabolol, anti-aging peptide, retinol, retinoic acid, retinyl ester, retinoic acid ester, adapalene, adapalene ester, and other retinoids.
  16. A method for inhibiting or reducing signs of photoaging or acne, comprising applying the composition of claim 7 topically to the skin of a subject requiring such an application.

Description

esters of triparotene The present invention relates to various topical compositions containing tryparotene fatty acid esters and one or more tryparotene fatty acid esters, methods for using these compositions, and processes for preparing these compositions. Topical compositions are applied to the skin, and when hydrolyzed on the skin, the shorter chain esters release short chain fatty acids such as octanoic acid and lauric acid, which are known to contribute to improved penetration in topical skin delivery. Particularly on the face, noticeable skin damage is one of the most common targets for dermatological and cosmetic treatments. Untreated facial skin damage can cause anxiety and psycho-emotional trauma. Facial skin damage is often caused by photoaging and can manifest as actinic keratosis, sunspots, loss of basal skin collagen and elastin, wrinkles, and sagging skin. In the early stages, photoaging can appear as enlarged freckles as well as inflamed erythema. Other facial skin damage can be caused by acne, which can lead to inflamed pores and post-acne scarring. Topical retinoids are the primary treatment for skin damage caused by photoaging and acne in both cosmetic and prescription drugs. These include first-generation retinoids related to vitamin A, such as retinol (retinyl alcohol) and retinoic acid. In addition, there are second-generation retinoids, which are further variations of vitamin A. While all of these substances are lipophilic and relatively easy to formulate into topical products, they have two major drawbacks: they cause severe erythema, scaling, and skin peeling, and they are teratogenic. Tryphalotene (4-[3-(3-tert-butyl-4-pyrrolidin-1-ylphenyl)-4-(2-hydroxyethoxy)phenyl]benzoic acid) is a fourth-generation retinoid used topically to treat acne as a selective retinoic acid receptor gamma (RAR-gamma) agonist. However, derivatives with different chemical properties are needed to provide enhanced efficacy. The present disclosure relates to tryphalotene fatty acid esters. In certain embodiments, upon hydrolysis in the skin, the shorter chain esters release short-chain fatty acids, such as octanoic acid and lauric acid, which can provide antimicrobial benefits to the skin. Furthermore, the shorter chains, such as lauric acid and longer chains, released upon ester hydrolysis are known to contribute to improved penetration in topical skin delivery. Summary of the Invention In various embodiments, the present invention relates to a compound of formula I: Chemical Formula I In the above formula, R1 is an unsubstituted hydrocarbyl having 7 to 17 carbon atoms. An additional aspect relates to a topical skin care composition comprising one or more compounds of Formula I in a cosmetically acceptable carrier. Another aspect relates to a method for inhibiting or reducing signs of photoaging or acne, comprising applying the composition described herein topically to the skin of a subject requiring treatment. Generally, the present invention relates to tryparotene fatty acid esters, various topical compositions containing one or more tryparotene fatty acid esters, methods for using these compositions, and processes for preparing these compositions. Topical compositions are applied to the skin, and upon hydrolysis in the skin, the shorter chain esters release short-chain fatty acids, such as octanoic acid and lauric acid, which can provide antimicrobial benefits to the skin. Furthermore, the shorter chains, such as lauric acid and longer chains, released upon ester hydrolysis are known to contribute to improved penetration in topical skin delivery. Accordingly, the present invention provides an active formulation that is a tryphalotene derivative that can be used for the treatment of acne. These fourth-generation retinoids comprise tryphalotene and esters of C8 - C18 fatty acids. For example, the tryphalotene esters of fatty acids comprise those of Formula I: Chemical Formula I In the above formula, R1 is an unsubstituted hydrocarbyl having 7 to 17 carbon atoms. The hydrocarbyl may be branched or linear, saturated or unsaturated. In various embodiments, R1 is a saturated or unsaturated, linear or branched, aliphatic hydrocarbyl group. Preferably, R1 is an unsubstituted branched or linear alkyl or alkenyl having 7 or more carbon atoms, e.g., a C7 - C17 carbon chain. If R1 is an alkenyl, the substituent has at least one double bond, but may optionally have two or more double bonds. Examples of acceptable hydrocarbyl groups ( R1 ) include C7 - C17 alkyl or alkenyl groups. Among these, C7 , C11 , and C15 alkyl and C17 alkenyl are preferred. In the compound of Formula I, the alkyl or alkenyl ester chain is preferably soluble in the oil phase and mutually soluble with lipophilic emollients typically used in topical skin products. The compound may be in the form of an amorphous solid (i.e., a non-crystalline solid). In certain embodiments, the compound is selected from the group consisting of the following: Chemi