Substituted imidazo[1,2-a]pyrazines and pyrazino[1,2-a]pyrimidines as topical agents for dermatological applications
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Publication Number
US-11639356-B2
Publication Date
2023-05-02
Expiration Date
Abstract
Provided are compounds of formula (I): or cosmeceutically acceptable or pharmaceutically acceptable salts thereof. Additionally provided are cosmeceutical and/or pharmaceutical compositions comprising the compounds of formula (I), or the cosmeceutically acceptable or pharmaceutically acceptable salts thereof. Also provided are therapeutic and/or cosmetic methods using the cosmeceutical and/or pharmaceutical compositions comprising the compounds of formula (I), or the cosmeceutically acceptable or pharmaceutically acceptable salts thereof, for modulating cyclic adenosine monophosphate response element binding (CREB)-binding protein (CBP)/β-catenin mediated signaling in treating skin related diseases, conditions, or disorders mediated by aberrant CBP/β-catenin signaling and cosmetic methods for treating skin conditions mediated by aberrant CBP/β-catenin signaling.
Core Innovation
The invention relates to compounds of formula (I) and related variants, including cosmeceutically acceptable and pharmaceutically acceptable salts, stereoisomers, isotopically labeled compounds, and prodrugs. The compounds are substituted imidazo[1,2-a]pyrazines and pyrazino[1,2-a]pyrimidines defined by constrained variables L, X, Y, Q, n, and R1-R3, with Q selected as benzyl, phenyl, or an 8- to 11-membered bicyclic aryl optionally containing 1, 2, or 3 heteroatoms selected from nitrogen, oxygen, and sulfur.
The invention targets modulation of the Wnt/β-catenin pathway and inhibition of CBP/β-catenin mediated signaling. The compounds are positioned for topical dermatological and cosmeceutical use, and the document links CBP/β-catenin inhibition to treatment of CBP/β-catenin mediated skin diseases and aging-related skin conditions.
The disclosed scope includes sub-formulas (Ia), (Ib), and (Ic), and Y is defined as H or C(O)R, including esterification forms described in the document context. The document also describes topical administration in human skin and example outcome disclosures including a SuperTOPFLASH™ luciferase assay indicating CBP/β-catenin inhibition.
Claims Coverage
The document provides one independent compound claim and independent topical cosmetic method claims directed to a formula (I) compound and a cosmeceutical composition containing it. Across the independent claims, the coverage centers on the defined formula (I) scaffold with constrained substituent variables and topical cosmetic treatment of skin conditions.
Compound of formula (I)
A compound of formula (I), or a cosmeceutically acceptable or pharmaceutically acceptable salt thereof, with constrained substituent variables L, X, Y, Q, n, and R1-R3, including benzyl, phenyl, or an 8- to 11-membered bicyclic aryl optionally containing 1, 2, or 3 heteroatoms selected from nitrogen, oxygen, and sulfur.
Topical cosmetic treatment using a compound of formula (I)
A method for cosmetically treating a skin condition in a mammalian subject by topically administering a cosmeceutically effective amount of a compound of formula (I), or a cosmeceutically acceptable salt thereof, with the same structural constraints.
Cosmeceutical composition for topical cosmetic treatment
A method for cosmetically treating a skin condition in a mammalian subject by topically administering a cosmeceutically effective amount of a cosmeceutical composition comprising a cosmeceutically acceptable excipient and a compound of formula (I), or a cosmeceutically acceptable salt thereof, with the same structural constraints.
Across the independent claims, the inventive coverage centers on compounds of formula (I) defined by constrained substituent variables, optionally as cosmeceutically or pharmaceutically acceptable salts, and on topical cosmetic treatment methods using those formula (I) compounds, including use in cosmeceutical compositions containing a cosmeceutically acceptable excipient.
Stated Advantages
Potent modulation of the Wnt/β-catenin pathway.
Inhibition of CBP/β-catenin mediated signaling.
Use for treating CBP/β-catenin mediated skin diseases.
Use for treating aging-related skin conditions.
Documented Applications
Treating CBP/β-catenin mediated skin diseases using topical administration of compounds of formula (I) or related variants.
Treating aging-related skin conditions, including wrinkles and hyperpigmentation, via topically administering the compounds described.
Cosmetically treating a skin condition in a mammalian subject by topical administration of a cosmeceutically effective amount of a compound of formula (I) or a cosmeceutically acceptable salt thereof.
Cosmetically treating a skin condition using a topical cosmeceutical composition comprising a cosmeceutically acceptable excipient and a compound of formula (I) or a cosmeceutically acceptable salt thereof.
Topical modulation of CBP/β-catenin-mediated signaling in skin, supported by disclosed SuperTOPFLASH™ luciferase assay results indicating CBP/β-catenin inhibition.
Human skin topical improvement over an 8-week period using a disclosed compound formulation.
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