Phenoxy-pyrrolidine derivative and its use and compositions
Inventors
Assignees
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Publication Number
US-8242286-B2
Publication Date
2012-08-14
Expiration Date
Abstract
The present invention is directed to the compound 2-(4-(hydroxymethyl)phenoxy)-1-(3-(2-(trifluoromethyl)phenoxy)pyrrolidin-1-yl)ethanone, its use as an inhibitor of stearoyl CoA desaturase and to pharmaceutical compositions containing this compound.
Core Innovation
The invention relates to a phenoxy-pyrrolidine derivative of Formula I, identified as (S)-2-(4-(hydroxymethyl)phenoxy)-1-(3-(2-(trifluoromethyl)phenoxy)pyrrolidin-1-yl)ethanone. The compound is identified as a stearoyl-CoA desaturase (SCD1) inhibitor. The document links the compound’s SCD1 inhibition to changes in lipid species that are associated with excess sebum production and related dermatologic and cosmetic conditions.
The problem addressed is excess sebum production and conditions associated therewith, including acne, oily skin and oily hair, shiny/greasy skin and greasy-looking hair, and seborrheic dermatitis. The document further describes reducing or preventing sebum synthesis as a therapeutic approach. It also describes reducing or preventing the synthesis of cholesterol esters and wax esters in the sebaceous glands.
The document also provides pharmaceutical embodiments in which the Formula I compound, or a pharmaceutically acceptable salt, is formulated as a pharmaceutical composition with a pharmaceutically acceptable carrier, vehicle, diluent, or excipient. The composition is described as usable in combination with a second therapeutic agent. Additionally, the document describes kit/article concepts packaging the compound for retail distribution with consumer instructions to alleviate conditions associated with excess sebum production.
Claims Coverage
The provided claim set includes multiple independent claims covering the Formula I compound and specific stereochemical embodiments, methods for reducing or preventing sebum synthesis and related lipid synthesis, methods of treating acne and selected sebum-associated conditions, and pharmaceutical compositions and kit concepts. Across the independent claims, the core inventive subject matter is centered on a specific SCD1-inhibiting phenoxy-pyrrolidine derivative defined by Formula I and administered therapeutically, optionally with a second therapeutic agent, to reduce or treat conditions associated with excess sebum production.
Formula I phenoxy-pyrrolidine compound
A compound of Formula I or a pharmaceutically acceptable salt thereof.
Reducing or preventing sebum synthesis by administering Formula I compound
A method of reducing or preventing the synthesis of sebum, comprising administering to a mammal in need thereof a therapeutically effective amount of the compound of Formula I or a pharmaceutically acceptable salt thereof.
Reducing or preventing cholesterol esters and wax esters in sebaceous glands
A method of reducing or preventing the synthesis of cholesterol esters and wax esters in the sebaceous glands of a mammal, comprising administering to a mammal in need thereof a therapeutically effective amount of the compound of Formula I or a pharmaceutically acceptable salt thereof.
Treating acne by administering Formula I compound
A method of treating acne, comprising administering to a mammal in need thereof a therapeutically effective amount of the compound of Formula I or a pharmaceutically acceptable salt thereof.
Specific (R)-configured phenoxy-pyrrolidinyl ethanone
The compound (R)-2-(4-(hydroxymmethy)phenoxy)-1-(3-(2-(trifluoromethly)phenoxy)pyrrolidin-1-yl)ethanone.
Pharmaceutical composition with (S) Formula I compound and pharmaceutically acceptable carrier
A pharmaceutical composition comprising the compound (S)-2-(4-(hydroxymethyl)phenoxy)-1-(3-(2-(trifluoromethyl)phenoxy)pyrrolidin-1-yl)ethanone, or a pharmaceutically acceptable salt of said compound, and a pharmaceutically acceptable carrier, vehicle, diluent or excipient.
Pharmaceutical composition with second therapeutic agent
A pharmaceutical composition comprising the compound (S)-2-(4-(hydroxymethyl)phenoxy)-1-(3-(2-(trifluoromethyl)phenoxy)pyrrolidin-1-yl)ethanone, or a pharmaceutically acceptable salt of said compound, a second therapeutic agent, and a pharmaceutically acceptable carrier, vehicle, diluent or excipient.
Treating or alleviating excess sebum-associated conditions
A method of treating or alleviating a condition associated with excess sebum production in a mammal in need of such treatment comprising administering to said mammal a therapeutically effective amount of (S)-2-(4-(hydroxymethyl)phenoxy)-1-(3-(2-(trifluoromethyl)phenoxy)pyrrolidin-1-yl)ethanone, or a pharmaceutically acceptable salt of said compound, alone or in combination with a second therapeutic agent.
Treating or alleviating selected sebum-associated dermatologic conditions
A method of treating or alleviating a condition selected from front acne, oily skin, oily hair, shiny skin, greasy-looking skin, greasy-looking hair, or seborrheic dermatitis in a mammal in need of such treatment comprising administering to said mammal a therapeutically effective amount of (S)-2-4-(hydroxymethyl)phenoxy)-1-(3-(2-(trifluoromethyl)phenoxy)pyrrolidin-2-yl)ethanone, or a pharmaceutically acceptable salt of said compound, alone or in combination with a second therapeutic agent.
Reducing or preventing stearoyl CoA desaturase activity
A method of reducing or preventing the activity of stearoyl CoA desaturase in a mammal in need of such treatment comprising administering to said mammal a therapeutically effective amount of (S)-2-(4-(hydroxymethyl)phenoxy)-1-(3-(2-(trifluoromethyl)phenoxy)pyrrolidin-1-yl)ethanone, or a pharmaceutically acceptable salt of said compound, alone or in combination with a second therapeutic agent.
Overall, the independent claims place the invention on a defined phenoxy-pyrrolidine derivative of Formula I, including an (S) embodiment, and methods of administering it to reduce or prevent sebum synthesis or related lipid synthesis, treat acne and selected sebum-associated skin and hair conditions, and reduce or prevent stearoyl CoA desaturase activity, optionally in combination with a second therapeutic agent, with separate coverage for pharmaceutical compositions and specific stereochemical naming.
Stated Advantages
Reduces or prevents sebum production by reducing or preventing sebum synthesis.
Reduces or prevents the synthesis of cholesterol esters and wax esters in the sebaceous glands.
Treats or alleviates acne.
Treats or alleviates conditions selected from oily skin, oily hair, shiny skin, greasy-looking skin, greasy-looking hair, and seborrheic dermatitis.
Reduces or prevents the activity of stearoyl CoA desaturase (SCD1).
Documented Applications
Reducing or preventing synthesis of sebum and alleviating conditions associated with excess sebum production.
Treating acne.
Treating or alleviating oily skin and oily hair, shiny/greasy skin and greasy-looking hair.
Treating seborrheic dermatitis.
Reducing or preventing synthesis of cholesterol esters and wax esters in sebaceous glands.
Pharmaceutical composition uses including administration in ingestion and application to skin or hair are described at the dependent level.
Retail kit/article packaging for consumer instructions to alleviate a condition associated with excess sebum production is described.
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