IP Library Granted Patent US 8,242,286
Granted Patent B2
US 8,242,286 · App. 12/670,010 · Granted Aug 14, 2012

Phenoxy-pyrrolidine derivative and its use and compositions

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Quick Facts
Patent No.
US 8,242,286
App. No.
12/670,010
Granted
Aug 14, 2012
Kind
B2
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.

Claims (25)

1. The compound of Formula I

or a pharmaceutically acceptable salt thereof.

2. A method of reducing or preventing the synthesis of sebum,comprising administering to mammal in need thereof a therapeutically effective amount of the compound of Formula I

or a pharmaceutical acceptable salt thereof.

3. A method of reducing or preventingthe 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.

4. 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.

5. The compound (R)-2-(4-(hydroxymethy)phenoxy)-1-(3-(2-(trifluoromethly)phenoxy)pyrrolidin-1-yl)ethanone.

6. The compound 2-(4-hydroxymethyl)phenoxy)-1-(3-(2-trifluoromethyl)phenoxy)pyrrolidin-1-yl)ethanone.

7. 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.

8. 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.

9. The composition of claims 7 wherein said composition is suitable for applying to the skin or hair.

10. The composition of claims 7 wherein said composition is suitable for ingestion.

11. 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.

12. A method of treating or alleviating a condition selected 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.

13. 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.

14. A kit comprising a compound according to claim 1 packaged for retail distribution, which advises a consumer how to utilize the compound to alleviate a condition associated with excess sebum production.

15. A kit comprising a compound according to claim 1 packaged for retail distribution, which advises a consumer how to utilize the compound to alleviate a condition selected from acne, oily skin, oily hair, shiny skin, greasy-looking skin, greasy looking hair, seborrheic dermatitis.

16. The method of claim 2 , wherein said mammal is a human.

17. The method of claim 3 , wherein said mammal is a human.

18. The method of claim 4 , wherein said mammal is a human.

19. The method of claim 11 , wherein said mammal is a human.

20. The method of claim 12 , wherein said mammal is a human.

21. The method of claim 13 , wherein said mammal is a human.

Assignments (7)
CHANGE OF NAME Recorded Oct 27, 2020
From: GDD THERAPEUTICS, INC.
To: LIPIDIO PHARMACEUTICALS INC.
Reel/Frame 054226/0049 →
MERGER AND CHANGE OF NAME Recorded Oct 26, 2020
From: GDD THERAPEUTICS, LLC; GDD THERAPEUTICS, INC.
To: GDD THERAPEUTICS, INC.
Reel/Frame 054209/0327 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 23, 2018
From: THESAN PHARMACEUTICALS, INC.
To: GDD THERAPEUTICS, LLC
Reel/Frame 046687/0622 →
CORRECTIVE ASSIGNMENT TO CORRECT THE INADVERTENT PATENT NUMBERS ADDED PREVIOUSLY RECORDED AT REEL: 034749 FRAME: 0689. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT . Recorded Jan 29, 2018
From: GOLDMAN SACHS LENDING PARTNERS LLC
To: BARCLAYS BANK PLC, AS SUCCESSOR AGENT
Reel/Frame 045177/0026 →
NOTICE OF SUCCESSION OF AGENCY Recorded Jan 9, 2015
From: GOLDMAN SACHS LENDING PARTNERS, LLC
To: BARCLAYS BANK PLC, AS SUCCESSOR AGENT
Reel/Frame 034749/0689 →
RELEASE OF SECURITY INTEREST Recorded Jan 10, 2014
From: GOLDMAN SACHS LENDING PARTNERS LLC
To: MEDICIS PHARMACEUTICAL CORPORATION
Reel/Frame 031944/0190 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 25, 2013
From: MEDICIS PHARMACEUTICAL CORPORATION
To: THESAN PHARMACEUTICALS, INC.
Reel/Frame 031280/0766 →