IP Library Granted Patent US 11,497,725
Granted Patent B2
US 11,497,725 · App. 17/028,674 · Granted Nov 15, 2022

Treatment for obesity

Inventors: Moise A. Khayrallah (Morrisville, NC); Gary Bream (Cary, NC); Stephen E. Butts (Holly Springs, NC)
Assignees: Axsome Malta Ltd.; SK Biopharmaceuticals Co., Ltd.
A61K31/27A61K9/0053A61K9/48
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Quick Facts
Patent No.
US 11,497,725
App. No.
17/028,674
Granted
Nov 15, 2022
Kind
B2
Abstract

The present invention relates to a method for treating or preventing obesity in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of certain carbamate compounds. The invention further relates to methods for reducing body weight and/or reducing food intake in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of certain carbamate compounds.

Claims (22)

1. A method for reducing body weight or body weight gain in a human subject in need thereof, comprising administering to the subject a therapeutically effective amount of a compound of Formula (I):

or a pharmaceutically acceptable salt or ester thereof;

wherein R is a member selected from the group consisting of alkyl of 1 to 8 carbon atoms, halogen, alkoxy of 1 to 3 carbon atoms, nitro, hydroxy, trifluoromethyl, and thioalkoxy of 1 to 3 carbon atoms;

x is an integer of 0 to 3, with the proviso that R may be the same or different when x is 2 or 3;

R 1 and R 2 are independently selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms, aryl, arylalkyl, cycloalkyl of 3 to 7 carbon atoms; or

R 1 and R 2 can be joined to form a 5 to 7-membered heterocycle that is unsubstituted or substituted with one or more alkyl or aryl groups, wherein the heterocycle can comprise 1 to 2 nitrogen atoms and 0 to 1 oxygen atom, wherein the nitrogen atoms are not directly connected with each other or with the oxygen atom;

said method comprises administering the compound of Formula (I) to the human subject in a dosing regimen comprising a daily dose of at least 200 mg/day, wherein the compound of Formula (I) or pharmaceutically acceptable salt thereof effects a decrease in body weight or body weight gain in the human subject by at least 0.6 kg from baseline at the 6th week of the dosing regimen.

2. The method of claim 1 , wherein x=0.

3. The method of claim 1 , wherein R 1 and R 2 are hydrogen and x=0.

4. The method of claim 1 , wherein the compound of Formula I is an enantiomer of Formula I substantially free of other enantiomers or an enantiomeric mixture wherein one enantiomer of Formula I predominates.

5. The method of claim 4 , wherein the enantiomer of Formula I predominates to the extent of about 98% or greater.

6. The method of claim 4 , wherein the enantiomer of Formula I is an enantiomer of Formula Ia:

or a pharmaceutically acceptable salt or ester thereof.

7. The method of claim 6 , wherein the enantiomer of Formula Ia is the (R) or (D) enantiomer.

8. The method of claim 6 , wherein the enantiomer of Formula Ia is the (S) or (L) enantiomer.

9. The method of claim 6 , wherein the enantiomer of Formula Ia predominates to the extent of about 98% or greater.

10. The method of claim 4 , wherein the enantiomer of Formula I substantially free of other enantiomers is the compound of Formula Ib or an enantiomeric mixture wherein the compound of Formula Ib predominates:

or a pharmaceutically acceptable salt or ester thereof.

11. The method of claim 10 , wherein the compound of Formula Ib predominates to the extent of about 98% or greater.

12. The method of claim 1 , wherein the compound of Formula I is administered orally.

13. The method of claim 1 , wherein the compound of Formula I is administered in the form of a capsule or tablet.

14. The method of claim 1 , wherein the compound of Formula I is administered in the form of a capsule at a dose of about 10 mg to about 1000 mg without any excipients.

Assignments (5)
SECURITY INTEREST Recorded May 9, 2025
From: AXSOME THERAPEUTICS, INC.; AXSOME MALTA LTD.
To: WILMINGTON TRUST, NATIONAL ASSOCIATION
Reel/Frame 071247/0836 →
RELEASE OF SECURITY INTEREST Recorded May 6, 2025
From: U.S. BANK TRUST COMPANY, NATIONAL ASSOCIATION, AS SUCCESSOR IN INTEREST TO U.S. BANK NATIONAL ASSOCIATION
To: JAZZ PHARMACEUTICALS IRELAND LIMITED
Reel/Frame 071034/0467 →
SECURITY INTEREST Recorded Sep 9, 2024
From: AXSOME MALTA LTD
To: HERCULES CAPITAL, INC.
Reel/Frame 068900/0023 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 16, 2022
From: JAZZ PHARMACEUTICALS IRELAND LIMITED
To: AXSOME MALTA LTD.
Reel/Frame 060223/0878 →
SECURITY AGREEMENT Recorded May 5, 2021
From: CAVION, INC.; CELATOR PHARMACEUTICALS, INC.; JAZZ PHARMACEUTICALS IRELAND LIMITED; JAZZ PHARMACEUTICALS, INC.
To: U.S. BANK NATIONAL ASSOCIATION
Reel/Frame 056151/0010 →