IP Library Granted Patent US 10,105,341
Granted Patent B2
US 10,105,341 · App. 15/594,070 · Granted Oct 23, 2018

Treatment for obesity

Inventors: Moise A. Khayrallah (Morrisville, NC); Gary Bream (Cary, NC); Stephen E. Butts (Holly Springs, NC)
Assignees: Jazz Pharmaceuticals International III Limited; SK Biopharmaceuticals Co., Ltd.
A61K31/27A61K9/0053A61K9/48
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Quick Facts
Patent No.
US 10,105,341
App. No.
15/594,070
Granted
Oct 23, 2018
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 (33)

1. A method for reducing or preventing body weight gain in a 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;

wherein the subject reduces body weight.

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 90% or greater.

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

7. 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.

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

9. The method of claim 7 , wherein the enantiomer of Formula Ia is the (S) or (L) enantiomer.

10. The method of claim 7 , wherein the enantiomer of Formula Ia predominates to the extent of about 90% or greater.

11. The method of claim 7 , wherein the enantiomer of Formula Ia predominates to the extent of about 98% or greater.

12. 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.

13. The method of claim 12 , wherein the compound of Formula Ib predominates to the extent of about 90% or greater.

14. The method of claim 12 , wherein the compound of Formula Ib predominates to the extent of about 98% or greater.

15. The method of claim 1 , wherein the effective amount of the compound of Formula I is from about 0.01 mg/kg/dose to about 150 mg/kg/dose.

16. The method of claim 1 , wherein the effective amount of the compound of Formula I is from about 1 mg/day to about 7000 mg/day.

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

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

19. 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.

20. A compound of Formula (I):

or a pharmaceutically acceptable salt 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.

Assignments (6)
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 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 3, 2019
From: JAZZ PHARMACEUTICALS INTERNATIONAL III LIMITED
To: JAZZ PHARMACEUTICALS IRELAND LIMITED
Reel/Frame 049666/0456 →
Continuity (4)
Continuation 14955646 · Dec 1, 2015
Continuation 14334694 · Jul 18, 2014
Provisional Application 61847593 · Jul 18, 2013
Related Publication 20170340596A1 · Nov 30, 2017
Cited By (13)
US 12,186,296 US 12,186,298 US 12,226,377 US 12,226,388 US 12,226,389 US 12,239,625 US 12,257,223 US 12,263,150 US 12,263,151 US 12,295,926 US 12,303,478 US 12,478,604 US 12,551,457