IP Library Granted Patent US 10,710,958
Granted Patent B2
US 10,710,958 · App. 16/338,925 · Granted Jul 14, 2020

Carbamoyl phenylalaninol compounds and uses thereof

Inventors: Fionn Hurley (Dublin, IE); Lawrence Patrick Carter (Palo Alto, CA)
Assignee: Jazz Pharmaceuticals Ireland Limited
C07C271/66C07C2601/16
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,710,958
App. No.
16/338,925
Granted
Jul 14, 2020
Kind
B2
Abstract

The present invention relates to carbamoyl phenylalaninol compounds and methods of using the same to treat disorders.

Claims (38)

1. A method of treating excessive daytime sleepiness or fatigue, in a subject in need thereof, comprising administering to the subject a compound of Formula I:

wherein

R is optionally substituted lower alkyl of 1 to 8 carbon atoms, halogen, optionally substituted alkoxy containing 1 to 3 carbon atoms, nitro, hydroxy, cyano, trifluoromethyl, or optionally substituted thioalkoxy containing 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 , R 2 , and R 3 are independently hydrogen, optionally substituted lower alkyl of 1 to 8 carbon atoms, optionally substituted aryl, optionally substituted arylalkyl, or optionally substituted cycloalkyl of 3 to 7 carbon atoms; or

R 2 and R 3 can he joined to form a 5 to 7-membered heterocycle optionally substituted with a member selected from the group consisting of alkyl and 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;

or a pharmaceuticallly acceptable salt thereof.

2. A method of treating nightmares and/or sleep-related disturbances associated with PTSD in a subject in need thereof, comprising administering to the subject a compound of Formula I:

wherein

R is optionally substituted lower alkyl of 1 to 8 carbon atoms, halogen, optionally substituted alkoxy containing 1 to 3 carbon atoms, nitro, hydroxy, cyano, trifluoromethyl, or optionally substituted thioaikoxy containing 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 , R 2 , and R 3 are independently hydrogen, optionally substituted lower alkyl of 1 to 8 carbon atoms, optionally substituted aryl, optionally substituted arylalkyl, or optionally substituted cycloalkyl of 3 to 7 carbon atoms; or

R 2 and R 3 can he joined to form a 5 to 7-membered heterocycle. optionally substituted with a member selected from the group consisting of alkyl and 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;

or a pharmaceutically acceptable salt thereof.

3. The method of claim 1 , wherein the compound is a compound of Formula II;

or a pharmaceutically acceptable salt thereof.

4. The method of claim 1 , wherein the compound is compound 1:

or a pharmaceutically acceptable salt thereof.

5. The method of claim 1 , wherein the compound is compound 2:

or a pharmaceutically acceptable salt thereof.

6. The method of claim 1 , comprising administering a composition comprising the compound.

7. The method of claim 1 , comprising administering a pharmaceutical composition comprising the compound and a pharmaceutically acceptable carrier.

8. The method of claim 7 , wherein the composition is a dosage form.

9. The method of claim 8 , wherein the composition is an immediate release oral dosage form.

10. The method of claim 9 , wherein the composition is a tablet or a capsule.

11. The method of claim 1 , wherein the subject has excessive daytime sleepiness.

12. The method of claim 1 , wherein the subject has fatigue.

13. The method of claim 2 , wherein the compound is a compound of Formula II:

or a pharmaceutically acceptable salt thereof.

14. The method of claim 2 , wherein the compound is compound I:

or a pharmaceutically acceptable salt thereof.

15. The method of claim 2 , wherein the compound is compound 2:

or a pharmaceutically acceptable salt thereof.

16. The method of claim 2 , comprising administering a composition comprising the compound.

17. The method of claim 2 , comprising administering a pharmaceutical composition comprising the compound and a pharmaceutically acceptable carrier.

18. The method of claim 17 , wherein the composition is a dosage form.

19. The method of claim 18 , wherein the composition is an immediate release oral dosage form.

20. The method of claim 19 , wherein the composition is a tablet or a capsule.

Assignments (7)
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 May 19, 2020
From: HURLEY, FIONN; CARTER, LAWRENCE PATRICK
To: JAZZ PHARMACEUTICALS IRELAND LIMITED
Reel/Frame 052708/0903 →
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 (2)
Provisional Application 62404917 · Oct 6, 2016
Related Publication 20190218175A1 · Jul 18, 2019
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