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

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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 →