IP Library Granted Patent US 9,656,961
Granted Patent B2
US 9,656,961 · App. 14/286,499 · Granted May 23, 2017

Methods for treating depressive symptoms

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Quick Facts
Patent No.
US 9,656,961
App. No.
14/286,499
Granted
May 23, 2017
Kind
B2
Abstract

The present application relates methods for treating a depressive symptom comprising administering an effective amount of a μ opioid receptor agonist or a pharmaceutically acceptable salt thereof to a subject in need thereof. Non-limiting examples of such agonist include the compounds of Formulas I, II, III, and IV, as well as the compounds of Table A.

Claims (31)

1. A method of treating a depressive symptom in a subject comprising administering to the subject a compound of Formula I:

or a pharmaceutically acceptable salt thereof, wherein

R 1 is cyclobutyl,

R 2 is H, hydroxyl, or methoxy; and

R 3 and R 4 are each, independently, H, hydroxyl, or NR 5 R 6 , wherein R 5 and R 6 are each independently H, alkyl or optionally substituted acyl, or alternatively, R 3 and R 4 , together with the carbon atom to which they are attached, form C═O or C═CH 2 ;

wherein the depressive symptom is selected from the group consisting of depressed mood, loss of pleasure, post-partum depression, adjustment disorders with depressed mood, bereavement, bipolar I disorder, bipolar II disorder, cyclothymia, dysthymia, depression, dysthymic disorder, mixed mania, post-traumatic stress disorder, and seasonal affective disorder.

2. The method according to claim 1 , wherein the compound of Formula I is:

or a pharmaceutically acceptable salt thereof.

3. The method of claim 1 , wherein the compound of Formula I exhibits an Emax of 5% to 45% in a GTPγS binding assay.

4. The method of claim 3 , wherein the Emax is 15% to 35% in a GTPγS binding assay.

5. The method of claim 3 , wherein the compound of Formula I has a low risk of opioid dependence, opioid addiction, or symptoms of opioid withdrawal.

6. The method of claim 1 , wherein the compound of Formula I exhibits a maximal dopamine efflux in the nucleus accumbens of 125% to 300% over base line in a rat.

7. The method of claim 1 , wherein the compound does not attenuate thermal pain in a rodent hot plate model when administered at a dose of at least 1 mg/kg.

8. The method of claim 1 , wherein the depressive symptom is depressed mood, loss of pleasure, or post-partum depression.

9. The method of claim 1 , wherein the depressive symptom is depression.

10. The method of claim 9 , wherein the depression is major depressive disorder (MDD) or treatment-resistant disorder (TRD).

11. A method of treating a depressive symptom in a subject comprising administering to the subject a compound of Formula I:

or a pharmaceutically acceptable salt thereof, wherein

R 1 is cyclobutyl,

R 2 is H, hydroxyl, or methoxy; and

R 3 and R 4 are each, independently, H, hydroxyl, or NR 5 R 6 , wherein R 5 and R 6 are each independently H, alkyl or optionally substituted acyl, or alternatively, R 3 and R 4 , together with the carbon atom to which they are attached, form C═O or C═CH 2 ;

wherein the depressive symptom is selected from the group consisting of acute stress disorder, anxiety disorder, Asperger syndrome, attention deficit, borderline personality disorder, fatigue, hyperactivity disorder, impulse control disorder, loss of appetite, obsessive-compulsive personality disorder (OCD), paranoid disorder, psychomotor changes, self-injury disorder, separation disorder, sleep disturbance, sleep disorder, substance-induced mood disorder, Tourette syndrome, tic disorder, and Trichotillomania.

12. The method of claim 11 , wherein the depressive symptom is acute stress disorder, Asperger syndrome, attention deficit, borderline personality disorder, hyperactivity disorder, impulse control disorder, obsessive-compulsive personality disorder (OCD), paranoid disorder, self-injury disorder, separation disorder, sleep disorder, substance-induced mood disorder, Tourette syndrome, tic disorder, or Trichotillomania.

13. The method of claim 11 , wherein the depressive symptom is an anxiety disorder, wherein the anxiety disorder is generalized anxiety disorder, panic, agoraphobia, acute stress, or post-traumatic stress disorder.

14. The method according to claim 11 , wherein the compound of Formula I is:

or a pharmaceutically acceptable salt thereof.

15. The method of claim 11 , wherein the compound of Formula I exhibits an Emax of 5% to 45% in a GTPγS binding assay.

16. The method of claim 15 , wherein the Emax is 15% to 35% in a GTPγS binding assay.

17. The method of claim 15 , wherein the compound of Formula I has a low risk of opioid dependence, opioid addiction, or symptoms of opioid withdrawal.

18. The method of claim 11 , wherein the compound of Formula I exhibits a maximal dopamine efflux in the nucleus accumbens of 125% to 300% over base line in a rat.

19. The method of claim 11 , wherein the compound does not attenuate thermal pain in a rodent hot plate model when administered at a dose of at least 1 mg/kg.

Assignments (5)
SECURITY INTEREST Recorded Feb 13, 2026
From: ALKERMES PHARMA IRELAND LIMITED
To: JPMORGAN CHASE BANK, N.A. AS ADMINISTRATIVE AGENT
Reel/Frame 074858/0405 →
RELEASE OF SECURITY INTEREST IN PATENTS PREVIOUSLY RECORDED AT REEL/FRAME (073213/0302) Recorded Feb 13, 2026
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: ALKERMES PHARMA IRELAND LIMITED
Reel/Frame 074858/0429 →
SECURITY INTEREST Recorded Oct 23, 2025
From: ALKERMES PHARMA IRELAND LIMITED
To: JPMORGAN CHASE BANK, N.A. AS ADMINISTRATIVE AGENT
Reel/Frame 073213/0302 →
SECURITY INTEREST Recorded Feb 7, 2018
From: ALKERMES PHARMA IRELAND LIMITED
To: MORGAN STANLEY SENIOR FUNDING, INC., AS COLLATERAL AGENT
Reel/Frame 044858/0280 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 26, 2014
From: BLUMBERG, LAURA COOK; DEAVER, DAN; EYERMAN, DAVID; WYNN, THOMAS
To: ALKERMES PHARMA IRELAND LIMITED
Reel/Frame 033187/0074 →