Granted Patent
B2
US 12,221,428 · App. 18/743,944 · Granted Feb 11, 2025
Use of deuterated empathogens as therapeutic agents
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Abstract
Provided are deuterated analogs of MDMA, including deuterated empathogens. In some embodiments, such compounds are monoamine releasers or inhibit monoamine transporters. In some aspects, features of the compounds provide stability, such as metabolic stability, and efficacy. Also provided are methods for the preparation of deuterated empathogens and pharmaceutical compositions comprising the same. Methods of using the deuterated empathogens, alone or in combination with other therapeutic agents, are provided. In some embodiments, deuterated empathogens are used to treat CNS disorders, such as mental health conditions and neurodegenerative disorders.
Claims (37)
1. A method of treating a mental health disorder in a subject, comprising administering to the subject a therapeutically effective amount of a compound of any of Formulas (IIIA), (IIIB), (IIIC), (IIIE), (IIIF), (IVA), (IVB), or (IVC):
wherein each Y is independently protium (H) or deuterium (D), and
wherein at least one Y is deuterium (D) and the remaining Ys are protium (H);
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof;
provided that the compound is not
and wherein the mental health disorder is a trauma- or stressor-related disorder, an anxiety disorder, or a depressive disorder.
2. The method of claim 1 , comprising administering a compound of any of Formulas (IIIA), (IIIB), (IIIC), (IIIE), or (IIIF):
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof;
provided that the compound is not
3. The method of claim 2 , comprising administering a compound of Formula (IIIA) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.
4. The method of claim 2 , comprising administering a compound of Formula (IIIB) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.
5. The method of claim 2 , comprising administering a compound of Formula (IIIE) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.
6. The method of claim 2 , comprising administering a compound of Formula (IIIE) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.
7. The method of claim 2 , comprising administering a compound of Formula (IIIF) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.
8. The method of claim 1 , comprising administering a compound of any of Formulas (IVA), (IVB), or (IVC):
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof;
provided that the compound is not
9. The method of claim 8 , comprising administering a compound of Formula (IVA) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.
10. The method of claim 8 , comprising administering a compound of Formula (IVB) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.
11. The method of claim 8 , comprising administering a compound of Formula (IVC) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.
12. The method of claim 1 , wherein the trauma- or stressor-related disorder is acute stress disorder (ASD).
13. The method of claim 1 , wherein the trauma- or stressor-related disorder is an adjustment disorder.
14. The method of claim 1 , wherein the trauma- or stressor-related disorder is post-traumatic stress disorder (PTSD).
15. The method of claim 1 , wherein the anxiety disorder is generalized anxiety disorder (GAD).
16. The method of claim 1 , wherein the depressive disorder is major depressive disorder (MDD).
17. The method of claim 1 , wherein the depressive disorder is treatment-resistant depression (TRD).
18. The method of claim 1 , wherein the depressive disorder is postpartum depression.
19. The method of claim 1 , wherein the depressive disorder is a depressive disorder due to a medical condition.
20. The method of claim 1 , wherein the compound is administered together with one or more sessions of psychotherapy or psychological support.
Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Dec 25, 2024
From: DALEY, PAUL F, DR.; COZZI, NICHOLAS V, DR.
To: ALEXANDER SHULGIN RESEARCH INSTITUTE, INC.
Reel/Frame 069677/0787 →
Continuity (4)
Division
18549374
Provisional Application
63236224
· Aug 23, 2021
Provisional Application
63236221
· Aug 23, 2021
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