Granted Patent B2

US 12,630,504 · App. 18/041,728 · Granted May 19, 2026

Inventors: Alex Belser (Brooklyn, NY); Clinton E. Canal (Atlanta, GA); Brett J. Greene (Fitchburg, MA); Joshua A. Hartsel (Lake Forest, CA); Alex Nivorozhkin (West Roxbury, MA); Michael Palfreyman (Waltham, MA); Francesco Salituro (Marlborough, MA)

Assignee: Cybin IRL Limited

C07C323/32A61K9/20A61K31/36A61K31/39A61P15/00A61P25/00A61P25/18C07B59/004C07C217/60C07C323/20C07D277/64C07D277/68C07D317/50C07D317/62C07B2200/05

Abstract

Claims (31)

1 . A compound having a structure of formula (II):

or a pharmaceutically acceptable salt, solvate, stereoisomer, or prodrug thereof,

wherein:

X 1 and X 2 are independently hydrogen, deuterium, or a substituted or unsubstituted C 1 -C 6 alkyl;

Y 1 and Y 2 are independently hydrogen, deuterium, or a substituted or unsubstituted C 1 -C 6 alkyl;

R 2 and R 3 are independently hydrogen, deuterium, halogen, a substituted or unsubstituted C 1 -C 6 alkyl, —OR a , or —SR a ;

R 6 and R 7 are independently hydrogen, an unsubstituted C 1 -C 6 alkyl, or a C 1 -C 6 alkyl substituted with one or more deuterium;

each R a is independently hydrogen, deuterium, or a substituted or unsubstituted C 1 -C 6 alkyl;

A is S; and

Z 1 and Z 2 are independently deuterium, or fluorine.

2 . The compound of claim 1 , wherein R 2 is —OR a .

3 . The compound of claim 1 , wherein X 1 and X 2 are hydrogen.

4 . The compound of claim 1 , wherein X 1 and X 2 are deuterium.

5 . The compound of claim 1 , wherein X 1 is hydrogen or deuterium, and X 2 is a substituted or unsubstituted C 1 -C 6 alkyl.

6 . The compound of claim 1 , wherein Z 1 and Z 2 are fluorine.

7 . The compound of claim 1 , wherein Z 1 and Z 2 are deuterium.

8 . The compound of claim 1 , which is selected from the group consisting of

or a pharmaceutically acceptable salt, solvate, stereoisomer, or prodrug thereof.

9 . A pharmaceutical composition, comprising the compound of claim 1 and a pharmaceutically acceptable excipient.

10 . The pharmaceutical composition of claim 9 , which is formulated for oral administration.

11 . The pharmaceutical composition of claim 9 , which is formulated for administration via inhalation.

12 . A method of treating a subject with a disease or disorder associated with a serotonin 5-HT 2 receptor, the method comprising:

administering to the subject a therapeutically effective amount of the compound of claim 1 .

13 . The method of claim 12 , wherein the disease or disorder associated with a serotonin 5-HT 2 receptor is a neuropsychiatric disease or disorder or an inflammatory disease or disorder.

14 . The method of claim 12 , wherein the disease or disorder associated with a serotonin 5-HT 2 receptor is a central nervous system (CNS) disorder.

15 . The method of claim 14 , wherein the central nervous system (CNS) disorder is selected from the group consisting of post-traumatic stress disorder (PTSD), major depressive disorder (MDD), treatment-resistant depression (TRD), suicidal ideation, suicidal behavior, major depressive disorder with suicidal ideation or suicidal behavior, non-suicidal self-injury disorder (NSSID), a bipolar disorder and related disorders, cyclothymic disorder, obsessive-compulsive disorder (OCD), generalized anxiety disorder (GAD), social anxiety disorder, a substance use disorder, anorexia nervosa, bulimia nervosa, binge eating disorder, Alzheimer's disease, cluster headache and migraine, attention deficit hyperactivity disorder (ADHD), pain, aphantasia, childhood-onset fluency disorder, major neurocognitive disorder, mild neurocognitive disorder, sexual dysfunction, chronic fatigue syndrome, Lyme disease, and obesity.

16 . The method of claim 14 , wherein the central nervous system (CNS) disorder is pain.

17 . The method of claim 14 , wherein the central nervous system (CNS) disorder is sexual dysfunction.

18 . The method of claim 12 , wherein the disease or disorder associated with a serotonin 5-HT 2 receptor is an autonomic nervous system (ANS) disorder.

19 . The method of claim 18 , wherein the autonomic nervous system (ANS) disorder is a pulmonary disorder or a cardiovascular disorder.

20 . The method of claim 12 , wherein the compound is administered orally, sublingually, buccally, topically, via injection, or via inhalation.

Assignments (1)

Continuity (3)

References Cited (163)