# US 12,110,272 B2 · Deuterated tryptamine derivatives and methods of use

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- Number: US 12,110,272 B2
- Document ID: US12110272B2
- Status: Granted
- Kind: B2
- Application number: 18/353,492
- Filed: 2023-07-17
- Published: 2023-11-09
- Granted: 2024-10-08
- Earliest claimed: 2020-05-19
- Assignees: Cybin IRL Limited
- Applicants: Cybin Irl Limited
- Inventors: Alex Nivorozhkin; Michael Palfreyman
- Web page: https://patentgrep.com/patent/US12110272B2

## CPC

- A61P 25/00: Drugs for disorders of the nervous system
- C07D 209/16: Tryptamines
- A61K 9/20: Pills, tablets, {discs, rods (A61K9/0004, A61K9/0007, A61K9/0056, A61K9/0065 take precedence; for reconstitution of a drink A61K9/0095)}
- A61K 9/2054: {Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose}
- A61K 31/4045: Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
- C07F 9/572: Five-membered rings
- A61K 9/2027: {obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates}
- A61K 9/2031: {obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers}
- A61K 9/2059: {Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin}
- C07B 59/002: {Heterocyclic compounds}
- C07B 2200/05: Isotopically modified compounds, e.g. labelled
- C07B 2200/07: Optical isomers
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

The present disclosure is directed to chemical compounds and to the use of such compounds in the treatment of diseases associated with a serotonin 5-HT2 receptor.

## Claims

### Claim 1

A method of treating generalized anxiety disorder (GAD) in a subject, comprising administering to the subject a therapeutically effective amount of a compound, which is:
or a pharmaceutically acceptable salt, solvate, or prodrug thereof.

### Claim 2 (depends on 1)

The method of claim 1, wherein the compound is
or a pharmaceutically acceptable salt or solvate thereof.

### Claim 3 (depends on 1)

The method of claim 1, wherein the compound is a pharmaceutically acceptable salt of

### Claim 4

A method of treating major depressive disorder (MDD) and/or treatment-resistant depression (TRD) in a subject, comprising administering to the subject a therapeutically effective amount of a compound, which is:
or a pharmaceutically acceptable salt, solvate, or prodrug thereof.

### Claim 5 (depends on 4)

The method of claim 4, wherein the subject has major depressive disorder (MDD).

### Claim 6 (depends on 5)

The method of claim 5, wherein the compound is
or a pharmaceutically acceptable salt or solvate thereof.

### Claim 7 (depends on 5)

The method of claim 5, wherein the compound is a pharmaceutically acceptable salt of

### Claim 8 (depends on 4)

The method of claim 4, wherein the subject has treatment-resistant depression (TRD).

### Claim 9 (depends on 8)

The method of claim 8, wherein the compound is
or a pharmaceutically acceptable salt or solvate thereof.

### Claim 10 (depends on 8)

The method of claim 8, wherein the compound is a pharmaceutically acceptable salt of

### Claim 11

A method of treating a bipolar disorder in a subject, comprising administering to the subject a therapeutically effective amount of a compound, which is:
or a pharmaceutically acceptable salt, solvate, or prodrug thereof.

### Claim 12 (depends on 11)

The method of claim 11, wherein the bipolar disorder is bipolar II disorder.

### Claim 13 (depends on 12)

The method of claim 12, wherein the compound is
or a pharmaceutically acceptable salt or solvate thereof.

### Claim 14 (depends on 12)

The method of claim 12, wherein the compound is a pharmaceutically acceptable salt of

### Claim 15

A method of treating a substance use disorder in a subject, comprising administering to the subject a therapeutically effective amount of a compound, which is:
or a pharmaceutically acceptable salt, solvate, or prodrug thereof.

### Claim 16 (depends on 15)

The method of claim 15, wherein the substance use disorder is alcohol use disorder.

### Claim 17 (depends on 16)

The method of claim 16, wherein the compound is
or a pharmaceutically acceptable salt or solvate thereof.

### Claim 18 (depends on 16)

The method of claim 16, wherein the compound is a pharmaceutically acceptable salt of