# US 12,180,176 B2 · Fluorinated empathogens

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- Number: US 12,180,176 B2
- Document ID: US12180176B2
- Status: Granted
- Kind: B2
- Application number: 18/549,377
- Filed: 2022-08-23
- Published: 2024-08-29
- Granted: 2024-12-31
- Earliest claimed: 2021-08-23
- Assignees: Alexander Shulgin Research Institute, Inc.
- Applicants: Alexander Shulgin Research Institute, Inc.
- Inventors: Nicholas V Cozzi; Paul F Daley
- Web page: https://patentgrep.com/patent/US12180176B2

## CPC

- C07D 317/58: Radicals substituted by nitrogen atoms (nitro radicals C07D317/52)
- A61K 31/357: having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
- A61P 25/24: Antidepressants
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Provided are fluorinated analogs of MDMA, including fluorinated 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 fluorinated empathogens and pharmaceutical compositions comprising the same. Methods of using the fluorinated empathogens, alone or in combination with other therapeutic agents, are provided. In some embodiments, fluorinated empathogens are used to treat CNS disorders, such as mental health conditions and neurodegenerative disorders.

## Claims

### Claim 1

A compound of any of Formulas (IIIA), (IIIC), (IIID), (IIIE), (IIIF), (IVA), (IVB), (IVC), (IVD), (IVE), or (IVF):
wherein each Y is independently protium (H) or fluorine (F), and
wherein at least one Y is fluorine (F) and the remaining Ys are protium (H);
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof;
provided that the compound is not
(3,4-methylenedioxy-N-trifluoroethylamphetamine, MDTFEA).

### Claim 2 (depends on 1)

The compound of claim 1, wherein the compound is any of Formulas (IIIA), (IIIC), (IIID), (IIIE), or (IIIF):
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.

### Claim 3 (depends on 2)

The compound of claim 2, which is a compound of Formula (IIIA) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.

### Claim 4 (depends on 2)

The compound of claim 2, which is a compound of Formula (IIIC) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.

### Claim 5 (depends on 2)

The compound of claim 2, which is a compound of Formula (IIID) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.

### Claim 6 (depends on 2)

The compound of claim 2, which is a compound of Formula (IIIE) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.

### Claim 7 (depends on 2)

The compound of claim 2, which is a compound of Formula (IIIF) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.

### Claim 8 (depends on 1)

The compound of claim 1, wherein the compound is any of Formulas (IVA), (IVB), (IVC), (IVD), (IVE), or (IVF):
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.

### Claim 9 (depends on 8)

The compound of claim 8, which is a compound of Formula (IVA) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.

### Claim 10 (depends on 8)

The compound of claim 8, which is a compound of Formula (IVB) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.

### Claim 11 (depends on 8)

The compound of claim 8, which is a compound of Formula (IVC) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.

### Claim 12 (depends on 8)

The compound of claim 8, which is a compound of Formula (IVD) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.

### Claim 13 (depends on 8)

The compound of claim 8, which is a compound of Formula (IVE) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.

### Claim 14 (depends on 8)

The compound of claim 8, which is a compound of Formula (IVF) selected from the group consisting of:
or a pharmaceutically acceptable salt, prodrug, hydrate, or solvate thereof.

### Claim 15 (depends on 1)

A pharmaceutical composition comprising a therapeutically effective amount of a compound of claim 1, and a pharmaceutically acceptable carrier, diluent, or excipient.