# US 12,180,137 B1 · Solid forms of enantiopure deuterium-enriched bupropion and methods of use thereof

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- Number: US 12,180,137 B1
- Document ID: US12180137B1
- Status: Granted
- Kind: B1
- Application number: 18/652,164
- Filed: 2024-05-01
- Granted: 2024-12-31
- Earliest claimed: 2024-05-01
- Assignees: DeuteRx, LLC
- Applicants: DeuteRx, LLC
- Inventors: Vincent Jacques; William Perrault
- Web page: https://patentgrep.com/patent/US12180137B1

## CPC

- C07C 225/06: and acyclic
- A61K 31/137: Arylalkylamines, e.g. amphetamine, epinephrine, salbutamol, ephedrine {or methadone}
- C07C 225/16: and containing six-membered aromatic rings
- C07B 2200/05: Isotopically modified compounds, e.g. labelled
- C07B 2200/07: Optical isomers
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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)
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

The present disclosure provides a crystalline form of enantiopure deuterium-enriched bupropion, pharmaceutical compositions, and methods of treating mood disorders, neurological disorders, movement disorders, cardiovascular disorders, metabolic disorders, and other disorders using a crystalline form of enantiopure deuterium-enriched bupropion.

## Claims

### Claim 1

A crystalline form of a compound represented by Formula (I):
wherein R1, R2, and R3 are each independently H or D, provided that the abundance of deuterium in each of R1, R2, and R3 is at least 30%, and wherein the crystalline form of the compound is characterized by an X-ray powder diffraction pattern comprising peaks at the following diffraction angles (2θ): 12.3°±0.2°, 15.3°±0.2°, and 15.8°±0.2°.

### Claim 2 (depends on 1)

The crystalline form of claim 1, wherein the crystalline form of the compound is characterized by an X-ray powder diffraction pattern further comprising one or more peaks at the following diffraction angles (2θ): 13.4°±0.2°, 14.1°±0.2°, 16.9°±0.2°, 17.3°±0.2°, 18.4°±0.2°, 18.8°±0.2°, 22.0°±0.2°, and 22.8°±0.2°.

### Claim 3 (depends on 1)

The crystalline form of claim 1, wherein the crystalline form of the compound has a melting point onset as determined by differential scanning calorimetry at about 225° C. to about 235° C.

### Claim 4 (depends on 1)

The crystalline form of claim 1, wherein the crystalline form of the compound is anhydrous.

### Claim 5 (depends on 1)

The crystalline form of claim 1, wherein the abundance of deuterium in R1 is at least 50%.

### Claim 6 (depends on 1)

The crystalline form of claim 1, wherein the abundance of deuterium in R2 is at least 50%.

### Claim 7 (depends on 1)

The crystalline form of claim 1, wherein the abundance of deuterium in R3 is at least 50%.

### Claim 8 (depends on 1)

The crystalline form of claim 1, wherein the abundance of deuterium in each of R1, R2, and R3 is at least 50%.

### Claim 9 (depends on 1)

The crystalline form of claim 1, wherein the abundance of deuterium in each of R1, R2, and R3 is at least 75%.

### Claim 10 (depends on 1)

The crystalline form of claim 1, wherein the abundance of deuterium in each of R1, R2, and R3 is at least 90%.

### Claim 11 (depends on 1)

The crystalline form of claim 1, wherein the abundance of deuterium in each of R1, R2, and R3 is at least 95%.

### Claim 12 (depends on 1)

The crystalline form of claim 1, wherein the crystalline form of the compound is characterized by a stereochemical purity of at least 75% enantiomeric excess at the carbon bearing variable R1.

### Claim 13 (depends on 1)

The crystalline form of claim 1, wherein the crystalline form of the compound is characterized by a stereochemical purity of at least 90% enantiomeric excess at the carbon bearing variable R1.

### Claim 14 (depends on 1)

The crystalline form of claim 1, wherein the crystalline form of the compound is characterized by a stereochemical purity of at least 95% enantiomeric excess at the carbon bearing variable R1.

### Claim 15 (depends on 1)

A pharmaceutical composition comprising a crystalline form of claim 1, and a pharmaceutically acceptable excipient.