# US 11,299,458 B2 · Crystalline compounds

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 11,299,458 B2
- Document ID: US11299458B2
- Status: Granted
- Kind: B2
- Application number: 16/993,648
- Filed: 2020-08-14
- Published: 2021-07-01
- Granted: 2022-04-12
- Earliest claimed: 2015-06-17
- Assignees: Otsuka America Pharmaceutical, Inc.
- Applicants: Otsuka America Pharmaceutical, Inc.
- Inventors: Anthony Alexander McKinney; Franklin Bymaster; Walter Piskorski; Fred J. Fleitz; Yonglai Yang; David A. Engers; Valeriya Smolenskaya; Venkat Kusukuntla
- Web page: https://patentgrep.com/patent/US11299458B2

## CPC

- C07D 209/52: condensed with a ring other than six-membered
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/30: for treating abuse or dependence
- C07C 211/17: containing only non-condensed rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

The present invention relates to crystalline forms of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane hydrochloride and compositions comprising the same and methods of making and using the same.

## Claims

### Claim 1

A process for making Crystalline Form B of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane hydrochloride, wherein the process comprises seeding a solution or slurry of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane hydrochloride with Crystalline Form B of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane hydrochloride, wherein the Crystalline Form B exhibits an X-ray powder diffraction (XRPD) pattern comprising d-spacing (Å) values of 14.6, 5.1, 4.7, 4.6, and 3.6.

### Claim 2 (depends on 1)

The process of claim 1, wherein the solution or slurry is seeded while the temperature of the solution or slurry is above room temperature.

### Claim 3 (depends on 1)

The process of claim 1, wherein the Crystalline Form B exhibits an X-ray powder diffraction (XRPD) pattern measured using an incident beam of Cu Kα radiation of wavelength 1.54059 Å substantially as shown in any figure selected from FIGS. 40 and 48.

### Claim 4 (depends on 2)

The process of claim 2, wherein the Crystalline Form B exhibits an X-ray powder diffraction (XRPD) pattern measured using an incident beam of Cu Kα radiation of wavelength 1.54059 Å substantially as shown in any figure selected from FIGS. 40 and 48.

### Claim 5 (depends on 1)

The process of claim 1 further comprising isolating the Crystalline Form B.

### Claim 6 (depends on 2)

The process of claim 2 further comprising isolating the Crystalline Form B.

### Claim 7 (depends on 3)

The process of claim 3 further comprising isolating the Crystalline Form B.

### Claim 8 (depends on 4)

The process of claim 4 further comprising isolating the Crystalline Form B.

### Claim 9

A process for making a pharmaceutical composition comprising Crystalline Form B of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane hydrochloride, wherein the process comprises isolating Crystalline Form B of (1R,5S)-1-(naphthalen-2-yl)-3-azabicyclo[3.1.0]hexane hydrochloride and admixing the isolated Crystalline Form B with a pharmaceutically acceptable diluent or carrier, wherein the Crystalline Form B exhibits an X-ray powder diffraction (XRPD) pattern comprising d-spacing (Å) values of 14.6, 5.1, 4.7, 4.6, and 3.6.

### Claim 10 (depends on 9)

The process of claim 9, wherein the Crystalline Form B exhibits an X-ray powder diffraction (XRPD) pattern measured using an incident beam of Cu Kα radiation of wavelength 1.54059 Å substantially as shown in any figure selected from FIGS. 40 and 48.