# US 2019/0169123 A1 · Crystal forms and production methods thereof

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- Number: US 2019/0169123 A1
- Document ID: US20190169123A1
- Status: Published application
- Kind: A1
- Application number: 16/209,263
- Filed: 2018-12-04
- Published: 2019-06-06
- Earliest claimed: 2017-12-05
- Assignees: Sunovion Pharmaceuticals Inc.
- Applicants: Sunovion Pharmaceuticals Inc.
- Inventors: John R. Snoonian; Harold Scott Wilkinson
- Web page: https://patentgrep.com/patent/US20190169123A1

## CPC

- C07D 207/09: Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

The various aspects present inventions provide various crystalline forms of (S)-(−)-amisulpride, (R)-(+)-amisulpride, and solvates thereof and methods of making same. In various aspects, the inventions also provide methods of resolving racemic amisulpride.

## Claims

### Claim at position 1

1-49. (canceled)

### Claim 50

A crystalline form of (R)-(+)-amisulpride characterized by a powder x-ray diffraction pattern comprising peaks, in terms of 2-theta, at 7.0±0.2°, 9.7±0.2°, and 15.4±0.2°.

### Claim 51 (depends on 50)

The crystalline (R)-(+)-amisulpride of claim 50, further characterized by the powder x-ray diffraction pattern further comprising peaks, in terms of 2-theta, at 9.3±0.2°, and 19.4±0.2°.

### Claim 52 (depends on 51)

The crystalline (R)-(+)-amisulpride of claim 51, further characterized by the powder x-ray diffraction pattern further comprising peaks, in terms of 2-theta, at 14.9±0.2°, 16.9±0.2°, and 20.1±0.2°.

### Claim 53 (depends on 52)

The crystalline (R)-(+)-amisulpride of claim 52, further characterized by the powder x-ray diffraction pattern further comprising peaks, in terms of 2-theta, at 19.0±0.2°, 21.0±0.2°, and 23.2±0.2°.

### Claim 54 (depends on 50)

The crystalline (R)-(+)-amisulpride of claim 50, characterized by a powder x-ray diffraction pattern substantially in accord with FIG. 2B.

### Claim 55 (depends on 50)

The crystalline (R)-(+)-amisulpride of claim 50, characterized by having a melting point at about 102±3° C.

### Claim 56 (depends on 50)

The crystalline (R)-(+)-amisulpride of claim 50, characterized by a differential scanning calorimetry thermogram comprising an endothermic event at 101±3° C.

### Claim 57 (depends on 50)

The crystalline (R)-(+)-amisulpride of claim 50, having a differential scanning calorimetry thermogram substantially in accord with FIG. 2A.

### Claim 58

A crystalline form of (S)-(−)-amisulpride characterized by a powder x-ray diffraction pattern comprising peaks, in terms of 2-theta, at 7.0±0.2°, 9.7±0.2°, and 15.4±0.2°.

### Claim 59 (depends on 58)

The crystalline (S)-(−)-amisulpride of claim 58, further characterized by the powder x-ray diffraction pattern further comprising peaks, in terms of 2-theta, at 9.3±0.2°, and 19.4±0.2°.

### Claim 60 (depends on 59)

The crystalline (S)-(−)-amisulpride of claim 59, further characterized by the powder x-ray diffraction pattern further comprising peaks, in terms of 2-theta, at 14.9±0.2°, 16.9±0.2°, and 20.2±0.2°.

### Claim 61 (depends on 60)

The crystalline (S)-(−)-amisulpride of claim 60, further characterized by the powder x-ray diffraction pattern further comprising peaks, in terms of 2-theta, at 19.1±0.2°, 21.0±0.2°, and 23.2±0.2°.

### Claim 62 (depends on 58)

The crystalline (S)-(−)-amisulpride of claim 58, characterized by a powder x-ray diffraction pattern substantially in accord with FIG. 3B.

### Claim 63 (depends on 58)

The crystalline (S)-(−)-amisulpride of claim 58 characterized by having a melting point at about 102±3° C.

### Claim 64 (depends on 58)

The crystalline (S)-(−)-amisulpride of claim 58, characterized by a differential scanning calorimetry thermogram comprising an endothermic event at 101±3° C.

### Claim 65 (depends on 58)

The crystalline (S)-(−)-amisulpride of claim 58, having a differential scanning calorimetry thermogram substantially in accord with FIG. 3A.

### Claim 66

A crystalline (R)-(+)-amisulpride or (S)-(−)-amisulpride characterized by single crystal x-ray diffraction having a P1 space group and cell formula units (Z) of 4.

### Claim 67 (depends on 66)

The crystalline form of (R)-(+)-amisulpride of claim 66, wherein the P1 space group has unit cell parameters: a is about 12.3 Å, b is about 12.8 Å, c is about 14.1 Å, α is about 64.0°, β is about 73.4°, and γ is about 75.9°.

### Claim 68 (depends on 66)

The crystalline form of (S)-(−)-amisulpride of claim 66, wherein the P1 space group has unit cell parameters: a is about 12.4 Å, b is about 12.8 Å, c is about 14.1 Å, α is about 64.2°, β is about 73.6°, and γ is about 75.8°.

### Claim 69 (depends on 50)

A pharmaceutical composition comprising the crystalline form of claim 50 and a pharmaceutically acceptable carrier or diluent.

### Claim 70 (depends on 58)

A pharmaceutical composition comprising the crystalline form of claim 58 and a pharmaceutically acceptable carrier or diluent.

### Claim 71 (depends on 66)

A pharmaceutical composition comprising the crystalline form of claim 66 and a pharmaceutically acceptable carrier or diluent.