# US 2021/0332016 A1 · Solid forms of an n-terminal domain androgen receptor inhibitor and uses thereof

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- Number: US 2021/0332016 A1
- Document ID: US20210332016A1
- Status: Published application
- Kind: A1
- Application number: 17/342,923
- Filed: 2021-06-09
- Published: 2021-10-28
- Earliest claimed: 2020-04-17
- Assignees: ESSA Pharma, Inc.
- Applicants: ESSA Pharma, Inc.
- Inventors: Han-Jie Zhou; Peter Virsik
- Web page: https://patentgrep.com/patent/US20210332016A1

## CPC

- C07D 239/69: Benzenesulfonamido-pyrimidines
- A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A61P 35/00: Antineoplastic agents
- C07D 239/42: One nitrogen atom (nitro radicals C07D239/30)
- C07B 2200/13: Crystalline forms, e.g. polymorphs
- 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
- C07B: GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR (preparation of carboxylic acid esters by telomerisation C07C67/47; telomerisation C08F)

## Abstract

The present invention relates to a crystalline form of Compound I, a salt, a solvate, or a solvate salt thereof or an amorphous form of Compound I, a salt, a solvate, or a solvate salt thereof. The present invention also provides compositions comprising the crystalline form and/or the amorphous form, therapeutic uses of the crystalline forms and/or the amorphous forms, and the compositions thereof.

## Claims

### Claim 1

An amorphous form of Compound I:
or a pharmaceutically acceptable salt, solvate, or solvate salt thereof.

### Claim 2 (depends on 1)

The amorphous form of claim 1, wherein Compound I is anhydrous or non-solvated.

### Claim 3 (depends on 1)

The amorphous form of claim 1, wherein Compound I is not present as a pharmaceutically acceptable salt.

### Claim 4 (depends on 1)

The amorphous form of claim 1 exhibiting an XRPD pattern substantially similar to FIG. 7 (third spectrum from bottom), provided that peaks at 27.3±0.2 and 31.7±0.2 degrees two-theta are excluded.

### Claim 5 (depends on 1)

The amorphous form of claim 1 which exhibits a differential scanning calorimetry (DSC) thermogram comprising an exotherm peak at about 91° C.

### Claim 6 (depends on 1)

The amorphous form of claim 1 which exhibits a differential scanning calorimetry (DSC) thermogram comprising an endotherm peak which onset at about 178° C.

### Claim 7 (depends on 1)

The amorphous form of claim 1 which exhibits a glass transition temperature at about 61° C.

### Claim 8 (depends on 1)

The amorphous form of claim 1 which exhibits a thermogravimetric analysis (TGA) thermogram comprising a change in slope which onset at about 280° C.

### Claim 9 (depends on 1)

The amorphous form of claim 1, wherein the amorphous form has a purity of about 95% or higher.

### Claim 10 (depends on 1)

The amorphous form of claim 1, wherein the amorphous form has a purity of about 99% or higher.

### Claim 11 (depends on 1)

The amorphous form of claim 1, wherein the amorphous form exhibits an X-ray powder diffraction (XRPD) pattern substantially similar to any one of the patterns shown in FIGS. 13 and 15.

### Claim 12 (depends on 11)

The amorphous form of claim 11 which exhibits an XRPD pattern substantially similar to a pattern labeled as SDD-A, SDD-B, SDD-C, SDD-D, or SDD-E in FIG. 13 or a pattern labeled as SDD-H, SDD-I, SDD-J, SDD-N, SDD-O, SDD-O, SDD-P, SDD-Q, or SDD-R in FIG. 15.

### Claim 13 (depends on 11)

The amorphous form of claim 11 which exhibits a glass transition temperature (Tg) in the range of about 60° C. to about 180° C. as measured by differential scanning calorimeter.

### Claim 14 (depends on 11)

The amorphous form of claim 11 which exhibits a glass transition temperature (Tg) in the range of about 60° C. to about 90° C. as measured by differential scanning calorimeter.

### Claim 15 (depends on 11)

The amorphous form of claim 11 having a purity in the range of about 80% to about 99%.

### Claim 16 (depends on 11)

The amorphous form of claim 11 having a purity of about 95% or higher.

### Claim 17 (depends on 11)

The amorphous form of claim 11 comprising less than 10% of crystalline form of Compound I or a pharmaceutically acceptable salt, solvate, stereoisomer or prodrug thereof.

### Claim 18 (depends on 11)

The amorphous form of claim 11 comprising less than 5% of crystalline form of Compound I or a pharmaceutically acceptable salt, solvate, stereoisomer or prodrug thereof.

### Claim 19 (depends on 1)

A composition comprising an amorphous form of claim 1 and a pharmaceutically acceptable carrier.

### Claim 20 (depends on 19)

The composition of claim 19, wherein the composition is a pharmaceutical solid dispersion composition.

### Claim 21 (depends on 19)

The composition of claim 19, further comprising one or more additional therapeutic agents.

### Claim 22

An amorphous form of Compound I:

### Claim 23 (depends on 22)

The amorphous form of claim 22 having a purity of about 95% or higher.

### Claim 24 (depends on 22)

A composition comprising an amorphous form of claim 22 and a pharmaceutically acceptable carrier.

### Claim 25 (depends on 24)

The composition of claim 24, wherein the composition is a pharmaceutical solid dispersion composition.