Crystalline forms of N-(4-(4-(cyclopropymethyl)piperazine-1-carbonyl)phenyl)quinoline-8-sulfonamide

Patent metadata

Field	Value
Publication number	US-11254652-B2
Application number	US-201816765456-A
Country	US
Kind code	B2
Filing date	Nov 21, 2018
Priority date	Nov 22, 2017
Publication date	Feb 22, 2022
Grant date	Feb 22, 2022

Abstract

Provided herein are amorphous and crystalline hemisulfate salt forms of the formula (I). Also provided are pharmaceutical compositions comprising the amorphous and crystalline hemisulfate salt forms, methods for their manufacture, and uses thereof for treating conditions associated with pyruvate kinase such as e.g., pyruvate kinase deficiency.

First claim

The invention claimed is:

1. A crystalline form of a compound having the formula:

wherein the crystalline form is crystalline Form A characterized by x-ray powder diffraction peaks at 2Θ angles (±0.2°) 9.9°, 15.8°, and 22.6°.

2. The crystalline form of claim 1 , wherein the compound is a solvate.

3. The crystalline Form A of claim 1 , wherein the crystalline form is characterized by x-ray powder diffraction peaks at 2Θ angles (±0.2°) 9.9°, 15.8°, and 22.6°; and at least one, at least two, or at least three additional x-ray powder diffraction peak at 2Θ angles (±0.2°) selected from 15.0°, 17.1°, 21.3°, and 21.9°.

4. The crystalline Form A of claim 3 , wherein the crystalline form is characterized by x-ray powder diffraction peaks at 2Θ angles (±0.2°) 9.9°, 11.4°, 15.0°, 15.3°, 15.8°, 17.1°, 17.7°, 21.3°, 21.9°, 22.6°, and 23.5°.

5. The crystalline Form A of claim 4 , wherein the crystalline form is characterized by x-ray powder diffraction peaks at 2Θ angles (±0.2°) 4.9°, 9.9°, 11.0°, 11.4°, 11.7°, 12.3°, 12.8°, 13.6°, 13.9°, 14.2°, 15.0°, 15.3°, 15.8°, 17.1°, 17.4°, 17.7°, 18.8°, 19.1°, 19.8°, 21.3°, 21.9°, 22.6°, 23.0°, 23.2°, 23.5°, 23.8°, 24.1°, 24.5°, 25.3°, 25.6°, 26.1°, 27.1°, 28.1°, and 29.8°.

6. A pharmaceutical composition comprising the crystalline form of claim 1 ; and a pharmaceutically acceptable carrier.

7. A tablet composition comprising the crystalline form of claim 1 ; and a pharmaceutically acceptable carrier.

8. A method of forming crystalline Form A of claim 1 , the method comprising reacting a compound of Formula 1:

with H 2 SO 4 in an alcoholic solution.

Assignees

• Agios Pharmaceuticals Inc

Inventors

• Sizemore Jacob P
• Guo Liting
• Mirmehrabi Mahmoud
• Su Yeqing

Classifications

• A61K9/2018

  Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates · CPC title

• A61P7/00

  Drugs for disorders of the blood or the extracellular fluid · CPC title

• A61K9/2013

  Organic compounds, e.g. phospholipids, fats · CPC title

• A61K9/2054

  Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose · CPC title

• A61P13/00

  Drugs for disorders of the urinary system · CPC title