Polymorphic forms of the sodium salt of 4-tert-butyl-N-[4-chloro-2-(1-oxy-pyridine-4-carbonyl)-phenyl]-benzene sulfonamide

• US 9,150,513 B2
• Filed: 07/20/2012
• Issued: 10/06/2015
• Est. Priority Date: 07/22/2011
• Status: Active Grant

• Current Assignee: ChemoCentryx, Inc. (Amgen Inc.)
• Original Assignee: ChemoCentryx, Inc. (Amgen Inc.)
• Inventors: Bis, Joanna, Igo, David H.
• Primary Examiner(s): CHANDRAKUMAR, NIZAL S
• Application Number:
  US14/234,279
• Publication Number:
  US 20140171473A1
• Time in Patent Office: 1,173 Days
• Field of Search: 546/328
• US Class Current: 1/1
• CPC Class Codes: A61K 31/44 Non condensed pyridines; Hydrogenated derivatives thereof
• CPC Class Codes: A61K 31/4425 Pyridinium derivatives, e.g. pralidoxime, pyridostigmine
• CPC Class Codes: A61K 45/06 Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
• CPC Class Codes: A61P 1/00 Drugs for disorders of the alimentary tract or the digestive system
• CPC Class Codes: A61P 1/04 for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
• CPC Class Codes: A61P 29/00 Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: C07B 2200/13 Crystalline forms, e.g. polymorphs
• CPC Class Codes: C07D 213/89 with hetero atoms directly attached to the ring nitrogen atom

Abstract

Disclosed are novel polymorphic solvated and desolvated forms of the sodium salt of 4-tert-butyl-N-[4-chloro-2-(1-oxy-pyridine-4-carbonyl)phenyl]-benzenesulfonamide. One embodiment of the present invention is directed to a crystalline sodium salt of 4-tert-butyl-N-[4-chloro-2-(1-oxy-pyridine-4-carbonyl)-phenyl]benzenesulfonamide (hereinafter “Compound A-1,4-dioxane/water solvate”), wherein the crystalline form is characterized by an X-ray powder diffraction pattern comprising diffraction angles (° 28), when measured using Cu Ku radiation, at about 4.0, 8.1, 10.1, 14.2, 16.2, 18.6, 20.3, 24.7, 25.0, and 26.5.

Claims

1. A crystalline form of a sodium salt of 4-tert-butyl-N-[4-chloro-2-(1-oxy-pyridine-4-carbonyl)-phenyl]-benzenesulfonamide in the form of a solvate, wherein the solvate consists of one unit of water and one unit of 1,4-dioxane.

2. The crystalline form of claim 1 characterized by an X-ray powder diffraction pattern substantially in accordance with FIG. 1.

3. The crystalline form of claim 1, wherein the crystalline form provides a Raman spectrum containing peaks at about 668, 743, 804, 1125, 1154, 1162, 1286, 1544, 1587, 1597, 1611, 1657, and 1672 cm⁻

1.

4. The crystalline form of claim 1, wherein the crystalline form provides a Raman spectrum substantially in accordance with FIG. 6.

5. A pharmaceutical composition comprising the crystalline form according to claim 1 and a pharmaceutically acceptable carrier.

6. A method of preparing a pharmaceutical composition comprising admixing the crystalline form according to claim 1 and a pharmaceutically acceptable carrier.

7. The crystalline form of claim 1, wherein the crystalline form differential scanning calorimetry themogram profile is substantially in accordance with FIG. 10.

8. The pharmaceutical composition of claim 5, further comprising a non-steroidal anti-inflammatory agent.

9. The pharmaceutical composition of claim 8, wherein the composition is adapted for oral administration.

10. The composition of claim 8 wherein the composition is in the form of a tablet or capsule.

11. The composition of claim 5, wherein the composition is in the form of a tablet or capsule.

12. The crystalline form of claim 1 characterized by an X-ray powder diffraction pattern containing diffraction angles, when measured using Cu K_α

radiation, at about 4.0, 8.1, 10.1, 14.2, 16.2, 18.6, 20.3, 24.7, 25.0, and 26.5 °

2θ

.

13. The crystalline form of claim 1, wherein the crystalline form is prepared from contacting the sodium salt of 4-tert-butyl-N-[4-chloro-2-(1-oxy-pyridine-4-carbonyl)-phenyl]-benzenesulfonamide with water, 1,4-dioxane, and sodium hydroxide.

14. The crystalline form of claim 13, characterized by an X-ray powder diffraction pattern containing diffraction angles, when measured using Cu K_α

radiation, at about 4.0, 8.1, 10.1, 14.2, 16.2, 18.6, 20.3, 24.7, 25.0, and 26.5 °

2θ

.

15. A pharmaceutical composition comprising the crystalline form according to claim 14 and a pharmaceutically acceptable carrier.