IP Library Granted Patent US 10,023,560
Granted Patent B2
US 10,023,560 · App. 15/702,281 · Granted Jul 17, 2018

Crystalline salt form of (S)-(2-(6 chloro-7-methyl-1H-benzo[d]imidazol-2-yl)-2-methylpyrrolidin-1-yl)(5-methoxy-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone as orexin receptor antagonist

Inventors: Christoph Boss (Allschwil, CH); Christine Brotschi (Allschwil, CH); Markus Gude (Allschwil, CH); Bibia Heidmann (Allschwil, CH); Thierry Sifferlen (Allschwil, CH); Markus Von Raumer (Allschwil, CH); Jodi T. Williams (Allschwil, CH)
Assignee: IDORSIA PHARMACEUTICALS LTD
C07D403/14C07B2200/13
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Quick Facts
Patent No.
US 10,023,560
App. No.
15/702,281
Granted
Jul 17, 2018
Kind
B2
Abstract

The invention relates to a crystalline form of (S)-(2-(6-chloro-7-methyl-1H-benzo[d]imidazol-2-yl)-2-methylpyrrolidin-1-yl)(5-methoxy-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone hydrochloride, processes for the preparation thereof, pharmaceutical compositions containing said crystalline form, and its use as medicament, especially as orexin receptor antagonist.

Claims (13)

1. A method of treatment of a sleep disorder, an anxiety disorder, or an addiction disorder, a cognitive dysfunction, a mood disorder, or an appetite disorder; comprising administering to a patient an effective amount of the compound (S)-(2-(6-chloro-7-methyl-1H-benzo[d]imidazol-2-yl)-2-methylpyrrolidin-1-yl)(5-methoxy-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone hydrochloride in crystalline form; wherein said crystalline form comprises peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 11.0°, 24.1° and 24.5°, wherein said X-ray powder diffraction diagram is obtained by using combined Cu Kα1 and Kα2 radiation, without Kα2 stripping; and the accuracy of the 2θ values is in the range of 2θ+/−0.2°.

2. The method of claim 1 , wherein said crystalline form comprises peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 9.2°, 11.0°, 13.8°, 15.1°, 16.3°, 16.8°, 19.8°, 24.1°, 24.5°, and 27.3°, wherein said X-ray powder diffraction diagram is obtained by using combined Cu Kα1 and Kα2 radiation, without Kα2 stripping; and the accuracy of the 2θ values is in the range of 2θ+/−0.2°.

3. The method of claim 1 , wherein said crystalline form essentially shows the X-ray powder diffraction pattern as depicted in FIG. 2 .

4. The method of claim 2 , wherein the sleep disorder is a dyssomnia, a parasomnia, a sleep disorders associated with a general medical condition, or a substance-induced sleep disorder.

5. The method of claim 4 , wherein the anxiety disorder is a post-traumatic stress disorder, an obsessive compulsive disorder, a panic attack, a phobic anxiety, or an avoidance.

6. A method of treatment of a sleep disorder; comprising administering to a patient an effective amount of the compound (S)-(2-(6-chloro-7-methyl-1H-benzo[d]imidazol-2-yl)-2-methylpyrrolidin-1-yl)(5-methoxy-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone hydrochloride in crystalline form; wherein said crystalline form comprises peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 11.0°, 24.1° and 24.5°, wherein said X-ray powder diffraction diagram is obtained by using combined Cu Kα1 and Kα2 radiation, without Kα2 stripping; and the accuracy of the 2θ values is in the range of 2θ+/−0.2°.

7. The method of claim 6 , wherein said crystalline form comprises peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 9.2°, 11.0°, 13.8°, 15.1°, 16.3°, 16.8°, 19.8°, 24.1°, 24.5°, and 27.3°, wherein said X-ray powder diffraction diagram is obtained by using combined Cu Kα1 and Kα2 radiation, without Kα2 stripping; and the accuracy of the 2θ values is in the range of 2θ+/−0.2°.

8. The method of claim 7 , wherein the sleep disorder is a dyssomnia, a parasomnia, a sleep disorder associated with a general medical condition, or a substance-induced sleep disorder.

9. The method of claim 7 , wherein the sleep disorder is an insomnia, a sleep-related dystonia; a restless leg syndrome; a sleep apnea; a jet-lag syndrome; a shift work sleep disorder, a delayed or advanced sleep phase syndrome, or an insomnia related to psychiatric disorders.

10. The method of claim 7 , wherein the sleep disorder is an insomnia.

11. A method of treatment of an anxiety disorder; comprising administering to a patient an effective amount of the compound (S)-(2-(6-chloro-7-methyl-1H-benzo[d]imidazol-2-yl)-2-methylpyrrolidin-1-yl)(5-methoxy-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone hydrochloride in crystalline form; wherein said crystalline form comprises peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 11.0°, 24.1° and 24.5°, wherein said X-ray powder diffraction diagram is obtained by using combined Cu Kα1 and Kα2 radiation, without Kα2 stripping; and the accuracy of the 2θ values is in the range of 2θ+/−0.2°.

12. The method of claim 11 , wherein said crystalline form comprises peaks in the X-ray powder diffraction diagram at the following angles of refraction 2θ: 9.2°, 11.0°, 13.8°, 15.1°, 16.3°, 16.8°, 19.8°, 24.1°, 24.5°, and 27.3°, wherein said X-ray powder diffraction diagram is obtained by using combined Cu Kα1 and Kα2 radiation, without Kα2 stripping; and the accuracy of the 2θ values is in the range of 2θ+/−0.2°.

13. The method of claim 12 , wherein the anxiety disorder is a post-traumatic stress disorder, an obsessive compulsive disorder, a panic attack, a phobic anxiety, or an avoidance.

Assignments (3)
PATENT SECURITY AGREEMENT Recorded Jun 25, 2026
From: IDORSIA PHARMACEUTICALS LTD
To: BIOPHARMA CREDIT PLC, AS COLLATERAL AGENT
Reel/Frame 076038/0461 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 25, 2018
From: ACTELION PHARMACEUTICALS LTD
To: IDORSIA PHARMACEUTICALS LTD
Reel/Frame 046244/0794 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 26, 2018
From: BOSS, CHRISTOPH; BROTSCHI, CHRISTINE; GUDE, MARKUS; HEIDMANN, BIBIA; SIFFERLEN, THIERRY; VON RAUMER, MARKUS; WILLIAMS, JODI T.
To: ACTELION PHARMACEUTICALS LTD
Reel/Frame 045351/0787 →
Priority Claims (1)
WO PCT/IB2013/060595 · Dec 3, 2013 · international
Continuity (2)
Division 15101832
Related Publication 20180002317A1 · Jan 4, 2018