IP Library Granted Patent US 10,329,287
Granted Patent B2
US 10,329,287 · App. 15/644,547 · Granted Jun 25, 2019

Benzimidazole-proline derivatives

Inventors: Christoph Boss (Allschwil, CH); Christine Brotschi (Allschwil, CH); Markus Gude (Allschwil, CH); Bibia Heidmann (Allschwil, CH); Thierry Sifferlen (Allschwil, CH); Jodi T. Williams (Allschwil, CH)
Assignee: IDORSIA PHARMACEUTICALS LTD
C07D417/14C07D401/14C07D403/04C07D403/14
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Quick Facts
Patent No.
US 10,329,287
App. No.
15/644,547
Granted
Jun 25, 2019
Kind
B2
Abstract

The present invention relates to compounds of the formula (II) wherein Ar 1 , R 1 , R 2 , R 3 , R 4a , R 4b and (R 5 ) n are as described in the description, to their preparation, to pharmaceutically acceptable salts thereof, and to their use as pharmaceuticals, to pharmaceutical compositions containing one or more compounds of formula (II), and especially to their use as orexin receptor antagonists.

Claims (33)

1. The compound [(S)-2-(5-Chloro-4-methyl-1H-benzoimidazol-2-yl)-2-methyl-pyrrolidin-1-yl]-(2-[1,2,3]triazol-2-yl-phenyl)-methanone; or a pharmaceutically acceptable salt thereof.

2. The compound [(S)-2-(5-Chloro-4-methyl-1H-benzoimidazol-2-yl)-2-methyl-pyrrolidin-1-yl]-(2-[1,2,3]triazol-2-yl-phenyl)-methanone in pharmaceutically acceptable salt form.

3. The compound [(S)-2-(5-Chloro-4-methyl-1H-benzoimidazol-2-yl)-2-methyl-pyrrolidin-1-yl]-(2-[1,2,3]triazol-2-yl-phenyl)-methanone in free form.

4. A pharmaceutical composition comprising, as active principle, the compound according to claim 1 , or a pharmaceutically acceptable salt thereof, and at least one therapeutically inert excipient.

5. A pharmaceutical composition comprising, as active principle, the compound according to claim 2 , and at least one therapeutically inert excipient.

6. A pharmaceutical composition comprising, as active principle, the compound according to claim 3 , and at least one therapeutically inert excipient.

7. A method to treat a disease or disorder selected from

a) a sleep disorder selected from an insomnia; a primary insomnia; an idiopathic insomnia; an insomnia associated with depression, emotional/mood disorders, aging, Alzheimer's disease or cognitive impairment; REM sleep interruptions; a breathing-related sleep disorder; a sleep apnea; a periodic limb movement disorder, a restless leg syndrome; a circadian rhythm sleep disorder; a shift work sleep disorder; and a jet-lag syndrome; and

b) an anxiety disorder selected from a post-traumatic stress disorder, an obsessive compulsive disorder, a panic attack, a phobic anxiety, and an avoidance;

comprising administering to a patient in need thereof, the compound of claim 1 in free or pharmaceutically acceptable salt form.

8. A method to treat a disease or disorder selected from

a) a sleep disorder selected from an insomnia; a primary insomnia; an idiopathic insomnia; an insomnia associated with depression, emotional/mood disorders, aging, Alzheimer's disease or cognitive impairment; REM sleep interruptions; a breathing-related sleep disorder; a sleep apnea; a periodic limb movement disorder, a restless leg syndrome; a circadian rhythm sleep disorder; a shift work sleep disorder; and a jet-lag syndrome; and

b) an anxiety disorder selected from a post-traumatic stress disorder, an obsessive compulsive disorder, a panic attack, a phobic anxiety, and an avoidance;

comprising administering to a patient in need thereof, the compound of claim 2 .

9. A method to treat a disease or disorder selected from

a) a sleep disorder selected from an insomnia; a primary insomnia; an idiopathic insomnia; an insomnia associated with depression, emotional/mood disorders, aging, Alzheimer's disease or cognitive impairment; REM sleep interruptions; a breathing-related sleep disorder; a sleep apnea; a periodic limb movement disorder, a restless leg syndrome; a circadian rhythm sleep disorder; a shift work sleep disorder; and a jet-lag syndrome; and

b) an anxiety disorder selected from a post-traumatic stress disorder, an obsessive compulsive disorder, a panic attack, a phobic anxiety, and an avoidance;

comprising administering to a patient in need thereof, the compound of claim 3 .

10. A method to treat a disease or disorder selected from

a) a sleep disorder selected from an insomnia; a primary insomnia; an idiopathic insomnia; an insomnia associated with depression, emotional/mood disorders, aging, Alzheimer's disease or cognitive impairment; REM sleep interruptions; a breathing-related sleep disorder; a sleep apnea; a periodic limb movement disorder, a restless leg syndrome; a circadian rhythm sleep disorder; a shift work sleep disorder; and a jet-lag syndrome;

b) an anxiety disorder; and

c) an addiction disorder;

comprising administering to a patient in need thereof, the compound of claim 1 in free or pharmaceutically acceptable salt form.

11. A method to treat a disease or disorder selected from

a) a sleep disorder selected from an insomnia; a primary insomnia; an idiopathic insomnia; an insomnia associated with depression, emotional/mood disorders, aging, Alzheimer's disease or cognitive impairment; REM sleep interruptions; a breathing-related sleep disorder; a sleep apnea; a periodic limb movement disorder, a restless leg syndrome; a circadian rhythm sleep disorder; a shift work sleep disorder; and a jet-lag syndrome;

b) an anxiety disorder; and

c) an addiction disorder;

comprising administering to a patient in need thereof, the compound of claim 2 .

12. A method to treat a disease or disorder selected from

a) a sleep disorder selected from an insomnia; a primary insomnia; an idiopathic insomnia; an insomnia associated with depression, emotional/mood disorders, aging, Alzheimer's disease or cognitive impairment; REM sleep interruptions; a breathing-related sleep disorder; a sleep apnea; a periodic limb movement disorder, a restless leg syndrome; a circadian rhythm sleep disorder; a shift work sleep disorder; and a jet-lag syndrome;

b) an anxiety disorder; and

c) an addiction disorder;

comprising administering to a patient in need thereof, the compound of claim 3 .

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 Apr 4, 2025
From: ACTELION PHARMACEUTICALS LTD
To: IDORSIA PHARMACEUTICALS LTD
Reel/Frame 070734/0448 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 22, 2017
From: BOSS, CHRISTOPH; BROTSCHI, CHRISTINE; GUDE, MARKUS; HEIDMANN, BIBIA; SIFFERLEN, THIERRY; WILLIAMS, JODI T.
To: ACTELION PHARMACEUTICALS LTD
Reel/Frame 044202/0385 →
Priority Claims (2)
EP 12170748 · Jun 4, 2012 · regional
EP 13158520 · Mar 11, 2013 · regional
Continuity (2)
Continuation 14405649
Related Publication 20170305897A1 · Oct 26, 2017