IP Library Granted Patent US 10,954,231
Granted Patent B2
US 10,954,231 · App. 15/844,264 · Granted Mar 23, 2021

Anxiolytic compounds

Inventors: Jonathan Bayldon Baell (Ivanhoe, AU); Brad Sleebs (Reservoir, AU); Bernard Luke Flynn (Donvale, AU); Ian Phillip Street (Macleod, AU); Nurul Quazi (Doncaster, AU); Chinh Thien Bui (North Balwyn, AU)
Assignee: Bionomics Limited
C07D471/04A61K31/4375A61K31/497A61K31/4985A61K31/5025A61K31/519A61K31/5377A61K45/06
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Quick Facts
Patent No.
US 10,954,231
App. No.
15/844,264
Granted
Mar 23, 2021
Kind
B2
Abstract

The present invention relates to chemical compounds of general formula (I): which may possess useful therapeutic activity in a range of central nervous system disorders, and in particular, anxiety disorders.

Claims (20)

1. A method for treating anxiety associated with autism spectrum disorders (ASD) in children, the method comprising administering to a patient in need thereof a compound of formula (If), or a pharmaceutically acceptable salt thereof:

wherein X represents O or NR″;

R″ is selected from H, optionally substituted alkyl, optionally substituted aryl, optionally substituted cycloalkyl, optionally substituted acyl, optionally substituted alkenyl, optionally substituted heterocyclyl, optionally substituted heteroaryl, optionally substituted oxysulfinyl, optionally substituted oxysulfonyl, optionally substituted sulfinyl, and optionally substituted sulfonyl;

Y represents OR′″ or NR 3 R 4 ;

R′″ is H or optionally substituted alkyl;

R represents H or optionally substituted alkyl;

R 1 represents optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted alkyl, optionally substituted acyl, optionally substituted aryl, optionally substituted heterocyclyl, or optionally substituted heteroaryl;

R 2 represents H, optionally substituted cycloalkyl, optionally substituted alkyl, optionally substituted acyl, optionally substituted aryl, optionally substituted alkenyl, optionally substituted heterocyclyl, optionally substituted heteroaryl, optionally substituted oxysulfinyl, optionally substituted oxysulfonyl, optionally substituted sulfinyl, or optionally substituted sulfonyl;

R 3 and R 4 each independently represent optionally substituted alkyl, or wherein NR 3 R 4 forms an optionally substituted N-containing heteroaryl or optionally substituted N-containing heterocyclyl; and

each R′ is independently selected from the group consisting of hydrogen, halogen, cyano, nitro, amino, optionally substituted alkyl, optionally substituted acyl, alkoxy, optionally substituted aryl, oxyacyl, acyloxy, optionally substituted arylalkyl, optionally substituted sulfinyl, optionally substituted sulfonyl, oxyacylamino, oxythioacyl, thioacyloxy, optionally substituted sulphinylamino, optionally substituted amino, optionally substituted sulphonylamino, optionally substituted thio, oxysulfinylamino, oxysulfonylamino, optionally substituted alkenyl, and optionally substituted alkynyl.

2. The method according to claim 1 , wherein each R′ is hydrogen.

3. The method according to claim 1 , wherein X is NR″; and

R″ is selected from H, optionally substituted alkyl, optionally substituted aryl, optionally substituted cycloalkyl, optionally substituted acyl, optionally substituted alkenyl, optionally substituted heterocyclyl, optionally substituted heterocyclyl, optionally substituted heteroaryl, optionally substituted oxysulfinyl, optionally substituted oxysulfonyl, optionally substituted sulfinyl, and optionally substituted sulfonyl.

4. The method according to claim 1 , wherein Y is NR 3 R 4 , and NR 3 R 4 forms an optionally substituted N-containing heteroaryl or optionally substituted N-containing heterocyclyl.

5. The method according to claim 1 , wherein R 1 is an optionally substituted cycloalkyl or optionally substituted cycloalkenyl.

6. The method according to claim 1 , wherein R 1 is a benzofused C 5 -C 7 cycloalkyl; wherein the benzene ring may be optionally substituted.

7. The method according to claim 1 , wherein the compound of formula (If) is:

or a pharmaceutically acceptable salt thereof.

8. The method according to claim 1 , wherein the anxiety associated with autism spectrum disorders (ASD) in children is selected from the group consisting of social anxiety disorder, generalized anxiety disorder, separation anxiety disorder, and obsessive compulsive disorder.

9. The method according to claim 7 , wherein the anxiety associated with autism spectrum disorders (ASD) in children is selected from the group consisting of social anxiety disorder, generalized anxiety disorder, separation anxiety disorder and obsessive compulsive disorder.

Assignments (6)
REASSIGNMENT AND RELEASE OF SECURITY INTEREST Recorded Apr 30, 2021
From: OXFORD FINANCE LLC
To: BIONOMICS, LTD
Reel/Frame 056106/0306 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 11, 2021
From: BUI, CHINH THIEN
To: BIONOMICS LIMITED
Reel/Frame 055231/0570 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 11, 2021
From: QUAZI, NURUL
To: THE WALTER & ELIZA HALL INSTITUTE OF MEDICAL RESEARCH
Reel/Frame 055231/0623 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 11, 2021
From: THE WALTER & ELIZA HALL INSTITUTE OF MEDICAL RESEARCH
To: BIONOMICS LIMITED
Reel/Frame 055231/0686 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 5, 2021
From: BAELL, JONATHAN BAYLDON; SLEEBS, BRAD; FLYNN, BERNARD LUKE; STREET, IAN PHILLIP
To: BIONOMICS LIMITED
Reel/Frame 055164/0842 →
SECURITY INTEREST Recorded May 8, 2020
From: BIONOMICS LTD
To: OXFORD FINANCE LLC, AS COLLATERAL AGENT
Reel/Frame 052615/0982 →
Continuity (7)
Continuation In Part 15398472 · Jan 4, 2017
Continuation 14533808 · Nov 5, 2014
Continuation 14030808 · Sep 18, 2013
Continuation 13617153 · Sep 14, 2012
Continuation 12311872
Provisional Application 60851983 · Oct 16, 2006
Related Publication 20180105523A1 · Apr 19, 2018
Cited By (1)
US 12,275,732