US 12,139,477 B2
Compounds, salts thereof and methods for treatment of diseases
Ethan S. Burstein, San Diego, CA (US); Roger Olsson, Bunkeflostrand (SE); Björn Gustav Borgström, Lund (SE); Karl Erik Jansson, Dalby (SE); Niklas Patrik Sköld, Lund (SE); Henrik Von Wachenfeldt, Malmö (SE); and Larisa Yudina Wahlström, Eslöv (SE)
Assigned to ACADIA Pharmaceuticals Inc., San Diego, CA (US)
Filed by ACADIA PHARMACEUTICALS INC., San Diego, CA (US)
Filed on May 27, 2022, as Appl. No. 17/827,092.
Application 17/827,092 is a division of application No. 16/797,611, filed on Feb. 21, 2020, granted, now 11,345,693.
Application 16/797,611 is a continuation in part of application No. PCT/US2018/000354, filed on Aug. 20, 2018.
Claims priority of provisional application 62/548,301, filed on Aug. 21, 2017.
Claims priority of application No. 1730225-8 (SE), filed on Aug. 24, 2017.
Prior Publication US 2022/0298151 A1, Sep. 22, 2022
Int. Cl. C07D 413/12 (2006.01); C07D 211/58 (2006.01); C07D 401/12 (2006.01); C07D 405/12 (2006.01); C07D 409/12 (2006.01); C07D 417/12 (2006.01)
CPC C07D 413/12 (2013.01) [C07D 211/58 (2013.01); C07D 401/12 (2013.01); C07D 405/12 (2013.01); C07D 409/12 (2013.01); C07D 417/12 (2013.01)] 30 Claims
 
1. A method for treating a disease in a patient comprising administering to the patient an effective amount of a compound of Formula (I):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt, hydrate, solvate, stereoisomer, or deuterated analogue thereof, wherein:
m and n are 1;
p and q are independently an integer selected from the group consisting of 0, 1, 2, 3, and 4;
R1 and R1d are fluoro;
R1a, R1b, and Rc are hydrogen;
R2, R2a, R2b, R2c and R2d are independently selected from the group consisting of hydrogen, deuterium, amino, hydroxyl, —OD, halogen, cyano, nitro, unsubstituted or substituted C1-6 alkyl, unsubstituted or substituted C1-6 haloalkyl, unsubstituted or substituted C1-6 hydroxyalkyl, unsubstituted or substituted C2-6 alkenyl, unsubstituted or substituted C2-6 alkenyloxy, unsubstituted or substituted C2-6 alkynyl, unsubstituted or substituted C2-6 alkynyloxy, unsubstituted or substituted C1-8 alkoxy, unsubstituted or substituted C3-6 cycloalkyl, unsubstituted or substituted C3-6 heteroalicyclyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl, wherein R2 is not hydrogen, hydroxy or benzyloxy; or R2 and R2b or R2c, taken together with the atoms to which they are attached form a ring system; or R2a and R2b, or R2c and R2d, taken together with the atoms to which they are attached form a ring system;
R3 is selected from hydrogen, deuterium, hydroxyl, —OD, unsubstituted or substituted C1-6 alkyl, unsubstituted or substituted C1-6 haloalkyl, unsubstituted or substituted C1-6 hydroxyalkyl, unsubstituted or substituted C2-6 alkenyl, unsubstituted or substituted C3-6 cycloalkyl, unsubstituted or substituted C3-6 heteroalicyclyl, substituted or unsubstituted aryl, and substituted or unsubstituted heteroaryl;
R4a, R4b, R5a, and R5b, are independently selected from the group consisting of hydrogen, deuterium, and unsubstituted or substituted C1-6 alkyl; wherein when m and n are 1 then R4a, R4b, R5a, R5b are hydrogen;
R6 is selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, oxo, —OD, cyano, substituted or unsubstituted C1-4 alkyl, and substituted or unsubstituted C1-4 alkoxy, substituted or unsubstituted aryl; or R6 and R3, taken together with the atoms to which they are attached form a ring system;
R7 is selected from the group consisting of hydrogen, deuterium, halogen, hydroxyl, oxo, —OD, cyano, substituted or unsubstituted C1-4 alkyl, and substituted or unsubstituted C1-4 alkoxy;
R8 is selected from the group consisting of hydrogen, deuterium, cyano, hydroxyl, —OD, substituted or unsubstituted C1-4 alkyl, substituted or unsubstituted C2-4 alkenyl, substituted or unsubstituted C3-6 cycloalkyl, and substituted or unsubstituted C1-4 alkoxy; and
X is O,
wherein the disease is selected from the group consisting of post-traumatic stress disorder (PTSD), autism, general anxiety disorder, panic attacks, psychosis, Alzheimer's disease dementia, Lewy body dementia, Parkinson's disease dementia, Parkinson's disease depression, vascular dementia, frontotemporal dementia, negative symptoms of schizophrenia, mild cognitive impairment (MCI), insomnia, major depression, and treatment-resistant depression.