US 12,331,070 B2
C7 substituted oxysterols and methods of use thereof
Francesco G. Salituro, Marlborough, MA (US); Albert Jean Robichaud, Boston, MA (US); Gabriel Martinez Botella, Wayland, MA (US); Andrew Griffin, L'ile Bizard (CA); Boyd L. Harrison, Princeton Junction, NJ (US); and Daniel La, Chestnut Hill, MA (US)
Assigned to Sage Therapeutics, Inc., Cambridge, MA (US)
Filed by Sage Therapeutics, Inc., Cambridge, MA (US)
Filed on Feb. 1, 2024, as Appl. No. 18/430,056.
Application 18/430,056 is a division of application No. 17/476,153, filed on Sep. 15, 2021, granted, now 11,926,646.
Application 17/476,153 is a division of application No. 16/338,315, granted, now 11,149,056, issued on Oct. 19, 2021, previously published as PCT/US2017/054657, filed on Sep. 30, 2017.
Claims priority of provisional application 62/402,797, filed on Sep. 30, 2016.
Claims priority of provisional application 62/402,789, filed on Sep. 30, 2016.
Prior Publication US 2024/0300995 A1, Sep. 12, 2024
Int. Cl. C07J 31/00 (2006.01); C07J 9/00 (2006.01)
CPC C07J 31/006 (2013.01) [C07J 9/005 (2013.01)] 4 Claims
 
1. A method of inducing sedation or anesthesia comprising administering to a subject an effective amount of a compound of Formula (B):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof, wherein:
each of R1A and R1B is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted carbocyclyl, wherein the carbocyclyl may be saturated or partially saturated, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or R1A and R1B, together with the carbon atom to which they are attached form a 3-8 membered ring;
n is 1 or 2;
each of R2A and R2B is independently hydrogen, halo, —ORC, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, wherein RC is hydrogen or substituted or unsubstituted alkyl, or R2A and R2B, together with the carbon atom to which they are attached form an oxo group, wherein R2A and R2B are not both simultaneously hydrogen;
R3 is substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, or —ORA, wherein RA is substituted or unsubstituted alkyl;
R4 is absent or hydrogen; and
custom character represents a single or double bond, wherein when one of custom character is a double bond, the other custom character is a single bond; when both of custom character are single bonds, then R4 is hydrogen; and when one of the custom character is a double bond, R4 is absent, or
a pharmaceutical composition comprising said compound of Formula (B) or pharmaceutically acceptable salt thereof, and
a pharmaceutically acceptable carrier.
 
2. A method of modulating an NMDA receptor in a subject, said method comprising administering to the subject in need thereof an effective amount of a compound of Formula (B):

OG Complex Work Unit Chemistry
or a pharmaceutically acceptable salt thereof,
wherein:
each of R1A and R1B is independently hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted carbocyclyl, wherein the carbocyclyl may be saturated or partially saturated, substituted or unsubstituted heterocyclyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, or R1A and R1B, together with the carbon atom to which they are attached form a 3-8 membered ring;
n is 1 or 2;
each of R2A and R2B is independently hydrogen, halo, —ORC, substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, substituted or unsubstituted aryl, or substituted or unsubstituted heteroaryl, wherein RC is hydrogen or substituted or unsubstituted alkyl, or R2A and R2B, together with the carbon atom to which they are attached form an oxo group, wherein R2A and R2B are not both simultaneously hydrogen;
R3 is substituted or unsubstituted alkyl, substituted or unsubstituted alkenyl, substituted or unsubstituted alkynyl, or —ORA, wherein RA is substituted or unsubstituted alkyl;
R4 is absent or hydrogen; and
custom character represents a single or double bond, wherein when one of custom character is a double bond, the other custom character is a single bond; when both of custom character are single bonds, then R4 is hydrogen; and when one of the custom character is a double bond, R4 is absent; or
a pharmaceutical composition comprising said compound of Formula (B) or pharmaceutically acceptable salt thereof, and
a pharmaceutically acceptable carrier.