US2021347812A1PendingUtilityA1

Neuroactive steroids, compositions, and uses thereof

Assignee: SAGE THERAPEUTICS INCPriority: Feb 20, 2015Filed: Jan 8, 2021Published: Nov 11, 2021
Est. expiryFeb 20, 2035(~8.6 yrs left)· nominal 20-yr term from priority
C07J 43/003C07J 7/007A61P 25/20C07J 7/0085A61K 31/58A61K 45/06C07J 21/008C07J 7/002C07J 13/007A61P 25/26A61P 25/00
69
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Claims

Abstract

Described herein are neuro-active steroids of the Formula (I): (I) or a pharmaceutically acceptable salt thereof; wherein R 1 , R 2 , R a , G, X, Y, Z, and n are as defined herein. Such compounds are envisioned, in certain embodiments, to behave as GABA modulators. Also provided are pharmaceutical compositions comprising a compound described herein and methods of use and treatment, e.g., such for inducing sedation and/or anesthesia.

Claims

exact text as granted — not AI-modified
1 - 66 . (canceled) 
     
     
         67 . A method for therapeutically treating a CNS-related disorder in a human subject in need thereof, comprising administering to the human subject a therapeutically effective amount of (a) a compound of Formula (I) or a pharmaceutically acceptable salt thereof or (b) a pharmaceutical composition comprising a compound of Formula (I) or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient, wherein: 
       
         
           
           
               
               
           
         
         each X, Y, and Z is independently CH or N; 
         G is —C(R 3a )(R 3b )(OR 1 ); 
         R 1  is C 1 -C 6  alkyl, C 1 -C 6  alkenyl, C 1 -C 6  alkynyl, carbocyclyl, heterocyclyl, aryl, or heteroaryl; 
         R 2  is C 1 -C 6  alkyl or C 1 -C 6  alkoxy; 
         each of R 3a  and R 3b  is independently —H, -D, or C 1 -C 6  alkyl; 
         R a  is cyano, halogen, nitro, C 1 -C 6  alkyl, C 1 -C 6  alkoxy, —S(O) m R b , —NR c R d , —C(O)R e , or —C(O)OR f ; 
         R b  is C 1 -C 6  alkyl, —NR c R d , or —OR f ; 
         each of R c  and R d  is independently —H, C 1 -C 6  alkyl, —C(O)R e , or —C(O)OR f ; 
         R e  is C 1 -C 6  alkyl or —NR g R h ; 
         R f  is —H or C 1 -C 6  alkyl; 
         each of R g  and R h  is independently —H or C 1 -C 6  alkyl; 
         m is 0, 1, or 2; 
         n is 0, 1, 2, 3, or 4; and 
         the compound is not selected from a compound selected from: 
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       and 
       wherein the CNS-related disorder is selected from anxiety disorder and seizure. 
     
     
         68 . The method of  claim 67 , wherein R 1  is C 1 -C 6  alkyl. 
     
     
         69 . The method of  claim 68 , wherein R 1  is —CH 3 , —CH 2 CH 3 , or —CH(CH 3 ) 2 . 
     
     
         70 . The method of  claim 67 , wherein R 2  is C 1 -C 6  alkyl. 
     
     
         71 . The method of  claim 70 , wherein R 2  is —CH 3 . 
     
     
         72 . The method of  claim 67 , wherein each of R 3a  and R 3b  is independently —H or -D. 
     
     
         73 . The method of  claim 67 , wherein each of R 3a  and R 3b  is independently —H. 
     
     
         74 . The method of  claim 67 , wherein one of R 3a  and R 3b  is —H, -D, or C 1 -C 6  alkyl, and the other of R 3a  and R 3b  is —H. 
     
     
         75 . The method of  claim 67 , wherein the compound Formula (I) is a compound of Formula (I-a): 
       
         
           
           
               
               
           
         
       
     
     
         76 . The method of  claim 75 , wherein X is N, and Y and Z are CH. 
     
     
         77 . The method of  claim 75 , wherein X and Z are N, and Y is CH. 
     
     
         78 . The method of  claim 75 , wherein X, Y, and Z are N. 
     
     
         79 . The method of  claim 75 , wherein R 1  is C 1 -C 6  alkyl. 
     
     
         80 . The method of  claim 75 , wherein R 2  is C 1 -C 6  alkyl. 
     
     
         81 . The method of  claim 75 , wherein each of R 3a  and R 3b  is independently —H or -D. 
     
     
         82 . The method of  claim 75 , wherein one of R 3a  and R 3b  is —H, -D, or C 1 -C 6  alkyl, and the other of R 3a  and R 3b  is —H. 
     
     
         83 . The method of  claim 75 , wherein one of R 3a  and R 3b  is -D or C 1 -C 6  alkyl, and the other of R 3a  and R 3b  is —H. 
     
     
         84 . The method of  claim 75 , wherein n is 1. 
     
     
         85 . The method of  claim 75 , wherein R a  is C 1 -C 6  alkyl or C 1 -C 6  alkoxy. 
     
     
         86 . The method of  claim 75 , wherein R a  is —S(O) m R b , —NR c R d , —C(O)R e , or —C(O)OR f . 
     
     
         87 . The method of  claim 75 , wherein R a  is halogen. 
     
     
         88 . The method of  claim 75 , wherein n is 1 or 2, and R a  is cyano, halogen, nitro, or C 1 -C 6  alkoxy. 
     
     
         89 . The method of  claim 67 , wherein the compound Formula (I) is a compound of Formula (I-b): 
       
         
           
           
               
               
           
         
       
     
     
         90 . The method of  claim 67 , wherein the compound is selected from: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       and a pharmaceutically acceptable salt thereof. 
     
     
         91 . The method of  claim 67 , wherein the CNS-related disorder is anxiety disorder. 
     
     
         92 . The method of  claim 91 , wherein the anxiety disorder is selected from generalized anxiety disorder (GAD), panic disorder, obsessive compulsive disorder (OCD), phobia, and post-traumatic stress disorder (PTSD). 
     
     
         93 . The method of  claim 67 , wherein the CNS-related disorder is seizure. 
     
     
         94 . A method for positively modulating a GABAA receptor in a subject in need thereof, comprising administering to the subject an effective amount of a pharmaceutical composition comprising a compound of Formula (I) or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient, wherein: 
       
         
           
           
               
               
           
         
         each X, Y, and Z is independently CH or N; 
         G is —C(R 3a )(R 3b )(OR 1 ); 
         R 1  is C 1 -C 6  alkyl, C 1 -C 6  alkenyl, C 1 -C 6  alkynyl, carbocyclyl, heterocyclyl, aryl, or heteroaryl; 
         R 2  is C 1 -C 6  alkyl or C 1 -C 6  alkoxy; 
         each of R 3a  and R 3b  is independently —H, -D, or C 1 -C 6  alkyl; 
         R a  is cyano, halogen, nitro, C 1 -C 6  alkyl, C 1 -C 6  alkoxy, —S(O) m R b , —NR c R d , —C(O)R e , or —C(O)OR f ; 
         R b  is C 1 -C 6  alkyl, —NR c R d , or —OR f ; 
         each of R c  and R d  is independently —H, C 1 -C 6  alkyl, —C(O)R e , or —C(O)OR f ; 
         R e  is C 1 -C 6  alkyl or —NR g R h ; 
         R f  is H or C 1 -C 6  alkyl; 
         each of R g  and R h  is independently —H or C 1 -C 6  alkyl; 
         m is 0, 1, or 2; 
         n is 0, 1, 2, 3, or 4; and 
         the compound is not selected from a compound selected from: 
       
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
       and
 wherein the subject has a CNS-related disorder selected from anxiety disorder and seizure. 
 
     
     
         95 . The method of  claim 94 , wherein the pharmaceutical composition is administered orally, subcutaneously, intravenously, or intramuscularly. 
     
     
         96 . The method of  claim 94 , wherein the pharmaceutical composition is administered chronically. 
     
     
         97 . The method of  claim 94 , wherein the CNS-related disorder is anxiety disorder. 
     
     
         98 . The method of  claim 97 , wherein the anxiety disorder is selected from generalized anxiety disorder (GAD), panic disorder, obsessive compulsive disorder (OCD), phobia, and post-traumatic stress disorder (PTSD). 
     
     
         99 . The method of  claim 94 , wherein the CNS-related disorder is seizure. 
     
     
         100 . The method of  claim 95 , wherein the pharmaceutical composition is administered orally. 
     
     
         101 . The method of  claim 95 , wherein the pharmaceutical composition is administered intravenously.

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