Arylcyclohexylamine derivatives and their use in the treatment of psychiatric disorders

Abstract

Provided herein are arylcyclohexylanine derivatives and their use in the treatment of psychiatric disorders.

1 - 20 . (canceled) 
     
     
         21 . A substantially enantiomerically pure compound selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof. 
       
     
     
         22 . The compound of  claim 21  or pharmaceutically acceptable salt thereof, wherein the compound is at least 90% enantiomerically pure. 
     
     
         23 . The compound of  claim 21  or pharmaceutically acceptable salt thereof, wherein the compound is at least 95% enantiomerically pure. 
     
     
         24 . The compound of  claim 21  or pharmaceutically acceptable salt thereof, wherein the compound is at least 99% enantiomerically pure. 
     
     
         25 . A compound selected from: 
       
         
           
           
               
               
           
         
         or pharmaceutically acceptable salt thereof. 
       
     
     
         26 . The compound of  claim 21 , wherein the compound is selected from: 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof. 
       
     
     
         27 . The compound of  claim 25 , wherein the compound is 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof. 
       
     
     
         28 . A pharmaceutical composition comprising a compound of  claim 21  or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable excipient. 
     
     
         29 . A method of treating depression, anxious depression, a mood disorder, an anxiety disorder, or a substance use disorder and any symptom or disorders associated therewith in a subject in need thereof, the method comprising administering to the subject in need thereof an effective amount of a compound of  claim 21  or a pharmaceutically acceptable salt thereof. 
     
     
         30 . A method of treating depression or anxious depression in a subject in need thereof, the method comprising administering to the subject in need thereof an effective amount of a compound of  claim 21  or a pharmaceutically acceptable salt thereof. 
     
     
         31 . A pharmaceutical composition comprising a compound of  claim 25  or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable excipient. 
     
     
         32 . A method of treating depression, anxious depression, a mood disorder, an anxiety disorder, or a substance use disorder and any symptom or disorders associated therewith in a subject in need thereof, the method comprising administering to the subject in need thereof an effective amount of a compound of  claim 25  or a pharmaceutically acceptable salt thereof. 
     
     
         33 . A method of treating depression or anxious depression in a subject in need thereof, the method comprising administering to the subject in need thereof an effective amount of a compound of  claim 25  or a pharmaceutically acceptable salt thereof. 
     
     
         34 . A composition comprising an enantiomeric mixture of a compound selected from the group consisting of: 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof, wherein the enantiomeric mixture has a significantly greater amount of the enantiomer having the lower binding affinity at the NMDA receptor MK-801 site. 
       
     
     
         35 . The composition of  claim 34 , wherein the compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof. 
       
     
     
         36 . A composition comprising an enantiomeric mixture of a compound selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof, wherein the enantiomeric mixture has a significantly greater amount of the enantiomer having the higher binding affinity at the NMDA receptor MK-801 site. 
       
     
     
         37 . The composition of  claim 36 , wherein the compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof. 
       
     
     
         38 . A method of treating depression, anxious depression, a mood disorder, an anxiety disorder, or a substance use disorder and any symptom or disorders associated therewith in a subject in need thereof, the method comprising administering to the subject in need thereof an effective amount of the composition of  claim 34  or a pharmaceutically acceptable salt thereof. 
     
     
         39 . A method of treating depression or anxious depression in a subject in need thereof, the method comprising administering to the subject in need thereof an effective amount of the composition of  claim 34  or a pharmaceutically acceptable salt thereof. 
     
     
         40 . A method of treating depression, anxious depression, a mood disorder, an anxiety disorder, or a substance use disorder and any symptom or disorders associated therewith in a subject in need thereof, the method comprising administering to the subject in need thereof an effective amount of the composition of  claim 36  or a pharmaceutically acceptable salt thereof. 
     
     
         41 . A method of treating depression or anxious depression in a subject in need thereof, the method comprising administering to the subject in need thereof an effective amount of the composition of  claim 36  or a pharmaceutically acceptable salt thereof. 
     
     
         42 . A method of treating depression, anxious depression, a mood disorder, an anxiety disorder, or a substance use disorder and any symptom or disorders associated therewith in a subject in need thereof, the method comprising administering to the subject in need thereof an effective amount of a composition comprising a substantially enantiomerically pure compound selected from the group consisting of: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
         43 . A method of treating depression, anxious depression, a mood disorder, an anxiety disorder, or a substance use disorder and any symptom or disorders associated therewith in a subject in need thereof, the method comprising administering to the subject in need thereof an effective amount of a composition comprising a compound selected from the group consisting of: 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof. 
       
     
     
         44 . The method of  claim 42 , wherein the compound is selected from the group consisting of: 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof. 
       
     
     
         45 . A substantially enantiomerically pure compound of the formula: 
       
         
           
           
               
               
           
         
         or a pharmaceutically acceptable salt thereof. 
       
     
     
         46 . A method of treating depression, anxious depression, a mood disorder, an anxiety disorder, or a substance use disorder and any symptom or disorders associated therewith in a subject in need thereof, the method comprising administering to the subject in need thereof an effective amount of the substantially enantiomerically pure compound of  claim 45  or a pharmaceutically acceptable salt thereof. 
     
     
         47 . A method of treating depression or anxious depression in a subject in need thereof, the method comprising administering to the subject in need thereof an effective amount of the substantially enantiomerically pure compound of  claim 45  or a pharmaceutically acceptable salt thereof.