Treatment Of Immune Dysregulation Using Cannabinoid Derivatives

Abstract

This invention discloses cannabinoid derivatives and pharmaceutical uses thereof.

1 . A method of treatment and/or preventing transmission of Human Immunodeficiency Virus (HIV), Simian Immuno deficiency Virus, Feline Immunodeficiency Virus and infectious diseases associated with immune dysregulation such as influenza by administering to a subject in need thereof a therapeutically effective dose of a cannabinoid derivative having the formula: 
       
         
           
           
               
               
           
         
       
       wherein,
 R 1  is: 
 a) a O—C 1-5  alkyl (preferably OCH 3 ) or alkanoyl, optionally substituted by mono- or di-methylamino or ethylamino groups, 
 b) 
 
       
         
           
           
               
               
           
         
         R 2  is: 
         a) H, OH, COOH, or a halogen 
         R 3  is: 
         a) (W) m —Y—(Z) n , wherein 
         W is a C 5-12  straight or branched (preferably 1S′CH 3 , 2R′CH 3  dimethyl)alkyl, alkenyl, alkynyl, group, or mixture thereof, optionally substituted with at least one halogen, 
         Y is a bond, O, S, SO, SO 2 , CO, NH, N(C 1-6  alkyl), or NCS, 
         R 7  is:
 a) C 1-6  alkoxy, C 1-6  alkylthio, C 1-6  alkyl, or C 1-6  haloalkyl, 
 b) C(Y)(Z)—O—C 1-4  alkyl, 
 c) C 1-6  alkyl-CO 2 —Y, or 
 d) ═O or ═S,
 wherein Y and Z are each independently H or C 1-6  alkyl; 
 
 
         Q is:
 a) N—W, wherein W is: 
 i) hydrogen, 
 
       
     
     
         2 . The method of  claim 1 , wherein ring C in Formula III of the cannabinoid is one of the following (the dashed lines representing a double bond at either the Δ6a-10a, Δ8-9, or Δ9-10 position): 
       
         
           
           
               
               
           
         
       
     
     
         3 . The method of  claim 2  wherein the double bond in ring C is in the 8a-9a position. 
     
     
         4 . The method of  claim 2  where there are no double bonds in ring C. 
     
     
         5 . The method of  claim 1 , wherein R 7  is a methyl. 
     
     
         6 . The method of  claim 1 , wherein the R 1  substituent is H, OH or OCH 3 . 
     
     
         7 . The method of  claim 1 , wherein the R 3  is 
       
         
           
           
               
               
           
         
       
       wherein W 1  is H, methyl, or ethyl, wherein W 2  and W 3  are each independently H or methyl, wherein at least one of W 1 , W 2 , and W 3  is other than H and/or halogenated, and wherein W 4  is a C 1-4  alkylor haloalkyl, optionally substituted with an aromatic ring. 
     
     
         8 . The method of  claim 1 , wherein the R 3  is a branched alkyl side chain, a 1′,1′-dimethylheptyl having the formula: 
       
         
           
           
               
               
           
         
       
     
     
         9 . A method of treatment of and/or preventing transmission of Human Immunodeficiency Virus (HIV), Simian Immuno deficiency Virus, Feline Immunodeficiency Virus and diseases associated with immune dysregulation such as influenza by administering to a subject in need thereof a therapeutically effective dose of a cannabinoid derivative, wherein said cannabinoid derivative is (6aR,10aR)-3-(1′,1′-dimethyl-heptyl)-1-methoxy-6,6,9-trimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromene having the formula: 
       
         
           
           
               
               
           
         
       
     
     
         10 . A method of treatment of and/or preventing transmission of Human Immunodeficiency Virus (HIV), Simian Immuno deficiency Virus, Feline Immunodeficiency Virus and treatment of diseases associated with immune dysregulation such as influenza by administering to a subject in need thereof a therapeutically effective dose of a cannabinoid derivative, wherein said cannabinoid derivative is (6aR,10aR)-3-(1,1-Dimethylheptyl)-6a,7,8,9,10,10a-hexahydro-1-methoxy-6,6-dimethyl-9-methylene-6H-dibenzo[b,d]pyran having the formula: