Sesame oil based injection formulations

Abstract

Injectable formulations comprising ethanol, sesame oil, and an Immune Response Modifier compound are disclosed. Methods of making the formulations and methods of using the formulations for treatment of a disease in a subject, e.g., neoplastic disease, comprising injecting the formulations into a subject hi need of treatment, are also provided.

1 - 2 . (canceled) 
     
     
         3 . The method according to  claim 18 , wherein the ethanol is present in a concentration of from about 3 wt-% to about 8 wt-%. 
     
     
         4 . The method according to  claim 18 , wherein the ethanol is present in a concentration of from about 6.5 wt-% to about 7.5 wt-%. 
     
     
         5 . The method according to  claim 18 , wherein the immune response modifier compound is present in a concentration of from about 0.1 mg/mL to about 10 mg/mL. 
     
     
         6 - 8 . (canceled) 
     
     
         9 . The method according to  claim 18 , wherein the total nitrogen content of the sesame oil is less than or equal to 1 ppm. 
     
     
         10 . The method according to  claim 18 , wherein the sesame oil contains no more than 0.05 wt-% of sesamin and no more than 0.05 wt-% of sesamolin. 
     
     
         11 - 16 . (canceled) 
     
     
         17 . The method according to  claim 18 , wherein the immune response modifier compound comprises N-(4-{[4-amino-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl]oxy}butyl)octadecanamide, or a pharmaceutically acceptable salt thereof. 
     
     
         18 . A method of delivering a pharmaceutical formulation, the method comprising injecting the formulation into a subject, wherein the pharmaceutical formulation comprises
 sesame oil having a hydroxyl value less than or equal to 2, an acid value less than or equal to 0.1, and a peroxide value less than or equal to 1;   ethanol; and   an immune response modifier compound of formula:   
       
         
           
           
               
               
           
         
       
       wherein:
 X is alkylene having up to 8 carbon atoms optionally interrupted or terminated by —O—; 
 R 2  is hydrogen, alkyl, alkoxyalkylenyl, alkylaminoalkylenyl, or hydroxyalkylenyl; 
 Y is —C(O)— or —S(O) 2 —; 
 R 1  is a linear or branched aliphatic group having 11-23 carbon atoms, optionally including one or more unsaturated carbon-carbon bonds; and 
 R is hydrogen, halogen, or hydroxyl; 
 
       or a pharmaceutically acceptable salt thereof. 
     
     
         19 . The method of  claim 18 , wherein the formulation is injected into a tumor mass. 
     
     
         20 . The method of  claim 18 , wherein the formulation is injected into a wart. 
     
     
         21 . The method of  claim 18 , wherein the formulation is injected into hypertrophic scar tissue. 
     
     
         22 . A method of treating a disease in a subject, comprising injecting into a subject in need of treatment of the disease a pharmaceutical formulation comprising
 sesame oil having a hydroxyl value less than or equal to 2, an acid value less than or equal to 0.1, and a peroxide value less than or equal to 1;   ethanol; and   an immune response modifier compound of formula:   
       
         
           
           
               
               
           
         
       
       wherein:
 X is alkylene having up to 8 carbon atoms optionally interrupted or terminated by —O—; 
 R 2  is hydrogen, alkyl, alkoxyalkylenyl, alkylaminoalkylenyl, or hydroxyalkylenyl; 
 Y is —C(O)— or —S(O) 2 —; 
 R 1  is a linear or branched aliphatic group having 11-23 carbon atoms, optionally including one or more unsaturated carbon-carbon bonds; and 
 R is hydrogen, halogen, or hydroxyl; 
 
       or a pharmaceutically acceptable salt thereof. 
     
     
         23 . The method of  claim 22 , wherein the disease is a neoplastic disease. 
     
     
         24 . The method of  claim 23 , wherein the formulation is injected into a tumor mass. 
     
     
         25 . The method according to  claim 23 , wherein the disease is selected from a head or neck cancer, breast cancer, lymphoma, melanoma, cutaneous T cell lymphoma, and bladder cancer. 
     
     
         26 . The method of  claim 22 , wherein the disease is a viral disease that causes warts. 
     
     
         27 . The method of  claim 26 , wherein the formulation is injected into a wart. 
     
     
         28 . A method of making a formulation according to claim  1 , comprising
 providing
 sesame oil having a hydroxyl value less than or equal to 2, an acid value less than or equal to 0.1, and a peroxide value less than or equal to 1; 
 ethanol; and 
 an immune response modifier compound of formula: 
   
       
         
           
           
               
               
           
         
         
           
             wherein: 
           
           X is alkylene having up to 8 carbon atoms optionally interrupted or terminated by —O—; 
           R 2  is hydrogen, alkyl, alkoxyalkylenyl, alkylaminoalkylenyl, or hydroxyalkylenyl; 
           Y is —C(O)— or —S(O) 2 —; 
           R 1  is a linear or branched aliphatic group having 11-23 carbon atoms, optionally including one or more unsaturated carbon-carbon bonds; and 
           R is hydrogen, halogen, or hydroxyl; 
           or a pharmaceutically acceptable salt thereof; 
         
         combining the IRM compound with the ethanol to form an ethanol-IRM compound solution; and 
         combining the ethanol-IRM compound solution with the sesame oil to form a sesame oil-ethanol-IRM compound formulation. 
       
     
     
         29 . The method of  claim 28 , further comprising the step of evaporating a portion of the ethanol from the sesame oil-ethanol-IRM compound formulation. 
     
     
         30 . (canceled)