Compositions comprising methylphenidate-prodrugs, processes of making and using the same

Abstract

The present technology is directed to d-threo-methylphenidate conjugates and a composition comprising d-threomethylphenidate conjugated to nicotinoyl-L-serine, or salt thereof. The present technology also relates to a composition comprising at least one conjugate of d-methylphenidate having at least two or more chiral centers. The composition is optically active. The present technology additionally relates to oral formulations and pharmaceutical kits comprising at least one d-threo-methylphenidate conjugate.

What is claimed: 
     
         1 . A method of treating a patient having Attention Deficit Hyperactivity Disorder (ADHD), comprising orally administering to the patient a pharmaceutically effective amount of a composition comprising serdexmethylphenidate and dexmethylphenidate in an amount of 26.1 mg serdexmethylphenidate and 5.2 mg dexmethylphenidate. 
     
     
         2 . The method of  claim 1 , wherein the serdexmethylphenidate has the following structure 
       
         
           
           
               
               
           
         
       
     
     
         3 . The method of  claim 1 , wherein the serdexmethylphenidate is in the form of serdexmethylphenidate chloride, and wherein the 26.1 mg serdexmethylphenidate is equivalent to 28 mg serdexmethylphenidate chloride. 
     
     
         4 . The method of  claim 3 , wherein the serdexmethylphenidate chloride has the following structure 
       
         
           
           
               
               
           
         
       
     
     
         5 . The method of  claim 1 , wherein the dexmethylphenidate is in the form of dexmethylphenidate hydrochloride, and wherein the 5.2 mg dexmethylphenidate is equivalent to 6 mg dexmethylphenidate hydrochloride. 
     
     
         6 . The method of  claim 1 , wherein the combined molar does of serdexmethylphenidate and dexmethylphenidate is equivalent to 20 mg of dexmethylphenidate hydrochloride. 
     
     
         7 . The method of  claim 6 , wherein the 20 mg of dexmethylphenidate hydrochloride is equivalent to 17.3 mg dexmethylphenidate free base. 
     
     
         8 . The method of  claim 1 , wherein the composition is in the form of a capsule or tablet. 
     
     
         9 . The method of  claim 8 , wherein the capsule is an immediate release capsule. 
     
     
         10 . The method of  claim 8 , wherein the capsule or tablet is contained in a blister pack, roll, or bulk bottle. 
     
     
         11 . The method of  claim 8 , wherein the capsule or tablet is administered as a dosage of 1 capsule or tablet every day. 
     
     
         12 . A method of treating a patient having Attention Deficit Hyperactivity Disorder (ADHD), comprising orally administering to the patient a pharmaceutically effective amount of a composition comprising serdexmethylphenidate and dexmethylphenidate in an amount of 39.2 mg serdexmethylphenidate and 7.8 mg dexmethylphenidate. 
     
     
         13 . The method of  claim 12 , wherein the serdexmethylphenidate has the following structure 
       
         
           
           
               
               
           
         
       
     
     
         14 . The method of  claim 12 , wherein the serdexmethylphenidate is in the form of serdexmethylphenidate chloride, and wherein the 39.2 mg serdexmethylphenidate is equivalent to 42 mg serdexmethylphenidate chloride. 
     
     
         15 . The method of  claim 14 , wherein the serdexmethylphenidate chloride has the following structure 
       
         
           
           
               
               
           
         
       
     
     
         16 . The method of  claim 12 , wherein the dexmethylphenidate is in the form of dexmethylphenidate hydrochloride, and wherein the 7.8 mg dexmethylphenidate is equivalent to 9 mg dexmethylphenidate hydrochloride. 
     
     
         17 . The method of  claim 12 , wherein the combined molar does of serdexmethylphenidate and dexmethylphenidate is equivalent to 30 mg of dexmethylphenidate hydrochloride. 
     
     
         18 . The method of  claim 17 , wherein the 30 mg of dexmethylphenidate hydrochloride is equivalent to 25.9 mg dexmethylphenidate free base. 
     
     
         19 . The method of  claim 12 , wherein the composition is in the form of a capsule or tablet. 
     
     
         20 . The method of  claim 19 , wherein the capsule is an immediate release capsule. 
     
     
         21 . The method of  claim 19 , wherein the capsule or tablet is contained in a blister pack, roll, or bulk bottle. 
     
     
         22 . The method of  claim 19 , wherein the capsule or tablet is administered as a dosage of 1 capsule or tablet every day. 
     
     
         23 . A method of treating a patient having Attention Deficit Hyperactivity Disorder (ADHD), comprising orally administering to the patient a pharmaceutically effective amount of a composition comprising serdexmethylphenidate and dexmethylphenidate in an amount of 52.3 mg serdexmethylphenidate and 10.4 mg dexmethylphenidate. 
     
     
         24 . The method of  claim 23 , wherein the serdexmethylphenidate has the following structure 
       
         
           
           
               
               
           
         
       
     
     
         25 . The method of  claim 23 , wherein the serdexmethylphenidate is in the form of serdexmethylphenidate chloride, and wherein the 52.3 mg serdexmethylphenidate is equivalent to 56 mg serdexmethylphenidate chloride. 
     
     
         26 . The method of  claim 25 , wherein the serdexmethylphenidate chloride has the following structure 
       
         
           
           
               
               
           
         
       
     
     
         27 . The method of  claim 23  wherein the dexmethylphenidate is in the form of dexmethylphenidate hydrochloride, and wherein the 10.4 mg dexmethylphenidate is equivalent to 12 mg dexmethylphenidate hydrochloride. 
     
     
         28 . The method of  claim 23 , wherein the combined molar does of serdexmethylphenidate and dexmethylphenidate is equivalent to 40 mg of dexmethylphenidate hydrochloride. 
     
     
         29 . The method of  claim 28 , wherein the 40 mg of dexmethylphenidate hydrochloride is equivalent to 34.6 mg dexmethylphenidate free base. 
     
     
         30 . The method of  claim 23 , wherein the composition is in the form of a capsule or tablet. 
     
     
         31 . The method of  claim 30 , wherein the capsule is an immediate release capsule. 
     
     
         32 . The method of  claim 30 , wherein the capsule or tablet is contained in a blister pack roll, or bulk bottle. 
     
     
         33 . The method of  claim 30 , wherein the capsule or tablet is administered as a dosage of 1 capsule or tablet every day.