Solid forms of fasoracetam

Abstract

The disclosure is directed to cocrystals of fasoracetam, including R-fasoracetam, and various coformers. Crystalline materials comprising fasoracetam, including R-fasoracetam, are also provided. The disclosure further includes pharmaceutical compositions and methods of treatment of the cocrystals and crystalline materials of the disclosure.

1 .- 3 . (canceled) 
     
     
         4 . A crystalline compound or cocrystal comprising fasoracetam and a coformer, wherein the coformer is an aromatic compound, which is optionally substituted with one, two, three, or four substituents selected from the group consisting of OH, NH 2 , alkyl, —NO 2 , and a carbonyl-containing moiety. 
     
     
         5 .- 12 . (canceled) 
     
     
         13 . The crystalline compound or cocrystal of  claim 4 , wherein the organic acid moiety is —COOH. 
     
     
         14 .- 16 . (canceled) 
     
     
         17 . The crystalline compound or cocrystal of  claim 4 , wherein the aromatic compound has two, three, or four substituents, each of which are independently selected from the group consisting of —OH, —NH 2 , alkyl, organic acid, ester, and —NO 2 . 
     
     
         18 .- 57 . (canceled) 
     
     
         58 . The crystalline compound or cocrystal of  claim 4 , wherein the aromatic compound is polycyclic, optionally wherein the aromatic compound comprises two six-membered rings or a six-membered ring and a five-membered ring. 
     
     
         59 .- 61 . (canceled) 
     
     
         62 . The crystalline compound or cocrystal of  claim 4 , wherein the aromatic compound comprises all carbon ring atoms. 
     
     
         63 . The crystalline compound or cocrystal of  claim 4 , wherein at least one ring atom of the aromatic compound is not carbon. 
     
     
         64 . The crystalline compound or cocrystal of  claim 4 , wherein at least one ring atom of the aromatic compound is nitrogen. 
     
     
         65 . The crystalline compound or cocrystal of  claim 58 , the polycyclic aromatic compound is optionally substituted with at least one substituent selected from the group consisting of OH, NH 2 , alkyl, —NO 2 , and a carbonyl-containing moiety. 
     
     
         66 .- 332 . (canceled) 
     
     
         333 . The crystalline compound or cocrystal of  claim 4 , wherein the aromatic compound contains an aromatic ring fused to at least one non-aromatic cyclic moiety. 
     
     
         334 .- 336 . (canceled) 
     
     
         337 . A pharmaceutical composition comprising a crystalline compound or cocrystal of  claim 4  and one or more pharmaceutically acceptable excipients. 
     
     
         338 . A method of treating attention-deficit hyperactive disorder (ADHD) in human subject in need thereof, the method comprising administering to the subject the crystalline compound or cocrystal of  claim 4 . 
     
     
         339 . The method of  claim 338 , wherein the subject has at least one copy number variation (CNV) in a metabotropic glutamate receptor (mGluR) network gene. 
     
     
         340 .- 371 . (canceled)