5-[4-[2-(n-methyl-n-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, maleic acid salt, hydrate as pharmaceutical

Abstract

A hydrate of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, maleic acid salt, characterised in that it: (i) comprises water in the range of from 0.4 to 2.5% w/w; and (ii) provides an infra red spectrum containing peaks at 1749, 1703, 1645, 1623, 1365 and 736 cm −1 ; and/or (iii) provides an X-ray powder diffraction (XRPD) pattern substantially as set out in FIG. II and/or (iv) provides a Raman spectrum containing peaks at 3106, 3069, 3002, 2961, 1750, 1718, 1684, 1385, 1335, 1229, 1078, 917, 428 and 349 cm −1 and/or (iv) provides a solid-state nuclear magnetic resonance spectrum containing chemical shifts substantially as set out in Table I; a process for the preparation of such a compound, a pharmaceutical composition containing such a compound and the use of such a compound or composition in medicine.

1 . A method for the treatment of Type II diabetes in a human or non-human mammal in need thereof, said method comprising administering to said human or non-human mammal an effective amount of a crystalline 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, maleic acid salt, hydrate wherein said hydrate contains water in the range of from 1.5 to 2.5% w/w and provides at least one of: 
 (i) an infra red spectrum containing peaks at 1749, 1703, 1645, 1623, 1365 and 736 cm −1 ;    (ii) an X-ray powder diffraction pattern substantially as set out in Table I;    (iii) a Raman spectrum containing peaks at 3106, 3069, 3002, 2961, 1750, 1718, 1684, 1385, 1335, 1229, 1078, 917, 428 and 349 cm −1 ; and    (iv) a solid-state  13 C nuclear magnetic resonance spectrum containing chemical shifts substantially at 35.7, 37.9, 50.3, 57.0, 65.6, 109.3, 112.9, 112.9, 119.7, 129.1, 133.2, 134.0, 136.1, 136.8, 143.0, 153.2, 157.4, 168.6, 171.7, 173.6, and 176.6 ppm.    
   
   
       2 . A method for the treatment of Type II diabetes in a human or non-human mammal in need thereof, said method comprising administering to said human or non-human mammal an effective amount of a crystalline 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, maleic acid salt, hydrate, wherein said hydrate contains water in the range of from 1.5 to 2.5% w/w and provides an X-ray powder diffraction pattern substantially in accordance with  FIG. 2 .  
   
   
       3 . A method for the treatment of Type II diabetes in a human or non-human mammal in need thereof, said method comprising administering to said human or non-human mammal an effective amount of a crystalline 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, maleic acid salt, hydrate, wherein said hydrate contains water in the range of from 1.5 to 2.5% w/w and provides a Raman spectrum substantially in accordance with  FIG. 3 .  
   
   
       4 . A method for the treatment of Type II diabetes in a human or non-human mammal in need thereof, said method comprising administering to said human or non-human mammal an effective amount of a crystalline 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, maleic acid salt, hydrate, wherein said hydrate contains water in the range of from 1.5 to 2.5% w/w and provides a solid state nuclear magnetic resonance spectrum substantially in accordance with  FIG. 4 .  
   
   
       5 . The method according to  claim 1 , wherein said hydrate contains water in the range of from 1.5 to 2.0% w/w.  
   
   
       6 . The method according to  claim 2 , wherein said hydrate contains water in the range of from 1.5 to 2.0% w/w.  
   
   
       7 . The method according to  claim 3 , wherein said hydrate contains water in the range of from 1.5 to 2.0% w/w.  
   
   
       8 . The method according to  claim 4 , wherein said hydrate contains water in the range of from 1.5 to 2.0% w/w.