Substituted thiazolidinedione derivative, process for its preparation and its pharmaceutical use

Abstract

A hydrate of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl)thiazolidine-2,4-dione, maleic acid salt, characterized in that it: (i) comprises water in the range of from 0.3 to 0.6 molar equivalents; and (ii) provides an infra red spectrum containing peaks at 1757, 1331, 1290, 1211 and 767 cm −1 ; and/or (iii) provides a Raman spectrum containing peaks at 1758, 1610, 1394, 1316 and 1289 cm −1 ; and/or (iv) provides a solid state nuclear magnetic resonance spectrum containing chemical shifts substantially as set out in Table I herein; and/or (v) provides an X-ray powder diffraction (XRPD) pattern substantially as set out in Figure IV herein; 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 - 17 . (canceled)  
   
   
       18 . A compound, which is a hydrate of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, maleic acid salt, wherein said compound comprises water in the range of from 0.3 to 0.6 molar equivalents and provides at least one of: 
 (i) an infrared spectrum containing peaks at 1757, 1331, 1290, 1211 and 767 cm −1 ;    (ii) a Raman spectrum containing peaks at 1758, 1610, 1394, 1316 and 1289 cm −1 ;    (iii) a solid state nuclear magnetic resonance spectrum containing chemical shifts substantially as set out in Table I; and    (iv) an X-ray powder diffraction pattern substantially as set out in Figure IV.    
   
   
       19 . A compound according to  claim 18 , wherein said compound comprises water in the range of from 0.3 to 0.5 molar equivalents.  
   
   
       20 . A compound, which is a hydrate of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, maleic acid salt, wherein said compound provides a Raman spectrum substantially in accordance with Figure II.  
   
   
       21 . A compound, which is a hydrate of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, maleic acid salt, wherein said compound provides a solid state  13 C nuclear magnetic resonance spectrum substantially in accordance with Figure III.  
   
   
       22 . A compound, which is a hydrate of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione, maleic acid salt, wherein said compound provides an X-ray powder diffraction pattern substantially as set out in Figure IV.  
   
   
       23 . A method for the treatment of Type II diabetes in a human or non-human mammal which comprises administering an effective, non-toxic, amount of the compound according to  claim 18  to a human or non-human mammal in need thereof.  
   
   
       24 . A method for the treatment of Type II diabetes in a human or non-human mammal which comprises administering an effective, non-toxic, amount of the compound according to  claim 20  to a human or non-human mammal in need thereof.  
   
   
       25 . A method for the treatment of Type II diabetes in a human or non-human mammal which comprises administering an effective, non-toxic, amount of the compound according to  claim 21  to a human or non-human mammal in need thereof.  
   
   
       26 . A method for the treatment of Type II diabetes in a human or non-human mammal which comprises administering an effective, non-toxic, amount of the compound according to  claim 22  to a human or non-human mammal in need thereof.  
   
   
       27 . A pharmaceutical composition comprising an effective, non-toxic amount of a compound according to  claim 18  and a pharmaceutically acceptable carrier therefor.  
   
   
       28 . A pharmaceutical composition comprising an effective, non-toxic amount of a compound according to  claim 20  and a pharmaceutically acceptable carrier therefor.  
   
   
       29 . A pharmaceutical composition comprising an effective, non-toxic amount of a compound according to  claim 21  and a pharmaceutically acceptable carrier therefor.  
   
   
       30 . A pharmaceutical composition comprising an effective, non-toxic amount of a compound according to  claim 22  and a pharmaceutically acceptable carrier therefor.