5'-4-'2-(n-methyl-n-(2-pyridyl)amino)ethoxy!benzyl!thiazolidine-2, 4-dione mesylate salt

Abstract

Disclosed are 5-[4-[2-(N-Methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione mesylate salts, or solvates thereof; processes for preparing such compounds, compositions comprising such compounds and the use of such compounds in medicine.

1 . A compound 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione mesylate salt, or solvate thereof.  
     
     
         2 . A compound according to  claim 1 , in the form of a novel polymorph.  
     
     
         3 . A compound according to  claim 1  or  claim 2 , characterised by data provided by at least one of the following: infra red, Raman, X-ray or nuclear magnetic resonance and melting point data, as provided herein, including partial spectral data provided herein  
     
     
         4 . A compound according to any one of  claims 1  to  3 , being Mesylate Form I, Mesylate Form II, Mesylate Form III or Mesylate Form IV, or a solvate thereof.  
     
     
         5 . A compound according to any one of  claims 1  to  3 , being Mesylate Form I characterised by 
 (i) an infra red spectrum containing peaks at about 1515, 670, 606 cm −1 ; and/or  
 (ii) a Raman spectrum containing peaks at about 887, 671 cm −1 ; and/or  
 (iii) an X-ray powder diffraction (XRPD) pattern containing peaks at about 17.4, 19.6, 20.0, 28.5°2θ.  
 
     
     
         6 . A compound according to any one of  claims 1  to  3 , being Mesylate Form II, characterised by 
 (i) an infra red spectrum containing peaks at about 674, 609 cm −1 ; and/or  
 (ii) a Raman spectrum containing peaks at about 883, 609 cm −1 ; and/or  
 (iii) an X-ray powder diffraction (XRPD) pattern containing peaks at about 20.2, 28.0, 28.8, 29.5°2θ.  
 
     
     
         7 . A compound according to any one of  claims 1  to  3 , being Mesylate Form III, characterised by 
 (i) an infra red spectrum containing peaks at about 1206, 603, 559, 545 cm −1 ; and/or  
 (ii) a Raman spectrum containing peaks at about 1205, 1179, 657, 557 cm −1 ; and/or  
 (iii) an X-ray powder diffraction (XRPD) pattern containing peaks at about 7.7, 14.8, 15.4, 16.9, 32.9°2θ.  
 
     
     
         8 . A compound according to any one of  claims 1  to  3 , Mesylate Form IV, characterised by 
 (i) an infra red spectrum containing peaks at about 1549, 759, 600 cm −1 ; and/or  
 (ii) a Raman spectrum containing peaks at about 1338, 1183, 990, 552 cm −1 ; and/or  
 (iii) an X-ray powder diffraction (XRPD) pattern containing peaks at about 6.2, 11.9, 15.9, 19.8, 22.7°2θ.  
 
     
     
         9 . A compound according to  claim 7 , being Mesylate Form IV, characterised in that it provides: 
 (i) an infrared spectrum substantially in accordance with FIG. 1; and    (ii) a Raman spectrum substantially in accordance with FIG. 2; and    (iii) an X-Ray powder diffraction pattern (XRPD) substantially in accordance with Table 1 or FIG. 3; and    (iv) a Solid State  13 C NMR spectrum substantially in accordance with FIG. 4.    
     
     
         10 . A compound according to any one of  claims 1  to  9 , in pure form.  
     
     
         11 . A compound according to any one of  claims 1  to  10 , in crystalline form.  
     
     
         12 . A compound according to any one of  claims 1  to  10 , in a solid pharmaceutically acceptable form.  
     
     
         13 . A process for preparing 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione mesylate salt, or solvate thereof. (“the Mesylate”) or a solvate thereof, characterised in that 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione (Compound (I)), or a salt thereof, dispersed or dissolved in a solvent, is reacted with a source of mesylate ion and thereafter, if required, a solvate of the resulting Mesylate is prepared; and the Mesylate or a solvate thereof is recovered.  
     
     
         14 . A pharmaceutical composition comprising 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione mesylate salt (“the Mesylate”) or solvate thereof, according to  claim 1 , and a pharmaceutically acceptable carrier therefor.  
     
     
         15 . 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione mesylate salt (“the Mesylate”) or solvate thereof, according to  claim 1 , for use as an active therapeutic substance.  
     
     
         16 . The use of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione mesylate salt (“the Mesylate”) or solvate thereof, according to  claim 1 , for the manufacture of a medicament for the treatment and/or prophylaxis of diabetes mellitus, conditions associated with diabetes mellitus and certain complications thereof.  
     
     
         17 . A method for the treatment and/or prophylaxis of diabetes mellitus, conditions associated with diabetes mellitus and certain complications thereof, in a human or non-human mammal which comprises administering an effective, non-toxic, amount of 5-[4-[2-(N-methyl-N-(2-pyridyl)amino)ethoxy]benzyl]thiazolidine-2,4-dione mesylate salt (“the Mesylate”) or solvate thereof, according to  claim 1 , to a human or non-human mammal in need thereof.