Novel crystalline compound useful as glk activator

Abstract

A novel crystalline form of 3-{[5-(azetidin-1-ylcarbonyl)pyrazin-2-yl]oxy}-5-[(1-methylethyl)oxy]-N-1H-pyrazol-3-ylbenzamide is described in the specification. This compound is a glucokinase (GLK or GK) activator and useful as a pharmaceutical agent in the treatment or prevention of a disease or medical condition mediated through GLK, leading to a decreased glucose threshold for insulin secretion. Processes for the manufacture of the crystalline form, pharmaceutical compositions comprising the crystalline form and the use of the crystalline form in medical treatment are also described.

1 . A crystalline form of the compound 3-{[5-(azetidin-1-ylcarbonyl)pyrazin-2-yl]oxy}-5-[(1-methylethyl)oxy]-N-1H-pyrazol-3-ylbenzamide having an X-ray powder diffraction pattern with peaks at least one of the following 2-theta values measured using CuKa radiation: 24.6° and 18.0°. 
   
   
       2 . The crystalline form as claimed in  claim 1  having an X-ray powder diffraction pattern with peaks at the following 2-theta values measured using CuKa radiation: 24.6° and 18.0°. 
   
   
       3 . The crystalline form as claimed in  claim 1  having an X-ray powder diffraction pattern with peaks at the following 2-theta values measured using CuKa radiation: 24.6°, 18.0° and 25.6°. 
   
   
       4 . The crystalline form as claimed in  claim 1  having an X-ray powder diffraction pattern with peaks at the following 2-theta values measured using CuKa radiation: 24.6°, 18.0°, 25.6° and 23.8°. 
   
   
       5 . The crystalline form as claimed in  claim 1  having an X-ray powder diffraction pattern with peaks at the following 2-theta values measured using CuKa radiation: 24.6°, 18.0°, 25.6°, 23.8° and 11.5°. 
   
   
       6 . The crystalline form as claimed in  claim 1  having an X-ray powder diffraction pattern with peaks at the following 2-theta values measured using CuKa radiation: 24.6°, 18.0°, 25.6°, 23.8°, 11.5° and 9.1°. 
   
   
       7 . The crystalline form as claimed in  claim 1  having an X-ray diffraction pattern substantially the same as the X-ray diffraction pattern shown in Figure A. 
   
   
       8 . A crystalline form of the compound 3-{[5-(azetidin-1-ylcarbonyl)pyrazin-2-yl]oxy}-5-[(1-methylethyl)oxy]-N-1H-pyrazol-3-ylbenzamide having a melting point of about 136.8° C. (onset). 
   
   
       9 . A pharmaceutical composition comprising the crystalline form as claimed in  claim 1 , together with a pharmaceutically acceptable carrier. 
   
   
       10 . A process for forming the crystalline form claimed in  claim 1  from a solution of form A or A′ in isopropanol. 
   
   
       11 - 14 . (canceled) 
   
   
       15 . A method of treating GLK mediated diseases by administering an effective amount of a compound of  claim 1  to a mammal in need of such treatment. 
   
   
       16 . The method of  claim 15  wherein the GLK mediated disease is type 2 diabetes.