Polymorphs of N-methyl-N-(3-{3-[2-thienylcarbonyl]-pyrazol-[1,5-alpha]-pyrimidin-7-yl}phenyl)acetamide and compositions and methods related thereto

Abstract

Polymorphs of N-methyl-N-(3-{3-[2-thienylcarbonyl]-pyrazol-[1,5-α]-pyrimidin-7-yl}phenyl)acetamide (Compound 1), and use of the same as a sedative-hypnotic, anxiolytic, anticonvulsant, and skeletal muscle relaxant agent. Processes for making the same, as well as related compositions and methods are also disclosed, particularly with regard to treatment of insomnia. A polymorph Form I possessing exception physical and heat stability is provided. A polymorph Form II

1 - 45 . (canceled)  
   
   
       46 . A method for treating insomnia in a patient in need thereof, comprising administering to the patient an effective amount of substantially pure polymorph Form I of N-methyl-N-(3-{3-[2-thienylcarbonyl]-pyrazol-[1,5-α]-pyrimidin-7-yl}phenyl)acetamide exhibiting a predominant endotherm at about 192-198° C. as measured by Differential Scanning Calorimeter, wherein said polymorph Form I comprises less than 6% by weight of a polymorph Form II.  
   
   
       47 . A method for inducing sleep in a patient in need thereof, comprising administering to the patient an effective amount of substantially pure polymorph Form I of N-methyl-N-(3-{3-[2-thienylcarbonyl]-pyrazol-[1,5-α]-pyrimidin-7-yl}phenyl)acetamide exhibiting a predominant endotherm at about 192-198° C. as measured by Differential Scanning Calorimeter, wherein said polymorph Form I comprises less than 6% by weight of a polymorph Form II.  
   
   
       48 . (canceled)  
   
   
       49 . (canceled)  
   
   
       50 . A method for treating insomnia in a patient in need thereof, comprising administering to the patient an effective amount of substantially pure polymorph Form II of N-methyl-N-(3-{3-[2-thienylcarbonyl]-pyrazol-[1,5-α]-pyrimidin-7-yl}phenyl)acetamide exhibiting a predominant endotherm at about 172-179° C. as measured by a Differential Scanning Calorimeter, wherein said polymorph Form II comprises less than 20% by weight of a polymorph Form I.  
   
   
       51 . A method for inducing sleep in a patient in need thereof, comprising administering to the patient an effective amount of substantially pure polymorph Form II of N-methyl-N-(3-{3-[2-thienylcarbonyl]-pyrazol-[1,5-α]-pyrimidin-7-yl}phenyl)acetamide exhibiting a predominant endotherm at about 172-179° C. as measured by a Differential Scanning Calorimeter, wherein said polymorph Form II comprises less than 20% by weight of a polymorph Form I.  
   
   
       52 . (canceled)  
   
   
       53 . (canceled)  
   
   
       54 . The method of  claim 46  wherein the polymorph Form I comprises less than 3% by weight of a polymorph Form II.  
   
   
       55 . The method of  claim 46  wherein the polymorph Form I comprises less than 1% by weight of a polymorph Form II.  
   
   
       56 . The method of  claim 47  wherein the polymorph Form I comprises less than 3% by weight of a polymorph Form II.  
   
   
       57 . The method of  claim 47  wherein the polymorph Form I comprises less than 1% by weight of a polymorph Form II.  
   
   
       58 . The method of  claim 50  wherein the polymorph Form II comprises less than 10% by weight of a polymorph Form I.  
   
   
       59 . The method of  claim 50  wherein the polymorph Form II comprises less than 5% by weight of a polymorph Form I.  
   
   
       60 . The method of  claim 51  wherein the polymorph Form II comprises less than 10% by weight of a polymorph Form I.  
   
   
       61 . The method of  claim 51  wherein the polymorph Form II comprises less than 5% by weight of a polymorph Form I.  
   
   
       62 . The method of  claim 46  wherein the polymorph Form I is administered in the form of a pill, capsule, or tablet.  
   
   
       63 . The method of  claim 47  wherein the polymorph Form I is administered in the form of a pill, capsule, or tablet.  
   
   
       64 . The method of  claim 50  wherein the polymorph Form II is administered in the form of a pill, capsule, or tablet.  
   
   
       65 . The method of  claim 51  wherein the polymorph Form II is administered in the form of a pill, capsule, or tablet.