Polymorphs of N-methyl-N-(3-{3-[2-thienylcarbonyl]-pyrazol-[1,5-alpha]-pyrimidin-7-yl}phenyl)acetamide and compositions and methods related thereto
AssigneeNeurocrine Biosciences, Inc.
InventorsWilliam J. Thiele, Patrick B. O'Donnell
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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
Claims53
A 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.
A 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.
A process for preparing substantially pure Form I of N-methyl-N-(3-{3-[2-thienylcarbonyl[-pyrazol-[1,5-α]-pyrimidin-7-yl}phenyl)acetamide, comprising the steps of:
- forming a solution of a crystallization solvent comprising acetone and N-methyl-N-(3-{3-[2-thienylcarbonyl[-pyrazol-[1,5-α]-pyrimidin-7-yl}phenyl)acetamide;
- and
- cooling the solution to form a mass of crystals, and collecting the crystals to the Form I.
A process for preparing substantially pure Form II of N-methyl-N-(3-{3-[2-thienylcarbonyl[-pyrazol-[1,5-α]-pyrimidin-7-yl}phenyl)acetamide comprising the steps of:
- forming a solution of a crystallization solvent comprising methanol and N-methyl-N-(3-{3-[2-thienylcarbonyl[-pyrazol-[1,5-α]-pyrimidin-7-yl}phenyl)acetamide;
- and
- cooling the solution to form a mass of crystals, and collecting the crystals to the Form II.
Dependencies are inferred from the claim text.