Teva Gyogyszergyar Zartkoruen Mukodo Reszvenytarsasag

Biogal Gyogyszergyar Rt.

Teva Gyogyszergyar Reszvenytarsasag

Erika Feher

Ferenc Korodi

Erika Magyar

Claude Singer

Provided are novel Zaleplon crystalline Forms II, III, IV and V, which are useful for the treatment of insomnia. Also provided are processes for making Forms I, II, and V using precipitation methods.

Process for purifying N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-ethylacetamide(zaleplon) and crystalline forms of zaleplon accessible with the process

A process for the production of N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-ethylacetamide (zaleplon) that involves reacting N-[3-[3-(dimethylamino)-1-oxo-2-propenyl]phenyl]-N-ethylacetamide or a salt thereof with 3-amino-4-cyanopyrazole or a salt thereof under acidic conditions in a reaction medium comprising a mixture of water and a water-miscible organic compound produces zaleplon in high yield and high purity. A regioisomer of zaleplon (N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-5-yl)phenyl]-N-ethylacetamide) is useful as a reference standard for monitoring the composition of production batches of zaleplon.

Process for the production of N-[3-(3-cyanopyrazolo[1,5-a] pyrimidin-7-yl) phenyl]-N-ethylacetamide (zaleplon)

Zaleplon can be separated from a regioisomer impurity by crystallization from selected solvents or by adding an anti-solvent to a solution of zaleplon and the regioisomer. Zaleplon crystalline Forms II, III, IV, and V are useful for the treatment of insomnia. These crystalline Forms are described along with processes for making them v crystallization from selected solvents.

Process for purifying N-[3-(3-cyanopyrazolo[1,5-a]pyrimidin-7-yl)phenyl]-N-ethylacetamide (zaleplon) and crystalline forms of zaleplon accessible with the process

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Debrecen, Hungary

Erika Feher