US RE49,697 E1
Crystalline N-[5-(aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamide mono mesylate monohydrate having a specific particle size distribution range and a specific surface area range for use in pharmaceutical formulations
Wilfried Schwab, Werder (DE); Alexander Birkmann, Wuppertal (DE); Kerstin Paulus, Ratingen (DE); Kurt Vogtli, Oberhofen (CH); Dieter Haag, Ramlinsburg (CH); Stephan Maas, Krefeld (DE); and Kristian Ruepp, Berlin (DE)
Assigned to AICURIS ANTI-INFECTIVE CURES AG, Wuppertal (DE)
Filed by AiCuris Anti-Infective Cures GmbH, Wuppertal (DE)
Filed on Nov. 25, 2020, as Appl. No. 17/104,028.
Application 15/683,127 is a division of application No. 14/840,690, filed on Aug. 31, 2015, granted, now 9,889,124, issued on Feb. 13, 2018.
Application 14/840,690 is a division of application No. 14/069,850, filed on Nov. 1, 2013, granted, now 9,119,786, issued on Sep. 1, 2015.
Application 14/069,850 is a continuation in part of application No. PCT/EP2012/068958, filed on Sep. 26, 2012.
Application 17/104,028 is a reissue of application No. 15/683,127, filed on Aug. 22, 2017, granted, now 10,137,117, issued on Nov. 27, 2018.
Claims priority of application No. 11007803 (EP), filed on Sep. 26, 2011.
This patent is subject to a terminal disclaimer.
Int. Cl. A61K 31/4439 (2006.01); A61K 9/14 (2006.01); A61K 9/16 (2006.01); A61K 31/10 (2006.01); A61K 45/06 (2006.01); C07D 417/12 (2006.01)
CPC A61K 31/4439 (2013.01) [A61K 9/145 (2013.01); A61K 9/16 (2013.01); A61K 31/10 (2013.01); A61K 45/06 (2013.01); C07D 417/12 (2013.01); Y10T 428/2982 (2015.01)] 32 Claims
OG exemplary drawing
 
[ 23. Crystalline N-[5-(aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)-phenyl]acetamide mono methanesulfonic acid monohydrate of the following formula and having a purity of >99%:

OG Complex Work Unit Chemistry
obtained by a process comprising the following steps
a) providing a mixture of an organic solvent and water containing N-[5-(aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]-acetamide,
b) adding methanesulfonic acid at an elevated temperature to the mixture of step a to obtain a supersaturated solution of the mesylate of N-[5-(aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]-acetamide,
c) optionally adding seed crystals of N-[5-(aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamide mono methane-sulfonic acid monohydrate at an elevated temperature between 30° C. and 90° C. to the supersaturated solution obtained in step b,
d) optionally stirring the supersaturated solution obtained in step b or step c,
e) cooling the supersaturated solution obtained in step b, step c or step d to room temperature,
f) filtering off the resulting crystals and washing the crystals with alcohol/water, and
g) optionally drying the crystals under vacuum at a temperature between 20° C. and 60° C. ]