US 12,275,722 B2
Process of reworking a crystalline form of a glycine transport inhibitor
Julia Regina Grimm, Mainz (DE); Katrin Baer, Mainz (DE); Albert Josef Barta, Warthausen (DE); Gisela Bodenbach, Niederburg (DE); Joe Ju Gao, Southbury, CT (US); Fredrik Lars Nordstrom, Ridgefield, CT (US); Michael Wiese, Gensingen (DE); Bing-Shiou Yang, Southbury, CT (US); Manabu Nakatani, Hyogo (JP); Masashi Adachi, Mino (JP); Kenji Egusa, Ikeda (JP); Roman Christian Messerschmid, Wiesbaden (DE); and Daniela Maria Schroeder, Biberach an der Riss (DE)
Assigned to Boehringer Ingelheim International GmbH, Ingelheim am Rhein (DE)
Filed by Boehringer Ingelheim International GmbH, Ingelheim am Rhein (DE)
Filed on Oct. 11, 2021, as Appl. No. 17/498,027.
Claims priority of application No. 20201550 (EP), filed on Oct. 13, 2020.
Prior Publication US 2022/0112183 A1, Apr. 14, 2022
Int. Cl. C07D 413/04 (2006.01); A61K 9/20 (2006.01); A61K 31/422 (2006.01)
CPC C07D 413/04 (2013.01) [A61K 9/2013 (2013.01); A61K 9/2018 (2013.01); A61K 9/2054 (2013.01); A61K 9/2095 (2013.01); A61K 31/422 (2013.01); C07B 2200/13 (2013.01)] 7 Claims
 
1. A process of reworking a crystalline compound of formula (I)

OG Complex Work Unit Chemistry
the process comprising:
i) drying a crystalline compound (I) in a tray dryer or in a pan dryer to provide a dry form of crystalline compound (I) having:
characteristic X-ray reflections at the following 2Θvalues:
4.1°, 4.6°, 10.0°, 16.7°, and 18.0°; or
characteristic 13C solid-state NMR chemical shifts selected from: 130.1 ppm, 46.6 ppm, and 25.0 ppm; or
at least three characteristic 19F solid-state nuclear magnetic resonance peaks at chemical shifts selected from −64.0, −65.6, −66.6, −78.2, and −79.1 ppm, and
ii) homogenizing the dry form of crystalline compound (I) from step (i), to provide a reworked form of crystalline compound (I).