US 12,145,933 B2
Hemi (L)-tartrate forms of 3-({5-chloro-1-[3-(methylsulfonyl)propyl]-1H-indol-2-yl}methyl)-1-(2,2,2-trifluoroethy)-1,3-dihydro-2H-imidazo[4,5-C]pyridin-2-one and pharmaceutical compositions comprising the same
Jan Jos L. Bevernage, Kuringen (BE); Jasmine Bogaerts, Mol (BE); Kristof Leonard Kimpe, Beerse (BE); and Eszter Tieger, Magyarlak (HU)
Assigned to Janssen Sciences Ireland Unlimited Company, County Cork (IE)
Filed by Janssen Sciences Ireland Unlimited Company, County Cork (IE)
Filed on Jun. 10, 2021, as Appl. No. 17/344,361.
Claims priority of application No. 20179407 (EP), filed on Jun. 11, 2020.
Prior Publication US 2021/0387984 A1, Dec. 16, 2021
Int. Cl. C07D 471/04 (2006.01); A61K 9/00 (2006.01); A61K 47/02 (2006.01); A61K 47/26 (2006.01); A61K 47/38 (2006.01)
CPC C07D 471/04 (2013.01) [A61K 9/0095 (2013.01); A61K 47/02 (2013.01); A61K 47/26 (2013.01); A61K 47/38 (2013.01); C07B 2200/13 (2013.01)] 19 Claims
 
1. A compound of formula

OG Complex Work Unit Chemistry
that is a hemi (L)-tartrate form of rilematovir,
wherein the compound is in crystalline form and
wherein the crystalline form is selected from Form 1, Form 2, Form 3, or mixtures thereof,
where:
Form 1 is characterized by an X-ray powder diffraction pattern comprising peaks at 12.4, 15.8, 16.2, 18.0, 20.2, 22.7, and 26.7 degrees two theta ±0.2 degrees two theta when measured using Cu Kα radiation;
Form 2 is characterized by an X-ray powder diffraction pattern comprising peaks at 14.4, 14.7, 16.4, 17.1, 19.0, 19.4, and 20.7 degrees two theta ±0.2 degrees two theta when measured using Cu Kα radiation; and
Form 3 is characterized by an X-ray powder diffraction pattern comprising peaks at 8.2, 12.2, 15.3, 15.5, 16.2, 16.5, and 18.8 degrees two theta ±0.2 degrees two theta when measured using Cu Kα radiation.