US 12,391,640 B2
Process of making a crystalline EDG-2 receptor antagonist
Denis Billen, Dublin (IE); Bênédicte Martin, Dublin (IE); and Michelle O'Mahony, Dublin (IE)
Assigned to HORIZON THERAPEUTICS IRELAND DAC, Dublin (IE)
Filed by HORIZON THERAPEUTICS IRELAND DAC, Dublin (IE)
Filed on Mar. 1, 2023, as Appl. No. 18/176,862.
Claims priority of provisional application 63/315,898, filed on Mar. 2, 2022.
Prior Publication US 2023/0295073 A1, Sep. 21, 2023
Int. Cl. C07C 231/24 (2006.01); C07C 231/12 (2006.01)
CPC C07C 231/24 (2013.01) [C07C 231/12 (2013.01); C07B 2200/13 (2013.01)] 14 Claims
OG exemplary drawing
 
1. A process for the preparation of a Crystalline Form 1 2-(4-methoxy-3-(3-methylphenethoxy)benzamido)-2,3-dihydro-1H-indene-2-carboxylic acid (Compound I):

OG Complex Work Unit Chemistry
the process comprising the steps of:
(1) adding a mixture comprising a compound of Formula 2:

OG Complex Work Unit Chemistry
wherein M is Na+, K+, or Li+;
in a solvent onto a slurry of citric acid; and
(2) isolating Crystalline Form 1 Compound I by filtration;
wherein Crystalline Form 1 of Compound I is characterized as having: an X-ray powder diffraction (XRPD) pattern with peaks at 5.2±0.2° 2-Theta, 9.0±0.2° 2-Theta, 14.4±0.2° 2-Theta, and 17.7±0.2° 2-Theta, as measured using Cu (Ka) radiation.