US 12,441,738 B2
Solid state forms of Relugolix
Hana Kantor, Ostrava (CZ); Roman Gabriel, Olomouc (CZ); Pavel Kolesa, Hlubocec (CZ); and Alexandr Jegorov, Dobra Voda (CZ)
Assigned to Assia Chemical Industries Ltd., Tel Aviv (IL)
Filed by Assia Chemical Industries Ltd., Tel Aviv (IL)
Filed on Apr. 6, 2022, as Appl. No. 17/714,268.
Application 17/714,268 is a continuation in part of application No. 16/980,507, granted, now 11,306,104, previously published as PCT/US2019/022169, filed on Mar. 14, 2019.
Claims priority of provisional application 62/661,752, filed on Apr. 24, 2018.
Claims priority of provisional application 62/642,649, filed on Mar. 14, 2018.
Prior Publication US 2022/0227784 A1, Jul. 21, 2022
Int. Cl. C07D 495/04 (2006.01); A61K 9/00 (2006.01)
CPC C07D 495/04 (2013.01) [A61K 9/0053 (2013.01); C07B 2200/13 (2013.01)] 17 Claims
 
1. A method comprising:
dissolving Relugolix Form F in a first solvent to form a solution, wherein the Relugolix Form F is characterized by data including at least one of:
an X-ray powder diffraction pattern substantially as depicted in FIG. 1 or in FIG. 7;
an X-ray powder diffraction pattern having peaks at 6.9, 7.5, 9.5, 13.9 and 18.1 degrees 2-theta±0.2 degrees 2-theta; an
FT-IR spectrum having peaks at 1720, 1680, 1626, 1595, 1528, 1460, 1412, 1313, 1237 and 1095 cm−1±4 cm−1; or
an FT-IR spectrum substantially as depicted in at least one of FIG. 6a or FIG. 6b;
contacting the solution with a second solvent to form a suspension;
cooling the suspension; and
recovering Relugolix Form B having a formula of 1-{4-[1-(2,6-difluorobenzyl)-5-dimethylaminomethyl-3-(6-methoxypyridazin-3-yl)-2,4-dioxo-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidin-6-yl]phenyl}-3-methoxyurea).