US 12,466,824 B2
Stable polymorphic form of 6-fluoro-9-methyl-9H-β-carboline and uses thereof
Hans Rommelspacher, Berlin (DE); Tomasz Zygmunt, Berlin (DE); and Reimar Schlingensiepen, Berlin (DE)
Assigned to AudioCure Pharma GmbH, Berlin (DE)
Appl. No. 17/633,544
Filed by AudioCure Pharma GmbH, Berlin (DE)
PCT Filed Aug. 7, 2020, PCT No. PCT/EP2020/072328
§ 371(c)(1), (2) Date Feb. 7, 2022,
PCT Pub. No. WO2021/028365, PCT Pub. Date Feb. 18, 2021.
Claims priority of application No. 19191150 (EP), filed on Aug. 9, 2019.
Prior Publication US 2022/0289741 A1, Sep. 15, 2022
Int. Cl. C07D 471/04 (2006.01); A61P 27/16 (2006.01)
CPC C07D 471/04 (2013.01) [A61P 27/16 (2018.01); C07B 2200/13 (2013.01)] 20 Claims
 
1. A crystalline polymorphic form of 6-fluoro-9-methyl-9H-B-carboline of the formula (I)

OG Complex Work Unit Chemistry
wherein the crystalline polymorphic form has the X-ray powder diffraction pattern comprising 2-theta angle values of 11.3, 17.1, 17.6, 18.0, 22.5, 23.2, and 29.4 degrees with a deviation ±0.2 degree.
 
8. A pharmaceutical composition comprising the crystalline polymorphic form of 6-fluoro-9-methyl-9H-β-carboline according to claim 1 together with at least one pharmaceutically acceptable carrier, excipient, solvent and/or diluent.