US 12,084,460 B2
Crystalline forms of a TLR7/TLR8 inhibitor
Nicole Bieri, Muttenz (CH); Andreas Kordikowski, Binningen (CH); Bin Li, Changshu (CN); Philipp Lustenberger, Allschwil (CH); Rita Ramos, Allschwil (CH); Vijay Sethuraman, Fremont, CA (US); and Sisi Zhang, Changshu (CN)
Assigned to Novartis AG, Basel (CH)
Appl. No. 17/056,351
Filed by NOVARTIS AG, Basel (CH)
PCT Filed May 16, 2019, PCT No. PCT/IB2019/054066
§ 371(c)(1), (2) Date Nov. 17, 2020,
PCT Pub. No. WO2019/220390, PCT Pub. Date Nov. 21, 2019.
Claims priority of application No. PCT/CN2018/087448 (WO), filed on May 18, 2018.
Prior Publication US 2021/0206783 A1, Jul. 8, 2021
Int. Cl. A61K 31/4162 (2006.01); A61K 31/5377 (2006.01); A61K 45/06 (2006.01); C07D 231/00 (2006.01); C07D 519/00 (2006.01); A61K 31/437 (2006.01); C07D 265/30 (2006.01); C07D 487/04 (2006.01)
CPC C07D 519/00 (2013.01) [A61K 31/4162 (2013.01); A61K 31/5377 (2013.01); A61K 45/06 (2013.01); C07D 231/00 (2013.01); A61K 31/437 (2013.01); C07B 2200/13 (2013.01); C07D 265/30 (2013.01); C07D 487/04 (2013.01)] 15 Claims
OG exemplary drawing
 
1. A crystalline form of the compound (S)—N-(4-((5-(1,6-dimethyl-1H-pyrazolo[3,4-b]pyridin-4-yl)-3-methyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-1-yl)methyl)bicyclo[2.2.2]octan-1-yl)morpholine-3-carboxamide in its free form, wherein the compound is a hydrate, and the crystalline form is characterized by one of the following characteristics:
(i) an x-ray powder diffraction pattern comprising representative peaks in terms of 2θ at 6.6±0.2°2θ, 16.0±0.2°2θ, and 17.3±0.2°2θ, measured at a temperature of about 25° C. and an x-ray wavelength, λ, of 1.5418 Å;
(ii) an x-ray powder diffraction pattern comprising four or more 20 values selected from the group consisting of 6.6±0.2°, 71±0,20, 10.6±0.2°, 13.2±0.2°, 14.3±0.2, 16.0±0.2°, 17.3±0.2°, 23.5±0.2°, 26.5±0.2 and 27.3±0.2°2θ, measured at a temperature of about 25° C. and an x-ray wavelength, λ, of 1.5418 Å; and
(iii) an x-ray powder diffraction pattern comprising five or more 2θ values selected from the group consisting of 6.6±0.2°, 7.1±0.20, 10.6±0.2°, 13.2±0.2°, 14.3±0.2°, 16.0±0.2°, 17.3±0.2°, 23.5±0.2°, 26.5±0.2 and 27.3±0.2°2θ, measured at a temperature of about 25° C. and an x-ray wavelength, λ, of 1.5418 Å.