US 10,889,577 B2
Solid forms of an sGC stimulator
Vasu Sethuraman, Waltham, MA (US); Ahmad Hashash, Southborough, MA (US); Song Xue, Newton, MA (US); Robert C. Livingston, Arlington, MA (US); and Kwame Wiredu Nti-Addae, Tewksbury, MA (US)
Assigned to Cyclerion Therapeutics, Inc., Cambridge, MA (US)
Appl. No. 16/315,226
Filed by Cyclerion Therapeutics, Inc., Cambridge, MA (US)
PCT Filed Jul. 6, 2017, PCT No. PCT/US2017/040827
§ 371(c)(1), (2) Date Jan. 4, 2019,
PCT Pub. No. WO2018/009609, PCT Pub. Date Jan. 11, 2018.
Claims priority of provisional application 62/359,466, filed on Jul. 7, 2016.
Prior Publication US 2019/0169179 A1, Jun. 6, 2019
Int. Cl. C07D 413/14 (2006.01)
CPC C07D 413/14 (2013.01) [C07B 2200/13 (2013.01)] 24 Claims
OG exemplary drawing
 
1. A crystalline solid form of Compound I:

OG Complex Work Unit Drawing
wherein:
(1) the crystalline solid form is crystalline free form Form E characterized by (i) peaks in the XRPD spectrum comprising: 7.4, 18.8-19.3, 21.1, 24.8 and 25.5 °2θ; (ii) peaks in the XRPD spectrum comprising: 7.4, 13.9, 15.1, 16.3, 17.6, 18.8-19.3, 21.1, 22.3-22.5, 24.8, 25.5 and 27.1 °2θ; (iii) an XRPD spectrum substantially similar to that shown in FIG. 2 or FIG. 6; (iv) a FT-Raman spectrum substantially similar to that shown in FIG. 10; (v) an IR spectrum that exhibits a peak maximum at 1690 cm−1; (vi) an IR spectrum that exhibits a peak maximum at 1515 cm−1; or (vii) an IR spectrum that exhibits band maxima at 1690 and 1515 cm−1;(2) the crystalline solid form is crystalline free form Form A characterized by (i) peaks in the XRPD spectrum comprising: 6.0, 18.3, 19.3, 20.2 and 22.0 °2θ; (ii) peaks in the XRPD spectrum comprising: 6.0, 8.5, 9.5, 12.4-12.9, 13.4, 17.1, 18.3, 19.3, 20.2, 22.0, 30.1 and 34.1 °2θ; (iii) peaks in the XRPD spectrum comprising: 6.0, 6.7, 8.5, 9.5, 10.9, 12.4-12.9, 13.4, 16.2, 17.1, 18.3, 19.3, 20.2, 22.0, 23.0, 24.1 to 24.8, 25.8, 30.1 and 34.1 °2θ; (iv) an XRPD spectrum substantially similar to that shown in FIG. 2 or in FIG. 3A; (v) peaks in the XRPD spectrum comprising: 6.1 (80.81% rel int), 9.6 (40.35%), 12.6 (41.26%), 13.6 (43.19%), 18.4 (53.57%), 19.4 (100.00%), 20.3 (57.01%) and 22.0 (56.64) °2θ; (vi) an XRPD spectrum substantially similar to that shown in FIG. 3C; (vii) a FT-Raman spectrum substantially similar to that shown in FIG. 10; or (viii) an IR spectrum that exhibits a band maximum at 1730 cm−1;(3) the crystalline solid form is crystalline free form Form D characterized by (i) peaks in the XRPD spectrum comprising: 17.1, 18.1, 18.8 and 25.0 °2θ; (ii) peaks in the XRPD spectrum comprising: 8.8, 17.1, 18.1, 18.8, and 25.0 °2θ; (iii) an XRPD spectrum substantially similar to that shown in FIG. 2 or FIG. 5A; (iv) peaks in the XRPD spectrum comprising: 4.7 (97.11% rel int), 8.3 (64.04%), 18.1 (80.97%), 18.6 (100.00%), and 26.8 (65.25) °2θ; (v) an XRPD spectrum substantially similar to that shown in FIG. 5C; (vi) a FT-Raman spectrum substantially similar to that shown in FIG. 10; (vii) an IR spectrum that exhibits a band maximum at 1665 cm−1; (viii) an IR spectrum that exhibits a band maximum at 1639 cm−1; (ix) an IR spectrum that exhibits a band maximum at 968 cm−1; or (x) an IR spectrum that exhibits band maxima at 1665, 1639 and 968 cm−1;(4) the crystalline solid form is crystalline free form Form B characterized by (i) peaks in the XRPD spectrum comprising: 8.8, 16.4, 17.2, 18.8-19.1, 20.1, and 21.1-21.6°2θ; (ii) peaks in the XRPD spectrum comprising: 8.8, 10.6, 12.6-13.0, 14.6, 16.4, 17.2, 18.8-19.1, 20.1, 21.1-21.6, 24.5, 25.3, 27.0-27.5, 28.9, 29.8 and 30.5°2θ; (iii) an XRPD spectrum substantially similar to that shown in FIG. 2 or FIG. 4A; (iv) an XRPD spectrum substantially similar to that shown in FIG. 4C; (v) peaks in the XRPD spectrum comprising: 7.0 (44.44% rel int), 8.9 (76.55%), 17.4 (57.67%), 19.1 (100.00%), 20.3 (49.78%), 21.8 (36.16%), and 25.5 (52.26) °2θ; (vi) a FT-Raman spectrum substantially similar to that shown in FIG. 10; or (vii) an IR spectrum that exhibits a peak maximum at 1200 cm−1;(5) the crystalline solid form is crystalline free form Form F characterized by peaks in the XRPD spectrum comprising: 5.3 (100.00% rel int), 8.6 (58.80%), 16.4 (62.95%), and 19.0 (48.51%) °2θ; or an XRPD spectrum substantially similar to that shown in FIG. 7;(6) the crystalline solid form is crystalline free form Form G characterized by peaks in the XRPD spectrum comprising: 10.7 (55.47% rel int), 13.9 (42.47%), 18.33 (100.00% %), and 21.6 (40.73%) °2θ; or an XRPD spectrum substantially similar to that shown in FIG. 8; or(7) the crystalline solid form is crystalline free form Form H characterized by (i) peaks in the XRPD spectrum comprising: 5.77 (89.22% rel int), 6.39 (100.00% %), 9.1 (84.17%), and 18.5 (67.04%) °2θ; (ii) characterized by peaks in the XRPD spectrum comprising: 5.77 (89.22% rel int), 6.39 (100.00% %), 9.1 (84.17%), 18.5 (67.04%), and 18.83 (67.04%) °2θ, or (iii) an XRPD spectrum substantially similar to that shown in FIG. 9.