Granted Patent
B2
US 12,486,252 · App. 18/132,722 · Granted Dec 2, 2025
Solid forms of a Cot inhibitor compound
Inventors:
Kassibla E. Dempah (San Francisco, CA); Bing Shi (Redwood City, CA); Ana F. Voica (Redwood City, CA); Kevin S. Williamson (San Mateo, CA)
Assignee:
Gilead Sciences, Inc.
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Abstract
Disclosed are solid forms of a Cot (cancer Osaka thyroid) inhibitor and corresponding methods of preparation thereof, wherein the Cot inhibitor has the following formula:
Claims (41)
1 . A solid form of Compound 1:
wherein the solid form is Freebase Form III characterized by an XRPD pattern comprising peaks at 7.7, 11.3, and 18.8 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
2 . The solid form of claim 1 , characterized by an XRPD pattern further comprising one or more peaks at 15.6, 21.0, and 24.9 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
3 . The solid form of claim 1 , characterized by an XRPD pattern further comprising one or more peaks at 16.7, 22.4, and 23.1 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
4 . The solid form of claim 1 , characterized by an XRPD pattern comprising peaks at 7.7, 11.3, 15.6, 16.7, 18.8, 21.0, 22.4, 23.1, and 24.9 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
5 . The solid form of claim 1 , characterized by an XRPD pattern as substantially shown in FIG. 5 .
6 . The solid form of claim 1 , characterized by a DSC curve as substantially shown in FIG. 6 .
7 . The solid form of claim 1 , characterized by a TGA thermogram as substantially shown in FIG. 6 .
8 . A solid form of an oxalate salt of Compound 1:
wherein the solid form is Oxalate Form II characterized by an XRPD pattern comprising peaks at 7.8, 13.4, and 20.7 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
9 . The solid form of claim 8 , characterized by an XRPD pattern further comprising one or more peaks at 6.4, 17.5, and 24.5 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
10 . The solid form of claim 8 , characterized by an XRPD pattern further comprising one or more peaks at 10.1, 23.6, and 30.6 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
11 . The solid form of claim 8 , characterized by an XRPD pattern comprising peaks at 6.4, 7.8, 10.1, 13.4, 17.5, 20.7, 23.6, 24.5, and 30.6 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
12 . The solid form of claim 8 , characterized by an XRPD pattern as substantially shown in FIG. 29 .
13 . The solid form of claim 8 , characterized by a DSC curve as substantially shown in FIG. 30 .
14 . The solid form of claim 8 , characterized by TGA comprising a weight loss of about 3%, about 3%, and about 16%.
15 . The solid form of claim 8 , characterized by a TGA thermogram as substantially shown in FIG. 31 .
16 . A solid form of an ethanedisulfonate salt of Compound 1:
wherein the solid form is characterized by an XRPD pattern comprising peaks at 5.5, 10.7, and 20.1 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
17 . The solid form of claim 16 , characterized by an XRPD pattern further comprising one or more peaks at 8.3, 10.4, and 16.8 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
18 . The solid form of claim 16 , characterized by an XRPD pattern further comprising one or more peaks at 18.0, 19.8, and 23.4 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
19 . The solid form of claim 16 , characterized by an XRPD pattern comprising peaks at 5.5, 8.3, 10.4, 10.7, 16.8, 18.0, 19.8, 20.1, and 23.4 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
20 . The solid form of claim 16 , characterized by an XRPD pattern as substantially shown in FIG. 32 .
21 . The solid form of claim 16 , characterized by a DSC curve as substantially shown in FIG. 33 .
22 . The solid form of claim 16 , characterized by a TGA thermogram as substantially shown in FIG. 34 .
23 . A solid form of a besylate salt of Compound 1:
wherein the solid form is Besylate Form I characterized by an XRPD pattern comprising peaks at 6.8, 9.9, and 14.5 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
24 . The solid form of claim 23 , characterized by an XRPD pattern further comprising one or more peaks at 8.3, 15.5, and 17.8 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
25 . The solid form of claim 23 , characterized by an XRPD pattern further comprising one or more peaks at 16.2, 24.6, and 27.2 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
26 . The solid form of claim 23 , characterized by an XRPD pattern comprising peaks at 6.8, 8.3, 9.9, 14.5, 15.5, 16.2, 17.8, 24.6, and 27.2 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
27 . The solid form of claim 23 , characterized by an XRPD pattern as substantially shown in FIG. 52 .
28 . The solid form of claim 23 , characterized by a DSC curve as substantially shown in FIG. 53 .
29 . The solid form of claim 23 , characterized by a TGA thermogram as substantially shown in FIG. 54 .
30 . A solid form of a besylate salt of Compound 1:
wherein the solid form is Besylate Form II characterized by an XRPD pattern comprising peaks at 6.1, 7.8, and 15.1 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
31 . The solid form of claim 30 , characterized by an XRPD pattern further comprising one or more peaks at 9.6, 16.1, and 21.3 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
32 . The solid form of claim 30 , characterized by an XRPD pattern further comprising one or more peaks at 18.7, 19.6, and 23.7 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
33 . The solid form of claim 30 , characterized by an XRPD pattern comprising peaks at 6.1, 7.8, 9.6, 15.1, 16.1, 18.7, 19.6, 21.3, and 23.7 degrees 2θ (±0.2 degrees 2θ), wherein the XRPD is made using Cu Kα radiation.
34 . The solid form of claim 30 , characterized by an XRPD pattern as substantially shown in FIG. 55 .
35 . The solid form of claim 30 , characterized by a DSC curve as substantially shown in FIG. 56 .
36 . The solid form of claim 30 , characterized by a TGA thermogram as substantially shown in FIG. 57 .
Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Jul 24, 2023
From: DEMPAH, KASSIBLA E.; SHI, BING; VOICA, ANA F.; WILLIAMSON, KEVIN S.
To: GILEAD SCIENCES, INC.
Reel/Frame 064363/0484 →
Continuity (3)
Provisional Application
63001810
· Mar 30, 2020
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