US 12,285,436 B2
Substituted pyridines as DNMT1 inhibitors
Andrew B. Benowitz, Stevenage (GB); David T. Fosbenner, Collegeville, PA (US); Bryan Wayne King, Collegeville, PA (US); Stuart Paul Romeril, Collegeville, PA (US); Megan Ketchum, Collegeville, PA (US); Todd Koretke, Collegeville, PA (US); Elizabeth Ann Moroz, Collegeville, PA (US); and Grace Price, Collegeville, PA (US)
Assigned to GlaxoSmithKline Intellectual Property Development Limited, (GB)
Filed by GlaxoSmithKline Intellectual Property Development Limited, Stevenage (GB)
Filed on Jul. 26, 2023, as Appl. No. 18/358,998.
Application 18/358,998 is a continuation of application No. 17/966,504, filed on Oct. 14, 2022, granted, now 11,771,711.
Application 17/966,504 is a continuation of application No. PCT/IB2022/051637, filed on Feb. 24, 2022.
Claims priority of provisional application 63/155,325, filed on Mar. 2, 2021.
Prior Publication US 2024/0180933 A1, Jun. 6, 2024
Int. Cl. A61K 31/675 (2006.01); A61K 31/44 (2006.01); A61P 35/02 (2006.01); C07D 213/85 (2006.01); C07F 9/58 (2006.01)
CPC A61K 31/675 (2013.01) [A61K 31/44 (2013.01); A61P 35/02 (2018.01); C07D 213/85 (2013.01); C07F 9/58 (2013.01); C07B 2200/13 (2013.01)] 6 Claims
 
1. An anhydrous crystalline glycine salt having a formula of

OG Complex Work Unit Chemistry
which provides an XRPD pattern substantially as set out in Table I:
TABLE I
 
XRPD Summay of Diffraction Angles and d-Spacing
Peak # Diff. Angle [°2θ] d-spacing [Å]
 
1 5.42 16.3027 
2 5.78 15.2672 
3 7.44 11.8749 
4 9.59 9.2110
5 10.56 8.3679
6 10.81 8.1745
7 11.55 7.6557
8 13.04 6.7854
9 14.46 6.1218
10 14.84 5.9641
11 15.56 5.6903
12 16.25 5.4518
13 17.01 5.2072
14 18.32 4.8394
15 18.82 4.7116
16 19.00 4.6665
17 19.20 4.6182
18 19.60 4.5246
19 20.49 4.3310
20 20.99 4.2287
21 21.18 4.1924
22 21.54 4.1216
23 21.69 4.0934
24 22.34 3.9755
25 22.65 3.9233
26 23.20 3.8313
27 23.95 3.7127
28 24.42 3.6426
29 24.99 3.5610
30 25.17 3.5354
31 26.22 3.3958
32 26.54  3.3559.