IP Library › Granted Patent US 12,570,641
Granted Patent B2
US 12,570,641 · App. 18/245,039 · Granted Mar 10, 2026

Solid forms of a CDK4 inhibitor

Inventors: Wesley Dewitt Clark (Gales Ferry, CT); Judith Gail Deal (Wildomar, CA); Brian Matthew Samas (Niantic, CT)
Assignee: Pfizer Inc.
C07D405/14C07B2200/13
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Quick Facts
Patent No.
US 12,570,641
App. No.
18/245,039
Granted
Mar 10, 2026
Kind
B2
Abstract

This invention relates to crystalline and amorphous forms of 1,5-anhydro-3-({5-chloro-4-[4-fluoro-2-(2-hydroxypropan-2-yl)-1-(propan-2-yl)-1H-benzimidazol-6-yl]pyrimidin-2-yl}amino)-2,3-dideoxy-D-threo-pentitol, to pharmaceutical compositions comprising such solid forms, and to use of such solid forms and pharmaceutical compositions for the treatment of cancer.

Claims (20)

1 . A crystalline form of 1,5-anhydro-3-({5-chloro-4-[4-fluoro-2-(2-hydroxypropan-2-yl)-1-(propan-2-yl)-1H-benzimidazol-6-yl]pyrimidin-2-yl}amino)-2,3-dideoxy-D-threo-pentitol (PF-07220060) monohydrate (Form 2), having a 19 F solid state NMR spectrum comprising resonance (ppm) values of: −126.1 and −125.6 ppm±0.2 ppm.

2 . A crystalline form of PF-07220060 monohydrate (Form 2), having a powder X-ray diffraction (PXRD) pattern comprising peaks at 2θ values of: 9.6, 11.8 and 14.7°2θ±0.2°2θ.

3 . The crystalline form of claim 2 , having a PXRD pattern further comprising a peak at a 2θ value of: 12.4°2θ±0.2°2θ.

4 . The crystalline form of claim 3 , having a PXRD pattern further comprising a peak at a 2θ value of: 21.0°2θ±0.2°2θ.

5 . The crystalline form of claim 2 , having a Raman spectrum comprising wavenumber (cm −1 ) values of: 1484, 1555 and 1587 cm −1 ±2 cm −1 .

6 . The crystalline form of claim 5 , having a Raman spectrum further comprising a wavenumber (cm −1 ) value of: 1387 cm −1 ±2 cm −1 .

7 . The crystalline form of claim 6 , having a Raman spectrum further comprising a wavenumber (cm −1 ) value of: 1395 cm −1 ±2 cm −1 .

8 . The crystalline form of claim 2 , having a 13 C solid state NMR spectrum comprising resonance (ppm) values of: 22.8 and 163.0 ppm±0.2 ppm.

9 . The crystalline form of claim 8 , having a 13 C solid state NMR spectrum further comprising one, two or three resonance (ppm) values selected from the group consisting of: 50.3, 109.8 and 129.1 ppm±0.2 ppm.

10 . The crystalline form of claim 2 , having a 19 F solid state NMR spectrum comprising a resonance (ppm) value of: −126.1 ppm±0.2 ppm.

11 . The crystalline form of claim 10 , having a 19 F solid state NMR spectrum further comprising a resonance (ppm) value of: −125.6 ppm±0.2 ppm.

12 . A crystalline form of PF-07220060 monohydrate (Form 2), having: (a) a powder X-ray diffraction (PXRD) pattern comprising peaks at 2θ values of: 9.6, 11.8 and 14.7°2θ±0.2°2θ; (b) a Raman spectrum comprising wavenumber (cm −1 ) values of: 1484, 1555 and 1587 cm −1 ±2 cm −1 ; (c) a 13 C solid state NMR spectrum comprising resonance (ppm) values of: 22.8 and 163.0 ppm±0.2 ppm; or (d) a 19 F solid state NMR spectrum comprising resonance (ppm) values of: −126.1 and −125.6 ppm±0.2 ppm; or any combination of (a), (b), (c) and (d).

13 . An anhydrous crystalline form of PF-07220060 (Form 6), having: (a) a powder X-ray diffraction (PXRD) pattern comprising peaks at 2θ values of: 8.5, 10.1 and 13.8°2θ±0.2°2θ; (b) a Raman spectrum comprising wavenumber (cm −1 ) values of: 1436, 1465 and 1566 cm −1 ±2 cm −1 ; (c) a 13 C solid state NMR spectrum comprising resonance (ppm) values of: 54.7, 112.6 and 132.8 ppm±0.2 ppm; or (d) a 19 F solid state NMR spectrum comprising resonance (ppm) values of: −132.4 and −131.1 ppm±0.2 ppm; or any combination of two or more of (a), (b), (c) and (d).

14 . An anhydrous crystalline form of PF-07220060 (Form 11), having a powder X-ray diffraction (PXRD) pattern essentially the same as in FIG. 15 .

15 . The crystalline form of claim 2 , wherein the crystalline form is substantially pure.

16 . An amorphous form of PF-07220060 (Form 8), having a 19 F solid state NMR spectrum comprising a resonance (ppm) value of: −127.5 ppm±0.5 ppm.

17 . The amorphous form of claim 16 , having a 13 C solid state NMR spectrum comprising resonance (ppm) values of: 20.9, 49.3 and 116.6 ppm±0.5 ppm.

18 . The amorphous form of claim 16 , having a PXRD peak at diffraction angles (2θ) from about 4 to about 40°2θ±0.5°2θ.

19 . A pharmaceutical composition comprising the crystalline form of any one of claims 1 to 11 and 12 to 15 , or the amorphous form of any one of claims 16 to 18 , and a pharmaceutically acceptable carrier or excipient.

20 . A method of treating cancer in a subject in need thereof, comprising administering to the subject a therapeutically effective amount of the crystalline form of any one of claims 1 to 11 and 12 to 15 , or the amorphous form of any one of claims 16 to 18 ; wherein the cancer is breast cancer.

Continuity (3)
Provisional Application 63240268 · Sep 2, 2021
Provisional Application 63078636 · Sep 15, 2020
Related Publication 20230357211A1 · Nov 9, 2023
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