IP Library › Granted Patent US 10,414,748
Granted Patent B2
US 10,414,748 · App. 15/567,433 · Granted Sep 17, 2019

Crystalline forms of 1-((2R,4R)-2-(1H-benzo[d]imidazol-2-yl)-1-methylpiperidin-4-yl)-3-(4-cyanophenyl)urea maleate

View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,414,748
App. No.
15/567,433
Granted
Sep 17, 2019
Kind
B2
Abstract

This invention relates to a crystalline form of 1-((2R,4R)-2-(1H-benzo[d]imidazol-2-yl)-1-methylpiperidin-4-yl)-3-(4-cyanophenyl)urea maleate, and to pharmaceutical compositions thereof, to intermediates and methods for the production and isolation of such crystalline forms and compositions, and to methods of using such crystalline forms and compositions in the treatment of abnormal cell growth in mammals, especially humans.

Claims (22)

1. A crystalline form of 1-((2R,4R)-2-(1H-benzo[d]imidazol-2-yl)-1-methylpiperidin-4-yl)-3-(4-cyanophenyl)urea maleate, having the structure:

and having a powder X-ray diffraction pattern comprising peaks at 2θ values of: 11.6, 12.1 and 19.6° 2θ±0.2° 2θ.

2. The crystalline form of claim 1 , having a powder X-ray diffraction pattern comprising peaks at 2θ values of: 11.6, 12.1, 17.0, 17.7 and 19.6° 2θ±0.2° 2θ.

3. The crystalline form of claim 1 , having a Raman spectrum comprising a wavenumber (cm −1 ) value of: 2219 cm −1 ±2 cm −1 .

4. The crystalline form of claim 1 , having a Raman spectrum comprising a wavenumber (cm −1 ) value of: 1612 cm −1 ±2 cm −1 .

5. The crystalline form of claim 1 , having a Raman spectrum comprising wavenumber (cm −1 ) values of: 1612 and 2219 cm −1 ±2 cm −1 .

6. The crystalline form of claim 1 , having a Raman spectrum comprising wavenumber (cm −1 ) values of: 1534, 1612 and 2219 cm −1 ±2 cm −1 .

7. The crystalline form of claim 1 , having a Raman spectrum comprising wavenumber (cm −1 ) values of: 1175, 1534, 1612 and 2219 cm −1 ±2 cm −1 .

8. The crystalline form of claim 1 , having a 13 C solid state NMR spectrum comprising a resonance (ppm) value of: 148.3 ppm±0.2 ppm.

9. The crystalline form of claim 1 , having a 13 C solid state NMR spectrum comprising resonance (ppm) values of: 57.8, 134.8 and 148.3 ppm±0.2 ppm.

10. The crystalline form of claim 1 , having a 13 C solid state NMR spectrum comprising resonance (ppm) values of: 57.8, 134.8, 144.7 and 148.3 ppm±0.2 ppm.

11. A crystalline form of 1-((2R,4R)-2-(1H-benzo[d]imidazol-2-yl)-1-methylpiperidin-4-yl)-3-(4-cyanophenyl)urea maleate, having the structure:

and having: (a) a powder X-ray diffraction pattern comprising peaks at 2θ values of: 11.6 and 12.1° 2θ±0.2° 2θ; and (b) a Raman spectrum comprising wavenumber (cm −1 ) values of: 1612 and 2219 cm −1 ±2 cm −1 .

12. A crystalline form of 1-((2R,4R)-2-(1H-benzo[d]imidazol-2-yl)-1-methylpiperidin-4-yl)-3-(4-cyanophenyl)urea maleate, having the structure:

and having: (a) a powder X-ray diffraction pattern comprising peaks at 2θ values of: 11.6 and 12.1° 2θ±0.2° 2θ; (b) a Raman spectrum comprising wavenumber (cm −1 ) values of: 1612 and 2219 cm −1 ±2 cm −1 ; and (c) a 13 C solid state NMR spectrum comprising a resonance (ppm) value of: 148.3 ppm±0.2 ppm.

13. The crystalline form of claim 1 , having: (a) a Raman spectrum comprising wavenumber (cm −1 ) values of: 1612 and 2219 cm −1 ±2 cm −1 ; and (b) a 13 C solid state NMR spectrum comprising a resonance (ppm) value of: 148.3 ppm±0.2 ppm.

14. A crystalline form of 1-((2R,4R)-2-(1H-benzo[d]imidazol-2-yl)-1-methylpiperidin-4-yl)-3-(4-cyanophenyl)urea maleate, having the structure:

and having: (a) a powder X-ray diffraction pattern comprising peaks at 2θ values of: 11.6 and 12.1° 2θ±0.2° 2θ; and (b) a 13 C solid state NMR spectrum comprising a resonance (ppm) value of: 148.3 ppm±0.2 ppm.

15. A pharmaceutical composition comprising the crystalline form of claim 1 , and a pharmaceutically acceptable carrier or excipient.

16. A pharmaceutical composition comprising the crystalline form of claim 11 , and a pharmaceutically acceptable carrier or excipient.

17. A pharmaceutical composition comprising the crystalline form of claim 12 , and a pharmaceutically acceptable carrier or excipient.

18. A pharmaceutical composition comprising the crystalline form of claim 14 , and a pharmaceutically acceptable carrier or excipient.

Assignments (1)
ASSIGNEE ADDRESS CORRECTION Recorded Mar 20, 2023
From: PFIZER INC.
To: PFIZER INC.
Reel/Frame 063119/0087 →