IP Library Granted Patent US 11,452,720
Granted Patent B2
US 11,452,720 · App. 16/923,498 · Granted Sep 27, 2022

Crystalline polymorphs of the free base of 2-hydroxy-6-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)benzaldehyde

Inventors: Zhe Li (San Diego, CA); Stephan D. Parent (South San Francisco, CA); Travis Houston (South San Francisco, CA)
Assignee: Global Blood Therapeutics, Inc.
A61K31/4439A61P1/04A61P11/00A61P25/28A61P35/00C07D401/04
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Quick Facts
Patent No.
US 11,452,720
App. No.
16/923,498
Granted
Sep 27, 2022
Kind
B2
Abstract

Disclosed are crystalline free base ansolvate forms of 2-hydroxy-6-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)benzaldehyde (or Compound 1), such as the free base Form I, Form II and Material N. Also disclosed are crystalline free base solvates of 2-hydroxy-6-((2-(1-isopropyl-1H-pyrazol-5-yl)pyridin-3-yl)methoxy)benzaldehyde (or Compound 1).

Claims (20)

1. A method for treating sickle cell disease, comprising administering to a patient in need thereof:

a composition comprising a crystalline ansolvate of Compound 1:

characterized by X-ray powder diffraction peaks (Cu Kα radiation) at 13.37°, 14.37°, 19.95° and 23.92° 2θ (each ±0.2° 2θ), wherein the composition is substantially free of other ansolvate polymorphs of Compound 1; and

another active agent.

2. The method of claim 1 , wherein the composition and the active agent are co-administered.

3. The method of claim 1 , wherein the composition and the active agent are administered in a single pharmaceutical composition.

4. The method of claim 1 , wherein the composition and the active agent are administered by the same route of administration.

5. The method of claim 1 , wherein the composition and the active agent are administered by different routes of administration.

6. The method of claim 1 , wherein the composition is administered orally.

7. The method of claim 4 , wherein the route of administration is oral.

8. The method of claim 1 , wherein the composition is substantially free of solvated polymorphs of Compound 1.

9. The method of claim 1 , wherein the composition comprises less than 10 mole % of amorphous forms of Compound 1.

10. A pharmaceutical composition comprising:

a composition comprising a crystalline ansolvate of Compound 1:

characterized by X-ray powder diffraction peaks (Cu Kα radiation) at 13.37°, 14.37°, 19.95° and 23.92° 2θ (each ±0.2° 2θ), wherein the composition is substantially free of other ansolvate polymorphs of Compound 1; and

another active agent.

11. The pharmaceutical composition of claim 10 , wherein the crystalline ansolvate of Compound 1 is characterized by an X-ray powder diffraction pattern (Cu Kα radiation) substantially similar to that of FIG. 5 .

12. The pharmaceutical composition of claim 10 , wherein the crystalline ansolvate of Compound 1 is characterized by an endothermic peak at 97±2° C. as measured by differential scanning calorimetry.

13. The pharmaceutical composition of claim 10 , wherein the composition is substantially free of solvated polymorphs of Compound 1.

14. The pharmaceutical composition of claim 10 , wherein the composition comprises less than 10 mole % of amorphous forms of Compound 1.

Assignments (6)
RELEASE OF SECURITY INTEREST Recorded Oct 6, 2022
From: BIOPHARMA CREDIT PLC, AS COLLATERAL AGENT
To: GLOBAL BLOOD THERAPEUTICS, INC.
Reel/Frame 061620/0186 →
SECOND AMENDED AND RESTATED PATENT SECURITY AGREEMENT Recorded Dec 22, 2021
From: GLOBAL BLOOD THERAPEUTICS, INC.
To: BIOPHARMA CREDIT PLC
Reel/Frame 058575/0921 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 2, 2021
From: LI, ZHE
To: GLOBAL BLOOD THERAPEUTICS, INC.
Reel/Frame 058272/0586 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 2, 2021
From: PARENT, STEPHAN D.; HOUSTON, TRAVIS
To: AMRI SSCI, LLC
Reel/Frame 058272/0590 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 2, 2021
From: AMRI SSCI, LLC
To: GLOBAL BLOOD THERAPEUTICS, INC.
Reel/Frame 058272/0598 →
AMENDED AND RESTATED PATENT SECURITY AGREEMENT Recorded Dec 9, 2020
From: GLOBAL BLOOD THERAPEUTICS, INC.
To: BIOPHARMA CREDIT PLC
Reel/Frame 054664/0871 →
Continuity (7)
Continuation 16163942 · Oct 18, 2018
Continuation 15801152 · Nov 1, 2017
Continuation 15236283 · Aug 12, 2016
Continuation 14616548 · Feb 6, 2015
Provisional Application 61937393 · Feb 7, 2014
Provisional Application 61937404 · Feb 7, 2014
Related Publication 20210161876A1 · Jun 3, 2021