IP Library › Granted Patent US 11,993,588
Granted Patent B2
US 11,993,588 · App. 17/469,535 · Granted May 28, 2024

Crystalline forms of a MAGL inhibitor

Inventors: Cheryl A. Grice (San Diego, CA); Todd K. Jones (San Diego, CA); Kurt G. Grimm (San Diego, CA); Jacqueline Lorayne Blankman (San Diego, CA); Channing Rodney Beals (San Diego, CA)
Assignee: H. LUNDBECK A/S
C07D403/10C07B2200/13
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Quick Facts
Patent No.
US 11,993,588
App. No.
17/469,535
Granted
May 28, 2024
Kind
B2
Abstract

Described herein is the MAGL inhibitor 1,1,1,3,3,3-hexafluoropropan-2-yl 4-(2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzyl)piperazine-1-carboxylate, including crystalline forms and pharmaceutically acceptable salts and solvates thereof.

Claims (6)

1. A crystalline form of 1,1,1,3,3,3-hexafluoropropan-2-yl 4-(2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzyl)piperazine-1-carboxylate free base, wherein the crystalline form of 1,1,1,3,3,3-hexafluoropropan-2-yl4-(2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzyl)piperazine-1-carboxylate free base has an X-ray powder diffraction (XRPD) pattern with characteristic peaks at 7.8° 2-Theta, 12.0° 2-Theta, 18.5° 2-Theta, 19.0° 2-Theta, 19.6° 2-Theta and 21.2° 2-Theta.

2. A crystalline form 1 of 1,1,1,3,3,3-hexafluoropropan-2-yl4-(2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzyl)piperazine-1-carboxylate mono-hydrochloride salt, wherein the crystalline form 1 has an X-ray powder diffraction (XRPD) pattern with characteristic peaks at 6.4° 2-Theta, 14.9° 2-Theta, 16.9° 2-Theta, 18.4° 2-Theta, and 20.9° 2-Theta.

3. A crystalline form 2 of 1,1,1,3,3,3-hexafluoropropan-2-yl4-(2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzyl)piperazine-1-carboxylate mono-hydrochloride salt, wherein the crystalline form 2 has an X-ray powder diffraction (XRPD) pattern with characteristic peaks at 8.6° 2-Theta, 14.3° 2-Theta, 15.6° 2-Theta, 19.0° 2-Theta, 19.8° 2-Theta, and 20.7° 2-Theta.

4. A crystalline form of 1,1,1,3,3,3-hexafluoropropan-2-yl 4-(2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzyl)piperazine-1-carboxylate bis-hydrochloride salt, wherein the crystalline form of 1,1,1,3,3,3-hexafluoropropan-2-yl4-(2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzyl)piperazine-1-carboxylate bis-hydrochloride salt has an X-ray powder diffraction (XRPD) pattern with characteristic peaks at 6.4° 2-Theta, 12.0° 2-Theta, 12.5° 2-Theta, 14.3° 2-Theta, 18.5° 2-Theta, and 22.8° 2-Theta.

5. A crystalline form of 1,1,1,3,3,3-hexafluoropropan-2-yl 4-(2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzyl)piperazine-1-carboxylate fumarate salt, wherein the crystalline form of 1,1,1,3,3,3-hexafluoropropan-2-yl4-(2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzyl)piperazine-1-carboxylate fumarate salt has an X-ray powder diffraction (XRPD) pattern with characteristic peaks at 13.6° 2-Theta, 14.1° 2-Theta, 14.3° 2-Theta, 20.0° 2-Theta, and 21.9° 2-Theta.

6. A crystalline form of 1,1,1,3,3,3-hexafluoropropan-2-yl 4-(2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzyl)piperazine-1-carboxylate mesylate salt, wherein the crystalline form of 1,1,1,3,3,3-hexafluoropropan-2-yl4-(2-(pyrrolidin-1-yl)-4-(trifluoromethyl)benzyl)piperazine-1-carboxylate mesylate salt has an X-ray powder diffraction (XRPD) pattern with characteristic peaks at 8.6° 2-Theta, 12.4° 2-Theta, 14.6° 2-Theta, 16.5° 2-Theta, 17.7° 2-Theta, and 19.7° 2-Theta.

Assignments (3)
CHANGE OF NAME Recorded Sep 14, 2021
From: LUNDBECK LA JOLLA RESEARCH CENTER, INC.
To: H. LUNDBECK A/S
Reel/Frame 057514/0193 →
CHANGE OF NAME Recorded Sep 10, 2021
From: ABIDE THERAPEUTICS, INC.
To: LUNDBECK LA JOLLA RESEARCH CENTER, INC.
Reel/Frame 057443/0578 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 9, 2021
From: GRICE, CHERYL A.; JONES, TODD K.; GRIMM, KURT G.; BLANKMAN, JACQUELINE LORAYNE; BEALS, CHANNING RODNEY
To: ABIDE THERAPEUTICS, INC.
Reel/Frame 057434/0169 →
Continuity (3)
Continuation 16349142
Provisional Application 62423126 · Nov 16, 2016
Related Publication 20220235037A1 · Jul 28, 2022