US 12,410,133 B2
Crystalline (r)-5-carbamoylpyridin-3-yl-2-methyl-4-(3-(trifluoromethoxy)benzyl)piperazine-1-carboxylate, compositions and methods of use thereof
Lianfeng Huang, Basking Ridge, NJ (US); Nancy Tsou, Edison, NJ (US); Nicole Suzanne White, San Diego, CA (US); Jun Xu, Suzhou (CN); and Qun Zhang, Suzhou (CN)
Assigned to Celgene Corporation, Summit, NJ (US); and Lundbeck La Jolla Research Center, Inc., San Diego, CA (US)
Filed by Celgene Corporation, Summit, NJ (US); and Lundbeck La Jolla Research Center, Inc., San Diego, CA (US)
Filed on May 5, 2023, as Appl. No. 18/143,765.
Application 17/338,182 is a division of application No. 16/569,578, filed on Sep. 12, 2019, granted, now 11,053,199, issued on Jul. 6, 2021.
Application 18/143,765 is a continuation of application No. 17/338,182, filed on Jun. 3, 2021, granted, now 11,680,046.
Claims priority of provisional application 62/731,014, filed on Sep. 13, 2018.
Prior Publication US 2023/0382861 A1, Nov. 30, 2023
This patent is subject to a terminal disclaimer.
Int. Cl. C07D 211/94 (2006.01); A61P 35/00 (2006.01)
CPC C07D 211/94 (2013.01) [A61P 35/00 (2018.01); C07B 2200/13 (2013.01)] 16 Claims
 
1. A single unit dosage form comprising a crystalline form of (R)-5-carbamoylpyridin-3-yl-2-methyl-4-(3-(trifluoromethoxy)benzyl)piperazine-1-carboxylate, wherein:
the crystalline form is Form A of (R)-5-carbamoylpyridin-3-yl-2-methyl-4-(3-(trifluoromethoxy)benzyl)piperazine-1-carboxylate, having an X-ray powder diffraction pattern comprising peaks at 18.1, 20.1, and 22.3 degrees 2θ±0.2 degrees 2θ;
the crystalline form is Form B of (R)-5-carbamoylpyridin-3-yl-2-methyl-4-(3-(trifluoromethoxy)benzyl)piperazine-1-carboxylate, having an X-ray powder diffraction pattern comprising peaks at 16.2, 18.2, and 19.2 degrees 2θ±0.2 degrees 2θ;
the crystalline form is Form C of (R)-5-carbamoylpyridin-3-yl-2-methyl-4-(3-(trifluoromethoxy)benzyl)piperazine-1-carboxylate, having an X-ray powder diffraction pattern comprising peaks at 18.0, 20.0, and 21.0 degrees 2θ±0.2 degrees 2θ;
the crystalline form is Form D of (R)-5-carbamoylpyridin-3-yl-2-methyl-4-(3-(trifluoromethoxy)benzyl)piperazine-1-carboxylate, having an X-ray powder diffraction pattern comprising peaks at 13.4, 21.0, and 23.8 degrees 2θ±0.2 degrees 2θ; or
the crystalline form is Form E of (R)-5-carbamoylpyridin-3-yl-2-methyl-4-(3-(trifluoromethoxy)benzyl)piperazine-1-carboxylate, having an X-ray powder diffraction pattern comprising peaks at 17.8, 21.3, and 22.8 degrees 2θ±0.2 degrees 2θ.