US 12,391,652 B2
Crystal of 3-(difluoromethyl)-1-methyl-n-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4- carboxamide
Tomoya Ukegawa, Sunto-Gun (JP); and Satoshi Watanabe, Takarazuka (JP)
Assigned to SUMITOMO CHEMICAL COMPANY, LIMITED, Tokyo (JP)
Appl. No. 17/772,191
Filed by SUMITOMO CHEMICAL COMPANY, LIMITED, Tokyo (JP)
PCT Filed Oct. 21, 2020, PCT No. PCT/JP2020/039524
§ 371(c)(1), (2) Date Apr. 27, 2022,
PCT Pub. No. WO2021/085263, PCT Pub. Date May 6, 2021.
Claims priority of application No. 2019-200115 (JP), filed on Nov. 1, 2019.
Prior Publication US 2022/0402878 A1, Dec. 22, 2022
Int. Cl. A01N 43/56 (2006.01); C07D 231/14 (2006.01)
CPC C07D 231/14 (2013.01) [A01N 43/56 (2013.01); C07B 2200/13 (2013.01)] 9 Claims
OG exemplary drawing
 
1. A racemic crystal of 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, which is selected from at least one of a group consisting of
a Ra1 type crystal form which in a powder x-ray diffraction due to Cu-Kα radiation, has a diffraction peaks 2θ of 7.1±0.2°, 8.6±0.2°, 8.9±0.2°, 9.1±0.2°, 13.3±0.2°, 14.0±0.2°, 14.3±0.2°, 14.8±0.2°, 16.0±0.2°, 16.4±0.2°, 20.3±0.2°, and 20.6±0.2°,
a Ra2 type crystal form which in a powder x-ray diffraction due to Cu-Kα radiation, has a diffraction peaks 20 of 4.3=0.2°, 8.5±0.2°, 10.8±0.2°, 11.4±0.2°, 12.4±0.2°, 12.8=0.2°, 15.1±0.2°, 16.1±0.2°, 16.8±0.2°, and 19.1±0.2°, and
a Ra3 type crystal form which in a powder x-ray diffraction due to Cu-Kα radiation, has a diffraction peaks 20 of 3.6±0.2°, 7.1±0.2°, 7.4±0.2°, 9.6±0.2°, 11.9-0.2°, 12.5±0.2°, 12.9±0.2°, 14.3±0.2°, 15.7±0.2°, and 17.9±0.2°.