US 12,134,619 B2
Crystalline salts or co-crystals of 2′,6-difluoro-5′-[3-(1-hydroxy-1-methylethyl)-imidazo[1,2-b][1,2,4]triazin-7-yl]biphenyl-2-carbonitrile with p-toluenesulofonic acid as GABAA positive allosteric modulators
Matthew Toczko, Raleight, NC (US); and Jed Hubbs, Cambridge, MA (US)
Assigned to NEUROCYCLE THERAPEUTICS, INC., San Diego, CA (US)
Filed by NeuroCycle Therapeutics, Inc., San Diego, CA (US)
Filed on Dec. 28, 2022, as Appl. No. 18/089,661.
Application 18/089,661 is a division of application No. 17/072,282, filed on Oct. 16, 2020, granted, now 11,542,263.
Application 17/072,282 is a continuation of application No. PCT/US2019/027880, filed on Apr. 17, 2019.
Claims priority of provisional application 62/659,226, filed on Apr. 18, 2018.
Prior Publication US 2023/0139418 A1, May 4, 2023
Int. Cl. A61K 31/53 (2006.01); C07D 487/04 (2006.01)
CPC C07D 487/04 (2013.01) [C07B 2200/13 (2013.01)] 21 Claims
 
1. A crystalline salt or co-crystal of 2′,6-difluoro-5′-[3-(1-hydroxy-1-methylethyl)imidazo[1,2-b][1,2,4]triazin-7-yl]biphenyl-2-carbonitrile with p-toluenesulfonic acid of the following formula:

OG Complex Work Unit Chemistry
wherein the crystalline salt or co-crystal is Form A; and
wherein the crystalline salt or co-crystal is characterized by an X-ray powder diffraction pattern comprising at least three characteristic peaks at angles (°2θ) selected from 7.0°±0.2 °2θ, 12.4°±0.2 °2θ, 12.6°±0.2 °2θ, 13.0°±0.2 °2θ, 14.1°±0.2 °2θ, 15.4°±0.2 °2θ, 15.7°±0.2 °2θ, 16.3°±0.2 °2θ, 17.5°±0.2 °2θ, 18.3°±0.2 °2θ, 19.0°±0.2 °2θ, 21.0°±0.2 °2θ, 22.3°±0.2 °2θ, 23.0°±0.2 °2θ, and 24.9°±0.2 °2θ, when measured using the parameters described in Table 1.