JP-2022533050-A5 -

Dates

Publication Date

20230523

Application Date

20200519

Description

Reference List US4543256 WO2001/078713 WO 02/100377 WO2009/026934 WO2009/026935 WO2010/097092 WO2019101917 Alexander et Crutcher, (1990) Trends in Neuroscience 13:266-71; Bibbiani et al. , Chase Experimental Neurology (2005), 192:73-78; Campbell et al. , Neuropharmacology (1982); 21(10):953-961; Cannon et al. , J. Heterocyclic Chem. (1980);17:1633-1636; Cavero and Guillon, J. Pharmacol. Toxicol. Methods (2014), 69:150-161; Delong, (1990) Trends in Neuroscience 13:281-5; Gerfen et al, Science (1990) 250:1429-32; Giardina and Williams; CNS Drug Reviews (2001), Vol. 7(3):305-316; Goswami et al. , J. Nutritional Biochem. (2003) 14:703-709; Grosset et al. , Acta Neurol Scand. (2013), 128:166-171; Hauser et al. , Movement Disorders (2016), Vol. 32(9):1367-1372; Liu et al. , J. Med. Chem. (2006), 49:1494-1498; Liu et al. , Bioorganic Med. Chem. (2008), 16:3438-3444; Nolen et al. , J. Pharm Sci. (1995), 84(6): 677-681; Poewe et al. , Nature Review, (2017) vol 3 article 17013:1-21; Remington, “The Science and Practice of Pharmacy”, 22nd revised edition (2013), Edited by Allen, Lloyd V. , Jr. Rothman et al. , Circulation (2000), 102: 2836-2841; Sprenger and Poewe, CNS Drugs (2013), 27:259-272; Sozio et al. , Exp. Open. Drug Disc. (2012);7(5):385-406; Stain-Texier et al. , Drug Metab. and Disposition (1998) 26 5): 383-387; Wiley-Interscience (publisher): Compendium of Organic Synthetic Methods, Vol. I-XII The present invention may include the following embodiments. [1] Formula (Id) The solid form of the compound, a) The zwitterionic form of the compound (Id); b) Alkali metal salts of the compound of formula (Id); and c) Halogenated salt of the compound of formula (Id) A solid form selected from among them. [2] The solid form according to claim 1, wherein the solid form is a crystalline form. [3] The solid form according to any one of claims 1 and 2, wherein the solid form is selected from the group consisting of the dihydrate of the zwitterion of compound (Id), the heptahydrate of the zwitterion of compound (Id), and the potassium salt of compound (Id). [4] The solid form according to any one of claims 1 to 3, wherein the solid form is the dihydrate of the zwitterion of compound (Id) or the potassium salt of compound (Id). [5] The solid form according to any one of claims 1 to 4, wherein the solid form is the dihydrate characterized by an X-ray powder diffraction pattern obtained using a CuKα1 line (λ = 1.5406 Å) that includes one or more XRPD peaks listed for the dihydrate in group (a) of Table 2. [6] The solid form according to any one of claims 1 to 5, wherein the solid form is the dihydrate characterized by an X-ray powder diffraction pattern obtained using a CuKα1 line (λ = 1.5406 Å) that includes the following 2θ angles ±0.2° 2θ: 10.4, 11.6, 12.3 and 13.1 and 13.6°. [7] The solid form according to any one of claims 6, wherein the X-ray powder diffraction pattern further includes one or more peaks selected from the group consisting of peaks with the following 2θ angles ±0.2° 2θ: 14.3, 15.6, 16.0, 16.8, and 18.5°. [8] The solid form according to any one of claims 2 to 7, wherein the solid form is a crystalline form characterized by an X-ray powder diffraction pattern essentially depicted in Figure 8a, obtained using CuKα1 line (λ = 1.5406 Å). [9] The solid form according to any one of claims 1 to 8, wherein when the solid form is heated from about 30°C to about 150°C (heating rate of 10°C/min), such as by measuring using thermogravimetric analysis, it exhibits a weight reduction of about 7.6% (by weight) relative to its initial weight. [10] The solid form according to any one of claims 1 to 2, wherein the solid form is the potassium salt characterized by an X-ray powder diffraction pattern obtained using a CuKα1 line (λ = 1.5406 Å) that includes one or more XRPD peaks listed for potassium salts in group (a) of Table 2. [11] The solid form according to claim 10, wherein the potassium salt has a crystalline form characterized by an XRPD obtained using a CuKα1 line (λ = 1.5406 Å) that includes the following 2θ angles ±0.2° 2θ: 3.0, 9.0, 12.6, 13.6, and 15.0°. [12] The solid form according to claim 11, wherein the X-ray powder diffraction pattern further includes one or more peaks selected from the group consisting of peaks with the following 2θ angles ±0.2° 2θ: 17.1, 18.0, 18.4, 18.8 and 19.4°. [13] The solid form according to any one of claims 1 to 3 and 11 to 12, which exhibits a weight reduction of less than 1% (by weight) relative to the initial weight when heated from about 20°C to about 150°C (heating rate of 10°C/min), such as by measuring using thermogravimetric analysis. [14] A solid form of the compound of formula (Id) according to any one of claims 1 to 13, for use as a pharmaceutical. [15] A pharmaceutical composition comprising a therapeutically effective amount of a compound of formula (Id) described in any one of claims 1 to 13 in solid form and one or more pharmaceutically acceptable excipients. [16]