IP Library › Granted Patent US 12,486,287
Granted Patent B2
US 12,486,287 · App. 17/426,882 · Granted Dec 2, 2025

Solid forms of a promoter of spinogenesis

Inventors: Stella T. Sarraf (Beverly Hills, CA); Elizabeth Büchler Vadas (Dorval, CA)
Assignee: Spinogenix, Inc.
C07D513/04A61K31/428C07D277/66A61P25/00A61P25/28C07B2200/13
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Quick Facts
Patent No.
US 12,486,287
App. No.
17/426,882
Granted
Dec 2, 2025
Kind
B2
Abstract

Provided herein are crystalline forms of 2-(2-(2-(2-(4-(benzo[d]thiazol-2-yl)phenoxy)ethoxy)ethoxy)ethoxy)ethan-1-ol (Compound I): Also provided are processes of manufacture and methods of using the crystalline forms.

Claims (4)

1 . Crystalline 2-(2-(2-(2-(4-(benzo[d]thiazol-2-yl)phenoxy)ethoxy)ethoxy)ethoxy)ethan-1-ol (Compound I Form I) characterized by an X-ray powder diffractogram comprising the following peaks (° 2θ±0.2° 2θ): 4.6, 20.8, and 23.7 as determined on a diffractometer using Cu-Kα radiation at a wavelength of 1.5406 Å.

2 . Compound I Form I according to claim 1 , wherein the diffractogram further comprises peaks (° 2θ±0.2° 2θ) at 9.2, 16.3, about 18.6, and 19.6.

3 . Compound I Form I according to claim 1 , characterized by a differential scanning calorimetry (DSC) curve that comprises an endotherm at 70° C. ±2° C.

4 . A pharmaceutical composition comprising the crystalline form of claim 1 and one or more pharmaceutically acceptable carriers.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 3, 2022
From: SARRAF, STELLA T.; VADAS, ELIZABETH BÜCHLER
To: SPINOGENIX, INC.
Reel/Frame 058879/0219 →
Continuity (2)
Provisional Application 62799644 · Jan 31, 2019
Related Publication 20220106330A1 · Apr 7, 2022
References Cited (48)
US 6576654B1 · Macias · 2003 [cited by applicant]
US 7666886B2 · Yang et al. · 2010 [cited by applicant]
US 8741883B2 · Yang et al. · 2014 [cited by applicant]
US 10675273B2 · Yang · 2020 [cited by applicant]
US 20090028787A1 · Gravenfors et al. · 2009 [cited by applicant]
US 20120253047A1 · Allegrini et al. · 2012 [cited by applicant]
US 20140080843A1 · Huang et al. · 2014 [cited by applicant]
US 20150299191A1 · Huang et al. · 2015 [cited by applicant]
US 20150366776A1 · Chung et al. · 2015 [cited by applicant]
US 20190000811A1 · Yang · 2019 [cited by applicant]
CN 101102796A · 2008 [cited by applicant]
CN 103554482A · 2014 [cited by applicant]
WO 2002016333A2 · 2002 [cited by applicant]
WO WO2014134287 · 2014 [cited by applicant]
WO WO2017120198 · 2017 [cited by applicant]
WO WO2019005682 · 2019 [cited by applicant]
WO WO2019028164A1 · 2019 [cited by examiner]
WO WO2020046991 · 2020 [cited by applicant]
WO WO2020160332 · 2020 [cited by applicant]
Brittain, H. G..; “Chapter 6: Methods for the Characterization of Polymorphs and Solvates”; in Polymorphism in Pharmaceutical Solids; EBSCO Publishing, 1999, pp. 227-278 (Year: 1999). [cited by examiner]
International Search Report & Written Opinion dated Apr. 1, 2020 for PCT/US2020/015967. 21 pages. [cited by applicant]
Kazemi, et al. A mild and efficient procedure for the synthesis of ethers from various alkyl halides. Iran. Chem. Commun. 1 (2013) 43-50. [cited by applicant]
PubChem CID 13456094. 2-(2-(2-(2-Hydroxyethoxy)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate. Feb. 8, 2007. 12 pages. [cited by applicant]
PubChem CID 19609441. 2-(4′-Heptyloxyphenyl)benzothiazole. Dec. 5, 2007. 8 pages. [cited by applicant]
Ciapetti, et al. Molecular Variations Based on Isosteric Replacements. The Practice of Medicinal Chemistry. Elsevier, Amsterdam, NL. Jan. 1, 2008; Chapter 8: pp. 181-241. [cited by applicant]
Cifelli, et al. Benzothiazole Amphiphiles Ameliorate Amyloid β-Related Cell Toxicity and Oxidative Stress. ACS Chem. Neurosci. 2016, 7, 6, 682-688. [cited by applicant]
Cifelli, et al. Benzothiazole Amphiphiles Promote the Formation of Dendritic of dendritic spines in primary hippocampal neurons. Journal of Biological Chemistry. Jun. 3, 2016; 291(23):11981-11992. [cited by applicant]
Extended European Search Report and Search Opinion dated Mar. 31, 2021 for EP Application No. 18840208.5. 12 pages. [cited by applicant]
Extended European Search Report and Search Opinion dated Sep. 27, 2022 for EP Application No. 20747738.1. 7 pages. [cited by applicant]
Habib, L.K. et al. (Dec. 10, 2010, e-published Oct. 5, 2010). “Inhibitors of catalase-amyloid interactions protect cells from beta-amyloid-induced oxidative stress and toxicity,” J Biol Chem 285(50):38933-38943. [cited by applicant]
Huang, et al. Inhibition of cholinesterase activity and amyloid aggregation by berberine-phenyl-benzoheterocyclic and tacrine-phenylbenzoheterocyclic hybrids. Bioorganic & Medicinal Chemistry. May 1, 2012; 20(3):3038-30… [cited by applicant]
Inbar, P. et al. (Oct. 2006). “Oligo(ethylene glycol) derivatives of thioflavin T as inhibitors of protein-amyloid interactions,” ChemBioChem 7(10):1563-1566. [cited by applicant]
International Search Report and Written Opinion dated Mar. 30, 2017 for PCT Application No. PCT/US2017/012139, 12 pages. [cited by applicant]
International Search Report and Written Opinion dated Sep. 12, 2018 for PCT Application No. PCT/US2018/044852, 9 pages. [cited by applicant]
Lee, N.J. et al. (Feb. 2016, e-published Dec. 8, 2015). “Hexa (ethylene glycol) derivative of benzothiazole aniline promotes dendritic spine formation through the RasGRF1-Ras dependent pathway,” Biochim Biophys Acta 186… [cited by applicant]
Mahou, et al. Versatile Route to Synthesize Heterobifunctional Poly(ethylene glycol) of Variable Functionality for Subsequent Pegylation. Polymers 2012, 4, 561-589. [cited by applicant]
Megill, A. et al. (May 29, 2013). “A tetra(ethylene glycol) derivative of benzothiazole aniline enhances Ras-mediated spinogenesis,” J Neurosci 33(22):9306-9318. [cited by applicant]
Prangkio, P. et al. (Dec. 2011, e-published Aug. 26, 2011). “Self-assembled, cation-selective ion channels from an oligo(ethylene glycol) derivative of benzothiazole aniline,” Biochim Biophys Acta 1808(12):2877-2885. [cited by applicant]
Prangkio, P. et al. (2012, e-published Oct. 15, 2012). “Multivariate analyses of amyloid-beta oligomer populations indicate a connection between pore formation and cytotoxicity,” PLoS One 7(1O):e47261. [cited by applicant]
Song, J.M. et al. (Feb. 2014, e-published Dec. 6, 2013). “A tetra(ethylene glycol) derivative of benzothiazole aniline ameliorates dendritic spine density and cognitive function in a mouse model of Alzheimer's disease,”… [cited by applicant]
Supplementary European Search Report and Search Opinion dated Jul. 19, 2019 for EP Application No. 17736233.2. 7 pages. [cited by applicant]
Wu, et al. Triethylene glycol-modified iridium(iii) complexes for fluorescence imaging of Schistosoma japonicum. Journal of Materials Chemistry. Jan. 1, 2017; 5(25):4973-4980. [cited by applicant]
Wu, et al. Supporting Information—Triethylene glycol-modified iridium(iii) complexes for fluorescence imaging of Schistosoma japonicum. Journal of Materials Chemistry. Jan. 1, 2017; pp. 1-3. [cited by applicant]
Xing, et al. Generation of halogenated hydrocarbons. Organic Chemistry. Shandong University Press. 2001. 4 pages. (In Chinese with Machine translation). [cited by applicant]
Yang, J. et al. (Jul. 26, 2002). “Catalytic oxidations of steroid substrates by artificial cytochrome p-450 enzymes,” J Org Chem 67(15):5057-5067. [cited by applicant]
Zhao, X. et al. (Oct. 20, 2010). “Amyloid-β peptide is a substrate of the human 20S proteasome,” ACS Chem Neurosci 1(10):655-660. [cited by applicant]
Nozaki et al., “Medicinal Chemistry,” 1995, first edition, pp. 98-99, published by Kagaku-Dojin Publishing Company. [cited by applicant]
Wermuth, “The Practice of Medicinal Chemistry,” 1998, Chapter 13: Conversion of molecules based on equivalent replacement, pp. 235-271, published by Technomics, Inc. [cited by applicant]