IP Library › Granted Patent US 12,459,888
Granted Patent B2
US 12,459,888 · App. 18/417,291 · Granted Nov 4, 2025

Isotope-enriched 3-amino-1-propanesulfonic acid derivatives and uses thereof

Inventors: Jiasheng Lu (Shanghai, CN); Jiamin Gu (Suzhou, CN); Xinyong Lv (Suzhou, CN); Guowei Song (Suzhou, CN); Dongdong Wu (Suzhou, CN); Daiqiang Hu (Suzhou, CN); Jun Gu (Suzhou, CN); Gang Chen (Suzhou, CN); Xiang Ji (Suzhou, CN); Xiuchun Zhang (Suzhou, CN); Jinchao Ai (Suzhou, CN); Xianqi Kong (Dollard-des-Ormeaux, CA)
Assignee: RISEN (SUZHOU) PHARMA TECH CO., LTD.
C07C309/14C07B59/001C07B59/002C07C309/15C07C309/59C07D233/61C07B2200/05
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Quick Facts
Patent No.
US 12,459,888
App. No.
18/417,291
Granted
Nov 4, 2025
Kind
B2
Abstract

There are provided isotope-enriched compounds of Formula (I) and pharmaceutically acceptable salts or esters thereof, as well as pharmaceutical compositions thereof and methods of use thereof for prevention and treatment of amyloid-β related diseases, such as Alzheimer's disease. R 1 R 2 X—CR 2 —CH 2 —CH 2 —SO 3 H   (I)

Claims (4)

1 . A compound which is

or a pharmaceutically acceptable salt or ester thereof.

2 . A pharmaceutical composition comprising the compound of claim 1 and a pharmaceutically acceptable carrier.

3 . A method for treatment of an amyloid-β related disease in a subject in need thereof comprising administering to the subject a therapeutically effective amount of the compound of claim 1 , such that the amyloid-β related disease is treated in the subject.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 20, 2024
From: LU, JIASHENG; GU, JIAMIN; LV, XINYONG; SONG, GUOWEI; WU, DONGDONG; HU, DAIQIANG; GU, JUN; CHEN, GANG; JI, XIANG; ZHANG, XIUCHUN; AI, JINCHAO; KONG, XIANQI
To: RISEN (SUZHOU) PHARMA TECH CO., LTD.
Reel/Frame 068341/0046 →
Priority Claims (1)
CN 201710168819.2 · Mar 21, 2017 · national
Continuity (5)
Continuation 17993389 · Nov 23, 2022
Continuation 17140450 · Jan 4, 2021
Continuation 16655311 · Oct 17, 2019
Continuation 15476255 · Mar 31, 2017
Related Publication 20240158343A1 · May 16, 2024
References Cited (67)
US 5840294A · Kisilevsky et al. · 1998 [cited by applicant]
US 5972328A · Kisilevsky et al. · 1999 [cited by applicant]
US 6310073B1 · Kisilevsky et al. · 2001 [cited by applicant]
US 6603008B1 · Ando et al. · 2003 [cited by applicant]
US 6670399B2 · Green et al. · 2003 [cited by applicant]
US 7253306B2 · Kong et al. · 2007 [cited by applicant]
US 7414076B2 · Kong et al. · 2008 [cited by applicant]
US 7517990B2 · Ito et al. · 2009 [cited by applicant]
US 7851641B2 · Findeis · 2010 [cited by applicant]
US 8044100B2 · Kong et al. · 2011 [cited by applicant]
US 8642801B2 · Kong et al. · 2014 [cited by applicant]
US 8748656B2 · Kong et al. · 2014 [cited by applicant]
US 8835500B2 · Laurin et al. · 2014 [cited by applicant]
US 8835654B2 · Kong et al. · 2014 [cited by applicant]
US 9499480B2 · Kong et al. · 2016 [cited by applicant]
US 10471029B2 · Tolar · 2019 [cited by applicant]
US 20060079578A1 · Laurin et al. · 2006 [cited by applicant]
US 20090076167A1 · Czamik · 2009 [cited by applicant]
US 20100120744A1 · Gant · 2010 [cited by applicant]
US 20120214745A1 · Naicker et al. · 2012 [cited by applicant]
JP 2010514674A · 2010 [cited by applicant]
WO 1994022437 · 1994 [cited by applicant]
WO 1996028187 · 1996 [cited by applicant]
WO 2009019534 · 2009 [cited by applicant]
WO 2015143447 · 2015 [cited by applicant]
WO 201727582 · 2017 [cited by applicant]
WO 2017044840 · 2017 [cited by applicant]
Alzheimer's disease [online] retrieved from the internet on Mar. 25, 2022 URL https:/www.mayoclinic.org/diseases-conditions/alzheimers-disease/symptoms-causes/syc-. [cited by examiner]
Chen, et al. Amyloid beta:structure,biology and structure-based therapeutic development.Acta Pharmacologica Sinica 2017:1205-1235. [cited by examiner]
Petition for Inter Partes Review of U.S. Pat. No. 10,472,323, Inter Partes Review No. IPR2021-00347, Dec. 18, 2020. [cited by applicant]
Exhibit 1002 for Inter Partes Review, Declaration of F. Peter Guengerich, Ph.D. [cited by applicant]
Exhibit 1010 for Inter Partes Review, P. Atkins et al., Chemical Principles, Third Edition (2005). [cited by applicant]
Exhibit 1012 for Inter Partes Review, Morgan, et al. “Old Drugs Yield New Discoveries: Examples from the Prodrug, Chiral Switch, and Site-Selective Deuteration Strategies” in Barratt and Frail, Drug Repositioning: Bring… [cited by applicant]
Exhibit 1013 for Inter Partes Review, L.E. Dyck, et al., “Effects of Deuterium Substitution on the Catabolismof β-Phenylethylamine: An In Vivo Study,” J. Neurochemistry, 46:2, 399-404, 399 (1986). [cited by applicant]
Exhibit 1018 for Inter Partes Review, T.R. Browne, ed., Stable Isotopes In Pharmaceutical Research (1997). [cited by applicant]
Exhibit 1019 for Inter Partes Review, V.E. Anderson, “Isotope effects on enzyme-catalyzed reactions,” Current Opinion in Structural Biology, 2:757-764 (1992). [cited by applicant]
Exhibit 1020 for Inter Partes Review, C. Hennig, et al., “Secondary Kinetic Isotope Effect in Nucleophilic Substitution,” J. Phys. Chem. A, 110:3071-79 (2006). [cited by applicant]
Exhibit 1022 for Inter Partes Review, J. Belleau et al., “Effect of Deuterium Substitution in Sympathomimetic Amines on Adrenergic Responses,” Science 133:102-104 (1961). [cited by applicant]
Exhibit 1024 for Inter Partes Review, J. Qiu, et al., “A New Class of Conformationally Rigid Analogues of 4-Amino-5-halopentanoic Acids, Potent Inactivators of γ-Aminobutyric Acid Aminotransferase,” J. Med. Chem. 43:706… [cited by applicant]
Exhibit 1025 for Inter Partes Review, J. Mayer et al., “Homotaurine Metabolized to 3-Sulfopropanoate in Cupriavidus necator H16.” J. Bacteriology, 191:6052-6058 (2009). [cited by applicant]
Exhibit 1021 for Inter Partes Review, O'Leary, “Multiple Isotope Effects on Enzyme-Catalyzed Reactions,” Annu. Rev. Biochem., 58:377-401 (1989). [cited by applicant]
Exhibit 1023 for Inter Partes Review, Caldwell, J., et al., “An Introduction to Drug Disposition: the Basic Principles of Absorption, Distribution, Metabolism, and Excretion,” Toxic Pathology, 23(2), 102-114, 110 (1995). [cited by applicant]
Exhibit 1026 for Inter Partes Review, T.S. Soper, et al., “Different Modes of Action of Inhibitors of Bacterial D-Amino Acid Transaminase.” J. Biol. Chem., 256:4263-68 (1981). [cited by applicant]
Exhibit 1028 for Inter Partes Review, Yu et al., “Stereospecific Deuterium Substitution at the α-Carbon Position of Dopamine,” Biochemical Pharmacology, 35:1027-36 (1986). [cited by applicant]
Exhibit 1031 for Inter Partes Review, Guengerich, F. P., “Kinetic deuterium isotope effects in cytochrome P450 reactions,” Methods in Enzymology, vol. 596, Chap. 9, pp. 217-238 (2017). [cited by applicant]
Exhibit 1034 for Inter Partes Review, R. I. Feldman and H Weiner, “Horse Liver Aldehyde Dehydrogenase,” J. Biol. Chem. 247 (1), 267-272 (1972). [cited by applicant]
Exhibit 1027 for Inter Partes Review, G. Burnett et al., “Mechanism-based Inaction of Pig Heart LAlanine Transaminase by L-Propargylglcine,” J. Biol. Chem., 255:3487-3497 (1980). [cited by applicant]
Exhibit 1029 for Inter Partes Review, P.H. Yu, “Deuterium Isotope Effect in γ-Aminobutyric Acid Transamination,” J. Neurochemistry, 48:440-446, 443 (1987). [cited by applicant]
Exhibit 1030 for Inter Partes Review, M.A. Rishavy, et al., “13C and 15N Kinetic Isotope Effects on the Reaction of Aspartate Aminotransferase,” Biochemistry, 27:7546-51 (2000). [cited by applicant]
Exhibit 1032 for Inter Partes Review, C. Walsh, Enzymatic Reaction Mechanisms, Freeman, New York, pp. 796-797, (1979). [cited by applicant]
Exhibit 1033 for Inter Partes Review, Miller et al., “Structure-Activity Relationships in the Oxidation of Para-Substituted Benzylamine Analogues by Recombinant Human Liver Monoamine Oxidase.” Biochemistry 38:41, 13670-… [cited by applicant]
Exhibit 1035 for Inter Partes Review, B. Yoval-Sánchez et al., “New insights into the half-of-the-sites reactivity of human aldehyde dehydrogenase 1A1,” Proteins 81 (8), 1330-1339 (2013). [cited by applicant]
Exhibit 1036 for Inter Partes Review, Guengerich, F. P., “Cytochrome P450 and Chemical Toxicology,” Chem. Res. Toxicol. 2008, 21, 1, 70-83. [cited by applicant]
Exhibit 1037 for Inter Partes Review, Alzheon Press Release, “Alzheon Presents Positive Results of ALZ-801 Clinical Studies that Lead to Advancement to Pivotal Phase 3 Study in Alzheimer's Patients with APOE4/4” (Jul. 2… [cited by applicant]
Exhibit 1014 for Inter Partes Review, Anslyn, et al. Modern Physical Organic Chemistry (2006). [cited by applicant]
Exhibit 1011 for Inter Partes Review, CRC Handbook of Chemistry and Physics, 95th Edition (2015). [cited by applicant]
Shoo, L. et al., The kinetic isotope effect in the search of deuterated drugs, Drug News & Perspectives 2010, 23(6), 398-404. [cited by applicant]
Foster, A.B. et al., Deuterium Isotope Effects in the Metabolism of Drugs and Xenobiotics: Implications for Drug Design, Advances in Drug Reseach, vol. 14, 1985. [cited by applicant]
Cecil Textbook of Medecine, 20th edition (1996), vol. 2, pp. 2050-2057. [cited by applicant]
Cecil Textbook of Medecine, 20th edition (1996), vol. 2., pp. 1992-1996. [cited by applicant]
FDA mulls drugs to slow late-stage Alzheimer's [online], retrieved on Sep. 23, 2003 from the Internet, URL: http://www.cnn.com/2003/HEALTH/conditions/09/24/Alzheimers.drug.ap/indexhtml. [cited by applicant]
Courtyn, J. et al., Synthesis of 11C-labelled acamprosate for PET studies., J. Labelled Cpd. Radiopharm, 2001, vol. 44, pp. 643-651. [cited by applicant]
International Search Report and Written Opinion issued in International application No. PCT/CA2018/050334 on Jun. 1, 2018. [cited by applicant]
Zornoza, T. et al., Evidence of a flip-flop phenomenon in acamprosate pharmacokinetics: an in vivo study in rats., Biopharm. Drug Dispos., 2006, vol. 27, pp. 305-311. [cited by applicant]
Zornoza, T. et al., Disposition of Acamprosate in the Rat: Influence of Probenecid, Biopharm. Drug Dispos., 2002, vol. 23, pp. 283-291. [cited by applicant]
Saivin, S. et al., Clinical Pharmacokinetics of Acamprosate, Clin. Pharmacokinet., 1998, vol. 35, pp. 331-345. [cited by applicant]
Chabenat, C. et al., Physicochemical, pharmacological and pharmacokinetic study of a new GABAergic compound, calcium acetylhomotaurinate, Methods ans Findings in Experimental and Clinical Pharmacology, 1998, vol. 10, pp… [cited by applicant]