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WO2025006964A3 - 2-(2-ethoxy-4-propylsulfanyl-5 methoxyphenyl)ethanaminium chloride - Google Patents

2-(2-ethoxy-4-propylsulfanyl-5 methoxyphenyl)ethanaminium chloride Download PDF

Info

Publication number
WO2025006964A3
WO2025006964A3 PCT/US2024/036128 US2024036128W WO2025006964A3 WO 2025006964 A3 WO2025006964 A3 WO 2025006964A3 US 2024036128 W US2024036128 W US 2024036128W WO 2025006964 A3 WO2025006964 A3 WO 2025006964A3
Authority
WO
WIPO (PCT)
Prior art keywords
propylsulfanyl
ethoxy
methoxyphenyl
ethanaminium chloride
chloride
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/US2024/036128
Other languages
French (fr)
Other versions
WO2025006964A2 (en
Inventor
Andrew R. Chadeayne
Alexander T. Shulgin
Nicholas V. Cozzi
Paul F. Daley
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Caamtech Inc
Alexander Shulgin Research Institute Inc
Original Assignee
Caamtech Inc
Alexander Shulgin Research Institute Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Caamtech Inc, Alexander Shulgin Research Institute Inc filed Critical Caamtech Inc
Publication of WO2025006964A2 publication Critical patent/WO2025006964A2/en
Publication of WO2025006964A3 publication Critical patent/WO2025006964A3/en
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/33—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring
    • C07C323/35—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group
    • C07C323/36—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to a carbon atom of the same non-condensed six-membered aromatic ring the thio group being a sulfide group the sulfur atom of the sulfide group being further bound to an acyclic carbon atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The disclosure relates to 2-[2-ethoxy-5-methoxy-4-(propylsulfanyl)phenyl]ethan-1-aminium chloride (2- (2-ethoxy-4-propylsulfanyl-5-methoxyphenyl)ethanaminium chloride), crystalline 2-(2-ethoxy-4- propylsulfanyl-5-methoxyphenyl)ethanaminium chloride, and specific crystalline forms thereof, including crystalline form 1 of 2-(2-ethoxy-4-propylsulfanyl-5-methoxyphenyl)ethanaminium chloride, to compositions containing the same, and to methods of treatment using them.
PCT/US2024/036128 2023-06-30 2024-06-28 2-(2-ethoxy-4-propylsulfanyl-5 methoxyphenyl)ethanaminium chloride Pending WO2025006964A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202363511260P 2023-06-30 2023-06-30
US63/511,260 2023-06-30

Publications (2)

Publication Number Publication Date
WO2025006964A2 WO2025006964A2 (en) 2025-01-02
WO2025006964A3 true WO2025006964A3 (en) 2025-03-27

Family

ID=93940045

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2024/036128 Pending WO2025006964A2 (en) 2023-06-30 2024-06-28 2-(2-ethoxy-4-propylsulfanyl-5 methoxyphenyl)ethanaminium chloride

Country Status (1)

Country Link
WO (1) WO2025006964A2 (en)

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
FLANAGAN THOMAS W., NICHOLS CHARLES D.: "Psychedelics as anti-inflammatory agents", INTERNATIONAL REVIEW OF PSYCHIATRY, vol. 30, no. 4, 4 July 2018 (2018-07-04), GB , pages 363 - 375, XP055970282, ISSN: 0954-0261, DOI: 10.1080/09540261.2018.1481827 *
FLYNN G.L., YALKOWSKY S.H.: "Correlation and Prediction of Mass Transport across Membranes I: Influence of Alkyl Chain Length on Flux-Determining Properties of Barrier and Diffusant", JOURNAL OF PHARMACEUTICAL SCIENCES, vol. 61, no. 6, 1 June 1972 (1972-06-01), pages 838 - 852, XP055831127, ISSN: 0022-3549, DOI: 10.1002/jps.2600610603 *
HALBERSTADT ADAM L., LUETHI DINO, HOENER MARIUS C., TRACHSEL DANIEL, BRANDT SIMON D., LIECHTI MATTHIAS E.: "Use of the head-twitch response to investigate the structure–activity relationships of 4-thio-substituted 2,5-dimethoxyphenylalkylamines", PSYCHOPHARMACOLOGY, vol. 240, no. 1, 1 January 2023 (2023-01-01), DE , pages 115 - 126, XP093295499, ISSN: 0033-3158, DOI: 10.1007/s00213-022-06279-2 *
HOSSAIN MITHU MD SADEQUE, ECONOMIDOU SOPHIA, TRIVEDI VIVEK, BHATT SAUMIL, DOUROUMIS DENNIS: "Advanced Methodologies for Pharmaceutical Salt Synthesis", CRYSTAL GROWTH & DESIGN, vol. 21, no. 2, 3 February 2021 (2021-02-03), US , pages 1358 - 1374, XP093097792, ISSN: 1528-7483, DOI: 10.1021/acs.cgd.0c01427 *
MC GRANE OWEN, SIMMONS JOSHUA, JACOBSON ERIC, SKINNER CARL: "Alarming Trends in a Novel Class of Designer Drugs", JOURNAL OF CLINICAL TOXICOLOGY, 16 November 2011 (2011-11-16), pages 1 - 3, XP093295502, ISSN: 2161-0495, DOI: 10.4172/2161-0495.1000108 *
OMARI DERAR M, AKKAM YAZAN, SALLAM ASSAYED: "Drug-Excipient Interactions: An Overview on Mechanisms and Effects on Drug Stability and Bioavailability", ANNALS OF THE ROMANIAN SOCIETY FOR CELL BIOLOGY, 1 January 2021 (2021-01-01), Arad, pages 8402 - 8429, XP093102914 *

Also Published As

Publication number Publication date
WO2025006964A2 (en) 2025-01-02

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