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WO2025052388A1 - Composés psychédéliques, leurs procédés de préparation et leurs utilisations - Google Patents

Composés psychédéliques, leurs procédés de préparation et leurs utilisations Download PDF

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Publication number
WO2025052388A1
WO2025052388A1 PCT/IL2024/050898 IL2024050898W WO2025052388A1 WO 2025052388 A1 WO2025052388 A1 WO 2025052388A1 IL 2024050898 W IL2024050898 W IL 2024050898W WO 2025052388 A1 WO2025052388 A1 WO 2025052388A1
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WIPO (PCT)
Prior art keywords
branched
straight
compound according
halogen
alkyl
Prior art date
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Application number
PCT/IL2024/050898
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English (en)
Inventor
Ahmad MASARWA
Rami YAKA
Avi PRIEL
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.)
Yissum Research Development Co of Hebrew University of Jerusalem
Original Assignee
Yissum Research Development Co of Hebrew University of Jerusalem
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Publication of WO2025052388A1 publication Critical patent/WO2025052388A1/fr
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Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/22—Anxiolytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring

Definitions

  • N,N-Dimethyltryptamine (DMT orN,N-DMT, SPL026) is a substituted tryptamine that occurs in many plants and animals, including humans, and which is both a derivative and a structural analog of tryptamine.
  • DMT is used as a psychedelic drug and prepared by various cultures for ritual purposes as an entheogen.
  • DMT has a rapid onset, intense effects, and a relatively short duration of action.
  • DMT can be inhaled, ingested, or injected and its effects depend on the dose, as well as the mode of administration. When inhaled or injected, the effects last a short period of time: about five to 15 minutes. Effects can last three hours or more.
  • DMT can produce vivid "projections" of mystical experiences involving euphoria and dynamic pseudohallucinations of geometric forms.
  • DMT is a functional analog and structural analog of other psychedelic tryptamines such as O-acetylpsilocin (4-AcO-DMT), psilocybin (4-PO-DMT), psilocin (4-HO-DMT), O-methylbufotenin (5-MeO-DMT), and bufotenin (5-HO-DMT).
  • O-acetylpsilocin (4-AcO-DMT
  • psilocybin 4-PO-DMT
  • psilocin (4-HO-DMT
  • O-methylbufotenin 5-MeO-DMT
  • bufotenin 5-HO-DMT
  • DMT Dimethyltryptamine
  • Sig- 1 Rs sigma- 1 receptors
  • the present invention provides a compound having the general formula (I):
  • R1 and R2 are each selected from H, straight or branched Cl - C5 alkyl, straight or branched C21 - C5 alkenyl, straight or branched C2 - C5 alkynyl, and a moiety of formula (II)
  • each of R13 - R22 are each selected from H, halogen (i.e. F, Cl, Br, I), straight or branched Cl - C8 alkoxy, straight or branched Cl - C8 alkyl, a chemical protecting group;
  • R7 - R12 are each selected from null, H or halogen
  • X is selected from C or N; wherein when X is N then R9 is null;
  • R1 and R2 are each straight or branched Cl - C3 alkyl then at least one of R7 - R12 is different than H.
  • R1 and R2 are each a straight or branched Cl - C5 alkyl, provided that when R1 and R2 are each straight or branched Cl - C3 alkyl then at least one of R7 - R12 is different than H.
  • At least one of R7 - R12 is a halogen.
  • R11 is halogen.
  • R11 is F.
  • R11 is Br.
  • R1 and R2 are each a straight or branched Cl - C5 alkyl; R3 - R6 are H; and R11 is halogen.
  • Rl, R3 - R12 are H and R2 is a moiety of formula (II)
  • each of R13 - R22 are each selected from H, halogen, straight or branched Cl - C8 alkoxy, straight or branched Cl - C8 alkyl, straight or branched C2 - C8 alkenyl, straight or branched C2 - C8 alkynyl.
  • Rl, R3 - R12 are H and R2 is a moiety of formula (II)
  • each of R13 - R22 are each selected from H, halogen, straight or branched Cl - C8 alkoxy, straight or branched Cl - C8 alkyl provided that at least one of R13 - R22 is different than H.
  • a compound of the invention is selected from: 9
  • the invention further provides a compound for use in the treatment of disease, symptom or condition selected from depression, including resistant depression, stress including PTSD (post-traumatic stress disorder), cerebral ischemia and any combinations thereof, wherein said compound having the general formula (I):
  • each of R13 - R22 are each selected from H, halogen, straight or branched Cl - C8 alkoxy, straight or branched Cl - C8 alkyl, a chemical protecting group; or R1 and R2 together with the nitrogen atom they are connected to form a 5 - 6 membered heterocyclic ring;
  • R7 - R12 are each selected from H, halogen.
  • R1 and R2 are each a straight or branched Cl - C5 alkyl.
  • R3 - R6 are H.
  • R7 - R12 is a halogen.
  • R11 is halogen.
  • halogen is selected from F, Cl, Br and I.
  • halogen is F.
  • halogen is Br.
  • R1 and R2 are each a straight or branched Cl - C5 alkyl; R3 - R6 are H; and R11 is halogen.
  • Rl, R3 - R12 are H and R2 is a moiety of formula (II) [00034] wherein each of R13 - R22 are each selected from H, halogen, straight or branched Cl - C8 alkoxy, straight or branched Cl - C8 alkyl, straight or branched C2 - C8 alkenyl, straight or branched C2 - C8 alkynyl.
  • Rl, R3 - R12 are H and R2 is a moiety of formula (II)
  • each of R13 - R22 are each selected from H, halogen, straight or branched Cl - C8 alkoxy, straight or branched Cl - C8 alkyl provided that at least one of R13 - R22 is different than H.
  • R3 - R12 are H; and Rl and R2 together with the nitrogen atom they are connected to form a 5 - 6 membered heterocyclic ring.
  • a compound of the invention is selected from: [00041] [00042] In another aspect the invention provides a compound having the general formula
  • R23 and R24 are each a phenyl, a straight or branched Cl - C5 alkyl substituted with at least one group selected from a phenyl, a halogenated phenyl, an indolyl, a halogenated indolyl; and R25 - R34 are each selected from H, straight or branched Cl - C5 alkoxy.
  • R25, R27, R29, R30, R32 R34 are each a straight or branched Cl - C5 alkoxy.
  • R23 and R24 are each a phenyl.
  • R23 and R24 are each straight or branched Cl - C5 alkyl substituted with at least one phenyl.
  • R23 and R24 are each straight or branched Cl - C5 alkyl substituted with at least one halogenated phenyl (i.e. a phenyl ring substituted by at least one halogen).
  • R23 and R24 are each straight or branched Cl - C5 alkyl substituted with at least one indolyl. [00049] In some embodiments, R23 and R24 are each straight or branched Cl - C5 alkyl substituted with at least one halogenated indolyl (i.e. a indolyl ring substituted by at least one halogen).
  • the invention further provides a composition comprising at least one compound as disclosed herein above.
  • the invention further provides a composition as disclosed herein above, for use in the treatment of disease, symptom or condition associated with cerebral ischemia.
  • the invention provides a method of treating a disease, symptom or condition associated with depression, including resistant depression; said method comprising administering to a subject in need thereof at least one compound as disclosed herein above and below.
  • the invention provides a method of treating a disease, symptom or condition associated with stress including PTSD; said method comprising administering to a subject in need thereof at least one compound as disclosed herein above and below.
  • the invention provides a method of treating a disease, symptom or condition associated with cerebral ischemia; said method comprising administering to a subj ect in need thereof at least one compound as disclosed herein above and below.
  • TRD treatment-resistant depression
  • Cerebral ischemia it should be understood to relate to brain ischemia which is a condition in which there is insufficient blood flow to the brain to meet metabolic demand. This condition leads to poor oxygen supply or cerebral hypoxia and thus leads to the death of brain tissue or cerebral infarction/ischemic stroke. Cerebral ischemia is a sub-type of stroke along with subarachnoid hemorrhage and intracerebral hemorrhage.
  • PTSD post-traumatic stress disorder
  • Symptoms of PTSD may include disturbing thoughts, feelings, or dreams related to the events, mental or physical distress to trauma-related cues, attempts to avoid trauma-related cues, alterations in the way a person thinks and feels, and an increase in the fight-or-flight response. These symptoms last for more than a month after the event. A person with PTSD is at a higher risk of suicide and intentional self-harm.
  • the term “ straight or branched Ci - Cs alkyl” should be understood to encompass any straight or branched saturated hydrocarbon chain having 1, 2, 3, 4, 5 carbon atoms, wherein only sigma bonds connect between the atoms of the chain, and wherein one hydrogen atom is removed from any carbon atom of the chain.
  • the term “straight or branched Ci - Cs alkyl” should be understood to encompass any straight or branched saturated hydrocarbon chain having 1, 2, 3, 4, 5, 6, 7, 8 carbon atoms, wherein only sigma bonds connect between the atoms of the chain, and wherein one hydrogen atom is removed from any carbon atom of the chain.
  • the term “straight or branched C2 - C5 alkenyl” should be understood to encompass any straight or branched unsaturated hydrocarbon chain having 2, 3, 4, 5 carbon atoms, wherein at least one double bond connects two carbon atoms at any point of the hydrocarbon chain, and wherein one hydrogen atom is removed from any carbon atom of the chain.
  • the term “straight or branched C2 - Cs alkenyl” should be understood to encompass any straight or branched unsaturated hydrocarbon chain having 2, 3, 4, 5, 6, 7, 8 carbon atoms, wherein at least one double bond connects two carbon atoms at any point of the hydrocarbon chain, and wherein one hydrogen atom is removed from any carbon atom of the chain.
  • the term “straight or branched C2 - C5 alkynyF should be understood to encompass any straight or branched unsaturated hydrocarbon chain having 2, 3, 4, 5 carbon atoms, wherein at least one triple bond connects two carbon atoms at any point of the hydrocarbon chain, and wherein one hydrogen atom is removed from any carbon atom of the chain.
  • the term “straight or branched C2 - Cs alkynyF should be understood to encompass any straight or branched unsaturated hydrocarbon chain having 2, 3, 4, 5, 6, 7, 8 carbon atoms, wherein at least one triple bond connects two carbon atoms at any point of the hydrocarbon chain, and wherein one hydrogen atom is removed from any carbon atom of the chain.
  • Ci-Cs alkoxyF refers to a functional group -OR wherein R is a Ci-Cs alkyl group.
  • the present invention relates to pharmaceutical compositions comprising a compound of the subject invention in admixture with pharmaceutically acceptable auxiliaries, and optionally other therapeutic agents.
  • the auxiliaries must be “acceptable” in the sense of being compatible with the other ingredients of the composition and not deleterious to the recipients thereof.
  • Such methods include the step of bringing in association compounds used in the invention or combinations thereof with any auxiliary agent.
  • auxiliary agent(s) also named accessory ingredient(s) include those conventional in the art, such as carriers, fillers, binders, diluents, disintegrants, lubricants, colorants, flavoring agents, anti-oxidants, and wetting agents.
  • compositions include aqueous and nonaqueous sterile injection.
  • the compositions may be presented in unit-dose or multi-dose containers, for example, sealed vials and ampoules, and may be stored in a freeze-dried (lyophilised) condition requiring only the addition of sterile liquid carrier, for example, water, prior to use.
  • sterile liquid carrier for example, water
  • transdermal administration e.g., gels, patches, or sprays can be contemplated.
  • Compositions or formulations suitable for pulmonary administration e.g., by nasal inhalation, include fine dust or mists, which may be generated by means of metered dose pressurized aerosols, nebulizers or insufflators.
  • composition will necessarily be dependent upon the therapeutic or nutritional effect to be achieved and may vary with the particular formula, the route of administration, and the age and condition of the individual subject to whom the composition is to be administered.
  • the term "effective amount” means the amount of a drug or pharmaceutical composition that will elicit the biological or medical response of a tissue, system, animal, or human that is being sought, for instance, by a researcher or clinician.
  • therapeutically effective amount means any amount which, as compared to a corresponding subject who has not received such amount, results in improved treatment, healing, prevention, or amelioration of a disease, disorder, or side effect, slowing the progression of, or a decrease in the rate of advancement of a disease or disorder, condition or symptom.
  • the term also includes within its scope amounts effective to enhance normal physiological function. DETAILED DESCRIPTION OF THE PRESENT INVENTION

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pain & Pain Management (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne des composés synthétiques présentant une bioactivité psychédélique, des compositions les comprenant, leurs procédés de préparation et leurs utilisations pour traiter des maladies, des symptômes et des troubles.
PCT/IL2024/050898 2023-09-07 2024-09-05 Composés psychédéliques, leurs procédés de préparation et leurs utilisations Pending WO2025052388A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US202363581088P 2023-09-07 2023-09-07
US63/581,088 2023-09-07

Publications (1)

Publication Number Publication Date
WO2025052388A1 true WO2025052388A1 (fr) 2025-03-13

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Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004056769A2 (fr) * 2002-12-20 2004-07-08 Ciba Specialty Chemicals Holding Inc. Synthèse d'amines et intermédiaires pour cette synthèse
US20090093513A1 (en) * 2007-10-09 2009-04-09 Hamann Mark T Method to Use Compositions Having Antidepressant Anxiolytic and Other Neurological Activity and Compositions of Matter
CN107098900A (zh) * 2017-04-07 2017-08-29 中国科学院兰州化学物理研究所苏州研究院 一种钯催化合成四氢β‑咔啉‑1‑酮类化合物的方法
WO2019081764A1 (fr) * 2017-10-26 2019-05-02 Consejo Superior De Investigaciones Científicas (Csic) Produit d'association pour le traitement de troubles neurologiques et/ou psychiatriques
WO2021168082A1 (fr) * 2020-02-18 2021-08-26 Gilgamesh Pharmaceuticals, Inc. Tryptamines spécifiques destinées à être utilisées dans le traitement de troubles de l'humeur
WO2022047579A1 (fr) * 2020-09-01 2022-03-10 Magicmed Industries Inc. Dérivés de psilocybine halogénés et leurs procédés d'utilisation
WO2022256554A1 (fr) * 2021-06-02 2022-12-08 University Of The Sciences Composés de tryptamine fluorés, analogues associés et méthodes les utilisant
WO2023115166A1 (fr) * 2021-12-24 2023-06-29 Psylo Pty Ltd Composés
WO2024138007A2 (fr) * 2022-12-21 2024-06-27 Caamtech, Inc. Dérivés de tryptamine

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004056769A2 (fr) * 2002-12-20 2004-07-08 Ciba Specialty Chemicals Holding Inc. Synthèse d'amines et intermédiaires pour cette synthèse
US20090093513A1 (en) * 2007-10-09 2009-04-09 Hamann Mark T Method to Use Compositions Having Antidepressant Anxiolytic and Other Neurological Activity and Compositions of Matter
CN107098900A (zh) * 2017-04-07 2017-08-29 中国科学院兰州化学物理研究所苏州研究院 一种钯催化合成四氢β‑咔啉‑1‑酮类化合物的方法
WO2019081764A1 (fr) * 2017-10-26 2019-05-02 Consejo Superior De Investigaciones Científicas (Csic) Produit d'association pour le traitement de troubles neurologiques et/ou psychiatriques
WO2021168082A1 (fr) * 2020-02-18 2021-08-26 Gilgamesh Pharmaceuticals, Inc. Tryptamines spécifiques destinées à être utilisées dans le traitement de troubles de l'humeur
WO2022047579A1 (fr) * 2020-09-01 2022-03-10 Magicmed Industries Inc. Dérivés de psilocybine halogénés et leurs procédés d'utilisation
WO2022256554A1 (fr) * 2021-06-02 2022-12-08 University Of The Sciences Composés de tryptamine fluorés, analogues associés et méthodes les utilisant
WO2023115166A1 (fr) * 2021-12-24 2023-06-29 Psylo Pty Ltd Composés
WO2024138007A2 (fr) * 2022-12-21 2024-06-27 Caamtech, Inc. Dérivés de tryptamine

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
COZZI NICHOLAS V ET AL: "Receptor binding profiles and quantitative structure-affinity relationships of some 5-substituted-N,N-diallyltryptamines", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, ELSEVIER, AMSTERDAM NL, vol. 26, no. 3, 18 December 2015 (2015-12-18), pages 959 - 964, XP029391908, ISSN: 0960-894X, DOI: 10.1016/J.BMCL.2015.12.053 *
DONG CHUNYANG ET AL: "Psychedelic-inspired drug discovery using an engineered biosensor", CELL, vol. 184, no. 10, 1 May 2021 (2021-05-01), Amsterdam NL, pages 2779 - 2792, XP093221468, ISSN: 0092-8674, Retrieved from the Internet <URL:https://doi.org/10.1016/j.cell.2021.03.043> DOI: 10.1016/j.cell.2021.03.043 *
HAN HUI ET AL: "Pd/Cu Cocatalyzed Oxidative Tandem C-H Aminocarbonylation and Dehydrogenation of Tryptamines: Synthesis of Carbolinones", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 84, no. 6, 22 February 2019 (2019-02-22), United States, pages 3357 - 3369, XP093221703, ISSN: 0022-3263, DOI: 10.1021/acs.joc.8b03266 *
MOHAMED IBRAHIM ET AL: "Marine Inspired 2-(5-Halo-1H-indol-3-yl)-N,N-dimethylethanamines as Modulators of Serotonin Receptors: An Example Illustrating the Power of Bromine as Part of the Uniquely Marine Chemical Space", MARINE DRUGS, vol. 15, no. 248, 1 January 2017 (2017-01-01), pages 1 - 14, XP055759175, DOI: 10.3390/md15080248 *
SIMON D. BRANDT ET AL: "Microwave-accelerated synthesis of psychoactive deuterated N , N -dialkylated-[ [alpha] , [alpha] , [beta] , [beta] -d 4 ]-tryptamines", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, vol. 51, no. 14, 1 November 2008 (2008-11-01), GB, pages 423 - 429, XP055724013, ISSN: 0362-4803, DOI: 10.1002/jlcr.1557 *

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