WO2024253775A1 - Énantiomères de mdma - Google Patents

Énantiomères de mdma Download PDF

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Publication number
WO2024253775A1
WO2024253775A1 PCT/US2024/026779 US2024026779W WO2024253775A1 WO 2024253775 A1 WO2024253775 A1 WO 2024253775A1 US 2024026779 W US2024026779 W US 2024026779W WO 2024253775 A1 WO2024253775 A1 WO 2024253775A1
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WO
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Prior art keywords
mdma
mda
enantiomer
composition
administering
Prior art date
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Ceased
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PCT/US2024/026779
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English (en)
Inventor
Robert Barrow
Daniel R. Karlin
Gennady N. SMAGIN
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Mind Medicine Inc
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Mind Medicine Inc
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Publication date
Priority claimed from US18/331,682 external-priority patent/US20230310368A1/en
Application filed by Mind Medicine Inc filed Critical Mind Medicine Inc
Publication of WO2024253775A1 publication Critical patent/WO2024253775A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
    • A61K31/36—Compounds containing methylenedioxyphenyl groups, e.g. sesamin

Definitions

  • the present invention relates to compositions and methods for providing psychiatric treatment with MDMA and MDA. More specifically, the present invention relates to compositions and methods for providing safer treatment with enantiomers of MDMA and MDA.
  • MDMA or related substances include, but is not limited to, substance-use disorder, depression, anxiety disorder (including social anxiety), anxiety with life-threatening disease, personality disorder including narcistic and antisocial disorder, autism and other developmental disorders and obsessive-compulsive disorder. MDMA or related substances can also be used to enhance individual or couple therapy.
  • MDMA and related substances are thought to produce positive therapeutic long-term effects in the context of MDMA/substance-assisted psychotherapy by producing acute subjective positive mood effects that also enhance the effectiveness of psychotherapy and can be beneficial on their own.
  • Such acute beneficial MDMA-effects include, but are not limited to, feelings of well-being, feelings of connectivity to others, feelings of increased trust, feelings of love, enhanced emotional empathy, and enhanced feelings of pro-sociality and prosocial behavior (Hysek et aL, 2014; Liechti et al., 2001 ; Schmid et aL, 2014; Vollenweider et aL, 1998a).
  • Prior art discloses the use of substances in substance-assisted psychotherapy including MDMA, psilocybin, and LSD (Carhart-Harris et aL, 2017; Liechti, 2017; Luoma et aL, 2020; Nichols et aL, 2017; Sessa et aL, 2019; Trope et aL, 2019).
  • MDMA is the only empathogen-type substance currently investigated for substance-assisted psychotherapy while psilocybin and LSD are psychedelics with a different effect profile and mode of action (Holze et al., 2020).
  • MDMA-like substances include many compounds that may share some similarity with MDMA based on their in vitro pharmacological profiles and based on reports of their subjective effects by recreational users (Oeri, 2020).
  • MDA 3,4-Methylenedioxamphetamine
  • MDMA can produce hyperpyrexia, neurocognitive defects, and increased rates of depression. MDMA can also be neurotoxic which limits its ability to be used chronically with repeat administration. Use of MDMA often impairs declarative memory, prospective memory, and higher cognitive skills. Neurocognitive deficits are associated with reduced SERT in the hippocampus, parietal cortex, and prefrontal cortex. EEG and ERP studies have shown localized reductions in brain activity during neurocognitive performance. Deficits in sleep, mood, vision, pain, psychomotor skill, tremor, neurohormonal activity, and psychiatric status, have also been demonstrated. These effects are seen more with higher doses or longer use. (Parrott, Neuroscience & Biobehavioral Reviews, Volume 37, Issue 8, 2013, Pages 1466-1484)
  • the present invention provides for a composition for use in psychotherapeutic or medical treatment of an R(-) enantiomer of MDMA or MDA.
  • the present invention provides for a method of treating an individual for a medical condition (especially autism and social anxiety disorders), by administering an effective amount of a composition of an R(-) enantiomer of MDMA or MDA and treating the individual.
  • the present invention also provides for a method of reducing neurotoxicity of MDMA and MDA, by administering an effective amount of a composition of an R(-) enantiomer of MDMA or MDA to an individual and reducing neurotoxicity of MDMA or MDA while treating the individual.
  • FIGURE 1 is a chart of project schedule
  • FIGURE 4 is a graph of number of vocalizations
  • FIGURE 5 is a diagram of a three chamber social interaction test
  • FIGURE 10 is a graph of an ultrasonic vocalization test. DETAILED DESCRIPTION OF THE INVENTION
  • the R(-) enantiomer MDMA or MDA can be administered in a dose of IOWOO mg.
  • MDMA and MDA are agonist agents that primarily release monoamines (serotonin, norepinephrine and dopamine) and possibly also oxytocin typically by interacting with the membrane monoamine transporters (serotonin, norepinephrine, or dopamine transporter) (Hysek et al., 2014; Hysek et aL, 2012b; Simmler et aL, 2013; Verrico et aL, 2007).
  • the prodrug compound includes a chemical modification to the enantiomer of MDMA or MDA, such as an amino acid covalently attached to an enantiomer of MDMA or MDA.
  • the addition of the amino acid makes the active compound inactive mainly by preventing interaction with monoamine transporter, which is the site of action but also affecting bioavailability/rate of absorption.
  • the amino acid can be any other natural or synthetic amino acid.
  • the invention is described with lysine as amino acid example combined with MDMA and MDA. However, the invention can use any other amino acid covalently bound to any other MDMA-like substance via the amine group of the MDMA-like substance to form a peptide bond. Any other chemical modification can also be used.
  • LIS20120157706A1 , WO2017098533A2 which is derived from the combination of lysine as amino acid and dexamphetamine as psychoactive substance.
  • bis-N-protected lysine or another amino acid is activated at the carboxyl group by introducing a leaving group such as O-succinimide.
  • this activated lysine derivative is then allowed to react with a primary or secondary amine such as MDA or MDMA, respectively, to form the corresponding amide in the presence of a suitable non-protic base such as triethylamine, N-methylmorpholine or diisopropylethylamine.
  • compositions are particularly useful in continual slow-release formulations, such as transdermal patches, which can provide a low dose over a long period of time.
  • the compositions can also be administered in an intranasal spray.
  • the composition can also be in a liquid dosage form such as, but not limited to, suspensions, solutions, emulsions, elixirs, tinctures, sprays, syrups, gels, magmas, liniments, lotions, ointments, pastes, drops, or inhalants.
  • the composition can be in a solid dosage form such as, but not limited to, capsules, films, lozenge, patch, powder, tablets, pellets, pills, or troches.
  • the compound of the present invention is administered and dosed in accordance with good medical practice, considering the clinical condition of the individual patient, the site and method of administration, scheduling of administration, patient age, sex, body weight and other factors known to medical practitioners.
  • the pharmaceutically "effective amount" for purposes herein is thus determined by such considerations as are known in the art. The amount must be effective to achieve improvement including but not limited to more rapid recovery, or improvement or elimination of symptoms and other indicators as are selected as appropriate measures by those skilled in the art.
  • the compound of the present invention can be administered in various ways. It should be noted that it can be administered as the compound and can be administered alone or as an active ingredient in combination with pharmaceutically acceptable carriers, diluents, adjuvants, and vehicles.
  • the compounds can be administered orally, subcutaneously, or parenterally including sublingual, buccal, inhalation, intravenous, intramuscular, and intranasal administration. Implants of the compounds are also useful.
  • the patient being treated is a warm-blooded animal and, in particular, mammals including man.
  • the pharmaceutically acceptable carriers, diluents, adjuvants, and vehicles as well as implant carriers generally refer to inert, non-toxic solid or liquid fillers, diluents or encapsulating material not reacting with the active ingredients of the invention.
  • the doses can be single doses or multiple doses over a period of several days, weeks or months.
  • the treatment generally has a length proportional to the length of the disease process and drug effectiveness and the patient species being treated.
  • the compound of the present invention When administering the compound of the present invention orally, it will generally be formulated in an immediate release capsule, immediate release tablet, modified release capsule or tablet (including enteric coatings), solution or suspension.
  • it When administering the compound of the present invention parenterally, it will generally be formulated in a sublingual or buccal orally dissolving tablet, dissolving film, intranasal powder, intranasal solution, inhaled powder, inhaled solution, transdermal patch, transdermal patch with microneedles or other permeation enhancers, or as a unit dosage injectable form (solution, suspension, emulsion).
  • the pharmaceutical formulations suitable for injection include sterile aqueous solutions or dispersions and sterile powders for reconstitution into sterile injectable solutions or dispersions.
  • the carrier can be a solvent or dispersing medium containing, for example, water, ethanol, polyol (for example, glycerol, propylene glycol, liquid polyethylene glycol, and the like), suitable mixtures thereof, and vegetable oils.
  • Proper fluidity can be maintained, for example, by the use of a coating such as lecithin, by the maintenance of the required particle size in the case of dispersion and by the use of surfactants.
  • Nonaqueous vehicles such as cottonseed oil, sesame oil, olive oil, soybean oil, corn oil, sunflower oil, or peanut oil and esters, such as isopropyl myristate, may also be used as solvent systems for compound compositions.
  • various additives which enhance the stability, sterility, and isotonicity of the compositions including antimicrobial preservatives, antioxidants, chelating agents, and buffers, can be added.
  • antibacterial and antifungal agents for example, parabens, chlorobutanol, phenol, sorbic acid, and the like.
  • isotonic agents for example, sugars, sodium chloride, and the like.
  • Prolonged absorption of the injectable pharmaceutical form can be brought about by the use of agents delaying absorption, for example, aluminum monostearate and gelatin. According to the present invention, however, any vehicle, diluent, or additive used would have to be compatible with the compounds.
  • Sterile injectable solutions can be prepared by incorporating the compounds utilized in practicing the present invention in the required amount of the appropriate solvent with various of the other ingredients, as desired.
  • a pharmacological formulation of the present invention can be administered to the patient in an injectable formulation containing any compatible carrier, such as various vehicle, adjuvants, additives, and diluents; or the compounds utilized in the present invention can be administered parenterally to the patient in the form of slow- release subcutaneous implants or targeted delivery systems such as monoclonal antibodies, vectored delivery, iontophoretic, polymer matrices, liposomes, and microspheres.
  • any compatible carrier such as various vehicle, adjuvants, additives, and diluents
  • the compounds utilized in the present invention can be administered parenterally to the patient in the form of slow- release subcutaneous implants or targeted delivery systems such as monoclonal antibodies, vectored delivery, iontophoretic, polymer matrices, liposomes, and microspheres.
  • Examples of delivery systems useful in the present invention include: 5,225,182; 5,169,383; 5,167,616; 4,959,217; 4,925,678; 4,487,603; 4,486,194; 4,447,233; 4,447,224; 4,439,196; and 4,475,196. Many other such implants, delivery systems, and modules are well known to those skilled in the art.
  • the present invention provides for a method of treating an individual for a medical disorder, by administering an effective amount of a composition of an R(-) enantiomer of MDMA or MDA to the individual and treating the individual.
  • the method can further include preventing or reducing side effects of neurotoxicity, hyperthermia and dependence/addiction experienced with racemic MDMA or MDA. Any of the prodrugs listed above can also be used.
  • compositions can be used in treating medical disorders or conditions including post-traumatic stress disorder, social anxiety, autism spectrum disorder, substance use disorder, depression, anxiety disorder, anxiety with lifethreatening disease, personality disorder including narcistic or antisocial personality disorder, schizophrenia, obsessive compulsive disorder, couple therapy, enhancement of any psychotherapy by inducing feelings of well-being connectivity, trust, love, empathy, openness, and pro-sociality, and enhancing therapeutic bond in any psychotherapy of patients or neurotic/healthy subjects.
  • medical disorders or conditions including post-traumatic stress disorder, social anxiety, autism spectrum disorder, substance use disorder, depression, anxiety disorder, anxiety with lifethreatening disease, personality disorder including narcistic or antisocial personality disorder, schizophrenia, obsessive compulsive disorder, couple therapy, enhancement of any psychotherapy by inducing feelings of well-being connectivity, trust, love, empathy, openness, and pro-sociality, and enhancing therapeutic bond in any psychotherapy of patients or neurotic/healthy subjects.
  • the present invention provides for a method of reducing neurotoxicity of MDMA and MDA, by administering an effective amount of a composition of an R(-) enantiomer of MDMA or MDA to an individual and reducing neurotoxicity of MDMA or MDA while treating the individual.
  • This method allows for daily administration of the R(-) enantiomer of MDMA or MDA to the individual while avoiding the unwanted side effects of neurotoxicity of racemic MDMA or MDA.
  • Any of the prodrugs listed above can also be used.
  • the present invention provides for a method of reducing hyperthermia of MDMA and MDA, by administering an effective amount of a composition of an R(-) enantiomer of MDMA or MDA to an individual and reducing hyperthermia of MDMA or MDA while treating the individual.
  • This method allows for daily administration of the R(-) enantiomer of MDMA or MDA to the individual while avoiding the unwanted side effects of hyperthermia of racemic MDMA or MDA.
  • Any of the prodrugs listed above can also be used.
  • the present invention provides for a method of reducing dependence and abuse liability of MDMA and MDA, by administering an effective amount of a composition of an R(-) enantiomer of MDMA or MDA to an individual and reducing the physical dependence and abuse liability of MDMA or MDA while treating the individual.
  • This method allows for daily administration of the R(-) enantiomer of MDMA or MDA to the individual while avoiding the unwanted side effects of dependence I abuse liability of racemic MDMA or MDA.
  • Any of the prodrugs listed above can also be used.
  • Fragile X syndrome is known as a monogenic cause of Autism Spectrum Disorders (ASD) and one of the most common inherited forms of intellectual disability. Patients with FXS not only suffer from intellectual disability, but also manifest core and secondary phenotypic traits of ASD such as hyperactivity, repetitive behaviors and problems with executive and language problems causing sociability impairments.
  • the Fmr1 -KO mouse has a neomycin resistance cassette replacing exon 5 of the fragile X mental retardation syndrome 1 (Fmr1 ) gene causing an increase in the number of CGG repeats that lead to hypermethylation of the Fmr1 gene, therefore inhibiting FMR protein production.
  • Fmr1 -K0 mice are bred on a C57BL/6J background.
  • the fragile X mouse model Fmr1 -KO presents strong ASD-like behaviors such as increased activity and hyperactivity, decreased anxiety, strong repetitive behavior as well as reduced social behavior and vocalization.
  • the Fmr1 -KO mouse model thus allows in vivo compound tests for the treatment of ASD-like behaviors.
  • the aim of the study is to examine the effects of R-MDMA, S-MDMA and RS-MDMA (separate racemic forms and a racemic mixture of MDMA) administered intraperitoneally in FMR1 knockout (KO) mice in comparison to vehicle treated FMR1 KO and C57BL/6J controls. Effects on general activity, repetitive behavior, social interaction and ultrasound vocalization are assessed after acute treatment.
  • Fmr1 breeder pairs (JAX Strain B6.129P2-Fmr1tm1 Cgr/J #003025) were purchased from Jackson laboratories and sent to QPS (homozygous females mated with hemizygous males). Breeder pairs were maintained at QPS for anticipated three breeding cycles (13 weeks in total) to obtain a total number of 96 male Fmr1 KO mice for the subsequent efficacy study.
  • mice received a three times treatment via intraperitoneal injection of either test compounds or vehicle (group A - F, Group allocation see TABLE 1 ).
  • S,R( ⁇ )-3,4-methylenedioxymethamphetamine is a substituted phenethylamine with structural and functional similarities to amphetamine-like psychostimulants and mescaline-like hallucinogens.
  • SR-MDMA S,R( ⁇ )-3,4-methylenedioxymethamphetamine
  • the Fmr1 KO mouse lacks FMRP protein due to a disruption in its Fmr1 gene and this mouse model is well established for the study of ASD/FXS with symptoms of social deficits and repetitive behaviors.
  • phenotypic traits such as hyperactivity and altered anxiety are observed in this model.
  • the Open Field was cleaned with 70% Isopropanol after each mouse to get rid of odor traces. Testing was performed under standard room lighting conditions during the light phase of the circadian cycle.
  • test animal On the testing day, the test animal was placed in the center of the box and was allowed to explore it for ten minutes with two empty stranger mouse cylinders on each side of the box for habituation.
  • mice were immediately tested for social recognition.
  • the already known mouse stayed in the left chamber and a new mouse was placed under the cylinder in the right chamber.
  • the test mouse was again placed in the middle chamber and, for 10 minutes, it was measured how much time it spent in each chamber and how much time it spent sniffing each mouse. Healthy mice will spend more time with the new mouse due to novelty.
  • Socially disturbed mice might not recognize the already known mouse and spend therefore similar amounts of time with each mouse. It might also be that a socially disturbed mouse does not prefer social contact and will therefore spend most of the time in the middle chamber.
  • mice were subcutaneously treated with 50 pl of B-estradiol 48 hours prior to testing (time sensitive). Furthermore, females received a subcutaneous injection of 50 pl progesterone (16 mg/ml- P-0130, Sigma) 4 hours before the testing (time critical, +45 minutes possible (not shorter)). The estrous cycle was induced this way in female mice, both before familiarization of male study animals, and testing days. To familiarize the male animals with female odors, they were exposed to females in the estrous cycle for 5 minutes a week before testing.
  • the Fmr1 knockout (KO) mouse lacks FMRP protein due to a disruption in its Fmr1 gene.
  • This mouse model has been widely used for the study of autism spectrum disorder (ASD) and Fragile X syndrome (FXS) which mimics the human disorder by measuring social deficits and repetitive behaviors.
  • ASD autism spectrum disorder
  • FXS Fragile X syndrome

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  • Health & Medical Sciences (AREA)
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  • Animal Behavior & Ethology (AREA)
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  • Engineering & Computer Science (AREA)
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  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
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  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

L'invention concerne une composition destinée à être utilisée dans un traitement psychothérapeutique ou médical à base d'un énantiomère R(-) de MDMA ou de MDA. L'invention concerne également une méthode de traitement d'un sujet contre un problème de santé (en particulier l'autisme et les troubles d'anxiété sociale), par administration d'une quantité efficace d'une composition à base d'un énantiomère R(-) de MDMA ou de MDA, et par traitement du sujet. L'invention concerne de même une méthode de réduction de la neurotoxicité de la MDMA et de la MDA, par administration d'une quantité efficace d'une composition à base d'un énantiomère R(-) de MDMA ou de MDA à un sujet, et de réduction de la neurotoxicité de la MDMA ou de la MDA pendant le traitement du sujet. L'invention concerne en outre une méthode de réduction de l'hyperthermie provoquée par la MDMA et la MDA. L'invention concerne par ailleurs une méthode de réduction de la dépendance physique à la MDMA et à la MDA ou du risque d'abus de celles-ci.
PCT/US2024/026779 2023-06-08 2024-04-29 Énantiomères de mdma Ceased WO2024253775A1 (fr)

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US18/331,682 2023-06-08
US18/331,682 US20230310368A1 (en) 2021-05-05 2023-06-08 Mdma enantiomers

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12611399B2 (en) 2021-05-04 2026-04-28 Definium Therapeutics US, Inc. Movement disorders

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022235530A1 (fr) * 2021-05-05 2022-11-10 Mind Medicine, Inc. Énantiomères de mdma
WO2022256720A2 (fr) * 2021-06-03 2022-12-08 Arcadia Medicine, Inc. Compositions entactogènes énantiomères et leurs méthodes d'utilisation
WO2023056102A1 (fr) * 2021-10-01 2023-04-06 ATAI Life Sciences AG Nouveaux promédicaments de mdma, mda et leurs dérivés
US20230233688A1 (en) * 2021-11-04 2023-07-27 Mind Medicine, Inc. Mdma prodrugs to assist psychotherapy

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2022235530A1 (fr) * 2021-05-05 2022-11-10 Mind Medicine, Inc. Énantiomères de mdma
WO2022256720A2 (fr) * 2021-06-03 2022-12-08 Arcadia Medicine, Inc. Compositions entactogènes énantiomères et leurs méthodes d'utilisation
WO2023056102A1 (fr) * 2021-10-01 2023-04-06 ATAI Life Sciences AG Nouveaux promédicaments de mdma, mda et leurs dérivés
US20230233688A1 (en) * 2021-11-04 2023-07-27 Mind Medicine, Inc. Mdma prodrugs to assist psychotherapy

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12611399B2 (en) 2021-05-04 2026-04-28 Definium Therapeutics US, Inc. Movement disorders

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