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NZ783166B2 - Therapeutic compositions comprising deuterated or partially deuterated n,n-dimethyltryptamine compounds - Google Patents
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NZ783166B2 - Therapeutic compositions comprising deuterated or partially deuterated n,n-dimethyltryptamine compounds - Google Patents

Therapeutic compositions comprising deuterated or partially deuterated n,n-dimethyltryptamine compounds

Info

Publication number
NZ783166B2
NZ783166B2 NZ783166A NZ78316620A NZ783166B2 NZ 783166 B2 NZ783166 B2 NZ 783166B2 NZ 783166 A NZ783166 A NZ 783166A NZ 78316620 A NZ78316620 A NZ 78316620A NZ 783166 B2 NZ783166 B2 NZ 783166B2
Authority
NZ
New Zealand
Prior art keywords
dimethyltryptamine
acceptable salt
pharmaceutically acceptable
dideutero
composition
Prior art date
Application number
NZ783166A
Other versions
NZ783166A (en
Inventor
Tiffanie Benway
Zelah Joel
Peter Rands
Original Assignee
Cybin Uk Ltd
Filing date
Publication date
Priority claimed from GBGB1907871.6A external-priority patent/GB201907871D0/en
Application filed by Cybin Uk Ltd filed Critical Cybin Uk Ltd
Publication of NZ783166A publication Critical patent/NZ783166A/en
Publication of NZ783166B2 publication Critical patent/NZ783166B2/en

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2300/00Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/404Indoles, e.g. pindolol
    • A61K31/4045Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/18Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/22Anxiolytics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/30Drugs for disorders of the nervous system for treating abuse or dependence
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05Isotopically modified compounds, e.g. labelled
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D209/00Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04Indoles; Hydrogenated indoles
    • C07D209/10Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C07D209/16Tryptamines

Abstract

The present invention relates to compositions comprising N,N-dimethyltryptamine, deuterated N,N-dimethyltryptamine and/or partially deuterated N,N-dimethyltryptamine. In particular, the present invention relates to compositions comprising a combination of N,N-dimethyltryptamine and 2% or more by weight of one or more deuterated N,N- dimethyltryptamine compound selected from a,a-dideutero-N,N-dimethyltryptamine and a,a,ß,ß-tetradeutero-N,N-dimethyltryptamine. Additional and alternative compositions of the present invention comprise a combination of N,N-dimethyltryptamine and 2% or more by weight of one or more partially deuterated N,N-dimethyltryptamine compound selected from a,ß,ß-trideutero-N,N-dimethyltryptamine, a,ß-dideutero-N,N- dimethyltryptamine, and a-deutero-N,N-dimethyltryptamine. Methods of synthesising compositions of the present invention, and methods of use of presently described compositions in treating psychiatric or psychocognitive disorders, such as major depressive disorder, are also provided.

Claims (14)

1. A composition comprising: (a) an a,a-dideutero-N,N -dimethyltryptamine compound, or a pharmaceutically acceptable salt thereof; (b) an a-protio, a-deutero-N,N -dimethyltryptamine compound, or a pharmaceutically acceptable salt thereof; and (c) N,N -dimethyltryptamine compound, or a pharmaceutically able salt thereof wherein the composition comprises 50% or more by weight of the a,a-dideutero-N,N - yltryptamine compound, or a pharmaceutically acceptable salt thereof, and the io, a-deutero-N,N -dimethyltryptamine compound, or a pharmaceutically acceptable salt thereof.
2. The ition of claim 1, which consists essentially of: (a) a,a-dideutero-N,N-dimethyltryptamine, or a pharmaceutically acceptable salt thereof; (b) a-protio, a-deutero-N,N-dimethyltryptamine, or a pharmaceutically acceptable salt thereof; and (c) N,N-dimethyltryptamine , or a pharmaceutically acceptable salt thereof, wherein the mean molecular weight of a-protio, a-deutero-N,N -dimethyltryptamine, a,adideutero-N ,N -dimethyltryptamine and N,N-dimethyltryptamine present in the composition is from 188.90 to 190.28.
3. The ition of claim 1 or claim 2, comprising 60% or more by weight of the a,a-dideutero-N,N -dimethyltryptamine compound, or a ceutically acceptable salt thereof, and the io, a-deutero-N,N -dimethyltryptamine compound, or a pharmaceutically acceptable salt thereof.
4. The composition of claim 1 or claim 2 wherein the a,a-dideutero-N,N - dimethyltryptamine compound is a,a-dideutero-N,N -dimethyltryptamine, or a pharmaceutically acceptable salt thereof.
5. The composition of any one of claims 1, 3 and 4 comprising an a-protio, ro-N ,N-dimethyltryptamine compound selected from the group consisting of a,ß,ß- 21406236_1 ters) P117886.NZ trideutero-N,N-dimethyltryptamine, a,ß-dideutero-N,N -dimethyltryptamine, and a-protio, a-deutero-N,N -dimethyltryptamine, and pharmaceutically able salts thereof.
6. The composition of any one of claims 1 to 5 comprising a-protio, a-deutero-N,N- dimethyltryptamine, or a pharmaceutically acceptable salt thereof.
7. The composition of any one of claims 1 to 6 having a purity of greater than or equal to 99% by HPLC, optionally a purity of greater than or equal to 99.9% by HPLC.
8. The ition of any one of claims 1 to 7, wherein the a-protio, a-deutero- N,N hyltryptamine and a,a-dideutero-N,N -dimethyltryptamine nds, and N,N-dimethyltryptamine are in the form of a pharmaceutically acceptable salt, optionally wherein the pharmaceutically acceptable salt is a te salt.
9. The composition of any one of claims 1 to 7, wherein the a-protio, a-deutero-N,N - yltryptamine and a,a-dideutero-N,N -dimethyltryptamine compounds, and N,N- yltryptamine are in the form of a fumarate salt.
10. The composition of any one of claims 1 to 9 for use in therapy.
11. Use of the composition of any one of claims 1 to 9 in the manufacture of a medicament for treating a psychocognitive disorder in a patient.
12. The use of claim 11, wherein the psychocognitive disorder is selected from the group consisting of (i) an obsessive compulsive disorder, (ii) a depressive disorder, (iii) an anxiety disorder, (iv) substance abuse, and (v) an avolition disorder.
13. The use of claim 12, wherein the disorder is major depressive disorder, ally wherein the disorder is treatment resistant depression.
14. Use of the ition of any one of claims 1 to 9 in the manufacture of a medicament for dimethyltryptamine-assisted psychotherapy in a patient. 21406236_1 (GHMatters) P117886.NZ A) Plasma B) Effect Site (Brain) 1; 240 "— DMT 1 20 f DMT Spa’CéL ‘x I
NZ783166A 2020-06-02 Therapeutic compositions comprising deuterated or partially deuterated n,n-dimethyltryptamine compounds NZ783166B2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GBGB1907871.6A GB201907871D0 (en) 2019-06-03 2019-06-03 Therapeutic compositions
PCT/EP2020/065244 WO2020245133A1 (en) 2019-06-03 2020-06-02 Therapeutic compositions comprising deuterated or partially deuterated n,n-dimethyltryptamine compounds

Publications (2)

Publication Number Publication Date
NZ783166A NZ783166A (en) 2025-06-27
NZ783166B2 true NZ783166B2 (en) 2025-09-30

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