# US 11,998,557 B2 · Halogenated psilocybin derivatives and methods of using

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- Number: US 11,998,557 B2
- Document ID: US11998557B2
- Status: Granted
- Kind: B2
- Application number: 17/903,080
- Filed: 2022-09-06
- Published: 2023-09-21
- Granted: 2024-06-04
- Earliest claimed: 2020-09-01
- Assignees: Enveric Biosciences Canada Inc.
- Applicants: Enveric Biosciences Canada Inc.
- Inventors: Jillian M. Hagel; Peter J. Facchini
- Web page: https://patentgrep.com/patent/US11998557B2

## CPC

- A61K 31/675: having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
- C07D 209/16: Tryptamines
- A61K 31/4045: Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
- C07F 9/5728: {condensed with carbocyclic rings or carbocyclic ring systems}
- C12N 9/0071: {acting on paired donors with incorporation of molecular oxygen (1.14)}
- C12N 9/0083: {Miscellaneous (1.14.99)}
- C12N 9/1007: {Methyltransferases (general) (2.1.1.)}
- C12N 9/1029: {transferring groups other than amino-acyl groups (2.3.1)}
- C12N 9/1205: {Phosphotransferases with an alcohol group as acceptor (2.7.1), e.g. protein kinases}
- C12N 9/88: Lyases (4.)
- C12N 15/52: Genes encoding for enzymes or proenzymes
- C12P 17/10: Nitrogen as only ring hetero atom
- C12Y 402/0102: Tryptophan synthase (4.2.1.20)
- C07K 2319/21: containing a His-tag
- C07K 2319/40: containing a tag for immunodetection, or an epitope for immunisation
- C07K 2319/41: containing a Myc-tag
- C07K 2319/42: containing a HA(hemagglutinin)-tag
- C07K 2319/43: containing a FLAG-tag
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- C12N: MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA (microbiological testing media C12Q1/00)
- C12P: FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {(brewing of beer C12C; producing vinegar C12J; producing specific peptides or proteins C07K; producing enzymes C12N9/00; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; measuring or testing processes involving enzymes or microorganisms C12Q; measuring or testing processes involving nucleic acid amplification reactions C12Q1/6844; fermentation processes to form a food composition, A21 or A23; compounds in general, see the relevant compound class, e.g. C01, C07)}
- C12Y: ENZYMES
- C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00)

## Abstract

Disclosed are novel halogenated psilocybin derivative compounds and pharmaceutical and recreational drug formulations containing the same. The compounds may be produced using a biosynthetic system which comprises cells comprising a psilocybin biosynthetic enzyme complement.

## Claims

### Claim 1

A pharmaceutical drug formulation comprising an effective amount of a chemical compound or salts thereof having the formula (I):
wherein, at least one of R2, R4, R5, R6, or R7 is a halogen atom, wherein each non-halogenated R2, R4, R5, R6, or R7 is a hydrogen atom, and wherein Ria is a hydrogen atom and R3b is an acyl group,
together with a pharmaceutically acceptable excipient, diluent, or carrier.

### Claim 2 (depends on 1)

A pharmaceutical drug formulation according to claim 1, wherein R7 is a halogen atom, and R2, R4, R5, or R6 is a hydrogen atom or a halogen atom.

### Claim 3 (depends on 1)

A pharmaceutical drug formulation according to claim 1, wherein R7 is a first halogen atom, and one of R2, R4, R5, or R6 is a second halogen atom, wherein each non-halogenated R2, R4, R5, or R6, is a hydrogen atom.

### Claim 4 (depends on 3)

A pharmaceutical drug formulation according to claim 3, wherein the first and second halogen atoms are non-identical halogen atoms.

### Claim 5 (depends on 4)

A pharmaceutical drug formulation according to claim 4, wherein the first halogen atom is a fluorine (F) atom, and the second halogen atom is one of a chlorine or bromine atom.

### Claim 6 (depends on 3)

A pharmaceutical drug formulation according to claim 3, wherein the first and second halogen atoms are identical halogen atoms.

### Claim 7 (depends on 1)

A pharmaceutical drug formulation according to claim 1, wherein R7 is a halogen atom, and each of R2, R4, R5, and R6 are a hydrogen atom.

### Claim 8 (depends on 1)

A pharmaceutical drug formulation according to claim 1, wherein the halogen atom is a fluorine (F) atom.

### Claim 9 (depends on 1)

A pharmaceutical drug formulation according to claim 1, wherein R7 is a fluorine atom and R2, R4, R5, or R6 is a hydrogen atom or a halogen atom.

### Claim 10 (depends on 1)

A pharmaceutical drug formulation according to claim 1, wherein R7 is a fluorine atom, wherein additionally one of R2, R4, R5, or R6 is a halogen atom, and wherein each non-halogenated R2, R4, R5, or R6, is a hydrogen atom.

### Claim 11 (depends on 10)

A pharmaceutical drug formulation according to claim 10, wherein both R7 and the additionally one of R2, R4, R5, or R6 are a fluorine (F) atom.

### Claim 12 (depends on 10)

A pharmaceutical drug formulation according to claim 10, wherein the additionally one of R2, R4, R5, or R6 which are a halogen atom, is a halogen atom other than a fluorine atom.

### Claim 13 (depends on 1)

A pharmaceutical drug formulation according to claim 1, wherein R7 is a fluorine (F) atom, and R2, R4, R5, and R6 are a hydrogen atom.

### Claim 14 (depends on 1)

A pharmaceutical drug formulation according to claim 1, wherein the acyl group is a —C(═O)C1-C20 alkyl group.

### Claim 15 (depends on 1)

A pharmaceutical drug formulation according to claim 1, wherein the acyl group is a —C(═O)C1-C6 alkyl group.

### Claim 16 (depends on 1)

A pharmaceutical drug formulation according to claim 1, wherein the acyl group is —C(═O)CH3 group.

### Claim 17 (depends on 1)

A pharmaceutical drug formulation according to claim 1, wherein R3b is a —C(═O)C1-C20 alkyl group, and R3a is a hydrogen atom.

### Claim 18 (depends on 1)

A pharmaceutical drug formulation according to claim 1, wherein R3b is a —C(═O)C1-C6 alkyl group, and R3a is a hydrogen atom.

### Claim 19 (depends on 1)

A pharmaceutical drug formulation according to claim 1, wherein R3b is a —C(═O)CH3 group, and R3a is a hydrogen atom.

### Claim 20 (depends on 1)

A pharmaceutical drug formulation according to claim 1, having the chemical formula:

### Claim 21

A chemical compound having the formula:

### Claim 22 (depends on 21)

A chemical compound according to claim 21, wherein the compound is at least about 95% pure.