# US 2024/0189331 A1 · Novel tryptamine oral film formulation

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- Number: US 2024/0189331 A1
- Document ID: US20240189331A1
- Status: Published application
- Kind: A1
- Application number: 18/276,918
- Filed: 2022-02-14
- Published: 2024-06-13
- Earliest claimed: 2021-02-12
- Assignees: Intelgenx Corp.
- Applicants: Intelgenx Corp.
- Inventors: Mobarik BILAL; Billal TIR; Nadine PAIEMENT
- Web page: https://patentgrep.com/patent/US20240189331A1

## CPC

- A61K 31/675: having nitrogen as a ring hetero atom, e.g. pyridoxal phosphate
- A61P 25/00: Drugs for disorders of the nervous system
- A61K 9/006: {Oral mucosa, e.g. mucoadhesive forms, sublingual droplets; Buccal patches or films; Buccal sprays}
- A61K 31/4045: Indole-alkylamines; Amides thereof, e.g. serotonin, melatonin
- A61K 47/02: Inorganic compounds
- A61K 47/10: Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
- A61K 47/12: Carboxylic acids; Salts or anhydrides thereof
- A61K 47/186: {Quaternary ammonium compounds, e.g. benzalkonium chloride or cetrimide}
- A61K 47/22: Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
- A61K 47/26: Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
- A61K 47/32: Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. carbomers {, poly(meth)acrylates, or polyvinyl pyrrolidone}
- A61K 47/38: Cellulose; Derivatives thereof
- C07D 209/16: Tryptamines
- C07F 9/5728: {condensed with carbocyclic rings or carbocyclic ring systems}
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- 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)

## Abstract

The present disclosure relates to oral film formulations, which provide a tryptamine active agent. The disclosure more particularly relates to oral film formulations with improved buccal absorption of tryptamine active agents. The present disclosure also relates to formulations and methods for treatment of various symptoms in a patient, such as the treatment of mental health conditions.

## Claims

### Claim 1

An oral film formulation comprising an active agent selected from psilocybin, psilocin, norpsilocin, bufotenin, bufotenidine, baeocystin, norbaeocystin, and aeruginascin, and salts thereof, and combinations thereof, a penetration enhancer, an acidifying agent, and a plasticizer, wherein the surface pH range of the oral film formulation is preferably between 1.5 and 5.

### Claim 2 (depends on 1)

The oral film formulation of claim 1, wherein the surface pH range is between 2 and 4.5.

### Claim 3 (depends on 1)

The oral formulation of claim 1, wherein the surface pH range is between 2.5 and 4.

### Claim 4 (depends on 1)

The oral formulation of claim 1, wherein the surface pH range is between 3 and 3.5.

### Claim 5 (depends on 3)

The oral film formulation of claim 3, wherein the penetration enhancer is a quaternary ammonium salt selected from benzalkonium chloride, cetylpyridinium chloride and Cetrimide, Cetyltrimethylammonium bromide.

### Claim 6 (depends on 1)

The oral film formulation of claim 1, wherein the acidifying agent is selected from phosphoric acid, citric acid, tartaric acid, malic acid, acetic acid, succinic acid, maleic acid, Hydrochloric acid, benzoic acid, fumaric acid, glucoronic acid, or lactic acid, and is preferably citric acid or phosphoric acid.

### Claim 7 (depends on 1)

The oral film formulation of claim 1, wherein the penetration enhancer is present in an amount of from about 0.1% to about 10% by weight, 1% to 3%, or preferable 0.5% to 5% by weight relative to the total dry weight of the oral film formulation.

### Claim 8 (depends on 1)

The oral film formulation of claim 1, wherein the active agent is present in an amount of from about 2 to 25% by weight or 5 to 20% by weight, relative to the total dry weight of the oral film formulation.

### Claim 9 (depends on 1)

The oral film formulation of claim 1, further comprising a mucoadhesive agent, wherein the mucoadhesive agent is selected from the group of hydroxypropylmethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, sodium alginate, sodium carboxymethyl cellulose, guar gum, karya gum, methylcellulose, polyethylene oxide, retene, tragacanth, and combinations of two or more thereof.

### Claim 10 (depends on 9)

The oral film formulation of claim 9, wherein the mucoadhesive agent is present in an amount of from about 0.5% to about 20% by weight, or about 1% to about 5% by weight, relative to the total dry weight of the oral film formulation,

### Claim 11 (depends on 1)

The oral film formulation of claim 1, wherein the plasticizer is present in an amount up to 25% by weight, such as from 0.5% to 25%, 1% to 20%, 2% to 15% or 5% to 10% by weight, relative to the total dry weight of the oral film formulation.

### Claim 12 (depends on 1)

The oral film formulation of claim 1, further comprising an antioxidant, wherein the antioxidant is present in an amount of from about 0.01% to 5% or 0.1% to 1% by weight, relative to the total dry weight of the oral film formulation.

### Claim 13 (depends on 1)

The oral film formulation of claim 1, further comprising at least one film forming polymer, wherein the at least one film forming polymer is selected from the group of hypromelose HPMC E50, copovidone (copolymers of N-vinyl-2-pyrrolidone and vinyl acetate), povidone (polyvinylpyrrolidone), polyethylene oxide, polyvinyl alcohol, polyethylene glycol, polyacrylic acid, methylmethacrylate copolymer, carboxyvinyl copolymers, polydextrose, pullulan, hydroxypropylmethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, carboxymethyl cellulose, sodium alginate, xanthan gum, tragancath gum, guar gum, acacia gum, arabic gum, starch, gelatin, and combinations of two or more thereof.

### Claim 14 (depends on 13)

The oral film formulation of claim 13, wherein the film forming polymer or combination of film forming polymers is present in an amount of from 10% to 90% by weight, 20% to 80% by weight, or 30% to 70% by weight, relative to the total dry weight of the oral film formulations.

### Claim 15

(canceled)

### Claim 16

(canceled)

### Claim 17 (depends on 1)

The oral film formulation of claim 1, further comprising a pore former.

### Claim 18

(canceled)

### Claim 19 (depends on 1)

The oral film formulation of claim 1, further comprising a sweetener.

### Claim 20 (depends on 1)

A method for treating depression, anxiety, migraines, addiction, dementias, Alzheimer's disease, eating disorders, obsessive compulsive disorder, Lyme disease syndrome, post-traumatic stress disorder, abuse disorders including opioid addiction, alcohol addiction, nicotine addiction, cannabinoid addiction, headache, central nervous system inflammation, and disorders of cognition and memory with the oral film formulation of claim 1, wherein the method comprises administrating the oral film formulation bucally.

### Claim 21

A method of using an acidifying agent and penetration agent for enhancing permeation of psilocybin, psilocin, norpsilocin, bufotenin, bufotenidine, baeocystin, norbaeocystin, and aeruginascin, and salts thereof, and combinations thereof, wherein the method comprises administering the oral film formulation buccally.

### Claim 22

An oral film formulation comprising an active agent, a penetration enhancer, an acidifying agent and a plasticizer, wherein the pH range of the oral film formulation is preferably between 1.5 and 5, and wherein the active agent is a tryptamine.

### Claim 23 (depends on 22)

A method for treating depression, anxiety, migraines, addiction, dementias, Alzheimer's disease, eating disorders, obsessive compulsive disorder, Lyme disease syndrome, post-traumatic stress disorder, abuse disorders including opioid addiction, alcohol addiction, nicotine addiction, cannabinoid addiction, headache, central nervous system inflammation, and disorders of cognition and memory with the oral film formulation of claim 22, wherein the method comprises administrating the oral film formulation buccally.

### Claim 24

(canceled)