# US 12,303,487 B2 · N-acylated fatty amino acids to reduce absorption variability in cannabinoid based compositions

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- Number: US 12,303,487 B2
- Document ID: US12303487B2
- Status: Granted
- Kind: B2
- Application number: 17/295,405
- Filed: 2019-11-19
- Published: 2021-12-23
- Granted: 2025-05-20
- Earliest claimed: 2018-11-19
- Assignees: Spoke Sciences, Inc.
- Applicants: Spoke Sciences, Inc.
- Inventors: Andrea Leone-Bay; Gregory Wesner
- Web page: https://patentgrep.com/patent/US12303487B2

## CPC

- A61K 31/658: {o-phenolic cannabinoids, e.g. cannabidiol, cannabigerolic acid, cannabichromene or tetrahydrocannabinol}
- A23L 33/105: Plant extracts, their artificial duplicates or their derivatives
- A61K 9/0053: {Mouth and digestive tract, i.e. intraoral and peroral administration}
- A61K 9/1617: {Organic compounds, e.g. phospholipids, fats}
- A61K 9/4858: {Organic compounds}
- A61K 31/20: having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A61K 36/3482: {Cannabis}
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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)
- A23L: FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF (preservation thereof A23B)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The current disclosure provides use of N-acylated fatty amino acids to reduce absorption variability in cannabinoid-based compositions.

## Claims

### Claim 1

A method of reducing cannabinoid blood absorption inter-subject variability, the method comprising:
administering to a plurality of subjects an oral formulation comprising a cannabinoid with an aqueous solubility of less than 0.1 mg/ml selected from:
Δ9-Tetrahydrocannabinol (THC), cannabidiol (CBD), cannabigerol (CBG), cannabichromene (CBC), cannabinol (CBN), cannabinodiol (CBDL), cannabicyclol (CBL), cannabivarin (CBV), tetrahydrocannabivarin (THCV), cannabidivarin (CBDV), cannabichromevarin (CBCV), cannabigerovarin (CBGV), cannabigerol monomethyl ether (CBGM), cannabinol propyl variant (CBNV), cannabitriol (CBO), and/or mixtures thereof;
and an N-acylated fatty amino acid or salt thereof having a formula:
wherein X is sodium or potassium, and Z is hydrogen,
wherein the weight/weight (w/w) ratio of cannabinoid/N-acylated fatty amino acid or salt thereof within the oral formulation is 1:6 or 1:10;
thereby reducing the cannabinoid blood absorption inter-subject variability,
wherein the reduced cannabinoid blood absorption inter-subject variability is evidenced by a coefficient of variation (% CV) of area under a plasma concentration-time curve that is less than 50%.

### Claim 2 (depends on 1)

The method of claim 1, wherein the oral formulation comprising the cannabinoid and the N-acylated fatty amino acid or salt thereof comprises a powder or an oral solution.

### Claim 3 (depends on 1)

The method of claim 1, wherein the oral formulation comprises
50 mg cannabidiol (CBD) and 300 mg N-acylated fatty amino acid or salt thereof;
10 mg Δ9-Tetrahydrocannabinol (THC) and 100 mg N-acylated fatty amino acid or salt thereof;
50 mg CBD and 500 mg N-acylated fatty amino acid or salt thereof; or
30 mg CBD and 300 mg N-acylated fatty amino acid or salt thereof.

### Claim 4 (depends on 1)

The method of claim 1, wherein the cannabinoid comprises cannabidiol (CBD).

### Claim 5 (depends on 1)

The method of claim 1, the N-acylated fatty amino acid or salt thereof comprises sodium N-[8-(2-hydroxybenzoyl) amino] caprylate (SNAC).

### Claim 6 (depends on 1)

The method of claim 1, wherein the oral formulation comprises a gelatin capsule.

### Claim 7 (depends on 1)

The method of claim 1, wherein the oral formulation further comprises flavonoid compounds, terpenes, or terpenoids.

### Claim 8 (depends on 2)

The method of claim 2, wherein the powder is formed by wet granulation.