# US 10,369,131 B2 · Ultrapure tetrahydrocannabinol-11-oic acids

> Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt

- Number: US 10,369,131 B2
- Document ID: US10369131B2
- Status: Granted
- Kind: B2
- Application number: 16/198,381
- Filed: 2018-11-21
- Published: 2019-03-28
- Granted: 2019-08-06
- Earliest claimed: 2013-02-12
- Assignees: Corbus Pharmaceuticals, Inc.
- Applicants: Corbus Pharmaceuticals, Inc.
- Inventors: Mark Tepper; Dean A. Frey; David Goeddel; Karl E. Reineke
- Web page: https://patentgrep.com/patent/US10369131B2

## CPC

- A61K 31/658: {o-phenolic cannabinoids, e.g. cannabidiol, cannabigerolic acid, cannabichromene or tetrahydrocannabinol}
- A61K 9/0014: {Skin, i.e. galenical aspects of topical compositions (non-active ingredients are additionally classified in A61K47/00; A61K9/0009, A61K9/0021, A61K9/7015, A61K9/7023 take precedence; cosmetic preparations A61K8/00, A61Q; preparations for wound dressings or bandages A61L26/00)}
- A61K 9/0019: {Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner (non-active ingredients are additionally classified in A61K47/00)}
- A61K 9/0048: {Eye, e.g. artificial tears}
- A61K 9/0053: {Mouth and digestive tract, i.e. intraoral and peroral administration}
- A61K 9/007: {Pulmonary tract; Aromatherapy}
- A61P 1/16: for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 13/12: of the kidneys
- A61P 17/00: Drugs for dermatological disorders
- A61P 17/02: for treating wounds, ulcers, burns, scars, keloids, or the like
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 37/06: Immunosuppressants, e.g. drugs for graft rejection
- 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)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

This application is in the field of medicinal chemistry and relates to ultrapure ajulemic acid, its synthesis, pharmaceutical compositions and methods of use thereof for the treatment and/or prevention of inflammation, pain, and fibrotic diseases including scleroderma, systemic sclerosis, scleroderma-like disorders, sine scleroderma, liver cirrhosis, interstitial pulmonary fibrosis, idiopathic pulmonary fibrosis, Dupuytren's contracture, keloids, chronic kidney disease, chronic graft rejection, and other scarring-wound healing abnormalities, post-operative adhesions, and reactive fibrosis.

## Claims

### Claim 1

A method of ameliorating one or more symptoms of an inflammatory disease in a subject in need thereof, wherein the inflammatory disease is dermatomyositis, the method comprising administering to the subject a pharmaceutical composition comprising one or more cannabinoids, wherein said one or more cannabinoids comprise at least 98% (w/w) (6aR,10aR)-3-(1′,1′-dimethylheptyl)-Δ8-tetrahydro-cannabinol-9-carboxylic acid (ajulemic acid), or a pharmaceutically acceptable salt thereof, and wherein no significant antinociception is observed in a hot plate test of mice following oral administration to the mice of 10 mg/kg of said one or more cannabinoids.

### Claim 2 (depends on 1)

The method of claim 1, wherein said pharmaceutical composition is administered orally, intravenously, topically, interstitially, by inhalation, via an implant, via a patch, or by ophthalmic administration.

### Claim 3 (depends on 2)

The method of claim 2, wherein said pharmaceutical composition is administered orally.

### Claim 4 (depends on 2)

The method of claim 2, wherein said pharmaceutical composition is administered topically.

### Claim 5 (depends on 2)

The method of claim 2, wherein said pharmaceutical composition is administered by ophthalmic administration.

### Claim 6 (depends on 2)

The method of claim 2, wherein said pharmaceutical composition is administered intravenously.

### Claim 7 (depends on 2)

The method of claim 2, wherein said pharmaceutical composition is administered by inhalation.

### Claim 8 (depends on 1)

The method of claim 1, wherein said pharmaceutical composition is administered in combination with one or more compounds.

### Claim 9 (depends on 1)

The method of claim 1, wherein said subject is a human.

### Claim 10 (depends on 1)

The method of claim 1, wherein said subject is non-human animal.

### Claim 11 (depends on 10)

The method of claim 10, wherein said non-human animal is a dog or a cat.

### Claim 12 (depends on 1)

The method of claim 1, wherein said pharmaceutical composition is a unit dosage formulation comprising about 0.5 mg to about 120 mg of said (6aR,10aR)-3-(1′,1′-dimethylheptyl)-Δ8-tetrahydro-cannabinol-9-carboxylic acid, or a pharmaceutically acceptable salt thereof, and wherein said unit dosage formulation is administered once daily.

### Claim 13 (depends on 1)

The method of claim 1, wherein said pharmaceutical composition is a unit dosage formulation comprising about 0.15 mg to about 40 mg of said (6aR,10aR)-3-(1′,1′-dimethylheptyl)-Δ8-tetrahydro-cannabinol-9-carboxylic acid, or a pharmaceutically acceptable salt thereof, and wherein said unit dosage formulation is administered up to three times daily.

### Claim 14 (depends on 1)

The method of claim 1, wherein said one or more cannabinoids comprise at least 99% (w/w) (6aR,10aR)-3-(1′,1′-dimethylheptyl)-Δ8-tetrahydro-cannabinol-9-carboxylic acid (ajulemic acid).

### Claim 15 (depends on 1)

The method of claim 1, wherein said one or more cannabinoids comprise less than 0.5% (w/w) 11-hydroxy-(6aR,10aR)-3-(1′,1′-dimethylheptyl)-Δ8-tetrahydro-cannabinol (HU-210).

### Claim 16 (depends on 15)

The method of claim 15, wherein said one or more cannabinoids comprise less than 0.1% (w/w) 11-hydroxy-(6aR,10aR)-3-(1′,1′-dimethylheptyl)-Δ8-tetrahydro-cannabinol (HU-210).