Ultrapure tetrahydrocannabinol-11-oic acids
View Patent ↗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.
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.
2. 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.
3. The method of claim 2 , wherein said pharmaceutical composition is administered orally.
4. The method of claim 2 , wherein said pharmaceutical composition is administered topically.
5. The method of claim 2 , wherein said pharmaceutical composition is administered by ophthalmic administration.
6. The method of claim 2 , wherein said pharmaceutical composition is administered intravenously.
7. The method of claim 2 , wherein said pharmaceutical composition is administered by inhalation.
8. The method of claim 1 , wherein said pharmaceutical composition is administered in combination with one or more compounds.
9. The method of claim 1 , wherein said subject is a human.
10. The method of claim 1 , wherein said subject is non-human animal.
11. The method of claim 10 , wherein said non-human animal is a dog or a cat.
12. 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.
13. 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.
14. 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).
15. 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).
16. 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).