Synthetic intermediates for novel cannabinoids and cannabinoid acids and their derivatives
US11685724B2 · kind B2 · utility
Assignee
Inventors
Key dates
| Filing date | May 6, 2022 |
| Grant date | Jun 27, 2023 |
| Priority date | — |
| Expiry date | May 6, 2042 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07C2601/16
- WIPO fieldPharmaceuticals
- WIPO sectorChemistry
Abstract
The present invention relates to intermediate compounds for the synthesis of novel cannabinoids 1 and 2, synthesized from simple starting materials using a cascade sequence of allylic rearrangement, aromatization and, for tetracyclic cannabinoids, further highly stereoselective and regioselective cyclization. These synthesized cannabinoids can more easily be obtained at high purity levels than cannabinoids isolated or synthesized via known methods. The cannabinoids 2 are obtained containing very low levels of isomeric cannabinoids such as the undesirable Δ8-tetrahydrocannabinol. The analogues with variation in aromatic ring substituents, whilst easily synthesized with the new methodology, would be much more difficult to make from any of the components of cannabis oil. Novel compounds of the formulas 3 and 6, useful as intermediates for the synthesis of the cannabinoids of advanced intermediates 4 and 5 as well as cannabinoids of the formulas 1 and 2, are disclosed.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.