Derivatives of cannabidiol-c4 for the treatment of epilepsy
OwnerAlan James SILCOCK, Karen Ka-Yen TSEinventors
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Abstract
The present invention relates to compounds that are pharmaceutically active and methods of preparation thereof. The compounds of the invention are 7-hydroxy-cannabidol-C4 (7-OH-CBD-C4) and 7-carboxy-cannabidiol-C4 (7-COOH-CBD-C4). The compounds of the invention are related to cannabidiol (CBD). CBD is a non-psychoactive cannabinoid which has been used to treat various diseases and disorders. While such treatments hold promise, there remains a need in the art for more effective treatments and this has been brought about by way of the compounds of the invention.
Claims47
A compound of formula (I), or a salt thereof:
A pharmaceutical composition comprising a compound of formula (I) or a salt thereof.
A compound of formula (I), or a salt thereof, for use a medicament.
A compound of formula (I), or a salt thereof, for use in a method of treatment.
A method of treatment comprising administering to a subject in need of treatment a therapeutically effective amount of a compound of formula (I) or a salt thereof.
A process for the production of a compound of formula (I) comprising the following steps:
- i) treating 3,5-dimethoxybenzyl bromide with a propyl Grignard reagent to produce 1-butyl-3,5-dimethoxybenzene;
- ii) treating 1-butyl-3,5-dimethoxybenzene with a demethylation reagent to produce 5-butylbenzene-1,3-diol;
- iii) coupling 5-butylbenzene-1,3-diol with (R)-isolimonenediol 7-O-acetate in the presence of acid to produce 7-acetoxy-CBD-C4;
- and
- iv) treating 7-acetoxy-CBD-C4 with a reducing agent to produce the compound of formula (I).
An intermediate formed in the process of the production of a compound of formula (I), wherein the intermediate is selected from:
A compound of formula (II) or a salt thereof:
A pharmaceutical composition comprising a compound of formula (II) or a salt thereof.
A compound of formula (II), or a salt thereof, for use a medicament.
A compound of formula (II), or a salt thereof, for use in a method of treatment.
A method of treatment comprising administering to a subject in need of treatment a therapeutically effective amount of a compound of formula (I) or a salt thereof.
A process for the production of a compound of formula (II) comprising the following steps:
- i) providing 7-hydroxy-CBD-C4 (a compound of formula (I));
- treating 7-hydroxy-CBD-C4 with an acylation reagent and a base to give 7-hydroxy-CBD-C4 di-O-acetate;
- iii) reacting 7-hydroxy-CBD-C4 di-O-acetate with an oxidising agent to give 7-formyl-CBD-C4 di-O-acetate;
- iv) oxidising 7-formyl-CBD-C4 di-O-acetate, such as with sodium chlorite and monosodium phosphate, to afford 7-carboxy-CBD-C4 di-O-acetate;
- and
- v) deprotection of carboxy-CBD-C4 di-O-acetate using a reducing agent to produce the compound of formula (II).
An intermediate formed in the process of the production of a compound of formula (II), wherein the intermediate is selected from:
Dependencies are inferred from the claim text.