US 2003/0166727 A1 · Pharmaceutical compositions comprising cannabidiol derivatives

Abstract

The present invention relates to cannabidiol derivatives and to pharmaceutical compositions comprising cannabidiol derivatives being antiinflammatory agents having analgesic, antianxiety, anticonvulsive, neuroprotective, antipsychotic and anticancer activity. The present invention also relates to a process for the preparation of cannabidiol derivatives. It also relates to the use of cannabidiol derivatives and of pharmaceutical compositions comprising same in the preparation of a medicament, in a method of the treatment of human beings with cannabidiol derivatives or with a pharmaceutical preparations comprising same.

Claims14

Dependent claims

Pharmaceutical compositions comprising a compound of general Formula I

2
In which R′ stands for COOH or CH2OH
R″ stands for
a. straight or branched alkyl of 5 to 12 carbon atoms;
b. a group —O—R′″, where R′″ is straight or branched alkyl of 5 to 9 carbon atoms, or a straight or branched alkyl substituted at the terminal carbon atom by a phenyl group;
c. a group —(CH2)n—O-alkyl, where n is an integer from 1 to 7 and the alkyl group contains 1 to 5 carbon atoms.

3 more elements

Process for the preparation of compounds of general formula I in which R′=CH2OH and R″=

a. straight or branched alkyl of 5 to 12 carbon atoms;
b. a group —O—R′″, where R′″ is straight or branched alkyl of 5 to 9 carbon atoms, or a straight or branched alkyl substituted at the terminal carbon atom by a phenyl group;
c. a group —(CH2)n—O-alkyl, where n is an integer from 1 to 7 and the alkyl group contains 1 to 5 carbon atoms.
which comprises.
a. blocking the phenolic groups of a compound of general formula I in which R′ stands for CH3 and R″ has the same meaning as above;
b. selective epoxidation of the ring double bond in the compound obtained in step a;
c. selective opening of the epoxide ring in the compound obtained in step b to form the corresponding allyl alcohol;
d. performing an allylic rearrangement of the compound obtained in step c to obtain the dimethoxy compound of the desired compound of general formula I;
and
e. demethoxylating the compound obtained in step d to form the desired compound of general formula I.

7 more elements

Dependencies are inferred from the claim text.

Pharmaceutical compositions comprising cannabidiol derivatives

Life of this patent

Pharmaceutical compositions comprising cannabidiol derivatives

Life of this patent

Abstract

Claims14