Process for the preparation of 3-substituted cannabinoid compounds
AssigneeE-Therapeutics PLC
InventorsVijaya Bhasker Gondi, James Thomson Loch, III, Nicholas John Holman, Steven James Collier
Life of this patent
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Abstract
There is described a method of preparing a compound of formula I, and optical isomers thereof; in which R1 is hydrogen or a protecting group; said method comprising oxidising verbenone and optical isomers thereof.
Claims21
A method of preparing a compound of formula I, and optical isomers thereof:
- in which R1 is hydrogen or a protecting group;
- said method comprising oxidising verbenone (4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one) and optical isomers thereof:
A method of preparing a 9-(hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo [c]chromen-1-ol cannabinoid which comprises reacting a compound of formula I in which R1 is hydrogen, with 5-(1,1-dimethylheptyl)resorcinol.
A method of preparing a 3-subtituted cannabinoid compounds which comprises reacting a compound of formula I with 5-substituted resorcinol.
A method of preparing a 9-(hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo [c]chromen-1-ol cannabinoid which comprises the steps of:
- oxidising a verbenone and optical isomers thereof;
- to produce 4-oxomyrtenol or protected 4-oxomyrtenol;
- (ii) optionally protecting the hydroxy group of 4-oxomyrtenol;
- (iii) reacting the 4-oxomyrtenol, or a protected derivative thereof, with 5-(1,1-dimethylheptyl)resorcinol to produce a 9-(hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo [c]chromen-1-ol cannabinoid, or a protected derivative thereof;
- and
- (iv) optionally deprotecting the protected derivative of the 9-(hydroxymethyl)-6,6-dimethyl-3-(2-m ethyloctan-2-yl)-6a, 7,10,10a-tetrahydrobenzo [c]chromen-1-ol cannabinoid.
A method of preparing a compound of formula I, and optical isomers thereof, which comprise formation of a dienol intermediate of formula II, and optical isomers thereof:
- in which R2 is a protecting group.
A compound of formula II and optical isomers thereof:
- in which R2 is a protecting group.
-19. (canceled)
A method of preparing a 9-(hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo [c]chromen-1-ol cannabinoid which comprises the steps of:
- (i) oxidising a compound of formula II and optical isomers thereof;
- in which R2 is a protecting group;
- to produce 4-oxomyrtenol or protected 4-oxomyrtenol;
- (ii) optionally protecting the hydroxy group of 4-oxomyrtenol;
- (iii) reacting the 4-oxomyrtenol, or a protected derivative thereof, with 5-(1,1-dimethylheptyl)resorcinol to produce 9-(hydroxymethyl)-6,6-dimethyl-3-(2-methyloctan-2-yl)-6a,7,10,10a-tetrahydrobenzo [c]chromen-1-ol cannabinoid, or a protected derivative thereof;
- and
- (iv) optionally deprotecting the protected derivative of 9-(hydroxymethyl)-6,6-dimethyl-3-(2-m ethyloctan-2-yl)-6a, 7,10,10a-tetrahydrobenzo [c]chromen-1-ol cannabinoid.
-26. (canceled)
Dependencies are inferred from the claim text.