Cannabinoid analogs and methods for their preparation
Inventors
Barr, Philip J. • Marlowe, Charles K. • Sun, Jianping • Kealey, James T.
Assignees
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Publication Number
US-12617747-B2
Publication Date
2026-05-05
Expiration Date
Abstract
Provided herein are cannabinoid analogs, including halogenated cannabinoid analogs, hydroxylated cannabinoid analogs, deuterated cannabinoid analogs, and tritiated cannabinoid analogs. The cannabinoid analogs can be prepared by partial or total expression in modified host cells, such as recombinantly modified yeast cells, optionally in combination with chemical synthetic steps.
Core Innovation
The disclosure provides cannabinoid derivative compounds defined by a Formula I structure, or salts or cannabinoid derivatives thereof, for formulation as pharmaceutical compositions. The Formula I definition fixes the prenyl moiety as 3,7-dimethylocta-2,6-dien-1-yl and specifies substituent classes through R1 and R2, with R1 selected from C1–C20 haloalkyl, C1–C20 hydroxyalkyl, C2–C20 alkenyl, deuterated C1–C20 alkyl, and tritiated C1–C20 alkyl, while R2 is selected from COOR2a and H, with R2a selected from H and C1–C6 alkyl.
The disclosed cannabinoid derivative classes include halogenated cannabidiolic acid, halogenated cannabidiol, halogenated α-tetrahydrocannabinolic acid, halogenated δ-tetrahydrocannabinolic acid, halogenated cannabichromenic acid, halogenated cannabichromene, halogenated cannabinol, halogenated cannabinodiol, halogenated cannabinolic acid, cannabivarin and halogenated cannabivarinic acid, cannabichromevarin and halogenated cannabichromevarinic acid, cannabidivarin and halogenated cannabidivarinic acid, cannabitriol and halogenated cannabitriol, and cannabicyclol. The document also defines Formula I and Ia; Formula IV and IVa; thioester and tetraketide intermediates Formula II and III; and Formula V and Va, together with decarboxylation and prenylation relationships mediated by a prenyltransferase such as a geranylpyrophosphate:olivetolate geranyltransferase.
Production is described in a modified recombinant host cell using polynucleotides encoding a synthase and a 2-alkyl-4,6-dihydroxybenzoic acid cyclase, including a truncated cyclase, as well as additional polynucleotides including an acyl-CoA synthetase and a prenyltransferase. The document further describes cannabinoid derivative selections shown in the document, including (-)-Δ8-trans-tetrahydrocannabinol (Δ8-THC) analogs, (-)-Δ8-trans-cannabivarin (Δ8-THCV) analogs, Δ8-THCA analogs, Δ8-THCVA analogs, and families such as the CBC/CBN family and CBV/CBVA, along with structural variants listed in the document.
Claims Coverage
The provided claim content centers on one independent claim, with dependent claims that narrow the composition and add a therapeutic method. Across the claim set, five core inventive features are present: the Formula I framework with a fixed 3,7-dimethylocta-2,6-dien-1-yl prenyl moiety, defined substituent classes for R1 and R2, formulation as a pharmaceutical composition with a pharmaceutically acceptable excipient, restricted cannabinoid derivative selections, and administration for cannabinoid-receptor-mediated treatment.
Pharmaceutical composition with Formula I cannabinoid derivative
A pharmaceutical composition comprising a compound according to Formula I, or a salt or cannabinoid derivative thereof, together with a pharmaceutically acceptable excipient.
Fixed prenyl moiety as 3,7-dimethylocta-2,6-dien-1-yl
The compound of Formula I has R3 as a prenyl moiety, wherein the prenyl moiety is 3,7-dimethylocta-2,6-dien-1-yl.
R1 substitution classes including haloalkyl, hydroxyalkyl, alkenyl, and isotopically labeled alkyl
The Formula I compound is defined with R1 selected from C1–C20 haloalkyl, C1–C20 hydroxyalkyl, C2–C20 alkenyl, deuterated C1–C20 alkyl, and tritiated C1–C20 alkyl.
R2 selection as COOR2a or H with constrained R2a
The Formula I compound is defined with R2 selected from COOR2a and H, wherein R2a is selected from H and C1–C6 alkyl.
Treatment of cannabinoid-receptor-mediated disease or condition by administering the composition
A method for treating a disease or condition mediated by cannabinoid receptor activity by administering an effective amount of a pharmaceutical composition containing a cannabinoid derivative or a pharmaceutically acceptable salt.
The claim coverage centers on a pharmaceutical composition of a Formula I cannabinoid-related compound, or salt or cannabinoid derivative, defined by constrained R1 and R2/R2a substituents and a fixed 3,7-dimethylocta-2,6-dien-1-yl prenyl group, together with a pharmaceutically acceptable excipient, restricted cannabinoid derivative selections, and administration for cannabinoid-receptor-mediated treatment.
Stated Advantages
Documented Applications
A method for treating a disease or condition mediated by cannabinoid receptor activity by administering an effective amount of a pharmaceutical composition containing a cannabinoid derivative or a pharmaceutically acceptable salt.
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