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US 12,617,749 B2Granted
Cannabinoid derivatives and precursors, and asymmetric synthesis for same
AssigneeKare Chemical Technologies Inc.
InventorsKamaluddin Abdur-Rashid, Wenli Jia, Kareem Abdur-Rashid
Life of this patent
Estimating the term…
Abstract
The present disclosure relates to new cannabinoid derivatives and precursors and catalytic asymmetric processes for their preparation. The disclosure also relates to pharmaceutical compositions and pharmaceutical and analytical uses of the new cannabinoid derivatives. The disclosure also relates to the deuterium, carbon-13 and carbon-14 containing derivatives of the compounds that can be prepared and purified prior to transformation to the desired individual deuterated cannabinoid products.
Claims10
A compound of Formula (I):
- wherein,
- the R1 groups are independently or simultaneously selected from the group consisting of hydrogen and deuterium;
- R3 to R4 are selected from the group consisting of hydrogen, deuterium, an optionally substituted C1-C20-alkyl group, an optionally substituted C2-C20-alkenyl group, an optionally substituted C2-C20-alkynyl group, an optionally substituted C3-C20-cycloalkyl group, an optionally substituted C6-C14-aryl group, an optionally substituted C5-C14-heteroaryl, and an optionally substituted acyl group, and one or more of the carbon atoms in the alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heteroaryl or acyl groups of R3 and R4 is optionally replaced with a heteroatom selected from the group consisting of O, S, N, P and Si, which, where possible, is optionally substituted, wherein the optional substituents are one or more groups selected from the group consisting of OH, halo and C1-C6-alkyl;
- Y is selected from the group consisting of O and NRc, in which Rc is selected from the group consisting of hydrogen atom, C1-C6-alkyl, C3-C6-cycloalkyl, C6-C10-aryl and C2-C6-alkenyl group;
- R2 is selected from the group consisting of a hydrogen atom, C1-C6-alkyl, C3-C6-cycloalkyl, C6-C10-aryl, C2-C6-alkenyl group and ORc;
- R5 and R6 are selected from the group consisting of hydrogen, deuterium, halide, an optionally substituted C1-C20-alkyl group, an optionally substituted C2-C20-alkenyl group, an optionally substituted C2-C20-alkynyl group, an optionally substituted C3-C20-cycloalkyl group, an optionally substituted C6-C14-aryl group, an optionally substituted C5-C14-heteroaryl, an optionally substituted acyl group, or an optionally substituted carboxylate group, and one or more of the carbon atoms in the alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heteroaryl, acyl or carboxylate groups of R5 and/or R6 is optionally replaced with a heteroatom selected from the group consisting of O, S, N, P and Si, which, where possible, is optionally substituted, wherein the optional substituents are one or more groups selected from the group consisting of OH, halo and C1-C6-alkyl;
- and
- X is selected from the group consisting of halide, sulfonate, carboxylate, carbonate and a group having the formula MWn, wherein M is selected from the group consisting of Li, Mg, Zn, Sn, B, and Si, W is selected from the group consisting of halide, OH, and OR, and R is selected from the group consisting of C1-C10-alkyl group and C6-C10-aryl group.
5 more elements
A compound of Formula (IV):
Dependencies are inferred from the claim text.