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US 12,759,990 B2Granted
THC derivatives, oral dosage forms comprising same, uses thereof for treating diseases and disorders and synthesis thereof
AssigneesBar-Ilan University, Eybna Technologies Ltd.
InventorsAmnon Albeck, Jacob Wolfman, Nadav Eyal
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Abstract
Provided herein are THC derivatives, formulations thereof, synthesis thereof and uses thereof through oral administration, for treatment of diseases and disorders.
Claims15
A THC derivative having the structure of Formula I:
- or enantiomer, acid, ester, a pharmaceutically acceptable salt, or prodrug thereof, wherein:
- R1 is a substituted methyl group CX3 wherein X is fluorine;
- and R2 and R3, independently, are selected from hydrogen and deuterium.
A pharmaceutical composition comprising a THC derivative having the structure of Formula II:
- or enantiomer, acid, ester, or a pharmaceutically acceptable salt, or prodrug thereof,
- wherein the compound comprises substituents R′1, R′2 and R′3 as shown in Formula (II), wherein R′1 is selected from a hydrogen and a substituted methyl group CX3 where X is fluorine;
- R′2 is hydrogen or deuterium;
- and R′3 is hydrogen or deuterium.
1 more element
A process of synthesizing 9-CD3-(8-D2)-THC, the process comprises the steps of:
- coupling (1R,6R)-6-(1-Hydroxy-1-methylethyl)-cyclohex-2-en-1-[(1,1-dimethylethyl)dimethylsilyloxy)]-4-(methyl-d3)-5-d2 (compound 15) with olivetol to provide 1,3-Dihydroxy-2-((1R,6R)-6-(1-Hydroxy-1-methylethyl)-4-(methyl-d3)-5-d2-cyclohex-2-en-1-yl)-5-pentylbenzene (compound 17);
- and
- cyclization of 1,3-Dihydroxy-2-((1R,6R)-6-(1-Hydroxy-1-methylethyl)-4-(methyl-d3)-5-d2-cyclohex-2-en-1-yl)-5-pentylbenzene (compound 17) to provide 9-CD3-(8-D2)-THC.
Dependencies are inferred from the claim text.