IP Library › Granted Patent US 12,630,492
Granted Patent B2
US 12,630,492 · App. 17/624,585 · Granted May 19, 2026

Cannabinoid derivatives

Inventors: Jeffrey Alan Omeara (Halton Hills, CA); Quang Huy To (Hamilton, CA)
Assignee: Canopy Growth Corporation
C07C43/267A61K31/658C07C43/275C07C43/315C07C65/28C07C69/28C07C69/96C07C271/16C07C271/28C07D205/04
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Quick Facts
Patent No.
US 12,630,492
App. No.
17/624,585
Granted
May 19, 2026
Kind
B2
Abstract

The present invention are directed to cannabinoid derivatives and compositions thereof.

Claims (194)

1 . A compound, which is:

6-(methoxymethoxy)-3′-methyl-4-pentyl-[1,1′-biphenyl]-2-ol;

6-((2-methoxyethoxy)methoxy)-3′-methyl-4-pentyl-[1,1′-biphenyl]-2-ol;

6-((2-methoxypropan-2-yl)oxy)-3′-methyl-4-pentyl-[1,1′-biphenyl]-2-ol;

6-((2,5,8,11,14-pentaoxahexadecan-15-yl)oxy)-3′-methyl-4-pentyl-[1,1′-biphenyl]-2-ol;

ethyl [3-hydroxy-2-(m-tolyl)-5-pentyl-phenoxy]methyl carbonate;

ethyl (1-((6-hydroxy-3′-methyl-4-pentyl-[1,1′-biphenyl]-2-yl)oxy)ethyl) carbonate;

1-((6-hydroxy-3′-methyl-4-pentyl-[1,1′-biphenyl]-2-yl)oxy)ethyl (2-methoxyethyl) carbonate;

[3-hydroxy-2-(m-tolyl)-5-pentyl-phenoxy]methyl 2,2-dimethylpropanoate;

((6-hydroxy-3′-methyl-4-pentyl-[1,1′-biphenyl]-2-yl)oxy)methyl 2-ethylbutanoate;

((6-hydroxy-3′-methyl-4-pentyl-[1,1′-biphenyl]-2-yl)oxy)methyl acetate;

methyl (((6-hydroxy-3′-methyl-4-pentyl-[1,1′-biphenyl]-2-yl)oxy)methyl)(methyl)carbamate;

2-methoxyethyl (((6-hydroxy-3′-methyl-4-pentyl-[1,1′-biphenyl]-2-yl)oxy)methyl)(methyl)carbamate;

2,5,8,11-tetraoxatridecan-13-yl (((6-hydroxy-3′-methyl-4-pentyl-[1,1′-biphenyl]-2-yl)oxy)methyl)(methyl)carbamate;

methyl (((6-hydroxy-3′-methyl-4-pentyl-[1,1′-biphenyl]-2-yl)oxy)methyl)(phenyl)carbamate;

methyl (((6-hydroxy-3′-methyl-4-pentyl-[1,1′-biphenyl]-2-yl)oxy)methyl)(4-nitrophenyl)carbamate;

6-((1-methoxycyclopentyl)oxy)-3′-methyl-4-pentyl-[1,1′-biphenyl]-2-ol;

6-(ethoxymethoxy)-3′-methyl-4-pentyl-[1,1′-biphenyl]2-ol;

6-((cyclohexyloxy)methoxy)-3′-methyl-4-pentyl-[1,1′-biphenyl]-2-ol;

6-(ethoxymethoxy)-3′-methyl-4-(2-methyloctan-2-yl)-[1,1′-biphenyl]-2-ol;

methyl (((6-hydroxy-3′-methyl-4-(2-methyloctan-2-yl)-[1,1′-biphenyl]-2-yl)oxy)methyl)(phenyl)carbamate;

((6-hydroxy-3′-methyl-4-(2-methyloctan-2-yl)-[1,1′-biphenyl]-2-yl)oxy)methyl pivalate;

ethyl (((6-hydroxy-3′-methyl-4-(2-methyloctan-2-yl)-[1,1′-biphenyl]-2-yl)oxy)methyl) carbonate;

((6-hydroxy-3′-methyl-4-propyl-[1,1′-biphenyl]-2-yl)oxy)methyl pivalate;

ethyl (((6-hydroxy-3′-methyl-4-propyl-[1,1′-biphenyl]-2-yl)oxy)methyl) carbonate;

6-(methoxymethoxy)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2-ol;

6-((2-methoxyethoxy)methoxy)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2-ol;

6-((2-methoxypropan-2-yl)oxy)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2-ol;

6-((2,5,8,11,14-pentaoxahexadecan-15-yl)oxy)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2-ol;

ethyl (((6-hydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2-yl)oxy)methyl) carbonate;

ethyl (1-((6-hydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2-yl)oxy)ethyl) carbonate;

1-((6-hydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2-yl)oxy)ethyl (2-methoxyethyl) carbonate;

((6-hydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2-yl)oxy)methyl pivalate;

((6-hydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2-yl)oxy)methyl 2-ethylbutanoate;

((6-hydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2-yl)oxy)methyl acetate;

methyl (((6-hydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2-yl)oxy)methyl)(methyl)carbamate;

2-methoxyethyl (((6-hydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2-yl)oxy)methyl)(methyl)carbamate;

2,5,8,11-tetraoxatridecan-13-yl(((6-hydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2-yl)oxy)methyl)(methyl)carbamate;

methyl (((6-hydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2-yl)oxy)methyl)(phenyl)carbamate;

methyl (((6-hydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2-yl)oxy)methyl)(4-nitrophenyl)carbamate;

6-((1-methoxycyclopentyl)oxy)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2-ol;

6-(ethoxymethoxy)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2-ol;

6-((cyclohexyloxy)methoxy)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2-ol;

6-(ethoxymethoxy)-5′-methyl-4-(2-methyloctan-2-yl)-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2-ol;

methyl (((6-hydroxy-5′-methyl-4-(2-methyloctan-2-yl)-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2-yl)oxy)methyl)(phenyl)carbamate;

((6-hydroxy-5′-methyl-4-(2-methyloctan-2-yl)-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2-yl)oxy)methyl pivalate;

ethyl (((6-hydroxy-5′-methyl-4-(2-methyloctan-2-yl)-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2-yl)oxy)methyl) carbonate;

((6-hydroxy-5′-methyl-2′-(prop-1-en-2-yl)-4-propyl-[1,1′-biphenyl]-2-yl)oxy)methyl pivalate;

ethyl (((6-hydroxy-5′-methyl-2′-(prop-1-en-2-yl)-4-propyl-[1,1′-biphenyl]-2-yl)oxy)methyl) carbonate;

6-(methoxymethoxy)-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-ol;

6-((2-methoxyethoxy)methoxy)-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-ol;

6-((2-methoxypropan-2-yl)oxy)-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-ol;

6-((2,5,8,11,14-pentaoxahexadecan-15-yl)oxy)-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-ol;

ethyl (((6-hydroxy-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl) carbonate;

ethyl (1-((6-hydroxy-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)ethyl) carbonate;

1-((6-hydroxy-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)ethyl (2-methoxyethyl) carbonate;

((6-hydroxy-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl pivalate;

((6-hydroxy-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl 2-ethylbutanoate;

((6-hydroxy-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl acetate;

methyl N-[[3-hydroxy-2-(3-methylcyclohex-2-en-1-yl)-5-pentyl-phenoxy]methyl]-N-methyl-carbamate;

2-methoxyethyl (((6-hydroxy-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl)(methyl)carbamate;

2,5,8,11-tetraoxatridecan-13-yl (((6-hydroxy-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl)(methyl)carbamate;

methyl (((6-hydroxy-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl)(phenyl)carbamate;

methyl (((6-hydroxy-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl)(4-nitrophenyl)carbamate;

6-((1-methoxycyclopentyl)oxy)-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-ol;

6-(ethoxymethoxy)-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-ol;

6-((cyclohexyloxy)methoxy)-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-ol;

6-(ethoxymethoxy)-5′-methyl-4-(2-methyloctan-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-ol;

methyl (((6-hydroxy-5′-methyl-4-(2-methyloctan-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl)(phenyl)carbamate;

((6-hydroxy-5′-methyl-4-(2-methyloctan-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl pivalate;

ethyl (((6-hydroxy-5′-methyl-4-(2-methyloctan-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl) carbonate;

((6-hydroxy-5′-methyl-4-propyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl pivalate;

ethyl (((6-hydroxy-5′-methyl-4-propyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl) carbonate;

6-(methoxymethoxy)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-ol;

6-((2-methoxyethoxy)methoxy)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-ol;

6-((2-methoxypropan-2-yl)oxy)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-ol;

6-((2,5,8,11,14-pentaoxahexadecan-15-yl)oxy)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-ol;

ethyl (((6-hydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl) carbonate;

ethyl (1-((6-hydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)ethyl) carbonate;

1-((6-hydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)ethyl (2-methoxyethyl) carbonate;

((6-hydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl pivalate;

((6-hydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl 2-ethylbutanoate;

((6-hydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl acetate;

methyl (((6-hydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl)(methyl)carbamate;

2-methoxyethyl (((6-hydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl)(methyl)carbamate;

2,5,8,11-tetraoxatridecan-13-yl (((6-hydroxy-2′,5′-dimethyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl)(methyl)carbamate;

methyl (((6-hydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl)(phenyl)carbamate;

methyl (((6-hydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl)(4-nitrophenyl)carbamate;

6-((1-methoxycyclopentyl)oxy)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-ol;

6-(ethoxymethoxy)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-ol;

6-((cyclohexyloxy)methoxy)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-ol;

6-(ethoxymethoxy)-5′-methyl-4-(2-methyloctan-2-yl)-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-ol;

methyl (((6-hydroxy-5′-methyl-4-(2-methyloctan-2-yl)-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl)(phenyl)carbamate;

((6-hydroxy-5′-methyl-4-(2-methyloctan-2-yl)-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl pivalate;

ethyl (((6-hydroxy-5′-methyl-4-(2-methyloctan-2-yl)-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl) carbonate;

((6-hydroxy-5′-methyl-2′-(prop-1-en-2-yl)-4-propyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl pivalate;

ethyl (((6-hydroxy-5′-methyl-2′-(prop-1-en-2-yl)-4-propyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2-yl)oxy)methyl) carbonate;

2,6-bis(methoxymethoxy)-3′-methyl-4-pentyl-1,1′-biphenyl;

bis((2-methoxyethoxy)methoxy)-3′-methyl-4-pentyl-1,1′-biphenyl;

2,6-bis((2-methoxypropan-2-yl)oxy)-3′-methyl-4-pentyl-1,1′-biphenyl;

15,15′-((3′-methyl-4-pentyl-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(2,5,8,11,14-pentaoxahexadecane);

diethyl (((3′-methyl-4-pentyl-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene)) bis(carbonate);

diethyl (((3′-methyl-4-pentyl-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(ethane-1,1-diyl)) bis(carbonate);

bis(2-methoxyethyl)(((3′-methyl-4-pentyl-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(ethane-1,1-diyl)) bis(carbonate);

[3-(2,2-dimethylpropanoyloxymethoxy)-2-(m-tolyl)-5-pentyl-phenoxy]methyl 2,2-dimethylpropanoate;

((3′-methyl-4-pentyl-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene) bis(2-ethylbutanoate);

((3′-methyl-4-pentyl-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene) diacetate;

dimethyl (((3′-methyl-4-pentyl-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene))bis(methylcarbamate);

bis(2-methoxyethyl) (((3′-methyl-4-pentyl-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene))bis(methylcarbamate);

di(2,5,8,11-tetraoxatridecan-13-yl) (((3′-methyl-4-pentyl-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene))bis(methylcarbamate;

dimethyl (((3′-methyl-4-pentyl-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene))bis(phenylcarbamate);

dimethyl (((3′-methyl-4-pentyl-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene))bis((4-nitrophenyl)carbamate);

2,6-bis((1-methoxycyclopentyl)oxy)-3′-methyl-4-pentyl-1,1′-biphenyl;

2,6-bis(ethoxymethoxy)-3′-methyl-4-pentyl-1,1′-biphenyl;

2,6-bis((cyclohexyloxy)methoxy)-3′-methyl-4-pentyl-1,1′-biphenyl;

2,6-bis(ethoxymethoxy)-3′-methyl-4-(2-methyloctan-2-yl)-1,1′-biphenyl;

dimethyl (((3′-methyl-4-(2-methyloctan-2-yl)-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene))bis(phenylcarbamate);

((3′-methyl-4-(2-methyloctan-2-yl)-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene) bis(2,2-dimethylpropanoate);

diethyl (((3′-methyl-4-(2-methyloctan-2-yl)-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene)) bis(carbonate);

((3′-methyl-4-propyl-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene) bis(2,2-dimethylpropanoate);

diethyl (((3′-methyl-4-propyl-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene)) bis(carbonate);

2,6-bis(methoxymethoxy)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1,1′-biphenyl;

2,6-((2-methoxyethoxy)methoxy)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1,1′-biphenyl;

2,6-bis((2-methoxypropan-2-yl)oxy)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1,1′-biphenyl;

15,15′-((5′-methyl-4-pentyl-(prop-1-en-2-yl)-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(2,5,8,11,14-pentaoxahexadecane);

diethyl (((5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene)) bis(carbonate);

diethyl (((5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(ethane-1,1-diyl)) bis(carbonate);

bis(2-methoxyethyl) (((5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(ethane-1,1-diyl)) bis(carbonate);

((5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene) bis(2,2-dimethylpropanoate);

((5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene) bis(2-ethylbutanoate);

((5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene) diacetate;

dimethyl (((5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene))bis(methylcarbamate);

bis(2-methoxyethyl) (((5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene)bis(methylcarbamate);

di(2,5,8,11-tetraoxatridecan-13-yl) (((5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene))bis(methylcarbamate;

dimethyl (((5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene))bis(phenylcarbamate);

dimethyl (((5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene))bis((4-nitrophenyl)carbamate);

2,6-bis((1-methoxycyclopentyl)oxy)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1,1′-biphenyl;

2,6-bis(ethoxymethoxy)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1,1′-biphenyl;

2,6-bis((cyclohexyloxy)methoxy)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1,1′-biphenyl;

2,6-bis(ethoxymethoxy)-5′-methyl-4-(2-methyloctan-2-yl)-2′-(prop-1-en-2-yl)-1,1′-biphenyl;

dimethyl (((5′-methyl-4-(2-methyloctan-2-yl)-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene))bis(phenylcarbamate);

((5′-methyl-4-(2-methyloctan-2-yl)-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene) bis(2,2-dimethylpropanoate);

diethyl (((5′-methyl-4-(2-methyloctan-2-yl)-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene)) bis(carbonate);

((5′-methyl-2′-(prop-1-en-2-yl)-4-propyl-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene) bis(2,2-dimethylpropanoate;

diethyl (((5′-methyl-2′-(prop-1-en-2-yl)-4-propyl-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene)) bis(carbonate);

bis(methoxymethoxy)-5-methyl-4′-pentyl-1,2,3,4-tetrahydro-1,1′-biphenyl;

2′,6′-bis((2-methoxyethoxy)methoxy)-5-methyl-4′-pentyl-1,2,3,4-tetrahydro-1,1′-biphenyl;

2′,6′-bis((2-methoxypropan-2-yl)oxy)-5-methyl-4′-pentyl-1,2,3,4-tetrahydro-1,1′-biphenyl;

15,15′-((5′-methyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(2,5,8,11,14-pentaoxahexadecane);

diethyl (((5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene)) bis(carbonate);

diethyl (((5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl))bis(oxy))ethane-1,1′-diyl))bis(carbonate);

bis(2-methoxyethyl) (((5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)oxy))(bis)(ethane-1,1-diyl) bis(carbonate);

((5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene)bis(2,2-dimethylpropanoate);

((5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene) bis(2-ethylbutanoate);

((5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene) diacetate;

dimethyl (((5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene))bis(methylcarbamate);

bis(2-methoxyethyl) (((5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene))bis(methylcarbamate);

di(2,5,8,11-tetraoxatridecan-13-yl) (((5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene))bis(methylcarbamate);

(((5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene))bis(phenylcarbamate);

dimethyl (((5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene))bis((4-nitrophenyl)carbamate);

2′,6′-bis((1-methoxycyclopentyl)oxy)-5-methyl-4′-pentyl-1,2,3,4-tetrahydro-1,1′-biphenyl;

2′,6′-bis(ethoxymethoxy)-5-methyl-4′-pentyl-1,2,3,4-tetrahydro-1,1′-biphenyl;

2′,6′-bis((cyclohexyloxy)methoxy)-5-methyl-4′-pentyl-1,2,3,4-tetrahydro-1,1′-biphenyl;

2′,6′-bis(ethoxymethoxy)-5-methyl-4′-(2-methyloctan-2-yl)-1,2,3,4-tetrahydro-1,1′-biphenyl;

dimethyl (((5′-methyl-4-(2-methyloctan-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene))bis(phenylcarbamate);

((5′-methyl-4-(2-methyloctan-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene) bis(2,2-dimethylpropanoate);

diethyl (((5′-methyl-4-(2-methyloctan-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene)) bis(carbonate);

((5′-methyl-4-propyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene) bis(2,2-dimethylpropanoate);

diethyl (((5′-methyl-4-propyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene)) bis(carbonate);

2′,6′-bis((2-methoxyethoxy)methoxy)-5-methyl-4′-pentyl-2-(prop-1-en-2-yl)-1,2,3,4-tetrahydro-1,1′-biphenyl;

2′,6′-bis((2-methoxypropan-2-yl)oxy)-5-methyl-4′-pentyl-2-(prop-1-en-2-yl)-1,2,3,4-tetrahydro-1,1′-biphenyl;

15,15′-((5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(2,5,8,11,14-pentaoxahexadecane);

diethyl (((5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene)) bis(carbonate);

diethyl (((5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(ethane-1,1-diyl)) bis(carbonate);

bis(2-methoxyethyl) (((5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(ethane-1,1-diyl)) bis(carbonate);

((5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene) bis(2,2-dimethylpropanoate);

((5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene) bis(2-ethylbutanoate);

((5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene) diacetate;

dimethyl (((5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene))bis(methylcarbamate);

bis(2-methoxyethyl) (((5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene))bis(methylcarbamate);

di(2,5,8,11-tetraoxatridecan-13-yl) (((5′-dimethyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene))bis(methylcarbamate);

dimethyl (((5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene))bis(phenylcarbamate);

dimethyl (((5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene))bis((4-nitrophenyl)carbamate);

2′,6′-bis((1-methoxycyclopentyl)oxy)-5-methyl-4′-pentyl-2-(prop-1-en-2-yl)-1,2,3,4-tetrahydro-1,1′-biphenyl;

2′,6′-bis(ethoxymethoxy)-5-methyl-4′-pentyl-2-(prop-1-en-2-yl)-1,2,3,4-tetrahydro-1,1′-biphenyl;

2′,6′-bis((cyclohexyloxy)methoxy)-5-methyl-4′-pentyl-2-(prop-1-en-2-yl)-1,2,3,4-tetrahydro-1,1′-biphenyl;

2′,6′-bis(ethoxymethoxy)-5-methyl-4′-(2-methyloctan-2-yl)-2-(prop-1-en-2-yl)-1,2,3,4-tetrahydro-1,1′-biphenyl;

dimethyl (((5′-methyl-4-(2-methyloctan-2-yl)-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene))bis(phenylcarbamate);

((5′-methyl-4-(2-methyloctan-2-yl)-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene) bis(2,2-dimethylpropanoate);

diethyl (((5′-methyl-4-(2-methyloctan-2-yl)-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene)) bis(carbonate);

((5′-methyl-2′-(prop-1-en-2-yl)-4-propyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene) bis(2,2-dimethylpropanoate); or

diethyl (((5′-methyl-2′-(prop-1-en-2-yl)-4-propyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diyl)bis(oxy))bis(methylene)) bis(carbonate),

or an enantiomer, diastereomer, racemate, or tautomer thereof, or a pharmaceutically acceptable salt, solvate or hydrate of the compound, enantiomer, diastereomer, racemate, or tautomer.

2 . A pharmaceutical composition comprising a compound of claim 1 , or an enantiomer, diastereomer, racemate, or tautomer thereof, or a pharmaceutically acceptable salt, solvate or hydrate of the compound, enantiomer, diastereomer, racemate, or tautomer, together with a pharmaceutically acceptable excipient, diluent, or carrier.

Assignments (6)
SECURITY INTEREST Recorded Jan 20, 2026
From: CANOPY GROWTH CORPORATION; TWEED INC.
To: JGB COLLATERAL LLC
Reel/Frame 073521/0250 →
RELEASE OF SECURITY INTEREST IN PATENT INTELLECTUAL PROPERTY Recorded Jan 9, 2026
From: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
To: CANOPY GROWTH CORPORATION
Reel/Frame 074281/0925 →
NOTICE OF GRANT OF SECURITY INTEREST Recorded Aug 15, 2024
From: CANOPY GROWTH CORPORATION
To: WILMINGTON TRUST, NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 068654/0264 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 10, 2023
From: OMEARA, JEFFREY ALAN; TO, QUANG HUY
To: DALRIADA DRUG DISCOVERY INC.
Reel/Frame 063598/0034 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 10, 2023
From: DALRIADA DRUG DISCOVERY INC.
To: 10607410 CANADA INC.
Reel/Frame 063598/0333 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 10, 2023
From: 10607410 CANADA INC.
To: CANOPY GROWTH CORPORATION
Reel/Frame 063598/0389 →
Continuity (4)
Provisional Application 62966421 · Jan 27, 2020
Provisional Application 62934318 · Nov 12, 2019
Provisional Application 62870743 · Jul 4, 2019
Related Publication 20220267239A1 · Aug 25, 2022
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