IP Library › Granted Patent US 12,195,429
Granted Patent B2
US 12,195,429 · App. 17/626,516 · Granted Jan 14, 2025

Cannabinoid derivatives

Inventors: Siawash Ahmar (Toronto, CA); Jeffrey Alan Omeara (Halton Hills, CA); Peter Martin Dove (Smiths Falls, CA)
Assignee: CANOPY GROWTH CORPORATION
C07D213/30C07C39/245C07C43/2055C07C43/225C07C255/53C07D203/10C07D207/333C07D209/12C07D231/12C07D235/18C07D239/26C07D241/12C07D249/08C07D257/04C07D261/08C07D263/14C07D271/06C07D271/113C07D277/26C07D295/033C07D303/14C07D305/06C07D307/42C07D309/32C07D333/16C07D333/56C07D473/00
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Quick Facts
Patent No.
US 12,195,429
App. No.
17/626,516
Granted
Jan 14, 2025
Kind
B2
Abstract

The current application relates to cannabinoid derivatives of formula (I) and pharmaceutical compositions comprising the same. The cannabinoid derivative can be used for the treatment of diseases associated with cannabinoid receptor such as pain, ADHD/ADD, alcohol use disorder, anxiety disorder, and dementias.

Claims (166)

1. A compound which is:

3′-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)-4-pentyl-[1,1′-biphenyl]-2,6-diol;

3′-methyl-3-(5-methyl-1,2,4-oxadiazol-3-yl)-4-pentyl-[1,1′-biphenyl]-2,6-diol;

3′-methyl-4-pentyl-3-(1H-tetrazol-5-yl)-[1,1′-biphenyl]-2,6-diol;

5-(2,6-dihydroxy-3′-methyl-4-pentyl-[1,1′-biphenyl]-3-yl)-1,3,4-oxadiazol-2 (3H)-one;

3′-methyl-3-(5-methyl-4H-1,2,4-triazol-3-yl)-4-pentyl-[1,1′-biphenyl]-2,6-diol;

3′-methyl-4-pentyl-3-(1H-pyrrol-3-yl)-[1,1′-biphenyl]-2,6-diol;

3′-methyl-4-pentyl-3-(1H-pyrrol-2-yl)-[1,1′-biphenyl]-2,6-diol;

3′-methyl-4-pentyl-3-(pyridin-2-yl)-[1,1′-biphenyl]-2,6-diol;

3′-methyl-4-pentyl-3-(pyrimidin-4-yl)-[1,1′-biphenyl]-2,6-diol;

3′-methyl-4-pentyl-3-(pyrazin-2-yl)-[1,1′-biphenyl]-2,6-diol;

3′-methyl-4-pentyl-3-(pyrimidin-2-yl)-[1,1′-biphenyl]-2,6-diol;

3′-methyl-4-pentyl-3-(pyridin-3-yl)-[1,1′-biphenyl]-2,6-diol;

3′-methyl-4-pentyl-3-(pyrimidin-5-yl)-[1,1′-biphenyl]-2,6-diol;

3′-methyl-4-pentyl-3-(pyridin-4-yl)-[1,1′-biphenyl]-2,6-diol;

3-(furan-2-yl)-3′-methyl-4-pentyl-[1,1′-biphenyl]-2,6-diol;

3′-methyl-4-pentyl-3-(thiophen-2-yl)-[1,1′-biphenyl]-2,6-diol;

3′-methyl-4-pentyl-3-(thiophen-3-yl)-[1,1′-biphenyl]-2,6-diol;

3′-methyl-4-pentyl-3-(thiazol-5-yl)-[1,1′-biphenyl]-2,6-diol;

3′-methyl-4-pentyl-3-(thiazol-4-yl)-[1,1′-biphenyl]-2,6-diol;

3-(indolin-2-yl)-3′-methyl-4-pentyl-[1,1′-biphenyl]-2,6-diol;

3-(1H-benzo[d]imidazol-2-yl)-3′-methyl-4-pentyl-[1,1′-biphenyl]-2,6-diol;

3′-methyl-4-pentyl-3-(9H-purin-8-yl)-[1,1′-biphenyl]-2,6-diol;

3′-methyl-3-(oxetan-2-yl)-4-pentyl-[1,1′-biphenyl]-2,6-diol;

3′-methyl-3-(oxetan-3-yl)-4-pentyl-[1,1′-biphenyl]-2,6-diol;

3′-methyl-3-(oxiran-2-yl)-4-pentyl-[1,1′-biphenyl]-2,6-diol;

3-(aziridin-2-yl)-3′-methyl-4-pentyl-[1,1′-biphenyl]-2,6-diol;

3-(aziridin-1-yl)-3′-methyl-4-pentyl-[1,1′-biphenyl]-2,6-diol;

3-(1H-indol-2-yl)-3′-methyl-4-pentyl-[1,1′-biphenyl]-2,6-diol;

3″-methyl-6′-pentyl-4-(pyridin-3-yl)-[1,1′:3′,1″-terphenyl]-2′,4′-diol;

3-(isoxazol-5-yl)-3′-methyl-4-pentyl-[1,1′-biphenyl]-2,6-diol;

3-(4,5-dihydrooxazol-2-yl)-3′-methyl-4-pentyl-[1,1′-biphenyl]-2,6-diol;

3′-methyl-4-pentyl-3-(4H-pyran-4-yl)-[1,1′-biphenyl]-2,6-diol;

3′-methyl-3-(1-methyl-1H-pyrazol-5-yl)-4-pentyl-[1,1′-biphenyl]-2,6-diol;

3-(benzo[b]thiophen-2-yl)-3′-methyl-4-pentyl-[1,1′-biphenyl]-2,6-diol;

3′-methyl-3-(2-methylpyridin-4-yl)-4-pentyl-[1,1′-biphenyl]-2,6-diol;

3-(3,5-dimethylisoxazol-4-yl)-3′-methyl-4-pentyl-[1,1′-biphenyl]-2,6-diol;

3′-methyl-4-pentyl-3-(1H-pyrazol-5-yl)-[1,1′-biphenyl]-2,6-diol;

4-(2′,4′-dimethoxy-3″-methyl-6′-pentyl-[1,1′:3′,1″-terphenyl]-3-yl) morpholine;

3-(2,6-dimethoxy-3′-methyl-4-pentyl-[1,1′-biphenyl]-3-yl)pyridine;

2′, 6′-dimethoxy-3-methyl-4′-pentyl-1,1′:3′,1″-terphenyl;

3′-methyl-4-pentyl-3-(1H-pyrazol-4-yl)-[1,1′-biphenyl]-2,6-diol;

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

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

5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-3-(1H-tetrazol-5-yl)-[1,1′-biphenyl]-2,6-diol;

5-(2,6-dihydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-3-yl)-1,3,4-oxadiazol-2(3H)-one;

5′-methyl-3-(5-methyl-4H-1,2,4-triazol-3-yl)-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2,6-diol;

5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-3-(1H-pyrrol-3-yl)-[1,1′-biphenyl]-2,6-diol;

5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-3-(1H-pyrrol-2-yl)-[1,1′-biphenyl]-2,6-diol;

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

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

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

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

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

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

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

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

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

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

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

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

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

3-(1H-benzo[d]imidazol-2-yl)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2,6-diol;

5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-3-(9H-purin-8-yl)-[1,1′-biphenyl]-2,6-diol;

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

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

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

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

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

3-(1H-indol-2-yl)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2,6-diol;

5″-methyl-6′-pentyl-2″-(prop-1-en-2-yl)-4-(pyridin-3-yl)-[1,1′:3′,1″-terphenyl]-2′,4′-diol;

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

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

5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-3-(4H-pyran-4-yl)-[1,1′-biphenyl]-2,6-diol;

5′-methyl-3-(1-methyl-1H-pyrazol-5-yl)-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2,6-diol;

3-(benzo[b]thiophen-2-yl)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-2,6-diol;

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

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

5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-3-(1H-pyrazol-5-yl)-[1,1′-biphenyl]-2,6-diol;

4-(2′,4′-dimethoxy-5″-methyl-6′-pentyl-2″-(prop-1-en-2-yl)-[1,1′:3′,1″-terphenyl]-3-yl) morpholine;

3-(2,6-dimethoxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-[1,1′-biphenyl]-3-yl) pyridine 2′,6′-dimethoxy-5-methyl-4′-pentyl-2-(prop-1-en-2-yl)-1,1′:3′,1″-terphenyl;

5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-3-(1H-pyrazol-4-yl)-[1,1′-biphenyl]-2,6-diol;

5′-methyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5′-methyl-3-(5-methyl-1,2,4-oxadiazol-3-yl)-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5′-methyl-4-pentyl-3-(1H-tetrazol-5-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5-(2,6-dihydroxy-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-3-yl)-1,3,4-oxadiazol-2 (3H)-one;

5′-methyl-3-(5-methyl-4H-1,2,4-triazol-3-yl)-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5′-methyl-4-pentyl-3-(1H-pyrrol-3-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5′-methyl-4-pentyl-3-(1H-pyrrol-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5′-methyl-4-pentyl-3-(pyridin-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5′-methyl-4-pentyl-3-(pyrimidin-4-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5′-methyl-4-pentyl-3-(pyrazin-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5′-methyl-4-pentyl-3-(pyrimidin-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5′-methyl-4-pentyl-3-(pyridin-3-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5′-methyl-4-pentyl-3-(pyrimidin-5-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5′-methyl-4-pentyl-3-(pyridin-4-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

3-(furan-2-yl)-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5′-methyl-4-pentyl-3-(thiophen-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5′-methyl-4-pentyl-3-(thiophen-3-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5′-methyl-4-pentyl-3-(thiazol-5-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5′-methyl-4-pentyl-3-(thiazol-4-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

3-(indolin-2-yl)-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

3-(1H-benzo[d]imidazol-2-yl)-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5′-methyl-4-pentyl-3-(9H-purin-8-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5′-methyl-3-(oxetan-2-yl)-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5′-methyl-3-(oxetan-3-yl)-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5′-methyl-3-(oxiran-2-yl)-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

3-(aziridin-2-yl)-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

3-(aziridin-1-yl)-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

3-(1H-indol-2-yl)-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5″-methyl-6′-pentyl-4-(pyridin-3-yl)-1″,2″,3″,4″-tetrahydro-[1,1′:3′,1″-terphenyl]-2′,4′-diol;

3-(isoxazol-5-yl)-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

3-(4,5-dihydrooxazol-2-yl)-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5′-methyl-4-pentyl-3-(4H-pyran-4-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5′-methyl-3-(1-methyl-1H-pyrazol-5-yl)-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

3-(benzo[b]thiophen-2-yl)-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5′-methyl-3-(2-methylpyridin-4-yl)-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

3-(3,5-dimethylisoxazol-4-yl)-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5′-methyl-4-pentyl-3-(1H-pyrazol-5-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

4-(2′,4′-dimethoxy-5″-methyl-6′-pentyl-1″,2″,3″,4″-tetrahydro-[1,1′:3′,1″-terphenyl]-3-yl) morpholine;

2′, 6′-dimethoxy-5-methyl-4′-pentyl-1,2,3,4-tetrahydro-1,1′:3′,1″-terphenyl;

5′-methyl-4-pentyl-3-(1H-pyrazol-4-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

3-(2,6-dimethoxy-5′-methyl-4-pentyl-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-3-yl) pyridine;

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

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

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

5-(2,6-dihydroxy-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-3-yl)-1,3,4-oxadiazol-2 (3H)-one;

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

3-(1H-benzo[d]imidazol-2-yl)-5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

5′-methyl-4-pentyl-2′-(prop-1-en-2-yl)-3-(9H-purin-8-yl)-1′,2′,3′,4′-tetrahydro-[1,1′-biphenyl]-2,6-diol;

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

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

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

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

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

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

5″-methyl-6′-pentyl-2″-(prop-1-en-2-yl)-4-(pyridin-3-yl)-1″,2″,3″,4″-tetrahydro-[1,1′:3′, 1″-terphenyl]-2′,4′-diol;

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

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

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

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

4-(benzothiophen-2-yl)-2-[6-isopropenyl-3-methyl-cyclohez-2-en-1-yl]-5-pentyl-benzene-1,3-diol;

2-(6-isopropenyl-3-methyl-cyclohex-2-en-1-yl)-4-(2-methyl-4-pyridyl)-5-pentyl-benzene-1,3-diol;

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

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

4-(2′,4′-dimethoxy-5″-methyl-6′-pentyl-2″-(prop-1-en-2-yl)-1″,2″,3″,4″-tetrahydro-[1,1′:3′,1″-terphenyl]-3-yl) morpholine;

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

2′,6′-dimethoxy-5-methyl-4′-pentyl-2-(prop-1-en-2-yl)-1,2,3,4-tetrahydro-1,1′:3′,1″-terphenyl; or

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

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: AHMAR, SIAWASH; OMEARA, JEFFREY ALAN; DOVE, PETER MARTIN
To: DALRIADA DRUG DISCOVERY INC.
Reel/Frame 063598/0941 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 10, 2023
From: DALRIADA DRUG DISCOVERY INC.
To: 10607410 CANADA INC.
Reel/Frame 063598/0983 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 10, 2023
From: 10607410 CANADA INC.
To: CANOPY GROWTH CORPORATION
Reel/Frame 063599/0012 →
Continuity (2)
Provisional Application 62873692 · Jul 12, 2019
Related Publication 20220324806A1 · Oct 13, 2022
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