US 12,195,429 B2Granted

Cannabinoid derivatives

AssigneeCanopy Growth Corporation

InventorsSiawash Ahmar, Jeffrey Alan Omeara, Peter Martin Dove

Life of this patent

Estimating the term…

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.

Claims2

Dependent claims

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.

162 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/626,516Filed 10 Jul 2020 · us provisional application
Priority: 12 Jul 2019
Published: US 2022/0324806 A113 Oct 2022
Granted: 14 Jan 2025
Term ends: Not estimatedThe source records don’t support an estimate.

Classification37 codes

C07C 39/42
Halogenated derivatives: containing six-membered aromatic rings and other rings
C07D 213/30
Radicals substituted by singly-bound oxygen or sulphur atoms: oxygen atoms
C07C 39/245
Halogenated derivatives: monocyclic polyhydroxylic containing halogens bound to ring carbon atoms
C07C 43/2055
The aromatic ring being a non-condensed ring: containing more than one ether bond

Family

Application62/873,692Us provisional application · filed 12 Jul 2019
US 2022/0324806 A1Pre-grant publication · published 13 Oct 2022
US 12,195,429 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

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.

162 more elements

Facts

Application

17/626,516Filed 10 Jul 2020 · us provisional application

Priority

12 Jul 2019

Published

US 2022/0324806 A113 Oct 2022

Granted

14 Jan 2025

Term ends

Not estimatedThe source records don’t support an estimate.

Classification37 codes

C07C 39/42
Halogenated derivatives: containing six-membered aromatic rings and other rings
C07D 213/30
Radicals substituted by singly-bound oxygen or sulphur atoms: oxygen atoms
C07C 39/245
Halogenated derivatives: monocyclic polyhydroxylic containing halogens bound to ring carbon atoms
C07C 43/2055
The aromatic ring being a non-condensed ring: containing more than one ether bond