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US 8,476,309 B2Granted
Benzofuran cannabinoid compounds and related methods of use
AssigneeUniversity of Tennessee Research Foundation
InventorsBob M. Moore, II, Steven Gurley, Suni Mustafa
Life of this patent
Estimating the term…
Abstract
Furanopyridine cannabinoid analog compounds of the formula I are disclosed. The compounds are useful to modify the activity of CB1 and CB2 receptors and treat conditions mediated by these receptors.
Claims21
A compound of the formula
- wherein
- one of R1 and R2 can be hydrogen and the other is selected from the group consisting of cycloalkyl, aryl, heteroaryl, heterocycloalkyl, arylalkyl, cycloalkylalkyl, heteralkylalkyl and heteroarylalkyl, wherein the ring portion of each can be optionally substituted with one, two, three, four or five substituents independently selected from a group consisting of halo, alkyl, alkoxy, hydroxyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, cyano, nitro, amino, alkylamino, dialkylamino, thiol, alkylthiol, trifluoromethyl, carboxy, alkylcarboxy, carbonyl, hydroxyalkyl, oxoalkyl, carboxyalkyl, cyanoalkyl and carbamoyl;
- R4 is selected from the group consisting of cycloalkyl, aryl, heteroaryl, heterocycloalkyl, arylalkyl, cycloalkylalkyl, heteralkylalkyl and heteroarylalkyl, wherein each the ring portion of each can be optionally substituted with one, two, three, four or five substituents independently selected from a group consisting of halo, alkyl, alkoxy, hydroxyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, cyano, nitro, amino, alkylamino, dialkylamino, thiol, alkylthiol, trifluoromethyl, carboxy, alkylcarboxy and carbamoyl;
- X is selected from the group consisting of S, CH2, CH(CH3), CH(OH), C(CH3)(OH), C(CH3)2, C(—U(CH2)1U—), C((CH2)1CH3)2, C(O), NH, S(O), S(O)2, C(O)NH, S(O)NH, and S(O)2NH;
- n is an integer from 1 to 6;
- U is selected from the group consisting of CH2, S, and O;
- and
- R3 is selected from the group consisting of H, OH, OCH3, O((CH2)1CH3), SH, SCH3, NH2, NHCH3, and N(CH3)2, and pharmaceutically acceptable salts thereof.
5 more elements
A compound of the formula
- wherein
- one of R1 and R2 can be hydrogen and the other is selected from the group consisting of cycloalkyl, aryl, heteroaryl, heterocycloalkyl, arylalkyl, cycloalkylalkyl, heteralkylalkyl and heteroarylalkyl, wherein the ring portion of each can be optionally substituted with one, two, three, four or five substituents independently selected from a group consisting of halo, alkyl, alkoxy, hydroxyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, cyano, nitro, amino, alkylamino, dialkylamino, thiol, alkylthiol, trifluoromethyl, carboxy, alkylcarboxy, carbonyl, hydroxyalkyl, oxoalkyl, carboxyalkyl, cyanoalkyl and carbamoyl;
- R4 is alkyl optionally substituted with one, two, three, four or five substituents independently selected from a group consisting of halo, alkyl, alkoxy, hydroxyl, aryl, heteroaryl, cycloalkyl, heterocycloalkyl, cyano, nitro, amino, alkylamino, dialkylamino, thiol, alkylthiol, trifluoromethyl, carboxy, alkylcarboxy and carbamoyl;
- X is selected from the group consisting of C(CH3)2 and C(—U(CH2)1U—);
- n is an integer from 1 to 6;
- U is selected from the group consisting of CH2, S, and O;
- and
- R3 is selected from the group consisting of H, OH, OCH3, O((CH2)nCH3), SH, SCH3, NH2, NHCH3, and N(CH3)2, and pharmaceutically acceptable salts thereof.
5 more elements
Dependencies are inferred from the claim text.