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US 11,472,787 B2Granted
Docosahexaenoic acid endocannabinoid epoxide derivative compositions
AssigneeThe Board of Trustees of the University of Illinois
InventorsAditi Das, Jahnabi Roy
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Abstract
The present disclosure provides novel compounds derived from docosahexaenoic acid endocannabinoid epoxides having anti-cancer, anti-inflammatory, anti-platelet aggregation and anti-angiogenic properties. Methods of synthesizing and using the compositions are also provided.
Claims20
A compound of formula (I), or a pharmaceutically acceptable salt thereof,
- wherein,
- one of L1 L2 L3 L4 L5 and L6 is
- and the others of L1 L2 L3 L4 L5 and L6 are
- is 3- to 6-membered ring, wherein at least one ring atom is a heteroatom selected from the group consisting of oxygen, nitrogen, and sulfur;
- R1 is hydrogen, C1-6alkyl, C1-6haloalkyl, —C1-6alkylene-Rx1, -G1, or —C1-6alkylene-G1;
- G1 is C3-8cycloalkyl, C3-8cycloalkenyl, aryl, heteroaryl, or heterocycle, wherein G1 is optionally substituted with 1, 2, 3, or 4 Rx1;
- R2 is C1-6alkyl, C1-6haloalkyl, —C1-6alkylene-Rx2, -G2, or —C1-6alkylene-G2;
- G2 is C3-8cycloalkyl, C3-8cycloalkenyl, aryl, heteroaryl, or heterocycle, wherein G2 is optionally substituted with 1, 2, 3, or 4 Rx2;
- Rx1 and Rx2 at each occurrence are independently cyano, —OH, —OC1-4alkyl, —OC(O)C1-4alkyl, —NH2, —NHC1-4alkyl, —N(C1-4alkyl)2, —NHC(O)C1-4alkyl, or —N(C1-4alkyl)C(O)C1-4alkyl;
- provided that R2 is not —CH2CH2OH when
- and the compound of formula (I) is not formula (I-ba), (I-ca), (I-da), (I-ea), or (I-fa), wherein X is O;
- and R2 is —C1-6alkylene-Rx2,
9 more elements
A compound of formula (i)
- wherein,
- R1 and R2 are independently —CH2CH2CH2OH, —CH(CH3)CH2OH,
- a carbon chain with 3, 4, 5 or 6 carbon atoms ending in CH3, —OH or —NH2, a saturated cyclic ring with 3, 4, 5 or 6 carbons with no substitutions, a saturated cyclic ring with 3, 4, 5 or 6 carbons with substitutions of —OH and —NH2, an unsaturated cyclic ring with 3, 4, 5 or 6 carbons with no substitutions, an unsaturated cyclic ring with 3, 4, 5 or 6 carbons with substitutions of —OH and —NH2, an aromatic group with no substitutions, an aromatic group with substitutions of —OH or —NH2, or a saturated or unsaturated cyclic ring containing N, O or S;
- and
- R3 is a 3, 4, 5, or 6 membered ring containing, nitrogen or sulfur.
2 more elements
A compound of formula (i)
- wherein,
- R1 and R2 are independently —CH2CH2CH2OH, —CH(CH3)CH2OH,
- a carbon chain with 3, 4, 5 or 6 carbon atoms ending in CH3, —OH or —NH2, a saturated cyclic ring with 3, 4, 5 or 6 carbons with no substitutions, a saturated cyclic ring with 3, 4, 5 or 6 carbons with substitutions of —OH and —NH2, an unsaturated cyclic ring with 3, 4, 5 or 6 carbons with no substitutions, an unsaturated cyclic ring with 3, 4, 5 or 6 carbons with substitutions of —OH and —NH2, an aromatic group with no substitutions, an aromatic group with substitutions of —OH or —NH2, or a saturated or unsaturated cyclic ring containing N, O or S;
- and
- R3 is a 4, 5, or 6 membered ring containing oxygen, nitrogen, or sulfur.
2 more elements
Dependencies are inferred from the claim text.