Fatty acids as anti-inflammatory agents
AssigneeUniversity of Pittsburgh—Of the Commonwealth System of Higher Education
InventorsBruce A. Freeman, Francisco J. Schopfer
Life of this patent
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Abstract
Compounds of formula I and their metabolites are potent mediators of an inflammatory response: where a, b, c, d, e, f, V, W, X, Y, Ra, Ra′, Rb, Rb′, Rc, and Rc′ are defined herein. In particular, the compounds of the invention are candidate therapeutics for treating inflammatory conditions.
Claims18
A method of treating an inflammatory condition comprising administering to the subject in need thereof a formulation comprising a therapeutically effective amount of a compound having the formula:
- wherein:
- R1 is a heterocyclyl;
- is an optional double bond;
- W is —OH, —C(O)H, —C(O), —C(O)Rp, —COOH, —COORp, —Cl, —Br, —I, —CF3, —CN, —SO3, —SO2Rp, —SO3H, —NH3+, —NH2Rp+, —NRpRqRt, —NO2, ═O, ═NRp, ═CF2, or —CHF;
- each V is, independently —CH or —C—, wherein:
- V is —CH— when W is —OH, —H, —C(O)H, —C(O), —C(O)Rp, —COOH, —COORp, —Cl, —Br, —I, —F, —CF3, —CN, —SO3, —SO2Rp, —SO3H, —NH3+, —NH2Rp+, —NRpRqRt or —NO2;
- or
- V is —C— when W is ═O, ═NRp, ═CF2 or ═CHF;
- Rp and Rq are each, independently, H, (C1-C8) alkyl, aryl, or (C1-C8) haloalkyl;
- Rt is (C1-C8) alkyl, aryl, or (C1-C8) haloalkyl;
- Rb and Rb′ are each independently, —H, —OH, —C(O)H, —C(O), —C(O)Rp, —COOH, —COORp, —Cl, —Br, —I, —F, —CF3, —CHF2, —CH2F, —CN, —SO3, —SO2Rp, SO3H, —NH3+, —NH2Rp+, —NRpRqRt or —NO2, wherein:
- Rb and Rb′ are not simultaneously non-hydrogen groups;
- a is an integer between 5 and 15 inclusive, c is an integer from 1 and 15 inclusive, and f is an integer between 5 and 15 inclusive;
- and
- a pharmaceutically acceptable carrier.
The method according to claim 10, wherein Rb and Rb′, are each, independently, —H, —OH, —CN, or —NO2.
A method of treating pulmonary inflammation in a subject comprising administering to a subject in need thereof a compound having a formula of:
- wherein:
- R1 is a heterocyclyl;
- is an optional double bond;
- W is —OH, —C(O)H, —C(O), —C(O)Rp, —COOH, —COORp, —Cl, —Br, —I, —CF3, —CN, —SO3, —SO2Rp, —SO3H, —NH3+, —NH2Rp+, —NRpRqRt, —NO2, ═O, ═NRp, ═CF2, or —CHF;
- each V is, independently —CH or —C—, wherein:
- V is —CH— when W is —OH, —H, —C(O)H, —C(O), —C(O)Rp, —COOH, —COORp, —Cl, —Br, —I, —F, —CF3, —CN, —SO3, —SO2Rp, —SO3H, —NH3+, —NH2Rp+, —NRpRqRt or —NO2;
- or
- V is —C— when W is ═O, ═NRp, ═CF2 or ═CHF;
- Rp and Rq are each, independently, H, (C1-C8) alkyl, aryl, or (C1-C8) haloalkyl;
- Rt is (C1-C8) alkyl, aryl, or (C1-C8) haloalkyl;
- Rb and Rb′ are each independently, —H, —OH, —C(O)H, —C(O), —C(O)Rp, —COOH, —COORp, —Cl, —Br, —I, —F, —CF3, —CHF2, —CH2F, —CN, —SO3, —SO2Rp, SO3H, —NH3+, —NH2Rp+, —NRpRqRt or —NO2, wherein:
- Rb and Rb′ are not simultaneously non-hydrogen groups;
- a is an integer between 5 and 15 inclusive, c is an integer from 1 and 15 inclusive, and f is an integer between 5 and 15 inclusive.
The method according to claim 144, wherein R1 is a heteroaryl or a heterocycloalkyl.
Dependencies are inferred from the claim text.