Nitrated lipids and methods of making and using thereof
AssigneesThe UAB Research Foundation, The State of Oregon Acting by and through the State Board of Higher Education on Behalf of the University of Oregon, University College Cardiff Consultants Limited, Morehouse School of Medicine
InventorsBruce A. Freeman, Francisco Schopfer, Valerie O'Donnell, Paul Baker, Yuqing E. Chen, Bruce Branchaud
Life of this patent
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Abstract
Described herein are nitrated lipids and methods of making and using the nitrated lipids.
Claims26
A method of treating renal inflammation, sickle cell disease, or pulmonary inflammation in a subject, comprising administering to the subject a compound comprising a lipid having the structure:
- wherein:
- R1 is selected from the group consisting of C1-C24 alkyl, C1-C24 alkenyl, and C1-C24 alkynyl;
- R2, R3, R7, and R8 are each independently selected from the group consisting of hydrogen, NO2, OH, and OOH, wherein at least one of R2, R3, R7, and R8 is NO2;
- R4 is C1-C24 alkyl, C1-C24 alkenyl, or C1-C24 alkenyl, wherein R4 comprises a terminal COOR6 and R6 is hydrogen, C1-C24 alkyl, or a pharmaceutically acceptable counterion;
- R5 is hydrogen or R4 and R5 collectively form ═C(R9)(R10), wherein R9 is C1-C24 alkyl, C1-C24 alkenyl, or C1-C24 alkynyl and R10 is hydrogen, NO2, OH, or OOH;
- and
- n is from 1 to 24,
- wherein the compound is substantially pure.
A method of treating renal inflammation comprising administering to a subject in need of treatment an effective amount of a pharmaceutical composition containing a compound of formula:
- wherein:
- R1 is C1-C24 alkyl, C1-C24 alkenyl, or C1-C24 alkynyl;
- R2, R3, R7, and R8 are each independently hydrogen, NO2, OH, or OOH, and at least one of R2, R3, R7, and R8 is NO2;
- R4 is C1-C24 alkyl, C1-C24 alkenyl, or C1-C24 alkenyl, and R4 comprises a terminal COOR6, and R6 is hydrogen, C1-C24 alkyl, or a pharmaceutically acceptable counterion;
- R5 is hydrogen or R4 and R5 collectively form ═C(R9)(R10), wherein R9 is C1-C24 alkyl, C1-C24 alkenyl, or C1-C24 alkynyl and R10 is hydrogen, NO2, OH, or OOH;
- and
- n is from 1 to 24, wherein the compound is substantially pure;
- and
- a pharmaceutically acceptable carrier, thickener, diluent, solvent, buffer, preservative, or surface active agent.
A method for treating pulmonary inflammation comprising administering to a patient in need of treatment an effective amount of a pharmaceutical composition containing a compound of formula:
- wherein:
- R1 is C1-C24 alkyl, C1-C24 alkenyl, or C1-C24 alkynyl;
- R2, R3, R7, and R8 are each independently hydrogen, NO2, OH, or OOH, and at least one of R2, R3, R7, and R8 is NO2;
- R4 is C1-C24 alkyl, C1-C24 alkenyl, or C1-C24 alkenyl, and R4 comprises a terminal COOR6, and R6 is hydrogen, C1-C24 alkyl, or a pharmaceutically acceptable counterion;
- R5 is hydrogen or R4 and R5 collectively form ═C(R9)(R10), wherein R9 is C1-C24 alkyl, C1-C24 alkenyl, or C1-C24 alkynyl and R10 is hydrogen, NO2, OH, or OOH;
- and
- n is from 1 to 24, wherein the compound is substantially pure;
- and
- a pharmaceutically acceptable carrier, thickener, diluent, solvent, buffer, preservative, or surface active agent.
A method for treating sickle cell disease comprising administering to a patient in need of treatment an effective amount of a pharmaceutical composition containing a compound of formula:
- wherein:
- R1 is C1-C24 alkyl, C1-C24 alkenyl, or C1-C24 alkynyl;
- R2, R3, R7, and R8 are each independently hydrogen, NO2, OH, or OOH, and at least one of R2, R3, R7, and R8 is NO2;
- R4 is C1-C24 alkyl, C1-C24 alkenyl, or C1-C24 alkenyl, and R4 comprises a terminal COOR6, and R6 is hydrogen, C1-C24 alkyl, or a pharmaceutically acceptable counterion;
- R5 is hydrogen or R4 and R5 collectively form ═C(R9)(R10), wherein R9 is C1-C24 alkyl, C1-C24 alkenyl, or C1-C24 alkynyl and R10 is hydrogen, NO2, OH, or OOH;
- and
- n is from 1 to 24, wherein the compound is substantially pure;
- and
- a pharmaceutically acceptable carrier, thickener, diluent, solvent, buffer, preservative, or surface active agent.
Dependencies are inferred from the claim text.