Trihydroxy polyunsaturated eicosanoid derivatives
AssigneeUniversity of Southern California
InventorNicos A. Petasis
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Abstract
The invention features methods for the preparation of naturally occurring trihydroxy polyunsaturated eicosanoids and their structural analogs. The invention further provides new derivatives and analogs of trihydroxy polyunsaturated eicosanoids that can be prepared according to these methods. The invention also provides compositions and methods using trihydroxy polyunsaturated eicosanoid derivatives for the prevention, amelioration and treatment of a variety of diseases or conditions associated with inflammation or inflammatory response, autoimmune diseases, rheumatoid arthritis, cardiovascular diseases, or abnormal cell proliferation or cancer.
Claims17
1-16. (canceled)
A method of ameliorating or treating a disease or condition associated with inflammatory response, cardiovascular disease, abnormal cell proliferation, or cancer, the method comprising administering to a subject an effective amount of a compound having a structure of general formula 46:
- wherein:
- A is hydroxy, alkoxy, aryloxy, amino, alkylamino, dialkylamino, or —OM, where M is a cation selected from ammonium, tetra-alkyl ammonium, Na, K, Mg, and Zn;
- Ra and Rb are independently selected from hydrogen, alkyl, aryl, heteroaryl, acyl, silyl, alkoxyacyl and aminoacyl;
- R2 is hydrogen, alkyl, perfluoroalkyl, aryl or heteroaryl;
- R5 is selected from i)-iv) as follows:
- i) CH2CH(R6)CH2, where R6 is hydrogen, alkyl, perfluoroalkyl, aryl, heteroaryl, fluoro, hydroxy or alkoxy;
- ii) CH2C(R6R7)CH2, where R6 and R7 are each independently alkyl, perfluoroalkyl, aryl, or fluoro, or R6 and R7 are connected together to form a carbocyclic or heterocyclic ring;
- iii) CH2OCH2, CH2C(O)CH2, or CH2CH2;
- and
- iv) a carbocyclic, heterocyclic, aryl or heteroaryl ring;
- and
- R8 and R9 are independently selected from hydrogen, alkyl, perfluoroalkyl, alkoxy, aryl and heteroaryl, or R8 and R9 are connected together to form a carbocyclic or heterocyclic ring.
A method of ameliorating or treating a disease or condition associated with, inflammatory response, cardiovascular disease, abnormal cell proliferation, or cancer, the method comprising administering to a subject an effective amount of a pharmaceutical composition comprising a pharmaceutically acceptable carrier and a compound having a structure of general formula 46:
- wherein:
- A is hydroxy, alkoxy, aryloxy, amino, alkylamino, dialkylamino, or —OM, where M is a cation selected from ammonium, tetra-alkyl ammonium, Na, K, Mg, and Zn;
- Ra and Rb are independently selected from hydrogen, alkyl, aryl, heteroaryl, acyl, silyl, alkoxyacyl and aminoacyl;
- R2 is hydrogen, alkyl, perfluoroalkyl, aryl or heteroaryl;
- R5 is selected from i)-iv) as follows:
- i) CH2CH(R6)CH2, where R6 is hydrogen, alkyl, perfluoroalkyl, aryl, heteroaryl, fluoro, hydroxy or alkoxy;
- ii) CH2C(R6R7)CH2, where R6 and R7 are each independently alkyl, perfluoroalkyl, aryl, or fluoro, or R6 and R7 are connected together to form a carbocyclic or heterocyclic ring;
- iii) CH2OCH2, CH2C(O)CH2, or CH2CH2;
- and
- iv) a carbocyclic, heterocyclic, aryl or heteroaryl ring;
- and
- R8 and R9 are independently selected from hydrogen, alkyl, perfluoroalkyl, alkoxy, aryl and heteroaryl, or R8 and R9 are connected together to form a carbocyclic or heterocyclic ring.
Dependencies are inferred from the claim text.