(EP2504311) The present invention provides arachidonic acid (AA) analogs and compositions containing those analogs as active agents for use in analgesic treatments. Various methods of manufacturing the inventive compounds are provided and pharmaceutical formulations, including injectable and oral dosages, are described. Certain analogs are additionally useful as antipyretic compositions and in related fever reducing treatments. (From US9096494 B2)
(EP2504311) 1. A compound having the structure: (see diagramm) wherein: R 1 is H, or a C 1-C 6 alkyl, C 2-C 6 alkenyl, C 3-C 6 cycloalkyl or C 3-C 6 cycloalkenyl which is unsubstituted or substituted with at least one hydroxyl group; and R 2 is H, or a C 1-C 3 allcyl; or R 1 and R 2 form a C 3-C 6 heterocyclic ring with the nitrogen bonded to said R 1 and R 2; R 3 is (see diagramm) in which: R 4 is H, or a C 1-C 6 alkyl, C 2-C 6 alkenyl, C 3-C 6 cycloalkyl or C 3-C 6 cycloalkenyl; R 5 is a C 1-C 6 alkyl, C 1-C 6 alkoxy, or C 2-C 6 alkyl ether which is unsubstituted or substituted with one or more of hydroxyl, phenyl, phenyloxy, or fluorine, or R 5 is NR 7R 8, or C(O)NR 7R 8 in which R 7 and R 8 are independently selected from H, a C 1-C 6 alkyl, C 2-C 6 alkenyl, C 3-C 6 cycloalkyl, or C 3-C 6 cycloalkenyl group; R 6 is H, or a C 1-C 6 alkyl, C 2-C 6 alkenyl, C 3-C 6 cycloalkyl, or C 3-C 6 cycloalkenyl group; and n is 0, 1 or 2; or a pharmaceutically acceptable salt thereof. 2. The compound according to claim 1, wherein R 3 is (see diagramm) 3. The compound according to any one of claims 1 or 2, wherein R 5 is a linear C 5 alkyl group. 4. The compound according to any one of claims 1-3, wherein R 1 is a cyclopropyl group and R 2 is H. 5. The compound according to any one of claims 1-4, wherein R 4 is a C3 isopropyl group. 6. The compound according to any one of claims 1-5, wherein n is 1. 7. The compound according to claim 1, wherein the compound has the structure: (see diagramm) 8. The compound according to claim 1, wherein the compound has a structure selected from the group consisting of: (see diagramm) 9. A compound having a structure selected from the group consisting of: (see diagramm) ; and 10. A composition comprising a compound according to any one of claims 1-9 and a pharmaceutically acceptable carrier. 11. The composition of claim 10, wherein said composition is in the form of an injectable dosage, an oral dosage, an oil-in-water emulsion, or an anhydrous emulsion. 12. The composition of claim 10, wherein said composition comprises a cyclodextrin. 13. The composition of claim 10, further comprising an anesthetic agent. 14. A kit for providing analgesia to a subject, comprising a compound according to any one of claims 1-9 and a delivery device to administer said compound to the subject. 15. Use of a compound according to any one of claims 1-9 for the manufacture of a medicament for providing analgesia in a subject. 16. A compound according to any one of claims 1-9 for use in providing analgesia in a subject. 17. Use of a compound according to any one of claims 1-9 for the manufacture of a medicament for reducing fever in a subject. 18. A compound according to any one of claims 1-9 for use in reducing fever in a subject. 19. A method of providing an arachidonic acid (AA) analog, comprising the steps of : (see diagramm) 20. A method of providing an arachidonic acid (AA) analog, comprising the steps of : (see diagramm)
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