# US 7,745,489 B2 · Compositions and methods for inhibition of phospholipase A2 mediated inflammation

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- Number: US 7,745,489 B2
- Document ID: US7745489B2
- Status: Granted
- Kind: B2
- Application number: 10/506,059
- Filed: 2003-03-07
- Published: 2005-07-07
- Granted: 2010-06-29
- Earliest claimed: 2002-03-07
- Assignees: The Regents of the University of California
- Inventors: Edward Dennis; Tony Yaksh; Karin Killermann Lucas; Camilla Svensson; David A. Six; George Kokotos; Violetta Constantinou-Kokotou
- Web page: https://patentgrep.com/patent/US7745489B2

## CPC

- C07C 235/80: having carbon atoms of carboxamide groups and keto groups bound to the same carbon atom, e.g. acetoacetamides
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07C 233/56: having carbon atoms of carboxamide groups bound to carbon atoms of carboxyl groups, e.g. oxamides
- C07C 237/22: having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated (peptides C07K)
- C07C 271/12: to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07D 207/08: with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D 309/30: Oxygen atoms, e.g. delta-lactones
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Specific, highly potent 2-oxo-amide based inhibitors of phospholipase A2 (PLA2) activity are provided. A role for PLA2 activity in spinally mediated inflammatory processes is established, and a method for treating hyperalgesia and other inflammatory conditions associated with PLA2 activity is provided.

## Claims

### Claim 1

A compound of the formula (I):
wherein:
R1 is an acidic moiety, selected from the group consisting of carboxyl, phosphate, phosphinate, sulfate, and sulfonate; each of R2 and R3 is a moiety independently selected from the group consisting of phenyl, benzyl, and a carbyl having between 1 and 13 carbons, the carbyl being selected from the group consisting of a linear or branched, saturated or unsaturated alkyl, alkenyl, and alkynyl;
n is an integer having a value of 3, m is an integer having a value of 0 to 3, and k is an integer having a value of 0 to 22;
and isomers, enantiomers, and pharmacologically or immunologically acceptable salts thereof.

### Claim 2

A pharmaceutical composition, comprising (4S)-4-[(2-oxododecanoyl)amino]octanoic acid, and a pharmaceutically acceptable carrier.

### Claim 3

A pharmaceutical composition, comprising 4-[(2-oxohexadecanoyl)amino]butanoic acid, and a pharmaceutically acceptable carrier.

### Claim 4

A pharmaceutical composition, comprising 4-[(2-oxooctanoyl)amino]butanoic acid, and a pharmaceutically acceptable carrier.

### Claim 5

A pharmaceutical composition, comprising (4R)-4-[(2-oxododecanoyl)amino]octanoic acid, and a pharmaceutically acceptable carrier.

### Claim 6

A pharmaceutical composition, comprising the compound of formula (II),
and a pharmaceutically acceptable carrier.

### Claim 7

A pharmaceutical composition, comprising the compound of formula (III),
and a pharmaceutically acceptable carrier.

### Claim 8

A pharmaceutical composition, comprising the compound of formula (IV),
and a pharmaceutically acceptable carrier.

### Claim 9

A pharmaceutical composition, comprising the compound of formula (V),
and a pharmaceutically acceptable carrier.

### Claim 10

A pharmaceutical composition, comprising the compound of formula (VI),
and a pharmaceutically acceptable carrier.

### Claim 11

A pharmaceutical composition, comprising the compound of formula (VII),
and a pharmaceutically acceptable carrier.

### Claim 12

A pharmaceutical composition, comprising the compound of formula (VIII),
and a pharmaceutically acceptable carrier.