# US 7,608,589 B2 · Peptidyl diacylglycerides

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- Number: US 7,608,589 B2
- Document ID: US7608589B2
- Status: Granted
- Kind: B2
- Application number: 11/459,772
- Filed: 2006-07-25
- Published: 2007-08-23
- Granted: 2009-10-27
- Earliest claimed: 2005-07-25
- Assignees: Therimunex Pharmaceuticals, Inc.
- Inventors: James D. Thacker
- Web page: https://patentgrep.com/patent/US7608589B2

## CPC

- C07K 7/08: having 12 to 20 amino acids (gastrins C07K14/595; somatostatins C07K14/655; melanotropins C07K14/68)
- A61K 9/0019: {Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner (non-active ingredients are additionally classified in A61K47/00)}
- A61K 38/08: Peptides having 5 to 11 amino acids {(A61K38/043 - A61K38/046 take precedence)}
- A61K 38/10: Peptides having 12 to 20 amino acids {(A61K38/043 - A61K38/046 take precedence)}
- A61K 38/17: from animals; from humans {(enzyme inhibitors A61K38/005)}
- A61P 31/04: Antibacterial agents
- A61P 37/04: Immunostimulants
- C07K 7/06: having 5 to 11 amino acids
- C07K 14/00: Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K 14/001: {by chemical synthesis}
- C07K: PEPTIDES (peptides in foodstuffs A23; obtaining protein compositions for foodstuffs, working-up proteins for foodstuffs A23J; preparations for medicinal purposes A61K; peptides containing beta-lactam rings C07D; cyclic dipeptides not having in their molecule any other peptide link than those which form their ring, e.g. piperazine-2,5-diones, C07D; ergot alkaloids of the cyclic peptide type C07D519/02; macromolecular compounds having statistically distributed amino acid units in their molecules, i.e. when the preparation does not provide for a specific; but for a random sequence of the amino acid units, homopolyamides and block copolyamides derived from amino acids C08G69/00; macromolecular products derived from proteins C08H1/00; preparation of glue or gelatine C09H; single cell proteins, enzymes C12N; genetic engineering processes for obtaining peptides C12N15/00; compositions for measuring or testing processes involving enzymes C12Q; investigation or analysis of biological material G01N33/00)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

Peptide and peptides that may be covalently linked to a lipid and methods of using such peptides and lipopeptides to prevent or treat disease are disclosed herein.

## Claims

### Claim 1

A method of stimulating an immune response in a subject in need thereof comprising:
administering an effective amount of an agent comprising a peptidyl glyceride of formula (I):
wherein X1 is a peptide of amino acid sequence YTSHNLCXCLNHSR (SEQ ID NO: 4) wherein X can be any natural amino acid attached to the glyceride (I) to form an ester with the C-terminal arginine (R), X2 is arachidonoyl, and X3 is stearoyl; and
stimulating an immune response in the subject.

### Claim 2 (depends on 1)

The method of claim 1, wherein stimulating an immune response further comprises stimulating an innate immune response.

### Claim 3 (depends on 1)

The method of claim 1, wherein stimulating an immune response further comprises stimulating tissue resident immune cells.

### Claim 4 (depends on 3)

The method of claim 3, wherein the tissue resident immune cells are selected from γδ T cells, monocytes, NK cells, neutrophils, CD5+ B-cells and combinations thereof.

### Claim 5 (depends on 3)

The method of claim 3, wherein the tissue resident immune cells are stimulated when contacted by the peptide.

### Claim 6 (depends on 1)

The method of claim 1, wherein stimulating an immune response comprises stimulating an immune response for at least about 3 days following administration.

### Claim 7 (depends on 1)

The method of claim 1, wherein the compound is substantially deposited in a fatty tissue of the subject.

### Claim 8 (depends on 1)

The method of claim 1, wherein administrating the agent comprises administering the agent by a method selected from enteral, parenteral, topical, mammary infusion and combinations thereof.

### Claim 9 (depends on 1)

The method of claim 1, wherein the agent is administered prior to exposure to a disease forming agent.

### Claim 10 (depends on 6)

The method of claim 6, wherein infection is substantially prevented.

### Claim 11 (depends on 1)

The method of claim 1, wherein the agent is administered prior to infection.

### Claim 12 (depends on 1)

The method of claim 1, wherein the agent is administered following exposure to a disease forming agent.

### Claim 13 (depends on 1)

The method of claim 1, wherein the agent is administered following infection.

### Claim 14

A compound comprising a peptide of amino acid sequence YTSHNLCXCLNHSR (SEQ ID NO: 4) or an inversion thereof, wherein X can be any natural amino acid.

### Claim 15 (depends on 14)

The compound of claim 14, wherein the peptide is covalently attached to a lipid.