# US 9,518,078 B2 · Disaccharide synthetic lipid compounds and uses thereof

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- Number: US 9,518,078 B2
- Document ID: US9518078B2
- Status: Granted
- Kind: B2
- Application number: 14/391,344
- Filed: 2013-04-12
- Published: 2015-04-23
- Granted: 2016-12-13
- Earliest claimed: 2012-04-12
- Assignees: Avanti Polar Lipids, Inc.; AC Immune SA
- Applicants: Avanti Polar Lipids, Inc.; Ac Immune SA
- Inventors: Walter A Shaw; Stephen W Burgess; Shengrong Li; David T Hickman; Maria Pilar Lopez-Deber
- Web page: https://patentgrep.com/patent/US9518078B2

## CPC

- C07H 13/06: Fatty acids
- A61K 9/127: Synthetic bilayered vehicles, e.g. liposomes or liposomes with cholesterol as the only non-phosphatidyl surfactant
- A61K 39/0007: {Nervous system antigens; Prions}
- A61K 39/39: characterised by the immunostimulating additives, e.g. chemical adjuvants
- A61K 2039/55555: {Liposomes; Vesicles, e.g. nanoparticles; Spheres, e.g. nanospheres; Polymers}
- A61K 2039/55572: {Lipopolysaccharides; Lipid A; Monophosphoryl lipid A}
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)
- 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)

## Abstract

Essentially pure compounds of the formulas (I) to (XXV) are provided. Compositions and methods for enhancing or stimulating an immune response are also provided. The compounds, provided are advantageous in that the compounds are essentially pure and free from contaminants encountered when such compounds are purified from natural sources.

## Claims

### Claim 1

An essentially pure compound having the structure:
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The essentially pure compound of claim 1, wherein the compounds is at least 95% pure with respect to the synthetic disaccharide lipid compounds as measured on a weight basis.

### Claim 3

An essentially pure compound having the structure:
or a pharmaceutically acceptable salt thereof.

### Claim 4 (depends on 3)

The essentially pure compound of claim 3, wherein the compounds is at least 95% pure with respect to the synthetic disaccharide lipid compounds as measured on a weight basis.

### Claim 5

A pharmaceutical composition comprising:
a. a pharmaceutically acceptable carrier;
b. an optional antigen; and
c. an essentially pure synthetic disaccharide lipid compound having the structure;
or a combination of the foregoing
or a pharmaceutically acceptable salt thereof.

### Claim 6 (depends on 5)

The pharmaceutical composition of claim 5, wherein the compound is at least 95% pure with respect to the synthetic disaccharide lipid compound as measured on a weight basis.

### Claim 7 (depends on 5)

The pharmaceutical composition of claim 5, wherein the compounds is at least 99% pure with respect to the synthetic disaccharide lipid compound as measured on a weight basis.

### Claim 8 (depends on 5)

The pharmaceutical composition of claim 5, wherein the composition comprises an antigen.

### Claim 9 (depends on 5)

The pharmaceutical composition of claim 5, wherein the composition further comprises a second adjuvant.

### Claim 10 (depends on 9)

The pharmaceutical composition of claim 9, wherein the second adjuvant is a mono-phosphorylated hexaacyl disaccharide.

### Claim 11 (depends on 5)

The pharmaceutical composition of claim 5, wherein the composition is a vaccine composition.

### Claim 12 (depends on 5)

The pharmaceutical composition of claim 5, wherein the composition is useful in stimulating or enhancing an immune response in a subject.

### Claim 13 (depends on 5)

The pharmaceutical composition of claim 5, wherein the pharmaceutically acceptable carrier is a liposome.