# US 4,395,394 A · Use of lipid amines formulated with fat or lipid emulsions as vaccine adjuvants

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- Number: US 4,395,394 A
- Document ID: US4395394A
- Status: Granted
- Kind: A
- Application number: 06/314,240
- Filed: 1981-10-23
- Granted: 1983-07-26
- Earliest claimed: 1979-10-26
- Assignees: Pfizer Inc.
- Inventors: John S. Wolff, III; George R. Hemsworth; Keith E. Jensen
- Web page: https://patentgrep.com/patent/US4395394A

## CPC

- A61K 31/13: Amines {(A61K31/04 takes precedence)}
- A61K 31/135: having aromatic rings {, e.g. ketamine, nortriptyline (methadone A61K31/137)}
- A61K 39/39: characterised by the immunostimulating additives, e.g. chemical adjuvants
- B82Y 5/00: Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
- A61K 2039/55511: {Organic adjuvants}
- A61K 2039/55566: {Emulsions, e.g. Freund's adjuvant, MF59}
- Y02A 50/30: Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
- 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)
- B82Y: SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE

## Abstract

N,N-higher alkyl-N',N'-bis(2-hydroxyethyl)-propanediamines and N,N-higher alkyl-xylylenediamines formulated with fat or lipid emulsions are useful as vaccine adjuvants of low toxicity. These compositions are useful in conjunction with known immunological substances in order to induce or enhance the immunogenic response. Preferred compositions employ N,N-higher alkyl-N',N'-bis(2-hydroxyethyl)propanediamines, particularly N,N-dioctadecyl-N',N'-bis(2-hydroxyethyl)-propanediamine in Intralipid.

## Claims

### Claim 1

A method of inducing or enhancing the immunogenic response of an antigen in man or an animal which comprises parenteral co-administration to said man or animal of said antigen and a pharmaceutical composition which comprises a compound of the formula ##STR2## or a pharmaceutically acceptable acid addition salt thereof wherein R.sub.1 and R.sub.2 are each alkyl of 12 to 20 carbon atoms;
and a lipid or fat emulsion comprising about 10% vegetable oil and about 1.2% phospholipids;
in an amount to effectively induce or enhance the immunogenic response of said antigen.

### Claim 2 (depends on 1)

A method of claim 1 wherein the compound is of the formula (I).

### Claim 3 (depends on 2)

A method of claim 2 wherein the compound is N,N-dioctadecyl-N,N'-bis(2-hydroxyethyl)propanediamine.

### Claim 4 (depends on 1)

A method of claim 1 wherein the lipid or fat emulsion comprises 10% soybean oil and 1.2% egg yolk phospholipids.

### Claim 5 (depends on 2)

A method of claim 2 wherein the lipid or fat emulsion comprises 10% soybean oil and 1.2% egg yolk phospholipids.

### Claim 6 (depends on 3)

A method of claim 3 wherein the lipid or fat emulsion comprises 10% soybean oil and 1.2% egg yolk phospholipids.

### Claim 7 (depends on 1)

A method of claim 1 wherein the antigen is a vaccine.

### Claim 8 (depends on 3)

A method of claim 3 wherein the antigen is a vaccine.

### Claim 9 (depends on 6)

A method of claim 6 wherein the antigen is a vaccine.

### Claim 10 (depends on 6)

A method of claim 6 wherein the antigen is derived from bacteria or rickettsia.

### Claim 11 (depends on 6)

A method of claim 6 wherein the antigen is pollen, dust or danders.

### Claim 12 (depends on 6)

A method of claim 6 wherein the antigen is a poison or venom derived from a poisonous insect or snake.