IP Library Granted Patent US 8,961,477
Granted Patent B2
US 8,961,477 · App. 10/595,073 · Granted Feb 24, 2015

Delivery of immune response modifier compounds

Inventors: James T. Wolter (Oakdale, MN); Ross M. Kedl (Denver, CO)
Assignee: 3M Innovative Properties Company
A61K9/0021A61K31/4745A61M37/0015A61M2037/0046
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Quick Facts
Patent No.
US 8,961,477
App. No.
10/595,073
Granted
Feb 24, 2015
Kind
B2
Abstract

Delivery of one or more immune response modifiers (IRMs) across a biological barrier by the use of a microneedle device.

Claims (34)

1. A method for the delivery of an immune response modifier (IRM) compound into or across a biological barrier comprising:

contacting a biological barrier with a microneedle device comprising at least one microneedle;

administering at least one IRM compound selected from the group consisting of amide substituted imidazoquinoline amines, sulfonamide substituted imidazoquinoline amines, urea substituted imidazoquinoline amines, aryl ether substituted imidazoquinoline amines, heterocyclic ether substituted imidazoquinoline amines, amido ether substituted imidazoquinoline amines, sulfonamido ether substituted imidazoquinoline amines, urea substituted imidazoquinoline ethers, thioether substituted imidazoquinoline amines, and 2-propyl[1,3]thiazolo[4,5-c]quinolin-4-amine; a pharmaceutically acceptable salt thereof; and combinations thereof, into or across the biological barrier; and

administering a vaccine;

wherein the vaccine is a protein, glycoprotein, or peptide vaccine; and

wherein the IRM compound is chemically linked to the vaccine and both the IRM compound and the vaccine are coated onto at least a portion of the microneedle device.

2. The method of claim 1 wherein the biological barrier is the skin and the at least one IRM compound is delivered intracutaneously.

3. The method of claim 1 wherein the IRM is a sulfonamide substituted imidazoquinoline amine selected from N-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide, N-[4-(4-amino-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide, and N-[4-(4-amino-2-propyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]methanesulfonamide.

4. The method of claim 1 wherein the IRM is N-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}cyclohexanecarboxamide.

5. The method of claim 1 wherein the IRM is a urea substituted imidazoquinoline amine selected from N-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}-N′-cyclohexylurea, and N-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethyl}-N′-isopropylurea.

6. The method of claim 1 wherein the at least one microneedle penetrates the biological barrier by no more than 500 μm.

7. The method of claim 1 wherein the microneedle device contacts the biological barrier for 30 seconds to 20 minutes.

8. The method of claim 1 wherein he IRM compound has a molecular weight of less than about 1000 daltons.

9. A method for the delivery of an immune response modifier (IRM) compound into or across a biological barrier comprising:

contacting a biological barrier with a microneedle device comprising at least one microneedle;

administering at least one IRM compound selected from the group consisting of N-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}methanesulfonamide; N-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}cyclohexanecarboxamide; N-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}-N′-cyclohexylurea, and N-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethyl}-N′-isopropylurea; a pharmaceutically acceptable salt thereof; and combinations thereof, into or across the biological barrier; and

administering a vaccine;

wherein the vaccine is a protein, glycoprotein, or peptide vaccine; and

wherein both the IRM compound and the vaccine are coated onto at least a portion of the microneedle device.

10. The method of claim 9 wherein the biological barrier is the skin and the at least one IRM compound and the vaccine are delivered intracutaneously.

11. The method of claim 9 wherein the at least one microneedle penetrates the biological barrier by no more than 500 μm.

12. The method of claim 9 wherein the microneedle device contacts the biological barrier for 30 seconds to 20 minutes.

13. The method of claim 9 wherein he IRM compound has a molecular weight of less than about 1000 daltons.

14. A method for the delivery of an immune response modifier (IRM) compound into or across a biological barrier comprising:

contacting a biological barrier with a microneedle device comprising at least one microneedle;

administering at least one IRM compound selected from the group consisting of urea substituted imidazoquinoline amines, sulfonamido ether substituted imidazoquinoline amines, and urea substituted imidazoquinoline ethers; a pharmaceutically acceptable salt thereof; and combinations thereof, into or across the biological barrier; and

administering a vaccine;

wherein the vaccine is a protein, glycoprotein, or peptide vaccine; and

wherein the IRM compound is chemically linked to the vaccine and both the IRM compound and the vaccine are coated onto at least a portion of the microneedle device.

15. The method of claim 14 wherein the biological barrier is the skin and the at least one IRM compound is delivered intracutaneously.

16. The method of claim 14 wherein the IRM is a urea substituted imidazoquinoline amine selected from N-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-1,1-dimethylethyl}-N′-cyclohexylurea, and N-{2-[4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethyl}-N′-isopropylurea.

17. The method of claim 14 wherein the at least one microneedle penetrates the biological barrier by no more than 500 μm.

18. The method of claim 14 wherein the microneedle device contacts the biological barrier for 30 seconds to 20 minutes.

19. The method of claim 14 wherein he IRM compound has a molecular weight of less than about 1000 daltons.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 30, 2006
From: WOLTER, JAMES T.; KEDL, ROSS M.
To: 3M INNOVATIVE PROPERTIES COMPANY
Reel/Frame 017219/0527 →
Continuity (2)
Provisional Application 60497628 · Aug 25, 2003
Related Publication 20060195067A1 · Aug 31, 2006