Delivery of immune response modifier compounds

• US 8,961,477 B2
• Filed: 08/25/2004
• Issued: 02/24/2015
• Est. Priority Date: 08/25/2003
• Status: Active Grant

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Wolter, James T., Kedl, Ross M.
• Primary Examiner(s): Tran, Susan
• Assistant Examiner(s): CRAIGO, WILLIAM A
• Application Number:
  US10/595,073
• Publication Number:
  US 20060195067A1
• Time in Patent Office: 3,835 Days
• Field of Search: None
• US Class Current: 604/265
• CPC Class Codes: A61K 31/4745 condensed with ring systems having nitrogen as a ring hetero atom, e.g. phenantrolines yohimbine derivatives, vinblastine A61K31/475; ergoline derivatives A61K31/48
• CPC Class Codes: A61K 9/0021 Intradermal administration, e.g. through microneedle arrays, needleless injectors mechanical aspects A61M
• CPC Class Codes: A61M 2037/0046 Solid microneedles
• CPC Class Codes: A61M 37/0015 by using microneedles
• CPC Class Codes: A61P 17/00 Drugs for dermatological disorders
• CPC Class Codes: A61P 17/12 Keratolytics, e.g. wart or anti-corn preparations
• CPC Class Codes: A61P 31/12 Antivirals
• CPC Class Codes: A61P 35/00 Antineoplastic agents

Abstract

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

Claims

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 μ

m.

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 μ

m.

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 μ

m.

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.