.

Pharmaceutical Business Intelligence

  • Anticipate P&T budget requirements
  • Evaluate market entry opportunities
  • Find generic sources and suppliers
  • Predict branded drug patent expiration

► Plans and Pricing

Upgrade to enjoy subscriber-only features like email alerts and data export. See the Plans and Pricing

DrugPatentWatch Database Preview

Details for Patent: 5,736,553

« Back to Dashboard

Details for Patent: 5,736,553

Title: Topical formulations and transdermal delivery systems containing 1-isobutyl-1H-imidazo[4,5-C]quinolin-4-amine
Abstract:Pharmaceutical formulations and adhesive-coated sheet materials for the topical and/or transdermal delivery of 1-isobutyl-1H-imidazo[4,5-c]-quinolin-4-amine, including creams, ointments and pressure-sensitive adhesive compositions. Pharmacological methods of using the formulations and the adhesive-coated sheet materials of the invention in the treatment of viral infections.
Inventor(s): Wick; Steven M. (Mahtomedi, MN), Schultz; Helen Jensen (Falcon Heights, MN), Nelson; Gregory R. (Hudson, MN), Mitra; Amit K. (Woodbury, MN), Berge; Stephen M. (Shoreview, MN)
Assignee: Riker Laboratories, Inc. (St. Paul, MN)
Filing Date:May 31, 1995
Application Number:08/471,440
Claims:1. A substantially non-irritating pharmaceutical formulation for topical and/or transdermal administration of 1 -isobutyl- 1H-imidazo[4,5 -c]quinolin-4-amine, which formulation comprises:

(a) a therapeutically effective amount of 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine;

(b) a pharmaceutically acceptable vehicle for said 1-isobutyl-1H-imidazo[4,5c]quinolin-4-amine, which vehicle comprises a fatty acid selected from the group consisting of isostearic acid, oleic acid and a mixture thereof in a total amount of about 3 percent to about 45 percent by weight based on the total weight of said formulation; and

(c) a pressure-sensitive acrylic adhesive copolymer comprising, as a major constituent, a hydrophobic monomeric acrylic or methacrylic acid ester of an alkyl alcohol, the alkyl alcohol containing 4 to 10 carbon atoms, said copolymer being present in an amount of about 55 percent to about 85 percent by weight based on the total weight of said formulation;

said formulation being further characterized in that, when tested according to the hairless mouse skin model the formulation provides a penetration of the agent of at least about 10 percent of the total amount of the agent contained in the formulation in 24 hours.

2. A formulation according to claim 1 in the form of a pressure-sensitive adhesive-coated sheet material comprising:

(a) a flexible backing; and

(b) a pressure-sensitive adhesive coating adhered to one surface of said backing and comprising a mixture of:

i) an acrylic copolymer comprising, as a major constituent, a hydrophobic monomeric acrylic or methacrylic acid ester of an alkyl alcohol, the alkyl alcohol containing 4 to 10 carbon atoms;

ii) 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine in an amount of about 0.5 percent to about 9 percent by weight based on the total weight of said adhesive coating; and

iii) a fatty acid selected from the group consisting of isostearic acid, oleic acid or a mixture thereof, said fatty acid being present in a total amount of about 10 percent to about 40 percent by weight based on the total weight of said adhesive coating.

3. A formulation according to claim 2, wherein said acrylic copolymer comprises A and B Monomers as follows:

A is a hydrophobic monomeric acrylic or methacrylic acid ester of an alkyl alcohol, the alkyl alcohol containing 4 to 10 carbon atoms, said A monomer being present in an amount by weight of about 80 percent to about 98 percent based on the total weight of all monomers in said copolymer; and

B is a reinforcing monomer selected from the group consisting of acrylic acid, methacrylic acid, an alkyl acrylate or methacrylate containing 1 to 3 carbon atoms in the alkyl group, acrylamide, methacrylamide, a lower alkyl-substituted acrylamide, diacetone acrylamide, N-vinyl-2-pyrrolidone, a vinyl ether, a substituted ethylene and a vinyl ester, said B monomer being present in an amount of about 2 percent to about 20 percent based on the total weight of all monomers in said copolymer.

4. A formulation according to claim 3, wherein said adhesive copolymer comprises about 2 percent to about 10 percent by weight of acrylamide and about 90 percent to about 98 percent by weight of isooctyl acrylate, based on the total weight of all monomers in said copolymer.

5. A formulation according to claim 2, wherein said 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine is present in an amount of about 3 percent to about 7 percent by weight based on the total weight of said adhesive coating.

6. A formulation according to claim 2, wherein said adhesive coating further comprises a skin penetration enhancer selected from the group consisting of isopropyl myristate, diisopropyl adipate, ethyl oleate, glyceryl monolaurate, ethyl oleate in combination with glyceryl monolaurate, ethyl oleate in combination with N,N-dimethyldodecylamine-N-oxide, glyceryl monolaurate in combination with N,N-dimethyldodecylamine-N-oxide, and ethyl oleate in combination with both glyceryl monolaurate and N,N-dimethyldodecylamine-N-oxide, said skin penetration enhancer being present in an amount of about 3 percent to about 25 percent by weight based on the total weight of said adhesive coating.

7. A formulation according to claim 6, wherein said skin penetration enhancer(s) is present in a total amount of about 3 percent to about 10 percent by weight based on the total weight of said adhesive coating.

8. A formulation according to claim 6, wherein said skin penetration enhancer comprises ethyl oleate in an amount of about 5 percent to about 8 percent by weight based on the total weight of said adhesive coating, glyceryl monolaurate in an amount between about 1 percent to about 2 percent by weight based on the total weight of said adhesive coating and N,N-dimethyldodecylamine-N-oxide in an amount of about 1 percent to about 3 percent by weight based on the total weight of said adhesive coating.

9. A pressure-sensitive adhesive-coated sheet material comprising:

a) a flexible backing; and

b) a pressure-sensitive adhesive coating adhered to one surface of said flexible backing and comprising a mixture of:

i) a pressure-sensitive acrylic adhesive copolymer comprising about 93 percent by weight, based on the total weight of the copolymer, of isooctyl acrylate and about 7 percent by weight, based on the total weight of the copolymer, of acrylamide;

ii) the compound 1-isobutyl-1H-imidazo[4,5-c]-quinolin-4-amine in an amount by weight of about 5 percent based on the weight of said adhesive coating;

iii) isostearic acid in an amount by weight of about 10 percent based on the weight of said adhesive coating;

iv) oleic acid in an amount by weight of about 20 percent based on the weight of said adhesive coating; and

v) as a skin penetration enhancing combination (1) ethyl oleate in an amount by weight of about 5 percent based on the weight of said adhesive coating (2) glyceryl monolaurate in an amount by weight of about 1.5 percent based on the weight of said adhesive coating; and (3) N,N-dimethyldodecylamine-N-oxide in an amount by weight of about 1 percent based on the weight of said adhesive coating.

10. A formulation according to claim 1, wherein said pressure-sensitive acrylic adhesive copolymer comprises:

about 60 to about 80 percent by weight of hydrophobic monomeric acrylic or methacrylic acid ester of an alkyl alcohol, the alkyl alcohol containing 4 to about 10 carbon atoms, based on the total weight of all monomers in the copolymer;

about 4 to about 9 percent by weight based on the total weight of all monomers in the copolymer of a reinforcing monomer selected from the group consisting of acrylic acid, methacrylic acid, an alkyl acrylate or methacrylate containing 1 to 3 carbon atoms in the alkyl group, acrylamide, methacrylamide, a lower alkyl-substituted acrylamide, diacetone acrylamide and N-vinyl-2-pyrrolidone; and

about 15 to about 35 percent by weight of vinyl acetate based on the total weight of all monomers in the copolymer.

11. A formulation according to claim 1, wherein said pressure-sensitive acrylic adhesive copolymer comprises:

about 70 to about 80 percent by weight of hydrophobic monomeric acrylic or methacrylic acid ester of an alkyl alcohol, the alkyl alcohol containing 4 to about 10 carbon atoms, based on the total weight of all monomers in the copolymer;

about 4 to about 9 percent by weight based on the total weight of all monomers in the copolymer of a reinforcing monomer selected from the group consisting of acrylic acid, methacrylic acid, an alkyl acrylate or methacrylate containing 1 to 3 carbon atoms in the alkyl group, acrylamide, methacrylamide, a lower alkyl-substituted acrylamide, diacetone acrylamide and N-vinyl-2-pyrrolidone; and

about 15 to about 25 percent by weight of vinyl acetate based on the total weight of all monomers in the copolymer.

12. A formulation according to claim 10 in the form of a pressure-sensitive adhesive-coated sheet material comprising:

(a) a flexible backing; and

(b) a pressure-sensitive adhesive coating adhered to one surface of said backing and comprising a mixture of:

i) an acrylic copolymer comprising:

about 60 to about 80 percent by weight of hydrophobic monomeric acrylic or methacrylic acid ester of an alkyl alcohol, the alkyl alcohol containing 4 to about 10 carbon atoms, based on the total weight of all monomers in the copolymer;

about 4 to about 9 percent by weight based on the weight of all monomers in the copolymer of a reinforcing monomer selected from the group consisting of acrylic acid, methacrylic acid, an alkyl acrylate or methacrylate containing 1 to 3 carbon atoms in the alkyl group, acrylamide, methacrylamide, a lower alkyl-substituted acrylamide, diacetone acrylamide and N-vinyl-2-pyrrolidone; and

about 15 to about 35 percent by weight of vinyl acetate based on the total weight of all monomers in the copolymer;

ii) 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine in an amount of about 0.5 percent to about 9 percent by weight based on the total weight of said adhesive coating; and

iii) a fatty acid selected from the group consisting of isostearic acid, oleic acid or a mixture thereof, said fatty acid being present in a total amount of about 10 percent to about 40 percent by weight based on the total weight of said adhesive coating.

13. A formulation according to claim 12, wherein said 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine is present in an amount of about 3 percent to about 7 percent by weight based on the total weight of said adhesive coating.

14. A formulation according to claim 12, wherein said adhesive coating further comprises a skin penetration enhancer selected from the group consisting of isopropyl myristate, diisopropyl adipate, ethyl oleate, glyceryl monolaurate, ethyl oleate in combination with glyceryl monolaurate, ethyl oleate in combination with N,N-dimethyldodecylamine-N-oxide, glyceryl monolaurate in combination with N,N-dimethyldodecylamine-N-oxide, and ethyl oleate in combination with both glyceryl monolaurate and N,N-dimethyldodecylamine-N-oxide, said skin penetration enhancer being present in an amount of about 3 percent to about 25 percent by weight based on the total weight of said adhesive coating.

15. A formulation according to claim 14, wherein said skin penetration enhancer(s) is present in a total amount of about 3 percent to about 10 percent by weight based on the total weight of said adhesive coating.

16. A formulation according to claim 14, wherein said skin penetration enhancer comprises ethyl oleate in an amount of about 5 percent to about 8 percent by weight based on the total weight of said adhesive coating, glyceryl monolaurate in an amount between about 1 percent to about 2 percent by weight based on the total weight of said adhesive coating and N,N-dimethyldodecylamine-N-oxide in an amount of about 1 percent to about 3 percent by weight based on the total weight of said adhesive coating.

17. A method of topical and/or transdermal administration of 1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine for treating a viral disease in a mammal, which method comprises

(1) placing a formulation according to claim 1 on the skin of a mammal; and

(2) allowing said formulation to remain in contact with the skin for a sufficient time to permit an effective amount of the 1-isobutyl-1H-imidazo[4,5-c]-quinolin-4-amine to penetrate the skin to achieve the antiviral effect.

18. A method of topical and/or transdermal administration of 1-isobutyl-1H-imidazo[4,5-c]-quinolin-4-amine to induce interferon biosynthesis in a mammal, which method comprises

(1) placing a formulation according to claim 1 on the skin of a mammal; and

(2) allowing said formulation to remain in effective amount of 1-isobutyl-1H-imidazo[4,5-c]-quinolin-4-amine to penetrate the skin to induce interferon biosynthesis.
« Back to Dashboard

For more information try a trial or see the database preview and plans and pricing

How are People Using DrugPatentWatch?

Drugs may be covered by multiple patents or regulatory protections. All trademarks and applicant names are the property of their respective owners or licensors. Although great care is taken in the proper and correct provision of this service, thinkBiotech LLC does not accept any responsibility for possible consequences of errors or omissions in the provided data. The data presented herein is for information purposes only. There is no warranty that the data contained herein is error free. thinkBiotech performs no independent verifification of facts as provided by public sources nor are attempts made to provide legal or investing advice. Any reliance on data provided herein is done solely at the discretion of the user. Users of this service are advised to seek professional advice and independent confirmation before considering acting on any of the provided information. thinkBiotech LLC reserves the right to amend, extend or withdraw any part or all of the offered service without notice.

`abc