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Claims for Patent: 5,045,317

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Claims for Patent: 5,045,317

Title: Enhancing the cutaneous penetration of pharmacologically active agents
Abstract:Method and compositions for enhancing the cutaneous penetration of topically or transdermally delivered pharmacologically active agent. The compositions include various urethane compounds as permeation enhancers, the urethane compounds formed from reaction of a monomeric organic diisocyanate with a hydroxy- or hydroxy/alkoxy-terminated linear alkylene or polyalkylene glycol or polyether.
Inventor(s): Chess; Samuel (Newport Beach, CA), McCullough; Jerry L. (Irvine, CA), Weinstein; Gerald D. (Irvine, CA)
Assignee: The Regents of the University of California (Alameda, CA)
Application Number:07/566,567
Patent Claims: 1. A composition for achieving enhanced cutaneous penetration of a dermally applied pharmacologically active agent, comprising:

(a) a therapeutically effective amount of a pharmacologically active agent; and

(b) a hydroxy-terminated urethane penetration enhancing compound having the formula: ##STR4## wherein: R is an alkylene or alkenylene radical containing from one to about 20 carbon atoms; or a cycloalkylene or cycloalkenylene radical containing from about 5 to about 10 carbon atoms, or a mononuclear or fused ring arylene radical containing from about 6 to about 10 carbon atoms, unsubstituted or substituted with one or more lower alkyl, lower alkoxy, lower alkoxy-substituted lower alkyl, nitro or amino groups or halogen atoms;

R.sup.1 is the same or different alkylene or alkenylene radical;

m is an integer selected so as to provide an (O--R.sup.1) moiety having a molecular weight of from about 40 to about 6,000; and

n and n' are the same or different integer of from 0 to 30, inclusive, correlated with m so as to provide a hydroxy-terminated urethane compound having a molecular weight of up to about 200,000.

2. The composition of claim 1, wherein each of n and n' is 0.

3. The composition of claim 1, wherein m is an integer selected so as to provide an (O--R.sup.1) moiety having a molecular weight of from about 40 to about 6000, correlated with n and n' so as to provide a hydroxy-terminated urethane penetration enhancing compound having a molecular weight of from about 220 to about 37,000.

4. The composition of claim 1, wherein m is an integer selected so as to provide an (O--R.sup.1) moiety having a molecular weight of from about 400 to about 2000, correlated with n and n' so as to provide a hydroxy-terminated urethane penetration enhancing compound having a molecular weight of from about 1000 to about 15,000.

5. The composition of claim 4 further containing a topical carrier.

6. The composition of claim 5 wherein the topical carrier comprises a liquid or nonliquid carrier, a gel, a cream, an ointment, a lotion, an aerosol or an emulsifier.

7. The composition of claim 6 wherein the hydroxy-terminated urethane penetration enhancing compound is present in an amount of from about 3 wt. % to about 90 wt. % of the composition.

8. The composition of claim 6 wherein the hydroxy-terminated urethane penetration enhancing compound is present in an amount of from about 10 wt. % to about 25 wt. % of the composition.

9. The composition of claim 8 wherein the pharmacologically active agent is methotrexate.

10. The composition of claim 9 wherein the topical carrier is a cream.

11. The composition of claim 9 wherein the topical carrier is an ointment.

12. The composition of claim 8 wherein the pharmacologically active agent is a steroid.

13. A composition of claim 12 wherein the steroid is hydrocortisone or a hydrocortisone derivative.

14. The method of claim 13 wherein the topical carrier is a cream.

15. A method for achieving enhanced penetration of a pharmacologically active agent, comprising applying to the skin, hair or other epithelial surface a composition containing:

(a) a locally administrable topical composition containing a topical carrier; and

(b) a hydroxy-terminated urethane compound having the formula: ##STR5## wherein: R is an alkylene or alkenylene radical containing from one to about 20 carbon atoms; or a cycloalkylene or cycloalkenylene radical containing from about 5 to 10 carbon atoms, or a mononuclear or fused ring arylene radical containing from about 6 to about 10 carbon atoms, unsubstituted or substituted with one or more lower alkyl, lower alkoxy, lower alkoxy-substituted lower alkyl, nitro or amino groups or halogen atoms;

R.sup.1 is the same or different alkylene or alkenylene radical;

m is an integer selected to as to provide an (O--R.sup.1) moiety having a molecular weight of from about 40 to about 6,000; and

n and n' are the same or different integer of from 0 to 30, inclusive, correlated with m so as to provide a hydroxy-terminated urethane compound having a molecular weight of from about 220 to about 200,000.

16. The method of claim 15 wherein each of n and n' is 0.

17. The method of claim 15 wherein m is an integer selected so as to provide an --O--R.sup.1 -- moiety having a molecular weight of from about 40 to about 6000, correlated with n and n' so as to provide a hydroxy-terminated urethane penetration enhancing compound having a molecular weight of from about 220 to about 37,000.

18. The method of claim 15, wherein m is an integer selected so as to provide an --O--R.sup.1 -- moiety having a molecular weight of from about 400 to about 2000, correlated with n and n' so as to provide a hydroxy-terminated urethane penetration enhancing compound having a molecular weight of from about 1000 to about 15000.

19. The method of claim 18, wherein the topical carrier comprises a liquid or nonliquid carrier, a gel, a cream, an ointment, a lotion, an aerosol or an emulsifier.

20. The method of claim 19 wherein the hydroxy-terminated urethane penetration enhancing compound is present in an amount of from about 3 wt. % to about 90 wt. % of the composition.

21. The method of claim 19, wherein the hydroxy-terminated urethane penetration enhancing compound is present in an amount of from about 10 wt. % to about 25 wt. % of the composition.

22. The method of claim 21, wherein the pharmacologically active agent is methotrexate.

23. The method of claim 21, wherein the topical carrier is a cream.

24. The method of claim 21 wherein the topical carrier is an ointment.

25. The method of claim 19, wherein the pharmacologically active agent is a steroid.

26. The method of claim 25 wherein the steroid is hydrocortisone or a hydrocortisone derivative.

27. The method of claim 26 wherein the topical carrier is a cream.

28. A composition for achieving enhanced penetration when applied to hair or nails comprising:

(a) an effective amount of a hair or nail medicant or care agent;

(b) a topical carrier up to about 75 wt. % of the composition; and

(c) a permeation enhancer in an amount from about 5 wt. % to about 25 wt. % of the composition and effective to enhance the penetration of the hair or nail medicant or hair agent, the enhancer being a hydroxy-terminated urethane compound having the formula: ##STR6## wherein: R is an alkylene or alkenylene radical containing from one to about 20 carbon atoms; or a cycloalkylene or cycloalkenylene radical containing from about 5 to about 10 carbon atoms, or a mononuclear or fused ring arylene radical containing from about 6 to about 10 carbon atoms, unsubstituted or substituted with one or more lower alkyl, lower alkoxy, lower alkoxy-substituted lower alkyl, nitro or amino groups or halogen atoms;

R.sup.1 is the same or different alkylene or alkenylene radical;

m is an integer selected so as to provide an (O--R.sup.1) moiety having a molecular weight of from about 40 to about 6,000; and

n and n' are the same or a different integer of from 0 to 30, inclusive, correlated with m so as to provide a hydroxy-terminated urethane compound having a molecular weight of from about 220 to about 200,000.

29. The composition as in claim 28 wherein the hair or nail medicant or care agent includes cutaneous growth enhancers, colorants or mascaras.
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