Compositions for prevention/prophylactic treatment of poison ivy dermatitis

Patent metadata

Field	Value
Publication number	US-10322103-B2
Application number	US-201615563597-A
Country	US
Kind code	B2
Filing date	Jan 12, 2016
Priority date	Apr 3, 2008
Publication date	Jun 18, 2019
Grant date	Jun 18, 2019

Abstract

The present invention, in one or more embodiments, comprises derivatives of 3-n-pentadecylcatechol (poison ivy urushiol saturated congener) and/or 3-n-heptadecyl catechol (poison oak urushiol saturated congener) as compositions for the prevention and/or prophylactic treatment of contact dermatitis caused by poison ivy and poison oak. The present invention is also directed towards processes for making such compounds. Disclosed are compounds which are effective for tolerizing and desensitizing a subject against allergens contained in plants of the Anacardiaceae and Ginkgoaceae families comprising urushiol esters of general formula (IA) [Formula should be entered here] tolerizing and desensitizing mammals, including humans, to allergens contained in plants of the Anacardiaceae and Ginkgoaceae families is attained by administering a formulation containing at least one urushiol ester compound.

First claim

The invention claimed is:

1. Urushiol esters effective for desensitizing a subject against contact dermatitis caused by allergens contained in plants of the Anacardiaceae and Ginkgoaceae families of the following formula (I)

wherein R 1 is an alkyl radical having 11 to 19 carbon atoms, or an unsaturated congener thereof; or mixtures thereof; and R 2 and R 3 are each independently a radical of an amino acid or a combination of amino acids or a radical of a dicarboxylic acid, with the proviso that when R 1 is heptadecyl or pentadecyl R 2 and R 3 cannot be alanine or alanine N-tert-butoxycarbonyl (t-BOC).

2. The urushiol esters of claim 1 , wherein R 1 is pentadecyl, heptadecyl or nonadecyl.

3. The urushiol esters of claim 1 , wherein the esters are esters of amino acids or combinations of amino acids.

4. The urushiol esters of claim 1 , wherein the esters are derived from a dicarboxylic acid.

5. A pharmaceutical formulation comprising at least one urushiol ester effective for desensitizing a subject against contact dermatitis caused by allergens contained in plants of the Anacardiaceae and Ginkgoaceae families of the following formula (I)

wherein R 1 is an alkyl radical having 11 to 19 carbon atoms, or an unsaturated congener thereof; or mixtures thereof; and R 2 and R 3 are each independently a radical of an amino acid or a combination of amino acids or a radical of a dicarboxylic acid, in sesame seed oil and about 2 to 12% by volume benzyl alcohol and about 0 to 10% by volume ethyl alcohol.

6. The pharmaceutical formulation of claim 5 , wherein the composition is adapted to be administered parenterally.

7. The urushiol ester of claim 1 , wherein the urushiol ester is 3-n-pentadecylcatechol-di-4-(4-aminophenyl)-butyrate, 3-n-heptadecylcatechol-di-4-(4-aminophenyl)-butyrate, 3-n-pentadecylcatechol-di-valinylvalinate or 3-n-heptadecylcatechol-di-valinylvalinate.

8. A pharmaceutical formulation according to claim 5 , wherein the urushiol ester is 3-n-pentadecylcatechol-di-4-(4-aminophenyl)-butyrate, 3-n-heptadecylcatechol-di-4-(4-aminophenyl)-butyrate, 3-n-pentadecylcatechol-di-valinylvalinate or 3-n-heptadecylcatechol-di-valinylvalinate.

9. The pharmaceutical formulation of claim 8 , wherein the composition is adapted to be administered parenterally.

10. The pharmaceutical formulation of claim 5 , wherein R 1 is pentadecyl, heptadecyl or nonadecyl.

11. The pharmaceutical formulation of claim 10 , wherein the composition is adapted to be administered parenterally.

12. The pharmaceutical formulation according to claim 5 , wherein the esters are esters of amino acids or combinations of amino acids.

13. The pharmaceutical formulation of claim 12 , wherein the composition is adapted to be administered parenterally.

14. The pharmaceutical formulation according to claim 5 , wherein the at least one urushiol ester is in sesame seed oil and about 2 to 12% by volume benzyl alcohol and about 5 to 10% by volume ethyl alcohol.

15. The pharmaceutical formulation of claim 14 , wherein the composition is adapted to be administered parenterally.

16. The pharmaceutical formulation according to claim 5 , wherein the at least one urushiol ester is an ester of a dicarboxylic acid.

17. The pharmaceutical formulation of claim 16 , wherein the composition is adapted to be administered parenterally.

18. The pharmaceutical formulation according to claim 16 , wherein the at least one urushiol ester is in sesame seed oil and about 2 to 12% by volume benzyl alcohol and about 5 to 10% by volume ethyl alcohol.

19. The pharmaceutical formulation of claim 18 , wherein the composition is adapted to be administered parenterally.

Assignees

• The Univ Of Mississippi
• Univ Mississippi

Inventors

• Elsohly Mahmoud
• Gul Waseem
• Ashfaq Mohammad Khalid

Classifications

• A61P37/08

  Antiallergic agents (antiasthmatic agents A61P11/06; ophthalmic antiallergics A61P27/14) · CPC title

• A61P37/02

  Immunomodulators · CPC title

• A61P37/00

  Drugs for immunological or allergic disorders · CPC title

• A61P29/00

  Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] · CPC title

• C07C237/04

  the carbon skeleton being acyclic and saturated · CPC title