US008486998B2

(12) United States Patent Elsohly et a1. (54)

(75) Inventors: Mahmoud A. Elsohly, Oxford, MS

(US); Waseem Gul, Oxford, MS (US); Mohammad Khalid Ashfaq, Oxford, MS (U S); Susan P. Manly, Oxford, MS

(Us) (73) Assignee: The University of Mississippi, University, MS (U S) Notice:

Subject to any disclaimer, the term of this patent is extended or adjusted under 35

U.S.C. 154(b) by 56 days.

(21) App1.No.:

12/936,204

(22) PCT Filed:

Apr. 3,2009

(86)

PCT N0.:

PCT/US2009/039472

§ 371 (0)0), (2), (4) Date:

Dec. 14, 2010

(87)

US 8,486,998 B2 Jul. 16, 2013

Epstein, W. L. 1994. Occupational poison ivy and oak dermatitis.

COMPOSITIONS FOR PREVENTION/PROPHYLACTIC TREATMENT OF POISON IVY DERMATITIS

(*)

(10) Patent N0.: (45) Date of Patent:

PCT Pub. No.: WO2009/146131

Dermatol Clin.12:511-516.

Gladman, A. C. 2006, Toxicodendron Dermatitus: Poison Ivy, Oak and Sumac. Wilderness and Enviromental Medicine, 17: 120-128. Symes, W. F. and Dawson, CR. 1954. Poison ivy urushiol. J. Am. Chem. Soc. 76:2959-2963.

Sunthankar, SV. and Dawson, CR. 1954. The structural identi?ca tion of the ole?nic components of Japanese Lac urushiol. J. Am. Chem. Soc. 76:5070-5074. MarkiewitZ, K. H. and Dawson, C. R. 1965. On the Isolation of

Allergenically Active Components of the Toxic Principle of Poison Ivy. J. Org. Chem. 30:1610-1613. Billets, S., Craig, J. C., Corbett, M. D. and Vickery, J. F. 1976. Component analysis of urushiol content of poison ivy and poison oak. Phytochemistry. 15: 533-535. Tyrnan, J. H. P. 1996. Studies in Organic Chemistry 52. p. 465-546. In Synthetic and Natural Phenols. Elsevier.

Xia, Z., Miyakoshi, T. andYoshida, T. 2004. Lipoxygenase-catalysed polymerization of phenolic lipids suggests a new mechanism for allergic contact dermatitis induced by urushiol and its analogs. Bio chemical and Biophysical Research Communication. 315:704-709. Byck, J. S. and Dawson, C. R. 1968. Assay of protein-quinone cou

pling involving compounds structurally related to the active principal ofpoison ivy. Anal. Biochem. 25:123-135. BeneZra, C. 1990. Molecular recognition in allergic contact dermatitis to natural products. Pure Appl. Chem. 62: 1251-1258. Kalish, R. S. 1991, Recent developments in the pathogenesiss of allergic contact dermatitis. Arch. Dermatol. 127:1558-1563.

PCT Pub. Date: Dec. 3, 2009

(Continued) (65)

Prior Publication Data

US 2011/0086900 A1

Apr. 14, 2011

Related US. Application Data

(60) Provisional application No. 61/042,118, ?led on Apr. 3, 2008. (51)

Int. Cl. A61K 31/215 C0 7D 205/00 (52) US. Cl. USPC

(58)

(2006.01) (2006.01)

........................................... .. 514/535; 560/20

Field of Classi?cation Search USPC

........................................... .. 560/20; 514/535

Primary Examiner * Shawquia Young (74) Attorney, Agent, or Firm * HershkovitZ & Associates, LLC

(57)

ABSTRACT

The present invention, in one or more embodiments, com

prises water-soluble derivatives of 3-n-pentadecylcatechol (poison ivy urushiol saturated congener) and/or 3-n-heptade cylcatechol (poison oak urushiol saturated congener) as com positions 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 mak ing such compounds. Disclosed are compounds which are

See application ?le for complete search history.

effective for toleriZing and desensitiZing a subject against allergens contained in plants of the Anacardiaceae and Gink

References Cited

goaceae families comprising water soluble urushiol esters of

(56)

general formula (I) ToleriZing and desensitiZing mammals, PUBLICATIONS Eisohly, et al. Document No. 99:175452 (1983).*

Praiser, D. M., Ceilley, R. I., Le?1 31kg

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Test #3, (Group II)

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Group IV, Treated with ELl-21-57-3 and then challenged with urushiol

(Skin reaction at 72 hrs)

FIG. 6'