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(12) United States Patent (10) Patent No.: US 8,980,942 B2 Stinchcomb Et Al

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(12) United States Patent (10) Patent No.: US 8,980,942 B2 Stinchcomb Et Al USOO8980942B2 (12) United States Patent (10) Patent No.: US 8,980,942 B2 Stinchcomb et al. (45) Date of Patent: Mar. 17, 2015 (54) PRODRUGS OF (58) Field of Classification Search TETRAHYDROCANNABINOL, CPC ............................ C07D 31 1/80; A61K31/352 COMPOSITIONS COMPRISING PRODRUGS USPC ........................................... 549/390; 514/454 OF TETRAHYDROCANNABINOLAND See application file for complete search history. METHODS OF USING THE SAME (75) Inventors: Audra Lynn Stinchcomb, Lexington, (56) References Cited KY (US); Miroslaw Jerzy Golinski, Lexington, KY (US); Dana Carmel U.S. PATENT DOCUMENTS Hammell, Georgetown, KY (US); 4,327,028 A 4, 1982 Kaplan Jeffrey Lynn Howard, Lexington, KY 4,933,363 A 6/1990 ElSohly (US) 5,684,161 A 11/1997 Imoto (73) Assignee: Zynerba Pharmaceuticals, Inc., (Continued) Radnor, PA (US) FOREIGN PATENT DOCUMENTS (*) Notice: Subject to any disclaimer, the term of this CA 96.7971 A 5, 1975 patent is extended or adjusted under 35 FR 2.081512 12/1971 U.S.C. 154(b) by 4 days. (Continued) (21) Appl. No.: 13/555,741 OTHER PUBLICATIONS (22) Filed: Jul. 23, 2012 A.J. Hampson et al., Cannabidiol and (-)A9-tetrahydrocannabinol are Neuroprotective Antioxidants, 95 Proceedings Natl Acad. Sci (65) Prior Publication Data ences 8268-73 (1998). US 2012/0289484A1 Nov. 15, 2012 (Continued) Related U.S. Application Data Primary Examiner — Noble Jarrell (62) Division of application No. 12/326,036, filed on Dec. Assistant Examiner — Raymond Covington 1, 2008, now Pat. No. 8,227,627. (74) Attorney, Agent, or Firm — Foley & Lardner LLP (60) Provisional application No. 60/991,555, filed on Nov. 30, 2007, provisional application No. 61/037,568, filed on Mar. 18, 2008. (57) ABSTRACT Described herein are A-THC prodrugs, methods of making (51) Int. Cl. A-THC prodrugs, formulations comprising A-THC pro CO7D 3II/80 (2006.01) drugs and methods of using A-THC. One embodiment A6 IK3I/35 (2006.01) described herein relates to the transdermal administration of A6 IK3I/352 (2006.01) a A-THC prodrug for treating and preventing diseases and/or (52) U.S. Cl. disorders. CPC ............ C07D 31 1/80 (2013.01); A61K3I/352 (2013.01) USPC ........................................... 514/454; 549/390 17 Claims, 6 Drawing Sheets ethic a rest at it is a is rary 23 i US 8,980,942 B2 Page 2 (56) References Cited Franjo Grotenhermen, Clinical Pharmacokinetics of Cannabinoids, 3:1 J. Cannabis Therapeutics 3-51 (2003). U.S. PATENT DOCUMENTS Franjo Grotenhermen, Pharmacokinetics and Pharmacodynamics of Cannabinoids, 42:4 Clinical Pharmacokinetics 327-360 (2003). 8,227,627 B2* 7/2012 Stinchcomb et al. ......... 549,390 G. Mucioli and D. Lambert, Current Knowledge on the Antagonists 2006/0264647 A1 11/2006 Field et al. and Inverse Agonists of Cannabinoid Receptors, 12 Current Medici 2008/0275237 A1 11/2008 Arslantas et al. nal Chemistry 1361-94 (2005). Gennaro, Alfonso, Remington: The Science and Practice of Phar FOREIGN PATENT DOCUMENTS macy, 20th ed., pp. 842-843 (2000). 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