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(12) United States Patent (10) Patent No.: US 8,318,728 B2 Chong (45) Date of Patent: Nov

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(12) United States Patent (10) Patent No.: US 8,318,728 B2 Chong (45) Date of Patent: Nov US008318728B2 (12) United States Patent (10) Patent No.: US 8,318,728 B2 Chong (45) Date of Patent: Nov. 27, 2012 (54) COMPOUNDS AND COMPOSITIONS FOR (56) References Cited TREATING CHEMICAL WARFARE AGENT INDUCED INURES U.S. PATENT DOCUMENTS 4,297,494 A 10/1981 Groman et al. (75) Inventor: Jayhong A. Chong, Brookline, MA (US) 4,871,742 A 10, 1989 Bonne et al. 4,960,773. A 10, 1990 KorbonitSet al. 5,068,236 A 11/1991 Suzuki et al. (73) Assignee: Hydra Biosciences, Inc., Cambridge, 6,545,002 B1 4/2003 Linden et al. MA (US) 6,608,069 B1 8/2003 Daluge et al. 7,135,475 B2 11/2006 Dunten et al. (*) Notice: Subject to any disclaimer, the term of this 2004.0053973 A1 3/2004 Ohkawa et al. 2006, O247226 A1 11/2006 Himmelsbach et al. patent is extended or adjusted under 35 2007/OO72851 A1 3/2007 Buchanan et al. U.S.C. 154(b) by 371 days. 2007/0219.222 A1 9, 2007 Moran et al. (21) Appl. No.: 12/466,187 FOREIGN PATENT DOCUMENTS WO 2007073505 A2 6, 2007 (22) Filed: May 14, 2009 OTHER PUBLICATIONS (65) Prior Publication Data Cassillas et al., J. Appl. Toxicol. 20, S145-S151 (2000).* US 2012/O108613 A1 May 3, 2012 International Search Report dated Jun. 14, 2010 for related applica tion PCT/US 10/35005. European Agency for the Evaluation of Medicinal Products. EMEA Related U.S. Application Data CPMP Guidance Document on the Use of Medicinal Products for the (60) Provisional application No. 61/127,666, filed on May Treatment of Patients Exposed to Terrorist Attacks with Chemical 14, 2008, provisional application No. 61/127,664, Agents. 2003, pp. 2-17. <www.ema.europa.eu/pdfs/human/ chemicalterrorism? 125503en.pdf>. filed on May 14, 2008, provisional application No. International Search Report dated Jun. 2, 2010 for related application 61/127,665, filed on May 14, 2008, provisional PCT/US 09.43971. application No. 61/127,723, filed on May 14, 2008, International Search Report dated Jun. 16, 2009 for International provisional application No. 61/127,787, filed on May Application No. PCT/US09/43985, 14, 2008, provisional application No. 61/127,790, filed on May 14, 2008, provisional application No. * cited by examiner 61/127,682, filed on May 14, 2008. Primary Examiner — Timothy Thomas (51) Int. Cl. Assistant Examiner — Jean Cornet A6 IK3I/54 (2006.01) (74) Attorney, Agent, or Firm — Lando & Anastasi LLP (52) U.S. Cl. .................. 514/227.8: 514/263.2: 514/371; 514/263.3: 514/367: 514/375; 514/262.1; (57) ABSTRACT 514/393 Compounds and compositions for treating injuries caused by (58) Field of Classification Search ............... 514/263.2, exposure to chemical warfare agents are described herein. 514/371, 263,367,375,262.1, 393 See application file for complete search history. 4 Claims, No Drawings US 8,318,728 B2 1. 2 COMPOUNDS AND COMPOSITIONS FOR each Risindependently H, C-C alkyl, arylalkyl, S(O)alkyl, TREATING CHEMICAL WARFARE acetyl, amidyl, or S(O)H; AGENT INDUCED INURES each R" is independently C-C alkyl, C-C alkenyl, C-C, alkynyl, cyclyl, heterocyclyl, aryl, heteroaryl, halo, CLAIM OF PRIORITY hydroxyl, alkoxy, aryloxy, arylalkoxy, amino, alkylamino, This application claims priority from U.S. Ser. No. 61/127, dialkylamino, thioyl, alkylthioyl, Sulfonyl, Sulfonamidyl, 666, U.S. Ser. No. 61/127,664, U.S. Ser. No. 61/127,665, U.S. amido, urea, Sulfonylurea, hydroxyl alkoxyl, alkoxy Ser. No. 61/127,723, U.S. Ser. No. 61/127,787, U.S. Ser. No. alkoxyl, acyl, nitro, cyano, each of which is independently 61/127,790, U.S. Ser. No. 61/127,682, all filed May 14, 2008, substituted with 1-3 R: all of which are incorporated herein by reference in their each R is independently C-C alkyl, C-C alkenyl, or entirety. C-C alkynyl, halo, hydroxyl, alkoxy, aryloxy, amino, alkylamino, dialkylamino, thioyl, Sulfonyl, Sulfonamidyl, BACKGROUND amido, urea, Sulfonylurea acyl, nitro, cyano, cyclyl, hetero cyclyl, aryl, or heteroaryl; The invention relates to compounds and compositions use 15 ful for treating injuries caused by chemical warfare and simi each m and n are independently 0, 1, 2, 3, 4, 5, or 6, wherein lar agents. m is at least 2 when L is connected to the methylene carbon A variety of ion channel proteins exist to mediate ion flux via a heteroatom, across cellular membranes. The proper expression and func each R is independently H, C-C alkyl, C-C alkenyl, or tion of ion channel proteins is essential for the maintenance of C-C alkynyl, halo, hydroxyl, alkoxy, aryloxy, arylalkoxy, cell function and intracellular communication. Numerous amino, alkylamino, dialkylamino, thioyl, alkylthioyl, Sul diseases and disorders are the result of misregulation of mem fonyl, Sulfonamidyl, amido, urea, Sulfonylurea, acyl, nitro, brane potential or aberrant calcium handling. Given the cen cyano, each of which is independently substituted with 1-3 tral importance of ion channels in modulating membrane R8. potential and ion flux in cells, identification of agents that can 25 In another aspect, the invention features a method of treat promote or inhibit particularion channels are of great interest, ing an injury resulting from exposure to a chemical warfare both as research tools and as therapeutic agents. agent in a Subject, such as a human, the method comprising administering to the Subject a compound of Formula (III) SUMMARY OF THE INVENTION or a salt thereof 30 The present invention provides compounds and composi tions for treating or preventing injuries resulting from chemi 3 Formula (III) cal warfare agents by modulating the activity of the TRPA1 R channel. In one aspect, the invention features a method of treating an 35 L? injury resulting from exposure to a chemical warfare agent in ( iii. a Subject, Such as a human, the method comprising adminis s ( tering to the Subject a compound of Formula (II) or a salt 21 thereof 1. M R9 40 O N N Formula (II) R3 wherein, r 45 R" is C-C alkyl, C-C alkenyl, or C-C alkynyl, each of O iii. L which is optionally substituted with 1-4 R: X is N or CR R is H. C-C alkyl, C-C alkenyl, or C-C alkynyl, each of which is optionally substituted with 1-4 R: 50 L is NRSO, SONR, OC(O)NR, NRC(O)O, NRC(O) J-2 NR, NRC(O), C(O)NR, O, C(O), S, S(O), S(O), NR CH2 cyclyl, aryl, heterocyclyl, or heteroaryl; wherein, R is cyclyl, heterocyclyl, aryl, heteroaryl, each of which is R" is C-C alkyl, C-C alkenyl, or C-C alkynyl, each of optionally substituted with 1-4 R7: which is optionally substituted with 1-4 R: 55 each R is independently halo, hydroxyl, alkoxy, amino, alky X is N or CR lamino, dialkylamino, cyano, nitro, amido, alkylamido, R is H. C-C alkyl, C-C alkenyl, or C-C alkynyl, each of dialkylamido, thioyl, Sulfonyl, cyclyl, heterocyclyl, aryl, or which is optionally substituted with 1-4 R: heteroaryl; L is NRSO, SONR, OC(O)NR, NRC(O)O, NRC(O) each Risindependently H, C-C alkyl, arylalkyl, S(O)alkyl, NR, NRC(O), C(O)NR, C(O), O, S, S(O), S(O), NR 60 acetyl, amidyl, or S(O)H; CH, cyclyl, aryl, heterocyclyl, or heteroaryl; each R" is independently C-C alkyl, C-C alkenyl, or R is cyclyl, heterocyclyl, aryl, heteroaryl, each of which is C-C alkynyl, halo, hydroxyl, alkoxy, aryl, heteroaryl, optionally substituted with 1-4 R7: cyclyl, aryloxy, arylalkoxy, amino, alkylamino, dialky each R is independently halo, hydroxyl, alkoxy, amino, alky lamino, thioyl, alkylthioyl, Sulfonyl, Sulfonamidyl, amido, lamino, dialkylamino, cyano, nitro, amido, alkylamido, 65 hydroxylalkoxyl, alkoxyalkoxyl, urea, Sulfonylurea, acyl, dialkylamido, thionyl, Sulfonyl, cyclyl, heterocyclyl, aryl, nitro, cyano, each of which is independently Substituted or heteroaryl; with 1-3 R: US 8,318,728 B2 3 4 each R is independently C-C alkyl, C-C alkenyl, or agent in a subject, Such as a human, the method comprising C-C alkynyl, halo, hydroxyl, alkoxy, aryloxy, amino, administering to the Subject a compound of Formula (V) or a alkylamino, dialkylamino, thioyl, Sulfonyl, Sulfonamidyl, salt thereof amido, urea, Sulfonylurea acyl, nitro, cyano, cyclyl, hetero cyclyl, aryl, or heteroaryl; each R is independently H, C-C alkyl, C-C alkenyl, or Formula (V) C-C alkynyl, halo, hydroxyl, alkoxy, aryloxy, arylalkoxy, amino, alkylamino, dialkylamino, thioyl, alkylthioyl, Sul fonyl, Sulfonamidyl, amido, urea, Sulfonylurea, acyl, nitro, cyano, each of which is independently substituted with 1-3 10 R; each m and n are independently 0, 1, 2, 3, 4, 5, or 6. In another aspect, the invention features a method of treat ing an injury resulting from exposure to a chemical warfare agent in a Subject, such as a human, the method comprising 15 administering to the Subject a compound of Formula (IV) or a salt thereof wherein, RandR are each independently C-C alkyl, C-C alkenyl, or C-C alkynyl, each of which is optionally substituted Formula (IV) with 1-4 R: L is NRSO, SONR, OC(O)NR, NRC(O)O, NRC(O) NR, NR°C(O), C(O)NR', O, C(O), S, S(O), S(O), NR CH2 cyclyl, aryl, heterocyclyl, or heteroaryl; R N 25 R is cyclyl, heterocyclyl, aryl, heteroaryl, each of which is NN M optionally substituted with 1-4 R7: each R is independently halo, hydroxyl, alkoxy, amino, alky Ousul N lamino, dialkylamino, cyano, nitro, amido, alkylamido, 9 dialkylamido, thioyl, Sulfonyl, cyclyl, heterocyclyl, aryl, or R 30 heteroaryl; each R is independently H, C1-C-6 alkyl, arylalkyl, S(O) wherein, alkyl, acetyl, amidyl, or S(O)H: R" and Rare eachindependently C-C alkyl, C-C alkenyl, each R" is independently C-C alkyl, C-C alkenyl, C-C, or C-C alkynyl, each of which is optionally substituted alkynyl, cyclyl, heterocyclyl, aryl, heteroaryl, halo, with 1-4 R: 35 hydroxyl, alkoxy, aryloxy, arylalkoxy, amino, alkylamino, L is NRSO,
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