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In They ''''' (58) Field of Classification Search S S CPC USOO926.0382B2 (12) United States Patent (10) Patent No.: US 9.260,382 B2 Yang et al. (45) Date of Patent: Feb. 16, 2016 (54) METHODS OF REDUCINGVIRULENCE IN 31/165 (2013.01); A61K 31/185 (2013.01); BACTERA A6 IK3I/192 (2013.01); A61 K3I/194 (2013.01); (75) Inventors: Ching-Hong Yang, Mequon, WI (US); (Continued) in they ''''' (58) Field of Classification search s s CPC ........... A61K 31/4015; A61K 31/4164: A61 K 3 1/1.75 (73) Assignees: Milwaukee,UWM Research WI (US); Foundation, Duke University, USPC ............... 548/311.1, 452: 514/396, 412, 617; Durham,urham, NC (US(US) See application file for complete search history.564/305 (*) Notice: Subject to any disclaimer, the term of this (56) References Cited patent is extended or adjusted under 35 U.S.C. 154(b) by 107 days. U.S. PATENT DOCUMENTS (21) Appl. No.: 13/579,373 5.447,903. A 9, 1995 Ort et al. 5,994,077 A 11/1999 Valdivia et al. (22) PCT Filed: Feb. 16, 2011 (Continued) (86). PCT No.: PCT/US2O11AO25082 FOREIGN PATENT DOCUMENTS S371 (c)(1), WO WO99,58714 11, 1999 (2), (4) Date: Aug. 16, 2012 WO O2O68610 9, 2002 (87) PCT Pub. No.: WO2011/103189 (Continued) PCT Pub. Date: Aug. 25, 2011 OTHER PUBLICATIONS O O HCAPLUS abstract of Appukkuttan, et al., Tetrahedron Letters, (65) Prior Publication Data HCAPLUS Accession # 2008: 1017175, published 2008.* US 2012/0322769 A1 Dec. 20, 2012 (Continued) Related U.S. Application Data Primary Examiner — Kamal Saeed (60) Provisional application No. 61/305,027, filed on Feb Assistant Examiner — Janet L. Coppins 16,roV1S1onal 2010, provisionalapplicauon applicationNo. UZNo. f, Illed61/332.385, on Feb. Attorney, Agent, or Firmin — MichaelMi Best & Friedrich- 0 filed on May 7, 2010. (51) Int. Cl. (57) ABSTRACT A6 IK3I/40 (2006.01) A method of reducing virulence in a bacterium comprising at A6 IK3I/405 (2006.01) least one of a GacS/GacA-type system, a HrpX/HrpY-type (Continued) system, a T3SS-type system, and a RSm-type system, the method comprising contacting the bacterium with an effec (52) U.S. Cl. tive amount of a compound described herein. CPC ............... C07C 259/06 (2013.01); A61 K3I/05 (2013.01); A61 K3I/I37 (2013.01); A61 K 21 Claims, 33 Drawing Sheets if HrpY N\ (+) hipS Y. dispE Hrps w (+)- Effectorf (+) -* hip?. RNA HrpL - Hop genes hal --- w Harpin iStaRRNA-RsmA \ (-) N hpN > (+ Hrp/Hre - 's- v. A hipA rine RNA RsnA hip/hire ^*) x sata risint B - / US 9.260,382 B2 Page 2 (51) Int. Cl. 213/56 (2013.01); C07D 233/64 (2013.01); A6 IK3I/4164 (2006.01) C07D 307/52 (2013.01); C07D 307/79 A 6LX3L/75 (2006.01) (2013.01); C07D 333/24 (2013.01); C07D C07C 259/06 (2006.01) 333/60 (2013.01); C07D 403/06 (2013.01); A6 IK3I/05 (2006.01) C07D405/06 (2013.01); C07F 9/3826 A6 IK3I/37 (2006.01) (2013.01); C07C 2101/02 (2013.01) A6 IK3I/65 (2006.01) A6 IK3I/85 (2006.01) (56) References Cited A6 IK3I/92 (2006.01) A6 IK3I/94 (2006.01) U.S. PATENT DOCUMENTS A6 IK3I/96 (2006.01) 7,026,155 B2 4/2006 Mahan et al. A6 IK3I/26 (2006.01) 7,196,085 B2 3/2007 Martin et al. 7,339,043 B2 3/2008 Cheung et al. St. 125 C 2002fOO86332 A1 7/2002 Mahan et al. (2006.01) 2002/0102246 A1 8/2002 Schneider et al. A6 IK3I/34 (2006.01) 2003/0176364 A1 9, 2003 Ninkov A6 IK3I/343 (2006.01) 2007/O128328 A1 6/2007 Tanada et al. A6 IK3I/38 (2006.01) 2009 OO12128 A1 1/2009 TSuchida et al. A6 IK3I/4035 (2006.01) 2010/0249234 A1 9/2010 Yang et al. A6 IK3I/404 (2006.01) FOREIGN PATENT DOCUMENTS A6 IK3I/472 (2006.01) A6 IK3I/478 (2006.01) WO WO 2008, 115118 9, 2008 A6 IK3I/4406 (2006.01) WO WO 2008/124836 10, 2008 A6 IK3I/4409 (2006.01) WO WO-2008, 134836 A2 * 10, 2008 ............. A61K 31 OO 3. 7. 9 3.08: OTHER PUBLICATIONS A6 IK3I/683 (2006.01) HCAPLUS abstract of Brewbaker, et al., J. Am. Chem. Society, C07C 2 II/29 (2006.01) HCAPLUS Accession # 1969:67319, published 1969.* C07C 215/54 (2006.01) HCAPLUS abstract of Di Fabio, et al., Bio & Med. Chem. Letters, CD7C233/65 (2006.01) HCAPLUS Accession # 2003:795121, published 2003.* C07C 235/34 (2006.01) HCAPLUS abstract of Eckhardt, et al., J. Clinical Chem & Clinical C07C 237/20 (2006.01) Biochem, HCAPLUS Accession # 1977:462286, published 1977.* CD7C 243/32 (2006.01) HCAPLUS abstract of Gadient, F., DE 2252080, HCAPLUS Acces C07C 259/08 (2006.01) HCAPLUSsion # RSE abstract of Griffith,My et al., 1973.*Bioorganic & Med.d. Chem.Ch C 3. O7 3. Letters, HCAPLUS Accession #1993:254814, published 1993.* ( .01) HCAPLUS abstract of Hori, et al., EP255695, HCAPLUS Accession CO7D 209/.4 (2006.01) # 1988:534833, published Feb. 10, 1988.* CO7D 209/248 (2006.01) HCAPLUS abstract of Jolidon et al., WO 2004007429, HCAPLUS CO7D 209/86 (2006.01) Accession # 2004:60452, published Jan. 22, 2004.* CO7D 213/56 (2006.01) HCAPLUS abstract of Joung et al., Cancer Research, HCAPLUS CO7D 233/64 (2006.01) Accession # 2006:459 139, published 2006.* C07D 307/52 (2006.01) HCAPLUS abstract of Lim et al., WO 2005040 101, HCAPLUS C07D 307/79 (2006.01) Accession # 2005:395258, published May 6, 2005.* HCAPLUS abstract of Mhatre et al., Indian J. Het. Chem. C '7, R HCAPLUS Accession # 2000:545303, published 2000.* ( ) HCAPLUS abstract of Tajima et al., WO 200601 1669, HCAPLUS CO7D 403/06 (2006.01) Accession # 2006:103803, published Feb. 2, 2006.* CO7D 405/06 (2006.01) HCAPLUS abstract of Thaler et al., J. Med. Chem, HCAPLUS C07F 9/38 (2006.01) Accession # 2009:1563803, published 2010.* (52)52) U.S. C. HCAPLUS abstract of Szmaszkovicz, J., U.S. Pat. No. 3,043,849, CPC ............. A6 IK3I/196 (2013.01); A61 K3I/216 HCAPLUS Accession # 1962:483164, published Jul. 10, 1962.* HCAPLUS abstract of Wagh et al., Asian J. Chem, HCAPLUS (2013.01); A61 K3I/255 (2013.01); A61 K Accession # 2007:854258, published 2007.* 3I/277 (2013.01); A61 K3I/341 (2013.01); International Search Report and Written Opinion of International A6 IK3I/343 (2013.01); A61 K3I/381 Searching Authority for Application No. PCT/US2008/059928 dated (2013.01); A61 K3I/404 (2013.01); A61 K Nov. 21, 2008 (16 pages). 31/4035 (2013.01); A61 K31/4172 (2013.01); Office Action from the US Patent and Trademark Office for U.S. A6 IK3I/4178 (2013.01); A61 K3I/4406 Appl. No. 12/595,148 dated Dec. 13, 2012 (12 pages). (2013.01); A61K3I/4409 (2013.01); A61 K First Office Action from the State Intellectual Property Office of 3 1/4439 (2013.01); A61 K3I/662 (2013.01): China for Application No. 2011800 19127.2 dated Sep. 30, 2013 (18 A61 K3I/683 (2013.01); C07C 211/29 pages). Aiello, D. et al., “Discovery and characterization of inhibitors of (2013.01); C07C 215/54 (2013.01); C07C Pseudomonas aeruginosa type III Secretion.” Antimicrob Agents 233/65 (2013.01); C07C 235/34 (2013.01); Chemother. (2010) 54: 1988-1999. C07C 237/20 (2013.01); C07C 243/32 Alfano, J.R. et al., “The pseudomonas Syringae Hrp pathogenicity (2013.01); C07C 259/08 (2013.01); C07C island has a tripartite mosaic structure composed of a cluster of type 309/24 (2013.01); C07C309/68 (2013.01); III Secretion genes bounded by exchangeable effector and conserved C07D 209/14 (2013.01); C07D 209/48 effector loci that contribute to parasitic fitness and pathogenicity in (2013.01); C07D 209/86 (2013.01); C07D plants.” Proc. Natl. Acad. 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Bahrani, F.K. et al., “Secretion of Ipa proteins by shigella flexneri: RNA in Erwinia carotovora subsp. carotovora by affecting its sta inducer molecules and kinetics of activation.” Inf. Immun. (1997) bility.” J. Bacteriol. (2002) 184:4089-4095. 65(10):4005-4010. Chellas-Gery, B. et al., “human Gcip interacts with Ct847, a novel Bailey, L. et al., “Small molecule inhibitors of type III secretion in chlamydia trachomatis type III Secretion Substrate, and is degraded in Yersinia block the chlamydia pneumoniae infection cycle.” FEBS a tissue-culture infection model.” Cell Microbiol. (2007) 9:2417 Lett. (2007) 581:587-595. 2430. Barnard, F.M. et al., “Global regulation of virulence and the stress Coburn, B. et al., “Type III secretion systems and disease.” Clin. response by Csra in the highly adapted human gastric pathogen Microbiol. Rev. (2007) 20:535-549. helicobacter pylon.” Mol. Microbiol. (2004) 51: 15-32. Collmer, A.
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