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(12) United States Patent (10) Patent No.: US 9,127.024 B2 Chellappan Et Al US009 127024B2 (12) United States Patent (10) Patent No.: US 9,127.024 B2 Chellappan et al. (45) Date of Patent: Sep. 8, 2015 (54) BORON-CONTAINING DIACYLHYDRAZINES 5,514,578 A 5/1996 Hogness et al. 5,530,021 A 6/1996 Yanagi et al. (71) Applicant: Intron Corporation, Blacksburg, VA 5,599,9045,530,028 A 2f19976/1996 LidlertEvans et al. ( ) 5,641,652 A 6/1997 Oro et al. 5,668,175 A 9, 1997 Evans et al. (72) Inventors: Sheela K. Chellappan, Clarksburg, MD 5,710,004 A 1/1998 Evans et al. (US); Robert E. Hormann, Melrose 5,723,329 A 3/1998 Mangelsdorf et al. Park, PA (US); Inna Shulman 5,880,333. A 3/1999 Goffet al. L s PA S s 5,919,667 A 7/1999 Gage et al. anghorne, PA (US) 5,945,400 A 8/1999 Scherman et al. 5.948,406 A 9, 1999 Stavinski et al. (73) Assignee: Intrexon Corporation, Blacksburg, VA 5,981, 196 A 11/1999 Stavinski et al. (US) 5,989,863. A 1 1/1999 Tang et al. 6,013,836 A 1/2000 Hsu et al. (*) Notice: Subject to any disclaimer, the term of this 6,025,483. A 2/2000 Yanofsky patent is extended or adjusted under 35 (Continued) U.S.C. 154(b) by 0 days. FOREIGN PATENT DOCUMENTS (21) Appl. No.: 14/212.526 CA 2 103 110 C 5, 1994 (22) Filed: Mar 14, 2014 CN 1245638 A 3, 2000 (Continued) (65) Prior Publication Data US 2014/0274954A1 Sep. 18, 2014 OTHER PUBLICATIONS Baker, Chem Soc Rev, 2011, 40, 4279-4285.* Related U.S. Application Data (Continued) (60) Provisional application No. 61/792,412, filed on Mar. 15, 2013. Primary Examiner — D M Seaman (51) Int. Cl. in C07F 5/04 (2006.01) Giro ". or Firm — Sterne, Kessler, C07F 5/02 (2006.01) u u YW (52) U.S. Cl. CPC. C07F5/04 (2013.01); C07F 5/025 (2013.01); (57) ABSTRACT C07F 5/027 (2013.01) (58) Field of Classification Search The present disclosure provides boron-containing diacylhy CPC ......... A01B 12/006; C07F 5/04; C07F 5/025; drazines having Formula I: CO7F 5/027 USPC .......................................................... 54.6/159 See application file for complete search history. I R2 (56) References Cited O 's- U.S. PATENT DOCUMENTS ls N R5 4 1. 4,631,211 A 12/1986 Houghten R N 4,814,349 A 3, 1989 Addor et al. O 4,859,609 A 8, 1989 Dullet al. 4,906,280 A 3, 1990 Sandler et al. 4,950,666 A 8, 1990 Peake et al. 4.954,655 A 9/1990 Kelly and the pharmaceutically acceptable salts and Solvates 4,981,784. A 1/1991 Evans et al. thereof, wherein R,R,R,R, and Rare defined as set 4,985,461 A 1/1991 Hsu et al. forth in the specification. The present disclosure also 38492. A 38. t s al provides the use of boron-containing diacylhydrazines 5.075471. A 12, 1991 Michelottietal. is ecdysone receptor-based inducible gene expression 5,117,057 A 5, 1992 Hsu et al. systems. Thus, the present disclosure is useful for appli 5,171,671. A 12/1992 Evans et al. cations such as gene therapy, treatment of disease, large 5,225,443 A 7/1993 Murphy et al. 5,283,173 A 2f1994 Fields et al. Scale production of proteins and antibodies, cell-based 5,344,958 A 9, 1994 Lidlert et al. Screening assays, functional genomics, proteomics, 5,354,762 A 8. 1994 Hsu et al. 1 metabolomics, and regulation of traits in transgenic 5,378,7265,358,966 A 10/19941/1995 James,Yanagi Jr.et al.et al. E. where control of gene expression levels is 5,424,333. A 6/1995 Wing S18). 5,429,952 A 7, 1995 Garner et al. 5,459,127 A 10/1995 Felgner et al. 5,482.962 A 1/1996 Hormann 38 Claims, 7 Drawing Sheets US 9,127.024 B2 Page 2 (56) References Cited JP 62-263150 A 11, 1987 JP 2-207066 A 8, 1990 U.S. PATENT DOCUMENTS JP 3-141245 A 6, 1991 JP 3-145447. A 6, 1991 6,096,787 A 8, 2000 Evans et al. JP 4-089471 A 3, 1992 6,107,286 A 8/2000 Byket al. JP 4-178380 A 6, 1992 6,117,639 A 9/2000 Germann et al. JP 4-235.177 A 8, 1992 6,147.282 A 1 1/2000 Goffet al. 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