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. 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