Absorbable α-cyanoacrylate compositions

US007534907B2 (12) Ulllted States Patent (10) Patent No.: US 7,534,907 B2 Liu (45) Date of Patent: May 19, 2009 (54) ABSORBABLE (X-CYANOACRYLATE 6,455,064 B1 * 9/2002 Narang et al. COMPOSITIONS 6,512,023 B1 1/2003 Malofsky et al. 6,579,469 B1 6/2003 Nicholson et al. (75) Inventor: Hongbo Liu, Hillsborough, NJ (US) 656205846 B1 9/2003 Jon“ et 91' 6,802,416 B1* 10/2004 D’Aless1o et al. Assigneet Inc., ( * ) Notice: Subject to any disclaimer, the term ofthis JP 08505383 T2 6/1996 patent is extended or adjusted under 35 W0 W0 99/55374 * 11/ 1999 U.S.C. 15403) by 0 days. W0 WO 99/55394 * 11/1999 W0 WO 00/26284 * 5/2000 (21) Appl. No.: 11/755,093 OTHER PUBLICATIONS (22) Filed: May 30, 2007 Paez et al. J. Mat. Science: Materials in Medicine 2004, 15, 109- 115.* (65) Prior Publication Data Margules et al. Med. & Biol. Eng. & Comput. 1980, 18, 549-553.* h:// d'al. '-bt.m/ d'al/ lt.* Us 2007/0224163 A1 sep. 27. 2007 iiliiiniiieoiii m§Zri$ WeRZ§§§° iI3§i?Es2°3§§Ziai°5§4‘§e (ETH 5189WOPCT) Int. mailed Aug. 3, 2006. Related U.S. Application Data * . d b . t (62) Division of application No. 11/088,587, filed on Mar. 0.1 e y exanlmer 24, 2005, now Pat, No, 7,238,828, Primary Examzner—Kamal A Saeed Assistant Examiner—Jason M Nolan (51) Int. Cl. (74) Attorney, Agent, or Firm—David R. Crichton A61K 31/785 (2006.01) C07C 255/19 (2006.01) (57) ABSTRACT C08G 63/91 (2006.01) . . . . . C08G 63/43 (2005.01) A monomer composition comprising at least one polymeriz- (52) U.S. Cl. .................. .. 558/442; 558/441; 424/78.27; able alkyl ester 01-eyanoaerylate monomer. Speelfieallys the 525/541 0L-cyanoacrylate monomer is an alkyl ester 0L-cyanoacrylate (58) Field of Classification Search ............... .. 558/441, menemer efthe general felmule heme e eleeeer R13 558/442; 424/78.27; 525/54.1 See application file for complete search history. (1) (56) References Cited CN JL U.S. PATENT DOCUMENTS H / 0\R 0/ R2 1 3,940,362 A 2/1976 Overhults H 0 3,995,641 A 12/1976 Kronenthal et al. R 4,313,865 A 2/1982 Teramoto et al. '3 4,560,723 A 12/1985 Millet et al. wherein R1 : —(—C—)—; 4,720,513 A 1/1988 Kameyama et al. | " 5,259,835 A * 11/1993 Clark et al. R4 5,328,687 A 7/1994 Leung et al. 5,514,371 A 5/1996 Leung et al. . 5,514,372 A 4 5/1996 Leung et 31. n is from 2 to 12; R3 and R4 are each an alkyl group or a 5,575,997 A 11/1996 Leung et 31. hydrogen, and at least one ofR3 or R4 is an alkyl group (e.g. 5,582,834 A 12/1996 Leung et al. linear or branched, or cyclic) having from 1, 2, 3, 4, 5, 6, 7, 8, 5,624,669 A 4/1997 Leung GU11 9, 10, 11, 12 and 13 carbon atoms; R2 is an alkyl group (e.g. 59285611 A 7/1999 Leung linear or branched, or cyclic) having from 1, 2, 3, 4, 5, 6, 7, 8, : * Efuig :ta’1’1' 9, 10, 11, 12 and 13 carbon atoms; and the combined number , , ar e . ~ ~ 6,372,313 B1,, 4/2002 D,A1eSSi0 et 31. ofcarbon atoms (N) in the spacer R1 is at least n+1. 6,425,704 B2 * 7/2002 Voiers et al. 6,428,233 B1 * 8/2002 Clark et al. 1 Claim, 2 Drawing Sheets U.S. Patent May 19, 2009 Sheet 1 of2 US 7,534,907 B2 \