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(12) United States Patent (10) Patent No.: US 8,314,077 B2 Webb Et Al

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(12) United States Patent (10) Patent No.: US 8,314,077 B2 Webb Et Al US008314077B2 (12) United States Patent (10) Patent No.: US 8,314,077 B2 Webb et al. (45) Date of Patent: *Nov. 20, 2012 (54) FATTY ACID-PHARMACEUTICAL AGENT (56) References Cited CONUGATES U.S. PATENT DOCUMENTS (75) Inventors: Nigel L. Webb, Bryn Mawr, PA (US); 3,539,573 A 11/1970 Schmutz Matthews O. Bradley, Laytonsville, 4,088.646 A * 5/1978 Ishida et al. .................. 544,313 4,097,597 A 6, 1978 Horrom et al. MD (US); Charles S. Swindell, Merion, 4,185,095 A 1/1980 Young PA (US); Victor E. Shashoua, 4,287.184 A 9/1981 Young Brookline, MA (US) 4,346,085 A 8, 1982 Growdon et al. 4,351,831 A 9, 1982 Growden et al. 4,407,744 A 10/1983 Young (73) Assignee: Luitpold Pharmaceuticals, Inc., 4.550,109 A 10, 1985 Folkers et al. Shirley, NY (US) 4,554,272 A 11/1985 Bocket al. 4,558,049 A 12/1985 Bernardi et al. 4,636,494. A 1/1987 Growdon et al. (*) Notice: Subject to any disclaimer, the term of this 4,684,646 A 8/1987 Chang et al. patent is extended or adjusted under 35 4,692,441 A 9, 1987 Alexander et al. U.S.C. 154(b) by 0 days. 4,704,393 A 1 1/1987 Wakabayashi et al. 4,729,989 A 3, 1988 Alexander This patent is Subject to a terminal dis 4,788,063 A 11/1988 Fisher et al. claimer. (Continued) (21) Appl. No.: 10/455.250 FOREIGN PATENT DOCUMENTS DE 2602175 7, 1976 (22) Filed: Jun. 5, 2003 (Continued) (65) Prior Publication Data OTHER PUBLICATIONS US 2004/0106589 A1 Jun. 3, 2004 Hardman, J. G., Editor-in-Chief of Goodman & Gilman's The Phar macological Basis of Therapeutics, Ninth Edition, pp. 1225-1233 and Related U.S. Application Data 1243-1252, 1996.* (Continued) (63) Continuation of application No. 09/730,450, filed on Dec. 5, 2000, now Pat. No. 6,576,636, which is a Primary Examiner — Phyllis G. Spivack continuation of application No. 08/651,428, filed on (74) Attorney, Agent, or Firm — Wolf, Greenfield & Sacks, May 22, 1996, now abandoned. P.C. (57) ABSTRACT (51) Int. C. The invention provides conjugates offatty acids and pharma A6 IK3I/7068 (2006.01) ceutical agents useful in treating noncentral nervous system (52) U.S. Cl. ......................................................... S14/49 conditions. Methods for selectively targeting pharmaceutical (58) Field of Classification Search ........................ None agents to desired tissues are provided. See application file for complete search history. 6 Claims, 14 Drawing Sheets 5 O -5 OO - OO -9 -8 -7 -6 -5 -4 LOG-10 OF SAMPLE CONCENTRATION (MOLAR) CCRF-CEM-O- SR. ----- RPM-8226--e- - - K-562- - -a - - HL-60 (TB)-(- - MOLT-4 D . US 8,314,077 B2 Page 2 U.S. PATENT DOCUMENTS 6,043,230 A 3/2000 Arimilli et al. 4.814,470 A 3, 1989 Colin et all 6,069,249 A 5/2000 Arimilli et al. 4,857,653 A 8/1989 Colin et al. 88s. 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