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USOO921 6151B2 (12) United States Patent (10) Patent No.: US 9.216,151 B2 Kelliher et al. (45) Date of Patent: *Dec. 22, 2015 (54) USE OF PUFAS FOR TREATING SKIN (58) Field of Classification Search NFLAMMATION CPC ........... A61K 8/36; A61K 8/37; A61 K31/20; A61K 31/201: A61K 31/202 (71) Applicant: Dignity Sciences Limited, Dublin (IE) USPC ........................................... 514/560:554/224 See application file for complete search history. (72) Inventors: Adam Kelliher, London (GB); Angus Morrison, Isle of Lewis (GB); Phil Knowles, Cumbria (GB) (56) References Cited (73) Assignee: Dignity Sciences Limited. (IE) U.S. PATENT DOCUMENTS 4,273,763. A 6, 1981 Horrobin (*) Notice: Subject to any disclaimer, the term of this 4,309.415 A 1/1982 Horrobin patent is extended or adjusted under 35 U.S.C. 154(b) by 0 days. (Continued) This patent is Subject to a terminal dis FOREIGN PATENT DOCUMENTS claimer. EP O1394.80 5, 1952 (21) Appl. No.: 14/316.375 EP OO35856 9, 1981 (Continued) (22) Filed: Jun. 26, 2014 OTHER PUBLICATIONS (65) Prior Publication Data US 2014/03093O4 A1 Oct. 16, 2014 Conrow et al., Org. Proc. Res. & Dev. 15:301-304 (2011). (Continued) Related U.S. Application Data (63) Continuation of application No. 14/203,837, filed on Primary Examiner — Deborah D Carr Mar. 11, 2014, which is a continuation of application (74) Attorney, Agent, or Firm — Perkins Coie LLP No. 13/461,472, filed on May 1, 2012, now Pat. No. 8.729.126, which is a continuation of application No. (57) ABSTRACT (Continued) The present invention provides a compound which is a poly (30) Foreign Application Priority Data unsaturated fatty acid (PUFA) derivative of formula (I), Apr. 29, 2009 (GB) ................................... O9074 13.9 O (51) Int. Cl. AOIN37/00 (2006.01) A6 IK3I/20 (2006.01) RO --- "Su-1N1 (Continued) (52) U.S. Cl. or a pharmaceutically acceptable salt, or Solvate thereof, for CPC ............. A61 K9/0014 (2013.01); A61 K3I/202 use in treating various skin disorders. (2013.01); A61 K3I/573 (2013.01); A61 K 45/06 (2013.01); C07C59/42 (2013.01) 19 Claims, 5 Drawing Sheets US 9.216,151 B2 Page 2 Related U.S. Application Data 2013/0267,598 A1 10/2013 Manku et al. 2013/0274338 A1 10/2013 Manku et al. 13/318,290, filed as application No. PCT/GB2010/ 2013/0331448 A1 12/2013 Manku et al. 000844 on Apr. 29, 2010, now Pat. No. 8,536,223. FOREIGN PATENT DOCUMENTS (60) Provisional application No. 61/177,811, filed on May 13, 2009. EP OO37175 10, 1981 EP OO78434 5, 1983 EP O087863 9, 1983 EP O087864 9, 1983 (51) Int. Cl. EP O087865 9, 1983 A23D 9/00 (2006.01) EP O 115419 8, 1984 A6 IK9/00 (2006.01) EP O 132089 1, 1985 A6 IK3I/202 EP O173478 3, 1986 (2006.01) EP 0309086 3, 1989 A 6LX3/573 (2006.01) EP O409559 1, 1991 A6 IK 45/06 EP O416855 3, 1991 (2006.01) EP 1852114 11, 2007 C07C 59/42 (2006.01) EP 250818O 10, 2012 JP 2006219.454 8, 2006 (56) References Cited JP 2006.306812 11, 2006 WO WO9816215 4f1998 U.S. PATENT DOCUMENTS WO WO9852556 11, 1998 WO WO2O10020603 4/2000 4,386,072 5, 1983 Horrobin et al. WO WOO 103696 1, 2001 4,388,324 6, 1983 Horrobin WO WOO2O1969 1, 2002 4,444,755 4, 1984 Horrobin WO WOO2O89791 11, 2002 4,826,877 5, 1989 Stewart et al. WO WOO2092O71 11, 2002 4,888,326 12, 1989 Horrobin WO WOO2O964.08 12/2002 4,898,885 2, 1990 Horrobin WO WO2007079224 7/2007 4,965,075 10, 1990 Horrobin et al. WO WO2O08070129 6, 2008 4,970,076 11, 1990 Horrobin WO WO 20080701.29 A2 * 6, 2008 ........... A61K 31,202 4,996,233 2, 1991 Horrobin WO WO2008114141 9, 2008 4,997,657 3, 1991 Horrobin et al. WO WO2010.125330 11, 2010 5,145,686 9, 1992 Horrobin et al. WO WO2010.125340 11, 2010 5, 198468 3, 1993 Horrobin WO WO2O13057284 4/2013 5,318,991 6, 1994 Horrobin et al. WO WO2O13057287 4/2013 5,324,748 6, 1994 Horrobin WO WO2013O82265 6, 2013 5,328,691 T. 1994 Horrobin et al. WO WO2O13112876 8, 2013 5,380,757 1, 1995 Horrobin WO WO2O13124479 8, 2013 5,552,150 9, 1996 Horrobin et al. WO WO2O14022816 2, 2014 5,562.913 10, 1996 Horrobin 5,580,556 12, 1996 Horrobin OTHER PUBLICATIONS 5,583, 159 12, 1996 Horrobin et al. 5,589,509 12, 1996 Horrobin Desbois et al., “Antibacterial free fatty acids: activities, mechanisms 5,614,208 3, 1997 Horrobin et al. of action and biotechnological potential. Appl. Microbiol. 5,618,558 4, 1997 Horrobin et al. 5,620,701 4, 1997 Horrobin et al. Biotechnol. (2010) 85:1629-1642. 5,663,202 9, 1997 Horrobin et al. 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