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(12) United States Patent (10) Patent No.: US 9,439,850 B2 Kelliher Et Al

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(12) United States Patent (10) Patent No.: US 9,439,850 B2 Kelliher Et Al USOO943985OB2 (12) United States Patent (10) Patent No.: US 9,439,850 B2 Kelliher et al. (45) Date of Patent: *Sep. 13, 2016 (54) USE OF PUFAS FOR TREATING SKIN (2013.01); A61 K3I/573 (2013.01); A61 K NFLAMMATION 45/06 (2013.01); C07C 59/42 (2013.01) (58) Field of Classification Search (71) Applicant: Dignity Sciences Limited, Dublin (IE) CPC ............. A61 K9/0014; A61K 31/002: A61 K (72) Inventors: Adam Kelliher, London (GB); Angus 31/573; A61K 45/06; C07C 51/42 Morrison, Isle of Lewis (GB); Phil USPC .......................................................... 514/560 Knowles, Cumbria (GB) See application file for complete search history. (73) Assignee: Dignity Sciences Limited, Dublin (IE) (56) References Cited (*) Notice: Subject to any disclaimer, the term of this U.S. PATENT DOCUMENTS patent is extended or adjusted under 35 4,273,763. A 6, 1981 Horrobin U.S.C. 154(b) by 0 days. 4,309.415 A 1/1982 Horrobin This patent is Subject to a terminal dis (Continued) claimer. FOREIGN PATENT DOCUMENTS (21) Appl. No.: 14/203,837 EP O1394.80 5, 1952 (22) Filed: Mar. 11, 2014 EP OO35856 9, 1981 (Continued) (65) Prior Publication Data OTHER PUBLICATIONS US 2014/O194399 A1 Jul. 10, 2014 Conrow et al., Org. Proc. Res. & Dev. 15:301-304 (2011). Related U.S. Application Data (Continued) (63) Continuation of application No. 13/461,472, filed on May 1, 2012, now Pat. No. 8,729.126, which is a Primary Examiner — Deborah D Carr continuation of application No. 13/318,290, filed as (74) Attorney, Agent, or Firm — Perkins Coie LLP application No. PCT/GB2010/000844 on Apr. 29, 2010, now Pat. No. 8,536,223. (57) ABSTRACT (60) Provisional application No. 61/177,811, filed on May The present invention provides a compound which is a 13, 2009. polyunsaturated fatty acid (PUFA) derivative of formula (I), (30) Foreign Application Priority Data Apr. 29, 2009 (GB) ................................... O9074 13.9 O (51) Int. Cl. RO --~~ A6 IK 9/00 (2006.01) A6 IK 3L/202 (2006.01) or a pharmaceutically acceptable salt, or Solvate thereof, for (Continued) use in treating various skin disorders. (52) U.S. Cl. CPC ........... A61K 9/0014 (2013.01); A61K 3 1/202 16 Claims, 5 Drawing Sheets US 9,439,850 B2 Page 2 (51) Int. Cl. EP 0309086 3, 1989 A 6LX 3/573 (2006.01) EP O409559 1991 A6 IK 45/06 (2006.01) E. 'S 28. 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 WOO 103696 1, 2001 4,386,072 A 5, 1983 Horrobin et al. 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Nutr. 2000:71(suppl):361S-6S. of psoriatic plaques under continuous systemic therapy.” Experi mental Dermatology 20:130-133 (2011). * cited by examiner U.S. Patent Sep. 13, 2016 Sheet 1 of 5 US 9,439,850 B2 Figure 1 U.S. Patent Sep. 13, 2016 Sheet 2 of 5 US 9,439,850 B2 Figure 2 U.S. Patent Sep.
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