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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. Elshof et al. “Biocatalytic large-scale production of 12(S)- 5,709,855 1, 1998 Bockow et al. hydroperoxy-9(Z), 117 octadecadienoic acid from hydrolysed saf 5,888,541 3, 1999 Horrobin et al. flower oil by a crude Soybean-flour extract as lipoxygenase source.” 6,069,168 5, 2000 Horrobin et al. Rec. Trav. Chim Pays-Bas, 115, 11-12, p. 499-504 (1996). 6,177,470 1, 2001 Horrobin et al. Elshofetal., “Biocatalytic hydroxylation of linoleic acid in a double 6.479,544 11, 2002 Horrobin fed batch system with lipoxygenase and cysteine.” 100:6. pp. 246 6,630,157 10, 2003 Horrobin et al. 7,202.276 4, 2007 Buchanan et al. 251 (1999). 7,888,393 2, 2011 Bettle, III Erythema, Retrieved online Feb. 11, 2014). Retrieved from 8,293,790 10, 2012 Manku et al. URL:<http://umm.edu/health/medical/altimed/condition? 8,536,223 9, 2013 Kelliher et al. erythema>. 2003/OO73930 4, 2003 Morrissey et al. Feldlaufer et al., “Antimicrobial activity offatty acids against Bacillus 2003. 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Kiistala, “Suction blister device for separation fo viable epidermis 2012/O142773 6, 2012 Kelliher et al. from dermis,” J. Invest. Dermatol. 50: 129-137 (1968). 2012fO213824 8, 2012 Kelliher et al. Miller et al., “Dietary Supplementation with Ethyl Ester Concen 2012fO232147 9, 2012 Manku et al. trates of Fish Oil (N-3) and Borage Oil (N-6) Polyunsaturated Fatty 2012fO264705 10, 2012 Manku et al. Acids Induces Epidermal Generation of Local Putative Anti-Inflam 2013/0101533 4, 2013 Manku et al. matory Metabolites.” The Journ. Of Invest. Dermatol., vol.96, No. 1, 2013/01O2575 4, 2013 Manku et al. pp. 98-103 (1991). US 9.216,151 B2 Page 3 (56) References Cited PCT/US2012/67030 International Search Report dated Feb. 5, 2013. PCT/US2013/023201 International Search Report dated Mar. 29, OTHER PUBLICATIONS 2013. 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    List of European Pharmacopoeia Reference Standards Effective from 2015/12/24 Order Reference Standard Batch n° Quantity Sale Information Monograph Leaflet Storage Price Code per vial Unit Y0001756 Exemestane for system suitability 1 10 mg 1 2766 Yes +5°C ± 3°C 79 ! Y0001561 Abacavir sulfate 1 20 mg 1 2589 Yes +5°C ± 3°C 79 ! Y0001552 Abacavir for peak identification 1 10 mg 1 2589 Yes +5°C ± 3°C 79 ! Y0001551 Abacavir for system suitability 1 10 mg 1 2589 Yes +5°C ± 3°C 79 ! Y0000055 Acamprosate calcium - reference spectrum 1 n/a 1 1585 79 ! Y0000116 Acamprosate impurity A 1 50 mg 1 3-aminopropane-1-sulphonic acid 1585 Yes +5°C ± 3°C 79 ! Y0000500 Acarbose 3 100 mg 1 See leaflet ; Batch 2 is valid until 31 August 2015 2089 Yes +5°C ± 3°C 79 ! Y0000354 Acarbose for identification 1 10 mg 1 2089 Yes +5°C ± 3°C 79 ! Y0000427 Acarbose for peak identification 3 20 mg 1 Batch 2 is valid until 31 January 2015 2089 Yes +5°C ± 3°C 79 ! A0040000 Acebutolol hydrochloride 1 50 mg 1 0871 Yes +5°C ± 3°C 79 ! Y0000359 Acebutolol impurity B 2 10 mg 1 -[3-acetyl-4-[(2RS)-2-hydroxy-3-[(1-methylethyl)amino] propoxy]phenyl] 0871 Yes +5°C ± 3°C 79 ! acetamide (diacetolol) Y0000127 Acebutolol impurity C 1 20 mg 1 N-(3-acetyl-4-hydroxyphenyl)butanamide 0871 Yes +5°C ± 3°C 79 ! Y0000128 Acebutolol impurity I 2 0.004 mg 1 N-[3-acetyl-4-[(2RS)-3-(ethylamino)-2-hydroxypropoxy]phenyl] 0871 Yes +5°C ± 3°C 79 ! butanamide Y0000056 Aceclofenac - reference spectrum 1 n/a 1 1281 79 ! Y0000085 Aceclofenac impurity F 2 15 mg 1 benzyl[[[2-[(2,6-dichlorophenyl)amino]phenyl]acetyl]oxy]acetate
  • (12) United States Patent (10) Patent No.: US 6,264,917 B1 Klaveness Et Al

    (12) United States Patent (10) Patent No.: US 6,264,917 B1 Klaveness Et Al

    USOO6264,917B1 (12) United States Patent (10) Patent No.: US 6,264,917 B1 Klaveness et al. (45) Date of Patent: Jul. 24, 2001 (54) TARGETED ULTRASOUND CONTRAST 5,733,572 3/1998 Unger et al.. AGENTS 5,780,010 7/1998 Lanza et al. 5,846,517 12/1998 Unger .................................. 424/9.52 (75) Inventors: Jo Klaveness; Pál Rongved; Dagfinn 5,849,727 12/1998 Porter et al. ......................... 514/156 Lovhaug, all of Oslo (NO) 5,910,300 6/1999 Tournier et al. .................... 424/9.34 FOREIGN PATENT DOCUMENTS (73) Assignee: Nycomed Imaging AS, Oslo (NO) 2 145 SOS 4/1994 (CA). (*) Notice: Subject to any disclaimer, the term of this 19 626 530 1/1998 (DE). patent is extended or adjusted under 35 O 727 225 8/1996 (EP). U.S.C. 154(b) by 0 days. WO91/15244 10/1991 (WO). WO 93/20802 10/1993 (WO). WO 94/07539 4/1994 (WO). (21) Appl. No.: 08/958,993 WO 94/28873 12/1994 (WO). WO 94/28874 12/1994 (WO). (22) Filed: Oct. 28, 1997 WO95/03356 2/1995 (WO). WO95/03357 2/1995 (WO). Related U.S. Application Data WO95/07072 3/1995 (WO). (60) Provisional application No. 60/049.264, filed on Jun. 7, WO95/15118 6/1995 (WO). 1997, provisional application No. 60/049,265, filed on Jun. WO 96/39149 12/1996 (WO). 7, 1997, and provisional application No. 60/049.268, filed WO 96/40277 12/1996 (WO). on Jun. 7, 1997. WO 96/40285 12/1996 (WO). (30) Foreign Application Priority Data WO 96/41647 12/1996 (WO).
  • Efficacy and Safety of Halometasone Cream to Treat Chronic Generalized Eczema and the Effects of Halometasone Cream on Serum Cortisol Levels

    Efficacy and Safety of Halometasone Cream to Treat Chronic Generalized Eczema and the Effects of Halometasone Cream on Serum Cortisol Levels

    Hindawi BioMed Research International Volume 2017, Article ID 3265024, 7 pages https://doi.org/10.1155/2017/3265024 Clinical Study Efficacy and Safety of Halometasone Cream to Treat Chronic Generalized Eczema and the Effects of Halometasone Cream on Serum Cortisol Levels Yan Li, Wei Xu, and Linfeng Li Department of Dermatology, Beijing Friendship Hospital, Capital Medical University, Beijing 100050, China Correspondence should be addressed to Wei Xu; [email protected] Received 19 August 2017; Accepted 19 October 2017; Published 9 November 2017 Academic Editor: Fabio Sonvico Copyright © 2017 Yan Li et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The aim of the study was to investigate the efficacy and safety ofhalometasone cream to treat chronic generalized eczema and the effects of halometasone cream on serum cortisol (COR) levels. Sixty consecutive outpatients diagnosed with chronic generalized eczema between January and April 2017 were included and divided into groups A, B, and C with a lesion area of 30%–40%, 41%–50%, and51%–60%,respectively.GroupsA,B,andCweretreatedwithhalometasonecreamwithadailydoseof15g,20g,and30gfor 7–14 days, respectively. Ten patients were randomly selected from each group for serum COR measurement at days 0, 7, and 14. On day 14, group B had significantly higher cure rate (47.1%)than groups A (17.9%)and C (13.3%) and significantly higher effectiveness rate (82.4%) than group C (40.0%) (all < 0.05). Serum COR levels were not affected in group A but were reduced significantly in groups B and C on days 7 and 14 (all < 0.05).