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(12) United States Patent (10) Patent No.: US 9,693,956 B2 Seigfried (45) Date of Patent: *Jul

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(12) United States Patent (10) Patent No.: US 9,693,956 B2 Seigfried (45) Date of Patent: *Jul USOO9693956B2 (12) United States Patent (10) Patent No.: US 9,693,956 B2 Seigfried (45) Date of Patent: *Jul. 4, 2017 (54) LIQUID COMPOSITIONS CAPABLE OF 5,556,638 A 9, 1996 Wunderlich et al. FOAMING AND INCLUDING ACTIVE 5,560,924 A 10, 1996 Wunderlich et al. 5,565,613 A 10/1996 Geisslinger et al. AGENTS, AND METHODS FOR MAKING OR 5,580,491 A 12/1996 Phillips et al. DEVELOPNG SAME 5,738,869 A 4/1998 Fischer et al. 5,747,058 A 5/1998 Tipton et al. (71) Applicant: MIKA Pharma GmbH 5,958,379 A 9/1999 Regenold et al. 5,976,566 A 11/1999 Samour et al. (72) Inventor: Bernd G. Seigfried, Limburgerhof 6,066,332 A 5, 2000 Wunderlich et al. 6,165,500 A 12/2000 Cevc (DE) 6,287,592 B1 9, 2001 Dickinson 6,309.663 B1 10/2001 Patel et al. (73) Assignee: MIKA Pharma GmbH 6.432,439 B1 8, 2002 Suzuki et al. 6,464,987 B1 10/2002 Fanara et al. (*) Notice: Subject to any disclaimer, the term of this 6,605,298 B1 8/2003 Leigh et al. 6,645,520 B2 11/2003 Hsu et al. patent is extended or adjusted under 35 6,835,392 B2 12/2004 Hsu et al. U.S.C. 154(b) by 0 days. 7,244447 B2 7/2007 Hsu et al. 7,473.432 B2 1/2009 Cevc et al. This patent is Subject to a terminal dis 9,005,626 B2 4/2015 Seigfried claimer. 2002fOO39756 A1 4/2002 Bang et al. 2003/OO78172 A1 4/2003 Guiramand et al. (21) Appl. No.: 14/633,929 2003/0170194 A1 9, 2003 Piotrowiak et al. 2004/OO37876 A1 2/2004 Geisslinger et al. (22) Filed: Feb. 27, 2015 (Continued) (65) Prior Publication Data FOREIGN PATENT DOCUMENTS US 2016/0022579 A1 Jan. 28, 2016 CA 22O1358 A1 4f1996 CA 2691 393 A1 12/2008 Related U.S. Application Data (Continued) (63) Continuation of application No. 12/838.737, filed on Jul. 19, 2010, now Pat. No. 9,005,626. OTHER PUBLICATIONS Author: Sonja Hoeller et al; Title: Multinuclear NMR characteri (30) Foreign Application Priority Data sation and dermal delivery of fluorinated drugs in Soybean microemulsion systems; Journal or Book Title: Journal of pharma Jul. 24, 2009 (DE) ........................ 10 2009 O34 603 ceutical sciences Volume and Issue No. 98, pp. 2686-2695; Publish online Dec. 22, 2008.* (51) Int. Cl. Brunner, M., et al., "Favourable Dermal Penetration of Disclofenac A6 IK 9/12 (2006.01) after Administration to the Skin Using a Novel Spray Gel Formu A6 IK 9/00 (2006.01) lation.” British Journal of Clinical Pharmacology (2005) pp. 1-5. Definition of phospholipid—download from http://www.biology A6 IK3I/I67 (2006.01) online.org/dictionary/Phospholipid, Feb. 25, 2014. A6 IK3I/92 (2006.01) Eisvogel, M., “Whipping up Cosmetic Foams', Cossma: Cosmetics, A6 IK3I/I96 (2006.01) Spray Technology, Marketing, Braun Fachverlage, Karlsruhe, DE, A6 IK 3/474 (2006.01) (2001, pp. 56, 58. A 6LX 3/573 (2006.01) Guo et al., “Enzymatic modificatiton of phospholipids for functional A6 IK3I/7048 (2006.01) applications and human nutrition'. Biotech Advances, 23:203-259 (52) U.S. Cl. (2005). CPC ............ A61K 9/122 (2013.01); A61K 9/0014 (Continued) (2013.01); A61K 31/167 (2013.01); A61 K 31/192 (2013.01); A61K 31/196 (2013.01); Primary Examiner — Yanzhi Zhang A61K 31/4174 (2013.01); A61K 3 1/573 (74) Attorney, Agent, or Firm — Goodwin Procter LLP (2013.01); A61 K3I/7048 (2013.01) (57) ABSTRACT (58) Field of Classification Search A liquid composition Suitable for topical use comprising is CPC .............................. A61 K9/0014; A61K 9/122 provided that includes a phospholipid foaming agent and at USPC ............................ 424/184.1, 278.1: 514/159 least one solvent; and a pharmaceutically acceptable active See application file for complete search history. agent; wherein the liquid composition is capable of mechanically foaming without an additional propellant; and (56) References Cited wherein upon mechanical foaming of 250 ml of the liquid U.S. PATENT DOCUMENTS composition results in a foam with a foam Volume of at least about 400 ml and a foam stability wherein at least about 50% 4,863,970 A 9, 1989 Patel et al. of the foam volume is still present after about 5 minutes at 4,975.425. A 12/1990 Barnett, Jr. 4,983,765 A 1/1991 Lukas et al. 25°C., as determined using a SITA foam measurement. Also 5,004,611 A 4/1991 Leigh provided herein are methods of making disclosed composi 5,200,198 A 4, 1993 Geisslinger et al. tions and methods of use. 5,206,029 A 4, 1993 Geisslinger et al. 5,369,131 A 11/1994 Poli et al. 12 Claims, 19 Drawing Sheets US 9,693,956 B2 Page 2 (56) References Cited EP 1092970 A2, 4, 2001 JP S50-070410 A 6, 1975 U.S. PATENT DOCUMENTS JP S54-073135 A 6, 1979 JP HO1-242521 A 9, 1989 2005/0043280 A1 2/2005 Geisslinger et al. JP 2008-540530 A 11, 2008 2005/0079139 A1 4/2005 Jacques et al. JP 2009-522349 A 6, 2009 2005/0220857 A1 10/2005 Purpura et al. WO WO-93/10760 A1 6, 1993 2005/0250666 A1* 11/2005 Gatlin ...................... C09K 8/38 WO WO-93/10771 A1 6, 1993 2007/0224153 A1 9, 2007 LiBrizzi ................. A61s51942 WOW. WO-OO,W.E. SOO19 A2R. 8, 2000E. 2007/0231353 A1 10, 2007 Gilbard et al. WO WO-OOf 7467O A1 12/2000 2008/0233183 A1* 9, 2008 McCook .................. A6K 814 WO WO-2006/121880 A 11/2006 424/450 WO WO-2007/080539 A2 7/2007 2009.0036339 A1 2/2009 Sans et al. W. W.23A, 72 2009,0162421 A1 6/2009 Geisslinger et al. 2009/0232743 A1* 9, 2009 Varanasi .............. A61K90014 424/45 OTHER PUBLICATIONS 2010.0143449 A1 6, 2010 Kolesnikov 2010, O189662 A1 7/2010 Neubourg Hoeller et al., “Multinuclear NMR characterisation and dermal 2011/02077652011/00591.17 A1 3/20118/2011 SeigfriedVan Den Bussche et al. deliveryry of fluorinatedIluorinated drugsarugs iin soybean-microemulsionbean-mi lsi systems,tems. JJ. 2011/0269704 Al 11/2011 Seigfried Pharma. Sci., 98:2686-2695 (2009). 2011/0269851 A1 11/2011 Bortlik et al. International Search Report for PCT/DE2010/000818 mailed on Jul. 2013/03092.15 A1 11/2013 Seigfried 7, 2011. Predel et al., “A randomized, double-blind, placebo-controlled FOREIGN PATENT DOCUMENTS multicentre study to evaluate the efficacy and safety of diclofenac 4% spray gel in the treatment of acute uncomplicated ankle sprain'. CA 27.52849 A1 1, 2011 J. Intl. Med. Res., 41(4): 1187-1202 (2013). DE 1952O659 A1 12/1996 Public Assessment Report—Diclofenac Sodium 4% Spray Gel, DE 1974OO95 C2 3, 1999 Mika Pharma GmbH (Mar. 20, 2006). DE 19949922 C1 5, 2001 Tarenflurbil, from Wikipedia, printed Mar. 26, 2010. DE 102010O2.7315 A1 1, 2011 Wendel, A., “Lecithin,” (1995) Kirk-Othmer Encyclopedia of EP O 0510561510 561 A1 * 10, 1992 Chemicalemical Technology.lechnology, fourFourth Edition,tion, vol. 15, pp. 192-210 EP O521398 A2 1, 1993 Written Opinion for PCT/DE2010/000818 dated Jan. 24, 2012 EP O565713 A1 10, 1993 (English Translation). EP O613728 A2 9, 1994 EP 0704206 A1 4, 1996 * cited by examiner U.S. Patent Jul. 4, 2017 Sheet 1 of 19 US 9,693,956 B2 12OO 1. mir-m-m-------------wave-m---saw-w-m--------- 5 600 -- 1st measurement : -- 2nd measurement s -- 3rd measurement >E 400 ---------------...------- ----------- - s S. 200 ------------------------------------------------ m O --------- -T- --- O.O 5.0 10.0 15.0 2O.O 25.O 3OO 35.0 time (min) Figure 1 U.S. Patent Jul. 4, 2017 Sheet 3 of 19 US 9,693,956 B2 1200 ----- ---------...- -------------------------------.W 1000 --- --------- 800 ------------- m --- --------- E 600 +--- for-o-o-o-o-o-o-o-o--- 1st measurement | - 2nd measurement E 400 ---or- --m-mw------umu -- 3rd measurement co i.e., now-in-a----...-ari wross-sect. E cas C 200 - --- --- O - --- -- -- f - 0.0 5.0 10.0 15.0 20.0 25.0 30.0 35.0 time (min) Figure 3 U.S. Patent Jul. 4, 2017 Sheet 4 of 19 US 9,693,956 B2 1 200 -- --- --- 1 OOO . mm ------. S ------------------------------------------------------------ o 6OO t ...-------------------,-,-,-, ... ... ------------------------- St eastreet 5 -o-, 2nd measurement O 400 --- m - 3rd measurement ors S. 2OO O - m-m- ------------- --- 50 1 OO 15.0 200 25.0 30.0 350 time (min) Figure 4 U.S. Patent Jul. 4, 2017 Sheet 5 of 19 US 9,693,956 B2 200 1000 g 600 . -as-, 2nd measurement -- 3rd measurement 4O O 200 O.O 50 10.0 15.0 200 250 30.0 35.0 time (min) Figure 5 U.S. Patent Jul. 4, 2017 Sheet 6 of 19 US 9,693,956 B2 1200 - 1 OOO - --- - 800 1st measurement -- 2nd measurement S ... 3rd measurement a 600 - - T" ...------- vmm-mm-um-m-m-m-m-ul S E 9 S its S. 200 - - - -m-m-m------ -------------w 0 - s ----------.......... r -----...- O.O 5.O 10.0 15.O 2O.O 25.0 3OO 35.0 time (min) Figure 6 U.S. Patent Jul. 4, 2017 Sheet 7 of 19 US 9,693,956 B2 1200 -...-ro 1 OOO now--- ----------- 800 S 600 - -- 1st measurementdumula-a-N-woma---------------- s -o-, 2nd measurement S 400 — -- 3rd measurement s S. 200 v-M- M-----------------------------M. O ...un- mm - error- r OO 5.O 10.0 150 200 250 30.0 350 time (min) Figure 7 U.S.
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