USOO9636405B2 (12) United States Patent (10) Patent No.: US 9,636.405 B2 Tamarkin et al. (45) Date of Patent: May 2, 2017 (54) FOAMABLE VEHICLE AND (56) References Cited PHARMACEUTICAL COMPOSITIONS U.S. PATENT DOCUMENTS THEREOF M (71) Applicant: Foamix Pharmaceuticals Ltd., 1,159,250 A 1 1/1915 Moulton Rehovot (IL) 1,666,684 A 4, 1928 Carstens 1924,972 A 8, 1933 Beckert (72) Inventors: Dov Tamarkin, Maccabim (IL); Doron 2,085,733. A T. 1937 Bird Friedman, Karmei Yosef (IL); Meir 33 A 1683 Sk Eini, Ness Ziona (IL); Alex Besonov, 2,586.287- 4 A 2/1952 AppersonO Rehovot (IL) 2,617,754. A 1 1/1952 Neely 2,767,712 A 10, 1956 Waterman (73) Assignee: EMY PHARMACEUTICALs 2.968,628 A 1/1961 Reed ... Rehovot (IL) 3,004,894. A 10/1961 Johnson et al. (*) Notice: Subject to any disclaimer, the term of this 3,062,715. A 1 1/1962 Reese et al. tent is extended or adiusted under 35 3,067,784. A 12/1962 Gorman pa 3,092.255. A 6/1963 Hohman U.S.C. 154(b) by 37 days. 3,092,555 A 6/1963 Horn 3,141,821 A 7, 1964 Compeau (21) Appl. No.: 13/793,893 3,142,420 A 7/1964 Gawthrop (22) Filed: Mar. 11, 2013 3,144,386 A 8/1964 Brightenback O O 3,149,543 A 9/1964 Naab (65) Prior Publication Data 3,154,075 A 10, 1964 Weckesser US 2013/0189193 A1 Jul 25, 2013 3,178,352. A 4 1965 Erickson (Continued) Related U.S. Application Data FOREIGN PATENT DOCUMENTS (63) Continuation of application No. 13/708,284, filed on AU 19878O257 9, 1986 Dec. 7, 2012, now abandoned, which is a continuation AU 7825.15 12/2005 of application No. 12/767,511, filed on Apr. 26, 2010, (Continued) now Pat. No. 8.362,091, which is a continuation of application No. 11/430,599, filed on May 9, 2006, OTHER PUBLICATIONS now Pat. No. 7.704,518, and a continuation-in-part of application No. 10/835,505, filed on Apr. 28, 2004, Sorbitan esters online retrieved on Jul. 1, 2016 from: http://www. now Pat. No. 7,820,145. drugfuture.com/chemdata sorbitan-esters.html 2 pages. Chapter 1 Meaning of HLB Advantages and Limitations 1980; 4 (60) Provisional application No. 60/679,020, filed on May pages. 9, 2005, provisional application No. 60/784,793, filed Sreenivasan et al. (Journal of the American Oil Chemists Society. on Mar. 21, 2006, provisional application No. 1956:33:61-66).* 6O753O O15 filed O Dec. 16 2003 provisional U.S. Appl. No. 60/815,948, filed Jun. 23, 2006, Tamarkin. vs. c. s s U.S. Appl. No. 60/818,634, filed Jul. 5, 2006, Friedman. application No. 60/492.385, filed on Aug. 4, 2003. U.S. Appl. No. 60/843,140, filed Sep. 8, 2006, Tamarkin. (51) Int. Cl. U.S. Appl. No. 61/248,144, filed Oct. 2, 2009, Tamarkin. A6 IK 47/10 (2017.01) U.S. Appl. No. 61/322,148, filed Apr. 8, 2010, Tamarkin. A6 IK 9/12 (2006.01) U.S. Appl. No. 61/363,577, filed Jul. 12, 2010, Eini. A6IL 9/01 (2006.01) (Continued) A61O 19/00 (2006.01) A6 IK 8/04 (2006.01) Primary Examiner — Ernst V Arnold A6 IK 9/00 (2006.01) (74) Attorney, Agent, or Firm — Finnegan, Henderson, A6 IK 47/4 (2017.01) Farabow, Garrett & Dunner LLP. A6 IK 47/38 (2006.01) AOIN 25/16 (2006.01) (57) ABSTRACT (52) U.S. Cl. Ahvgroscopicygroscop1c ppharmaceutical compositionp includes at least CPC .............. A61K 47/10 (2013.01); A0IN 25/16 one hygroscopic Substance at a concentration Sufficient to (2013.01); A61K 8/046 (2013.01); A61 K provide an Aw value of less than 0.9 or about 0.9 to about 9/0014 (2013.01); A61K 9/0034 (2013.01); 0.7 and an antiinfective agent. A foamble pharmaceutical A61K 9/12 (2013.01); A61K 9/122 (2013.01); carrier includes about 50% to about 98% of a polar solvent A61K 47/14 (2013.01); A61K 47/38 (2013.01); selected from the group consisting of a polyol and PEG: 0% A61O 19/00 (2013.01); YIOS 514/945 to about 48% of a secondary polar solvent; about 0.2% to (2013.01) about 5% byy weight of a surface-active agent;9. about 0.01% (58) Field of Classification Search to about 5% by weight of at least one polymeric agent; and CPC ...... A61K 47/10; A61K 8/046; A61K 9/0014: a liquefied or compressed gas propellant at a concentration A61K 9/0034; A61 K9/12: A61 K 9/122; of about 3% to about 25% by weight of the total composi A61L 9/01: A61L 9/042: A61Q 19/00; tion. Y1OS 514/945 See application file for complete search history. 25 Claims, 1 Drawing Sheet US 9,636.405 B2 Page 2 (56) References Cited 4,214,000 A 7/1980 Papa 4,226,344 A 10, 1980 Booth et al. U.S. PATENT DOCUMENTS 4,229,432 A 10, 1980 Geria 4,230,701 A 10, 1980 Hollick et al. 3,236,457 A 2, 1966 Kennedy et al. 4,241,048 A 12/1980 Durbak et al. 3,244,589 A 4, 1966 Sunnen 4,241,149 A 12/1980 Labes et al. 3,252,859 A 5, 1966 Silver 4,252,787 A 2, 1981 Sherman et al. 3,261,695 A 7, 1966 Sienkiewicz 4,254,104 A 3, 1981 Suzuki et al. 3,262,867 A 7, 1966 Lehmann 4,268.499 A 5, 1981 Keil 3,263,869 A 8, 1966 Corsette 4,271,149 A 6, 1981 Winicov et al. 3,298.919 A 1/1967 Bishop et al. 4.278,206 A 7/1981 Prussin 3,301,444 A 1, 1967 Wittke 4,292,250 A 9, 1981 DeLuca et al. 3,303,970 A 2f1967 Breslau et al. 4,292,326 A 9, 1981 Nazzaro-Porro et al. 3,330,730 A 7, 1967 Hernandez 4,299,826 A 11/1981 Luedders 3,333,333 A 8, 1967 Noack 4,305,936 A 12/1981 Klein 3,334,147 A 8, 1967 Brunelle et al. 4,309,995 A 1/1982 Sacco 3,342,845. A 9/1967 Sayigh et al. 4,310,510 A 1/1982 Sherman et al. 3,346,451 A 10/1967 Collins et al. 4.323,582 A 4/1982 Siegel et al. 3,366,494. A 1, 1968 Bower et al. 4.323,694. A 4, 1982 Scala, Jr. 3,369,034 A 2f1968 Chalmers 4.325,939 A 4, 1982 Shah 3,377,004 A 4, 1968 Wittke 4.329,990 A 5, 1982 Sneider 3,383,280 A 5, 1968 Kuehns 4,335,120 A 6, 1982 Holick et al. 3,384,541 A 5, 1968 Clark et al. 4.338,211 A * 7/1982 Stiros ....................... A61K 8/42 3,395,214 A 7, 1968 Mummert 510, 159 3,395.215 A 7, 1968 Schubert 4,352,808 A 10, 1982 Rane et al. 3,401,849 A 9/1968 Weber, III 4,363,806 A 12/1982 Bergström et al. 3.419,658 A 12/1968 Sanders 4.385,161 A 5/1983 Caunt et al. 3.456,052 A 7, 1969 Gordon 4,386,104 A 5/1983 Nazzaro-Porro 3,527,559 A 9, 1970 Sliwinski 4,393,066 A 7/1983 Garrett et al. 3,540,448 A 11/1970 Sunnen 4.427,670 A 1/1984 Ofuchi et al. 3,559,890 A 2f1971 Brooks et al. 4,439,416 A 3, 1984 Cordon et al. 3,561,262 A 2f1971 Borucki 4,439,441 A 3/1984 Hallesy et al. 3,563,098 A 2/1971 Weber, III 4,440,320 A 4, 1984 Wernicke 3,574,821 A 4, 1971 Pfirrmann 4,447.486 A 5/1984 Hoppe et al. 3,577,518 A 5/1971 Shepherd 4,469,674. A 9, 1984 Shah et al. 3,667,461 A 6, 1972 Zamarra 4,508,705 A 4, 1985 Chaudhuri et al. 3,751,562 A 8, 1973 Nichols 4,522,948 A 6, 1985 Walker 3,770,648 A 11/1973 Mackles 4,529,601 A 7/1985 Broberg et al. 3,787,566 A 1/1974 Gauvreau 4,529,605 A 7, 1985 Lynch et al. 3,819,524 A 6, 1974 Schubert et al. 4,552,872 A 11/1985 Cooper et al. 3,824.303 A * 7/1974 Lanzet et al. ................... 424/47 4,574,052 A 3/1986 Gupte et al. 3,841,525 A 10/1974 Siegel 4,576,961 A 3, 1986 Lorck et al. 3,849,569 A 11/1974 Mead 4,595,526 A 6, 1986 Lai 3,849,580 A 11/1974 Weinstein et al. 4,603,812 A 8, 1986 Stoesser et al. 3,865,275 A 2f1975 De Nunzio 4,607,101 A 8, 1986 Bernstein 3,866,800 A 2, 1975 Schmitt 4,627,973 A 12/1986 Moran et al. 3,878,118 A 4, 1975 Watson 4,628,063 A 12/1986 Haines et al. 3,882,228 A 5/1975 Boncey et al. 4,661,340 A 4, 1987 Nagy née Kricsfalussy et al. 3,886,084 A 5, 1975 Vassiliades 4,661.524. A 4, 1987 Thomson et al. 3,890,305 A 6, 1975 Weber et al.