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(12) United States Patent (10) Patent No.: US 7,556,820 B2 Ramirez Et Al

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(12) United States Patent (10) Patent No.: US 7,556,820 B2 Ramirez Et Al US007556820B2 (12) United States Patent (10) Patent No.: US 7,556,820 B2 Ramirez et al. (45) Date of Patent: Jul. 7, 2009 (54) STABLE ORGANIC PEROXIDE 4,906,617 A 3/1990 Jacquet et al. COMPOSITIONS 4,923,900 A 5, 1990 De Villez 4,925,666 A 5/1990 Decker, Jr. et al. (75) Inventors: José E. Ramirez, Trumbull, CT (US); 4.959,205 A 9, 1990 Brunner et al. Joseph R. Faryniarz, Middlebury, CT 4,960,772 A 10/1990 Sebag et al. (US) 5,019,567 A 5/1991 Philippe et al. 5,023,090 A 6, 1991 Levin ......................... 424,520 (73) Assignee: JR Chem, LLC, Key West, FL (US) 5,086,075 A 2, 1992 DeVillez (*) Notice: Subject to any disclaimer, the term of this 5,409,917 A 4, 1995 Robinson et al. patent is extended or adjusted under 35 5,466,446 A 1 1/1995 Stiefel et al. U.S.C. 154(b) by 0 days. 5,505,949 A * 4/1996 Benitez ...................... 424/401 5,514,670 A 5/1996 Friedman et al. (21) Appl. No.: 12/264,517 5,545.407 A 8/1996 Hall et al. 5,585,109 A * 12/1996 Hayward et al. ............ 424/450 (22) Filed: Nov. 4, 2008 5,607.980 A 3/1997 McAtee et al. O O 5,612,324 A 3/1997 Guang Lin et al. (65) Prior Publication Data 5,614,201 A * 3/1997 Slavtcheffet al. ........... 424/401 US 2009/007617OA1 Mar. 19, 2009 5,621,006 A 4, 1997 Yu et al. O O 5,632,996 A 5/1997 Ramirez et al. Related U.S. Application Data 5,637,354 A 6/1997 Segalla (63) Continuation-in-part of application No. 1 1/986,442, 5,690,946 A 1 1/1997 Koulbanis et al. filed on Nov. 21, 2007, now Pat. No. 7,445,729, which 5,733,886 A 3/1998 Baroody et al. is a continuation of application No. 1 1/476,527, filed 5,767,098 A 6/1998 Klein et al. on Jun. 28, 2006, now abandoned. 5,789,445 A 8/1998 Schweiger (60) Provisional application No. 60/695.223, filed on Jun. 5,879,716 A 3, 1999 Katz et al. 29, 2005. (51) Int. Cl. A6 IK 8/22 (2006.01) (Continued) A6 IK 8/38 (2006.01) COB IS/It (2006.01) FOREIGN PATENT DOCUMENTS C09K I5/08 (2006.01) WO WOO3O3951.0 A1 5/2003 (52) U.S. Cl. ....................... 424/401; 424/404: 514/714; 514/859; 514/846; 514/937; 514/718; 252/186.26; 252/186.42; 252/404; 252/.407 (58) Field of Classification Search ................. 424/404; OTHER PUBLICATIONS 514/714 See application file for complete search history. 1995 U.S. Pharmacopeia/National Formulary USP 23/NF 18, pp. 179-180. (56) References Cited U.S. PATENT DOCUMENTS (Continued) Primary Examiner Joseph D. Anthony 3,538,011 11, 1970 Van der Klaauw (74) Attorney, Agent, or Firm—Carter, DeLuca, Farrell & 3,887,652 6, 1975 Carrocket al. Schmidt, LLP 4,056,611 1 1/1977 Young s 4,318,907 3/1982 Kligman et al. 4,350,681 9, 1982 Fulton, Jr. (57) ABSTRACT 4,387,107 6, 1983 Klein et al. 4.416,873 11, 1983 Puchalski et al. 4,440,885 4, 1984 Tamosauskas Benzoyl peroxide compositions are stabilized against decom 4497,794 2f1985 Klein et al. position by the use of antioxidants, resulting in increased 4,520,133 5, 1985 Dines et al. shelflife of products made using the compositions. Treatment 4,593,046 6, 1986 Gruber of truncal acne Vulgaris with a combination of actives, namely 4,608,392 8/1986 Jacquet et al. benzoyl peroxide and salicylic acid, is provided via regimens 4,609,674 9/1986 Gupte that include applying Such benzoyl peroxide compositions to 4,640,932 2, 1987 Fong et al. an area of the body afflicted with acne, after a waiting period 4,664,847 5, 1987 Williams rinsing the benzoyl peroxide-treated area (e.g., by shower s: g 8. Stal ing), drying the rinsed area, and then applying a topical, at 4,767,750 8/1988 Jacquet et al. S.Filly neutralized salicylic acid composition to the 4,803,228 2/1989 Jacquet et al. 4,844,886 7, 1989 Hartmann et al. 4,857,302 8, 1989 Decker, Jr. et al. 2 Claims, No Drawings US 7,556,820 B2 Page 2 U.S. PATENT DOCUMENTS 7,153,888 B2 12/2006 Schwarz et al. 7,390,431 B2 * 6/2008 Faryniarz et al........ 252/18626 5,894,019 A 4/1999 Hesse et al. 7,445,729 B2 * 1 1/2008 Faryniarz et al........ 252/18626 5,910,312 A * 6/1999 Fried .......................... 424/401 2002fOO48558 A1 4/2002 Niemiec et al. 5,912.255. A 6/1999 Bussell 2003/0064084 A1 4/2003 Bhagwat et al. 5,916,574 A 6, 1999 Fried et al. 2004/0101566 A1 5/2004 Cooper et al. 5.948,416 A 9/1999 Wagner et al. 2004/0156873 A1* 8/2004 Gupta ........................ 424/401 5,993,833. A 11/1999 De Lacharriere et al. 2004/0170659 A1 9/2004 Bhagwat et al. 5.997,885. A 12/1999 Koulbanis et al. 2004/021 1938 A1 10, 2004 Bocket al. 6,117.843 A 9/2000 Baroody et al. 2004/0223900 A1 11/2004 Khabashesku et al. 6,120,756 A * 9/2000 Markowitz ................. 424.70.1 2006, O135822 A1 6/2006 Schwarz et al. 6,277,892 B1 8/2001 Deckner et al. 2006/0202160 A1* 9/2006 Faryniarz et al. ....... 252/186.42 6,369,247 B1 4/2002 Miller et al. 2006/0204530 A1* 9, 2006 Ramirez et al. ............. 424/401 6,433,024 B1 8/2002 Popp et al. 2007/0001145 A1* 1/2007 Faryniarz et al. 252/186.42 6,448,233 B1 9/2002 Lefevre et al. 2007/0003504 A1 1/2007 Ramirez et al. .......... 424.70.13 6,482.431 B2 11/2002 Smith 6,596,287 B2 7/2003 Deckers et al. 6,713,075 B2 3/2004 Bekele OTHER PUBLICATIONS 6,737,070 B1 5, 2004 Burkhart T.W. Graham Solomons, Fundamentals of Organic Chemistry, 1997. 6,740,330 B1 5/2004 Bernstein John Wiley & Sons, Inc., Fifth Edition, pp. 620-621, 640-641, 668, 6,762,158 B2 7/2004 Lukenbach et al. T60. 6,878,378 B1 4/2005 Yamaki et al. 6,896,890 B2 5/2005 Singh et al. * cited by examiner US 7,556,820 B2 1. 2 STABLE ORGANIC PEROXDE 10:1. The composition may include a solvent in which the COMPOSITIONS organic peroxide is soluble. Furthermore, the organic peroX ide, such as benzoyl peroxide, may be a liquid in which CROSS REFERENCE TO RELATED antioxidant is soluble. In other embodiments, the organic APPLICATION peroxide may be a solid in which antioxidant can be dis persed. This application is a continuation-in-part of U.S. applica In embodiments, regimens for the treatment of truncal acne tion Ser. No. 11/986,442 filed Nov. 21, 2007, now U.S. Pat. Vulgaris in accordance with the present disclosure include No. 7,445,729 which is a continuation and claims priority applying a composition containing benzoyl peroxide to an benefit of U.S. application Ser. No. 1 1/476,527 filed Jun. 28, 10 area of afflicted with acne, after a waiting period rinsing the 2006 which claims priority to U.S. Provisional Application benzoyl peroxide-treated area (e.g., by showering), drying No. 60/695,223 filed Jun. 29, 2005. The entire disclosures of the rinsed area and then applying a topical neutralized sali these prior applications are incorporated herein by reference. cylic acid composition to the afflicted area. The present regi men thus provides treatment with a combination of actives, BACKGROUND 15 namely benzoyl peroxide and salicylic acid. Despite the tem porary nature of the application of the benzoyl peroxide com 1. Technical Field position, an effective amount of benzoyl peroxide is absorbed This disclosure relates to the preparation of compositions by the skin. Even after rinsing, sufficient benzoyl peroxide containing stable organic peroxide in Solution. The composi remains within the skin at the afflicted area to work in concert tions are useful for topical application to human skin and/or with the Subsequently applied salicylic acid. Advantageously, allow stable organic peroxides to be utilized in new product since the benzoyl peroxide is absorbed by the skin and no forms. Products (e.g., industrial, pharmaceutical or consumer longer on the Surface, the present regimen effectively treats based products) formulated using these compositions exhibit truncal acne without discoloring or staining clothing. extended shelflife. Such compositions also have unique pro cessing capabilities. 25 These and other aspects of this disclosure will be evident 2. Background of Related Art upon reference to the following detailed description. Organic peroxides are used in many products. For example, benzoyl peroxide is used in pharmaceutical and DETAILED DESCRIPTION OF PREFERRED consumer products as an active ingredient for therapeutic EMBODIMENTS treatments. Organic peroxides are unstable. This instability is 30 a desired trait when these materials are used for free radical Compositions in accordance with this disclosure include at initiation. When organic peroxides are used for purposes least one antioxidant in combination with one or more organic other than free radical initiation, however, it is desirable to peroxides. The antioxidant may be any of the type materials have the material be as stable as possible. Instability is prob that are soluble in the solvent carrier for the desired organic lematic and leads to short shelf lives, required expiration 35 peroxide, and/or soluble or dispersible in the organic peroX dating, higher product costs, special storage considerations, ide itself.
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