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(12) United States Patent (10) Patent No.: US 9,511,042 B2 Falla Et Al

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(12) United States Patent (10) Patent No.: US 9,511,042 B2 Falla Et Al USOO951 1 042B2 (12) United States Patent (10) Patent No.: US 9,511,042 B2 Falla et al. (45) Date of Patent: Dec. 6, 2016 (54) N-ACYL AMINO ACID DERIVATIVES FOR JP 08-3375.15 12/1996 TREATING SKIN CONDITIONS SUCH AS E. SI36 758 CELLULTE JP 2007-15384.5 6, 2007 JP 2007-314464 A 12/2007 (75) Inventors: Timothy J. Falla, Woodinville, WA RU 224.5358 C2 1/2005 (US); Lijuan Zhang, Kenmore, WA WO 90.14429 A1 11, 1990 (US) WO 2004/069240 A2 8, 2004 WO 2006/0298.18 A2 3, 2006 WO WO20060298.18 * 3, 2006 (73) Assignee: setts biomedix INC. Bothell, WO 2006/082978 A1 8/2006 (*) Notice: Subject to any disclaimer, the term of this OTHER PUBLICATIONS patent is extended or adjusted under 35 Kono, Mitsuyoshi et al.JP2006183039. Jul. 2006. Machine Trans U.S.C. 154(b) by 64 days. lation. Caruso et al. (Journal of Plastic, Reconstructive & Aesthetic Surgery (21) Appl. No.: 13/703,292 (2008) 61, 1321-1324).* Thomas et al. EP1938789. Jul 2008. (22) PCT Fed: Jun. 28, 2011 Patani et al. (Chemical Reviews, 1996, vol. 96, No. 8).* Enzo Emanuele, M.D. (Cellulite: Advances in treatment: Facts and (86). PCT No.: PCT/US2O11AO42123 controversies. Clinics in Dermatology (2013) 31, 725-730).* See Luebberding et al. Cellulite: An Evidence-Based Review. Am J S 371 (c)(1), Clin Dermatol (2015) 16:243-256.* (2), (4) Date: Dec. 10, 2012 Notification of Transmittal of the International Search Report and The Written Opinion of the International Searching Authority, or the (87) PCT Pub. No.: WO2O12AOO3176 Declaration, dated Aug. 24, 2011, 16 pages. Article from Nutrition & Metabolism, Biomed Central; by Guo Wen PCT Pub. Date: Jan. 5, 2012 et al., entitled “Modulation of Adipocyte Lipogenesis by Octanoate: Involvement of Reactive Oxygen Species'; vol. 3, No. 1, Jul. 27. (65) Prior Publication Data 2006; 8 pages. Article from Tetrahedron Letters, by Jin Zhuang et al., entitled US 2013 FOO96143 A1 Apr. 18, 2013 “Copper Mediated Oxidation of Amides to Imides by Selectfluor': vol. 52, No. 16, Apr. 20, 2011, pp. 1956-1959. Related U.S. Application Data Fujimoto, Y., et al., 2006. Long Chain fatty acids induce lipid droplet formation in a cultured human hepatocyte in a manner (60) Provisional application No. 61/361,179, filed on Jul. deopendent of acyl-CoA synthesis. Biol. Pharm. Bull. 29 (11) 2, 2010. 2174-21.80. Guo, W., et al., 2006. Modulation of adipogensis by octanoate: (51) Int. Cl. involvement of reactive oxygen species. Nutrition & Metabolism A6 IK 8/44 (2006.01) 3(30) 1-8. A6 IK 8/42 (2006.01) Han, J., et al., 2002. Octanoate attenuates adipogenesis in 3T3 C07C 237/12 (2006.01) preadipocytes. J. Nutr. 132:904-910. A6 IK3I/98 (2006.01) pubchem.ncbi.nim.nih.gov/summary/summary.cgi?sid=47288.15. A6 IK 3L/20 (2006.01) pubchem.ncbi.nim.nih.gov/summary/summary.cgi?sid=37555064. pubchem.ncbi.nim.nih.gov/summary/summary.cgi?sid=75.064649. A61O 19/06 (2006.01) Newew Zealand ExaminatiExamination Report dated Dec. 11, 2013, relating to A6 IK 45/06 (2006.01) New Zealand Application No. 605804. (52) U.S. Cl. Kawase, Tokuzo et al., “A Novel Synthesis of N-Alkoxycarbonyl CPC ............... A61K 31/198 (2013.01); A61K 8/42 Amino Acids and Surfactant Properties of Their Sodium Salts.” (2013.01); A61K 8/44 (2013.01); A61 K3I/20 Journal of Oleo Science, 59, (4) 191-201 (2010). (2013.01); A61K 45/06 (2013.01); A61O 19/06 (Continued) (2013.01); C07C 237/12 (2013.01) (58) Field of Classification Search Primary Examiner — Jeffrey S Lundgren CPC ............................. C07C 237/07; CO7C 237/12 Assistant Examiner — Chris Simmons See application file for complete search history. (74) Attorney, Agent, or Firm — Thomas Law PLLC (56) References Cited (57) ABSTRACT U.S. PATENT DOCUMENTS The invention relates to Small molecules having biological and therapeutic activity. Particularly, the invention relates to 5,510,531 A 4/1996 Higuchi et al. Small molecules having lipolytic and anti-adipogenic activ 2003/0018081 A1 1/2003 Piomelli et al. ity. Two examples of Such molecules are 4-methyl-2-(oc 2005, OO19372 A1 1/2005 Corkey et al. tanoylamino) pentanoic acid and N-isopentyloctanamide. The invention further relates to methods of preventing or FOREIGN PATENT DOCUMENTS treating skin conditions such as cellulite using Small mol EP OSOO332 A2 8, 1992 ecules having lipolytic and anti-adipogenic activity. EP 1938789 * 7/2008 JP HO2-2681.45 A 11, 1990 20 Claims, 6 Drawing Sheets US 9,511,042 B2 Page 2 (56) References Cited OTHER PUBLICATIONS Sivagnanam, G. Mesotherapy. The french connection. J Pharmacol Pharmacother serial online 2010 cited Dec. 10, 2015; 1:4-8. Available from: http://www.jpharmacol.com/text.asp?2010/1/1/4/ 64529. Caruso, M.K. et al...An evaluation of mesotherapy solutions for inducing lipolysis and treating cellulite.J Plast Reconstr Aesthet Surg (2007), doi:10.1016/j.bips.2007.03.039. RU2013 104424, “Official Action,” mailed Feb. 2, 2016, 6 pgaes. PH1-2012-502423, “Substantive Examination Report,” mailed Mar. 31, 2016, 2 pages. RU2013 104424, “Decision of Grant,” mailed Apr. 22, 2016, 14 pageS. KR10-2013-7001965, "Decision for Patent Grant,' mailed Jun. 14, 2016, 3 pages. JP2013-5 18561, “Notice of Reasons for Refusal, mailed Feb. 2, 2016, 7 pages. Zhang, et al., “Effect of Amide Constituents from Pepper on Adipogenesis in 3T3-L1 Cells.” Bioorganic & Medicinal Chemistry Letters 18 (2008), pp. 3272-3277. Isopentyl caprylamide, RN: 546098-90-2. Datasheet online Toxnet, 2003 retrieved on Sep. 15, 2016). Retrieved from the Internet: <URL: https://chem.nlm.nih.gov/chemidplus/rn/546098 90-2 1 page. JP2013-5 18561. Notice of Reasons for Refusal, mailed Aug. 30. 2016, 5 pages. PH1/2012/502423. Subsequent Substantive Examination Report, mailed Aug. 18, 2016, 2 pages. * cited by examiner U.S. Patent Dec. 6, 2016 Sheet 2 of 6 US 9,511,042 B2 4-Methyl-2-(Octanoylamino) pentanoic acid C14H2NO 3 MW-2S 7 N-isopentyloctanamide U.S. Patent Dec. 6, 2016 Sheet 3 of 6 US 9,511,042 B2 ss s s Ss FIG 3 U.S. Patent Dec. 6, 2016 Sheet 4 of 6 US 9,511,042 B2 s ES isopoti?sio: 33. U.S. Patent Dec. 6, 2016 Sheet S of 6 US 9,511,042 B2 §§§§§ F.G. 6 U.S. Patent Dec. 6, 2016 Sheet 6 of 6 US 9,511,042 B2 MTT tissue viability assay for HB2031 and HB2032 Glycerin HE231 HB2032 Glycerin HE231 HE232 Glycerin HE231 HB2032 FG, 7 US 9,511,042 B2 1. 2 N-ACYL AMNO ACID DERVATIVES FOR would require producing agents that (i) are non-prescription TREATING SKIN CONDITIONS SUCH AS drugs, (ii) are more natural in origin, (iii) exhibit good skin CELLULTE penetration qualities, and (iv) have increased lipolytic activ ity over the currently available molecules. This application is a Section 371, United Stated national stage filing of PCT/US2011/042123 filed 28 Jun. 2011 SUMMARY OF THE INVENTION which claims benefit of priority to U.S. 61/361,179, filed 2 Jul. 2010, each of which is herein incorporated by reference An embodiment of the instant invention can be directed to in its entirety. a method of treating the skin of a mammal, comprising 10 administering to the skin of a mammal a composition. The FIELD OF THE INVENTION composition may comprise a pharmaceutically acceptable carrier and a pharmaceutically effective amount of a com The invention relates to Small molecules having biologi pound or its pharmaceutically acceptable salt. The com cal and therapeutic activity. Particularly, the invention pound in turn may comprise the formula R—C(O)—NH relates to Small molecules having lipolytic and anti-adipo 15 R where R comprises a chain of 5 to 35 carbon atoms, the genic activity. Two examples of Such molecules are R—C(O) portion of the formula is a fatty acyl group, and 4-methyl-2-(octanoylamino) pentanoic acid and N-isopen R2 comprises an organic group. tyloctanamide. The invention further relates to methods of In certain embodiments of the invention, the NH R. preventing or treating skin conditions such as cellulite using portion of the R—C(O)—NH R formula may comprise Small molecules having lipolytic and anti-adipogenic activ an amino acid. In this case the R group comprises the 1ty. alpha-carbon, carboxyl group and side group of the amino acid; the NH group is linked to the alpha-carbon of the BACKGROUND OF THE INVENTION amino acid. In other embodiments of the invention, the NH R portion of the R—C(O)—NH R formula may Cellulite can result from the accumulation of degraded 25 comprise an analog of an amino acid, in which case the fatty tissue in the skin. One or several factors contributing to analog differs from the amino acid by lacking the carboxylic this disorder include poor arterial or venous circulation, group linked to the amino acid alpha-carbon. In this case, the hormonal disturbances and problems with lymphatic drain R group comprises the alpha-carbon and side group of the age. One condition underlying cellulite production is exces amino acid; the NH group is linked to the alpha-carbon of sive fat storage in skin adipocytes. By becoming heavily 30 amino acid analog. The side group of the amino acid or laden with fat (lipids in the form of triglycerides), the amino acid analog may be hydrophobic. The amino acid in adipocytes swell and become hypertrophic, sometimes to a these embodiments (either full amino acid or the above high degree.
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