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(12) United States Patent (10) Patent No.: US 9,713,596 B2 Hong Et Al

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(12) United States Patent (10) Patent No.: US 9,713,596 B2 Hong Et Al USOO9713596B2 (12) United States Patent (10) Patent No.: US 9,713,596 B2 Hong et al. (45) Date of Patent: Jul. 25, 2017 (54) BAKUCHOL COMPOSITIONS FOR FOREIGN PATENT DOCUMENTS TREATMENT OF POST INFLAMMATORY DE 1900 435 7, 1970 HYPERPGMENTATION DE 3417234 A1 * 11, 1985 JP H1171231 A * 3, 1999 ............... A61K 7.00 (75) Inventors: Mei Feng Hong, Lacey, WA (US); Qi JP 2000-327581 A 11 2000 Jia, Olympia, WA (US); Lidia Alfaro JP 2005325 120 A 11/2005 KR 2000-0007648 A 2, 2000 Brownell, Tacoma, WA (US) WO 2006/122160 A2 11/2006 WO 2008. 140673 A1 11, 2008 (73) Assignee: Unigen, Inc., Lacey, WA (US) (*) Notice: Subject to any disclaimer, the term of this OTHER PUBLICATIONS patent is extended or adjusted under 35 Ohno, O. Watabe, T., Kazuhiko, N., Kawagoshi, M., Uotsu, N., U.S.C. 154(b) by 0 days. Chiba, T., Yamada, M., Yamaguchi, K., Yamada, K., Miyamoto, K., Uemura, D. Inhibitory Effects of Bakuchiol, Bavachin, an (21) Appl. No.: 13/365,172 Isobavachalcone Isolated from Piper loungum on Melainin Produc (22) Filed: Feb. 2, 2012 tion in B 16 Mouse Melanoma Cells. Biosci. Biotechnol. Biochem. 74 (7), 1504-1506 (2010).* Prior Publication Data Hiroyuki Haraguchi, Junji Inoue, Yukiyoshi Tamura and Kenji (65) Mizutani.Antioxidative Components of Psoralea corylifolia US 2012/O2O1769 A1 Aug. 9, 2012 (Leguminosae). Phytother. Res. 16, 539-544 (2002).* Petra Clara Arck, et al. Towards a “free radical theory of graying: melanocyte apoptosis in the aging human hair follicle is an indicator Related U.S. Application Data of oxidative stress induced tissue damage. The FASEB Journal, vol. 20, No. 9, pp. E908-E920 and 1567 to 1569. Jul. 2006.* (63) Continuation-in-part of application No. S. Adhikari, et al. Antioxidant Activity of Bakuchiol: Experimental PCT/US2011/026594, filed on Mar. 1, 2011. Evidences and Theoretical Treatments on the Possible Involvement of the Terpenoid Chain. Chem. Res. Toxicol. 2003, 16, 1062-1069.* Erica C. Davis, MD and Valerie D. Callender. “Postinflammatory (60) Provisional application No. 61/438,890, filed on Feb. Hyperpigmentation: A Review of the Epidemiology, Clinical Fea 2, 2011. tures, and Treatment Options in Skin of Color,” J. Clinical and Aesthetic Dermatology 3(7), Jul. 2010, pp. 20-31.).* (51) Int. C. Article “Bakutrol (C) . Nutraceuticals World, Sep. 10, 2010, down A6IP 29/00 (2006.01) loaded Sep. 22, 2014 from the website: http://www. A6 IK3I/60 (2006.01) nutraceutical Sworld.com/issues/2010-10/view Suppliers-corner/ bakutrol?. A6 IK 8/34 (2006.01) Product Information data sheet for BakutrolTM from Unigen, down A6 IK3I/05 (2006.01) loaded Sep. 22, 2014, from the website: http://www.unigen.net/ A61O 19/02 (2006.01) products/bakutrol.* A61O 1702 (2006.01) Gary M. White. Recent findings in the epidemiologic evidence, (52) U.S. C. classification, and Subtypes of acne Vulgaris. J. Am. Acad. CPC .............. A6 IK3I/05 (2013.01); A61K 8/347 Dermatol., vol.39, No. 2, Part 3, pp. S34-S37.* Machine translation of JPH 1171231A to English.* (2013.01); A61 K3I/60 (2013.01); A61O 19/02 Agathiyar paripooranam 400, by Agasthiyar Pub: Rathina Nayakar (2013.01); A61 K 2800/30 (2013.01) & Sons, Thirumagal Vilakku Press, Chennai (1964) p. 65. F. ID: (58) Field of Classification Search GD02.85. None See application file for complete search history. (Continued) (56) References Cited Primary Examiner — Frederick Krass U.S. PATENT DOCUMENTS Assistant Examiner — Michael P. Cohen (74) Attorney, Agent, or Firm — Seed IP Law Group LLP 3,553,236 A 1/1971 Hascher et al. 5,882,672 A 3/1999 Kojima et al. 6,054,584 A 4/2000 Ma et al. (57) ABSTRACT 6,348,204 B1 2/2002 Touzan ......................... 424/401 6,350,476 B1 2, 2002 Hou 6,750,248 B2 6/2004 Yong et al. Methods for treating excess pigmentation, including treat 6,878,381 B2 * 4/2005 Collington .................... 424/401 ment of post inflammatory hyperpigmentation (PIH), are 7,714,026 B2 5, 2010 Lin et al. disclosed. The disclosed methods comprise administration 2004.0043,089 A1 3, 2004 Rabie of a composition comprising bakuchiol Substantially free of 2005, OO48008 A1 3/2005 Gupta furanocoumarins to a mammal. Compositions comprising 2005/0256.209 A1 11, 2005 Lin et al. 2006/025 1749 A1* 11/2006 Jia ........................ A61K90014 bakuchiol and methods for their preparation are also dis 424,757 closed. 2008/0286217 A1* 11/2008 Chaudhuri ...................... 424,59 2010.0189669 A1* 7, 2010 Hakozaki ........................ 424,60 2011/0223267 A1 9/2011 Jia et al. 27 Claims, 7 Drawing Sheets US 9,713.596 B2 Page 2 (56) References Cited Ferrandiz et al., “Effect of Bakuchiol on Leukocyte Functions and Some Inflammatory Responses in Mice,” J. Pharm. Pharmacol. 48(9):975-980, 1996. OTHER PUBLICATIONS Fischer et al., “Chemopreventative Activity of Celecoxib, a Specific Anuboga Vaithiya Navaneetham, by Abdulla Sahib Pub:Palani Cyclooxygenase-2 Inhibitor, and Indomethacin Against Ultraviolet Thandayuthapani Devasthanam Publication, Directorate of Indian Light-Induced Skin Carcinogenesis.” Molecular Carcinogenesis Systems of Medicine, Chennai. (1975) p. 518, F. ID: KS01/121. 25:231-240, 1999. Arkaprakasah by Lankapatiravana—Edited and translation by Fogh et al., “Modulation of Eicosanoid Formation by Lesional Skin Indradeva Tripathi; Krishnadas Academy, Varanasi, Edn. 1, 1995 of Psoriasis: an Ex vivo Skin Model.” Acta Derm Venereol 73:191 AD, p. 44 F. ID: AK14/54A. 193, 1993. Backhouse et al., “Active constituents isolated from Psoralea Goebel et al., “Procainamide, a Drug Cuasing Lupus, Induces glandulosa L. with anti-inflammatory and antipyretic activities.” Prostaglandin H Synthase-2 and Formulation of T Cell-Sensitizing Drug Metabolites in Mouse Macrophages.” Chem. Res. Toxicol. Journal of Ethno-Pharmacology 78:27-31, 2001. 12:488-500, 1999. Bapat et al., “Preparation and in vitro evaluation of radioiodinated Haraguchi et al., “Inhibition of Mitochondrial Lipid Peroxidation by bakuchiol as an anti tumor agent.' Applied Radiation and Isotopes Bakuchiol a Meroterpene from Psoralea corylifolia, ' Planta Med 62:389-393, 2005. 66(6):569-571, 2000. Bayaaz-e-Kabir vol. II, Mohammad Azam Kahn, Daftar-al-Maseeh Hsu et al., “Bakuchiol, an antibacterial component of Psoralidium Karol Bagh, New Delhi, 1938, p. 108, F. ID: MA3/388. tenuiflorum.” Natural Product Research 23(8):781-788, 2009. Bhaisajya Ratnavali by Govinda Dasa Edited by Rajeshvaradutta Iwamura et al., “Cytotoxicity of Corylifoliae Fructus. II.' Shastri, Translated by Ambikaduttashastri: Chaukhamba Sanskrit Cytotoxicity of Bakuchiol and the Analogues.” The Laboratory of Sansthan, Varanasi, Edn. 14' , 2001 This book contains back Scientific and Industrial Research Kinki University, Japan references from 1000 B.C. to 18' century), p. 271, F. ID: AK/1080. 109(12):962-965, 1989. Bharata Bhaisajya Ratnakara Compiled by Naginadasa Office Action, dated Jan. 13, 2013, for corresponding Japanese Chaganalala Saha, Translated by Gopinath Gupta—vol-III: B Jain Patent Application No. 2008-511297, 2 pages. Publishers, New Delhi, Edn. 2". Reprint, Aug. 1999. This book Kaiyadevanighantau (Pathyapathyavibodhakah) by Kaiyadeva contains back references from 1000 B.C. to 20" century), p. 611 F. Edited and translated by P.V. Sharma and Guru Prasad Sharma, ID: RD516. Chaukhambha Orientalia, Varanasi, Edn. 1, 1979, p. 130-131, F. Bharata Bhaisajya Ratnakara Compiled by Naginadasa ID: RS6,257 A. Chaganalala Saha, Translated by Gopinath Gupta—vol-II: B Jain Kaiyadevanighantau (Pathyapathyavibodhakah) by Kaiyadeva Publishers, New Delhi, Edn. 2". Reprint, Aug. 1999. This book Edited and translated by P.V. Sharma and Guru Prasad Sharma, contains back references from 1000 B.C. to 20" century), p. 424 F. Chaukhambha Orientalia, Varanasi, Edn. 1, 1979, p. 131, F. ID: ID: P.1500. RS/3125B. Bharata Bhaisajya Ratnakara Compiled by Naginadasa Katsura, et al., “In Vitro Antimicrobial Activities of Bakuchiol Chaganalala Saha, Translated by Gopinath Gupta—vol-IV: B Jain against Oral Microorganisms,” Antimicrobial Agents and Chemo Publishers, New Delhi, Edn. 2". Reprint, Aug. 1999. This book therapy 45( 11):3009-3013, 2001. contains back references from 1000 B.C. To 20" century), p. 621 F. Khazaain-al-Advia, vol. I by Mohd Najmul Ghani Khan, Nadeem ID: RS. 1714. Yunus Printer/Sheikh Mohd Basheer & Sons, Lahore, 1911 AD, p. Bharata Bhaisajya Ratnakara Compiled by Naginadasa 680-681, F. ID: NA2/289. Chaganalala Saha, Translated by Gopinath Gupta—vol.-III: B. Jain Khazaain-al-Advia, vol. I by Mohd Najmul Ghani Khan, Nadeem Publishers, New Delhi, Edn. 2". Reprint, Aug. 1999. This book Yunus Printer/Sheikh Mohd Basheer & Sons, Lahore, 1911 AD, p. contains back references from 1000 B.C. to 20" century), p. 562 F. 680, F. ID: NA2/289A. ID: RD360. Khazaain-al-Advia, vol. I by Mohd Najmul Ghani Khan, Nadeem Buckman et al., “COX-2 expression is induced by UVB exposure in Yunus Printer/Sheikh Mohd Basheer & Sons, Lahore, 1911 AD, p. human skin: Implications for the development of skin cancer.” 681, F. ID: NA2/289R. Carcinogenesis 19(5):723-729, 1998. Khazaain-al-Advia, vol. III by Mohd Najmul Ghani Khan, Nadeem Chen et al., “Synthesis and structure-immunosuppressive activity Yunus Printer/Sheikh Mohd Basheer & Sons, Lahore, 1926 AD, p. relationships of bakuchiol and its derivatives.” Bioorganic & 612, F. ID: JA6/589Z30. Medicinal Chemistry 16:2403-2411, 2008. Kim et al., “In vitro Protein Tyrosine Phosphatase 1B Inhibitory Cho et al., “Bakuchiol: A Hepatoprotective Compound of Psoralea Phenols from the Seeds of Psoralea corylifolia, ' Planta Med corylifolia on Tacrine-Induced Cytotoxicity in Hep G2 Cells.” 71(1):87-99, 2005. Planta Med 67(8):750-751, 2001. Korean Office Action dated Oct. 31, 2012, for corresponding Church et al., “Are cysteinyl leukotrienes involved in allergic Korean Application No. 10-2007-7028470, 4 pages. responses in human skin?” Clin Exp Allergy 32: 1013-1019, 2002. Kowal-Bielecka, et al., “Evidence of 5-Lipoxygenase Overexpres Cuendet et al., “The Role of Cyclooxogenase and Lipoxygenase in sion in the Skin of Patients With Systemic Sclerosis.” Arthritis & Cancer Chemoprevention.” Drug Metabolism and Drug Interac Rheumatism 44(8): 1865-1875, 2001.
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