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WO 2013/050902 Al 11 April 2013 (11.04.2013) P O P C T

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WO 2013/050902 Al 11 April 2013 (11.04.2013) P O P C T (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization I International Bureau (10) International Publication Number (43) International Publication Date WO 2013/050902 Al 11 April 2013 (11.04.2013) P O P C T (51) International Patent Classification: (74) Agent: CELESTINO, Marco; Viale Giovanni Pisano, 3 1, A61K 36/185 (2006.01) A61K 36/534 (2006.01) 1-56123 Pisa (IT). A61K 36/28 (2006.01) A61P 17/02 (2006.01) (81) Designated States (unless otherwise indicated, for every A61K 36/61 (2006.01) A01N 65/00 (2009.01) kind of national protection available): AE, AG, AL, AM, A61K 36/36 (2006.01) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, (21) International Application Number: BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, PCT/IB2012/055081 DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, (22) International Filing Date: KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, 24 September 2012 (24.09.2012) ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, (25) Filing Language: Italian NO, NZ, OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, (26) Publication Language: English TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, (30) Priority Data: ZM, ZW. PI201 1A000101 23 September 201 1 (23.09.201 1) IT (84) Designated States (unless otherwise indicated, for every (72) Inventor; and kind of regional protection available): ARIPO (BW, GH, (71) Applicant : DEL CORSO, Simone [IT/IT]; Via Sesia, 9, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, 1-56 122 Pisa (IT). UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, (72) Inventors: BIANUCCI, Anna Maria; Via Tagliamento, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, ΓΓ, LT, LU, LV, 12, 1-56122 Pisa (ΓΓ). BORGHINI, Alice; Via Vecchializ- MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, ia, 48, 1-56017 San Giuliano Terme (pi) (ΓΓ). PIETRA, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, Daniele; Via Vecchializia, 48, 1-56017 San Giuliano Ter ML, MR, NE, SN, TD, TG). me (pi) (IT). Published: — with international search report (Art. 21(3)) [Continued on next page] (54) Title: JOJOBA OIL HELICHRYSUM EXTRACT AND COMPOSITIONS THEREOF, IN PARTICULAR, FOR TREATING A SKIN CONDITION 200· 5 - 50 125 100 - 75 - 50 25 - 0 - -2,5 -2.0 -1.5 -1.0 0.0 Concentrazione (Log % o (57) Abstract: A method for making an extract of a plant of the genus Helichrysum in Jojoba oil or wax, in which a step is provided of joining the Helichrysum, preferably the upper parts of the plant, with a Jojoba wax having an acid number higher than 0.3, in par © ticular higher than 0.32, more in particular higher than 0.36. Such method makes it possible to obtain an extract with a high flavon - oid content useful for stimulating the keratinocytes of the epidermis, characterised by a content of Chrysin higher than 80 mg kg of © fatty acids having 20 carbon atoms with one unsaturation, in particular higher than 84 mg/kg, more in particular, higher than 104 mg/kg and/or makes it possible to obtain an extract with a low contained of allergens, characterised by a ratio between the amounts o of Limonene and β- Selinene lower than 0.4, in particular lower than 0.08, more in particular, lower than 0.06. The step of joining is preferably obtained by a dynamic process, for example by percolation or by centrifugation. A medical or cosmetic composition com prising such an extract for treating or preventing a disease and/or a condition that requires a stimulation of cell proliferation of kerat - o inocytes, among which wounds, burns, skin ulcers, scars, skin aging, stretch marks, wrinkles and others. An insect -repellent compos - ition comprising the extract. w o 2013/050902 A llll II II 11III III III I II 11 II 11III II I II before the expiration of the time limit for amending the claims and to be republished in the event of receipt of amendments (Rule 48.2(h)) TITLE JOJOBA OIL HELICHRYSUM EXTRACT AND COMPOSITIONS THEREOF, IN PARTICULAR FOR TREATING A SKIN CONDITION DESCRIPTION Field of the invention The present invention relates to an extract of a plant of the genus Helichrysum in Jojoba oil, and to a method for producing such extract. Furthermore, the invention relates to a medicament, to a medical device or to a cosmetic that contains an extract of a plant of the genus Helichrysum in Jojoba oil, and that is suitable for treating particular skin diseases and/or conditions in a human being or in an animal. The invention relates also to a composition containing such an extract, having an insect-repellent effect. Prior Art In the past, many attempts have been made to develop synthetic drugs or natural remedies for treating various skin diseases. However, the extracts obtained from a variety of types of plants, or from different parts of a same plant, have respective different characteristics and effects. In particular, the use is known of compositions containing derivatives of plants of the genus Helichrysum and Jojoba wax as a medicinal herb and as a cosmetic product. Helichrysum The genus Helichrysum belongs to the family of the Asteraceae and comprises about six hundred species of flower plants. Various species of Helichrysum are known that contain potentially useful substances for treating skin diseases, for instance substances that have an antioxidant power. Among these species, Helichrysum italicum or angustifolium, is particularly used, which grows spontaneously in Southern Europe. Helichrysum italicum grows in a rocky environment, up to about 800 metres of altitude. It has a bushy look, a silver-green colour, and may achieve a height of 30-40 cm. It flowers from the end of spring to the beginning of autumn. The flowers are gathered in flower-heads that have an outer wrapper consisting of dark yellow petals and have a conical central receptacle that houses flowers one by one. The flowers are light yellow and have a tubular shape. Helichrysum italicum contains many types of substances such as volatile compounds, flavonoids, terpenoids, etc. Other species of the genus Helichrysum that contain substances potentially useful for treating skin diseases are, for instance, H . frigidum, H . lithoreum, H. melitense, H . montelinasanum, H . nebrodense, H . rupestre (var. errerae), H . Rupestre (var. melitense), H . rupestre (var. messerii), H . Rupestre (var. Pendulum), H. rupestre (var. rupestre), H . saxatile, H . Siculum, H . Stoechas. Chrysin and other flavonoids The antioxidant, anti-inflammatory and antimicrobial properties of such flavonoids as Chrysin, Galangin, Pinocembrin are well known. These flavonoids are known to be present in many plants of the genus Helichrysum. More in detail, Chrysin (5,7-Dihydroxy-2-phenyl-4H-benzo[b]pyran-4-one) can attenuate apoptosis, reduce reactive oxygen species (ROS), and also lower the expression of cyclooxygenase-2 (COX-2) that is caused by UVB and UVA. Chrysin reverses in a predominant way the expression of Aquaporin 3 (AQP-3) caused by the UVB. It reverses in a predominant way the activation of JNK and inhibited slightly the activation of p38 caused by the UVA and by the UVB. The topical application of Chrysin is followed by an effective percutaneous absorption and does not generate irritation to the skin. Globally, the results have shown significant benefits of Chrysin on the protection of keratinocytes against injuries induced by cytotoxic factors such as UVA and UVB. See Wu, Nan-Lin et al., Chrysin Protects Epidermal Keratinocytes from UVA- and UVB-lnduced Damage, Journal of Agricultural and Food Chemistry, 201 1 59 8391-8400. FR 2906716 describes the use of Chrysin in cosmetic compositions for treatment of the greasy skin, and its effectiveness in inhibiting the proliferation of human sebocytes. US 2005/0049206 describes some flavonoids and extracts that contain them, which have pharmaceutical properties useful in the therapy of fibrotic diseases, for protecting or treating or repairing fibrotic damaged tissues. European Journal of Medicinal Chemistry, 46, 1, 201 1, 393-398 deals with Chrysin and analogues thereof as immunosuppressive and potentially useful agents against such diseases as psoriasis. Volatile compounds of Helichrysum WO 2007/066305 describes analgesic effects of a composition containing at least one sesquiterpene in the human or animal body. Trans-2-decenal ((E)-2-Decenale) and Nonanal aldehydes have insect- repellent properties. See, for instance, US 2007/01 54504, JP 2006/327957, which describe their use against Dermatophagoides farinae, and US 6,524,605, which describes compositions comprising a monoterpenoid or a sesquiterpenoid that is effective as a repellent for arthropods such as cockroaches, mosquitoes, ticks, spiders, and the like. Furthermore, trans-2-decenal and Nonanal aldehydes are classified in the Cosing database as cosmetic ingredients, in particular as perfume agents. Jojoba Jojoba oil or Jojoba wax are obtained from Jojoba or Simmondsia chinensis seeds, a plant that has a shrubby look and grows in some desert areas of Northern America. Jojoba oil is present in the seeds, in a weight percentage normally higher than 50%. See, for instance, D.J. Undersander, et al., Jojoba. Alternative Field Crops Manual, 1990. Jojoba wax has a structure very similar to human sebum, with which it is completely miscible. For this reason, it is tolerated by human skin far better than other vegetable oils, and does not obstruct the pores.
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