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(12) United States Patent (10) Patent No.: US 9,060,943 B2 Vielhaber Et Al

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(12) United States Patent (10) Patent No.: US 9,060,943 B2 Vielhaber Et Al US009060943B2 (12) United States Patent (10) Patent No.: US 9,060,943 B2 Vielhaber et al. (45) Date of Patent: Jun. 23, 2015 (54) COMPOSITIONS COMPRISING (58) Field of Classification Search TRANS-TERT BUTYL. CYCLOHEXANOLAS CPC ....... A61Q 19/02: A61Q 17/04; A61Q 15700; SKN RRITATION-REDUCINGAGENT A61Q 11/00; A61Q 19/004; A61O 19/005; A61Q 19/04; A61Q 19/06; A61Q 19/08; (75) Inventors: Gabriele Vielhaber, Paris (FR); Heiko A61Q 5/02: A61Q 13/00; A61Q 17/00; Oertling, Holzminden (DE); Claudia A61Q 19/00; A61Q 1/02: A61Q 5/00 Gömann, Warbsen (DE); Antje Köhler, See application file for complete search history. Holzminden (DE); Michael Krohn, Lorsch (DE); Holger Zinke, (56) References Cited Heppenheim (DE) U.S. PATENT DOCUMENTS (73) Assignee: SYMRISE AG, Holzminden (DE) 2.927,127 A 3, 1960 Somerville et al. 5,540,853 A * 7/1996 Trinh et al. ................... 510,101 (*) Notice: Subject to any disclaimer, the term of this 5,858,958 A 1/1999 Holzner patent is extended or adjusted under 35 6,027,668 A 2/2000 Holzner U.S.C. 154(b) by 345 days. 2007/0021319 A1 1/2007 Kohleet al. ....................... 512/2 (21) Appl. No.: 13A263,016 FOREIGN PATENT DOCUMENTS y x- - - 9 CN 1175900 A 3, 1998 (22) PCT Filed: Apr. 9, 2009 CN 1188.098 A 7, 1998 EP O75591O 1, 1997 (86). PCT No.: PCT/EP2009/054336 JP S5929618 A 2, 1984 JP H115O1081 A 1, 1999 S371 (c)(1), JP 2004107208 A 4, 2004 (2), (4) Date: Dec. 30, 2011 WO WO 97.22332 6, 1997 WO WO-9722332 A1 6, 1997 WO WO-2007042472 A1 4/2007 (87) PCT Pub. No.: WO2009/087242 WO WO 2008.117254 10, 2008 PCT Pub. Date: Jul. 16, 2009 OTHER PUBLICATIONS (65) Prior Publication Data Symrise GmbH & Co. KG, “Trans-tert-butyl cyclohexanol as skin US 2012/O121737 A1 May 17, 2012 irritation-reducing agent. Research Disclosure, Mason Publications, s vol. 542, No. 17, Jun. 1, 2009, p. 595, XP007139063. (51) Int. Cl. Notification of the First Office Action, Chinese Application No. 200980 159616.0, issued Nov. 15, 2012 (English Translation). g: i C International Search Report and Written Opinion of the International ( .01) Searching Authority for PCT/EP2009/054336 sent Aug. 1, 2010. A23C II/It (2006.01) Second Office Action, Chinese Application No. 200980 159616.0, A2.3L I/30 (2006.01) issued by the State Intellectual Property Office (SIPO) on Apr. 17. A2.3L 2/02 (2006.01) 2013, together with the reporting letter from the Chinese patent A2.3L 2/39 (2006.01) associates. A6 IK 8/02 (2006.01) Office Action from the Japanese Patent Office issued in parallel A6 IK3I/045 (2006.01) Japanese Application No. 2012-503873 together with the English A6 IK 45/06 (2006.01) translation, received on Nov. 25, 2013. Office Action from the Japanese Patent Office issued in parallel A61O 39; (2006.01) Japanese Application No. 2012-503873 together with the English C3 (O 3.08: translation, on Dec. 22, 2014. A61O 17/04 (2006.01) * cited by examiner A61 O 19/00 (2006.01) Continued A61 O 19/02 (2006.01) (Continued) A61 O 19/04 (2006.01) (52) U.S. Cl Primary Examiner — Terry A. McKelvey CPC ................. A61K 8/34 (2013.01); A23C 9/1307 Assistant Examiner Catheryne Chen (2013.01), A23C 1 1/103 (2013.01), A23L I/30 (74) Attorney, Agent, or Firm — Novak Druce Connolly (2013.01); A23L 2/02 (2013.01); A23L 2/39 Bove + Quigg LLP (2013.01); A61 K8/0216 (2013.01); A61 K 8/0229 (2013.01); A61K3I/045 (2013.01); (57) ABSTRACT A61K 45/06 (2013.01); A61 K 2800/75 The present invention primarily relates to the use of trans (2013.01); A61 K 2800/874 (2013.01); A61 K tert-butyl cyclohexanol as skin irritation-reducing agent as 2800/92 (2013.01); A61O 5/02 (2013.01); well as compositions (formulations) having a skin irritation A61O 1 1/00 (2013.01); A61O 15/00 (2013.01); reducing action comprising trans-tert-butyl cyclohexanol as A61O 17/04 (2013.01); A61 O 19/004 skin irritation-reducing agent. (2013.01); A61O 19/005 (2013.01); A61O 19/02 (2013.01); A61 O 19/04 (2013.01) 19 Claims, No Drawings US 9,060,943 B2 1. 2 COMPOSITIONS COMPRISING prevalence for self-declared sensitive skin had been reported TRANS-TERT BUTYL. CYCLOHEXANOLAS to be about 50% in the EU, USA and Japan and 36% in China. SKN RRITATION-REDUCINGAGENT People having sensitive skin for example observe facial discomfort with burning, stinging and similar skin sensation. CROSS-REFERENCE TO RELATED Sensitive skin can be caused by rapid changes in temperature, APPLICATIONS wind or by some cosmetics. It clearly is a neurological phe nomenon not correlating with allergic hypersensitivity or This application is a National Phase filing under 35 U.S.C. atopic dermatitis. People having sensitive skin often show an S371 of PCT/EP2009/054336, filed Apr. 9, 2009, the entire enhanced density of TRPV1 receptors on skin nerves and a 10 higher sensitivity towards capsaicin is also frequently contents of which is incorporated herein by reference. observed (which decreases with age due to decrease of skin The present invention primarily relates to the use of trans ennervation). 4-tert-butyl cyclohexanol as skin irritation-reducing (sooth Delicate skin describes a skin having a reduced irritation ing) agent as well as compositions (formulations) and prod threshold for irritants, such as hyper-reactive and intolerant, ucts having a skin irritation-reducing (soothing) action 15 and also atopic skin. In the case of humans with delicate, comprising trans-4-tert-butyl cyclohexanol as skin irritation sensitive or easily injured skin, a phenomenon called "sting reducing agent. ing” (“to sting' becoming injured, burn, be painful) can be It also relates to a medicament (pharmaceutical composi observed. Typical adverse phenomena associated with the tion) for treatment of skin irritations and/or pain conditions terms 'stinging or “sensitive skin' are reddening of the skin, and the use of such a formulation or of such a medicament for tingling, prickling, skin tightness and burning of the skin. prophylaxis (prevention) of skin irritation and/or treatment of They can be caused by stimulating environmental conditions, skin irritations for medical and/or other than medical, in Such as e.g. massage, action of Surfactants, influence of particular cosmetic, purposes. weather, such as heat, cold, dryness and also damp heat, In some Subjects, especially humans with sensitive skin, thermal radiation and UV radiation, e.g. from the Sun, or certain Substances may cause skin irritation, said skin irrita 25 psychological stress. tion being perceived as a stinging effect or burning sensation A “sensitive' scalp is likewise characterized by reddening if the Substance applied on the skin, especially on the face. of the skin, tingling, prickling, burning. Triggers are, for Examples of such substances used in the field of cosmetics are example, soap, shampoos or other hair care compositions, skin lighteners, skintanning agents, antibacterial agents, anti Surfactants, hard water having high lime concentrations and/ dandruff agents, antiacne agents, compounds against ageing 30 or mechanical stress. Erythemas and hyperseborrhoea (ex of the skin, emulsifiers, detergents, deodorizing agents, anti cessive production of sebum) of the scalp and dandruff are perspirants, skin warming agents, hair removing agents, abra often associated with the phenomena described. sives, anti-cellulite agents or certain classes of chemical com In about 10-20% of the population of industrial countries, pounds, e.g. phenol derivatives or C-hydroxy acids. with an increasing trend, atopy is to be observed, a hypersen Thus, the present invention moreover relates to a process 35 sitivity, of familial origin, of the skin and mucous membranes for the preparation of a formulation or of a medicament (phar to environmental Substances with an increased readiness to maceutical composition) having a skin irritation-reducing develop hyperSensitivity reactions of the immediate type (al action, a cosmetic ortherapeutic method for prophylaxis (pre lergies) to Substances from the natural environment. Atopy is vention) of skin irritations, a cosmetic or therapeutic method presumed to be of genetic origin. Atopy can manifest itself as for treatment of skin irritations, a method for prophylaxis of 40 atopic dermatitis. In this case, the skin barrier is damaged and the skin-irritating action and a method for reducing, eliminat the skin is often inflamed. ing or Suppressing the skin-irritating action of a Substance or The erythematous action of the ultraviolet part of sunlight Substance mixture able to cause skin irritation. or artificial radiation on the skin is generally known. While In the cosmetics and pharmaceuticals industry, there is a rays having a wavelength of less than 290 nm (the so-called constant need for agents having a skin irritation-reducing 45 UVC range) are absorbed by the ozone layer in the earth's action. atmosphere, rays in the range between 290 nm and 320 nm, The skin, in particular the epidermis, as a barrier organ of the so-called UVB range, cause erythema, simple Sunburn or the human organism is subjected to external influences to a even more or less severe burns. particular extent. Many intrinsic (e.g. genetic predisposition) Erythematous skin symptoms also occur as concomitant and extrinsic (e.g. damage to the skin barrier, action of UV 50 symptoms with certain skin diseases or irregularities. For light, irritating or allergy-inducing Substances) factors can example, the typical skin rash of the symptoms of acne is lead to skin irritation. In connection with this invention, skin regularly reddened to a greater or lesser degree and impairs irritation is to be understood as meaning any change to the the well-being of those affected even in mild cases.
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