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(19) TZZ __T (11) EP 2 416 766 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A61K 31/045 (2006.01) A61K 45/06 (2006.01) 09.04.2014 Bulletin 2014/15 A61K 8/34 (2006.01) A61P 17/00 (2006.01) A61P 17/16 (2006.01) A61Q 19/00 (2006.01) (2006.01) (2006.01) (21) Application number: 09701247.0 A23L 1/30 A23L 2/02 A23L 2/39 (2006.01) A23C 9/13 (2006.01) A23C 11/10 (2006.01) A61Q 5/02 (2006.01) (22) Date of filing: 09.04.2009 A61Q 11/00 (2006.01) A61Q 15/00 (2006.01) A61Q 17/04 (2006.01) A61Q 19/02 (2006.01) A61K 8/02 (2006.01) A61Q 19/04 (2006.01) (86) International application number: PCT/EP2009/054336 (87) International publication number: WO 2009/087242 (16.07.2009 Gazette 2009/29) (54) COMPOSITIONS COMPRISING TRANS-TERT-BUTYL CYCLOHEXANOL AS SKIN IRRITATION- REDUCING AGENT ZUSAMMENSETZUNGEN MIT TRANS-TERT-BUTYL-CYCLOHEXANOL ALS MITTEL ZUR REDUZIERUNG VON HAUTREIZUNGEN COMPOSITIONS COMPRENANT DU TRANS-TERT-BUTYL CYCLOHEXANOL EN TANT QU’AGENT RÉDUISANT L’IRRITATION CUTANÉE (84) Designated Contracting States: • KROHN, Michael AT BE BG CH CY CZ DE DK EE ES FI FR GB GR 64653 Lorsch (DE) HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL • ZINKE, Holger PT RO SE SI SK TR 64646 Heppenheim (DE) (43) Date of publication of application: (74) Representative: Eisenführ Speiser 15.02.2012 Bulletin 2012/07 Patentanwälte Rechtsanwälte PartGmbB Postfach 10 60 78 (73) Proprietor: Symrise AG 28060 Bremen (DE) 37603 Holzminden (DE) (56) References cited: (72) Inventors: EP-A2- 0 755 910 WO-A1-97/22332 • VIELHABER, Gabriele WO-A1-2008/117254 US-A- 2 927 127 75008 Paris (FR) • OERTLING, Heiko • SYMRISE GMBH & CO KG ET AL: "Trans-tert- 1012 Lausanne (CH) butyl cyclohexanol as skin irritation-reducing • GÖMANN, Claudia agent" RESEARCH DISCLOSURE, MASON 37640 Warbsen (DE) PUBLICATIONS, HAMPSHIRE, GB, vol. 542, no. • PFEIFFER, Antje 17, 1 June 2009 (2009-06-01) , page 595, 37603 Holzminden (DE) XP007139063 ISSN: 0374-4353 Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 2 416 766 B1 Printed by Jouve, 75001 PARIS (FR) EP 2 416 766 B1 Description [0001] The present invention primarily relates to the use of trans-4-tert-butyl cyclohexanol as skin irritation-reducing (soothing) agent as well as compositions (formulations) and products having a skin irritation-reducing (soothing) action 5 comprising trans-4-tert-butyl cyclohexanol as skin irritation-reducing agent. [0002] It also relates to a medicament (pharmaceutical composition) for treatment of skin irritations and/or pain con- ditions and the use of such a formulation or of such a medicament for prophylaxis (prevention) of skin irritation and/or treatment of skin irritations for medical and/or other than medical, in particular cosmetic, purposes. [0003] In some subjects, especially humans with sensitive skin, certain substances may cause skin irritation, said skin 10 irritation being perceived as a stinging effect or burning sensation if the substance applied on the skin, especially on the face. Examples of such substances used in the field of cosmetics are skin lighteners, skin tanning agents, antibacterial agents, antidandruff agents, antiacne agents, compounds against ageing of the skin, emulsifiers, detergents, deodorizing agents, antiperspirants, skin warming agents, hair removing agents, abrasives, anti-cellulite agents or certain classes of chemical compounds, e.g. phenol derivatives or α-hydroxy acids. 15 [0004] Thus, the present invention moreover relates to a process for the preparation of a formulation or of a medicament (pharmaceutical composition) having a skin irritation-reducing action, a cosmetic or therapeutic method for prophylaxis (prevention) of skin irritations, a cosmetic or therapeutic method for treatment of skin irritations, a method for prophylaxis of the skin-irritating action and a method for reducing, eliminating or suppressing the skin-irritating action of a substance or substance mixture able to cause skin irritation. 20 [0005] In the cosmetics and pharmaceuticals industry, there is a constant need for agents having a skin irritation- reducing action. [0006] The skin, in particular the epidermis, as a barrier organ of the human organism is subjected to external influences to a particular extent. Many intrinsic (e.g. genetic predisposition) and extrinsic (e.g. damage to the skin barrier, action of UV light, irritating or allergy-inducing substances) factors can lead to skin irritation. In connection with this invention, 25 skin irritation is to be understood as meaning any change to the skin which induces sensorial malaise in humans and/or is characterized by the symptoms a dry, reddened and/or inflamed skin. The term sensorial malaise here also includes states such as pain. Skin irritation can include, in particular, phenomenologically different skin states: delicate skin, sensitive skin, including sensitive scalp, easily injured skin, atopic skin, irritated skin or inflamed skin, which manifests itself in an in each case higher severity in a reddening of the skin, so-called erythema. 30 [0007] The problem of "delicate skin" affects a growing number of adults and children. It is now assumed that up to 50 % of the population have a delicate skin. [0008] Sensitive skin is one of the most common disturbing skin conditions and can have high influence on life quality. The prevalance for self-declared sensitive skin had been reported to be about 50 % in the EU, USA and Japan and 36% in China. 35 [0009] People having sensitive skin for example observe facial discomfort with burning, stingingand similar skin sen- sation. Sensitive skin can be caused by rapid changes in temperature, wind or by some cosmetics. It clearly is a neurological phenomenon not correlating with allergic hypersensitivity or atopic dermatitis. People having sensitive skin often show an enhanced density of TRPV1 receptors on skin nerves and a higher sensitivity towards capsaicin is also frequently observed (which decreases with age due to decrease of skin ennervation). 40 [0010] Delicate skin describes a skin having a reduced irritation threshold for irritants, such as hyper-reactive and intolerant, and also atopic skin. In the case of humans with delicate, sensitive or easily injured skin, a phenomenon called "stinging" ("to sting" = becoming injured, burn, be painful) can be observed. Typical adverse phenomena associated with the terms "stinging" or "sensitive skin" are reddening of the skin, tingling, prickling, skin tightness and burning of the skin. They can be caused by stimulating environmental conditions, such as e.g. massage, action of surfactants, 45 influence of weather, such as heat, cold, dryness and also damp heat, thermal radiation and UV radiation, e.g. from the sun, or psychological stress. [0011] A "sensitive" scalp is likewise characterized by reddening of the skin, tingling, prickling, burning. Triggers are, for example, soap, shampoos or other hair care compositions, surfactants, hard water having high lime concentrations and/or mechanical stress. Erythemas and hyperseborrhoea (excessive production of sebum) of the scalp and dandruff 50 are often associated with the phenomena described. [0012] In about 10-20 % of the population of industrial countries, with an increasing trend, atopy is to be observed, a hypersensitivity, of familial origin, of the skin and mucous membranes to environmental substances with an increased readiness to develop hypersensitivity reactions of the immediate type (allergies) to substances from the natural envi- ronment. Atopy is presumed to be of genetic origin. Atopy can manifest itself as atopic dermatitis. In this case, the skin 55 barrier is damaged and the skin is often inflamed. [0013] The erythematous action of the ultraviolet part of sunlight or artificial radiation on the skin is generally known. While rays having a wavelength of less than 290 nm (the so-called UVC range) are absorbed by the ozone layer in the earth’s atmosphere, rays in the range between 290 nm and 320 nm, the so-called UVB range, cause erythema, simple 2 EP 2 416 766 B1 sunburn or even more or less severe burns. [0014] Erythematous skin symptoms also occur as concomitant symptoms with certain skin diseases or irregularities. For example, the typical skin rash of the symptoms of acne is regularly reddened to a greater or lesser degree and impairs the well-being of those affected even in mild cases. 5 [0015] Erythemas also occur to an increased extent in the nappy region of infants, and all the more so of babies (nappy dermatitis). Incontinence, a condition which occurs to an increased extent especially in old age, is also often associated with erythemas and reddening of the skin as a consequence of continual exposure to moisture and irritants (incontinence dermatitis). [0016] A large number of active compounds having a skin irritation-reducing action are indeed already employed in 10 the technical fields referred to, but alternatives nevertheless continue to be sought. In the connection with this invention skin irritation-reducing action is to be understood as meaning the moderation, reduction, elimination or prevention of skin irritations, in particular that of the skin symptoms described above. The skin irritation-reducing action here is based in particular on soothing of the skin, inhibition of inflammation and/or alleviation of reddening. In this text, the term "skin " also includes the term "mucous membrane". In the search for alternative agents, however, it should be remembered 15 that the substances used must be toxicologically acceptable, tolerated well by the skin and stable (in particular in the conventional cosmetic and/or pharmaceutical formulations), should have the lowest possible intrinsic odour and the lowest possible intrinsic colour and must be inexpensive to prepare.
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