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Thymol and Carvacol for Use in Medicine Thymol Und Carvacol Zur Verwendung in Der Medizin Thymol Et Carvacol Destinés À Un Usage Médical

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Thymol and Carvacol for Use in Medicine Thymol Und Carvacol Zur Verwendung in Der Medizin Thymol Et Carvacol Destinés À Un Usage Médical (19) *EP003191086B1* (11) EP 3 191 086 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: A61K 31/05 (2006.01) A61K 36/00 (2006.01) (2006.01) (2006.01) 05.05.2021 Bulletin 2021/18 A61P 21/00 A61P 43/00 (21) Application number: 15771359.5 (86) International application number: PCT/US2015/049685 (22) Date of filing: 11.09.2015 (87) International publication number: WO 2016/040801 (17.03.2016 Gazette 2016/11) (54) THYMOL AND CARVACOL FOR USE IN MEDICINE THYMOL UND CARVACOL ZUR VERWENDUNG IN DER MEDIZIN THYMOL ET CARVACOL DESTINÉS À UN USAGE MÉDICAL (84) Designated Contracting States: (56) References cited: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB EP-A1- 2 277 395 WO-A1-2010/019034 GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO FR-A1- 2 872 683 US-A- 5 599 561 PL PT RO RS SE SI SK SM TR US-A1- 2011 281 956 US-A1- 2013 018 102 US-B1- 9 044 390 (30) Priority: 11.09.2014 US 201462049139 P • GREASER M L ET AL: "Effects of diethyl ether (43) Date of publication of application: and thymol on the ultrastructural and 19.07.2017 Bulletin 2017/29 biochemical properties of purified sarcoplasmic reticulum fragments from skeletal muscle", (73) Proprietor: University of Iowa Research BIOCHIMICA ET BIOPHYSICA ACTA (BBA) - Foundation BIOMEMBRANES, ELSEVIER, AMSTERDAM, NL, Iowa City, Iowa 52242-5500 (US) vol. 193, no. 1, 14 October 1969 (1969-10-14), pages 73-81, XP023351571, ISSN: 0005-2736, (72) Inventor: SAH, Rajan DOI: 10.1016/0005-2736(69)90060-1 [retrieved on Iowa City, Iowa 52242-5500 (US) 1969-10-14] (74) Representative: Reitstötter Kinzebach Patentanwälte Sternwartstrasse 4 81679 München (DE) 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 3 191 086 B1 Printed by Jouve, 75001 PARIS (FR) 1 EP 3 191 086 B1 2 Description vent skeletal muscle atrophy in the chronically ill or im- mobilized; 3) improve overall metabolic health by in- Background creasing basal metabolic rate via increased lean body weight and reduced adiposity in the obese; or 4) prevent [0001] Thymol (2-isopropyl-5-methylphenol, IPMP) is 5 the negative effects of prolonged space flight on skeletal a natural monoterpene phenol found predominantly in oil muscle (atrophy). of thyme, and extracted from Thymus vulgaris (common [0007] Additionally, obesity is a major public health thyme) and various other kinds of plants. Thymol pro- problem in the United States and worldwide, predispos- vides the distinctive, strong flavor of the culinary herb ing to systemic inflammation which culminates in diabe- thyme (made from T vulgaris) and is present in other 10 tes, heart disease, pulmonary disease and arthritis - re- spices, as well. sulting in a huge burden of disease and disability. Regular [0002] Thymol is part of a naturally occurring class of exercise and maintenance of muscle endurance and lean compounds known as biocides, with strong antimicrobial muscle mass are known to have significant beneficial attributes. Biocides are a class of compounds shown to metabolic effects in these conditions. There is also cur- have antimicrobial and antifungal properties. Thymol has 15 rently a need for compounds that can substitute for ex- been used in alcohol solutions and in dusting powders ercise, or significantly enhance the effects of mild, rela- for the treatment of tinea or ringworm infections, and was tively sedentary activity to increase muscle endurance, used in the US to treat hookworm infections. It is also metabolic rate, lean muscle mass and counter obesity. used as a preservative in halothane, an anesthetic, and as an antiseptic in mouthwash. When used to reduce 20 Summary plaque and gingivitis, thymol has been found to be more effective when used in combination with chlorhexidine [0008] The scope of the invention is defined by the than when used purely by itself. claims. Any subject-matter falling outside the scope of [0003] Carvacrol (2-methyl-5-isopropylphenol) is a the claims is provided for information purposes only. natural monoterpene phenol found in oregano, which 25 [0009] It has been discovered that thymol and carvac- gives the spice its characteristic odor. Carvacrol is also rol increase calcium cycling in skeletal muscle (both known for its antibacterial properties. Its low toxicity to- C2C12 myotubes and isolated primary mouse muscle gether with its pleasant taste and smell suggests its use fibers) by activating either TRPV3 ion channels and/or as a food additive to prevent bacterial contamination. It via activation of the sarcoplasmic reticulum calcium re- is a potent activator of the human ion channels transient 30 lease channel. In C2C12 myotubes, these compounds receptor potential V3 (TRPV3) and A1 (TRPA1). Appli- increase myotube size and increase the expression of cation of carvacrol on the human tongue, as well as ac- genes associated with mitochondrial biogenesis, oxida- tivation of TRPV3, causes a sensation of warmth. In ad- tive metabolism and muscle endurance. In vivo, it has dition, carvacrol also activates, but then rapidly desensi- been determined that sedentary mice supplemented with tizes, the pain receptor TRPA1; this explains its pungen- 35 Thymol for 5 weeks have a significantly improved exer- cy. Carvacrol has also been shown to be protective in cise capacity, increased muscle mass and enhanced obesity (Cho S, et.al. J Nutri Biochem 2012) and diabetes thermogenesis compared to vehicle treated mice. (Ezhumalai M. et al. Mol Cell Biochem 2014) in mouse [0010] Accordingly these compounds can be used to: models, though the mechanisms remain unclear 1) enhance skeletal muscle endurance and performance EP2277395 uses carvacrol as an absorption enhancer 40 in sedentary patients and in the elderly; 2) prevent skel- in nutritional supplements used to build muscle mass. etal muscle atrophy in the chronically ill or immobilized; [0004] FR2872683 discloses the use of carvacrol to 3) improve overall metabolic health by increasing basal enhance the growth of chickens. metabolic rate via increased lean body weight and re- [0005] Muscle loss/atrophy is a condition associated duced adiposity in the obese; or 4) prevent the negative with several causes, such as aging (sarcopenia), cancer 45 effects of prolonged space flight on skeletal muscle (at- and other diseases (cachexia), chronic illness/immobili- rophy). zation and poor nutrition. Muscle atrophy occurs by a [0011] The compounds thymol and carvacrol are also change in the normal balance between protein synthesis useful as substitutes for exercise, to enhance the effects and protein degradation. During atrophy, there is a down- of mild, relatively sedentary activity, or to increase muscle regulation of protein synthesis pathways, and an activa- 50 endurance, metabolic rate, or lean muscle mass, or to tion protein degradation. Loss of muscle is a result of counter obesity. diverse conditions and is typically a signal of poor out- [0012] In one aspect, the invention relates to the non- comes for a number of conditions. The preservation of therapeutic use of carvacrol or a pharmaceutically ac- muscle aids in patient survival and recovery as well as ceptable salt thereof for enhancing muscular recovery or overall well-being. 55 improving the effects of exercise on muscle endurance [0006] Currently there is a need for agents that are or muscle mass. useful to: 1) enhance skeletal muscle endurance and per- [0013] In a further aspect, the invention relates to car- formance in sedentary patients and in the elderly; 2) pre- vacrol or a pharmaceutically acceptable salt thereof for 2 3 EP 3 191 086 B1 4 use in treating sarcopenia. [0024] Further disclosed herein is thymol or carvacrol, [0014] In a further aspect, the invention relates to the or a pharmaceutically acceptable salt or prodrug thereof non-therapeutic use of thymol or a pharmaceutically ac- for increasing lean body mass, increasing metabolic rate, ceptable salt thereof for enhancing muscular recovery or or promoting fat weight loss. improving the effects of exercise on muscle endurance 5 [0025] Further disclosed herein is thymol or carvacrol, or muscle mass. or a pharmaceutically acceptable salt or prodrug thereof [0015] In a further aspect, the invention relates to thy- for promoting weight-loss. mol or a pharmaceutically acceptable salt thereof for use [0026] Further disclosed herein is the use of thymol or in treating sarcopenia. carvacrol, or a pharmaceutically acceptable salt or pro- [0016] Disclosed herein is a method comprising mod- 10 drug thereof to prepare a medicament for modulating ulating muscle atrophy, performance, recovery, genera- muscle atrophy, performance, recovery, generation, or tion, or maintenance in an animal in need thereof by ad- maintenance in an animal in need thereof. ministering thymol or carvacrol, or a pharmaceutically [0027] Further disclosed herein is the use of thymol or acceptable salt or prodrug thereof to the animal. Further carvacrol, or a pharmaceutically acceptable salt or pro- disclosed herein is a method comprising restoring dia- 15 drug thereof to prepare a medicament for restoring dia- phragm endurance or strength to assist in extubation of phragm endurance or strength to assist in extubation of a mechanically ventilated patient by administering thymol a mechanically ventilated patient. or carvacrol, or a pharmaceutically acceptable salt or pro- [0028] Further disclosed herein is the use of thymol or drug thereof to the patient. Further disclosed herein is a carvacrol, or a pharmaceutically acceptable salt or pro- method comprising enhancing muscular recovery in a 20 drug thereof to prepare a medicament for enhancing rehabilitating patient in need thereof by administering thy- muscular recovery in a rehabilitating patient.
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