WO1996014840A1 - Utilisation du lactate de menthyle comme analgesique - Google Patents

Utilisation du lactate de menthyle comme analgesique Download PDF

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Publication number
WO1996014840A1
WO1996014840A1 PCT/EP1995/004334 EP9504334W WO9614840A1 WO 1996014840 A1 WO1996014840 A1 WO 1996014840A1 EP 9504334 W EP9504334 W EP 9504334W WO 9614840 A1 WO9614840 A1 WO 9614840A1
Authority
WO
WIPO (PCT)
Prior art keywords
menthyl lactate
topical
composition
weight
concentration
Prior art date
Application number
PCT/EP1995/004334
Other languages
English (en)
Inventor
Richard Louis Braun
Robert Caroselli
Theodore Clemente, Jr.
Sandra Ervy Sandbeck
Original Assignee
Zyma S.A.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Zyma S.A. filed Critical Zyma S.A.
Priority to AU38708/95A priority Critical patent/AU3870895A/en
Publication of WO1996014840A1 publication Critical patent/WO1996014840A1/fr

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin

Definitions

  • the invention relates to the field of analgesics and in particular to topical analgesics.
  • the invention further relates to the field of menthol esters.
  • Menthol has been used in various topical preparations as a counterirritant, as an aesthetic agent (for its fragrance), and as a plasticizer in denture adhesive compositions. Unfortunately, the aroma of menthol has been a significant hinderance to its use in any meaningful amount other than where its fragrance is desired.
  • compositions containing effective counter-irritant amounts of menthol 1.25% to 16% according to the FDA monograph for menthol
  • the aroma from menthol can be overpowering.
  • menthol esters have been prepared. Most of these esters have disagreeable odors, making them truly unsuitable for use in a topical product. These odors are as disagreeable as, or more so than, menthol itself, especially in amounts which are equimolar with monograph counter-irritant effective amounts of menthol.
  • Menthyl lactate is a known compound available e.g. from Haarmann & Reimer GmbH (Germany) under the name FRESCOLAT, Type ML. Two thirds of its molecular weight is attributable to the menthol moiety.
  • the manufacturer's product literature indicates that it is a "cooling agent” and that it can be used in body care and cosmetic products in which "long lasting cooling and freshness are desired". According to the manufacturer, menthyl lactate is virtually odorless, not suffering from the "mint note” that is otherwise customary in the case of other menthol derivatives.
  • the compound is recommended for use as a flavor in concentrations of 0.005% to 0.2% and in cosmetic and other external products in concentrations ranging from 0.2% to 2.0%.
  • menthyl lactate as per the product literature is therefore 2.0% by weight, which would correspond 1.3% by weight of the menthol moiety. Nowhere is there any indication or suggestion that menthyl lactate should be used as a topical pain reliever or at concentrations substantially in excess of those indicated by the product literature.
  • An object of the invention is to provide a topical pain reliever for external treatment.
  • Another object of the invention is to provide a substantially odor-free composition having topical analgesic properties.
  • menthol lactate as the topical pain relieving active agent.
  • a topical or mucous membrane suitable composition to the skin of said animal, wherein said composition comprises a topical or mucous membrane pain relieving effective amount of menthyl lactate.
  • the invention relates to the use of menthyl lactate (for the manufacture of a topical composition) for achieving topical pain relief.
  • the topical composition may either be a pharmaceutical one or a veterinary one, preferably a pharmaceutical one.
  • the topical composition is preferably applied to the skin or a mucous membrane of the subject to be treated.
  • Menthyl lactate is the lactate ester of menthol and has the structural formula
  • the compound is available commercially under the name FRESCOLAT, Type ML from Haarmann & Reimer GmbH (Germany). It can also be readily made by processes known in the art by esterifiying the hydroxy group of menthol with lactic acid.
  • menthyl lactate is present in compositions compatible with this use in amounts which range from about 2.0% to about 22% by weight of the total composition, preferably about 6.0% to about 18%, more preferably about 9.0% to about 15%, by weight of the total composition.
  • the remainder of the composition may be any suitable topical carrier which is compatible with menthyl lactate.
  • the external topical preparations of the invention can be applied to any portion of the skin. However, application to the external genetalia, or the eyelids, or lips is not suggested, recommended, or usually desired.
  • Typical external topical carriers and additives suitable for use in the present invention include, but are not limited to, carriers such as lanolin, white petrolatum, propylene glycol (preferably up to about 10%, more preferably about 2% to about 8%), paraffin, an alcohol selected from ethanol and isopropyl alcohol (preferably up to about 30%, more preferably about 10% to about 25%), and water (preferably up to about 80%, more preferably about 45% to about 75%); surfactants such as TWEEN (preferably TWEEN 80) (preferably up to about 2.2%, more preferably about 0.2% to about 2.0%), and glyceryl stearate; thickeners such as accacia, methylcellulose, tragacanth, or a carbomer (preferably carbomer 980 or carbomer 940) (preferably up to about 1.5%, more preferably about 0.5% to about 1.2%); pH adjusters such as triethanolamine (preferably up to 2.4%, more preferably about 0.5% to about 2.0%); and fragrance (preferably up to about 5.5%, more
  • compositions for use in the present invention may take any appropriate form for the intended application area including, but not limited to, solutions, suspensions, powders, creams, ointments, impregnated bandages, etc.
  • the present invention formulations are applied generally as needed anywhere from once to 6 or more times a day, depending on the degree of relief required and the nature of the pain involved.
  • the patient can suitably self regulate the frequency with which the compositions need be applied.
  • the Carbomer 980 is dispersed in approximately 90-99% of the water in a mixing tank.
  • the propylene glycol is then added to the dispersion.
  • a separate tank mix together and dissolve the alcohol, TWEEN 80, fragrance, eucalyptus oil, and menthyl lactate.
  • the second mixture is then added to the first mixture with continued mixing.
  • a third tank the triethanolamine is dissolved in the remaining water.
  • the third mixture is then added to the first mixing tank with continued mixing.

Landscapes

  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Preparation (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Utilisation du lactate de menthyle dans la fabrication d'une composition topique permettant d'obtenir un effet analgésique topique, et procédé d'obtention d'un effet analgésique topique consistant à appliquer de manière topique, à la surface de la peau d'un mammifère tel que l'homme, une dose analgésique efficace topique de lactate de menthyle.
PCT/EP1995/004334 1994-11-14 1995-11-04 Utilisation du lactate de menthyle comme analgesique WO1996014840A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU38708/95A AU3870895A (en) 1994-11-14 1995-11-04 Use of menthyl lactate as a pain reliever

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US33942894A 1994-11-14 1994-11-14
US08/339,428 1994-11-14

Publications (1)

Publication Number Publication Date
WO1996014840A1 true WO1996014840A1 (fr) 1996-05-23

Family

ID=23328966

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1995/004334 WO1996014840A1 (fr) 1994-11-14 1995-11-04 Utilisation du lactate de menthyle comme analgesique

Country Status (2)

Country Link
AU (1) AU3870895A (fr)
WO (1) WO1996014840A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997042944A1 (fr) * 1996-05-13 1997-11-20 Novartis Consumer Health S.A. Composition topique
EP1250940A1 (fr) * 2001-04-17 2002-10-23 The Procter & Gamble Company Article absorbant contenant un agent pouvant transmettre une sensation à l' utilisateur
EP1250941A1 (fr) * 2001-04-17 2002-10-23 The Procter & Gamble Company Articles contenant un agent rafraichissant sans odeur de menthe
US6972010B2 (en) 2001-04-17 2005-12-06 The Procter & Gamble Company Absorbent article comprising an agent able to convey a perception to the wearer, without the need to create the external condition perceived
US8273367B2 (en) 2001-04-17 2012-09-25 The Procter And Gamble Company Articles comprising a mint odor-free cooling agent
US8282607B2 (en) * 2003-05-14 2012-10-09 Chattem, Inc. Sleeve and micro-encapsulated topical analgesic for pain relief
JP2012197300A (ja) * 2005-01-04 2012-10-18 Teikoku Pharma Usa Inc 冷却局所用貼付製剤
EP3108880A1 (fr) 2015-06-26 2016-12-28 Natures Innovation, Inc. Analgésiques à base de venins de serpent
US10543236B2 (en) 2013-07-26 2020-01-28 Natures Innovation Inc. Analgesics based on snake venoms

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2608226A1 (de) * 1976-02-28 1977-09-08 Haarmann & Reimer Gmbh Mittel mit physiologischer kuehlwirkung

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2608226A1 (de) * 1976-02-28 1977-09-08 Haarmann & Reimer Gmbh Mittel mit physiologischer kuehlwirkung

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
SAKATA I ET AL: "SYNTHESIS AND PROPERTIES OF MENTHYL GLYCOSIDES", AGRIC BIOL CHEM, 43 (2). 1979. 307-312. *

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997042944A1 (fr) * 1996-05-13 1997-11-20 Novartis Consumer Health S.A. Composition topique
CN100540063C (zh) * 2001-04-17 2009-09-16 宝洁公司 包括不含薄荷气味的凉爽剂的制品
EP1250941A1 (fr) * 2001-04-17 2002-10-23 The Procter & Gamble Company Articles contenant un agent rafraichissant sans odeur de menthe
WO2002083191A1 (fr) * 2001-04-17 2002-10-24 The Procter & Gamble Company Article absorbant comprenant un agent capable de donner une sensation a un utilisateur
WO2002083192A1 (fr) * 2001-04-17 2002-10-24 The Procter & Gamble Company Articles comprenant un agent de rafraichissement sans odeur de type menthe
US6972010B2 (en) 2001-04-17 2005-12-06 The Procter & Gamble Company Absorbent article comprising an agent able to convey a perception to the wearer, without the need to create the external condition perceived
EP1250940A1 (fr) * 2001-04-17 2002-10-23 The Procter & Gamble Company Article absorbant contenant un agent pouvant transmettre une sensation à l' utilisateur
US8273367B2 (en) 2001-04-17 2012-09-25 The Procter And Gamble Company Articles comprising a mint odor-free cooling agent
US8282607B2 (en) * 2003-05-14 2012-10-09 Chattem, Inc. Sleeve and micro-encapsulated topical analgesic for pain relief
JP2012197300A (ja) * 2005-01-04 2012-10-18 Teikoku Pharma Usa Inc 冷却局所用貼付製剤
US10543236B2 (en) 2013-07-26 2020-01-28 Natures Innovation Inc. Analgesics based on snake venoms
US11090340B2 (en) 2013-07-26 2021-08-17 Nature's Innovation, Inc. Analgesics based on snake venoms
EP3108880A1 (fr) 2015-06-26 2016-12-28 Natures Innovation, Inc. Analgésiques à base de venins de serpent

Also Published As

Publication number Publication date
AU3870895A (en) 1996-06-06

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