WO1996014840A1 - Use of menthyl lactate as a pain reliever - Google Patents
Use of menthyl lactate as a pain reliever Download PDFInfo
- 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
Links
- UJNOLBSYLSYIBM-WISYIIOYSA-N [(1r,2s,5r)-5-methyl-2-propan-2-ylcyclohexyl] (2r)-2-hydroxypropanoate Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)[C@@H](C)O UJNOLBSYLSYIBM-WISYIIOYSA-N 0.000 title claims abstract description 25
- 229940124641 pain reliever Drugs 0.000 title claims description 6
- 239000000203 mixture Substances 0.000 claims abstract description 31
- 230000000699 topical effect Effects 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 241001465754 Metazoa Species 0.000 claims description 6
- 239000012049 topical pharmaceutical composition Substances 0.000 claims 1
- 241000124008 Mammalia Species 0.000 abstract description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical class CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 15
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 10
- 229940041616 menthol Drugs 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000003205 fragrance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- 229940085237 carbomer-980 Drugs 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 229940044949 eucalyptus oil Drugs 0.000 description 3
- 239000010642 eucalyptus oil Substances 0.000 description 3
- 210000004400 mucous membrane Anatomy 0.000 description 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
- 229920000053 polysorbate 80 Polymers 0.000 description 3
- 229940035676 analgesics Drugs 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000002085 irritant Substances 0.000 description 2
- -1 lactate ester Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 235000019645 odor Nutrition 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 239000004166 Lanolin Substances 0.000 description 1
- 235000006679 Mentha X verticillata Nutrition 0.000 description 1
- 235000002899 Mentha suaveolens Nutrition 0.000 description 1
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 229960001631 carbomer Drugs 0.000 description 1
- 229940049638 carbomer homopolymer type c Drugs 0.000 description 1
- 229940043234 carbomer-940 Drugs 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 210000000744 eyelid Anatomy 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229940075529 glyceryl stearate Drugs 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000019388 lanolin Nutrition 0.000 description 1
- 229940039717 lanolin Drugs 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229940025703 topical product Drugs 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
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
The use of menthyl lactate for the manufacture of a topical composition for achieving topical pain relief is disclosed. Furthermore, the invention concerns a method of achieving topical pain relief which method comprises topically applying to the external skin of a mammal including man a topical pain relieving effective amount of menthyl lactate.
Description
Use Of Menthyl Lactate As A Pain Reliever
Field Of The Invention
The invention relates to the field of analgesics and in particular to topical analgesics. The invention further relates to the field of menthol esters.
Background Of The Invention
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.
In 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.
Various 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%. The maximum recommended amount of 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.
Objects Of The Invention
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.
Summary Of The Invention
These and other objects of the invention can be achieved by using menthol lactate as the topical pain relieving active agent.
Detailed Description Of The Invention
The invention concems a method of achieving topical (= external) pain relief, in an animal in need thereof comprising the application of 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. "Animal" preferably means warm-blooded animal (= mammal) and includes man.
Moreover, 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.
For use as a topical pain reliever, 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 preferably about 0.2% to about 5.0%, most preferably about 0.5% to about 4.0%), especially eucalyptus oil (preferably up to 5.5%, more preferably about 0.2% to about 5.0%), and the like, and mixtures thereof.
The 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 following example is intended to exemplify, but not to limit the invention.
Example 1 :
Ingredient Amount
Carbomer 980 0.8%
Purified Water 67.2%
Propylene Glycol 5.0%
Menthyl Lactate 9.0%
Eucalyptus Oil 0.5%
SD 3A Alcohol (= ι ca. 95 Vol% ethanol denatured with ca. , 5 Vol% methanol) 15.0%
TWEEN 80 0.5%
Triethanolamine 1.0%
Fragrance 1.0%
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. In 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. In 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.
Claims
1. The use of menthyl lactate for the manufacture of a topical composition for achieving topical pain relief.
2. The use according to claim 1 wherein the menthyl lactate is incorporated into the topical composition in a concentration of from about 2.0% to about 22% by weight of the total composition.
3. The use according to claim 1 wherein the menthyl lactate is incorporated into the topical composition in a concentration of from about 6.0% to about 18% by weight of the total composition.
4. The use according to claim 1 wherein the menthyl lactate is incorporated into the topical composition in a concentration of from about 9.0% to about 15% by weight of the total composition.
5. A method of achieving topical pain relief in an animal in need thereof comprising topically applying to the external skin of said animal a topical pain relieving effective amount of menthyl lactate.
6. The method of claim 5 wherein said menthyl lactate is applied in a concentration of from about 2.0% to about 22% by weight of the total composition.
7. The method of claim 5 wherein said menthyl lactate is applied in a concentration of from about 6.0% to about 18% by weight of the total composition.
8. The method of claim 5 wherein said menthyl lactate is applied in a concentration of from about 9.0% to about 15% by weight of the total composition.
9. A topical pharmaceutical composition for achieving topical pain relief consisting essentially of menthyl lactate and at least one topically acceptable carrier.
10. Menthyl lactate for use as a topical pain reliever.
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 (en) | 1996-05-23 |
Family
ID=23328966
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP1995/004334 WO1996014840A1 (en) | 1994-11-14 | 1995-11-04 | Use of menthyl lactate as a pain reliever |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU3870895A (en) |
| WO (1) | WO1996014840A1 (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997042944A1 (en) * | 1996-05-13 | 1997-11-20 | Novartis Consumer Health S.A. | Topical composition |
| EP1250940A1 (en) * | 2001-04-17 | 2002-10-23 | The Procter & Gamble Company | An absorbent article comprising an agent able to convey a perception to the wearer |
| EP1250941A1 (en) * | 2001-04-17 | 2002-10-23 | The Procter & Gamble Company | Articles comprising a mint odor-free cooling agent |
| 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 (en) * | 2005-01-04 | 2012-10-18 | Teikoku Pharma Usa Inc | Cooling topical patch preparation |
| EP3108880A1 (en) | 2015-06-26 | 2016-12-28 | Natures Innovation, Inc. | Analgesics based on snake venoms |
| US10543236B2 (en) | 2013-07-26 | 2020-01-28 | Natures Innovation Inc. | Analgesics based on snake venoms |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2608226A1 (en) * | 1976-02-28 | 1977-09-08 | Haarmann & Reimer Gmbh | AGENTS WITH PHYSIOLOGICAL COOLING EFFECT |
-
1995
- 1995-11-04 AU AU38708/95A patent/AU3870895A/en not_active Abandoned
- 1995-11-04 WO PCT/EP1995/004334 patent/WO1996014840A1/en active Application Filing
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2608226A1 (en) * | 1976-02-28 | 1977-09-08 | Haarmann & Reimer Gmbh | AGENTS WITH PHYSIOLOGICAL COOLING EFFECT |
Non-Patent Citations (1)
| Title |
|---|
| SAKATA I ET AL: "SYNTHESIS AND PROPERTIES OF MENTHYL GLYCOSIDES", AGRIC BIOL CHEM, 43 (2). 1979. 307-312. * |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997042944A1 (en) * | 1996-05-13 | 1997-11-20 | Novartis Consumer Health S.A. | Topical composition |
| CN100540063C (en) * | 2001-04-17 | 2009-09-16 | 宝洁公司 | The goods that comprise the cool agent that does not contain mint smell |
| EP1250941A1 (en) * | 2001-04-17 | 2002-10-23 | The Procter & Gamble Company | Articles comprising a mint odor-free cooling agent |
| WO2002083191A1 (en) * | 2001-04-17 | 2002-10-24 | The Procter & Gamble Company | An absorbent article comprising an agent able to convey a perception to the wearer |
| WO2002083192A1 (en) * | 2001-04-17 | 2002-10-24 | The Procter & Gamble Company | Articles comprising a mint odor-free cooling agent |
| 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 (en) * | 2001-04-17 | 2002-10-23 | The Procter & Gamble Company | An absorbent article comprising an agent able to convey a perception to the wearer |
| 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 (en) * | 2005-01-04 | 2012-10-18 | Teikoku Pharma Usa Inc | Cooling topical patch preparation |
| 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 (en) | 2015-06-26 | 2016-12-28 | Natures Innovation, Inc. | Analgesics based on snake venoms |
Also Published As
| Publication number | Publication date |
|---|---|
| AU3870895A (en) | 1996-06-06 |
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