WO1994020087A1 - Throat compositions - Google Patents
Throat compositions Download PDFInfo
- Publication number
- WO1994020087A1 WO1994020087A1 PCT/US1993/002884 US9302884W WO9420087A1 WO 1994020087 A1 WO1994020087 A1 WO 1994020087A1 US 9302884 W US9302884 W US 9302884W WO 9420087 A1 WO9420087 A1 WO 9420087A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- weight
- composition according
- mixture
- benzocaine
- range
- Prior art date
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
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
- A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
- A61K31/245—Amino benzoic acid types, e.g. procaine, novocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
Definitions
- This invention relates to throat compositions.
- it relates to topical anaesthetic compositions for sore throat treatment based on benzocaine and which are in the form of single phase aqueous mixtures.
- Benzocaine the ethyl ester of p-amino benzoic acid
- benzocaine is only very slightly soluble in water
- formulators have generally used non-aqueous solvents to solubilize the material, for example the polyethylene glycol esters taught in US-A-3322624, and the benzyl alcohol formulations taught in US-A-2187597.
- Attempts to solubilize benzocaine in water using various surface active agents have also been made - see US-A- 3624224.
- the resulting preparations have generally been found to be unstable with the benzocaine crystallising or settling out, the problem being particularly acute at benzocaine concentrations over 0.5%.
- Benzocaine itself is also susceptible to hydrolysis in aqueous systems.
- compositions comprising defined levels of humectant, water and lower alcohol.
- humectant selected from polyethylene glycol having a molecular weight of less than 1500, propylene glycol, glycerol and mixtures thereof; and c) from about 43% to about 74.9% by weight of a mixture of water and lower (C1-C4) alcohol in a weight ratio of from about
- compositions herein contain, as essential ingredients, benzocaine, humectant, and a water/alcohol mixture, all in defined proportions and ratios critical for achieving the necessary physical stability, chemical stability and anaesthetic efficacy.
- compositions of the invention comprise from about 0.1 % to about 2%, preferably from about 0.5% to about 1 %, and more preferably from about 0.6% to about 0.8% by weight of benzocaine; from about 25% to about 55%, preferably from about 35% to 50%, and more preferably from about 40% to about 48% by weight of humectant; and from about 43% to about 74.9%, preferably from about 49% to about 64%, and more preferably from about 51 % to about 59% by weight of the mixture of water and lower alcohol.
- the water/alcohol mixture itself is in a weight ratio of from about 0.3:1 to about 3:1 , preferably from about 0.4:1 to about 2.5:1 , and especially from about 0.6:1 to about 1 :1.
- compositions of the invention comprise from about 10% to about 55%, more preferably from about 15% to about 30% by weight thereof of water, and from about 15% to about 55%, preferably from about 20% to about 40% by weight thereof of lower alcohol, for example, propanol, isopropanol, butanol or ethanol.
- lower alcohol for example, propanol, isopropanol, butanol or ethanol.
- composition of the. humectant is critical herein, being selected from polyethylene glycol having a molecular weight of less than about 1500, preferably less than about 1000, and especially in the range from about 130 to about 600 (for example PEG 300), propylene glycol, glycerol and mixtures thereof.
- the molecular weight of the polyethylene glycol is selected to achieve optimum formulation stability, viscosity and spray characteristics.
- the humectant comprises a mixture of polyethylene glycol and propylene glycol in a weight ratio in the range from about 8:1 to about 1 :8, preferably from about 3:1 to about 1 :3, more preferably from about 2:1 to about 1 :2;
- the humectant comprises a mixture of polyethylene glycol and glycerol in a weight ratio in the range from about 8:1 , preferably from about 3:1 to about 1 :3, more preferably from about 2:1 to about 1 :2; or
- the humectant comprises a mixture of propylene glycol and glycerol in a weight ratio in the range from about 8:1 to about 1 :8, preferably from about 3:1 to about 1 :3, more preferably from about 2:1 to about 1 :2.
- the humectant comprises a mixture of polyethylene glycol, propylene glycol and glycerol in a weight ratro in the range from about 8:1 :1 to about 1 :8:1 to about 1 :1 :8, preferably from about 3:1 :1 to about 1 :3:1 to about 1 :1 :3, more preferably from about 2:1 :1 to about 1 :2:1 to about 1 :1 :2.
- compositions of the invention have no need of and are preferably free of surfactant emulsifiers (especially nonionic and anionic surfactants), although cationic surfactants (eg quaternary ammonium compounds) can be added in levels of from about 0.1 % to about 2% for their germicidal activity.
- surfactant emulsifiers especially nonionic and anionic surfactants
- cationic surfactants eg quaternary ammonium compounds
- Suitable quaternary ammonium compounds include the alkylarylether dimethylbenzylammonium chlorides, an example of which is 2-[2-(p- octylcresoxy) ethoxy] ethyl dimethylbenzylammonium chloride, available under the name of methylbenzethonium chloride or Hyamine 10X and the corresponding p-octylphenoxy compound available as benzethonium chloride, and the aikyldimethylbenzyl ammonium chlorides available under the name benzalkonium chloride.
- alkylarylether dimethylbenzylammonium chlorides an example of which is 2-[2-(p- octylcresoxy) ethoxy] ethyl dimethylbenzylammonium chloride, available under the name of methylbenzethonium chloride or Hyamine 10X and the corresponding p-octylphenoxy compound available as benzethonium chloride, and the ai
- alkyltrimethyi ammonium chlorides such as cetyltrimethylammonium chloride available under the trade name Cetab; alkyldimethylethylammo ⁇ ium halides; alkylpyridinium chloride, such as cetylpyridinium chloride; alkylimidazoiinium chloride such as alkylhydroxyethylimidazolinium chloride; alkyldimethyldichiorobenzylammonium chlorides; acyicoiaminoformylinethyl pyridinium chloride available under the name of Emulsept; and aikarylmethyipyridinium chloride such as polyalkyinaphthaiene methylpyridinium chloride available under the trade name Emcol.
- alkyl is understood to encompass Cs to
- Ci8 preferably CI Q t0 Cl 6 atkyl radicals including mixtures within this range, this being the range in which quaternary ammonium compounds are considered to have good germicidal activity.
- compositions of this invention can optionally contain one or more other known therapeutic agents, particularly those commonly utilized in cough/cold preparations, such as, for example, a decongestant such as pseudoephedrine hydrochloride, phen ⁇ lephedrine hydrochioride and ephedrine hydrochloride; an analgesic such as acetaminophen and ibuprofen; an expectorant such as glyceryl guaiacolate, terpin hydrate and ammonium chloride; and an antihistamine such as chlorpheniramine maleate, doxylamine succinate, brompheniramine maleate and diphenhydramine hydrochloride.
- a decongestant such as pseudoephedrine hydrochloride, phen ⁇ lephedrine hydrochioride and ephedrine hydrochloride
- an analgesic such as acetaminophen and ibuprofen
- an expectorant such as glyceryl
- compositions of the invention are preferably formulated to have a pH in the range from about 4 to about 8, more preferably from about 6 to about 7.5, this pH preferably being maintained through the use of an appropriate pH buffer, eg sodium phosphate, sodium hydrogen phosphate (NaH2PO4) or sodium citrate.
- an appropriate pH buffer eg sodium phosphate, sodium hydrogen phosphate (NaH2PO4) or sodium citrate.
- Sodium hydrogen phosphate is the preferred buffer.
- ingredients well known to the pharmacist's art may also be included in amounts generally known for these ingredients, for example, natural or artificial sweeteners, flavoring agents and colorants to provide a palatable and pleasant looking final product; antioxidants, for example, butylated hydroxy anisole or butyiated hydroxy toluene, and
- SUBSTITUTE SHEET preservatives for example, methyl or propyl paraben or sodium benzoate to prolong and enhance shelf life.
- compositions of the invention can be prepared in any convenient form, for example, as a mouthrinse, gargle or aerosol, but highly preferred compositions herein are formulated as a non-aerosol pump spray.
- Spray compositions herein preferably have a viscosity in the range of about 1 to about 100 cps, preferably from about 1 to 50 cps, (viscosity being measured using a Brookfield RVT, Spindle RV1 at 100 rpm and 25 °C) and the spray pump is preferably of a finger actuated pump design.
- the compositions are applied topically in a unit dosage of from about 0.5 to about 10, preferred from about 1 to about 5 mg benzocaine per dose. In the preferred spray pump activator, there are approximately 3 sprays to the unit dose.
- compositions combine improved physical stability, together with excellent chemical stability and anaesthetic efficacy.
Abstract
A single phase topical anaesthetic compositions for sore throat treatment comprising: a) from about 0.1 % to about 2 % by weight of benzocaine; b) from about 25 % to about 55 % by weight of humectant selected from polyethylene glycol having a molecular weight of less than 1500, propylene glycol, glycerol and mixtures thereof; c) from about 43 % to about 74.9 % by weight of a mixture of water and lower (C1-C4) alcohol in a weight ratio of from about 0.3:1 to 3:1. The compositions display improved physical stability, benzocaine chemical stability and anaesthetic efficacy.
Description
THROAT COMPOSITIONS
TECHNICAL FIELD This invention relates to throat compositions. In particular, it relates to topical anaesthetic compositions for sore throat treatment based on benzocaine and which are in the form of single phase aqueous mixtures.
BACKGROUND OF THE INVENTION Benzocaine, the ethyl ester of p-amino benzoic acid, is a known local anaesthetic which has been administered topically in the form of ointments, lotions, sprays, gels and as an impregnant in first aid pads. Since benzocaine is only very slightly soluble in water, formulators have generally used non-aqueous solvents to solubilize the material, for example the polyethylene glycol esters taught in US-A-3322624, and the benzyl alcohol formulations taught in US-A-2187597. Attempts to solubilize benzocaine in water using various surface active agents have also been made - see US-A- 3624224. However, the resulting preparations have generally been found to be unstable with the benzocaine crystallising or settling out, the problem being particularly acute at benzocaine concentrations over 0.5%. Benzocaine itself is also susceptible to hydrolysis in aqueous systems.
It has now been found that aqueous single phase, topical anaesthetic formulations having improved physical stability, (reduced solid phase separation and discolouration) together with excellent benzocaine chemical stability, taste characteristics and efficacy (retention and absorption of the active) at low concentrations of benzocaine, are provided by compositions comprising defined levels of humectant, water and lower alcohol.
SUMMARY OF THE INVENTION According to the present invention there is provided a single phase topical anaesthetic composition for sore throat treatment comprising:
a) from about 0.1 % to about 2% by weight of benzocaine; b) from about 25% to about 55% by weight of humectant selected from polyethylene glycol having a molecular weight of less than 1500, propylene glycol, glycerol and mixtures thereof; and c) from about 43% to about 74.9% by weight of a mixture of water and lower (C1-C4) alcohol in a weight ratio of from about
0.3:1 to about 3:1.
All percentages herein are be weight of total composition, unless otherwise specified.
The compositions herein contain, as essential ingredients, benzocaine, humectant, and a water/alcohol mixture, all in defined proportions and ratios critical for achieving the necessary physical stability, chemical stability and anaesthetic efficacy.
In particular the compositions of the invention comprise from about 0.1 % to about 2%, preferably from about 0.5% to about 1 %, and more preferably from about 0.6% to about 0.8% by weight of benzocaine; from about 25% to about 55%, preferably from about 35% to 50%, and more preferably from about 40% to about 48% by weight of humectant; and from about 43% to about 74.9%, preferably from about 49% to about 64%, and more preferably from about 51 % to about 59% by weight of the mixture of water and lower alcohol.
The water/alcohol mixture itself is in a weight ratio of from about 0.3:1 to about 3:1 , preferably from about 0.4:1 to about 2.5:1 , and especially from about 0.6:1 to about 1 :1. in preferred embodiments, the compositions of the invention comprise from about 10% to about 55%, more preferably from about 15% to about 30% by weight thereof of water, and from about 15% to about 55%, preferably from about 20% to about 40% by weight thereof of lower alcohol, for example, propanol, isopropanol, butanol or ethanol.
The composition of the. humectant is critical herein, being selected from polyethylene glycol having a molecular weight of less than about 1500, preferably less than about 1000, and especially in the range from about 130 to about 600 (for example PEG 300), propylene glycol, glycerol and mixtures thereof. The molecular weight of the polyethylene glycol is selected to achieve optimum formulation stability, viscosity and spray characteristics.
Preferred herein are those compositons in which:
a) the humectant comprises a mixture of polyethylene glycol and propylene glycol in a weight ratio in the range from about 8:1 to about 1 :8, preferably from about 3:1 to about 1 :3, more preferably from about 2:1 to about 1 :2;
b) the humectant comprises a mixture of polyethylene glycol and glycerol in a weight ratio in the range from about 8:1 , preferably from about 3:1 to about 1 :3, more preferably from about 2:1 to about 1 :2; or
SUBSTITUTE SHEET
c) the humectant comprises a mixture of propylene glycol and glycerol in a weight ratio in the range from about 8:1 to about 1 :8, preferably from about 3:1 to about 1 :3, more preferably from about 2:1 to about 1 :2.
in highly preferred embodiments herein, the humectant comprises a mixture of polyethylene glycol, propylene glycol and glycerol in a weight ratro in the range from about 8:1 :1 to about 1 :8:1 to about 1 :1 :8, preferably from about 3:1 :1 to about 1 :3:1 to about 1 :1 :3, more preferably from about 2:1 :1 to about 1 :2:1 to about 1 :1 :2.
The compositions of the invention have no need of and are preferably free of surfactant emulsifiers (especially nonionic and anionic surfactants), although cationic surfactants (eg quaternary ammonium compounds) can be added in levels of from about 0.1 % to about 2% for their germicidal activity. Suitable quaternary ammonium compounds include the alkylarylether dimethylbenzylammonium chlorides, an example of which is 2-[2-(p- octylcresoxy) ethoxy] ethyl dimethylbenzylammonium chloride, available under the name of methylbenzethonium chloride or Hyamine 10X and the corresponding p-octylphenoxy compound available as benzethonium chloride, and the aikyldimethylbenzyl ammonium chlorides available under the name benzalkonium chloride. Other suitable germicidal quaternary ammonium compounds are alkyltrimethyi ammonium chlorides such as cetyltrimethylammonium chloride available under the trade name Cetab; alkyldimethylethylammoπium halides; alkylpyridinium chloride, such as cetylpyridinium chloride; alkylimidazoiinium chloride such as alkylhydroxyethylimidazolinium chloride; alkyldimethyldichiorobenzylammonium chlorides; acyicoiaminoformylinethyl pyridinium chloride available under the name of Emulsept; and
aikarylmethyipyridinium chloride such as polyalkyinaphthaiene methylpyridinium chloride available under the trade name Emcol. In the foregoing compounds the term " alkyl" is understood to encompass Cs to
Ci8» preferably CI Q t0 Cl 6 atkyl radicals including mixtures within this range, this being the range in which quaternary ammonium compounds are considered to have good germicidal activity.
The compositions of this invention can optionally contain one or more other known therapeutic agents, particularly those commonly utilized in cough/cold preparations, such as, for example, a decongestant such as pseudoephedrine hydrochloride, phenγlephedrine hydrochioride and ephedrine hydrochloride; an analgesic such as acetaminophen and ibuprofen; an expectorant such as glyceryl guaiacolate, terpin hydrate and ammonium chloride; and an antihistamine such as chlorpheniramine maleate, doxylamine succinate, brompheniramine maleate and diphenhydramine hydrochloride.
The compositions of the invention are preferably formulated to have a pH in the range from about 4 to about 8, more preferably from about 6 to about 7.5, this pH preferably being maintained through the use of an appropriate pH buffer, eg sodium phosphate, sodium hydrogen phosphate (NaH2PO4) or sodium citrate. Sodium hydrogen phosphate is the preferred buffer.
Other optional ingredients well known to the pharmacist's art may also be included in amounts generally known for these ingredients, for example, natural or artificial sweeteners, flavoring agents and colorants to provide a palatable and pleasant looking final product; antioxidants, for example, butylated hydroxy anisole or butyiated hydroxy toluene, and
SUBSTITUTE SHEET
preservatives, for example, methyl or propyl paraben or sodium benzoate to prolong and enhance shelf life.
The compositions of the invention can be prepared in any convenient form, for example, as a mouthrinse, gargle or aerosol, but highly preferred compositions herein are formulated as a non-aerosol pump spray.
Spray compositions herein preferably have a viscosity in the range of about 1 to about 100 cps, preferably from about 1 to 50 cps, (viscosity being measured using a Brookfield RVT, Spindle RV1 at 100 rpm and 25 °C) and the spray pump is preferably of a finger actuated pump design. The compositions are applied topically in a unit dosage of from about 0.5 to about 10, preferred from about 1 to about 5 mg benzocaine per dose. In the preferred spray pump activator, there are approximately 3 sprays to the unit dose.
SUBSTITUTE SHEET
The invention is illustrated by the following non-limiting Examples:
Examples I to V
III IV V
Benzocaine 0.7 0.7 0.8 0.7 0.5
Cetylpyridinium chloride 0.1 0.1 - - -
Ethanol [96%] 20 35 30 20 10
PEG 300 10 15 18 20 10
Propylene glycol 10 15 14 10 20
Glycerol 10 15 18 10 10
Flavor 0.03 0.03 0.03 0.03 0.03
Sweetener 0.2 0.2 0.2 0.2 0.2
Sodium hydrogen phosphate 1.5 1.5 1.5 1.5 1.5
Water —To 100
PH Adjust to pH 6.5
The compositions combine improved physical stability, together with excellent chemical stability and anaesthetic efficacy.
Claims
A single phase topical anaesthetic composition for sore throat treatment comprising:
a) from about 0.1 % to about 2% by weight of benzocaine;
b) from about 25% to about 55% by weight of humectant selected from polyethylene glycol having a molecular weight of less than 1500, propylene glycol, glycerol and mixtures thereof;
c) from about 43% to about 74.9% by weight of a mixture of water and lower (C1-C4) alcohol in a weight ratio of from about
0.3:1 to 3:1.
A composition according to Claim 1 comprising from about 0.5% to about 1 %, preferably from about 0.6% to about 0.8% by weight of benzocaine.
A composition according to Claim 1 or 2 wherein the humectant is present in a level of from about 35% to about 50%, preferably from about 40% to about 48% by weight.
A composition according to any of Claims 1 to 3 comprising from about 49% to about 64%, preferably from about 51 % to about 59% by weight of the mixture of water and lower alcohol.
5. A composition according to any of Claims 1 to 4 wherein the water and lower alcohol are in a weight ratio in the range from about 0.4:1 to about 2.5:1 , preferably from about 0.6: 1 to about 1 :1.
6. A composition according to any of Claims 1 to 5 comprising from about 10% to about 55%, preferably from about 15% to about 30% by weight thereof of water.
7. A composition according to any of Claims 1 to 6 wherein the humectant comprises a mixture of polyethylene glycol and propylene glycol in a weight ratio in the range from about 8:1 to about 1 :8, preferably from about 3:1 to about 1 :3, more preferably from about 2:1 to about 1 :2.
8. A composition according to any of Claims 1 to 7 wherein the humectant comprises a mixture of polyethylene glycol and glycerol in a weight ratio in the range from about 8:1 to about 1 :8, preferably from about 3:1 to about 1 :3, more preferably from about 2:1 to about 1 :2.
9. A composition according to any of Claims 1 to 8 wherein the humectant comprises a mixture of propylene glycol and glycerol in a weight ratio in the range from about 8:1 to about 1 :8, preferably from about 3: 1 to about 1 :3, more preferably from about 2:1 to about 1 :2.
10. A composition according to any of Claims 1 to 9 wherein the humectant comprises a mixture of polyethylene glycol, propylene glycol and giyceroi in a weight ratio in the range from about 8: 1 : 1 to about 1 :8: 1 to about 1 :1 :8, preferably from about 3:1 :1 to about
SUBSTITUTE SHEET
1 :3:1 to about 1 :1 :3, more preferably from about 2:1 :1 to about 1 :2:1 to about 1 :1 :2.
11. A composition according to any of Claims 1 to 10 additionally comprising a cationic surfactant.
12. A composition according to any of Claims 1 to 1 1 having a pH in the range from about 4 to 8, preferably from about 6 to about 7.5.
13. A composition according to any of Claims 1 to 12 in the form of a spray.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU40315/93A AU4031593A (en) | 1993-03-11 | 1993-03-11 | Throat compositions |
| PCT/US1993/002884 WO1994020087A1 (en) | 1993-03-11 | 1993-03-11 | Throat compositions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US1993/002884 WO1994020087A1 (en) | 1993-03-11 | 1993-03-11 | Throat compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1994020087A1 true WO1994020087A1 (en) | 1994-09-15 |
Family
ID=22236454
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1993/002884 WO1994020087A1 (en) | 1993-03-11 | 1993-03-11 | Throat compositions |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU4031593A (en) |
| WO (1) | WO1994020087A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5547657A (en) * | 1994-10-11 | 1996-08-20 | Eastman Chemical Company | Low-irritation anesthetic and antiseptic mouth rinse |
| WO2008109427A2 (en) * | 2007-03-02 | 2008-09-12 | Combe International Ltd. | Anesthetic spray composition |
| US20160000731A1 (en) * | 2014-07-02 | 2016-01-07 | Xlear, Inc. | Sore-throat compositions and related methods |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4091090A (en) * | 1974-07-08 | 1978-05-23 | Johnson & Johnson | Potentiated anesthetics |
| US4344965A (en) * | 1978-10-13 | 1982-08-17 | Raymond Stone | Anesthetic compositions containing benzocaine |
| US4474748A (en) * | 1979-09-26 | 1984-10-02 | Johnson & Johnson | Medicaments potentiated with phenyl alkanols |
| US4913894A (en) * | 1987-09-11 | 1990-04-03 | Colgate-Palmolive Company | Appetite suppressant dentifrice |
| US4933362A (en) * | 1989-06-06 | 1990-06-12 | Jack Loomstein | Sunburn treatment composition |
-
1993
- 1993-03-11 AU AU40315/93A patent/AU4031593A/en not_active Abandoned
- 1993-03-11 WO PCT/US1993/002884 patent/WO1994020087A1/en active Application Filing
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4091090A (en) * | 1974-07-08 | 1978-05-23 | Johnson & Johnson | Potentiated anesthetics |
| US4344965A (en) * | 1978-10-13 | 1982-08-17 | Raymond Stone | Anesthetic compositions containing benzocaine |
| US4474748A (en) * | 1979-09-26 | 1984-10-02 | Johnson & Johnson | Medicaments potentiated with phenyl alkanols |
| US4913894A (en) * | 1987-09-11 | 1990-04-03 | Colgate-Palmolive Company | Appetite suppressant dentifrice |
| US4933362A (en) * | 1989-06-06 | 1990-06-12 | Jack Loomstein | Sunburn treatment composition |
Non-Patent Citations (2)
| Title |
|---|
| CHEMICAL ABSTRACTS, 111:64036j, 1989, CHARKOUDIAN et al. * |
| CHEMICAL ABSTRACTS, 95:127576, 1981, SCHERICO LTD. * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5547657A (en) * | 1994-10-11 | 1996-08-20 | Eastman Chemical Company | Low-irritation anesthetic and antiseptic mouth rinse |
| WO2008109427A2 (en) * | 2007-03-02 | 2008-09-12 | Combe International Ltd. | Anesthetic spray composition |
| WO2008109427A3 (en) * | 2007-03-02 | 2008-10-30 | Combe Inc | Anesthetic spray composition |
| US20160000731A1 (en) * | 2014-07-02 | 2016-01-07 | Xlear, Inc. | Sore-throat compositions and related methods |
Also Published As
| Publication number | Publication date |
|---|---|
| AU4031593A (en) | 1994-09-26 |
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