US20020120014A1 - Rhinologically active substances - Google Patents

Rhinologically active substances Download PDF

Info

Publication number
US20020120014A1
US20020120014A1 US09/988,860 US98886001A US2002120014A1 US 20020120014 A1 US20020120014 A1 US 20020120014A1 US 98886001 A US98886001 A US 98886001A US 2002120014 A1 US2002120014 A1 US 2002120014A1
Authority
US
United States
Prior art keywords
carbon atoms
denotes
ethyl
ether
active substances
Prior art date
Legal status (The legal status 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 status listed.)
Abandoned
Application number
US09/988,860
Other languages
English (en)
Inventor
Horst Surburg
Arnold Machinek
Hubert Loges
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Haarmann and Reimer GmbH
Original Assignee
Haarmann and Reimer GmbH
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 Haarmann and Reimer GmbH filed Critical Haarmann and Reimer GmbH
Assigned to HAARMANN & REIMER GMBH reassignment HAARMANN & REIMER GMBH ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: LOGES, HUBERT, MACHINEK, ARNOLD, SURBURG, HORST
Publication of US20020120014A1 publication Critical patent/US20020120014A1/en
Priority to US10/626,178 priority Critical patent/US7414079B2/en
Priority to US12/175,156 priority patent/US8569383B2/en
Abandoned legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00—Chewing gum
    • A23G4/06—Chewing gum characterised by the composition containing organic or inorganic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/31—Hydrocarbons
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/203—Alicyclic compounds
    • 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
    • A61K31/075—Ethers or acetals
    • 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
    • A61K9/0056—Mouth soluble or dispersible forms; Suckable, eatable, chewable coherent forms; Forms rapidly disintegrating in the mouth; Lozenges; Lollipops; Bite capsules; Baked products; Baits or other oral forms for animals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/02—Nasal agents, e.g. decongestants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/12—Mucolytics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/16—Central respiratory analeptics

Definitions

  • the invention relates to rhinologically active substances which give rise to a refreshing and clearing feeling in the area of the mouth, the throat and the airways, and to preparations which comprise these compounds.
  • 1,8-Cineole is a substance which is used in large amounts as a rhinologically active substance in pharmaceutical preparations, oral care preparations, such as toothpastes and mouthwashes, and confectionery products, such as cough sweets and chewing-gum, especially because of its property of producing a cooling-refreshing and thus clearing feeling in the region of the mouth, the throat and the airways.
  • 1,8-cineole eucalyptol
  • Lower alkyl ethers of isobornane here particularly of methyl isobornyl ether (Food Chem. Toxicol. 30 (Suppl.), 53S (1992), and of bomane, for example bornyl methyl ether and bornyl ethyl ether, (U.S. Pat. No. 4,131,687) have already been known for a relatively long time as fragrance and aroma substances having fresh, herb-like, rosemary-like or eucalyptus-like sensory properties.
  • 1,8-cineole eucalyptol
  • x is 0 or 1
  • R 1 denotes an alkyl group having 1 to 4 carbon atoms
  • R 2 denotes a methyl or ethyl group
  • R 3 denotes a monocyclic carbon system having 5, 6, 7 or 8 carbon atoms that can be unsubstituted or substituted with further alkyl groups having 1 to 4 carbon atoms or alkenyl groups having 2 to 4 carbon atoms.
  • the inventive new rhinologically active substances are acyclic ethers.
  • the alkyl group having 1 to 4 carbon atoms can be methyl, ethyl, propyl, isopropyl, butyl or isobutyl.
  • the alkenyl group having 2 to 4 carbon atoms can be vinyl, 2-propenyl, allyl or 2-buten-1-yl.
  • the radical R 3 can be unsubstituted or can be substituted, for example, with 1 to 3 methyl groups or with 1 isopropyl group or with 1 methyl group and 1 isopropyl group or with 1 methyl group and 1, 2-propenyl group.
  • inventive rhinologically active substances exhibit an activity comparable to 1,8-cineole (eucalyptol) with respect to a refreshing clearing feeling in the mouth, pharyngeal cavity and the airways, without producing an unpleasant taste sensation.
  • inventive rhinologically active compounds exhibit an activity comparable to 1,8-cineole (eucalyptol), with respect to a refreshing clearing feeling in the mouth, pharyngeal cavity and the airways, was surprising and not predictable to the extent that the inventive ethers do not have a cyclic structure like 1,8-cineole (eucalyptol), but have an acyclic structure.
  • Preferred rhinologically active compounds in the context of the present invention are compounds of the formula
  • x can have the value 0 or 1
  • R 1 denotes a methyl or ethyl group
  • R 2 denotes a methyl or ethyl group
  • R 3 denotes a monocyclic carbon system having 6 or 7 carbon atoms that can be unsubstituted or substituted with further alkyl groups having 1 to 3 carbon atoms and/or alkenyl groups having 3 carbon atoms.
  • the present flavor compounds render pleasantly tasting flavor compounds, which have the activity of causing a refreshing clearing feeling in the mouth, pharyngeal cavity and the airways.
  • the inventive rhinologically active compounds are selected from the group of l-menthyl methyl ether, d-menthyl methyl ether, dl-menthyl methyl ether, menthyl ethyl ether, menthyl propyl ether, menthyl isobutyl ether, isopulegyl methyl ether, 2-isopropylcyclohexyl methyl ether, 2-isopropylcyclohexyl ethyl ether, 3,3,5-trimethylcyclohexyl methyl ether, 1-(3,3-dimethylcyclohexyl)-ethyl ethyl ether, 1-(3,3-dimethylcyclohexyl)ethyl propyl ether, and 1-(3,3-dimethyl
  • Preparation of the acyclic ethers for the inventive rhinologically active compounds is known per se. It can be performed, for example, by etherification of the corresponding alcohols with alkylating agents, such as alkyl halides, alkyl tosylates, alkyl mesylates or alkyl halides in the presence of an equivalent amount of a basic compound. Particularly advantageous here is etherification by the phase-transfer process, which is described, for example, in Angew. Chem.
  • the alcohol to be etherified is vigorously stirred in a nonpolar solvent in the presence of a phase-transfer catalyst, for example tetrabutylammonium iodide, with a 2.5-fold excess of 50% strength sodium hydroxide solution and 1.2-fold excess of an alkylating agent is added. After a customary cleanup, the corresponding ether is obtained, which is separated off from unreacted alcohol by distillation or liquid chromatography.
  • a phase-transfer catalyst for example tetrabutylammonium iodide
  • the inventive rhinologically active compounds can be combined with one another in pure form, or, in a preferred form, can be combined with aroma substances or flavor substances.
  • Suitable aroma substances are both complex natural raw materials, such as extracts and essential oils produced from plants, and fractions and homogeneous substances produced therefrom, and also homogeneous synthetically or biotechnologically produced aroma substances.
  • Examples of natural raw materials are, for example: peppermint oils, spearmint oils, Mentha arvensis oils, aniseed oils, clove oils, citrus oils, cinnamon bark oils, winter green oils, cassia oils, davana oils, spruce needle oils, eucalyptus oils, fennel oils, galbanum oils, ginger oils, camomile oils, cumin oils, rose oils, geranium oils, sage oils, yarrow oils, star anise oils, thyme oils, juniper berry oils, rosemary oils, angelica root oils, and fractions of these oils.
  • Examples of homogeneous aroma substances are, for example: anethole, menthol, menthone, isomenthone, menthyl acetate, menthofuran, mint lactone, eucalyptol, limonene, eugenol, pinene, sabinene hydrate, 3-octanol, carvone, gamma-octalactone, gamma-nonalactone, germacrene-D, viridiflorol, 1,3E,5Z-undecatriene, isopulegol, piperitone, 2-butanone, ethyl formate, 3-octyl acetate, isoamyl isovalerate, hexanol, hexanal, cis-3-hexenol, linalool, alpha-terpineol, cis and trans carvyl acetate, p-cymol, damascen
  • Examples of other flavor substances which can be advantageously combined with the inventive rhinologically active substances are, for example, substances having a physiologically cooling action, that is to say substances which cause an impression of cold in the mucous membranes.
  • substances having a cooling action are, for example, l-menthol, 1-isopulegol, menthone glycerol acetal, menthyl lactate, substituted menthane-3-carboxamides (for example N-ethylmenthane-3-carboxamide), 2-isopropyl-N,2,3-trimethylbutanamide, substituted cyclohexanecarboxamides, 3-menthoxy-1,2-propanediol, 2-hydroxyethylmenthyl carbonate, 2-hydroxypropylmenthyl carbonate, N-acetylglycine menthyl ester, menthylhydroxycarboxylic esters (for example menthyl 3-hydroxybutyrate), menthyl monosuccinate, 2-mercapto
  • inventive rhinologically active substances can be present in the aroma or flavor substance compositions at a content of 0.1 to 100% by weight. Preference is given to a content of 0.1 to 70% by weight; more preference is given to a content of 0.5 to 40% by weight.
  • aroma or flavor substance compositions comprising the inventive rhinologically active substances can be used in pure form, as solutions, or else in specially prepared form, and incorporated into ready-to-use products.
  • Suitable solvents are, for example, ethyl alcohol, 1,2-propylene glycol, triacetin, benzyl alcohol and fatty oils, for example coconut oil or sunflower seed oil.
  • the aroma or flavor substance compositions comprising the inventive rhinologically active substances can also comprise additives and aids, for example preservatives, pigments, antioxidants, anticaking agents, thickeners, etc.
  • the aroma or flavor substance compositions comprising the inventive rhinologically active substances can be bound to a carrier, spray-dried or else encapsulated.
  • the aroma or flavor substance compositions can be bound on or in a carrier, for example sodium chloride, sugar, starches or sugar melts.
  • the spray-dried form is produced from the liquid compositions by producing an emulsion with addition of defined amounts of a carrier, preferably biopolymers such as starch, modified starches, maltodextrin and gum arabic.
  • a carrier preferably biopolymers such as starch, modified starches, maltodextrin and gum arabic.
  • This emulsion is dried in spray-dryers by very fine distribution with uniform temperature application. A powder results having the desired loading of liquid composition.
  • the encapsulated form is also produced from the liquid compositions by adding a carrier.
  • a carrier Various technologies exist by which capsules can be produced. The most familiar are extrusion, spray-granulation and coacervation. The particle sizes customarily extend from 10 ⁇ m to 5 mm. The most familiar capsule materials are various starches, maltodextrin and gelatin. In these capsules, the liquid or solid aroma or flavor substance compositions are enclosed and can be released by various mechanisms such as use of heat, pH shift or chewing pressure.
  • the inventive rhinologically active substances are suitable for producing preparations of the most varied flavors, particularly for use in aroma compositions having a cooling-refreshing mint-like flavor.
  • the mint compositions are essentially characterized by a content of peppermint oils, Mentha arvensis oils, spearmint oils, eucalyptus oils, 1,8-cineole (eucalyptol), menthol and substances having a physiologically cooling activity.
  • composition constituents of the mint compositions can vary here generally between 0.1 and 99.9%
  • Mint compositions which are preferably used are those having 1 to 90% by weight of menthol, 1 to 60% by weight of menthone, 1 to 90% by weight of peppermint or Mentha arvensis oils, 1 to 90% by weight of spearmint oils, 1 to 90% by weight of eucalyptol or eucalyptol-containing eucalyptus oils, 0.5 to 70% by weight of the inventive rhinologically active substances, for example menthyl methyl ether, isopulegyl methyl ether or the like and 0.5 to 70% by weight of substances having a physiologically cooling action.
  • Mint compositions which are preferably used are those having 20 to 60% by weight of menthol, 5 to 30% of menthone, 5 to 60% by weight of peppermint or Mentha arvensis oils, 5 to 60% by weight of spearmint oils, 2 to 50% by weight of eucalyptol or eucalyptol-containing eucalyptus oils, 0.5 to 40% by weight of the inventive rhinologically active substances, for example menthyl methyl ether, isopulegyl methyl ether or the like and 1 to 30% by weight of substances having a physiological cooling action.
  • Substances having a physiological cooling action can be the above-described, in which case they are used individually or as mixtures. If mixtures are used, these are generally mixtures, for example, of menthone glycerol acetal, menthyl lactate, substituted menthyl-3-carboxamides (for example N-ethylmenthyl-3-carboxamide), 2-hydroxyethylmenthyl carbonate and 2′-hydroxypropylmenthyl carbonate.
  • mixtures which have 1 to 99% by weight of menthone glycerol acetal, 1 to 99% by weight of menthyl lactate, 1 to 99% by weight of N-ethylmenthyl-3-carboxamide, 1 to 99% by weight of 2-hydroxyethylmenthyl carbonate and 1 to 99% by weight of hydroxypropylmenthyl carbonate.
  • mint compositions can be modified in flavor, with the content by weight of the added aroma substances generally being 0.001 to 50% by weight, based on the weight fraction of minty compounds and cooling compounds. Preference is given to an addition of 0.01 to 30% by weight, preferably an addition of 0.1 to 10% by weight, based on the weight fraction of the minty and cooling substances.
  • the content of the eucalyptus oils and of 1,8-cineole (eucalyptol) and thus the strong medicinal flavor note can be reduced, without reducing the refreshing clearing feeling in the mouth, pharyngeal cavity and the airways.
  • the perception of freshness which is produced by the inventive rhinologically active substances in the airways, in the mouth and in the pharyngeal cavity is of longer duration than that caused by 1,8-cineole (eucalyptol).
  • compositions comprising the inventive rhinologically active substances can advantageously be used, especially in oral care compositions, such as toothpastes and mouthwashes, chewing-gum, foods, such as confectionery and sweets for sucking, luxury consumption merchandise, such as tobacco, pharmaceutical preparations, nasal sprays.
  • the content of the preparations comprising the inventive rhinologically active substances is, in ready-to-use mouthwashes 0.01 to 1% by weight, preferably 0.1 to 0.3% by weight.
  • mouthwash concentrates the content of the compositions comprising the inventive rhinologically active substances is between 0.01 and 20% by weight, preferably 0.1 to 10% by weight, and more preferably 3 to 5% by weight.
  • toothpastes and chewing-gum the compositions comprising the inventive rhinologically active substances are used at a concentration between 0.1 and 5% by weight, preferably 0.5 to 2% by weight, and more preferably between 0.8 and 1.5% by weight.
  • the content of the compositions comprising the inventive rhinologically active substances is between 0.01 and 2% by weight, preferably 0.05 to 1 % by weight; and more preferably between 0.1 and 0.5%.
  • Toothpastes that are flavored with the compositions comprising the inventive rhinologically active substances generally consist of an abrasive system (abrasives or polishes), for example silicic acids, calcium carbonates, calcium phosphates, aluminum oxides and/or hydroxyl apatites; surface-active substances, for example sodium lauryl sulphate, sodium lauryl sarcosinate and/or cocamidopropylbetaine; humectants, for example glycerol and/or sorbitol; thickeners, for example carboxymethyl cellulose, polyethylene glycols, carrageenans and/or Laponites®, sweeteners, for example saccharin; stabilizers; and active compounds, for example sodium fluoride, sodium monofluorophosphate, tin difluoride, quaternary ammonium fluorides, zinc citrate, zinc sulphate, tin pyrophosphate, tin dichloride, mixtures of various pyrophosphate
  • Chewing-gum that is flavored with the compositions comprising the inventive rhinologically active substances generally consists of a chewing-gum base, that is to say a chewing mass which becomes plastic on chewing; sugars of various types; sugar substitutes; sweeteners; sugar alcohols; humectants; thickeners; emulsifiers; and stabilizers.
  • inventive rhinologically active substances or the compositions comprising the inventive rhinologically active substances are particularly suitable for freshening the breath and neutralizing or reducing bad breath.
  • inventive rhinologically active substances or the compositions comprising the rhinologically active substances in oral care products leads to unpleasant, especially bitter, taste impressions being masked or neutralized, as are caused, for example, by substances such as triclosan, zinc citrate, zinc sulphate, polyphosphates and pyrophosphates, bicarbonates, strontium salts and potassium salts, tin pyrophosphate, tin chloride, aluminum lactate, hydrogen peroxide, fluorides, vitamins, cetylpyridinium chloride, and emulsifiers, for example, particularly sodium lauryl sulphate, sodium lauryl sarcosinate and cocamidopropylbetaine, and sweeteners, for example aspartame, saccharin, acesulfame-K, sorbitol; xylitol, cyclamates (for example sodium cyclamate), sucralose
  • a further positive property of the inventive rhinologically active substances which must be emphasized is their stability in toothpastes based on chalk or bicarbonate which, because of their alkaline pH, are difficult to flavor.
  • inventive rhinologically active substances and the compositions comprising the inventive rhinologically active substances are also suitable, however, for use in pharmaceutical preparations, for example, nasal drops and nasal sprays or embrocations.
  • compositions comprising the inventive rhinologically active substances are suitable, in particular, for masking the bitter taste of medicaments.
  • the flavoring was incorporated at a concentration of 1.3% by weight into a standard toothpaste mix based on silicic acid.
  • the toothpaste was tested under conditions of practice by an expert panel trained in sensory testing. The results showed that the flavoring gave a taste impression of high intensity and long-lasting duration, a pronounced markedly refreshing, clearing feeling being perceived in the airways, in the mouth and in the pharyngeal cavity.
  • the flavoring was incorporated at a concentration of 1.5% by weight into a sugar-free standard chewing-gum base.
  • the chewing gum was tested for a sensory quality by a trained expert panel. It was found that addition of l-menthyl methyl ether gave a markedly refreshing clearing feeling in the airways, in the mouth and in the pharyngeal cavity, and the taste roundness and intensity of the peppermint flavoring was markedly increased.

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Food Science & Technology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Polymers & Plastics (AREA)
  • Nutrition Science (AREA)
  • Pulmonology (AREA)
  • Inorganic Chemistry (AREA)
  • Physiology (AREA)
  • Zoology (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Otolaryngology (AREA)
  • Birds (AREA)
  • Cosmetics (AREA)
  • Confectionery (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
  • Graft Or Block Polymers (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Chemical And Physical Treatments For Wood And The Like (AREA)
  • Fats And Perfumes (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)
US09/988,860 2000-11-24 2001-11-21 Rhinologically active substances Abandoned US20020120014A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US10/626,178 US7414079B2 (en) 2000-11-24 2003-07-24 Utilization of rhinologically active substances
US12/175,156 US8569383B2 (en) 2000-11-24 2008-07-17 Utilization of rhinologically active substances

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10058459A DE10058459A1 (de) 2000-11-24 2000-11-24 Rhinologica
DE10058459.4 2000-11-24

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US10/626,178 Division US7414079B2 (en) 2000-11-24 2003-07-24 Utilization of rhinologically active substances

Publications (1)

Publication Number Publication Date
US20020120014A1 true US20020120014A1 (en) 2002-08-29

Family

ID=7664566

Family Applications (3)

Application Number Title Priority Date Filing Date
US09/988,860 Abandoned US20020120014A1 (en) 2000-11-24 2001-11-21 Rhinologically active substances
US10/626,178 Expired - Lifetime US7414079B2 (en) 2000-11-24 2003-07-24 Utilization of rhinologically active substances
US12/175,156 Expired - Lifetime US8569383B2 (en) 2000-11-24 2008-07-17 Utilization of rhinologically active substances

Family Applications After (2)

Application Number Title Priority Date Filing Date
US10/626,178 Expired - Lifetime US7414079B2 (en) 2000-11-24 2003-07-24 Utilization of rhinologically active substances
US12/175,156 Expired - Lifetime US8569383B2 (en) 2000-11-24 2008-07-17 Utilization of rhinologically active substances

Country Status (14)

Country Link
US (3) US20020120014A1 (de)
EP (1) EP1341512B1 (de)
JP (1) JP2004513960A (de)
KR (1) KR20030068158A (de)
AT (1) ATE418871T1 (de)
AU (1) AU2002223676A1 (de)
BR (1) BR0115581B1 (de)
CA (1) CA2429618A1 (de)
CZ (1) CZ20031771A3 (de)
DE (2) DE10058459A1 (de)
HU (1) HUP0303043A3 (de)
PL (1) PL362208A1 (de)
RU (1) RU2295950C2 (de)
WO (1) WO2002041861A1 (de)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004073672A1 (en) * 2003-02-18 2004-09-02 Quest International Services B.V. Improvements in or relating to flavour compositions
US20060029628A1 (en) * 2004-04-23 2006-02-09 Joerg Kleinwaechter Use of a volatile cooling sensate on fibrous tissues to provide a sensation of rhinological decongestion
US20060073195A1 (en) * 2004-04-23 2006-04-06 Joerg Kleinwaechter Tissue including a volatile rhinological composition
EP1698331A1 (de) * 2005-02-28 2006-09-06 The Procter & Gamble Company Verwendung einer flüchtigen, rhinologisch wirksamen Zusammensetzung auf faserigen Gewebe zur Erleichterung der nasalen Atmung
US20070148283A1 (en) * 2005-12-23 2007-06-28 Cadbury Adams Usa Llc Compositions providing a sensation substantially similar to that provided by menthol
US8518919B2 (en) 2004-11-24 2013-08-27 Meda Pharmaceuticals Inc. Compositions comprising azelastine and methods of use thereof
US20160128918A1 (en) * 2014-11-11 2016-05-12 Colgate-Palmolive Company Use of benzyl alcohol as a defoaming agent
US10064817B2 (en) 2004-11-24 2018-09-04 Meda Pharmaceuticals Inc. Compositions comprising azelastine and methods of use thereof
US20210337848A1 (en) * 2020-05-01 2021-11-04 The Procter & Gamble Company Mint Flavor Compositions
WO2022023330A1 (en) * 2020-07-28 2022-02-03 Basf Se Cyclic compounds as aroma chemicals

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1716837B1 (de) * 2005-02-28 2017-06-07 The Procter & Gamble Company Verwendung von einem Kältegefühl erzeugenden flüchtigen Material auf faserigen Stoffen um eine rhinologische Dekongestion zu erreichen
DE102005056054B3 (de) * 2005-11-24 2007-05-24 Luetgebrune, Thomas, Dr.med. Pharmazeutische Zusammensetzung zur Behandlung und/oder Prävention von mindestens einer Atemwegserkrankung
DE102008043586A1 (de) 2007-11-12 2009-05-14 Symrise Gmbh & Co. Kg Riechstoffakkorde zur Bekämpfung der Wahrnehmung von Körpergeruch
EP2133102B1 (de) 2008-03-19 2014-12-03 Symrise AG Geruchsreduzierende Stoffe
EP2168957B1 (de) 2009-03-06 2012-02-15 Symrise AG Alkylsubstituierte Tetrahydropyrane als Aromastoffe
BRPI0924661B1 (pt) 2009-04-28 2018-12-11 Symrise Ag Ômega-ciclo-hexilalcan-1-óis, seus métodos de produção, suas composições, suas formulações cosméticas, uso dos mesmos como ativos microbianos e método parareduzir a taxa de crescimento de corynebacterium xerosis e/ou staphylococcus epidermidis e/ou brevibacterium epidermidis
FR2948661B1 (fr) * 2009-07-31 2011-07-29 Arkema France Composition a base de sulfure organique a odeur masquee
KR101261230B1 (ko) * 2010-11-29 2013-05-07 한림제약(주) 모메타손 푸로에이트 및 아젤라스틴 염산염을 포함하는 비내 투여용 약학 조성물
EP2662434B2 (de) 2012-05-10 2023-08-16 Symrise AG Verwendung bestimmter Verbindungen zum Verstärken von Gerüchen
EP2801263B1 (de) * 2013-05-09 2021-04-14 Symrise AG Verfahren zur Herstellung einer kühlende Zusammensetzung in Form eines Granulats
EP3072877B1 (de) * 2013-12-26 2018-08-15 Kao Corporation Ester
EP2966159B1 (de) 2014-07-07 2017-02-22 Symrise AG Mischungen mit angereichten E-Isomeren von ungesättigten makrocyclischen Moschusverbindungen
EP2966158B2 (de) 2014-07-07 2024-03-13 Symrise AG Isomerenmischungen von ungesättigten makrocyclischen Moschusverbindungen
CN112969444A (zh) 2018-11-12 2021-06-15 西姆莱斯有限公司 1-乙基-4，4-二甲基环己烷衍生物作为香味物质的用途
CN112969774A (zh) 2018-11-13 2021-06-15 西姆莱斯有限公司 具有铃兰香味的加香成分
US20220049183A1 (en) 2018-12-20 2022-02-17 Symrise Ag Alicyclic musk fragrance compounds
WO2023213381A1 (en) 2022-05-03 2023-11-09 Symrise Ag Novel fragrance compounds

Family Cites Families (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3128772A (en) * 1962-11-19 1964-04-14 Brown & Williamson Tobacco Smoking tobacco additives in the form of menthyl ethers
US3947570A (en) * 1972-11-06 1976-03-30 Colgate-Palmolive Company Oral product
CH578312A5 (de) * 1973-06-07 1976-08-13 Firmenich & Cie
DE2658567C2 (de) * 1976-12-23 1986-09-18 Henkel KGaA, 4000 Düsseldorf Verwendung von cis- und trans-3,3,5-Trimethylcyclohexyl-ethylether und deren Gemischen als Riechstoffe, sowie diese enthaltende Riechstoffkompositionen
US4131687A (en) * 1978-01-27 1978-12-26 International Flavors & Fragrances Inc. Flavoring with terpenyl ethers
US4275080A (en) * 1978-01-27 1981-06-23 International Flavors & Fragrances Inc. Flavoring with 8-p-cymenyl-ethyl ether
US4476142A (en) * 1982-12-20 1984-10-09 Warner-Lambert Company Peppermint oil flavored compositions
DE3629603A1 (de) * 1986-08-30 1988-03-03 Basf Ag 2-tert-butyl-4-methyl-cyclohexanolderivate, deren herstellung und verwendung als riechstoffe
US4873266A (en) * 1987-01-16 1989-10-10 American Home Products Corp. Menthone enhancement of transdermal drug delivery
US5166412A (en) * 1990-08-28 1992-11-24 Firmenich S.A. Esters and their use in perfumery
CA2147883C (en) * 1992-10-29 2000-06-13 Akira Nakagawa Cyclohexanol derivative, cool feeling and cool feeling composition containing the same, process for producing the derivative and intermediate therefor
US6123950A (en) * 1994-12-22 2000-09-26 The Procter & Gamble Company Silicone compositions
US6294154B1 (en) * 1994-12-22 2001-09-25 Procter And Gamble Company Oral compositions containing dimethicone copolyols
GB9505518D0 (en) 1995-03-18 1995-05-03 Procter & Gamble Perfumed bleaching compositions
US5695746A (en) * 1995-07-28 1997-12-09 Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. Liquid dentifrice with mouthwash fresh taste
US6231900B1 (en) * 1995-08-19 2001-05-15 The Procter & Gamble Company Confectionery product and preparation thereof
US5610133A (en) * 1995-08-31 1997-03-11 International Flavors & Fragrances Inc. Alkyl-substituted-C1 -C3 alkoxy-C6 -cycloaliphatic compounds, organoleptic uses thereof and processes for preparing same
JP3219995B2 (ja) 1996-02-08 2001-10-15 高砂香料工業株式会社 清涼感改善剤
US6083525A (en) 1996-05-10 2000-07-04 Fust; Charles A. Compositions for freshening nostrils and sinus cavities
JPH11152235A (ja) * 1997-08-20 1999-06-08 Toray Ind Inc 光学異性体の吸着分離方法およびメントール誘導体
JP2000239142A (ja) 1999-02-19 2000-09-05 Shiseido Co Ltd 冷感化粧料
DE60107580T2 (de) 2000-08-14 2005-05-25 Quest International Services B.V. Riechstoffe
MXPA03001374A (es) 2000-08-14 2003-06-06 Quest Int Produccion de 3-alquilcicloalcanoles.

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004073672A1 (en) * 2003-02-18 2004-09-02 Quest International Services B.V. Improvements in or relating to flavour compositions
US20060029628A1 (en) * 2004-04-23 2006-02-09 Joerg Kleinwaechter Use of a volatile cooling sensate on fibrous tissues to provide a sensation of rhinological decongestion
US20060073195A1 (en) * 2004-04-23 2006-04-06 Joerg Kleinwaechter Tissue including a volatile rhinological composition
US8343534B2 (en) * 2004-04-23 2013-01-01 The Procter & Gamble Company Tissue including a volatile rhinological composition
US9919050B2 (en) 2004-11-24 2018-03-20 Meda Pharmaceuticals Inc. Compositions comprising azelastine
US8518919B2 (en) 2004-11-24 2013-08-27 Meda Pharmaceuticals Inc. Compositions comprising azelastine and methods of use thereof
US10064817B2 (en) 2004-11-24 2018-09-04 Meda Pharmaceuticals Inc. Compositions comprising azelastine and methods of use thereof
EP1698331A1 (de) * 2005-02-28 2006-09-06 The Procter & Gamble Company Verwendung einer flüchtigen, rhinologisch wirksamen Zusammensetzung auf faserigen Gewebe zur Erleichterung der nasalen Atmung
WO2006093537A1 (en) * 2005-02-28 2006-09-08 The Procter & Gamble Company Use of a volatile rhinological effective composition on fibrous tissues to provide a sensation of sinusoidal relieve
US20070148283A1 (en) * 2005-12-23 2007-06-28 Cadbury Adams Usa Llc Compositions providing a sensation substantially similar to that provided by menthol
US20160128918A1 (en) * 2014-11-11 2016-05-12 Colgate-Palmolive Company Use of benzyl alcohol as a defoaming agent
CN105581914A (zh) * 2014-11-11 2016-05-18 高露洁-棕榄公司 苯甲醇作为消泡剂的用途
US10071035B2 (en) * 2014-11-11 2018-09-11 Colgate-Palmolive Company Use of benzyl alcohol as a defoaming agent
US20210337848A1 (en) * 2020-05-01 2021-11-04 The Procter & Gamble Company Mint Flavor Compositions
CN115484922A (zh) * 2020-05-01 2022-12-16 宝洁公司 薄荷风味物组合物
WO2022023330A1 (en) * 2020-07-28 2022-02-03 Basf Se Cyclic compounds as aroma chemicals

Also Published As

Publication number Publication date
PL362208A1 (en) 2004-10-18
EP1341512B1 (de) 2008-12-31
DE10058459A1 (de) 2002-06-06
KR20030068158A (ko) 2003-08-19
WO2002041861A1 (de) 2002-05-30
US20050027017A1 (en) 2005-02-03
DE50114628D1 (de) 2009-02-12
RU2295950C2 (ru) 2007-03-27
JP2004513960A (ja) 2004-05-13
ATE418871T1 (de) 2009-01-15
US20080274064A1 (en) 2008-11-06
BR0115581A (pt) 2003-09-09
CZ20031771A3 (cs) 2003-11-12
HUP0303043A2 (hu) 2003-12-29
HUP0303043A3 (en) 2006-06-28
BR0115581B1 (pt) 2014-01-28
AU2002223676A1 (en) 2002-06-03
US8569383B2 (en) 2013-10-29
CA2429618A1 (en) 2002-05-30
EP1341512A1 (de) 2003-09-10
US7414079B2 (en) 2008-08-19

Similar Documents

Publication Publication Date Title
US8569383B2 (en) Utilization of rhinologically active substances
EP2168957B1 (de) Alkylsubstituierte Tetrahydropyrane als Aromastoffe
EP0452273B1 (de) Mischung von Ameisensäureestern und pfefferartigen Bestandteilen als ein oral konsumierbares Chloroform-Ersatzmittel
US9446267B2 (en) Products comprising a flavoring agent composition
EP2033688B1 (de) Oxalsäurederivate und deren Verwendung als physiologische Kühlwirkstoffe
CN1124126C (zh) 清凉剂组合物
EP2187871B1 (de) Pellitorin enthaltende gemische und ihre verwendungen
US20080000614A1 (en) Hot flavor and skin sensation composition
EP2364689B1 (de) Mentholhaltige Zahnputz-Zusammensetzung mit reduzierter Bitterwahrnehmung
US20050244561A1 (en) Carvone acetals used as flavourings
CN109310130B (zh) 清凉物质混合物
DE10225350A1 (de) Aromakompositionen mit Frischewirkung
DE10227734A1 (de) Neue Phenylester

Legal Events

Date Code Title Description
AS Assignment

Owner name: HAARMANN & REIMER GMBH, GERMANY

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:SURBURG, HORST;MACHINEK, ARNOLD;LOGES, HUBERT;REEL/FRAME:012639/0378;SIGNING DATES FROM 20020111 TO 20020114

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION