WO2004101472A2 - Nouveaux derives de fragrance - Google Patents

Nouveaux derives de fragrance Download PDF

Info

Publication number
WO2004101472A2
WO2004101472A2 PCT/US2004/014399 US2004014399W WO2004101472A2 WO 2004101472 A2 WO2004101472 A2 WO 2004101472A2 US 2004014399 W US2004014399 W US 2004014399W WO 2004101472 A2 WO2004101472 A2 WO 2004101472A2
Authority
WO
WIPO (PCT)
Prior art keywords
product
reaction
double bond
thiirane
mixture
Prior art date
Application number
PCT/US2004/014399
Other languages
English (en)
Other versions
WO2004101472A3 (fr
Inventor
Luca Turin
Original Assignee
Flexitral Inc.
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 Flexitral Inc. filed Critical Flexitral Inc.
Priority to AU2004238835A priority Critical patent/AU2004238835A1/en
Priority to CA002524897A priority patent/CA2524897A1/fr
Priority to JP2006532874A priority patent/JP2007516956A/ja
Priority to GB0524992A priority patent/GB2419593B/en
Priority to EP04760941A priority patent/EP1625106A4/fr
Publication of WO2004101472A2 publication Critical patent/WO2004101472A2/fr
Publication of WO2004101472A3 publication Critical patent/WO2004101472A3/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D301/00—Preparation of oxiranes
    • C07D301/02—Synthesis of the oxirane ring
    • C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
    • C07D301/14—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with organic peracids, or salts, anhydrides or esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D331/00—Heterocyclic compounds containing rings of less than five members, having one sulfur atom as the only ring hetero atom
    • C07D331/02—Three-membered rings
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0069—Heterocyclic compounds
    • C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
    • C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes

Definitions

  • the present invention relates generally to the field of fragrances. More particularly, the present invention relates to improved derivatives of conventional aromachemicals, i.e., fragrance compounds that provide perfumes and other articles with properties and advantages not shared by the conventional derivatives from which they are derived. These derivatives find utility in any and all applications requiring the themes supplied by the conventional fragrances from which they are derived.
  • the invention also relates to mixtures of these derivatives, methods for their preparation and their use as perfume materials for application to a variety of substrates.
  • fragrances used as ingredients in perfumes and in a varied range of other products.
  • perfumes for application in laundry detergents, fabric softeners, rinse conditioners and other products intended for use on textile fibers primarily contain fragrances.
  • the invention is directed toward the derivitization of fragrance molecules or aromachemical molecules having at least one double bond, wherein at least one double bond has been converted to an oxirane or thiirane.
  • the inventive method may be described as the conversion of the double bond to an oxirane group and then, if desired, to a thiirane group according to the following scheme:
  • the invention is predicated on the discovery that replacing the double bond of a fragrance compound with an oxirane or a thiirane group enables the molecule to bind to a metal ion without changing the molecule's odor characteristics. Calculations suggest that the thiirane group is optimal in this respect.
  • This ability to bind metal ions is advantageous because the receptor proteins responsible for odorant detection incorporate a zinc ion at their binding site. Metal-binding ability thereby increases the affinity of the derivative for the receptor, and therefore its potency as an odorant.
  • the electronic structure of oxygen and especially sulfur enables them to coordinate metal ions.
  • the conversion of the double bond to the oxirane is achieved by oxidation, for example, by reaction with a peracid such as meta- chloroperbenzoic acid (mCPBA), peroxybenzoic acid, oxygen with an Ag catalyst or t-butyl hydroperoxide in the presence of Ti(IV) isopropoxide (Sharpless reaction).
  • a peracid such as meta- chloroperbenzoic acid (mCPBA), peroxybenzoic acid, oxygen with an Ag catalyst or t-butyl hydroperoxide in the presence of Ti(IV) isopropoxide (Sharpless reaction).
  • the oxirane can then be used to prepare the corresponding thiirane by reacting it, for example, with triphenylphosphine sulfide-picric acid, thiourea, potassium thiocyanate on silica gel.
  • the thiirane may be prepared directly from a double bond by reaction with succinimide-N-sulfenyl
  • suitable articles of manufacture in which the derivatives of the invention may be incorporated include perfumes and colognes, candles, air fresheners, detergent compositions and disinfectants.
  • Figure 1 depicts the structural formulae of several thiiranes that can be produced according to the invention.
  • the derivatives of the invention can be used, for example, as fragrances in any applications in which the fragrances from which they were derived are applied.
  • the derivatives of the invention can be included in virtually any article of manufacture that can include conventional fragrances, whether natural or artificial. Examples include bleach, detergents, flavorings and fragrances, beverages, including alcoholic beverages, and the like.
  • the derivatives can be used in applications like soaps, shampoos, body deodorants and antiperspirants, solid or liquid detergents for treating textiles, fabric softeners, detergent compositions and/or all-purpose cleaners for cleaning dishes or various surfaces, for both household and industrial use.
  • the use of the compounds is not limited to the above-mentioned products, as they be used in other current uses in perfumery, namely the perfuming of soaps and shower gels, hygiene or hair-care products, as well as of body deodorants, air fresheners and cosmetic preparations, and even in fine perfumery, namely in perfumes and colognes. These uses are described in more detail below.
  • the compounds can be used as perfuming ingredients, as single compounds or as mixture thereof, preferably at a range of at least about 30% by weight of the perfume composition, more preferably at a range of at least about 60% by weight of the composition.
  • the compounds can even be used in their pure state or as mixtures, without added components.
  • the olfactive characteristics of the individual compounds are also present in mixtures thereof, and mixtures of these compounds can be used as perfuming ingredients. This may be particularly advantageous where separation and/or purification steps can be avoided by using compound mixtures.
  • the derivatives can be used alone or in admixture with other perfuming ingredients, solvents or adjuvants of current use in the art.
  • the nature and the variety of these co-ingredients do not require a more detailed description here, which, moreover, would not be exhaustive, and the person skilled in the art will be able to choose the latter through its general knowledge and as a function of the nature of the product to be perfumed and of the desired olfactive effect.
  • perfuming ingredients typically belong to chemical classes as varied as alcohols, aldehydes, ketones, esters, ethers, acetates, nitrites, terpene hydrocarbons, sulfur- and nitrogen containing heterocyclic compounds, as well as essential oils of natural or synthetic origin.
  • alcohols aldehydes, ketones, esters, ethers, acetates, nitrites, terpene hydrocarbons, sulfur- and nitrogen containing heterocyclic compounds, as well as essential oils of natural or synthetic origin.
  • the proportions in which the derivatives can be incorporated in the various products vary within a large range of values. These values depend on the nature of the article or product that one desires to perfume and the odor effect searched for, as well as on the nature of the co-ingredients in a given composition when the compounds are used in admixture with perfuming co-ingredients, solvents or adjuvants of current use in the art.
  • the derivatives are typically present at concentrations between about 0.1 and about 10%, or even more, by weight of these compounds relative to the weight of the perfuming composition in which they are incorporated. Far lower concentrations than those mentioned above can be used when the compounds are directly applied for perfuming the various consumer products cited beforehand.
  • the compounds can also be used in body deodorants and antiperspirants, for example, those containing aluminum salts. These embodiments are described in more detail below.
  • compositions herein include a detersive surfactant and optionally, one or more additional detergent ingredients, including materials for assisting or enhancing cleaning performance, treatment of the substrate to be cleaned, or to modify the aesthetics of the detergent composition (e.g., perfumes, colorants, dyes, etc.).
  • additional detergent ingredients including materials for assisting or enhancing cleaning performance, treatment of the substrate to be cleaned, or to modify the aesthetics of the detergent composition (e.g., perfumes, colorants, dyes, etc.).
  • Non-limiting examples of synthetic detersive surfactants useful herein typically at levels from about 0.5% to about 90%, by weight, include the conventional Cl-18 alkyl benzene sulfonates ("LAS") and primary, branch-chain and random CIO-20 alkyl sulfates ("AS”), and the like.
  • Preferred compositions incorporating only synthetic detergents have a detergent level of from about 0.5% to 50%.
  • Compositions containing soap preferably comprise from about 10% to about 90% soap.
  • compositions herein can contain other ingredients such as enzymes, bleaches, fabric softening agents, dye transfer inhibitors, suds suppressors, and chelating agents, all well known within the art.
  • the derivatives described herein can be incorporated into beverages and impart various flavorings to the beverages.
  • the beverage composition can be a cola beverage composition, and can also be coffee, tea, dairy beverage, fruit juice drink, orange drink, lemon-lime drink, beer, malt beverages, or other flavored beverage.
  • the beverages can be in liquid or powdered form.
  • the beverage compositions can also include one or more flavoring agents; artificial colorants; vitamin additives; preservatives; caffeine additives; water; acidulants; thickeners; buffering agents; emulsifiers; and or fruit juice concentrates.
  • Artificial colorants which may be used include caramel color, yellow 6 and yellow 5.
  • Useful vitamin additives include vitamin B2, vitamin B6, vitamin B 12, vitamin C (ascorbic acid), niacin, pantothenic acid, biotin and folic acid.
  • Suitable preservatives include sodium or potassium benzoate. Salts which may be used include sodium, potassium and magnesium chloride. Exemplary emulsifiers are gum arabic and purity gum, and a useful thickener is pectin.
  • Suitable acidulants include citric, phosphoric and malic acid, and potential buffering agents include sodium and potassium citrate.
  • the beverage is a carbonated cola beverage.
  • the pH is generally about 2.8 and the following ingredients can be used to make the syrup for these compositions: Flavor Concentrate, including one or more of the derivatives described herein (22.22 ml), 80% Phosphoric Acid (5.55 g), Citric Acid (0.267 g), Caffeine (1.24 g), artificial sweetener, sugar or com syrup (to taste, depending on the actual sweetener) and Potassium Citrate (4.07 g).
  • Flavor Concentrate including one or more of the derivatives described herein (22.22 ml), 80% Phosphoric Acid (5.55 g), Citric Acid (0.267 g), Caffeine (1.24 g), artificial sweetener, sugar or com syrup (to taste, depending on the actual sweetener) and Potassium Citrate (4.07 g).
  • the beverage composition can be prepared, for example, by mixing the foregoing syrup with carbonated water in a proportion of 50 ml syrup to 250 ml of
  • Flavored food and pharmaceutical compositions including one or more of the derivatives described herein can also be prepared.
  • the derivatives can be incorporated into conventional foodstuffs using techniques well known to those of skill in the art.
  • the derivatives can be incorporated within polymeric particles, which can, in turn, be dispersed within and/or over a surface of an orally-deliverable matrix material, which is usually a solid or semi-solid substrate.
  • the derivatives can be released into the orally-deliverable polymeric matrix material as the composition is chewed and held in the mouth, thus prolonging the flavor of the composition.
  • the flavor can be made available as the product is consumed or be released into the matrix material as the composition is further processed.
  • the relative amounts of the additives can be selected to provide simultaneous release and exhaustion of the compounds.
  • the flavored composition includes an orally-deliverable matrix material; a plurality of water insoluble polymeric particles dispersed in the orally-deliverable matrix material, where the polymeric particles individually define networks of internal pores and are non-degradable in the digestive tract; and one or more derivatives as described herein entrapped within the internal pore networks.
  • the derivatives are released as the matrix is chewed, dissolved in the mouth, or undergoes further processing selected from the group consisting of liquid addition, dry blending, stirring, mixing, heating, baking, and cooking.
  • the orally-deliverable matrix material can be selected from the group consisting of gums, latex materials, crystallized sugars, amorphous sugars, fondants, nougats, jams, jellies, pastes, powders, dry blends, dehydrated food mixes, baked goods, batters, doughs, tablets, and lozenges.
  • a flavorless gum base can be combined with a suitable derivative as described herein to a desired flavor concentration.
  • a blade mixer is heated to about 11 OF, the gum base is preheated so that it is softened, and the gum base is then added to the mixer and allowed to mix for approximately 30 seconds.
  • the flavored derivative is then added to the mixer and mixed for a suitable amount of time.
  • the gum can be then removed from the mixer and rolled to stick thickness on waxed paper while warm.
  • the derivatives described herein are incorporated into a system which can release a fragrance in a controlled manner.
  • These include substrates such as air fresheners, laundry detergents, fabric softeners, deodorants, lotions, and other household items.
  • the fragrances are generally one or more derivatives of essential oils as described herein, each present in different quantities.
  • U.S. Pat. No. 4,587,129 the contents of which are hereby incorporated by reference in their entirety, describes a method for preparing gel articles which contain up to 90% by weight of fragrance or perfume oils.
  • the gels are prepared from a polymer having a hydroxy (lower alkoxy) 2-alkeneoate, a hydroxy (lower alkoxy) lower alkyl 2-alkeneoate, or a hydroxy poly (lower alkoxy)lower alkyl 2-alkeneoate and a polyethylenically unsaturated crosslinking agent.
  • These materials have continuous slow release properties, i.e., they release the fragrance component continuously over a long period of time.
  • all or a portion of those derivatives that include an aldehyde group can be modified to include an acetal group, which can cause the formulations to release fragrance over a period of time as the acetal hydrolyzes to fo ⁇ n the aldehyde compound.
  • Fig. 1 The invention is equally applicable to all unsaturated cyclic or acyclic fragrance compounds, e.g., the terpenes and their aldehyde and ketone derivatives.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Fats And Perfumes (AREA)
  • Epoxy Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Cosmetics (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne une méthode de dérivatisation d'un composé chimique aromatique ou de fragrance, qui contient dans sa structure moléculaire au moins une double liaison pouvant améliorer les caractéristiques de liaison du composé aux ions métalliques, sans influer sensiblement sur les caractéristiques olfactives du composé. La méthode consiste à convertir la (les) double(s) liaison(s) en un groupe oxirane ou thiirane.
PCT/US2004/014399 2003-05-08 2004-05-07 Nouveaux derives de fragrance WO2004101472A2 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
AU2004238835A AU2004238835A1 (en) 2003-05-08 2004-05-07 Novel fragrance derivatives
CA002524897A CA2524897A1 (fr) 2003-05-08 2004-05-07 Nouveaux derives de fragrance
JP2006532874A JP2007516956A (ja) 2003-05-08 2004-05-07 新規な芳香誘導体
GB0524992A GB2419593B (en) 2003-05-08 2004-05-07 Novel fragrance derivatives
EP04760941A EP1625106A4 (fr) 2003-05-08 2004-05-07 Nouveaux derives de fragrance

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US46866603P 2003-05-08 2003-05-08
US60/468,666 2003-05-08

Publications (2)

Publication Number Publication Date
WO2004101472A2 true WO2004101472A2 (fr) 2004-11-25
WO2004101472A3 WO2004101472A3 (fr) 2006-11-23

Family

ID=33452222

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2004/014399 WO2004101472A2 (fr) 2003-05-08 2004-05-07 Nouveaux derives de fragrance

Country Status (9)

Country Link
EP (1) EP1625106A4 (fr)
JP (1) JP2007516956A (fr)
KR (1) KR20060032136A (fr)
CN (1) CN1925826A (fr)
AU (1) AU2004238835A1 (fr)
CA (1) CA2524897A1 (fr)
GB (1) GB2419593B (fr)
WO (1) WO2004101472A2 (fr)
ZA (1) ZA200508991B (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006092595A1 (fr) * 2005-03-02 2006-09-08 Flexitral, Inc Thiiranes macrocycliques
EP1831143A2 (fr) * 2004-12-22 2007-09-12 Flexitral, Inc. Derives ameliores de citral et de citronellal

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2902495A (en) * 1956-04-09 1959-09-01 Glidden Co Treatment of certain derivatives of 2,6-dimethyl-octane and intermediates
US3166575A (en) * 1961-03-15 1965-01-19 Givaudan Corp 2(2-methyl-1-propene)-yl-4-methyl-tetrahydro-pyrans and 2(2-methyl-2-propene)-yl-4-methyl-tetrahydro-pyrans
US3927083A (en) * 1972-06-15 1975-12-16 Int Flavors & Fragrances Inc Bicyclic compounds and processes for making and using same
DE2617816A1 (de) * 1976-04-23 1977-11-10 Henkel & Cie Gmbh Verwendung von epoxynitrilen als riechstoffe sowie diese enthaltende riechstoffkompositionen
US4162258A (en) * 1977-04-06 1979-07-24 The Lion Dentifrice Co., Ltd. Novel compounds spiro[5-isopropylbicyclo[3.1.0]hexane-2,2'-oxiranes], process for the production of the novel compounds, and process for the production of sabinene hydrates therefrom
JPS5466663A (en) * 1977-11-01 1979-05-29 Lion Dentifrice Co Ltd Method of manufacturing spiro*55isopropyl bicyclo*3*1*0*hexanee2*22oxilane*
IL63433A (en) * 1980-08-06 1986-04-29 Univ Leland Stanford Junior Method of asymmetrical epoxidation
JPS5735508A (en) * 1980-08-12 1982-02-26 Nippon Petrochem Co Ltd Perfumery composition containing glycidic acid ester
DE3170206D1 (en) * 1980-12-23 1985-05-30 Firmenich & Cie Use of sulphur terpene derivatives as perfuming and flavouring agents
CH650771A5 (fr) * 1981-11-04 1985-08-15 Firmenich & Cie Procede pour la preparation de 3,7-dimethyl-6-phenylsulfinyl-1,7-octanediol et son utilisation en tant qu'intermediaire pour la preparation d'oxyde de rose.
US4620945A (en) * 1983-08-01 1986-11-04 International Flavors & Fragrances Inc. Mixtures of one or more t-mercapto terpene isomers and α-terpineol, β-phenylethyl alcohol, 3-methyl-1-phenyl-pentanol-5 and/or butanoyl cyclohexane derivatives, organoleptic uses thereof and process for preparing same
DE3406999A1 (de) * 1984-02-27 1985-09-05 Hoffmann, Hans Martin Rudolf, Prof.PhD, DSc., 3004 Isernhagen Oxygenierte tetramethyllimonen-derivate
JPS60190774A (ja) * 1984-03-09 1985-09-28 Sagami Chem Res Center エポキシアルコ−ルの製造方法
JPH06726B2 (ja) * 1985-07-19 1994-01-05 株式会社クラレ 含窒素テルペンアルコ−ル類及びこれを有効成分とする抗アレルギ−剤
JPH04120071A (ja) * 1990-09-10 1992-04-21 Dainippon Ink & Chem Inc オキシ化合物の製法
JP3434526B2 (ja) * 1992-12-01 2003-08-11 三井化学株式会社 エポキシ基含有化合物、α−ヒドロキシカルボニル化合物またはα−ヒドロキシカルボニル化合物のアルキルシリルもしくはアリールシリル誘導体の製造方法
ES2160044B1 (es) * 1999-03-16 2002-06-16 Univ Valencia Politecnica Oxidacion de *-pineno.
DE10055092A1 (de) * 2000-11-07 2002-05-08 Haarmann & Reimer Gmbh Verfahren zur Herstellung von Linalooloxid oder von Linalooloxid enthaltenden Gemischen
CA2519859A1 (fr) * 2003-03-13 2004-09-30 Flexitral, Inc. Muscs macrocycliques

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of EP1625106A4 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1831143A2 (fr) * 2004-12-22 2007-09-12 Flexitral, Inc. Derives ameliores de citral et de citronellal
EP1831143A4 (fr) * 2004-12-22 2009-12-09 Flexitral Inc Derives ameliores de citral et de citronellal
WO2006092595A1 (fr) * 2005-03-02 2006-09-08 Flexitral, Inc Thiiranes macrocycliques

Also Published As

Publication number Publication date
CA2524897A1 (fr) 2004-11-25
EP1625106A2 (fr) 2006-02-15
EP1625106A4 (fr) 2010-09-08
JP2007516956A (ja) 2007-06-28
CN1925826A (zh) 2007-03-07
GB0524992D0 (en) 2006-01-18
GB2419593A (en) 2006-05-03
KR20060032136A (ko) 2006-04-14
WO2004101472A3 (fr) 2006-11-23
AU2004238835A1 (en) 2004-11-25
ZA200508991B (en) 2007-07-25
GB2419593B (en) 2007-10-10

Similar Documents

Publication Publication Date Title
AU2004230923A1 (en) Fragrance compositions comprising benzo(4,5)thieno(3,2-b)pyran-2-one
EP1687261A1 (fr) Oxy-nitriles
ZA200508991B (en) Novel fragrance derivatives
WO2006087571A2 (fr) Produits aromachimiques
EP1601752B1 (fr) Muscs macrocycliques
AU2004241286B2 (en) Alkoxy alkylsulfanyl phenols
AU2004207775B2 (en) Improved jasmine aromachemicals
US20060204464A1 (en) Macrocyclic thiiranes
US20060189509A1 (en) Alkoxy alkylsulfanyl phenols
WO2004103935A2 (fr) Derives cycliques de l'acide carbothioique
WO2004108867A2 (fr) Cyclohexene carboamides et carbothioamides
WO2007040516A1 (fr) Nouveaux cyclohexène-carboamides et -carbothioamides
WO2005048941A2 (fr) Nouveaux oxy-nitriles substitues
US20080260669A1 (en) Aromachemicals
EP2046772A1 (fr) Salicylate de thiophénéméthyle et composés parents en tant que arômes et parfums
WO2007102016A1 (fr) Utilisation de musc cyclique ou polycyclique contenant un groupe aldéhyde

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DPEN Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed from 20040101)
WWE Wipo information: entry into national phase

Ref document number: 2004238835

Country of ref document: AU

WWE Wipo information: entry into national phase

Ref document number: 2524897

Country of ref document: CA

Ref document number: 543398

Country of ref document: NZ

WWE Wipo information: entry into national phase

Ref document number: 2005/08991

Country of ref document: ZA

Ref document number: 200508991

Country of ref document: ZA

WWE Wipo information: entry into national phase

Ref document number: 1020057021229

Country of ref document: KR

Ref document number: 2006532874

Country of ref document: JP

WWE Wipo information: entry into national phase

Ref document number: 2236/KOLNP/2005

Country of ref document: IN

ENP Entry into the national phase

Ref document number: 2004238835

Country of ref document: AU

Date of ref document: 20040507

Kind code of ref document: A

WWE Wipo information: entry into national phase

Ref document number: 20048142929

Country of ref document: CN

WWP Wipo information: published in national office

Ref document number: 2004238835

Country of ref document: AU

WWE Wipo information: entry into national phase

Ref document number: 2004760941

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 0524992.5

Country of ref document: GB

Ref document number: 0524992

Country of ref document: GB

WWE Wipo information: entry into national phase

Ref document number: PA/a/2006/000379

Country of ref document: MX

WWP Wipo information: published in national office

Ref document number: 2004760941

Country of ref document: EP

WWP Wipo information: published in national office

Ref document number: 1020057021229

Country of ref document: KR