Pyran derivatives, method for preparing and using them in perfumery and for aromatisation

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to new pyran derivatives of general formula (I), wherein Y represents a 5-, 6- or 7-member ring, preferentially a 5- member ring, methyl- or ethyl- mono- or polysubstituted and optionally unsaturated; R1, R2, R3, R4 represent (each independently) a hydrogen atom or a linear or branched C1-5-alkyl group; X is present or absent when X is present, all R5, R6, R7, R8, R9 are present, while X is a hydrogen atom or the group OZ wherein Z is a hydrogen atom or the group R10 or the group C(O)R10; when X is absent, there is a double bond at a carbon atom in the 4th position, and R7, R8 and R9, and one of R5 or R6 are present (if R6 is present, then R5 is absent, and conversely), or one of R5, R6 and R7, and one of R8 or R9 are present (if R8 is present, then R9 is absent, and conversely), or R7 represent a group =C(R11)(R12), and R5, R6, R8, R9 are present; each of the groups R5-R12, when present, independently represent a hydrogen atom or a linear or branched C1-5-alkyl or C2-5-alkenyl group. The invention also relates to method for making these compounds, a pharmaceutical composition and using at least one pyran of formula (I) as a perfuming agent.

EFFECT: preparing new pyran derivatives.

14 dwg, 1 tbl, 4 ex

 

The technical field to which the invention relates.

The present invention relates to the field of aromatic and flavoring substances. In particular, the present invention relates to the derivatives of Piran, the way they are received and used in perfumes and for flavoring.

The level of technology

The terms "aroma/smell" and "sweet stuff" is here used interchangeably when talking about the compounds or mixtures of compounds, which should be a pleasant olfactory sensation.

The terms "kusayama" and "flavoring agent" are here used interchangeably when talking about the compounds or mixtures of compounds that should cause gustatory and olfactory sensations. Also in the context of this invention, the term "aroma" refers to the flavoring of any liquid or solid substance to humans or animals, in particular beverages, dairy products, ice cream, soups, sauces, gravy, dishes, meat products, cooking supplies, savoury crackers, biscuits, etc., skakovyh products. It also implies the aromatization of beer, wine and tobacco products.

The term "organoleptic connection, as, for example, aromatic and flavoring substances, there is used in relation to compounds according to this invention, which cause in the Usovo and/or olfactory sensation and thus are perceived as having a characteristic odor and/or kusayama.

The term "masking" refers to the weakening or disappearance of the feeling of odor and/or bad taste caused by one or more individual compounds included in the composition of the product.

The term "isomers" in the context of this invention means a molecule with the same chemical formula, i.e. with the same set of atoms of the same elements in the same quantities, but with a different arrangement of these atoms. The term "isomer" includes structural isomers, geometric isomers, optical isomers and stereoisomers.

The term "alkyl" or "alkyl group" in the context of this invention means any linear or branched saturated hydrocarbon chain, preferably containing 1, 2, 3, 4 or 5 carbon atoms and called here C1-5is an alkyl group, such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl.

The term "alkenyl" or "Alchemilla group" in the context of this invention means any linear or branched mono - or polyunsaturated hydrocarbon chain containing preferably 2, 3, 4 or 5 carbon atoms and called here2-5-alkenylphenol group, such as ethynyl, propenyl, butenyl or pentenyl.

The term "cycloalkyl" or "cycloalkyl group" in the context of this invention means any cyclic(closed) saturated hydrocarbon chain, containing preferably 5, 6 or 7 carbon atoms, such as, for example, cyclopentyl, cyclohexyl and cycloheptyl, substituted or not substituted alkyl or alkenylphenol group described above.

The term "cycloalkenyl" or "cycloalkenyl group" in the context of this invention means any cyclic (closed) mono - or. polyunsaturated hydrocarbon chain containing preferably 5, 6 or 7 carbon atoms, such as, for example, cyclopentenyl, cyclohexenyl and cycloheptenyl, substituted or not substituted alkyl or alkenylphenol group described above.

The term "cycloalkylcarbonyl" in the context of the present invention is substituted acetaldehyde containing cycloalkyl group.

The term "cycloalkylcarbonyl" in the context of the present invention is substituted acetaldehyde containing cycloalkenyl group.

Derivatives tetrahydropyrane and dihydropyran belong to an important group of aromatic ingredients, and has done much work in order to get known compounds, as, for example, Roztocze (Rose Oxide) and the like derived from a linear or branched alkyl and alkanolamides, as described in U.S. patent 3681263 and in the publication WO 04/009749, or from Benzylalcohol, as described in the publication SN 655932.

In a similar manner for the production of aroma is of Satarov interest ethers and esters of pranolol, as described in the U.S. patents 4963285 and 4962090.

U.S. patent 2452977 relates to a method for producing cyclic compounds; in this method, the unsaturated alcohol interacts with the aldehyde with the formation of cyclic compounds containing an oxygen atom as part of a ring. Some of the resulting compounds are Piranesi.

The need for new compounds is very important for the development of the production of aromatic and flavoring substances, which recently faced with stricter international regulations and requirements regarding the use of certain materials, as well as concern about the environment and consumers ' desire to get better products. Therefore, an urgent task is to obtain new aromatic compounds.

Further investigation derived Piran with the aim to identify novel aromatic compounds, the Applicant focused on the lateral cyclic circuits, namely cycloalkylation and cycloalkylation as source material.

None of the documents mentioned above are not offered the option of using cycloalkylcarbonyl or cycloalkylcarbonyl to obtain derivatives of Piran, and in view of the novelty of the resulting derivatives of Piran in this is blast equipment no information about their possible olfactory or organoleptic properties.

Disclosure of inventions

The present invention relates to the derivatives of Piran General formula (I)

where

- Y represents a 5-, 6 - or 7-membered ring, preferably a 5-membered ring, optionally methyl - or ethyl - mono - or polyamidine and optionally unsaturated;

- R1, R2, R3, R4 are (each independently) a hydrogen atom or a linear or branched C1-5-alkyl or C2-5-alkenylphenol group;

- X is present or absent;

- when X is present,

- R5, R6, R7, R8, R9 are all present, and X represents a hydrogen atom or a group OZ, where Z is a hydrogen atom or a group R10 or a group C(O)R10;

- when X is absent, there is a double bond at the carbon atom in the 4-th position and

- present R7, R8 and R9, and one of R5 or R6 (if present R6, R5 is absent, and Vice versa), or

- there are R5, R6 and R7, and one of R8 or R9 (if there is R8, R9 is absent, and Vice versa), or

- R7 represents a group =C(R11)(R12), and there are R5, R6, R8, R9,

- each of the groups R5-R12, when they are present, independently represents a hydrogen atom or a linear or branched C1-5-alkyl or C2-5-alkenylphenol group.

Preferably Y represents a 5-, 6 - or 7-membered ring, methyl - or ethyl-mono - or polyamidine optionally unsaturated.

On demo of the embodiments of the present invention, the preferred derivatives pyrans according to this invention have the General formula (I), where

- Y represents a five-membered ring; the specified ring is saturated or contains one double bond; optionally specified ring is methyl or ethyl mono - or polyamidine;

preferably Y represents the structure:

where

- R'1, R'2 and R'3 are (each independently) a hydrogen atom or a metal group or ethyl group, and at least one of the substituents R'1, R'2 and R'3 is a methyl or ethyl group,

dotted lines represent a double bond which is present or absent;

- R1, R2, R3, R4 are (each independently) a hydrogen atom or a linear or branched C1-5-alkyl or C2-5-alkenylphenol group;

- X is present or absent;

- when X is present,

- R5, R6, R7, R8, R9 are all present, and X represents a hydrogen atom or a group OZ, where Z is a hydrogen atom or a group R10 or a group C(O)R10;

- when X is absent, there is a double bond at the carbon atom in the 4-th position and

- present R7, R8 and R9, and one of R5 or R6 (if present R6, R5 is absent, and Vice versa), or

- there are R5, R6 and R7, and one of R8 or R9 (if there is R8, R9 is absent, and Vice versa), or

- R7 represents a group =C(R11)(R12), and there are R5, R6, R8, R9;

- each of the groups R5-R12, when they are present, PR is dstanley independently a hydrogen atom or a linear or branched C 1-5-alkyl or C2-5-alkenylphenol group.

In one particular embodiment, the present invention relates to the derivatives of Piran General formula (I)as described above, where

- Y represents one of the groups Y1, Y2), (Y3) or (Y4)

- R1, R2, R3, R4 are (each independently) a hydrogen atom or a linear or branched C1-5-alkyl or C2-5-alkenylphenol group;

- X is present or absent;

- when X is present,

- R5, R6, R7, R8, R9 are all present, and X represents a hydrogen atom or a group OZ, where Z is a hydrogen atom or a group R10 or a group C(O)R10;

- when X is absent, there is a double bond at the carbon atom in the 4-th position and

- present R7, R8 and R9, and one of R5 or R6 (if present R6, R5 is absent, and Vice versa), or

- there are R5, R6 and R7, and one of R8 or R9 (if there is R8, R9 is absent, and Vice versa), or

- R7 represents a group =C(R11)(R12), and there are R5, R6, R8, R9;

- each of the groups R5-R12, when they are present, independently represents a hydrogen atom or a linear or branched C1-5-alkyl or C2-5-alkenylphenol group.

In another preferred embodiment of the derivatives of Piran General formula (I)as described above are those in which

- Y represents a 5-, 6 - or 7-membered ring, predpochtite is the super 5-membered ring, optionally methyl - or ethyl - mono - or polyamidine and, optionally, unsaturated, or Y represents the group (Y1), (Y2), (Y3) or (Y4),

one of R3 or R4 represent a hydrogen atom, and the other metal group,

- R7 represents a group CH2while X is absent; or

- R7 represents a metal group, when X is present or absent; when R7 represents a metal group and X is present, X represents a hydrogen atom or a group OZ, where Z represents a hydrogen atom or a group R10 or a group C(O)R10; when R7 represents a metal group, and X is absent, when the hydrogen atom in the 4-th position has a double bond and

- R8, and R9 are present and one of R5 or R6 is present, but the other is missing or

- R5, and R6 are present, and one of R8 or R9 is present but the other is missing,

- R1, R2 and R10 are (each independently) a hydrogen atom or a linear or branched C1-5-alkyl or C2-5-alkenylphenol group,

when R5, R6, R8 and R9 are, each of them independently represents a hydrogen atom.

In another embodiment of the present invention, the preferred derivatives of Piran General formula (I)described above, chosen from the group comprising 4-metal-2-(2,2,3-trimethyl-cyclopent-3-animetal)-tetrahydropyran, 4-methyl-6-(2,2,3-trimethyl-cyclopent-3-animetal)-3,6-dihydro-2 is-Piran, 4-methyl-2-(2,2,3-trimethyl-picopen-3-animetal)-3,6-dihydro-2H-Piran, 4-methyl-2-(2,2,3-trimethyl-cyclopentylmethyl)-tetrahydropyran, 4-methylene-2-(2,2,3-trimethyl-cyclopentylmethyl)-tetrahydropyran, 4-methyl-6-(2,2,3-trimethyl-cyclopentylmethyl)-3,6-dihydro-2H-Piran, 4-methyl-2-(2,2,3-trimethyl-cyclopentylmethyl)-3,6-dihydro-2H-Piran, 4-methyl-4-(3-methyl-but-3-enyloxy)-2-(2,2,3-trimethyl-cyclopentylmethyl)-tetrahydropyran.

According to another embodiment of the derivatives of Piran in this invention have the General formula (I), where

- Y represents a 5-, 6 - or 7-membered ring, optionally methyl - or ethyl - mono - or polyamidine and rich; or

- Y represents a 5 - or 7-membered ring, optionally methyl - or ethyl - mono - or polyamidine and polyunsaturated; or

- Y represents a 5 - or 6-membered ring, optionally methyl - or ethyl - mono - or polyamidine, mono - or Dimensione, provided that the double bond is not in position G, or

- Y represents a 7-membered ring, optionally methyl - or ethyl - mono - or polyamidine, monounsaturated; or

- R1, R2, R3, R4 are (each independently) a hydrogen atom or a linear or branched C1-5-alkyl or C2-5-alkenylphenol group, and

- X is present or absent;

- when X is present,

- R5, R6, R7, R8, R9 are all present, and X represents the atom in which Orada or a group OZ, where Z is a hydrogen atom or a group R10 or a group C(O)R10;

- when X is absent, there is a double bond at the carbon atom in the 4-th position and

- present R7, R8 and R9, and one of R5 or R6 (if present R6, R5 is absent, and Vice versa), or

- there are R5, R6 and R7, and one of R8 or R9 (if there is R8, R9 is absent, and Vice versa), or

- R7 represents a group =C(R11)(R12), and there are R5, R6, R8, R9;

- each of the groups R5-R12, when they are present, independently represents a hydrogen atom or a linear or branched C1-5-alkyl or C2-5-alkenylphenol group.

In a second aspect the present invention relates to a method for producing derivatives of Piran according to this invention; the method characterized by the fact that the compound of General formula (A)

where

- Y represents a 5-, 6 - or 7-membered ring, preferably a 5-membered ring, optionally methyl - or ethyl - mono - or polyamidine and, optionally, unsaturated,

- R1 and R2 are (each independently) a hydrogen atom or a linear or branched C1-5-alkyl or C2-5-alkenylphenol group interacts in the presence of an acid with a compound of General formula (In)

where R3, R4, R5, R6, R7, R8 and R9 are (each independently) a hydrogen atom or a linear or times twinney C 1-5-alkyl or C2-5-alkenylphenol group.

One of the embodiments of the present invention the method according to this invention includes the additional step of conversion of the aldehyde (a) acetal of General formula (C)

where

- Y represents a 5-, 6 - or 7-membered ring, preferably a 5-membered ring, optionally methyl - or ethyl - mono - or polyamidine and, optionally, unsaturated,

- R1 and R2 are (each independently) a hydrogen atom or a linear or branched C1-5-alkyl or C2-5-alkenylphenol group,

- Z represents a group R10, where R10 is a linear or branched C1-5-alkyl or C2-5-Alchemilla group, before interaction with alcohol (In).

One of the embodiments of the present invention, (a) and/or (b) and/or (C) used in the form of optically pure isomer.

In another embodiment this invention relates to the above method, when the compound (A) or compound (C) reacts in the presence of acid with the compound (b) and of the resulting mixture to separate different compounds of formula (I), where X is absent or represents a group of OZ in which Z represents a hydrogen atom or a linear or branched C1-5-alkyl or C2-5-alkenylphenol group.

Differently embodied the Yu of the present invention compound (A) reacts in the presence of acid with compound (V) and the resulting mixture of compounds of formula (I), where X represents a group HE is separated from the compounds of formula (I), where X is absent, and then subjected to esterification reaction to obtain compounds of formula (I), where X represents the group O(OC)R10. The esterification reaction can be carried out by conventional methods known to experts in this field of technology.

According to another embodiment of this invention, the compound (A) reacts in the presence of acid with compound (V) and the resulting mixture of compounds of formula (I), where X represents a group HE is separated from the compounds of formula (I), where X is absent, and then subjected to alkylation reaction to obtain compounds of formula (I), where X is represented by a group OZ, where Z is a linear or branched C1-5-alkyl or C2-5-alkenylphenol group. The alkylation reaction can be carried out by conventional methods known to experts in this field of technology.

In another specific embodiment, the present invention relates to the above method, when the compound (A) reacts with the compound (b) and the resulting mixture derived Piran is subjected to dehydration reaction in the presence of acids; as a result of this method are the compounds of formula (I)in which X is absent and a double bond when the atom is in the 4th position.

Stage under the Oia can be carried out by conventional methods, well-known specialists in this field of technology.

Another aspect of the present invention is a composition comprising at least one compound of the formula (II) and/or at least one compound of the formula (III) and/or at least one compound of the formula (IV) and optionally (V) and/or (VI)

where

- Y represents a 5-, 6 - or 7-membered ring, preferably a 5-membered ring, optionally methyl - or ethyl - mono - or polyamidine and, optionally, unsaturated,

- R1, R2, R3, R4, R5, R6, R7, R8, R9 are (each independently) a hydrogen atom or a linear or branched C1-5-alkyl or C2-5-alkenylphenol group,

- Z represents a hydrogen atom or a linear or branched C1-5-alkyl or C2-5-alkenylphenol group, or a group C(O)R10, where R10 is a linear or branched C1-5-alkyl or C2-5-Alchemilla group.

This invention relates to compounds of formula (I)described above, but also to any of their various isomers.

In this latter aspect the present invention relates to the use of the above described compounds of formula (I).

In the first embodiment of the present invention relates to the use of at least one of the compounds or compositions described above, in the field of perfumery works to get pas pulirovaniya bases and concentrates, fragrances, perfumes and similar products; compositions for topical use; cosmetic compositions, such as creams for the face and body cleansers and other skin treatments, powders, oils and balms for the hair, shampoos, oils and bath salts, shower gels and bath, Soaps, antiperspirants and deodorants, creams and lotions to the for and after shaving, toothpastes, mouthwashes and ointments, oral, lipsticks; cleansing products, such as softening means, detergents, air fresheners and household cleaners. Thus, the present invention relates also to a fragrant compositions comprising at least one compound of formula (I) or one or more isomers of the compounds of formula (I).

In the second embodiment of the present invention relates to the use of at least one compound or composition, described above, as flavoring agents to obtain flavored compositions or products, such as beverages, dairy products, ice cream, soups, sauces, gravy, dishes, meat products, cooking AIDS, savoury crackers, biscuits, etc. or skakovyh products, as well as beer, wine and tobacco products. Thus, the present invention also relates to perfumed compositions comprising at least one is connected to the e of the formula (I) or one or more isomers of the compounds of formula (I).

In the third embodiment of the present invention relates to the use of compounds or compositions described above, as agents, masking odors and/or tastes, and to any pharmaceutical, cosmetic or food compositions containing at least one compound of formula (I) or one or more isomers of the compounds of formula (I). Thus, this invention also relates to any composition containing at least one of the above described compound of formula (I) in combination with any suitable excipients, especially pharmaceutical, cosmetic or food exipients.

Compounds according to this invention can be applied by themselves or in combination with other commonly used fragrance and/or flavoring ingredients, solvents, additives or braces that are the specialist in this field can be selected in accordance with the desired effect and nature parfumernogo or aromatizing products. The present invention includes, for example, any composition comprising one or more isomers of the compounds of formula (I). In the preferred embodiment of the present invention relates to compositions containing at least two or three isomers of compounds of formula (I).

In another embodiment in the applications described above, the compounds of this invention Ave the change in concentration from 0.001% to 99% (weight/weight), in particular from 0.1% to 50% (weight/weight), in particular from 0.1% to 30% (weight/weight). Specialists in the art it is known that these values depend on the nature of the composition/ products, which you want to impart odour and/or taste and smell; from the desired intensity of smell and/or taste; from the nature of the other ingredients present in a given composition or product. In the preferred embodiment of the compounds of this invention are used in amounts effective to excite the olfactory sense. Under amount, effective for the excitation of the olfactory sense, means the level (concentration) or the number of odoriferous/flavor compounds in the material, which included the compound causes the desired feeling.

The following examples disclose methods for producing compounds according to this invention and their use. These examples are presented here only for illustrative purpose and should not be considered as limiting the scope of invention.

The implementation of the invention

Example 1. Getting

4-methylene-2-(2,2,3-trimethyl-cyclopent-3-animetal)-tetrahydropyran(A), 4-methyl-6-(2,2,3-trimethyl-cyclopent-3-animetal)-3,6-dihydro-2H-Piran (In), 4-methyl-2-(2,2,3-trimethyl-cyclopent-3-animetal)-3,6-dihydro-2H-Piran(C)

The mixture campolongo aldehyde (1 equivalent) and 3-methyl-3-butene-1 is a (2 equivalent) in toluene with a catalytic amount of PTSA heated under reflux to remove the water formed. Upon completion of the reaction (3 hours) the mixture is cooled and diluted with toluene. After washing with a saturated solution of bicarbonate and with brine the organic phase is dried over MgSO4, filtered and the solvent is evaporated, so it's a crude oily substance.

The distilled product (82°C/0.8 mm Hg) consists of a mixture of isomers (A), (b) and (C) in the ratio 27:16:57.

He has a strong citrus (bitter orange, bitter orange) and "green" (galván, peas) smell.

Various isomers receive individually by thin fractional distillation with a Packed column with a partial reverse of condensation.

Each isomer is represented by a mixture of two diastereoisomers.

1H-NMR (CDCl3, 200 MHz): total proton signals δ (ppm) to 0.75 (s, 3H), of 0.97 (s, 3H), 1,25-2,5 (m, 7H), to 1.59 (s, 3H), 5,22 (m, 1H).

The characteristic proton signals:

(A) δ (ppm) 1,25-2,5 (m, 2H), 3,2-3,7 (m, 3H), 4,7 (m, 2H).

(B) δ (ppm) 1,68 (s, 3H), 3,9-4,2 (m,3H), 5,32 (m, 1H).

(C) δ (ppm) 1,68 (s, 3H), of 3.2 to 3.7 (m, 1H), 3,9-4,2 (m, 2H), 5,4 (m, 1H).

IR spectrum (film, cm-1): 796m, 1014m, 1095m, 1122s, 1138m, 1360m, 1382m, 1437m, 1445m, 1463m, 2864s, 2930s, 2955s.

Mass spectrum [e/m (%)]: 220 (M+, 12), 149 (5), 135 (4), 119 (8), 108 (100), 93 (59), 79 (19), 67 (35), 53 (20), 41 (48).

Example 2. Getting 4-methyl-2-(2,2,3-trimethyl-cyclopentylmethyl)-tetrahydro-Piran

The mixture of isomers obtained in Example 1 is processed normally when the hydrogen pressure in ethanol with a catalytic amount of palladium on coal (5%), that will give the desired tetrahydropyran. The crude product obtained after filtration of the reaction mixture with Clarcel®, purified by distillation (88°C/0.7 mm Hg). It consists of four pairs of diastereoisomers (2 major and 2 minor, in the ratio 36:42:10:12). He has a bit of a dry scent of bitter orange and wood with some modicum of musk.

1H-NMR (CDCl3, 200 MHz): total proton signals δ (ppm) 0,46 and of 0.48 (s, 3H), 0,65-of 0.87 (m, 6H), 0,90-1,30 (m, 4H), 1.30 and of 2.20 (m, 9H), 3,10-of 3.75 (m, 2H),

Major isomer: Characteristic proton signals δ (ppm) of 0.90 (d, J=6,1 Hz) and of 0.91 (d, J=6.2 Hz: 3H); of 3.85 to 4.0 (m, 1H).

Minor isomers: Characteristic proton signals δ (ppm) of 1.01 (d, 1H, J=7,l Hz) and of 1.02 (d, 1H, J=7,1 Hz): 3H); 3,10-of 3.75 (m, 1H).

13C-NMR (CDCl3, 60 MHz):

Major isomer: 13,9 and 14,26; 22,36 and 24,40; 25,37 and 25,46; 28,11 and 28,39; 30,14 and 30,26; 30,27 and 30,41; 34,75 and 34,82; 37,40 and 37,51; 40,21 and 41,87; 42,03 and 42,35; 44,90 and 44,96; 46,11 and 47,01; 67,99 and 68,12; 76,37 and 77,18.

Minor isomers (sample data)): 13,90 and 14,26; 18,72 and MT 19 : 18; 24,78 and 24,94; 28,0 and weighing 28.32; 32.4 and 32,62; 35,44 and 35,96; 37,19 and 38,82; 44,87; 47,4.

IR spectrum (film, cm-1): 1095 s, 1177 m, 1366 m, 1374 m, 1386 m, 1456 m, 1466 m, 2838 m, 2869 s, 2926 s, 2952 s.

Mass spectrum [e/m (%)]: 224 (M+, 1), 99 (100), 55 (18), 43 (19), 41 (17).

Example 3. Getting

4-methylene-2-(2,2,3-trimethyl-cyclopentylmethyl)-tetrahydropyran(A), 4-methyl-6-(2,2,3-trimethyl-cyclopentylmethyl)-3,6-dihydro-2H-Piran(In), 4-methyl-2-(2,2,3-trimethyl-cyclopentylmethyl)-3,6-dihydro-2H-Piran (

The mixture of isomers (A), (b) and (C) in the ratio of 63:14:23 was obtained according to Example 1, on the basis of hydrogenated campolongo aldehyde.

Its scent is similar to that described in Example 1.

The main isomers (A):

1H-NMR (CDCl3, 200 MHz): δ (ppm) 0,45-0,55 (m, 3H); 0,75-0,85 (m, 6H); 1,0-1,3 (m, 2H); from 1.3 to 1.55 (m, 3H); of 1.55 to 2.0 (m, 5H); 2,0-2,4 (m, 2H); 3.1 to 3.4 (m, 2H); 3,9-of 4.05 (m, 1H); the 4.65-4.75 in (m, 2H),

13C-NMR (CDCl3, 60 MHz): δ (ppm) 13,89 and 14,23; 25,34 and 25,46; 28,04 and 28,43; 30,11 and 30,24; 35,22 and of 35.27; 37,20; 40,81 and 42,24; 44,87 and 44,95; 46,05 and 47,07; 46,14 and 46,19; 68,55 and 68,64; 77,63 and 78,54; 108,01 and 108,17; 144,75 and 144,97.

(C) Isomers (Characteristic proton signals): δ (ppm) 3,9-of 4.05 (m, 3H); the 5.25 and 5.30 (m, 1H),

13C-NMR (CDCl3, 60 MHz, the sample data): δ (ppm) 63,12 and 63,44; 72,53 and 72,72; 123,67 and 125,10.

(C) Isomers (Characteristic proton signals): δ (ppm) 3,4-of 3.65 (m, 1H); 3.95 to to 4.15 (m, 2H),

13C-NMR (CDCl3, 60 MHz, the sample data): δ (ppm) 65,76 and 65,84; 73,39 and 73,72; 119,65 and 119,74.

Example 4: 4-methyl-4-(3-methyl-but-3-enyloxy)-2-(2,2,3-trimethyl-cyclo-panelmeter)-tetrahydropyran

4-Methyl-4-(3-methyl-but-3-enyloxy)-2-(2,2,3-trimethyl-cyclo-panelmeter)-tetrahydropyran received under the conditions used in Example 3, and was separated from other derivatives by thin fractionation.

It consists of a mixture of isomers of TRANS/CIS (60:40).

Has a gentle scent of bitter orange.

The main di the stereoisomers, TRANS-isomer:

1H-NMR (CDCl3, 200 MHz): δ (ppm) 0,49 (s, 3H); of 0.82 (d, 3H, J=10.1 Hz); 0,83 (s, 3H); 1,0-1,9 (m, 12H); of 1.28 (s, 3H); 1,74 (s, 3H); 2,24 (t, 2H, 7=7,1 Hz); the 3.2 to 3.5 (m, 2H); 3.50 for each (t, 2H, J=7.2 Hz); 4,74 (m, 2H).

13C-NMR (CDCl3, 60 MHz): δ (ppm) 13,91 and 14,29; 21,12 and 21,34; 23,0; 25,38 and 25,46; 28,08 and 28,25; 30,11 and 30,23; 37,24 and 37,35; 37,4 and 37,49; 38,65; 42,08 and 42,39; 43,11 and 44,41; 44,88 and 44,98; 46,11 and 47.0; 58,95; 65,05 and 65,13; 72,60 and 72,66; 73,79 and 74,74; 111,15; 143,24.

Mass spectrum [e/m (%)]: 308 (M+, 1), 293(2), 223(23), 109(10), 99(72), 97(10), 69(100), 55(10), 43(11), 41(36).

IR spectrum (film, cm-1): 642 w, 887 m, 1078 m, 1104 s, 1144 m, 1177 m, 1251 w, 1271 w, 1374 m, 1453 m, 1466 m, 1650 w, 2869 s, 2951 s.

Minor diastereoisomer, CIS-isomers:

1H-NMR (CDCl3, 200 MHz)sample data: δ (ppm) to 0.48 (s, 3H); 1.27mm ('s. 3H); to 3.49 (t, 2H, J=7,2 Hz).

13C-NMR (CDCl3, 60 MHz)sample data: δ (ppm) 111,36; 143,39.

Mass spectrum [e/m (%)]: 308 (M+, 1), 293 (9), 223 (11), 222 (11), 221 (37), 112 (25), 109 (12), 99 (26), 97 (28), 95 (12), 69 (100), 55 (16), 43 (17), 41 (50).

IR spectrum (film, cm-1): 642 w, 887 m, 1078 m, 1104 s, 1144 m, 1177 m, 1251 w, 1271 w, 1374 m, 1453 m, 1466 m, 1650 w, 2869 s, 2951 s.

Example 5. Perfume composition containing the mixture of (A)/(B)/(C)obtained in example 1.

A base perfume composition prepared as described from the following ingredients:

ABRAC arylacetic5
Benzoylacetate5
Bergamese the t 70
Geraniaceae7
Lineolated45
Terminalarea60
Acetamidophenol5
Phenethyl alcohol130
Benzaldehyde2
Aldehyde C102
Cyclomancy aldehyde®25
Anisaldehyde20
Velvion®5
Globanon®5
Methylbenzoate2
Honey ketone5
Amillenial100
Floral®45
Essential oil of wood, guaiac wood2
Methyldihydromorphine40
Ionon alpha30
Ionon beta10
Mayol®30
Methylisourea2
Neroline®15
The linalool oxide3
Terpineol85
Tetrahydropyranol30
Vanilla1
The acetophenone 10%DPG5
Phenylacetic acid, 10% DPG2
The citronellal With 10% DPG2
Indolarome® 10%DPG5
800

To this base composition of the type "honeysuckle" was added 10 parts (weight/weight) mixture of isomers (A)/(B)/(C)obtained in Example 1. Thus obtained new song had a more "green" note, reminding petitgrain essential oil with a hint of orange flower. In addition, a mixture of (A)/(B)/(C) gives the composition of fresh is here. These interesting features of the new compositions are valuable for alcoholic drinks, and gels for the soul and the bases for creams.

1. Derived Piran General formula (I)

where Y represents a 5-, 6 - or 7-membered ring, preferably a 5-membered ring, methyl - or ethyl - mono - or polyamidine and optionally unsaturated;
R1, R2, R3, R4 are (each independently) a hydrogen atom or a linear or branched C1-5is an alkyl group, and
X is present or absent;
when X is present,
R5, R6, R7, R8, R9 are all present, and X represents a hydrogen atom or a group OZ, where Z is a hydrogen atom or a group R10 or a group C(O)R10;
when X is absent, there is a double bond at the carbon atom in the 4-th position and
present R7, R8 and R9, and one of R5 or R6 (if present R6, R5 is absent, and Vice versa), or
there are R5, R6 and R7, and one of R8 or R9 (if there is R8, R9 is absent, and Vice versa), or
R7 represents a group =C(R11)(R12), and there are R5, R6, R8, R9;
each of the groups R5-R12, in addition to the group R10, when they are present, independently represents a hydrogen atom or a linear or branched C1-5is an alkyl group, and the group of R10 is independently a hydrogen atom or a linear or branched C1-5is an alkyl group or a C2-C5-alkenylphenol group.

2. About svodnoe Piran General formula (I) according to claim 1, where
Y represents a 5-membered ring; the specified ring is saturated or contains one double bond; the specified ring methyl - or ethyl - mono - or polyamidine;
R1, R2, R3, R4 are (each independently) a hydrogen atom or a linear or branched C1-5is an alkyl group, and
X is present or absent;
when X is present,
R5, R6, R7, R8, R9 are all present, and X represents a hydrogen atom or a group OZ, where Z is a hydrogen atom or a group R10 or a group C(O)R10;
when X is absent, there is a double bond at the carbon atom in the 4-th position and
present R7, R8 and R9, and one of R5 or R6 (if present R6, R5 is absent, and Vice versa), or
there are R5, R6 and R7, and one of R8 or R9 (if there is R8, R9 is absent, and Vice versa), or
R7 represents a group =C(R11)(R12), and there are R5, R6, R8, R9;
each of the groups R5-R12, in addition to the group R10, when they are present, independently represents a hydrogen atom or a linear or branched C1-5is an alkyl group, and the group of R10 is independently a hydrogen atom or a linear or branched C1-5is an alkyl group or a C2-C5-alkenylphenol group.

3. Derived Piran General formula (I) according to claim 1, where
Y represents one of the groups Y1, Y2), (Y3) or (Y4)

R1, R2, R3, R4 are (each independently) a hydrogen atom, or l is nanou or branched C 1-5is an alkyl group;
X is present or absent;
when X is present,
R5, R6, R7, R8, R9 are all present, and X represents a hydrogen atom or a group OZ, where Z is a hydrogen atom or a group R10 or a group C(O)R10;
when X is absent, there is a double bond at the carbon atom in the 4-th position and
present R7, R8 and R9, and one of R5 or R6 (if present R6, R5 is absent, and Vice versa), or
there are R5, R6 and R7, and one of R8 or R9 (if there is R8, R9 is absent, and Vice versa), or
R7 represents a group C(R11)(R12), and there are R5, R6, R8, R9;
each of the groups R5-R12, in addition to the group R10, when they are present, independently represents a hydrogen atom or a linear or branched C1-5is an alkyl group, and the group of R10 is independently a hydrogen atom or a linear or branched C1-5is an alkyl group or a C2-C5-alkenylphenol group.

4. Derived Piran General formula (I) according to any one of claims 1 to 3, where
Y is defined according to any one of claims 1 to 3,
R3 represents a hydrogen atom, a R4 - metal group or, on the contrary, R4 represents a hydrogen atom, and R3 - metal group,
R7 represents the group =CH2while X is absent; or
R7 represents a metal group, when X is present or absent;
when R7 represents a metal group and X is present, X is a hydrogen atom is whether the group OZ, where Z represents a hydrogen atom or a group R10 or a group C(O)R10; when R7 represents a metal group, and X is absent, when the hydrogen atom in the 4-th position has a double bond and
R8 and R9 are present, and R5 and R6 one is present but the other is missing or
R5 and R6 are present, and R8 and R9 is one, but the other missing
R1, R2 are (each independently) a hydrogen atom or a linear or branched C1-5is an alkyl group,
and the group R10 is independently a hydrogen atom or a linear or branched C1-5is an alkyl group or a C2-C5-alkenylphenol group;
when R5, R6, R8 and R9 are, each of them independently represents a hydrogen atom.

5. Derived Piran General formula (I) according to claim 1, where these derivatives are chosen from the group consisting of 4-methylene-2-(2,2,3-trimethyl-cyclopent-3-animetal)-tetrahydropyran, 4-methyl-6-(2,2,3-trimethyl-cyclopent-3-animetal)-3,6-dihydro-2H-Piran, 4-methyl-2-(2,2,3-trimethyl-cyclopent-3-animetal)-3,6-dihydro-2H-Piran, 4-methyl-2-(2,2,3-trimethyl-cyclopentylmethyl)-tetrahydropyran, 4-metal-2-(2,2,3-trimethyl-cyclopentylmethyl)-tetrahydropyran, 4-methyl-6-(2,2,3-trimethyl-cyclopentylmethyl)-3,6-dihydro-2H-Piran, 4-methyl-2-(2,2,3-trimethyl-cyclopentylmethyl)-3,6-dihydro-2H-Piran, 4-methyl-4-(3-methyl-but-3-enyloxy)-2-(2,2,3-trimethyl-cyclo-pentamethyl)-tetrahydropyran.

6. Ways is the deriving of Piran formula (I), according to any one of claims 1 to 5, consists in the fact that the compound of General formula (A)

where Y represents a 5-, 6 - or 7-membered ring, preferably a 5-membered ring, methyl - or ethyl - mono - or polyamidine and, optionally, unsaturated,
R1 and R2 are (each independently) a hydrogen atom or a linear or branched C1-5is an alkyl group,
interacts in the presence of an acid with a compound of General formula (In)

where R3, R4, R5, R6, R7, R8 and R9 are (each independently) a hydrogen atom or a linear or branched C1-5is an alkyl group.

7. The method according to claim 6, which includes the additional step of conversion of the aldehyde (a) acetal of General formula (C)

where Y represents a 5-, 6 - or 7-membered ring, preferably a 5-membered ring, optionally methyl - or ethyl - mono - or polyamidine and, optionally, unsaturated,
R1 and R2 are (each independently) a hydrogen atom or a linear or branched C1-5is an alkyl group,
Z represents a group R10, where R10 is a linear or branched C1-5-alkyl or C2-5-Alchemilla group, before interaction with alcohol (In).

8. The method according to PP and 7, in which the compound (A) or compound (C) reacts with the compound (C) in prisutstvie the acid with the formation of the compounds of formula (I), where X represents a group OZ, a Z is a hydrogen atom or a linear or branched C1-5-alkyl or C2-5-alkenylphenol group.

9. The method according to claim 6, in which the compound (A) reacts with the compound (V) in the presence of acid, and the compound of General formula (I), where X presents IT, is separated from the compounds of formula (I), where X is absent, and then subjected to esterification reaction to obtain compounds of formula (I), where X presents OC(O)R10.

10. The method according to claim 6, in which the compound (A) reacts with the compound (V) in the presence of acid, and the compound of General formula (I), where X presents IT, is separated from the compounds of formula (I), where X is absent, and then subjected to alkylation reaction to obtain compounds of formula (I), where X is represented by a group OZ, where Z is a linear or branched C1-5-alkyl or C2-5-Alchemilla group.

11. Aromatic composition containing at least one compound of the formula (II) and/or at least one compound of the formula (III) and/or at least one compound of the formula (IV) and optionally the compound of formula (V) and/or the compound of formula (VI)

where Y represents a 5-, 6 - or 7-membered ring, preferably a 5-membered ring, methyl - or ethyl - mono - or polyamidine and, if necessary, unsaturated,
R1, R2, R3, R4, R5, R6, R7, R8,R9 are (each independently) a hydrogen atom or a linear or branched C 1-5is an alkyl group,
Z represents a hydrogen atom or a linear or branched C1-5-alkyl or C2-5-alkenylphenol group, or a group C(O)R10, where R10 is a linear or branched C1-5-alkyl or C2-5-Alchemilla group.

12. The application of the derived Piran according to any one of claims 1 to 5 or a composition according to claim 11 in perfume for obtaining perfumed bases and concentrates, perfumes, spirits and similar products; compositions for topical use; cosmetic compositions selected from the group consisting of creams, facial and body cleansers and other skin treatments, powders, oils and balms for the hair, shampoos, oils and bath salts, shower gels and bath, Soaps, antiperspirants and deodorants, creams and lotions before, and after shave, toothpaste, rinse and ointment for mouth, lipstick lip; cleansing products selected from the group consisting of softening means, detergents, air fresheners and household cleaners.

13. The application of the derived Piran according to any one of claims 1 to 5 or a composition according to claim 11 as agents, masking odors, in relation to pharmaceutical and cosmetic compositions.

14. The application of the derived Piran according to any one of claims 1 to 5 or a composition according to claim 11 in combination with other aromatic ingredients, solvents, additives or f is csatorna.



 

Same patents:

FIELD: chemistry.

SUBSTANCE: invention relates to campholene derivatives of general formula (I), a fragrant or aromatic flavouring composition and use thereof in perfumery to obtain perfumed bases and concentrates, as aromatic agents for producing flavouring compositions or products, as agents which mask smell and/or taste, including in a combination with other perfumery or aromatic ingredients, solvents and additives. In general formula (I) , R1, R2, R3, R4 and R5 each independently denote a hydrogen atom or a linear or branched C1-C5 alkyl or C2-C5 alkenyl group, - Y denotes CN, C(O)R6 or a CR6(ORα)(ORβ) group, where R6 denotes a hydrogen atom or a linear or branched C1-C5 alkyl or C2-C5 alkenyl group, and Rα and Rβ simultaneously denote a linear or branched C1, C2, C3, C4 or C5 alkyl or C2, C3, C4 or C5 alkenyl group, the - 5-member ring is saturated or contains a double bond between C3' and C4' in formula (I), and the side chain, if necessary, contains a double bond between C1 and C2 and/or between C3 and C4, under the condition that said derivative is not 3-methyl-6-(2,2,3-trimethyl-cyclopent-3-enyl)-hex-4-enal.

EFFECT: use of campholene derivatives to obtain perfumed bases and concentrates.

10 cl, 1 tbl, 2 dwg, 20 ex

FIELD: machine building.

SUBSTANCE: essential oil distillation plant comprises tight steam boiler with boiling kettle communicated by steam duct with cooler and separating flask. To intensify distillation and increase process efficiency, said boiling kettle is furnished with a set of grated cartridges arranged there inside. Said boiler has steam chamber made at its bottom communicated with tapered perforated hollow rods and branch pipes to allow steam inside cartridges. Said tapered hollow rods and branch pipes feed steam to cartridges and guide them in mounting into boiling kettle. Boiling kettle center section accommodates perforated essential oil vapors collector. Aforesaid cartridge is provided with tapered steam distributor with ring arranged atop and discharge loop at cartridge bottom.

EFFECT: higher efficiency and simplified design.

3 cl, 1 dwg

FIELD: instrument making.

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EFFECT: invention allows intensifying the removal process of ethereal oils and mechanising loading-unloading operations of silver fir branches.

3 cl, 2 dwg

FIELD: instrument making.

SUBSTANCE: silver fir branches processing plant includes tight container, oven, steam boiler, steam distributor arranged at the container bottom, cooler and Florentina. Tight container is made in the form of the cylinder connected in lower part to convergent flattened cone, and in upper part to the cover plate made in the form of flattened cone equipped with ultrasonic vibrating system with cross-shaped wave guide of bending vibrations and additional wave guide of longitudinal vibrations; at that, intensity of vibrations of ultrasonic frequency is set within 140-150 dB, and steam distributor is equipped with pulsator controlling the pulse steam supply to the container at frequency of 2 Hz.

EFFECT: plant has higher efficiency and allows improving the quality of the obtained silver fir oil.

3 cl, 2 dwg

FIELD: wood working industry.

SUBSTANCE: plant in the upper part of a distillation chamber additionally comprises a nozzle with an outgoing upper steam distributor made in the form of a horizontal pipe arranged along the perimetre of the chamber with holes, through which the stock is treated with steam. The nozzle from the outside is connected to a steam line outgoing from the boiler. In the chamber cover there is a nozzle for additional feeding of stock after shrinkage without chamber unsealing, which eliminates losses of essence oil due to volatilisation. The chamber is heat-insulated.

EFFECT: invention makes it possible to increase productivity, yield and quality of essence oil.

2 dwg

FIELD: food industry.

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3 cl, 1 dwg, 7 tbl, 14 ex

FIELD: food industry.

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3 cl, 1 dwg, 7 tbl, 14 ex

FIELD: medicine.

SUBSTANCE: invention relates to cosmetic industry, in particular to composition for oral cavity care. Product for oral cavity care, containing agent for oral cavity care, which possesses chemical reducing ability, taste system, containing fragrance(s) or extract(s), in fact free of sulphur-containing compounds, which include dimethyl sulfoxide, dimethyl sulfide, dimethyl disulfide and dimethyl sulfone, which are precursors of formation of unpleasant smell and taste sensations, and suitable for introduction into oral cavity, agent for oral cavity care being selected from source of tin(2) ions and phenol resins from sources selected from tea, cranberry, pomegranate and oak bark.

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7 cl, 3 tbl, 5 ex

FIELD: chemistry.

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2 tbl, 4 ex

FIELD: tobacco industry.

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11 cl, 4 dwg, 6 ex

FIELD: chemistry.

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37 cl, 30 dwg, 7 tbl

FIELD: organic chemistry, biochemistry, medicine.

SUBSTANCE: invention describes compound of the general formula (3): wherein R15 represents a heterocyclic group chosen from 3-7-membered saturated or 4,7-membered unsaturated monocyclic heterocyclic group comprising 1-4 atoms chosen from nitrogen atom, oxygen atom and sulfur atom, or 7-14-membered polycyclic heterocyclic group comprising 1-4 atoms chosen from nitrogen atom, oxygen atom and sulfur atom that can comprises a substitute; R16 represents a cycloalkyl group comprising 3-7 carbon atoms, monocyclic aromatic hydrocarbon group comprising 6-14 carbon atoms, or heterocyclic group chosen from 3-7-membered saturated or 4-7-membered unsaturated monocyclic heterocyclic group comprising 1-4 atoms chosen from nitrogen atom, oxygen atom and sulfur atom that can comprises a substitute; R17 represents a monocyclic aromatic hydrocarbon group comprising 6-14 carbon atoms or heterocyclic group chosen from 4-7-membered saturated monocyclic heterocyclic group comprising 1-4 atoms chosen from nitrogen atom, oxygen atom and sulfur atom that can comprises a substitute; R18 represents hydrogen atom or (C1-C)-alkyl group; X represents -S-, -SO- or -SO2; or N-oxide or S-oxide of this compound; their salt; or solvate of above described compound. Proposed compounds possess the inhibitory activity against producing/secretion of β-amyloid protein and can be used in treatment of such diseases as Alzheimer's disease, Down's disease and other diseases associated with amyloid deposition.

EFFECT: valuable medicinal properties of inhibitors.

7 cl, 1 tbl, 410 ex

FIELD: organic chemistry, chemical technology, medicine, biochemistry, pharmacy.

SUBSTANCE: invention relates to new derivatives of sulfonamides of the formula (I) or their pharmaceutically acceptable salts wherein R1 means -OH or -NHOH; R2 means hydrogen atom; R3 means alkyl, alkoxyalkyl, arylalkyl, pyridylalkyl or morpholinylalkyl; A means piperidyl or tetrahydrofuranyl; n = 0; E means a covalent bond; (C1-C4)-alkylene, -C(=O)-, -C(=O)O- or -SO2-; X means hydrogen atom, alkyl, aryl, arylalkyl, alkoxyalkyl, morpholinyl or tetrahydropyranyl; each among G and G' means -C(R5)=C(R5') wherein R5 and R5' mean hydrogen atom; M means the group -CH-; z means the group -(CR7R7')a-L-R8 wherein a = 0 and each among R7 and R7' means hydrogen atom; L means a covalent bond; R8 means halogen atom or alkoxy-group. Compounds of the formula (I) are inhibitors of metalloproteases and can be used for treatment of arthritis, cancer tumors and other diseases.

EFFECT: valuable medicinal properties of compounds.

15 cl, 7 tbl, 56 ex

The invention relates to a new method of producing compounds of the formula I

< / BR>
where a represents a C1-C6is alkyl, aryl, mono - or Disaese F, Cl, Br, och3C1-C3-alkyl or benzyl, - inhibitors of 5-lipoxygenase, are useful for the treatment or relief of inflammatory diseases, Allergy and cardiovascular diseases

FIELD: chemistry.

SUBSTANCE: present invention relates to organic electroluminescent devices based on compounds of formula

where Y, Z is selected from N, P, P=O, C=O, O, S, S=O and SO2; Ar1, Ar2, Ar3 are selected from benzene, naphthaline, anthracene, phenanthrene, pyridine, pyrene or thiophene, optionally substituted with R1; Ar4, Ar5, Ar6, Ar7 are selected from benzene, naphthaline, anthracene, phenanthrene, pyridine, pyrene, thiophene, triphenylamine, diphenyl-1-naphthylamine, diphenyl-2-naphthylamine, phenyldi(1-naphthyl)amine, phenyldi(2-naphthyl)amine or spirobifluorene, optionally substituted with R1; E is a single bond, N(R1), O, S or C(R1)2; R1 denotes H, F, CN, alkyl, where the CH2 can be substituted with -R2C=CR2 -, -C=C-, -O- or -S-, and H can be substituted with F, optionally substituted aryl or heteroaryl, where R1 can form a ring with each other; R2 denotes H, aliphatic or aromatic hydrocarbon; X1, X4, X2, X3 are selected from C(R1)2, C=O, C=NR1, O, S, S=O, SO2, N(R1), P(R1), P(=O)R1, C(R1)2-C(R1)2, C(R1)2-C(R1)2-C(R1)2, C(R1)2-O and C(R1)2-O-C(R1)2; n, o, p, q, r and t are equal to 0 or 1; s = 1.

EFFECT: obtaining novel compounds - emission layer dopants, and novel electroluminescent devices based on said compounds which emit a blue colour.

18 cl, 91 ex, 6 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to use of tetrahydropyran (tetrahydropyranone), substituted in the beta-position relative to the carbon atom in the ring, as a fragrant substance. This compound has the following formula: where: the substitute R denotes a linear alkyl radical CH3-(CH2)n- in which n=2-10 inclusively, (CH3)2CH- or C6H5-(CH2)m-, where m=0 or 1; or , where: A denotes -CH2- or -CO-, to a method of producing the said compounds and compositions such as perfume, topical, particularly cosmetic compositions and everyday conditioning agents.

EFFECT: wider field of use of the compounds.

12 cl, 6 ex, 5 tbl

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: claim describes substituted anthranylamides of the general formula (I): wherein A means group =NR7; W means oxygen atom; D, E, F, G, X, Z, R1, R2, R7 and R9 have values given in the description and their isomers and salts also. Also, claim describes intermediate compounds used in preparing indicated anthranylamides. Also, invention relates to medicinal agents, their compositions and their using. Proposed compounds can be used in treatment of diseases associated with persistent angiogenesis that can be cause of different diseases, such as psoriasis, arthritis, for example, rheumatic arthritis, hemangioma, angiofibroma, ophthalmic diseases, for example, diabetic retinopathy, neovascular glaucoma, kidney diseases, for example, glomerulonephritis, diabetic nephropathy, malignant nephrosclerosis, thrombosis microangiopathy, rejection of transplants and glomerulopathy, fibrosis diseases, for example, hepatic cirrhosis, diseases associated with proliferation of mesangial cells and arteriosclerosis that can result to progression of these diseases. Invention provides the development of the corresponding medicinal agent designated for treatment of abovementioned diseases. The development of the preparation allows expanding assortment of agents used in treatment of such diseases.

EFFECT: valuable medicinal properties of compounds.

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: claim describes substituted anthranylamides of the general formula (I): wherein A means group =NR7; W means oxygen atom; D, E, F, G, X, Z, R1, R2, R7 and R9 have values given in the description and their isomers and salts also. Also, claim describes intermediate compounds used in preparing indicated anthranylamides. Also, invention relates to medicinal agents, their compositions and their using. Proposed compounds can be used in treatment of diseases associated with persistent angiogenesis that can be cause of different diseases, such as psoriasis, arthritis, for example, rheumatic arthritis, hemangioma, angiofibroma, ophthalmic diseases, for example, diabetic retinopathy, neovascular glaucoma, kidney diseases, for example, glomerulonephritis, diabetic nephropathy, malignant nephrosclerosis, thrombosis microangiopathy, rejection of transplants and glomerulopathy, fibrosis diseases, for example, hepatic cirrhosis, diseases associated with proliferation of mesangial cells and arteriosclerosis that can result to progression of these diseases. Invention provides the development of the corresponding medicinal agent designated for treatment of abovementioned diseases. The development of the preparation allows expanding assortment of agents used in treatment of such diseases.

EFFECT: valuable medicinal properties of compounds.

FIELD: chemistry.

SUBSTANCE: invention relates to use of tetrahydropyran (tetrahydropyranone), substituted in the beta-position relative to the carbon atom in the ring, as a fragrant substance. This compound has the following formula: where: the substitute R denotes a linear alkyl radical CH3-(CH2)n- in which n=2-10 inclusively, (CH3)2CH- or C6H5-(CH2)m-, where m=0 or 1; or , where: A denotes -CH2- or -CO-, to a method of producing the said compounds and compositions such as perfume, topical, particularly cosmetic compositions and everyday conditioning agents.

EFFECT: wider field of use of the compounds.

12 cl, 6 ex, 5 tbl

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