Complexes with inclusion of cyclodextrin and methods of their obtaining

FIELD: chemistry.

SUBSTANCE: method of obtaining complex with inclusion of cyclodextrin can include dry mixing of cyclodextrin and hydrocolloid for formation of dry mixture and mixing solvent and guest with dry mixture for formation of complex with inclusion of cyclodextrin. In some versions of realisation method of obtaining complex with inclusion of cyclodextrin can include mixing of cyclodextrin and hydrocolloid for formation of first mixture, mixing of first mixture with solvent for formation of second mixture and mixing of quest with second mixture for formation of third mixture.

EFFECT: elaboration of efficient method of obtaining complex with inclusion of cyclodextrin.

41 cl, 17 ex

 

The level of invention

The following U.S. patents disclose the use of cyclodextrins to form complexes with various guest molecules and fully incorporated into the present description by reference: U.S. Pat. U.S. No. 4296137, 4296138 and 4348416, Borden (taste the dressing for use in chewing gum, toothpastes, cosmetics, etc.); 4265779, Gandolfo et al. (foam inhibitors in the compositions of detergents); 3816393 and 4054736, Hyashi et al. (prostaglandins for use as pharmaceuticals); 3846551, Mifune et al. (insecticidal and acaricidal compositions); 4024223, Noda et al. (menthol, methyl salicylate, and the like); 4073931, Akito et al. (nitroglycerin); 4228160, Szjetli et al. (indometacin); 4247535, Bernstein et al. (inhibitors of complement); 4268501, Kawamura et al. (anti-asthma drugs); 4365061, Szjetli et al. (complexes of strong inorganic acids); 4371673, Pitha (retinoids); 4380626, Szjetli et al. (hormonal plant growth regulator), 4438106, Wagu et al. (long-chain fatty acids, applicable to reduce cholesterol); 4474822, Sato et al. (complexes tea concentrate); 4529608, Szietli et al.(honey flavor); 4547365, Kuno et al.(active complexes for perms); 4596795, Pitha (sex hormones); 4616008, Hirai et al. (antibacterial complexes); 4636343, Shibanai (insecticidal complexes); 4663316, Ninger et al. (antibiotics); 4675395, Fukazawa et al. (hinokitiol); 4732759 and 4728510, Shibanai et al. (bath additives); 4751095, Karl et al. (aspartame); 456051 (coffee extract); 4632832, Okonogi et al. (instant powder); 5571782, 5660845 and 5635238, Trinh et al. (perfumes/fragrances, flavors, and pharmaceuticals); 4548811, Kubo et al. (perming lotion); 6287603, Prasad et al. (perfumes/fragrances, flavors, and pharmaceuticals); 4906488, Pera (odorants, flavorings, medicines and pesticides); and 6638557, Qi et al. (fish fats).

Cyclodextrins are also described in the following publications, which are also included in the present description by reference: (1) Reineccius, T.A., et al. “Encapsulation of flavors using cyclodextrins: comparison of flavor retention in alpha, beta, and gamma types.”Journal of Food Science.2002; 67(9): 3271-3279; (2) Shiga, H., et al. “Flavor encapsulation and release characteristics of spray-dried powder by the blended encapsulant of cyclodextrin and gum arabic.”Marcel Dekker, Incl., www.dekker.com.2001; (3) Szente L., et al. “Molecular Encapsulation of Natural and Synthetic Coffee Flavor with β-cyclodextrin.”Journal of Food Science.1986; 51(4): 1024-1027; (4) Reineccius, G.A., et al. “Encapsulation of Artificial Flavors by β-cyclodextrin.”Perfumer &Flavorist (ISSN 0272-2666) An Allured Publication.1986: 11(4): 2-6; and (5) Bhandari, B.R., et al. “Encapsulation of lemon oil by paste method using β-cyclodextrin: encapsulation efficiency and profile of oil volatiles.”J.Agric. Food Chem.1999; 47: 5194-5197.

The invention

Some embodiments of the invention relate to a method for producing a complex with cyclodextrin inclusion. This method may include dry blending cyclodextrin and an emulsifier for the formation of the dry mixture and mixing a solvent and a guest with a dry mixture for the formation of a complex with the inclusion cyclodox is Rina.

In some embodiments, the invention features a method of obtaining a complex with cyclodextrin inclusion. This method can include mixing the cyclodextrin and an emulsifier for the formation of the first mixture, mixing the first mixture with the solvent for the formation of the second mixture and mixing the guest with the second mixture for formation of the third mixture.

Some embodiments of the invention relate to a method for producing a complex with cyclodextrin inclusion. This method may include dry blending cyclodextrin and pectin for the formation of the first mixture, mixing the first mixture with water for the formation of the second mixture and mixing of diacetyl with the second mixture for formation of the third mixture.

Other features and aspects of the invention will become obvious to specialists in this area when considering the following detailed description, claims and drawings.

Brief description of drawings

Fig. 1 is a schematic illustration of a molecule of cyclodextrin having a cavity and a guest molecule inside the cavity.

Fig. 2 is a schematic illustration of the nanostructures formed by self-organization cyclodextrins molecules and guest molecules.

Before discussing the details of any of the embodiments trail is t be understood, that the invention is not limited in its application to details of construction and arrangement of the components presented in the following description or illustrated in the drawings. The invention includes other embodiments of capable of practical implementation and execution of other ways. Thus, it should be understood that the phraseology and terminology used in this description is given for the purpose of description and should not be construed as restrictive. The use of the words “including”, “containing” or “having” and their variants intended to cover the components listed below, or their equivalents, as well as additional components.

Detailed description

The present invention is mainly directed to complexes with the inclusion of dextrin and methods for their preparation. Some complexes with the inclusion of dextrin according to the invention provide for the encapsulation of volatile and reactive molecules guest. In some embodiments, the implementation of the encapsulation of guest molecules can provide at least one of the following effects: (1) inhibition of leakage of volatile or reactive guest of a commercial product, which can lead to failure of the intensity of flavor in a commercial product; (2) the removal of guest molecules from the interaction of the of conduct and reaction with other components, that ought to interrupt the specified education; (3) stabilization of the guest molecule from degradation (e.g. hydrolysis, oxidation and so on); (4) selective extraction of guest molecules from other products or compounds; (5) enhance the water solubility of the guest molecule; (6) improving or enhancing the taste or smell of a commercial product; (7) thermal protection of a guest in a microwave oven and conventional baking applications; (8) a slow or extended release of the fragrance or smell (for example, variants of implementation using diacetyl as guest molecules in complex with the inclusion cyclodextrin can be ensured perception of melted butter); and (9) secure the preservation of the guest molecules.

The term “cyclodextrin” in the framework of the invention can be attributed to cyclic dextrin molecule, which is formed by enzymatic conversion of starch. Specific enzymes, for example, various forms cyclopyrrolones (CGT) can destroy the spiral patterns that are present in starch, with the formation of certain cyclodextrins molecules containing a three-dimensional ring polyglucose with, for example, 6, 7 or 8 glucose molecules. For example, α-CGT can turn the starch into α-cyclodextrin containing 6 units of glucose, β-CGT can turn the starch in β-cyclodextrin containing 7 is Diniz glucose, and γ-CGT can turn the starch in γ-cyclodextrin containing 8 units of glucose. Cyclodextrins include, but without limitation only by them at least one component of α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin or combinations thereof.

A three-dimensional cyclic structure (i.e. macrocyclic structure) cyclodextrins molecules 10 is schematically shown in Fig. 1. Cyclodextrine molecule 10 comprises an outer part 12, which includes primary and secondary hydroxyl groups and which is hydrophilic. Cyclodextrine molecule 10 also includes a three-dimensional cavity 14, which consists of carbon atoms, hydrogen atoms and essential communications, and which is hydrophobic. Hydrophobic cavity 14 cyclodextrins molecules can act as the host/the host component and contain many molecules or 16 guests, which contain a hydrophobic portion for the formation of a complex with a cyclodextrin inclusion.

The term “guest” in the framework of the invention, can be attributed to any molecule, from which at least a portion may be retained or captured within a three-dimensional cavity present in cyclodextrines molecule, and it includes without limitation at least one component of a flavor, odorant, pharmaceuticals, food products containing d is the additives, which increases its nutritional value, or combinations thereof.

Examples of flavors/flavoring additives may include, without limitation, the flavors on the basis of aldehydes, ketones or alcohols. Examples of aldehyde flavorings may include without limitation at least one flavoring from: acetaldehyde (Apple); benzaldehyde (cherry, almond); anisic aldehyde (licorice, anise); cinnamic aldehyde (thicket cinnamon); citral, i.e., alpha-citral (lemon, lime, true); neral, i.e. beta citral (lemon, lime, true); decanal (orange, lemon); ethylaniline (vanilla, cream); heliotropine, i.e. piperonal (vanilla, cream); vanillin (vanilla, cream); and-amiloride aldehyde (spicy fruity flavors); Butyraldehyde (butter, cheese); valeraldehyde (butter, cheese); citronellal (modifiers, many types); decennale (citrus fruits); aldehyde C-8 (citrus fruits); aldehyde C-9 (citrus fruits); aldehyde C-12 (citrus fruits); 2-ethylbutyraldehyde (berry fruits); hexenal, i.e. TRANS-2 (berry fruits); tolylaldehyde (cherry, almond); veratraldehyde (vanilla); 2,6-dimethyl-5-heptenal, ie, melons TM (melon); 2,6-dimethyloctane (green fruit); 2-dodecenal (citrus, Mandarin); and combinations thereof.

Examples of ketone flavorings may include without limitation at least one flavoring from: carve is a (caraway); 1-carvone (spearmint); diacetyl (butter, cheese, cream); benzophenone (fruit and spicy aromas, vanilla); methyl ethyl ketone (berry fruits); maltol (berry fruits), Menton (mints), methylmercaptan, ethylbutylamine, dipropylamine, methylhexanamine, ethylmercaptan (berry fruits, stone fruits); pyruvic acid (aromas of toasted nuts in large quantities); acetarsol (hawthorn heliotrope); dihydrocarvone (spearmint); 2,4-dimethylacetophenone (peppermint); 1,3-diphenyl-2-propanone (almonds); acetosella (iris and Basil, spicy smell); isaacman (Jasmine); d-isometries (iris, violet); isobutyrylacetate (brandy-like smell); zingerone (ginger); pulegone (peppermint-camphor); d-piperitone (mint); 2-nonanone (rose, smell like tea); and combinations thereof.

Examples of alcohol flavoring agents may include without limitation at least one flavor: anise alcohol or p-methoxybenzylthio alcohol (fruity, peach); benzyl alcohol (fruit); carvacrol or 2-p-seminola (burning warm smell); caveola; cinnamic alcohol (floral scent); citronellol (retopology); decanol; dihydrocarvone (spicy pepper); tetrahydropyranyl or 3,7-dimethyl-1-octanol (smell the roses); eugenol (clove); p-Menta-1,8-Dien-7-ol or parallelotope alcohol (color is but-pine); and their combinations.

Examples of odorants may include without limitation at least one odorant from natural flavorings, synthetic fragrances, synthetic essential oils, natural essential oils and their combinations.

Examples of synthetic fragrances may include without limitation at least one flavor of terpene hydrocarbons, esters, ethers, alcohols, aldehydes, phenols, ketones, acetals, oximo and their combinations.

Examples of terpene hydrocarbons may include without limitation at least one terpene hydrocarbon of lime terpenes, lemon terpenes, dimer limonene and their compositions.

Examples of esters may include without limitation at least one ester of γ-undecalactone, ethylethylenediamine, allelopathy, abililities, leventina, amylacetate, benzoylacetate, benzyl benzoate, benzylaniline, benzoylpropionate, butyl acetate, benzylmalonate, benzylpenicillin, terracotta, citronellate, citronellate, p-cresolate, 2-tert-pentylcyclohexyl, cyclohexylacetate, CIS-3-hexaniacinate, CIS-3-hexanicotinate, dimethylbenzylamine, diethylphthalate, δ-decorated.buffet, ethylbutyrate, ethyl acetate, ethylbenzoic, venchiarutti, geranylacetone, γ-datecalc is she, methyldihydromorphine, isobutylacetate, β-isopropoxybenzonitrile, minalrestat, methylbenzoate, o-tert-butylcyclohexylamine, methyl salicylate, telebrasil, atlantogenata, methylphenylacetic, generateresource, phenylethylenediamine, phenylethylamine, methylphenylcarbinol, 3,5,5-trimethylhexanoate, techinicality, triethylcitrate, p-tert-butylcyclohexylamine, vetiverlatina and their combinations.

Examples of ethers may include without limitation at least one simple ester of p-kresimirova ether, diphenyl ether, 1,3,4,6,7,8-hexahydro-4,6,7,8,8-HEXAMETHYL-cyclopent-β-2-benzopyran, penalitatilor ether and combinations thereof.

Examples of the alcohols may include without limitation at least one alcohol from n-oktilovom alcohol, n-danilovogo alcohol, β-phenylethylenediamine, dimethylphenylcarbinol, orbitaldegeneracy, dimethyloctane, hexyleneglycol, alcohol from vegetable raw materials, nerol, Phenoxyethanol, γ-phenylpropionic alcohol, β-phenethyl alcohol, methylphenylcarbinol, terpineol, tetrahydroaluminate, tetrahydroindole, 9-mission-1-ol and their compositions.

Examples of the aldehydes may include without limitation at least one aldehyde of the n-nonrendered, underanalyzed, methylnoradrenaline, anisopodidae, benzaldehyde, ciclamino aldehyde, 2-hexidecimal and mexikoring aldehyde, phenylacetaldehyde, 4-(4-hydroxy-4-methylpentyl)-3-cyclohexen-1-carboxaldehyde, p-tert-butyl-a-methylhydrocinnamic aldehyde, hydroxycitronellal, α-amiloride aldehyde, 3,5-dimethyl-3-cyclohexen-1-carboxaldehyde and their combinations.

Examples of phenols may include, without limitation, methyleugenol.

Examples of the ketones may include without limitation at least one ketone of 1-carvone, α-damascone, ionone, 4-tert-pentylcyclohexanone, 3-amyl-4-acetonecyanohydrin, Mentone, methylionone, p-tert-arylcyclohexylamine, acetylserine and their combinations.

Examples of acetals may include, without limitation, phenylacetaldehyde.

Examples Asimov may include without limitation 5-methyl-3-heptanone.

Guest may also include without limitation at least one component of fatty acids, lactones, terpenes, diacetyl, dimethyl sulfide, Proline, furaneol, linalool, acetylphenyl, natural essences (for example, orange, tomato, Apple, cinnamon, raspberry etc), essential oils (e.g., orange, lemon, lime, etc. and their combinations.

The term “complex with cyclodextrin inclusion” in the context of the invention refers to the complex, which is formed to maintain is the key at least portions of one or more guest molecules with one or more molecules of cyclodextrin (encapsulation at the molecular level) by the seizure or retention of the guest molecule inside a three-dimensional the cavity. Guest may be held in position by the van der Waals inside the cavity using at least one of the hydrogen bonds and hydrophilic-hydrophobic interactions. Guest can be released from the cavity, when the complex with the inclusion cyclodextrin is dissolved in water.

The term “hydrocolloid” in the framework of the invention typically refers to a substance that forms a gel with water. The hydrocolloid may include without limitation at least one hydrocolloid from xanthan gum, pectin, Arabic gum, tragakant, the guar resin, carrageenan, carob and their combinations.

The term “pectin” in the framework of the invention relates to a hydrocolloid polysaccharide, which can be found in plant tissues (for example, in ripe fruits and vegetables). Pectin may include without limitation at least one pectin from beet pectin, fruit pectin (for example, from the peel of citrus), and combinations thereof. Used pectin may have a different molecular mass.

Complexes with the inclusion of dextrin according to the invention can be used in many applications, including without limitation at least one of the following: food (e.g., popcorn, cereals, coffee, sweet bread, chocolate brownies with nuts, bakery products etc), the same is atelinae gum, candy, flavorings, perfumes, medicines, foods containing additives, which increase their nutritional value, cosmetics, agricultural applications (e.g., herbicides, pesticides etc), emulsions for pictures, and combinations thereof. In some embodiments, the implementation of the inclusion complexes with cyclodextrin can be used as an intermediate excretory matrix, intended for additional processing, separation and drying (for example, applied with waste streams).

Complexes with the inclusion of dextrin can be used to improve the stability of the guest, turning it into a free-flowing powder or otherwise changes its solubility, delivery or effectiveness. The number of guest molecules, which can be encapsulated, is directly related to the molecular weight of the molecules of the guest. In some embodiments, the implementation of one mole of the cyclodextrin capsulebuy one mole of molecules of the guest. According to this molar ratio and only as an example, in variants of the implementation with the use of diacetyl (molecular weight 86 Dalton), as a guest, and β-cyclodextrin (molecular weight of 1135 daltons), the maximum theoretical retention is (86/(86+1135))=? 7.04 baby mortality wt.%.

In some embodiments, the implementation of the cyclodextrin can be the t itself organize solution in the form of nanostructures, such as nano-structure 20, shown in Fig. 2, which may include three mole guest on two mol of cyclodextrin molecules. For example, in variants of the implementation with the use of diacetyl as a guest of 10.21 wt.% retention of diacetyl is possible. Other agents that enhance the complex, such as pectin, can facilitate the process of self-organization and can maintain a 3:2 molar ratio guest:cyclodextrin throughout drying. In some embodiments, the implementation due to the self-organization of the cyclodextrin molecules in nano-structures 5:3 molar ratio guest:cyclodextrin is possible.

The inclusion complexes with cyclodextrin formed in solution. The drying process temporarily locks at least a portion of the guest in the cavity of the cyclodextrin and produces free-flowing powder.

Hydrophobic (water-insoluble) nature cyclodextrins cavity is mainly to catch like (hydrophobic) molecules are most easily compared with the cost of more water-soluble (hydrophilic) molecules guests. This phenomenon can give the imbalance of the components compared to conventional spray drying, and low total output.

In some embodiments of the invention the competition between hydrophilic and hydrophobic effects eliminate the selection key is of evich ingredients for separate encapsulation. For example, in the case of fragrance oil fatty acids and lactones form complexes with the inclusion of dextrin easier than diacetyl. However, these compounds are not the key compounds that have the main impact associated with oil, and they will reduce the overall yield of diacetyl and other water-soluble and volatile ingredients. In some embodiments, the implementation of the key ingredient in the fragrance oil (i.e. diacetyl) do the maximum to create a highly efficient, more stable and more economical product. As an example, in the case of lemon aromas, most components of lemon aroma will capsulitis equally well in the cyclodextrin. However, terpenes (a component of lemon flavor) give a small contribution to the aroma and comprise approximately 90% of the mixture of lemon flavor, while citral is a key ingredient fragrance of lemon flavoring. In some embodiments, the implementation of citral capsulebuy individually. In the selection of key ingredients (e.g., diacetyl, citral, etc.) to separate encapsulation reduces the complexity of the source material, which allows to optimize the stage of design and economy of the process.

In some embodiments, the implementation of the mainstreaming process for the formation of a complex with a cyclodextrin inclusion Pref is changed to completion by adding a molar excess of the guest. For example, in some embodiments, the implementation of the guest unite with cyclodextrin at a molar ratio of guest:cyclodextrin, equal to 3:1.

In some embodiments, the implementation of control the viscosity of the suspension, emulsion or mixture, obtained by mixing cyclodextrin and guest molecules in solution, and compatibility with conventional spray drying install without other approvals, such as the high concentration of solids. The emulsifier (e.g., thickener, gelling the polysaccharide hydrocolloid may be added to maintain uniform contact between the cyclodextrin and the guest and to aid in the process of inclusion. In particular, you can use the hydrocolloids with low molecular weight. One of the preferred hydrocolloids is a pectin. Emulsifiers can help the process of inclusion without consuming large heat or co-solvents (e.g. ethanol, acetone, isopropanol and so on) to improve the solubility.

In some embodiments, the implementation of the water content in the suspension, emulsion or mixture reduces to essentially force a guest to behave as hydrophobic compound. This process can increase the retention of even a relatively hydrophilic guests, such as acetaldehyde, diacetyl, dimethyl sulfide, etc. to Reduce the water content m is likely also to maximize the performance of the spray drying apparatus and to reduce the possibility of leakage of volatile guests in the process, which can reduce overall performance.

In some embodiments of the invention, the complex with the inclusion of dextrin can be obtained in the following way, which may include some or all of the following stages:

(1) Dry blending cyclodextrin and an emulsifier (e.g., pectin);

(2) the Connection of the dry mixture of a cyclodextrin and an emulsifier with hot liquid or solvent, such as water in the reactor and stirring;

(3) Adding a guest and mixing (e.g., within about 5 to 8 hours);

(4) cooling of the reactor (for example, placement in a cooling jacket);

(5) Mixing the mixture (for example, for about 12 to 36 hours);

(6) Emulsification (e.g., instant tank mixer /in-tank lightning mixer or stand mixer with powerful shredding drops/high shear drop-in mixer);

and

(7) Drying of the complex with the inclusion cyclodextrin to obtain a powder.

Optional these stages should be followed in order. In addition, the above method has shown that it must be very acceptable, as this method can be implemented using a variety of temperature, time, mixing, and other parameters of the method.

In some embodiments, the implementation of stage 1 in the above-described method may be performed using eservoirs mixer in the reactor, to be added to hot water in stage 2. For example, in some embodiments, the implementation of the above method is performed using a 1000 gallon reactor equipped with a jacket for temperature control, and acting on one line mixer with powerful shredding drops, and the reactor is directly connected to the spray drying apparatus. In some embodiments, the implementation of a cyclodextrin and an emulsifier can be mixed dry in the separation apparatus (e.g., ribbon mixer) and then added to the reactor, in which to complete the remaining stages of the above method.

Can be used in different mass percent of the emulsifier to the cyclodextrin, including without limitation the mass percentage of the emulsifier:cyclodextrin, equal to at least about 0.5%, especially at least about 1%, and more preferably at least about 2%. In addition, can be used emulsifier:cyclodextrin mass percent, less than about 10%, especially less than about 6%, and more preferably, less than about 4%.

Stage 2 in the above-described method may be performed in a reactor which is equipped with a jacket for heating, cooling or both. The size of the reactor can affect the value of the products. For example, you can use 100 gallon R is the actor. The reactor can have a paddle stirrer and condenser.

In some embodiments, the implementation of stage 1 is completed in the reactor and in stage 2 hot deionized water added to the dry mixture of cyclodextrin and pectin in the same reactor.

Stage 3 can be performed in a closed reactor or the reactor can be temporarily exposed to the environment while adding the guest and the reactor after addition of the guest can be reclosed

Stage 4 can be performed using a cooling system which includes a cooling jacket. For example, the reactor can be cooled propylene glycol refrigerant and cooling water jacket.

Mixing in stage 2, mixing in stage 3 and the mixing stage 5 may be executed by one of the methods: shaking, stirring, tumbling or combinations thereof.

At stage 6 the mixture of cyclodextrin, emulsifier, water and a guest can be converted into an emulsion using at least one of the mixers: mixer with powerful shredding drops (for example, ROSS-brand mixer at 10,000 rpm, RPM for 90 seconds), instant mixer, or by simple mixing with the subsequent transfer pump homogenization, which is a spray drying device, or combinations thereof.

Step 7 in the above-described method can b shall be made at least one way: air drying, vacuum drying, spray drying (for example, through a nozzle of the spray drying device, a drying device with rotating disks, and so on), drying in an oven or combinations thereof.

The method presented above can be used to obtain inclusion complexes with cyclodextrin with many features for various applications. For example, some embodiments of the present invention provide a complex with cyclodextrin inclusion with the guest containing diacetyl, which can be used for various food products as a flavoring oils (for example, air corn, bakery products etc). In addition, some embodiments of give a complex with cyclodextrin inclusion with the guest containing citral, which can be used for acid resistant drinks. In addition, some embodiments of give a complex with the inclusion of a cyclodextrin with a combination of aromatic molecules as guests, which can simulate oil the aroma of diacetyl. For example, a complex with a cyclodextrin inclusion may alternatively include at least one component of dimethyl sulfide (volatile sulfur compound), Proline (amino acid) and furaneol (amplifier sweet taste) as guest. Complex with cyclodextrin inclusion without Diaz the tilapia can be used to provide fragrance oils in food products, such as the products described above.

Various features and aspects of the invention are presented in the following examples.

Example 1. Complex with cyclodextrin inclusion of β-cyclodextrin and diacetyl and how to obtain it

At atmospheric pressure in a 100 gallon reactor was mixed 49895,1600 g (110,02 pound) of β-cyclodextrin in dry form with 997,9 g (2,20 lb) of beet pectin (2 wt.% pectin: β-cyclodextrin; XPQ EMP 5 beet pectin available from the company Degussa-France) to obtain a dry mixture. 100 gallon reactor was supplied with jacket for heating and cooling, paddle stirrer and condenser. To the reactor was filed propylene glycol refrigerant at approximately 40°F (4,5°C). Propylene glycol cooling system is initially off and the shirt acts to some extent as an insulator for the reactor. 124737,9 g (275,05 pound) hot deionized water was added to the dry mixture of β-cyclodextrin and pectin. The water had a temperature of approximately 118°F (48°C). The mixture was stirred for approximately 30 minutes using a paddle stirrer of the reactor. The reactor is then temporarily opened and added 11226,4110 g (24,75 pound) of diacetyl. The reactor was again closed and the mixture was stirred for 8 hours without heating. Then the jacket of the reactor was connected to propylene glycol cooling system. The refrigerant is included in the rough is about 40°F (4,5°C) and the mixture was stirred for approximately 36 hours. The mixture was then emulsiable with powerful grinding tank mixer, such as mixer commonly used in transactions with spray drying. The mixture is then dried by spray drying nozzle device having a temperature in the inlet hole of approximately 410°F (210°C) and the temperature at the outlet is approximately 221°F (105°C). Was achieved percentage retention of diacetyl in complex with cyclodextrin inclusion, equal 18,37 wt.%. The moisture content measured as 4.0 percent. Complex with cyclodextrin inclusion contained less than 0.3% of the surface of diacetyl, and the particle size of the complex with the cyclodextrin inclusion corresponded to 99.7% sieve 80 mesh.

Example 2. Complex with cyclodextrin inclusion of α-cyclodextrin and diacetyl and how to obtain it

β-cyclodextrin of example 1 was replaced with α-cyclodextrin and dry mixed with 1 wt.% pectin (1 wt.% pectin: β-cyclodextrin; XPQ EMP 5 beet pectin available from the company Degussa-France). The mixture was processed and dried by the method shown in example 1. The percentage retention of diacetyl in complex with cyclodextrin inclusion was 11.4 wt.%.

Example 3. Complex with cyclodextrin inclusion of β-cyclodextrin and orange concentrate and method thereof

Orange concentrate, water waste from production is DSTV juice was added as the aqueous phase to a dry mixture of β-cyclodextrin and 2 wt.% pectin obtained by the method of example 1. Without adding an additional quantity of water, the solids content of approximately 28%. The complex with the inclusion cyclodextrin was obtained by the method of example 1. The dry complex with the inclusion contained about 3 to 4 wt.% acetaldehyde, from about 5 to 7 wt.% ethylbutyrate, from about 2 to 3 wt.% linalool and other citrus reinforcing components. The resulting complex with the inclusion cyclodextrin can be used in the above drinks.

Example 4. Complex with cyclodextrin inclusion of β-cyclodextrin and acetylphenyl and how to obtain it

Molar excess acetylphenyl was added to a dry mixture of β-cyclodextrin and 2 wt.% pectin in water by the method of example 1. The percentage retention acetylphenyl in complex with cyclodextrin inclusion was 9,27 wt.%. This mixture can be used in the above systems oils that do not contain diacetyl.

Example 5. The product with the aroma of orange oil and the method of its production

Orange oil (i.e., Orange Bresil; 75 g) was added to the aqueous phase, containing 635 g of water, 403,75 g maltodextrin and 21.25 g of beet pectin (available from the company Degussa-France, product number XPQ EMP-5). Orange oil was added to the aqueous phase with gentle stirring, with subsequent strong premesis the tion at 10,000 rpm for formation of the mixture. The mixture was then passed through a homogenizer at 250 bar for the formation of the emulsion. The emulsion was dried using a spray drying device brand NIRO with a temperature of approximately 180°With the inlet and with a temperature of approximately 90°With the release for the formation of dry product. The percentage retention of taste then considered as the ratio of oil content (in grams) per 100 g of dry product to the oil content in the initial mixture. The percentage retention of orange oil was approximately 91.5 per cent.

Example 6. The product with the aroma of orange oil and the method of its production

Orange oil (75 g) was added to the aqueous phase, containing 635 g of water, 297,50 g maltodextrin and 127,50 g Arabian gum (available from the firm of Colloids Naturels International). Orange oil was added to the aqueous phase and then dried according to the method of example 5. The percentage retention of the aroma was approximately 91.5 per cent.

Example 7. The product with the aroma of orange oil and the method of its production

Orange oil (75 g) was added to the aqueous phase, containing 635 g of water, 297,50 g maltodextrin, 123,25 g Arabian gum (available from the firm of Colloids Naturels International) and 4.25 g depolimerizovannogo citrus pectin. Orange oil was added to the aqueous phase and then dried according to the method of example 5. The percentage retention of the aroma was approximately 96.9 percent.

the example 8. The product with the aroma of orange oil and the method of its production

Orange oil (75 g) was added to the aqueous phase, containing 635 g of water, 297,50 g maltodextrin, 123,25 g Arabian gum (available from the firm of Colloids Naturels International) and 4.25 g of beet pectin (available from the company Degussa-France, product number XPQ EMP-5). Orange oil was added to the aqueous phase and then dried according to the method of example 5. The percentage retention of the aroma was approximately 99%.

Example 9. The product with the aroma of orange oil and the method of its production

Orange oil (75 g) was added to the aqueous phase, containing 635 g of water, 403,75 g maltodextrin and 21.25 g depolimerizovannogo citrus pectin. Orange oil was added to the aqueous phase and then dried according to the method of example 5. The percentage retention of the aroma was approximately 90,0%.

Example 10. The product with the aroma of orange oil and the method of its production

Orange oil (75 g) was added to the aqueous phase, containing 635 g of water, 340,00 g maltodextrin and 85,00 g Arabian gum (available from the firm of Colloids Naturels International). Orange oil was added to the aqueous phase and then dried according to the method of example 5. The percentage retention of the aroma was approximately 91,0%.

Example 11. The product with the aroma of orange oil and the method of its production

Orange oil (75 g) was added to aq the phase, containing 635 g of water and 425,00 g of maltodextrine. Orange oil was added to the aqueous phase and then dried according to the method of example 5. The percentage retention of the aroma was approximately 61,0%.

Example 12. The product with the aroma of orange oil and the method of its production

Orange oil (75 g) was added to the aqueous phase, containing 635 g of water, 420,75 g maltodextrin and 4.25 g of pectin. Orange oil was added to the aqueous phase and then dried according to the method of example 5. The percentage retention of the aroma was approximately 61.9%of.

Example 13. The product with the aroma of orange oil and the method of its production

Orange oil (75 g) was added to the aqueous phase, containing 635 g of water, 403,75 g maltodextrin; 21.50 g of pectin. Orange oil was added to the aqueous phase and then dried according to the method of example 5. The percentage retention of the aroma was approximately 71.5%of the.

Example 14. The product with the aroma of orange oil and the method of its production

Orange oil (75 g) was added to the aqueous phase, containing 635 g of water, 420,75 g maltodextrin and of 4.75 g depolimerizovannogo citrus pectin. Orange oil was added to the aqueous phase and then dried according to the method of example 5. The percentage retention of the aroma was approximately 72,5%.

Example 15. The product with the aroma of orange oil and the method of its production

Orange mA is lo (75 g) was added to the aqueous phase, containing 635 g of water, 420,75 g maltodextrin and of 4.75 g of beet pectin (available from the company Degussa-France, product number XPQ EMP-5). Orange oil was added to the aqueous phase and then dried according to the method of example 5. The percentage retention of the aroma was approximately 78,0%.

Example 16. The product with the aroma of orange oil and the method of its production

Orange oil (75 g) was added to the aqueous phase, containing 635 g of water, 414,40 g maltodextrin and or 10.60 g depolimerizovannogo citrus pectin. Orange oil was added to the aqueous phase and then dried according to the method of example 5. The percentage retention of the aroma was approximately 85,0%.

Example 17. The product with the aroma of orange oil and the method of its production

Orange oil (75 g) was added to the aqueous phase, containing 635 g of water, 414,40 g maltodextrin and or 10.60 g of beet pectin (available from the company Degussa-France, product number XPQ EMP-5). Orange oil was added to the aqueous phase and then dried according to the method of example 5. The percentage retention of the aroma was approximately 87,0%.

Various features and aspects of the invention are represented in the following claims.

1. The method of producing complex with cyclodextrin inclusion, including:
dry blending cyclodextrin and hydrocolloid for the formation of a dry mixture; and
the mixing of solvent and hostas dry mixture for the formation of a complex with a cyclodextrin inclusion; and
drying complex with cyclodextrin inclusion.

2. The method according to claim 1, where the mixing of solvent and a guest with a dry mixture for the formation of a complex with a cyclodextrin inclusion gives a mixture containing the complex with cyclodextrin inclusion, and the method further includes drying the mixture.

3. The method according to claim 2, where the drying includes at least one drying of air drying, vacuum drying, spray drying, drying in an oven, and combinations thereof.

4. The method according to claim 2, additionally comprising emulsification of a mixture of at least one tank of the mixer and mixer with powerful shredding drops, before drying the mixture.

5. The method according to claim 2, where the mixture comprises a quantity of solvent, and the method further includes reducing the amount of the solvent mixture before drying the mixture.

6. The method according to claim 1, where the guest and mixing of the solvent with a dry mixture comprises mixing the solvent and dry the mixture, and then mixing a guest with them.

7. The method according to claim 1, where the hydrocolloid comprises at least one component from among xanthan resin, pectin, Arabic gum, tragakant, the guar resin, carrageenan, carob, and combinations thereof.

8. The method according to claim 1, where the hydrocolloid comprises pectin.

9. The method of claim 8, where the pectin comprises at least one component from among beet pectin, fruit is about pectin, and combinations thereof.

10. The method according to claim 1, where the solvent contains water.

11. The method of claim 8, where the cyclodextrin comprises at least one component from among α-cyclodextrin, β-cyclodextrin, γ-cyclodextrin, and combinations thereof.

12. The method according to claim 1, where the guest includes at least one component of flavor, odorant, pharmaceuticals, food products containing additives which increase its nutritional value, and combinations thereof.

13. The method according to item 12, where the flavoring includes at least one component from among aldehyde, ketone, alcohol, and combinations thereof.

14. The method according to item 12, where the odorant includes at least one component from among natural flavors, synthetic fragrances, synthetic essential oils, natural essential oils and their combinations.

15. The method according to claim 1, where the guest includes at least one component from among fatty acids, lactones, terpenes, diacetyl, dimethyl sulfide, Proline, furaneol, linalool, acetylphenyl, natural essences, essential oils, and combinations thereof.

16. The method according to claim 1, where the guest includes diacetyl.

17. The method according to claim 1, where the complex with cyclodextrin inclusion is characterized at least in part, a nanostructure containing a cyclodextrin and a guest component.

18. The method according to 17, where the nanostructure includes m is regular attitude guest: cyclodextrin, equal to at least about 3:2.

19. The method according to claim 1, where the guest and mixing of the solvent with a dry mixture comprises mixing a guest and cyclodextrin in a molar ratio of guest:cyclodextrin, equal to at least approximately 3:1.

20. The method according to claim 1, where the complex with the inclusion cyclodextrin obtained without additional heating or without co-solvents.

21. The method according to claim 1, where the connection of the guest and solvent with a dry mixture comprises mixing the guest solvent and dry the mixture.

22. The method according to item 21, where the guest stirring, the dry mixture and solvent occurs within approximately 5 to 8 hours

23. The method according to claim 1, where the mixing of solvent and a guest with a dry mixture for the formation of a complex with a cyclodextrin inclusion involves the formation of a mixture containing the complex with cyclodextrin inclusion, and the method further includes cooling the mixture.

24. The method according to item 23, where the cooled mixture includes the start of the cooling jacket.

25. The method according to claim 1, where the guest and mixing of the solvent with dry mixture is performed in a closed reactor.

26. The method according to claim 1, where the dry blending cyclodextrin and hydrocolloid includes dry blending cyclodextrin and hydrocolloid in mass percentage relationship hydrocolloid:cyclodextrin, equal to at least about 0.5 wt.%.

27. Pic is b according to claim 1, where dry blending cyclodextrin and hydrocolloid includes dry blending cyclodextrin and hydrocolloid in mass percentage relationship hydrocolloid:cyclodextrin less than about 10 wt.%.

28. The complex with the inclusion cyclodextrin obtained according to the method of claim 1.

29. Complex with cyclodextrin inclusion on p, where the mass percentage of the visitor to a cyclodextrin complex with cyclodextrin inclusion equal to at least about 10 wt.%.

30. Complex with cyclodextrin inclusion on p, where the complex with the inclusion cyclodextrin is used in at least one of the following applications: food, gum, candy, flavorings, perfumes, medicines, foods containing additives, which increase their nutritional value, cosmetics, agricultural applications, emulsions for photographic systems, waste streams, and combinations thereof.

31. The method of producing complex with cyclodextrin inclusion, including:
mixing cyclodextrin and hydrocolloid for the formation of the first mixture;
mixing the first mixture with the solvent for the formation of the second mixture;
the guest mix with the second mixture for formation of the third mixture; and drying complex with cyclodextrin inclusion.

32. The method according to p, where the connection cyclodextrin and Hydra the colloid includes dry drying.

33. The method according to p, where the hydrocolloid comprises at least one component from among xanthan resin, pectin, Arabic gum, tragakant, the guar resin, carrageenan, carob, and combinations thereof.

34. The method according to p, where the emulsifier comprises pectin.

35. The method according to p, where the guest includes at least one component of flavor, odorant, pharmaceuticals, food products containing additives which increase its nutritional value, and combinations thereof.

36. The method according to p, where the guest includes diacetyl.

37. The complex with the inclusion cyclodextrin obtained by the method p.

38. The method of producing complex with cyclodextrin inclusion, including:
dry blending cyclodextrin and pectin for the formation of the first mixture;
mixing the first mixture with water for the formation of the second mixture;
mixing of diacetyl with the second mixture for formation of the third mixture; and
drying complex with cyclodextrin inclusion.

39. The method according to § 38, where the cyclodextrin and pectin are mixed dry in mass percentage relationship pectin:cyclodextrin, equal to at least about 0.5 wt.%.

40. The method according to § 38, where the cyclodextrin and pectin are mixed dry in mass percentage relationship pectin:cyclodextrin, less than about 10 wt.%.

41. The complex with the inclusion of the cycle is dextrin, obtained by the method according to § 38.



 

Same patents:

FIELD: chemistry.

SUBSTANCE: molar ratio of cyclodextrin to the acid in the complex comprises 1:1. The complex is obtained by introduction of concentrated water cyclodextrin solution heated to boiling point to glacial acetic acid of room temperature, with further separation and drying of crystalline sediment. Complex of α- or β-cyclodextrin with acetic acid is stable in dry state, but in water solution it is decomposed into components. Obtained solution gains properties of dilated acetic acid, and therefore can be used as flavouring in food concentrates, as preservation agent, solution acidity regulator, and as buffer component in biochemistry and analytical chemistry.

EFFECT: enhanced efficiency of composition.

3 cl, 4 ex, 1 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to cyclodextrin-containing polymeric compounds, which are carriers for delivery of therapeutics, and pharmaceutical preparations based on them. Invention also relates to method of treating subjects with therapeutically effective quantity of said cyclodextrin-containing polymeric compound. Claimed cyclodextrin-containing polymers improve medication stability, increase its solubility and reduce toxicity of therapeutics when used in vivo. Furthermore, by selecting from a variety of linker groups and targeting ligands of said polymers it is possible to realise controlled delivery of therapeutic agents.

EFFECT: obtaining cyclodextrin-containing polymer compounds, improving medication stability, increasing its solubility and reducing toxicity of therapeutics when used in vivo.

56 cl, 13 dwg, 7 tbl, 46 ex

FIELD: chemical technology.

SUBSTANCE: invention relates to the inclusion complex of cyclodextrins with elemental sulfur. Complex can be prepared using different homologues of cyclodextrins, for example, beta- and gamma-cyclodextrins and hydroxypropylated forms of gamma- and beta-cyclodextrins. Proposed complex can be used as a biologically active compound for medicinal, veterinary and agricultural designation. Invention provides the possibility for further preparing true solutions of elemental sulfur in water in the concentration up to 250-300 mg/l.

EFFECT: improved preparing method, valuable properties of complex.

7 cl, 7 ex

FIELD: chemical technology.

SUBSTANCE: invention describes a method for preparing immobilized β-cyclodextrin. Method involves pretreatment of organic and inorganic sorbents - polyvinyl alcohol and sorbitol based on silica with glutaraldehyde for incorporation of aldehyde group molecules into sorbents, washing out with water and dimethylsulfoxide on glass porous filter, drying on glass porous filter followed by addition of prepared sorbents to dimethylsulfoxide solution containing dissolved β-cyclodextrin in the ratio sorbent : β-cyclodextrin : dimethylsulfoxide = 1.0:(0.4- 2.0);10, respectively, stirring the prepared suspension at temperature 25-70°C for 30-180 min, washing out and drying. Method provides preparing an insoluble sorbent with immobilized β-cyclodextrin used for removing cholesterol or its derivatives.

EFFECT: improved preparing method.

5 ex

FIELD: organic chemistry, medicine.

SUBSTANCE: invention describes a derivative of 6-mercaptocyclodextrin of the general formula (I):

wherein n = 0-7; n = 1-8 and m + n = 7 or 8; R represents (C1-C6)-alkylene substituted optionally with 1-3 OH-groups, or (CH2)o-phenylene-(CH2)p wherein o and p = 0-4 independently; X represents COOH, CONHR1, NHCOR2, SO2OH, PO(OH)2, O(CH2-CH2-O)q-H, OH or tetrazole-5-yl; R1 represents hydrogen atom (H) or (C1-C3)-alkyl; R2 represents carboxyphenyl; q = 1-3; or its pharmaceutically acceptable salt in mixture with pharmaceutically acceptable accessory substances. Also, invention describes a set and pharmaceutical composition for reversing drug-induced neuromuscular blocking comprising derivative of 6-mercaptocyclodextrin of the general formula (I), and a method for reversing drug-induced neuromuscular blockade in patient that involves parenteral administration to indicated patient the effective dose of 6-mercaptocyclodextrine derivative of the general formula (I) by cl. 1.

EFFECT: valuable medicinal properties of agents.

11 cl, 1 tbl, 20 ex

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FIELD: organic chemistry, medicine.

SUBSTANCE: invention describes a derivative of 6-mercaptocyclodextrin of the general formula (I):

wherein n = 0-7; n = 1-8 and m + n = 7 or 8; R represents (C1-C6)-alkylene substituted optionally with 1-3 OH-groups, or (CH2)o-phenylene-(CH2)p wherein o and p = 0-4 independently; X represents COOH, CONHR1, NHCOR2, SO2OH, PO(OH)2, O(CH2-CH2-O)q-H, OH or tetrazole-5-yl; R1 represents hydrogen atom (H) or (C1-C3)-alkyl; R2 represents carboxyphenyl; q = 1-3; or its pharmaceutically acceptable salt in mixture with pharmaceutically acceptable accessory substances. Also, invention describes a set and pharmaceutical composition for reversing drug-induced neuromuscular blocking comprising derivative of 6-mercaptocyclodextrin of the general formula (I), and a method for reversing drug-induced neuromuscular blockade in patient that involves parenteral administration to indicated patient the effective dose of 6-mercaptocyclodextrine derivative of the general formula (I) by cl. 1.

EFFECT: valuable medicinal properties of agents.

11 cl, 1 tbl, 20 ex

FIELD: chemical technology.

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EFFECT: improved preparing method.

5 ex

FIELD: chemical technology.

SUBSTANCE: invention relates to the inclusion complex of cyclodextrins with elemental sulfur. Complex can be prepared using different homologues of cyclodextrins, for example, beta- and gamma-cyclodextrins and hydroxypropylated forms of gamma- and beta-cyclodextrins. Proposed complex can be used as a biologically active compound for medicinal, veterinary and agricultural designation. Invention provides the possibility for further preparing true solutions of elemental sulfur in water in the concentration up to 250-300 mg/l.

EFFECT: improved preparing method, valuable properties of complex.

7 cl, 7 ex

FIELD: chemistry.

SUBSTANCE: invention relates to cyclodextrin-containing polymeric compounds, which are carriers for delivery of therapeutics, and pharmaceutical preparations based on them. Invention also relates to method of treating subjects with therapeutically effective quantity of said cyclodextrin-containing polymeric compound. Claimed cyclodextrin-containing polymers improve medication stability, increase its solubility and reduce toxicity of therapeutics when used in vivo. Furthermore, by selecting from a variety of linker groups and targeting ligands of said polymers it is possible to realise controlled delivery of therapeutic agents.

EFFECT: obtaining cyclodextrin-containing polymer compounds, improving medication stability, increasing its solubility and reducing toxicity of therapeutics when used in vivo.

56 cl, 13 dwg, 7 tbl, 46 ex

FIELD: chemistry.

SUBSTANCE: molar ratio of cyclodextrin to the acid in the complex comprises 1:1. The complex is obtained by introduction of concentrated water cyclodextrin solution heated to boiling point to glacial acetic acid of room temperature, with further separation and drying of crystalline sediment. Complex of α- or β-cyclodextrin with acetic acid is stable in dry state, but in water solution it is decomposed into components. Obtained solution gains properties of dilated acetic acid, and therefore can be used as flavouring in food concentrates, as preservation agent, solution acidity regulator, and as buffer component in biochemistry and analytical chemistry.

EFFECT: enhanced efficiency of composition.

3 cl, 4 ex, 1 tbl

FIELD: chemistry.

SUBSTANCE: method of obtaining complex with inclusion of cyclodextrin can include dry mixing of cyclodextrin and hydrocolloid for formation of dry mixture and mixing solvent and guest with dry mixture for formation of complex with inclusion of cyclodextrin. In some versions of realisation method of obtaining complex with inclusion of cyclodextrin can include mixing of cyclodextrin and hydrocolloid for formation of first mixture, mixing of first mixture with solvent for formation of second mixture and mixing of quest with second mixture for formation of third mixture.

EFFECT: elaboration of efficient method of obtaining complex with inclusion of cyclodextrin.

41 cl, 17 ex

FIELD: chemistry.

SUBSTANCE: method of intensifying antiaggregant activity in an experiment involves use of a chemical compound which is a conjugate of beta-cyclodextrin with acetylsalicylic acid.

EFFECT: wider range of agents for increasing antiaggregant activity.

1 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to a novel clathrate complex of β-cyclodextrin with 1-{[6-bromo-1-methyl-5-methoxy-2-phehylthiomethyl-1-H-indol-3-yl]carbonyl}-4-benzylpiperazine of formula : with molar ratio 1-{[6-bromo-1-methyl-5-methoxy-2-phehylthiomethyl-1-H-indol-3-yl]carbonyl}-4-benzylpiperazine: β-cyclodextrin from 1:1 to 1:10, synthesis method and use thereof as an antiviral agent for treating influenza. The disclosed method involves mixing solutions of β-cyclodextrin and 1-{[6-bromo-1-methyl-5-methoxy-2-phehylthiomethyl-1-H-indol-3-yl]carbonyl}-4-benzylpiperazine in molar ratio from 1:1 to 1:10 while stirring and heating to temperature not higher than 70°C and then maintaining said conditions until a homogeneous solution is obtained and extraction of the obtained complex.

EFFECT: clathrate complex is a novel effective anti-influenza virus agent which is obtained using a novel efficient method.

13 cl, 2 ex, 3 tbl, 11 dwg

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to a new β-cyclodextrine clathrate complex (an inclusion compound) with 5-hydroxy-4-aminomethyl-1-cyclohexyl(or cycloheptyl)-3-alkoxycarbonylindole derivative: β-cyclodextrine 1:1 to 1:5, preferentially at the relation of 1:1 to 1:3 of general formula (I): wherein X means - hydrogen, chlorine, iodine, n=1 or 2, R3-C1-C3 alkyl, ALK means C1-C6 alkyl group, R1, R2 are independently specified in C1-C4-alkyl, preferentially methyl, or R1 and R2 together with a nitrogen atom (i.e. group - NR1R2) means the groups described by formulas: wherein Bn is benzyl, a Ph is phenyl with the molar ratio of 5-hydroxy-4-aminomethyl-1-cyclohexyl(or cycloheptyl)-3-alkoxycarbonylindole derivative: β-cyclodextrine 1:1 to 1:5, preferentially 1:1 to 1:3, especially preferentially in the relation of 1:2. The clathrate complex may represent nanoparticles of size not less than 100 nm. There are preferential clathrate complexes wherein 5-hydroxy-4-aminomethyl-1-cyclohexyl(or cycloheptyl)-3-alkoxycarbonylindole derivative represents 1-cyclohexyl-4-aminomethyl-5-hydroxy-2-methyl-1H-indole-3-carboxylic acid ethyl ester. The new clathrate complexes possess antiviral action and exhibit high activity versus influenza viruses. The invention also involves a pharmaceutical composition and a drug based on the clathrate complexes. Besides, the invention refers to liquid-phase and solid-phase synthesis of the clathrate complexes.

EFFECT: preparing the compounds which possess antiviral action and exhibit high activity versus influenza viruses.

20 cl, 2 ex, 2 tbl, 8 dwg

FIELD: chemistry.

SUBSTANCE: invention relates to a novel chemically stable antioxidant compound which contains a lipophilic cationic moiety linked by a linking moiety to an antioxidant molecule and an anionic component for said cationic moiety, where the antioxidant compound is a mitoquinone, selected from: 10-(6'-ubiquinone)propyltriphenylphosphonium, 10-(6'-ubiquinonyl)pentyltriphenylphosphonium, 10-(6'-ubiquinonyl)decyltriphenylphosphonium, and 10-(6'-ubiquinonyl)pentadecyltriphenylphosphonium, having general formula I: or quinol form thereof, where R1, R2 and R3 denote CH3, the C atom in (C)n is saturated and n equals 3, 5, 10 or 15, and Z denotes an anionic component which is selected from a group consisting of methanesulphonate and ethanesulphonate. The invention also relates to a pharmaceutical composition for reducing oxidative stress in a cell, containing said compound and optionally containing β-cyclodextrin, a method of reducing oxidative stress in a cell and a method of producing an antioxidant compound.

EFFECT: improved properties of compounds.

25 cl, 31 dwg, 13 tbl, 11 ex

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