Antibacterial pyrocatechols and related methods

FIELD: medicine, pharmaceutics.

SUBSTANCE: present invention refers to preparing a mouthwash containing water, a moisturiser in the amount of 5 wt % to 15 wt % and 0.01 wt % - 5 wt % of a compound presented by the structure (III), wherein R1 and R2 are independently specified in hydrogen atoms, C2-6 -alkenyl group and C1-6 - alkyl group; and the compound (III) is dissolved in ethanol.

EFFECT: invention involves a method for reducing bacterial population on the substrate by substrate contact with the composition containing the compound of the structure (IV), wherein R1 and R2 are independently specified in the substituted or unsubstituted methyl group, substituted or unsubstituted ethyl group and substituted or unsubstituted butyl group.

11 cl, 1 tbl, 5 ex

 

The prior art of the PRESENT INVENTION

Effective and safe antibacterial agents are important in the field of personal hygiene, especially to care for the oral cavity. The number of illnesses associated with the activity of bacteria in the mouth. Plaque, gingivitis, periodontitis and dental calculus are several known conditions associated with bacteria in the mouth.

For prevention or treatment of these painful conditions antibacterial agent is often administered in a composition for caring for the oral cavity. Report that often the data antibacterial agents have poor activity, for example, do not provide a steady decrease in the population of bacteria or metabolic products of bacteria, including compounds volatile sulfur ("VSC"). In some cases, otherwise, effective agents can be introduced into the composition due to factors such as limited solubility and, therefore, limited bioavailability, the positive charge (which limits the use in products for oral care mouth) and low levels of security.

A BRIEF DESCRIPTION of the PRESENT INVENTION

The present invention relates to a compound or composition for the care of the oral cavity, containing the compound represented by structure (I):

in which R3represents a hydrogen atom or represents a structure (II):

in which m represents an integer from 0 to 100, R is independently selected from a first hydrocarbon structure containing 1-50 carbon atoms, and R1and R2independently selected from a hydrogen atom and the second hydrocarbon structure containing 1-10 carbon atoms.

Also included are methods of using the compounds of structure (I), including a way to reduce the population of bacteria on the substrate including the contact of the substrate with the compound represented by structure (I).

Alternate the present invention relates to a method of maintaining and/or improving the overall health of a mammal, comprising the contact surface of the oral cavity of a mammal with a composition which contains a compound represented by structure (I).

DETAILED DESCRIPTION of the PRESENT INVENTION

As used in the present invention, the ranges are used as the legend for a description of all variables that are included in this range. Any value in this range can be selected as the boundary values of the range.

The present invention relates to the compound (I), which is represented by the structure:

in the cat the Roy R 3represented by structure (II):

The symbol "m" in the structure (I) represents an integer from 0 to 100, from 1 to 20, 1 to 15, or 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10. R may independently represent any hydrocarbon structure, known or developed in the art. It may be preferable that the hydrocarbon structure R had 1-50 carbon atoms, 1-20 carbon atoms or 1 to 10 carbon atoms. In addition, if desired, R may be an alkyl group, alkoxy group, alkinoos group, alkyne group, and/or alanovoy group.

The compound (I) contains R1and R2that represent independently a hydrogen atom or the second hydrocarbon structure containing 1-10 carbon atoms. R1and R2can be the same in each monomer of the compound (I), or they may be different. R1and R2can be independently selected from alkyl groups, alkoxy groups, alkinoos group, alkyne group and/or alanovoy group.

Hydrocarbon structure, any R, R1, R2and R3can independently represent a ring structure, chain structure, linear structure, a branched structure, or their combination. Any of the carbon atoms in the hydrocarbon structures R, R1, R2and R3and/or all of the compound (I) can be independently samestyle unsubstituted any functional group (or groups), known in the art. Methyl, ethyl, bucilina, hydroxy, alkyl and halogen groups may be preferred functional groups.

The present invention may include a compound of structure (III):

where R1and R2independently selected from a hydrogen atom, alkenylphenol group and alkyl group or structure (IV):

The compounds described above, can be synthesized by any suitable means or method of synthesis or, you can select or clear from natural sources. For example, the compound of the present invention can be obtained by simple acylation according to the Friedel-Crafts source pyrocatechol with subsequent restoration to obtain the desired final product.

The present invention includes a composition for caring for the oral cavity containing at least one of the compounds represented by the formulas above, and a suitable carrier. The media may include all the components of the oral composition, except for the active agent, such as, for example, inactivated ingredients, environment. The media may be or may contain water, glycerin, salt, copolymer polivinilovogo ether and maleic anhydride, propylene glycol, polyethylene glycol, chitosan, polymer/copoly the ' polyvinylformal acid, colloidal silicon dioxide, polymers, marine colloids, resins, acrylate polymers, cellulose polymers, starches, gelatin, oils, surfactants, substances that dissolve when hit in the mouth, textile substrates and fibers, and other excipients. The carrier may be in the form of a gel, liquid, paste, granules, tablets for sucking, chewing gum, chewy candy, foam and spray (aerosol or neurotologic) and solids.

The compound (III) of the present invention may be present in any amount in the composition for the care of the oral cavity. It may be desirable to its content ranged from about 0,001% by weight to about 10% by weight relative to the total weight of the composition for the care of the oral cavity, for example from 0.01% by weight to about 5% by weight or from about 0.1% by weight to about 2% by weight. The effective amount may vary depending on the oral composition. For example, in toothpaste, gels, teeth, dental elixirs, tablets for resorption and tooth powders, the effective amount may be at least about 0.01% by weight or at least about 0.05% by weight.

If desired, the connection or oral composition of the present invention m is should be applied to and/or to impregnate the unit to care for the oral cavity, such as a thread or floss, brush, element for cleaning soft tissue and/or language, capacitor, and/or orthodontic or prosthetic implants or elements.

In addition to antibacterial compounds a number of active ingredients and functional substances can enter into the composition for the care of the oral cavity. These substances include, but are not limited to, abrasives, moisturizers, surfactants, drugs that prevent the formation of concretions, thickeners, viscosity modifiers, antikrizni agents, flavouring agents, dyes, additional antimicrobial agents, antioxidants, anti-inflammatory components, etc. these substances can be added to the pastes, liquids for rinsing the mouth, resins, tablets for sucking, threads, and other forms of compositions for caring for the oral cavity according to known methods.

According to some variants of implementation, in which the media composition for the care of the oral cavity is a solid or paste, oral composition contains acceptable to the teeth with an abrasive substance, which is used for cleaning tooth enamel or provides whitening effect. Non-limiting examples include silicon abrasives, such as silica gel and precipitated silica. Commercial options for implementation on the given ZEODENT 115, marketed by J. M. Huber, Edison, N.J., United States of America and SYLODENTXWA, SYLODENT783 or SYLODENTXWA 650 Davison Chemical Division of W.R. Grace & Co., New York, N.Y., United States of America. Other suitable abrasives for teeth include, but are not limited to, metaphosphate sodium, metaphosphate potassium, tricalcium phosphate, digidrirovanny dicalcium phosphate, aluminum silicate, soda aluminum oxide, bentonite, or other substances containing silicon, or combinations thereof.

According to some variants of the implementation arrangement for the care of the oral cavity contains at least one wetting agent, suitable, for example, to prevent solidification of toothpaste under the action of air. You can use any orally acceptable wetting agent, including, but not limited to, polyhydric alcohols such as glycerin, sorbitol, xylitol and low molecular weight PEG. In some embodiments, the implementation of one or more humectants are present in a total amount from about 1% by weight to about 70% by weight, for example from about 1% by weight to about 50% by weight, from about 2% by weight to about 25% by weight, or from about 5% by weight to about 15% by weight.

Composition for the care of the oral cavity may also contain at least one surfactant. In some the options for implementation of the surfactant can provide increased stability, to facilitate cleaning of the tooth surface due to the cleansing properties and foam when mixing, for example, in the process of cleaning teeth brushed with a composition of the present invention. You can apply any orally acceptable surfactant, most of which are anionic, nonionic or amphoteric. Suitable anionic surfactants include, but are not limited to, water-soluble salts of C8-20of alkyl sulphates, sulfonated monoglycerides C8-20fatty acids, sarcosinate, taurate and the like. Illustrative examples of data and other classes may include sodium lauryl sulfate, coconut monoglyceride sodium, laurylsarcosine sodium, laurelsatin sodium, eurekabuild sodium and dodecylbenzenesulfonate sodium. Suitable nonionic surfactants may include, but not be limited to, poloxamer, polyoxyethylenesorbitan esters, ethoxylates fatty alcohol, apes, oxides of tertiary amines, tertiary phosphine oxides, diallylsulfide and the like. Suitable amphoteric surfactants may include, but not be limited to, derivatives of C8-20aliphatic secondary and tertiary amines containing an anionic group such as carboxylate, sulfate, sulfonate, phosphate or Fofana is. A suitable example is cocamidopropylbetaine. In some embodiments, the implementation of one or more surfactants present in a total amount from about 0.01% by weight to about 10% by weight; for example, from about 0.05% by weight to about 5% by weight; or from about 0.1% by weight to about 2% by weight. In another embodiment, the composition comprises orally

acceptable agent that prevents the formation of concretions. One or more data agents may be present in different variants of implementation. Suitable drugs that prevent the formation of concretions may include, but not be limited to, phosphates and polyphosphates (for example pyrophosphates), polyaminopropyl-acid (AMPS), citrate trihydrate zinc, polypeptides, such as poliasparaginovaya or polyglutamine acid, poly-olefin, the sulfonates, polyolefin phosphates, diphosphonates such as azacycloheptane-2,2-diphosphonates (e.g., azalmaga-tan-2,2-diphosphonic acid), N-methylethanolamine-2,3-divos-background acid, ethane-1-hydroxy-1,1-diphosphonic acid and ethane-1-amino-1,1-diphosphonate, phosphonocrotonate acid, and salts of any of these agents, for example, alkali metal salts and ammonium salts. Suitable inorganic phosphate and polyphosphate salts may include, for example, oneonone, dienone and trigonalnye phosphates of sodium, sodium tripolyphosphate (STPP), Tetra-polyphosphate, pyrophosphate, mono-, di-, tri - and tetranitride, dihydro-disodium pyrophosphate, trimetaphosphate sodium, sodium hexametaphosphate and sodium can not necessarily be replaced by potassium or ammonium, in some embodiments, implementation.

Composition for caring for the oral cavity of the present invention may contain polycarboxylate polymers. Polycarboxylate polymers may include polymers or copolymers of monomers containing carboxyl groups such as acrylic acid, methacrylic acid, and maleic acid or anhydride. Non-limiting examples may include

polivinilbutilovy ether/maleic anhydride (PVM.E/MA) copolymer, such as a polymer, available under the trademark GANTREZfrom ISP, Wayne, N.J., United States of America. Still other suitable agents that prevent the formation of concretions may include reagents, stabilizers, including hydroxycarbonate acids such as citric, fumaric, malic, glutaric, and oxalic acids and their salts, and aminopolycarboxylate acids such as ethylenediaminetetraacetic acid (EDTA).

In some embodiments, the implementation of the composition of the present invention contains at least one thickener. In some embodiments, implementing the tvline, the thickener can give the required degree of density and/or the degree of grinding composition for the care of the oral cavity. You can use any orally acceptable thickening agent, including, but not limited to, carbomer, also known as carboxyvinyl polymers, carrageenan, cellulosic polymers such as hydroxyethylcellulose, carboxymethylcellulose (CMC) and their salts, e.g., CMC sodium, natural resin, such as punish, xanthan gum, Arabic gum and tragakant, colloidal magnesium silicate-aluminum, colloidal silica and the like. In some embodiments, the implementation, one or more thickeners are present in a total amount from about 0.01% by weight to about 15% by weight; for example, from about 0.1% by weight to about 10% by weight; or from about 0.2% by weight to about 5% by weight.

According to some variants of the implementation arrangement for the care of the oral cavity contains at least one viscosity modifier. In some embodiments, the implementation, a viscosity modifier inhibits the precipitation or separation of ingredients or facilitate the distribution by shaking the liquid composition. You can use any orally acceptable viscosity modifier, including, but not limited to, mineral oil, petrolatum, clay and organo-modificirowan the e clay, the silicon oxide and the like. In some embodiments, the implementation, one or more viscosity modifiers are present in a total amount from about 0.01% by weight to about 10% by weight; such as from about 0.1% by weight to about 5% by weight.

In another embodiment, the composition comprises orally acceptable source of fluoride ions. In some embodiments, implementation, there is one or more sources. Suitable sources of fluoride ions include fluoride, monophosphate and fertilitate salt, and amine fluorides, including olaflur (N'-octadecyltrimethylammonium-N,N,N'-Tris(2-ethanol)dihydrofolic). Can fit any given salt, which is acceptable oral, including, but not limited to, salts of alkali metals (e.g. potassium, sodium), ammonium salts, salts of tin and indium, and the like. In some embodiments, implement, apply water-soluble salts which release fluoride ions. According to some variants of implementation, one or more salt, releasing fluoride ions present in an amount to provide a total amount of fluoride ions is equal to from about 100 ppm to about 20,000 parts per million; from about 200 ppm to about 5000 parts per million; or from about 500 parts is per million to about 2500 parts per million. In some embodiments, the implementation, in which sodium fluoride is the only source of fluoride ions, the composition for the care of the oral cavity contains from about 0.01% by weight to about 5% by weight; from about 0.05% by weight to about 1% by weight; or from about 0.1% by weight to about 0.5% by weight of sodium fluoride.

Other components may include, but not be limited to, flavoring agents, dyes, and other active ingredients such as antioxidants and anti-inflammatory agents. In some embodiments, implementation, these additional agents are administered in oral compositions according to known methods.

The present invention includes methods of reducing, eliminating or preventing the reproduction of a population of bacteria on the substrate, including gram-negative, gram-positive, and/or a mixture of both. The method includes contact any of the compounds and/or compositions of the present invention with the selected substrate. The duration of contact can be short (from a few seconds up to several hours) or the substrate can be coated, impregnated or otherwise on the substrate can be attached to the compound or composition of the present invention. The substrate can be any in the art, including plastic, polymeric resins, films, metals, fibers, textiles, wood, paper, porcelain or ceramics. The substrate may be the whole or part of any device, tool, equipment or device with which you want to control the population of bacteria, including, for example, clothing such as disposable diapers, underwear, footwear, medical devices, surgical instruments, medical implants, stationery, bags for diapers, feminine products, toilet accessories, tableware, cooking appliances, trash bin, pipes, doors, handsets, computer keyboards, railings, floors, operating surfaces, hard surfaces, equipment for animals, such as carrying, toys and litter tray; the surface of the kitchen and bathroom, wall, money, laboratory equipment, and/or eye and dental equipment, devices, implants, and tools, such as contact lenses, false teeth and glasses; and epidermal and epithelial surfaces. In the mouth the substrate can be peliculas, enamel and/or oral epithelium.

The present invention also includes methods of maintaining and/or improving the General health of the mammal. These methods include the contact surface of the oral cavity (such as detinova, amalina, gingival, epithelial, pellicularia surface) with a composition or compound (I) in the present invention.

Example 1

Received a sample solution for rinsing the mouth, in which the selected compound (I), where m=0, R represents an allyl group, and R1and R2represent hydrogen atoms, was dissolved in ethanol and then was the composition as shown in table 1.

Example 2

The corresponding placebo formula of example 1 was obtained according to the composition as shown in table 1 below.

Example 3

Received a sample solution for rinsing the mouth, in which the selected compound (I), where m=1, R represents an allyl group, and R1and R2represent hydrogen atoms (compound III), was dissolved E ethanol and then was the composition as shown in table 1.

Example 4

Received a sample solution for rinsing the mouth, in which the selected compound (I), where m=1, R represents boutelou group, and R1and R2represent hydrogen atoms (compound IV), was dissolved in ethanol and then was the composition as shown in table 1.

Example 5

The corresponding placebo formula of example 3 was obtained according to the composition as shown in table 1 below.

Table 1:
An example of the composition of the solution for mouthwash
Ingr dient Example 1Example 2Example 3Example 4Example 5
water81,7349%81,7849%81,7349%81,7349%81,7849%
ethanol1010101010
glycerin88888
PEG-40 sorbitan0,1250,1250,1250,1250,125
diisostearate
Aromatic0,080,0,0800,0800,0800,08
additive
Saccharin sodium0,0100,0100,0100,0100,010
Dye, 1%0,00010,00010,00010,00010,0001
solution
The compound (I)0,05%0,00%0,05%0,05%0,00%
Total100%100%100%100%100%
number

The compositions of examples 1, 3, 4, and 2, 5 used for in vitro studies on the ability to reduce bad breath. Each composition was made in the oral environment containing the VSC. The solution for rinsing the oral cavity, containing 0.03% TCN also made in the oral environment containing the VSC.

The percentage reduction in VSC in the oral environment was measured for each composition. In this case, any reduction in unpleasant mouth odor, as expected, is the result of excellent antibacterial activity, especially against gram-negative bacteria such asF. nucleatumand P. melnngenica,which, as is well known, synthesize VSC in the presence of amino acids containing sulfur. A very strong influence on the breath demonstrate the compositions of examples 1, 3, 4.

1. Composition for the preparation of an agent intended for rinsing of the mouth containing water, humectant in an amount of 5 to 15 wt.% and 0.01-5 wt%. compounds represented by structure (III)

in which R1and R2independently selected from hydrogen, C2-6-alkenylphenol group and C1-6is an alkyl group; and the compound (III) dissolved in ethanol.

2. The composition according to claim 1, where the compound of structure (III) is a structure (IV)

3. The composition according to claim 1, where R1and R2n is dependent selected from substituted or unsubstituted metal group, substituted or unsubstituted ethyl group, and a substituted or unsubstituted butilkoi group.

4. The composition according to claim 1, in which the compound (III) is present in an amount of 0.01-2% by weight.

5. The composition according to claim 1, additionally containing an orally acceptable carrier selected from a gel, liquid, powder, a substance that dissolves upon contact with the oral environment, the textile substrate, fibers and paste.

6. The composition according to claim 1, additionally containing an agent selected from a copolymer polivinilovogo ether and maleic anhydride, propylene glycol, polyethylene glycol, chitosan, polymer/copolymers polyvinylformal acid.

7. The way to reduce the population of bacteria on the substrate including the contact of the substrate with a composition according to claim 1.

8. The method according to claim 7, comprising the contacting of the substrate with a compound of structure (IV)

9. The method according to claim 7, where R1and R2independently selected from substituted or unsubstituted metal group, substituted or unsubstituted ethyl group, and a substituted or unsubstituted butilkoi group.

10. The composition according to claim 1, which additionally contains as a humectant glycerin.

11. The composition according to claim 2, which further comprises sorbitan diisostearate PEG-40, flavor, saccharin sodium and dye.



 

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FIELD: medicine.

SUBSTANCE: intratympanic composition used for treating an ear disease contains: (a) an antimicrobial agent consisting of a number of particles; and (b) a polyoxyethylene and polyoxypropylene copolymer; the composition (i) is a liquid at room temperature; (ii) has a gelling point within the range of 19C to 42C; (iii) has a gel viscosity of 15000 sP to 1000000 sP; (iv) has an osmolarity less than 1000 mOsm/l; and the intratympanic composition release the antimicrobial agent in an ear for at least 5 days, and it is introduced at room temperature.

EFFECT: effective treatment of the ear diseases; the composition is non-toxic and has a non-irritating effect on the ear structures, provides the permanent prolonged release of the active agent with a reduced dose rate and reduces the risk of a potential tympanum damage.

13 cl, 9 tbl, 5 dwg, 30 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to indolyl-substituted derivatives of thiadiazinones prepared from oxamic acid thiohydrazide of general formula: , wherein R represents H; R1 represents pyridinyl; phenyl substituted by alkyl C1-C5, Hal, CF3; R2 represents H; alkyl C1-C5; -CH2COOR4; benzyl substituted by Hal, OR4; benzoyl substituted by Hal, OR4, while R4 represents unsubstituted alkyl C1-C4.

EFFECT: there are prepared new compound which can find application in medicine for developing the therapeutic agent possessing pathogenic bacteria inhibitory activity.

2 cl, 2 dwg, 2 tbl, 13 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to pharmaceutical industry and represents an antibacterial composition of chitosan and a gel former, containing polyvinyl alcohol, and/or glycerol, and/or polyethylene glycol and/or polyvinyl pyrrolidone, differing by the fact that the antibacterial agent is presented by low-molecular water-soluble chitosan of molecular weight 3.5 to 4.9 kDa in the amount of 0.01 to 10 wt %; the gel former is polyvinyl alcohol 2 to 15 wt %, and/or glycerol 10 to 90 wt %, and/or polyethylene glycol 1 to 20 wt %, and/or polyvinyl pyrrolidone 10 to 50 wt %; water is the rest.

EFFECT: invention provides high solubility and antibacterial activity of chitosan in the wide range of the medium acidity.

5 ex, 4 tbl, 3 dwg

FIELD: medicine, pharmaceutics.

SUBSTANCE: group of inventions refers to medicine and is used to preparing the cell cultures of Lactobacillus reuteri, containing reuterin to be kept inside the cells. The method involves the fermentation of cell cultures, the addition of 1,2-propanediol or glycerol to the reuterin-producing cell systems Lactobacillus reuteri in the beginning of the fermentation, the addition of glycerol to the cell cultures of Lactobacillus reuteri during the production and preservation of the cells Lactobacillus reuteri. The product prepared by the declared method contains the kept cells Lactobacillus reuteri with reuterin kept in the cells.

EFFECT: group of inventions allows producing the large amounts of reutrin-loaded Lactobacillus reuteri to be used for the purpose of both preventing and treating diseases, and as a food additive.

9 cl, 9 dwg, 5 ex

FIELD: chemistry.

SUBSTANCE: present invention relates to a polymyxin derivative having a total of three positive charges at physiological pH and where the terminal moiety (D) of the derivative contains a total of 1-5 carbon atoms; a method for production thereof; a composite product containing at least two such derivatives; a pharmaceutical composition containing a polymyxin derivative; a method of sensitising gram-negative bacteria to an antibacterial agent; a method of producing novel antibiotics.

EFFECT: invention also relates to use of the polymyxin derivative in producing a medicine for sensitising gram-negative bacteria to antibacterial agents.

23 cl, 8 tbl, 8 ex

FIELD: medicine.

SUBSTANCE: invention refers to veterinary science, particularly biotechnology. The method for prevention of cattle is as follows: A protective Brucella antigen complex in a dose of 5 to 10 mg dissolved in 5 ml 0.9% sodium chloride is administered to the animals. The animals are re-immunised 10 months later with detecting the latent infection on the 15th and 180th days, and finding the adult non-responsive and immune deficient animals by the agglutination reaction on the 15th day with a 5 IU titer. The immunisation is combined with animal's blood sampling and brucellosis analysis. Using the Brucella antigen complex in a dose of 5-10 mg in the presented method for prevention of cattle brucellosis contributes to the protection against brucellosis using commercial vaccines, identifies the latently infected animals, provides an ability to test a specific immune status, increases the efficacy of diagnostic and veterinary-sanitary measures and eliminates the potential risk for live vaccines.

EFFECT: combined immunisation and blood sampling for brucellosis analysis can reduce the period of the non-immune state of the body, reduces the effects of stress factors on food-producing animals and increases the cost-effectiveness of specific interventions.

4 tbl, 1 ex

FIELD: medicine.

SUBSTANCE: invention refers to microbiology and veterinary science and aims at treating experimental malleus. Golden hamsters that are animals highly malleus-sensitive, are infected with B.mallei c 5 in dose 104 microbial cells that corresponds to 103 Dim. The treatment starts either 4 hours later and represents an emergency prevention, or 24 h and 48 h later. An antibacterial agent is presented by meropenem in the liposomal form 15 mg in 0.5 ml, in dose 50 mg/kg/day; the preparation is administered intraperitoneally 5 times every 72 hours.

EFFECT: using the method improves the survival rates in animals suffering acute malleus.

2 cl, 2 ex, 2 tbl

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