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Compositions for treating and preventing oral infections

Compositions for treating and preventing oral infections
IPC classes for russian patent Compositions for treating and preventing oral infections (RU 2504378):
A61P15/02 - for disorders of the vagina
A61K36/185 - PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J0003000000; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L)
A61K31/473 -
A61K31/343 -
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FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to a composition for oral hygiene and for treating and preventing pathological conditions related to the dentofacial system, implants and complications following the oral surgeries. The above composition contains benzophenanthridine alkaloids, benzofuran compounds and catechine polyphenols.

EFFECT: composition possesses antibacterial, antifungal and antienzymic activity that exceeds total activities of the different ingredients if used separately.

14 cl, 2 tbl, 1 ex

 

SUMMARY of the INVENTION

The present invention relates to compositions containing benzophenantridin alkaloids, compounds benzofuran and catechin polyphenols, which are useful for the treatment and prevention of infections of the oral cavity.

The compositions of the present invention have antibacterial, antifungal and antitermination activities, which are useful for oral hygiene and for the treatment and prevention of pathological conditions of different origin, associated with dentofacial system, implants and complications after surgery of the oral cavity.

These compositions can be introduced in the form of tablets that dissolve slowly in the mouth, or in the form of a liquid mouthwash or chewing gum.

PRIOR art

The formation of bacterial or fungal films in the mouth very often gives rise to such disorders as caries, Peoria and periodontal and gingival infections. In particular, the formation of bacterial or fungal films is very common in implantology, when the denture care, as well as in elderly dental patients in General.

In the literature it was reported that benzophenantridin alkaloids possess antibacterial and antifungal activity, in cast the STI against gram-positive bacteria, and can destroy the bacterial film and, thus, to do the pathogen is sensitive to inhibitory compounds or antibiotics.

It is also known that compounds benzofuran with Polignano structure inhibit the formation of bacterial or fungal films or destroy already formed film, thereby preventing their re-education; such compounds detected in extracts of Krameria triandra, Eupomatia laurina and Piper sp, in particular automatisoida and 2-(2',4'-dihydroxyphenyl)-5-propenylbenzene.

Enzymes, such as α-amylase, glucosidase and takadiastase present in the oral cavity, assist in the breakdown of carbohydrates; however, this leads to the formation of glucose, which adversely affects the oral health because it promotes the formation of bacterial films in the oral cavity. Therefore, inhibitors of these enzymes help to prevent formation of bacterial films.

Procyanidins, in particular, oligomers of catechin, etherified Gallic acid are inhibitors of glucosidase and takadiastase.

Polyphenols extracted from Vitis vinifera, are powerful inhibitors of α-amylase and glucosidase.

Description of the INVENTION

The present invention relates to compositions containing:

a) benzophenantridin alkaloids;

b) connection benzofuro is a; and

c) the polyphenols catechin with antibacterial, antifungal and antitermination activities that reduce the formation of bacterial and fungal films in the oral cavity, thus reducing halitosis and the formation of plaque.

Preferred benzophenantridin alkaloids are chelerythrine and sanguinarine, and the preferred compounds of benzofuran are connected to Polignano structure detected in extracts of Krameria triandra, Eupomatia laurina and Piper sp, in particular, automatisoida and 2-(2',4'-dihydroxyphenyl)-5-propenylbenzene.

According to the invention compounds of benzofuran have the following formula

where R can represent hydrogen or alkyl linear or branched chain containing from 2 to 6 carbon atoms, or alkyl substituted amino group, a nitro-group, R preferably represents hydrogen or C1-C3alkyl.

These compounds benzofuran known and can be obtained by standard methods, for example by reaction of phenol, which is appropriately substituted with obtaining 2-phenoxy-2',4'-dimethoxyacetophenone in conditions that are described in Chimie Therapeutique 1973, 8, 398, followed by cyclization in the presence of polyphosphoric acid in xylene and hydrolysis of methoxy - and hydroxy groups.

N is the expected detected the composition according to the invention have very strong antibacterial, antifungal and antitermination activity that exceeds the sum of the activities of the various components at their separate introduction. This effect may occur due to the synergistic mechanism of action, which occurs between the various components of the considered complex.

Therefore, the composition of the invention can be used for oral hygiene and for the treatment and prevention of pathological conditions of different origin that are associated with dental system, dental implants and complications after surgery of the oral cavity.

More specifically, the present invention relates to compositions containing:

a) benzophenantridin alkaloids, selected from sanguinarine and/or chelerythrine and/or derivatives thereof;

b) compounds of benzofuran as defined above;

c) a Monomeric or oligomeric catechin polyphenols.

The contents of the various components in the compositions according to the invention will be within the following limits by weight in a single dose):

a) benzophenantridin alkaloids: from 0.5 mg to 10 mg;

b) benzofuran: from 5 to 25 mg;

c) compounds of polyphenols: from 10 to 100 mg.

In a particularly preferred aspect of the content of various components to the positions will be located in the following intervals (by weight in a single dose):

a) benzophenantridin alkaloids: 2.5 to 5 mg;

b) compounds of benzofuran: from 3 to 10 mg;

c) compounds of polyphenols: from 40 to 50 mg

Benzophenantridin alkaloids sanguinarine and chelerythrine may be present in free form or in salt form, as such, essentially in pure form or in the form of extracts of Sanguinaria canadensis, Macleaya cordata or Macleaya macrocarpa. In a preferred aspect benzophenantridin alkaloids will be present in salt form luteal acid. It is proved that these salts obtained by reaction of sulphates and chlorides of alkaloids with sodium or potassium salt luteal acid and crystallization, is particularly effective to achieve the objectives of the present invention.

The above compounds with benzofuranol structure may be present as such or in the form of the containing extracts, such as extracts of Krameria triandra, Eupomatia laurina and Piper sp. Proven especially active compounds isolated from Krameria triandra are automationid 6 and realigning 2-(2,4-dihydroxyphenyl)-5-(E)-propenylbenzene, which showed antibacterial and antifungal activity against many strains of gram-positive bacteria, fungi and anaerobic bacteria.

Compounds of polyphenols may be present in the form of Monomeric units, such as ka is Ehin, epicatechin and gallocatechin, and their esters of Gallic acid on C3the hydroxyl or oligomeric units, preferably of up to five units. In a particularly preferred aspect, the oligomeric units will be tarifitsirovana Gallic acid C3. Compounds of polyphenols may also be present in the form of extracts from seeds or aerial parts Vitis vinifera, Aesculus hippocastanum, Camellia sinensis, Theobroma cacao, etc. These compounds is particularly indicated for oral hygiene, halitosis and gum infections.

The composition of the invention can be conveniently prepared in the form of a melt in the mouth tablets, liquids for mouth rinses, gels for application to the oral cavity, chewing gum, etc. These compounds may be obtained in accordance with well known standard methods, such as those described in "Remington''s Pharmaceutical Handbook", Mack Publishing Co., N. Y., USA, together with suitable excipients.

The compositions according to the invention is administered to patients up to 5 times in 24 hours for several days, depending on how the disorder to be treated. Only for oral hygiene number of techniques can be reduced to 2 after the main meals.

The following examples illustrate the invention without limiting its scope.

Example 1 - Getting connection benzofuran

Stage A. Obtaining 2-phenoxy-2',4'-DIMET is xecution (a)

A solution of 2-bromo-2',4'-dimethoxyacetophenone (5 g, of 19.1 mmol) in 25 ml of 2-butanone was added to a suspension of phenol (1.8 g, 19,1 mmol), K2CO3(2.6 g, 19,1 mmol) and KI (of 41.5 mg, 0.25 mmol) to 20.0 ml of the same solvent. Then the solution was boiled under reflux for 20 hours. The mixture was filtered and the solvent evaporated under vacuum. The obtained residue was dissolved in EtOAc and washed with 10% aqueous NaOH solution and then with water. The organic extract was dried over Na2SO4, filtered and evaporated under vacuum. In the end, the crude residue was washed Et2O and dried under reduced pressure to obtain 4.4 g (yield: 84%) specified in the connection header.

Stage B. Obtaining 2-(2',4'-acid)benzofuran (b)

12 g of polyphosphoric acid was added to a solution of compound obtained in stage A (4.4 g, 16.2 mmol) in 130,0 ml of xylene. The mixture was boiled under reflux for 2 hours and then left to cool at room temperature. Then the solution decantation and evaporated under reduced pressure. The obtained residue (3.7 g, yield: 90%) was used in the next stage without additional purification.

Stage C. Obtain (2',4'-dihydroxyphenyl)benzofuran (1)

The mixture of compounds obtained in stage B (3.7 g, 14.5 mmol), and pyridine hydrochloride (11.1 g, 96,4 mmol) was heated to 225°C for 45 minutes. The resulting CR is sny product was poured into 10% HCl. The mixture was washed several times EtOAc; the combined organic layers were dried over Na2SO4and evaporated. To highlight, the residue was purified column chromatography (hexane/EtOAc=7:3). After crystallization from benzene yield the final compound was 41% (1,36 g).

Example composition 1 - Melt in the mouth tablets

Benzophenantridin alkaloid 2.5 mg
Connection benzofuran 10.0 mg
The extract of Vitis vinifera 50.0 mg
Xylitol 500.0 mg

Mannitol 400,0 mg
Licorice flavoring 50.0 mg
Magnesium stearate 10.0 mg
Acesulfame K 5.0 mg

Example of composition of 2 - Gel for mouth

Benzophenantridin alkaloid 3.0 mg
Connection benzo is uranium 10.0 mg
Extract Camellia sinensis 50.0 mg
Glycerin 400,0 mg
Liquid sorbitol 200.0 mg
Hydroxyethylcellulose 30.0 mg
Mint flavor 20.0 mg
Methyl parahydroxybenzoate 10,mg
Acesulfame K 5.0 mg
Purified water in sufficient quantity to 2.0 g

1. The composition for oral hygiene and for the treatment and prevention of pathological conditions associated with dental system, dental implants complications after surgery of the oral cavity that contains:
a) benzophenantridin alkaloids
b) compounds of benzofuran formula

where R can represent hydrogen or alkyl linear or branched chain containing from 2 to 6 carbon atoms, or alkyl substituted amino group, a nitro-group;
c) catechin polyphenols.

2. The composition according to claim 1, which contains:
a) endophenotyping alkaloids, selected from sanguinarine or chelerythrine, and/or derivatives thereof;
b) compounds of benzofuran as specified in claim 1, or containing extracts;
c) a Monomeric or oligomeric catechin polyphenols.

3. The composition according to claim 1, where the content of the various components within the following intervals (by weight in a single dose):
a) benzophenantridin alkaloids: from 0.5 mg to 10 mg;
b) compounds of benzofuran: from 5 to 25 mg;
c) compounds of polyphenols: from 10 to 100 mg.

4. The composition according to claim 2, where the contents of the various components within the following intervals (by weight in a single dose):
a) benzophenantridin alkaloids: from 0.5 to 10 mg;
b) compounds of benzofuran: from 5 to 25 mg;
c) compounds of polyphenols: from 10 to 100 mg.

5. The composition according to claim 3, where the content of the various components within the following intervals (by weight in a single dose):
a) benzophenantridin alkaloids: 2.5 to 5 mg;
b) compounds of benzofuran: from 3 to 10 mg;
c) compounds of polyphenols: from 40 to 50 mg

6. The composition according to claim 4, where the contents of the various components within the following intervals (by weight in a single dose):
a) benzophenantridin alkaloids: 2.5 to 5 mg;
b) compounds of benzofuran: from 3 to 10 mg;
c) compounds of polyphenols: from 40 to 50 mg

7. Composition according to any one of the preceding paragraphs, where benzophenantridin alkaloid is sanguinarine and chelerythrine are present in free form or in salt form, as such, essentially, in pure form or in the form of extracts of Sanguinaria canadensis, Macleaya cordata or Macleaya macrocarpa.

8. The composition according to claim 7, where benzophenantridin alkaloids are present in salt form luteal acid.

9. The composition according to claims 1 to 6, where connections benzofuran present as such or in the form of the containing extracts.

10. The composition according to claim 9, where the connection benzofuran are present in the form of extracts of Krameria triandra, Eupomatia laurina and Piper sp.

11. Composition according to claims 1-6, where the connection of the polyphenols present in the form of Monomeric units, such as catechin, epicatechin and gallocatechin, and their complex Gallic esters of C3the hydroxyl or oligomeric units.

12. The composition according to claim 9, where the connection of the polyphenols present in the form of extracts of the seeds and aerial parts of Vitis vinifera, Aesculus hippocastanum, Camellia sinensis, or Theobroma cacao.

13. The composition according to claim 1 in the form of a melt in the mouth tablets, liquids for mouth rinses, gels for application to the oral cavity, chewing gum.

14. Application:
a) benzophenantridin alkaloids;
b) 2-(2,4-dihydroxyphenyl)-5-propenylbenzene; and
c) polyphenols catechin;
to obtain oral compositions for oral hygiene and for the treatment and prevention of pathological conditions associated with dental system, dental implants complications after surgery cavity RT is.

 

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