Method of obtaining sanguinarine and chelerythrine sulphates

FIELD: chemistry.

SUBSTANCE: method of obtaining sanguinarine and chelerythrine sulphates includes extraction of milled overground part of macleaya microcarpa and/or macleaya cordata with water aliphatic alcohol, removal of water aliphatic alcohol in vacuum, alkalinisation of water distillation residue with hydrophobic solvent, processing organic phase with sulphuric acid, filtration, washing and drying of target product, with extraction of milled raw material being carried out with water aliphatic alcohol in presence of methanesulphoacid, and solution of alkaloid bases in hydrophobic organic solvent is additionally filtered through layer of hydrophobic solvent, and target product is subjected to boiling in acetone.

EFFECT: method makes it possible to increase quality of finished product, simplify technology of production of sanguinarine and chelerythrine sulphates, and reduce the process duration.

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The invention relates to chemical-pharmaceutical industry, namely to methods for sulfates sanguinarine and chelerythrine from vegetable raw materials. Target product refers to drugs of plant origin that have antimicrobial activity, and was named sangviritrin.

Sangviritrin is a mixture of acidic sulfates two benzo[C]phenanthridine alkaloids sanguinarine and chelerythrine.

Known methods for producing these alkaloids from various herbal remedies containing benzo[C]phenanthridinium alkaloids, for example Sanguinariacana-densis[Log PlantPhysiol. 1939, 14(2): 377-380. GlennA. Greathouse "Alkaloids from sanguinaria canadensis and their influence on growth of phymatotric humomnivorum"].

A method of obtaining sanguinarine of the terrestrial part of Maclay cordate (Macleayacordata), Maclay small (Macleayamicrocarpa), consisting in the extraction of the crushed raw material is treated with hydroxide ammonium, dichloroethane, filtration, subsequent processing of the extract diluted sulfuric acid, the separation of the fallen bisulfate alkaloids and recrystallization from acidified alcohol (Patent RF № 571268, IPC AC 35/78, from 29.08.1975).

However, this approach involves the use of aggressive aqueous solution of ammonia, and is very toxic and environmentally hazardous dichloroethane.

Known SP is a way to get sanguinarine, in which powdered aerial part of Maclay small-fruited or Maklai heart is extracted with a hydrophobic solvent in the presence of an alkaline agent, beset bisulfate target alkaloids, carry out a cleaning mixture of salts of alkaloids processing filtered and padmalochan aqueous solution with an organic solvent followed by treatment of the organic phase with an aqueous solution of sulfuric acid. As extractant at the stage of solid-phase extraction using ethyl acetate or dichloromethane, the extraction was carried out by the sequential processing of multiple servings of raw materials one volume of the extractant on the counterflow principle. When cleaning as the alkaline agent in the extraction step using an aqueous solution of ammonia or potash, as a solvent is ethyl acetate or toluene. Extraction schittko carried out at 50-60ºC with a speed that prevents the formation of sludge target alkaloids. The extract obtained was filtered, washed with water and treated with a solution of sulfuric acid. Separate the precipitate by filtration and wash it with acetone (RF Patent No. 2141837, IPC AC 35/78, 19.05.1997).

However, this method is characterized by complexity and multi-stage. In addition, when used as a solvent of ethyl acetate required alkaline hydrolysis and difficult regeneration. Using dichloroethane as in the previous analogue not always justified due to its toxicity and aggression to the environment.

The closest to the problem at hand and the technical nature of the claimed is the method of receiving sanguinarine (RF Patent No. 2089212, IPC A61K 35/78, from 06.10.1995), in which the crushed grass, Maclay small-fruited, Maclay cordate extracted with aqueous aliphatic alcohol in the presence of hydroxide ammonium, remove the alcohol in vacuo, treated with an aqueous phase of a hydrophobic solvent, such as dichloroethane, methylene chloride, toluene, ethyl acetate, treated organic phase is diluted with sulfuric acid, separating technical sangviritrin. Next dissolve technical sangviritrin in water, filtered, alkalinized by hydroxide of ammonia, extracted with a hydrophobic solvent used in the previous phase, the organic phase is washed with water, then precipitated target product by dilute sulfuric acid, separating the target product by filtration, washed it with acetone and dried. The content of the target alkaloids in the technical product is 91-97%, after purification increases to 96.5-99%, respectively. This method is characterized by multi-stage and, as a consequence, high complexity, power consumption and does not meet the requirements of ecology, involve the use of current the ranks of the reactants.

Objective of the claimed invention to provide a novel method of producing sulfates sanguinarine and chelerythrine, allowing to simplify the technological process, while improving the quality of the finished product, reducing the consumption of toxic reagents and reducing the number of non-regenerating waste.

Technical result - improving technology and environmentally friendly method of producing sulfates sanguinarine and chelerythrine. This is achieved by improving the quality of the finished product, by minimizing the extraction of by-products.

The problem is solved in that in the method of producing sulfates sanguinarine and chelerythrine, including extraction of powdered aerial parts of Maclay small-fruited and/or Maklai cordate aqueous aliphatic alcohol, removing the aqueous aliphatic alcohol in a vacuum, alkalization of water VAT residue, extraction of water VAT residue hydrophobic solvent, the processing of the organic phase with sulfuric acid, filtering, washing and drying of the target product, the extraction of the crushed material spend aqueous aliphatic alcohol in the presence of methansulfonate, and the solution of the grounds of alkaloids in the hydrophobic organic solvent is additionally filtered through a layer of hydrophilic sorbent, while the target PR the product is subjected to boiling in acetone.

Appropriate treatment with sulfuric acid is carried out in a solution of concentrated sulfuric acid in ethyl acetate.

Optimal extraction administered in two consecutive stages lasting no more than 3 hours.

Preferably as an aqueous aliphatic alcohol use 80% aqueous ethanol.

Suitable as the organic solvent to use methylene chloride or chloroform, or ethyl acetate, or dichloromethane, or toluene. As the hydrophobic organic solvent can be used and others not miscible with water and organic solvents such as thinners, benzene, or four-chloride carbon or trichloroethylene, or butyl acetate, or disutility ether, or tetrachlorethylene.

Optimally alkalization of water VAT residue to conduct an alkaline reagent, for example, hydroxide, or carbonate, or bicarbonate of sodium or potassium.

Preferably as a sorbent to use alumina or silica gel.

Suitable target product is washed with an organic solvent used at the stage of liquid-phase extraction.

The way to declare the distinguishing characteristics in the analysis of patent and scientific literature is not found.

The use of the new system of the extractant on the head stage technology - water-Ali is adicheskogo alcohol in the presence of methansulfonate - allows you to achieve a higher degree of extraction of the target alkaloids in less time. The use of acidic extractant on the basis of the aqueous aliphatic alcohol with the addition of methansulfonate minimizes the extraction of by-products (such as chlorophyll, resin and so on), which greatly facilitates the selection of the target product, due to the fact that methansulfonate target alkaloids possess sufficient solubility. This consequently reduces the time required for extraction. So, instead of 4 extraction for 2 hours (as in the prototype), the extraction process can be carried out in two stages lasting no more than 3 hours.

Introduction in the process of obtaining sulfates sanguinarine and chelerythrine stage purification by passing the solution of the grounds of alkaloids in an organic solvent through a layer of hydrophilic sorbent allows for significant simplification of the further production process and to improve the quality of the finished product. High purity of the final product is ensured primarily by the fact that all impurities more polar than the target alkaloids, held hydrophilic sorbent and did not go into solution during the filtration through a bed of sorbent, for example, aluminum oxide or silica gel. Filtration through a layer of sorbent is from homogeneous solution in an organic solvent,which significantly facilitates the process due to significantly lower the viscosity of the solution. In addition, upon acidification of the grounds of alkaloids in an organic solvent, and subsequent boiling in acetone, filtered precipitate of a mixture of sulfates of alkaloids are separated Malopolskie impurities. The selection in the inventive process of the desired product of high purity, bypassing the stage of isolation of the intermediate product technical quality significantly reduces the number of process steps and, as a consequence, the total duration of the process.

The method of producing sulfates sanguinarine and chelerythrine implemented as follows.

Crushed grass, Maclay heart-shaped and/or Maklai small-fruited extracted with aqueous aliphatic alcohol, for example ethanol, or methanol, or propanol, or isopropanol, or butanol in the presence of methansulfonate (2 times in 3 hours). This is followed by evaporation of the ethanol from the water-alcohol extract under reduced pressure and the bath temperature not exceeding 50°C, alkalization of water VAT residue with an alkaline reagent, for example, hydroxide, or carbonate, or bicarbonate of sodium or potassium. Extraction of bases of the target alkaloids produced by treatment with an organic solvent, for example methylene chloride, or chloroform, or ethyl acetate, or dichloromethane, or toluene. As the hydrophobic organic solvent can IP altoviti and others, not miscible with water and organic solvents such as thinners, benzene, or carbon tetrachloride or trichloroethylene, or butyl acetate, or disutility ether, or tetrachlorethylene. The next stage combined extracts are passed through a layer of hydrophilic adsorbent, such as silica gel or alumina. Then the resulting solution is acidified with a solution of concentrated sulfuric acid in an organic solvent. The precipitation was filtered, washed with a hydrophobic organic solvent used at the stage of liquid-phase extraction, then acetone, and dried. The residue is boiled in acetone, filtered, washed in acetone, filtered and dried.

The implementation of the method is confirmed by the following examples.

Example 1. Crushed grass, Maclay (50.0 g) is poured into a glass flask was prepared a solution of 2 ml of methansulfonate in 500 ml of 80% aqueous ethanol and the extraction is carried out for 3 h at room temperature, under stirring by a mechanical stirrer. The first extract is drained, pour raw materials in the same extractant in the merged volume of the extract (approximately 500 ml) and extracted as in the first case. The extracts are evaporated under reduced pressure and the bath temperature not exceeding 50°C to a minimum volume (about 100 ml). VAT residue alkalinized saturated water is the first solution of sodium bicarbonate to pH 9, transferred into a separating funnel and treated with methylene chloride 3 times 120 ml 2 x 30 ml), the combined extracts are passed through a layer of aluminum oxide by gravity. Washed sorbent additional 30 ml of methylene chloride. The combined eluent is acidified with vigorous stirring a solution of 0.15 ml of concentrated sulfuric acid in 1.5 ml of ethyl acetate. Loose orange precipitate is stirred for 15 minutes at room temperature and filtered on a Buechner funnel.

The filter cake was washed with methylene chloride (2×5 ml) and then acetone (5 ml), and dried on the filter. Then the precipitate is transferred into odnogolosy flask of 20 ml, add 10 ml of acetone and refluxed under stirring for 20 minutes. The hot suspension is filtered on a Buechner funnel and washed with acetone (10 ml). Received light orange substance dried on the filter, and then in a drying Cabinet at 60°C to constant weight (~2 hours). Obtain 0.64 g (yield of 1.28% in the calculation of the original dry plant material) of the desired product purity of 99.2%.

Example 2. Spend the extraction of raw materials, as described in example 1. Time 1 and 2 extraction for 3 hours as hydrophobic extractant reason alkaloids used dichloroethane. The number of liquid-phase extraction three. Obtain 0.51 g (yield of 1.02% (based on the original dry plant material) of the desired product purity 99,0%.

Example 3. The extraction is carried out as described in example 1. Time 1 and 2 extraction for 3 hours as hydrophobic extractant reason alkaloids using ethyl acetate. Gain of 0.62 g (yield of 1.24% in the calculation of the original dry plant material) of the desired product purity of 99.1%.

Example 4. The extraction is carried out as described in example 1. Time 1 and 2 extraction for 3 hours as hydrophobic extractant reason alkaloids using toluene. Obtain 0.35 g (yield 0.70% based on the original dry plant material) of the desired product purity 99,0%.

Example 5. The extraction is carried out as described in example 1. Time 1 and 2 extraction for 3 hours as hydrophobic extractant reason alkaloids using chloroform. As the sorbent using silica gel. Get to 0.60 g (yield of 1.20% (based on the original dry plant material) of the desired product purity of 99.1%

Example 6. The extraction is carried out as described in example 1. Time 1 and 2 extraction for 3 hours as hydrophobic extractant reason alkaloids using ethyl acetate. As the sorbent using silica gel. Gain of 0.58 g (yield of 1.16% (based on the original dry plant material) of the desired product purity of 99.5%.

Example 7. Spend the extraction of raw materials, as described in example 1, except that a charge of 100 g of dry raw materials, and for extraction using 1000 ml of 80% is canola, containing 4 ml of methansulfonate. Time 1 and 2 extraction for 3 hours as hydrophobic extractant reason alkaloids using methylene chloride. Gain of 1.30 g (yield of 1.30% (based on the original dry plant material) of the desired product purity of 99.5%.

Example 8. The extraction is carried out as described in example 1. Time 1 and 2 extraction for 3 hours as hydrophobic extractant reason alkaloids using benzene. As sorbent use aluminum oxide. Obtain 0.55 g (yield of 1.10% (based on the original dry plant material) of the desired product purity of 99.3%.

Example 9. The extraction is carried out as described in example 1. Time 1 and 2 extraction for 3 hours as hydrophobic extractant reason alkaloids using carbon tetrachloride. As sorbent use aluminum oxide. Obtain 0.50 g (yield of 1.00% (based on the original dry plant material) of the desired product purity of 99.4%.

Example 10. The extraction is carried out as described in example 1, but using methanol instead of water and ethanol. Time 1 and 2 extraction for 3 hours as hydrophobic extractant reason alkaloids using butyl acetate. As the sorbent using silica gel. Get to 0.60 g (yield of 1.20% (based on the original dry plant material) of the desired product purity of 99.4%.

Example 11. The extraction is carried out as described is about in example 1, but using 70% aqueous propanol ethanol instead of water. Time 1 and 2 extraction for 3 hours as hydrophobic extractant reason alkaloids using diethyl ether. As the sorbent using silica gel. Get to 0.60 g (yield of 1.20% (based on the original dry plant material) of the desired product purity of 99.4%.

Example 12. The extraction is carried out as described in example 1, but using 60% aqueous isopropanol instead of water and ethanol. Time 1 and 2 extraction for 3 hours as hydrophobic extractant reason alkaloids using diethyl ether. As the sorbent using silica gel. Gain of 0.58 g (yield of 1.16% (based on the original dry plant material) of the desired product purity of 99.1%.

Example 13. The extraction is carried out as described in example 1, but using water-rich butanol ethanol instead of water. Time 1 and 2 extraction for 3 hours as hydrophobic extractant reason alkaloids used disutility ether. As the sorbent using silica gel. Obtain 0.50 g (yield of 1.00% (based on the original dry plant material) of the desired product purity 99,0%.

Example 14. The extraction is carried out as described in example 1. Time 1 and 2 extraction for 3 hours as hydrophobic extractant reason alkaloids used tetrachlorethylene. As sorbent use aluminum oxide. Get 55 g (yield of 1.10% (based on the original dry plant material) of the desired product purity of 99.3%.

The purity of the target product according to examples 1-14 was confirmed by analysis using high-performance liquid chromatography (HPLC), and was a 99.0-99.5% pure). The ratio of alkaloids sanguinarine:gelatin in the target product was changed in the range from 1:100 to 100:1 depending on the feedstock composition.

The inventive method of producing sulfates sanguinarine and chelerythrine in comparison with the known methods for producing sulfates sanguinarine and chelerythrine can achieve the following advantages: to obtain a product of higher purity, to minimize the use of chlorine-containing solvents, to reduce the number of non-regenerating waste, and reduce the overall length of the process, to improve the working conditions of the staff, to reduce the requirements to the quality of the raw material content of the target product and related compounds due to the high reproducibility of the method of obtaining the target product.

1. The method of producing sulfates sanguinarine and chelerythrine, including extraction of powdered aerial parts of Maclay small-fruited and/or Maklai cordate aqueous aliphatic alcohol, removing the aqueous aliphatic alcohol in a vacuum, alkalization of water VAT residue, extraction of water VAT residue hydrophobic solvent, the processing of the organic phase with sulfuric acid,filtering, washing and drying of the target product, characterized in that the extraction of the crushed material spend aqueous aliphatic alcohol in the presence of methansulfonate, and the solution of the grounds of alkaloids in the hydrophobic organic solvent is additionally filtered through a layer of hydrophilic sorbent, and the target product is subjected to boiling in acetone.

2. The method according to p. 1, characterized in that the treatment with sulfuric acid is carried out in a solution of concentrated sulfuric acid in ethyl acetate.

3. The method according to p. 1, characterized in that the extraction is carried out by consecutive stages lasting no more than 3 hours.

4. The method according to p. 1, characterized in that as the aqueous aliphatic alcohol use 80% aqueous ethanol.

5. The method according to p. 1, characterized in that as the hydrophobic organic solvent used methylene chloride, or chloroform, or ethyl acetate, or dichloromethane, or toluene.

6. The method according to p. 1, characterized in that as the alkaline reagent is used hydroxide, or carbonate, or bicarbonate of sodium or potassium.

7. The method according to p. 1, characterized in that the sorbent using alumina or silica gel.

8. The method according to p. 1, characterized in that the target product is washed with an organic solvent used at the stage of liquid-phase extraction.



 

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2 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: group of inventions refers to organic chemistry, namely to a compound of formula I and to their pharmaceutically acceptable salt or their ester, wherein W means C(H)2, C(H)2-C(H)2 or C(H)(CH3); X is specified in a group consisting of: (1) O, (2) N(H), (4) S, (5) S(O) and (6) S(O)2; Y means carbon or nitrogen; R1 is specified in a group consisting of: (1) hydrogen, (2) halogen, (3) methyl optionally substituted by fluorine, (4) C1-7alkoxygroup optionally substituted by fluorine, (5) cyano group and (6) C1-7alkylsulphonyl; R2 means hydrogen, fluorine, chlorine or C1-7alkoxygroup; R3 means hydrogen, fluorine, chlorine, bromine or methyl; R4 is specified in a group consisting of: (1) hydrogen, (2) halogen, (3) C1-7alkyl optionally substituted by fluorine, (4) C3-7cycloalkyl, and (5) ethenyl; R5 and R6 are independently from each other specified in a group consisting of: (1) hydrogen, (2) halogen, (3) C1-7alkyl, (4) cyanogroup and (5) C3-7cycloalkyl; R7 means cyano group or S(O)2-R8, wherein R8 is specified in a group consisting of: (1) C1-7alkyl, (2) C3-7cycloalkyl, (4) C1-7alkylamino group, (5) C1-7dialkylamino group, (6) lower heterocycloalkyl optionally substituted by halogen, C1-7alkyl, or C1-7alkoxycarbonyl and (7) 2-oxa-6-azaspiro[3.3]hept-6-yl, wherein lower heterocycloalkyl means a saturated or partially unsaturated non-aromatic ring fragment containing 3 to 7 atoms bound together to form a ring structure, wherein one, two or three ring atoms are heteroatoms, whereas the rest ring atoms are carbon atoms; and pharmaceutically acceptable esters represent methyl and ethyl acid esters of formula I acceptable as prodrugs. The invention also refers to a pharmaceutical composition based on the compound of formula .

EFFECT: prepared are new compounds possessing the CRTH2 receptor antagonist or partial agonist activity.

23 cl, 90 ex

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