Method for preparing octa-4,5-carboxyphthalocyanine cobalt sodium salt

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to medicine and chemical-pharmaceutical industry, namely industrial chemistry, and concerns a method for preparing octa-4,5-carboxyphthalocyanine sodium salt (a substance of the preparation teraphthal).

EFFECT: method provides preparing high-purity octa-4,5-carboxyphthalocyanine sodium salt free from residual low-molecular impurities, oligomer products and residual chlorides, reducing the labour content of production, and increasing yield.

1 ex

 

The invention relates to the field of chemical technologies, and in particular to an improved method of obtaining sodium salt 2,3,9,10,16,17,23,24 - octacarbonyl acid phthalocyanine cobalt (OCTA-4,5-carboxyfullerene cobalt - octacarbonyl-PcCo),the substance of the drug terephthal), which is a drug for the catalytic ("dark") cancer therapy, based on the generation in combination with ascorbic acid reactive oxygen directly into the tumor by chemical means without the use of physical action.

A method of obtaining sodium salt OCTA-4,5-carboxyfullerene cobalt (2304582 C07D 487/22, 2007, prototype) by fusing the dianhydride pyromellitic acid salt of cobalt in the presence of urea and subsequent alkaline hydrolysis of the resulting tetraamide OCTA-4,5-carboxyfullerene cobalt, and formed after hydrolysis of the salt cleanse from impurities, in particular oligomeric products, method of column chromatography with alumina, followed by deposition octacarbonyl acid, its washing method repeated decantation until the complete settling of the suspension, washing is repeated until the conductivity of decantate 75-80×10-2Cm/m After the last decanting the suspension is concentrated in a centrifuge, then the resulting paste is placed on a suction filter and washed distill the trated water repulpable to get 3-5%water suspension. Instead of washing with distilled water with repulpable on the suction filter is clean from residual inorganic salts carried out by electrodialysis OCTA-4,5-carboxyfullerene cobalt after partial neutralization to pH 5.2-5.5 with a current density of 0.15-0.25 A/DM2the temperature of 20-35°C and concentration of 1.5-3.0%, followed by complete neutralization to pH 8.7, processing resulting solution salt octacarbonyl-PcCo activated charcoal, filtering and drying the filtrate in the spray dryer. The yield of the target product is 19-20% per dianhydride pyromellitic acid. The basic substance content is 97.0%, the chloride content is 0.08%.

The disadvantages of the method are great complexity and duration of the process (up to two to three months), the low yield of the target product.

The present invention is to reduce labor costs and time to obtain salt octacarbonyl-PcCo high purity and increasing the yield of the target product.

To solve this problem using the method of its obtaining, consisting of the following stages:

- getting tetraamide octacarbonyl-PcCo the fusion of dianhydride pyromellitic acid salt of cobalt in the presence of urea;

- obtaining salt octacarbonyl-PcCo alkaline hydrolysis of cetrimide;

- clear the form is Asia after hydrolysis of the salt from the residual low-molecular impurities by precipitating and washing octacarbonyl PcCo method diafiltration on ultrafilter when the pH of the suspension 2,0÷4,0, to the optical density of permeate at ≤0.3 at a wavelength of 212 nm;

- the selection of the monomer by the method of diafiltration on ultrafilter suspension at pH 4,5÷7,0 with preconcentration using nanofilters and returning permeate at the previous stage;

- washing of the obtained monomer from pyromellitic acid and other low molecular weight impurities by the method of diafiltration on Ultrafiltered solution of hydrochloric acid at a pH of suspension of 2,5÷4,0 and then deionized water and/or nanofilter deionized water at pH 7.0÷8,0;

- neutralization of the suspension of octacarbonyl PcCo to pH ≈8.0 and washed with deionized water using nanofilters method diafiltration solution Na salt of ions of Cl-until the conductivity of permeate 3,8-4,8×10-4Cm/m

- concentration using nanofiltration resulting solution Na salt followed by complete neutralization to pH 8.5-8.7 aqueous sodium hydroxide solution, filtering and selection of the target product by drying the filtrate.

The proposed method is carried out using the installation for the purification of salt and separating the monomer whose schema is presented in figure 1, where 1 is the capacity for the original salt solution, 2 - capacity for selected solution of the monomer, 3 - pump, 4 - ultra-filter, 5, 6, 7, 8, 9, 12, 13, 14, 16, 17, 18, 19, 20 - communication lines (pipelines), 10 - pump, 11 - nanofilter, 15 - ultravolt is.

Example 1.

A mixture of 2.39 M pyromellitic anhydride, 23.6 M urea, 0.41 M cobalt chloride and 16.0 g of ammonium molybdate are heated with stirring 1.5 hours at 140-150°C and 3 h at 200-205°C. the Melt is cooled, crushed and boiled with 30 liters of water in about 3 hours, then boiled with 10%hydrochloric acid, the suspension is filtered, the precipitate washed with water until the pH of wash water is not less than 6.5, then alcohol, squeezed and dried. Get 1.3 kg of cetrimide (molar extinction coefficient in dimethylsulfoxide not less than 50,000).

The resulting tetramed (1.3 kg) is boiled with 25%alcoholic solution of sodium hydroxide (30 l), the hot suspension is filtered, the precipitate washed on the filter with alcohol until a colorless filtrate, squeezed and dried. The obtained potassium salt of octacarbonyl-PcCo is dissolved in water and loaded into the container 1 installation for the purification of salt and separating the monomer whose schema is presented in figure 1. Then if the pump 3 and open the bypass line 5 salt solution (pH 10) acidified with 10%hydrochloric acid to a pH of 2.5 to 4.0, close the line 5, open the line 6 and 7 and begin to circulate the contents of the tank 1 through an ultra-filter 4, serving in the capacity of a 1 solution of hydrochloric acid (pH≈3) and then deionized water and taking in this permit on line 8 into the waste water. Thus lead leaching method diafiltration, without raising the pH of the suspension to enter the 4.5 and controlling the optical density of permeate at a wavelength of 212 nm, which should not be greater than 0.3. After reaching permeate optical density not greater than 0.3 stop leaching of salt, close the line 8, open line 9, alkalinized product in the tank 1 to pH 4.5÷7,0 and begin the removal of the monomer along the line 9 into the container 2. The accumulation of a solution of the monomer in the vessel 2 includes a pump 10, lines 12, 13 and 14, and concentrate the solution of monomer with nanofilter 11, returning the resulting permit on line 14 into the container 1. Thus removed from the original salt all or part of the monomer. The control process carried out by spectrophotometric method and absence of the dimer in the filtrate (λ max 825-830 nm).

Selected into the tank 2 through an ultra-filter 4 together with low molecular weight organic and inorganic impurities monomer is washed by the method of diafiltration on Ultrafiltered solution of hydrochloric acid at a pH of suspension of 2,5÷4,0 and deionized water and/or nanofilter deionized water at pH 7.0÷8,0.

To do this, if the pump 10 and open the bypass line 19 the monomer solution acidified with 10%hydrochloric acid to a pH of 2.5 to 4.0, close the line 19, open line 16 and 17 and begin to circulate the contents of the vessel 2 through an ultra-filter 15, serving in the capacity of 2 a solution of hydrochloric acid (pH≈3) and then deionized water and taking in this permit on line 18 into the waste water. Therefore clicks the zoom lead leaching method diafiltration, without raising the pH of the suspension is higher than 4.5 and controlling the optical density of permeate at a wavelength of 212 nm, which should not be higher than 0.1, and the ratio of optical densities in the liquid phase washed product at a wavelength of 228 and a wavelength of 680 not more than 0.5.

Then neutralize the suspension of octacarbonyl PcCo to pH≈8.0 and using nanofilters method diafiltration finally washed solution Na salt octacarbonyl PcCo from ions of Cl-until the conductivity of permeate 3,8-4,8×10-4Cm/m Neutralization are in an aqueous solution of caustic soda during the operation of pump 10 and open the bypass line 19. After neutralization, close the line 19, open line 12 and 13, and begin to circulate the contents of the vessel 2 through nanofilter 11, serving in the capacity of 2 deionized water and taking in this permit on line 20 into the waste water. Then the purified solution of Terentieva salt octacarbonyl-PcCo concentrate using nanofilter, DataRowView to pH 8.5-8,7, unloaded from the installation, filtered, the filtrate dried, yielding the desired product with a yield of 40% based on dianhydride pyromellitic acid; the basic substance content of not less than 97.0%, the chloride content is 0.08%. The process duration is 2-3 weeks.

Example 2. The process is carried out by analogy with example 1, but allocated into the tank 2 through an ultra-filter 4 instead of the f with a low molecular weight organic and inorganic impurities monomer is washed by the method of diafiltration on nanofilter deionized water at pH 7.0÷8,0.

To do this, if the pump 10 open line 12 and 13, and begin to circulate the contents of the vessel 2 through nanofilter 11, serving in the capacity of 2 deionized water and taking in this permit on line 20 into the waste water. Thus lead leaching solution of monomer by the method of diafiltration, and controlling the optical density of permeate at a wavelength of 212 nm, which should not be higher than 0.1, and the ratio of optical densities in the liquid phase washed product at a wavelength of 228 and a wavelength of 680 not more than 0.5. Before the end of the cleanup process carry out control measurements of electrical conductivity of permeate, which should be 3,8-4,8×10-4Cm/m

Then the purified solution of Terentieva salt octacarbonyl-PcCo concentrate using nanofilter, DataRowView to pH 8.5-8,7, unloaded from the installation, filtered, the filtrate dried, yielding the desired product with a yield of 40% based on dianhydride pyromellitic acid; the basic substance content of not less than 97.0%, the chloride content is 0.08%. The process duration is 2-3 weeks.

Thus the proposed method can significantly reduce the total time of the process, to increase the output while obtaining a product with a high degree of purity.

The method of obtaining sodium salt OCTA-4,5-carboxyfullerene cobalt alloyed who eat dianhydride pyromellitic acid salt of cobalt in the presence of urea and subsequent alkaline hydrolysis of the resulting tetraamide OCTA-4,5-carboxyfullerene cobalt and clearance formed after hydrolysis of salts of impurities, in particular oligomeric products, residual low molecular weight impurities and inorganic salts by washing with a solution of hydrochloric acid or distilled water, followed by neutralization in an aqueous solution of sodium hydroxide, filtering and selection of the target product by drying, wherein the clearance formed after hydrolysis of the salt from the residual low molecular weight impurities is carried out by precipitation and washing octacarbonyl PcCo method diafiltration on ultrafilter when the pH of the suspension 2,0÷4,0 to the optical density of permeate at ≤0.3 at a wavelength of 212 nm, followed by separation at a pH of suspension 4,5÷7,0 monomer, concentrating it on nanofilter and returning permeate in the previous stage, the washing of the obtained monomer from low molecular weight impurities by the method of diafiltration on Ultrafiltered solution of hydrochloric acid at a pH of suspension of 2,5÷4,0 and deionized water and/or nanofilter deionized water at pH 7.0÷8,0, neutralization of the suspension to pH≈8.0 and the washing solution using nanofilters deionized water from ions of Cl-until the conductivity of permeate 3,8-4,8·10-4Cm/m, followed by concentrating the obtained solution Na salt octacarbonyl PcCo with NF and its complete neutralization to pH 8.5-8,7 aqueous solution of caustic soda.



 

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