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

FIELD: chemistry of metalloorganic compounds, chemical technology.

SUBSTANCE: invention relates to an improved method for synthesis of octa-4,5-carboxyphthalocyanine cobalt sodium salt, or 2,3,9,10,16,17,23,24-octacarboxylic acid of phthalocyanine cobalt (terephthal) of the formula (I) . Terephthal is a synthetic preparation used in catalytic ("dark") therapy of cancer based on generation of oxygen reactive species in tumor directly by chemical manner and in combination with ascorbic acid being without using the physical effect. Method for preparing octa-4,5-carboxyphthalocyanine cobalt sodium salt involves melting pyromellitic acid dianhydride with cobalt salt in the presence of urea followed by alkaline hydrolysis of prepared octa-4,5-carboxyphthalcyanine cobalt tetraimide. Salt formed after hydrolysis is purified from impurities, in particularly, from oligomeric compounds by column chromatography method on aluminum oxide, following precipitation of octacarboxylic acid, its, its washing out, concentrating and purifying from residual inorganic salts by washing out with distilled water and by neutralization with sodium hydroxide aqueous solution also, treatment with apyrogenic activated carbon, filtration and drying the end substance. Purification of octa-4,5-carboxyphthalocyanine cobalt from residual inorganic salt is carried out preferably by electrodialysis method after its partial neutralization to pH 5.2-5.5 at current density 0.15-0.25 A/dm2, temperature 20-35°C and the concentration 1.5-3.0% followed by complete neutralization to pH 8.7, treatment of obtained octacarboxy-PcCo salt solution with activated carbon, filtration and drying filtrate in a spray drier. Proposed method provides preparing octa-4,5-carbocyphthalocyanine cobalt salt of high purity degree and free of oligomeric compounds and residual chlorides.

EFFECT: improved method of synthesis.

5 ex

 

The invention relates to the field of chemical technology, namely the method of obtaining sodium salt OCTA-4,5-carboxyfullerene cobalt (taratala), which is a synthetic drug for the catalytic ("dark") cancer therapy (Abirkin, Osipkov, Bscit, Lghting and other Ross. Chem. Log. 1998 (5), p.140-146). This method is based on generation in combination with ascorbic acid reactive oxygen directly into the tumor without the use of physical action.

Himself OCTA-4,5-carboxylation cobalt (2,3,9,10,16,7,23,24-octacarbonyl acid phthalocyanine cobalt, or octacarbonyl-RSO) can be obtained by interaction of octylaniline cobalt with potassium hydroxide in aqueous ethylene glycol at a temperature of 160°within 24 hours, the selection of the target product in an acidic environment and its subsequent clearance [Y.Orihashi, M.Nishikawa, H.Ohno, E.Tsuchida. Bull. Chem. Soc. Jpn. 1987, Vol.60, No. 10, pp.3731-3738]. However, this method is complicated by the difficulty of synthesis pyromellitimide - source connection for obtaining octylaniline cobalt.

Also known is a method of obtaining octacarbonyl-Rsso of dianhydride pyromellitic acid by fusing it with the salt of cobalt in the presence of urea, alkaline hydrolysis forming tetraamide with the formation of salt octacarbonyl-Rsso and then have podci is the group (D.R.Boston, J.C.Bailar, Jr. Inorg. Chem. 1972. Vol.11, pp.1578-1584). The downside of it is the low purity of the desired products, as well as the salt and the acid caused in particular by the presence of organic impurities,

impurities, including oligomeric nature, resulting from the further interaction of cetrimide OCTA-4,5-carboxyfullerene with the dianhydride pyromellitic acid, and inorganic salts.

The present invention is to obtain salt octacarbonyl-Rsso high purity, containing no impurities oligomeric nature and inorganic salts. To solve this problem using the method of its obtaining, consisting of the following stages:

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

- obtaining salt octacarbonyl-RSA alkaline hydrolysis of cetrimide;

- cleaning salt octacarbonyl-Rsso from organic impurities, including oligomeric products, method of column chromatography on aluminium oxide;

- deposition of octacarbonyl-RSA, its purification from inorganic salts;

- neutralization of octacarbonyl-RSA aqueous sodium hydroxide solution, the processing solution of sodium salt of (taratala) pyrogen-free activated is glam, filtering and drying in a spray dryer.

Put in the invention, the problem can be solved by clearing of residual inorganic salts by washing with distilled water, and the electrodialysis of solutions octacarbonyl-Rsso. To implement the latter obtained after concentrating octacarbonyl-RSA partially neutralized aqueous solution of caustic soda to a pH of 5.2-5.5 and the resulting pH of TETRANITRATE Sol octacarbonyl-RSA subjected to electrodialysis purification from residual inorganic salts. At higher pH increases the solubility of octacarbonyl-RSA due to neutralization of the remaining free carboxyl groups, however, formed of multiply charged anions, octacarbonyl-RSA poison anion-exchange membrane, reducing the performance of the cleaning process.

The process of electrodialysis is carried out at a current density of 0.15-0.25 A/DM2the temperature of 20-35°and the salt concentration of octacarbonyl-RSA 1.5-3.0%. The increase in current density above 0.25 A/DM2reduces the current output of the anions of the salt in the transfer of electricity, which leads to blocking of the working surface anion-exchange membranes and the deterioration of their work. Thus, with increasing current density from 0.15 to 0.4 A/DM2the current output is reduced from 19.5 to 4.5%, and the consumption of the process against the melts from 3.5 to 9.5 kWh/kg The temperature at which carry out the electrodialysis process in accordance with the invention, limited to the top thermal resistance of the anion exchange membranes, and at temperatures below 20°With reduced mobility suspensions, increases the voltage at electrodialyzer, which leads to an increase in the intensity of the process.

The optimal concentration of the solutions for electrodialysis purification salt octacarbonyl-RSA is 1.5-3.0%. When it achieves a better consumption of the process - 3.5-4.7 kWh/kg and the specific productivity of the apparatus is 250-320 g/m2·h compared to more dilute solutions (0.7%): 7.5 kWh/kg and 160 g/m2·h respectively. At concentrations above 3.0% reduced mobility of the suspension, which lowers the efficiency of the process. So, at current density of 0.25 A/DM2and the salt concentration of octacarbonyl-RSA 4.0% the energy intensity of the cleaning process is 8.8 kWh/kg, and the specific performance of the device - 126 g/m2·h

After the electrodialysis-purified salt solution, octacarbonyl-RSA neutralized with sodium hydroxide to pH 8.5-8.6, process pyrogen-free activated carbon, sterilized by ultrafiltration and produce terephthal drying in the spray dryer. The output of taratala at the stage of purification by electrodialysis is 94.0-95.0%, nigerianisation in the selected product is not more than 0.1%, and the duration of cleanup 3.5-7.0 hours.

The proposed method is illustrated by the following examples.

Example 1

Tetraonid octacarbonyl-Rsso.

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 DMSO not less than 50,000).

Potassium salt of octacarbonyl-Rsso.

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 salt is cleaned from impurities, in particular oligomeric products, method of column chromatography. To this salt solution (concentration of 8-10%) in deionized water and acidified with 10%hydrochloric acid to a pH of 8.0-8.3, loaded onto a column (diameter 80 mm, height 75 cm) with 4 kg of alumina (TU 6-09-426-75) and elute phosphate buffer, pH 8). Selected fraction with Rf0.9 (one spot on the plate Silufol), which is filtered through stekloboya FSB. To improve the output is Yes, the target product is taken a second fraction, contains a mixture of oligomers, which again chromatographytandem remove additional amounts of the desired product.

Sodium salt of octacarbonyl-Rsso.

Suspension Plava of cetrimide (300 g) in 6 l of 10%aqueous sodium hydroxide solution is boiled under stirring, the hot suspension is filtered, the precipitate washed on the filter with hot 10%aqueous solution of caustic soda, pasta, drained, then washed with alcohol and dried. The obtained sodium salt cleanse method column chromatography similar to the potassium salt.

Octacarbonyl-Rsso.

The purified salt solution (potassium or sodium) acidified with conc. hydrochloric acid to a pH of about 2, the precipitate acid repeatedly decanted deionized water after 20-30 minutes mixing and complete settling of the suspension (about 12 hours). Rinse repeat until you obtain the conductivity 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 with distilled water repulpable to get 3-5%water suspension.

Sodium salt of octacarbonyl-RSO (Terephthal).

Produced by neutralization of the suspension cleared octacarbonyl-RSA 10%aqueous sodium hydroxide solution to pH 8.5-8.6. For a complete neutralization of the mixture stirred at 20-25°With,check the pH of the solution and, if necessary, DataRowView, the solution is treated with pyrogen-free activated carbon, filtered through stekloboya FSB, then through the filter of "Vladipor" (0.2 μm), dried in the spray dryer type "Mobile minor 2000" when the input temperature 170±10°and an output - 90±5°C. final drying is carried out in an oven at 105-110°C. the Yield obtained Taratala is 19-20% per dianhydride pyromellitic acid. Electronic absorption spectrum (in water, pH 7.3-8.3), λmaxnm: 674±2, 332±2. The basic substance content is 97.0%, the ratio of the specific absorption - 1200 cm-1g-1the chloride content is 0.08%. Found, %: C 42.60, 42.54; N 1.04, 1.03; 9.97 N, 9.79. Calculated, %: C40H8CoN8Na8O16. With 43.70; H 0.73; N, 10.19.

Example 2

In a glass container equipped with a stirrer, a load of 900 g of paste untreated, octacarbonyl-Rsso obtained after centrifugation (example 1)add 3000 ml of distilled water and with stirring, add 10%aqueous sodium hydroxide solution to pH 5.5. When the pH value is formed movable close to the solution of suspension of Terentieva salt octacarbonyl-Rsso containing 2.15% phthalocyanine and 1.0-1.5% of sodium chloride, which is subjected to electrodialysis purification in a multi-chambered apparatus - electrodialyzer filter presnogo type consisting of ion-exchange membranes of the type MA-40 and MK-40 ol the interstitial frames of paronite and separators-energizers. Cathode and anode are plate stainless steel AISI 18CR10NITI with the working surface 4 DM2. Electrodialyzer consists of three anion-exchange and five cation-exchange membranes with the working surface 4 DM2forming three chambers "clean" and four cameras "concentration", and two electrode chambers.

A suspension of salt octacarbonyl-RSA with inorganic impurities by the pump is passed through the camera "desalting", at the same time through the tract "concentration" pumped piped water, and through the electrode chambers with 5%sodium hydroxide solution in a closed loop.

At a temperature of 20°through electrodialyzer pass a constant current density of 0.25 A/DM2to achieve the solution of the chloride concentration 0.0015%. Cleaning time is 4.0 hours, while the current output corresponds to 14.0%, the degree of demineralization of 95%.

The purified solution of Terentieva salt octacarbonyl-RSO (4000 ml) is neutralized 120 ml 9.6%-aqueous sodium hydroxide solution to pH 8.5-8.6. Resulting salt solution, octacarbonyl-RSA treated with activated charcoal, filtered, the filtrate is dried in the spray dryer. Get 77.0 g of the target product, the output 83.70% per loaded octacarbonyl-Rsso. The content of the basic substance is 97.8%, the ratio of the specific absorption - 1212 cm-1g-1

Example 3

Analogously to example 2 pasta octacarbonyl-RSO (example 1) is subjected to electrodialysis purification at current density of 0.15 A/DM2and a temperature of 35°until the chloride content 0.0014%. While the current output is 18.5%, and the degree of demineralization 95.3%, duration electrodialysis purification 6 o'clock

After further processing, as in example 1, get 78.1 g of the target product. The substance is 84.9%. The content of the basic substance - 98.0%, the ratio of the specific absorption 1123 cm-1·g-1the content of chloride - 0.075%.

Example 4

Analogously to example 2 pasta octacarbonyl-RSA with its concentration of 3.1% and a concentration of sodium chloride 0.045% is subjected to electrodialysis purification at current density of 0.25 A/DM2and a temperature of 20°to the chloride content of 0.003%. When this output current is 20.0%, and the degree of demineralization 93.3%, duration electrodialysis purification 3.5 hours

After further processing, as in example 1, get 106.8 g (83.5%) of the desired product. The content of the basic substance - 97.7%, the ratio of the specific absorption 1092 cm-1g-1the content of chloride - 0.085%.

Example 5

Analogously to example 2 pasta octacarbonyl-RSA with a concentration of 1.52% and the concentration of sodium chloride 0.019% is subjected to electrodialysis purification tightly when the ti current 0.15 A/DM 2and a temperature of 20°to chloride 0.0004%. While the current output is 9.7%, the degree of demineralization 98.0%, duration electrodialysis purification 7 PM

After further processing, as in example 1, get 52.1 g (82.0%) of the desired product. The content of the basic substance - 97.5%, the ratio of the specific absorption 1093 cm-1·g-1the content of chloride - 0.095%.

Thus, the proposed method for OCTA-4,5-carboxyfullerene cobalt has the advantage compared with the nearest method is similar in that it provides purification of the target product from organic impurities, including oligomeric nature, and residual inorganic salts, which allows to derive the substance of the drug Terephthal for catalytic treatment.

The method of obtaining sodium salt OCTA-4,5-carboxyfullerene cobalt

the fusion of dianhydride pyromellitic acid salt of cobalt in the presence of urea and subsequent alkaline hydrolysis of the resulting tetraamide OCTA-4,5-carboxyfullerene (RS) cobalt, characterized in that formed after hydrolysis of the salt cleanse from impurities, in particular oligomeric products, method of column chromatography with alumina, followed by deposition of octacore the si-Rsso of concentrated hydrochloric acid, her washing, concentration and purification from residual inorganic salts by washing with distilled water or by electrodialysis at pH of 5.2 to 5.5, the current density of 0.15-0.25 a/DM2the temperature of 20-35°and the concentration of 1,5-3,0%, followed by neutralization with an aqueous solution of caustic soda, by treatment of the solution with activated carbon, filtration and drying of the target product in the spray dryer.



 

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