Preparation possessing antitoxic activity and containing complex compound, methyluracil derivative with organic acid, and method for preparing it

FIELD: medicine.

SUBSTANCE: preparation shows an antitoxic activity, and can be used as an antidote for nitrite and nitrate poisoning. A complex compound of 5-hydroxy-6-methyluracil with ascorbic acid (5-hydroxy-6-methyluracil ascorbate) is described by formula: The preparation contains the complex compound in an amount of 0.3-0.4 wt %, and ascorbic acid - the rest. The method for producing the preparation consists in a reaction of 5-hydroxy-6-methyluracil and ascorbic acid taken in the relation of ascorbic acid: 5-hydroxy-6-methyluracil equal to 1:(0.0015-0.0022), in water as a solvent at a temperature of 20-40°C for 30-60 minutes. The complex compound is produced as shown by infra-red and NMR spectra. The antitoxic activity of 5-hydroxy-6-methyluracil on nitrite has been unknown before.

EFFECT: water removal from the reaction mixture under low pressure.

2 cl, 2 tbl, 1 ex

 

The invention relates to medicine, in particular to pharmacology, and drugs with antioxidant activity and containing the complex compound derived methyluracil with an organic acid, specifically compound 5-hydroxy-6-methyluracil with ascorbic acid (5-hydroxy-6-methyluracil ascorbate) formula:

This drug can be used as an antidote in the complex of therapeutic measures in the administration of nitrites and nitrates.

Known immunomodulatory drugs [patent RU 2292892, CL AC 31/513, AK 47/12, OR 37/04, publ. 10.02.2007,] containing diazepan (pair-pair-(2,4-Dioxo-6-methylpyrimidine-5-sulphonamido)-diphenylsulfone) or sulphite (N,N'-(Sulfonyl-1,4-phenylene)-bis-(N",N"-dimethylformamidine)-1,2,3,4-tetrahydro-6-methyl-2,4-dioxo-5-pyrimidinemethanol) and ascorbic acid in a ratio of components: diazepan (soliton)/acid=1,65/(1,0-0,5). These drugs exhibit high together with immunomodulating activity. However, both tools can only be used in the treatment of several diseases involving immune defficiency of the body, and the results of their research antitoxic no action.

Known compound 6-methyluracil with succinic acid, showing antigipoksicheskoe activity [patent RU 2259357, CL C07D 239/22, publ. 27.08.2005,]. This compound has a higher antihypoxic activity in comparison with reference drugs and low toxicity. The disadvantage is that information about the antitoxic action of this complex compound is absent. However, we can assume that its antitoxic effect will be less pronounced than in the claimed product, as antitoxic effect of 6-methyluracil is less pronounced than that of its derivative 5-hydroxy-6-methyluracil, and succinic acid is not among the antidotes for poisoning by nitrites and nitrates.

The closest to describing the technical essence and the achieved result is a drug that has antihypoxic activity and containing the complex compound derived methyluracil with an organic acid, the derivative methyluracil use of 1,3-bis(2-hydroxyethyl)-5-hydroxy-6-methyluracil, and as the organic acid is fumaric acid [patent RU 2330025, CL C07D 239/60, AK 31/513, A61P 9/10, publ. 27.07.2008,]. The complex compound has the formula:

The drug having antihypoxic activity and containing the complex compound derived methyluracil with an organic acid, obtained by the interaction of equimolar number of the qualities of 1,3-bis(2-hydroxyethyl)-5-hydroxy-6-methyluracil with fumaric acid in the environment of a solvent at a temperature of 60-70°C for 2-3 hours, removal of the solvent from the reaction mixture and obtain a product. As the solvent used ethanol. This compound compared with the reference drugs has a higher antihypoxic activity and low toxicity when injected into the stomach and intraperitoneally. However, the antitoxic action of complex compounds 1,3-bis(2-hydroxyethyl)-5-hydroxy-6-methyluracil with fumaric acid is not given.

The task, which directed the claimed technical solution is to expand the Arsenal of pharmacological agents with low toxicity, with higher antioxidant activity.

The problem is solved by obtaining the drug, possess antioxidant activity and containing the complex compound derived methyluracil with an organic acid, where as derived methyluracil used 5-hydroxy-6-methyluracil, the organic acid is ascorbic acid, and the product contains compound 5-hydroxy-6-methyluracil with ascorbic acid of the formula:

in the amount of 0.3-0.4% of the mass. and ascorbic acid - the rest.

A method of producing a drug that has antitoxic activity and containing the complex compound derived METI the uracil with an organic acid, is their interaction in the environment of the solvent, followed by removing the solvent from the reaction mixture and the product, as derived methyluracil using 5-hydroxy-6-methyluracil, the organic acid is ascorbic acid, and the solvent is water, the source reagents are taking in a molar ratio of ascorbic acid : 5-hydroxy-6-methyluracil 1:(0,0015-0,0022), the interaction is carried out at a temperature of 20-40°C for 30-60 minutes, and the solvent is carried out under reduced pressure.

It is known that ascorbic acid is used as antidote for poisoning by nitrite and nitrate, 5-hydroxy-6-methyluracil reduces the level of methemoglobin in mice when the administration of sodium nitrite.

Acute toxicity of the preparation was studied on white mice-males weighing 20±2 g Three animal groups of 10 animals each once in the stomach through a tube introduced the drug in doses of 2000 mg/kg, 4000 mg/kg and 6000 mg/kg (table.1). Observations of the animals were within two weeks. Take into account survival (mortality) mice, coat condition, physical activity, frequency of intake of food and water, reflex activity.

It is established that the drug does not cause visible signs of intoxication and death of mice within 14 days of observation, and no significant effect on the General condition of the animals. In accordance with GOST 12.1.007-76 the drug in the stomach belongs to low-hazard substances. Dose that causes 50% mortality of mice, 5-hydroxy-6-methyluracil more than 10,000 mg/kg and for ascorbic acid - 3367 mg/kg

Toxicity after a single intraperitoneal administration of the drug in doses of 100 mg/kg, 500 mg/kg 1100 mg/kg was studied on white mice-males weighing 20±2 g (table.1). Statistical group consisted of 10 animals. Observations of the animals were within two weeks. It is established that the drug does not cause the death of the mice during its introduction into the abdominal cavity in the above doses and does not affect the General condition of the animals. According to the classification of the toxicity of substances, when introduced into the abdominal cavity of the animal, the study drug belongs to class 5 toxicity - "practically nontoxic".

Antitoxic activity of the drug is studied in a model of acute poisoning of mice with sodium nitrite. To study the antitoxic activity used white mice-males weighing 20±2 g Statistical group consisted of 8 animals. Acute poisoning caused by the introduction into the skin of the back of a 4% solution of sodium nitrite at a dose of 250 mg/kg of Choice this before the s was due to the preliminary Toxicological study of sodium nitrite. With the introduction of this dose in the conditions of the experiments was observed 100% mortality of animals. The lifespan of mice was 17-18 min (average of 17.5 min) (table.2). The subcutaneous route of administration of sodium nitrite due to the instability of this compound in the gastrointestinal tract, which makes it impossible for the introduction of a specific number it another way.

The drug at a dose of 200 mg/kg was administered to experimental animals in the abdominal cavity in the form of a 0.5% aqueous solution in a preventive mode for 30 minutes before the start of registration of the investigated compounds and therapeutic 15-20 min after injection of sodium nitrite in a toxic dose. As a reference drug for the evaluation of antioxidant activity in models of acute poisoning with sodium nitrite used ascorbic acid, which used the same drug.

Antitoxic activity of the preparation was assessed by the life expectancy (in minutes) in experimental mice. Assessment of the reliability of the results was performed using t-student criterion. The results of the experiments are presented in table.2.

Table 1
Sharp shock, which was mentioned drug (composition: compound 5-hydroxy-6-methyluracil with ascorbic acid 0.3% wt., ascorbic acid 99.7% of the mass.) for white mice, various routes of administration in the body
A group of miceDose, mg/kgThe number of miceThe route of administration of medicationSurvival, %
110010in the abdominal cavity100
250010in the abdominal cavity100
3110010in the abdominal cavity100
4200010in the stomach100
5400010in the stomach100
6600010in the stomach100
Table 2
The influence of the drug (composition: compound 5-hydroxy-6-methyluracil with ascorbic acid is - 0.3% wt., ascorbic acid 99.7% of the mass.) on the lifespan of mice in a model of acute poisoning with sodium nitrite
Series of experienceOptions experienceThe number of miceLife expectancy
minin %p*
1Sodium nitrite8of 17.5100
2The drug, prophylactic administration840,2228,3<0,001
3Drug treatment introduction822,0125,7<0,05
4Ascorbic acid, prophylactic administration832,5185,6<0,001
P* - significance level

The drug is highly protective (preventive) activity in acute poisoning with sodium nitrite. The positive effect of ascorbic acid (200 mg/kg), recommended as an antidote to poisoning nitrite and nitrate, were less pronounced than the study drug.

therapeutic use of the drug compared with prophylactic less effective: the average life expectancy of poisoned mice by prophylactic administration to mice of the drug 40.2 min (228,3%), and therapeutic applications only 22,0 min (125,7%). Ascorbic acid in these conditions, the effect is not given.

The essence of the technical solution is illustrated by the following example.

Example 1. The synthesis of the drug.

To a solution of 2.5 g (0,0142 mol) of ascorbic acid in 50 ml of water was added 0,0031 g (0,000022 mol) of 5-hydroxy-6-methyluracil. The molar ratio of ascorbic acid : 5-hydroxy-6-methyluracil 1:0,0015. The reaction mixture was stirred for 40 minutes at 25°C. In the course of interaction was observed color change of the reaction mass. From the reaction mixture water was removed by evaporation under reduced pressure of 20 mm RT.article and obtained with a quantitative yield of product containing ascorbic acid and a complex compound 5-hydroxy-6-Metalurh the sludge with ascorbic acid. The preparation contains the compound 5-hydroxy-6-methyluracil with ascorbic acid in the amount of 0.3% of the mass. and ascorbic acid in the amount of 99.7% of the mass. The drug has a purple color.

Confirmation of the formation of complex compound data IR and13With NMR spectroscopy:

The IR spectrum of ascorbic acid, (v cm-1): 780, 1378, 1462 (furan ring), 1750 (RCOOR), 1198 (cyclic ether compounds), 1024, 1066, 1120, 1138 (C=O), 3214, 3310, 3406, 3528 (OH).

The IR spectrum of the complex compounds, (v cm-1): 760, 826, 874, 1024, 1042, 1366, 1402 (furan ring), 1636, 1654, 1684, 1756 (C=O, =N-C=O), 3016 (NH), 3214, 3316, 3406, 3526 (OH).

13From the NMR spectrum of ascorbic acid (δ M. D.): 62,10 (CH2OH); 70,61 (CHOH); 90,59 (C5); 160,37 (C2); 185,20 (C3); 194,76 (C4).

13From the NMR spectrum of the complex compounds (δ M. D.): 62,40 (CH2OH); 69,20 (CHOH); 77,10 (C5); 163,45 (C2); 128,60 (C3); 176,53 (C4).

The formation of the complex is confirmed by the shifts of the signals of the furan ring and the carbonyl group of ascorbic acid in IR and13From the NMR spectra.

The optimal condition for the creation of a drug that has antitoxic activity and containing the compound 5-hydroxy-6-methyluracil with ascorbic acid, is the temperature of 20-40°C and a duration of 30-60 minutes At temperatures below 20°C the speed of interaction between 5-hydroc and-6-methyluracil and ascorbic acid minor, and at temperatures over 40°C is the destruction of the complex compound 5-hydroxy-6-methyluracil with ascorbic acid. The interaction of reagents with a duration of less than 30 minutes is not enough for the formation of complex compounds, and process more than 60 minutes is impractical because of the additional time and energy costs.

The molar ratio of ascorbic acid : 5-hydroxy-6-methyluracil in the product is equal to 1:(0,0015-0,0022). This ratio is optimal, since the mixing ratio of ascorbic acid : 5-hydroxy-6-methyluracil < 1:0,0015 antitoxic action of the drug is weaker. By increasing the ratio of ascorbic acid : 5-hydroxy-6-methyluracil more than 1:0,0022 strengthening the antitoxic action of the drug is not observed, but at the same time increase the material cost of reagents.

From the reaction mixture water was removed by evaporation under reduced pressure, which allows the removal of water from the reaction mixture at temperatures below 40°C.

Thus, it follows from the presented results of the research, the proposed drug with antioxidant activity and containing the complex compound derived methyluracil with an organic acid, has more in the high antioxidant activity and low toxicity when injected into the stomach and intraperitoneally and allows you to expand the Arsenal of pharmacological agents with low toxicity, with a higher antioxidant activity.

1. The drug that has antitoxic activity and containing the complex compound derived methyluracil with an organic acid, characterized in that as a derivative methyluracil using 5-hydroxy-6-methyluracil, and as the organic acid is ascorbic acid, the preparation contains the compound of the following formula:

in the amount of 0.3-0.4% of the mass. and ascorbic acid - the rest.

2. The way to obtain the drug under item 1, with the use of interaction derived methyluracil with an organic acid in the environment of the solvent, followed by removing the solvent from the reaction mixture and the product, characterized in that as a derivative methyluracil using 5-hydroxy-6-methyluracil, the organic acid is ascorbic, and the solvent is water, the source reagents are taking in a molar ratio of ascorbic acid : 5-hydroxy-6-methyluracil 1:(0,0015-0.0022), the interaction is carried out at a temperature of 20-40°C for 30-60 minutes, and the solvent is carried out under reduced pressure.



 

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