Methyluracil derivative and organic acid complex and method for production thereof

FIELD: chemistry.

SUBSTANCE: invention relates to a novel complex of 5-hydroxy-6-methyluracil with 5-aminosalicylic acid of formula . The compound has anti-inflammatory activity and can be used as a basic active substance when producing novel medicinal preparations having anti-inflammatory action. The invention also relates to a method of obtaining said complex. The method includes reacting 5-hydroxy-6-methyluracil with 5-aminosalicylic acid in equimolar amounts in an aqueous medium at room temperature for 24 hours, followed by removal of water from the reaction mixture and obtaining the product.

EFFECT: wider range of pharmacological preparations with low toxicity, having higher anti-inflammatory activity.

2 cl, 1 tbl, 1 ex

 

The invention relates to medicine, in particular to pharmacology, namely to complex compounds derived methyluracil with an organic acid, specifically complex to the compound of 5-hydroxy-6-methyluracil 5-aminosalicylic acid of the formula:

exhibiting anti-inflammatory activity. This compound can be used as the main active ingredient in the creation of new drugs that have anti-inflammatory action

Known compound 6-methyluracil with succinic acid, manifesting antihypoxic activity [patent RU 2259357, CL C07D 239/22, publ. 27.08.2005,]. This compound has low toxicity and higher antihypoxic activity compared with 6-methyluracil and succinic acid. The drawback of this coupling is that the anti-inflammatory effect of 6-methyluracil expressed weaker than its derivative 5-hydroxy-6-methyluracil.

Known compound 5-hydroxy-6-methyluracil with sodium succinate [patent RU 2475482, CL C07D 239/60, OR 43/00, publ. 20.02.2013,]. This compound has a higher antihypoxic activity in models of acute himicheskoi hypoxia and acute gistologicheskoe hypoxia compared with PE is eventName drugs and low toxicity when injected into the stomach and intraperitoneally. The disadvantage of the considered complex compounds is that 5-hydroxy-6-methyluracil is mixed with sodium succinate in the ratio of 1:10, and a considerable excess of sodium succinate may cause allergic reactions.

The closest to describing the technical essence and the achieved result is a 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, A61K 31/513, A61P 9/10, publ. 27.07.2008,]. The complex compound has the formula:

Compound derived methyluracil with organic acid is obtained by reacting equimolar amounts 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, removing the solvent from the reaction mixture and the 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, anti-inflammatory complex compounds 1,3-b is(2-hydroxyethyl)-5-hydroxy-6-methyluracil with fumaric acid has not been studied.

The task, which directed the claimed technical solution is to expand the Arsenal of pharmacological agents with low toxicity, which has a higher anti-inflammatory activity.

The problem is solved by obtaining the complex compounds derived methyluracil with an organic acid, where as derived methyluracil used 5-hydroxy-6-methyluracil, and organic acid - 5-aminosalicylic acid of the formula:

The method of obtaining complex compounds derived methyluracil with organic acid is in the interaction them in equimolar amounts in the environment of the solvent, the subsequent removal of the solvent from the reaction mixture with the product, as derived methyluracil using 5-hydroxy-6-methyluracil, organic acid - 5-aminosalicylic acid, and solvent - water interaction was performed at room temperature within 24 hours.

It is known that 5-hydroxy-6-methyluracil has anti-inflammatory action, which is associated with its ability to suppress the activity of proteolytic enzymes, 5-aminosalicylic acid as an inhibitor of prostaglandin synthesis, also has anti-inflammatory activity.

Acute toxicity of complex compound 5-hydroxy-6-methyluracil 5-aminosalicylic acid has been studied in 12 mice weighing 16-18 g compound was dissolved in TWEEN-85 and distilled water, was administered orally in two doses: 5000 mg/kg 8000 mg/kg during the first day of the animals in both groups were alive with no visible signs of toxicity of the complex. On the basis of the received data according to the classification GOST 12.1.007-76 compound 5-hydroxy-6-methyluracil 5-aminosalicylic acid belongs to the class IV hazardous compounds.

Anti-inflammatory activity of complex compound 5-hydroxy-6-methyluracil 5-aminosalicylic acid was studied on a model of acute inflammation caused by the introduction under the aponeurosis of the foot mice 1% solution carragenin. Experiments were performed on 48 outbred mice of both sexes weighing 18-20 g compound 5-hydroxy-6-methyluracil 5-aminosalicylic acid is administered orally in doses of 50 mg/kg and 100 mg/kg 1 hour before and 1 and 2 hours after playing inflammation. As comparative drugs were used starting compound: 5-hydroxy-6-methyluracil and 5-aminosalicylic acid, which was introduced in a similar way at a dose of 50 mg/kg Control animals were injected intragastrically equivalent volume of water. After until is reaches a "peak" moment of swelling, animals were euthanized ether anesthesia. Feet cut off in the area of the ankle joint and weighed. About anti-inflammatory activity was assessed by the severity of swelling experienced paws compared with healthy foot and inhibition of inflammation compared to the control without treatment (table).

Table
The influence of compounds on acute swelling of the paws of mice caused a 1% solution carragenin (N=8)
ConnectionDose, mg/kgThe severity of edema, %Inhibition of inflammation, %
Compound(5-hydroxy-6-methyluracil: 5-aminosalicylic acid =1:1)5056,6±4,1*26,4
Compound (5-hydroxy-6-methyluracil: 5-10049,1±2,236,2

aminosalicylic acid =1:1)
Compound (5-hydroxy-6-methyluracil:5-amines illowa acid =1:2) 5055,7±3,123,0
5-Hydroxy-6-methyluracil5066,7±3,013,3
5-Aminosalicylic acid5061,5±6,620,0
Control-76,9±4,5-
Note: N - number of animals in the group.
* - Significantly relative to the control at P<0,01, where P is the signicance level

The study showed that in the groups of animals that were injected compound 5-hydroxy-6-methyluracil 5-aminosalicylic acid in doses of 50 mg/kg and 100 mg/kg, the percentage of the severity of edema was, respectively, 1.4 and 1.6 times less than that of the control group. The claimed compound in a dose of 50 mg/kg inhibited inflammation by 26.4%, and at a dose of 100 mg/kg - 36.2%. Comparators (5-hydroxy-6-methyluracil and 5-aminosalicylic acid) reduces the severity of swelling, respectively, 1.2 and 1.3 times in comparison with control. The percentage inhibition of inflammation in these groups accounted for the Il of 13.3% and 20.0%, respectively.

Thus, the model carragenine inflammation compound 5-hydroxy-6-methyluracil 5-aminosalicylic acid in doses of 50 mg/kg and 100 mg/kg showed anti-inflammatory activity (P<0.01) compared with the parent compounds.

As follows from table 5-aminosalicylic acid showed a higher tendency to inhibition of inflammation than 5-hydroxy-6-methyluracil, therefore, was investigated anti-inflammatory activity of complex compound 5-hydroxy-6-methyluracil 5-aminosalicylic acid in which the molar ratio of the components 5-hydroxy-6-methyluracil:5-aminosalicylic acid is 1:2 (table). The table shows that the percent severity of edema and inhibition of inflammation was at the level of complex compound 5-hydroxy-6-methyluracil 5-aminosalicylic acid in which the molar ratio of the components 5-hydroxy-6-methyluracil: 5-aminosalicylic acid is 1:1.

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

Example 1.

To a solution of 2.0 g (0,013 mol) of 5-aminosalicylic acid in 200 ml of water was added 1.8 g (0,013 mol) of 5-hydroxy-6-methyluracil. The reaction mixture was stirred for 1 day at room temperature. From the reaction mixture water was removed by evaporation and was obtained with quantitative yield of integrated the e compound 5-hydroxy-6-methyluracil 5-aminosalicylic acid.

IR spectrum (ν, cm1): 646, 790, 1070(=N-), 1090, 1228, 1276, 1318 (ν CN), 1378 (δsCH3), 1426, 1462 (CH2CH3), 1600, 1650, 1690, 1710 (C=O, =N-C=O), 2536, 2854, 2938 (ν CH), 2950, 3082, 3560 (HE).

13C NMR spectrum (δ, M. D.): 18.22 (CH3), 153.04, 164.22 (C=O), 171.83 (COOH), 156.93 (C-OH), 131.31 (C-NH2).

The optimal condition for the process of obtaining complex compound 5-hydroxy-6-methyluracil 5-aminosalicylic acid is room temperature and duration of interaction 24 hours. Temperatures above and below room require additional energy costs for heating and cooling the reaction mixture, respectively. The interaction of reagents with a duration of less than 24 hours is not enough for the formation of complex compounds and the process for more than 24 hours is impractical because of the additional time and energy costs.

The optimal molar ratio of the components in the complex compound is the molar ratio of 5-hydroxy-6-methyluracil: 5-aminosalicylic acid is 1:1. Complex compounds of other elements (table). have the same anti-inflammatory properties, but to receive them spent more reagents.

Thus, it follows from the presented results of the research, the proposed compound 5-hydroxy-6-methyluracil 5-aminosalicylate acid of the formula:

has a higher anti-inflammatory activity than the original 5-hydroxy-6-methyluracil and 5-aminosalicylic acid, low toxicity and allows you to expand the Arsenal of pharmacological agents with low toxicity, which has a higher anti-inflammatory activity.

1. Compound derived methyluracil with an organic acid, characterized in that as a derivative methyluracil used 5-hydroxy-6-methyluracil, and organic acid - 5-aminosalicylic acid of the formula:

2. The method of obtaining complex compounds derived methyluracil with organic acid is in the interaction them in equimolar amounts in the environment of the solvent, the subsequent removal of the solvent from the reaction mixture to obtain the product, characterized in that as a derivative methyluracil using 5-hydroxy-6-methyluracil, organic acid - 5-aminosalicylic acid, and solvent - water interaction is carried out at room temperature for 24 hours.



 

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