Complexes of azithromycin with antiulcer and antimicrobial activity

 

(57) Abstract:

Usage: in the chemistry of complex compounds of organic antibiotics with metals, in particular in a method of producing a complex chelate compounds of azithromycin with two-and/or trivalent metals selected from the group of Mg (+2), Al (+3), Fe (+3), Rh (+3), Zn (+2), Bi (+3), for the production of anti-inflammatory medicines. The inventive method provides for the interaction of azithromycin in the form of a free base or hydrochloride salt of the corresponding two - or trivalent metal in a ratio equal to 1 2, in aqueous or aqueous-alcoholic medium at room temperature at pH 8 to 11. table 2.

The invention relates to new complexes of azithromycin with antacids activity.

Described (Belgian patent 892357) formation of complex compounds With+2macrolide antibiotics, including erythromycin, representing a starting material to obtain N-methyl-11-Aza-10-deoxo-10-digitaria - mizina A (generic name: azithromycin; brand name SumamedR (Pliva, Zagreb, Yugoslavia), while in J. Pharm. Pharmac. 18 (1966) 727 argues that with other IO the connection. On the contrary, we found that azithromycin forms complex compounds with divalent metals, resulting in obtaining products with high antibiotic activity.

It was known that, among other things, the gel Al-Mg is used as an antacid in the treatment of duodenal ulcers or gastric ulcers, giving relief to the gastric mucosa and maintaining the pH in the gastric juice in the range from 4.5 to 5.5. With the same objective also used some antibiotics to eliminate the microorganisms Helicobacter pylori and ampylobacter jejvni, which represent one of the factors causing the development and relapse of duodenal ulcers or stomach. As it was suggested that Helicobacter pylori lives in the area of the mucosa membrane of the stomach used higher doses and duration of treatment with different antibiotics. Even the azithromycin is not exception.

It was discovered and it is the aim of the invention that the complex compounds of azithromycin with bivalent and/or trivalent metals in the form of gels can be used to obtain a new antiulcer drugs.

H ,m< / BR>
Complex compounds according to groups II and III, which form physiologically tolerated connection.

In particular, you must specify Mg+2, Al+3, Fe+3Rh+3La+3and Bi+3.

The method of obtaining complex compounds of azithromycin is carried out by introducing into the reaction antibiotic in the form of free bases or salts, especially of hydrochloride, with salts of divalent and/or trivalent metals, such as Mg+2, Al+3, Fe+3Rh+3La+3and Bi+3in particular chloride, in a ratio of 2:1, at room temperature, in aqueous solution or in water-alcohol mixture, at pH 8,0-11,0, or hydroxide and/or metal carbonate, basic metal salicylates or gels that are used as antacids such as aluminium hydroxide-magnesium carbonate, sucralfate, wimalasuriya, in the ratio of 1:1 to 1:4. The process is most appropriate to conduct base-antibiotic alcohol, such as methanol or ethanol. The product emit the usual manner, for example by evaporation of the solvent (alcohol) from the reaction mixture under reduced pressure and separating the product by filtration.

This product is introduced by known methods in farmatsevticheskiy of azithromycin in the form of gels, as with other gels, which are used as antacids funds are held for 24 h in the mucosa of the stomach in rats at concentrations from 1.5 to 60 times (table.1 and 2), which exceeds the minimum inhibitory and bactericidal concentrations for Helicobacter pylori and mpylobacter jejvni; accordingly, these drugs more than recommended for the treatment of gastrointestinal diseases such as gastric ulcers or duodenal ulcers than the original azithromycin. It was shown in the Toxicological studies that the technology of preparation of medicines do not change the toxicity of the active component.

P R I m e R 1. 50 ml (0.02 mol) of a solution of azithromycin in 95% ethanol was dissolved 0,067 g AlCl3(0.01 M solution against Al+3and after adjusting the pH to 8.6 with 0.1 N. Paon, it was stirred for 1 h at room temperature in a stream of nitrogen. After adding 30 ml of water the reaction mixture is evaporated under reduced pressure to about half its volume, after which it was stirred for two hours and the pH is kept constant (pH-stat) at 8.9 using 0.1 G. of NaOH. A white precipitate was aspirated, washed with 3 to 10 ml of water and dried, which gave 0.68 g protano: 1,77%

Received: 1,73%

Activity: 852 E/mg Sarcina Lutea was ATSS 9341.

P R I m m e R 2. In accordance with the method described in example 1, with the only exception that AlCl3replaced by adding 0,136 g FeCl36N2O, and the pH was maintained at the level of 9.0, got 0,72 g light gray product (92,5%); so pl. 130-133aboutC.

Analysis: GE (method atomic absorption spectrometry):

Calculated: 3,59%

Found: 3,71%

Activity: 840 U/mg Sarcina Lutea was ATSS 9341.

P R I m e R 3. 0,750 g of azithromycin were loaded into a 100 ml vessel and dissolved in 50 ml of water by adding 1N Hcl (about pH of 6.0). Then added 0,136 g FeCl36H2O and stirred while gradually bringing the pH to 8.9 with 0.1 G. of NaOH. The reaction mixture was stirred for 2 h at a constant pH value, then a light gray product was aspirated, washed with 310 ml of water and dried. Received 0,70 g (89.9 percent). Analysis of the product was identical to the analysis of example 2.

P R I m e R 4. According to the process described in example 1, with the only exception that AlCl3was replaced by adding 0,132 g of RhCl33H2O received 0,67 g light gray product (83.6 percent); so pl. 120-123aboutC.

Analysis: Rh (polarographic method; 1M pyridine 1 is U/mg Sarcina Lutea was ATSS 9341.

P R I m e R 5. According to the process described in example 1, with the only exception that AlCl3was replaced by adding 0,186 g NaCl37H2Oh, and the pH was maintained at a level of 9.2, received 0.66 g of white product (80,5%); so pl. 118-122aboutC.

Analysis: La (absorption spectrometry method):

Calculated: of 8.47%

Found: 8,10%

Activity: 830 U/mg Sarcina Lutea was ATSS 9341.

P R I m e R 6. According to the process described in example 1, with the only exception that AlCl3was replaced by adding 0,158 g BiCl3received 0,70 g of the product (82,0%).

Analysis: Bi (method atomic absorption spectrometry):

Calculated: 12,25%

Found: 12,00%

Activity: 812 E/mg Sarcina Lutea was ATSS 9341.

P R I m e R 7. According to the process described in example 3, with the only exception that FeCl3was replaced by adding is 0.102 g MgCl26H2O, and the pH was maintained at a level of 8.6 was obtained 0.55 g (75,0%) of white product.

Analysis: Mg (method of atomic absorption spectrometry):

Calculated: 1,22%

Found: 1,54%

Activity: 850 U/mg Sarcina Lutea was ATSS 9341.

Physico-chemical characteristics of the products obtained according to examples 1, 2, 4, 5, 6, 7.

P R I m e R 8. White amorphous powder which, what about insoluble in N. hexane, petroleum ether and water;

analysis on Al (method of atomic absorption spectrometry):

Calculated: 1,77%

Found: 1,73%

Activity: 852 E/mg ATSS 9341.

P R I m e R 9. Lightly brown amorphous powder;

So pl. 130-133aboutC;

Soluble in methanol, ethanol, acetone, chloroform, methylene chloride and dimethylformamide, but insoluble in N. hexane, petroleum ether and water;

analysis on Fe (method of atomic absorption spectrometry):

Calculated: 3,59%

Found: 3,71%

Activity: 840 U/mg was ATSS 9341.

P R I m e R 10. Lightly brown amorphous powder;

So pl. 120-123aboutC;

Soluble in methanol, ethanol, acetone, chloroform, methylene-chloride in dimethylformamide, but insoluble in N. hexane, petroleum ether and water;

analysis on R (polarographic method 1 mol of pyridine 1 mol KCl), E1/2-0,40 on CE):

Calculated: 642%

Found: 6,15%

Activity: 834 E/mg ATSS 9341.

P R I m e R 11. White amorphous powder;

So pl. 118-122aboutC;

Soluble in methanol, ethanol, acetone, chloroform, methylene chloride and dimethylformamide, but insoluble in, hexane, petroleum ether and water;

analysis (a method of spectrometry atonally amorphous powder;

So pl. 126-130aboutC;

Soluble in methanol, ethanol, acetone, chloroform, methylene chloride and dimethylformamide, but soluble in N. hexane, petroleum ether and water;

analysis (method of atomic absorption spectrometry):

Calculated: 12,25%

Found: 12,00%

Activity: 812 E/mg ATSS 9341.

P R I m e p 13. White amorphous powder;

So pl. 121-124aboutC;

Soluble in methanol, ethanol, acetone, chloroform, methylene chloride and dimethylformamide, but soluble in N. hexane, petroleum ether and water;

analysis on Mo (method of atomic absorption spectrometry):

Calculated: 1,22%

Found: 1,54%

Activity: 850 U/mg was ATSS 9341.

Complexes of azithromycin General formula

< / BR>
where M is metal ion of the group of Mg(II), Al(III), Fe(III), Rh(III), Zn(III), Bi(III);

colourless or slightly coloured substances, soluble in methanol, ethanol, acetone, chloroform, methylene chloride and dimethylformamide, but insoluble in N. hexane, petroliana ether and water, obtained by the interaction of azithromycin in the form of a free base or hydrochloride salt of the corresponding divalent and/or trivalent metal, preferably chloride, in a weight ratio of 2 to 1 when it is in with magnesium is a white amorphous powder with so pl. 121-124oC and magnesium content of 1.54% complex azithromycin with aluminum white amorphous powder with so pl. 125-128oAnd aluminium content of 1.73% complex azithromycin with iron slightly brown powder with so pl. 130-133oC and iron content 3,71% complex azithromycin with rhodium slightly brown amorphous powder with so pl. 120-123oAnd the content of rhodium 6,15% complex azithromycin with lanthanum - white amorphous powder with so pl. 118-122oAnd the content of lanthanum 8,10% and a complex of bismuth with azithromycin white amorphous powder with so pl. 126-130oAnd the content of bismuth 12,0 having antiulcer and antimicrobial activity.

 

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