CS226935B1 - N-(2-(p-tert.butylphenoxyacetoxy)ethyl)-n,n-dimethylalkyl-ammonium bromides and method of preparing same - Google Patents

Description

The present invention relates to N- (2- (p-tert-butylphenoxyacetoxy) ethyl) -N, N-dimethylalkylammonium bromides of the formula

CH _and C ³ ~ I

CH,

CH wherein R is an alkyl chain having a carbon number of 8 to 16 and a process for their preparation.

Organic ammonium salts have become extremely important since Domagk v

In 1932, he introduced benzododecinium, a compound that had significant antimicrobial effects. It is known that organic ammonium salts containing at least one long alkyl chain in their molecule exhibit antimicrobial effects and have found use in practice.

The compounds of the invention are novel substances not previously described in the chemical literature and have been found to have unknown effects on microorganisms.

Process for their preparation starting from S _{N 2} reaction of (2-dimethylaminoethyl) - (p-1-terc.butylfenóxyjacetátu brómalkánom. The advantage of this method of preparation compared with the other of _CH3

O-CH 2 C-O-CH 2 -N-R-Br-CH, methods are that the reaction is carried out in methanol or methyl cyanide under various conditions of temperature and reaction time to give products of high purity and high yields.

The examples illustrate but do not limit the preparation of the compounds of the invention, at the same time characterizing the selected compounds and reporting their antimicrobial activity as determined by dilution assay directly in the culture medium. Efficacy is reported as the minimum inhibitory concentration (MIC) in µg / ml on Staphylococcus aureus, Escherichia coli and Candida albicans strains.

Example 1

To 0.05 mol of (2-dimethylaminoethyl) - (p-t-226935 butylphenoxy) acetate dissolved in 5 ml of dry methyl cyanide is added at room temperature 0.05 mol of 1-bromodecane and the reaction mixture is heated at 40 ° C for 18 hours. cooling, the methyl cyanide is distilled off and the crude product, N- [2- (p-tert-butylphenoxyacetoxy) ethyl] -N, N-decyldimethylammonium bromide, is recrystallized to constant melting point from dry acetone, mp 77-78 ° C; analysis (calculated / found:

C 62.46 / 62.01, H 9.27 / 9.51, N 2.80 / 2.40; yield 86% of theory;

MIC: 2, 8, 40.

Example 2

The procedure was as described in Example 1 except that 1-bromododecane was used in the reaction, the solvent was methanol, the bath temperature was 100 ° C, and the reaction time was 6 hours. The product N- [2- (p-tert-butylphenoxyacetoxy) ethyl] -N, N-dimethyldodecylammonium bromide had mp 114-115 ° C;

elemental analysis (calculated / found:

C 63.70 / 63.42, H 9.55 / 9.80, N 2.69 / 2.55; yield 87% of theory;

MIC: 8, 50, 3.

Example 3

The procedure is identical to that of Example 1, with 1-bromo-tetradecane, methyl cyanide solvent, reaction temperature 80 ° C and reaction time 12 hours. The N- [2- (p-tert-butylphenoxyacetoxy) ethyl] -N, N-dimethylteitradecylammonium bromide product had mp 110-111 ° C; elemental analysis (calculated / found:

C 64.69 / 64.42, H 9.77 / 9.97, N 2.51 / 2.66; yield 83% of theory;

MIC: 6, 80, 20.

All the compounds thus prepared were white crystalline, low hygroscopic substances, soluble in polar and insoluble in non-polar solvents. In addition to elementary analysis, they were also identified by spectral methods.

Claims (2)

SUBJECT 1. N- [2- (p-tert-butylphenoxyacetoxy) ethyl] -1,5-dimethylalkylammonium bromides of the formula VYNALEZU CH and CH-C- ³ I CH, CH, O-CH 2 CO- (CH ₂ ) _z -NR CHn Wherein R is an alkyl chain having a carbon number of 8 to 16. 2. A process for the preparation of compounds of the general formula as in 1, characterized by reacting (2-dimethylaminoethyl) - (p-tert-butylphenoxy) acetate of the formula: CH C H <rC - O - CMg C - O iC i CH, with 1-bromoalkane of the general formula R-Br, where R is the same as in 1, in a dry methyl cyanide or methanol medium at temperatures of 40 ° C for 100 ° C for 6-18 hours.