CS230340B1 - N,n-bis/alkyldimethyl/p-3-aza-3-dodecyl-1,5-pentadiammonium bromides and method of preparing same - Google Patents

Description

(54) N, N '-bis (alkyldimethyl) -3-aza-3-dodecyl-1,5-pentanediammonium dibromides and process for their preparation

2

The invention relates to N, N '-bis (alkyldimethyl) -3-aza-3-dodecyl-1,5-pentanediammonium dibromides of the general formula

CH

© R-N - (CH 2) 2 N (CH2) 2

CH3 (CH2) 11CH3

CH3

I - © N — R 2 Br

CH3 wherein R is an alkyl chain having a carbon number of 3 to 12 and a method of preparation consisting in the reaction of bis (2-dimethylaminoethyl) dodecylamine with 1-bromoalkane in methyl cyanide, ethanol or methanol at the boiling point of the solvent for 2 hours.

Finally, the compounds exhibit activity against Gram-positive, Gram-negative bacteria and yeast and are therefore useful for disinfection as antimicrobial active compounds. In addition, they have post-active properties.

The invention relates to N, N'-bis (alkyldimethyl) -3-aza-3-dodecyl-1,5-pentanediammonium dibromides of the general formula

CH3

© R-N - (CH 2) 2 N (CH2) 2

CIL C12H25

CH3 - © N — R 2 Br

CH 3 wherein R represents an alkyl chain having a carbon number of 3 to 12 and a process for their preparation.

It is known that some organic mono and bisammonium salts derived from both aliphatic and aromatic and heterocyclic amines have found widespread use in both industry and medicine. Compounds containing at least one long alkyl chain in the molecule also benefit from their preferred surface-active properties. In addition, many of the organic ammonium salts also exhibit biological effects. So eg. Ajatin (benzyldimethyldodecylammonium bromide) or Septonex (2-) ethoxycarbonyl (pentadecyl) trimethylammonium bromide are some of the most widespread disinfectants. Compounds of the bisammonium salt group such as e.g. hexamethonium (N, N‘-histrimethyl-l, 6-hexanediammonium dibromide) or decamethonium (N, N‘-bistrimethyl-l, 10-decanediammonium dibromide) are ganglioplegic and respiratory compounds, respectively. curareform effect. Similar azamethonium (3-aza-N, N-bis (ethyldimethyl) -3-methyl-1,5-pentanediammonium dibromide or dichloride, respectively) is one of the highly potent ganglioplegics.

The compounds of the present invention have not been described in the chemical literature to date and have been found to have unknown effects on microorganisms. In the most effective of these, their antimicrobial activity is higher than that of Ajatin and comparable to Septonex.

Compounds of this type can be prepared in a variety of ways, most often utilizing the reaction of halogenated hydrocarbon derivatives with the corresponding tertiary amines under various reaction conditions and in various solvents. Variable purity products are visualized in a fluctuating yield.

The process according to the invention consists in reacting bis (2-dimethylaminoethyl) -dodecylamine with 1 to 14 carbon atoms in 1 to 14 carbon atoms in a medium of methyl cyanide, ethanol or methanol at the boiling point of the solvent for 2 hours to produce products in high yield. .

In the examples I illustrate! but not limiting the method of preparation, the present invention is described and selected compounds are characterized. Antimicrobial activity expressed as minimum inhibitory concentration (MIC) v, wg / cm ³ for Staphylococcus aureus, Escherichia coli and Camdida albicans is also reported.

Example 1

0.1 mol of bis (2-dimethylaminoethyl) dodecylamine and 0.2 mol of 1-bromopropane are dissolved in 30 ml of methyl cyanide and heated under reflux for 2 hours. Then the solvent is distilled off and the product, N, N'-bis (dimethylpropyl) -3-aza-3-dodecyl-1,5-pentanediammonium dibromide, is recrystallized to a constant melting point from acetone. T. t. Mp 123-125 ° C; yield 90% of theory; Rf ₍ acetone: 1 M HCl: 1, Silufol, detection by Dragendorf reagent in Munier modification) = 0.61; MIC: 5.30.20.

Example 2

The procedure was the same as in Example 1 except that 1-bromopentane was used in the reaction and the reaction medium was ethanol. The product is N, N'-bis (dimethylpentyl) -3-aza-3-dodecyl-1,5-pentanediammonium dibromide, mp 128-130 ° C; yield 75% of theory; _Rf = 0.61; MIC 8,30,6.

Example 3

The procedure was the same as in Example 1 except that 1-bromononane was used in the reaction and the reaction medium was methanol. The product is N, N'-bis (dimethylnonyl-3-aza-3-dodecyl-1,5-pentanediammonium dibromide, mp 134-136 ° C; yield 84% of theory; R _f = 0.63; MIC: 6.20, 20. Example 4

The procedure is the same as in Example 1 except that 1-bromododecane was used in the reaction and the reaction medium was ethanol. The product is N, N'-bis (dodecyldlmethyl) -3-aza-1,5-pentanediammonium dibromide, mp 138-140 ° C; yield 94% of theory; _Rf = 0.44; MIC: 50,100.30.

Claims (2)

OBJECT OF THE INVENTION N, N '-bis (alkyldimethyl) -3-aza-3-dodecyl-1,5-pentanediammonium dibromides of the formula CH3 I R - N - [CH 2] 2 '- N - (CH 2) CH 3 (CH 2 CH 2 CH CH ₃ I - © N — R CH3 Wherein R represents an alkyl chain having a carbon number of 3 to 12. 2. A process for the preparation of compounds of the general formula as in 1, characterized by reacting bis (2-dimethylaminoethyl) dodecylamine of the formula: CHs CH3 N - (CH ₂ ) 2 -N- (CH 2) 2 -N CH3 (CH2J11CH3 CH3 having 1 to 14 carbon atoms in the chain of 1 to 14 carbon atoms in the medium of methyl cyanide, ethanol or methanol at the boiling point of the solvents for 2 hours.