CS229093B1 - N,n-bis/alkyldiemethyl/-3-aza-3-methyl-1,5-pentanediammoniumdibromides and method of preparing same - Google Patents

Abstract

The invention relates to N, N, N -bis (glycidimethyl) - -3-aza-3-methyl-1,5-pentanediammonium dibromides formula ch3 ch3 R-N®- (CH-) O-N- (CH -) - NN-R 2Br. I I I CH3 ch3 ch3 AND wherein R is an alkyl chain number of carbon 8 to 16 and the method of their preparation, which comes from the reaction of bis (2-dimethylaminoethylmethylamine) with 1-bromoalkanes in a medium of cyanide, ethanol or methanol at the boiling point of the solvent during 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 also exhibit surface-active properties Properties.

Description

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

_R N - (CH _O ) n - N - (CH n) _O - N NR 2 Br

I ^{2 2} 1 ^{2 2} I

CH ₃ CH ₃ CH ₃ wherein R is an alkyl chain having a carbon number of 8 to 16 and a Process in the preparation.

It is known that some non-aromatic organic mono-and bisammonium salts with long alkyl chains have found widespread use in industry due to their surface-active properties or biological effects. So eg. benzyldodecyldimethylammonium bromide (Ajatin), similar to 2 - [(ethoxycarbonyl) pentadecyl] trimethylammonium bromide (Septonex), is currently one of the most widespread disinfection agents. Similar N, N * -bistrimethyl-1,6-hexanediammonium dibromide (hexametonium) and N, N'-bistrimethyl-1,1O-decanediammonium dibromide (decametonium) are among the compounds with pronounced ganglioblocking and respiratory depletion, respectively. curareform effect. Also one of the bis (2-aminoethyl) amine-3-aza-N, N-bis (ethyldimethyl) -3-methyl-1,5-pentenediammonium dibromide derivatives, respectively. Dichloride (azamethonium) is one of the oldest but highly effective ganglioplegics.

The compounds of the present invention have not been described in the chemical literature until now 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 or Septonex.

Compounds of this type can be prepared by conventional methods, most commonly using the reaction of halogenated hydrocarbon derivatives with the corresponding tertiary amines under controlled conditions and in diluent solvents. Variable purity products are produced in a fluctuating extract.

The preparation methods of the invention have the advantage that the reaction is carried out in a medium of methyl cyanide, ethanol or methanol at the boiling point of the solvent for 2 hours, whereby high purity products are obtained in high yield.

In the examples, which illustrate but do not limit the method of preparation, the invention is described and selected compounds are characterized. Antimicrobial activity expressed as minimum inhibitory concentration (MIC) in yug / ml on Staphyloooccus aureus, Escherichia coli, and Candida albicans is also reported.

*

Example 1

0.1 mol of bis (2-dimethylaminoethyl) methylamine and 0.2 mol of 1-bromononane are dissolved in 30 ml of methyl cyanide. The reaction mixture is heated at reflux for 2 hours, then the solvent is evaporated off under vacuum, the crude product is freed from residual moisture and recrystallized to constant melting point from acetone. There was thus obtained 3-aza-N, N'-bis (dimethylnonyl) -3-methyl-1,5-pentanediammonium dibromide, m.p. Mp 223-224 ° C; yield 82% of theory, (acetone: 1N HCl 1: 1, Silufol, detection by Dragendorf reagent in Munier's modification) = 0.74; MIC: 1,

400, 100.

Example 1 a d 2

The procedure is the same as in Example 1, except that ethanol is used as the solvent instead of methyl cyanide and 1-bromo-decane is used as a substrate instead of 1-bromonane. 3-Aza-N, N ' -bis (dimethylundecyl) -3-methyl-1,5-pentanediammonium dibromide was obtained with mp 228-229 [deg.] C .; yield 83% of theory; _Rf = 0.62; MIC: 4, 20, 30.

Example 3

The procedure is the same as in Example 1 except that methanol is used instead of methyl cyanide and 1-bromohexadecane is used as a substrate instead of 1-bromonane. 3-Aza-N, N-bis (hexadecyldimethyl) -3-methyl-1,5-pentanediammonium dibromide was obtained with mp 223.5-225 ° C; yield 77%; _Rf = 0.06; MIC: 70, 600, 400.

Claims (2)

N, N'-bisalkyldimethyl-D-S-aza-S-methyl-1,5-pentanediammonium dibromides of the general formula: CH. CH. I (+) (Q) 1 Q RN ^W - (CH 2) -N- (CH 2) -, -NR 2 BrO I I I CH ₃ CH ₃ CH wherein R is an alkyl chain with a number of carbon atoms between 8 to 16. 2. A process for the preparation of compounds of the general formula as in 1, characterized by reacting bis (2-dimethylaminoethyl) methylamine of the formula CH, CH, I I N- (CH 2), -N- (CH 2), -N 1 ^{2 2} I CH ₃ CH ₃ CH ₃ with 1-bromoalkane having 8 to 16 carbon atoms in the chain in a medium of methyl cyanide, ethanol or methanol at the boiling point of the solvent for 2 hours.