CS245099B1 - N,n'-bis(alkyldimethyl)-3-oxa-1,5-pentandiamoniumdibromides and method of their preparation - Google Patents

Description

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

R (CH 3) 2 N (CH 2) 2 O (CH 2) 2 N (CH 3) 2 R 2 Br - wherein R represents a linear alkyl chain having a carbon number of 6, 7, 9 to 16 and a process for preparing these compounds by reacting of the corresponding N, N-dimethylalkylamine with 3-oxa-1,5-dibromopentane in methyl cyanide medium at the boiling point of the solvent for 12 to 48 hours, optionally by reaction of N, N'-bis-diinetyl-3-oxa-1,5-pentanediamine with 1-bromoalkanes in methyl cyanide at 20-60 ° C for 12 hours.

Finally, the compounds have a broad-spectrum antimicrobial effect on gram-positive, gram-negative bacteria and yeasts, and at the same time possess significant surfactant properties. The most effective of these are useful as disinfectants with detergent properties in pharmacy, cosmetics, light industry, etc., wherever either their surfactant properties or antimicrobial effects can be utilized, or a combination of both.

The present invention relates to N, N‘-bis (alkyldimethyl) -3-oxa-1,5-pentanediammonium dibromides of the formula

R (CH 3) 2 N (CH 2) 2 O (CH 2) 2 N (GH 3) 2 R 2 Br 2 wherein R represents a linear alkyl chain having a carbon number of 6, 7, 9 to 16 and a process for preparing these compounds.

The ganglioplegic effect of bisammonium salts containing up to six carbon atoms in the linker chain has been well known for a long time. Such compounds have also found application in clinical practice (pentamethonium, hexamethonium, pentolinium), as well as compounds with isostere interchange at the 3-position (NCHs, Sj, such as pendiomide, thiamethone. Oxygen analogues in the form of chlorides, bromides and iodides From the long-chain isomers, octyl in the form of bromide and octadecyl in the form of chloride are known, the two derivatives having a ganglioplegic effect and a surface activity.

However, the compounds of the invention have not yet been described in the chemical literature and have been found to have unknown surfactant properties and effects against microorganisms of different types.

A process for preparing these bisammonium salts consists in reacting 3-oxa-1,5-dibromopentane with the corresponding N, N-dimethylalkylamines or N, N'-bis (dimethyl) -3-oxa-1,5-pentanediamine with 1-bromoalkanes in the environment methyl cyanide at 20 ° C to the boiling point of the solvent for 12 to 48 hours Thin layer chromatography, partition chromatography, elemental analysis and IR spectroscopy confirmed that high purity compounds were formed.

The examples illustrate but do not limit the method of preparation of the compounds of the invention. Besides theory, mp _Rf value (slllkagel, system acetone - 1 N HC1 1: 1, detection Dragendorfovým agent in Munierovej modification], the IR spectral characteristics (as measured by nujol mull, vlnopočet in cm ^1), said well as critical concentration of micelle formation (mol dm ^-3 ), maximum reduction of surface tension at Ck (/ _c , niN.ni ¹ ), as well as antimicrobial k

activity against Staphylococcus aureus, Escherichia coli and Candida albicans expressed as the minimum inhibitory concentration in µg.

. cm ^-3 .

Example 1

0.075 mol of 3-oxa-1,5-dibromopentane is dissolved in 30 cm ^{3 of} methyl cyanide, 0.15 mol of Ν, Ν-dimethylhexylamine is added and the reaction mixture is allowed to react at the boiling point of the solvent for 12 hours. The volatiles were then evaporated and the product was recrystallized to a constant melting point from acetone-ethanol. N, N'-bis (hexyldimethyl) -3-oxa-1,5-pentanediammonium dibromide is obtained in 93.9% yield, mp 222-224 ° C;

R (= 0.65;

[nu] C-O 1145, 1125;

Pcn 723;

C _k = - 9.89. 10 ~ ² ;

Yc = 36.2; to

MIC: 1,000, 4,000, 2,000.

Example 2

The procedure was the same as in Example 1 except that N, N'-bisdimethyl-3-oxa-1,5-pentanediamine and 1-bromononane were used in the reaction and the reaction was carried out at 20 ^° C. N'-bis (nonyldimethyl) -3-oxa-1,5-pentanediammonium dibromide in 97.6% yield;

t. t. 255-257 ° C;

_Rf = 0.61;

[nu] C-o-c 1144, 1 127;

Pch 720;

C _k = 2.22. 10 ~ ² ;

Yc = 37.4; to

MIC: 10, 90, 100.

Example 3

The procedure is the same as in Example 2, except that 1-bromo-decanoe was used in the reaction instead of 1-bromo-nano and the temperature was maintained at about 60 ° C. N, N‘-bis (undecyldimethyl) -3-oxa-1,5-pentanediammonium dibromide was obtained in a yield of 91.4%;

t. t. 256-258 ° C;

Rf = 0.58;

[nu] C-O-c 1143, 1128;

Pcn 719;

C _k = 2.59.10-3;

Zc = 37.5;

MIC: 4, 20, 9.

Example 4

The procedure is the same as in Example 1, except that N, N-dimethylhexadecylamine is used instead of esto, Ν-dimethylhexylamine and the reaction mixture is allowed to react for 48 hours. N, N‘-bis (hexadecyldimethyl) -3-oxa-1,5-pentanediammonium dibromide is obtained in a yield of 92.3%;

t. t. Mp 234-236 ° C;

_Rf = 0.44;

v _c- o 1130, 1117;

Pcii 718;

C _k = 6.38.10 ⁶ ;

Zc = 42.9;

MIC: 80, 300, 90.

Claims (3)

1. N, N‘-Bis (alkyldimethyl) -3-oxa-1,5-pentanediammonium dibromides of the general formula: R _(CH3) 2 N © (CH 2) 2 O (CH 2) 2 © N (OH3) 2 R 2 Br wherein R © is a straight chain alkyl having a carbon number 6, 7, 9 to 16. 2. A process for the preparation of compounds of the general formula as in 1, characterized in that 3-oxa-1,5-dibromopentane of the formula is reacted. Br - (CH2) 2-O- (CH2) 2-Br with Ν, Ν-dimethylalkylamines of general formula Wherein R has the same meaning as in point 1, at the boiling point of methyl cyanide, which serves as a solvent for 12 to 48 hours. 3. A process for the preparation of compounds of formula (I) as defined in claim 1, which comprises reacting N, N'-bisdimethyl-3-oxa-1,5-pentanediamine of formula (CH3) 2N (CH2) 20 (OH2) 2N (CH3). 2 with 1-bromoalkanes of the general formula R-Br wherein R is the same meaning as in point 1, in methyl cyanide at 20 to 60 ° C for 12 hours.