CS229093B1 - N, N "-bis (alkyldimethyl) -3-aza-3-methyl-1,5-pentanediammonium dibroniides and their method of preparation - Google Patents

Abstract

The invention relates to N,N,/-bis(glycyldimethyl)-3-aza-3-methyl-1,5-pentanediammonium dibromides of the general formula ch3 ch3 R-N®-(CH~)0-N-(CH-)-- ©N-R 2 Br © I I I CH3 ch3 ch3 I where R denotes an alkyl chain with the number of carbon atoms from 8 to 16 and the method of their preparation, which it is based on the reaction of bis(2-dimethylaminoethyl)methylamine with 1-bromoalkanes in the environment of methyl cyanide, ethanol or methanol at the boiling temperature of the solvent for 2 hours. Finally, the compounds show an effect against gram-positive, gram-negative bacteria and yeasts and are therefore useful for disinfection as antimicrobial compounds. In addition, they also exhibit surface-active properties.

Description

229093 2

The present invention relates to N, K '' - bis (alkyldimethyl) -3-aza-3-methyl-1,5-pentanediammonium dibromide of the general formula R-N (R) -N- (CH) O-N-R 2 Br ©

Where R represents an alkyl chain having from 8 to 16 carbon atoms and a preparation thereof.

It is known that some non-aromatic organic long-chain alkyl mono- and bis-ammonium salts have been extensively used in the industry due to their surface-active properties or biological effects. For example, benzyldodecyldimethylammonium bromide (Ajatine), similar to 2 - [(ethoxycarbonyl) pentadecyl] trimethylammonium bromide (Septonex), is among the most widely disinfected. Similar N, N ' -bistrimethyl-1,6-hexanediammonium dibromide (hexamethonium) and N, N ' -bistrimethyl-1,10-decanediammonium dibromide (decamethonium) belong to the compounds with a pronounced gangllo blocking and / or decomposition. curative effect. One of the bis (2-aminoethyl) amine-3-aza-N, N ' -bis (ethyldimethyl) -3-methyl-1,5-pentanediammonium dibromide or dichloride (azamethonium) derivatives is also one of the oldest but highly effective gang-lioplegik.

The compounds of the present invention have not been described in the chemical literature to date and have not yet been known to have an effect on microorganisms. In the most effective of these, their antimicrobial activity is enhanced, such as the efficacy of Ajatin or Septonex.

Compounds of this type can be prepared by various methods, the reaction of halogen derivatives of hydrocarbons with the corresponding tertiary amines under conditions of high dilution and solvent is most often used. Variable purity products of variable purity are produced.

The preparation according to the invention has the advantage that the reaction is carried out in medium methyl cyanide, ethanol or methanol at the boiling point of the solvent for 2 hours, producing high-purity high-yield products. In the examples which illustrate, but do not limit, the method of preparation, the invention is disclosed and selected compounds are characterized. Antimicrobial activity expressed as the minimum inhibitory concentration (MIC) in yug / ml is also reported for Staphylococcusaureus, Escherichia coli and Candida albicans. 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 was heated to reflux for 2 hours, then dissolved in vacuo, the crude product was stripped of residual moisture and recrystallized to a constant melting point from acetone. 3-Aza-N, N ' -bis (dimethylnonyl) -3-methyl-1,5-pentanediamine dibromide is formed. 223-224 ° C (yield 82% of theory); (system acetone: 1 N HC11: 1, Silufol, detection by Dragendorf reagent in Munier modification) = 0.74; MIC: 1, 400, 100.

Claims (2)

3 229093 Example 2 The working procedure is the same as in Example 1 except that ethanol is used as the solvent instead of cyanide and 1-bromo-undecane as the substrate instead of 1-bromononane. -bis (dimethylundecyl) -3-methyl-1,5-pentanediammonium dibromide with tt 228-229 ° C; yield 83% of theory; Rf = 0.62; MIC: 4, 20, 30. Example 3 The working procedure is the same as in Example 1 except that it used methanol as the solvent instead of cyanide and 1-bromo-hexadecane was used as the substrate instead of 1-bromononane. 3-Aza-N, N ' -bis (hexadecyldimethyl) -3-methyl-1,5-pentanediammonium dibromides mp 223.5-225 ° C, 77% yield, Rf = 0.06, MIC: 70.600, 400 OBJECT OF THE INVENTION 1. N, N'-bisalkyldimethylD-S-aza-S-methyl-1,5-pentanediammonium dibromides of the general formula .CH, CH, I (+) (¢) 1 Q RN W- (CH 2) -, - N- (CH 2) 2 -NR 2 Br OIII CH 3 CH 3 CH 2 where R represents an alkyl chain having from 8 to 16 carbon atoms. 2. A process for the preparation of compounds of formula (1), characterized in that the bis (2-dimethylaminoethyl) methylamine of the formula CH-CH1-N- (CH2) -N- (CH3) -N- (2) is reacted. CH3 CH3 CH3 is a 1-bromoalkane containing 8 to 16 carbon atoms in the chain in the medium of cyanide, ethanol or methanol at the boiling point of the solvent for 2 hours.