CS239430B1 - N, N'-bis ((alkoxycarbonylmethyl) dimethyl) -1,2-ethanediammonium dibromides and their method of preparation - Google Patents
N, N'-bis ((alkoxycarbonylmethyl) dimethyl) -1,2-ethanediammonium dibromides and their method of preparation Download PDFInfo
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Abstract
Vynález sa týká N,N -bis/(alkoxykarbonylmetyl)dlmetyl/-1,2-eténdiemónlumdibromldov všeobecného vzorca CH, CH, R-0-C-CH2-+N-CH2-CH2-N+-CH2-C-0-R 2 Br CH, CH, kde R znamená lineárny alebo rozvětvený alkylový reťasec s počtom atomov uhlíka 6 až 16 alebo p-terc.butylfenyl a apOsobu přípravy týchto zlúčenín, ktorý spočívá v reakcií príeluSného esteru kyseliny bromoctovej s N,N -bisdimetyl-1,2-etándiamlnom v prostředí metylkyanidu pri teplotách 20 až 80 °C. Pinálne zlúčeniny majú výrazné povrchovoaktlvne vlastnosti a antimikróbny účinok tak na grampozltívne a gramnegatívne baktérie ako aj na kvasinky a preto sú použitelné, najúcinnejSle z nich, na dezinfekclu, konzerváciu, ako pomocné povrchovoaktlvne látky a pod..The invention relates to N,N -bis/(alkoxycarbonylmethyl)dimethyl/-1,2-ethenediamine dibromides of the general formula CH, CH, R-O-C-CH2-+N-CH2-CH2-N+-CH2-C-O-R 2 Br CH, CH, where R represents a linear or branched alkyl chain with 6 to 16 carbon atoms or p-tert.butylphenyl and a method for preparing these compounds, which consists in reacting the corresponding bromoacetic acid ester with N,N -bisdimethyl-1,2-ethanediamine in a methyl cyanide environment at temperatures of 20 to 80 °C. Pineal compounds have significant surface-active properties and antimicrobial effects on both gram-positive and gram-negative bacteria and yeasts, and are therefore useful, most effectively, for disinfection, preservation, as auxiliary surfactants, etc.
Description
239430 2
Vynález sa týká H,N'-bie/(alkoxykarbonyl)dimetyl/-1,2-etándiamóniumdibromidov vše-obecného vzorca
kde R znamená lineárny alebo rozvětvený alkylový retazec a počtom atoaov uhlíka 6 až 16alebo p-terc.butylfenyl a spOsobu přípravy týchto zlúčenín.
Je známe, Se dlhoreťazcové organické amoniové soli výkazujú okrem velmi dobrýchpovrchovoaktívnych vlastností aj výrazné biologické účinky. NaSli použitle ako vysoko-účinné dezinfekčné prostriedky v zdravotnickéj praxi, v komunálněj hygienie, vo farmácii,v kozmetike, ale aj v 1'ahkom a ťažkom priemysle.
Popři vysokej dezinfekčněj účinnosti majú vSak aj rad negativných vedlejších účinkovako napr. poměrně vysoků toxicitu a dráždivosť. Preto je snahou modifikovat molekulytakýchto zlúčenín skupinami blízkými organizmu (esterová, amidová, hydroxylová, amino,atň.) a eielom zachovat ich vysokú biologická aktivitu ale znížiť vedlajSie nežiaduceúčinky. V chemickej literatáre boli opísané dialkylestery N,N'-bis(karboxymetyl)-N,N,N',N'--tetrametyléndlamoniumdichloridy, z kterých decylderivát sa používá pod názvom Ethoniumako lokálně anestetikum s antimikrobnym účinkom. NaSiel tiež využitie v analytickej chérail,pri prlprave a úpravě vlastností polymérov, pri elektroforetickom nanáSenl kovov na povrchyz umělých hmOt, v biochémii.
Zlúčeniny, ktoré sú predmetom vynálezu nie sú v chemickej literatáre doteraz opísanéa zistili sa u nich doteraz neznáme bilogické účinky.
Organické amoniové soli sa pripravujú najčastejSie substitučnou nikleofilnou reakcioupříslušných halogénderivátov s terciárnymi amlnmi za rOznych podmienok, pričom výtažkyako aj čistota produktov sú variabilné.
Zlúčeniny, ktoré sú predmetom vynálezu sa připravili reakciou esterov kyseliny brom-octovej β N,N -bisdimetyl-1,2-etándlamlnom v prostředí metylkyanidu pri teplotách 20 až80 °C počas 2 ai 4 h. Výhodou spčsobu podl’a vynálezu je, Se vznikájú produkty takmerv kvantitatívnom výtažku, velmi čisté v poměrně krátkom čase. Připravené soli sú ne-hygroskopické, nižšie homology sú dobré rozpustné vo vodě a polárných rozpúStadlách,nerozpustné v nepolárných rozpúStadlách. Příklad ilustruje vSeobecnú metodu přípravy zlúčenín podlá vynálezu, ktoré sú cha-rakterizované v tabulko. Je uvedená aj antimikrobna aktivita vyjádřená ako minimálnainhibičná koncentrácia (MIC) v /ug.cm“^ resp. mmol.dm-^ na kmene Staphylococcus aureus(s.a.), Escherichia coli (E.c.) a Candida albicans (C.a.). V porovnaní s Ajatlnom (benzyldodecyldimetylaméniumbromid) sú najúčinnejSie zlúčeniny,ktoré sú predmetom vynálezu, účinnejšie na grampozitívne baktérie S. aureus 2-x, na gra-negatívne baktérie E. coli 4-x, aktivita na kvasinky C. albicans je srovnatelná. Okremantimlkróbneho účinku sa stanovila aj povrchová aktivita zo zmien povrchového napštia v závislosti na koncentrácli. V tabulke je uvedená hodnota Y q (zníženie povrchového napatia na medzifázovom roz-hraní voda - vzduch pri kritickéj koncentrácli tvorby miciel C^). sa stanovila aj 3 239430 konduktoawtrieky a straní asien voditoatl v sívialoati na měnách konctntrícle a primárníhodnota a oboch aeraní jo uvedení v tabulko. Taktiet eú uvedení spektrálné cbaraktarlatikyalúCenín, ktorá aú předaňte· vynálesu. Hodnoty a překovej analýay holi v ráaci chybyaetody 10,3 4. Příklad V 30 ca^ aetylkyanidu aa roapuatl 0,1 aol M,N -biadimtyl-1,2-etándiaaínu a pcaaly•a přidá 0,2 aol esteru kyseliny bróaoctovej. Saakcia je exoteraioká a tplota aa aa-aovoXne avýSi a pdvodnýoh 20 na M *C, kde aa udráuje 2 h. Po ochladení a odpaření roa-púátadla aa aíaka produkt, který aa kryitaliaujedo konátantnej teploty topenia ao meaiaceton - aetanol. Ciatota aa okrm překovej analýay, iC-spektier sledovala a) tenkovratevnouchreaatoerafiou (celulóaa) v aúatave butanol - kyselina octová - voda, detekcia Dra<en-dorfovýa Činidla·. 239430 oaot"Omo<woNo^Q0to<o»"O<no^ot»Q£oetOř*^· ·-’·- - — © *- O O <-©>Μ©ΟΙ©Ζ|Α(* o;
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239430 2
The present invention relates to H, N'-bia [(alkoxycarbonyl) dimethyl] -1,2-ethanediammonium dibromides of the general formula
wherein R is a linear or branched alkyl chain and a number of carbon atoms of 6 to 16 or p-tert-butylphenyl and a process for preparing such compounds.
It is known that, in addition to very good surface-active properties, long-chain organic ammonium salts also exhibit significant biological effects. NaSli has been used as a highly effective disinfectant in medical practice, in community hygiene, in pharmacy, in cosmetics, but also in the industry and in the heavy industry.
However, in addition to the high disinfection efficiency, a number of negative side effects, such as relatively high toxicity and irritability, have also been reported. Therefore, it is desirable to modify the molecules of such compounds by groups close to the organism (ester, amide, hydroxyl, amino, etc.) to maintain their high biological activity but to reduce the side-effects. In the chemical literature, dialkyl esters of N, N'-bis (carboxymethyl) -N, N, N ', N' - tetramethylenedlammonium dichlorides have been described, of which the decyl derivative is used under the name Ethonium as a topical anesthetic with antimicrobial activity. It has also been used in analytical chemistry, in the preparation and conditioning of polymers, in the electrophoretic deposition of metals on the surface of artificial plastics, in biochemistry.
The compounds of the invention not previously described in the chemical literature have been found to have no known biological effects.
The organic ammonium salts are most often prepared by the substitution nickelophilic reaction of the respective halogenated derivatives with tertiary amines under different conditions, and the product purity is variable.
The compounds of the present invention were prepared by reacting bromoacetic acid esters with N, N-bis-dimethyl-1,2-ethanediamine in methyl cyanide at 20 to 80 ° C for 2 to 4 hours. the products of takmerv are produced quantitatively, very clean in a relatively short time. The salts prepared are non-hygroscopic, the lower homologues are good water-soluble and polar solvents insoluble in non-polar solvents. The example illustrates a general method for preparing compounds of the invention which are characterized in a table. Antimicrobial activity, expressed as minimal inhibitory concentration (MIC) in /ug.cm, is also shown. mmol.dm- to strains of Staphylococcus aureus (sa), Escherichia coli (Ec) and Candida albicans (Ca). Compared to Ajatl (benzyldodecyldimethylammonium bromide), the most effective compounds of the present invention are more potent on Gram-positive bacteria S. aureus 2-x, on negative E. coli bacteria 4-x, the activity on C. albicans is comparable. In addition to the antimicrobial effect, surface activity was also determined from surface tension changes in a concentration-dependent manner. In the table, the value of Y q (reduction of surface tension at the interfacial extent of water-air at critical concentration of formation of micelles) is shown. 3 239430 Conductoawrots were also determined and the Asien voditoatl in sivialoati on currencies and primary value, and both aerani yo were listed in the table. Taktiet eu introduction of spectral cbaractarlatikyalúCénin, which to transmit. Values and overhang analysis of the rod at error 10,3 4. Example V of 30 c a-ethyl cyanide and roapuatl of 0.1 aol of M, N-biadimtyl-1,2-ethanediaine and add and add 0.2 aol of bromoacetic acid ester. The reaction is exothermic and aa and aa-avoxy and 20 to M < + > C, where aa is measured for 2 hours. After cooling and evaporation of the roating agent and any product which has a constant melting point and acetone-acetone. Cotaota and a cross-over analysis, iC-spectra followed by a) thin-cell chromatography (cellulose) in butanol-acetic acid-water, detection of Dra-enorphine reagent. 239430 oaot "Omo <woNo ^ Q0to <o» "O <no ^ ot» Q £ oetOr * ^ · · - '- - - © * - OO <- ©> © ΟΙ © Ζ | Α (* o;
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS843553A CS239430B1 (en) | 1984-05-14 | 1984-05-14 | N, N'-bis ((alkoxycarbonylmethyl) dimethyl) -1,2-ethanediammonium dibromides and their method of preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS843553A CS239430B1 (en) | 1984-05-14 | 1984-05-14 | N, N'-bis ((alkoxycarbonylmethyl) dimethyl) -1,2-ethanediammonium dibromides and their method of preparation |
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| Publication Number | Publication Date |
|---|---|
| CS355384A1 CS355384A1 (en) | 1985-05-15 |
| CS239430B1 true CS239430B1 (en) | 1986-01-16 |
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| Application Number | Title | Priority Date | Filing Date |
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| CS843553A CS239430B1 (en) | 1984-05-14 | 1984-05-14 | N, N'-bis ((alkoxycarbonylmethyl) dimethyl) -1,2-ethanediammonium dibromides and their method of preparation |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0427224A1 (en) * | 1989-11-08 | 1991-05-15 | Kao Corporation | Novel polycationic compound and bleach composition containing the same |
-
1984
- 1984-05-14 CS CS843553A patent/CS239430B1/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0427224A1 (en) * | 1989-11-08 | 1991-05-15 | Kao Corporation | Novel polycationic compound and bleach composition containing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| CS355384A1 (en) | 1985-05-15 |
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