CS230340B1 - N,n-bis/alkyldimethyl/p-3-aza-3-dodecyl-1,5-pentadiammonium bromides and method of preparing same - Google Patents
N,n-bis/alkyldimethyl/p-3-aza-3-dodecyl-1,5-pentadiammonium bromides and method of preparing same Download PDFInfo
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- CS230340B1 CS230340B1 CS2183A CS2183A CS230340B1 CS 230340 B1 CS230340 B1 CS 230340B1 CS 2183 A CS2183 A CS 2183A CS 2183 A CS2183 A CS 2183A CS 230340 B1 CS230340 B1 CS 230340B1
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- Czechoslovakia
- Prior art keywords
- bis
- aza
- dodecyl
- alkyldimethyl
- pentadiammonium
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 10
- 150000001649 bromium compounds Chemical class 0.000 title 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 8
- -1 bis (2-dimethylaminoethyl) dodecylamine Chemical compound 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 230000000845 anti-microbial effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- KHSLHYAUZSPBIU-UHFFFAOYSA-M benzododecinium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 KHSLHYAUZSPBIU-UHFFFAOYSA-M 0.000 description 2
- FXQJFHYFOGHZTB-UHFFFAOYSA-M carbethopendecinium bromide Chemical compound [Br-].CCCCCCCCCCCCCCC([N+](C)(C)C)C(=O)OCC FXQJFHYFOGHZTB-UHFFFAOYSA-M 0.000 description 2
- 230000002005 ganglioplegic effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- UWDJNLFBSSXKIX-UHFFFAOYSA-M (2-ethoxy-2-oxoethyl)-dimethyl-pentadecylazanium bromide Chemical compound [Br-].CCCCCCCCCCCCCCC[N+](C)(C)CC(=O)OCC UWDJNLFBSSXKIX-UHFFFAOYSA-M 0.000 description 1
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 1
- AYMUQTNXKPEMLM-UHFFFAOYSA-N 1-bromononane Chemical compound CCCCCCCCCBr AYMUQTNXKPEMLM-UHFFFAOYSA-N 0.000 description 1
- YZWKKMVJZFACSU-UHFFFAOYSA-N 1-bromopentane Chemical compound CCCCCBr YZWKKMVJZFACSU-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- NKOTXYPTXKUCDL-UHFFFAOYSA-N 4-(trifluoromethyl)pyrimidin-2-amine Chemical compound NC1=NC=CC(C(F)(F)F)=N1 NKOTXYPTXKUCDL-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229950000405 decamethonium Drugs 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- NHWGPUVJQFTOQX-UHFFFAOYSA-N ethyl-[2-[2-[ethyl(dimethyl)azaniumyl]ethyl-methylamino]ethyl]-dimethylazanium Chemical compound CC[N+](C)(C)CCN(C)CC[N+](C)(C)CC NHWGPUVJQFTOQX-UHFFFAOYSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229950002932 hexamethonium Drugs 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 description 1
- HLXQFVXURMXRPU-UHFFFAOYSA-L trimethyl-[10-(trimethylazaniumyl)decyl]azanium;dibromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCCCCCCC[N+](C)(C)C HLXQFVXURMXRPU-UHFFFAOYSA-L 0.000 description 1
- PYIHTIJNCRKDBV-UHFFFAOYSA-L trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;dichloride Chemical compound [Cl-].[Cl-].C[N+](C)(C)CCCCCC[N+](C)(C)C PYIHTIJNCRKDBV-UHFFFAOYSA-L 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
(54) N,N“-bis(alkyldimetyl)-3-aza-3-dodecyl-l,5-pentándiam6niumdibromidy a sposob ich pripravy(54) N, N '-bis (alkyldimethyl) -3-aza-3-dodecyl-1,5-pentanediammonium dibromides and process for their preparation
22
Vynález sa týká N,N“-bís(alkyldimetyI)-3-aza-3-dodecyl-l,5-pentándiamóniumdibromidov všeobecného vzorcaThe invention relates to N, N '-bis (alkyldimethyl) -3-aza-3-dodecyl-1,5-pentanediammonium dibromides of the general formula
CHsCH
R—N©—(CH2)2—N-(CH2)2—© R-N - (CH 2) 2 N (CH2) 2
CH3 (CH2)llCH3CH3 (CH2) 11CH3
CH3CH3
I —©N—R 2 Br©I - © N — R 2 Br
CH3 kde R značí alkylový reťazec s počtom atómov uhlíka 3 až 12 a sposobu leh pripravy, ktorý spočívá na reakcii bis(2-dimetylaminoetyljdodecylamínu s 1-brómalkánom v prostředí metylkyanidu, etanolu alebo metanolu pri teplote varu rozpúšťadla počas 2 hodin.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.
Finálně zlúčeniny vykazujú účinok voči grampozitívnym, gramnegatívnym baktériam a 'kvasinkám a preto sú použitelné na dezinfekciu ako antimikróbne účinné zlúčeniny. Okrem toho vykazujú povrebovoaktívne vlastnosti.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.
Vynález sa týká N,N“-bis(alkyldimetyl)-3-aza-3-dodecyl-l,5-pentáindiamóniumdibromidov všeobecného vzorcaThe invention relates to N, N'-bis (alkyldimethyl) -3-aza-3-dodecyl-1,5-pentanediammonium dibromides of the general formula
CH3CH3
R—N©—(CH2)2—N—(CH2)2—© R-N - (CH 2) 2 N (CH2) 2
CIL C12H25CIL C12H25
CH3 — ©N—R 2 Br©CH3 - © N — R 2 Br
CH3 kde R značí alkylový retazec s počtom atómov uhlíka 3 až 12 a sposobu ich přípravy.CH 3 wherein R represents an alkyl chain having a carbon number of 3 to 12 and a process for their preparation.
Je známe, že niektoré organické mono aj bisamóniové soli odvodené tak od alifatických ako i aromatických a heterocyklických amínov našli široké použitie tak v priemysle ako i v medicíně. U zlúčenín, ktoré obsahujú v molekule najmenej jeden dlhý alkylový retazec sa využívajú aj ich výhodné povrchovoaktívne vlastnosti. Popři tom mnohé z organických amóniových solí vykazujú aj biologické účinky. Tak napr. Ajatín (benzyldimetyldodecylamóniumbromid) alebo Septonex (2-) etoxykarbonyl (pentadecyl) trimetylamónlumbromid sú jedny z najrozšírenejších dezinficiencií. Zlúčeniny zo skupiny bisamóniových solí ako sú napr. hexametónium (N,N‘-histrimety'l-l,6-hexándiamóniumdibromid) alebo dekametónium (N,N‘-bistrimetyl-l,10-dekándiamóniumdibromid) patria medzi zlúčeniny s ganglioplegickým, resp. kurareformným účinkom. Podobné azametónium (3-aza-N,“-bis(etyldimetylj-3-metyl-l,5pentándiamóniumdibrcmid resp. dichlorid je jedným z vysokoúčinných ganglioplegík.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.
Zlúčeniny, ktoré sú predmetom vynálezu, sú látky doteraz v chemickej literatúre neopísané a zistill sa u nich doteraz neznáme účinky na mikroorganizmy. U najúčinnejších z nich je ich antimikróbna aktivita vyššia ako je účinnost Ajatinu a zrovnatefná so Septonexom.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.
Zlúčeniny tohoto typu sa dajú připravovat roznymi sposobmi, najčastejšie sa využívá reakcia halogénderivátov uhlOvodíkov s příslušnými terciárnymi amínmi za rozny-ch reakčných podmienok a v různých rozpúšťadlách. Viznikajú produkty variabilně] čistoty v kolísavom výtažku.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.
Sposob přípravy podfa vynálezu spočívá v reakcii bis (2-dimetylaminoetyl j-dodecylamínu s 1-brómalkánom obsahujúcom v reťazci 1 až 14 atómov uhlíka v prostředí metylkyanidu, etanolu alebo metanolu pri teplote varu rozpúštadlá počas 2 hodin, pričom vznikajú produkty vo vysokom výtažku vysokej čistoty.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. .
V příkladech, ktoré ilustruji! ale neobmedzujú metodu přípravy je uvedený sposob podlá vynálezu a sú charakterizované vybrané zlúčeniny. Je uvedená aj antimikróbna aktivita vyjádřená ako minimálna inhibičná koncentrácia (MIC] v ,wg/cm3 na mikroorganizmy Staphylococcus aureus, Escherichia coli a Camdida albicans.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.
Příklad 1Example 1
V 30 ml metylkyanidu sa rozpustí 0,1 mol bis (2-dimetylaminoetyl) dodecylamínu a 0,2 mol 1-brórnpropánu a zahrieva sa pod spatným tokom 2 hodiny. Potom sa rczpúšťadlo oddestiluje a produkt, ktorým je N,N“-bis(dimetylpropyl)-3-aza-3-dodecyl-l,5-pentándiamóniumdibromid sa prekryštalizuje do konštantnej teploty topenia z acetonu. T. t. 123 až 125°C; výťažok 90 % teorie; Rf (sústava aceton : 1 M HC1 : 1, Silufol, detekcia Dragendorfovým činidlom v Munierovej modifikácii) = 0,61; MIC: 5,30,20.0.1 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.
Příklad 2Example 2
Pracovný postup je ten istý ako v příklade 1 s tým rozdielom, že do reakcie sa použil 1-brómpentán a reakčným prostředím bol etanol. Produktom je N, N“-bis(dimetylpentyl) -3-aza-3-dodecyl-l,5-pentándiamóniumdibromid s t. t. 128 až 130 °C; výťažok 75 % teorie; Rf = 0,61;MIC 8,30,6.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.
Příklad 3Example 3
Pracovný postup je ten istý ako v příklade 1 s tým rozdielom, že do reakcie sa použil 1-brómnonán a reakčným prostředím bol metanol. Produktom je N,N“-bis(dimetylnonyl-3-aza-3-dodecyl-l,5-pentándiamóniumdibromid s t. t. 134 až 136 °C; výťažok 84 % teorie; Rf = 0,63; MIC: 6,20,20. Příklad 4The 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
Pracovný postup je ten istý ako v příklade 1 s tým rozdielom, že do reakcie sa použil 1-brómdodekán a reakčným prostředím bol etanol. Produktom je N, N“-bis(dodecyldlmetyl) -3-aza-l,5-pentándiamóniumdibromid s t. t. 138 až 140 °C; výťažok 94 % teorie; Rf = 0,44; MIC: 50,100,30.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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS2183A CS230340B1 (en) | 1983-01-03 | 1983-01-03 | N,n-bis/alkyldimethyl/p-3-aza-3-dodecyl-1,5-pentadiammonium bromides and method of preparing same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS2183A CS230340B1 (en) | 1983-01-03 | 1983-01-03 | N,n-bis/alkyldimethyl/p-3-aza-3-dodecyl-1,5-pentadiammonium bromides and method of preparing same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS230340B1 true CS230340B1 (en) | 1984-08-13 |
Family
ID=5331645
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS2183A CS230340B1 (en) | 1983-01-03 | 1983-01-03 | N,n-bis/alkyldimethyl/p-3-aza-3-dodecyl-1,5-pentadiammonium bromides and method of preparing same |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS230340B1 (en) |
-
1983
- 1983-01-03 CS CS2183A patent/CS230340B1/en unknown
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