CS232134B1 - N,h,-bis/acylezyetyl/-n,n,n,n 3-pentametyl-3-aza-1,5-pentanediamoniumdibromides and method of its preparation - Google Patents
N,h,-bis/acylezyetyl/-n,n,n,n 3-pentametyl-3-aza-1,5-pentanediamoniumdibromides and method of its preparation Download PDFInfo
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- CS232134B1 CS232134B1 CS834031A CS403183A CS232134B1 CS 232134 B1 CS232134 B1 CS 232134B1 CS 834031 A CS834031 A CS 834031A CS 403183 A CS403183 A CS 403183A CS 232134 B1 CS232134 B1 CS 232134B1
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- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 9
- -1 2-bromoethyl ester alkane Chemical class 0.000 claims description 7
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 150000003863 ammonium salts Chemical class 0.000 description 4
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000002253 acid Substances 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 125000005999 2-bromoethyl group Chemical group 0.000 description 1
- AHELICBDMBDYSN-UHFFFAOYSA-N 2-bromoethyl hexanoate Chemical compound CCCCCC(=O)OCCBr AHELICBDMBDYSN-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241001362550 Fabiola Species 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- CYDRXTMLKJDRQH-UHFFFAOYSA-N benzododecinium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 CYDRXTMLKJDRQH-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- FXQJFHYFOGHZTB-UHFFFAOYSA-M carbethopendecinium bromide Chemical compound [Br-].CCCCCCCCCCCCCCC([N+](C)(C)C)C(=O)OCC FXQJFHYFOGHZTB-UHFFFAOYSA-M 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000008394 flocculating agent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 210000000609 ganglia Anatomy 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000036540 impulse transmission Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 230000002232 neuromuscular Effects 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 150000003867 organic ammonium compounds Chemical class 0.000 description 1
- 230000001734 parasympathetic effect Effects 0.000 description 1
- 230000002445 parasympatholytic effect Effects 0.000 description 1
- UKODFQOELJFMII-UHFFFAOYSA-N pentamethyldiethylenetriamine Chemical compound CN(C)CCN(C)CCN(C)C UKODFQOELJFMII-UHFFFAOYSA-N 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
Description
Autor vynálSMU DEVINSKY FERDINAND ing. CSc., MASAROVÁ LUBOMÍRA,Author of the DEVINSKY FERDINAND ing. CSc., MASAR LUBOMIRA,
LACKO IVAN ing., BITTEREROVÁ FABIOLA PhDr., BRATISLAVA (54) N,N‘-bis (acyloxyetyl)-N,N,N‘,N‘,3-pentametyl-3-aza-l,5-pentándiamóniumdibromidy a sposob ich přípravyLACKO IVAN ing., BITTERER FABIOLA PhDr., BRATISLAVA (54) N, N'-bis (acyloxyethyl) -N, N, N ', N', 3-pentamethyl-3-aza-1,5-pentanediammonium dibromides of preparation
Vynález sa týká N,N‘-bis (acyloxyetyl)-N,N,N‘,N‘,3-pentametyl-3-aza-l,5-pentándíamióniumdibromidov všeobecného vzorca o ch3 The invention relates to N, N'-bis (acyloxyethyl) -N, N, N ', N', 3-pentamethyl-3-aza-1,5-pentanediammonium dibromides of the general formula 3
II III I
R—C—O- (CH2) 2-N© - (CH2 )2—N— , , I ch3 ch3 ch3 o — (CH2)2—®N—(CH2}2—O—C—R 2Br® ch3 kde R značí alkylový alebo alkenylový reťazec s poičtom atómov uhlíka 5 až 17 a sposobu přípravy týchto zlúčenín, ktorý spočívá na reakcii N,N-bis(2-dimetylamínoetyl)metylamínu s 2-brómetylestermi alkán a alkénikarbioxyloivých kyselím v prostředí mietylkyainidu počas 2 až 24 hodin pri teplote 20 až 85 °C.R-C-O- (CH2) 2-N © - (CH 2) 2 N, I CH 3 CH 3 CH 3 O - (CH 2) 2 -®N- (CH2} 2 O -C-R 3 wherein 2Br® chloro R is alkyl or alkenyl of poičtom carbon atoms 5 to 17 and methods of preparing these compounds, which comprises the reaction of N, N-bis (2-dimethylaminoethyl) methylamine with 2-brómetylestermi alkane and alkénikarbioxyloivých acid in methyl cyanide for 2 to 24 hours at 20 to 85 ° C.
Finálně zlúčeniny vykazujú účinok voči grampozitívnym, gramnegatívnym baktériám a kvasinkám, tvoria vo vodných roztokoch mlčely a preto sú použitelné ako povrchovoaktívne iantimiiKrótoe účinné zlúčeniny.Finally, the compounds exhibit activity against Gram-positive, Gram-negative bacteria and yeast, form silent in aqueous solutions and are therefore useful as surface active iantimia of Crote active compounds.
Vynález sa týká N,N‘-bis(acyloxyetylj-N,N,N‘,N‘,3-pentametyl-3-aza-l,5-pentándiamúniiumdibromidoiv všeobecného vzorcaThe present invention relates to N, N‘-bis (acyloxyethyl) -N, N, N‘, N N, 3-pentamethyl-3-aza-1,5-pentanediammonium dibromido compounds of the general formula
O CI13 r_C—O—(CH2)2—N© —(CH2j2—N— ci-i3 ch3 ch3 o — (CH2)2—©N—(CH2)2—O—C—R 2Br©The CI1 r_C 3-O- (CH2) 2-N © - (CH 2 N 2 S and C 3 CH 3 CH 3 O - (CH 2) 2 - © N- (CH 2) 2 O —C — R 2 Br ?.
CH3 kde R značí alkylový ,alebo alkenytový refazec s počtom atómov uhlíka 5 až 17 a sposobu ich přípravy.CH 3 wherein R represents an alkyl or alkenyl chain having a carbon number of 5 to 17 and a process for their preparation.
Je známe, že niektoré organické amóniové soli, ktoré vo svojej molekule obsahujú dlhý alkylový reťazec majú detergenčné vlastnosti a biologické účinky. Preto našli použitie v mnohých odvetviach priemyslu akio je napr. potravinářsky, textilný, papierenský, banský, využívajú sa ako inhibitory korózio, odvodňované povrchu, pomocné látky v stavebníctve, v kozmetike, farmácii, atd.It is known that some organic ammonium salts which contain a long alkyl chain in their molecule have detergent properties and biological effects. Therefore, they have found use in many sectors of the industry. food, textile, paper, mining, they are used as corrosion inhibitors, surface dewatering, construction aids, cosmetics, pharmacy, etc.
Ich antibakteriálne účinky sa využívajú na dezinfekciu Či už v nemocniciach, školách, komunálnych zariadenlach, velkochovoch napr. hydiny, rýb a pod.Their antibacterial effects are used for disinfection whether in hospitals, schools, municipal facilities, large-scale farms, eg. poultry, fish etc.
Do skupiny amóniových solí patří napr. aj acetylcholín, ktorý je pre vyššie organizmy životné důležitý, pretože působí ako mediátor přenosu nervového vzruchu na efektoroch parasympatitea, vo vegetatívnych gangliách a na nervosvalovej platničke.The group of ammonium salts includes e.g. also acetylcholine, which is vital for higher organisms, because it acts as a mediator of nerve impulse transmission on parasympathetic effectors, vegetative ganglia and neuromuscular plate.
Medzi organické amóniové zlúčeniny patria i niektoré cholinorgiká, parasympatolytiká gainglioibloikujúce a kurareforminé látky. Do· skupiny ganglioblokujúcich zlúčenín patří aj Penidiiomid-N,N“-bis(etyldimietyl)-3-metylaza-l,5-pentándiamóniumdibromid-zlúčehiina odvodená od dietyléntriamímu [ DETA; N-,N-bis (2-amimoetyl j aminu ].Organic ammonium compounds also include some cholinorgics, parasympatholytics, gaingliblo-blocking agents and curareformin substances. The group of ganglioblocking compounds also includes Penidiiomide-N, N'-bis (ethyldimethyl) -3-methylaza-1,5-pentanediammonium dibromide compound derived from diethylenetriamine [DETA; N-, N-bis (2-amimoethyl amine).
DETA a jeho deriváty sú jedny z najpoužívanejších polyamínov napr. pri výrobě a stužovaní epoxidových živíc, farbení umělých vlákien, našli použitie aj ako antistatiká, pri výrobě papiera, emulgátory, zjemňovače vlákien, flokulačné činidlá, atd.DETA and its derivatives are some of the most widely used polyamines, e.g. in the production and reinforcement of epoxy resins, artificial fiber dyeing, they have also found use as antistatic agents, in paper manufacture, emulsifiers, fiber refiners, flocculating agents, etc.
Zlúčemlny, ktoré sú predmetom: vynálezu, sú nové, doteraz v cbeanickej literatúre nieopísané a zistili sa u nich doteraz neznáme účinky na mikroorganizmy. U najúčinnejších z nich je ich aktivita vyššia ako Ajatínu a zrovnatelná so Septonexom, ktoré sú v súčasnosti najrozšínenejšie deziníicienciá zo skupiny organických amóniových solí.The compounds object of the invention are novel, not yet described in the ceanean literature, and have been found to have unknown effects on microorganisms. For the most effective, their activity is higher than Ajatin and comparable to Septonex, which are currently the most widespread disinitiatives of the organic ammonium salt group.
Organické amóniové soli sa pripravujú najčastejšie reakciou haiogénderivátov růzmej štruktúry s příslušnými terc.amínmi za různých reakčných podmienok. Vznikajú produkty vartabilnej čistoty v kolísavom, výtažku.Organic ammonium salts are most often prepared by reacting halo-derivatives of different structure with the corresponding tertiamine under different reaction conditions. Vartable purity products are produced in a fluctuating, extract.
Sposob přípravy podlá vynálezu spočívá v reakcii N,N-bís(2-dimetylamíi3iOieÍtylJmetyiamínu s 2-brómetylestermi alkán alebo alkénkarboxylovej kyseliny v prostre-dí metylkyaoidu pri teplotách 20 až 85 °C počas 2 až 24 hodin, pričom vznikajú produkty vo velmi dobrých výťažkoch vyhovujúcej čistoty.The process according to the invention consists in reacting N, N-bis (2-dimethylaminoethylthietylethylamine) with 2-bromoethyl esters of alkane or alkene carboxylic acid in methyl cyanide at temperatures of 20 to 85 ° C for 2 to 24 hours, yielding products in very good yields satisfactory. purity.
V příkladech, ktoré ilustrujú ale neobmedzujú metodu přípravy je uvedený spůsob podlá vynálezu, sú charakterizované vybrané zlúčeniny, je uvedená aj kritická koncentrácia tvorby miciel (Ckj a antimikróbna aktivita vyjádřená ako minimálna inhibičná koncentrácia (MIC, ^g/cm3) . Ck je vyjádřená v mol/dm3. MIC sa sledovala na Staphylococcus aureus, Escherichia coli a Caudida albicans.In the examples which illustrate but do not limit the method for preparing said sorting option of the invention are characterized by selected compounds is provided and the critical concentration of micelle-forming (C to I antimicrobial activity, expressed as minimum inhibitory concentration (MIC, .mu.g / cm 3). C k is expressed in mol / dm 3 MIC was monitored for Staphylococcus aureus, Escherichia coli and Caudida albicans.
IČ-spektrálne charakteristiky boli určené zmeraním vzoriek v KBr tabletách, (cm-1).IR spectral characteristics were determined by measuring samples in KBr tablets, (cm -1 ).
Příklad 1Example 1
2-brómetylester kyseliny hexánovej (0,1 mrul) sa rozpustí v 30 ml suchého metylkyanidu a přidá sa 0,05 mol N,N-bis(2-dimetylaimíinoeitylj mety laminu. Reakčná zmes sa ziahrieva 2 hodiny pod spatným tokám (85 °C). Po spracovaní reakčného produktu kryštalizáciou zo zmesi aceton—metanol sa získal N,N‘-bis(hexyl'Oxyietyl}-N,N,N‘,]\r,3-pentametyl-3-aza-l,5-pentándiamóniumdiibromid s ,t. t. 191 až 192 °C, výťažok 71 % teórie, Rf (sústava CHCla—CH3OH—H2O 75 : 22 : 3, silikagél, detekcia Drageindorlovým činidloím v Munierovej modifikaci!) = 0,40,Dissolve 2-bromoethyl hexanoate (0.1 µl) in 30 ml dry methyl cyanide and add 0.05 mol of N, N-bis (2-dimethylaminoimityl) methylamine and heat the reaction mixture at reflux for 2 hours (85 ° C). After working up the reaction product by crystallization from acetone-methanol, N, N'-bis (hexyl'Oxyethyl} -N, N, N ', 1', 3-pentamethyl-3-aza-1,5-pentanediammonium diibromide was obtained p, mp 191-192 DEG C., yield 71% of theory, R f (system 3 OH-CHCl-H2O 75: 22: 3, silica gel, the detection Drageindorlovým činidloím Munierovej modification?) = 0.40,
IČ:Company ID:
v (C=O) 1741 a 1723; v(C—O—C) 1152 a 1140; p(CH,j 715;v (C = O) 1741 and 1723; v (C-O-C) 1152 and 1140; p (CH, J 715;
v(N—Cíi3) 2757;v (N-Cl 3 ) 2757;
Ck = 4,8 . ΙΟ’2;C k = 4.8. ΙΟ '2;
MIC: > 1000, > 1000, > 1000.MIC: > 1000, > 1000, > 1000.
Příklad 2Example 2
Pracovny postup jse ten istý ako v příklade) 1 s tým rozdielom, že do reakcie sa použil 2-brómetylester kyseliny dekánovej a reakčný čas bol 12 hodin. Získal sa N,N‘-bis(dekanoylioxyetyl j -N,N,N‘,N‘,3-pentametyl-3-aza-l,5-peintáindiamóniiumdibromid s t. it. 209 až 211 QC, výtažek 71 % teórie, Rf — = 0,57,The procedure was the same as in Example 11 except that 2-bromoethyl decanoic acid was used in the reaction and the reaction time was 12 hours. To give N, N ' -bis (dekanoylioxyetyl j-N, N, N ', N ", 3-pentamethyl-3-aza-l, 5-a peintáindiamóniiumdibromid i. It. 209-211 Q C, extract 71% Rf - 0.57,
IC:IC:
v(C=O) 1739 a 1723, v(C—O—C) 1156 a 1138, p(CH,j 720, v(N—CH;J) 2751,v (C = O) 1739 and 1723, v (C-O-C) 1156 and 1138, p (CH, j 720, v (N-CH ; J ) 2751,
Ck = 2,2 . ΙΟ3,C k = 2.2. ΙΟ 3 ,
MIC: 7, 40, 30.MIC: 7, 40, 30.
Příklad 3Example 3
Pracovný postup je ten istý ako v príkla2 3 ;The procedure is the same as in Example 23;
de 1 s týim rozdielom, že do reakcie sa použil 2-brómetyIester kyseliny 10-undeeénove) a reakcia prebiehala pri teplote 20 °C 18 hodin. Získal sa N.N^bisflO-undec&noyloxyetyl)-N,N,N‘,N‘,3-pemtametyl-3-a>za-l,5-p&ntáindiamjóniiumidibromid s t. t. 203 až 204 °C, výťažiok 71 % teorie, Rf = 0,58,de 1 except that 2-bromoethyl ester of 10-undenenoic acid was used in the reaction and the reaction was run at 20 ° C for 18 hours. Obtained NN ^ bisflO-undec & noyloxyetyl) -N, N, N ', N ", 3-pemtametyl-3-a> a-l, 5-p & ntáindiamjóniiumidibromid with mp 203-204 DEG C., výťažiok 71%, Rf = 0.58.
IC:IC:
v(C=O) 1736 a 1728, v(C—O—C) 1160 a 1142, p(CH2) 710, v(N—CH3) 2751, v(=CH) 3027, v(C=C) 1627,v (C = O) 1736 and 1728, v (C-O-C) 1160 and 1142, p (CH 2 ) 710, v (N-CH 3 ) 2751, v (= CH) 3027, v (C = C) ) 1627,
Ó(=CH2) 912,Δ (= CH 2 ) 912,
Ck = 1,9.10-3,C k = 1,9.10-3
MIC: 20, 60, 50.MIC: 20, 60, 50.
Příklad 4Example 4
Pracovny postup je ten istý ako v príklade 3 s tým rozdielom, že do reakcie sa použil 2-bró.metyle.ster kyseliny cis-9-oktadecénovej (olejovej) a reakčný čas bol 24 hodin. Získal sa N,N‘-bis(oleyloxyetyl)-N;N,N‘,Ni,3-pentametyl-3-a.z,a-l,5-pentándiamóniumdibromid s t, t. 196 až 198 °C, výťažok 64 % teorie,The procedure was the same as in Example 3 except that 2-bromoethyl methyl ester of cis-9-octadecenoic acid (oleic) was used in the reaction and the reaction time was 24 hours. N, N'-bis (oleyloxyethyl) -N was obtained ; N, N ', N 1 , 3-pentamethyl-3-az, 1, 5-pentanediammonium dibromide st, m.p. 196-198 ° C, 64% yield,
IČ:Company ID:
v (C=O) 1728, v(C—O—Cj 1140, p(CH2) 704, v(N— CH3) 2749, v(—CH) 2994, v(C—C) 1607,v (C = O) 1728, v (C-O-C 1140, p (CH 2 ) 704, v (N-CH 3 ) 2749, v (CH) 2994, v (C-C) 1607,
R£ = 0,75, Rp = 0.75,
p. = qq 10-6p. = qq 10-6
MIC: 200, >1000, >1000.MIC: 200, > 1000, > 1000.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS834031A CS232134B1 (en) | 1983-07-03 | 1983-07-03 | N,h,-bis/acylezyetyl/-n,n,n,n 3-pentametyl-3-aza-1,5-pentanediamoniumdibromides and method of its preparation |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS834031A CS232134B1 (en) | 1983-07-03 | 1983-07-03 | N,h,-bis/acylezyetyl/-n,n,n,n 3-pentametyl-3-aza-1,5-pentanediamoniumdibromides and method of its preparation |
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| Publication Number | Publication Date |
|---|---|
| CS403183A1 CS403183A1 (en) | 1984-05-14 |
| CS232134B1 true CS232134B1 (en) | 1985-01-16 |
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| Application Number | Title | Priority Date | Filing Date |
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| CS834031A CS232134B1 (en) | 1983-07-03 | 1983-07-03 | N,h,-bis/acylezyetyl/-n,n,n,n 3-pentametyl-3-aza-1,5-pentanediamoniumdibromides and method of its preparation |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS232134B1 (en) |
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1983
- 1983-07-03 CS CS834031A patent/CS232134B1/en unknown
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| CS403183A1 (en) | 1984-05-14 |
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