DE2833135A1 - Substd. oligo amidine derivs. used as microbistatic - for use as preserving agent in cosmetic and antimicrobial prods. such as lotions, soaps and deodorants - Google Patents
Substd. oligo amidine derivs. used as microbistatic - for use as preserving agent in cosmetic and antimicrobial prods. such as lotions, soaps and deodorantsInfo
- Publication number
- DE2833135A1 DE2833135A1 DE19782833135 DE2833135A DE2833135A1 DE 2833135 A1 DE2833135 A1 DE 2833135A1 DE 19782833135 DE19782833135 DE 19782833135 DE 2833135 A DE2833135 A DE 2833135A DE 2833135 A1 DE2833135 A1 DE 2833135A1
- Authority
- DE
- Germany
- Prior art keywords
- oligocarbamidines
- substituted
- antimicrobial
- substd
- weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
Abstract
Description
"Verwendung von substituierten Oligocarbamidinen als"Use of substituted oligocarbamidines as
Mikrobistatika sowie diese enthaltende antimikrobielle Mittel" Die Erfindung betrifft die Verwendung substituierter Oligocarbamidine als Mikrobistatika sowie antimikrobielle Mittel mit einem Gehalt an diesen Verbindungen.Microbistatics and antimicrobial agents containing them "Die The invention relates to the use of substituted oligocarbamidines as microbistatics as well as antimicrobial agents containing these compounds.
Es wurde gefunden, daß Verbindungen der allgemeinen Formel in der R für einen Alkylenrest mit 2 - 8 C-Atomen oder einen mehrwertigen Arenalkylrest der Formel in der R' und. R" ein Wasserstoffatom oder eine niedere Alkylgruppe mit 1 - 4 C-Atomen und n die Zahlen 2 oder 3 darstellen, wobei die Gruppe CH2 - in verschiedenen Positionen am Ring stehen kann, ferner Y und Y' für ein Wasserstoffatom, ein Halogenatom oder eine niedere Alkylgruppe mit 1 - 4 C-Atomen, X( ) für das Anion einer anororganischen oder organischen Säure, vorzugsweise ein Halogenidanion und m für die Zahlen 2 oder 3 stehen, sehr gute mikrobistatische Wirksamkeit aufweisen und sich zur Herstellung antimikrobieller Mittel sowie zur Konservie rung insbesondere kosmetischer Produkte hervorragend eignen.It has been found that compounds of the general formula in which R stands for an alkylene radical with 2-8 carbon atoms or a polyvalent arenalkyl radical of the formula in the R 'and. R "represents a hydrogen atom or a lower alkyl group with 1-4 carbon atoms and n represents the numbers 2 or 3, where the group CH2 - can be in different positions on the ring, furthermore Y and Y 'represent a hydrogen atom, a halogen atom or a lower alkyl group with 1 - 4 carbon atoms, X () for the anion of an inorganic or organic acid, preferably a halide anion and m for the numbers 2 or 3, have very good microbiological effectiveness and are suitable for the production of antimicrobial agents and for preservation particularly suitable for cosmetic products.
Als erfindungsgemäß zu verwendende Produkte sind z.B.As products to be used according to the invention there are e.g.
folgende Verbindungen zu nennen: 1,2-Bis-(p-carbamidino-phenoxy)-äthan-dihydroehlorid, -propan-dihydrochlorid, 1,3-Bis- (p-carbamidino-phenoxy) -propan-dihydrochlorid, -butan-dihydrochlorid, 1,3-Bis- (m-carbamidino-phenoxy) -propan-dihydrochlorid, 1,4-Bis-(m-carbamidino-phenoxy)-butan-dihydrochlorid, 1,6-Bis - (p-carbamidino-phenoxy) -hexan-dihydrochlorid, 1,8-Bis- (m-carbamidino-phenoxy) -octan-dihydrochlorid, 1,3-Bis-(4'-carbamidino-2',6'-dibromphenoxy)-propandihydrochlorid, 1,6-Bis-(4'-carbamidino-2',6'-dichlorphenoxy)-hexan-dihydrochlorid, 1,6-Bis-(4'-carbamidino-2'-methyl-phenoxy)-hexan-dihydrochlorid, 1,-Bis-(4'-carbamidino-2' ,6'-dibromphenoxymethyl)-benzol-dihydrochlorid, 1,3-Bis-(m-carbamidino-phenoxymethyl)-benzol-dihydrochlorid, 1,3-Bis-(m-carbamidino-phenoxymethyl)-4ß6-dichlor-benzol-dihydrochlorid, 1,3,5-Tris-(m-carbamidinophenoxymethyl)-benzol-dihydrochlorid, ,4,6-Tris-(pcarbamidino-phenoxymethyl) -mesitylen-trihydrochlorid. the following compounds should be mentioned: 1,2-bis (p-carbamidino-phenoxy) -ethane dihydrochloride, propane dihydrochloride, 1,3-bis (p-carbamidino-phenoxy) propane dihydrochloride, -butane dihydrochloride, 1,3-bis (m-carbamidino-phenoxy) -propane dihydrochloride, 1,4-bis- (m-carbamidino-phenoxy) -butane-dihydrochloride, 1,6-bis- (p-carbamidino-phenoxy) -hexane dihydrochloride, 1,8-bis- (m-carbamidino-phenoxy) -octane-dihydrochloride, 1,3-bis- (4'-carbamidino-2 ', 6'-dibromophenoxy) propane dihydrochloride, 1,6-bis- (4'-carbamidino-2 ', 6'-dichlorophenoxy) -hexane-dihydrochloride, 1,6-bis- (4'-carbamidino-2'-methyl-phenoxy) -hexane-dihydrochloride, 1, -Bis- (4'-carbamidino-2 ', 6'-dibromophenoxymethyl) -benzene-dihydrochloride, 1,3-bis (m-carbamidino-phenoxymethyl) -benzene-dihydrochloride, 1,3-bis (m-carbamidinophenoxymethyl) -4ß6-dichlorobenzene-dihydrochloride, 1,3,5-tris- (m-carbamidinophenoxymethyl) -benzene-dihydrochloride, , 4,6-tris (pcarbamidino-phenoxymethyl) -mesitylene trihydrochloride.
Die Herstellung der erfindungsgemäß zu verwendenden substituierten Oligocarbamidine kann nach allgemein bekannten Methoden der organischen Chemie erfolgen.The preparation of the substituted to be used according to the invention Oligocarbamidines can be carried out according to generally known methods of organic chemistry.
So können beispielsweise Hydroxybenzonitrile der Formel mit Oligohalogenverbindungen der Formel R - (Hal)m, in der Y, Y', R und m die vorgenannte Bedeutung haben, zu den entsprechenden Oligonitrilen der Formel alkyliert werden. Die Nitrile lassen sich dann mit Methanol oder Äthanol und Chlorwasserstoff in die Oligoimidsäureester überführen, die dann anschließend mit Ammoniak in die Oligocarbamidine mit einem Chlorion als Anion umgewandelt werden.For example, hydroxybenzonitriles of the formula with oligohalogen compounds of the formula R - (Hal) m, in which Y, Y ', R and m have the aforementioned meaning, to the corresponding oligonitriles of the formula be alkylated. The nitriles can then be converted into the oligoimidic acid esters with methanol or ethanol and hydrogen chloride, which are then converted into the oligocarbamidines with a chlorine ion as the anion using ammonia.
Ein großer Teil der erfindungsgemäß zu verwendenden substituierten Oligocarbamidine ist als Substanz und in der Herstellung bereits literaturbekannt, ohne daß es zu ihrem Einsatz als antimikrobeille Verbindungen gekommen ist. Eine antimikrobielle Wirksamkeit der Verbindungen wird in der Literatur bisher nicht erwähnt.A large part of the substituted to be used according to the invention Oligocarbamidine is already known from the literature as a substance and in its production. without their being used as antimicrobial compounds. One Antimicrobial effectiveness of the compounds is not yet known in the literature mentioned.
Die erfindungsgemäß zu verwendenden Verbindungen besitzen eine gute Hemmwirkung bei Bakterien und Pilzen.The compounds to be used according to the invention have a good one Inhibitory effect on bacteria and fungi.
Da die erfindungsgemäß zu verwendenden substituierten Oligocarbamidine farblose kristalline, geruchsneutrale Produkte von guter physiologischer Verträglichkeit darstellen, die in wasserhaltigen Formulierungen vom pH-Wert 5 - 8 stabil sind, werden sie besonders vorteilhaft im Bereich der Kosmetik und Hygiene eingesetzt, beispielsweise zur Konservierung kosmetischer Produkte wie Cremes, Lotionen, Shampoos, aber auch zur Herstellung antimikrobieller Produkte wie Seifen, Handreinigungsmittel, Bade- und Duschzusätze und Deodorantien aller Ausführungsarten,wie z,B. Sprays oder Deo-Stifte.Since the substituted oligocarbamidines to be used according to the invention colorless crystalline, odorless products with good physiological compatibility that are stable in water-based formulations with a pH of 5 - 8, they are used particularly advantageously in the field of cosmetics and hygiene, for example for the preservation of cosmetic products such as creams, lotions, shampoos, but also for the production of antimicrobial products such as soaps, hand cleansers, Bath and shower additives and deodorants of all types, such as e.g. Sprays or Deodorant pens.
Die mit den erfindungsgemäß zu verwendenden substituierten Oligocarbamidinen zu konservierenden Kosmetika als auch die erfindungsgemäßen antimikrobiellen Mittel können in flüssiger, pastenartiger und fester Zubereitungsform vorliegen. Ihr Gehalt an den substituierten Oligocarbamidinen beträgt für den Einsatz als Konservierungsmittel 0,01 bis 0,5 Gewichtsprozent und beim Einsatz als antimikrobielle Mittel 0,1 bis 5 Gewichtsprozent, bezogen auf die gesamte Zubereitung.Those with the substituted oligocarbamidines to be used according to the invention cosmetics to be preserved and the antimicrobial agents according to the invention can be in liquid, paste-like and solid preparation form. Your salary on the substituted oligocarbamidines for use as preservatives 0.01 to 0.5 percent by weight and when used as antimicrobial agents 0.1 to 5 percent by weight, based on the total preparation.
Die nachfolgenden Beispiele sollen den Gegenstand der Erfindung näher erläutern, ohne ihn jedoch darauf zu beschränken.The following examples are intended to illustrate the subject matter of the invention in greater detail explain without, however, limiting it to them.
Beispiele Für die Untersuchung auf antimikrobielle Wirksamkeit wurde zunächst eine Reihe von substituierten Oligocarbamidinen gemäß Literaturangaben hergestellt. Examples of testing for antimicrobial effectiveness was made initially a number of substituted oligocarbamidines according to the literature manufactured.
Es handelte sich dabei um folgende Produkte: A) 1,3-Bis-(p-carbamidino-phenoxy)-propan-dihydrochlorid hergestellt gemäß den Angaben in J. Chem. Soc.The products involved were as follows: A) 1,3-bis (p-carbamidino-phenoxy) -propane dihydrochloride prepared as described in J. Chem. Soc.
(London) 1942, 110 über die Reaktion von 1,3-Dibrompropan mit p-Hydroxybenzonitril. (London) 1942, 110 on the reaction of 1,3-dibromopropane with p-hydroxybenzonitrile.
B) i,3-Bis-(4 ' -carbamidino-2( , 6'-dibromphenoxy) -propandihydrochlorid erhalten nach Angaben im J. Med. Chem 18, 477 (1975) in analoger Weise.B) i, 3-bis (4'-carbamidino-2 (, 6'-dibromophenoxy) propane dihydrochloride obtained according to information in J. Med. Chem 18, 477 (1975) in an analogous manner.
C) 1,6-Bis-(p-carbamidino-phenoxy)-hexan-dihydrochlorid hergestellt gemäß Angaben im J. Chem. Soc. (London) 1942, 110 über die Reaktion von 1,6-Dibromhexan mit p-Hydroxybenzonitril.C) 1,6-bis (p-carbamidino-phenoxy) -hexane dihydrochloride prepared according to information in J. Chem. Soc. (London) 1942, 110 on the reaction of 1,6-dibromohexane with p-hydroxybenzonitrile.
D) 1> 1,4-Bis-(p-carbamidino-phenoxymethyl)-benzoldihydrochlorid hergestellt gemäß Angaben im J. Med. Chem. 19, 638 (1976) über die Reaktion von a,a'-Dibrom-p-xylol mit p-Hydroxybenzonitril.D) 1> 1,4-bis (p-carbamidino-phenoxymethyl) -benzene dihydrochloride prepared according to information in J. Med. Chem. 19, 638 (1976) about the reaction of a, a'-dibromo-p-xylene with p-hydroxybenzonitrile.
E) 1,3,5-Tris-(m-carbamidino-phenoxymethyl)-benzoltrihydrochlorld erhalten gemäß den Angaben in Biochim. Biophys. Acta 445, 729 (1976) über die analoge Reaktion von 1,3,4-Tris-brommethyl-benzol mit m-Hydroxybenzonitril.E) 1,3,5-tris (m-carbamidino-phenoxymethyl) -benzene trihydrochloride obtained according to the information in Biochim. Biophys. Acta 445, 729 (1976) via the analog Reaction of 1,3,4-tris-bromomethyl-benzene with m-hydroxybenzonitrile.
Alle genannten Verbindungen stellen farblose, kristalline Produkte ohne Eigengeruch dar.All of the compounds mentioned are colorless, crystalline products without its own odor.
Zur Ermittlung der antimikrobiellen Wirksamkeit vorstehender Verbindungen wurde die Hemmwirkung gegenüber folgenden Testkeimen bestimmt: 1) Staphylococcus epidermis 2) Staphylococcus aureus 3) Pseudomonas aeruginosa 4) Escherichia coli 5) Candida albicans.To determine the antimicrobial effectiveness of the above compounds the inhibitory effect on the following test germs was determined: 1) Staphylococcus epidermis 2) Staphylococcus aureus 3) Pseudomonas aeruginosa 4) Escherichia coli 5) Candida albicans.
Die Hemmkonzentrationen der zu untersuchenden Produkte wurden mit Hilfe des Verdünnungstestes gemäß den Richtlinien für die Prüfung chemischer Desinfektionsmittel, herausgegeben von der Deutschen Gesellschaft für Hygiene und Mikrobiologie (1959), ermittelt. Die gewünschten Prüfkonzentrationen wurden durch Mischen von abgemessenen Mengen der Substanzlösungen geeigneter Konzentrationen mit Bouillon in sterilen Röhrchen hergestellt, wobei das Gesamtvolumen jeweils 10 ml betrug. Anschließend wurden die Röhrchen mit 0,1 ml Testkeimsuspension der genannten Keime beimpft. Die beimpften Röhrchen wurden 3 Tage bei 370C im Brutschrank bebrütet. Anschließend wurde festgestellt, welche dem Nährmedium zugefügte Substanzkonzentration das Wachstum der Keime gerade noch unterbinden konnte. Dieser so ermittelte Wert wurde als Hemmkonzentration bezeichnet. Die Untersuchungen wurden in folgenden Konzentrationsintervallen durchgeführt: 1 000 ppm, 750 ppm, 500 ppm, 250 ppm, 100 ppm, 50 ppm, 25 ppm, 10 ppm, 5 ppm.The inhibitory concentrations of the products to be investigated were with Help with the dilution test in accordance with the guidelines for testing chemical disinfectants, published by the German Society for Hygiene and Microbiology (1959), determined. The desired test concentrations were measured by mixing Quantities of substance solutions of suitable concentrations with bouillon in sterile Tubes made, the total volume of each 10 ml. Afterward the tubes were inoculated with 0.1 ml test germ suspension of the germs mentioned. the inoculated tubes were incubated for 3 days at 370C in an incubator. Afterward it was determined which substance concentration added to the nutrient medium stimulates growth which could just prevent germs. This value determined in this way was used as the inhibitory concentration designated. The tests were carried out at the following concentration intervals: 1,000 ppm, 750 ppm, 500 ppm, 250 ppm, 100 ppm, 50 ppm, 25 ppm, 10 ppm, 5 ppm.
Bei diesem Verdünnungstest wurden die in der nachstehenden Tabelle 1 aufgeführten Hemmkonzentrationen für die einzelnen Produkte bei den vorgenannten Keimen ermittelt.In this dilution test, those in the table below were used 1 listed inhibitory concentrations for the individual products for the aforementioned Germs determined.
Tabelle 1 Verdünnungstest, Hemmkonzentration in ppm.Table 1 Dilution test, inhibitory concentration in ppm.
Substanz Testkeim 1 2 3 4 5 A <10 <10 500 250 50 B <10 <10 500 250 50 C <10 <10 50 50 <10 D <10 10 500 500 50 E 10 10 50 50 50 Der Tabelle ist die gute Hemmwirkung der substituierten Oligocarbamidine gegen Bakterien und Pilze zu entnehmen.Substance test germ 1 2 3 4 5 A <10 <10 500 250 50 B <10 <10 500 250 50 C <10 <10 50 50 <10 D <10 10 500 500 50 E 10 10 50 50 50 The table shows the good inhibitory effect of the substituted oligocarbamidines against bacteria and mushrooms.
Einige antimikrobiell wirksame Mittel mit einem Gehalt an substituierten Oligocarbamidinen sind in den nachfolgenden Beispielen beschrieben.Some antimicrobial agents containing substituted Oligocarbamidines are described in the following examples.
Desinfizierendc Handaraschnaste Natriumlaurylsulfat mit ca. 35 % Waschaktivsubstanz 52 Gew.-Teile Kokosfettsäuremonoäthanolamid 3 " Bimsstein, fein gemahlen 44 " Substanz A 1 Gelr.-Teil An Stelle der Substanz A können mit gleich gutem Erfolg die Produkte B, C, D, E eingesetzt werden.Disinfecting hand arachnaste sodium lauryl sulphate with approx. 35% active washing substance 52 parts by weight coconut fatty acid monoethanolamide 3 "pumice stone, finely ground 44" substance A 1 gel part Instead of substance A, the products can be used with equally good success B, C, D, E can be used.
Antimikrobielle Seife Bei der üblichen Herstellung einer Toiletteseife aus einem Gemisch von 60 % Kokosfettsäure und 40 % Talgfettsäure arbeitet man in der Schneckenpresse zusammen mit dem Farbstoff und dem Parfüm solche Mengen der Verbindung B ein, daß die fertige Seife 2 Gewichtsprozent davon enthält. Die Wirkung der antimikrobiellen Substanz wird noch gesteigert, wenn man außerdem soviel eines Komplexbildners wie NTA, EDTA oder EHDP einarbeitet, daß deren Anteil in der Seife 8 Gewichtsprozent ausmacht.Antimicrobial soap In the usual manufacture of a toilet soap from a mixture of 60% coconut fatty acid and 40% tallow fatty acid one works in the screw press together with the dye and the perfume such amounts of the Compound B implies that the finished soap contains 2 percent by weight thereof. The effect the antimicrobial substance is increased if you also have that much one Complexing agents such as NTA, EDTA or EHDP are incorporated into the soap 8 percent by weight.
An die Stelle der Verbindung B können auch die Produkte A, C> D, E treten.Instead of the compound B, the products A, C> D, E kick.
Deodorant-Spray 2-Octyldodecanol 6,5 Gew.-Teile Substanz C 1 Gew.-Teil Parfüm 0,5 Gear.-Teile Äthanol 42,0 " Treibgas 50,0 Mit gleich gutem Erfolg kann die Substanz C durch die Produkte A, B> D,E ersetzt werden.Deodorant spray 2-octyldodecanol 6.5 parts by weight of substance C 1 part by weight Perfume 0.5 gear parts Ethanol 42.0 "Propellant 50.0 Can be equally successful Substance C can be replaced by products A, B> D, E.
Deodorarlt-Sti.ft Stearylalkohol 10 Gew.-Teile 2-Octyldodecanol 10 Kokosfettsäuremonoäthanolamid 10 II Stearinsäuremonoäthanolamid 15 Carnaubawachs 2 Paraffin 7200 11 II Parfümöl 2 l,2-Propylenglykol 38 Substans Z r) 2 An Stelle der Substanz D können mit gleich gutem Erfolg die Produkte A, B, C, E in entsprechender Menge eingearbeitet werden.Deodorarlt-Sti.ft stearyl alcohol 10 parts by weight 2-octyldodecanol 10 Coconut fatty acid monoethanolamide 10 II Stearic acid monoethanolamide 15 Carnauba wax 2 Paraffin 7200 11 II Perfume oil 2 l, 2-propylene glycol 38 Substans Z r) 2 At Instead of substance D, products A, B, C, E can be used with equal success appropriate amount to be incorporated.
Tagescreme mit konservierendem Zusatz Kolloiddisperses Gemisch aus 90.Gew.-Kolloiddisperses Gemisch aus 90.Gew.-Teilen Cetylstearylalkohol und 10 Gew.-Teilen Natriumcetylstearylsulfat 8,0 Gew.-Teile 2-Octyldodecanol 2,5 " Stearinsäure 6,5 Triäthanolarnin 0,4 " " Glycerin 5,° Substanz E 0,1 Parfümöl 2,0 " Wasser 75,5 " fl An Stelle der Substanz E können auch die Substanzen A - D zur Konservierung verwendet werden.Day cream with a preservative additive colloidal mixture of 90 parts by weight colloidal disperse mixture of 90 parts by weight of cetostearyl alcohol and 10 parts by weight Sodium cetyl stearyl sulfate 8.0 parts by weight 2-octyldodecanol 2.5 "stearic acid 6.5 Triethanolamine 0.4 "" Glycerin 5, ° Substance E 0.1 Perfume oil 2.0 "Water 75.5" fl Instead of substance E, substances A - D can also be used for preservation will.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782833135 DE2833135A1 (en) | 1978-07-28 | 1978-07-28 | Substd. oligo amidine derivs. used as microbistatic - for use as preserving agent in cosmetic and antimicrobial prods. such as lotions, soaps and deodorants |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782833135 DE2833135A1 (en) | 1978-07-28 | 1978-07-28 | Substd. oligo amidine derivs. used as microbistatic - for use as preserving agent in cosmetic and antimicrobial prods. such as lotions, soaps and deodorants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2833135A1 true DE2833135A1 (en) | 1980-02-07 |
Family
ID=6045608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782833135 Ceased DE2833135A1 (en) | 1978-07-28 | 1978-07-28 | Substd. oligo amidine derivs. used as microbistatic - for use as preserving agent in cosmetic and antimicrobial prods. such as lotions, soaps and deodorants |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2833135A1 (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000015212A2 (en) * | 1998-09-17 | 2000-03-23 | The University Of North Carolina At Chapel Hill | Antifungal activity of dicationic molecules |
| EP1685836A2 (en) * | 1998-09-17 | 2006-08-02 | University Of North Carolina At Chapel Hill | Antifungal activity of dicationic molecules |
| US9375411B2 (en) | 2012-12-21 | 2016-06-28 | Verlyx Pharma Inc. | Uses and methods for the treatment of liver diseases or conditions |
| CN112566631A (en) * | 2018-06-14 | 2021-03-26 | 乔治亚州大学研究基金会 | Amidines and amidine analogs for the treatment of bacterial infections and potentiation of antibiotics |
| US11098009B2 (en) | 2016-12-22 | 2021-08-24 | Verlyx Pharma Inc. | Amidine substituted analogues and uses thereof |
| CN113754564A (en) * | 2021-08-02 | 2021-12-07 | 湖南大学 | Antibacterial amidine oligomer with anti-drug resistance and preparation method and application thereof |
-
1978
- 1978-07-28 DE DE19782833135 patent/DE2833135A1/en not_active Ceased
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000015212A2 (en) * | 1998-09-17 | 2000-03-23 | The University Of North Carolina At Chapel Hill | Antifungal activity of dicationic molecules |
| WO2000015212A3 (en) * | 1998-09-17 | 2001-08-16 | Univ North Carolina | Antifungal activity of dicationic molecules |
| US6326395B1 (en) | 1998-09-17 | 2001-12-04 | Duke University | Antifungal activity of dicationic molecules |
| EP1685836A2 (en) * | 1998-09-17 | 2006-08-02 | University Of North Carolina At Chapel Hill | Antifungal activity of dicationic molecules |
| EP1685836A3 (en) * | 1998-09-17 | 2007-05-09 | University Of North Carolina At Chapel Hill | Antifungal activity of dicationic molecules |
| US9827211B2 (en) | 2012-12-21 | 2017-11-28 | Verlyx Pharma Inc. | Uses and methods for the treatment of liver diseases or conditions |
| US9375411B2 (en) | 2012-12-21 | 2016-06-28 | Verlyx Pharma Inc. | Uses and methods for the treatment of liver diseases or conditions |
| US11098009B2 (en) | 2016-12-22 | 2021-08-24 | Verlyx Pharma Inc. | Amidine substituted analogues and uses thereof |
| CN112566631A (en) * | 2018-06-14 | 2021-03-26 | 乔治亚州大学研究基金会 | Amidines and amidine analogs for the treatment of bacterial infections and potentiation of antibiotics |
| EP3806836A4 (en) * | 2018-06-14 | 2022-07-20 | Georgia State University Research Foundation, Inc. | Amidines and amidine analogs for the treatment of bacterial infections and potentiation antibiotics |
| CN113754564A (en) * | 2021-08-02 | 2021-12-07 | 湖南大学 | Antibacterial amidine oligomer with anti-drug resistance and preparation method and application thereof |
| CN114773250A (en) * | 2021-08-02 | 2022-07-22 | 湖南大学 | Antibacterial amidine oligomer with anti-drug resistance and preparation method and application thereof |
| CN114933550A (en) * | 2021-08-02 | 2022-08-23 | 湖南大学 | Antibacterial peptide mimics with polyphenyl indole amidine and preparation method and application thereof |
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