DE19735776A1 - New neutral or cationic phospholipid analogues - Google Patents

New neutral or cationic phospholipid analogues

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Publication number
DE19735776A1
DE19735776A1 DE19735776A DE19735776A DE19735776A1 DE 19735776 A1 DE19735776 A1 DE 19735776A1 DE 19735776 A DE19735776 A DE 19735776A DE 19735776 A DE19735776 A DE 19735776A DE 19735776 A1 DE19735776 A1 DE 19735776A1
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Prior art keywords
phospho
dimethyl
glycero
compound
dihydroxypropyl
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DE19735776A
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German (de)
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Hans-Joerg Prof Dr Eibl
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Max Planck Gesellschaft zur Foerderung der Wissenschaften eV
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Max Planck Gesellschaft zur Foerderung der Wissenschaften eV
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Priority claimed from DE19622224A external-priority patent/DE19622224A1/en
Application filed by Max Planck Gesellschaft zur Foerderung der Wissenschaften eV filed Critical Max Planck Gesellschaft zur Foerderung der Wissenschaften eV
Priority to DE19735776A priority Critical patent/DE19735776A1/en
Priority to PCT/EP1998/005252 priority patent/WO1999009037A1/en
Priority to DE59805997T priority patent/DE59805997D1/en
Priority to US09/486,039 priority patent/US6344576B1/en
Priority to JP2000509716A priority patent/JP4550271B2/en
Priority to AU92632/98A priority patent/AU9263298A/en
Priority to EP98945258A priority patent/EP1019417B1/en
Priority to AT98945258T priority patent/ATE226210T1/en
Priority to DK98945258T priority patent/DK1019417T3/en
Priority to PT98945258T priority patent/PT1019417E/en
Priority to ES98945258T priority patent/ES2181269T3/en
Publication of DE19735776A1 publication Critical patent/DE19735776A1/en
Priority to US10/025,778 priority patent/US6545169B1/en
Priority to US10/377,617 priority patent/US6828453B2/en
Priority to US10/969,020 priority patent/US7595411B2/en
Priority to JP2009219177A priority patent/JP4714289B2/en
Priority to US12/567,992 priority patent/US7939683B2/en
Priority to US13/084,876 priority patent/US8497388B2/en
Ceased legal-status Critical Current

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    • A61K9/00—Medicinal preparations characterised by special physical form
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    • A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/24—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing atoms other than carbon, hydrogen, oxygen, halogen, nitrogen or sulfur, e.g. cyclomethicone or phospholipids
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    • A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Liposomes
    • A61K9/1271—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers
    • A61K9/1272—Non-conventional liposomes, e.g. PEGylated liposomes, liposomes coated with polymers with substantial amounts of non-phosphatidyl, i.e. non-acylglycerophosphate, surfactants as bilayer-forming substances, e.g. cationic lipids
    • C—CHEMISTRY; METALLURGY
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
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Abstract

Phospholipid analogues (I) and liposomes containing (I) are new. Phospholipid analogues of formula (I) are new. A = (a) -OCH2-CH(OR2)-CH2OR1 or -OCH(CHOR2)-CH2OR1; (b) -OCH2-(CH2)s-CH2OR1, -OCH((CH2)sH)-CH2OR1 or -OCH2-CH(OR2)-(CH2)sH; or (c) OR; R1,R2 = H or optionally substituted, saturated or unsaturated alkyl or acyl, the total number of C in acyl and alkyl being 16-44; s = 0-8; R = 12-30C alkyl (optionally unsaturated, with predominantly cis-double bonds); R3 = (a) 1,2-dihydroxypropyl, (b) 1-3C alkyl if z is other than 0 or (c) 1-3C alkyl if n is other than 2 and z = 0; m = 1 or 2; x = 0-8; y = 1 if z = 1-5 or y = 1-4 if z = 1; z = 0-5. An Independent claim is included for liposomes containing phospholipids and/or alkyl-phospholipids, optionally cholesterol and 1-50 molar % of (I) or its salt (based on the total of these lipid components).

Description

Die Erfindung betrifft neue phospholipidanaloge Verbindungen, die als Liposomenbestandteile zum Transport von Arzneimitteln, als Lösungsvermittler für in Wasser schlecht lösliche Arzneimittel und auch als Wirkstoffe selbst gegen Erkrankungen wie Krebs und Leishmaniose eingesetzt werden können, diese neuen Verbindungen enthaltende Liposomen, Arzneimittelzusammensetzungen, welche diese Liposomen enthalten, und Verfahren zur Herstellung von Arzneimitteln.The invention relates to novel phospholipid analogues which are known as Liposomal components for transporting medicines, as Solubilizers for poorly soluble in water drugs and also as Active substances themselves against diseases such as cancer and leishmaniasis can be used containing these new compounds Liposomes, drug compositions containing these liposomes contain, and method of preparation of medicaments.

Insbesondere betrifft die Erfindung Phosphatidylverbindungen, die einen definierten hydrophilen Rest enthalten, sowie Liposomen, die eine verkürzte oder verlängerte Lebensdauer im Serum aufweisen und gezielt von bestimmten Zellen, beispielsweise Tumorzellen, aufgenommen werden können.In particular, the invention relates to phosphatidyl compounds which have a contain defined hydrophilic residue, as well as liposomes, which are a truncated or prolonged serum life and targeted by certain cells, for example tumor cells can.

Herkömmliche Liposomen weisen im Serum eine Verweilzeit von bis zu 5 Stunden auf. Insbesondere bei der Verwendung von Liposomen als Träger für pharmazeutische Wirkstoffe ist jedoch eine möglichst lange Verweilzeit Liposomen im Blutkreislauf wünschenswert, insbesondere aber in Verbindung mit einer Aufnahme in ausgewählte Zielzellen.Conventional liposomes have a residence time of up to 5 in serum Hours up. Especially when using liposomes as a carrier for pharmaceutical active ingredients, however, the longest possible residence time Liposomes in the bloodstream desirable, but especially in Connection with a recording in selected target cells.

Es wurden daraufhin die sogenannten "Stealth-Liposomen" entwickelt, die eine verlängerte Lebensdauer aufweisen. Diese "Stealth-Liposomen" sind auf der Basis von Phosphatidylverbindungen aufgebaut, die einen verlängerten Polyethylenglykolrest enthalten. Der Polyethylenglykolrest erwies sich für die angestrebte verlängerte Lebensdauer am wirksamsten bei Molekulargewichten zwischen 2000 und 3000. Ein wesentlicher Nachteil dieser "Stealth-Liposomen" bzw. der Phosphatidylverbindungen mit Polyethylenglykolrest liegt allerdings darin, daß es sich nicht um exakt definierte Verbindungen handelt, da die Polyethylenglykolreste unterschiedliche Kettenlängen aufweisen. Die sogenannten "Stealth-Liposomen" besitzen infolge des Phosphatrestes jedoch immer eine negative Oberflächenladung in der Liposomenmembran. Aufgabe der eigenen älteren Patentanmeldung 196 22 224.9 war deshalb die Bereitstellung von Verbindungen, die die Lebensdauer von Liposomen erhöhen und eine exakt angebbare Zusammensetzung aufweisen, wobei ebenfalls Phosphatester und damit negative Ladungen verwendet wurden.Thereupon the so-called "stealth liposomes" were developed have a prolonged life. These are "stealth liposomes" built on the basis of phosphatidyl compounds, the one contain extended polyethylene glycol radical. The polyethylene glycol radical proved most effective in achieving the desired extended life Molecular weights between 2000 and 3000. A major disadvantage this "stealth liposomes" or the phosphatidyl compounds with Polyethylene glycol residue is, however, that it is not exactly defined compounds, since the polyethylene glycol radicals  have different chain lengths. The so-called "stealth liposomes" However, due to the phosphate radical always have a negative Surface charge in the liposome membrane. Abandonment of their own older ones Patent application 196 22 224.9 was therefore the provision of Compounds that increase the life span of liposomes and a precise have specifiable composition, wherein also phosphate esters and thus negative charges were used.

Aufgabe der vorliegenden Erfindung ist es dagegen, Verbindungen bereitzustellen, welche diese negative Oberflächenladung vermeiden und die Oligoglycerin- oder Zuckerreste über ein Stickstoffatom in die Struktur einbinden. Durch die positive Ladung am Stickstoffrest wird die negative Ladung am Phosphat ausgeglichen oder sogar überkompensiert, wenn 2 Stickstoffatome im Molekül verwendet werden. Diese Aufgabe wird erfindungsgemäß gelöst durch eine Verbindung einer allgemeinen Formel I
The object of the present invention, however, is to provide compounds which avoid this negative surface charge and incorporate the oligoglycerol or sugar residues into the structure via a nitrogen atom. The positive charge on the nitrogen residue compensates or even overcompensates the negative charge on the phosphate when 2 nitrogen atoms are used in the molecule. This object is achieved by a compound of general formula I.

worin A
where A

ist, wobei R1 und R2 unabhängig voneinander Wasserstoff, einen gesättigten oder ungesättigten Acyl- oder Alkylrest bedeuten, der gegebenenfalls verzweigt oder/und substituiert sein kann, wobei die Summe der Kohlenstoffatome in Acyl und Alkyl zwischen 16 und 44 C-Atomen liegt,
where R 1 and R 2 independently of one another represent hydrogen, a saturated or unsaturated acyl or alkyl radical which may optionally be branched or / and substituted, the sum of the carbon atoms in acyl and alkyl being between 16 and 44 C atoms,

ist, wobei R1 und R2 die gleiche Bedeutung wie in a besitzen; s eine ganze Zahl von 0 bis 8 darstellt,
c = RO- ist, wobei R einen gesättigten oder ungesättigten Alkylrest vorwiegend mit cis-Doppelbindung von 12 bis 30 Kohlenstoffatomen bedeutet,
n eine ganze Zahl von 2 bis 8 darstellt,
R3
a = 1,2-Dihydroxypropyl sein kann oder
b = Alkyl mit 1 bis 3 C-Atomen sein kann, wenn z < 0 ist oder
c = Alkyl mit 1 bis 3 C-Atomen sein kann, wenn n ≠ 2 und z = 0 ist,
m = 1 oder 2 ist,
x = eine ganze Zahl von 0 bis 8 darstellt,
y = 1 für z = 1 bis 5 ist oder = 1 bis 4 ist für z = 1
z = eine ganze Zahl von 0 bis 5 darstellt.wherein R 1 and R 2 have the same meaning as in a; s represents an integer from 0 to 8,
c = RO-, where R is a saturated or unsaturated alkyl radical predominantly having a cis double bond of 12 to 30 carbon atoms,
n represents an integer from 2 to 8,
R 3
a = 1,2-dihydroxypropyl may be or
b = alkyl having 1 to 3 carbon atoms, when z <0 or
c = alkyl having 1 to 3 C atoms, if n ≠ 2 and z = 0,
m = 1 or 2,
x = an integer from 0 to 8,
y = 1 for z = 1 to 5 or = 1 to 4 for z = 1
z = represents an integer from 0 to 5.

Die in den hier beschriebenen Substanzen verwendeten Strukturelemente können beliebig variiert und maßgeschneidert der jeweiligen Verwendung angepaßt werden.The structural elements used in the substances described herein can be varied and tailored to the particular use be adjusted.

Über den Strukturparameter A können vorwiegend die apolaren Anteile der Moleküle variiert werden, z. B. über die Kettenlänge der Fettsäuren und der Alkylreste. Eine Modifikation der polaren Anteile ist über die Phosphatgruppe, das Stickstoffatom und die damit verknüpften Oligoglycerine möglich. About the structure parameter A can mainly the apolar parts of Molecules are varied, for. B. on the chain length of the fatty acids and the Alkyl radicals. A modification of the polar parts is about Phosphate group, the nitrogen atom and the associated Oligoglycerols possible.  

Die durch die allgemeine Formel I erfaßten Verbindungen besitzen hervorragende biologische Eigenschaften und finden Verwendung als
The compounds covered by the general formula I have excellent biological properties and are used as

  • 1) Liposomenbestandteile zur gezielten Anreicherung von Wirkstoffen Zielzellen,1) Liposome components for the targeted accumulation of active substances Target cells,
  • 2) Lösungsvermittler für schwer intravenös applizierbare Substanzen, wie z. B. Taxol,2) solubilizers for substances which are difficult to administer intravenously, such as Taxol,
  • 3) Wirkstoffe gegen Krebs und Protozoenerkrankungen.3) anti-cancer and protozoan drugs.

Die Verbindungen, die in den verschiedenen Anwendungsbereichen besondere Bedeutung besitzen, werden nun im Detail beschrieben. Dabei gibt es Überschneidungen, da disubstituierte Glycerine mit dem Strukturmerkmal A sowohl membranstabilisierende Eigenschaften (R1 + R2 < 20 C-Atome) wie auch membrandestabilisierende Eigenschaften (R1 + R2 < 20 C-Atome) besitzen können. Insbesondere die Grenzbereiche zwischen Membran- und Mizellbildnern können hier von besonderem Interesse sein.The compounds which are of particular importance in the various fields of application will now be described in detail. There are overlaps, since disubstituted glycerols with the structural feature A both membrane-stabilizing properties (R 1 + R 2 <20 C-atoms) as well as membrane destabilizing properties (R 1 + R 2 <20 C-atoms) may possess. In particular, the boundary regions between membrane and micelle formers may be of particular interest here.

Allen Strukturen gemeinsam ist die einfache Herstellung der neuartigen Moleküle, die durch Umsetzung von primären oder sekundären Aminen mit Epoxiden erfolgen kann. So entsteht aus 1,2-Dipalmitoyl-sn-glycero-3- phospho-(N-methyl)-ethanolamin mit Benzylglycidol nach katalytischer Debenzylierung und Methylierung am Stickstoff ein Phospholipid mit lecithinartiger Struktur, das als Liposomenbestandteil verwendet wird.Common to all structures is the simple production of the novel Molecules obtained by reaction of primary or secondary amines with Epoxides can be done. This results in 1,2-dipalmitoyl-sn-glycero-3 phospho (N-methyl) -ethanolamine with benzylglycidol after catalytic Debenzylation and methylation on nitrogen a phospholipid with lecithin-like structure used as a liposome component.

Verbindungen mit nur einer langen Alkyl- oder Acylkette besitzen andere interessante Eigenschaften, wenn sie über primäre oder sekundäre Amine mit Epoxiden verknüpft werden, wie aus nachfolgender Beschreibung hervorgeht. Es sind ausgezeichnete Lösungsvermittler fuhr schlecht intravenös applizierbare Wirkstoffe und sogar direkte Wirkstoffe gegen Krebs und Leishmaniose. Compounds with only one long alkyl or acyl chain have others interesting properties when using primary or secondary amines be linked with epoxides, as from the following description evident. They are excellent solubilizers went bad Intravenously applicable agents and even direct agents against Cancer and Leishmaniasis.  

Der dieser Erfindung zugrundeliegende schrittweise Aufbau der hydrophilen Reste der Phosphatidylverbindungen der Formel I ermöglicht es, eine genau definierte Zusammensetzung der Verbindungen zu erhalten.The underlying this invention stepwise construction of the hydrophilic Residues of the phosphatidyl compounds of the formula I allows a precisely to obtain defined composition of the compounds.

Es handelt sich also bei der erfindungsgemäßen Verbindung der Formel nicht um ein Gemisch verschiedener Moleküle unbestimmter Zusammensetzung und Kettenlänge, sondern es kann gezielt eine gewünschte Struktur erhalten werden. Dies bedeutet, falls das gewünschte Produkt ein N,N-Dimethyl-N-(2-hydroxypropyl-3,1-O,O-dihydroxypropyl)- ammoniumderivat ist mit y = 1 und z = 2 in der Formel I, daß die Verbindung chemisch definiert ist und keine Anteile mit y = 1 und z = 1 oder y = 1 und z = 3 usw. enthält. Bevorzugt werden Hydroxypropylderivate einer ganz bestimmten Kettenlänge verwendet, die wesentlichen frei von anderen Kettenlängen sind.It is therefore in the compound of the formula of the invention not a mixture of different molecules indefinite Composition and chain length, but it can target one desired structure can be obtained. This means, if the desired Product an N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) - is ammonium derivative with y = 1 and z = 2 in the formula I, that the Compound is chemically defined and no shares with y = 1 and z = 1 or y = 1 and z = 3 and so on. To be favoured Hydroxypropylderivate a very specific chain length used, the are substantially free of other chain lengths.

Erfindungsgemäß stellt die Verbindung der Formel I eine einheitliche Verbindung definierter Struktur dar. Bevorzugt ist die Verbindung hinsichtlich des Wertes von z größer als 99% einheitlich. Es ist jedoch auch möglich, die Verbindung mit einer Einheitlichkeit von mehr als 99,9% hinsichtlich des Wertes von z bereitzustellen.According to the invention, the compound of the formula I is a uniform Compound of defined structure. Preferred is the compound uniform with respect to the value of z greater than 99%. It is, however possible the connection with a uniformity of more than 99.9% with regard to the value of z.

Bevorzugt handelt es sich bei der Verbindung um Hydroxypropylderivate am Stickstoff mit 1 bis 5 Hydroxypropyleinheiten, bevorzugt mit 1 bis 3 Hydroxypropyleinheiten. Es handelt sich dabei bevorzugt um 1,3-verknüpfte lineare Oligoglycerinreste, die über einen 2-Hydroxypropylrest mit dem Stickstoffatom verknüpft sind.Preferably, the compound is hydroxypropyl derivatives on Nitrogen with 1 to 5 hydroxypropyl units, preferably with 1 to 3 Hydroxypropyl units. These are preferably 1,3-linked linear Oligoglycerinreste connected via a 2-hydroxypropyl with the Nitrogen atom are linked.

Die Reste R1 und R2 stellen erfindungsgemäß bevorzugt unabhängig voneinander Wasserstoff, einen gesättigten oder ungesättigten Acyl- oder Alkylrest dar, der gegebenenfalls verzweigt oder/und substituiert sein kann, wobei die Summe der Kohlenstoffatome in Acyl und Alkyl zwischen 16 und 44 liegt. The radicals R 1 and R 2 according to the invention are preferably independently of one another hydrogen, a saturated or unsaturated acyl or alkyl radical which may optionally be branched or / and substituted, the sum of the carbon atoms in acyl and alkyl being between 16 and 44.

Ein weiterer Gegenstand der Erfindung sind Liposomen, die Phospholipide oder/und Alkylphospholipide, gegebenenfalls Cholesterin und 1 bis 50 Mol-% einer Verbindung der allgemeinen Formel I beinhalten.Another object of the invention are liposomes, the phospholipids or / and alkyl phospholipids, optionally cholesterol and 1 to 50 mol% a compound of general formula I include.

Die Phospholipide oder/und Alkylphospholipide können beispielsweise Diacylglycerophosphoverbindungen definierter Struktur sein. Allgemein können diese Bestandteile der Lipide als Verbindungen definierter Struktur eingesetzt werden.The phospholipids and / or alkyl phospholipids can be, for example Diacylglycerophosphoverbindungen be defined structure. General These components of lipids can be defined as compounds of defined structure be used.

Im Falle y < 1 stammt der Rest -CH2(CHOH)y-CH2-OH bevorzugt aus Zuckeralkoholen, die für y = 2, 3 Hydroxylgruppen, für y = 3, 4 Hydroxylgruppen und für y = 4, 5 Hydroxylgruppen aufweisen. Beispiele solcher Reste sind Mannitderivate für y = 4, Lyxitderivate für y = 3 und Threitderivate für y = 2.In the case y <1, the radical -CH 2 (CHOH) y -CH 2 -OH preferably originates from sugar alcohols which have y = 2, 3 hydroxyl groups, y = 3, 4 hydroxyl groups and y = 4, 5 hydroxyl groups. Examples of such radicals are mannitol derivatives for y = 4, lyxite derivatives for y = 3 and threiter derivatives for y = 2.

Die erfindungsgemäßen Liposomen weisen eine deutlich veränderte Halbwertszeit in der Blutzirkulation auf. Die Liposomen mit m = 1 sind nach außen neutral und zeigen erhöhte Verweilzeiten im Blut, während die Liposomen mit m = 2 infolge der positiven Überschußladung in der Membran nur ganz kurz zirkulieren.The liposomes of the invention have a markedly altered Half-life in the blood circulation. The liposomes with m = 1 are after neutral on the outside and show increased residence times in the blood, while the Liposomes with m = 2 due to the positive excess charge in the Only circulate the membrane very briefly.

Ein weiterer Gegenstand der Erfindung ist eine pharmazeutische Zusammensetzung, die die oben beschriebenen Liposomen und in den Liposomen eingeschlossen einen oder mehrere pharmazeutische Wirkstoffe gegebenenfalls zusammen mit pharmazeutisch üblichen Verdünnungs-, Hilfs-, Träger- und Füllstoffen enthält.Another object of the invention is a pharmaceutical Composition containing the liposomes described above and in the Liposomes include one or more pharmaceutical agents optionally together with pharmaceutically customary diluents, auxiliaries, Contains carriers and fillers.

Als Wirkstoffe können in der Regel alle Wirkstoffe verwendet werden, die sich mittels Liposomen überhaupt ins Plasma einbringen lassen. Bevorzugte Wirkstoffgruppen sind einerseits Cytostatika, insbesondere Anthracyclin- Antibiotika, wie etwa Doxorubicin, Epirubicin oder Daunomycin, wobei Doxorubicin besonders bevorzugt ist. Weitere bevorzugte Cytostatika sind Idarubicin, Hexadecylphosphocholin, 1-Octadecyl-2-methyl-rac-glycero-3- phosphocholin, 5-Fluoruracil, cis-Platinkomplexe wie Carboplatin und Novantron sowie Mitomycine.As active ingredients, as a rule, all active substances can be used which can be brought into the plasma by means of liposomes. preferred On the one hand, active ingredient groups are cytostatic drugs, in particular anthracycline Antibiotics, such as doxorubicin, epirubicin or daunomycin, wherein Doxorubicin is particularly preferred. Further preferred cytostatics are  Idarubicin, hexadecylphosphocholine, 1-octadecyl-2-methyl-rac-glycero-3 phosphocholine, 5-fluorouracil, cis-platinum complexes such as carboplatin and Novantrone and mitomycins.

Weitere bevorzugte Wirkstoffgruppen sind immunmodulierende Substanzen wie etwa Cytokine, wobei unter diesen wiederum die Interferone und insbesondere das α-Interferon besonders bevorzugt sind, antimykotisch wirksame Substanzen (z. B. Amphotericin B) und Wirkstoffe gegen Protozoenerkrankungen (Malaria, Trypanosomen- und Leishmanien- Infektionen). Ebenfalls bevorzugt ist Taxol als Wirkstoff.Further preferred groups of active substances are immunomodulating substances such as cytokines, among which, in turn, the interferons and in particular the α-interferon are particularly preferred, antimycotic active substances (eg amphotericin B) and active substances against Protozoan diseases (malaria, trypanosome and leishmania) Infections). Also preferred is taxol as the active ingredient.

Eine weitere bevorzugte Wirkstoffgruppe sind lytische Wirkstoffe, wie sie in der DE 41 32 345 A1 beschrieben sind. Bevorzugt sind Miltefosin, Edelfosin, Ilmofosin sowie SRI62-834. Insbesondere bevorzugt sind Alkylphosphocholine auch mit erweiterten Alkylketten, z. B. Erucylphosphocholin und Erucylphosphocholine mit erweitertem Phospho- Stickstoffabstand.Another preferred group of drugs are lytic agents, as they are are described in DE 41 32 345 A1. Miltefosine is preferred, Edelfosin, Ilmofosin and SRI62-834. Particularly preferred Alkylphosphocholines also with extended alkyl chains, eg. B. Erucylphosphocholine and erucylphosphocholines with extended phosphorous Nitrogen ratio.

Ein weiterer Gegenstand der vorliegenden Erfindung ist die Verwendung von erfindungsgemäßen Liposomen zur Herstellung eines Antitumormittels, wobei der Wirkstoff besonders bevorzugt Doxorubicin ist.Another object of the present invention is the use of liposomes according to the invention for the preparation of an antitumor agent, wherein the active ingredient is particularly preferably doxorubicin.

Noch ein weiterer Gegenstand der vorliegenden Erfindung ist die Verwendung der erfindungsgemäßen Liposomen zur Herstellung eines Mittels zur Beeinflussung der Zellproliferation, wobei der Wirkstoff ein Cytokin, besonders bevorzugt α-Interferon ist.Yet another object of the present invention is the Use of the liposomes according to the invention for the preparation of a By means of influencing cell proliferation, wherein the active ingredient Cytokine, particularly preferred is α-interferon.

Die erfindungsgemäßen Liposomen werden nach an sich bekannten Methoden hergestellt mit hierfür gängigen Vorrichtungen. Typischerweise kann eine die verschiedenen Komponenten des Liposoms einschließlich 1 bis 50 Mol-% einer Verbindung der Formel I enthaltende Lösung in eine Lipidsuspension überführt werden, die dann unter hohem Druck durch Düsen oder durch Lochscheiben gepreßt wird, wobei durch die Größe der Öffnungen in der Lochscheibe die Größe der erhaltenen Liposomen geregelt werden kann. Geeignete Maßnahmen zur Überführung einer Lipidsuspension in Liposomen sind dem Fachmann bekannt. Bevorzugt werden 5 bis 55 Mol-% einer Verbindung der allgemeinen Formel I mit 35 bis 60 Mol-% Cholesterin und 40 bis 60 Mol-% Phospholipiden oder/und Alkylphospholipiden in eine Lipidsuspension überführt, die dann durch geeignete Maßnahmen auf an sich bekannte Weise in Liposomen umgewandelt wird. Solch bekannte Verfahren können auch zur Herstellung einer pharmazeutischen Zubereitung, die die erfindungsgemäßen Liposomen und einen oder mehrere pharmazeutische Wirkstoffe enthält, verwendet werden. Zum Einschluß wasserunlöslicher Wirkstoffe wird der Wirkstoff dabei zusammen mit den Lipidbestandteilen gelöst, während zum Einschluß wasserlöslicher Wirkstoffe der Lipidfilm mit einer wäßrigen Lösung versetzt wird, die den wasserlöslichen Wirkstoff enthält.The liposomes according to the invention are known per se Methods made with this common devices. typically, One may be the various components of the liposome including 1 to 50 mol% of a compound of formula I containing solution in a Lipidsuspension are transferred, which then under high pressure through  Nozzle or is pressed through perforated discs, wherein by the size of the Openings in the perforated disc regulated the size of the obtained liposomes can be. Suitable measures for the transfer of a lipid suspension in liposomes are known in the art. Preference is given to 5 to 55 mol% a compound of general formula I with 35 to 60 mol% Cholesterol and 40 to 60 mol% phospholipids or / and Alkylphospholipiden converted into a lipid suspension, which then by appropriate measures in per se known manner in liposomes is converted. Such known methods can also be used for the production a pharmaceutical preparation containing the liposomes of the invention and one or more pharmaceutical agents become. To include water-insoluble drugs, the active ingredient thereby dissolved together with the lipid components, while inclusion water-soluble active ingredients of the lipid film is mixed with an aqueous solution which contains the water-soluble active ingredient.

Die Ausgangsphospholipide werden nach in der Literatur beschriebenen Verfahren hergestellt (DE 31 30 867 A1; Eibl et al., Chem. Phys. Lipids 28 (1981), 1-5, 41 (1986), 53-63 und 47 (1988), 47-53. Insbesondere kann hier auf Verfahren zurückgegriffen werden, die in der PCT/EP97/00749-An­ meldung vom 17.02.1997 beschrieben worden sind. So können die erfindungsgemäßen Verbindungen der Formel I auf folgende Weise hergestellt werden:
Beispiel (A = a; n = 2; m = 1; y = 1; z = 2)
(Reaktion von 1,2-Diplamitoyl-sn-glycero-3-phospho-(N-methyl)-ethanolamin mit 1,2-Isopropyliden-glycero-glycidol).
The starting phospholipids are prepared by methods described in the literature (DE 31 30 867 A1; Eibl et al., Chem. Phys. Lipids 28 (1981), 1-5, 41 (1986), 53-63 and 47 (1988), In particular, it is possible here to use processes which have been described in PCT / EP97 / 00749 application of 17 February 1997. Thus, the compounds of the formula I according to the invention can be prepared in the following manner:
Example (A = a, n = 2, m = 1, y = 1, z = 2)
(Reaction of 1,2-Diplamitoyl-sn-glycero-3-phospho- (N-methyl) -ethanolamine with 1,2-isopropylidene-glycero-glycidol).

Entsprechende Umsetzungen können durchgeführt werden, die Verbindungen mit n = 3-10; m = 1; y = 1; z = 1-5. Ausgangsverbindungen für x = 2 und 3 sind Kephaline und N-Methylkephaline, deren Darstellung ausführlich beschrieben wurde. Die Umsetzungen mit den entsprechenden Glycidolen, deren Herstellung in der deutschen Patentanmeldung "Phosphatidyloligoglycerine" 196 22 224 beschrieben ist, führt zu den gewünschten Produkten, wobei die Addition einem 2-Phasensystem THF - Na2CO3/NaHCO3 1 : 1 (0,5 M in H2O; pH 9-10) durchgeführt wird. Bei diesen pH-Werten wird jedoch keine Hydrolyse der Fettsäureester beobachtet. Corresponding reactions can be carried out, the compounds with n = 3-10; m = 1; y = 1; z = 1-5. Starting compounds for x = 2 and 3 are cephalins and N-methylkephalines, the preparation of which has been described in detail. The reactions with the corresponding glycidols, whose preparation is described in the German patent application "Phosphatidyloligoglycerine" 196 22 224, leads to the desired products, wherein the addition of a 2-phase system THF - Na 2 CO 3 / NaHCO 3 1: 1 (0, 5M in H 2 O, pH 9-10). At these pH values, however, no hydrolysis of the fatty acid esters is observed.

Zur Darstellung der Dioleoylverbindungen muß 1,2-Dioleyol-sn-glycero-3- phospho-(N-methyl)-ethanolamin hergestellt werden. Dies wird durch folgendes Reaktionsschema erreicht:
To prepare the dioleoyl compounds, 1,2-dioleyol-sn-glycero-3-phospho- (N-methyl) -ethanolamine must be prepared. This is achieved by the following reaction scheme:

Analog werden allgemein ungesättigte Verbindungen hergestellt. Analogously, generally unsaturated compounds are prepared.  

Entsprechend können Verbindungen mit n = 4-8 hergestellt werden, da die entsprechenden endständigen Alkanolamine käuflich erworben und in die N-BOC geschützten Verbindungen umgewandelt werden können.Accordingly, compounds with n = 4-8 can be produced since the corresponding terminal alkanolamines are purchased and sold in the N-BOC protected compounds can be converted.

In der Folge werden Beispiele zur Synthese von Liposomenbestandteilen beschrieben, die die experimentelle Breite der vorliegenden Anmeldung belegen. Es können, wie aus den Beispielen hervorgeht, beliebige Fettsäureester- und Alkyletherkombinationen hergestellt werden, die in Kettenlänge, Anzahl der cis-Doppelbindungen und Verzweigungsgrad variieren.The following are examples of the synthesis of liposome components described the experimental breadth of the present application occupy. It can, as the examples show, any Fatty acid ester and alkyl ether combinations are prepared in Chain length, number of cis double bonds and degree of branching vary.

Die Rf-Werte der Beispielsverbindungen 1 bis 279 wurden im System CHCl3/CH3OH (Eisessig/H2O: 100/60/20/5 Volumenanteile bestimmt. Sie liegen gruppenweise sehr dicht beisammen und zwar wie folgt:
The Rf values of the example compounds 1 to 279 were determined in the system CHCl 3 / CH 3 OH (glacial acetic acid / H 2 O: 100/60/20/5 by volume) and are very close in groups as follows:

RFRF Verbindungen Nr.Connections no. 0,10-0,150.10-0.15 129-135129-135 0,15-0,200.15-0.20 117-128; 167-172; 209-216;117-128; 167-172; 209-216; 0,20-0,250.20-0.25 70-84; 98-116; 151-166; 197-20870-84; 98-116; 151-166; 197-208 0,25-0,300.25-0.30 45-69; 136-150; 183-196; 262-27245-69; 136-150; 183-196; 262-272 0,30-0,350.30-0.35 24-44; 173-182; 255-261; 273-27924-44; 173-182; 255-261; 273-279 0,35-0,400.35-0.40 1-241-24 0,40-0,450.40 to 0.45 85-9785-97 0,30-0,400.30-0.40 217-240217-240 0,20-0,300.20-0.30 241-254241-254

BeispieleExamples A) Herstellung von Erucoyl-propandiol-(1,3)-phospho-N,N,N- trimethyl-propylammonium (Beispiel 176)A) Preparation of erucoyl-propanediol- (1,3) -phospho-N, N, N- trimethyl-propylammonium (Example 176) Erucoyl-propandiol-(1.3)Erucoyl-propanediol (1.3)

Propandiol-(1.3), 153 g (MG 76.1; 2 Mol) wird in 1 l THF gelöst, mit 60 g Triethylamin (MG 101.2; 0.6 Mol) und 7.3 g 4-Dimethylaminopyridin (MG 122.2; 0.06 Mol) versetzt und in einem Wasserbad auf 20°C temperiert. Unter stetem Rühren werden 178 g Erucoylchlorid (MG 357.0; 0.5 Mol) in 500 ml THF langsam so zugetropft, daß die Temperatur 30°C im Reaktions­ gemisch nicht übersteigt. Nach dem Eintropfen wird noch 30 Minuten auf 30°C erwärmt, mit 1.5 l Diisopropylether und 1.5 l 1 N HCl versetzt. Nach gutem Schütteln und Phasenseparation wird die obere Etherphase nochmals mit 1% NaCl-Lösung gewaschen und in Vakuum bei 45°C einrotiert. Der Rückstand wird in 2 l Hexan aufgenommen und auf -20°C gekühlt. Die weißen Kristalle werden abgesaugt und im Vakuum getrocknet. Die Ausbeute reinem Erucoyl-propandiol-(1.3) beträgt 123 g (MG 396.7; 62%). Die Substanz ist dünnschichtchromatographisch rein (Rf-Wert 0.3 in Ether/Pentan/Essigsäure 200/200/2; Volumenanteile).
Propandiol (1.3), 153 g (MW 76.1, 2 mol) is dissolved in 1 l of THF, treated with 60 g of triethylamine (MW 101.2, 0.6 mol) and 7.3 g of 4-dimethylaminopyridine (MW 122.2, 0.06 mol) and in a Water bath at 20 ° C tempered. With constant stirring, 178 g of erucoyl chloride (MW 357.0, 0.5 mol) in 500 ml of THF are slowly added dropwise so that the temperature does not exceed 30 ° C in the reaction mixture. After dropwise addition, the mixture is warmed to 30 ° C. for a further 30 minutes, admixed with 1.5 l of diisopropyl ether and 1.5 l of 1N HCl. After shaking well and phase separation, the upper ether phase is washed again with 1% NaCl solution and concentrated in vacuo at 45 ° C. The residue is taken up in 2 l of hexane and cooled to -20 ° C. The white crystals are filtered off with suction and dried in vacuo. The yield of pure erucoyl-propanediol (1.3) is 123 g (MW 396.7, 62%). The substance is pure by thin-layer chromatography (Rf value 0.3 in ether / pentane / acetic acid 200/200/2, volume fractions).

Mikroanalyse
C25H48O3:
Berechnet:
C 75.70; H 12.20; O 12.10;
Gefunden:
C 75.81; H 12.16; O -.microanalysis
C 25 H 48 O 3 :
Calculated:
C 75.70; H 12.20; O 12.10;
Found:
C 75.81; H 12.16; O -.

Erucoyl-propandiol-(1.3)-phospho-N-methyl-propylammoniumErucoyl-propanediol (1.3) -phospho-N-methyl-propylammonium

Phosphoroxychlorid, 24.2 g (MG 153.33; 0.16 Mol) in 15 ml THF wird in einem Eisbad auf 0°C gekühlt. Man versetzt tropfenweise unter Rühren mit einer Lösung von Erucoyl-propandiol-(1.3), 60 g (MG 396.7; 0.15 Mol) und 17.2 g Triethylamin (MG 101.19; 0.17 Mol) in 250 ml THF, so daß die Temperatur im Reaktionsgemisch 15°C nicht übersteigt. Mach dem Eintropfen der Lösung wird die Temperatur des Reaktionsgemisches auf 20°C gebracht und 30 Minuten weitergerührt.Phosphorus oxychloride, 24.2 g (MW 153.33, 0.16 mol) in 15 ml of THF is added in a Ice bath cooled to 0 ° C. It is added dropwise with stirring with a Solution of erucoyl-propanediol- (1.3), 60 g (MW 396.7, 0.15 mol) and 17.2 g Triethylamine (MW 101.19, 0.17 mol) in 250 ml of THF, so that the temperature in the reaction mixture does not exceed 15 ° C. Make the solution drip the temperature of the reaction mixture is brought to 20 ° C and 30 minutes further stirred.

Die Umwandlung des gebildeten Erucoyl-propandiol-(1.3)-phosphorsäure­ dichlorids in das Zielprodukt erfolgt durch Umsetzung mit N-Methyl­ propanolamin über einen intermediären Sechsring. Dazu wird das Reaktions­ gemisch unter Rühren mit einer Losung von 16 g M-Methyl-propanolamin (MG 89.14; 0.18 Mol) und 35.4 g Triethylamin (MG 101.19; 0.35 Mol) in 250 ml THF tropfenweise so versetzt, daß die Temperatur 35°C nicht übersteigt. Nach dem Eintropfen wird das Reaktionsgemisch noch 30 Minuten bei 25°C gehalten. Das ausgefallene Triethylaminhydrochlorid wird abfiltriert. Das Filtrat enthält das Zwischenprodukt (Rf 0.25 in CHCl3/­ Essigester 1 : 1; Volumenanteile), das durch Zusatz von 60 ml 2 N HCl unter Ringöffnung in Erucoyl-propandiol-(1.3)-phospho-N-methyl-propyl­ ammonium (Rf 0.45 in CHCl3/CH3OH/Eisessig/H2O 100/80/10/5, Volumenteile) umgewandelt wird. Die THF-Lösung des Produktes wird mit 200 ml 0.2 M Natriumphosphatlösung (pH ∼ 8.0) versetzt und auf pH 6-7 gebracht. Man fällt das Produkt durch Zugabe von 1 l Aceton aus und isoliert die Kristalle durch Absaugen bei 4°C. Erucoyl-propandiol-(1.3)-phospho-N- methyl-propylammonium ist manchmal leicht verunreinigt. Zur Reinigung kann eine Chromatographie an Kieselgel mit CHCl3/CH3OH/H2O eingesetzt werden. Die Ausbeute an reinem Produkt - bezogen auf Erucoyl-propandiol-(1.3) - beträgt 65 g (MG 547.8; 79%).
The conversion of the erucoyl-propanediol (1.3) -phosphorsäure dichlorids formed in the target product by reaction with N-methyl propanolamine via an intermediate six-membered ring. For this purpose, the reaction mixture is added dropwise with stirring to a solution of 16 g of M-methyl-propanolamine (M.W. 89.14, 0.18 mol) and 35.4 g of triethylamine (M.W. 101.19, 0.35 mol) in THF 250 ml, so that the temperature is 35.degree does not exceed. After the dropwise addition, the reaction mixture is kept at 25 ° C. for a further 30 minutes. The precipitated triethylamine hydrochloride is filtered off. The filtrate contains the intermediate (Rf 0.25 in CHCl 3 / ethyl acetate 1: 1, volume fractions), which by adding 60 ml of 2N HCl with ring opening in erucoyl-propanediol- (1.3) -phospho-N-methyl-propyl ammonium (Rf 0.45 in CHCl 3 / CH 3 OH / glacial acetic acid / H 2 O 100/80/10/5, parts by volume). The THF solution of the product is mixed with 200 ml of 0.2 M sodium phosphate solution (pH ~ 8.0) and brought to pH 6-7. The product is precipitated by addition of 1 l of acetone and the crystals are isolated by suction at 4 ° C. Erucoylpropanediol- (1.3) -phospho-N-methyl-propylammonium is sometimes slightly contaminated. For purification, chromatography on silica gel with CHCl 3 / CH 3 OH / H 2 O can be used. The yield of pure product - based on erucoyl-propanediol (1.3) - is 65 g (MW 547.8, 79%).

Mikroanalyse
C29H58NO6P:
Berechnet:
C 63.59; H 10.67; N 2.56; O 17.53; P 5.66;
Gefunden:
C 63.34; H 10.49; N 2.49; O -; P 5.59.microanalysis
C 29 H 58 NO 6 P:
Calculated:
C 63.59; H 10.67; N 2.56; O 17:53; P 5.66;
Found:
C 63.34; H 10.49; N 2.49; O -; P 5.59.

Erucoyl-propandiol-(13)-phospho-N.N.N-trimethyl-propylammoniumErucoyl-propanediol (13) -phospho-N.N.N-trimethyl-propylammonium

Erucoyl-propandiol-(1.3)-phospho-N-methyl-propylammonium, 54.8 g (MG 547.8; 0.1 Mol) werden mit 800 ml THF und 83 g K2CO3 (0.6 Mol) in 800 ml H2O versetzt. Man erwärmt auf 50°C und erhält eine zweiphasige Lösung. Man tropft unter starkem Rühren 74.5 g Toluolsulfonsäuremethylester (MG 186.23; 0.4 Mol) in 200 ml THF ein und kocht unter Rückfluß. Die Reaktion ist nach 60 Minuten beendet. Erucoyl-propandiol-(1.3)- phospho-N.N.N-trimethyl-propylammonium als Produkt (Rf-Wert 0.1 in CHCl3/CH3OH/Eisessig/H2O 100/80/10/5, Volumenanteile) wird aus der THF-Phase mit 1.2 l Aceton ausgefällt, der Niederschlag in 300 ml CHCl3 aufgenommen, filtriert und nochmals mit 1.2 l Aceton gefällt. Ist das Produkt nicht ganz rein, kann zur Aufreinigung eine Chromatographie an Kieselgel mit CHCl3/CH3OH/H2O eingesetzt werden. Die Ausbeute an reinem Produkt - bezogen auf die N-methyl-Verbindung beträgt 49 g (MG 575.8; 85%).
Erucoylpropanediol- (1.3) -phospho-N-methyl-propylammonium, 54.8 g (MW 547.8, 0.1 mol) are treated with 800 ml of THF and 83 g of K 2 CO 3 (0.6 mol) in 800 ml of H 2 O. The mixture is heated to 50 ° C and receives a two-phase solution. 74.5 g of methyl toluenesulphonate (MW 186.23, 0.4 mol) in 200 ml of THF are added dropwise with vigorous stirring, and the mixture is refluxed. The reaction is complete after 60 minutes. Erucoylpropanediol- (1.3) - phosphono-N, N-trimethyl-propylammonium as product (Rf value 0.1 in CHCl 3 / CH 3 OH / glacial acetic acid / H 2 O 100/80/10/5, volume fractions) is extracted from the THF Phase precipitated with 1.2 l of acetone, the precipitate was taken up in 300 ml of CHCl 3 , filtered and precipitated again with 1.2 l of acetone. If the product is not completely pure, chromatography on silica gel with CHCl 3 / CH 3 OH / H 2 O can be used for the purification. The yield of pure product - based on the N-methyl compound is 49 g (MW 575.8, 85%).

Mikroanalyse
C31H62NO6P:
Berechnet:
C 64.66; H 10.85; N 2.43; O 16.67; P 5.38;
Gefunden:
C 64.38; H 10.81; N 2.39; O -; P 5.27. microanalysis
C 31 H 62 NO 6 P:
Calculated:
C 64.66; H 10.85; N 2.43; O 16.67; P 5.38;
Found:
C 64.38; H 10.81; N 2.39; O -; P 5.27.

B) Herstellung von Erucoyl-propandiol-(1,3)-phospho-N,N-dimethyl-N- (hydroxypropyl-dihydroxypropyl)-propylammonium (Beispiel 155)B) Preparation of erucoyl-propanediol- (1,3) -phospho-N, N-dimethyl-N- (Hydroxypropyl-dihydroxypropyl) -propylammonium (Example 155)

Zur Herstellung dieser Verbindung kann das Zwischenprodukt Erucoyl­ propandiol-(1.3)-phospho-N-methyl-propylammonium eingesetzt werden. Es wird in einer Reaktion zuerst mit einem Epoxyd umgesetzt und direkt weiter zum Endprodukt methyliert.For the preparation of this compound, the intermediate erucoyl propanediol (1.3) phospho-N-methyl-propylammonium be used. It is first reacted with an epoxide in a reaction and directly further methylated to the final product.

Erucoyl-propandiol-(1.3)-phospho-N-methyl-propylammonium, 54.8 g (MG 547.8; 0.1 Mol) werden mit 800 ml THF und 83 g K2CO3 (0.6 Mol) in 800 ml H2O versetzt. Man erwärmt auf 50°C und erholt eine zweiphasige Lösung. Man tropft unter starkem Rühren eine Lösung aus 21 g 1.2-Iso­ propyliden-glycero-3.1-glycidol (MW 188.2; 0.11 Mol) in 200 ml THF ein und erhöht die Temperatur auf 60°C. Das Reaktionsgemisch wird 2 Stunden unter leichtem Rückfluß gekocht und mit 37 g Toluolsulfonsäuremethylester (MG 186.23; 0.2 Mol) in 100 ml THF versetzt. Nach 2 Stunden Kochen unter Rückfluß ist die Reaktion beendet. Die THF-Phase wird bei 45°C weitgehend einrotiert und der Rückstand zur Entfernung der Isopropylidenschutzgruppe mit 300 ml 70% Essigsäure auf 60-65°C erhitzt. Man versetzt das Reaktions­ gemisch mit einem Gemisch aus 1 l CHCl3/1 l CH3OH/ 1 l 1%ige NaCl-Lösung, schüttelt gut durch und entfernt das Lösungsmittel aus der unteren CHCl3-Phase in Vakuum. Der Rückstand wird in 400 ml CHCl3 aufgenommen und mit 1.6 l Aceton gefällt. Zur Reinigung kann eine Chromatographie an Kieselgel mit CHCl3/CH3OH/H2O eingesetzt werden. Man erhält 46 g Erucoyl-propandiol-(1.3)-phospho-N.N-dimethyl-N-(hydroxypropyl- 3.1-dihydroxypropyl)-propylammonium (MG 709.94; 65%).Erucoylpropanediol- (1.3) -phospho-N-methyl-propylammonium, 54.8 g (MW 547.8, 0.1 mol) are treated with 800 ml of THF and 83 g of K 2 CO 3 (0.6 mol) in 800 ml of H 2 O. It is heated to 50 ° C and recovered a two-phase solution. A solution of 21 g of 1,2-isopropylidene-glycero-3,1-glycidol (MW 188.2, 0.11 mol) in 200 ml of THF is added dropwise with vigorous stirring, and the temperature is raised to 60.degree. The reaction mixture is boiled for 2 hours under light reflux and treated with 37 g of methyl toluenesulphonate (MW 186.23, 0.2 mol) in 100 ml of THF. After 2 hours of refluxing, the reaction is complete. The THF phase is largely concentrated by rotary evaporation at 45 ° C. and the residue is heated to 60-65 ° C. with 300 ml of 70% acetic acid to remove the isopropylidene protective group. Is added to the reaction mixture with a mixture of 1 L of CHCl 3 / CH 3 OH 1 l / 1 l 1% NaCl solution, shaken well and the solvent is removed from the lower phase CHCl 3 in vacuo. The residue is taken up in 400 ml of CHCl 3 and precipitated with 1.6 l of acetone. For purification, chromatography on silica gel with CHCl 3 / CH 3 OH / H 2 O can be used. This gives 46 g of erucoyl-propanediol- (1.3) -phosphono-N, N-dimethyl-N- (hydroxypropyl-3.1-dihydroxypropyl) -propylammonium (MW 709.94, 65%).

Alle nachstehend aufgeführten Verbindungen können nach diesen allgemeinen Vorschriften zur Herstellung sowohl am Stickstoff hydroxylierter wie auch nicht hydroxylierter Verbindung dargestellt werden. All compounds listed below may be according to these general Regulations for the preparation of both the hydroxylated on the nitrogen as well non-hydroxylated compound.  

Beispiele für zweikettige Glycero-phosoho-N,N-dimethyl-N- dihydroxypropylalkylammonium-VerbindungenExamples of two-chain glycerol-phosoho-N, N-dimethyl-N- dihydroxypropylalkylammonium compounds

(A = a; n = 2-6; R3 (A = a; n = 2-6; R 3

, CH3 , CH 3

; m = 1; x = 0; y = 1; z = 1)
; m = 1; x = 0; y = 1; z = 1)

1) 1,2-Dipalmitoyl-sn-glycero-3-phospho-N,N-dimethyl-N- dihydroxypropyl-ethylammonium (n = 2)
(R1, R2 = CO-(CH2)14-CH3)
C42H84NO10P (794, 10)
2) 1,2-Distearoyl-sn-glycero-3-phospho-N,N-dimethyl-N-dihydroxypropyl- ethylammonium (n = 2)
(R1, R2 = CO-(CH2)16-CH3)
C46H92NO10P (850,20)
3) 1,2-Dimyristoyl-sn-glycero-3-phospho-N,N-dimethyl-N- dihydroxypropyl-ethylammonium (n = 2)
(R1, R2 = CO-(CH2)12-CH3)
C38H76NO10P (737,99)
4) 1,2-Dierucyl-sn-glycero-3-phospho-N,N-dimethyl-N-dihydroxypropyl- ethylammonium (n = z)
(R1, R2 = CO-(CH2)11-CH=CH-(CH2)7-CH3)
C54H104NO10P (958,39)
5) 1,2-Dioleoyl-sn-glycero-3-phospho-N,N-dimethyl-N-dihydroxypropyl- ethylammonium (n = 2)
(R1, R2 = CO-(CH2)7-CH=CH-(CH2)7-CH3)
C46H88NO10P (846,17)
6) 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-N,N-dimethyl-N- dihydroxypropyl-ethylammonium (n = 2)
(R1 = CO-(CH2)16-CH3; R2 = CO-(CH2)17-CH=CH(CH2)7-CH3)
C46H90NO10P (848,19)
7) 1-Stearoyl-2-myristoyl-sn-glycero-3-phospho-N,N-dimethyl-N- dihydroxypropyl-ethylammonium (n = 2)
(R1 = CO-(CH2)16-CH3; R2 = CO-(CH2)12-CH3)
C42H84NO10P (794,10)
8) 1-Stearoyl-2-lauroyl-sn-glycero-3-phospho-N,N-dimethyl-N- dihydroxypropyl-ethylammonium (n = 2)
(R1 = CO-(CH2)16-CH3; R2 = CO-(CH2)10-CH3)
C40H80NO10P (766,04)
9) 1-Lauroyl-2-stearoyl-sn-glycero-3-phospho-N,N-dimethyl-N- dihydroxypropyl-ethylammonium (n = 2)
(R1 = CO-(CH2)10-CH3; R2 = CO-(CH2)16-CH3)
C40H80NO10P (766,04)
10) 1-Erucoyl-2-oleoyl-sn-glycero-3-phospho-N,N-dimethyl-N- dihydroxypropyl-ethylammonium (n = 2)
(R1 = CO-(CH2)11-CH=CH-(CH2)7-CH3)
(R2 = CO-(CH2)7-CH=CH-(CH2)7-CH3)
C50H96NO10P (902,28)
11) 1-Oleoyl-2-erucyl-sn-glycero-3-phospho-N,N-dimethyl-N- dihydroxypropyl-ethylammonium (n = 2)
(R1 = CO-(CH2)7-CH=CH-(CH2)7-CH3)
(R2 = CO-(CH2)11-CH=CH-(CH2)7-CH3)
C50H96NO10P (902,28)
12) 1,2-Dipalmitoyl-sn-glycero-3-phospho-N,N-dimethyl-N- dihydroxypropyl-ethylammonium (n = 3)
(R1, R2 = Cl-(CH2)14-CH3)
C43H86NO10P (808,12)
13) 1,2-Dierucyl-sn-glycero-3-phospho-N,N-dimethyl-N-dihydroxypropyl- ethylammonium (n = 3)
(R1, R2 = CO-(CH2)11-CH=CH-(CH2)7-CH3)
C55H106NO10P (972,413)
14) 1,2-Dioleoyl-sn-glycero-3-phospho-N,N-dimethyl-N-dihydroxypropyl- ethylammonium (n = 3)
(R1, R2 = CO-(CH2)7-CH=CH-(CH2)7-CH3)
C47H90NO10P (860,20)
15) 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-N,N-dimethyl-N- dihydroxypropyl-ethylammonium (n = 3)
(R1 = CO-(CH2)16-CH3; R2=CO-(CH2)7-CH=CH-(CH2)7- CH3)
C47H92NO10P (862,21)
16) 1-Stearoyl-2-lauroyl-sn-glycero-3-phospho-N,N-dimethyl-N- dihydroxypropyl-ethylammonium (n = 3)
(R1 = CO-(CH2)16-CH3; R2 = CO-(CH2)10-CH3)
C41H82NO10P (780,07)
17) 1,2-Dipalmitoyl-sn-glycero-3-phospho-N,N-dimethyl-N- dihydroxypropyl-butylammonium (n = 4)
(R1, R2 = CO-(CH2)14-CH3)
C44H88NO10P (822,15)
18) 1,2-Dioleoyl-sn-glycero-3-phospho-N,N-dimethyl-N-dihydroxypropyl- butylammonium (n = 4)
(R1, R2 = CO-(CH2)7-CH=CH-(CH2)7-CH3)
C48H92NO10P (874,23)
19) 1,2-Dierucyl-sn-glycero-3-phospho-N,N-dimethyl-N-dihydroxypropyl- butylammonium (n = 4)
(R1, R2 = CO-(CH2)7-CH=CH-(CH2)7-CH3)
C56H108NO10P (986,44)
20) 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-N,N-dimethyl-N- dihydroxypropyl-butylammonium (n = 4)
(R1 = CO-(CH2)16-CH3; R2 = CO-(CH2)7-CH = CH-(CH2)7- CH3)
C48H94NO10P (876,24)
21) 1-Stearoyl-2-lauroyl-sn-glycero-3-phospho-N,N-dimethyl-N- dihydroxypropyl-butylammonium (n = 4)
(R1 = CO-(CH2)16-CH3; R2 = CO-(CH2)10-CH3)
C42H84NO10P (794,10)
22) 1,2-Dipalmitoyl-sn-glycero-3-phospho-N,N-dimethyl-N- dihydroxypropyl-hexylammonium (n = 6)
(R1, R2 = CO-(CH2)14-CH3)
C42H84NO10P (794,10)
23) 1,2-Dioleoyl-sn-glycero-3-phospho-N,N-dimethyl-N-dihydroxypropyl- hexylammonium (n = 6)
(R1, R2 = CO-(CH2)7-CH=CH-(CH2)7-CH3)
C50H96NO10P (902,28)
24) 1,2-Dierucyl-sn-glycero-3-phospho-N,N-dimethyl-N-dihydroxypropyl- hexylammonium (n = 6)
(R1, R2 = CO-(CH2)11-CH=CH-(CH2)7-CH3)
C58H112NO10P (1014,49)1) 1,2-dipalmitoyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium (n = 2)
(R 1 , R 2 = CO- (CH 2 ) 14 -CH 3 )
C 42 H 84 NO 10 P (794, 10)
2) 1,2-distearoyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium (n = 2)
(R 1 , R 2 = CO- (CH 2 ) 16 -CH 3 )
C 46 H 92 NO 10 P (850.20)
3) 1,2-Dimyristoyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium (n = 2)
(R 1 , R 2 = CO- (CH 2 ) 12 -CH 3 )
C 38 H 76 NO 10 P (737.99)
4) 1,2-Dierucyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium (n = z)
(R 1 , R 2 = CO- (CH 2 ) 11 -CH = CH- (CH 2 ) 7 -CH 3 )
C 54 H 104 NO 10 P (958.39)
5) 1,2-Dioleoyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium (n = 2)
(R 1 , R 2 = CO- (CH 2 ) 7 -CH = CH- (CH 2 ) 7 -CH 3 )
C 46 H 88 NO 10 P (846,17)
6) 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium (n = 2)
(R 1 = CO- (CH 2 ) 16 -CH 3 ; R 2 = CO- (CH 2 ) 17 -CH = CH (CH 2 ) 7 -CH 3 )
C 46 H 90 NO 10 P (848,19)
7) 1-stearoyl-2-myristoyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium (n = 2)
(R 1 = CO- (CH 2 ) 16 -CH 3 ; R 2 = CO- (CH 2 ) 12 -CH 3 )
C 42 H 84 NO 10 P (794.10)
8) 1-Stearoyl-2-lauroyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium (n = 2)
(R 1 = CO- (CH 2 ) 16 -CH 3 ; R 2 = CO- (CH 2 ) 10 -CH 3 )
C 40 H 80 NO 10 P (766.04)
9) 1-Lauroyl-2-stearoyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium (n = 2)
(R 1 = CO- (CH 2 ) 10 -CH 3 ; R 2 = CO- (CH 2 ) 16 -CH 3 )
C 40 H 80 NO 10 P (766.04)
10) 1-Erucoyl-2-oleoyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium (n = 2)
(R 1 = CO- (CH 2 ) 11 -CH = CH- (CH 2 ) 7 -CH 3 )
(R 2 = CO- (CH 2 ) 7 -CH = CH- (CH 2 ) 7 -CH 3 )
C 50 H 96 NO 10 P (902.28)
11) 1-Oleoyl-2-erucyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium (n = 2)
(R 1 = CO- (CH 2 ) 7 -CH = CH- (CH 2 ) 7 -CH 3 )
(R 2 = CO- (CH 2 ) 11 -CH = CH- (CH 2 ) 7 -CH 3 )
C 50 H 96 NO 10 P (902.28)
12) 1,2-dipalmitoyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium (n = 3)
(R 1 , R 2 = Cl- (CH 2 ) 14 -CH 3 )
C 43 H 86 NO 10 P (808.12)
13) 1,2-Dierucyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium (n = 3)
(R 1 , R 2 = CO- (CH 2 ) 11 -CH = CH- (CH 2 ) 7 -CH 3 )
C 55 H 106 NO 10 P (972,413)
14) 1,2-Dioleoyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium (n = 3)
(R 1 , R 2 = CO- (CH 2 ) 7 -CH = CH- (CH 2 ) 7 -CH 3 )
C 47 H 90 NO 10 P (860.20)
15) 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium (n = 3)
(R 1 = CO- (CH 2 ) 16 -CH 3 ; R 2 = CO- (CH 2 ) 7 -CH = CH- (CH 2 ) 7 -CH 3 )
C 47 H 92 NO 10 P (862.21)
16) 1-Stearoyl-2-lauroyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium (n = 3)
(R 1 = CO- (CH 2 ) 16 -CH 3 ; R 2 = CO- (CH 2 ) 10 -CH 3 )
C 41 H 82 NO 10 P (780.07)
17) 1,2-dipalmitoyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-butylammonium (n = 4)
(R 1 , R 2 = CO- (CH 2 ) 14 -CH 3 )
C 44 H 88 NO 10 P (822,15)
18) 1,2-Dioleoyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-butylammonium (n = 4)
(R 1 , R 2 = CO- (CH 2 ) 7 -CH = CH- (CH 2 ) 7 -CH 3 )
C 48 H 92 NO 10 P (874.23)
19) 1,2-Dierucyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-butylammonium (n = 4)
(R 1 , R 2 = CO- (CH 2 ) 7 -CH = CH- (CH 2 ) 7 -CH 3 )
C 56 H 108 NO 10 P (986.44)
20) 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-butylammonium (n = 4)
(R 1 = CO- (CH 2 ) 16 -CH 3 ; R 2 = CO- (CH 2 ) 7 -CH = CH- (CH 2 ) 7 -CH 3 )
C 48 H 94 NO 10 P (876.24)
21) 1-Stearoyl-2-lauroyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-butylammonium (n = 4)
(R 1 = CO- (CH 2 ) 16 -CH 3 ; R 2 = CO- (CH 2 ) 10 -CH 3 )
C 42 H 84 NO 10 P (794.10)
22) 1,2-dipalmitoyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-hexylammonium (n = 6)
(R 1 , R 2 = CO- (CH 2 ) 14 -CH 3 )
C 42 H 84 NO 10 P (794.10)
23) 1,2-Dioleoyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-hexylammonium (n = 6)
(R 1 , R 2 = CO- (CH 2 ) 7 -CH = CH- (CH 2 ) 7 -CH 3 )
C 50 H 96 NO 10 P (902.28)
24) 1,2-Dierucyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-hexylammonium (n = 6)
(R 1 , R 2 = CO- (CH 2 ) 11 -CH = CH- (CH 2 ) 7 -CH 3 )
C 58 H 112 NO 10 P (1014.49)

Beispiele für zweikettige Glycero-phosoho-N,N-dimethyl-N-(2-hydroxypropyl- 3,1-O,O-dihydroxypropyl)-alkylammonium-VerbindungenExamples of two-chain glycerophospho-N, N-dimethyl-N- (2-hydroxypropyl) 3,1-O, O-dihydroxypropyl) alkylammonium compounds

(A = a; n = 2-6; R3 (A = a; n = 2-6; R 3

, O3 , O 3

; m = 1; x = 0; y = 1; z = 2)
; m = 1; x = 0; y = 1; z = 2)

25) 1,2-Dipalmitoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(2- hydroxypropyl-3,1-O,O-dihydroxypropyl)-ethylammonium (n = 2)
(R1; R2 = CO-(CH2)14-CH3)
C45H90NO12P (868,18)
26) 1,2-Distearoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(2- hydroxypropyl-3,1-O,O-dihydroxypropyl)-ethylammonium (n = 2)
(R1, R2 = CO-(CH2)16-CH3)
C49H98NO12P (924,28)
27) 1,2-Dierucoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(2- hydroxypropyl-3,1-O,O-dihydroxypropyl)-ethylammonium (n = 2)
(R1, R2 = CO-(CH2)11-CH=CH-(CH2)7-CH3)
C57H110NO12P (1032,47)
28) 1,2-Dioleoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(2-hydroxypropyl- 3,1-O,O-dihydroxypropyl)-ethylammonium (n = 2)
(R1, R2 = CO-(CH2)7-CH=CH-(CH2)7-CH3)
C49H94NO12P (920,25)
29) 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(2- hydroxypropyl-3,1-O,O-dihydroxypropyl)-ethylammonium (n = 2)
(R1 = CO-(CH2)16-CH3; R2 = CO-(CH2)7-CH = CH-(CH2)7- CH3)
C49H96NO12P (922,27)
30) 1-Stearoyl-2-lauroyl-sn-glycero-3-phospho-N,N-dimethyl-N-(2- hydroxypropyl-3,1-O,O-dihydroxypropyl)-ethylammonium (n = 2)
(R1 = CO-(CH2)16-CH3; R2 = CO-(CH2)10-CH3)
C43H86NO12P (840,12)
31) 1-Erucoyl-2-oleoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(2- hydroxypropyl-3,1-O,O-dihydroxypropyl)-ethylammonium (n = 2)
(R1 = CO-(CH2)11-CH=CH-(CH2)7-CH3;
R2 = CO-(CH2)7-CH=CH-(CH2)7-CH3)
C53H102NO12P (976,36)
32) 1-Oleoyl-2-erucoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(2- hydroxypropyl-3,1-O,O-dihydroxypropyl)-ethylammonium (n = 2)
(R1 = CO-(CH2)7-CH=CH-(CH2)7-CH3;
R2 = CO-(CH2)11-CH=CH-(CH2)7-CH3)
C53H102NO12P (976,36)
33) 1,2-Dipalmitoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(2- hydroxypropyl-3,1-O,O-dihydroxypropyl)-propylammonium (n = 3)
(R17 R2 = CO-(CH2)14-CH3)
C45H92NO12P (882,20)
34) 1,2-Distearoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(2- hydroxypropyl-3,1-O,O-dihydroxypropyl)-propylammonium (n = 3)
(R1, R2 = CO-(CH2)16-CH3)
C50H100NO12P (938,31)
35) 1,2-Dierucoyl-sn-glycero-3.phospho-N,N-dimethyl-N-(2- hydroxypropyl-3,1-O,O-dihydroxypropyl)-propylammonium (n = 3)
(R11 R2 = CO-(CH2)11-CH=CH-(CH2)7-CH3)
C58H112NO12P (1046,49)
36) 1,2-Dioleoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(2-hydroxypropyl- 3,1-O,O-dihydroxypropyl)-propylammonium (n = 3)
(R1, R2 = CO-(CH2)7-CH=CH-(CH2)7-CH3)
C50H96NO12P (934,28)
37) 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(2- hydroxypropyl-3,1-O,O-dihydroxypropyl)-propylammonium (n = 3)
(R1 = CO-(CH2)16-CH3; R2 = CO-(CH2)7-CH=CH-(CH2)7-CH3)
C50H98NO12P (936,29)
38) 1-Stearoyl-2-lauroyl-sn-glycero-3-phospho-N,N-dimethyl-N-(2- hydroxypropyl-3,1-O,O-dihydroxypropyl)-propylammonium (n = 3)
(R1 = CO-(CH2)16-CH3; R2 = CO-(CH2)10-CH3)
C44H88NO12P (854,15)
39) 1,2-Dioleoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(2-hydroxypropyl- 3,1-O,O-dihydroxypropyl)-butylammonium (n = 4)
(R1, R2 = CO-(CH2)7-CH=CH-(CH2)7-CH3)
C51H98NO12P (948,30)
40) 1,2-Dierucoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(2- hydroxypropyl-3,1-O,O-dihydroxypropyl)-butylammonium (n = 4)
(R1, R2 = CO-(CH2)11-CH=CH-(CH2)7-CH3)
C59H114NO12P (1060,52)
41) 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(2- hydroxypropyl-3,1-O,O-dihydroxypropyl)-butylammonium (n = 4)
(R1 = CO-(CH2)16-CH3; R2 = CO-(CH2)7-CH=CH-(CH2)7- CH3)
C51H100NO12P (950,32)
42) 1-Stearoyl-2-lauroyl-sn-glycero-3-phospho-N,N-dimethyl-N-(2- hydroxypropyl-3,1-O,O-dihydroxypropyl)-butylammonium (n = 4)
(R1 = CO-(CH2)16-CH3; R2 = CO-(CH2)10-CH3)
C45H90NO12P (868,175)
43) 1,2-Dioleoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(2-hydroxypropyl- 1,3-O,O-dihydroxypropyl)-hexylammonium (n = 6)
(R2, R2 = CO-(CH2)7-CH=CH-(CH2)7-CH3)
C53H102NO12P (976,358)
44) 1,2-Dierucoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(2- hydroxypropyl-3,1-O,O-dihydroxypropyl)-hexylammonium (n = 6)
(R1, R2 = CO-(CH2)11-CH=CH-(CH2)7-CH3)
C61H118NO12P (1088,57)25) 1,2-Dipalmitoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -ethylammonium (n = 2)
(R 1 , R 2 = CO- (CH 2 ) 14 -CH 3 )
C 45 H 90 NO 12 P (868.18)
26) 1,2-distearoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -ethylammonium (n = 2)
(R 1 , R 2 = CO- (CH 2 ) 16 -CH 3 )
C 49 H 98 NO 12 P (924.28)
27) 1,2-Dierucoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -ethylammonium (n = 2)
(R 1 , R 2 = CO- (CH 2 ) 11 -CH = CH- (CH 2 ) 7 -CH 3 )
C 57 H 110 NO 12 P (1032.47)
28) 1,2-Dioleoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -ethylammonium (n = 2)
(R 1 , R 2 = CO- (CH 2 ) 7 -CH = CH- (CH 2 ) 7 -CH 3 )
C 49 H 94 NO 12 P (920,25)
29) 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -ethylammonium (n = 2)
(R 1 = CO- (CH 2 ) 16 -CH 3 ; R 2 = CO- (CH 2 ) 7 -CH = CH- (CH 2 ) 7 -CH 3 )
C 49 H 96 NO 12 P (922.27)
30) 1-Stearoyl-2-lauroyl-sn-glycero-3-phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -ethylammonium (n = 2)
(R 1 = CO- (CH 2 ) 16 -CH 3 ; R 2 = CO- (CH 2 ) 10 -CH 3 )
C 43 H 86 NO 12 P (840,12)
31) 1-Erucoyl-2-oleoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -ethylammonium (n = 2)
(R 1 = CO- (CH 2 ) 11 -CH = CH- (CH 2 ) 7 -CH 3 ;
R 2 = CO- (CH 2 ) 7 -CH = CH- (CH 2 ) 7 -CH 3 )
C 53 H 102 NO 12 P (976.36)
32) 1-Oleoyl-2-erucoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -ethylammonium (n = 2)
(R 1 = CO- (CH 2 ) 7 -CH = CH- (CH 2 ) 7 -CH 3 ;
R 2 = CO- (CH 2 ) 11 -CH = CH- (CH 2 ) 7 -CH 3 )
C 53 H 102 NO 12 P (976.36)
33) 1,2-dipalmitoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -propylammonium (n = 3)
(R 17 R 2 = CO- (CH 2 ) 14 -CH 3 )
C 45 H 92 NO 12 P (882.20)
34) 1,2-distearoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -propylammonium (n = 3)
(R 1 , R 2 = CO- (CH 2 ) 16 -CH 3 )
C 50 H 100 NO 12 P (938.31)
35) 1,2-Dierucoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -propylammonium (n = 3)
(R 11 R 2 = CO- (CH 2 ) 11 -CH = CH- (CH 2 ) 7 -CH 3 )
C 58 H 112 NO 12 P (1046.49)
36) 1,2-Dioleoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -propylammonium (n = 3)
(R 1 , R 2 = CO- (CH 2 ) 7 -CH = CH- (CH 2 ) 7 -CH 3 )
C 50 H 96 NO 12 P (934.28)
37) 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -propylammonium (n = 3)
(R 1 = CO- (CH 2 ) 16 -CH 3 ; R 2 = CO- (CH 2 ) 7 -CH = CH- (CH 2 ) 7 -CH 3 )
C 50 H 98 NO 12 P (936.29)
38) 1-Stearoyl-2-lauroyl-sn-glycero-3-phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -propylammonium (n = 3)
(R 1 = CO- (CH 2 ) 16 -CH 3 ; R 2 = CO- (CH 2 ) 10 -CH 3 )
C 44 H 88 NO 12 P (854.15)
39) 1,2-Dioleoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -butylammonium (n = 4)
(R 1 , R 2 = CO- (CH 2 ) 7 -CH = CH- (CH 2 ) 7 -CH 3 )
C 51 H 98 NO 12 P (948.30)
40) 1,2-Dierucoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -butylammonium (n = 4)
(R 1 , R 2 = CO- (CH 2 ) 11 -CH = CH- (CH 2 ) 7 -CH 3 )
C 59 H 114 NO 12 P (1060.52)
41) 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -butylammonium (n = 4)
(R 1 = CO- (CH 2 ) 16 -CH 3 ; R 2 = CO- (CH 2 ) 7 -CH = CH- (CH 2 ) 7 -CH 3 )
C 51 H 100 NO 12 P (950.32)
42) 1-Stearoyl-2-lauroyl-sn-glycero-3-phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -butylammonium (n = 4)
(R 1 = CO- (CH 2 ) 16 -CH 3 ; R 2 = CO- (CH 2 ) 10 -CH 3 )
C 45 H 90 NO 12 P (868,175)
43) 1,2-Dioleoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (2-hydroxypropyl-1,3-O, O-dihydroxypropyl) -hexylammonium (n = 6)
(R 2 , R 2 = CO- (CH 2 ) 7 -CH = CH- (CH 2 ) 7 -CH 3 )
C 53 H 102 NO 12 P (976,358)
44) 1,2-Dierucoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -hexylammonium (n = 6)
(R 1 , R 2 = CO- (CH 2 ) 11 -CH = CH- (CH 2 ) 7 -CH 3 )
C 61 H 118 NO 12 P (1088.57)

Beispiele für zweikettige Glycero-phospho-N,N-dimethyl-N-(2-hydroxypropyl- 3,1-O,O-2-hydroxypropyl-3,1-O,O-dihydroxypropyl)-alkylammonium- VerbindungenExamples of two-chain glycero-phospho-N, N-dimethyl-N- (2-hydroxypropyl) 3,1-O, O-2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -alkylammonium links

(A = a; n = 2-8; R3 (A = a; n = 2-8; R 3

, CH3 , CH 3

; m = 1; x = 0; y = 1; z = 3)
; m = 1; x = 0; y = 1; z = 3)

45) 1,2-Dipalmitoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(2- hydroxypropyl-3,1-O,O-2-hydroxypropyl-3,1-dihydroxypropyl)- ethylammonium (n = 2)
(im weiteren Text wird N-(2-hydroxypropyl-3,1-O,O-2-hydroxypropyl- 3,1-dihydroxypropyl) abgekürzt als N-(HP1-HP2-diHP3)
C48H96NO14P (942,25)
46) 1,2-Distearoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1HP2-diHP3)- ethylammonium (n = 2)
C52H104NO14P (998,36)
47) 1,2-Dierucoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- ethylammonium (n = 2)
C60H116NO14P (1106,54)
48) 1,2-Dioleoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- ethylammonium (n = 2)
C52H100NO14P (994,33)
49) 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-N,N-dimethyl-N(HP1-HP2- diHP3)-ethylammonium (n = 2)
C52H102NO14P (996,35)
50) 1-Stearoyl-2-lauroyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2- diHP3)-ethylammonium (n = 2)
C46H92NO14P (914,20)
51) 1-Palmitoyl-2-lauroyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2- diHP3)-ethylammonium (n = 2)
C44H88NO14P (886,15)
52) 1,2-Dipalmitoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2- diHP3)-propylammonium (n = 3)
C49H98NO14P (956,28)
53) 1,2-Distearoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- propylammonium (n = 3)
C53H106NO14P (1012,39)
54) 1,2-Dierucoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- propylammonium (n = 3)
C61H118NO14P (1120,57)
55) 1,2-Dioleoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- propylammonium (n = 3)
C53H102NO14P (1008,36)
56) 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2- diHP3)-propylammonium (n = 3)
C53H104NO14P (1010,37)
57) 1-Stearoyl-2-lauroyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2- diHP3)-propylammonium (n = 3)
C47H94NO14P (928,23)
58) 1-Palmitoyl-2-lauroyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2- diHP3)-propylammonium (n = 3)
C45H90NO14P (900,17)
59) 1,2-Dipalmitoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2- diHP3)-butylammonium (n = 4)
C50H100NO14P (970,31)
60) 1,2-Distearoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- butylammonium (n = 4)
C54H108NO14P (1026,41)
61) 1,2-Dierucoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- butylammonium (n = 4)
C62H120NO14P (1134,60)
62) 1,2-Dioleoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- butylammonium (n = 4)
C54H104NO14P (1022,38)
63) 1,2-Dipalmitoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2- diHP3)-hexylammonium (n = 6)
C52H104NO14P (998,36)
64) 1,2-Distearoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- hexylammonium (n = 6)
C56H112NOP14P (1054,47)
65) 1,2-Dierucoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- hexylammonium (n = 6)
C64H124NO14P (1162,65)
66) 1,2-Dioleoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- hexylammonium (n = 6)
C56H108NO14P (1050,44)
67) 1,2-Distearoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- octylammonium (n = 8)
C58H116NO14P (1082,52)
68) 1,2-Dioleoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- octylammonium (n = 8)
C58H112NO14P (1078,49)
69) 1,2-Dierucoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- octylammonium (n = 8)
C66H128NO14P (1190,70) 45) 1,2-dipalmitoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-2-hydroxypropyl-3,1-dihydroxypropyl) -ethylammonium ( n = 2)
(hereinafter, N- (2-hydroxypropyl-3,1-O, O-2-hydroxypropyl-3,1-dihydroxypropyl) is abbreviated as N- (HP 1 -HP 2 -diHP 3 )
C 48 H 96 NO 14 P (942.25)
46) 1,2-distearoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 HP 2 -diHP 3 ) -ethylammonium (n = 2)
C 52 H 104 NO 14 P (998.36)
47) 1,2-Dierucoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -ethylammonium (n = 2)
C 60 H 116 NO 14 P (1106.54)
48) 1,2-Dioleoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -ethylammonium (n = 2)
C 52 H 100 NO 14 P (994.33)
49) 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-N, N-dimethyl-N (HP 1 -HP 2 -diHP 3 ) -ethylammonium (n = 2)
C 52 H 102 NO 14 P (996.35)
50) 1-Stearoyl-2-lauroyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -ethylammonium (n = 2)
C 46 H 92 NO 14 P (914,20)
51) 1-palmitoyl-2-lauroyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -ethylammonium (n = 2)
C 44 H 88 NO 14 P (886.15)
52) 1,2-dipalmitoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -propylammonium (n = 3)
C 49 H 98 NO 14 P (956.28)
53) 1,2-distearoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -propylammonium (n = 3)
C 53 H 106 NO 14 P (1012.39)
54) 1,2-Dierucoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -propylammonium (n = 3)
C 61 H 118 NO 14 P (1120.57)
55) 1,2-Dioleoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -propylammonium (n = 3)
C 53 H 102 NO 14 P (1008.36)
56) 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -propylammonium (n = 3)
C 53 H 104 NO 14 P (1010.37)
57) 1-stearoyl-2-lauroyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -propylammonium (n = 3)
C 47 H 94 NO 14 P (928.23)
58) 1-palmitoyl-2-lauroyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -propylammonium (n = 3)
C 45 H 90 NO 14 P (900,17)
59) 1,2-dipalmitoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -butylammonium (n = 4)
C 50 H 100 NO 14 P (970.31)
60) 1,2-distearoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -butylammonium (n = 4)
C 54 H 108 NO 14 P (1026.41)
61) 1,2-Dierucoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -butylammonium (n = 4)
C 62 H 120 NO 14 P (1134.60)
62) 1,2-Dioleoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -butylammonium (n = 4)
C 54 H 104 NO 14 P (1022.38)
63) 1,2-dipalmitoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -hexylammonium (n = 6)
C 52 H 104 NO 14 P (998.36)
64) 1,2-distearoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -hexylammonium (n = 6)
C 56 H 112 NOP 14 P (1054.47)
65) 1,2-Dierucoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -hexylammonium (n = 6)
C 64 H 124 NO 14 P (1162.65)
66) 1,2-Dioleoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -hexylammonium (n = 6)
C 56 H 108 NO 14 P (1050.44)
67) 1,2-distearoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -octylammonium (n = 8)
C 58 H 116 NO 14 P (1082.52)
68) 1,2-Dioleoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -octylammonium (n = 8)
C 58 H 112 NO 14 P (1078.49)
69) 1,2-Dierucoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -octylammonium (n = 8)
C 66 H 128 NO 14 P (1190.70)

Beispiele für zweikettige Glycero-phospho-N,N-dimethyl-N-(2-hydroxypropyl- 3,1-O,O-2-hydroxypropyl-3,1-O,O-2-hydroxypropyl-3,1-O,O-dihydroxypropyl)- alkylammonium-VerbindungenExamples of two-chain glycero-phospho-N, N-dimethyl-N- (2-hydroxypropyl) 3,1-O, O-2-hydroxypropyl-3,1-O, O-2-hydroxypropyl-3,1-O, O-dihydroxypropyl) - alkylammonium compounds

(A = a; n = 2, 3; R3 (A = a; n = 2, 3; R 3

, O3 , O 3

; m = 1; x = 0; y = 1; z = 4)
; m = 1; x = 0; y = 1; z = 4)

70) 1,2-Dipalmitoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(2- hydroxypropyl-3,1-O,O-2-hydroxypropyl-3,1-O,O-hydroxypropyl-3,1- dihydroxypropyl)-ethylammonium (n = 2)
(im weiteren Text wird N[2-hydroxypropyl-3,1-O,O-2-hydroxypropyl- 3,1-O,O-dihydroxypropyl-3,1-O,O-dihydroxypropyl] abgekürzt als N- (HP1-HP2-HP3-diHP4) angegeben.
C51H102NO16P (1016,33)
71) 1,2-Distearoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-HP3- diHP4)-ethylammonium (n = 2)
C55H110NO16P (1072,44)
72) 1,2-Dierucoyl-sn-glycero-3-phospho-N,N-di-ethyl-N-(HP1-HP2-HP3- diHP4)-ethylammonium (n = 2)
C63H122NO16P (1180,62)
73) 1,2-Dioleoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-HP3- diHP4)-ethylammonium (n = 2)
C55H106NO16P (1068,41)
74) 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2- HP3-diHP4)-ethylammonium (n = 2)
C55H108NO16P (1070,42)
75) 1-Stearoyl-2-lauroyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2- HP3-diHP4)-ethylammonium (n = 2)
C49H98NO16P (988,28)
76) 1-Palmitoyl-2-lauroyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2- HP3-diHP4)-ethylammonium (n = 2)
C47H94NO16P (960,23)
77) 1,2-Dipalmitoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-HP3- diHP4)-propylammonium (n = 3)
C52H104NO16P (1030,36)
78) 1,2-Distearoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-HP3- diHP4)-propylammonium (n = 3)
C56H112NO16P (1086,47)
79) 1,2-Dierucoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-HP3- diHP4)-propylammonium (n = 3)
80) 1,2-Dioleoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-HP3- diHP4)-propylammonium (n = 3)
C56H108NO16P (1082,43)
81) 1-Stearoyl-2-lauroyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2- HP3-diHP4)-propylammonium (n = 3)
C50H100NO16P (1002,31)
82) 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2- HP3-diHP4)-propylammonium (n = 3)
C56H110NO16P (1084,45)
83) 1-Arachinoyl-2-oleoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2- HP3-diHP4)-propylammonium (n = 3)
C58H114NO16P (1112,50)
84) 1-Behenoyl-2-oleoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2- HP3-diHP4)-propylammonium (n = 3)
C60H118NO16P (1140,56)70) 1,2-dipalmitoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-2-hydroxypropyl-3,1-O, O-hydroxypropyl -3,1-dihydroxypropyl) -ethylammonium (n = 2)
(Hereinafter, N [2-hydroxypropyl-3,1-O, O-2-hydroxypropyl-3,1-O, O-dihydroxypropyl-3,1-O, O-dihydroxypropyl] is abbreviated as N- (HP 1 -HP 2 -HP 3 -diHP 4 ).
C 51 H 102 NO 16 P (1016.33)
71) 1,2-distearoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -HP 3 -diHP 4 ) -ethylammonium (n = 2)
C 55 H 110 NO 16 P (1072.44)
72) 1,2-Dierucoyl-sn-glycero-3-phospho-N, N-di-ethyl-N- (HP 1 -HP 2 -HP 3 -diHP 4 ) -ethylammonium (n = 2)
C 63 H 122 NO 16 P (1180.62)
73) 1,2-Dioleoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -HP 3 -diHP 4 ) -ethylammonium (n = 2)
C 55 H 106 NO 16 P (1068.41)
74) 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 - HP 3 -diHP 4 ) -ethylammonium (n = 2)
C 55 H 108 NO 16 P (1070.42)
75) 1-Stearoyl-2-lauroyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 - HP 3 -diHP 4 ) -ethylammonium (n = 2)
C 49 H 98 NO 16 P (988.28)
76) 1-Palmitoyl-2-lauroyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -HP 3 -diHP 4 ) -ethylammonium (n = 2)
C 47 H 94 NO 16 P (960.23)
77) 1,2-dipalmitoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -HP 3 -diHP 4 ) -propylammonium (n = 3)
C 52 H 104 NO 16 P (1030.36)
78) 1,2-distearoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -HP 3 -diHP 4 ) -propylammonium (n = 3)
C 56 H 112 NO 16 P (1086.47)
79) 1,2-Dierucoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -HP 3 -diHP 4 ) -propylammonium (n = 3)
80) 1,2-Dioleoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -HP 3 -diHP 4 ) -propylammonium (n = 3)
C 56 H 108 NO 16 P (1082.43)
81) 1-Stearoyl-2-lauroyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 - HP 3 -diHP 4 ) -propylammonium (n = 3)
C 50 H 100 NO 16 P (1002.31)
82) 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 - HP 3 -diHP 4 ) -propylammonium (n = 3)
C 56 H 110 NO 16 P (1084.45)
83) 1-arachinoyl-2-oleoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 - HP 3 -diHP 4 ) -propylammonium (n = 3)
C 58 H 114 NO 16 P (1112.50)
84) 1-Behenoyl-2-oleoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 - HP 3 -diHP 4 ) -propylammonium (n = 3)
C 60 H 118 NO 16 P (1140.56)

Beispiele für zweikettige Glycero-phospho-Verbindungen, die nicht am Stickstoff hydroxyliert sindExamples of two-chain glycerophospho compounds that are not Nitrogen are hydroxylated

(A = a; n = 2-6; m = 1; x = 1; z = 0)
(A = a, n = 2-6, m = 1, x = 1, z = 0)

85) 1,2-Dioleoyl-sn-glycero-3-phospho-N,N,N-trimethyl-propylammonium
C45H86NO8P (800,15)
86) 1,2-Dioleoyl-sn-glycero-3-phospho-N,N,N-trimethyl-butylammonium
C46H88NO8P (814,17)
87) 1,2-Dioleoyl-sn-glycero-3-phospho-N,N,N-trimethyl-pentylammonium
C47H90NOP (828,20)
88) 1,2-Dioleoyl-sn-glycero-3-phospho-N,N,N-trimethyl-hexylammonium
C48H92NO8P (842,23)
89) 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-N,N,N-trimethyl- propylammonium
C45H88NO8P (802,16)
90) 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-N,N,N-trimethyl- butylammonium
C46H90NO8P (816,19)
91) 1-Palmitoyl-2-lauroyl-sn-glycero-3-phospho-N,N,N-trimethyl- propylammonium
C37H74NO8P (691,97)
92) 1-Oleoyl-2-lauroyl-sn-glycero-3-phospho-N,N,N-trimethyl- propylammonium
C39H76NO8P (718,00)
93) 1-Erucoyl-2-oleoyl-sn-glycero-3-phospho-N,N,N-trimethyl- propylammonium
C49H94NO8P (856,26)
94) 1-Erucoyl-2-oleoyl-sn-glycero-3-phospho-N,N,N-trimethyl- butylammonium
C50H96NO8P (870,28)
95) 1-Erucoyl-2-oleoyl-sn-glycero-3-phospho-N,N,N-trimethyl- hexylammonium
C52H100NO8P (898,34)
96) 1-Nervonoyl-2-lauroyl-sn-glycero-3-phospho-N,N,N-trimethyl- propylammonium
C45H88NO8P (802,16)
97) 1-Nervonoyl-2-oleoyl-sn-glycero-3-phospho-N,N,N-trimethyl- propylammonium
C51H98NO8P (884,31)85) 1,2-dioleoyl-sn-glycero-3-phospho-N, N, N-trimethyl-propylammonium
C 45 H 86 NO 8 P (800.15)
86) 1,2-Dioleoyl-sn-glycero-3-phospho-N, N, N-trimethyl-butylammonium
C 46 H 88 NO 8 P (814,17)
87) 1,2-Dioleoyl-sn-glycero-3-phospho-N, N, N-trimethyl-pentylammonium
C 47 H 90 NO P (828.20)
88) 1,2-Dioleoyl-sn-glycero-3-phospho-N, N, N-trimethyl-hexylammonium
C 48 H 92 NO 8 P (842.23)
89) 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-N, N, N-trimethyl-propylammonium
C 45 H 88 NO 8 P (802.16)
90) 1-Stearoyl-2-oleoyl-sn-glycero-3-phospho-N, N, N-trimethyl-butylammonium
C 46 H 90 NO 8 P (816,19)
91) 1-palmitoyl-2-lauroyl-sn-glycero-3-phospho-N, N, N-trimethyl-propylammonium
C 37 H 74 NO 8 P (691.97)
92) 1-Oleoyl-2-lauroyl-sn-glycero-3-phospho-N, N, N-trimethyl-propylammonium
C 39 H 76 NO 8 P (718.00)
93) 1-Erucoyl-2-oleoyl-sn-glycero-3-phospho-N, N, N-trimethyl-propylammonium
C 49 H 94 NO 8 P (856.26)
94) 1-Erucoyl-2-oleoyl-sn-glycero-3-phospho-N, N, N-trimethyl-butylammonium
C 50 H 96 NO 8 P (870.28)
95) 1-Erucoyl-2-oleoyl-sn-glycero-3-phospho-N, N, N-trimethyl-hexylammonium
C 52 H 100 NO 8 P (898.34)
96) 1-Nervonoyl-2-lauroyl-sn-glycero-3-phospho-N, N, N-trimethyl-propylammonium
C 45 H 88 NO 8 P (802.16)
97) 1-Nervonoyl-2-oleoyl-sn-glycero-3-phospho-N, N, N-trimethyl-propylammonium
C 51 H 98 NO 8 P (884.31)

2) Lösungsvermittler2) Solubilizers

Es hat sich gezeigt, daß bestimmte Substanzen aus den hier vorgestellten Verbindungen insbesondere diejenigen, weiche ethanollöslich sind, ausgezeichnete Lösungsvermittler für in Wasser schwerlösliche Substanzen sind. So kann man beispielsweise Taxol auf einfache Weise in eine intravenös applizierbare Form bringen. Ebenso erwiesen sich z. B. Taxoter, Cyclosporin, Cholesterin und deren Derivate, Steroide, Cortison und Analoga, Erucylphosphocholin (Auflösung der gelartigen Strukturen) als gut lösbar.It has been shown that certain substances from the presented here Compounds especially those which are ethanol soluble, excellent solubilizers for water-insoluble substances are. For example, taxol can be easily transformed into a take intravenously administered form. Likewise, z. B. Taxo, Cyclosporine, cholesterol and its derivatives, steroids, cortisone and Analogs, erucylphosphocholine (dissolution of gel-like structures) as well solvable.

Insbesondere haben sich hier Substanzen bewährt, die zwischen Phosphat und Ammonium einen Abstand von 3 C-Atomen besitzen (n = 3 in der allgemeinen Formel I), z. B. die Substanzen aus den Beispielen 14, 85, 111, 139, 144, 176. Hervorragend geeignet für diese Zwecke ist eine einfache Substanz, 1-Erucoyl-propandiol-(1,3)-phospho-N,N,N-trimethyl­ propylammonium (176). Diese Substanz kann einfach in hohen Ausbeuten Tonnenmaßstab hergestellt werden. In particular, substances have proven useful here between phosphate and ammonium have a distance of 3 C atoms (n = 3 in the general formula I), for. B. the substances from Examples 14, 85, 111, 139, 144, 176. Excellent for this purpose is a simple one Substance, 1-erucoyl-propanediol- (1,3) -phospho-N, N, N-trimethyl propylammonium (176). This substance can easily be in high yields Ton scale.  

Taxol zur intravenösen AnwendungTaxol for intravenous use

Man stelle eine Lösung von 0,3 g Taxol und 1,75 g Substanz Nr. 176 in 7,95 g absolutem Ethanol her. Die Lösung wird steril filtriert und bis zur Verwendung bei 4°C aufbewahrt.Prepare a solution of 0.3 g taxol and 1.75 g substance # 176 7.95 g of absolute ethanol. The solution is sterile filtered and until the Use stored at 4 ° C.

Für eine intravenöse Gase wird die Stammlösung 1 : 10 oder 1 : 100 mit physiologischer Kochsalzlösung verdünnt.For intravenous gases, the stock solution is 1: 10 or 1: 100 diluted with physiological saline.

Beispiele für einkettige Glycero-phospho-N,N-dimethyl-N-dihydroxypropyl- alkylammonium-VerbindungenExamples of one-chain glycero-phospho-N, N-dimethyl-N-dihydroxypropyl alkylammonium compounds

(A = a; n = 2-6; R3 (A = a; n = 2-6; R 3

, CH3 , CH 3

; m = 1, x = 0, y = 1, z = 1)
; m = 1, x = 0, y = 1, z = 1)

98) 1-Palmitoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(diHP)- ethylammonium (n = 2)
C26H54NO9P (555,69)
99) 1-Stearoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(diHP)- ethylammonium (n = 2)
C28H58NO9P (583,74)
100) 1-Arachinoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(diHP)- ethylammonium (n = z)
C30H62NO9P (611,79)
101) 1-Behenyol-sn-glycero-3-phospho-N,N-dimethyl-N-(diHP)- ethylammonium (n = z)
C32H66NO9P (639,85)
102) 1-Erucoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(diHP)- ethylammonium (n = z)
C32H64NO9P (637,83)
103) 1-Nervonoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(diHP)- ethylammonium (n = z)
C34H68NO9P (665,88)
104) 1-O-Hexadecyl-sn-glycero-3-phospho-N,N-dimethyl-N-(diHP)- ethylammonium (n = z)
105) 1-O-Octadecyl-sn-glycero-3-phospho-N,N-dimethyl-N-(diHP)- ethylammonium (n = z)
C28H60NO8P (569,76)
106) 1-O-Eicosanyl-sn-glycero-3-phospho-N,N-dimethyl-N-(diHP)- ethylammonium (n = z)
C30H64NO8P (597,81)
107) 1-O-Behenyl-sn-glycero-3-phospho-N,N-dimethyl-N-(diHP)- ethylammonium (n = z)
C32H68NO8P (625,86)
108) 1-Palmitoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(diHP)- propylammonium (n = 3)
C27H56NO9P (569,71)
109) 1-Stearoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(diHP)- propylammonium (n = 3)
C29H60NO9P (597,77)
110) 1-Behenoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(diHP)- propylammonium (n = 3)
C33H68NO9P (653,87)
111) 1-Erucoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(diHP)- propylammonium (n = 3)
C33H66NO9P (651,86)
112) 1-Nervonoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(diHP)- propylammonium (n = 3)
C35H70NO9P (679,91)
113) 1-Stearoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(diHP)- butylammonium (n = 4)
C30H62NO9P (611,79)
114) 1-Erucoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(diHP)- butylammonium (n = 4)
C34H68NO9P (665,88)
115) 1-Stearoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(diHP)- hexylammonium (n = 6)
C32H66NO9P (639,85)
116) 1-Erucoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(diHP)- hexylammonium (n = 6)
C36H72NO9P (693,94) 98) 1-palmitoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (diHP) -ethylammonium (n = 2)
C 26 H 54 NO 9 P (555.69)
99) 1-stearoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (diHP) -ethylammonium (n = 2)
C 28 H 58 NO 9 P (583.74)
100) 1-arachinoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (diHP) -ethylammonium (n = z)
C 30 H 62 NO 9 P (611.79)
101) 1-Behenyl-sn-glycero-3-phospho-N, N-dimethyl-N- (diHP) -ethylammonium (n = z)
C 32 H 66 NO 9 P (639.85)
102) 1-Erucoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (diHP) -ethylammonium (n = z)
C 32 H 64 NO 9 P (637.83)
103) 1-Nervonoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (diHP) -ethylammonium (n = z)
C 34 H 68 NO 9 P (665.88)
104) 1-O-hexadecyl-sn-glycero-3-phospho-N, N-dimethyl-N- (diHP) -ethylammonium (n = z)
105) 1-O-octadecyl-sn-glycero-3-phospho-N, N-dimethyl-N- (diHP) -ethylammonium (n = z)
C 28 H 60 NO 8 P (569.76)
106) 1-O-Eicosanyl-sn-glycero-3-phospho-N, N-dimethyl-N- (diHP) -ethylammonium (n = z)
C 30 H 64 NO 8 P (597.81)
107) 1-O-Behenyl-sn-glycero-3-phospho-N, N-dimethyl-N- (diHP) -ethylammonium (n = z)
C 32 H 68 NO 8 P (625.86)
108) 1-palmitoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (diHP) -propylammonium (n = 3)
C 27 H 56 NO 9 P (569.71)
109) 1-stearoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (diHP) -propylammonium (n = 3)
C 29 H 60 NO 9 P (597.77)
110) 1-Behenoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (diHP) -propylammonium (n = 3)
C 33 H 68 NO 9 P (653.87)
111) 1-Erucoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (diHP) -propylammonium (n = 3)
C 33 H 66 NO 9 P (651.86)
112) 1-Nervonoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (diHP) -propylammonium (n = 3)
C 35 H 70 NO 9 P (679.91)
113) 1-stearoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (diHP) -butylammonium (n = 4)
C 30 H 62 NO 9 P (611.79)
114) 1-Erucoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (diHP) -butylammonium (n = 4)
C 34 H 68 NO 9 P (665.88)
115) 1-stearoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (diHP) -hexylammonium (n = 6)
C 32 H 66 NO 9 P (639.85)
116) 1-Erucoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (diHP) -hexylammonium (n = 6)
C 36 H 72 NO 9 P (693.94)

Beispiele für einkettige Glycero-phospho-N,N-dimethyl-N-(2-hydroxypropyl- 3,1-O,O-dihydroxypropyl)-alkylammonium-VerbindungenExamples of one-chain glycero-phospho-N, N-dimethyl-N- (2-hydroxypropyl) 3,1-O, O-dihydroxypropyl) alkylammonium compounds

(A = 0; n = 2-6; R3 (A = 0, n = 2-6, R 3

, CH3 , CH 3

; m = 1; x = 0; y = 1; z = 2)
; m = 1; x = 0; y = 1; z = 2)

117) 1-Stearoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-diHP2)- ethylammonium (n = 2)
C31H64NO11P (657,82)
118) 1-Arachinoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-diHP2)- ethylammonium (n = 2)
C33H68NO11P (685,87)
119) 1-Erucoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-diHP2)- ethylammonium (n = z)
C35H70NO11P (711,91)
120) 1-Nervonoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-diHP2)- ethylammonium (n = 2)
C37H74NO11P (739,96)
121) 1-O-Octadecyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-diHP2)- ethylammonium (n = 2)
C31H66NO10P (643,83)
122) 1-O-Behenyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-diHP2)- ethylammonium (n = z)
C35H74NOP (699,94)
123) 1-Stearoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-diHP2)- propylammonium (n = 3)
C32H66NO11P (671,84)
124) 1-Erucoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-diHP2)- propylammonium (n = 3)
C36H72NO11P (725,94)
125) 1-Erucoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-diHP2)- butylammonium (n = 4)
C37H74NO11P (739,98)
126) 1-Erucoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-diHP2)- hexylammonium (n = 6)
C39H78NO11P (768,04)
127) 1-Nervonoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-diHP2)- propylammonium (n = 3)
C38H76NO11P (754,01)
128) 1-Nervonoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-diHP2)- butylammonium (n = 4)
C39H78NO11P (768,04)117) 1-stearoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -ethylammonium (n = 2)
C 31 H 64 NO 11 P (657.82)
118) 1-arachinoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -ethylammonium (n = 2)
C 33 H 68 NO 11 P (685.87)
119) 1-Erucoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -ethylammonium (n = z)
C 35 H 70 NO 11 P (711.91)
120) 1-Nervonoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -ethylammonium (n = 2)
C 37 H 74 NO 11 P (739.96)
121) 1-O-Octadecyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -ethylammonium (n = 2)
C 31 H 66 NO 10 P (643,83)
122) 1-O-Behenyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -ethylammonium (n = z)
C 35 H 74 NO P (699.94)
123) 1-stearoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -propylammonium (n = 3)
C 32 H 66 NO 11 P (671.84)
124) 1-Erucoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -propylammonium (n = 3)
C 36 H 72 NO 11 P (725.94)
125) 1-Erucoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -butylammonium (n = 4)
C 37 H 74 NO 11 P (739.98)
126) 1-Erucoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -hexylammonium (n = 6)
C 39 H 78 NO 11 P (768.04)
127) 1-Nervonoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -propylammonium (n = 3)
C 38 H 76 NO 11 P (754.01)
128) 1-Nervonoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -butylammonium (n = 4)
C 39 H 78 NO 11 P (768.04)

Beispiele für einkettige Glycero-phospho-N,N-dimethyl-N-(2-hydroxypropyl- 3,10-O,O-2-hydroxypropyl-3,1-O,O-dihydroxypropyl)-alkylammonium- VerbindungenExamples of one-chain glycero-phospho-N, N-dimethyl-N- (2-hydroxypropyl) 3,10-O, O-2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -alkylammonium links

(A = a; n = 2-6; R3 (A = a; n = 2-6; R 3

, CH3 , CH 3

; n = 1; x = 0; y = 1; z = 3)
; n = 1; x = 0; y = 1; z = 3)

129) 1-Stearoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1HP2-diHP3)- ethylammonium (n = 2)
C34H70NO13P (731,90)
130) 1-Erucoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- ethylammonium (n = 2)
C38H76NO13P (785,99)
131) 1-Nervonoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- ethylammonium (n = 2)
C40H80NO13P (814,04)
132) 1-Erucoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- propylammonium (n = 3)
C39H78NO13P (800,01)
133) 1-Nervonoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- propylammonium (n = 3)
C41H82NO13P (828,07)
134) 1-Erucoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- butylammonium (n = 4)
C40H80NO13P (814,04)
135) 1-Erucoyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- hexylammonium (n = 6)
C42H84NO13P (842,09)129) 1-stearoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 HP 2 -diHP 3 ) -ethylammonium (n = 2)
C 34 H 70 NO 13 P (731.90)
130) 1-Erucoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -ethylammonium (n = 2)
C 38 H 76 NO 13 P (785.99)
131) 1-Nervonoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -ethylammonium (n = 2)
C 40 H 80 NO 13 P (814.04)
132) 1-Erucoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -propylammonium (n = 3)
C 39 H 78 NO 13 P (800.01)
133) 1-Nervonoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -propylammonium (n = 3)
C 41 H 82 NO 13 P (828.07)
134) 1-Erucoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -butylammonium (n = 4)
C 40 H 80 NO 13 P (814.04)
135) 1-Erucoyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -hexylammonium (n = 6)
C 42 H 84 NO 13 P (842.09)

Beispiele für einkettige Glycero-phospho-Verbindungen, die nicht am Stickstoff hydroxyliert sindExamples of single-chain glycero-phospho compounds not on Nitrogen are hydroxylated

(A = a; n = 3; R3 (A = a; n = 3, R 3

, CH3 , CH 3

; m = 1; x = 1; z =
; m = 1; x = 1; z =

136) 1-Palmitoyl-sn-glycero-3-phospho-N,N,N-trimethyl-propylammonium (n = 3)
C25H52NO7P (509,66)
137) 1-Stearoyl-sn-glycero-3-phospho-N,N,N-trimethyl-propylammonium (n = 3)
C27H56NO7P (537,71)
138) 1-Behenoyl-sn-glycero-3-phospho-N,N,N-trimethyl-propylammonium (n = 3)
C31H64NO7P (593,82)
139) 1-Erucoyl-sn-glycero-3-phospho-N,N,N-trimethyl-propylammonium (n = 3)
C31H62NO7P (591,81)
140) 1-Nervonoyl-sn-glycero-3-phospho-N,N,N-trimethyl-propylammonium (n = 3)
C33H66NO7P (61 9,86)136) 1-Palmitoyl-sn-glycero-3-phospho-N, N, N-trimethyl-propylammonium (n = 3)
C 25 H 52 NO 7 P (509.66)
137) 1-stearoyl-sn-glycero-3-phospho-N, N, N-trimethyl-propylammonium (n = 3)
C 27 H 56 NO 7 P (537.71)
138) 1-Behenoyl-sn-glycero-3-phospho-N, N, N-trimethyl-propylammonium (n = 3)
C 31 H 64 NO 7 P (593.82)
139) 1-Erucoyl-sn-glycero-3-phospho-N, N, N-trimethyl-propylammonium (n = 3)
C 31 H 62 NO 7 P (591.81)
140) 1-Nervonoyl-sn-glycero-3-phospho-N, N, N-trimethyl-propylammonium (n = 3)
C 33 H 66 NO 7 P (61 9,86)

Beispiele für ω,ω'-Alkandiol-phospho-N,N-dimethyl-N-dihydroxypropyl­ alkylammonium-VerbindungenExamples of ω, ω'-alkanediol phospho-N, N-dimethyl-N-dihydroxypropyl alkylammonium compounds

(A = b; n = 2-4; R3 (A = b; n = 2-4; R 3

, CH3 , CH 3

; m = 1; x = 0; y = 1; z = 1)
; m = 1; x = 0; y = 1; z = 1)

141) 1-Stearoyl-ethylenglykol-phospho-N,N-dimethyl-N-dihydroxypropyl- ethylammonium (n = 2)
C27H56NO8P (553,71)
142) 1-Behenoyl-propandiol-(1,3)-phospho-N,N-dimethyl-N- dihydroxypropyl-ethylammonium (n = 2)
C32H66NO8P (623,85)
143) 1-Stearoyl-propandiol-(1,3)-phospho-N,N-dimethyl-N-dihydroxypropyl- ethylammonium (n = 2)
C28H58NO8P (567,74)
144) 1-Erucoyl-propandiol-(1,3)-phospho-N,N-dimethyl-N-dihydroxypropyl- ethylammonium (n = 2)
C32H64NO8P (621,83)
145) 1-Erucoyl-propandiol-(1,3)-phospho-N,N-dimethyl-N-dihydroxypropyl- propylammonium (n = 3)
C33H66NO8P (635,86)
146) 1-Erucoyl-propandiol-(1,3)-phospho-N,N-dimethyl-N-dihydroxypropyl- butylammonium (n = 4)
C34H68NO8P (649,88)141) 1-stearoyl-ethylene glycol-phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium (n = 2)
C 27 H 56 NO 8 P (553.71)
142) 1-Behenoyl-propanediol- (1,3) -phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium (n = 2)
C 32 H 66 NO 8 P (623,85)
143) 1-Stearoyl-propanediol- (1,3) -phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium (n = 2)
C 28 H 58 NO 8 P (567.74)
144) 1-Erucoyl-propanediol- (1,3) -phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium (n = 2)
C 32 H 64 NO 8 P (621.83)
145) 1-Erucoyl-propanediol- (1,3) -phospho-N, N-dimethyl-N-dihydroxypropyl-propylammonium (n = 3)
C 33 H 66 NO 8 P (635.86)
146) 1-Erucoylpropanediol- (1,3) -phospho-N, N-dimethyl-N-dihydroxypropyl-butylammonium (n = 4)
C 34 H 68 NO 8 P (649.88)

Beispiele für Alkandiol-(1,2)-phospho-N,N-dimethyl-N-dihydroxypropyl- alkylammonium-VerbindungenExamples of alkanediol- (1,2) -phospho-N, N-dimethyl-N-dihydroxypropyl- alkylammonium compounds

(A = b; n = 2-4; R3 (A = b; n = 2-4; R 3

, CH3 , CH 3

; m = 1; x = 0; y = 1; z = 1)
; m = 1; x = 0; y = 1; z = 1)

147) 2-Erucoyl-prnpandiol-(1,2)-phospho-N,N-dimethyl-N-dihydroxypropyl- ethylammonium
C32H64NO8P (621,33)
148) 1-Erucoyl-propandiol-(1,2)-phospho-N,N-dimethyl-N-dihydroxypropyl- ethylammonium
C32H64NO8P (621,33)
149) 2-Erucoyl-propandiol-(1,2)-phospho-N,N-dimethyl-N-dihydroxypropyl- propylammonium
C33H66NO8P (635,86)
150) 1-Erucoyl-propandiol-(1,2)-phospho-N,N-dimethyl-N-dihydroxypropyl- butylammonium
C34H68NO8P (649,88)147) 2-Erucoyl-prandipiol- (1,2) -phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium
C 32 H 64 NO 8 P (621.33)
148) 1-Erucoyl-propanediol- (1,2) -phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium
C 32 H 64 NO 8 P (621.33)
149) 2-Erucoyl-propanediol- (1,2) -phospho-N, N-dimethyl-N-dihydroxypropyl-propylammonium
C 33 H 66 NO 8 P (635.86)
150) 1-Erucoyl-propanediol- (1,2) -phospho-N, N-dimethyl-N-dihydroxypropyl-butylammonium
C 34 H 68 NO 8 P (649.88)

Beispiele für ω,ω'-Alkandiol-phospho-N,N-dimethyl-N-(2-hydroxypropyl)-3,1- O,O-dihydroxypropyl)-alkylammonium-VerbindungenExamples of ω, ω'-alkanediol phospho-N, N-dimethyl-N- (2-hydroxypropyl) -3,1- O, O-dihydroxypropyl) alkylammonium compounds

(A = b; n = 2-4; R3 (A = b; n = 2-4; R 3

, CH3 , CH 3

; m = 1, x = 0; y = 1; z = 2)
; m = 1, x = 0; y = 1; z = 2)

151) 1-Stearoyl-ethylenglykol-phospho-N,N-dimethyl-N-(2-hydroxypropyl- 3,1-O,O-dihydroxypropyl)-ethylammonium
C30H62NO10P (627,79)
152) 1-Behenoyl-propandiol-(1,3)-phospho-N,N-dimethyl-N-(2- hydroxypropyl-3,1-O,O-dihydroxypropyl)-ethylammonium
C35H72NO10P (697,93)
153) 1-Stearoyl-propandiol-(1,3)-phospho-N,N-dimethyl-N-(2- hydroxypropyl)-3,1-O,O-dihydroxypropyl-ethylammonium
C31H64NO10P (641,82)
154) 1-Erucoyl-propandiol-(1,3)-phospho-N,N-dimethyl-N-(2-hydroxypropyl- 3,1-O,O-dihydroxypropyl)-ethylammonium
C35H70NO10P (695,91)
155) 1-Erucoyl-propandiol-(1,3)-phospho-N,N-dimethyl-N-(2-hydroxypropyl- 3,1-O,O-dihydroxypropyl)-propylammonium
C36H72NO10P (709,94)
156) 1-Erucoyl-propandiol-(1,3)-phospho-N,N-dimethyl-N-(2-hydroxypropyl- 3,1-O,O-dihydroxypropyl)-butylammonium
C37H74NO10P (723,96)
157) 1-Erucoyl-butandiol-(1,4)-phospho-N,N-dimethyl-N-(2-hydroxypropyl- 3,1-O,O-dihydroxypropyl)-propylammonium
C37H74NO10P (723,96)
158) 1-Erucoyl-hexandiol-(1,6)-phospho-N,N-dimethyl-N-(2-hydroxyprnpyl- 3,1-O,O-dihydroxypropyl)-propylammonium
C39H78NO10P (752,02)
159) 1-Erucoyl-octandiol-(1,8)-phospho-N,N-dimethyl-N-(2-hydroxypropyl)- 3,1-O,O-dihydroxypropyl)-propylammonium
C41H82NO10P (780,07)151) 1-stearoyl-ethylene glycol phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -ethylammonium
C 30 H 62 NO 10 P (627.79)
152) 1-Behenoylpropanediol- (1,3) -phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -ethylammonium
C 35 H 72 NO 10 P (697.93)
153) 1-Stearoyl-propanediol- (1,3) -phospho-N, N-dimethyl-N- (2-hydroxypropyl) -3,1-O, O-dihydroxypropyl-ethylammonium
C 31 H 64 NO 10 P (641.82)
154) 1-Erucoylpropanediol- (1,3) -phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -ethylammonium
C 35 H 70 NO 10 P (695.91)
155) 1-Erucoylpropanediol- (1,3) -phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -propylammonium
C 36 H 72 NO 10 P (709.94)
156) 1-Erucoyl-propanediol- (1,3) -phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -butylammonium
C 37 H 74 NO 10 P (723.96)
157) 1-Erucoyl-butanediol- (1,4) -phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -propylammonium
C 37 H 74 NO 10 P (723.96)
158) 1-Erucoyl-hexanediol- (1,6) -phospho-N, N-dimethyl-N- (2-hydroxyprnpyl-3,1-O, O-dihydroxypropyl) -propylammonium
C 39 H 78 NO 10 P (752.02)
159) 1-Erucoyl-octanediol- (1,8) -phospho-N, N-dimethyl-N- (2-hydroxypropyl) -3,1-O, O-dihydroxypropyl) -propylammonium
C 41 H 82 NO 10 P (780.07)

Beispiele für Alkandiol-(1,2)-phospho-N,N-dimethyl-N-(2-hydroxypropyl-3,1- O,O-dihydroxypropyl)-alkylammonium-VerbindungenExamples of alkanediol- (1,2) -phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1- O, O-dihydroxypropyl) alkylammonium compounds

(A = b; n = 2-4; R3 (A = b; n = 2-4; R 3

, CH3 , CH 3

; m = 1; x = 0; y = 1; z = 2)
; m = 1; x = 0; y = 1; z = 2)

160) 2-Erucoyl-propandiol-(1,2)-phospho-N,N-dimethyl-N-(2-hydroxypropyl- 3,1-O,O-dihydroxypropyl)-ethylammonium
C35H70NO10P (695,91)
161) 1-Erucoyl-propandiol-(1,2)-phospho-N,N-dimethyl-N-(2-hydroxypropyl- 3,1-O,O-dihydroxypropyl)-ethylammonium
(C35H70NO10P (695,91)
162) 2-Erucoyl-propandiol-(1,2)-phospho-N,N-dimethyl-N-(2-hydroxypropyl- 3,1-O,O-dihydroxypropyl)-propylammonium
C36H72NO10P (709,94)
163) 1-Erucoyl-propandiol-(1,2)-phospho-N,N-dimethyl-N-(2-hydroxypropyl- 3,1-O,O-dihydroxypropyl)-butylammonium
C37H74NO10P (723,96)
164) 1-Erucoyl-butandiol-(1,2)-phospho-N,N-dimethyl-N-(2-hydroxypropyl- 3,1-O,O-dihydroxypropyl)-propylammonium
C37H74NO10P (723,96)
165) 1-Erucoyl-hexandiol-(1,2)-phospho-N,N-dimethyl-N-(2-hydroxypropyl- 3,1-O,O-dihydroxypropyl)-propylammonium
C39H78NO10P (752,02)
166) 1-Erucoyl-octandiol-(1,2)-phospho-N,N-dimethyl-N-(2-hydroxypropyl- 3,1-O,O-dihydroxypropyl)-propylammonium
C41H82NO10P (780,07)160) 2-Erucoyl-propanediol- (1,2) -phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -ethylammonium
C 35 H 70 NO 10 P (695.91)
161) 1-Erucoylpropanediol- (1,2) -phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -ethylammonium
(C 35 H 70 NO 10 P (695.91)
162) 2-Erucoyl-propanediol- (1,2) -phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -propylammonium
C 36 H 72 NO 10 P (709.94)
163) 1-Erucoylpropanediol- (1,2) -phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -butylammonium
C 37 H 74 NO 10 P (723.96)
164) 1-Erucoyl-butanediol- (1,2) -phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -propylammonium
C 37 H 74 NO 10 P (723.96)
165) 1-Erucoylhexanediol- (1,2) -phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -propylammonium
C 39 H 78 NO 10 P (752.02)
166) 1-Erucoyl-octanediol- (1,2) -phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-dihydroxypropyl) -propylammonium
C 41 H 82 NO 10 P (780.07)

Beispiele für ω,ω'-Alkandiol-N,N-dimethyl-N-(2-hydroxypropyl-3,1-O,O-2- hydroxypropyl-3,1-O,O-dihydroxypropyl)-alkylammonium-VerbindungenExamples of ω, ω'-alkanediol-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O-2- hydroxypropyl-3,1-O, O-dihydroxypropyl) alkylammonium compounds

(Abkürzung: HP = 2-Hydroxypropyl,
diHP = Dihydroxypropyl)
(A = b; n = 2-6; R, CH3 (Abbreviation: HP = 2-hydroxypropyl,
diHP = dihydroxypropyl)
(A = b; n = 2-6; R, CH 3

; m = 1; x = 0; y = 1; z = 3)
; m = 1; x = 0; y = 1; z = 3)

167) 1-Oleoyl-ethylenglykol-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- ethylammonium
C34H68NO12P (713,88)
168) 1-Erucoyl-propandiol-(1,3)-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- ethylammonium
C38H76NO12P (769,99)
169) 1-Oleoyl-propandiol-(1,3)-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- propylammonium
C35H70NO12P (727,91)
170) 1-Erucoyl-propandiol-(1,3)-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- propylammonium
C39H78NO12P (784,01)
171) 1-Erucoyl-propandiol-(1,3)-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- butylammonium
C40H80NO12P (798,04)
172) 1-Erucoyl-propandiol-(1,3)-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- hexylammonium
C42H84NO12P (826,10) 167) 1-Oleoyl-ethylene glycol-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -ethylammonium
C 34 H 68 NO 12 P (713.88)
168) 1-Erucoyl-propanediol- (1,3) -phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -ethylammonium
C 38 H 76 NO 12 P (769.99)
169) 1-Oleoyl-propanediol- (1,3) -phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -propylammonium
C 35 H 70 NO 12 P (727.91)
170) 1-Erucoyl-propanediol- (1,3) -phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -propylammonium
C 39 H 78 NO 12 P (784.01)
171) 1-Erucoyl-propanediol- (1,3) -phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -butyl-ammonium
C 40 H 80 NO 12 P (798.04)
172) 1-Erucoyl-propanediol- (1,3) -phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -hexylammonium
C 42 H 84 NO 12 P (826.10)

Beispiele für Alkandiol-phospho-Verbindungen, die nicht am Stickstoff hydroxyliert sindExamples of alkanediol phospho compounds that are not nitrogen are hydroxylated

(A = b; n = 2-6; R, CH3 (A = b; n = 2-6; R, CH 3

; m = 1; x = 1; z = 0)
; m = 1; x = 1; z = 0)

173) 1-Erucoyl-ethylenglykol-phospho-N,N,N-trimethyl-propylammonium
C30H60NO6P (561,78)
174) 1-Arachinoyl-propandiol-(1,3)-phospho-N,N,N-trimethyl- propylammonium
C29H69NO6P (549,77)
175) 1-Stearoyl-propandiol-(1,3)-phospho-N,N,N-trimethyl- propylammonium
C27H56NO6P (521,71)
176) 1-Erucoyl-propandiol-(1,3)-phospho-N,N,N-trimethyl-propylammonium
C31H62NO6P (575,81)
177) 1-Erucoyl-propandiol-(1,3)-phospho-N,N,N-trimethyl-butylammonium
C32H64NO6P (589,83)
178) 1-Erucoyl-propandiol-(1,3)-phospho-N,N,N-trimethyl-pentylammonium
C33H66NO6 (603,86)
179) 1-Erucoyl-propandiol-(1,2)-phospho-N,N,N-trimethyl-propylammonium
C31H62NO6P (575,81)
180) 2-Erucoyl-propandiol-(1,2)-phospho-N,N,N-trimethyl-propylammonium
C31H62NO6P (575,81)
181) 1-Erucoyl-propandiol-(1,2)-phospho-N,N,N-trimethyl-butylammonium
C32H64NO6P (589,83)
182) 1-Erucoyl-propandiol-(1,2)-phospho-N,N,N-trimethyl-hexylammonium
C34H68NO6P (617,92)173) 1-Erucoyl-ethylene glycol phospho-N, N, N-trimethyl-propylammonium
C 30 H 60 NO 6 P (561.78)
174) 1-Arachinoyl-propanediol- (1,3) -phospho-N, N, N-trimethyl-propylammonium
C 29 H 69 NO 6 P (549.77)
175) 1-Stearoyl-propanediol- (1,3) -phospho-N, N, N-trimethyl-propylammonium
C 27 H 56 NO 6 P (521.71)
176) 1-Erucoyl-propanediol- (1,3) -phospho-N, N, N-trimethyl-propylammonium
C 31 H 62 NO 6 P (575.81)
177) 1-Erucoyl-propanediol- (1,3) -phospho-N, N, N-trimethyl-butylammonium
C 32 H 64 NO 6 P (589.83)
178) 1-Erucoyl-propanediol- (1,3) -phospho-N, N, N-trimethyl-pentylammonium
C 33 H 66 NO 6 (603.86)
179) 1-Erucoyl-propanediol- (1,2) -phospho-N, N, N-trimethyl-propylammonium
C 31 H 62 NO 6 P (575.81)
180) 2-Erucoyl-propanediol- (1,2) -phospho-N, N, N-trimethyl-propylammonium
C 31 H 62 NO 6 P (575.81)
181) 1-Erucoyl-propanediol- (1,2) -phospho-N, N, N-trimethyl-butylammonium
C 32 H 64 NO 6 P (589.83)
182) 1-Erucoyl-propanediol- (1,2) -phospho-N, N, N-trimethyl-hexylammonium
C 34 H 68 NO 6 P (617.92)

3) Wirkstoffe3) active ingredients

In früheren Untersuchungen wurde festgestellt, daß Alkylphosphocholine nur dann antitumorale Wirksamkeit besitzen, wenn der Phosphat- Ammoniumabstand zwei C-Atome beträgt, also Phosphocholin (n = 2 in der allgemeinen Formel I) entspricht. Verbindungen mit dem Abstand n < 2 waren unwirksam. Bei diesen früheren Untersuchungen wurden die Wirkstoffe oral appliziert.Previous studies have found that alkylphosphocholines have antitumoral activity only if the phosphate Ammonium distance is two C atoms, ie phosphocholine (n = 2 in the general formula I). Connections with the distance n <2 were ineffective. In these earlier studies, the Active ingredients applied orally.

Überraschenderweise haben wir nun festgestellt, daß Erucylphospho- Verbindungen mit Phosphat-Ammoniumabständen < 2 exzellente, den Alkylphosphocholinen sogar überlegene Antitumorwirksamkeit besitzen, wenn diese Substanzen intravenös angewendet werden, wie folgender Vergleich zeigt:Surprisingly, we have now discovered that erucylphosphorous Compounds with phosphate-ammonium distances <2 excellent, den Alkylphosphocholines even have superior antitumor activity, when these substances are used intravenously, as follows Comparison shows:

Erucylphosnhocholin (n = 2 in allgemeiner Formel I)Erucylphosnhocholin (n = 2 in general formula I)

Die Substanz bildet in Wasser gelartige Strukturen und ist deshalb in höheren Konzentrationen intravenös nur schwer anwendbar. The substance forms gel-like structures in water and is therefore in higher concentrations intravenously difficult to apply.  

Eurcylphosphocholin besitzt im Tiermodell Methylnitrosoharnstoff- induziertes Mammakarzinom nur eine geringe Langzeitwirkung. Bereits 7 Tage nach Absetzen der Therapie wird wieder Tumorwachstum beobachtet.Eurocylphosphocholine has methylnitrosourea in the animal model induced breast cancer only a small long-term effect. Already 7 Days after discontinuation of the therapy tumor growth is again observed.

Erucyl-phospho-N,N,N-trimethyl-propylammonium (n = 3)Erucyl-phospho-N, N, N-trimethyl-propylammonium (n = 3)

Die Substanz ist in Wasser leicht löslich, bildet keine Gele und kann problemlos intravenös verabreicht werden. Sie kann deshalb auch als Lösungsvermittler Verwendung finden. Insbesondere auffällig und eindrucksvoll ist aber ihre Langzeitwirkung in obigem Tiermodell. Selbst 4 Wochen nach Absetzen der Therapie ist kein neues Tumorwachstum zu beobachten.The substance is readily soluble in water, does not form gels and can easily administered intravenously. It can therefore also as Solvent finder use. In particular conspicuous and but impressive is their long-term effect in the above animal model. Even 4 Weeks after cessation of therapy, no new tumor growth is due observe.

Beispiele für Alkyl-phospho-N,N-dimethyl-N-dihydroxypropyl­ alkylammonium-VerbindungenExamples of alkyl phospho-N, N-dimethyl-N-dihydroxypropyl alkylammonium compounds

(A = c; n = 2-6; R3 (A = c; n = 2-6; R 3

, CH3 , CH 3

; m = 1; x = 0; y = 1; z = 1)
; m = 1; x = 0; y = 1; z = 1)

183) Hexadecyl-phospho-N,N-dimethyl-N-dihydroxypropyl-ethylammonium
C23H50NO6P (467,62)
184) Octadecyl-phospho-N,N-dimethyl-N-dihydroxypropyl-ethylammonium
C25H54NO6P (495,68)
185) Erucyl-phospho-N,N-dimethyl-N-dihydroxypropyl-ethylammonium
C29H60NO6P (549,77)
186) Erucyl-phospho-N,N-dimethyl-N-dihydroxypropyl-propylammonium
C30H62NO6P (563,80)
187) Erucyl-phospho-N,N-dimethyl-N-dihydroxypropyl-butylammonium
C31H64NO6P (577,82)
188) Erucyl-phospho-N,N-dimethyl-N-dihydroxypropyl-hexylammonium
C33H68NO6P (605,88)
189) Oleyl-phospho-N,N-dimethyl-N-dihydroxypropyl-ethylammonium
C25H52NO6P (493,66)
190) Oleyl-phospho-N,N-dimethyl-N-dihydroxypropyl-propylammonium
C26H54NO6P (507,69)
191) Oleyl-phospho-N,N-dimethyl-N-dihydroxypropyl-butylammonium
C27H56NO6P (521,21)
192) (Z-11)-Eicosenyl-phospho-N,N-dimethyl-N-dihydroxypropyl- ethylammonium
C27H56NO6P (521,21)
193) (Z-11)-Eicosenyl-phospho-N,N-dimethyl-N-dihydroxypropyl- propylammonium
C28H58NO6P (535,74)
194) (Z-11)-Eicosenyl-phospho-N,N-dimethyl-N-dihydroxypropyl- butylammonium
C29H60NO6P (549,77)
195) (Z-11)-Eicosenyl-phospho-N,N-dimethyl-N-dihydroxypropyl- pentylammonium
C30H62NO6P (563,80)
196) (Z-11)-Eicosenyl-phospho-N,N-dimethyl-N-dihydroxypropyl- hexylammonium
C31H64NO6P (577,82)183) hexadecylphospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium
C 23 H 50 NO 6 P (467.62)
184) octadecylphospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium
C 25 H 54 NO 6 P (495.68)
185) Erucyl phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium
C 29 H 60 NO 6 P (549.77)
186) Erucyl phospho-N, N-dimethyl-N-dihydroxypropyl-propylammonium
C 30 H 62 NO 6 P (563.80)
187) Erucyl-phospho-N, N-dimethyl-N-dihydroxypropyl-butylammonium
C 31 H 64 NO 6 P (577.82)
188) Erucyl phospho-N, N-dimethyl-N-dihydroxypropyl hexylammonium
C 33 H 68 NO 6 P (605.88)
189) Oleyl-phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium
C 25 H 52 NO 6 P (493.66)
190) Oleyl-phospho-N, N-dimethyl-N-dihydroxypropyl-propylammonium
C 26 H 54 NO 6 P (507.69)
191) Oleyl-phospho-N, N-dimethyl-N-dihydroxypropyl-butylammonium
C 27 H 56 NO 6 P (521.21)
192) (Z-11) -eicosenylphospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium
C 27 H 56 NO 6 P (521.21)
193) (Z-11) -eicosenylphospho-N, N-dimethyl-N-dihydroxypropylpropylammonium
C 28 H 58 NO 6 P (535.74)
194) (Z-11) -eicosenylphospho-N, N-dimethyl-N-dihydroxypropyl-butylammonium
C 29 H 60 NO 6 P (549.77)
195) (Z-11) -eicosenylphospho-N, N-dimethyl-N-dihydroxypropylpentylammonium
C 30 H 62 NO 6 P (563.80)
196) (Z-11) -eicosenyl phospho-N, N-dimethyl-N-dihydroxypropyl hexylammonium
C 31 H 64 NO 6 P (577.82)

Beispiele für Alkyl-phospho-N,N-dimethyl-N-(2-hydroxypropyl-1,2- dihydroxypropyl)-alkylammoniumExamples of alkyl phospho-N, N-dimethyl-N- (2-hydroxypropyl-1,2- dihydroxypropyl) -alkylammonium

(A = c; n = 2-6; R3 (A = c; n = 2-6; R 3

, CH3 , CH 3

; m = 1; x = 0; y = 1; z = 2)
; m = 1; x = 0; y = 1; z = 2)

197) Hexadecyl-phospho-N,N-dimethyl-N-(HP1-diHP2)-ethylammonium
C26H56NO8P (541,70)
198) Octadecyl-phospho-N,N-dimethyl-N-(HP1-diHP2)-ethylammonium
C28H60NO8P (569,76)
199) Erucyl-phospho-N,N-dimethyl-N-(HP1-diHP2)-ethylammonium
C32H66NO8P (623,85)
200) Erucyl-phospho-N,N-dimethyl-N-(HP1-diHP2)-propylammonium
C33H68NO8P (637,87)
201) Erucyl-phospho-N,N-dimethyl-N-(HP1-diHP2)-butylammonium
C34H70NO8P (651,90)
202) Erucyl-phospho-N,N-dimethyl-N-(HP1-diHP2)-hexylammonium
C36H74NO8P (679,95)
203) Oleyl-phospho-N,N-dimethyl-N-(HP1-diHP2)-ethylammonium
C28H58NO8P (567,74)
204) Oleyl-phospho-N,N-dimethyl-N-(HP1-diHP2)-propylammonium
C29H60NO8P (581,77)
205) Oleyl-phospho-N,N-dimethyl-N-(HP1-diHP2)-butylammonium
C30H62NO8P (595,79)
206) (Z-11)-Eicosenyl-phospho-N,N-dimethyl-N-(HP1-diHP2)-ethylammonium
C30H62NO8P (595,79)
207) (Z-11)-Eicosenyl-phospho-N,N-dimethyl-N-(HP1-diHP2)- propylammonium
C30H64NO8P (609,82)
208) (Z-11)-Eicosenyl-phospho-N,N-dimethyl-N-(HP1-diHP2)-butylammonium
C32H66NO8P (623,85)197) hexadecyl phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -ethylammonium
C 26 H 56 NO 8 P (541.70)
198) octadecyl phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -ethylammonium
C 28 H 60 NO 8 P (569.76)
199) Erucyl phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -ethylammonium
C 32 H 66 NO 8 P (623,85)
200) Erucyl phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -propylammonium
C 33 H 68 NO 8 P (637.87)
201) Erucyl-phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -butylammonium
C 34 H 70 NO 8 P (651.90)
202) Erucyl phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -hexylammonium
C 36 H 74 NO 8 P (679.95)
203) Oleyl-phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -ethylammonium
C 28 H 58 NO 8 P (567.74)
204) Oleyl-phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -propylammonium
C 29 H 60 NO 8 P (581.77)
205) Oleyl-phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -butylammonium
C 30 H 62 NO 8 P (595.79)
206) (Z-11) -eicosenylphospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -ethylammonium
C 30 H 62 NO 8 P (595.79)
207) (Z-11) -eicosenyl phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) propylammonium
C 30 H 64 NO 8 P (609.82)
208) (Z-11) -eicosenyl phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -butylammonium
C 32 H 66 NO 8 P (623,85)

Beispiele für Alkyl-phospho-N,N-dimethyl-N-(2-hydroxypropyl-3,1-O,O- hydroxypropyl-3,1-O,O-1,2-dihydroxypropyl)-alkylammonium-VerbindungenExamples of alkyl phospho-N, N-dimethyl-N- (2-hydroxypropyl-3,1-O, O- hydroxypropyl-3,1-O, O-1,2-dihydroxypropyl) alkylammonium compounds

(A = c; n = 2-4; R3 (A = c; n = 2-4; R 3

, CH3 , CH 3

; m = 1; x = 0; y = 1; z = 3)
; m = 1; x = 0; y = 1; z = 3)

209) Hexadecyl-phospho-NN-dimethyl-N-(HP1-HP2-diHP3)-ethylammonium
C29H62NO10P (615,78)
210) Octadecyl-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)-ethylammonium
C31H66NO10P (643,83)
211) Oleol-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)-ethylammonium
C31H64NO10P (641,82)
212) (Z-11)-Eicosenyl-phospho-N,N-dimethyl-N-(HPi1-HP2-diHP3)- ethylammonium
C33H68NO10P (669,87)
213) (Z-11)-Eicosenyl-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- propylammonium
C34H70NO10P (683,90)
214) (Z-11)-Eicosenyl-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)- butylammonium
C35H72NO10P (697,93)
215) Erucyl-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)-ethylammonium
C35H72NO10P (697,93)
216) Erucyl-phospho-N,N-dimethyl-N-(HP1-HP2-diHP3)-propylammonium
C36H74NO10P (711,95)209) hexadecyl phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -ethylammonium
C 29 H 62 NO 10 P (615.78)
210) Octadecyl phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -ethylammonium
C 31 H 66 NO 10 P (643,83)
211) Oleol phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -ethylammonium
C 31 H 64 NO 10 P (641.82)
212) (Z-11) -eicosenyl phospho-N, N-dimethyl-N- (HPi 1 -HP 2 -diHP 3 ) -ethylammonium
C 33 H 68 NO 10 P (669.87)
213) (Z-11) -eicosenyl phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) propylammonium
C 34 H 70 NO 10 P (683.90)
214) (Z-11) -eicosenylphospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -butylammonium
C 35 H 72 NO 10 P (697.93)
215) Erucyl-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -ethylammonium
C 35 H 72 NO 10 P (697.93)
216) Erucyl-phospho-N, N-dimethyl-N- (HP 1 -HP 2 -diHP 3 ) -propylammonium
C 36 H 74 NO 10 P (711.95)

Beispiele für Alkylphospho-Verbindungen, die am Stickstoff keine Dihydroxyalkylreste tragenExamples of alkylphosphorous compounds which do not react with nitrogen Dihydroxyalkylreste carry

(A = a; n = 3-6; R3 (A = a; n = 3-6, R 3

, CH3 , CH 3

; m = 1, x = 1-3; z = 0)
; m = 1, x = 1-3; z = 0)

217) Erucyl-phospho-N,N,N-trimethyl-propylammonium
C26H58NO4P (503,74)
218) Erucyl-phospho-N,N-dimethyl-N-ethyl-propylammonium
C29H60NO4P (517,77)
219) Erucyl-phospho-N,N-dimethyl-N-propyl-propylammonium
C30H62NO4P (531,80)
220) Erucyl-phospho-N,N-dimethyl-N-allyl-propylammonium
C30H60NO4P (529,78)
Rf-Werte der Substanzen 217-240 im beschriebenen System: Rf 0,30-0,40
221) (Z)-10-Docosenyl-2-phospho-N,N,N-trimethyl-propylammonium
C28H58NO4P (503,74)
222) (Z)-10-Docosenyl-2-phospho-N,N-dimethyl-N-ethyl-propylammonium
C29H60NO4P (517,77)
223) Erucyl-phospho-N,N,N-trimethyl-butylammonium
C29H60NO4P (517,77)
224) Erucyl-phospho-N,N-dimethyl-N-ethyl-butylammonium
C30H62NO4P (531,80)
225) Erucyl-phospho-N,N-dimethyl-N-propyl-butylammonium
C31H64NO4P (545,82)
226) (Z)-10-Docosenyl-2-phospho-N,N,N-trimethyl-butylammonium
C29H60NO4P (517,77)
227) (Z)-11-Eicosenyl-phospho-N,N,N-trimethyl-propylammonium
C26H54NO4P (475,69)
228) (Z)-11-Eicosenyl-phospho-N,N-dimethyl-N-ethyl-propylammonium
C27H56NO4P (489,72)
229) (Z)-11-Eicosenyl-phospho-N,N-diethyl-N-methyl-propylammonium
C28H58NO4P (503,74)
230) (Z)-11-Eicosenyl-phospho-N,N-dimethyl-N-propyl-propylammonium
C28H58NO4P (503,74)
231) (Z)-11-Eicosenyl-phospho-N,N,N-trimethyl-butylammonium
C27H56NO4P (489,72)
232) (Z)-11-Eicosenyl-phospho-N,N-dimethyl-N-ethyl-butylammonium
C28H58NO4P (503,74)
233) (Z)-11-Eicosenyl-phospho-N,N-dimethyl-N-propyl-butylammonium
C29H60NO4P (517,77)
234) (Z)-11-Eicosenyl-phospho-N,N-dimethyl-N-alkyl-butylammonium
C29H58NO4P (575,75)
235) Oleyl-phospho-N,N,N-trimethyl-propylammonium
C24H50NO4P (447,64)
236) Oleyl-phospho-N,N-dimethyl-N-ethyl-propylammonium
C25H52NO4P (461,66)
237) Oleyl-phospho-N,N-dimethyl-N-propylen-propylammonium
C26H54NO4P (475,69)
238) Oleyl-phospho-N,N,N-trimethyl-butylammonium
C25H52NO4P (461,66)
239) Oleyl-phospho-N,N-dimethyl-N-ethyl-butylammonium
C26H54NO4P (475,69)
240) Oleyl-phospho-N,N-dimethyl-N-propyl-butylammonium
C27H56NO4P (489,72) 217) Erucyl phospho-N, N, N-trimethyl-propylammonium
C 26 H 58 NO 4 P (503.74)
218) Erucyl-phospho-N, N-dimethyl-N-ethyl-propylammonium
C 29 H 60 NO 4 P (517.77)
219) Erucyl phospho-N, N-dimethyl-N-propyl-propylammonium
C 30 H 62 NO 4 P (531.80)
220) Erucyl-phospho-N, N-dimethyl-N-allyl-propylammonium
C 30 H 60 NO 4 P (529.78)
Rf values of substances 217-240 in the described system: Rf 0.30-0.40
221) (Z) -10-docosenyl-2-phospho-N, N, N-trimethyl-propylammonium
C 28 H 58 NO 4 P (503.74)
222) (Z) -10-docosenyl-2-phospho-N, N-dimethyl-N-ethyl-propylammonium
C 29 H 60 NO 4 P (517.77)
223) Erucyl-phospho-N, N, N-trimethyl-butylammonium
C 29 H 60 NO 4 P (517.77)
224) Erucyl phospho-N, N-dimethyl-N-ethyl-butylammonium
C 30 H 62 NO 4 P (531.80)
225) Erucyl-phospho-N, N-dimethyl-N-propyl-butylammonium
C 31 H 64 NO 4 P (545.82)
226) (Z) -10-docosenyl-2-phospho-N, N, N-trimethyl-butylammonium
C 29 H 60 NO 4 P (517.77)
227) (Z) -11-Eicosenyl phospho-N, N, N-trimethyl-propylammonium
C 26 H 54 NO 4 P (475.69)
228) (Z) -11-Eicosenyl phospho-N, N-dimethyl-N-ethyl-propylammonium
C 27 H 56 NO 4 P (489.72)
229) (Z) -11-Eicosenyl phospho-N, N-diethyl-N-methyl-propylammonium
C 28 H 58 NO 4 P (503.74)
230) (Z) -11-Eicosenyl phospho-N, N-dimethyl-N-propyl-propylammonium
C 28 H 58 NO 4 P (503.74)
231) (Z) -11-eicosenylphospho-N, N, N-trimethyl-butylammonium
C 27 H 56 NO 4 P (489.72)
232) (Z) -11-Eicosenyl phospho-N, N-dimethyl-N-ethyl-butylammonium
C 28 H 58 NO 4 P (503.74)
233) (Z) -11-Eicosenyl phospho-N, N-dimethyl-N-propyl-butylammonium
C 29 H 60 NO 4 P (517.77)
234) (Z) -11-Eicosenyl phospho-N, N-dimethyl-N-alkyl-butylammonium
C 29 H 58 NO 4 P (575.75)
235) Oleyl phospho-N, N, N-trimethyl-propylammonium
C 24 H 50 NO 4 P (447.64)
236) Oleyl-phospho-N, N-dimethyl-N-ethyl-propylammonium
C 25 H 52 NO 4 P (461.66)
237) Oleyl-phospho-N, N-dimethyl-N-propylene-propylammonium
C 26 H 54 NO 4 P (475.69)
238) Oleyl-phospho-N, N, N-trimethyl-butylammonium
C 25 H 52 NO 4 P (461.66)
239) Oleyl-phospho-N, N-dimethyl-N-ethyl-butylammonium
C 26 H 54 NO 4 P (475.69)
240) Oleyl-phospho-N, N-dimethyl-N-propyl-butylammonium
C 27 H 56 NO 4 P (489.72)

Wirkstoffe, die auf alkylierten (Ether)-Lysolecithinen aufgebaut und am Stickstoff hydroxyliert sindActive ingredients based on alkylated (ether) -Lysolecithinen and am Nitrogen are hydroxylated

(A = a; n = 2-4; R3 (A = a; n = 2-4; R 3

, CH3 , CH 3

; m = 1; x = 0; y = 1; z = 1, 2)
; m = 1; x = 0; y = 1; z = 1, 2)

241) 1-O-Octadecyl-2-O-methyl-sn-glycero-3-phospho-N,N-dimethyl-N- dihydroxypropyl-ethylammonium
C29H62NO8P (583,78)
242) 3-O-Octadecyl-2-O-methyl-sn-glycero-1-phospho-N,N-dimethyl-N- dihydroxypropyl-ethylammonium
C29H62NO8P (583,78)
243) 1-O-Octadecyl-2-O-tert-butyl-sn-glycero-3-phospho-N,N-dimethyl-N- dihydroxypropyl-ethylammonium
C32H68NO8P (625,86)
244) 3-O-Octadecyl-2-O-tert.butyl-sn-glycero-3-phospho-N,N-dimethyl-N- dihydroxypropyl-ethylammonium
C32H68NO8P (625,86)
245) 1-O-Octadecyl-2-O-methyl-sn-glycero-3-phospho-N,N-dimethyl-N- dihydroxypropyl-propylammonium
C30H64NO8P (597,81)
246) 1-O-Octadecyl-2-O-methyl-sn-glycero-3-phospho-N,N-dimethyl-N- dihydroxypropyl-butylammonium
C31H66NO8P (611,84)
247) 1-O-Erucyl-2-O-methyl-sn-glycero-3-phospho-N,N-dimethyl-N- dihydroxyprnpyl-ethylammonium
C33H68NO8P (637,87)
248) 1-O-Erucyl-2-O-methyl-sn-glycero-3-phospho-N,N-dimethyl-N- dihydroxypropyl-propylammonium
C34H70NO8P (651,90)
249) 1-O-Octadecyl-2-O-methyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HPi1- diHP2)-ethylammonium
C32H68NO10P (657,86)
250) 1-O-Octadecyl-2-O-tert.butyl-sn-glycero-3-phospho-N,N-dimethyl-N- (HP1-diHP2)-ethylammonium
C35H74NO10P (699,94)
251) 1-O-Octadecyl-2-O-methyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1- diHP2)-propylammonium
C33H70NO10P (671,89)
252) 1-O-Octadecyl-2-O-tert.butyl-sn-glycero-3-phospho-N,N-dimethyl-N- (HP1-diHP2)-propylammonium
C36H76NO10P (713,97)
253) 1-O-Octadecyl-2-O-tert.butyl-sn-glycero-3-phospho-N,N-dimethyl-N- (HP1-diHP2)-butylammonium
C37H78NO10P (727,99)
254) 1-O-Erucyl-2-O-methyl-sn-glycero-3-phospho-N,N-dimethyl-N-(HP1- diHP2)-butylammonium
C38H78NO10P (739,01)241) 1-O-octadecyl-2-O-methyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium
C 29 H 62 NO 8 P (583.78)
242) 3-O-octadecyl-2-O-methyl-sn-glycero-1-phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium
C 29 H 62 NO 8 P (583.78)
243) 1-O-octadecyl-2-O-tert-butyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium
C 32 H 68 NO 8 P (625.86)
244) 3-O-octadecyl-2-O-tert-butyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium
C 32 H 68 NO 8 P (625.86)
245) 1-O-octadecyl-2-O-methyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-propylammonium
C 30 H 64 NO 8 P (597.81)
246) 1-O-octadecyl-2-O-methyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-butylammonium
C 31 H 66 NO 8 P (611,84)
247) 1-O-Erucyl-2-O-methyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxyprnpyl-ethylammonium
C 33 H 68 NO 8 P (637.87)
248) 1-O-Erucyl-2-O-methyl-sn-glycero-3-phospho-N, N-dimethyl-N-dihydroxypropyl-propylammonium
C 34 H 70 NO 8 P (651.90)
249) 1-O-octadecyl-2-O-methyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HPi 1 -diHP 2 ) -ethylammonium
C 32 H 68 NO 10 P (657.86)
250) 1-O-octadecyl-2-O-tert-butyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -ethylammonium
C 35 H 74 NO 10 P (699.94)
251) 1-O-octadecyl-2-O-methyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -propylammonium
C 33 H 70 NO 10 P (671.89)
252) 1-O-octadecyl-2-O-tert-butyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -propylammonium
C 36 H 76 NO 10 P (713.97)
253) 1-O-octadecyl-2-O-tert-butyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -butylammonium
C 37 H 78 NO 10 P (727.99)
254) 1-O-Erucyl-2-O-methyl-sn-glycero-3-phospho-N, N-dimethyl-N- (HP 1 -diHP 2 ) -butylammonium
C 38 H 78 NO 10 P (739.01)

Wirkstoffe, die auf alkylierten (Ether)-Lysolecithinen aufgebaut sind und am Stickstoff nicht hydroxyliert sindActive substances which are based on alkylated (ether) -lysolecithins and on Nitrogen are not hydroxylated

(A = a; n = 3, 4; R3 (A = a; n = 3, 4; R 3

, CH3 , CH 3

; m = 1; x = 1; z = 0)
; m = 1; x = 1; z = 0)

255) 1-O-Erucyl-2-O-methyl-sn-glycero-3-phospho-N,N,N-trimethyl­ propylammonium
C32He6NO6P (591,85)
256) 1-O-Erucyl-3-O-methyl-sn-glycero-2-phopsho-N,N,N-trimethyl­ propylammonium
C32H66NO6P (591,85)
257) 1-O-(Z)-11-Eicosenyl-2-O-methyl-sn-glycero-3-phospho-N,N,N- trimethyl-propylammonium
C30H62NO6P (563,80)
258) 1-O-(Z)-11-Eicosenyl-2-O-tert.butyl-sn-glycero-3-phospho-N,N,N- trimethyl-propylammonium
C33H68NO6P (605,88)
259) 1-O-Oleyl-2-O-tert.butyl-sn-glycero-3-phospho-N,N,N-trimethyl- propylammonium
C31H64NO6P (577,82)
260) 1-O-(Z)-11-Eicosenyl-2-O-tert.butyl-sn-glycero-3-phospho-N,N,N- butylammonium
C34H70NO6P (619,90)
261) 1-O-Oleyl-2-O-tert.butyl-sn-glycero-3-phospho-N,N,N-trimethyl- butylammonium
C32H66NO6P (591,85)255) 1-O-Erucyl-2-O-methyl-sn-glycero-3-phospho-N, N, N-trimethylpropylammonium
C 32 He 6 NO 6 P (591.85)
256) 1-O-Erucyl-3-O-methyl-sn-glycero-2-phosphophen-N, N, N-trimethylpropylammonium
C 32 H 66 NO 6 P (591.85)
257) 1-O- (Z) -11-Eicosenyl-2-O-methyl-sn-glycero-3-phospho-N, N, N-trimethyl-propylammonium
C 30 H 62 NO 6 P (563.80)
258) 1-O- (Z) -11-eicosenyl-2-O-tert-butyl-sn-glycero-3-phospho-N, N, N-trimethyl-propylammonium
C 33 H 68 NO 6 P (605.88)
259) 1-O-Oleyl-2-O-tert-butyl-sn-glycero-3-phospho-N, N, N-trimethyl-propylammonium
C 31 H 64 NO 6 P (577.82)
260) 1-O- (Z) -11-eicosenyl-2-O-tert-butyl-sn-glycero-3-phospho-N, N, N-butylammonium
C 34 H 70 NO 6 P (619.90)
261) 1-O-oleyl-2-O-tert-butyl-sn-glycero-3-phospho-N, N, N-trimethyl-butylammonium
C 32 H 66 NO 6 P (591.85)

Wirkstoffe, die auf Alkandiolphospho-Verbindungen aufgebaut und am Stickstoff hydroxyliert sindActive substances based on alkanediolphospho compounds and on Nitrogen are hydroxylated

(A = b: n = 2, 3; R3 (A = b: n = 2, 3, R 3

, CH3 , CH 3

: m = 1; x = 0; v = 1; z = 1)
: m = 1; x = 0; v = 1; z = 1)

262) 1-O-Erucyl-ethylenglykol-phospho-N,N-dimethyl-N-dihydroxypropyl- ethylammonium
C31H64NO7P (593,82)
263) 1-O-Erucyl-propandiol-(1,3)-phospho-N,N-dimethyl-N-dihydroxypropyl- ethylammonium
C32H66NO7P (607,85)
264) 1-O-Erucyl-propandiol-(1,2)-phospho-N,N-dimethyl-N-dihydroxypropyl- ethylammonium
C32H66NO7P (607,85)
265) 2-O-Erucyl-propandiol-(1,2)-phospho-N,N-dimethyl-N-dihydroxypropyl- ethylammonium
C32H66NO7P (607,85)
266) 1-O-(Z)-11-Eicosenyl-propandiol-(1,2)-phospho-N,N-dimethyl-N- dihydroxypropyl-ethylammonium
C30H62NO7P (579,49)
267) 2-O-(Z)-11-Eicosenyl-propandiol-(1,2)-phospho-N,N-dimethyl-N- dihydroxypropyl-ethylammonium
C30H62NO7P (579,49)
268) 1-O-Oleyl-propandiol-(1,2)-phospho-N,N-dimethyl-N-dihydroxypropyl- ethylammonium
C28H58NO7P (551,74)
269) 2-O-Oleyl-propandiol-(1,2)-phospho-N,N-dimethyl-N-dihydroxypropyl- ethylammonium
C28H58NO7P (551,74)
270) 2-O-Octadecyl-propandiol-(1,2)-phospho-N,N-dimethyl-N- dihydroxypropyl-ethylammonium
C28H60NO7P (553,76)
271) 1-O-Octadecyl-propandiol-(1,2)-phospho-N,N-dimethyl-N- dihydroxypropyl-propylammonium
C29H62NO7P (626,24)
272) 2-O-Octadecyl-propandiol-(1,2)-phospho-N,N-dimethyl-N- dihydroxypropyl-propylammonium
C29H62NO7P (626,24)262) 1-O-Erucyl-ethylene glycol-phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium
C 31 H 64 NO 7 P (593.82)
263) 1-O-Erucyl-propanediol- (1,3) -phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium
C 32 H 66 NO 7 P (607.85)
264) 1-O-Erucyl-propanediol- (1,2) -phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium
C 32 H 66 NO 7 P (607.85)
265) 2-O-Erucyl-propanediol- (1,2) -phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium
C 32 H 66 NO 7 P (607.85)
266) 1-O- (Z) -11-eicosenylpropanediol- (1,2) -phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium
C 30 H 62 NO 7 P (579.49)
267) 2-O- (Z) -11-eicosenylpropanediol- (1,2) -phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium
C 30 H 62 NO 7 P (579.49)
268) 1-O-Oleyl-propanediol- (1,2) -phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium
C 28 H 58 NO 7 P (551.74)
269) 2-O-oleyl-propanediol- (1,2) -phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium
C 28 H 58 NO 7 P (551.74)
270) 2-O-octadecyl-propanediol- (1,2) -phospho-N, N-dimethyl-N-dihydroxypropyl-ethylammonium
C 28 H 60 NO 7 P (553.76)
271) 1-O-octadecyl-propanediol- (1,2) -phospho-N, N-dimethyl-N-dihydroxypropyl-propylammonium
C 29 H 62 NO 7 P (626.24)
272) 2-O-Octadecyl-propanediol- (1,2) -phospho-N, N-dimethyl-N-dihydroxypropyl-propylammonium
C 29 H 62 NO 7 P (626.24)

Wirkstoffe, die auf Alkandiolphospho-Verbindungen aufgebaut und am Stickstoff nicht hydroxyliert sindActive substances based on alkanediolphospho compounds and on Nitrogen are not hydroxylated

(A = b; n = 3; R3 (A = b; n = 3, R 3

, CH3 , CH 3

; m = 1; x = 1; z = 0)
; m = 1; x = 1; z = 0)

273) 1-O-Erucyl-propandiol-(1,2)-phospho-N,N,N-trimethyl- propylammonium
C31H64NO5P (562,82)
274) 1-O-Erucyl-propandiol-(1,2)-phospho-N,N,N-trimethyl- propylammonium
C31H64NO5P (562,82)
275) 1-O-(Z)-11-Eicosenyl-propandiol-(1,3)-phospho-N,N,N-trimethyl- propylammonium
C29H60NO5P (533,77)
276) 1-O-Oleyl-propandiol-(1,2)-phospho-N,N,N-trimethyl-propylammonium
C27H66NO5P (505,72)
277) 2-O-Oleyl-propandiol-(1,2)-phospho-N,N,N-trimethyl-propylammonium
C27H56NO5P (505,72)
278) 1-O-Octadecyl-propandiol-(1,2)-phospho-N,N,N-propylammonium
C27H58NO5P (507,73)
279) 2-O-Octadecyl-propandiol-(1,2)-phospho-N,N,N-trimethyl- propylammonium
C27H58NO5P (507,73)273) 1-O-Erucyl-propanediol- (1,2) -phospho-N, N, N-trimethyl-propylammonium
C 31 H 64 NO 5 P (562.82)
274) 1-O-Erucyl-propanediol- (1,2) -phospho-N, N, N-trimethyl-propylammonium
C 31 H 64 NO 5 P (562.82)
275) 1-O- (Z) -11-eicosenyl-propanediol- (1,3) -phospho-N, N, N-trimethyl-propylammonium
C 29 H 60 NO 5 P (533.77)
276) 1-O-oleyl-propanediol- (1,2) -phospho-N, N, N-trimethyl-propylammonium
C 27 H 66 NO 5 P (505.72)
277) 2-O-oleyl-propanediol- (1,2) -phospho-N, N, N-trimethyl-propylammonium
C 27 H 56 NO 5 P (505.72)
278) 1-O-Octadecyl-propanediol- (1,2) -phospho-N, N, N-propylammonium
C 27 H 58 NO 5 P (507.73)
279) 2-O-octadecyl-propanediol- (1,2) -phospho-N, N, N-trimethyl-propylammonium
C 27 H 58 NO 5 P (507.73)

Claims (27)

1. Verbindung der allgemeinen Formel (I)
worin A
ist, wobei R1 und R2 unabhängig voneinander Wasserstoff, einen gesättigten oder ungesättigten Acyl- oder Alkylrest bedeuten, der gegebenenfalls verzweigt oder/und substituiert sein kann, wobei die Summe der Kohlenstoffatome in Acyl und Alkyl zwischen 16 und 44 C-Atomen liegt,
ist, wobei R1 und R2 die gleiche Bedeutung wie in a besitzen; s eine ganze Zahl von 0 bis 8 darstellt,
c = RO- ist, wobei R einen gesättigten oder ungesättigten Alkylrest vorwiegend mit cis-Doppelbindung, von 12 bis 30 Kohlenstoffatomen bedeutet,
n eine ganze Zahl von 2 bis 8 darstellt,
R3
a = 1,2-Dihydroxypropyl sein kann oder
b = Alkyl mit 1 bis 3 C-Atomen sein kann, wenn z < 0 ist oder = Alkyl mit 1 bis 3 C-Atomen sein kann, wenn n ≠ 2 und z = 0 ist,
m = 1 oder 2 ist,
x = eine ganze Zahl von 0 bis 8 darstellt,
y = 1 für z = 1 bis 5 ist oder = 1 bis 4 ist für z = 1
z = eine ganze Zahl von 0 bis 5 darstellt.1. Compound of the general formula (I)
where A
where R 1 and R 2 independently of one another represent hydrogen, a saturated or unsaturated acyl or alkyl radical which may optionally be branched or / and substituted, the sum of the carbon atoms in acyl and alkyl being between 16 and 44 C atoms,
wherein R 1 and R 2 have the same meaning as in a; s represents an integer from 0 to 8,
c = RO-, where R is a saturated or unsaturated alkyl radical predominantly having a cis double bond, from 12 to 30 carbon atoms,
n represents an integer from 2 to 8,
R 3
a = 1,2-dihydroxypropyl may be or
b = alkyl having 1 to 3 carbon atoms, if z <0 or = alkyl having 1 to 3 carbon atoms, if n ≠ 2 and z = 0,
m = 1 or 2,
x = an integer from 0 to 8,
y = 1 for z = 1 to 5 or = 1 to 4 for z = 1
z = represents an integer from 0 to 5. 2. Verbindung der allgemeinen Formel I mit A = a; n = 2-6; R3, CH3; m = 1; x = 0; y = 1; z = 1.2. Compound of the general formula I where A = a; n = 2-6; R 3, CH 3; m = 1; x = 0; y = 1; z = 1. 3. Verbindung der allgemeinen Formel I mit A = a; n = 2-6; R3, O3; m = 1; x = 0; y = 1; z = 2.3. Compound of the general formula I where A = a; n = 2-6; R 3, O 3; m = 1; x = 0; y = 1; z = 2. 4. Verbindung der allgemeinen Formel I mit A = a; n = 2-8; R3, CH3; m = 1; x = 0; y = 1; z = 3.4. Compound of the general formula I where A = a; n = 2-8; R 3, CH 3; m = 1; x = 0; y = 1; z = 3. 5. Verbindung der allgemeinen Formel I mit A = a; n = 2, 3; R3, O3; m = 1; x = 0; y = 1; z = 4.5. Compound of the general formula I with A = a; n = 2, 3; R 3, O 3; m = 1; x = 0; y = 1; z = 4. 6. Verbindung der allgemeinen Formel I mit A = a; n = 2-6; m = 1; x = 1; z = 0.6. Compound of the general formula I where A = a; n = 2-6; m = 1; x = 1; z = 0. 7. Verbindung der allgemeinen Formel I mit A = a; n = 2-6; R3, CH3; m = 1, x = 0, y = 1, z = 1. 7. Compound of the general formula I where A = a; n = 2-6; R 3, CH 3; m = 1, x = 0, y = 1, z = 1. 8. Verbindung der allgemeinen Formel I mit A = 0; n = 2-6; R3, CH3; m = 1; x = 0; y = 1; z = 2.8. Compound of general formula I with A = 0; n = 2-6; R 3, CH 3; m = 1; x = 0; y = 1; z = 2. 9. Verbindung der allgemeinen Formel I mit A = a; n = 2-6; R3, CH3; n = 1; x = 0; y = 1; z = 3.9. Compound of the general formula I where A = a; n = 2-6; R 3, CH 3; n = 1; x = 0; y = 1; z = 3. 10. Verbindung der allgemeinen Formel I mit A = a; n = 3; R3, CH3; m = 1; x = 1; z = 0.10. Compound of the general formula I where A = a; n = 3; R 3, CH 3; m = 1; x = 1; z = 0. 11. Verbindung der allgemeinen Formel I mit A = b; n = 2-4; R3, CH3; m = 1; x = 0; y = 1; z = 1.11. Compound of the general formula I where A = b; n = 2-4; R 3, CH 3; m = 1; x = 0; y = 1; z = 1. 12. Verbindung der allgemeinen Formel I mit A = b; n = 2-4; R3, CH3; m = 1; x = 0; y = 1; z = 1.12. Compound of the general formula I where A = b; n = 2-4; R 3, CH 3; m = 1; x = 0; y = 1; z = 1. 13. Verbindung der allgemeinen Formel I mit A = b; n = 2-4; R3, CH3; m = 1, x = 0; y = 1; z = 2.13. Compound of the general formula I where A = b; n = 2-4; R 3, CH 3; m = 1, x = 0; y = 1; z = 2. 14. Verbindung der allgemeinen Formel I mit A = b; n = 2-4; R3, CH3; m = 1; x = 0; y = 1; z = 2.14. Compound of the general formula I where A = b; n = 2-4; R 3, CH 3; m = 1; x = 0; y = 1; z = 2. 15. Verbindung der allgemeinen Formel I mit A = b; n = 2-6; R, CH3; m = 1; x = 0; y = 1; z = 3.15. Compound of the general formula I where A = b; n = 2-6; R, CH 3 ; m = 1; x = 0; y = 1; z = 3. 16. Verbindung der allgemeinen Formel I mit A = b; n = 2-6; R, CH3; m = 1; x = 1; z = 0.16. Compound of the general formula I where A = b; n = 2-6; R, CH 3 ; m = 1; x = 1; z = 0. 17. Verbindung der allgemeinen Formel I mit A = c; n = 2-6; R3, CH3; m = 1; x = 0; y = 1; z = 1.17. Compound of the general formula I where A = c; n = 2-6; R 3, CH 3; m = 1; x = 0; y = 1; z = 1. 18. Verbindung der allgemeinen Formel I mit A = c; n = 2-6; R3, CH3; m = 1; x = 0; y = 1; z = 2. 18. Compound of the general formula I where A = c; n = 2-6; R 3, CH 3; m = 1; x = 0; y = 1; z = 2. 19. Verbindung der allgemeinen Formel I mit A = c; n = 2-4; R3, CH3; m = 1; x = 0; y = 1; z = 3.19. Compound of the general formula I where A = c; n = 2-4; R 3, CH 3; m = 1; x = 0; y = 1; z = 3. 20. Verbindung der allgemeinen Formel I mit A = a; n = 2-4; R3, CH3; m = 1; x = 0; y = 1; z = 1, 2.20. Compound of the general formula I where A = a; n = 2-4; R 3, CH 3; m = 1; x = 0; y = 1; z = 1, 2. 21. Verbindung der allgemeinen Formel I mit A = a; n = 3, 4; R3, CH3; m = 1; x = 1; z = 0.21. Compound of the general formula I where A = a; n = 3, 4; R 3, CH 3; m = 1; x = 1; z = 0. 22. Verbindung der allgemeinen Formel I mit A = b; n = 2, 3; R3, CH3; m = 1; x = 0; y = 1; z = 1.22. Compound of the general formula I where A = b; n = 2, 3; R 3, CH 3; m = 1; x = 0; y = 1; z = 1. 23. Verbindung der allgemeinen Formel I mit A = b; n = 3; R3, CH3; m m = 1; x = 1; z = 0.23. Compound of the general formula I where A = b; n = 3; R 3, CH 3; mm = 1; x = 1; z = 0. 24. Liposome, die Phospholipide oder/und Alkylphospholipide, gegebenenfalls Cholesterin und 1 bis 50 Mol-% einer Verbindung der allgemeinen Formel (I) von Anspruch 1 oder deren Salze enthalten, wobei das Cholesterin, die Phospholipide, die Alkylphospholipide und die Verbindung der Formel (I) zusammen 100 Mol-% ergeben.24. Liposomes containing phospholipids and / or alkylphospholipids, optionally cholesterol and 1 to 50 mol% of a compound of contain general formula (I) of claim 1 or salts thereof, the cholesterol, the phospholipids, the alkylphospholipids and the compound of the formula (I) together give 100 mol%. 25. Verwendung einer Verbindung der allgemeinen Formel (I) von Anspruch 1 als Gentransportvehikel.25. Use of a compound of general formula (I) of Claim 1 as a gene delivery vehicle. 26. Verwendung einer Verbindung der allgemeinen Formel (I) von Anspruch 1 als Lösungsmittel für wasserunlösliche Wirkstoffe.26. Use of a compound of general formula (I) of Claim 1 as a solvent for water-insoluble active ingredients. 27. Verwendung nach Anspruch 26, dadurch gekennzeichnet, daß R1 einen Erucasäurerest darstellt.27. Use according to claim 26, characterized in that R 1 represents an erucic acid residue.
DE19735776A 1996-06-03 1997-08-18 New neutral or cationic phospholipid analogues Ceased DE19735776A1 (en)

Priority Applications (17)

Application Number Priority Date Filing Date Title
DE19735776A DE19735776A1 (en) 1996-06-03 1997-08-18 New neutral or cationic phospholipid analogues
ES98945258T ES2181269T3 (en) 1997-08-18 1998-08-18 COMPOSTS ANALOGS TO PHOSPHOLIPIDS.
AT98945258T ATE226210T1 (en) 1997-08-18 1998-08-18 PHOSPHOLIPIDE ANALOGOUS COMPOUNDS
PT98945258T PT1019417E (en) 1997-08-18 1998-08-18 PHOSPHOLIPID ANALYSIS COMPOUNDS
DE59805997T DE59805997D1 (en) 1997-08-18 1998-08-18 PHOSPHOLIPID ANALOG CONNECTIONS
US09/486,039 US6344576B1 (en) 1997-08-18 1998-08-18 Phospholipid-analogous compounds
JP2000509716A JP4550271B2 (en) 1997-08-18 1998-08-18 Phospholipid analog
AU92632/98A AU9263298A (en) 1997-08-18 1998-08-18 Phospholipid analogue compounds
EP98945258A EP1019417B1 (en) 1997-08-18 1998-08-18 Phospholipid analogue compounds
PCT/EP1998/005252 WO1999009037A1 (en) 1997-08-18 1998-08-18 Phospholipid analogue compounds
DK98945258T DK1019417T3 (en) 1997-08-18 1998-08-18 Phospholipid analogues
US10/025,778 US6545169B1 (en) 1997-08-18 2001-12-26 Phospholipid-analogous compounds
US10/377,617 US6828453B2 (en) 1997-08-18 2003-03-04 Phospholipid-analogous compounds
US10/969,020 US7595411B2 (en) 1997-08-18 2004-10-21 Phospholipid-analogous compounds
JP2009219177A JP4714289B2 (en) 1997-08-18 2009-09-24 Phospholipid analog
US12/567,992 US7939683B2 (en) 1997-08-18 2009-09-28 Phospholipid-analogous compounds
US13/084,876 US8497388B2 (en) 1997-08-18 2011-04-12 Phospholipid-analogous compounds

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DE19622224A DE19622224A1 (en) 1996-02-16 1996-06-03 Phosphatidyl oligoglycerols
DE19735776A DE19735776A1 (en) 1996-06-03 1997-08-18 New neutral or cationic phospholipid analogues

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002009678A2 (en) * 2000-07-31 2002-02-07 Ottawa Heart Institute Research Corporation Charged phospholipid compositions and methods for their use
WO2003103625A2 (en) * 2002-06-11 2003-12-18 Carlo Ghisalberti Dermocosmetic treatment by metabolic phospholipids
WO2010000352A2 (en) 2008-07-01 2010-01-07 Braun Gmbh Small electrical appliance for removing hairs

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002009678A2 (en) * 2000-07-31 2002-02-07 Ottawa Heart Institute Research Corporation Charged phospholipid compositions and methods for their use
WO2002009678A3 (en) * 2000-07-31 2003-04-10 Ottawa Heart Inst Res Corp Charged phospholipid compositions and methods for their use
US6828306B2 (en) 2000-07-31 2004-12-07 Ottawa Heart Institute Research Corporation Charged lipid compositions and methods for their use
US7390783B2 (en) 2000-07-31 2008-06-24 Ottawa Heart Institute Research Corporation Charged phospholipid compositions and methods for their use
WO2003103625A2 (en) * 2002-06-11 2003-12-18 Carlo Ghisalberti Dermocosmetic treatment by metabolic phospholipids
WO2003103625A3 (en) * 2002-06-11 2004-04-29 Carlo Ghisalberti Dermocosmetic treatment by metabolic phospholipids
WO2010000352A2 (en) 2008-07-01 2010-01-07 Braun Gmbh Small electrical appliance for removing hairs

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