Patent Description:
The number of bacteria that are becoming resistant to conventional antibacterial drugs is growing, and therefore new drugs are needed to treat diseases caused by these resistant bacteria (<NPL>; <NPL>).

First-generation lipophosphonoxins with activity against gram-positive bacteria have been recently described (<NPL>, <CIT>, patent <CIT>). Furthermore, the mechanism of their action, consisting of the selective disruption of the bacterial membrane, has also been described (<NPL>). This was followed by second-generation lipophosphonoxins (<NPL>, <CIT>, <CIT>, <CIT>, <CIT>).

Lipophosphonoxins (LPPOs) are bactericidal substances with rapid kinetics, and they are not genotoxic. The maximum tolerated dose (MTD) in mice when administered orally is very high (> <NUM>/kg) and the bacteria are unable to develop resistance. Lipophosphonoxins are chemically stable over a wide pH range and do not pass through the monolayer of CACO-<NUM> cells, which means that they are unlikely to be absorbed when administered orally.

LPPOs belong to a growing family of antibacterial peptidomimetics, such as cationic steroid antibiotics (<NPL>; <NPL>; <NPL>), lipophilic derivatives of norspermidine (<NPL>), arylamide foldamers (<NPL>; <NPL>) or the promising synthetic bactericidal antimicrobial peptide LTX -<NUM> (<NPL>. <NPL>), which degrades the membranes of harmful microorganisms. Although these compounds are structurally heterogeneous, they are all amphiphilic molecules containing a lipophilic moiety and a hydrophilic moiety, usually carrying a positive charge. Lipophosphonoxins also share this structural motif, however, the main advantage of lipophosphonoxins lies in their modular structure, enabling the systematic tuning of their biological properties.

<CIT> discloses phosphoric acid esters as protonated antimicrobial agents. These compounds differ significantly from phosphonoxines.

This invention describes novel lipophosphonoxins of the general formula I which have strong antibacterial effects against gram-positive and gram-negative bacteria. The advantage of these compounds is, in addition to easy preparation, also the large degree of modularity of their structure, which enables additional adaptation of their biological properties.

The invention therefore relates to lipophosphonoxins of the general formula
<CHM>
wherein.

Preferably, the Y substituent is selected from:
<CHM>
<CHM>
wherein n, o, p, R<NUM>, R<NUM>, R<NUM> are as described herein. Preferably, R<NUM>, R<NUM>, R<NUM> are H or methyl.

Preferably, the X substituent is selected from:
<CHM>
wherein m is <NUM>-<NUM>.

Preferably, Z is
<CHM>
wherein q is <NUM> to <NUM>.

Said salts include salts with inorganic or organic anions and in particular, but not exclusively, pharmaceutically acceptable salts suitable for physiological administration.

Pharmaceutically acceptable salts may be salts derived from inorganic or organic acids. A person skilled in the art will be able to determine which salts are pharmaceutically acceptable; in particular, they are salts with one or more desirable physical properties such as increased pharmaceutical stability at various temperatures and humidities, the desired solubility in water or oil, or are non-toxic.

Suitable pharmaceutically acceptable salts of the compounds of this invention preferably include anions derived from inorganic acids such as hydrochloric, hydrobromic, hydrofluoric, boric, fluoroboric, phosphoric, metaphosphoric, nitric, carbonic, sulfuric and sulfurous acids and from organic acids such as acetic acid, benzene sulfonic, benzoic, citric, ethanesulfonic, fumaric, gluconic, glycolic, isethionic, lactic, lactobionic, maleic, malonic, methanesulfonic, trifluoromethanesulfonic, succinic, toluenesulfonic, tartaric and trifluoroacetic acids. Suitable organic acids generally include, for example, the following classes of organic acids: aliphatic, cycloaliphatic, aromatic, arylaliphatic, heterocyclic, carboxylic and sulfonic acids.

Specific examples of suitable organic acids include acetate, trifluoroacetate, formate, propionate, succinate, glycolate, gluconate, digluconate, hyaluronate, lactate, malate, tartrate, citrate, ascorbate, glucuronate, maleate, fumarate, pyruvate, aspartate, glutamate, benzoate, anthranilate, stearate, salicylate, p-hydroxybenzoate, phenylacetate, mandelate, pamoate, methane sulfonate, ethanesulfonate, benzenesulfonate, pantothenate, toluenesulfonate, <NUM>-hydroxyethanesulfonate, sulfanilate, cyclohexylaminosulfonate, <NUM>-hydroxybutyrate, galactarate, galacturonate, adipate, alginate, butyrate, camphorate, camphorsulfonate, cyclopentanepropionate, dodecyl sulfate, glycoheptanoate, glycerophosphate, heptanoate, hexanoate, nicotinate, <NUM>-naphthalenesulfonate, oxalate, palmoate, pectinate, <NUM>-phenylpropionate, picrate, pivalate, thiocyanate and undecanoate.

The compounds of formula I contain several chiral centers (especially in the L groups and in some R<NUM> groups). The existence of a chiral center allows the compound to exist as one of two possible optical isomers ((R) - or (S)-enantiomer), or as a racemic mixture of both. In this case, where other chiral centers are present, all diastereomers and mixtures of diastereomers formed are also included in the range of the lipophosphonoxins of general formula I described in this invention.

The invention furthermore relates to lipophosphonoxins of the general formula I or their diastereomers or to pharmaceutically acceptable salts and hydrates, and/or mixtures of such compounds, for use as medicaments.

The invention furthermore relates to lipophosphonoxins of the general formula I or their diastereomers or to pharmaceutically acceptable salts and hydrates, and/or mixtures of such compounds, for use as antibacterial drugs.

The invention also relates to a pharmaceutical composition, preferably to an antibacterial drug composition, comprising at least one lipophosphonoxin of the general formula I or diastereomer or a pharmaceutically acceptable salt or hydrate thereof, and/or a mixture of such compounds as the active ingredient.

The invention furthermore relates to a disinfectant for non-therapeutic purposes and/or to a selective culture medium comprising at least one lipophosphonoxin of general formula I or a diastereomer or a pharmaceutically acceptable salt or hydrate thereof, and/or mixtures of such compounds as the active ingredient.

The invention also relates to the use of lipophosphonoxins of general formula I or their diastereomers or pharmaceutically acceptable salts or hydrates, and/or mixtures of such compounds, for the preparation of an antibacterial drug.

Finally, the invention relates to the use of lipophosphonoxins of general formula I or their diastereomers or pharmaceutically acceptable salts and hydrates, and/or mixtures of such compounds, as active ingredients of disinfectants for non-therapeutic purposes, and/or selective culture media for in vitro cultivation of bacteria, fungi or eukaryotic cell lines.

A medicament / drug is any substance or combination of substances intended to treat or prevent disease in humans or animals, and any substance or combination of substances which may be administered to humans or animals to establish a medical diagnosis or to restore, ameliorate or modify physiological functions of humans or animals.

The compounds of this invention exhibit antibacterial effects against strains of Escherichia coli, Pseudomonas aeruginosa, Enterococcus faecalis, Staphylococcus aureus, Staphylococcus haemolyticus, Enterococcus faecium, Staphylococcus epidermidis, Enterobacter kobei, and even against strains resistant to existing antibiotics.

Compared to the first-generation LPPOs (<NPL>, patent <CIT>, patent <CIT>) and the second-generation LPPOs (<NPL>, <CIT>, <CIT>, <CIT>), the herein presented third-generation lipophosphonoxins (LPPOs) exhibit a wider spectrum of antibacterial activity, higher selectivity and easier preparation. The biggest benefit over the prior art is the fact that they exhibit significantly lower hemolytic activities as well as very low binding to serum albumins.

The greatest benefit of the claimed compounds is their surprisingly high potency, even against dangerous multi-resistant bacterial strains occurring in a hospital environment. In addition, the structure of the third-generation LPPOs is even more modular than the first- and second-generation LPPOs, allowing the fine tuning of physical and biological properties.

The higher degree of modularity of the structure of third-generation LPPOs compared to first- and second-generation LPPOs, enabled by their easy synthesis and assembly of individual modules, provides extensive structural variations of the compounds of this invention that can be used to modulate their biological activity.

Formula (I) includes the compounds listed in Examples <NUM>-<NUM> and <NUM>-<NUM>.

Methyl phosphonate (<NUM> mmol) is dissolved in <NUM> % aqueous pyridine (<NUM>) and the reaction mixture is stirred at <NUM> for <NUM>. The reaction mixture is concentrated in vacuo at temperature below <NUM>, the residue is dissolved in ethanol (<NUM>) and passed through a column of Dowex <NUM> v H+ form (<NUM>). The column is washed with EtOH (<NUM>). The solvent is removed in vacuo. Product is obtained by column chromatography on silica gel using linear gradient of solvent system H1 (ethyl acetate, acetone, ethanol, water <NUM>:<NUM>:<NUM>:<NUM>) in ethyl acetate.

Mono alkyl vinylphosphonate (<NUM> mmol) is randered dry by co-evaporation with EtOH (<NUM>/mmol) and toluene (<NUM>), dissolved in DCM (<NUM>) and cooled to -<NUM> under argon atmosphere.

Oxalylchloride (<NUM> mol/L) in DCM (<NUM>) is slowly added and the reaction mixture is stirred at rt for <NUM>. Catalytic ammount of DMF (<NUM>µL) is added and the reaction mixture is stirred until gass evolution ceassed. Hydroxyderivative (<NUM> mmol) is then added folowed by addition of triethylamine (<NUM> mmol). The reaction mixture is stirred at rt for <NUM> under argon atmosphere. The reaction mixture is extracted with sat. NaHCO<NUM> (<NUM>) and sat. NaCl (<NUM>). Organic phase is dried over Na<NUM>SO<NUM> and concentrated in vacuo. Product is obtained by column chromatography using linear gradient of acetone in toluene or linear gradient of ethanol in chloroform.

Mono alkyl vinylphosphonate (<NUM> mmol) and hydroxyderivative (<NUM> mmol) is randered anhydrous by co-evaporation with DCM (2x10 ml) and dissolved in the same solvent (<NUM>). Methylimidazole (<NUM> mmol) and TPSCl (<NUM> mmol) were added and the reaction mixture is stirred at re under argon atmosphere for <NUM>-<NUM>. Progress of the reaction is followed by TLC using mixture of acetone/toluene (<NUM>:<NUM>). The reaction mixture is diluted with DCM (<NUM>) and washed subsequently with sat. soln NaHCO<NUM> (<NUM>) and brine (<NUM>). Organic phases were combined, dried over Na<NUM>SO<NUM> and concentrated in vacuo. Product is obtained by column chromatography using linear gradient of acetone in toluene or linear gradient of ethanol in chloroform.

Mono alkyl vinylphosphonate (<NUM> mmol) and tetrabutylammonium hydroxide (<NUM> mmol) is randered anhydrous by co-evaporation with ethanol (2x <NUM>) and DMF (<NUM>) and dissolved in DMF (<NUM>). α,ω-Dibromalkan (<NUM> mmol) is added and the reaction mixture is stirred under argon atmosphere at <NUM> for <NUM>-<NUM>. Progress of the reaction is followed by TLC using mixture of acetone/toluene (<NUM>:<NUM>). The reaction mixture is concentrated in vacuo and product is obtained by column chromatography using linear gradient of acetone in toluene.

The mixture of vinylphosphonate dimer (<NUM> mmol) and secondary amine (<NUM> mmol) in n-butanol (<NUM>/mmol) is stirred at <NUM> for <NUM>-<NUM> in sealed flask. Progress of the reaction is followed by TLC using mixture of EtOH/CHCl<NUM> (<NUM>:<NUM>). The reaction mixture is concentrated in vacuo and product is obtained by column chromatography using linear gradient of ethanol in chloroform.

Starting Boc derivative (<NUM> mmol) is dissolved in <NUM> methanolic HCl (<NUM>). The reaction mixture is stirred at rt for <NUM>. The reaction mixture is concentrated in vacuo and product is obtained by precipitation from anhydrous ethyl acetate. If necessary, the final product is repurified by preparative HPLC on reversed phase using linear gradient of methanil in <NUM> % aqueous TFA.

Butyl vinylphosphonate is prepared from mono methyl vinylphosphonate (<NUM>, <NUM> mmol) and <NUM>-butanol using general method B2 and general method A in <NUM>% (<NUM>,<NUM>, <NUM>,<NUM> mmol) overall yield in the form of colorless oil.

<NUM>H NMR (<NUM>, CDCl<NUM>): <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>,), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (s, <NUM>).

<NUM>C NMR (<NUM>, CDCl<NUM>): <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>).

<NUM>P{<NUM>H} NMR (<NUM>, CDCl<NUM>): <NUM>.

IR νmax (KBr) <NUM> (vw), <NUM><NUM>), <NUM> (s), <NUM> (m), <NUM> (m), <NUM> (w, vbr), <NUM> (w, vbr), <NUM> (m, vbr), <NUM> (w, vbr), <NUM> (m, vbr), <NUM> (m), <NUM> (w), <NUM> (m), <NUM> (w), <NUM> (m), <NUM> (w), <NUM> (s), <NUM> (s), <NUM> (vs), <NUM> (vs), <NUM> (w).

HR-MS(ESI+) For C<NUM>H<NUM>O<NUM>NaP (M+Na)+ calcd <NUM>, found <NUM>.

Pentyl vinylphosphonate is prepared from mono methyl vinylphosphonate (<NUM>, <NUM> mmol) and <NUM>-pentanol using general method B2 and general method A in <NUM>% (<NUM> g, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>H NMR (<NUM>, CDCl<NUM>): <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (d, <NUM>, JH,P = <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>).

<NUM>C NMR (<NUM>, CDCl<NUM>): <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>).

IR νmax (KBr) <NUM> (vw), <NUM> (s), <NUM> (s), <NUM> (m), <NUM> (m), <NUM> (w), <NUM> (w), <NUM> (w), <NUM> (vw), <NUM> (m), <NUM> (w), <NUM> (w), <NUM> (s), <NUM> (w), <NUM> (vs), <NUM> (vs), <NUM> (vs), <NUM> (s), <NUM> (s), <NUM> (w), <NUM> (m).

HR-MS(ESI+) For C<NUM>H<NUM>O<NUM>P (M+H)+ calcd <NUM>, found <NUM>.

Hexyl vinylphosphonate is prepared from mono methyl vinylphosphonate (<NUM>, <NUM> mmol) and <NUM>-hexanol using general method B2 and general method A in <NUM>% (<NUM> g, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>H NMR (<NUM>, CDCl<NUM>): <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM>, <NUM>-<NUM> (m, <NUM>), <NUM> (s, <NUM>).

<NUM>C NMR (<NUM>, CDCl<NUM>): <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>).

IR νmax (KBr) <NUM> (vw), <NUM> (s), <NUM> (s), <NUM> (s), <NUM> (s), <NUM> (m, vbr), <NUM> (m, vbr), <NUM> (m,vbr), <NUM> (m, vbr), <NUM> (m, vbr), <NUM> (w), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (s), <NUM> (s), <NUM> (vs), <NUM> (vs), <NUM> (vs), <NUM> (w).

Heptyl vinylphosphonate is prepared from mono methyl vinylphosphonate (<NUM>, <NUM> mmol) and <NUM>-heptanol (<NUM>, <NUM> mmol) using general method B1 and general method A in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>H NMR (<NUM>, Chloroform-d) δ <NUM> (s, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (q, J = <NUM>, <NUM>), <NUM> (p, J = <NUM>, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>).

<NUM>P NMR (<NUM>, Chloroform-d) δ <NUM>.

<NUM>C NMR (<NUM>, Chloroform-d) δ <NUM>, <NUM> (d, J= <NUM>), <NUM> (d, J= <NUM>), <NUM>, <NUM> (d, J= <NUM>), <NUM>, <NUM>, <NUM>, <NUM>.

IR νmax(film) <NUM> (w), <NUM> (m), <NUM> (s), <NUM> (m), <NUM> (m), <NUM> (w, br), <NUM> (w), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (s), <NUM> (s), <NUM> (s), <NUM> (vs), <NUM> (vs), <NUM> (m), <NUM> (m), <NUM> (m).

HR-MS (ESI-): For C<NUM>H<NUM>O<NUM>P (M - H)- m/z calculated <NUM>, found <NUM> ± <NUM> ppm.

Octyl vinylphosphonate is prepared from mono methyl vinylphosphonate (<NUM>, <NUM> mmol) and <NUM>-octanol using general method B1 and general method A in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>H NMR (<NUM>, Chloroform-d) δ <NUM>-<NUM> (m, <NUM>), <NUM> (q, J = <NUM>, <NUM>), <NUM> (dt, J = <NUM>, <NUM>, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>).

<NUM>C NMR (<NUM>, Chloroform-d) δ <NUM> (d, J = <NUM>), <NUM> (d, J = <NUM>), <NUM> (d, J = <NUM>), <NUM>, <NUM> (d, J = <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM>.

IR νmax(CHCl<NUM>) <NUM> (vw), <NUM> (s), <NUM> (vs), <NUM> (s), <NUM> (s), <NUM> (w, vbr), <NUM> (w, vbr), <NUM> (m, vbr), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (w), <NUM> (m), <NUM> (s), ~<NUM> (s, sh), <NUM> (vs), <NUM> (vs), <NUM> (w), <NUM> (w).

HR-MS (APCI+): For C<NUM>H<NUM>O<NUM>P (M + H)+ m/z calculated <NUM>, found <NUM> ± <NUM> ppm.

Decyl vinylphosphonate is prepared from mono methyl vinylphosphonate (<NUM>, <NUM> mmol) and <NUM>-octanol (<NUM>, <NUM> mmol) using general method B1 and general method A in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>H NMR (<NUM>, Chloroform-d) δ <NUM> (brs, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (q, J = <NUM>, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>).

<NUM>C NMR (<NUM>, Chloroform-d) δ <NUM>, <NUM> (d, J = <NUM>), <NUM> (d, J = <NUM>), <NUM>, <NUM> (d, J = <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>.

IR νmax(CHCl<NUM>) <NUM> (vw), <NUM> (vs), <NUM> (vs), <NUM> (s), <NUM> (vs), <NUM> (m, br), <NUM> (m, vbr), <NUM> (m, br), <NUM> (m, br, sh), <NUM> (m, vbr), <NUM> (s), <NUM> (s), <NUM> (m), <NUM> (s), <NUM> (m), <NUM> (m), <NUM> (vs), <NUM> (vs, br), <NUM> (vs, br), <NUM> (m).

HR-MS(ESI+): For C<NUM>H<NUM>O<NUM>NaP (M + Na)+ m/z calculated <NUM>, found <NUM> ± <NUM> ppm; for C<NUM>H<NUM>O<NUM>P (M + H)+ m/z calculated <NUM>, found <NUM> ± <NUM> ppm.

Phenethyl vinylphosphonate is prepared from mono methyl vinylphosphonate (<NUM>, <NUM> mmol) and phenethyl bromide (<NUM> %, <NUM>, <NUM> mmol) using general method C and general method A in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>H NMR (<NUM>, Chloroform-d) δ <NUM> (brs, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (q, J = <NUM>, <NUM>), <NUM> (t, J = <NUM>, <NUM>).

<NUM>C NMR (<NUM>, Chloroform-d) δ <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, J = <NUM>), <NUM> (d, J = <NUM>), <NUM> (d, J = <NUM>).

IR νmax(film) <NUM> (w), <NUM> (w), <NUM> (w), <NUM> (w), <NUM> (w), <NUM> (m), <NUM> (m), <NUM> (w), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (s), <NUM> (m), <NUM> (m), <NUM> (s), <NUM> (vs), <NUM>(s), <NUM> (vs), <NUM> (m), <NUM> (s), <NUM> (m).

HR-MS(ESI+): For C<NUM>H<NUM>O<NUM>NaP (M + Na)+ m/z calculated <NUM>, found <NUM> ± <NUM> ppm. For C<NUM>H<NUM>O<NUM>P (M + H)+ m/z calculated <NUM>, found <NUM> ± <NUM> ppm.

<NUM>-(Adamantan-<NUM>-yl)ethyl vinylphosphonate is prepared from mono methy vinylphosphonate (<NUM>, <NUM> mmol) and <NUM>-(adamantan-<NUM>-yl)ethanol using general method B1 and general method A in overall <NUM>% yield (<NUM>, <NUM> mmol) in the form of white foam.

<NUM>H NMR (<NUM>, CDCl<NUM>): <NUM>H NMR (<NUM>, CDCl<NUM>) δ <NUM> - <NUM> (m, <NUM>); <NUM>,<NUM> (m, <NUM>); <NUM> - <NUM> (m, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> - <NUM> (m, <NUM>); <NUM> - <NUM> (m, <NUM>).

<NUM>P{<NUM>H} NMR (<NUM>, CDCl<NUM>): δ <NUM>.

IR νmax(CHCl<NUM>) <NUM> (vw), <NUM> (m, sh), <NUM> (s), <NUM> (vs), <NUM> (s), <NUM>-<NUM> (vw), <NUM> (w, vbr), <NUM> (w), <NUM> (m), <NUM> (m), <NUM> (vw), <NUM> (m), <NUM> (m), <NUM> (s), <NUM> (m), <NUM> (s), <NUM> (s), <NUM> (s, sh), <NUM> (s), <NUM> (s), <NUM> (s), <NUM> (m), <NUM> (w).

HR-MS (ESI-): For C<NUM>H<NUM>O<NUM>P (M - H)- m/z calcd <NUM>, found <NUM>.

(Adamantan-<NUM>-yl)methyl vinylphosphonate is prepared from mono methy vinylphosphonate (<NUM>, <NUM> mmol) and (adamantan-<NUM>-yl)methanol using general method B1 and general method A in overall <NUM>% yield (<NUM>, <NUM> mmol) bezbarvého oleje.

<NUM>H NMR (<NUM>, Chloroform-d) δ <NUM> (s, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (s, <NUM>), <NUM>,<NUM> (d, J = <NUM> Hz, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (s, <NUM>).

<NUM>C NMR (<NUM>, Chloroform-d) δ <NUM>, <NUM> (d, J = <NUM>,<NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, J = <NUM>), <NUM> (d, J = <NUM>).

IR νmax (CHCl<NUM>) <NUM> (vw), <NUM> (vs, sh), <NUM> (vs), <NUM> (vs), <NUM>, <NUM>, <NUM> (m, vbr), <NUM>, <NUM> (m, vbr), <NUM> (m, vbr), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (w), <NUM> (w), <NUM> (m), <NUM> (s), <NUM> (s), <NUM> (m), <NUM> (s), <NUM> (vs, br), <NUM> (vs), <NUM> (vs), <NUM> (vs), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (w).

<NUM>-(Cyclohexyl)propyl vinylphosphonate is prepared from mono methyl vinylphosphonate (<NUM>, <NUM> mmol) and <NUM>-(cyclohexyl)propanol (<NUM>, <NUM> mmol) general method B2 and general method A in <NUM>% (<NUM>-<NUM>, <NUM>-<NUM> mmol) overall yield in the form of colorless oil.

<NUM>H NMR (<NUM>, Chloroform-d) δ <NUM>-<NUM> - <NUM>-<NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (s, <NUM>).

<NUM>C NMR (<NUM>, Chloroform-d) δ <NUM>, <NUM>, <NUM> (d, J = <NUM>,<NUM>), <NUM>, <NUM>, <NUM>, <NUM>,<NUM> (d, J = <NUM>,<NUM>), <NUM>, <NUM>, <NUM>, <NUM> (d, J = <NUM>), <NUM> (d, J = <NUM>).

IR νmax (CHCl<NUM>) <NUM> (vw), <NUM> (vs), <NUM> (s), <NUM> (w, vbr), <NUM> (m, vbr), <NUM> (m, vbr), <NUM> (m), <NUM> (w), <NUM> (w), <NUM> (m), <NUM> (m), <NUM> (w), <NUM> (s), <NUM> (s), <NUM> (s), <NUM> (s), <NUM> (vs), <NUM> (vs).

HR- TOF MS CI+ For C<NUM>H<NUM>O<NUM>P (M+H)+ calcd <NUM>, found <NUM>.

(Z)-non-<NUM>-en-<NUM>-yl vinylphosphonate is prepared from mono methyl vinylphosphonate (<NUM>, <NUM> mmol) and (Z)-non-<NUM>-en-<NUM>-ol using general method B1 and general method A in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>H NMR (<NUM>, Methanol-d<NUM>) δ <NUM> - <NUM> (m, <NUM>), <NUM> - <NUM> (m, <NUM>), <NUM> (qd, J = <NUM>, <NUM>, <NUM>), <NUM> (qd, J = <NUM>, <NUM>, <NUM>), <NUM> (q, J = <NUM> Hz, <NUM>), <NUM> (ddd, J = <NUM>, <NUM>, <NUM>, <NUM>), <NUM> (dtt, J = <NUM>, <NUM>, <NUM>, <NUM>), <NUM> - <NUM> (m, <NUM>).

<NUM>C NMR (<NUM>, Methanol-d<NUM>) δ <NUM>, <NUM>, <NUM> (d, J = <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM> (d, J = <NUM>), <NUM>, <NUM> (d, J = <NUM>).

<NUM>P NMR (<NUM>, Methanol-d<NUM>) δ <NUM>.

IR νmax (KBr) <NUM> (vw), <NUM> (s), <NUM> (s), <NUM> (m), <NUM> (s), <NUM> (w), <NUM> (w, vbr), <NUM> (m, br), <NUM> (m, vbr), <NUM> (w), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (w), <NUM> (m), <NUM> (s), <NUM> (s, sh), <NUM> (s), <NUM> (vs), <NUM> (vs).

(Z)-hept-<NUM>-en-<NUM>-yl vinylphosphonate is prepared from mono methyl vinylphosphonate (<NUM>, <NUM> mmol) and <NUM>-hexanol using general method B2 and general method A in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>H NMR (<NUM>, CDCl<NUM>): <NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (q, <NUM>, Jvic= <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (s, <NUM>).

<NUM>C NMR (<NUM>, CDCl<NUM>): <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>).

IR νmax (KBr) <NUM> (w), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (s), <NUM>-<NUM> (w, vbr), <NUM> (w), <NUM> (w), <NUM> (w), <NUM> (w), <NUM> (w), <NUM> (m), <NUM> (vw), <NUM> (w), <NUM> (m), <NUM> (m, sh), <NUM> (m), <NUM> (vs), <NUM> (vs), <NUM> (vs), <NUM> (w).

HR-ESI(ESI+) For C<NUM>H<NUM>O<NUM>P (M-H)- calcd <NUM>, found <NUM>.

(Z)-oct-<NUM>-en-<NUM>-yl vinylphosphonate is prepared from mono methyl vinylphosphonate (<NUM>, <NUM> mmol) and (Z)-oct-<NUM>-en-<NUM>-ol using general method B2 and general method A in <NUM>% (<NUM>, <NUM> mmol)
<NUM>H NMR (<NUM>, CDCl<NUM>): <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (q, <NUM>, Jvic =<NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (s, <NUM>). <NUM>C NMR (<NUM>, CDCl<NUM>): <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>).

IR νmax (KBr) <NUM> (w), <NUM> (s), <NUM> (s), <NUM> (s), <NUM> (s), <NUM> (m, br), <NUM> (m, vbr), <NUM> (m, vbr), <NUM> (m, vbr), <NUM> (m, vbr), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (s), <NUM> (m), <NUM> (m), <NUM> (s), <NUM> (s), <NUM> (s), <NUM> (vs), <NUM> (vs), <NUM> (w).

Isobutyl vinylphosphonate is prepared from mono methyl vinylphosphonate (<NUM>, <NUM> mmol) and isobutyl alcohol (<NUM>, <NUM> mmol) using general method B1 and general method A in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>H NMR (<NUM>, Chloroform-d) δ <NUM> (brs, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM> (dt, J = <NUM>, <NUM>, <NUM>), <NUM> (d, J = <NUM>, <NUM>).

<NUM>C NMR (<NUM>, Chloroform-d) δ <NUM>, <NUM> (d, J = <NUM>), <NUM> (d, J = <NUM>), <NUM> (d, J = <NUM>), <NUM> (d, J = <NUM>).

IR νmax(CHCl<NUM>) <NUM> (w), <NUM> (m), <NUM> (m), <NUM> (w), <NUM> (m, br), <NUM> (m, br), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (w), <NUM> (m), <NUM> (s), <NUM> (vs), <NUM> (s), <NUM> (m), <NUM> (m), <NUM> (m). HR-MS(ESI+): For C<NUM>H<NUM>O<NUM>NaP (M + Na)+ m/z calculated <NUM>, found <NUM> ± <NUM> ppm.

Di((Z)-oct-<NUM>-en-<NUM>-yl) propan-<NUM>,<NUM>-diyl bis(vinylphosphonate) is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol) and <NUM>,<NUM>-dibromopropane (<NUM>, <NUM> mmol) using general method C in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>H NMR (<NUM>, CDCl<NUM>): <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>).

<NUM>C NMR (<NUM>, CDCl<NUM>): <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>), <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>). <NUM>P{<NUM>H} NMR (<NUM>, CDCl<NUM>): <NUM>.

IR νmax (KBr) <NUM> (w), <NUM> (m), <NUM> (s), <NUM> (s), <NUM> (m), <NUM> (m), <NUM> (w), <NUM> (m), <NUM> (w), <NUM> (m, sh), <NUM> (vs), <NUM> (w), <NUM> (s), <NUM> (vs), <NUM> (s, sh), <NUM> (m), <NUM> (m). HR-MS(ESI+) For C<NUM>H<NUM>O<NUM>P<NUM> (M+H)+ calcd <NUM>, found <NUM>.

Di((Z)-oct-<NUM>-en-<NUM>-yl) pentane-<NUM>,<NUM>-diyl bis(vinylphosphonate) is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol) and <NUM>,<NUM>-dibromopropane (<NUM>, <NUM> mmol) using general method C in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

Hexan-<NUM>,<NUM>-diyl di((Z)-oct-<NUM>-en-<NUM>-yl) bis(vinylphosphonate) is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol) and <NUM>,<NUM>-dibromohexane (<NUM>, <NUM> mmol) using general method C in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>C NMR (<NUM>, CDCl<NUM>): <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>).

IR νmax (KBr) <NUM> (w), <NUM> (m), <NUM> (s), <NUM> (s), <NUM> (m), <NUM> (m), <NUM> (w), <NUM> (w), <NUM> (m), <NUM> (m), <NUM> (m, sh), <NUM> (s), <NUM> (s), <NUM> (s), <NUM> (s, sh), <NUM> (m), <NUM> (m), <NUM> (m). HR-MS(ESI+) For C<NUM>H<NUM>O<NUM>P<NUM> (M+H)+ calcd <NUM>, found <NUM>.

Di((Z)-hept-<NUM>-en-<NUM>-yl) hexane-<NUM>,<NUM>-diyl bis(vinylphosphonate) is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol) and <NUM>,<NUM>-dibromohexane (<NUM>, <NUM> mmol) using general method C in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>H NMR (<NUM>, CDCl<NUM>): <NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>).

<NUM>C NMR (<NUM>, CDCl<NUM>): <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>). <NUM>P{<NUM>H} NMR (<NUM>, CDCl<NUM>): <NUM>.

IR νmax (KBr) <NUM> (vw), <NUM> (m), <NUM> (s), <NUM> (m), <NUM> (m), <NUM> (w), <NUM> (w), <NUM> (m), <NUM> (m), <NUM> (m, sh), <NUM> (vs), <NUM> (vs), <NUM> (vs), <NUM> (vs), <NUM> (s, sh), <NUM> (m), <NUM> (m). HR-MS(ESI+) For C<NUM>H<NUM>O<NUM>P<NUM> (M+H)+ calcd <NUM>, found <NUM>.

Di((Z)-hept-<NUM>-en-<NUM>-yl) pentane-<NUM>,<NUM>-diyl bis(vinylphosphonate) is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol) and <NUM>,<NUM>-dibromopentane (<NUM>, <NUM> mmol) using general method C in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>H NMR (<NUM>, CDCl<NUM>): <NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>).

<NUM>C NMR (<NUM>, CDCl<NUM>): <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>, <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>).

IR νmax (KBr) <NUM> (vw), <NUM> (m), <NUM> (s), <NUM> (m), <NUM> (m), <NUM> (w), <NUM> (w), <NUM> (m), <NUM> (m, sh), <NUM> (w), <NUM> (m), <NUM> (s), <NUM> (vs), <NUM> (vs), <NUM> (vs), <NUM> (s, sh), <NUM> (m). HR-MS(ESI+) For C<NUM>H<NUM>O<NUM>NaP<NUM> (M+Na)+ calcd <NUM>, found <NUM>.

Hexane-<NUM>,<NUM>-diyl dihexyl bis(vinylphosphonate) is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol) and <NUM>,<NUM>-dibromohexane (<NUM>, <NUM> mmol) using general method C in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>H NMR (<NUM>, CDCl<NUM>): <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>).

<NUM>CNMR (<NUM>, CDCl<NUM>): <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>, <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>, <NUM>), <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>).

IR νmax (KBr) <NUM> (vw), <NUM> (s), <NUM> (s), <NUM> (m), <NUM> (m), <NUM> (w), <NUM> (m), <NUM> (m, sh), <NUM> (m, sh), <NUM> (m), <NUM> (w), <NUM> (m), <NUM> (s), <NUM> (s), <NUM> (s), <NUM> (vs, sh), <NUM> (vs), <NUM> (m).

HR-MS(ESI+) For C<NUM>H<NUM>O<NUM>P<NUM> (M+H)+ calcd <NUM>, found <NUM>.

Dihexyl octane-<NUM>,<NUM>-diyl bis(vinylphosphonate) is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol) and <NUM>,<NUM>-dibromooctane (<NUM>, <NUM> mmol) using general method C in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>C NMR (<NUM>, CDCl<NUM>): <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>).

IR νmax (KBr) <NUM> (vw), <NUM> (s), <NUM> (s), <NUM> (m), <NUM> (w), <NUM> (w), <NUM> (w), <NUM> (w, sh), <NUM> (w), <NUM> (m), <NUM> (m), <NUM> (s), <NUM> (s), <NUM> (s, sh), <NUM> (vs), <NUM> (vs), <NUM> (w). HR-MS(ESI+) For C<NUM>H<NUM>O<NUM>P<NUM> (M+H)+ calcd <NUM>, found <NUM>.

Decane-<NUM>,<NUM>-diyl dihexyl bis(vinylphosphonate) is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol) and <NUM>,<NUM>-dibromodecane (<NUM>, <NUM> mmol) using general method C in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>C NMR (<NUM>, CDCl<NUM>): <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>).

IR νmax (KBr) <NUM> (vw), <NUM> (s), <NUM> (vs), <NUM> (m), <NUM> (m), <NUM> (w), <NUM> (m), <NUM> (w), <NUM> (w), <NUM> (m), <NUM> (w), <NUM> (w), <NUM> (s), <NUM> (s), <NUM> (s, sh), <NUM> (vs), <NUM> (vs), <NUM> (w). HR-MS(ESI+) For C<NUM>H<NUM>O<NUM>P<NUM> (M+H)+ calcd <NUM>, found <NUM>.

Dihexyl tetradecane-<NUM>,<NUM>-diyl bis(vinylphosphonate) is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol) and <NUM>,<NUM>-dibromotetradecane (<NUM>, <NUM> mmol) using general method C in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>H NMR (<NUM>, CDCl<NUM>): <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>).

<NUM>C NMR (<NUM>, CDCl<NUM>): <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>).

IR νmax (KBr) <NUM> (vw); <NUM> (s), <NUM> (vs), <NUM> (m), <NUM> (s), <NUM> (w), <NUM> (m), <NUM> (w), <NUM> (w), <NUM> (m), <NUM> (w), <NUM> (w), <NUM> (s), <NUM> (s), <NUM> (s), <NUM> (vs), <NUM> (vs), <NUM> (w), <NUM> (w).

Octan-<NUM>,<NUM>-diyl dipentyl bis(vinylphosphonate) is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol) and <NUM>,<NUM>-dibromooctane (<NUM>, <NUM> mmol) using general method C in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>C NMR (<NUM>, CDCl<NUM>): <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>, <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>, <NUM>), <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>).

IR νmax (KBr) <NUM> (vw), <NUM> (s), <NUM> (s), <NUM> (m), <NUM> (m), <NUM> (w), <NUM> (m), <NUM> (m), <NUM> (w), <NUM> (w), <NUM> (s), <NUM> (w), <NUM> (m, sh), <NUM> (s), <NUM> (vs), <NUM> (vs), <NUM> (w). HR-MS(ESI+) For C<NUM>H<NUM>O<NUM>NaP<NUM> (M+Na)+ calcd <NUM>, found <NUM>.

Decane-<NUM>,<NUM>-diyl dipentyl bis(vinylphosphonate) is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol) and <NUM>,<NUM>-dibromodecane (<NUM>, <NUM> mmol) using general method C in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>C NMR (<NUM>, CDCl<NUM>): <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>, <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>, <NUM>), <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>).

IR νmax (KBr) <NUM> (vw), <NUM> (s), <NUM> (vs), <NUM> (s), <NUM> (w), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (w,sh), <NUM> (m), <NUM> (vs), <NUM> (vs), <NUM> (s), <NUM> (m), <NUM> (vs).

HR-MS(ESI+) For C<NUM>H<NUM>O<NUM>NaP<NUM> (M+Na)+ calcd <NUM>, found <NUM>.

Dodecane-<NUM>,<NUM>-diyl dipentyl bis(vinylphosphonate) is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol) and <NUM>,<NUM>-dibromododecane (<NUM>, <NUM> mmol) using general method C in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>H NMR (<NUM>, CD<NUM>OD): <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>).

<NUM>C NMR (<NUM>, CD<NUM>OD): <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>).

<NUM>P{<NUM>H} NMR (<NUM>, CD<NUM>OD): <NUM>.

IR νmax (KBr) <NUM> (vw), <NUM> (w), <NUM> (s), <NUM> (vs), <NUM> (s), <NUM> (s), <NUM> (w), <NUM> (m), <NUM> (m), <NUM> (w), <NUM> (m), <NUM> (w), <NUM> (m), <NUM> (vs), <NUM> (vs), <NUM> (vs, sh), <NUM> (vs), <NUM> (m). HR-MS(ESI+) For C<NUM>H<NUM>O<NUM>NaP<NUM> (M+Na)+ calcd <NUM>, found <NUM>.

Dipentyl tetradecane-<NUM>,<NUM>-diyl bis(vinylphosphonate) is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol) and <NUM>,<NUM>-dibromotetradecane (<NUM>, <NUM> mmol) using general method C in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>C NMR (<NUM>, CD<NUM>OD): <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>, <NUM>), <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>).

IR νmax (KBr) <NUM> (vw), <NUM> (s), <NUM> (vs), <NUM> (m), <NUM> (s), <NUM> (m), <NUM> (w, sh), <NUM> (w), <NUM> (m), <NUM> (s), <NUM> (s), <NUM> (vs, sh), <NUM> (vs).

Dibutyl octane-<NUM>,<NUM>-diyl bis(vinylphosphonate) is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol) and <NUM>,<NUM>-dibromooctane (<NUM>, <NUM> mmol) using general method C in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>H NMR (<NUM>, CDCl<NUM>): <NUM> (t, <NUM>, Jvic = <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>).

<NUM>C NMR (<NUM>, CDCl<NUM>): <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>).

IR νmax (KBr) <NUM> (vw), <NUM> (s), <NUM> (s), <NUM> (m), <NUM> (m), <NUM> (w), <NUM> (m), <NUM> (m), <NUM> (w), <NUM> (m), <NUM> (w, sh), <NUM> (m), <NUM> (s), <NUM> (s), <NUM>9vs, br), <NUM> (vs), <NUM> (m), <NUM> (m). HR-MS(ESI+) For C<NUM>H<NUM>O<NUM>NaP<NUM> (M+Na)+ calcd <NUM>, found <NUM>.

<NUM>C NMR (<NUM>, CDCl<NUM>: <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>).

IR νmax (KBr) <NUM> (vw), <NUM> (vw), <NUM> (s), <NUM> (vs), <NUM> (s), <NUM> (w), <NUM> (m), <NUM> (m), <NUM> (m, sh), <NUM> (vs), <NUM> (vs), <NUM> (vs), <NUM> (vs), <NUM> (m, sh), <NUM> (m).

Dibutyl dodecane-<NUM>,<NUM>-diyl bis(vinylphosphonate) is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol) and <NUM>,<NUM>-dibromododecane (<NUM>, <NUM> mmol) using general method C in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>C NMR (<NUM>, CDCl<NUM>): <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>).

Dibutyl tetradecane-<NUM>,<NUM>-diyl bis(vinylphosphonate) is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol) and <NUM>,<NUM>-dibromododecane (<NUM>, <NUM> mmol) using general method C in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>H NMR (<NUM>, CDCl<NUM>): <NUM>. (t, <NUM>, Jvic = <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>).

IR νmax (KBr) <NUM> (w), <NUM> (m), <NUM> (m), <NUM> (s), <NUM> (m), <NUM> (m), <NUM> (w), <NUM> (w, sh), <NUM> (w), <NUM> (m), <NUM> (m, sh), <NUM> (m), <NUM> (s), <NUM> (s), <NUM> (m, sh), <NUM> (w), <NUM> (w). HR-MS(ESI+) For C<NUM>H<NUM>O<NUM>NaP<NUM> (M+Na)+ calcd <NUM>, found <NUM>.

hexane-<NUM>,<NUM>-diyl di((Z)-non-<NUM>-en-<NUM>-yl) bis(vinylphosphonate) is prepared from compound in Example <NUM> (<NUM>, <NUM>. 61mmol) and <NUM>,<NUM>-dibromhexane (<NUM>, <NUM> mmol) using general method C in <NUM>% (<NUM>,<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>H NMR (<NUM>, Chloroform-d) δ <NUM> (t, J = <NUM>, <NUM>); <NUM> - <NUM> (m, <NUM>); <NUM> - <NUM> (m, <NUM>); <NUM> - <NUM> (qd, J = <NUM>, <NUM>,<NUM>, <NUM>); <NUM> - <NUM> (m, <NUM>); <NUM> (qd, J = <NUM>, <NUM>, <NUM>); <NUM>-<NUM> (m, <NUM>); <NUM> - <NUM> (m, <NUM>).

<NUM>C NMR (<NUM>, CDCl<NUM>) δ <NUM>; <NUM>; <NUM>; <NUM>; <NUM> (d, J = <NUM>); <NUM>; <NUM> (d, J = <NUM>); <NUM>; <NUM> (d, J = <NUM>); <NUM> (d, J = <NUM>); <NUM>; <NUM>; <NUM>; <NUM>; <NUM> (d, J = <NUM>); <NUM>; <NUM> (d, J = <NUM>).

IR νmax (CHCl<NUM>) <NUM> (vw), <NUM> (s), <NUM> (s), <NUM> (m), <NUM> (m), <NUM> (vw), <NUM> (w), <NUM> (w), <NUM> (w, sh), <NUM> (vw), <NUM> (w), <NUM> (w), <NUM> (w), <NUM> (s), <NUM> (m, sh), <NUM> (s), <NUM> (vs), <NUM> (s, sh).

HR-MS(ESI+) For C<NUM>H<NUM>O<NUM>P<NUM> (M+H)+ vcalcd <NUM>, found <NUM>.

Diisobutyl tetradecane-<NUM>,<NUM>-diyl bis(vinylphosphonate) is prepared from the compound from Example <NUM> (<NUM>, <NUM> mmol) and <NUM>,<NUM>-dibromotetradecane, (<NUM>, <NUM> mmol) using general method C in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>H NMR (<NUM>, Chloroform-d) δ <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (tt, J = <NUM>, <NUM>, <NUM>), <NUM> (dp, J = <NUM>, <NUM>, <NUM>), <NUM> (dt, J = <NUM>, <NUM>, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (d, J = <NUM>, <NUM>).

<NUM>C NMR (<NUM>, Chloroform-d) δ <NUM>, <NUM> (d, J = <NUM>), <NUM> (d, J = <NUM>), <NUM> (d, J = <NUM>), <NUM> (d, J = <NUM>), <NUM>, <NUM>, <NUM>, <NUM> (d, J = <NUM>), <NUM>, <NUM>, <NUM>.

IR νmax(CHCl<NUM>) <NUM> (vw), <NUM> (s), <NUM> (vs), <NUM> (m), <NUM> (s), <NUM> (w), <NUM> (m), ~<NUM> (w, sh), <NUM> (m), <NUM> (w), <NUM> (m), <NUM> (s), ~<NUM> (s, sh), <NUM> (vs), ~<NUM> (s, sh).

HR-MS(ESI+): For C<NUM>H<NUM>O<NUM>P<NUM> (M + H)+ m/z calculated <NUM>, found <NUM> ± <NUM> ppm. For C<NUM>H<NUM>O<NUM>NaP<NUM> (M + Na)+ m/z calculated <NUM>, found <NUM> ± <NUM> ppm.

Diisobutyl dodecane-<NUM>,<NUM>-diyl bis(vinylphosphonate) is prepared from the compound from Example <NUM> (<NUM>, <NUM>) and <NUM>,<NUM>-dibromododecane, (<NUM> %, <NUM>µL, <NUM> mmol) using general method C in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>H NMR (<NUM>, Chloroform-d) δ <NUM>-<NUM> (m, <NUM>), <NUM> (q, J = <NUM>, <NUM>), <NUM> (td, J = <NUM>, <NUM>, <NUM>), <NUM> (dt, J = <NUM>, <NUM>, <NUM>), <NUM> (dt, J = <NUM>, <NUM>, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (d, J = <NUM>, <NUM>).

<NUM>C NMR (<NUM>, Chloroform-d) δ <NUM>, <NUM> (d, J = <NUM>), <NUM> (d, J = <NUM>), <NUM> (d, J = <NUM>), <NUM> (d, J = <NUM>), <NUM>, <NUM>, <NUM> (d, J= <NUM>), <NUM>, <NUM>, <NUM>.

IR νmax(CHCl<NUM>) <NUM> (vw), <NUM> (s), <NUM> (vs), <NUM> (m), <NUM> (s), <NUM> (w), <NUM> (s), <NUM> (s), <NUM> (m), <NUM> (m), <NUM> (vs), <NUM> (w), <NUM> (vs, sh), <NUM> (vs, vbr), ~<NUM> (vs, sh), ~<NUM> (s, sh), <NUM> (m). HR-MS(ESI+): For C<NUM>H<NUM>O<NUM>NaP<NUM> (M + Na)+ m/z calculated <NUM>, found <NUM> ± <NUM> ppm.

Hexan-<NUM>,<NUM>-diyl dihexyl bis((<NUM>-(bis(<NUM>-aminopropyl)amino)ethyl)phosphonate) hexahydrochloride is prepared from the compound from Example <NUM> using general methods C, D, and E, in ther form of white amorphous solide in <NUM>% (<NUM>, <NUM>. 41mmol) overall yield.

<NUM>H NMR (<NUM>, CD<NUM>OD): <NUM> - <NUM> (m, <NUM>, CH<NUM>(CH<NUM>)<NUM>CH<NUM>O); <NUM> - <NUM> (m, <NUM>, CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM> - <NUM> (m, <NUM>, CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM> - <NUM> (m, <NUM>, NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM> - <NUM> (m, <NUM>, PCH<NUM>CH<NUM>N); <NUM> (t, <NUM>, Jvic = <NUM>, NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM> - <NUM> (m, <NUM>, NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM> - <NUM> (m, <NUM>, PCH<NUM>CH<NUM>N); <NUM> - <NUM> (m, <NUM>, CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O).

<NUM>C NMR (<NUM>, CD<NUM>OD): <NUM> (CH<NUM>(CH<NUM>)<NUM>CH<NUM>O); <NUM>, <NUM> (d, JC,P = <NUM>, PCH<NUM>CH<NUM>N); <NUM> (NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM>, <NUM>, <NUM>, <NUM> (CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>, CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM> (CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM> (NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM> (PCH<NUM>CH<NUM>N); <NUM> (NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>, CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O).

IR νmax (CHCl<NUM>) <NUM> (vs), <NUM> (vs), <NUM> (s), <NUM> (s, br), <NUM> (m, br), <NUM> (m, br), <NUM> (w, br), <NUM> (m, br), <NUM> (w, br), <NUM> (m), <NUM> (w, br), <NUM> (w, sh), <NUM> (m, sh), <NUM> (m, br), <NUM> (m), <NUM> (m, sh), <NUM> (s).

HR-MS(ESI+): For C<NUM>H<NUM>O<NUM>P<NUM> (M + <NUM>)<NUM>+ z=<NUM> m/z calcd <NUM>, found <NUM>.

Hexan-<NUM>,<NUM>-diyl dioctyl bis((<NUM>-(bis(<NUM>-aminopropyl)amino)ethyl)phosphonate) hexahydrochloride is prepared fro the compound from Example <NUM> using general methods C, D, and E, in ther form of white amorphous solide in <NUM>% (<NUM>, <NUM>.

<NUM>C NMR (<NUM>, CD<NUM>OD): <NUM> (CH<NUM>(CH<NUM>)<NUM>CH<NUM>O); <NUM>, <NUM> (d, JC,P = <NUM>, PCH<NUM>CH<NUM>N); <NUM> (NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>, CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM> (CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM> (NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM> (PCH<NUM>CH<NUM>N); <NUM> (NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>, CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O).

HR-MS(ESI+): For C<NUM>H<NUM>N<NUM>O<NUM>P<NUM> (M+<NUM>)<NUM>+ z=<NUM> m/z calcd <NUM>, found <NUM>.

Octane-<NUM>,<NUM>-diyl dipentyl bis((<NUM>-(bis(<NUM>-aminopropyl)amino)ethyl)phosphonate) hexahydrochloride is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol)
using general methods D and E, in the form of a white amorphous solid in overall yield <NUM>% (<NUM>, <NUM> mmol).

<NUM>H NMR (<NUM>, CD<NUM>OD): <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (t, <NUM>, Jvic = <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>).

<NUM>C NMR (<NUM>, CD<NUM>OD): <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>).

IR νmax (KBr) <NUM> (s), <NUM> (s), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m, sh), <NUM> (m, sh), <NUM> (s), <NUM> (s).

HR-MS(ESI+): For C<NUM>H<NUM>N<NUM>O<NUM>P<NUM> (M+H)+ calcd <NUM>, found <NUM>.

Dihexyl octane-<NUM>,<NUM>-diyl bis((<NUM>-(bis(<NUM>-aminopropyl)amino)ethyl)phosphonate) hexahydrochloride is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol)
using general methods D and E, in the form of a white amorphous solid in overall yield <NUM>% (<NUM>, <NUM> mmol).

<NUM>H NMR (<NUM>, CD<NUM>OD): <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (t, <NUM>, Jvic = <NUM>,<NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>,<NUM>-<NUM>,<NUM> (m, <NUM>).

<NUM>C NMR (<NUM>, CD<NUM>OD): <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>, <NUM>).

IR νmax (KBr) <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (w), <NUM> (w), <NUM> (m), <NUM> (w), <NUM> (w), <NUM> (m), <NUM> (m).

HR-MS(ESI+): For C<NUM>H<NUM>N<NUM>O<NUM>P<NUM> (M+<NUM>)<NUM>+ calcd <NUM>, found <NUM>.

Decane-<NUM>,<NUM>-diyl diisobutyl bis(vinylphosphonate) is prepared from the compound from Example <NUM> (<NUM>, <NUM> mmol) and <NUM>,<NUM>-dibromodecane (<NUM> %, <NUM>µL, <NUM> mmol) using general method C in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of colorless oil.

<NUM>H NMR (<NUM>, Chloroform-d) δ <NUM>-<NUM> (m, <NUM>), <NUM> (q, J = <NUM>, <NUM>), <NUM> (td, J = <NUM>, <NUM>, <NUM>), <NUM> (dp, J = <NUM>, <NUM>, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (d, J = <NUM>, <NUM>).

<NUM>C NMR (<NUM>, Chloroform-d) δ <NUM> (d, J = <NUM>), <NUM> (d, J = <NUM>), <NUM> (d, J = <NUM>), <NUM> (d, J = <NUM>), <NUM> (d, J = <NUM> Hz), <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, J = <NUM>).

IR νmax(CHCl<NUM>) <NUM> (vw), <NUM> (s), <NUM> (vs), <NUM> (m), <NUM> (s), <NUM> (w), <NUM> (s), <NUM> (s), <NUM> (m), <NUM> (s), <NUM> (vs), <NUM> (w), ~<NUM> (s, sh), <NUM> (vs, br), ~<NUM> (vs, sh), ~<NUM> (s, sh), <NUM> (m). HR-MS(ESI+): For C<NUM>H<NUM>O<NUM>NaP<NUM> (M + Na)+ m/z calculated <NUM>, found <NUM> ± <NUM> ppm.

Diisobutyl decane-<NUM>,<NUM>-diyl bis((<NUM>-(bis(<NUM>-aminopropyl)amino)ethyl)phosphonate) hexahydrochloride is prepared from the compound from Example <NUM> (<NUM>, <NUM> mmol) using general methods D and E in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of white amorphous powder.

<NUM>H NMR (<NUM>, Methanol-d<NUM>) δ <NUM> (q, J = <NUM>, <NUM>), <NUM> (tt, J = <NUM>, <NUM>, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (h, J = <NUM>, <NUM>), <NUM> (dt, J = <NUM>, <NUM>, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (d, J = <NUM>, <NUM>).

<NUM>C NMR (<NUM>, Methanol-d<NUM>) δ <NUM> (d, J = <NUM>), <NUM> (d, J = <NUM>), <NUM>, <NUM>, <NUM> (d, J = <NUM>), <NUM>, <NUM> (d, J = <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>.

IR νmax(KBr tab. <NUM>) <NUM> (s), <NUM> (s), <NUM> (m), <NUM>-<NUM> (vs, vbr), <NUM>-<NUM> (m, vbr), <NUM> (m), <NUM> (m), <NUM> (s), <NUM> (m), <NUM> (m), <NUM> (vs), <NUM> (vs), ~<NUM> (m, sh), <NUM> (m), <NUM> (m), <NUM> (w).

HR-MS(ESI+): For C<NUM>H<NUM>O<NUM>N<NUM>P<NUM> (M + H)+ m/z calculated <NUM>, found <NUM> ± <NUM> ppm.

Dibutyl decane-<NUM>,<NUM>-diyl bis((<NUM>-(bis(<NUM>-aminopropyl)amino)ethyl)phosphonate) hexahydrochloride is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol)
using general methods D and E, in the form of a white amorphous solid in <NUM>% overall yield (<NUM>, <NUM> mmol).

<NUM>C NMR (<NUM>, CD<NUM>OD): <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>).

IR νmax (KBr) <NUM> (vs), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m sh), <NUM> (m, sh), <NUM> (m), <NUM> (vs), <NUM> (m, sh).

Decane-<NUM>,<NUM>-diyl dipentyl bis((<NUM>-(bis(<NUM>-aminopropyl)amino)ethyl)phosphonate) hexahydrochloride is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol)
using general methods D and E, in the form of a white amorphous solid in <NUM>% overall yield (<NUM>, <NUM> mmol).

<NUM>H NMR (<NUM>, CD<NUM>OD): <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>,<NUM>-<NUM>,<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (t, <NUM>, Jvic = <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>).

<NUM>C NMR (<NUM>, CD<NUM>OD): <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>,<NUM>), <NUM>,<NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>, <NUM>).

IR νmax (KBr) <NUM> (s), <NUM> (m, sh), <NUM>-<NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (s), <NUM>-<NUM> (s).

Decane-<NUM>,<NUM>-diyl dihexyl bis((<NUM>-(bis(<NUM>-aminopropyl)amino)ethyl)phosphonate) tetrahydrochloride is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol)
using general methods D and E, in the form of a white amorphous solid in <NUM>% overall yield (<NUM>, <NUM> mmol).

<NUM>C NMR (<NUM>, CD<NUM>OD): <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>, <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>).

IR νmax (KBr) <NUM> (m), <NUM> (w), <NUM> (w), <NUM> (w), <NUM> (w), <NUM> (w, sh), <NUM> (w), <NUM> (w), <NUM> (m), <NUM> (m).

Decan-<NUM>,<NUM>-diyl dioktyl bis((<NUM>-(bis(<NUM>-aminopropyl)amino)ethyl)- phosphonate) tetrahydrochloride se is prepared from the compound from Example <NUM> using general methods C, D, and E, in the form of a white amorphous solid in overall yield <NUM> % (<NUM>, <NUM> mmol).

<NUM>C NMR (<NUM>, CD<NUM>OD): <NUM> (CH<NUM>(CH<NUM>)<NUM>CH<NUM>O); <NUM> (d, JC,P = <NUM>, PCH<NUM>CH<NUM>N); <NUM> (NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM>, <NUM> (d, JC,P = <NUM>, CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM> (CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM> (NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM> (PCH<NUM>CH<NUM>N); <NUM> (NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM> (d, JC,P = <NUM>, CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O).

HR-MS(ESI+) For C<NUM>H<NUM>N<NUM>O<NUM>P<NUM> (M+<NUM>)<NUM> calcd <NUM>, found <NUM>.

Decan-<NUM>,<NUM>-diyl didecyl bis((<NUM>-(bis(<NUM>-aminopropyl)amino)ethyl)- phosphonate) tetrahydrochloride is prepared from the compound from Example <NUM> using general methods C, D, and +E, in the form of a white amorphous solid in overall yield <NUM> % (<NUM>, <NUM>.

<NUM>C NMR (<NUM>, CD<NUM>OD): <NUM> (CH<NUM>(CH<NUM>)<NUM>CH<NUM>O); <NUM> (d, JC,P = <NUM>, PCH<NUM>CH<NUM>N); <NUM> (NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM>, <NUM> (d, JC,P = <NUM>, CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM> (CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM> (NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM> (PCH<NUM>CH<NUM>N); <NUM> (NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM> (d, JC,P = <NUM>, CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O).

IR νmax (KBr) <NUM> (vs), <NUM> (vs), <NUM> (vs), <NUM> (m, br), <NUM> (m, br), <NUM> (s, br), <NUM> (w, br), <NUM> (m, sh), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m, sh), <NUM> (w), <NUM> (w), <NUM> (w, sh), <NUM> (vw), <NUM> (w), <NUM> (s), <NUM> (m), <NUM> (s, sh), <NUM> (s), <NUM> (w).

HR-MS(ESI+) For C<NUM>H<NUM>N<NUM>O<NUM>P<NUM> (M+<NUM>)<NUM>+ calcd <NUM>, found <NUM>.

Dodecane-<NUM>,<NUM>-diyl diisobutyl bis((<NUM>-(bis(<NUM>-aminopropyl)amino)ethyl)phosphonate) hexahydrochloride is prepared from the compound from Example <NUM> (<NUM>, <NUM> mmol) using general methods D and E in <NUM>% (<NUM>, <NUM>,<NUM>µmol) overall yield in the form of white amorphous powder.

<NUM>H NMR (<NUM>, Methanol-d<NUM>) δ <NUM> (dt, J = <NUM>, <NUM>, <NUM>), <NUM> (td, J = <NUM>, <NUM>, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (dp, J = <NUM>, <NUM>, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (d, J = <NUM>, <NUM>).

<NUM>C NMR (<NUM>, Methanol-d<NUM>) δ <NUM> (d, J = <NUM>), <NUM> (d, J = <NUM>), <NUM>, <NUM>, <NUM> (d, J = <NUM>), <NUM>, <NUM>, <NUM> (d, J = <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>.

IR νmax(KBr tab. <NUM>) <NUM>-<NUM> (vs, vbr), <NUM> (s), <NUM> (s), <NUM> (m), <NUM>-<NUM> (m), <NUM> (m), <NUM> (w), <NUM> (m), <NUM> (w), <NUM> (w), <NUM> (m), <NUM> (s), ~<NUM> (w, sh), <NUM> (m), <NUM> (w), <NUM> (vw). HR-MS(ESI+): For C<NUM>H<NUM>O<NUM>N<NUM>P<NUM> (M + H)+ m/z calculated <NUM>, found <NUM> ± <NUM> ppm.

Dibutyl dodecane-<NUM>,<NUM>-diyl bis((<NUM>-(bis(<NUM>-aminopropyl)amino)ethyl)phosphonate) hexahydrochloride is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol)
using general methods D and E, in the form of a white amorphous solid in overall yield <NUM> % (<NUM>, <NUM> mmol).

<NUM>C NMR (<NUM>, CD<NUM>OD): <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>, <NUM>).

IR νmax (KBr) <NUM> (s), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m, sh), <NUM> (m, sh), <NUM> (m), <NUM> (s), <NUM> (s),.

HR-MS(ESI+) For C<NUM>H<NUM>N<NUM>O<NUM>P<NUM> (M+H)+ calcd <NUM>, found <NUM>.

Dodecane-<NUM>,<NUM>-diyl dipentyl bis((<NUM>-(bis(<NUM>-aminopropyl)amino)ethyl)phosphonate) hexahydrochloride is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol)
using general methods D and E, in the form of a white amorphous solid in overall yield <NUM> % (<NUM>, <NUM> mmol).

<NUM>C NMR (<NUM>, CD<NUM>OD): <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>, <NUM>) <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>, <NUM>).

IR νmax (KBr) <NUM> (vs), <NUM> (m, sh), <NUM> (m, sh), <NUM> (m), <NUM> (m), <NUM> (s), <NUM> (m, sh), <NUM> (m, sh), <NUM> (s, sh), <NUM> (s).

Dodecan-<NUM>,<NUM>-diyl dioctyl bis((<NUM>-(bis(<NUM>-aminopropyl)amino)ethyl)phosphonate) tetrahydrochloride is prepared from compound in Example <NUM> using general methods C, D, and E, in the form of a white amorphous solid in overall yield <NUM> % (<NUM>, <NUM> mmol).

<NUM>C NMR (<NUM>,<NUM>, CD<NUM>OD): <NUM> (CH<NUM>(CH<NUM>)<NUM>CH<NUM>O); <NUM> (d, JC,P = <NUM>, PCH<NUM>CH<NUM>N); <NUM> (NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM>, <NUM> (d, JC,P = <NUM>, CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM> (CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM> (NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM> (PCH<NUM>CH<NUM>N); <NUM> (NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM> (d, JC,P = <NUM>, CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O).

HR-MS(ESI+) For C<NUM>H<NUM>N<NUM>O<NUM>P<NUM> (M+<NUM>)<NUM>+ z=<NUM> calcd <NUM>, found <NUM>.

Bis(<NUM>-benzylethyl)-dodecane-<NUM>,<NUM>-diyl bis((<NUM>-(bis(<NUM>-aminopropyl)amino)ethyl) phosphonate) hexahydrochloride is prepared from the compound from Example <NUM> (<NUM>, <NUM> mmol) and bis(<NUM>-tert-butyloxycarbonylaminopropyl)amine (<NUM>, <NUM> mmol) using general methods C, D and E in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of white amorphous powder.

<NUM>H NMR (<NUM>, CD<NUM>OD): <NUM>-<NUM> (m, <NUM>, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM>-<NUM> (m, <NUM>, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM>-<NUM> (m, <NUM>, NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM>-<NUM> (m, <NUM>, PCH<NUM>CH<NUM>N); <NUM> (t, <NUM>, Jvic = <NUM>, OCH<NUM>CH<NUM>Ph); <NUM> (t, <NUM>, Jvic = <NUM>, NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM>-<NUM> (m, <NUM>, NCH<NUM>CH<NUM>CH<NUM>NH<NUM>, PCH<NUM>CH<NUM>N); <NUM>-<NUM> (m, <NUM>, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM>-<NUM> (m, <NUM>, OCH<NUM>CH<NUM>Ph).

<NUM>C NMR (<NUM>, CD<NUM>OD): <NUM> (d, JC,P = <NUM>, PCH<NUM>CH<NUM>N); <NUM> (NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM>, <NUM>, <NUM>, <NUM> (OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM> (d, JC,P = <NUM>, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM> (d, JC,P = <NUM>, OCH<NUM>CH<NUM>Ph); <NUM> (NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM> (PCH<NUM>CH<NUM>N); <NUM> (NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM> (d, JC,P = <NUM>, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM> (d, JC,P = <NUM>, OCH<NUM>CH<NUM>Ph).

IR vmax (KBr) <NUM> (s, sh), <NUM> (s), <NUM> (vs), <NUM> (s), <NUM> (m, sh), <NUM> (m, vbr), <NUM> (m, vbr), <NUM> (w, vbr), <NUM> (m), <NUM> (m, sh), <NUM> (w, sh), <NUM> (m), <NUM>, <NUM> (m), <NUM> (w, br), <NUM> (m, sh), <NUM> (m), <NUM> (w), <NUM> (m), <NUM> (s), <NUM> (s), <NUM> (vw), <NUM> (w), <NUM> (m).

HR-MS(ESI+): For C<NUM>H<NUM>O<NUM>N<NUM>P<NUM> (M + H)+ m/2z calculated <NUM>, found <NUM> ± <NUM> ppm.

Tetradecane-<NUM>,<NUM>-diyl diisobutyl bis((<NUM>-(bis(<NUM>-aminopropyl)amino)ethyl)phosphonate) hexahydrochloride is prepared from the compound from Example <NUM> (<NUM>, <NUM> mmol) using general methods D and E in <NUM>% (<NUM>, <NUM> mmol) overall yield in the form of white amorphous powder.

<NUM>H NMR (<NUM>, Methanol-d<NUM>) δ <NUM> (dt, J = <NUM>, <NUM>, <NUM>), <NUM> (td, J = <NUM>, <NUM>, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (t, J = <NUM>, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (h, J = <NUM>, <NUM>, <NUM>), <NUM> (dp, J = <NUM>, <NUM>, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (d, J = <NUM>, <NUM>). <NUM>P NMR (<NUM>, Methanol-d<NUM>) δ <NUM>.

<NUM>C NMR (<NUM>, Methanol-d<NUM>) δ <NUM> (d, J = <NUM>), <NUM> (d, J = <NUM>), <NUM>, <NUM>, <NUM> (d, J = <NUM>), <NUM>, <NUM>, <NUM>, <NUM> (d, J = <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>. IR vmax(KBr tab. <NUM>) <NUM>-<NUM> (vs, vbr), <NUM> (s), <NUM> (vs), <NUM> (s), <NUM>-<NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (w), <NUM> (s), <NUM> (vs), <NUM> (m), <NUM> (w), ~<NUM> (w, sh). HR-MS(ESI+): For C<NUM>H<NUM>O<NUM>N<NUM>P<NUM> (M + H)+ m/z calculated <NUM>, found <NUM> ± <NUM> ppm.

Dibutyl tetradecane-<NUM>,<NUM>-diyl bis((<NUM>-(bis(<NUM>-aminopropyl)amino)ethyl)phosphonate) hexahydrochloride is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol)
using general methods D and E, in the form of a white amorphous solid in overall yield <NUM> % (<NUM>, <NUM> mmol).

<NUM>C NMR (<NUM>, CD<NUM>OD): <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>).

IR vmax (KBr) <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m).

HR-MS(ESI+): For C<NUM>H<NUM>N<NUM>O<NUM>P<NUM> (M+H)+calcd <NUM>, found <NUM>.

Tetradecane-<NUM>,<NUM>-diyl dipentyl bis((<NUM>-(bis(<NUM>-aminopropyl)amino)ethyl)phosphonate) hexahydrochloride is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol)
using general methods D and E, in the form of a white amorphous solid in overall yield <NUM> % (<NUM>, <NUM> mmol).

<NUM>C NMR (<NUM>, CD<NUM>OD): <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>, <NUM>), <NUM>, <NUM>, <NUM> (NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM>, <NUM> (d, JC,P = <NUM>, <NUM>, CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O).

<NUM>P{<NUM>H} NMR (<NUM>, CD<NUM>OD): <NUM>.

IR vmax (KBr) <NUM> (s), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m, sh), <NUM> (m), <NUM> (vs).

Dihexyl tetradecan-<NUM>,<NUM>-diyl bis((<NUM>-(bis(<NUM>-aminopropyl)amino)ethyl)phosphonate) tetrahydrochloride is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol) and bis (<NUM>-tert-butyloxykarbonylaminopropyl)amine (<NUM>, <NUM> mmol) using general methods D and E, in the form of a white amorphous solid in overall yield <NUM> % (<NUM>, <NUM> mmol).

<NUM>H NMR (<NUM>, CD<NUM>OD): <NUM>-<NUM> (m, <NUM>, CH<NUM>(CH<NUM>)<NUM>CH<NUM>O); <NUM>-<NUM> (m, <NUM>, CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM>-<NUM> (m, <NUM>, CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM>-<NUM> (m, <NUM>, NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM>-<NUM> (m, <NUM>, PCH<NUM>CH<NUM>N); <NUM> (t, <NUM>, Jvic = <NUM>, NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM>-<NUM> (m, <NUM>, NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM>-<NUM> (m, <NUM>, PCH<NUM>CH<NUM>N); <NUM>-<NUM> (m, <NUM>, CH<NUM>(CH<NUM>)<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O).

<NUM>C NMR (<NUM>, CD<NUM>OD): <NUM> (CH<NUM>(CH<NUM>)<NUM>CH<NUM>O); <NUM> (d, JC,P = <NUM>, PCH<NUM>CH<NUM>N); <NUM> (NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (CH<NUM>CH<NUM> CH<NUM>CH<NUM>CH<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM> (d, JC,P = <NUM>, CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O); <NUM> (CH<NUM>CH<NUM>CH<NUM>CH<NUM>CH<NUM>CH<NUM>O); <NUM> (NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM> (PCH<NUM>CH<NUM>N); <NUM> (NCH<NUM>CH<NUM>CH<NUM>NH<NUM>); <NUM>, <NUM> (d, JC,P = <NUM>, CH<NUM>(CH<NUM>)<NUM>CH<NUM>O, OCH<NUM>CH<NUM>(CH<NUM>)<NUM>CH<NUM>CH<NUM>O).

IR vmax (KBr) <NUM> (s), <NUM> (s), <NUM> (s), <NUM> (m), <NUM> (m, sh), <NUM> (m ,sh). <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (s), <NUM> (m), <NUM> (s).

HR-MS(ESI+): For C<NUM>H<NUM>N<NUM>O<NUM>P<NUM> (M+<NUM>)<NUM> calcd <NUM>, found <NUM>.

Dihexyl octane-<NUM>,<NUM>-diyl bis((<NUM>-(bis(<NUM>-aminoethyl)amino)ethyl)phosphonate) hexahydrochloride is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol)
using general methods D and E, in the form of a white amorphous solid in <NUM>% overall yield (<NUM>, <NUM> mmol).

<NUM>H NMR (<NUM>, CD<NUM>OD): <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>).

IR vmax (KBr) <NUM> (m), <NUM> (s), <NUM> (m), <NUM> (m), <NUM> (s), <NUM> (m, sh), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (s), <NUM> (m, sh), <NUM> (s).

HR-MS(ESI+): For C<NUM>H<NUM>N<NUM>O<NUM>P<NUM> (M+H)+calcd <NUM>, nalezeno <NUM>.

Dibutyl decane-<NUM>,<NUM>-diyl bis((<NUM>-(bis(<NUM>-aminoethyl)amino)ethyl)phosphonate) hexahydrochloride is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol)
using general methods D and E, in the form of a white amorphous solid in <NUM>% overall yield (<NUM>, <NUM> mmol).

<NUM>C NMR (<NUM>, CD<NUM>OD): <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM><NUM>, <NUM>, <NUM> (d, JC,P = <NUM>).

IR vmax (KBr) <NUM> (m), <NUM> (m), <NUM> (m, sh), <NUM> (m, br), <NUM>, (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m, sh), <NUM> (m, sh).

Hexane-<NUM>,<NUM>-diyl di((Z)-oct-<NUM>-en-<NUM>-yl) bis((<NUM>-(bis(<NUM>-aminopropyl)amino)ethyl)phosphonate) hexahydrochloride is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol)
using general methods D and E, in the form of a white amorphous solid in <NUM>% overall yield (<NUM>, <NUM> mmol).

<NUM>H NMR (<NUM>, CD<NUM>OD): <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (t, <NUM>, Jvic = <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>).

<NUM>C NMR (<NUM>, CD<NUM>OD): <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM> (dd, JC,P = <NUM>, <NUM>), <NUM>, <NUM>.

<NUM>P{<NUM>H} NMR (<NUM>,<NUM>, CD<NUM>OD): <NUM>.

IR vmax (KBr) <NUM> (m, br), <NUM> (s), <NUM> (vs), <NUM> (vs), <NUM> (s), <NUM>-<NUM> (vs, vbr), <NUM> (m), <NUM> (m), <NUM> (w, sh), <NUM> (m), <NUM> (s), <NUM> (s).

HR-MS(ESI+): For C<NUM>H<NUM>O<NUM>N<NUM>P<NUM> (M+<NUM>)<NUM>+ calcd <NUM>, found <NUM>.

Di((Z)-oct-<NUM>-en-<NUM>-yl) pentane-<NUM>,<NUM>-diyl bis((<NUM>-(bis(<NUM>-aminopropyl)amino)ethyl)phosphonate) hexahydrochloride is prepared from compound in Example <NUM> (<NUM>, <NUM> mmol)
using general methods D and E, in the form of a white amorphous solid in <NUM>% overall yield (<NUM>, <NUM> mmol).

<NUM>H NMR (<NUM>, CD<NUM>OD): <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (<NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM> (t, <NUM>, Jvic = <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>), <NUM>-<NUM> (m, <NUM>).

<NUM>C NMR (<NUM>, CD<NUM>OD): <NUM>, <NUM> (d, JC,P = <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM> (d, JC,P = <NUM>), <NUM>, <NUM>, <NUM>, <NUM>, <NUM> (d, JC,P = <NUM>), <NUM> (dd, JC,P = <NUM>), <NUM>, <NUM>.

IR vmax (KBr) <NUM> (s, br), <NUM> (m, sh), <NUM> (m), <NUM> (m), <NUM> (m), <NUM> (m), <NUM>-<NUM> (m, br), <NUM> (w), <NUM> (w), <NUM> (w), <NUM> (w, sh), <NUM> (w), <NUM> (m).

HR-MS(ESI+):For C<NUM>H<NUM>O<NUM>N<NUM>P<NUM> (M+<NUM>)<NUM>+ calcd <NUM>, found <NUM>.

Antibacterial activity is measured using a standard microdilution method determining the minimum inhibitory concentration (MIC) of a test sample that results in the inhibition of bacterial growth. Disposable microtiter plates are used for testing. Samples are dissolved in infusion medium from brain and heart (BHI, HiMedia Laboraties Pvt. , Czech Republic) and Mueller-Hinton broth (HiMedia Laboraties, see above) to a final concentration ranging from <NUM>µg/ml to <NUM>µg/ml. Plates are inoculated with a standard amount of test bacteria - the density of the inoculum in the well corresponds to <NUM><NUM>-<NUM> CFU/ml (colony forming units / ml, i.e. the number of viable bacterial cells / ml). MIC values are read after <NUM>/<NUM> hours of incubation at <NUM> as the minimum inhibitory concentration of the test substance at which bacterial growth is inhibited. The minimum bactericidal concentration (MBC) is characterized as the minimum concentration of the sample required to achieve irreversible inhibition, i.e. to kill the bacteria after a defined incubation period. MBC is determined by the inoculation method. Using an applicator, <NUM>µl from the well of a microtiter plate with a defined concentration of the test substance is taken to inoculate the surface of blood agar (Trios, Czech Republic). MBC is determined as the lowest concentration that inhibits the visible growth of the bacterium used on agar.

Blood from three donors is mixed and centrifuged (<NUM>, <NUM>, <NUM>). The erythrocytes obtained are washed three times with NaCl solution (<NUM> mmol. l-<NUM>) and then used for experiments. Sample stock solutions are prepared in DMSO so that the final concentration of DMSO in NaCl is <NUM> % (v/v). NaCl solution with the appropriate volume of DMSO serves as the negative control. <NUM>% Triton-X100 is the positive control. The erythrocytes obtained are diluted to <NUM>% with NaCl solution and pipetted into Eppendorf tubes (<NUM>µl) with constant stirring. Samples and positive and negative controls are added to the erythrocytes prepared in this way and incubated (<NUM> hours, <NUM>). The tubes are stirred during the incubation. After centrifugation (<NUM>, <NUM>), haemolytic activity is monitored by haemoglobin determination. The HC<NUM> value is calculated from the measured absorbance values. The test is performed in triplets in three independent replicates. Iron Fe<NUM>+ in haemoglobin is oxidized with potassium ferricyanide to iron Fe<NUM>+ in methaemoglobin, which produces stable cyanomethaemoglobin with potassium cyanide, the concentration of which is determined spectrophotometrically. After the incubation of the erythrocytes with the substances, the cells are centrifuged (<NUM>, <NUM>), then Drabkin's solution (<NUM>µl) is added to the supernatant (<NUM>µl) and after incubation (<NUM>), the absorbance at <NUM> is measured.

The toxicity testing of soluble samples was performed on a Balb/c 3T3 mouse fibroblast cell line. The cryopreserved cells are taken out from the deep-freezer, left for <NUM> at room temperature and then sterile transferred to a <NUM><NUM> flask with <NUM> of culture medium (DMEM, penicillin <NUM> U. ml-<NUM>, L-glutamine <NUM> mmol. l-<NUM>, streptomycin <NUM>. l-<NUM>, fetal calf serum <NUM>%, neonatal calf serum <NUM>%). The cells are stored in an incubator saturated with water vapour at <NUM> and in an atmosphere of <NUM>% CO<NUM>, the medium is changed every <NUM> - <NUM>. After reaching the monolayer, the cells are washed with sterile PBS (<NUM>), released by incubation with <NUM>% trypsin solution with EDTA (<NUM>; <NUM>-<NUM>, <NUM>), <NUM> of culture medium is added, and the samples are centrifuged (<NUM>, <NUM> rpm, room temperature). The pellet is resuspended in <NUM> of culture medium and the cells are transferred to a <NUM><NUM> culture flask and further cultured. After reaching the monolayer, the cells are washed with sterile PBS (<NUM>), released by incubation with <NUM>% trypsin solution with EDTA (<NUM>; <NUM>-<NUM>; <NUM>), and resuspended in <NUM> of culture medium. The suspension is centrifuged (<NUM>; <NUM> rpm; room temperature). The pellet is resuspended in <NUM> of culture medium and the cells are used in experiments.

Stock solutions are prepared in DMSO so that the final concentration of DMSO in the medium is <NUM> % (v/v). Control cells are prepared by incubation with an appropriate volume of DMSO.

Cell concentrations are determined by trypan blue staining. The cells are diluted in culture medium and plated in <NUM>-well plates at a concentration of <NUM>×<NUM><NUM> cells/ml at <NUM> per well. After incubating the culture for <NUM> hours (Jouan incubator - controlled atmosphere <NUM> % air, <NUM> % CO<NUM>, steam saturation, <NUM>), the culture medium is changed to serum-free medium containing the test substances and incubated for <NUM> hours in the incubator under the above conditions. After <NUM> of incubation (<NUM>, <NUM> % CO<NUM>), cell damage is monitored by determining mitochondrial dehydrogenase activity (MTT assay). The IC<NUM> value is calculated from the measured absorbance values. The test is performed in three independent replicates.

The yellow tetrazolium salt of MTT is reduced by mitochondrial dehydrogenases of metabolically active cells to a purple, water-insoluble formazan dye, the concentration of which, after dissolution in an organic solvent, is determined spectrophotometrically at <NUM> (Sieuwerts, <NUM>).

Claim 1:
Lipopolyphosphonoxin of the general formula I
<CHM>
wherein:
the X substituent is independently selected from the following structures:
<CHM>
<CHM>
wherein m = <NUM>-<NUM>;
the Y substituent is independently selected from the following structures:
<CHM>
wherein n = <NUM>-<NUM>, , and o = <NUM>-<NUM>, and p = <NUM>-<NUM>, and
R<NUM>, R<NUM>, R<NUM>, R<NUM>, and R<NUM> are independently selected from the group consisting of: H-, CH<NUM>-, CH<NUM>CH<NUM>, propyl, isopropyl, isobutyl, tert-butyl, CH<NUM>O-, CH<NUM>CH<NUM>O-, propoxy, isopropoxy, isobutyloxy or tert-butyloxy;
and
the Z substituent is selected from the following structures:
<CHM>
wherein q = <NUM>-<NUM>, and r = <NUM>-<NUM>, and s = <NUM>-<NUM>,
or a diastereomer or a mixture of diastereomers of the compound of formula I, or a pharmaceutically acceptable salt or hydrate thereof.