CA2399947A1 - Phosphororganic compounds and the use thereof - Google Patents

Phosphororganic compounds and the use thereof Download PDF

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CA2399947A1
CA2399947A1 CA002399947A CA2399947A CA2399947A1 CA 2399947 A1 CA2399947 A1 CA 2399947A1 CA 002399947 A CA002399947 A CA 002399947A CA 2399947 A CA2399947 A CA 2399947A CA 2399947 A1 CA2399947 A1 CA 2399947A1
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hydroxy
acid amide
viruses
oxo
butyric acid
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Hassan Jomaa
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Jomaa Pharmaka GmbH
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing aromatic radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
    • A01N57/24—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing heterocyclic radicals
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P13/00—Herbicides; Algicides
    • A01P13/02—Herbicides; Algicides selective
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/66—Phosphorus compounds
    • A61K31/662—Phosphorus acids or esters thereof having P—C bonds, e.g. foscarnet, trichlorfon
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A61P33/06—Antimalarials
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
    • 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/302—Acyclic unsaturated acids
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
    • C07F9/306—Arylalkanephosphinic acids, e.g. Ar-(CH2)n-P(=X)(R)(XH), (X = O,S, Se; n>=1)
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    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/3808—Acyclic saturated acids which can have 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
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C07F9/5304—Acyclic saturated phosphine oxides or thioxides
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    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
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    • C07F9/5333—Arylalkane phosphine oxides or thioxides
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572—Five-membered rings
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572—Five-membered rings
    • C07F9/5728—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
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    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
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    • C07F9/58—Pyridine rings
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
    • C07F9/6503—Five-membered rings
    • C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
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    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
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Abstract

The invention concerns the use of phosphororganic compounds of general formu la (I), wherein A represents propylene, 2-oxopropylene or 3-oxopropylene. The invention also concerns the use of said compounds for therapeutic and prophylactic treatment of infections in humans and animals caused by virus, bacteria, fungi and parasites and to their use as fungicides, bactericides a nd herbicides.

Description

WO01/60829 original PCT/EP0001313 _1_ Org_anophosphorus compounds and the use thereof The invention concerns organophosphorus compounds and their salts, esters, and amides as well as their use for the therapeutic and prophylactic treatment of infections in humans and animals, caused by viruses, bacteria, fungi and parasites, and the use thereof as a fungicide, bactericide and herbicide in plants. According to the invention the organophosphorus com-pounds include phosphinoyl derivatives, phosphinic acid derivatives and phosphoric acid derivatives.
There is a serious need for the provision of preparations to enhance the treatment of humans and animals and the protection of plants, which preparations not only possess a strong effi-cacy but in contrast to other pharmaceutical compositions and plant protective agents, show reduced side effects and lower environmental impact and therefore represent a lower risk to health for humans.
The object of the present invention therefore is to provide a substance, which can be univer-sally used in infections by viruses, bacteria, fungi and parasites in humans and animals and as 2o a fungicide, bactericide and herbicide in plants and fulfils the conditions given above.
This object is achieved in a completely surprising manner by the group of substances defined in claim 1. This group of substances demonstrates- an anti-infectious effect against viruses, bacteria, fungi, unicellular and multicellular parasites as well as a fungicidal and herbicidal effect in plants.
The organophosphorus compounds according to the present invention correspond to general formula (I):
Rl' 0 10 .
N-C-A-P-R2 (I) / I

in which A represents propylene, 2-oxopropylene or 3-oxopropylene, in which RI is selected from the group consisting of hydrogen, substituted and unsubstituted alkyl, substituted and unsubstituted hydroxyalkyl, substituted and unsubstituted alkenyl, sub-stituted and unsubstituted a.lkinyl, substituted and unsubstituted aryl, substituted and unsub-stituted acyl, substituted and unsubstituted cycloalkyl, substituted and unsubstituted aralkyl, W 001/60829 amended PCT/EP0001313 [substituted and unsubstituted] heterocyclic residue, halogen and OX1, wherein Xl is selected from the group consisting of hydrogen, substituted and unsubstituted alkyl, substituted and unsubstituted hydroxyalkyl, substituted and unsubstituted alkenyl, sub-s stituted and unsubstituted alkinyl, substituted and unsubstituted aryl, substituted and unsub-stituted acyl, substituted and unsubstituted cycloalkyl, substituted and unsubstituted aralkyl, substituted and unsubstituted heterocyclic residue and in which R2 and R3 are the same or different and are selected from the group consisting of hydrogen, substituted and unsubstituted alkyl, substituted and unsubstituted hydxoxyalkyl, 1 o substituted and unsubstituted aryl, substituted and unsubstituted acyl, substituted and unsub-stituted aralkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted alkinyl, substituted and unsubstituted cycloalkyl, substituted and unsubstituted heterocyclic residue, halogen, OX2 or OX3, wherein X2 or X3 may be the same or different and are selected from the group consisting of 15 hydrogen, substituted and unsubstituted alkyl, substituted and unsubstituted hydroxyalkyl, substituted and unsubstituted aryl, substituted and unsubstituted aralkyl, substituted and un-substituted alkenyl, substituted and unsubstituted alkinyl, substituted and unsubstituted cyclo-allcyl, substituted and unsubstituted heterocyclic residue, a silyl, a cation of an organic and inorganic base, in particular a metal of the first, second, or third main group of the periodic 20 system, ammonium, substituted ammonium and ammonium compounds, which derive from ethylene diamine or amino acid, and their pharmaceutically acceptable salts, esters and amides and salts of the esters with the exception of N-hydroxy-4-phosphonobutyric acid amide and the salts thereof.
25 Preferably Rl is selected from the group consisting of a hydrogen residue, a methyl residue, an ethyl residue and a phenyl residue.
Furthermore R2 and R3 are preferred being the same or different and being selected from the group consisting of a methyl residue, an ethyl residue, OX2 and OX3, wherein X2 and X3 es-3o pecially preferably are selected from the group, consisting of sodium, a methyl residue, a ethyl residue and a phenyl residue.
Special features of the above definitions and suitable examples thereof are given below:

-2a-"Acyl" ist ein Substituent, der von einer Sauce stammt, wie von einer organischen Carbonsau-re, Kohlensaure, Carbaminsaure oiler der den einzelnen vorstehenden Sauren entsprechenden Thiosaure oiler Imidsaure, oiler von einer organischen Sulfonsaure, wobei diese Sauren je "Acyl" is a substituent which originates from an acid, such as from an organic carboxylic acid, carbonic acid, carbamic acid or the thioacid or imidic acid corresponding to the indi-go vidually present acids ~or from an organic sulfonic acid, wherein in each case these acids [comprise aliphatic, aromatic and/or heterocyclic groups in the molecule as well as carbamoyl or carbamimidoyl.]

WO01/60829 origin:al PCT/EPOOOI313 Suitable examples of these acyl groups were given below.
Acyl residues originating from aliphatic acid are designated as aliphatic acyl groups and in-clude:
alkanoyl (for example formyl,, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, piva-loyl etc.);
alkenoyl (for example acryloyl, methacryloyl, crotonoyl etc.);
alkylthioalkanoyl (for example methylthioacetyl, ethylthioacetyl etc.);
alkanesulfonyl (for example mesyl, ethanesulfonyl, propanesulfonyl etc.);
alkoxycarbonyl (for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopro-to poxycarbonyl, butoxycarbonyl, isobutoxycarbonyl etc.);
alkylcarbamoyl (for example methylcarbamoyl etc.);
(N-alkyl)thiocarbamoyl (for example (N-methyl)thiocarbamoyl etc.);
alkylcarbamimidoyl (for example methylcarbamimidoyl etc.);
axalo;
15 alkoxalyl (for example methoxalyl, ethoxalyl, propoxalyl etc.).
In the above examples of aliphatic aryl groups, the aliphatic hydrocarbon moiety, in particular the alkyl group or alkane radical, may optionally comprise one or more suitable substituents, such as amino, halogen (for example fluorine, chlorine, bromine etc.), hydroxy, hydroxy-2o imino, carboxy, alkoxy (for example methoxy, ethoxy, propoxy etc.);
alkoxycarbonyl, acyla-mino (for example benzyloxycarbonylamino etc.), acyloxy (for example acetoxy, benzyloxy etc.) and the like; preferred aliphatic acyl radicals having such substituents which may be mentioned are alkanoyls substituted, for example, with amino, carboxy; amino and carboxy, halogen, acylamino or the like.
Aromatic acyl radicals are deemed to comprise those acyl radical which originate from an acid with a substituted or unsubstituted aryl group, wherein the aryl group may comprise phenyl, toluyl, xylyl, naphthyl and the like; suitable examples are stated below:
aroyl (for example benzoyl, toluoyl, xyloyl, naphthoyl, phthaloyl etc.);
3o aralkanoyl (for example phenylacetyl etc.);
aralkenoyl (for example cinnamoyl elc.);
aryloxyalkanoyl (for example phenoxyacetyl etc.);
arylthioalkanoyl (fox example phenylthioacetyl etc.);
arylaminoalkanoyl (for example N-phenylglycyl etc.);
arenesulfonyl (for example benzenesulfonyl, tosyl or toluenesulfonyl, naphthalenesulfonyl etc.);
aryloxycarbonyl (fox example phenoxycarbonyl, naphthyloxycarbonyl etc.);
aralkoxycarbonyl (for example benzyloxycarbonyl etc.);

WO01/60829 original PCT/EP0001313 arylcarbamoyl (for example phenylcarbamoyl, naphthylcarbamoyl etc.);
arylglyoxyloyl (for example phenylglyoxyloyl etc.).
In the above examples of acyl radicals, the aromatic hydrocarbon moiety (in particular the aryl radical) and/or the aliphatic hydrocarbon moiety (in particular the alkane radical) may optionally comprise one or more suitable substituents, such as those which have already been stated as suitable substituents for the alkyl group or the alkane radical.
Aromatic acyl radicals having particular substituents which may in particular be mentioned and constitute examples of preferred aromatic acyl radicals are amyl substituted with halogen and hydroxy or with to halogen and acyloxy, and aralkanoyl substituted with hydroxy, hydroxyimino, dihaloalka-noyloxyimino, together with arylthiocarbamoyl (for example phenylthiocarbamoyl etc.);
arylcarbamimidoyl (for example phenylcarbamimidoyl etc.).
A heterocyclic acyl radical is taken to mean an acyl radical which originates from an acid with a heterocyclic group; these include:
heterocyclic carbonyl, in which the heterocyclic radical is an aromatic or aliphatic 5- to 6-membered heterocycle with at least one heteroatom from the group comprising nitrogen, oxy-2o gen and sulphur (for example thiophenyl, furoyl, pyrrolocarbonyl, nicotinoyl etc.);
alkanoyl heterocycle, in which the heterocyclic radical is 5- to 6-membered and comprises at least one heteroatom from the group comprising nitrogen, oxygen and sulphur (for example thiophenylacetyl, furylacetyl, imidazolylpropionyl, tetrazolylacetyl, 2-(2-amino-4-thiazolyl)-2s 2-methoxyiminoacetyl etc.) and the like.
In the above examples of heterocyclic acyl radicals, the heterocycle and/or the aliphatic hy-drocarbon moiety may optionally comprise one or more suitable substituents, such as those as have been stated to be suitable for alkyl and alkane groups.
"Alkyl" is a straight- or branched-chain alkyl radical having up to 26 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert.-butyl, pentyl, hexyl and the like.
"Hydroxyalkyl" is a straight- or branched-chain alkyl radical having up to 26 carbon atoms, which at least comprises one hydroxy group, preferably one or two hydroxy groups.
"Alkenyl" includes straight- or branched-chain alkenyl groups with up to 26 carbon atoms, for example vinyl, propenyl (for example 1-propenyl, 2-propenyl), 1-methylpropenyl, 2-WO01/60829 original PCT/EP0001313 methylpropenyl, butenyl, 2-ethylpropenyl, pentenyl, hexenyl.
"Alkinyl" includes straight- or branched-chain alkinyl radicals having up to 26 carbon atoms.
Cycloalkyl preferably represents an optionally substituted C3_~-cycloalkyl;
possible substitu-ents are e.g. alkyl, alkenyl, alkinyl, alkoxy (for example methoxy, ethoxy etc.), halogen (for example fluorine, chlorine, bromine etc.), vitro and the like:
Aryl is an aromatic hydrocarbon radical such as phenyl, naphthyl etc., which may optionally to contain one or more suitable substituents such as alkoxy (for example methoxy, ethoxy etc.), halogen (for example fluorine, chlorine, bromine etc.), vitro and the like.
"Aralkyl" includes mono-, di-, triphenylalkyls such as benzyl, phenethyl, benzhydryl, trityl and the like, wherein the aromatic part may optionally contain one or more suitable substitu-t5 ents such as alkoxy (for example methoxy, ethoxy etc.), halogen (for example fluorine, chlo-rive, bromine etc.), vitro and the like.
The radicals X2 and X3 may also be selected such, that esters form on the phosphono group or the phosphino group. Suitable examples of such esters according to formula (I) are generally 2o suitable mono and diesters, for example alkylesters (for example methylester, ethylester, pro-pylester, isopropylester, butylester, isobutylester, hexylester etc.);
aralkyl ester (benzyl ester, phenethyl ester, benzohydryl ester, trityl ester etc.);
aryl ester (for example phenyl ester, toluyl ester, naphthyl ester etc.);
aroylalkyl ester (for ex-ample phenacyl ester etc.); and silylester (for example of trialkylhalogensilyl, dialkyldihalo-25 gensilyl, alkyltrihalogensilyl, dialkylarylhalogensilyl, trialkoxyhalogensilyl, dialkylaralkyl-halogensilyl, dialkoxydihalogensilyl, trialkoxyhalogensilyl etc.) and the like.
With the above ester the alkane and/or arene part may optionally contain at least one suitable substituent such as halogen, alkoxy, hydroxy, vitro or the like.
As described above methyl, ethyl and phenyl esters are especially preferred.
Further, XZ and X3 may be a metal of the first, second, or third main group of the periodic system, ammonium, substituted ammonium, or ammonium compounds, which derive from ethylene diamine or amino acids. In other words the salt compounds of the phosphorous or-ganic compounds with organic or inorganic bases (for example sodium salt, potassium salt, calcium salt, aluminum salt, ammonium salt, magnesium salt, triethylamine salt, ethanola-mine salt, dicyclohexylamine salt, ethylenediamine salt, N,N'-dibenzylethylene diamine salt etc.) as well as salts with amino acids (for example arginine salt, a.spartic acid salt, glutamic acid salt etc.) and the like are formed. The sodium salt is preferred.
The compounds according to the invention in accordance with formula (I) may be present in their protonized form as an ammonium salt of organic or inorganic acids, such as hydrochlo-ric acid, hydrobromic acid, sulfur acid, nitric acid, methanesulfonic acid, p-toluene sulfonic acid, acetic acid, lactic acid, malefic acid, fumaric acid, oxalic acid, tartaric acid, benzoic acid, etc..
The compounds according to the invention in accordance with formula (I) permit the emer-gence of spatial isomers for groups containing double bonds or chiral groups Rl, R2, R3, Xl, X2, X3 or A. The use of the compounds according to the invention includes all spatial isomers both as pure substances and in form of their mixtures.
In the following the preferred compounds are listed:
N-hydroxy-N- o , a methyl-4-phosphono- ~ P~ OH
2o butyric acid amide ~ ONa monosodium salt OH
N-hydroxy-N- / o 0 phenyl-4-phosphono- ~ ~ . P' OH
butyric acid amide ~ oi~a monosodium salt off N-hydroxy-N- 0 0 (2-hydroxyethyl)- HO~ P~ OH
3o 4-phosphono- ~ a~a butyric acid amide monosodium salt WO01/60829 original PCT/EP0001313 N-(1-carboxypropyl)-N-hydroxy-4-phosphono- 0 OH 0 0 butyric acid amide ~. P~ OH
s monosodium salt N ONa OH
N-hydroxy-N- ~ N 0 ~ I I
(4-imidazolyl)-4- HN
phosphonobutyric acid to amide monosodium salt OH
N-ethyl-N-hydroxy-4-ethylphosphono butyric ~ ~ ~Et N ONa acid amide monosodium salt o ff is N-benzyl-N-hydroxy-4- p 0 ethylphosphono butyric acid ~ Ip amide monosodium salt ~ oEt ~ ~ ~ ONa OH
20 N-allyle-N-hydroxy p 0 4-ethylphosphono-butyric acid amide ~ ~ II
monosodium salt ~N P~ OEt I ONa OH
2s N-hydroxy-N-(3-(3-phenylpropionyl)-4-ethylphosphonobutyric p1 acid amide monosodium salt ~ oEt ONa 3o N-(4-fluorobenzyl)-N- o hydroxy-4-ethylphosphono- IPA oEt butyric acid amide mono- I ~ \N ONa sodium salt / OH
F
3s N-hydroxy-N-h-propyl- 0 hos hono-4-liethylp p ~N ~ oEt butyric acid amide oEt OH

WO01/60829 original PCT/EP0001313 -g_ r N-hydroxy-N- ~ ~ P~''~OEt ortho-tolyl-4-diethyl- j OEt phosphonobutyric acid amide OH

N-but-3-inyl-N-hydroxy-4-diethylphosphono- j oEtEt butyric acid amide OH
N-(1-carboxy-2-methyl- 0 OH
O O
to propyl)-N-hydroxy-4- II
diethylphosphono- ~ N P~ oEt OH
butyric acid amid OEt H
N-hydroxy-N-(2-{4-hydroxy- N~, O O
15 indol-3-yl)-ethyl)-4-diethyl- ~ ~ ,~ iP1 phosphonobutyric acid amide ~ ~ ~E Et , OH
OH
N-hydroxy-N-isopropyl-4-dimethyl- O O
2o phosphinoxido-. I (P
butyric acid amide ~OH
N-meta-ethylbenzyl- O
O
N-hydroxy-4-dimethyl- I I
25 phosphinoxido-I
butyric acid amide ~ off N-cyclohex-2-enyl- O
O
N-hydroxy-4-dimethyl- ~
3o phosphinoxido- N \
butyric acid amide off N-( 1-carboxy-2-methyl- o OH
O O
butyl) N-hydroxy-4- Pt 1 35 dimethylphosphinoxido- ~ 'N \
butyric acid amide OH

WO01/60829 original PCT/EP0001313 N-carbamoyl-N-hydroxy- O 0 I I
4-dimethylphosphinoxido- ~ P
H.,N' -N
butyric acid amide OH
O
N-h-butyl-N-hydroxy-4- O
II
(P-methyl-phosphinato)-' c acid amide ~ ~ P\ off butyri OH
1 o N-hydroxy-N-(para-isopropylbenzyl)-4- 0 N P\ OH
(P-methyl-phosphinato)-butyric acid amide I / o ff 15 N-hydroxy-N-(4,4,4-trifluorobutyl)-4- O
I I
(P-methyl-phosphinato)- P~ OH
butyric acid amide F C~~N
~. . off 2o N-carboxymethyl N-hydroxy-4-(P-methyl- - 0 OH
phosphinato)- IPA off N
butyric acid amide off 25 N-ethoxycarbonyl- 0 0 II
N-hydroxy-4- p~ off (P-methyl-phosphinato)- /~'0 N
butyric acid amide OH
3o N-isobutyl-N-hydroxy- O 0 4-oxo-4- hos hono- IPA OH
p p N ~ ~ ONa butyric acid amide mono- ~ I p OH
sodium salt 35 N-ortho-chlorphenyl-N- /' I O 0 drox -4-oxo-4- hosphono- ' ~ IPA OH
hY Y p ~N v ~ ONa butyric acid amide monosodium salt W001/60829 original PCT/EP0001313 N-cyclohexyl-N-hydroxy-4-oxo-4-phosphono- 0 O
butyric acid amide ~ ' P~ OH
monosodium salt ~ V ~ ONa OH O
N-(1-carboxyethyl)-N-hydroxy-4-oxo-4- 0 OH 0 O
phosphonobutyric acid OH
amide monosodium salt ~ oNa N-hydroxy-N-(2-(N-hydroxy-carbamoyl)-ethyl)-4-oxo-4- ~ 0 0 phosphono butyric acid amide HN~N P~ OH
I ONa monosodium salt OH OH O
N-tert.-butyl-N-hydroxy- O Q
4-ethylphosphono- ~ p~ oEt 4-oxo-butyric acid amide ~ j1 v ~ ONa off o monosodium salt ZO
OzN
N para-nitrophenyl-N- ~ ( 0 0 hydroxy-4-ethyl-phosphono- \ N P~ oEt 4-oxo-butyric acid amide ONa monosodium salt O
N-(4-oxocyclohexyl)-N- O 0 hydroxy-4-ethyl-phosphono- ~'-OEt 4-oxo-butyric acid amide OH O ONa monosodium salt N-(1-carboxy-1-methyl- 0 0 ethyl)-N-hydroxy-4-ethyl- P~ OEt ONa phosphono-4-oxo-butyric acid off amide monosodium salt N-(3-chloro-2,2-dimethylpropyl)- , . O
N ~ OEt N-hydroxy-4-ethyiphosphono ~ \~ ONa -4-oxo-butyric acid amide monosodium salt ~~ OH 0 W001160829 originnl PCT/EP0001313 N-hydroxy-N-n-pentyl-o O
I I
4-diethylphosphono-4-oxobutyric acid amide N P~ oEt OEt N-hydroxy-N-(3-acetyl-4-methoxy-phenyl)-4- O
o O
diethyl-phosphono-4-oxo-butyric acid amide O ~ N ~ P QE Et 1 o N-hydroxy-N-(3-methylcyclohexyl) ~ o O
4-diethylphosphono- ~ N P~ OEt 4-oxo-butyric acid amide off o OEt 15 N-(5-amino-1-carboxy- O OH
pentyl)-N-hydroxy-4-o Ii diethyl-phosphono-4- N ~~ oEt oxo-butyric acid amide o ff o oEt NH-2o N-hydroxy-N-(3- o O
(N-morpholino)propyl)-~N'~N P~ OEt 4-diethyl-phosphono- I oEt 4-oxo-butyric acid amide o J OH O
O o 25 N-hydroxy-N-isobutyl-4-dimethyl- N IP ~' phosphono-4-oxo- OH O
butyric acid amide 3o N-beta-naphthyl- / / I O lol N-hydroxy-4-dimethyl-N
phosphinoxido-4-oxo- OH o butyric acid amide HO
35 N-(4-hydroxymethyl-2-phenyl- O O o 1,3-dioxane-4-yl)-N-hydroxy- -~ N , 4-dimethylphosphinoxido- O
off o 4-oxo-butyric acid amide WO01/60829 original PCT/EP0001313 N-(1-carboxy-3-methyl- O OH
butyl)-N-hydroxy-4-dimethyl-phosphinoxido- \ N
4-oxo-butyric acid amide off O
N-(2-furyl)-N-hydroxy-0 (O ~
4-dimethylphosphinoxido-4=
oxo butyric acid amide OH O
to N-(3-methyl-pentyl)-N-hydroxy-4-(P-methyl- 0 phosphinato)-4-oxo- N P~ OH
butyric acid amide OH 0 15 N-hydroxy-N-(meta- / p O
pyridyl)-4-(P-methyl- N~ Ip pH
N
phosphinato)-4-oxo-butyric acid amide off o cN o 2o N-hydroxy-N-(1-cyano-cyclohexyl)-4-(P-methyl- N p~ OH
phosphinato)-4-oxo- ~ OH 0 butyric acid amide 0 off o 25 N-(1-carboxy-pentyl)-N-hydroxy-4-(P-methyl- N ~ off phosphinato)-4-oxo- OH o butyric acid amide / ~ ~0 0 3o N-(N-phenyl-carbamoyl)-N' _N ~ OH
N-hydroxy-4-(P-methyl- H
phosphinato)-4-oxo- OH
butyric acid amide 35 N-hydroxy-N-h-octyl-3- ~~ off oxo-4-phosphono-butyric N oNa acid amide monosodium salt OH

W001/60829 original PCT/EP0001313 N-hydroxy-N-(2-indolyl)- -- 0 0 0 3-oxo-4-phosphonobutyric acid amide monosodium salt N N P ONa ON
N-hydroxy-N-dec-9-enyl 3-oxo-4-phosphono- 0 0 0 butyric acid amide / N p 0Na monosodium salt 1o N-(1-carboxy-3-methyl-O OHO O
thiopropyl)-N-hydroxy-3-oxo-4-phosphono butyric ~ P~ OH
N
acid amide monosodium salt S ~ oNa ON
15 N-hydroxy-N-(2,2,2-trichlor-ethyl)-3-oxo-4-phosphono- O 0 0 P~ OH
butyric acid amide Ct3C N ONa monosodium salt OH
2o N-decyl-N-hydroxy- 0 0 D
3-oxo-4-ethylphosphono ~ wN P~ oEt butyric acid amide . ~ o ff ONa monosodium salt ' 25 N-(2-fluorenyl)-N- ., ~ / ~ . ~ o O
hydroxy-3-oxo-4-cthyl- ~, ~~ oEt phosphonobutyric acid ~ ONa amide monosodium salt OH
3 o N-( 1-adamantyl)- 0 0 N-hydroxy-3-oxo-4-ethyl- N p ONa t phosphono-butyric acid OH
amide monosodiumsalt p 0~ O
3s N-(1,4-dioxan-2-yl)- O N~.~/~~ OEt ONa N-hydroxy-3-oxo-4-ethylphosphonobutyric 0 acid amide monosodium salt WO01/60829 original PCT/EP0001313 N-(N-(2,4-dimethyl-phenyl)-carbamoyl)-N-hydroxy-3-oxo- /~ O 0 O O
4-ethylphosphonobutyric acid amide monosodium salt ~ H N ~ OEt OH ONa N-(3-methyl-hex-2-yl)-N-hydroxy-3-oxo-4-II
diethylphosphono-OEt butyric acid amide OEt OH
N-meta-tolyl-N-hydroxy- ~ O 0 II
3-oxo-4-diethyl phosphonobutyric acid amide \ N P of Et OH
N-(3-acetylaminopropyl)-N-hydroxy-3-oxo-4- O O O o diethylphosphono- ~N/~/~N ply OEt butyric acid amide H oEt OH
2o N-(2-Pyrrolidon-4-yl)-N-hydroxy-3-oxo-4- O O O j II
diethylphosphono- ~H~N p~ OEt butyric acid amide IOH OEt N-(2-(methylsulfoxido)-II o 0 0 ethyl)-N-hydroxy-3-oxo-4-diethylphosphono- ~ ~N P ~E Et I
butyric acid amide OH
3o N-dodecyl-N-hydroxy- 0 O O
3-oxo-4-dimethyl p N
phosphinoxido- I
butyric acid amide OH
HO
N para-hydroxyphenyl- ~ 0 O 0 I I
N-hydroxy-3-oxo-4- '~ ~ N P
dimethylphosphinoxido- I
butyric acid amide OH

W001160829 original PCT/EP0001313 N-(2-propionylethyl)- O 0 N-hydroxy-3-oxo-4- 0~/~, N
dimethylphosphinoxido- ~ off butyric acid amide HO O OH
N-(1-carboxy-2-(3,4- 0 O ~I
dihydroxyphenyl)-ethyl)-HO 'N
N-hydroxy-3-oxo-4-dimethyl- off to phosphinoxido-butyric acid amide N-(3-phosphonopropyl)- Hp ~ f II
P
N-hydroxy-3-oxo-4-dimethyl- II~ I
phosphinoxido-butyric acid amide O OH
15 monosodium salt N-(3-ethyl-4-methyl-pentyl)- 0 O II
N-hydroxy-3-oxo-4- N P~ OH
(P-methyl-phosphinato)- ~ off 2o butyric acid amide N-(3-hydroxy-3-phenyl- ' - OH 0 0 0 ro yl)-N-hydroxy-3-oxo- I N IPA OH
P P
4-(P-methyl-phosphinato)- ~ off 25 butyric acid amide N-(2-(2-methoxy-ethoxy)- P~ off ethyl)-N-hydroxy-3-oxo- ~0~0 4-(P-methyl-phosphinato)- OH
3o butyric acid amide II
N-(4-imidazolyl-methyl)- N N P~ OH
N-hydroxy-3-oxo-4-(P-methyl-phosphinato)- N OH
H
35 butyric acid amide o ! 0 0 0 p\ OH
OH
o ,....-, N-(2-(7-(2-(N,N-diethylamino)-ethoxy)-fluorene-9-on-2-yloxy)-ethyl)-N-hydroxy-3-oxo-4-(P-methyl-phosphinato)-butyric acid amide.
Further preferred compounds are listed in the examples.
The compound N-hydroxy-N-methyl-4-phosphonobutyric acid amide monosodium salt is especially preferred.
The phosphorous organic compounds are in particular suited for the therapeutic and prophy-lactic treatment of infections in humans and animals caused by viruses, bacteria, unicellular and multicellular parasites and fungi. According to the invention unicellular parasites are protozoa according to the narrow definition of parasitology.
2o The compounds are effective against unicellular parasites (protozoa), in parkicular against pathogens of malaria and the sleeping sickness as well as Chagas' disease, toxoplasmosis, amoebic dysentery, leishmaniasis, trichomoniasis, sarcocystosis, acanthamebiasis, naegleria-sis, coccidiosis, giardiasis and Iambliosis.
Therefore, they are particularly suitable as malaria prophylactics and as prophylactics of sleeping sickness as well as the Chagas' disease, toxoplasmosis, amoebic dysentery, Ieishma-niasis, trichomoniasis, pneumocystosis, balantidiasis, cryptosporidiasis, sarcocystosis, acan-thamebiasis, naegleriasis, coccidiosis, giardiasis and lambliosis.
3o The active agents according to the invention may in particular be used against the following bacteria:
Bacteria of the family Propionibacteriaceae, in particular the genus Propionibacterium, in particular the species Propionibacterium acnes; bacteria of the family Actinomycetaceae, in particular the genus Actinomyces; bacteria of the genus Corynebacterium, in particular the species Corynebacterium diphteriae and Corynebacterium pseudotuberculosis;
bacteria of the family Mycobacteriaceae, the genus Mycobacterium, in particular the species Mycobacterium WO01/60829 origi~tal PCT/EP0001313 leprae, Mycobacterium tuberculosis, Mycobacterium bovis and Mycobacterium avium; bacte-ria of the family Chlamydiaceae, in particular the species Chlamydia trachomatis and Chla-mydia psittaci; bacteria of the genus Listeria, in particular the species Listeria monocytoge-nes; bacteria of the species Erysipelthrix rhusiopathiae; bacteria of the genus Clostridium;
bacteria of the genus Yersinia, the species Yersinia pestis, Yersinia pseudotuberculosis, Yer-sinia enterocolitica and Yersinia ruckeri; bacteria of the family Mycoplasmataceae, the genus Mycoplasma and Ureaplasma, in particulax the species Mycoplasma pneumoniae;
bacteria of the genus Brucella; bacteria of the genus Bordetella; bacteria of the family Neiseriaceae, in particular the genuses Neisseria and Moraxella, in particular the species Neisseria meningiti-des, Neisseria gonorrhoeae and Moraxella bovis; bacteria of the family Vibrionaceae, in par-ticular the genuses Vibrio, Aeromonas, Plesiomonas and Photobacterium, in particular the species Vibrio cholerae, Vibrio anguillarum and Aeromonas salmonicidas;
bacteria of the genus Campylobacter, in particular the species Campylobacter jejuni, Campylobacter coli and Campylobacter fetus; bacteria of the genus Helicobacter, in particular the species Helicobac-ter pylori; bacteria of the families Spirochaetaceae and the Leptospiraceae, in particular the genus Treponema, Borrelia and Leptospira, in particular Borrelia burgdorferi;
bacteria of the genus Actinobacillus; bacteria of the family Legionellaceae, the genus Legionella; bacteria of the family Rickettsiaceae and family Bartonellaceae; bacteria of the genus Nocardia and Rho-dococcus; bacteria of the genus Dermatophilus; bacteria of the family Pseudomonadaceae, in 2o particular the genuses Pseudomonas and Xanthomonas; bacteria of the family Enterobacteria-ceae, in particular the genuses Escherichia; Klebsiella, Proteus, Providencia, Salmonella, Ser-ratia and Shigella; bacteria of the family Pasteurellaceae, in particular the genus Haemophilus;
bacteria of the family Micrococcaceae, in particular the genus Micrococcus and Staphylococ-cus; bacteria of the family Streptococcaceae, in particular the genus Streptococcus and Ente-rococcus and bacteria of the family Bacillaceae, in particular the genus bacillus and clostrid-gum.
Therefore the phosphorous organic compounds are suitable for treatment of diphtheria, acne vulgaris, listeriosis, erysipelas in animals, gas gangrene in humans and in animals, diseases in 3o hlunans and animals caused by clostridium septicum, tuberculosis in humans and animals, leprosy, and further mycobacteriosis in humans and animals, paratuberculosis in animals, pestis, mesenterial lymphadenitis and pseudotuberkulosis in humans and animals, cholera, legionnaires disease, borrelioses in humans and animals, leptospiroses in humans and animals, syphilis, campylobacter enteritides in humans and animals, moraxella keratoconjunctivitis and serositis in animals, brucelloses in animals and in humans, anthrax in humans and animals, actinomycosis in humans and animals, streptotrichosis, psittakosis/ornithosis in animals, Q-fever, ehrlichiosis.

WO01/60829 original PCT/EP0001313 Further, the use is advantageous in helicobacter eradication therapy of ulcera of the gastroin-testinal tract.
Further combinations with an additional antibiotic may also be used for treatment of the above mentioned diseases. As combined preparations with other antiinfective agents in par-ticular isoniazide, rifarnpicin, ethambutol; pyrazinamide, streptomycin, protionamide and dapsone are suitable for the treatment of tuberculosis The active agents according to the present invention may furthermore be used in particular in to infections with following viruses:
Parvoviridae: parvo viruses, dependo viruses, Denso viruses; Adenoviridae:
adeno viruses, mastadeno viruses, aviadeno viruses; Papovaviridae: papova viruses, in particular papilloma viruses (so called wart viruses), Polyoma viruses, in particular JC virus, BK
virus, and miopa-pova viruses; herpes viruses: all herpes viruses, in particular herpes simplex viruses, the i5 varizella-zoster viruses, human cytomegalo virus, Epstein-Barr viruses, all human herpes vi-ruses, human herpes virus 6, human herpes virus 7, human herpes virus 8;
Poxviridae: pox viruses, orthopox, parapox, molluscum contagiosum virus, avipox viruses, capripox viruses, leporipox viruses; all primary hepatotropic viruses, Hepatitis viruses:
hepatitis A viruses, . ' hepatitis B viruses, hepatitis C viruses, hepatitis D viruses, hepatitis E
viruses, hepatitis F vi-2o ruses, hepatitis G viruses; Hepadna viruses: all hepatitis viruses, hepatitis B virus, hepatitis D
viruses; Picornaviridae: picorna viruses, all entero viruses, all polio viruses, alI coxsackie vi-ruses, all echo viruses, all rhino viruses, hepatitis A virus, aphtho viruses;
Calciviridae: hepa-titis E viruses; Reoviridae: reo viruses, orbi viruses, rots viruses;
Togaviridae: toga viruses, alpha viruses, rubi viruses, pesti viruses, rubella virus; Flaviviridae: flavi viruses, ESME vi-25 rus, hepatitis-C-Virus; Orthomyxoviridae: all influenza viruses;
Paramyxoviridae: paramyxo viruses, morbilli virus, pneumo virus, measles virus, mumps virus;
Rhabdoviridae: rhabdo viruses, rabies virus, lyssa virus, viscula stomatitis virus; Corona. viridae:
corona viruses;
Bunyaviridae: bunya viruses, nairo virus, phlebo virus, uuku virus, hanta virus; Arenaviridae:
arena viruses, lymphocytic choriomeningitis-virus; Retroviridae: retro viruses, all HTL vi-3o ruses, human T-cell leukaemia virus, oncorna viruses, spuma viruses, lenti viruses, all HI-viruses; Filoviridae: Marburg and Ebola virus; Slow-virus-infections, priors;
Onco viruses, leukemia viruses.
The phosphororganic compounds according to the invention are therefore suitable for fighting 35 the following viral infections:
Eradication of papilloma viruses to prevent tumors, in particular tumors in the sexual organs caused by papilloma viruses in humans, eradication of JC viruses and BK
viruses, eradication of herpes viruses, eradication of human herpes viruses 8 for the treatment of Kaposi' s sar-W001/60829 original PCTlEP0001313 coma, eradication of cytomegalo viruses before transplants, eradication of Eppstein-Barr vi-ruses before transplants and to prevent tumors associated with Eppstein-Barr viruses, eradica-tion of hepatitis viruses for the treatment of chronic liver diseases and for the prevention of tumors of the liver and cirrhosis of the liver, eradication of coxsackie viruses patients with cardiomyopathy, eradication of coxsackie viruses in diabetes mellitus patients, eradication of immune system debilitating viruses in humans and animals, treatment of secondary infections in AIDS-patients, treatment of inflammations of viral origin of the respiratory tract (larynx papillomas, hyberplasias, rhinitis, pharyngitis, bronchitis, pneumonias), of the sensory organs (Keratoconjunctivitis), of the nervous system (poliomyelitis, meningoenzephalitis, encephali-to tis, subacute sklerosing panencephalitis SSPE, progressive multifocal leukoencephalopathie, lymphocytic choriomeningitis), of the gastro-intestinal tract (stomatitis, gingivostomatitis, oesophagitis, gastritis, gastroenteritis, diarrhoea-causing diseases), the liver and the gall blad-der system (hepatitis, cholangitis, hepatocellular carcinoma), of the lymphatic tissue (mono-nucleosis, Iymphadenitis), of the haematopoetic system, of the sexual organs (mumpsorchitis), of the skin (warts, dermatitis, herpes labialis, heat rush, herpes zoster, shingles), of the mu-cons membranes (papillomas, conjunctiva papillomas, hyperplasias, dysplasias), of the heart/blood vessel system (arteriitis, myocarditis, endocarditis, pericarditis), the kid-ney/urinary tract systems, of the sexual organs (anogenital lesions, warts, genital warts, acute condylomas, displasias, papillomas, cervix dysplasias, condylomata acuminata, epidermodys-2o plasia verruci formis), of the organs of motion (myositis, myalgien), treatment of foot and mouth diseases in cloven-hoofed animals, of Colorado tick fever; of Dengue-syndrome, of haemorrhagic fever, of early summer meningoencephalitis (FSME) and of yellow fever.
The described compounds, i.e. the phosphorous organic compounds according to formula (I)-and esters and amides thereof formed on the phosphono group or the phosphino group as well as salts thereof show a strong cytotoxic efficacy against bacteria, fungi, viruses, unicellular and multicellular parasites. Therefore the compounds according to the invention are usable in the treatment of infectious diseases caused by viruses, bacteria, parasites, and fungi in humans and animals. The compounds also are suited for use in prophylactics of diseases due to vi-3o ruses, bacteria, parasites; and fungi, in particular in prophylactics of malaria and in prophy-Iactics of the sleeping sickness.
The phosphorous organic compounds according to the invention which generally include pharmaceutically acceptable salts, amides, esters, a salt of such an esters or else compounds which upon application provide the compounds use according to the invention metabolic products or decomposition products, also called "prodrugs" may all be prepared for admini-stration Like known anti-infectious agents in any suitable manner (mixed with non-toxic pharmaceutically acceptable carriers).

WO01/60829 original PCT/EP0001313 Pharmaceutically acceptable salts of the aminohydrophosphonic acid derivative include salts, which form the compounds of formula (I) in their protonised form as an ammonium salt of inorganic or organic acids, such as hydrochloric acid, sulfur acid, citric acid, malefic acid, fu-maric acid, tartaric acid, p-toluene sulfonic acid.
Salts which are formed by suitable selection of X2 and X3 are especially suited, such as so-dium salt, potassium salt, calcium salt, ammonium salt, ethanolamine salt, triethylamine salt, dicyclohexylamine salt and salts of amino acid such as arginine salt, aspartic acid salt, glu-tamic acid salt.
The pharmaceutically effective preparations may be prepared in the form of pharmaceutical preparations in dispensing units. This means that the preparations can be present in the form of individual parts, for example tablets, dragees, capsules, pills, suppositories and ampoules, the active ingredient content of which corresponds to a fraction or a multiple of a single dose.
The dispensing units can, for example, contain 1, 2, or 4 single doses or i/2, 1/3 or 1/4 of a sin-gle dose. A single dose preferably contains the quantity of active ingredient which is admin-istered during one application and which usually corresponds to a whole, a half or third of a.
quarter of a daily dose.
Non-toxic, inert pharmaceutically suitable carriers are understood to mean solid, semi-solid or liquid diluents, fillers and formulation auxiliary agents of all kinds.
Tablets, dragees, capsules, pills, granules, suppositories, solutions, suspensions and emul-sions, pastes, ointments, gels, creams, lotions, powders and sprays axe mentioned as preferred pharmaceutical preparations. Tablets, dragees, capsules, pills and granules may contain in addition to the conventional excipients the active ingredient, such as (a) fillers and diluents, for example starches, lactose, cane sugar, glucose, mannitol and silicic acid, (b) binders, for example carboxymethylcellulosis, alginate, gelatine, polyvinylpyrrolidone, (c) moisture-3o retaining agents, for example glycerol, (d) dispersing agents, for example agar-agar, calcium carbonate and sodium carbonate, (e) solution retarders, for example paraffin and (f) resorption accelerators, for example quaternary ammonium compounds, (g) wetting agents, for example cetyl alcohol, glycerol monostearate, (h) adsorption agents, e.g. kaolin and betonite and (i) lubricants, for example talcum, calcium and magnesium stearate and solid polyethylene gly-col or mixtures of the substances listed under (a) to (i).
The tablets, dragees, capsules, pills and granules may be provided with the conventional coatings and casings optionally comprising opaquing agents and may also be put together so WO01/60829 original PCT/EP0001313 that they release the active ingredient or active ingredients only or preferably in a specific part of the intestinal optionally with sustain release, wherein polymer substances and waxes for example may be used as embedding compounds.
The active ingredient or the active ingredients may optionally also be present in microencap-sulated form with one or more of the above mentioned excipients.
In addition to the active ingredient or the active ingredients suppositories may also contain the conventional water soluble or water insoluble excipients, for example polyethylene glycols, 1 o fats, for example cacoa fat and higher esters (for example C 14- alcohol with C 16-fatty acid) or mixtures of these substances.
In addition to the active ingredients ointments, pastes, creams and gels may contain the con-ventional excipients, for example animal and vegetable fats, waxes, paraffins, starch, traga-15 canth, cellulose derivative, polyethylene glycols, silicones, bentonites, silicic acid, talcum and zinc oxide or mixtures of these substances.
In addition to the active ingredients powders and sprays may contain the conventional excipi-ents, for example lactose, talcum, silicic acid, aluminium hydroxide, calcium silicate and 2o polyamide powder or mixtures of these substances. Sprays may additionally contain the con-ventional blowing agents, for example chlorofluorohydrocarbons.
In addition to the active ingredients solutions and emulsions may contain the conventional excipients such as solvents, solubilisers and emulgators, for example water, ethyl alcohol, 25 isopropyl alcohol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propyle-neglycol, 1,3-butyleneglycol, dimethylformamide, oils, in particular cotton seed oil, peanut oil, corn oil, olive oil, castor oil and sesame oil, glycerol, glycerol formal, tetrahydrofurfuryl alcohol, polyethyleneglycols and fatty acid esters of sorbitan or mixtures of these substances.
3o The solutions and emulsions may also be present in sterile and blood isotonic form for paren-teral application.
In addition to the active ingredients suspensions may contain conventional excipients such as liquid diluents, for example water, ethyl alcohol, propylene glycol, suspending agents, for 35 example ethoxylated isostearyl alcohols, polyoxyethylene sorbitol and sorbitan esters, micro-crystalline cellulose, aluminium metahydroxide, bentonite, agar-agar and tragacanth or mix-tures of these substances.

WO01/60829 original PCT/EP0001313 The above-mentioned formulations can also contain dyes, preservatives and odour and flavour improving additives, for example peppermint oil and eucalyptus oil and sweeteners, for ex-ample saccharine.
The active agents of formula (I) should be present in the above listed pharmaceutical prepara-tions preferably in a concentration of approximately 0.1 to 99.5 % by weight, preferably of approximately 0.5 to 95 % by weight of the total mixture.
In addition to the compounds of formula (I) the pharmaceutical preparations may also contain 1o further pharmaceutical agents.
Furthermore the phosphorous organic compounds may be present in the pharmaceutical preparations in combination with sulfonamide, sulfadoxin, artemisinin, atovaquon, chinin, chloroquine, hydroxychloroquine, mefloquin, halofantrin, pyrimethamine, armesin, tetracy-15 cline, doxycyclin, proguanil, metronidazol, praziquantil, niclosamide, mebendazol, pyrantel, tiabendazole, diethylcarbazin, piperazin, pyrivinum, metrifonate, oxamniquin, bithionol or suramin or several of these substances.
The above listed pharmaceutical preparations are produced in the conventional manner by 2o known methods, for example by mixing the active ingredient or active ingredients with the excipient or excipients.
The above-mentioned preparations can be used in humans and animals either orally, rectally, parentally, (intravenously, intramuscularly, subcutaneously), intracisternally, intravaginally, 25 intraperitoneally, topically (powder, ointment, drops) and for the treatment of infections in cavities, orifices. Suitable preparations axe injection solutions, solutions and suspensions for oral treatment, gels, infusions, emulsions, ointments or drops.
Ophthalmological and derma-togical formulations, silver and other salts, eardrops, eye ointments, powders or solutions can be used for topical treatment. With animals the absorption can occur via the food or drinking 3o water in suitable formulations. Furthermore gels, powders, tablets, sustain release tablets, premixes, concentrates, granules, pellets, tablets, boli, capsules, aerosoles, sprays, inhalers can be used with humans and animals. The compounds according to the invention can fur-thermore be incorporated into other carrier materials such as, for example, plastic materials (plastic chains for topical treatment), collagen or bone cement.
In general it has proved advantageous both in human and veterinary medicine to administer the active ingredient or ingredients of formula (I) in total quantities of approximately 0.05 to approximately 600, preferably 0.5 to 200 mg/kg body weight per 24 hours, optionally in the WO01l60829 original PCT/EP0001313 form of several individual doses in order to achieve the desired results. An individual dose contains the active ingredient or ingredients preferably in quantities of approximately 1 to approximately 200, in particular 1 to 60 mg/kg body weight. It may, however, be necessary to deviate from the above-mentioned dosages and this is dependent on the nature and the body weight of the patient to be treated, the nature and the severity of the disease, the nature and the method and the application of the pharmaceutical compositions as well as the time scale or interval within the administration takes place.
Thus in some cases it may be su~cient to get by with less than the above mentioned quantity to of active ingredient, whilst in other cases the above-stated quantity of active ingredient must be exceeded. The person skilled in the art may determine the optimum dosage and method of application of the active ingredient in each case by virtue of his expert experience.
The compounds according to the invention may be administered in animals in the conven-15 tional concentrations and preparations together with the feed or feed preparations or the drinking water.
Furthermore compounds according to the invention may be excellently used as bactericides, fungicides and herbicides in plants. The compounds according to the invention especially 2o show good herbicidal activity. Consequently the invention also concerns a method for con-trolling undesired plant growth in cultivation of useful plants, wherein their area under culti-vation is treated with an active amount of a compound according to the invention of formula (I) or an agent containing such a derivative.
25 The activity of substances is determined in a test system. This system is based on the meas-uring of the inhibition of growth of bacteria, parasites, viruses, fungi or plants in vitro. To this end, test procedures are used, some of which are known to the person skilled in the .art. To determine the anti-malaria activity, for example, the inhibition of the growth of malaria para-sites in blood cultures is determined. The determining of the anti-bacterial activity, fox exam-3o ple is based on the measurement of the inhibition of the growth of bacteria on culture media and in liquid cultures. The determining of the anti-viral activity is based on the inhibition of the formation of viral elements in cell cultures. The determining of fungicidal activity is based on the inhibition of the growth of fungi on culture media and in liquid cultures. Some of the micro-organism which should be investigated can only be investigated in animal models. In 35 this case we will use the corresponding model.
Substances which demonstrate an efficacy in the in vitro measuring system will be further investigated in in vivo models. The anti-parasitic, antiviral or fungicide activity will be further evaluated in the appropriate animal model.
The screening of herbicidal activity is determined by algae systems and measurement of the isoprene emission of plants at standard conditions.
Principally a person skilled in the art knows which way of synthesis for preparing the sub-stances according to the invention he has to choose. In the following some ways of synthesis 1 o for compounds of the invention are given by example.
Example 1 N-Hvdroxy-4-(diethvlnhosphonol-butyric acid amide (la) 2.52 g (10 mmol) of 4-phosphonobutyric acid triethyl ester are dissolved in 20 ml of water-~5 free methanol. A solution of 11 mmol of hydroxylamine in water-free methanol (filtered from 765 mg (11 mmol) of hydroxylamine hydrochloride and 253 mg (11 mmol) of sodium in methanol) is added dropwise at 0°C. 10 mmol of sodium methanolate (from 230 mg (10 mmol) of sodium) in water-free methanol are added to the resulting mixture at 0°C. It is stirred at room temperature over night. Subsequently, the mixture is filtered, the residue on 2o the filter is taken up in little water, HCl is added until weak acid reaction is observed and is allowed to stand over a period of three weeks. N-hydroxy-4-(diethylphosphono}-butyric acid amide (la) is obtained as colorless crystals and in riloderate yield.
Example 2 25 N-Hvdroxx-N-methyl-4-(dieth~phosphonol-butyric acid amide (2a) In a procedure corresponding to example 1, wherein N-methylhydroxylamine is used instead of hydroxylamine N-hydroxy-N-methyl-4-(diethylphosphono)-butyric acid amide (2a) is ob-tained as colorless crystals and in moderate yield.

Example 4 N-Hvdroxy-N-meth~phosphonobutyric acid amide {2b) 3.06 g (20 mmol) trixnethylbromsilan are added dropwise to a solution of 5 mmol of N-s hydroxy-N-methyl-4-(diethylphosphono)-butyric acid amide (2a) in 50 ml of dry acetonitrile cooled to 0°C. It is stirred at room temperature for 3 hours.
Subsequently, the solvent is stripped out in vacuum and the residue is taken up in 20 ml of iced water. The mixture is stirred for 1 hour at room temperature and is extracted twice with 20 ml of ether, respectively.
A pH value of 4.5 is adjusted with 2 M NaOH. Subsequently, water is stripped out under vac-lo uum at 50°C maximum in a Rotavapor rotary evaporator. The solid residue is crystallized from methanol/ethyl acetate. N-hydroxy-N-methyl-4-phosphonobutyric acid amide (2b) is obtained in the form of colorless crystals and in medium yield.
Example 5 15 4-!Diethyl phosphono -~ ~-hvdroxvacetoacetic acid amide (3a! (or N-h~xv-3-oxo-4-ldieth,~Tlphosphono,Ltvric acid amide!
2.78 g (1 Ommol) of 4-diethyl phosphonomethyl-2,2-dimethyl-1,3-dioxene-4-one (prepared according to Org. Synth. Coll. Vol. VIII, 192-196) is introduced in a pressure vessel. A solu-tion of 11 mmol hydroxylamine (filtered from 765 mg (11 mmol) hydroxylamine hydrochlo-2o ride and 253 mg (11 mmol) sodium in methanol) in water-free methanol is added dropwise at 0°C. 10 mmol of sodium methanolate {from 230 mg (10 mmol) of sodium in water-free methanol) is added to the resulting mixture at 0°C. The vessel is closed and the mixture is heated to 60-70°C over a period of 2 hours. After cooling the produced precipitate is filtered.
The residue on the filter is taken up in little water, HCl is added until weak acid reaction and 25 allowed to stand in a refrigerator over night. 4-(Diethyl phosphono)-N-hydroxyacetoacetic acid amide (3a) is obtained in the form of colorless crystals and in moderate yield.
Example 6 ~Dieth, l~~nhosphonol-N-h~droxy N-methXlacetoacetic acid amide f4a~or N-hvdroxy-N-30 methyl-3-oxo-4.-ldieth~phosphonoy-butyric acid amide) According to the procedure corresponding to example 5 wherein N-methylhydroxylamine instead of hydroxylamine is used 4-(diethyl phosphono)-N-hydroxy-N-methylacetessig acid amide (4a) is obtained as colorless crystals and at moderate yield.

-25a-Example 7 N-H~v-4-phosnhonoacetoacetic acid amide l3bl for N-h~v-3-oxo-4-phosphono-butyric acid amidel 3.06 g (20 mmol) trimethyl bromosilane is added to a solution of 1.27 g (5 mmol) of 4-(Diethylphosphono)-N-hydroxy acetoacetic acid amide (3a) in 50 ml dry acetonitrile cooled to 0°C. It is stirred at room temperature for 3 hours. Then the solvent is stripped off in vac-uum and the residue is taken up in 20 ml of iced water. The mixture is stirred at room tem-perature for 1 hour and extracted twice with 20 ml ether respectively. A pH
value of 4.5 is 1o adjusted with 2 M NaOH. Then water is stripped out under vacuum at 50°C maximum in a Rotavapor rotary evaporator. The solid residue is crystallized from methanol/ethyl acetate. N-hydroxy-4-phosphonoacetoacetic acid amide (3b) is obtained in the form of a colorless pow-der at good yield.
Example 8 N-Hvdroxy-N-methyl-4-phosphonoacetoacetic acid amide (4bl~or N-hvdroxv-N-methyl-3-oxo-4-phosphonobutyric acid amidel According to a procedure corresponding to example 7 starting from 4-(diethylphosphono)-N-hydroxy-N-methylacetoacetic acid amide (4a) N-hydroxy-N-methyl-4-phosphonoacetoacetic 1 o acid amide (4b) is obtained in the form of colorless crystals and in medium yield.
In the following the activities of different compounds according to the invention compounds are stated as examples:
The following substances have been tested:
15 substance 2: N-hydroxy-N-methyl-4-phosphonobutyric acid amide monosodium salt substance 3: N-hydroxy-N-phenyl-4-phosphonobutyric acid amide monosodium salt substance 4: N-hydroxy-4-(P-methyl-phosphinato)butyric acid amide monosodium salt substance 5: N-hydroxy-N-methyl-3-oxo-4-(P-methyl-phosphinato)butyric acid amide mono-sodium salt 2o substance 6: N-hydroxy-3-oxo-4-(P-methyl-phosphinato)butyric acid amide monosodium salt substance 7: N-hydroxy-N-methyl-3-oxo-4-phosphonobutyric acid amide monosodium salt substance $: N-hydroxy-3-oxo-4-phosphonobutyric acid amide monosodium salt substance 9: N-hydroxy-4-diphenyl phosphonobutyric acid amide substance 10: N-hydroxy-N-phenyl-4-diphenyl phosphonobutyric acid amide 25 substance 11: N-hydroxy-N-benzyl-4-phosphonobutyric acid amide monosodium salt substance 12: N-hydroxy-N-benzyl-3-oxo-4-dimethyl phosphonobutyric acid amide Experiments show that the activity of the compounds in bacteria, parasites, fungi and plants is based on an inhibition of the 1-deoxy-D-xylulose-5-phosphate-(DOXP)-metabolic pathway 3o which is present in these organisms, however, which could not have been proved for humans.
Thus, the following example shows the activity of the compounds according to the invention on DOXP-reductoisomerase.
Example 9 35 Inhibition of enzyme DOXP-reductoisomerase from Escherichia coli and Helicobacter pylori DOXP-reductoisomerase of Escherichia coli has been exprimed as recombinant protein in E.coli. The activity of DOXP-reductoisomerase was determined in a composition containing I 00 mM of Tris-HCl (pH=7.5), 1 mM of MnCl2, 0.3 mM of NADPH and 1 mM of DOXP.

The oxidation has been measured in a spectrophotometer at 365 nm. For performing the studies of inhibition the activity of DOXP-reductoisomerase in presence of the compounds 1 and 2 was measured in different concentrations between 0.1 nmol 1-1 and 100 pmol hl. The concentration was determined from the measured values, at which the enzyme was half maximally inhibited (ICso). In like manner the activity of DOXP
reductoisomerase of Helico-bacter pylori has been determined. The results, i.e. IC50-values are listed in table I.
l0 Table I
substance no. Escherichia coli Helicobacter pylori IC50 (nM) ' IC50 nlV~

Ezample 10 Inhibition of growth of bacteria species Pseudomonas aeruginosa and Escherichia coli Antibacterial activity of the above stated compounds A dilution series comprising the concentrations 32, 16, 8, 4, 2, 1 and 0 mg 1'1 of the individual compounds 2 to 8 and 11 and 12 in LB-medium is introduced into culture microtubes in a volume of 0.5 ml. Each of the tubes was inoculated with 10 ~1 of an overnight culture of E.
2o coli Kl2 and shaken overnight at 37°C. Bacterial growth was accessed on the basis of turbid-ity of the mediums. The results are listed in Table II.
Antibacterial activity with regard to P. aeruginosa was determined in the same manner. The results are also listed in Table II.

Table II
substance no. Escherichia coli Pseudomonas aeruginosa MIC (mg/1) MIC (m ) g 1 1 Ezample 11 Inhibition of Plasmodium falciparum growth causative organism of malaria tropica) The antimalarial activity of substances 2 to 12 was determined using in vitro cultures of the causative organism of malaria Plasmodium falciparum. 200 ~.l of a asynchronous Plasmodium falciparum culture with a 0.4 % parasitemia and 2 % haematocrit were loaded into each of the wells of a 96 well microtitre plate. A serial dilution series of the compounds was then pre-pared in steps of three between concentrations of 100 ~.mol fI and 0.14 nmol f1. The plates are incubated at 3.7°C, 3 % COZ and 5 % 02 over a period of 48 hours.
30 ~,1 of medium sup-plemented with 27 ~Ci m11 [3H]-hypoxanthine were then added to each well.
After 24 hours' incubation, the parasites were harvested by filtration through glass fiber filters and the incor-porated radioactivity was measured. Inhibition of parasite growth was measured as the per-centage inhibition of tritium incorporation relative to a comparison without substance. The half maximum inhibition concentration (IC50) of the substance has been determined by ex-trapolation of the values. The results are listed in Table III.

able III
substance no. Plasmodium falcipaYUm IC50 (nlV1) The inhibition of growth of the different plants is stated in the following tables as percentage.
The pictures of damages mean:
C: chlorosis - In dicot plants brightening of the subsequent leafs (degradation of chlorophyll 10 = white coloring of the leafs, whereby the growth is totally inhibited).
In monocot plants the picture of damage is not quite as remarkable as in dicot plants. The brightening is only present in the shoot tips.
I: general white coloring of leafs.

W 001/60$29 original PCT/EP0001313 Ezample 13 Herbicidal activity of monosodium salt of 4~hosphono-N-h~droxy-N-meth~but~ric acid amide The herbicidal activity is tested as in example 12, however with N-4-phosphono-N-hydroxy-N-methylbutyric acid amide monosodium salt as the active ingredient. The results are listed in tables VII to IX.
Table VII
to HYDRO ire-emergence used amount of tested substance: 4000 g/ha species of plant visual bonitur: damage/ picture of damage inhibition of the plants in comparison to the non-treated control (%) rice 20 I

Lepidium ~ 30 C

Eschinochios 0 Solanum 0 W001160$29 original PCT/EP0001313 Table VIII
EARTH_pre-emergence nenr~ amnn7lt of tPCtPI~ substance: 2000 gJha species of plant visual bonitos: damage/ picture of damage inhibition of plants on comparison to the non treated control %) maize (zea ma s) 0 sugar beet (beta vul 30 aris) slender foxtail 0 (alopecurus m osuroides) wild oats (avena atua) 0 yellow nutsedge #

(cy erus esculentus green foxtail (setaYia 0 viridis) velvet leaf (abutilon 0 then hrasti) redroot amaranth (amaranthus0 retr-of lexus) cleavers ( alium a Brine) wild mustard (sina is 50 arvensis) common cockleburs (xanthium0 strumarium) WO01/60829 original PCT/EP0001313 Table IX
EARTH post-emergence used amount of tested substance: 2000 ~/ha visual bonitur: damage/ picture of inhibition damage of plants on comparison to the non treated control (%) maize (zea mays) 70 C

sugar beet (beta vulgaris)50 slender foxtail 70 C
(alo ecurus myosuroides) wild oats avena atua) 70 C

yellow nutsedge #
(cy eras esculentus) green foxtail (setaria 95 C
viridis) velvet leaf (abutilon ~ 30 C
theo hrasti) redroot amaranth (amaranthus0 ret roflexus) cleavers ( alium a Brine)70 C

wild mustard (sina is 90 C
arvensis) common cockleburr (xanthium50 C
strumarium)

Claims (16)

1. Organophosphorus compounds of general formula (I) in which A represents propylene, 2-oxopropylene or 3-oxopropylene, in which R1 is selected from the group consisting of hydrogen, substituted and unsub-stituted alkyl, substituted and unsubstituted hydroxyalkyl, substituted and unsubsti-tuted alkenyl, substituted and unsubstituted alkinyl, substituted and unsubstituted aryl, substituted and unsubstituted acyl, substituted and unsubstituted cycloalkyl, substi-tuted and unsubstituted aralkyl, substituted and unsubstituted heterocyclic residue, halogen and OX1, wherein X1 is selected from the group consisting of hydrogen, substituted and unsub-stituted alkyl, substituted and unsubstituted hydroxyalkyl, substituted and unsubsti-tuted alkenyl, substituted and unsubstituted alkinyl, substituted and unsubstituted aryl, substituted and unsubstituted acyl, substituted and unsubstituted cycloalkyl, substi-tuted and unsubstituted aralkyl, substituted and unsubstituted heterocyclic residue and in which R2 and R3 are the same or different and are selected from the group consisting of hydrogen, substituted and unsubstituted alkyl, substituted and unsubstituted hy-droxyalkyl, substituted and unsubstituted aryl, substituted and unsubstituted acyl, sub-stituted and unsubstituted aralkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted alkinyl, substituted and unsubstituted cycloalkyl, substituted and un-substituted heterocyclic residue, halogen, OX2 or OX3, wherein X2 or X3 may be the same or different and are selected from the group, con-sisting of hydrogen, substituted and unsubstituted alkyl, substituted and unsubstituted hydroxyalkyl, substituted and unsubstituted aryl, substituted and unsubstituted aralkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted alkinyl, substituted and unsubstituted cycloalkyl, substituted and unsubstituted heterocyclic residue, a si-lyl, a cation of an organic and inorganic base, in particular a metal of the first, second, or third main group of the periodic system, ammonium, substituted ammonium and ammonium compounds, which derive from ethylene diamine or amino acid, and their pharmaceutically acceptable salts, esters and amides and salts of the esters with the exception of N-hydroxy-4-phosphonobutyric acid amide and the salts thereof.
2. Compounds according to claim 1, characterized in that R1 is selected from the group consisting of a hydrogen residue, a methyl residue, an ethyl residue and a phenyl resi-due.
3. Compounds according to claim 1 or claim 2, characterized in that R2 and R3 are the same or different and are selected from the group consisting of a methyl residue, an ethyl residue, OX2 and OX3.
4. Compounds according to claim 2, characterized in that X2 and X3 are the same or dif-ferent and are selected from the group consisting of sodium, a methyl residue, an ethyl residue and a phenyl residue.
5. Compounds according to claim 1, characterized in that they are selected from the group consisting of N-hydroxy-N-methyl-4-phosphonobutyric acid amide monosodium salt, N-hydroxy-N-phenyl-4-phosphonobutyric acid amide monosodium salt, N-hydroxy-N-(2-hydroxyethyl)-4-phosphonobutyric acid amide monosodium salt, N-(1-carboxypropyl)-N-hydroxy-4-phosphonobutyric acid amide monosodium salt, N-hydroxy-N-(4-imidazolyl)-4-phosphonobutyric acid amide monosodium salt, N-ethyl-N-hydroxy-4-ethylphosphonobutyric acid amide monosodium salt, N-benzyl-N-hydroxy-4-ethylphosphonobutyric acid amide monosodium salt, N-allyle-N-hydroxy-4-ethylphosphonobutyric acid amide monosodium salt, N-hydroxy-N-(3-(3-phenylpropionyl)-4-ethylphosphonobutyric acid amide monoso-dium salt, N-(4-fluorobenzyl)-N-hydroxy-4-ethylphosphono-butyric acid amide monosodium salt, N-hydroxy-N-n-propyl-4-diethylphosphonobutyric acid amide, N-hydroxy-N-ortho-tolyl-4-diethyl-phosphonobutyric acid amide, N-but-3-inyl-N-hydroxy-4-diethylphosphonobutyric acid amide, N-(1-carboxy-2-methyl-propyl)-N-hydroxy-4-diethylphosphonobutyric acid amide, N-hydroxy-N-(2-{4-hydroxy-indol-3-yl)-ethyl)-4-diethyl-phosphonobutyric acid amide, N-hydroxy-N-isopropyl-4-dimethyl-phosphinoxido-butyric acid amide, N-meta-ethylbenzyl-N-hydroxy-4-dimethyl-phosphinoxido-butyric acid amide, N-cyclohex-2-enyl-N-hydroxy-4-dimethyl-phosphinoxido-butyric acid amide, N-(1-carboxy-2-methyl-butyl)-N-hydroxy-4-dimethylphosphinoxidobutyric acid amide, N-carbamoyl-N-hydroxy-4-dimethylphosphinoxidobutyric acid amide, N-n-butyl-N-hydroxy-4-(P-methyl-phosphinato)-butyric acid amide, N-hydroxy-N-(para-isopropylbenzyl)-4-(P-methyl-phosphinato)-butyric acid amide, N-hydroxy-N-(4,4,4-trifluorbutyl)-4-(P-methyl-phosphinato)-butyric acid amide, N-carboxymethyl-N-hydroxy-4-(P-methyl-phosphinato)-butyric acid amide, N-ethoxycarbonyl-N-hydroxy-4-(P-methyl-phosphinato)-butyric acid amide, N-isobutyl-N-hydroxy-4-oxo-4-phosphono-butyric acid amide monosodium salt, N-ortho-chlorophenyl-N-hydroxy-4-oxo-4-phosphono-butyric acid amide monosodium salt, N-cyclohexyl-N-hydroxy-4-oxo-4-phosphono-butyric acid amide monosodium salt, N-(1-carboxyethyl)-N-hydroxy-4-oxo-4-phosphonobutyric acid amide monosodium salt, N-hydroxy-N-(2-(N-hydroxy-carbamoyl)-ethyl)-4-oxo-4-phosphono-butyric acid amide monosodium salt, N-tert-butyl-N-hydroxy-4-ethylphosphono-4-oxo-butyric acid amide monosodium salt, N-para-nitrophenyl-N-hydroxy-4-ethyl-phosphono-4-oxo-butyric acid amide monoso-dium salt, N-(4-oxocyclohexyl)-N-hydroxy-4-ethyl-phosphono-4-oxo-butyric acid amide monoso-dium salt, N-(1-carboxy-1-methyl-ethyl)-N-hydroxy-4-ethyl-phosphono-4-oxo-butyric acid amide monosodium salt, N-(3-chloro-2,2-dimethyl-propyl)-N-hydroxy-4-ethylphosphono-4-oxo-butyric acid amide monosodium salt, N-hydroxy-N-n-pentyl-4-diethyl-phosphono-4-oxo-butyric acid amide, N-hydroxy-N-(3-acetyl-4-methoxy-phenyl)-4-diethyl-phosphono-4-oxo-butyric acid amide, N-hydroxy-N-(3-methylcyclohexyl)-4-diethylphosphono-4-oxo-butyric acid amide, N-(5-amino-1-carboxy-pentyl)-N-hydroxy-4-diethyl-phosphono-4-oxo-butyric acid amide, N-hydroxy-N-(3-(N-morpholino)propyl)-4-diethyl-phosphono-4-oxo-butyric acid amide, N-hydroxy-N-isobutyl-4-dimethyl-phosphono-4-oxo-butyric acid amide, N-beta-naphthyl-N-hydroxy-4-dimethyl-phosphinoxido-4-oxo-butyric acid amide, N-(4-hydroxymethyl-2-phenyl-1,3-dioxan-4-yl)-N-hydroxy-4-dimethyl-phosphinoxido-4-oxo-butyric acid amide, N-(1-carboxy-3-methyl-butyl)-N-hydroxy-4-dimethyl-phosphinoxido-4-oxo-butyric acid amide, N-(2-furyl)-N-hydroxy-4-dimethylphosphinoxido-4-oxo-butyric acid amide, N-(3-methyl-pentyl)-N-hydroxy-4-(P-methyl-phosphinato)-4-oxo-butyric acid amide, N-hydroxy-N-(meta-pyridyl)-4-(P-methyl-phosphinato)-4-oxo-butyric acid amide, N-hydroxy-N-(1-cyano-cyclohexyl)-4-(P-methyl-phosphinato)-4-oxo-butyric acid amide, N-(1-carboxy-pentyl)-N-hydroxy-4-(P-methyl-phosphinato)-4-oxo-butyric acid amide, N-(N-phenyl-carbamoyl)-N-hydroxy-4-(P-methyl-phosphinato)-4-oxo-butyric acid amide, N-hydroxy-N-n-octyl-3-oxo-4-phosphonobutyric acid amide monosodium salt, N-hydroxy-N-(2-indolyl)-3-oxo-4-phosphonobutyric acid amide monosodium salt, N-hydroxy-N-dec-9-enyl-3-oxo-4-phosphono-butyric acid amide monosodium salt, N-(1-carboxy-3-methylthio-propyl)-N-hydroxy-3-oxo-4-phosphonobutyric acid amide monosodium salt, N-hydroxy-N-(2,2,2-trichlorethyl)-3-oxo-4-phosphono-butyric acid amide monosodium salt, N-decyl-N-hydroxy-3-oxo-4-ethylphosphono-butyric acid amide monosodium salt, N-(2-fluorenyl)-N-hydroxy-3-oxo-4-ethylphosphono-butyric acid amide monosodium salt, N-(1-adamantyl)-N-hydroxy-3-oxo-4-ethyl-phosphono-butyric acid amide monosodium salt, N-(1,4-dioxane-2-yl)-N-hydroxy-3-oxo-4-ethylphosphonobutyric acid amide mono-sodium salt, N-(N-(2,4-dimethyl-phenyl)-carbamoyl)-N-hydroxy-3-oxo-4-ethylphosphono-butyric acid amide-monosodium salt, N-(3-methyl-hex-2-yl)-N-hydroxy-3-oxo-4-diethylphosphono-butyric acid amide, N-meta-Tolyl-N-hydroxy-3-oxo-4-diethylphosphono-butyric acid amide, N-(3-acetylaminopropyl)-N-hydroxy-3-oxo-4-diethylphosphono-butyric acid amide, N-(2-pyrrolidone-4-yl)-N-hydroxy-3-oxo-4-diethylphosphono-butyric acid amide, N-(2-(methylsulfoxido)-ethyl)-N-hydroxy-3-oxo-4-diethylphosphonobutyric acid am-ide, N-dodecyl-N-hydroxy-3-oxo-4-dimethylphosphinoxido-butyric acid amide, N-papa-hydroxyphenyl-N-hydroxy-3-oxo-4-dimethylphosphinoxido-butyric acid amide, N-(2-propionylethyl)-N-hydroxy-3-oxo-4-dimethylphosphinoxido-butyric acid amide, N-(1-carboxy-2-(3,4-dihydroxyphenyl)-ethyl)-N-hydroxy-3-oxo-4-dimethyl-phos-phinoxido-butyric acid amide, N-(3-phosphonopropyl)-N-hydroxy-3-oxo-4-dimethylphosphinoxido-butyric acid amide monosodium salt, N-(3-ethyl-4-methyl-pentyl)-N-hydroxy-3-oxo-4-(P-methyl-phosphinato)-butyric acid amide, N-(3-hydroxy-3-phenyl-propyl)-N-hydroxy-3-oxo-4-(P-methyl-phosphinato)-butyric acid amide, N-(2-(2-methoxy-ethoxy)-ethyl)-N-hydroxy-3-oxo-4-(P-methyl-phosphinato)-butyric acid amide, N-(4-imidazolyl-methyl)-N-hydroxy-3-oxo-4-(P-methyl-phosphinato)-butyric acid am-ide, N-(2-(7-(2-(N,N-diethylamino)-ethoxy)-fluoren-9-on-2-yloxy)-ethyl)-N-hydroxy-3-oxo-4-(P-methyl-phosphinato)-butyric acid amide, N-hydroxy-4-phosphono-butyric acid amide monosodium salt, N-hydroxy-4-(P-methyl-phosphinato)-butyric acid amide monosodium salt, N-hydroxy-N-methyl-3-oxo-4-(P-methyl-phosphinato)-butyric acid amide monosodium salt, N-hydroxy-3-oxo-4-(P-methyl-phosphinato)-butyric acid amide-monosodium salt, N-hydroxy-N-methyl-3-oxo-4-phosphono-butyric acid amide-monosodium salt, N-hydroxy-3-oxo-4-phosphono-butyric acid amide-monosodium salt, N-hydroxy-4-diphenylphosphono-butyric acid amide, N-hydroxy-N-phenyl-4-diphenylphosphono-butyric acid amide, N-hydroxy-N-benzyl-4-phosphono-butyric acid amide monosodium salt, N-hydroxy-N-benzyl-3-oxo-4-dimethylphosphonobutyric acid amide, N-hydroxy-4-(diethylphosphono)-butyric acid amide, N-hydroxy-N-methyl-4-(diethylphosphono)-butyric acid amide, N-hydroxy-4-phosphono-N-hydroxybutyric acid amide, N-hydroxy-N-methyl-4-phosphono-butyric acid amide, N-hydroxy-3-oxo-4-(diethylphosphono)-butyric acid amide), N-hydroxy-N-methyl-3-oxo-4-(diethylphosphono)-butyric acid amide, N-hydroxy-3-oxo-4-phosphono-butyric acid amide), N-hydroxy-N-methyl-3-oxo-4-phosphono-butyric acid amide), N-hydroxy-3-oxo-4-phosphonobutyric acid amide, N-hydroxy-N-methyl-3-oxo-4-phosphonobutyric acid amide, N-hydroxy-4-oxo-4-(P-methyl-phosphonato) butyric acid amide, N-hydroxy-4-ethylphosphonobutyric acid amide.
6. Compounds according to one of the preceding claims characterized in that they are se-lected from the group consisting of N-hydroxy-4-phosphonobutyric acid amide mono-sodium salt and N-hydroxy-N-methyl-4-phosphonobutyric acid amide monosodium salt.
7. Pharmaceutical preparation, characterized by an effective content of an at least one organophosphorus compound according to one of claims 1 to 6 together with a pharmaceutically acceptable excipient.
8. Pharmaceutical preparation according to claim 7, characterized by at least one further pharmaceutical active ingredient.
9. Pharmaceutical preparation according to one of claims 7 or 8, characterized by one or more ingredients out of the group which consists of sulfonamide, sulfadoxin, artemisinin, atovaquon, chinin, chloroquine, hydroxychloroquin, mefloquin, halofantrin, pyrimethamine, armesin, tetracycline, doxycyclin, proguanil, metronidazol, praziquan-til, niclosamide, mebendazol, pyrantel, tiabendazole, diethylcarbazin, piperazin, pyrivi-num, metrifonate, oxamniquin, bithionol and suramin.
10. Use of organophosphorus Compounds according to one of claims 1 to 6 for the treat-ment of infectious processes in humans and animals caused by viruses, bacteria, fungi or parasites and as a fungicide, bactericide or herbicide in plants.
11. Use according to claim 10 for the treatment of infections caused by bacteria, viruses, fungi or uni- or multi-cellular parasites.
12. Use according to claim 10 for the treatment of infections caused by bacteria selected from the group consisting of bacteria which are selected from the group consisting of Bacteria of the family Propionibacteriaceae, in particular the genus Propionibacterium, in particular the species Propionibacterium acnes; bacteria of the family Actinomyceta-ceae, in particular the genus Actinomyces; bacteria of the genus Corynebacterium, in particular the species Corynebacterium diphteriae and Corynebacterium pseudotuber-culosis; bacteria of the family Mycobacteriaceae, the genus Mycobacterium, in particu-lar the species Mycobacterium leprae, Mycobacterium tuberculosis, Mycobacterium bovis and Mycobacterium avium; bacteria of the family Chlamydiaceae, in particular the species Chlamydia trachomatis and Chlamydia psittaci; bacteria of the genus Liste-ria, in particular the species Listeria monocytogenes; bacteria of the species Ery-sipelthrix rhusiopathiae; bacteria of the genus Clostridium; bacteria of the genus Yer-sinia, the species Yersinia pestis, Yersinia pseudotuberculosis, Yersinia enterocolitica and Yersinia ruckeri; bacteria of the family Mycoplasmataceae, the genus Mycoplasma and Ureapiasma, in particular the species Mycoplasma pneumoniae; bacteria of the ge-nus Brucella; bacteria of the genus Bordetella; bacteria of the family Neiseriaceae, in particular the genuses Neisseria and Moraxella, in particular the species Neisseria meningitides, Neisseria gonorrhoeae and Moraxella bovis; bacteria of the family Vi-brionaceae, in particular the genuses Vibrio, Aeromonas, Plesiomonas and Photobacte-rium, in particular the species Vibrio cholerae, Vibrio anguillarum and Aeromonas sal-monicidas; bacteria of the genus Campylobacter, in particular the species Campylobac-ter jejuni, Campylobacter coli and Campylobacter fetus; bacteria of the genus Helico-bacter, in particular the species Helicobacter pylori; bacteria of the families Spirochae-taceae and the Leptospiraceae, in particular the genus Treponema, Borrelia and Lepto-spira, in particular Borrelia burgdorferi; bacteria of the genus Actinobaeillus; bacteria of the family Legionellaceae, the genus Legionella; bacteria of the family Rickettsiaceae and family Bartonellaceae; bacteria of the genus Nocardia and Rhodococcus;
bacteria of the genus Dermatophilus; bacteria of the family Pseudomonadaceae, in particular the genuses Pseudomonas and Xanthomonas; bacteria of the family Enterobacteriaceae, in particular the genuses Escherichia, Klebsiella, Proteus, Providencia, Salmonella, Serra-tia and Shigella; bacteria of the family Pasteurellaceae, in particular the genus Haemo-philus; bacteria of the family Micrococcaceae, in particular the genus Micrococcus and Staphylococcus; bacteria of the family Streptococcaceae, in particular the genus Strep-tococcus and Enterococcus and bacteria of the family Bacillaceae, in particular the ge-nus bacillus and clostridium, and in the helicobacter eradication therapy of ulcers of the gastro-intestinal tract.
13. Use according to claim 10 for the treatment of infections caused by viruses selected from the group consisting of viruses of the parvoviridae, in particular parvo viruses, de-pendo viruses, denso viruses, viruses of the genus adenoviridae, in particular adeno vi-ruses, mastadeno viruses, aviadeno viruses, viruses of the genus papovaviridae, in par-ticular papova viruses, in particular papilloma viruses (so called wart viruses), polyoma viruses, in particular JC-virus, BK-virus, and miopapova viruses, viruses of the genus herpes viridae, in particular herpes simplex viruses, the varizella-zoster viruses, human cytomegalo virus, Epstein-Barr viruses, human herpes virus 6, human herpes virus 7;
human herpes virus 8, viruses of the genus poxviridae, in particular pox viruses, ortho-pox, parapox, molluscum contagiosum virus, avipox viruses, capripox viruses, lepori-pox viruses, primary hepatotropic viruses, in particular hepatitis viruses, such as hepati-tis A viruses, hepatitis B viruses, hepatitis C viruses, hepatitis D viruses, hepatitis E vi-ruses, hepatitis F viruses, hepatitis G viruses, hepadna viruses, in particular all hepatitis viruses, such as hepatitis B virus, hepatitis D viruses, viruses of the genus picornaviri-dae, in particular picorna viruses, all entero viruses, all polio viruses, all coxsackie vi-ruses, all echo viruses, all rhino viruses, hepatitis A virus, aphtho viruses, viruses of the genus Calciviridae, in particular hepatitis E viruses, viruses of the genus Reoviridae, in particular reo viruses, orbi viruses, rots viruses, viruses of the genus togaviridae, in par-ticular toga viruses, alpha viruses, rubi viruses, pesti viruses, rubella virus, viruses of the genus flaviviridae, in particular flavi viruses, FSME virus, hepatitis C
virus, viruses of the genus orthomyxoviridae, in particular influenza viruses, viruses of the genus Paramyxoviridae, in particular paramyxo viruses, morbilli virus, pneumo virus, measles virus, mumps virus, viruses of the genus rhabdoviridae, in particular rhabdo viruses, ra-bies virus, lyssa virus, viscula stomatitis virus, viruses of the genus corona viridae, in particular corona viruses, viruses of the genus bunyaviridae, in particular bunya viruses, nairo virus, phlebo virus, uuku virus, hanta virus, viruses of the genus arenaviridae, in particular arenaviruses, lymphocytic choriomeningitis virus, viruses of the genus retro-viridae, in particular retro viruses, all HTL viruses, human T-cell leukaemia virus, on-corna viruses, spuma viruses, lenti viruses, all HI-viruses, viruses of the genus filoviri-dae, in particular Marburg and Ebola virus, Slow viruses, prions, onko viruses and leu-kemia viruses.
14. Use according to claim 10 for the prophylactics and treatment of infections caused by unicellular parasites, namely pathogens of malaria, the sleeping sickness, the Chagas' disease, the toxoplasmosis, amoebic dysentery, leishmaniasis; trichomoniasis, pnema-cystosis, balantidiosis, cryptosporidiosis, sarcocystosis, acanthamebiasis, naegleriasis, coccidiosis, giardiasis and lambliosis.
15. Method for therapeutic and prophylactic treatment of infectious diseases caused by bacteria, fungi or parasites wherein a therapeutically effective amount of a compound according to one of claims 1 to 6 is administered to a person being taken ill with an in-fection caused by bacteria, fungi or parasites.
16. Method for combating undesired plant growth, characterized in that useful plants or their area under cultivation are treated with an active amount of a compound according to one of claims 1 to 6 or with an agent containing such a derivative.
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US10758553B2 (en) 2014-09-12 2020-09-01 UNION therapeutics A/S Antibacterial use of halogenated salicylanilides
US11285164B2 (en) 2014-09-12 2022-03-29 UNION therapeutics A/S Antibacterial use of halogenated salicylanilides
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US11331327B2 (en) 2014-09-12 2022-05-17 UNION therapeutics A/S Antibacterial use of halogenated salicylanilides
US10463680B2 (en) 2015-05-29 2019-11-05 UNION therapeutics A/S Halogenated salicylanilides for treating clostridium infections
US10857164B2 (en) 2015-05-29 2020-12-08 UNION therapeutics A/S Halogenated salicylanilides for treating Clostridium infections
US11529361B2 (en) 2015-05-29 2022-12-20 UNION therapeutics A/S Halogenated salicylanilides for treating Clostridium infections
US11419834B2 (en) 2019-02-25 2022-08-23 Rhode Island Hospital Methods for treating diseases or infections caused by or associated with H. pylori using a halogenated salicylanilide

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