Phosphorous organic compounds and their use

Details Phosphorous organic compounds and their use Phosphorous organic compounds and their use

2002-09-11

2004-11-02

Vollano, Jean F. (Department: 1621)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Phosphorus containing other than solely as part of an...

C562S808000, C564S014000, C568S008000

Reexamination Certificate

active

06812224

ABSTRACT:

The invention relates to phosphorous organic compounds and their salts, esters, and amides as well as their use for preparing pharmaceutical compositions for 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 phosphorous organic compounds comprise phosphinoyl derivatives, phosphinic acid derivatives and phosphonic 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 efficacy but in contrast to other pharmaceutical compositions and plant protective agents, contain reduced side effects and lower environmental impact and therefore represent a lower risk to health for humans.
The object of the present invention is therefore to provide a substance which can be universally used in infections by viruses, bacteria, fungi, and parasites in humans and animals and as 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, bactericidal and herbicidal effect in plants.
The phosphorous organic compounds according to the invention correspond to general formula (I):
in which R
1
and R
2
are the same or different and are selected from the group, which consists of hydrogen, substituted and unsubstituted alkyl, substituted and unsubstituted hydroxyalkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted alkinyl, substituted and unsubstituted aryl, substituted and unsubstituted acyl, substituted and unsubstituted cycloalkyl, substituted and unsubstituted aralkyl, substituted and unsubstituted heterocyclic radicals, halogen, OX
1
and OX
2
,
wherein X
1
and X
2
may be the same or different and are selected from the group, which consists of hydrogen, substituted and unsubstituted alkyl, substituted and unsubstituted hydroxyalkyl, substituted and unsubstituted alkenyl, substituted and unsubstituted alkinyl, substituted and unsubstituted aryl, substituted and unsubstituted acyl, substituted and unsubstituted cycloalkyl, substituted and unsubstituted aralkyl, substituted and unsubstituted heterocyclic radicals, B is selected from the group, which consists of ether group (II)
wherein A
1
and A
2
, out of which A
2
also may be absent, are the same or different and are selected from the group, which consists of alkylene radicals, alkenylene radicals and hydroxyalkylene radicals, keto group (III)
wherein A
3
and A
4
, out of which one or both may be absent, are the same or different, are selected from the group, which consists of alkylene radicals, alkenylene radicals and hydroxyalkylene radicals, and 5 and 6 membered cyclic, in particular heterocyclic compounds, which contain additionally to carbon at least one heteroatom as a ring member, wherein the heteroatom is selected from the group, which consists of oxygen and nitrogen,
wherein R
3
and R
4
are the same or different and are selected from the group, which consists of hydrogen, substituted and unsubstituted alkyl having up to 26 carbon atoms, substituted and unsubstituted hydroxyalkyl having up to 26 carbon atoms, substituted and unsubstituted aryl, substituted and unsubstituted acyl, substituted and unsubstituted aralkyl, substituted and unsubstituted alkenyl having up to 26 carbon atoms, substituted and unsubstituted alkinyl having up to 26 carbon atoms, substituted and unsubstituted cycloalkyl, substituted and unsubstituted heterocyclic radicals, halogen, OX
3
or OX
4
, wherein X
3
or X
4
may be the same or different and are selected from the group, which consists of hydrogen, substituted and unsubstituted alkyl having up to 26 carbon atoms, substituted and unsubstituted hydroxyalkyl having up to 26 carbon atoms, substituted and unsubstituted aryl, substituted and unsubstituted aralkyl, substituted and unsubstituted alkenyl having up to 26 carbon atoms, substituted and unsubstituted alkinyl having up to 26 carbon atoms, substituted and unsubstituted cycloalkyl, substituted and unsubstituted heterocyclic radicals, 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 system, ammonium, substituted ammonium and ammonium compounds which derive from ethylene diamine or amino acids,
and their pharmaceutically acceptable salts, esters and amides and salts of the esters.
Compounds which correspond to formula (IV) are particularly preferred
wherein
R
2
is selected from the group, which consists of acetyl and formyl,
A
1
is selected from the group, which consists of methylene, ethylene, ethenylene, hydroxyethylene, 2-hydroxypropylene, and
R
3
is selected from the group, which consists of hydrogen, methyl, ethyl, hexadecyl, octadecyl and OX
3
, and X
3
and X
4
are selected from the group, which consists of hydrogen, sodium, potassium, methyl, ethyl, hexadecyl, and octadecyl and, as far as both are present, may be the same or different.
Preferably the chain —A
1
—O—C(ZY)— consists of one oxygen atom and two or three carbon atoms (substituents not included), particularly preferably two carbon atoms.
Out of the ether compounds those compounds are particularly preferred which are selected from the group, which consists of ((N-formyl-N-hydroxyamino)-methoxy)-methylphosphonic acid disodium salt, ((N-acetyl-N-hydroxyamino)-methoxy)-methyl phosphonic acid disodium salt, (2-(N-formyl-N-hydroxyamino)-etheneoxy)methylphosphonic acid disodium salt, (2-(N-acetyl-N-hydroxyamino)etheneoxy)-methyl-phosphonic acid disodium salt, (3-(N-formyl-N-hydroxyamino)-2-hydroxypropoxy)-methylphosphonic acid disodium salt, (3-(N-acetyl-N-hydroxyamino)-2-hydroxypropoxy)-methylphosphonic acid disodium salt.
Furthermore compounds are preferred, which correspond to formula (V)
wherein
R
2
is selected from the group, which consists of acetyl and formyl,
A
1
is selected from the group, which consists of methylene, ethylene, ethenylene, hydroxymethylen, hydroxyethylene and 2-hydroxypropylene,
A
2
is absent or methylene,
R
3
is selected from the group, which consists of hydrogen, methyl, ethyl, hexadecyl, octadecyl and OX
3
, and
X
3
and X
4
are selected from the group, which consists of hydrogen, sodium, potassium, methyl, ethyl, hexadecyl and octadecyl and, as far as both are present, may be the same or different.
Preferably the chain —A
1
—CO—A
2
— consists of two to four carbon atoms (substituents not included), particularly preferably of three carbon atoms.
Out of these compounds 2-(N-formyl-N-hydroxyamino)-1-oxoethylphosphonic acid disodium salt, 2-(N-acetyl-N-hydroxyamino)-1-oxoethylphosphonic acid disodium salt, 3-(N-formyl-N-hydroxyamino)-1-oxopropylphosphonic acid disodium salt, 3-(N-acetyl-N-hydroxyamino)-1-oxopropylphosphonic acid disodium salt, 3-(N-formyl-N-hydroxyamino)-1-oxo-2-propenylphosphonic acid disodium salt, 3-(N-acetyl-N-hydroxyamino)-1-oxo-2-propenylphosphonic acid disodium salt, 4-(N-formyl-N-hydroxyamino)-1-oxo-3-hydroxybutylphosphonic acid disodium salt, 4-(N-acetyl-N-hydroxyamino)-1-oxo-3-hydroxybutylphosphonic acid disodium salt, 3-(N-formyl-N-hydroxyamino)-2-oxopropylphosphonic acid disodium salt, 3-(N-acetyl-N-hydroxyamino)-2-oxoproylphosphonic acid disodium salt, 4-(N-formyl-N-hydroxyamino)-3-oxo-2-hydroxy-2-methylbutylphosphonic acid disodium salt, 4-(N-acetyl-N-hydroxyamino)-3-oxo-2-hydroxy-2-methylpropylphosphonic acid disodium salt, 4-(N-formyl-N-hydroxyamino)-3-oxo-2-hydroxy-2-(hydroxymethyl)-butyl-phosphonic acid disodium salt, 4-(N-acetyl-N-hydroxyamino)-3-oxo-2-hydroxy-2-(hydroxymethyl)-propylphosphonic acid disodium salt prove to be particularly preferred.
In the cyclic compounds the amino group and the phosphorus

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