Organophosphorus compounds and the use thereof

Details Organophosphorus compounds and the use thereof Organophosphorus compounds and the use thereof

2001-05-25

2003-03-18

Tsang, Cecilia (Department: 1626)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

C558S166000, C558S169000, C558S175000

Reexamination Certificate

active

06534489

ABSTRACT:

This invention relates to organophosphorus compounds and to the salts, esters and amides thereof and to the use thereof for the therapeutic and prophylactic treatment of infections in humans and animals which are caused by viruses, bacteria, fungi and parasites, to the use thereof as a fungicide, bactericide and herbicide in plants. According to the invention, the organophosphorus compounds comprise phosphinoyl derivatives, phosphinic acid derivatives and phosphonic acid derivatives.
In order to widen the range of options for treating humans and animals and for protecting plants, there is an urgent requirement to provide agents which are not only highly active but, unlike other pharmaceutical preparations or phytosanitary agents, also exhibit reduced side-effects and thus constitute a reduced risk to human health.
DE 27 33 658 A has already disclosed phosphonic acid derivatives of the formula R
1
—N(OR
2
)—A—P(O)(OH)
2
, in which R
1
denotes hydrogen or acyl, R
2
denotes hydrogen, Ar-lower-alkyl or acyl and A is a lower alkylene, lower alkenylene or lower hydroxyalkylene group, preferably formyl, acetyl or trimethylene, together with the esters and pharmaceutical salts thereof. These compounds are used for the therapeutic treatment of infections which are caused by bacteria.
The object of the present invention is accordingly to provide alternative substances which are usable in infections by bacteria and also in infections by-viruses, fungi and parasites in humans and animals and as a fungicide, bactericide and herbicide in plants and which meet the above-stated requirements.
This object is utterly surprisingly achieved by the group of substances defined in claim
1
. This group of substances exhibits antiinfective action against viruses, bacteria, fungi, uni- and multicellular parasites.
The organophosphorus compounds according to the invention are of the general formula (I):
in which R
1
and R
2
are identical or different and are selected from the group which consists of hydrogen, substituted and unsubstituted C
1-9
alkyl, substituted and unsubstituted hydroxy-C
1-9
-alkyl, substituted and unsubstituted C
1-9
alkenyl, substituted and unsubstituted C
1-9
alkynyl, substituted and unsubstituted aryl, substituted and unsubstituted acyl, substituted and unsubstituted cycloalkyl, substituted and unsubstituted aralkyl, substituted and unsubstituted heterocyclic residue, halogen, OX
1
and OX
2
,
wherein X
1
and X
2
may be identical or different and are selected from the group which consists of hydrogen, substituted and unsubstituted C
1-9
alkyl, substituted and unsubstituted hydroxy-C
1-9
-alkyl, substituted and unsubstituted C
1-9
alkenyl, substituted and unsubstituted C
1-9
alkynyl, substituted and unsubstituted aryl, substituted and unsubstituted acyl, substituted and unsubstituted cycloalkyl, substituted and unsubstituted aralkyl, substituted and unsubstituted heterocyclic residue,
in which A is of the following formula (II):
wherein one or more of the carbon atoms selected from the group C
3
, C
4
, C
5
together with their substituents may also be absent, and at least one substituent present in the range from B
1
to B
10
is a C
3-8
-cycloalkyl-(C
0-9
)-alkyl group, wherein both the C
3-8
cycloalkyl group and the C
0-9
alkyl group may comprise one or more double bonds and one or two carbon atoms of the cycloalkyl group may be replaced by nitrogen, oxygen or sulfur atoms, and wherein both the cycloalkyl group and the alkyl group may be substituted with hydroxy, halogen, amino, oxo groups with branched or unbranched C
1-9
alkyl groups and C
2-9
alkenyl groups, wherein the C
1-9
alkyl group and C
2-9
alkenyl groups may be substituted with hydrogen, hydroxy, amino, halogen and oxo groups, and the remaining substituents B
1
to B
10
present are selected from the group which consists of hydrogen, hydroxy, halogen, amino groups, C
1-26
alkyl residues, C
1-26
alkoxy residues, C
1-26
-alkoxy-C
1-26
-alkyl residues or both substituents of a C atom together form an oxo group, wherein each C
1-26
alkyl residue and each C
1-26
alkoxy residue may be branched or unbranched and be saturated or unsaturated with one or more double bonds and may be substituted with hydroxy, amino, halogen and oxo groups,
in which R
3
and R
4
are identical or different and are selected from the group which consists of substituted and unsubstituted C
1-26
alkyl, substituted and unsubstituted hydroxy-C
1-26
-alkyl, substituted and unsubstituted aryl, substituted and unsubstituted acyl, substituted and unsubstituted cycloalkyl, substituted and unsubstituted aralkyl, substituted and unsubstituted C
1-26
alkenyl, substituted and unsubstituted C
1-26
alkynyl, substituted and unsubstituted cycloalkyl, substituted and unsubstituted heterocyclic residue, halogen, OX
3
and OX
4
,
wherein X
3
and X4 are identical or different and are selected from the group which consists of hydrogen, substituted and unsubstituted C
1-26
alkyl, substituted and unsubstituted hydroxy-C
1-26
-alkyl, substituted and unsubstituted aryl, substituted and unsubstituted aralkyl, substituted and unsubstituted C
1-26
alkenyl, substituted and unsubstituted C
1-26
alkynyl, substituted and unsubstituted cycloalkyl, substituted and unsubstituted heterocyclic residue, a silyl, a cation of an organic and inorganic base, in particular a metal of main groups I, II or III of the periodic system, ammonium, substituted ammonium and ammonium compounds derived from ethylenediamine or amino acids, and the pharmaceutically acceptable salts, esters and amides thereof and salts of the esters.
In particular, compounds of the following formula (III) are suitable:
wherein X
1
is preferably a hydrogen and R
2
an acyl residue, particularly preferably a formyl residue or acetyl residue.
X
3
and X
4
OX
3
and OX
4
, and X
3
and X
4
are preferably hydrogen, a metal of main groups I, II or III of the periodic system, ammonium, substituted ammonium or ammonium compounds derived from ethylenediamine or amino acids. In other words, the salt compounds of the organophosphorus compounds are formed with organic or inorganic bases (for example sodium salt, potassium salt, calcium salt, aluminium salt, ammonium salt, magnesium salt, triethylamine salt, ethanolamine salt, dicyclohexylamine salt, ethylenediamine salt, N,N′-dibenzylethylenediamine salts) as well as salts with amino acids (for example arginine salt, aspartic acid salt, glutamic acid salt etc.) and the like.
The carbon chain of A with the formula (II) preferably consists of three carbon atoms C
1
, C
2
, C
3
.
Further preferred compounds are those in which the carbon chain of A with the formula (II) consists of four carbon atoms C
1
, C
2
, C
3
, C
4
and B
7
and B
8
or both are a hydroxy group. In this case, methylene groups are also preferred for R
3
and R
4
.
It is furthermore preferred that B
1
and B
2
together form an oxo group. In this case, the carbon chain in A consists of four carbon atoms C
1
, C
2
, C
3
, C
4
.
It is furthermore preferred that B
7
and B
8
together form an oxo group. In this case, the carbon chain in A likewise consists of four carbon atoms C
1
, C
2
, C
3
, C
4
.
The carbon chain preferably consists of the 5 carbon atoms C
1
, C
2
, C
3
, C
4
, C
5
, wherein B
1
and B
2
together form an oxo group and at least one substituent of B
9
or B
10
is a hydroxyl group or B
9
and B
10
together also form an oxo group.
Special features of the above definitions and suitable examples thereof are given below:
“Acyl” is a substituent which originates from an acid, such as from an organic carboxylic acid, carbonic acid, carbamic acid or the thio acid or imidic acid corresponding to the above individual acids, or from an organic sulfonic acid, wherein these acids in each case comprise aliphatic, aromatic and/or heterocyclic groups in the molecule together with carbamoyl or carbamimidoyl.
Suitable examples of these acyl groups are given below.
Aliphatic acyl groups are defined as acyl residues originating from an aliphatic acid and include the followin

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