Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Phosphorus containing other than solely as part of an...
Reexamination Certificate
2000-12-08
2004-01-20
Padmanabhan, Sreeni (Department: 1617)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Phosphorus containing other than solely as part of an...
C514S075000
Reexamination Certificate
active
06680308
ABSTRACT:
This application is a 371 of PCT/EP99/02462, filed Apr. 13, 1999.
The invention relates to the use of organophosphorus compounds and their salts, esters and amides for the therapeutic and prophylactic treatment of infections which are caused by viruses, fungi and parasites in humans and animals. According to the invention the organophosphorus compounds comprise phosphonic acid derivatives, phosphinoyl derivates and phosphinic acid derivatives.
The suitability of aminohydrocarbyl phosphonic acid derivates and some of their esters and salts for use in pharmaceutical compositions is already known. Up until now however only their antimicrobial efficacy against bacteria in humans and animals and against fungi in plants has been described (DE 27 33 658 A1, U.S. Pat. No. 4,143,135, U.S. Pat. No. 4,182,758 and U.S. Pat. No. 4,206,156, U.S. Pat. No. 4,994,447, U.S. Pat. No. 4,888,330, U.S. Pat. No. 4,210,635, U.S. Pat. No. 3,955,958, U.S. Pat. No. 4,196,193, U.S. Pat. No. 4,268,503, U.S. Pat. No. 4,330,529, U.S. Pat. No. 5,189,030, U.S. Pat. No. 3,764,677, U.S. Pat. No. 3,764,676). Furthermore substances from this group have been described as herbicides (U.S. Pat. No. 4,693,742, U.S. Pat. No. 5,002,602, U.S. Pat. No. 4,131,448, U.S. Pat. No. 3,977,860, U.S. Pat. No. 4,062,669), as algaecides (U.S. Pat. No. 3,887,353), as means for regulating plant growth (U.S. Pat. No. 4,127,401, U.S. Pat. No. 4,120,688, U.S. Pat. No. 3,961,934, U.S. Pat. No. 4,431,438, U.S. Pat. No. 3,853,530, U.S. Pat. No. 4,205,977, U.S. Pat. No. 4,025,332, U.S. Pat. No. 3,894,861) and as reagents in dye production (U.S. Pat. No. 4,051,175). In DE 27 33 658 A1 the use of aminohydrocarbyl phosphonic acid derivatives for the treatment of bacterial diseases has been described. Whilst the document speaks of a microbial efficacy against pathogenic microorganisms in the introduction to the description, from the overall context however it is clear that the invention relates exclusively to bacteria. Thus on page 16, second paragraph “antimicrobial efficacy” is defined as “antibacterial efficacy”.
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 therefore represent a lower risk to health for humans.
The object of the present invention is therefore to provide a substance which fulfils the conditions given above in the case of infections caused by viruses, fungi and parasites in humans and animals.
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, fungi and unicellular and multicellular parasites. In the context of this invention the strictly scientific definition of parasites is to be used. This means that unicellular parasites are understood to mean protozoa exclusively.
The organophosphorus compounds used according to the invention correspond to the 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 radical, halogen, OX
1
and OX
2
, wherein X
1
and X
2
can 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,
A is selected from the group which consists of an alkylene radical, an alkenylene radical and a hydroxyalkylene radical,
R
3
and R
4
are selected independently 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 acyl, substituted and unsubstituted aralkyl, substituted and unsubstituted C
1-26
-alkenyl, substituted and unsubstituted C
1-26
-alkinyl, substituted and unsubstituted cycloalkyl, substituted and unsubstituted heterocyclic radical, halogen, OX
3
and OX
4
,
wherein X
3
and X
4
are selected independently from the group which consists of hydrogen, substituted and unsubstituted C
1-26
-alkyl, substituted and unsubstituted hydroxyl-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
-alkinyl, substituted and unsubstituted cycloalkyl, substituted and unsubstituted heterocyclic radical, 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 esters. Phosphonic acid derivatives are particularly preferred.
In particular compounds which contain the following Formula (II) are suitable:
wherein,
X
1
is selected from the group which consists of hydrogen, substituted or unsubstituted acyl, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, substituted or unsubstituted aralkyl, substituted or unsubstituted cycloalkyl, substituted and unsubstituted heterocyclic radical;
R
2
, R
3
, R
4
and A contain the same meaning as in Formula (I)
A is particularly preferably a chain of three carbon atoms which bind the nitrogen atom to the phosphorus atom.
Compounds of Formula (II) are particularly preferred in which R
2
=acyl, in particular an acetyl, R
3
=hydrogen, methyl or ethyl, R
4
=hydrogen, methyl, ethyl or OX
4
with X
4
=hydrogen, sodium, potassium, methyl, ethyl, X
1
═H and A=alkylene, alkenylene or hydroxyalkylene. Particularly good results are achieved with R
2
=formyl or acetyl and A=propylene, propenylene or hydroxypropylene.
Furthermore compounds are particularly preferred in which R
3
is an alkyl, hydroxyalkyl, alkinyl, or alkenyl group with 16 or 18 carbon atoms or OX
3
, wherein X
3
is an alkyl, alkinyl, hydroxyalkyl or alkenyl group with 16 or 18 carbon atoms, R
4
is an alkyl, alkinyl, hydroxyalkyl or alkenyl group with 16 or 18 carbon atoms or OX
4
, wherein X
4
is an alkyl, alkinyl, hydroxyalkyl or alkenyl group with 16 or 18 carbon atoms.
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 thioacid or imidic acid corresponding to the individually present acids, or from an organic sulphonic acid, wherein these acids comprise in each case aliphatic, aromatic and/or heterocyclic groups in the molecule and carbamoyl or carbamimidoyl.
Suitable examples of these acyl groups will be given below.
Acyl radicals originating from an aliphatic acid are designated as aliphatic acyl groups and include:
Alkanoyl (for example formyl, acetyl, propionyl, butyryl, isobutyryl, valeryl, isovaleryl, pivaloyl etc.);
Alkenoyl (for example acryloyl, methacryloyl, crotonoyl etc.);
Alkylthioalkanoyl (for example methylthioacetyl, ethylthioacetyl etc.);
Alkane sulphfonyl (for example mesyl, ethane sulphonyl, propane sulphonyl etc.);
Alkoxycarbonyl (for example methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxycarbon
Hui San-ming
Padmanabhan Sreeni
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