Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Radical -xh acid – or anhydride – acid halide or salt thereof...
Reexamination Certificate
2000-06-15
2001-08-14
Carlson, Karen Cochrane (Department: 1653)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Radical -xh acid, or anhydride, acid halide or salt thereof...
C514S566000, C514S836000, C424S409000, C424S405000, C604S290000, C604S294000
Reexamination Certificate
active
06274625
ABSTRACT:
This invention relates to the use of an amino acid derivative as an anti-fungal and/or anti-bacterial compound.
Compounds having anti-microbial activity are desirable in many applications to prevent the growth of microbe contaminants. Anti-microbial activity includes anti-bacterial activity and anti-fungal activity.
Bacteria and fungi are prevalent in the environment. It has been known for very many years that compounds may be active against either bacteria or fungi. This activity is as a result of one of many mechanisms. A few compounds have been isolated which are active against both bacteria and fungi.
Anti-microbial compounds have uses in many applications.
The presence of bacteria and/or fungi may, for example, result in spoilage of food products including agricultural food products such as micronutrients, may contaminate water, either rendering drinking water unfit for consumption or allowing microbial growth in apparatus through which water may be introduced. Furthermore, the presence of bacteria and/or fungi on the fabrics or the body is not desirable and the bacteria and/or fungi may be removed with detergents compositions or personal care products.
WO 97/02010 teaches a number of chelants which may act as anti-bacterial compounds. These chelants are derivatives of succinic acid, glutaric acid and phosphonic acid. WO 97/02010 only teaches that these compounds are anti-bacterial. No indication is given as to whether these compounds have any other anti-microbial, for example anti-fungal, activity.
The present invention aims to provide a compound or a composition having anti-fungal activity or anti-fungal and anti-bacterial activity. Moreover, in a further aspect, the present invention aims to provide a compound or a composition having anti-bacterial activity and preferably improved anti-bacterial activity.
The present invention provides use of an amino acid derivative in free acid or salt form, in which the nitrogen atoms of two or more amino acid molecules are linked by a hydrocarbyl or substituted hydrocarbyl group, as an anti-fungal compound.
The present invention further provides use of an amino acid derivative in free acid or salt form, in which the nitrogen atoms of two or more amino acid molecules are linked by a hydrocarbyl or substituted hydrocarbyl group, as an anti-fungal and anti-bacterial compound.
In a further aspect, the present invention provides use of an amino acid derivative in free acid or salt form, in which the nitrogen atoms of two or more amino acid molecules are linked by a hydrocarbyl or substituted hydrocarbyl group, as an anti-bacterial compound, with proviso that the amino acid derivative is other than a chelant selected from derivatives of succinic acid, glutaric acid and phosphonic acid.
In yet a further embodiment, the present invention provides use of an amino acid derivative in free acid or salt form, in which the nitrogen atoms of two or more amino acid molecules are linked by a hydrocarbyl or substituted hydrocarbyl group, and in which the amino acid derivative is optically active, as an anti-bacterial compound.
The present invention also covers anti-fungal and/or anti-fungal and anti-bacterial compositions comprising the compounds of the present invention including processes for making the same and uses of the same.
The present invention is advantageous as it overcomes the aforementioned problems associated with the prior art.
In the present specification, unless otherwise indicated, the term anti-microbial means having a microbiostatic effect ie. preventing further microbial growth and/or means having a microbicidal effect ie. killing microbes already present.
In the present specification, unless otherwise indicated, the term anti-bacterial means having a bacteriostatic effect ie. preventing further bacterial growth and/or means having a bactericidal effect ie. killing bacteria already present.
In the present specification, unless otherwise indicated, the term anti-fungal means having a fungistatic effect ie. preventing further fungal growth and/or means having a fungicidal effect ie. killing fungi already present.
In the present specification the term microbe is given its usual meaning, for example as defined in
The Penguin Dictionary of Biology, Eighth Edition
(1992). The term microbe includes bacteria, fungi and yeasts.
In the present specification the term bacteria is given its usual meaning, for example as defined in
The Penguin Dictionary of Biology, Eighth Edition
(1992).
In the present specification the term fungi is given its usual meaning, for example as defined in
The Penguin Dictionary of Biology, Eighth Edition
(1992). The term fungi includes yeasts.
Preferably, the compound used in accordance with the present invention has at least one chiral centre.
Preferably, the compound used in accordance without the present invention has at least two chiral centres.
Preferably, the compound used in accordance with the present invention has at least one (S) chiral centre.
Preferably, the compound used in accordance with the present invention has at least two (S) chiral centres.
Preferably, the compound used in accordance with the present invention is optically active.
The compound used in accordance with the present invention may be a derivative of any one or more of the 26 or so naturally occurring amino acids listed in standard textbooks. Preferably, the amino acid or derivative thereof is a naturally occurring amino acid or derivative thereof.
The amino acid derivative may be any one or more of a “neutral” amino acid, a “basic” amino acid or an “acidic” amino acid.
Examples derivatives of neutral amino acids that may be used in the present invention include derivatives of glycine, alanine, valine, leucine, norleucine, phenylalanine, tyrosine, serine, cystine, threonine, methionine, di-iodotyrosine, thyroxine, dibromotyrosine, tryptophan, proline and hydroxyproline.
Examples derivatives of basic amino acids that may be used in the present invention include derivatives of ornithine, arginine, lysine and histidine.
Examples of derivatives of acidic amino acids that may be used in the process of the present invention include derivatives of aspartic acid, glutamic acid and b-hydroxyglutamic acid.
The preferred derivatives of amino acids for the process of the present invention are derivatives of those with two carboxyl groups and one amino group—i.e. the acidic amino acids listed above. Aspartic acid and glutamic acid are the most preferred of the three.
Specific optical isomers, particularly the L-form, are desirable.
Preferably the compound is selected from the group consisting of L-aspartic acid, L-glutamic acid or L-phenylalanine, including derivatives thereof.
In an alternative embodiment, the present invention relates to the uses or compositions described herein, wherein the amino acid derivative is partially or completely substituted by a second amino acid or derivative thereof, said amino acid or derivative thereof being an acid compound (or salt thereof) comprising at least two nitrogen groups and at least one carboxylic acid group (or salt thereof).
Preferably, the second amino acid is an amino acid derivative as described herein.
Preferably, the compound used in accordance with the present invention comprises at least one succinate group.
Preferably, the compound used in accordance with the present invention comprises at least one ethylene bridge linking two or more amino acids.
Preferably, the compound used in accordance with the present invention is ethylenediamine disuccinic acid (EDDS).
Preferably, the compound used in accordance with the present invention is (S,S) ethylenediamine disuccinic acid [(S,S) EDDS].
The term “EDDS” includes racemic EDDS or optically active isomers thereof, such as (S,S)EDDS, and active salts and active derivatives thereof. Preferably the term means (S,S)EDDS or salts thereof. Preferably the EDDS is (S,S)EDDS.
The finding by the applicant that EDDS, derivatives thereof and in particular (S,S) EDDS act as described above, namely as an anti-fungal and/or anti-bacterial agent,
Brewer Mark
Patel Rajeshkumar
Woolley Steve
Associated Octel Company Limited
Carlson Karen Cochrane
Fay Sharpe Fagan Minnich & McKee LLP
Robinson Patricia
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