Organic compounds -- part of the class 532-570 series – Organic compounds – Silicon containing
Reexamination Certificate
1998-03-24
2001-03-06
Jones, Dameron (Department: 1625)
Organic compounds -- part of the class 532-570 series
Organic compounds
Silicon containing
C556S401000, C556S404000, C424S400000, C424S401000
Reexamination Certificate
active
06197986
ABSTRACT:
The present invention concerns compounds containing biologically active silicon, which are under solid form, as well as pharmaceutical and cosmetic composition containing these compounds.
BACKGROUND OF THE INVENTION
The compounds containing biologically active silicon are organo silicon compounds and more especially silanols bearing several Si—OH bonds. Silanols are described in the prior art as constituting a form of silicon assimilable by the organism, given that they have the property of existing as oligomer soluble form in aqueous solution with a low molecular weight (EP-0 289 366).
Until now, biologically active silicon compounds have been available only as diluted solutions, since they polymerize when too much concentrated, and until now, all attempts to obtain these compounds by eliminating water have invariably led to their polymerization and thus to the loss of their biological properties. The fact that these organo silicon compounds of the prior art exist only as diluted solutions limits their use and particularly make impossible their incorporation in cosmetic or pharmaceutical compositions under non aqueous form or tablets or pills to be administered orally.
Thus, to notably remedy these drawbacks, one of the main goal of the invention is to obtain a biologically active organo silicon compound under a solid form.
SUMMARY OF THE INVENTION
The organo silicon compound according to the invention has the following general formula (I):
R
4
—Si (OR
1
) (OR
2
) (R
3
) (I)
wherein
R
1
and R
2
each one independently represent an atom of hydrogen or an alkyl group,
R
3
represents an hydrogen atom, an hydroxyl group, an amine group, an alkyl group, an alcoxy or a carboxylate group,
and at least one of the OR
1
, OR
2
or R
3
groups represents an hydroxyl group,
R
4
represents an alkyl group substituted or not by a functional group such as, notably, an alkyl phosphate group or an alkyl phosphonate group, or any other group for which the R
4
—Si bond is not hydrolyzable, and the said compound:
is under solid form,
and/or is possibly associated with at least one stabilizer,
and/or is possibly associated with at least one dispersant.
Preferably, the compound according to the invention is a compound of formula (I) wherein R
4
represents a diethylphosphatoethyl group and/or OR
1
, OR
2
and R
3
groups represent each an hydroxyl group.
According to an embodiment of the invention, the stabilizer is a carboxylic acid, an amino acid or a derived amino acid, a peptide or a protein, an alcohol or a polyol, a polysaccharide, and/or their salts.
Preferably, the carboxylic acid and/or its salt is aspartic acid, glutamic acid, lactic acid, salicylic acid, theophylline acetic acid, carboxylic pyrrolidinone acid and/or their salts.
Preferably, the amino acid and/or its salt is arginine, serine, threonine, hydroxyproline, acetylmethionine, acetyl tyrosine and/or their salts.
Preferably, the peptide is a polypeptide derived from elastin proteins, spirulina, collagen, or vegetal proteins, e.g. oat or wheat proteins.
Advantageously, this polypeptide is hydrolized elastin proteins, hydrolysed spirulina, hydrolysed collagen, or hydrolysed vegetal proteins, e.g. oat or wheat proteins.
Preferably, the protein is an elastin protein, spirulina protein, collagen protein, or a vegetal protein, e.g. oat or wheat protein.
Advantageously, the polyol is lactose.
Preferably, the polysaccharide is a glycosaminoglycanne, a mucopolysaccharide such as particularly hyaluronic acid, pectin or alginic acid.
According to another embodiment of the invention, the dispersant is a polyamiole, a carbohydrate, a polysaccharide, a polyoxethylene such as polyethylene glycol or a non water soluble (or weakly water soluble) fatty compound e.g. a triglyceride.
Another goal of the invention is to propose a pharmaceutical or a cosmetic composition including such a compound, in association with any suitable excipient, and being administered orally, in order to be used in ambulatory medication which does not require the realization of previous medical treatment.
The invention will be better understood after the lecture of the following detailed description; its purpose is to illustrate and to explain, without limitation, the invention.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS
The compound according to the invention conforms to the general formula (I) wherein R
1
and R
2
each one independently represent an hydrogen atom or an alkyl group, preferably a C
1-4
alkyl group, R
3
represents an hydrogen atom, an hydroxyl group, an amine group, an alkyl group, preferably a C
1-4
alkyl group, an alkoxy group, preferably a C
1-4
alkoxy or carboxylate group preferably bonded to the silicon through an oxygen atom, and at least one of the OR
1
, OR
2
or R
3
group represents an hydroxyl group, R
4
represents a substituted or unsubstituted alkyl group e.g. an alkylophosphate group, preferably a C
1-4
alkyl phosphate or an alkyl phosphonate group preferably a C
1-4
alkyl phosphonate, or any other group for which the R
4
—Si bond is not hydrolyzable, this compound having a main characteristic, which is to be in a solid form. This compound can also, but not necessarily be associated with at least a stabilizer. It can also, but not necessarily, be associated besides, or alternatively with at least one dispersant.
The preferred compounds of the invention are the ones of formula (I) wherein R
4
represents a diethylphosphatoethyl group. Among these compounds, the diethylphosphatoethylsilanetriol can be distinguished as the most preferred compound.
One characteristic of the compound according to the invention is that a part of the substituents of the silicon atom can, in contact with a molecule of water, hydrolyse spontaneously in order to form a supplementary Si—OH bond, which will contribute to reinforce the in vivo activity of the said compounds.
The stabilizer is a polar compound which can form weak bonds (hydrogen bonds) or strong bonds (covalent bonds) with the organo silicon compound. The stabilizer opposes the formation of a siloxane Si—O—Si bond leading to insoluble or slightly water soluble polysiloxanes compounds. It will contribute to avoid the polymerization of the organo silicon compound.
For example, the stabilizer can be a carboxylic acid or its salt, e.g. aspartic acid, glutamic acid, lactic acid, salicylic acid, theophylline acetic acid, pyrrolidone carboxylic acid and/or their salts.
The stabilizer can also be an amino acid or a derived amino acid and/or their salts. Among these amino acids, serine, threonine, hydroxyproline, acetylmetionine, acetyl tyrosine and/or their salts are preferred.
Hydroxyproline is especially interesting, notably because of its regenerating activity of the connective tissue. It is naturally present in great quantity in collagen.
As well, acetyl tyrosine is notably interesting for its role in melanogenesis.
Thus, the stabilizer can also be a peptide or a protein. Among peptides, polypeptides derived from elastin, spirulina, collagen as well as polypeptides derived from vegetal proteins e.g. oat and wheat proteins are preferred. Advantageously, among these polypeptides those which result from the lysis or hydrolysis of proteins have been chosen. Notably, good results in matter of stabilization are obtained with hydrolyzed wheat protein.
As well, the stabilizer can be a protein, and in this case, elastin, spirulina and collagen proteins as well as vegetal proteins e.g. oat and wheat proteins, are preferred.
The stabilizer can also be an alcohol or a polyol such as lactose. The stabilizer can also be a polysaccharide. Among polysaccharides, glucosaminoglycanes, mucopolysaccharides e.g. hyaluronic acid, pectin and alginic acid are preferred.
A good stabilizer, for example, is the above mentioned hyaluronic acid, which is in fact the acidic mucopolysaccharide resulting from the reaction between N-acetyl-glucosamine and the glucuronic acid.
All these compounds are chosen as stabilizers because they have the above mentioned properties, and also because they are commonly used in
Gueyne Jean
Seguin Marie-Christine
EXSYMOL S.A.M.
Jones Dameron
Lydon James C.
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