Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Reexamination Certificate
1997-07-18
2002-01-29
Gitomer, Ralph (Department: 1623)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
C514S844000, C514S860000, C514S863000, C514S864000, C536S120000, C536S123120, C536S124000
Reexamination Certificate
active
06342486
ABSTRACT:
The present invention is directed to polymer glucan ether derivatives, to a method for the manufacturing of such glucan ether derivatives as well as to the use of these glucan ether derivatives.
Glucan is a 1,3-beta-polyglucose and is obtained by an alkaline and acid pulping from yeast cells, as this is described, for example, in the U.S. Pat. No. 5,397,773, the U.S. Pat. No. 5,250,436 or the U.S. Pat. No. 5,223,491.
The main disadvantage of the thus isolated glucan is that the glucan has an extremely low solubility in aqueous systems, so that it was only a limited use, for example, in aqueous pharmaceutical and/or cosmetical preparations.
The present invention has the object of providing a polymer compound on the basis of glucan, this polymer compound having an essentially better solubility in aqueous systems than glucan.
This object is realized according to the invention by a polymer glucan ether derivative with the significant characteristics of patent claim
1
.
The inventive polymer glucan ether derivatives have, in addition to the monomer units of the formula I, also such monomer units of the general formula II.
Hereby the monomer units of the formula I are connected with the monomer units of the formula II by a 1,3-beta-glycosidic bond, whereby in formula II
X means a —CH
2
—COO-group, a —CH
2
—CH
2
—COO-group, a
and/or a —CH
2
—CH
2
—SO
3
-group and Me means hydrogen, an alkali- and/or an alkaline-earth metal.
The inventive polymer glucan ether derivatives have a superior water solubility, whereby, depending on the group X and on the group Me in formula II, this water solubility is higher by the factor 100 to about 500 than the water solubility of the glucan. This extremely high water solubility of the inventive glucan ether derivatives, which absolutely lies at up to 80 g per liter of water, leads to the fact that the inventive glucan ether derivatives can be easily used as active substance in pharmaceutical and/or cosmetical preparations, whereby such pharmaceutical and/or cosmetical preparations are applied preferably in a topical manner and used for the therapy and/or the prophylaxis of skin diseases, skin damages, skin irritations and skin aging, as this is subsequently explained in detail.
The inventive glucan ether derivatives can also be manufactured in a relatively simple and very gentle way, as this is subsequently described in the inventive method.
The inventive glucan ether derivatives preferably have a molecular weight of between 20,000 and 2,000,000, preferably between 50,000 and 500,000.
The good water solubility of the inventive glucan ether derivatives does not only depend on the group designated with X and Me and mentioned above in the formula II, but also on the average degree of substitution, whereby the average degree of substitution for the inventive glucan ether derivatives varies between 0.4 and 0.9, preferably between 0.6 and 0.8. Particularly when the medium average degree of substitution is 0.75 and when in the formula II X means a —CH
2
—COO-group and Me means sodium, such a carboxymethyl glucan sodium has a perfect water solubility which lies in the range of about 40 g/l of water. For that reason this special glucan ether derivative is preferably used for the manufacturing of topically applicable, pharmaceutical and/or cosmetical composition, as this is subsequently explained in detail.
In respect to the inventive glucan ether derivatives, the residue designated with Me in the formula II can basically mean hydrogen, an alkali metal and/or an alkaline-earth metal. Particularly when in formula II Me means an alkali metal, preferably sodium, such a concrete glucan ether derivative has a high skin tolerance, so that this glucan ether derivative does not cause skin irritations, even not for sensitive users.
This is also the case for such glucan ether derivatives for which in the formula II X means a —CH
2
—COO-group and/or the —CH
2
—C
2
—SO
3
-group, whereby it could be noted that these specific glucan ether derivatives furthermore have, in addition to the good water solubility and high skin tolerance, ideal characteristics of an active substance, so that such glucan ether derivatives are used preferably in topically applicable, pharmaceutical and/or cosmeticate preparations which are used for the therapy and/or the prophylaxis of skin diseases, akin damages, skin irritations and skin aging.
The present invention is furthermore directed to a method with which the above mentioned glucan ether derivatives can be manufactured in a particularly simple way.
This object is realized according to the invention by a method with the significant characteristics of patent claim
1
.
The inventive method for the manufacturing of polymer glucan ether derivatives comprising in addition to the monomer units of the formula I also such monomer units of the general formula II,
whereby the monomer units of the formula I are connected with the monomer units of the formula II by a 1,3-beta-glycosidic bond and whereby in formula II
X means a —CH
2
—COO-group, a —CH
2
—CH
2
—COO-group, a
and/or a —CH
2
—CH
2
—SO
3
-group and Me means hydrogen, an alkali- and/or an alkaline-earth metal, provides that
a) a purified and mainly lipid-free glucan is treated in a low alcohol, preferably in isopropanol, by adding an alkaline solution,
b) hereafter a part of the alkaline solution is removed,
c) the emerging suspension is heated to a temperature of between 40° C. and 60° C. and subsequently converted at this temperature into a glucan ether derivative by adding an aqueous solution of a salt of a haloacid or a halogen sulpho acid of the following formulas III
whereby in the formulas III Y means a halogen and Me means an alkali- and/or alkaline-earth metal,
d) after a reaction time of one hour to four hours the thus formed glucan ether derivative is washed and
e) the washed glucan ether derivative is gently dried.
Firstly, the inventive method has the essential advantage that it can be carried out in a relatively simple way and with a low requirement of equipments. Moreover, it was noted that, according to the above described inventive method, the polymer glucan ether derivatives indicated in the formulas I and II can be manufactured in a particular gentle way and with a high purity, so that correspondingly the inventive glucan ether derivatives are rapidly available. In the inventive method undesired side reactions do also not occur, as for example an undesired splitting of the 1,3-beta-glycosidic bond, which leads to the fact that the inventive glucan ether derivatives can be reproducibly manufactured and that they do not comprise undesired side products. The inventive glucan ether derivatives can thus be perfectly used for pharmaceutical and/or cosmetical preparations, as this is subsequently described in detail.
Generally in the inventive method the treatment, which is mentioned in the above indicated step a), of the purified and mainly lipid-free glucan, can be carried out at any temperature, whereby, however, it is particularly advantageous when this treatment of the purified and mainly lipid-free glucan is carried out at room temperature, meaning at a temperature range of between about 16° C. and 22° C. This has the corresponding advantage that undesired side reactions are avoided already in the first reaction step a) of the inventive manufacturing method, so for example an undesired hydrolysis of the 1,3-beta-glycosidic bond, so that correspondingly the reproducibility and the yield of the inventive method is furtherly improved.
If in the inventive method the above mentioned reaction step indicated under point a) is carried out at room temperature, the reaction time is varied, between about 10 hours and 25 hours, preferably between 12 hours and 20 hours, depending on the yield to be obtained of the polymer glucan ether derivative to be synthesized and its purity.
In the inventive method it is described for the above mentioned first reaction step a) that the purified and mainly lipid-free glucan is suspended in a low alcohol. Herefore a C
1
-C
4
-alcohol, preferably
Suter Franz
Zülli Fred
Gitomer Ralph
Khare Devesh
Mibelle AG Cosmetics
Proskauer Rose LLP
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