Drug – bio-affecting and body treating compositions – Preparations characterized by special physical form – Cosmetic – antiperspirant – dentifrice
Reexamination Certificate
2001-10-04
2004-02-03
Krass, Frederick (Department: 1614)
Drug, bio-affecting and body treating compositions
Preparations characterized by special physical form
Cosmetic, antiperspirant, dentifrice
C424S078030, C514S613000, C514S579000, C514S625000, C514S626000, C514S627000, C514S663000, C514S667000, C514S668000, C514S673000
Reexamination Certificate
active
06685953
ABSTRACT:
TECHNICAL FIELD
The present invention relates to dermatologic preparations capable of exerting excellent effects of maintaining normal barrier functions of the horny layer, restoring and reinforcing damaged barrier functions, heightening water retention of the horny layer and remedying skin chapping; and novel diamide derivatives having such effects.
BACKGROUND ART
When the water retention capacity or barrier functions of the horny layer are weakened by some internal or external reasons, the skin suffers from troubles such as chapping and acceleration of aging. It is therefore highly important to maintain and reinforce the water retention capacity and barrier functions of the horny layer for our healthy daily life.
The present applicant has formerly proposed dermatologic preparations comprising an amide derivative represented by the following formula (3):
(wherein, R
a
represents a linear or branched, saturated or unsaturated hydrocarbon group having 10 to 40 carbon atoms, R
b
represents a linear or branched divalent hydrocarbon group having 3 to 39 carbon atoms, R
c
represents a hydrogen atom, a linear or branched, saturated or unsaturated hydrocarbon group having 10 to 40 carbon atoms or an acyl group) as a dermatologic preparation capable of essentially improving (maintaining, reinforcing) the barrier functions of the horny layer (Japanese Patent Application Laid-Open (Kokai) No. 4-128256).
Although these amide derivatives exert the above-described excellent effects, they still involve some problems in miscibility or mixing stability because they do not always have sufficient solubility in bases and solution stability. Moreover, preparation of such amide derivatives requires multi-stage reaction, inevitably causing an increase in their production cost.
An object of the present invention is therefore to provide a compound capable of essentially improving the water retention capacity and barrier functions of the horny layer, having improved miscibility or mixing stability, and being available efficiently at a low cost; and a dermatologic preparation which contains the above-described compound and, by maintaining and reinforcing the water retention capacity and barrier functions of the horny layer, exerts effects of preventing or remedying skin troubles such as chapping, protecting the hair with its penetrated component, improving touch feel of the hair and preventing or remedying chapping of the scalp.
DISCLOSURE OF THE INVENTION
The present invention provides a dermatologic preparation, humectant or skin-barrier-function reinforcing agent, which comprises a diamide derivative represented by the following formula (1):
(wherein R
1
represents a linear or branched hydrocarbon group having 1 to 22 carbon atoms which may be substituted by one or more hydroxy and/or alkoxy groups, R
2
represents a linear or branched divalent hydrocarbon group having 1 to 12 carbon atoms, and R
3
represents a linear or branched divalent hydrocarbon group having 1 to 42 carbon atoms).
The present invention also provides a diamide derivative represented by the following formula (2):
(wherein, R
1
represents a linear or branched hydrocarbon group having 1 to 22 carbon atoms which may be substituted by one or more hydroxy and/or alkoxy groups, R
2
represents a linear or branched divalent hydrocarbon group having 1 to 12 carbon atoms, and R
3a
represents an alkylene group or an alkenylene group having 1 to 4 double bonds, which alkylene or alkenylene group may be linear or branched and has 11 to 42 carbon atoms).
Best Mode for Carrying out the Invention
In the diamide derivatives (1) and (2), preferred as R
1
are linear or branched C
1-22
alkyl groups which may have 1 to 3 substituents selected from a hydroxy group and C
1-6
alkoxy groups. Of these, C
1-18
alkyl groups, C
1-18
mono- or di-hydroxyalkyl groups, (C
1-6
alkoxy-substituted)-(C
1-18
alkyl) groups, and (hydroxy- and C
1-6
alkoxy-substituted)-(C
1-18
alkyl) groups are preferred, of which C
1-18
alkyl groups, C
2-12
mono- or di-hydroxyalkyl groups, (C
1-6
alkoxy-substituted)-(C
2-12
alkyl) groups, and (hydroxy- and C
1-6
alkoxy-substituted)-(C
2-12
alkyl) groups are more preferred. Specific examples include methyl, ethyl, propyl, butyl, hexyl, dodecyl, 2-methylpropyl, 2-ethylhexyl, methyl-branched isostearyl, 2-hydroxyethyl, 9-hydroxynonyl, 2,3-dihydroxypropyl, 2-methoxyethyl, 2-hydroxy-3-methoxypropyl and 9-methoxynonyl groups. Of these, 2-hydroxyethyl, methyl, dodecyl and 2-methoxyethyl groups are more preferred.
As R
2
, linear or branched C
1-12
alkylene groups are preferred, with linear or branched C
2-6
alkylene groups being more preferred. Specific examples include ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, methylmethylene (ethylidene), 1-methylethylene, 2-methylethylene, 1-methyltrimethylene, 2-methyltrimethylene, 1,1-dimethylethylene and 2-ethyltrimethylene groups, of which ethylene and trimethylene groups are more preferred.
In the formula (1), linear or branched divalent hydrocarbon groups having 2 to 34 carbon atoms are preferred as R
3
, with alkylene groups and alkenylene groups having 1 to 4 double bonds each of which may be linear or branched and has 2 to 34 carbon atoms, particularly, alkylene groups and alkenylene groups having 1 to 4 double bonds each of which may be linear or branched and has 2 to 24 carbon atoms being preferred. Specific examples include ethylene, trimethylene, tetramethylene, hexamethylene, heptamethylene, octamethylene, decamethylene, undecamethylene, dodecamethylene, tridecamethylene, tetradecamethylene, hexadecamethylene, octadecamethylene, tricosamethylene, hexacosamethylene, triacontamethylene, 1-methylethylene, 2-ethyltrimethylene, 1-methylheptamethylene, 2-methylheptamethylene, 1-butylhexamethylene, 2-methyl-5-ethylheptamethylene, 2,3,6-trimethylheptamethylene, 6-ethyldecamethylene, 7-methyltetradecamethylene, 7-ethylhexadecamethylene, 7,12-dimethyloctadecamethylene, 8,11-dimethyloctadecamethylene, 7,10-dimethyl-7-ethylhexadecamethylene, 1-octadecylethylene, 9,10-dioctyloctadecamethylene, 8,9-dinonylhexadecamethylene, ethenylene, 1-octadecenylethylene, 7,11-octadecadienylene, 7-ethenyl-9-hexadecamethylene, 7,12-dimethyl-7,11-octadecadienylene, 8,11-dimethyl-7,11-octadecadienylene, 9,10-dioctyl-7,11-octadecadienylene and 8,9-dinonyl-6,10-hexadecadienylene groups. Of these, 7,12-dimethyloctadecamethylene, 7,12-dimethyl-7,11-octadecadienylene, octadecamethylene, octamethylene, decamethylene, undecamethylene and tridecamethylene groups are more preferred.
In the formula (2), preferred as R
3a
are alkylene groups and alkenylene groups having 1 to 4 double bonds each of which may be linear or branched and has 12 to 34 carbon atoms, with alkylene groups and alkenylene groups having 1 to 4 double bonds each of which may be linear or branched and has 12 to 24 carbon atoms being more preferred. Of these, 7,12-dimethyloctadecamethylene, 7,12-dimethyl-7,11-octadecadienylene, octadecamethylene and tridecamethylene groups are still more preferred.
In the diamide derivatives (2) of the present invention, particularly preferred are compounds of the formula (2) having, as R
1
, R
2
and R
3a
, the groups within the above-described more preferred ranges in combination, respectively. In the diamide derivatives (1) to be used for the dermatologic preparations of the present invention, particularly preferred are compounds of the formula (1) having, as R
1
, R
2
and R
3
, groups within the above-described more preferred ranges in combination, respectively.
Particularly preferred examples of the diamide derivatives (1) to be used for the dermatologic preparations of the present invention include:
Particularly preferred examples of the diamide derivatives (2) of the present invention include the above-exemplified compounds (A) to (C), (F) to (J) and (L).
The diamide derivatives (1) to be used for the dermatologic preparations of the present invention can be prepared by a known amide synthesis method. A preparation process, for example, in accordance with the follo
Hoshino Masahide
Kameyama Akiyo
Nishizawa Yoshinori
Saito Hiroaki
Sugai Yoshiya
Kao Corporation
Krass Frederick
Ostrup Clinton
LandOfFree
External preparation compositions does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with External preparation compositions, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and External preparation compositions will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3339786