Drug – bio-affecting and body treating compositions – Live hair or scalp treating compositions
Reexamination Certificate
1998-10-13
2001-01-23
Low, Christopher S. F. (Department: 1654)
Drug, bio-affecting and body treating compositions
Live hair or scalp treating compositions
C424S070110, C424S401000, C514S231200, C514S235800, C514S238800, C514S239200, C514S255030, C514S315000, C514S483000, C514S553000, C514S880000, C132S202000, C560S115000
Reexamination Certificate
active
06177067
ABSTRACT:
BACKGROUND OF THE INVENTION
This invention relates to the hair revitalization of mammals and, more particularly, to the use of novel 2,2-dimethylpropanediol derivatives for purposes of hair revitalization.
Conventionally, hair revitalizing tonic compositions containing various components such as certain vitamins, amino acids, female hormones, and plant extracts having a vasodilative effect or an anti-inflammatory effect have been used for the prophylaxis and treatment of alopecia or, prevention or treatment of hair loss. Moreover, a variety of other compounds have also been proposed for use as active ingredients, but they are not always satisfactory from the viewpoint of efficacy. Meanwhile, a large number of 2-substituted glycerol derivatives having antiallergic and anti-inflammatory effects have been synthesized (see, for example, Published Japanese Translation of PCT International Publication No. 501612/'91), and much attention is focused on their excellent effects.
However, there is a still continuing need for a more excellent hair revitalizing tonic composition. Accordingly, it is an object of the present invention to provide a hair revitalizing tonic composition containing, among others, a chemically synthesized compound having a hair growth promotion or stimulation effect, as well as the use of such a compound in a hair revitalizing method.
SUMMARY OF THE INVENTION
The present inventors have synthesized various compounds and examined their hair growth promotion effects. As a result, it has now been found that novel dimethylpropanediol derivatives having two methyl groups at the 2-position have an excellent hair growth promotion effect.
According to the present invention, there is provided a hair revitalizing tonic composition comprising a novel 2,2-dimethylpropanediol derivative of the following formula (I) or a salt thereof which is present in an amount effective for the hair revitalization of mammals, together with a pharmaceutically or cosmetically acceptable vehicle or other component.
Formula (I):
wherein R
1
and R
2
are each independently a C
1-30
hydrocarbon group which is optionally substituted, or a five- or six-membered heterocyclic group which contains 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and which is optionally substituted, R
3
is hydrogen, an alkyl group which is optionally substituted, an acyl group, an alkoxycarbonyl group, a phenoxycarbonyl group, or a carbamoyl group which is optionally substituted, and a and b are each independently 0 or 1.
According to another feature of the present invention, there is provided a hair revitalizing method for mammals which comprises topically applying a compound of formula (I) or a pharmaceutically or cosmetically acceptable salt thereof to the skin or hair of a mammal.
Furthermore, there is provided the use of a compound of formula (I) in the preparation of a hair revitalizing tonic composition as described above.
The compounds represented by the above formula (I) and salts thereof exhibit a significantly excellent hair growth promotion effect and, moreover, a hair loss prevention effect and a dandruff and itchy scalp suppression effect. Accordingly, the term “hair revitalization” or “hair revitalizing action” as used herein means at least one of the above-described effects.
DETAILED DESCRIPTION OF THE INVENTION
The compounds of formula (I) are more specifically described hereinbelow.
The C
1-30
hydrocarbon groups represented by R
1
and R
2
in formula (I) include, for example, C
1-30
alkyl groups, C
3-8
cycloalkyl groups, C
2-10
alkenyl groups, C
2-10
alkynyl groups, C
3-10
cycloalkenyl groups, C
6-14
aryl groups and C
7-16
aralkyl groups.
Examples of the C
1-30
alkyl groups include straight-chain alkyl groups such as methyl, ethyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl and triacontyl; and branched alkyl groups such as isopropyl, isobutyl, sec-butyl, tert-butyl, 2-methylpentyl, 3-methylpentyl, 4-isocapryl, 4-ethylpentyl, 6-methyldecyl, 9-methyldecyl, 6-ethylnonyl, 5-propyloctyl, 11-methyldodecyl, 12-methyldodecyl, 4-methyltetradecyl, 13-methyltetradecyl, 14-ethylhexadecyl, 10-methyloctadecyl, 15-ethylpentadecyl, 10-methyidocosyl, 2-pentyloctadecyl, 22-methyltricosyl, 12-hexyloctadecyl, 6-methyltetracosyl, 24-methylheptacosyl, 2-decylhexadecyl, 2-nonyloctadecyl, 2-dodecyloctadecyl, 3-methyltetracosyl and 3-methyltricosyl.
Preferred examples of the groups represented by R
1
and R
2
are straight-chain or branched C
6-30
alkyl groups which are optionally substituted, and more preferred examples thereof are straight-chain or branched C
6-22
alkyl groups, or more preferred examples thereof are straight-chain or branched C
8-20
or C
12-25
alkyl groups.
Examples of the C
3-8
cycloalkyl groups include cyclopropyl, cyclopentyl and cyclohexyl. Examples of the C
2-10
alkenyl groups include vinyl, allyl, 2-methylallyl, 2-butenyl, 3-butenyl, 3-octenyl, 2-nonenyl and 4-decenyl. Examples of the C
2-10
alkynyl groups include ethynyl, 2-propynyl and 3-hexynyl.
Examples of the C
3-10
cycloalkenyl groups include cyclopropenyl, cyclopentenyl and cyclohexenyl. Examples of the C
6-14
aryl groups include phenyl and naphthyl. Examples of the C
7-16
aralkyl groups include benzyl, phenylethyl and naphthylethyl.
The foregoing groups represented by R
1
and R
2
may have one or more (e.g., one to five) substituents at any substitutable position or positions in the carbon chain or carbon ring. Specific examples of the substituents include halogen (e.g., fluorine, chlorine, bromine and iodine) and C
3-8
cycloalkyl, hydroxyl, mercapto, oxo, thioxo, cyano, carbamoyl, carboxyl, C
1-4
alkoxycarbonyl (e.g., methoxycarbonyl and ethoxycarbonyl), sulfo, C
1-4
alkoxy (e.g., methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy and tertbutoxy), phenoxy, halogenophenoxy (e.g., o-, m- or p-chlorophenoxy and o-, m- or p-bromophenoxy), lower (C
1-4
) alkylthio (e.g., methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio and tert-butylthio), phenylthio, C
1-4
alkylsulfinyl (e.g., methylsulfinyl and ethylsulfinyl), C
1-4
alkylsulfonyl (e.g., methylsulfonyl and ethylsulfonyl) and C
1-10
loalkyl groups (e.g., difluoromethyl, trifluoromethyl, trifluoroethyl and trichloroethyl). Other specific examples of the substituents for the hydrocarbon groups include amino; substituted amino such as C
1-6
acylamino (e.g., acetylamino and propionylamino), C
1-30
alkylamino (e.g., methylamino, ethylamino, n-propylamino, isopropylamino, n-butylamino, isobutylamino, s-butylamino, t-butylamino, pentylamino, hexylamino, heptylamino, octylamino, nonylamino, decylamino, undecylamino, dodecylamino, tridecylamino, tetradecylamino, pentadecylamino, hexadecylamino, heptadecylamino, octadecylamino, nonadecylamino, icosylamino, henicosylamino, docosylamino, tricosylamino, tetracosylamino, pentacosylamino, hexacosylamino, heptacosylamino, octacosylamino, nonacosylamino and triacontylamino), di-C
1-4
alkylamino-(e.g., dimethylamino, diethylamino, N-methyl-N-ethylamino and N-methyl-N-propylamino); C
1-5
acyl (e.g., C
1-5
alkanoyl such as formyl, acetyl and propionyl); and benzoyl group.
Further specific examples of the substituents for the hydrocarbon groups include five- and six-membered heterocyclic groups which contain 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms and which are optionally substituted, such as pyrrolidyl, piperidyl, morpholino, thiomorpholino, 2- or 3-thienyl, 2- or 3-furyl, 3-, 4- or 5-pyrazolyl, 2-, 4- or 5-thiazolyl, 3-, 4- or 5-isothiazolyl, 2-, 4- or 5-oxazolyl, 3-, 4- or 5-isoxazolyl, 2-, 4- or 5-imidazolyl, 1,2,3- or 1,2,4-triazolyl, 1H- or 2H-tetrazolyl, 2-, 3- or 4-pyridyl, 2-, 4- or 5-pyrimidyl, 3- or 4-pyridazinyl, quinolyl, imidazoquinolyl and indolyl.
These heterocyclic groups are usually linked to C
1-2
hydrocarbon groups. These het
Fukunishi Hirotada
Kobayashi Koji
Magara Tsunao
Tajima Masahiro
Tsuji Yoshiharu
Gupta Anish
Low Christopher S. F.
Shiseido Company Ltd.
Wenderoth , Lind & Ponack, L.L.P.
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