Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
1999-09-17
2001-03-20
Shah, Mukund J. (Department: 1624)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Heterocyclic carbon compounds containing a hetero ring...
C514S235800, C514S254050, C514S394000, C514S395000, C544S139000, C544S370000, C548S304700, C548S306100, C548S307400, C548S308100, C548S309400, C548S309700
Reexamination Certificate
active
06204264
ABSTRACT:
RELATED APPLICATIONS
This application claims the priority of Japanese Patent Application No. 10-266709 filed on Sep. 21, 1998, which is incorporated herein by reference.
FIELD OF THE INVENTION
The present invention relates to a benzimidazole derivative and, in particular, to a benzimidazole derivative that has excellent hair growth effect.
BACKGROUND OF THE INVENTION
At the present time, scalp abnormality due to activation of androgen in an organ such as hair root or sebaceous gland, lowering of blood stream toward hair follicle, excess secretion of sebum, generation of peroxide and the like has been considered as a cause of baldness or hair loss. Accordingly, a compound or composition that can remove or reduce the above-mentioned problems has been generally included into a hair growth promoting composition to promote hair growth and regrowth and to prevent hair loss, for a long time (in the present invention, “hair growth promoting composition” includes hair regrowth promoting composition, and the like).
At present, compounds or crude drug extracts having various functions have been compounded to the hair growth promoting composition. These functions include blood flow promoting action, topical stimulation, hair follicle activating action, antiandrogen action, antiseborrheic action and the like have been known. Examples of drugs having blood flow promoting action include swertia herb extract, vitamin E and its derivative, and benzyl nicotinate. Examples of drugs which promote blood circulation by topical stimulation include capsicum tincture, cantharides tincture, camphor and vanillic acid nonylamide. Examples of drugs having hair follicle activating action include hinokitiol, placental extract, photosensitizing dye, pantothenic acid and derivative thereof. Examples of drugs having antiandrogen action include estradiol and estrone. Examples of drugs having antiseborrheic action include sulfur, thioxolone and vitamin B
6
.
In addition to these drugs, salicylic acid, resorcine and the like that have corneocyte desquamating action and antibacterial action can be compounded to hair growth promoting composition for the purpose of preventing dandruff. Further, glycyrrhizic acid, menthol and the like can be compounded in order to prevent inflammation of scalp. Furthermore, amino acids, vitamins, extracts of crude drugs and the like can be compounded so as to aliment to hair follicle and activate enzyme activity.
Meanwhile, for example, D(L)-pantolactone (Unexamined Japanese Patent Publication No. Hei 8-26942), 2(1H)-pyridone derivative (Unexamined Japanese Patent Publication No. Hei 8-20521), N
G
-nitro-L-arginine (Unexamined Japanese Patent Publication No. Hei 7-316023), 3-methyleneisoindolin-1-one derivative (Unexamined Japanese Patent Publication No. Hei 7-316022), indole derivative (Unexamined Japanese Patent Publication No. Hei 7-304736) are disclosed in recent patents as drugs having hair regrowth effect, hair growth effect, and hair loss protecting effect.
However, although the drugs described above are compounded to the conventional hair growth promoting compositions, they do not always exhibit sufficient hair regrowth and growth promoting effect.
SUMMARY OF THE INVENTION
In view of the foregoing problem in the prior art, an object of the present invention is to provide a compound, which is excellent in hair growth and regrowth promoting effect on human hair, and a hair growth promoting composition comprising the same as an active ingredient.
As a result of diligent studies of the inventors for attaining the above mentioned objects, it has been found that certain benzimidazole derivative and its salt have excellent hair growth and regrowth promoting effect, thereby accomplishing the present invention.
Namely, a benzimidazole derivative or a salt thereof in accordance with the present invention is expressed by the following Formula (I):
wherein each of A and B is R
1
or —(CH
2
)
n
—NR
2
R
3
, wherein when A is R
1
, B is —(CH
2
)
n
—NR
2
R
3
and when A is —(CH
2
)
n
—NR
2
R
3
, B is R
1
;
R
1
is a hydrocarbon group of C
10-30
;
R
2
and R
3
individually represent a hydrogen atom, a lower alkyl group, a phenyl group or a benzyl group, or —NR
2
R
3
may be a heterocycle having 3-7 members; wherein when B is —(CH
2
)
n
—NR
2
R
3
and m=1, —(CONR
5
)
m
—B may be the following Group (W):
wherein R
2
is a hydrogen atom, a lower alkyl group, a phenyl group or a benzyl group and ring E is a heterocycle of 6 or 7 members;
R
4
is selected from the group consisting of a hydrogen atom, a halogen atom, a cyano group, a trifluoromethyl group, a lower alkyl group, a lower acyl group, a carboxyl group, a lower alkoxycarbonyl group, a carbamoyl group, a lower alkylcarbamoyl group, an amino group, a lower alkylamino group, a lower acylamino group, a hydroxy group, a lower alkoxy group and a lower acyloxy group;
R
5
is a hydrogen atom, a lower alkyl group, a lower acyl group or a lower alkylcarbamoyl group; wherein when B is —(CH
2
)
n
—NR
2
R
3
and m=1, —(CONR
5
)
m
—B may be said Group (W);
m is 0 or 1; and
n is an integer of 0-5.
A hair growth promoting composition in accordance with the present invention is characterized by comprising said benzimidazole derivative or the pharmacologically acceptable salt thereof as an effective ingredient.
An external preparation for skin in accordance with the present invention is characterized by comprising said benzimidazole derivative or the pharmacologically acceptable salt thereof.
A method for promoting hair growth in accordance with the present invention is characterized by applying an effective amount of said benzimidazole derivative or the pharmacologically acceptable salt thereof on the skin of mammals and, in particular, on human scalp.
REFERENCES:
patent: 10 78 132 (1960-03-01), None
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patent: 59-181262 (1984-10-01), None
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patent: 07304736 (1995-11-01), None
patent: 07316023 (1995-12-01), None
patent: 07316022 (1995-12-01), None
patent: 08026942 (1996-01-01), None
patent: 08020521 (1996-01-01), None
patent: WO 97/35540 (1997-10-01), None
Iemura, Synthesis of 2-(4-substituted-1piperazinyl)benzimidazoles as H1-Antihistaminic Agents, J. Med. Chem., 29(7), pp. 1178-1183, 1986.*
Garnovski, Competitive Coordination of 2-aminoazoles and 2-aminoazines, Koord. Khim., 14(3), pp. 299-306, 1988.*
Iemura, R. et al., “Synthesis of 2-(4-Substituted-1 piperazinyl) benzimidazoles as H1Antihistaminic Agents”, J. Med Chem. vol. 29, No. 7, pp. 1178-1183.
Pozharskii AF et al., “Benzimidazole derivatives. XXVII. Synthesis and reaction of some N-derivative so benzimidazole, containing branched and high-molecular-weight substituents in position 1, with nucleophilic reagents”, p. 486, Chemical Abstracts vol. 076, No. 21, Abstract No. 126865y, 1972.
Garnovskii DA et al., Competitive coordination of 2-aminoazoles and 2-aminoazines, p. 808, col. 2, Chemical Abstracts vol. 109, No. 10, 1988.
American Chemical Society, Abstract, CA61:3091f, with STN International Registry File Search Results, RN 94297-44-6, 88637-07-4 and RN 61981-81-5 (Mar. 31, 1997). Total of 7 pages filed.
Fukunishi Hirotada
Kobayashi Koji
Tajima Masahiro
Umishio Kenichi
Schroeder Ben
Shah Mukund J.
Shiseido Co. Ltd.
Snider Ronald R.
Snider & Associates
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