Drug – bio-affecting and body treating compositions – Topical sun or radiation screening – or tanning preparations
Reexamination Certificate
2000-08-02
2002-08-27
Dees, Jose′ G. (Department: 1616)
Drug, bio-affecting and body treating compositions
Topical sun or radiation screening, or tanning preparations
C424S059000, C512S002000, C512S008000, C512S025000, C512S026000, C512S027000, C568S822000
Reexamination Certificate
active
06440400
ABSTRACT:
This application is a 371 of PCT/JP99/00412 Feb. 1, 1999.
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a novel trimethylcyclohexane derivative and a melanin production inhibitor and/or a fragrance fixative comprising this trimethylcyclohexane derivative as a main component, as well as a dermal formulation comprising these melanin production inhibitor and/or a fragrance fixative.
2. Description of the Related Art
An irradiation of a ray such as UV light to skin causes a sunburn and a change in the color of the skin tissue into black as a result of the production and the deposition of melanin in a chromatophore which is triggered by a irritative effect of the exposure to the UV or a hormone and the like. Freckles and liver spots reflect the fixative and the deposition of melanin throughout the entire layer of a local epidermis.
Such melanin synthesis in a epidermis is believed to be attributable to melanin production as a result of an oxidative polymerization of a tyrosine catalyzed by a tyrosinase which is an oxidase biosynthesized in a chromatophore.
An inhibition of the process of such melanin production and deposition is an aim of the development of a whitening agent and has been a subject in various studies.
The effect of vitamin C, cysteine, kojic acid, arbutin, glutathione, hydroquinone or an extract from a naturally occurring material as a substance capable of inhibiting tyrosinase activity and thus suppressing melanin production and as a substance capable of decoloring and whitening melanin once produced has already been established. Nevertheless, none of these substances is satisfactory in terms of stability, safety and odor, and has a sufficient whitening effect, and no satisfactory whitening agent has been obtained.
Other compounds having melanin production inhibiting effects which have been reported are tetrahydroionol and derivatives thereof (JP-A-8-73334, JP-A-8-73335, JP-A-8-73336 and JP-A-8-73359) and &bgr;-ionone and a dihydro form thereof (JP-A-8-198747). However, the melanin production inhibiting effect of any of these compounds is not satisfactory. In addition, their relatively intense odors pose a requirement of an effort to reduce the adverse effect on the fragrance of a final product.
Also known are the trimethylcyclohexane derivatives represented by Formula (3) and Formula (4):
wherein A represents C═O or CH—OH, R
4
represents ethyl, n-propyl and isobutyl, and,
wherein R
5
represents ethyl, n-propyl, n-butyl and isobutyl.
A compound of Formula (3) is described only as an intermediate or a by-product in synthesizing a fragrance compound, 1-alkyl-substituted-3-(2′,2′,6′-trimethylcyclohexan-1-yl)propan-1-ol (JP-B-3-80780, JP-A-4-226930), while a compound of Formula (4) is described only as a fragrance (JP-A-4-21642, JP-B-7-25709). Since any of the compounds described is an intensely fragrant substance, it can not be used as a fragrance fixative. None of the publications described above contain an inhibitory effect on melanin production by a viable chromatophore.
On the other hand, a conventional method for formulating fragrant substances to prepare an excellent fragrance composition involves an incorporation of various fixatives which adjust the aroma profile and the fixative of a fragrant substance into a fragrance for the purpose of sustaining an intended fragrance.
Those employed typically are dipropylene glycol, triethyl citrate, benzyl benzoate and the like, but these fixatives do not have satisfactory fixative effects.
SUMMARY OF THE INVENTION
An objective of the invention is to provide a novel trimethylcyclohexane derivative useful as a melanin production inhibitor or as a fragrance fixative. Another object of the invention is to provide a melanin production inhibitor and/or a fragrance fixative comprising this trimethylcyclohexane derivative as a main component. Still another object of the invention is to provide a dermal formulation comprising such melanin production inhibitor and/or fragrance fixative.
The inventors made an effort to solve the problems encountered currently as discussed above and finally discovered that a novel trimethylcyclohexane derivative represented by Formula (1):
wherein A represents C═O or CH—OH, n represents 2, R
1
represents hydrogen or a methyl group, R
2
represents a straight or branched, saturated or unsaturated hydrocarbon group having 3 to 10 carbon atoms, and a dotted line represents a saturated or unsaturated carbon-carbon bond, can solve the problems, thus establishing the invention.
Thus, the inventors discovered that Compound (1) represented by Formula (1) shown above has a potent inhibitory effect on melanin production by a viable chromatophore, that a melanin production inhibitor consisting of Compound (1) is excellent in terms of stability and safety and can exhibit an extremely higher melanin production inhibiting effect when compared with a conventional product, that Compound (1) has an ability of sustaining the fragrant component of a fragrance for a prolonged period and that a fragrance fixative consisting of Compound (1) can promote the intended aroma characteristics and the fragrance fixative markedly.
In addition, it was also discovered that Compound (1) which is odorless itself does not exert any influence on the smell of a dermal formulation containing it and is stable and safe in a formulation or a base, and has an excellent melanin production inhibiting effect and an excellent fragrance fixative effect.
A novel trimethylcyclohexane derivative (1) represented by the above Formula (1), a melanin production inhibitor and/or a fragrance fixative comprising this compound, and a dermal formulation comprising such melanin production inhibitor and/or a fragrance fixative are described below.
(1) A trimethylcyclohexane derivative represented by Formula (1):
wherein A represents C═O or CH—OH, n represents 2, R
1
represents hydrogen or a methyl group, R
2
represents a straight or branched, saturated or unsaturated hydrocarbon group having 3 to 10 carbon atoms, and a dotted line represents a saturated or unsaturated carbon-carbon bond.
(2) A trimethylcyclohexane derivative wherein R
2
in Formula (1) according to Section (1) described above is selected from the group consisting of n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, isopropyl, isobutyl, sec-butyl, tert-butyl, allyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methyl-l-propenyl, 2-methyl-2-propenyl, 1-ethyl-1-ethenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 2,6-dimethylheptyl, 2,6-dimethyl-1-heptenyl, 2,6-dimethyl-5-heptenyl and 2,6-dimethyl-1,5-heptadienyl groups.
(3) A trimethylcyclohexane derivative wherein R
2
in Formula (1) according to Section (1) described above is selected from the group consisting of n-propyl, n-butyl, isopropyl, isobutyl, sec-butyl, tert-butyl, allyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methyl-1-propenyl, 2-methyl-2-propenyl, 1-ethyl-1-ethenyl, 1-methyl-1-propenyl and 1-methyl-2-propenyl groups.
(4) A melanin production inhibitor comprising one or more of trimethylcyclohexane derivatives according to Sections (1) to (3) described above.
(5) A fragrance fixative comprising one or more of trimethylcyclohexane derivatives according to Sections (1) to (3) described above.
(6) A dermal formulation comprising one or more melanin production inhibitors and/or fragrance fixatives according to Sections (4) to (5) described above.
(7) A melanin production inhibitor comprising one or more trimethylcyclohexane derivatives represented by Formula (2):
wherein A represents C═O or CH—OH, n represents 0, R
1
represents hydrogen or a methyl group, R3 represents a straight or branched, saturated or unsaturated hydrocarbon group having 2 to 4 carbon atoms, and a dotted line represents a saturated or unsaturated carbon-carbon bond.
(8) A dermal formulation comprising one or more melanin production inhibitors according to Section (7) described above.
The present invention is described in further detail below.
R
Aida Takashi
Ishida Kenya
Matsuda Hiroyuki
Tamai Eiko
Tokoro Kazuhiko
Dees Jose′ G.
Kubovcik & Kubovcik
Lamm Marina
Takasago International Corporation
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