1,3-diphenylpropane derivatives having inhibitory activity again

Details 1,3-diphenylpropane derivatives having inhibitory activity again 1,3-diphenylpropane derivatives having inhibitory activity again

1998-11-06

2000-07-25

McKane, Joseph

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549413, 549408, 568367, 568664, C07C 43205, C07C 49303, C07C 49603, C07D31158

Patent

active

060938366

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

The present invention relates to a novel 1,3-diphenylpropane derivative having an inhibitory activity against tyrosinase represented by the following formula (I): ##STR2## in which - - represents double or single bond, or can be substituted by C.sub.1 -C.sub.5 alkyl and which contains oxygen as the hetero atom, C.sub.1 -C.sub.5 alkyl.
The present invention also relates to novel processes for preparation of the compound of formula (I) as defined above.


BACKGROUND ART

Melanin is prepared through the conversion of Tyrosine into DOPA, Dopaquinone by the action of Tyrosinase located in the chromatophore then through the non-enzymatic oxidation. Melanin is distributed over the skin and has an important function to protect the body from various stimuli. However, it has been reported that excess production of melanin is closely related to melanoma and may also induce melanistic skin freckles, etc. Accordingly, a variety of cosmetics and medicaments for the prevention of excess production of melanin are actively developed in these days.
As the preventive agent for the excess production of melanin, hydroquinone has been mainly used heretofore. This compound, however, also exhibits side effects such as degeneration or lethal mutation of melanin, damage of the cellular function, etc., and therefore the use of hydroquinone in cosmetics is now prohibited in Korea, Japan, etc.(see, J. Soc. Cosmet. Chem., 42, 361, 1991). In addition, arbutin, a sugar derivative of hydroquinone, was commercialized but has been identified as having little whitening effect, and ascorbic acid, kojic acid, etc. have so poor product stability that they can only be restrictively used. While, extracts from licorice root, mori cortex radicis, etc. have been widely known to have a skin-whitening effect since ancient times. But, those extracts occasionally have poor effect according to the place of production it is difficult to keep the quality of the product constant(see, Fragrance J., 6, 59, 1990). Carzinol F extracted from a paper mulberry tree(see, Chem. Parm, Bull., 34(5), 1968, 1986; Cosmetics & Toiletries, 101, 51, 1995) was recently commercialized due to its good inhibitory activity against tyrosinase. However, this substance also has the problem that it is difficult to keep the quality of the product constant because carzinol F is an extract too. Sufficient data on stimulating property and stability of carzinol F are not available and it has a demerit that it cannot be easily synthesized because of the prenylcatechol group included therein.


DISCLOSURE OF INVENTION

Thus, the present inventors have intensively studied to develop a novel compound having an excellent inhibitory acitivity against tyrosinase in a small quantity. Further, the desired compound should be easily synthesized from the starting material and be stable. During the study, the present inventors analyzed the effect and structure of various natural substances known to have a whitening effect. As a result, we have developed a novel 1,3-diphenylpropane derivative of formula (I), which satisfies the purpose as mentioned above, and thus completed the present invention.
Therefore, it is an object of the present invention to provide a novel 1,3-dipenylpropane derivative represented by the following formula (I): ##STR3## in which - - represents double or single bond, or can be substituted by C.sub.1 -C.sub.5 alkyl and which contains oxygen as the hetero atom, C.sub.1 -C.sub.5 alkyl.
Among the foregoing definitions for the substituents of the compound of formula (I), the term "alkyl" defines straight or branched saturated hydrocarbon radicals such as methyl, ethyl, n-propyl, isopropyl or several butyl isomers when it is used alone or in the composite form such as "alkyloxy" or "alkoxyalkyl".
It is another object of the present invention to provide novel processes for preparing the compound of formula (I).


BEST MODE FOR CARRYING OUT THE INVENTION

Among the novel compound of formula (I), as defined above, the preferred compounds include those wherein R.sub.1 r

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