Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
2001-04-25
2003-03-25
Trinh, Ba K. (Department: 1625)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C549S403000
Reexamination Certificate
active
06538021
ABSTRACT:
The invention relates to a process for the preparation of compounds of the formula I
in which R
1
is H or (CH
2
)
m
OH, R
2
is H or (CH
2
)
n
OH, R
3
is H or (CH
2
)
p
OH, and m, n and p in each case, independently of one another are 2 to 8.
The compound of the formula I in which R
1
, R
2
and R
3
are H is luteolin. For the purposes of the present invention, he compounds of the formula I in which at least one of the radicals R
1
, R
2
or R
3
has a meaning other than H are referred to as luteolin derivatives.
Luteolin has various advantageous properties. Luteolin is an excellent antioxidant and a very good free-radical scavenger. In addition, it inhibits both enzymatic, nonenzymatic and CCl
4
-induced lipid peroxldations. Luteolin has a favorable influence on the card ovascular system and can prevent the development of arteriosclerosis. The anticancer effect of luteolin is evident inter alia from the considerable antiproliferative activity against various human tumor cell lines. Anti-inflammatory, antiviral, antibacterial and radioprotective properties of luteolin have also been reported. As an inhibitor of the enzyme aldose reductase, luteolin can also have a preventative effect against the development of diabetic cataracts.
The luteolin derivatives of the formula I have similarly advantageous properties to luteolin itself.
Known processes for the preparation of compounds of the formula I have the disadvantage that they involve, for example, two or more synthesis stages and/or produce unsatisfactory yields of product. For example, it has hitherto only been possible to isolate luteolin from plants or to prepare it by multistage syntheses. The synthesis from suitable chalcones and hesperidin is possible only with unsatisfactory yields [U. Achterrath-Tuckermann et al., Planta Med. 39 (1980) 38; D. Nagarathnam et al., J. Org. Chem. 56 (1991) 4884; Y.-H. Lu et al., Yao Hsueh Hsueh Pao 15 (1980) 477; G. Litkei et al., Liebigs Ann. 9 (1995) 1711; Y. Xing et al., Zhongguo Yiyao Gongye Zazhi 25 (1994) 484].
The object was therefore to develop a process for the preparation of the compounds of the formula I which avoids or at least reduces the disadvantages of known processes, in particular permits a single-stage preparation of the compounds of the formula I from readily available precursors and/or permits the preparation of the compounds of the formula I in relatively high yield.
Surprisingly, we have found that this object is achieved if the process for the preparation of the compounds of the formula I
in which R
1
is H or (CH
2
)mOH, R
2
is H or (CH
2
)nOH, R
3
is H or (CH
2
)
p
OH, and m, n and p in each case, independently of one another, are 2 to 8, is carried out such that compounds of the formula II
in which R
1
, R
2
and R
3
in each case, independently of one another, have the meanings given in formula I, and
are reduced with sodium dithinite Na
2
S
2
O
4
in an aqueous alkaline medium.
The invention thus provides a process for the preparation of compounds of the formula I
in which R
1
is H or (CH
2
)
m
OH, R
2
is H or (CH
2
)
n
OH, R
3
is H or (CH
2
)
p
OH, and m, n and p are in each case, independently of one another, 2 to 8, characterized in that compounds of the formula II
in which R
1
, R
2
and R
3
in each case, independently of one another, have the meanings given in formula I, and
are reduced with sodium dithionite Na
2
S
2
O
4
in an aqueous alkaline medium.
The process according to the invention is notable in particular for the fact that the preparation of the compounds of the formula I takes place in a simple manner and/or in higher yields than was possible by processes known hitherto.
The present invention also provides foodstuffs which have been enriched with one or more compounds of the formula I, and also the use of the compounds of the formula I as food supplements.
The foodstuffs which can be enriched according to the present invention with one or more compounds of the formula I include all materials suitable for consumption by animals or for consumption by humans, for example vitamins and provitamins thereof, fats, minerals or amino acids. Foodstuffs which can be enriched according to the present invention with one or more compounds of the formula I are, for example, also foodstuffs originating from a single natural source, for example sugar, unsweetened juice, nectar or puree of a single plant species, for example unsweetened apple juice (e.g. including a mixture of different types of apple juice), grapefruit juice, orange juice, stewed apples, apricot nectar, tomato juice, tomato sauce, tomato puree, etc. Further examples of foodstuffs which can be enriched according to the present invention with one or more compounds of the formula I are corn or grain of a single plant species and materials prepared from such plant species, for example grain syrup, rye flour, wheatmeal or oat bran. Mixtures of such foodstuffs are also suitable for being enriched according to the present invention by one or more compounds of the formula I, for example multivitamin preparations, mineral substance mixtures or sugared juice. Further examples of foodstuffs which can be enriched according to the present invention with one or more compounds of the formula I which may be mentioned are foodstuff preparations, for example prepared cereals, bakery products, mixed drinks, foodstuffs prepared specifically for children, such as yoghurt, diet foodstuffs, low-calorie foodstuffs or animal feed.
The foodstuffs which can be enriched according to the present invention with one or more compounds of the formula I thus include all palatable combinations of carbohydrates, lipids, proteins, inorganic elements, trace elements vitamins, water and active metabolites of slants and animals.
The foodstuffs which can be enriched according to the present invention with one or more compounds of the formula I, and the food supplements which contain one or more compounds of the formula : are preferably used orally, e.g. in the form of foods, pills, tablets, capsules, powders, syrups, solutions or suspensions.
The foodstuffs according to the Invention enriched with one or more compounds of the formula I can be prepared using techniques which are well known to the person skilled In the art.
Furthermore, the invention provides cosmetic or pharmaceutical formulations which comprise one or more compounds of the formula I, and the use of one or more compounds of the formula I in cosmetic or pharmaceutical formulations. The cosmetic formulations which comprise one or more compounds of the formula I, and the use of one or more compounds of the formula I in cosmetic formulations is preferred.
Whilst about 30 years ago sunlight was regarded as therapeutic and safe because of the synthesis of vitamin D, in recent years, opinion in this connection has changed considerably, not only from a medical viewpoint. The potential dangers associated both with natural and artificial irradiation with sunlight has been pushed into the foreground of awareness. In particular, a change in behavior has been brought about as a result of knowledge about the effect of sunlight on skin aging and the development of skin cancer.
As is known, the skin is sensitive to solar rays, which may cause ordinary sunburn or an erythema, but also burns of greater or lesser severity.
Solar rays too, however, also have other negative effects: they cause the skin to lose its elasticity and form wrinkles and thus lead to premature aging. In some cases, dermatoses can also be observed, and in extreme cases, skin cancer can result.
It is also desirable to protect hair against photochemical damage in order to prevent changes in shades, bleaching or damage of a mechanical nature.
As is known, the most harmful part of solar rays is formed from the ultraviolet rays having a wavelength of less than 400 nm. It is also known that, as a result of the presence of the ozone layer in the earth's atmosphere, which absorbs some solar radiation, the lower limit of the ultraviolet rays which reach the earth's surface is about 280 nm.
Buchholz Herwig
Kraus Christine
Lichtenberg Alice
Rosskopf Ralf
Merck Patent Gesellschaft
Millen White Zelano & Branigan P.C.
Trinh Ba K.
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