Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
1999-10-18
2001-04-24
McKane, Joseph K. (Department: 1613)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C549S412000
Reexamination Certificate
active
06222051
ABSTRACT:
TECHNICAL FIELD
The present invention relates, in general, to novel alpha-tocopherol 4-aminobenzoic acid ester compounds and to a method for preparing the same and, more particularly, to novel alpha-tocopherol 4-aminobenzoic acid ester compounds which have the biological effects of alpha-tocopherol and 4-aminobenzoic acid, both, in vivo and to a method for preparing the same.
BACKGROUND ART
4-aminobenzoic acid derivatives are generally represented by the following formula II:
wherein R
1
and R
2
, which may be the same or different, each is a hydrogen atom or a linear or branched C
1
~C
4
alkyl chain.
Of the compounds represented by the formula II, the 4-aminobenzoic acid in which R
1
and R
2
each is a hydrogen atom, is now found to play a role as a growth-promoting factor and to have a pharmacological activity of helping in the formation of red blood cells and the metabolism of the human body. In addition, it is reported that the 4-aminobenzoic acid aids to maintain healthy skin and to prevent the decoloration of the hair.
Vitamin E (DL-alpha-tocopherol), represented by the following formula III, is widely used as an antioxidant for living organisms:
Recently, vitamin E has been recognized to be clinically effective in various fields and the demand for vitamin E is increasing. As seen in the formula III, free tocopherol, a compound possessing a benzene ring to which hydroxy group binds, is unstable because it itself is easily oxidized in vitro.
Tocopherol quinone, an oxidized product of vitamin E, no longer has the biological activity of vitamin E. Thus, in order to prevent the in vitro oxidation of vitamin E, it must be converted to other derivative forms which conserve the biological activity of vitamin E. Representatives are esters. Examples of such esters include &agr;-tocopherol acetate, &agr;-tocopherol acid succinate, and &agr;-tocopherol palmitate. These derivatives are advantageous in storage and transportation because they are stable relative to free &agr;-tocopherol itself.
Because these esters have pharmaceutically acceptable stability in addition to being very easy to handle, they are effectively used as replacements for &agr;-tocopherol. Upon oral administration, the vitamin E esters are absorbed into the intestinal track and hydrolyzed completely, that is, into free tocopherol and acids by pancreatic enzymes and intestinal enzymes. Thus, the vitamin E esters are absorbed in the form of free tocopherol into the living body. In other words, the vitamin E esters are converted into free vitamin E by digestive enzymes in the living body, so that the biological effect they have on the living body is practically equivalent to that of vitamin E.
DISCLOSURE OF THE INVENTION
Therefore, it is an object of the present invention to provide novel pharmaceutically active compounds which have the equal biological activity to that of vitamin E but a more beneficial effect on the living body.
It is another object of the present invention to provide a method for preparing such a type of compounds.
In accordance with an embodiment of the present invention, there is provided a type of compounds represented by the following formula I:
wherein R
1
and R
2
, which may be the same or different, each is a hydrogen atom or a linear or branched C
1
~C
4
alkyl chain.
In accordance with another embodiment of the present invention, there is provided a method for preparing the compound of the formula I, in which a 4-aminobenzoic acid derivative, represented by the following formula II:
wherein R
1
and R
2
are as defined above, is reacted with an alpha-tocopherol, represented by the following formula III:
in a reaction solvent and in the presence of a base catalyst.
REFERENCES:
patent: 166 221 A2 (1986-01-01), None
Jung Hee-Young
Lee Si-Joon
Abelman ,Frayne & Schwab
McKane Joseph K.
SK Corporation
Solola Taofiq A.
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