Vitamin E derivatives

Details Vitamin E derivatives Vitamin E derivatives

2000-06-15

2002-05-14

Russel, Jeffrey E. (Department: 1653)

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Peptide containing doai

C514S019300, C514S458000, C530S331000, C530S332000, C530S345000, C549S410000

Reexamination Certificate

active

06387882

ABSTRACT:

TECHNICAL FIELD
The present invention relates to novel water soluble vitamin E derivatives, method for their production, and their use. In further detail, the present invention relates to novel vitamin E derivatives which are made up of vitamin E maleate (or fumarate) and an S-linked SH compound attached to it, as well as such novel vitamin E derivatives which further include an amino acid or its ester or an amine linked via an acid amide bond, a method for their production, and to hepatopathy suppressing, anticataract, cerebral metabolism improving and antioxidant pharmaceutical compositions and cosmetic compositions containing one of them.
BACKGROUND ART
Vitamin E (&agr;, &bgr;, &ggr;, &dgr;-tocopherol) has an antioxidant activity and it has been suggested recently that the compound is effective against cataract. While vitamin E by itself is insoluble in water, there are known water-soluble vitamin E derivatives created by the present inventors such as a phosphodiester compound consisting of vitamin E and vitamin C (ascorbic acid) (Japanese Patent Publication No. H02-44478, Japanese Patent Publication No. H05-23274), as well as a vitamin E glycidyl glutathione compound (Japanese Laid-open Patent Application No. H08-34779).
The present inventors, as a result of further investigations for a novel water-soluble vitamin E derivative, have succeeded in synthetically producing the water-soluble vitamin E derivatives of the present invention. The present invention is accomplished based on these and still further investigations.
DISCLOSURE OF INVENTION
The present invention relates to:
(1) a vitamin E derivative represented by the following formula (I) wherein: R
1
and R
2
are the same or different and each denotes hydrogen or methyl, R
3
denotes one of the S-linked SH compounds as defined hereinbelow or an ester thereof (except cysteamine), and R
4
denotes hydroxyl, one of the N-substituted amino acids defined hereinbelow or an ester thereof (except aminoethylsulfonic acid and aminoethylsulfinic acid) or the amine defined hereinbelow, or a pharmacologically acceptable salt thereof (hereinafter referred to as “the present compound”),
(2) a mono-tocopheryl maleate (or fumarate) represented by the following formula (IV) wherein: R
1
and R
2
are the same or different and each denotes hydrogen or methyl,
(3) a method for preparation of a vitamin E derivative as defined in (2) above or a pharmacologically acceptable salt thereof which comprises reacting vitamin E with maleic anhydride,
(4) a method for preparation of a vitamin E derivative as defined in (1) above or a pharmacologically acceptable salt thereof which comprises: reacting vitamin E with maleic anhydride to produce mono-tocopheryl maleate (or fumarate) and then subjecting the thus produced mono-tocopheryl maleate (or fumarate) to an addition reaction with a compound selected from the group of SH compounds consisting of glutathione, &ggr;-glutamylcysteine, cysteine, penicillamine, esters thereof, and cysteamine,
(5) a method for preparation of a vitamin E derivative as defined in (1) above or a pharmacologically acceptable salt thereof which comprises: reacting vitamin E with maleic anhydride to produce mono-tocopheryl maleate (or fumarate) and then subjecting the thus produced mono-tocopheryl maleate (or fumarate) to a condensation reaction with a compound selected from the group of amino acids consisting of glycine, &bgr;-alanine, &ggr;-aminobutyric acid, 5-aminovaleric acid, &egr;-aminocaproic acid, anthranilic acid, tranexamic acid, proline, esters thereof, aminoethylsulfonic acid and aminoethylsulfinic acid or with serotonin by mixed acid anhydride method to produce a corresponding acid amide of the monotocopheryl maleate (or fumarate), and then subjecting the product to an addition reaction with a compound selected from the group of SH compounds consisting of glutathione, &ggr;-glutamylcysteine, cysteine, penicillamine, esters thereof, and cysteamine,
(6) a hepatopathy suppressing pharmaceutical composition comprising the compound as defined in (1) above or a pharmacologically acceptable salt thereof,
(7) an anticataract pharmaceutical composition comprising the compound as defined in (1) above or a pharmacologically acceptable salt thereof,
(8) a cerebral metabolism improving pharmaceutical composition comprising the compound as defined in (1) above or a pharmacologically acceptable salt thereof,
(9) an antioxidant pharmaceutical composition comprising the compound as defined in (1) above or a pharmacologically acceptable salt thereof, and
(10) a cosmetic composition comprising the compound as defined in (1) above or a pharmacologically acceptable salt thereof.


REFERENCES:
patent: 3657279 (1972-04-01), Higashi et al.
patent: 4564686 (1986-01-01), Ogata
patent: 4665204 (1987-05-01), Wirth
patent: 4914197 (1990-04-01), Yamamoto et al.
patent: 5606080 (1997-02-01), Ogata et al.
patent: 5811083 (1998-09-01), Pelle et al.
patent: 02-44478 (1990-10-01), None
patent: 05-23274 (1993-04-01), None
patent: 08-34779 (1996-02-01), None

Affiliated with

Also associated with

Rating

Vitamin E derivatives does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Vitamin E derivatives, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Vitamin E derivatives will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-2915706