Gymnemic acid derivatives, process for the preparation...

Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives

Reexamination Certificate

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C514S026000, C514S027000, C514S033000

Reexamination Certificate

active

06833443

ABSTRACT:

This application is the national phase under 35 U.S.C. § 371 of PCT International Application No. PCT/CN00/00010 which has an International filing date of Jan. 21, 2000, which designated the United States of America and was not published in English.
1. Field of the Invention
This invention relates to new Gymnemic acid derivatives, their preparation, pharmaceutical composition or extract which contains them, and their medical use, especially the use in the prevention or treatment of the diseases associated with hyperglycemia, hyperlipidemia and platelets aggregation.
2. Background of the Related Art
A lot of studies on Gymnemic Acid derivatives have been done and all of these Gymnemic acid derivatives are from the plant called Gymnema cane, which is classified as Gymnema sylvestre. R. Br. In India, it has been used to treat swelling, snake venom toxin, malaria, as a diuretic or to lower blood sugar level. Yet the Gymnemic acid derivatives and their biological activity mentioned in this invention haven't been reported up to this date.
SUMMARY OF THE INVENTION
The object of this invention is to find new Gymnemic acid derivatives and develop their medical use.
The inventors have found out new Gymnemic acid derivatives of formula I or II and also their medical use, especially in treating hyperglycemia, hyperlipidemia and platelets aggregation. The invention is now performed based on the discovery mentioned above.
In the first part, this invention concerns Gymnemic Acid derivatives formula I or II,
wherein, R
1
is H or the radical represented by the following formula
R
3
is H, and R
2
symbolizes the following radical,
or R
3
symbolizes the following radical,
and R
2
is H or the following radical,
or a pharmaceutical base addition salt thereof.
The second part of this invention relates to pharmaceutical composition which contains at least one kind of Gymnemic Acid derivative of formula I and/or II or pharmaceutical base addition salt thereof as active ingredient, pharmaceutical carrier and excipient.
The third part of the invention involves Gymnemic Acid extract 12.5-40 wt % of which is Gymnemic Acid derivative of formula l and/or II.
Another part of this invention relates to pharmaceutical composition for the prevention or treatment of the diseases associated with hyperglycemia, hyperlipidemia and platelets aggregation, which contains at least one kind of gymnemic acid derivative of formula I and/or II or pharmaceutical base addition salt thereof as an active ingredient, pharmaceutical carrier and excipient.
Another part of the invention relates to a pharmaceutical composition for the prevention or treatment of diabetes, which includes at least one kind of Gymnemic Acid derivative of formula I and/or II or pharmaceutical base addition salt thereof as an active ingredient, a pharmaceutical carrier and an excipient.
Another part of this invention relates to a pharmaceutical composition for the prevention or treatment of higher blood lipid level, which contains at least one kind of gymnemic acid derivative of formula I and/or II or a pharmaceutical base addition salt thereof as an active ingredient, pharmaceutical carrier and an excipient.
Another part of this invention relates to pharmaceutical composition for the prevention or treatment of platelets aggregation, which contains at least one kind of gymnemic acid derivative of formula I and/or II or pharmaceutical base addition salt thereof as an active ingredient, pharmaceutical carrier and excipient.
Another part of this invention relates to the preparation of Gymnemic Acid derivative of formula I and If or pharmaceutical base addition salt thereof, which includes the following steps:
a) extracting the plant Gymnema cane with ethane under reflux and then concentrating;
b) extracting concentrated liquid in step a) with cyclohexane, then extracting with n-butanol, concentrating to dryness under reduced pressure, and then obtaining a paste;
c) subjecting the paste in step b) to silica column chromatography with chloroform:methanol=90:10-50:5 or 90:10-60:40 (v/v) as elute, obtaining gymnemic acid derivative of formula I and residue;
d) subjecting the residue in step c) to C
18
column chromatography with methanol/water=20/80−40/60 (v/v) as eluant, obtaining gymnemic acid derivative of formula II;
e) if desired, converting the obtained gymnemic acid derivative of formula I or II into pharmaceutical base addition salt with an inorganic or organic base.
Another part of this invention relates to a method of preparation of the extract containing Gymnemic Acid derivative of formula I and II which ranges from 12.5-40 wt %, which includes the following steps:
a) extracting Gymnema cane leaves with 60-95% ethanol and concentrating,
b) extracting concentrated liquid in step a) with cyclohexane, then extracting with n-butanol, and then concentrating the extract under reduced pressure.
Another aspect of the invention relates to use of Gymnemic Acid derivative of formula I and II or the extract containing Gymnemic Acid derivative of formula I and II for the manufacture of medicament for the prevention or treatment of the diseases and conditions associated with hyperglycemia, hyperlipidemia and platelets aggregation.
Finally, this invention relates to the method of preventing or treating the diseases and conditions associated with hyperglycemia, hyperlipidemia and platelets aggregation, which includes administrating a prophylactic or effective quantity of Gymnemic Acid derivative of formula I and II to a patient suffering from diseases or conditions associated with hyperglycemia, hyperlipidemia and platelets aggregation.
The term “patient” in the invention refers to a mammal, including a human being, and especially a human being.
DETAILED DESCRIPTION OF THE INVENTION
This invention relates to Gymnemic Acid derivative of formula I and II,
wherein, R
1
is H or the radical represented by the following formula
R
3
is H, and R
2
is the following group,
or R
3
is the following group,
and R
2
is H or the following group,
or the pharmaceutical base addition salt.
According to the invention, the pharmaceutical base addition salt of Gymnemic acid of formula I or II includes a salt formed with pharmaceutical inorganic or organic base. The inorganic base, for example, includes alkali or alkali earth metal hydroxide, alkali metal or alkali earth metal carbonate or bicarbonate, alkali metal may be selected from Li, Na, K, alkali earth metal may be selected from Ba, Mg, Ca etc. The organic base, for example, may be triethyl amine etc.
According to this invention, the Gymnemic acid compound preferably is a
According to the invention, the Gymnemic acid compound is preferably a Gymnemic Acid compound of formula I wherein R
1
is the following radical.
According to the invention, the Gymnemic acid compound is preferably a Gymnemic Acid compound of formula II wherein R
3
is H and R
2
is the following radical.
According to the invention, the Gymnemic acid compound is preferably a Gymnemic Acid compound of formula II wherein R
3
is H and R
2
is the following radical.
According to the present invention, the Gymnemic acid compound is preferably a Gymnemic Acid compound of formula II wherein R
3
is the following radical and R
2
is H.
According to the invention, the Gymnemic acid compound is preferably Gymnemic Acid compound of formula II wherein both R
3
and R
2
are the following radicals respectively.
According to the invention, the pharmaceutical composition contains at least one kind of Gymnemic Acid derivative of formula I and/or II, a pharmaceutical carrier and an excipient. For example, the pharmaceutical composition may include, for example, 1.25-2.10 wt % compound A, 0.89-1.5 wt % compound B, 2.40-3.80 wt % compound C, 2.10-3.40 wt % compound D, 2.74-4.60 wt % compound E, and 3.24-5.4 wt % compound F (compounds A, B, C, D, E and F as defined in examples below.). This pharmaceutical composition can be. administrated by gastrointestinal, parenteral or topical administration, such as oral, muscle, subcutaneous, p

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