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US 4,783,454 AGranted
Process for producing harringtonine and homoharringtonine
OwnerYaguang Liuinventor
Life of this patent
Estimating the term…
Abstract
A new pharmaceutical composition for treating nonlymphatic leukemia, such as granulocytic and monocytic leukemia comprising Harringtonine, Homoharringtonine, Anethole, Oleanolic acid and Ginsenoside and method of making the same.
Claims4
A process for producing harringtonine comprising:
- (a) extracting a ground plant selected from the group consisting of Cephalotaxus fortunei Hook, C. sinensis Li, C. hainanensis and C. wilsoniana, with 90% ethanol at room temperature for 24 hours;
- (b) filtering the above mixture and separating a filtrate A from a filtercake;
- (c) percolating the filtercake with ethanol and collecting a filtrate B;
- (d) combining filtrates A and B and distilling them under reduced pressure to recover ethanol and an aqueous residue;
- (e) adjusting the pH of the residue to 2.5;
- (f) separating solids from the resulting mixture by filtration to yield a filtrate;
- (g) adjusting the pH of the filtrate to pH 9.5;
- (h) extracting the alkaline solution of step (g) with chloroform, and distilling the chloroform extract to recover alkaloids;
- (i) dissolving the alkaloids in citric acid, and adjusting pH of two equal portions of the acid solution portions to 8, and 9;
- (j) extracting the portions of pH 8 and 9 with chloroform;
- (k) distilling the chloroform extract to yield raw harringtonine;
- and
- (l) purifying said harringtonine by recrystallizing the same in pure ethanol and recrystallizing the same in diethyl ether.
10 more elements
A process for producing homoharringtonine comprising:
- (a) extracting a ground plant selected from the group consisting of Cephalotaxus fortunei Hook, C. sinensis Li, C. hainanensis and C. wilsoniana with 90% ethanol at room temperature for 24 hours;
- (b) filtering the above mixture and separating a filtrate A from a filtercake;
- (c) percolating the filtercake with ethanol and collecting a filtrate B;
- (d) combining filtrates A and B and distilling them under reduced pressure to recover ethanol and an aqueous residue;
- (e) adjusting the pH of the residue to 2.5;
- (f) separating solids from the resulting mixture by filtration to yield a filtrate;
- (g) adjusting the pH of the filtrate of step (f) to 9.5;
- (h) extracting the alkaline solution of step (g) five times with chloroform, combining all the chloroform extracts and distilling them to recover alkaloids;
- (i) dissolving the alkaloids in citric acid, and adjusting the resulting solution to pH 7;
- (j) passing the solution of step (i) through a chromatographic column packed with alumina, flushing said column with chloroform and subsequently with a chloroform-methanol mixture to yield a mixture of harringtonine and homoharringtonine;
- and
- (k) separating the homoharringtonine from harringtonine by countercurrent distribution with chloroform and pH 5 buffer.
9 more elements
A process for producing harringtonine and homoharringtonine comprising:
- (a) extracting a ground plant selected from the group consisting of Cephalotaxus fortunei Hook, C. sinensis Li, C. hainanensis and C. wilsoniana with 90% ethanol at room temperature for 24 hours;
- (b) filtering the above mixture and separating a filtrate A from a filtercake;
- (c) percolating the filtercake with ethanol and collecting a filtrate B;
- (d) combining filtrates A and B and distilling them under reduced pressure to recover ethanol and an aqueous residue;
- (e) adjusting the pH of the residue to 2.5;
- (f) separating solids from the resulting mixture by filtration to yield a filtrate;
- (g) adjusting the pH of the filtrate of step (f) to 9.5;
- (h) extracting the alkaline solution of step (g) five times with chloroform, combining all the chloroform extracts and distilling them to recover alkaloids;
- (i) dissolving the alkaloids in citric acid, dividing the solution into three portions, and adjusting the pH of the three portions to 7, 8, and 9;
- (j) extracting the portions of pH 8 and 9 with chloroform;
- (k) distilling the chloroform extract to yield raw harringtonine;
- (l) purifying said harringtonine by crystallizing the same in pure ethanol and recrystallizing the same in diethyl ether;
- (m) combining the portion of pH 7 of step (i) and the mother liquors resulting from step (l).
- (n) passing the solution of step (m) through a chromatographic column packed with alumina, flushing said column with chloroform and subsequently with a chloroform-methanol mixture to yield a mixture of harringtonine and homoharringtonine;
- and
- (o) separating the homoharringtonine from harringtonine by countercurrent distribution with chloroform and pH 5 buffer.
13 more elements
Dependencies are inferred from the claim text.