Drug – bio-affecting and body treating compositions – Conjugate or complex of monoclonal or polyclonal antibody,... – Conjugate includes potentiator; or composition comprising...
Patent
1981-11-02
1984-06-05
Brown, Johnnie R.
Drug, bio-affecting and body treating compositions
Conjugate or complex of monoclonal or polyclonal antibody,...
Conjugate includes potentiator; or composition comprising...
424180, 536 5, 536 181, A61K 3171, A61K 31705, C07H 1524, C07J 1700
Patent
active
044527861
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to novel compounds obtained from Marsdenia cundurango Reichenbach fil. and represented by the general formula (I) given below, processes for their preparation, antitumor agents comprising them and compositions containing them. ##STR3## where X together with the 13 and 14 position carbon atoms is a group selected from the group consisting of ##STR4##
The compounds of the above general formula are named condurango glycoside A.sub.o, condurango glycoside C.sub.o, condurango glycoside B.sub.o, 20-O-methyl-condurango glycoside D.sub.o, 20-iso-O-methyl-condurango glycoside D.sub.o and condurango glycoside D.sub.o when X is ##STR5## respectively.
BACKGROUND ART
Marsdenia cundurango Reichenbach fil. belonging to the family Asclepiadaceae is a shrub of somewhat winding type growing naturally on and between mountains in the northwest of South America. Its bark is employed as an aromatic but bitter stomachic at the time of digestive disorder and/or anorexia, usually in the form of fluidextract (Commentary for the ninth Japanese Pharmacopeia)
The components of the bark of Marsdenia cundurango Reichenbach fil. include condurangogenin-A, condurangogenin-C and many other pregnane type compounds and their esters and glycosides, and the extraction, separation, structures and so on of them have been reported in, for example, the following documents. R. Tschesche et al., Tetrahedron, 21, p. 1777 (1965); 21, p. 1797 (1965); 23, p. 1461 (1967); and 24, p. 4359 (1968). M. Pailar et al., Monatshefte fur Chemie, 106, p. 37 (1975). Hiroshi Mitsuhashi et al., Chem. Pharm. Bull., 16, p. 2522 (1968). But details are still unclear in many respects.
As a result of study, the inventors of the present inventinon have found novel compounds represented by the above general formula (I) which have antitumor activity. The present invention has been completed on the basis of this finding.
DISCLOSURE OF THE INVENTION
In carrying out the present invention, the bark of Marsdenia cundurango Reichenbach fil. is preferred. This bark may be one commercially available, but is preferably one well dried and finely divided after its collection.
In view of the nature of the preparation of extracts, the order of the use of solvents is not critical in carrying out the present invention, and it may be changed according to convenience. A preferred embodiment of the process of the present invention is as follows:
First Operation
Marsdenia cundurango Reichenbach fil. if finely divided and extracted with an organic solvent, and the extract is concentrated to dryness under reduced pressure. As the organic solvent, methanol, ethanol, isopropanol or any other lower alcohol may be employed, but methanol is preferred.
Here, prior to the extraction, Marsdenia cundurango Reichenbach fil. may be defatted with an aliphatic hydrocarbon such as pentane, hexane, heptane, ligroine or petroleum ether. This pre-treatment is desired to be effected using hexane in an amount 4-7 times (v/w) that of Marsdenia cundurango Reichenbach fil.
In an embodiment of this extraction operation, first the extraction is effected by allowing the starting material-solvent mixture to stand at room temperature for from several hours to 12 hours or more. Then, the mixture is filtered to yield a filtrate. The residue is subjected to the same extraction-filtration repeatedly, and all the filtrates are combined and concentrated to dryness under reduced pressure to yield an extract.
The extraction is usually effected at normal temperatures, but may be effected while heating in order to shorten the extraction time. This extraction with heating is preferably carried out on a water bath at a water bath temperature of 35.degree.-55.degree. C. for 4-6 hours using a reflux condenser. It may be effected according to the percolation method.
The amount of the solvent used is 2-5 times (v/w) that of Marsdenia cundurango Reichenbach fil. The extraction residue is preferably subjected to extraction under the same conditions three or more times using the solven
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Abe Shigeru
Hayashi Koji
Mitsuhashi Hiroshi
Mizuno Den'ichi
Narita Toshiharu
Brown Johnnie R.
Zenyaku Kogyo Kabushiki Kaisha
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