Novel 7 .beta.-hydroxy-4-pregnene-3,20-dione derivatives and met

Details Novel 7 .beta.-hydroxy-4-pregnene-3,20-dione derivatives and met Novel 7 .beta.-hydroxy-4-pregnene-3,20-dione derivatives and met

1988-09-26

1991-07-02

Friedman, Stanley J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Cyclopentanohydrophenanthrene ring system containing

552563, C07J 700

Patent

active

050287222

DESCRIPTION:

BRIEF SUMMARY
DESCRIPTION

1. Technical Field
This invention relates to novel pregnene derivatives used as intermediates for the synthesis of progesterone derivatives having ovulation-inhibiting activity. A group of these compounds is expected to be used in the field of medicine. Cell differentiation activity is also found on a part of these compounds and hence utilization as drugs is also expected in this area.
2. Background Art
A variety of pregnene derivatives has already been found to date. However, pregnene derivatives of this invention are novel compounds and biological activities of these compounds have naturally been unknown.


DISCLOSURE OF INVENTION

The present inventors have researched the action of microorganisms belonging to Acremonium sp., e.g., a strain of mold fungi, in a substrate of 4-pregnene-3,20-dione. As a result, it has been found that two types of novel pregnene derivatives specified in this invention are produced.
The present inventors have further subjected one of the derivatives produced above to a reaction with acid anhydrides and found that esters of these derivatives can be obtained.
The pregnene derivatives of this invention can be used as intermediates for the manufacture of progesterone derivatives. These pregnene derivatives including the above mentioned esters exhibit also cell differentiation activity.
The pregnene derivatives of this invention are specified in claim 1, and representative examples of these derivatives have the following chemical names.
7.beta.,15.beta.,17.alpha.-Trihydroxy-4-pregnene-3,20-dione (the 1st compound of this invention described in claim 2).
7.beta.-Hydroxy-4-pregnene-3,15,20-trione (the 2nd compound of this invention described in claim 3).


BRIEF DESCRIPTION OF DRAWINGS

FIGS. 1-4 relate to the 1st compound of this invention.
FIG. 1 illustrates an EI mass spectrum.
FIG. 2 shows an infrared absorption spectrum.
FIG. 3 shows a proton nuclear magnetic resonance spectrum.
FIG. 4 illustrates a .sup.13 C-nuclear magnetic resonance spectrum.
FIGS. 5-7 relate to the 2nd compound of this invention.
FIG. 5 illustrates an EI mass spectrum.
FIG. 6 illustrates a proton nuclear magnetic resonance spectrum.
FIG. 7 shows a .sup.13 C-nuclear magnetic resonance spectrum.


BEST MODE FOR CARRYING OUT THE INVENTION

This invention is to provide a novel pregnene derivatives which is used as an intermediate for the manufacture of progesterone derivatives having progestin activities such as ovulation-inhibiting activity and also has itself cell differentiation activity. This invention will hereinafter be illustrated in detail by way of examples.


Culture of microorganisms and conversion of substrate by the microorganisms

Acremonium strictum NN106 preserved in Hungarian National Institute of Hygiene (FERM P-9143), which is a strain of mold fungi was cultured with shaking in a medium containing carbon sources such as malt extract, peptone, nitrogen sources such as soybean meal, and inorganic salts. In carrying out the culture, the strain was inoculated on 100 ml of a culture medium having, for example, a below described composition in a Erlenmeyer flask of 500 ml volume. The culture was incubated and shaken simultaneously in a incubator with a rotary shaker at a rate of 200 rpm for 48 hours at 24.degree. C.


______________________________________ Malt extract 30 g Peptone 20 g Soybean meal 10 g Potassium phosphate, monobasic 5 g Magnesium sulfate 5 g Purified water 1000 ml ______________________________________
The above strain was deposited as FERM p-9143 in Fermentation Research Institute of the Agency of Industrial Science and Technology on Jan. 21, 1987.
4-Pregnene-3,20-dione as a substrate was dissolved in dimethylformamide in advance so as to obtain a substrate concentration of 0.1 g/ml.
To the culture solution obtained above, 2 ml of the above substrate solution was added and a reaction was carried out for 24-48 hours under the same conditions as above.
After completing the reaction, solid matters and cells were removed from the resultant culture soluti

REFERENCES:
Chemical Abstracts; vol. 110 (1989); #133693q; Yoshihama et al.
Chemical Abstracts; vol. 112 (1990); #51952a; Yoshihama et al.
Chemical Abstracts; vol. 98 (1983); #51853m; Murherjee et al.
Chemical Abstracts; vol. 97 (1982); #69011z; Mahato et al.
Tsuda, K. et al., Chemical Abstracts 55, No. 17, 16903 f-i (1961).
Meinwald, J. et al., J. Chem. Ecol. 13, 35-38 (1987).

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