Steroid compounds and process of preparing the same

Details Steroid compounds and process of preparing the same Steroid compounds and process of preparing the same

1988-05-03

1989-10-17

Robinson, Douglas W.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

26039747, C07J 100

Patent

active

048748552

ABSTRACT:
Disclosed are steroid compounds represented by general formula (I) ##STR1## wherein X and W together as >W-X represent a carbonyl group (>C.dbd.O) or a hydroxymethylene group (>CH(OH)), the hydroxy moiety of the hydroxymethylene group being of .beta.-arrangement, and OR.sup.1 and OR.sup.2 independently represent an ester residue, and Y and Z together as --Y--Z-- represent a --(PpSe)CH--CH.sub.2 -- group where Pp represent a phenyl group or a 2-pyridyl group, or Y and Z each represent an ethenylene group or a 1-bromoethylene group.
Also disclosed is a process of preparing the compound (I) includes reacting 6.beta., 9.alpha.-difluoro-5.alpha.,17.alpha.,21-trihydroxypregna-3,11,20-trione-17 ,21-diesters or 6.beta.,9.alpha.-difluoro-5.alpha.,11.beta.,17.alpha.,21-tetrahydroxypregn a-3,20-dione-17,21-diesters as starting compound with an organic selenenyl halide selected from the group consisting of 2-pyridylselenenyl chloride, 2-pyridylselenenyl bromide, phenylselenenyl chlolride and phenylselenenyl bromide.
Further disclosed is a process of preparing 2-bromo-6.beta.,9.alpha.-difluoro-11.beta.,17.alpha.,21-trihydroxy-1,4-pre gnadien-3,20-di-one-17,21-diester represented by general formula (VII) ##STR2## wherein OR.sup.1 and OR.sup.2 independently represent an ester residue, which comprises reacting with hydrogen chloride, or with thionyl chloride in the presence of a basic substance, the compound (V), and optionally reducing with a reducing agent when >W-X represents a carbonyl group.

REFERENCES:
patent: 4226862 (1980-10-01), Riva et al.
patent: 4525303 (1985-06-01), Takagaki et al.
Chemical Abstracts; vol. 87 (1977); #102538v; Gaffuri.

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