PROCESS FOR PREPARING 6alpha,9alpha-DIFLUORINATED STEROIDS AND INTERMEDIATE COMPOUNDS

摘要

FIELD: medicine. SUBSTANCE: invention describes new process for preparing 6alpha,9alpha-difluorinated steroids of formula I: 6alpha,9alpha wherein R is hydrogen atom or ester residue. The process comprises treating compound of formula II: with oxidative destructing agent to give compound of formula III: wherein functional ketone group in position 3 is protected in the form of enol ether or ester, and functional acid group is optionally protected in position in the form of ester to give compound of formula IV: 17beta, wherein R is as defined above, and is ether or ester enol residue which is treated with electrophilic fluorinating agent to give compound of formula V: R1, compound is treated with nucleophilic fluorinating agent to give compound of formula I which is, when R is ester residue, optionally saponified to give corresponding acid. The process is advantageous in that only functional ketone group is protected in position 3 in the form of enol ether or ester to give compound of formula IV. The invention also describes new compounds of formula VI: wherein R is as defined in formula I, X is hydrogen or fluorine atom, and Y bonded with dotted lines is essentially system of 3-keto , or X is hydrogen atom, and Y bonded with dotted lines is essentially system of Δ4 in which 3-OR1 Δ3,5 is as defined in formula I. Compounds are useful as intermediate compounds for preparing steroidal drugs. EFFECT: more efficient preparation process. 10 cl, 4 ex