Intermediates for 3-keto-19-nor-.DELTA..sup.4,9 -steroids
AssigneeRoussel Ulcaf
InventorsDaniel Philibert, Jean G. Teutsch, Germain Costerousse, Roger Deraedt
Life of this patent
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Abstract
Novel 3-keto-19-nor-.DELTA..sup.4,9 -steroids of the formula ##STR1## and their non-toxic, pharmaceutically acceptable acid addition salts possessing a remarkable antiglucocorticoidal activity.
Claims1
A compound of the formula ##STR24## wherein R.sub.1 ' is selected from the group consisting of thienyl, thienyl substituted with at least one member of the group consisting of halogen and alkyl and haloalkyl of 1 to 6 carbon atoms, furyl, cycloalkyl of 3 to 6 carbon atoms, naphthyl, phenylphenyl, alkyl of 1 to 6 atoms, alkenyl of 2 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms containing several double bonds and phenyl, phenyl substituted with at least one member of the group consisting of halogen, --OH, protected hydroxy, --CF.sub.3, alkyl and alkoxy of 1 to 6 carbon atoms, alkenyloxy of 2 to 6 carbon atoms, phenoxy and alkylthio of 1 to 6 carbon atoms and alkylthio of 1 to 6 carbon atoms oxidized to sulfoxide or sulfonyl, R.sub.2 is selected from the group consisting of methyl and ethyl, R.sub.3 " is selected from the group consisting of hydrogen, alkyl of 1 to 6 carbon atoms, substituted alkyl of 1 to 6 carbon atoms, alkenyl and alkynyl of 2 to 6 carbon atoms, substituted alkenyl and alkynyl of 2 to 6 carbon atoms, the substituents being at least one member selected from the group consisting of alkylamino, dialkylamino and halogen, --OH, acetyl, acetyl protected in the form of a ketal, hydroxyacetyl, esterified carboxyalkyl of 2 to 4 carbon atoms and acyloxyalkyl and R.sub.4 ' is selected from the group consisting of hydrogen, --OH, alkyl of 1 to 12 carbon atoms and alkenyl and alkynyl of 2 to 12 carbon atoms, substituted alkyl, alkenyl and alkynyl, the substituents being a member of the group consisting of alkylamino, dialkylamino, halogen, alkylthio, alkoxy, trialkylsilyl and cyano with the alkyls of 1 to 6 carbon atoms or R.sub.3 " is --CN and R.sub.4 ' is a blocked --OH in the form of an easily cleavable ether, R.sub.5 is selected from the group consisting of hydrogen and --CH.sub.3 in the .alpha.- or .beta.-position, K is blocked ketone in the form of a ketal, thioketal, oxime or methyloxime except the products wherein K is (1,2-ethanediyl)-acetal, R.sub.5 is hydrogen and
- a) R.sub.2 is methyl and .alpha.) R.sub.3 " is --CN, R.sub.4 ' is trimethylsilyloxy and R.sub.1 ' is selected from the group consisting of phenyl, methyl, ethyl, propyl, isopropyl, tert.-butyl, vinyl, allyl, isopropenyl, -o- and p-methoxyphenyl, thienyl, and p-fluorophenyl or p-trifluoromethylphenyl or .beta.) R.sub.3 " is --OH, R.sub.4 ' is ethynyl or methyl and R.sub.1 ' is selected from the group consisting of ethyl, propyl, vinyl, isopropenyl, allyl, isopropyl, thienyl, phenyl and o- and p-methylphenyl or .gamma.) R.sub.3 " is acetyl, i) R.sub.4 ' is --OH and R.sub.1 ' is ethyl, vinyl or phenyl or ii) R.sub.4 ' is methyl and R.sub.1 ' is vinyl and .delta.) R.sub.3 " is OH, R.sub.4 ' is ethynyl and R.sub.1 ' is p-fluorophenyl;
- b) R.sub.2 is ethyl, R.sub.3 " is --OH, R.sub.1 ' is vinyl and R.sub.4 ' is hydrogen and with the proviso that K does not represent an ethylene ketal, propylene ketal, dimethyl ketal or diethyl ketal radical when R.sub.5 is hydrogen R.sub.2 is methyl, R.sub.3 " is hydroxy, R.sub.4 ' is methyl and R.sub.1 ' is methyl.
Dependencies are inferred from the claim text.