The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.
The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.
Patent No.:
Date of Patent:
Nov. 12, 1991
Filed:
Nov. 16, 1989
Daniel Philibert, Saint-Hilaire, FR;
Jean G Teutsch, Pantin, FR;
Germain Costerousse, Saint-Maurice, FR;
Roger Deraedt, Pavillons-sous-Bois, FR;
Roussel Uclaf, Paris, FR;
Abstract
Novel 3-keto-19-nor-.DELTA..sup.4,9 -steroids of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of naphthyl, phenylphenyl, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms optionally containing additional unsaturations, phenoxy, furyl, cycloalkyl of 3 to 6 carbon atoms, thienyl optionally substituted with at least one member of the group consisting of halogen and alkyl and haloalkyl of 1 to 6 carbon atoms and phenyl optionally substituted with at least one member of the group consisting of --OH, halogen, --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 optionally oxidized to the sulfoxide or sulfone, R.sub.2 is selected from the group consisting of methyl and ethyl, R.sub.3 is selected from the group consisting of hydrogen, optionally substituted alkyl of 1 to 6 carbon atoms, optionally substituted alkenyl and alkynyl of 2 to 6 carbon atoms, --OH, acetyl, hydroxyacetyl, carboxyalkoxy of 2 to 4 carbon atoms optionally esterified or salified and hydroxyalkyl of 1 to 6 carbon atoms optionally esterified, R.sub.4 is selected from the group consisting of hydrogen, alkylthio and alkoxy of 1 to 12 carbon atoms, trialkylsilyl of 1 to 6 carbon atoms, --CN, --OH and alkyl, alkenyl and alkynyl of up to 12 carbon atoms optionally substituted with at least one member of the group consisting of halogen and alkylamino and dialkylamino of 1 to 6 alkyl carbon atoms, R.sub.5 is selected from the group consisting of hydrogen and methyl in the .alpha.- or .beta.-position, X is .dbd.0 or hydroxyimino or alkoxyimino of 1 to 4 carbon atoms in the syn or anti form and A and B are an epoxy or a second bond in the 9(10) position and their non-toxic, pharmaceutically acceptable acid addition salts where R.sub.4 is an amino group, with the proviso that A and B are not a second bond in the 9(10)-position when X is .dbd.0 and R.sub.5 is hydrogen and a) R.sub.2 is methyl and .alpha.) R.sub.3 is --OH and i) R.sub.1 is ethyl or phenyl and R.sub.4 is hydrogen or ii) R.sub.1 is ethyl, propyl, isopropyl, vinyl, allyl, isopropenyl, phenyl, 4-fluorophenyl, methoxyphenyl or thienyl and R.sub.4 is ethynyl or iii) R.sub.1 is propyl, isopropyl, vinyl, allyl, isopropenyl, 4-methoxyphenyl or thienyl and R.sub.4 is methyl and .beta.) R.sub.3 is acetyl and i) R.sub.1 is ethyl, vinyl or phenyl and R.sub.4 is --OH or ii) R.sub.1 is vinyl and R.sub.4 is methyl and b) R.sub.2 is ethyl and R.sub.1 is vinyl, R.sub.3 is --OH and R.sub.4 is hydrogen possessing a remarkable antiglucocorticoidal activity.