19-nor-steroids
AssigneeRoussel Uclaf
InventorsAndre Claussner, Daniel Philibert, Lucien Nedelec, Patrick Van De Velde, Francois Nique, Jean-Georges Teutsch
Life of this patent
Estimating the term…
Abstract
A 19-nor-steroid having a formula selected from the group consisting of ##STR1## wherein the A and B rings have a structure selected from the group consisting of ##STR2##
Claims14
A compound of the formula ##STR77## the A and B rings have the structure ##STR78## R.sub.3 is selected from the group consisting of hydrogen, alkyl of 1 to 4 carbon atoms and acyl of an organic carboxylic acid of 1 to 7 carbon atoms, R.sub.17 and R'.sub.17 together form --O or R.sub.17 is --OH or acyloxy and R'.sub.17 is selected from the group consisting of hydrogen, alkyl of 1 to 8 carbon atoms and alkenyl and alkynyl of 2 to 8 carbon atoms, all optionally substituted with at least one member of the group consisting of halogen, alkoxy, alkylthio --NH.sub.2, mono or dialkylamino, optionally oxidized aminoalkyl, dialkylaminalkyl, dialkylamino alkoxy, --OH, acyloxy, free esterified carboxy, --CN, --CF.sub.3, phenyl, furyl, thienyl, benzyl X is selected from the group consisting of --CH.sub.2 -- or CH.sub.2 O--, arylene and arylenoxy linked to the C ring through a carbon atoms, Y is selected from the group consisting of a simple bond and a saturated and unsaturated aliphatic of 1 to 18 carbon atoms optionally interrupted with at least one member of the group consisting of arylene, --O-- and optionally oxidized --S-- and optionally terminated with arylene, Z is a Simple bond or --CH.sub.2 O-- linked to Y by a carbon atoms, R.sub.A and R.sub.A ' being individually selected from the group consisting of hydrogen and alkyl of 1 to 8 carbon atoms optionally substituted with at least one member of the group consisting of aryl, alkylamino, dialkylamino, --OH, halogen and esterified carboxyl or R.sub.A and R.sub.A ' taken together with the nitrogen to which they are attached form a 5 to 6 member heterocycle optionally containing at least one additional heteroatom selected from the group consisting of --S--, --O-- and --N-- optionally substituted with alkyl of 1 of 4 carbon atoms with the proviso 1) that both R.sub.A and R.sub.A ' are not hydrogen and 2) that when Z and Y are both simple bond, X is not --CH.sub.2 -- or CH.sub.2 O--.
A compound of the formula ##STR80## wherein n is 1 or 2 and wherein when n is 1, K is oxygen, R.sub.18 is --OH or optionally salified ##STR81## is methyl, R.sub.A is selected from the group consisting of isopropyl, n-butyl and heptafluorobutyl, X' is selected from the group consisting of methylene, phenylene and phenoxy attached to the steroid by a carbon atom, Y' is selected from the group of ##STR82## q is an integer from 5 to 7, n' is 0, 1 or 2 and Z' is a simple bond and when n is 2, K is --O-- or --S--, R.sub.18 and R'.sub.18 form .dbd.O or R.sub.18 is --OH or acyloxy, and R'.sub.18 is selected from the group consisting of hydrogen and optionally substituted alkyl, alkenyl and alkynyl of up to 8 carbon atoms, X' is selected from the group consisting of --CH.sub.2 --, --CH.sub.2 O--, arylene and aryleneoxy and arylenethio connected to the steroid by a carbon atom, Y' is selected from the group consisting of a simple bond and optionally unsaturated aliphatic of 1 to 18 carbon atoms optionally interrupted with arylene or --O-- or --S--, --SO-- or --SO.sub.2 -- and optionally terminated with arylene, Z' is a simple bond with the proviso that when Y' and Z' are both a simple bond, X' is not --CH.sub.2 -- or --CH.sub.2 O-- and R.sub.B and R'.sub.B are individually selected from the group consisting of hydrogen and alkyl of 1 to 8 carbon atoms optionally substituted with a member of the group consisting of aryl, alkylamino, dialkylamino, --OH, halogen and esterified carboxy or taken together with the nitrogen to which they are attached form an optionally unsaturated 5- or 6-member heterocycle optionally containing at least one additional heteroatom of --O--, --S-- or nitrogen optionally substituted with a member of the group consisting of alkyl of 1 of 4 carbon atoms, aryl of 6 to 10 carbon atoms and aralkyl of 7 and 10 carbon atoms, with the proviso that at least one of R.sub.B and R'.sub.B is not hydrogen and at least one of the following conditions is met, n is 2 or K is --S-- or X' is arylenethio attached to the steroid by a carbon atom or R.sub.B and R'.sub.B with the nitrogen is a 5- or 6-member heterocycle substituted by aryl or aralkyl.
A compound selected from the group consisting of N-(2-dimethylaminoethyl)-17.beta.-hydroxy-N-methyl-3-oxo-11.beta.-.DELTA.. sup.4,9 -estradien-undecanamide;
- N-butyl-4-(3,17.beta.-dihydroxy-.DELTA..sup.1,3,5(10) -estratrien-11.beta.-yl)-N-methyl-benzene octanamide;
- 3,17.beta.-dihydroxy-N-methyl-N-isopropyl-11.beta.-.DELTA..sup.1,3,5(10) -estratrien-undecanamide;
- N-butyl-3,17.beta.-dihydroxy-N-methyl-19-nor-11.beta.-17.alpha.-.DELTA..su p.1,3,5(10) -pregnatrien-20-yne)-undecanamide;
- 3,17.beta.-dihydroxy-N-methyl-N-isopropyl-19nor-17.alpha.-.DELTA..sup.1,3, 5(10) -pregna-.gamma.trien-20-yn-11.beta.-undecanamide;
- -(8-(3,17.beta.-dihydroxy-.DELTA..sup.1,3,5(10) -estratrien-11.beta.-yl)-octyl!-oxy!-N-methyl-N-isopropyl acetamide;
- N-butyl-8-4-(3,17.beta.-dihydroxy-.DELTA..sup.1,3,5(10) -estratrien-11.beta.-yl)-phenoxy!-N-methyl octanamide;
- N-butyl-5-4-(3,17.beta.-dihydroxy-.DELTA..sup.1,3,5(10) -estratrien-11.beta.-yl)-phenoxy!-pentyloxy!-N-methyl acetamide;
- 2-7-4-(3,17.beta.-dihydroxy-.DELTA..sup.1,3,5(10) -estratrien-11.beta.-yl)-phenyl!-6-heptylyl!-oxy!-N-butyl-N-methyl acetamide;
- 3,17.beta.-dihydroxy-N-(2,2,3,3,4,4,4-heptafluorobutyl)-N-methyl-.DELTA..s up.1,3,5(10) -estratrien-11.beta.-yl undecanamide and 8-4-(3,17.beta.-dihydroxy-.DELTA..sup.1,3,5(10) -estratrien-11.beta.-yl)-phenyl!-N-butyl-N-methyl octynamide.
Dependencies are inferred from the claim text.