US5149696A
Expired / Lapsed
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19→nor→steroids
Assignee: Aventis Pharma SA
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Filing: 1990-02-23
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Granted: 1992-09-22
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Expires: 2010-02-23
Abstract
Abstract Novel 19-nor-steroids of the formula <IMAGE> I wherein the A and B rings have a structure selected from the group consisting of <IMAGE> <IMAGE> having hormonal properties and their preparation and intermediates.
Inventors
- 👤 Andre Claussner
- 👤 Lucien Nedelec
- 👤 Daniel Philibert
- 👤 Patrick Van De Velde
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 13:44
CPC Classifications
C; C07; C07J; C07J1/00; C07J41/00; C07J41/0033; C07J41/0077; C07J41/0083; A; A61; A61P; A61P5/00; C07J43/00; C07J43/003
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
293 words
Novel 19-nor-steroids of the formula ##STR55## wherein the A and B rings have a structure ##STR56## R 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 17 and R' 17 together form ═0 or R 17 is --OH or acyloxy and R' 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 2 , mono- or dialkylamino, optionally oxidized amino-alkyl, dialkylaminoalkyl, dialkylaminoalkoxy, --OH, acyloxy, free or esterified carboxy, --CN, --CF 3 , phenyl, furyl, thienyl, benzyl, X is selected from the group consisting of --CH 2 --, --CH 2 O--, phenylene and phenylenoxy linked to the C ring through a carbon atom, Y is selected from the group consisting of a simple bond and saturated and unsaturated aliphatic of 1 to 18 carbon atoms optionally interrupted with at least one member of the group consisting of phenylene, --O--and optionally oxidized --S-- and optionally terminated with phenylene, Z is a simple bond or --CH 2 --O-- linked to Y by a carbon atom, R A and R' 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 with the proviso 1) that both of R A and R' A are not hydrogen and 2) when Z and Y are both simple bonds, X is not --CH 2 -- or --CH 2 --O--.
Claim 2
Dependent Claim
293 words
Novel 19-nor-steroids of the formula ##STR55## wherein the A and B rings have a structure ##STR56## R 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 17 and R' 17 together form ═0 or R 17 is --OH or acyloxy and R' 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 2 , mono- or dialkylamino, optionally oxidized amino-alkyl, dialkylaminoalkyl, dialkylaminoalkoxy, --OH, acyloxy, free or esterified carboxy, --CN, --CF 3 , phenyl, furyl, thienyl, benzyl, X is selected from the group consisting of --CH 2 --, --CH 2 O--, phenylene and phenylenoxy linked to the C ring through a carbon atom, Y is selected from the group consisting of a simple bond and saturated and unsaturated aliphatic of 1 to 18 carbon atoms optionally interrupted with at least one member of the group consisting of phenylene, --O--and optionally oxidized --S-- and optionally terminated with phenylene, Z is a simple bond or --CH 2 --O-- linked to Y by a carbon atom, R A and R' 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 with the proviso 1) that both of R A and R' A are not hydrogen and 2) when Z and Y are both simple bonds, X is not --CH 2 -- or --CH 2 --O--.
Claim 3
Dependent Claim
11 words
A compound of claim 1 wherein Z is a simple bond.
Claim 4
Dependent Claim
10 words
A compound of claim 1 wherein R 17 is --OH.
Claim 5
Dependent Claim
15 words
A compound of claim 1 wherein R 17 ' is hydrogen or ethynyl or propynyl.
Claim 6
Dependent Claim
26 words
A compound of claim 1 wherein X is --CH 2 -- and Y is linear alkylene of 5 to 10 carbon atoms optionally interrupted by --O--.
Claim 7
Dependent Claim
26 words
A compound of claim 1 wherein X is phenylene and Y is an aliphatic linear chain of 3 to 10 carbon atoms optionally interrupted by --O--.
Claim 8
Dependent Claim
27 words
A compound of claim 1 wherein X is phenylenoxy and Y is a linear alkylene of 3 to 10 carbon atoms optionally interrupted by --O-- or --S--.
Claim 9
Dependent Claim
49 words
A compound of claim 1 wherein R A and R A ' are both methyl or R A is methyl and R A ' is selected from the group consisting of isopropyl, dimethylaminoethyl, benzyl and heptafluorobutyl or R A ' is butyl and R A is hydrogen or methyl.
Claim 10
Dependent Claim
21 words
A antiestrogenic composition comprising an antiestrogenically effective amount of at least one compound of claim 1 and an inert pharmaceutical carrier.
Claim 11
Dependent Claim
26 words
A method of inducing hormonal activity in warm-blooded animals comprising administering to warm-blooded animals an antiestrogenically effective amount of at least one compound of claim 1.
Claim 12
Dependent Claim
58 words
A compound of claim 1 selected from the group consisting of N-butyl-4-(3,17β-dihydroxy-Δ 1 ,3,5(10) -estratrien-11β-yl)-N-methyl-benzene octanamide; 3,17β-dihydroxy-N-methyl-N-isopropyl-Δ 1 ,3,5(10) -estratrien-11β-yl-undecananide; N-butyl-N-methyl-3,17β-dihydroxy-19-nor-17α-Δ 1 ,3,5, (10) -pregnatrien-20-yne-11β-yl-undecanamide; N-methyl-N-isopropyl-3,17β-dihydroxy-19-nor-17α-Δ 1 ,3,5, (10) -pregnatrien-20-yne-11β-yl-undecanamide; [(8-l (3,17β-dihydroxy-Δ 1 ,3,5(10) estratrien-11β-yl)-octyl)-oxy]-N-methyl-N-isopropylacetamide; N-butyl-8-[4-(3,17β-dihydroxy-Δ 1 ,3,5(10) -estratrien-11β-yl)-phenoxy]-N-methyl octanamide; N-butyl-[5-[4-(3,17β-dihydroxy-Δ 1 ,3,5(10) -estratrien-11β-yl)-phenoxy]-pentyloxy]-N-methylacetamide; 2-[[7-[4-(3,17β-dihydroxy-Δ 1 ,3,5(10) -estratrien-11β-yl)-phenyl]-6-heptylyl]-oxy]-N-butyl-N-methyl acetamide; 3,17β-dihydroxy-N-(2,2,3,3,4,4,4-heptafluorobutyl)-N-methyl-Δ.sup.1,3,5(10) -estratrien-11β-yl undecanamide and 8-[4-(3,17β-dihydroxy-Δ 1 ,3,5(10) -estratrien-11β-yl)-phenyl]-N-butyl-N-methyl octynamide.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-09-22 | 1996-03-23 | 1996-09-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-09-22 | 2000-03-23 | 2000-09-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-09-22 | 2004-03-23 | 2004-09-22 | $7700.00 | Window Closed / Lapsed |