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Details for Patent: 5,006,518

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Details for Patent: 5,006,518

Title: Novel 17.beta.-hydroxy-19-nor-steroids
Abstract:Novel 19-nor steroids of the formula ##STR1## wherein R' is selected from the group consisting of propyl, propenyl, iodoethenyl, iodoethynyl or --C.tbd.C--CH.sub.2 --Hal.sub.1, Hal.sub.1 is selected from the group consisting of fluorine, chlorine and bromine and their non-toxic, pharmaceutically acceptable acid addition salts having a remarkable antiglucocorticoid and antiprogestomimetic activity.
Inventor(s): Moguilewsky; Martine (Paris, FR), Nedelec; Lucien (Le Raincy, FR), Nique; Francois (Pavillons-Sous-Bois, FR), Philibert; Daniel (La Varenne Saint-Hilaire, FR)
Assignee: Roussel Uclaf (Paris, FR)
Filing Date:Dec 30, 1988
Application Number:07/292,475
Claims:1. A compound selected from the group consisting of 19-nor steroids of the formula ##STR12## wherein R' is selected from the group consisting of propyl, prop-1-enyl, iodoethenyl, iodoethynyl or --C.tbd.C--CH.sub.2 --Hal.sub.1, Hal.sub.1 is selected from the group consisting of fluorine, chlorine and bromine and their non-toxic, pharmaceutically acceptable acid addition salts.

2. A compound of claim 1 selected from the group consisting of 17.alpha.-(3-chloro-1-propynyl)-11.beta.-[4-(dimethylamino)-phenyl]-.DELTA ..sup.4,9 -estradien-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

3. A compound of claim 1 selected from the group consisting of 11.beta.-[4-(dimethylamino)-phenyl]-17.alpha.-(3-fluoro-1-propynyl)-.DELTA ..sup.4,9 -estradien-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

4. A compound of claim 1 selected from the group consisting of 11.beta.-[4-(dimethylamino)-phenyl]-21-iodo-19-nor-17.alpha.-.DELTA..sup.4 ,9 -pregnadien-20-yn-17.beta.-ol-3-one and its non-toxic, pharmaceuticaly acceptable acid addition salts.

5. A compound of claim 1 selected from the group consisting of (E) 11.beta.-[4-(dimethylamino)-phenyl]21-iodo-19-nor-17.alpha.-.DELTA..sup.4, 9,20 -pregnatrien-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

6. A compound of claim 1 selected from the group consisting of (Z) 11.beta.-[4-(dimethylamino)-phenyl]21-iodo-19-nor-17.alpha.-.DELTA..sup.4, 9,20 -pregnatrien-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

7. A compound of claim 1 selected from the group consisting of 11.beta.-[4-(dimethylamino)-phenyl]-17.alpha.-[(Z)-1-propenyl]-.DELTA..sup .4,9 -estradien-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

8. A compound of claim 1 selected from the group consisting of 11.beta.-[4-(dimethylamino)-phenyl]-17.alpha.-propyl-.DELTA..sup.4,9 -estradien-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

9. A compound of claim 1 selected from the group consisiting of 17.alpha.-(3-bromo-1-propynyl)-11-.beta.[4-(dimethylamino)-phenyl]-.DELTA. .sup.4,9 -estradien-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

10. An antiglucocorticoid composition comprising an antiglucocorticoidally effective amount of at least one compound of claim 1 and an inert pharmaceutical carrier.

11. A composition of claim 10 wherein the active compound is selected from the group consisting of 17.alpha.-(3-chloro-1-propynyl)-11.beta.-[4-(dimethylamino)-phenyl]-.DELTA ..sup.4,9 -estradien-17.beta.-ol-3-one, 11.beta.-[4-(dimethylamino)-phenyl]-17.alpha.-(3-fluoro-1-propynyl)-.DELTA ..sup.4,9 -estradien-17.beta.-ol-3-one, 11.beta.-[4-(dimethylamino)-phenyl]-21-iodo-19-nor-17.alpha.-.DELTA..sup.4 ,9 -pregnadien-20-yn-17.beta.-ol-3-one, (E) 11.beta.-[4-(dimethylamino)-phenyl]-21-iodo-19-nor-17.alpha.-.DELTA..sup.4 ,9,20 -pregnatrien-17.beta.-ol-3-one, (Z) 11.beta.-[4-(dimethylamino)-phenyl]-21-iodo-19-nor-17.alpha.-.DELTA..sup.4 ,9,20 -pregnatrien-17.beta.-ol-3-one, 11.beta.-[4-(dimethylamino)-phenyl]-17.alpha.-[(Z)-1-propenyl)-.DELTA..sup .4,9 -estradien-17.beta.-ol-3-one, 11.beta.-[4-(dimethylamino)-phenyl)]-17.alpha.-propyl-.DELTA..sup.4,9 -estradien-17.beta.-ol-3-one and 17.alpha.-(3-bromo-1-propynyl)-11.beta.-[4-(dimethylamino)-phenyl]-.DELTA. .sup.4,9 -estradien-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

12. A composition of claim 10 wherein the active compound is selected from the group consisting of 11.beta.-[4-(dimethylamino)-phenyl]-17.alpha.-(3-fluoro-1-propynyl)-.DELTA ..sup.4,9 -estradien-17.beta.-ol-3-one, (Z) 11.beta.-[4-(dimethylamino)-phenyl]-21-iodo-19-nor-17.alpha.-.DELTA..sup.4 ,9,20 -pregnatrien-17.beta.-ol-3-one and 11.beta.-[4-(dimethylamino)-phenyl]-17.alpha.-[(Z)-1-propenyl]-.DELTA..sup .4,9 -estradien-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

13. An abortifacient composition for animals comprising an abortifaciently effective amount of the compound of claim 1 and pharmaceutical carrier.

14. A composition of claim 13 comprising an effective amount of the compounds of claim 3 and 11.

15. A composition of claim 13 for animals comprising an effective amount of the compound of claim 12.

16. A method of inducing antiglucocorticoid activity in warm-blooded animals comprising administering to warm-blooded animals an antiglucocorticoidally effective amount of at least one compound of claim 1.

17. A method of claim 16 wherein the active compound is selected from the group consisting of 17.alpha.-(3-chloro-1-propynyl)-11.beta.-[4-(dimethylamino)-phenyl]-.DELTA ..sup.4,9 -estradien-17.beta.-ol-3one, 11.beta.-[4-(dimethylamino)-phenyl]-17.alpha.-(3-fluoro-1-propynyl)-.DELTA ..sup.4,9 -estradien-17.beta.-ol-3-one, 11.beta.-[4-(dimethylamino)-phenyl]-21-iodo-19-nor-17.alpha.-.DELTA..sup.4 ,9 -pregnadien-20-yn-17.beta.-ol-3-one, (E) 11.beta.-[4-(dimethylamino)-phenyl]-21-iodo-19-nor-17.alpha.-.DELTA..sup.4 ,9,20 -pregnatrien-17.beta.-ol-3-one, (Z) 11.beta.-[4-(dimethylamino)-phenyl]-21-iodo-19-nor-17.alpha.-.DELTA..sup.4 ,9,20 -pregnatrien-17.beta.-ol-3-one, 11.beta.-[4-(dimethylamino)-phenyl]-17.alpha.-[(Z)-1-propenyl)-.DELTA..sup .4,9 -estradien-17.beta.-ol-3-one, 11.beta.-[4-(dimethylamino)-phenyl)]-17.alpha.-propyl-.DELTA..sup.4,9 -estradien-17.beta.-ol-3-one and 17.alpha.-(3-bromo-1-propynyl)-11.beta.-[4-(dimethylamino)-phenyl]-.DELTA. .sup.4,9 -estradien-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

18. A method of claim 16 wherein the active compound is selected from the group consisting of 11.beta.-[4-(dimethylamino)-phenyl]-17.alpha.-(3-fluoro-1-propynyl)-.DELTA ..sup.4,9 -estradien-17.beta.-ol-3-one, (Z) 11.beta.-[4-(dimethylamino)-phenyl]-21-iodo-19-nor-17.alpha.-.DELTA..sup.4 ,9,20 -pregnatrien-17.beta.-ol-3-one and 11.beta.-[4-(dimethylamino)-phenyl]-17.alpha.-[(Z)-1-propenyl]-.DELTA..sup .4,9 -estradien-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

19. A method of inducing abortion in pregnant female warm-blooded animals comprising administering to pregnant fermale warm-blooded animals an abortion effective amount of the compound of claim 1.

20. A method of claim 19 comprising administering to pregnant female warm-blooded animals an abortion effective amount of the compound of claim 3 and 11.

21. A method of claim 19 comprising administering to pregnant female warm-blooded animals an abortion effective amount of the compound of claim 7.

22. An anti-progestomimetic composition comprising an anti-progestomimetically effective amount of at least one compound of claim 1 and an inert pharmaceutical carrier.

23. A method of inducing anti-progestomimetic activity in warm-blooded animals comprising administering to warm blooded animals an anti-progestomimetically effective amount of at least one compound of claim 1.
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