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Details for Patent: 4,634,695

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Details for Patent: 4,634,695

Title: Steroid derivatives
Abstract:Novel 19-nor steroids and 19-nor-D-homo-steroids of the formula ##STR1## wherein R.sub.1 is an organic radical of 1 to 18 carbon atoms containing at least one atom selected from the group consisting of nitrogen, phosphorous and silicon with the atom immediately adjacent to the 11-carbon atom being carbon, R.sub.2 is a hydrocarbon of 1 to 8 carbon atoms, X is selected from the group consisting of a pentagonal ring and a hexagonal ring optionally substituted and optionally containing a double bond, B and C together form a double bond or an epoxy group, the C.dbd.A group at position 3 is selected from the group consisting of C.dbd.O, ketal, which may be open or closed ##STR2## are selected from the group consisting of alkyl of 1 to 8 carbon atoms and aralkyl of 7 to 15 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having anti-glucocorticoid activity and a process for their preparation.
Inventor(s): Torelli; Vesperto (Maisons-Alfort, FR), Teutsch; Jean G. (Pantin, FR), Philibert; Daniel (La Varenne Saint Hilaire, FR)
Assignee: Roussel Uclaf (Paris, FR)
Filing Date:Jan 22, 1985
Application Number:06/693,682
Claims:1. A compound selected from the group consisting of 11.beta.-(4-dimethylamino-phenyl)-13.beta.-ethyl-17.alpha.-(prop-1-ynyl)-. DELTA..sup.4,9 -gonadiene-17.beta.-ol-3-one, 11.beta.-(4-dimethylamino-phenyl)-17.alpha.-(3-hydroxy-prop-1-ynyl)-.DELTA ..sup.4,9 -estradiene-17.beta.-ol-3-one, 11.beta.-(4-aminophenyl)-17.alpha.-(prop-1-ynyl)-.DELTA..sup.4,9 -estradiene-17.beta.-ol-3-one, 11.beta.-(4-methylamino-phenyl)-17.alpha.-(prop-1-ynyl)-.DELTA..sup.4,9 -estradiene-17.beta.-ol-3-one, N-[4-{17.alpha.-(prop-1-ynyl)-.DELTA..sup.4,9 -estradiene-17.beta.-ol-3-one-11.beta.-yl}]-phenyl-acetamide, 11.beta.-(4-dimethylamino-phenyl)-19-nor-17.alpha.-.DELTA..sup.4,9 -pregnadiene-17.beta.-ol-3-one-20-yne-21-carboxylic acid and its salts with non-toxic, pharmaceutically acceptable cations and their non-toxic, pharmaceutically acceptable acid addition salts.

2. A compound of claim 1 selected from the group consisting of 11.beta.-(4-dimethylamino-phenyl)-13.beta.-ethyl-17.alpha.-(prop-1-ynyl)-. DELTA..sup.4,9 -gonadiene-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-hydroxy-prop-1-ynyl)-.DELTA ..sup.4,9 -estradiene-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-amino-phenyl)-17.alpha.-(prop-1-ynyl)-.DELTA..sup.4,9 -estradiene-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

5. A compound of claim 1 selected from the group consisting of 11.beta.-(4-methylamino-phenyl)-17.alpha.-(prop-1-ynyl)-.DELTA..sup.4,9 -estradiene-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 N-[4-{17.alpha.-(prop-1-ynyl)-.DELTA..sup.4,9 -estradiene-17.beta.-ol-3-one-11.beta.-yl}]-phenyl-acetamide 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)-19-nor-17.alpha.-.DELTA..sup.4,9 -pregnadiene-17.beta.-ol-3-one 20-yne-21-carboxylic acid and its salts thereof with non-toxic, pharmaceutically acceptable cations and its non-toxic, pharmaceutically acceptable acid addition salts.

8. An antiprogestomimetic composition comprising an antiprogestomimetically effective amount of at least one compound of claim 1 and an inert pharmaceutical carrier.

9. A composition of claim 8 wherein the compound is selected from the group consisting of 11.beta.-(4-dimethylaminophenyl)-13.beta.-ethyl-17.alpha.-(prop-1-ynyl)-.D ELTA..sup.4,9 -gonadiene-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

10. A composition of claim 8 wherein the compound is selected from the group consisting of 11.beta.-(4-dimethylaminophenyl)-17.alpha.-(3-hydroxy-prop-1-ynyl)-.DELTA. .sup.4,9 -estradiene-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

11. A composition of claim 8 wherein the compound is selected from the group consisting of 11.beta.-(4-amino-phenyl)-17.alpha.-(prop-1-ynyl)-.DELTA..sup.4,9 -estradiene-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

12. A composition of claim 8 wherein the compound is selected from the group consisting of 11.beta.-(4-methylamino-phenyl)-17.alpha.- (prop-1-ynyl)-.DELTA..sup.4,9 -estradiene-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

13. A composition of claim 8 wherein the compound is selected from the group consisting of N-[4-{17.alpha.-(prop-1-ynyl)-.DELTA..sup.4,9 -estradiene-17.beta.-ol-3-one-11.beta.-yl}]-phenyl-acetamide and its non-toxic, pharmaceutically acceptable acid addition salts.

14. A composition of claim 8 wherein the compound is selected from the group consisting of 11.beta.-(4-dimethylaminophenyl)-19-nor-17.alpha.-.DELTA..sup.4,9 -pregnadiene-17.beta.-ol-3-one 20-yne-21-carboxylic acid and its salts thereof with non-toxic, pharmaceutically acceptable cations and its non-toxic, pharmaceutically acceptable acid addition salts.

15. A method of inducing menses in warm-blooded animals comprising administering to warm-blooded animals an antiprogestomimetically effective amount of at least one compound of claim 1.

16. A method of claim 15 wherein the compound is selected from the group consisting of 11.beta.-(4-dimethylaminophenyl)-13.beta.-ethyl-17.alpha.-(prop-1-ynyl)-.D ELTA..sup.4,9 -gonadiene-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

17. A method of claim 15 wherein the compound is selected from the group consisting of 11.beta.-(4-dimethylamino-phenyl)-17.alpha.-(3-hydroxy-prop-1-ynyl)-.DELTA ..sup.4,9 -estradiene-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

18. A method of claim 15 wherein the compound is selected from the group consisting of 11.beta.-(4-amino-phenyl)-17.alpha.-(prop-1-ynyl)-.DELTA..sup.4,9 -estradiene-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

19. A method of claim 15 wherein the compound is selected from the group consisting of 11.beta.-(4-methylamino-phenyl)-17.alpha.-(prop-1-ynyl)-.DELTA..sup.4,9 -estradiene-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

20. A method of claim 15 wherein the compound is selected from the group consisting of N-[4-{17.alpha.-(prop-1-ynyl)-.DELTA..sup.4,9 -estradiene-17.beta.-ol-3-one-11.beta.-yl}]-phenyl-acetamide and its non-toxic, pharmaceutically acceptable acid addition salts.

21. A method of claim 15 wherein the compound is selected from the group consisting of 11.beta.-(4-dimethylamino-phenyl)-19-nor-17.alpha.-.DELTA..sup.4,9 -pregnadiene-17.beta.-ol-3-one 20-yne-21 -carboxylic acid and its salts thereof with non-toxic, pharmaceutically acceptable cations and its non-toxic, pharmaceutically acceptable acid addition salts.

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

23. A composition of claim 22 wherein the compound is selected from the group consisting of 11.beta.-(4-dimethylaminophenyl)-13.beta.-ethyl-17.alpha.-(prop-1-ynyl)-.D ELTA..sup.4,9 -gonadiene-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

24. A composition of claim 22 wherein the compound is selected from the group consisting of 11.beta.-(4-dimethylaminophenyl)-17.alpha.-(3-hydroxy-prop-1-ynyl)-.DELTA. .sup.4,9 -estradiene-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

25. A composition of claim 22 wherein the compound is selected from the group consisting of 11.beta.-(4-amino-phenyl)-17.alpha.-(prop-1-ynyl)-.DELTA..sup.4,9 -estradiene-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

26. A composition of claim 22 wherein the compound is selected from the group consisting of 11.beta.-(4-methylamino-phenyl)-17.alpha.-(prop-1-ynyl)-.DELTA..sup.4,9 -estradiene-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

27. A composition of claim 22 wherein the compound is selected from the group consisting of N-[4-{17.alpha.-(prop-1-ynyl)-.DELTA..sup.4,9 -estradiene-17.beta.-ol-3-one-11.beta.-yl}]-phenyl-acetamide and its non-toxic, pharmaceutically acceptable acid addition salts.

28. A composition of claim 22 wherein the compound is selected from the group consisting of 11.beta.-(4-dimethylaminophenyl)-19-nor-17.alpha.-.DELTA..sup.4,9 -pregnadiene-17.beta.-ol-3-one 20-yne-21-carboxylic acid and its salts thereof with non-toxic, pharmaceutically acceptable cations and its non-toxic, pharmaceutically acceptable acid addition salts.

29. 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.

30. A method of claim 29 wherein the compound is selected from the group consisting of 11.beta.-(4-dimethylamino-phenyl)-13.beta.-ethyl-17.alpha.-(prop-1-ynyl)-. DELTA..sup.4,9 -gonadiene-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

31. A method of claim 29 wherein the compound is selected from the group consisting of 11.beta.-(4-dimethylamino-phenyl)-17.alpha.-(3-hydroxy-prop-1-ynyl)-.DELTA ..sup.4,9 -estradiene-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

32. A method of claim 29 wherein the compound is selected from the group consisting of 11.beta.-(4-amino-phenyl)-17.alpha.-(prop-1-ynyl)-.DELTA..sup.4,9 -estradiene-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

33. A method of claim 29 wherein the compound is selected from the group consisting of 11.beta.-(4-methylamino-phenyl)-17.alpha.-(prop-1-ynyl)-.DELTA..sup.4,9 -estradiene-17.beta.-ol-3-one and its non-toxic, pharmaceutically acceptable acid addition salts.

34. A method of claim 29 wherein the compound is selected from the group consisting of N-[4-{17.alpha.-(prop-1-ynyl)-.DELTA..sup.4,9 -estradiene-17.beta.-ol-3-one-11.beta.-yl}]-phenyl-acetamide and its non-toxic, pharmaceutically acceptable acid addition salts.

35. A method of claim 29 wherein the compound is selected from the group consisting of 11.beta.-(4-dimethylamino-phenyl)-19-nor-17.alpha.-.DELTA..sup.4,9 -pregnadiene-17.beta.-ol-3-one 20-yne-21-carboxylic acid and its salts thereof with non-toxic, pharmaceutically acceptable cations and its non-toxic, pharmaceutically acceptable acid addition salts.
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