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Claims for Patent: 4,472,393

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Claims for Patent: 4,472,393

Title: 3,20-Dioxo-1,4-pregnadiene-17.alpha.-ol 17-aromatic heterocycle carboxylates
Abstract:This invention relates to novel 3,20-dioxo-1,4-pregnadiene-17.alpha.-ol 17-aromatic heterocyclic carboxylates, to pharmaceutical formulations thereof, and their use in the treatment and control of inflammatory conditions.
Inventor(s): Shapiro; Elliot L. (Cedar Grove, NJ)
Assignee: Schering Corporation (Kenilworth, NJ)
Application Number:06/403,276
Patent Claims: 1. A 3,20-dioxo-1,4-pregnadiene of the following formula: ##STR3## X is a member selected from the group consisting of hydrogen and halogen having an atomic weight less than 100;

Y is a member selected from the group consisting of (H,H) provided X is hydrogen, oxygen, (H,.beta.OH), and (H,.beta.-halogen) provided X is chlorine or bromine, said .beta.-halogen having an atomic weight of less than 100 and being at least as electronegative as X;

Z is hydrogen, CH.sub.3, chlorine, or fluorine;

V is an acyl radical of an aromatic heterocyclic carboxylic acid selected from the group consisting of thiophenecarboxylic acid, pyrrolecarboxylic acid and furancarboxylic acid, and methyl and halogen-substituted derivatives thereof;

W is a member selected from the group consisting of (H,H); (H, lower alkyl); (H, OV.sub.1) wherein V.sub.1 is a member selected from the group consisting of hydrogen and an acyl radical of an acid selected from the group consisting of a hydrocarboncarboxylic acid having up to 12 carbon atoms, benzoic acid substituted by a halogen or methoxy group, retinoic acid, and isonicotinic acid; .dbd.CHT wherein T is a member selected from the group consisting of hydrogen, lower alkyl, fluorine, and chlorine;

G is hydrogen, a halogen having an atomic weight less than 100, or OV.sub.2 wherein V.sub.2 is a member selected from the group consisting of hydrogen, an acyl radical of a hydrocarboncarboxylic acid having up to 12 carbon atoms, benzoic acid substituted by a halogen or methoxy group, retinoic acid, isonicotinic acid, and the acid radical of phosphoric acid and mono- and dialkali and alkaline earth metal salts thereof;

and the 6-dehydro and 1,2-dihydro analogs of the foregoing.

2. A 3,20-dioxo-1,4-pregnadiene of claim 1.

3. A compound of claim 2 wherein V is furan carbonyl.

4. A compound of claim 2 wherein V is thiophene carbonyl.

5. A compound of claims 3 or 4 wherein Z is fluorine.

6. A compound of claims 3 or 4 wherein G is chlorine.

7. A compound of claims 3 or 4 wherein G is lower alkanoyloxy.

8. A compound of claim 5 wherein W is .alpha.-methyl.

9. A compound of claim 6 wherein W is .alpha.-methyl.

10. A compound of claim 7 wherein W is .alpha.-methyl.

11. A compound of claim 1 having the following formula: ##STR4## wherein W' is (H,H) or (H,CH.sub.3); X' is fluorine or chlorine; Y' is (H,.beta.OH) or (H,.beta.-halogen) provided X' is chlorine, said .beta.-halogen having an atomic weight of less than 100 and being at least as electronegative as X'; Z' is hydrogen or fluorine; V' is furan carbonyl or thiophene carbonyl; and G' is chlorine or OV.sub.2 ', wherein V.sub.2 ' is a member of the group consisting of hydrogen or an acyl radical of a hydrocarboncarboxylic acid having up to 12 carbon atoms, benzoic acid substituted by a halogen or methoxy group, retinoic acid, isonicotinic acid, and the acid radical of phosphoric acid and mono- and dialkali and alkaline earth metal salts thereof.

12. A compound according to claim 11 wherein V' is furan carbonyl.

13. A compound according to claim 11 wherein V' is thiophene carbonyl.

14. A compound according to claim 12 or 13 wherein W' is (H,.alpha.-methyl).

15. A compound of claim 14 wherein G' is chlorine.

16. A compound according to claim 15 wherein X' and Y' are each chlorine.

17. A compound according to claim 15 wherein X' is fluorine and Y' is (H,.beta.OH).

18. A compound according to claim 15 wherein X' is chlorine and Y' is (H,.beta.OH)

19. A compound according to claim 14 wherein G' is lower alkanoyloxy.

20. A compound according to claim 19 wherein X' and Y' are each chlorine.

21. A compound according to claim 19 wherein X' is fluorine and Y' is (H,.beta.OH).

22. A compound according to claim 18 wherein V' is 2-furan carbonyl, said compound being 9.alpha.,21-dichloro-16.alpha.-methyl-1, 4-pregnadiene-11.beta.,17.alpha.-diol-3, 20-dione 17-(2'-furoate).

23. A compound according to claim 16 wherein V' is 2-furan carbonyl, said compound being 9.alpha.,11.beta.,21-trichloro-16.alpha.-methyl-1, 4-pregnadiene-17.alpha.-ol-3,20-dione 17-(2'-furoate).

24. A compound according to claim 21 wherein V' is 2-furan carbonyl and V.sub.2 ' is acetyl, said compound being 9.alpha.-fluoro-16.alpha.-methyl-1, 4-pregnadiene-11.beta.,17.alpha.,21-triol-3,20-dione 17-2'-furoate) 21-acetate.

25. A compound according to claim 16 wherein V' is 2-thiophene carbonyl, said compound being 9.alpha.,11.beta.,21-trichloro-16.alpha.-methyl-1, 4-pregnadiene-17.alpha.-ol-3,20-dione 17-(2'-thenoate).

26. A compound according to claim 18 wherein V' is 2-thiophene carbonyl, said compound being 9.alpha.,21-dichloro-16.alpha.-methyl-1, 4-pregnadiene-11.beta.,17.alpha.-diol-3, 20-dione 17-(2'-theonate).

27. A compound according to claim 21 wherein V' is 2-thiophene carbonyl and V.sub.2 ' is acetyl, said compound being 9.alpha.-fluoro-16.alpha.-methyl-1, 4-pregnadiene-11.beta.,17.alpha.,21-triol-3, 20-dione 17-(2'-thenoate) 21-acetate.

28. A pharmaceutical composition for use in the treatment of inflammation which comprises an anti-inflammatorily effective amount of a 3,20-dioxo-1,4-pregnadiene-17.alpha.-ol 17-aromatic heterocyclic carboxylate of claim 1 together with a non-toxic, pharmaceutically acceptable carrier.

29. A pharmaceutical composition of claim 28 for use in the treatment of inflammation which comprises a topical, anti-inflammatorily effective amount of the compound of claim 11.

30. The method of treating an inflammatory condition in a warm-blooded animal responsive to treatment with anti-inflammatory agents which comprises administering to said animal a non-toxic, anti-inflammatorily effective amount of a 3,20-dioxo-1,4-pregnadiene-17.alpha.-ol 17-aromatic heterocyclic carboxylate of claim 1 together with a non-toxic, pharmaceutically acceptable carrier.

31. The method according to claim 30 for the treatment of a topical inflammatory condition which comprises applying to the inflamed area in a concentration effective for the topical treatment of inflammation a 3,20-dioxo-1,4-pregnadiene-17.alpha.-ol 17-aromatic heterocyclic carboxylate of claim 11, together with a non-toxic, pharmaceutically acceptable carrier.
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