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Details for Patent: 4,235,998

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Details for Patent: 4,235,998

Title: 2-Decarboxy-2-aminomethyl-9-deox y-5,9.alpha.-epoxy-4,5-didehydro-PGF.sub.1 compounds
Abstract:The present invention relates to novel 2- decarboxy-2-aminomethyl-9-deoxy-5,9.alpha.-epoxy-4,5-didehydro-PGF.sub.1 compounds, which are useful for inducing a variety of prostacyclin-like pharmacological effects. Accordingly, these compounds are useful pharmacological agents for the same purposes for which prostacyclin is employed.
Inventor(s): Johnson; Roy A. (Kalamazoo, MI)
Assignee: The Upjohn Company (Kalamazoo, MI)
Filing Date:Sep 07, 1979
Application Number:06/073,451
Claims:1. A compound of the formula ##STR3## wherein W.sub.1 is .alpha.-OH:.beta.H, .alpha.H:.beta.-OH, oxo, methylene, .alpha.-H:.beta.-H, .alpha.-CH.sub.2 OH:.beta.-H;

wherein L is -(CH.sub.2).sub.d -C(R.sub.2).sub.2,

wherein d is zero to 5, R.sub.2 is hydrogen, methyl, or fluoro, being the same or different with the proviso that one R.sub.2 is not methyl when the other is fluoro;

wherein Q is oxo, .alpha.-H:.beta.-H, .alpha.-OH:.beta.-R.sub.8 or .alpha.-R.sub.8 :.beta.-OH

wherein R.sub.8 is hydrogen or alkyl of one to 4 carbon atoms, inclusive;

wherein R.sub.9 is hydrogen, methyl, or ethyl, and wherein R.sub.18 is hydrogen, alkyl of one to 4 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, or phenyl substituted with alkyl of one to 4 carbon atoms, inclusive;

wherein R.sub.5 and R.sub.6 are hydrogen, alkyl of one to 4 carbon atoms, inclusive, or fluoro, being the same or different, with the proviso that one of R.sub.5 and R.sub.6 is fluoro only when the other is hydrogen or fluoro and the further proviso that neither R.sub.5 nor R.sub.6 is fluoro when Z is oxa (--O--); wherein Z represents an oxa atom (--O--), a valence bond or alkylene of one to 9 carbon atoms, inclusive, with one to 6 carbon atoms, inclusive between CR.sub.5 R.sub.6 - and the phenyl ring;

wherein T is alkyl of one to 4 carbon atoms, inclusive, fluoro, chloro, trifluoromethyl, or --OR.sub.7, wherein R.sub.7 is alkyl of one to 4 carbon atoms, inclusive, and s is zero, one, 2, or 3, with the proviso that not more than two T's are other than alkyl and when s is 2 or 3 the T's are either the same or different; and

wherein X is

(1) trans-CH.dbd.CH--,

(2) cis-CH.dbd.CH--,

(3) --C.dbd.C--, or

(4) --CH.sub.2 CH.sub.2 --;

including the lower alkanoates thereof.

2. A compound according to claim 1, wherein W.sub.1 is .alpha.-H:.beta.-OH.

3. A compound according to claim 1, wherein W.sub.1 is oxo.

4. A compound according to claim 1, wherein W.sub.1 is methylene.

5. A compound according to claim 1, wherein W.sub.1 is .alpha.-H-.beta.-H.

6. A compound according to claim 5, wherein L is --(CH.sub.2).sub.n --, n being 2, 3, or 4, and wherein Q is oxo or .alpha.-OH:.beta.-R.sub.8, wherein R.sub.8 is limited to hydrogen, methyl, or ethyl.

7. A compound according to claim 1, wherein W.sub.1 is .alpha.CH.sub.2 OH:.beta.-H.

8. A compound according to claim 1, wherein W.sub.1 is .alpha.-OH:.beta.-H.

9. A compound according to claim, 8, wherein L is --(CH.sub.2).sub.n --, n being 2, 3, or 4, and wherein Q is oxo or .alpha.-OH:.beta.-R.sub.8, wherein R.sub.8 is hydrogen, methyl, or ethyl.

10. A compound according to claim 9, wherein L is --CH.sub.2 CH.sub.2 --.

11. A compound according to claim 10, wherein R.sub.5 and R.sub.6 are hydrogen.

12. A compound according to claim 11, wherein s is zero.

13. A compound according to claim 8, wherein X is --C.tbd.C--.

14. A compound according to claim 8, wherein X is --CH.sub.2 CH.sub.2 --.

15. A compound according to claim 8, wherein X is trans-CH.dbd.CH--.

16. A compound according to claim 8, wherein X is cis-CH.dbd.CH--.

17. A compound according to claim 11, wherein s is one.

18. A compound according to claim 17, wherein X is --CH.sub.2 CH.sub.2 --.

19. A compound according to claim 17, wherein X is trans-CH.tbd.CH--.

20. A compound according to claim 17, wherein X is cis-CH.dbd.CH--.

21. A compound according to claim 10, wherein R.sub.5 and R.sub.6 are methyl.

22. A compound according to claim 21, wherein s is zero.

23. A compound according to claim 22, wherein X is --CH.sub.2 CH.sub.2 --.

24. A compound according to claim 22, wherein X is trans-CH.dbd.CH--.

25. A compound according to claim 22, wherein X is cis-CH.dbd.CH--.

26. A compound according to claim 10, wherein R.sub.5 and R.sub.6 are fluoro.

27. A compound according to claim 26, wherein s is zero.

28. A compound according to claim 27, wherein X is --CH.sub.2 CH.sub.2 --.

29. A compound according to claim 27, wherein X is trans-CH.dbd.CH--.

30. A compound according to claim 8, wherein L is --CH.sub.2 CF.sub.2, and wherein Q is oxo or .alpha.-OH:.beta.-R.sub.8, wherein R.sub.8 is hydrogen, methyl, or ethyl.

31. A compound according to claim 30, wherein R.sub.5 and R.sub.6 are hydrogen.

32. A compound according to claim 31, wherein s is zero.

33. A compound according to claim 32, wherein X is --CH.sub.2 CH.sub.2 --.

34. A compound according to claim 32, wherein X is trans-CH.dbd.CH--.

35. A compound according to claim 32, wherein X is cis-CH.dbd.CH--.

36. A compound according to claim 30, wherein R.sub.5 and R.sub.6 are methyl.

37. A compound according to claim 36, wherein s is zero.

38. A compound according to claim 37, wherein X is --CH.sub.2 CH.sub.2 --.

39. A compound according to claim 37, wherein X is trans-CH.dbd.CH--.

40. A compound according to claim 37, wherein X is cis-CH.dbd.CH--.

41. A 4E compound of the formula ##STR4## wherein W.sub.1 is .alpha.-OH:.beta.-H, .alpha.-H:.beta.-OH, oxo, methylene, .alpha.-H:.beta.-H, .alpha.-CH.sub.2 OH:.beta.-H;

wherein L is -(CH.sub.2).sub.d -C(R.sub.2).sub.2,

wherein d is zero to 5, R.sub.2 is hydrogen, methyl, or fluoro, being the same or different with the proviso that one R.sub.2 is not methyl when the other is fluoro;

wherein Q is oxo, .alpha.-H:.beta.-H, .alpha.-OH:.beta.-R.sub.8 or .alpha.-R.sub.8 :.beta.-OH

wherein R.sub.8 is hydrogen or alkyl of one to 4 carbon atoms, inclusive;

wherein R.sub.9 is hydrogen, methyl, or ethyl, and wherein R.sub.18 is hydrogen, alkyl of one to 4 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, or phenyl substituted with alkyl of one to 4 carbon atoms, inclusive;

wherein R.sub.5 and R.sub.6 are hydrogen, alkyl of one to 4 carbon atoms, inclusive, or fluoro, being the same or different, with the proviso that one of R.sub.5 and R.sub.6 is fluoro only when the other is hydrogen or fluoro and the further proviso that neither R.sub.5 nor R.sub.6 is fluoro when Z is oxa (--O--); wherein Z represents an oxa atom (--O--), a valence bond or alkylene of one to 9 carbon atoms, inclusive, with one to 6 carbon atoms, inclusive between CR.sub.5 R.sub.6 - and the phenyl ring;

wherein T is alkyl of one to 4 carbon atoms, inclusive, fluoro, chloro, trifluoromethyl, or -OR.sub.7, wherein R.sub.7 is alkyl of one to 4 carbon atoms, inclusive, and s is zero, one, 2, or 3, with the proviso that not more than two T's are other than alkyl and when s is 2 or 3 the T's are either the same or different; and

wherein X is

(1) trans-CH.dbd.CH--,

(2) cis-CH.dbd.CH--,

(3) --C.tbd.C--, or

(4) --CH.sub.2 CH.sub.2 --;

including the lower alkanoates thereof.
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