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Details for Patent: 4,158,667

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Details for Patent: 4,158,667

Title: 6-Keto PGF analogs
Abstract:Prostaglandin (PG.sub.1) derivatives having (1) a 6-keto feature, for example ##STR1## or (2) a 9-deoxy-6,9-epoxy feature together with a 5-halo or 6-hydroxy feature, for example ##STR2## said derivatives having pharmacological activity. Processes for preparing them and the appropriate intermediates are disclosed.
Inventor(s): Axen; Udo F. (Plainwell, MI)
Assignee: The Upjohn Company (Kalamazoo, MI)
Filing Date:Jul 28, 1977
Application Number:05/819,857
Claims:1. A compound of the formula ##STR108## or a mixture comprising that compound and the enantiomer thereof wherein R.sub.20 is ##STR109## wherein L is

(1) --(CH.sub.2).sub.d --C(R.sub.2).sub.2 --

(2) --(ch.sub.2 --o--ch.sub.2 --y-- or

(3) --CH.sub.2 CH.dbd.CH--

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, and Y is a valence bond, --CH.sub.2 -- or --(CH.sub.2).sub.2 --,

wherein Q is ##STR110## wherein R.sub.8 is hydrogen or alkyl of one to 4 carbon atoms, inclusive, wherein R.sub.8 is (a) hydrogen, (b) alkyl of one to 12 carbon atoms, inclusive, (c) cycloalkyl of 3 to 10 carbon atoms, inclusive, (d) aralkyl of 7 to 12 carbon atoms, inclusive, (e) phenyl, (f) phenyl substituted with one, 2, or 3 chloro or alkyl of one to 4 carbon atoms, inclusive, ##STR111## wherein R.sub.10 is phenyl, p-bromophenyl, p-biphenylyl, p-nitrophenyl, p-benzamidophenyl, or 2-naphthyl, and wherein R.sub.11 is hydrogen or benzoyl, or (n) a pharmacologically acceptable cation, wherein R.sub.59 is ##STR112## wherein C.sub.g H.sub.2g is alkylene of one to 9 carbon atoms, inclusive, with one to 5 carbon atoms, inclusive, in the chain between --CR.sub.5 R.sub.6 -- and terminal methyl, 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

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.

2. A compound according to claim 1 wherein R.sub.20 is ##STR113##

3. A compound according to claim 1 wherein R.sub.20 is ##STR114##

4. A compound according to claim 1 wherein R.sub.20 is ##STR115##

5. A compound according to claim 1 wherein R.sub.20 is ##STR116##

6. A compound according to claim 1 wherein R.sub.20 is ##STR117##

7. 6-Keto-11-deoxy-PGF.sub.1.alpha., methyl ester, a compound according to claim 6.

8. A compound according to claim 1 wherein R.sub.20 is ##STR118##

9. 6-Keto-11.beta.-PGF.sub.1.alpha., a compound according to claim 8.

10. 6-Keto-11.beta.-PGF.sub.1.alpha., methyl ester, a compound according to claim 8.

11. A compound according to claim 1 wherein R.sub.20 is ##STR119## wherein L is --(CH.sub.2).sub.n, n being 3, 4, or 5, wherein Q is ##STR120## wherein R.sub.8 is limited to hydrogen, methyl, or ethyl, and wherein R.sub.4 is n-pentyl, 1,1-dimethylpentyl or 1,1-difluoropentyl.

12. A compound according to claim 11 wherein X is --C.tbd.C--. ##STR121##

13. 6-Keto-13,14-didehydro-15(S)-PGF.sub.1.alpha., a compound according to claim 12.

14. 6-Keto-13,14-didehydro-15(R)-PGF.sub.1.alpha., a compound according to claim 12.

15. A compound according to claim 11 wherein X is --CH.sub.2 CH.sub.2 --.

16. 6-Keto-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 15.

17. 6-Keto-13,14-dihydro-PGF.sub.1.alpha., methyl ester, a compound according to claim 15.

18. 6,15-Diketo-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 15.

19. A compound according to claim 11 wherein X is trans-CH.dbd.CH--.

20. A compound according to claim 19 wherein R.sub.3 is ##STR122##

21. A compound according to claim 19 wherein R.sub.3 is ##STR123## wherein R.sub.10 and R.sub.11 are as defined in claim 1.

22. A compound according to claim 19 wherein R.sub.3 is hydrogen, alkyl of one to 12 carbon atoms, inclusive, or a pharmacologically acceptable cation.

23. 6-Keto-2a,2b-dihomo-PGF.sub.1.alpha., a compound according to claim 19.

24. A compound according to claim 22 wherein R.sub.3 is hydrogen, methyl, or a pharmacologically acceptable cation.

25. 6-Keto-PGF.sub.1.alpha., a compound according to claim 24.

26. 6-Keto-PGF.sub.1.alpha., methyl ester, a compound according to claim 24.

27. 6-Keto-PGF.sub.1.alpha., methyl ester, 11,15-diacetate, a compound according to claim 24.

28. 6,15-Diketo-PGF.sub.1.alpha., a compound according to claim 24.

29. 6-Keto-17,18-didehydro-PGF.sub.1.alpha., a compound according to claim 1.

30. 6-Keto-17,18-didehydro-PGF.sub.1.alpha., methyl ester, a compound according to claim 1.
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