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Details for Patent: 4,181,808

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Details for Patent: 4,181,808

Title: 5-Keto prostaglandin F.alpha. analogs
Abstract:Prostaglandin (PG.sub.1 derivatives having (1) a 5-keto feature, for example ##STR1## or (2) a 9-deoxy-5,9-epoxy feature together with a 4-halo or 5-hydroxy feature, for example ##STR2## or a 4,5-didehydro feature, for example in an enol ether of the formula ##STR3## said derivatives having pharmacological activity. Processes for preparing them and the appropriate intermediates are disclosed.
Inventor(s): Johnson; Roy A. (Kalamazoo, MI)
Assignee: The Upjohn Company (Kalamazoo, MI)
Filing Date:Aug 11, 1978
Application Number:05/932,898
Claims:1. A compound of the formula ##STR33## wherein R.sub.20 is ##STR34## wherein L is (1) --(CH.sub.2)d-C(R.sub.2).sub.2 --

(2) --O--CH.sub.2 --Y-- or

(3) --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 ##STR35## wherein R.sub.8 is hydrogen or alkyl of one to 4 carbon atoms, inclusive, wherein R.sub.3 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, ##STR36## 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.60 is ##STR37## wherein C.sub.g H.sub.2.sbsb.g 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,

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 --, and

wherein wavy line (.about.) indicates attachment in alpha or beta configuration.

2. A compound according to claim 1 wherein R.sub.20 is ##STR38##

3. A compound according to claim 1 wherein R.sub.20 is ##STR39##

4. A compound according to claim 1 wherein R.sub.20 is ##STR40##

5. A compound according to claim 1 wherein R.sub.20 is ##STR41##

6. 5-Keto-11-deoxy-PGF.sub.1.alpha., methyl ester, a compound according to claim 5.

7. A compound according to claim 1 wherein R.sub.20 is ##STR42##

8. A compound according to claim 1 wherein R.sub.20 is ##STR43##

9. A compound according to claim 1 wherein R.sub.20 is ##STR44##

10. A compound according to claim 9 wherein L is --(CH.sub.2)n, n being 2, 3, or 4, wherein Q is ##STR45## 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.

11. A compound according to claim 10 wherein X is --C.tbd.C--.

12. A compound according to claim 10 wherein X is --CH.sub.2 CH.sub.2 --.

13. 5-Keto-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 12.

14. 5-Keto-13,14-dihydro-PGF.sub.1.alpha., methyl ester, a compound according to claim 12.

15. 5,15-Diketo-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 12.

16. A compound according to claim 10 wherein X is trans--CH.dbd.CH--.

17. A compound according to claim 16 wherein R.sub.3 is hydrogen, alkyl of one to 12 carbon atoms, inclusive, or a pharmacologically acceptable cation.

18. 5-Keto-PGF.sub.1.alpha., a compound according to claim 17.

19. 5-Keto-PGF.sub.1.alpha., methyl ester, a compound according to claim 17.

20. 5,15-Diketo-PGF.sub.1.alpha., a compound according to claim 17.
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