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Details for Patent: 4,123,441

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Details for Patent: 4,123,441

Title: Enlarged-hetero-ring prostacyclin 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:Jul 28, 1977
Application Number:05/819,856
Claims:1. A 4Z compound of formula ##STR110## 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 ##STR111## wherein R.sub.8 is hydrogen or alkyl of one to 4 carbon atoms, inclusive, wherein R.sub.59 is (a) hydrogen, (b) alkyl of one to 12 carbon atoms, inclusive,

or (c) a pharmacologically acceptable cation; wherein R.sub.4 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.dbd.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 5 wherein L is --(CH.sub.2).sub.n --, n being 2, 3, or 4, wherein Q is ##STR117## 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.

7. (4Z)-9-Deoxy-5,9.alpha.-epoxy-.DELTA..sup.4 -11-deoxy-PGF.sub.1, methyl ester, a compound according to claim 6.

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

9. A compound according to claim 1 wherein R.sub.20 is ##STR119##

10. A compound according to claim 1 wherein R.sub.20 is ##STR120##

11. A compound according to claim 10 wherein L is --(CH.sub.2).sub.n --, n being 2, 3, or 4, wherein Q is ##STR121## wherein R.sub.8 is 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--.

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

14. (4Z)-9-Deoxy-5,9.alpha.-epoxy-.DELTA..sup.4 -13,14-dihydro-PGF.sub.1, methyl ester, a compound according to claim 13.

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

16. (4Z)-9-Deoxy-5,9.alpha.-epoxy-.DELTA..sup.4 -PGF.sub.1, methyl ester, a compound according to claim 15.

17. (4Z)-9-Deoxy-5,9.alpha.-epoxy-.DELTA..sup.4 -PGF.sub.1, sodium salt, a compound according to claim 15.

18. (4Z)-9-Deoxy-5,9.alpha.-epoxy-.DELTA..sup.4 -PGF.sub.1, tetramethylammonium salt, a compound according to claim 15.

19. (4Z)-9-Deoxy-5,9.alpha.-epoxy-.DELTA..sup.4 -15-keto-PGF.sub.1, methyl ester, a compound according to claim 15.

20. (4Z)-9-Deoxy-5,9.alpha.-epoxy-.DELTA..sup.4 -15-deoxy-PGF.sub.1, methyl ester, a compound according to claim 10.

21. A 4E compound of the formula ##STR122## 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 ##STR123## wherein R.sub.8 is hydrogen or alkyl of one to 4 carbon atoms, inclusive, wherein R.sub.59 is (a) hydrogen, (b) alkyl of one to 12 carbon atoms, inclusive, a pharmacologically acceptable cation;

wherein R.sub.4 is ##STR124## 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; 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.

22. (4E)-9-Deoxy-5,9.alpha.-epoxy-.DELTA..sup.4 -PGF.sub.1, methyl ester, a compound according to claim 21.
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