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Details for Patent: 4,178,441

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Details for Patent: 4,178,441

Title: Enlarged-hetero-ring prostacylin analogs
Abstract:Prostaglandin (PG.sub.1) derivatives having (1) a 6-keto feature, together with a 9-deoxy-9-hydroxymethyl feature for example ##STR1## or (2) a 9-deoxy-6,9-epoxymethano feature together with a 5-halo or 6-hydroxy feature, for example ##STR2## or a 5,6-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): Kelly; Robert C. (Kalamazoo, MI)
Assignee: The Upjohn Company (Kalamazoo, MI)
Filing Date:Aug 21, 1978
Application Number:05/935,296
Claims:1. A 5Z compound of the formula ##STR20## wherein R.sub.20 is ##STR21## 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 ##STR22## wherein R.sub.8 is hydrogen or alkyl of one to 4 carbon atoms, inclusive, wherein

R.sub.60 is (a) cycloalkyl of 3 to 10 carbon atoms, inclusive, (b) aralkyl of 7 to 12 carbon atoms, inclusive, (c) phenyl, (d) phenyl substituted with one, 2, or 3 chloro or alkyl of one to 4 carbon atoms, inclusive, ##STR23## 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, 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 5E compound of the formula ##STR24## wherein R.sub.20 is ##STR25## 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 ##STR26## wherein R.sub.8 is hydrogen or alkyl of one to 4 carbon atoms, inclusive,

wherein R.sub.60 is (a) cycloalkyl of 3 to 10 carbon atoms, inclusive, (b) aralkyl of 7 to 12 carbon atoms, inclusive, (c) phenyl, (d) phenyl substituted with one, 2, or 3 chloro or alkyl of one to 4 carbon atoms, inclusive, ##STR27## 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, 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.

3. A compound according to claim 1 wherein R.sub.20 is ##STR28##

4. A compound according to claim 1 wherein R.sub.20 is ##STR29##

5. A compound according to claim 1 wherein R.sub.20 is ##STR30##

6. A compound according to claim 1 wherein R.sub.20 is ##STR31##

7. A compound acccording to claim 6 wherein L is --(CH.sub.2).sub.n --, n being 3, 4, or 5, wherein Q is ##STR32## wherein R.sub.8 is limited to hydrogen, methyl, or ethyl, and wherein ##STR33## is n-pentyl, 1,1-dimethylpentyl or, 1,1-difluoropentyl.

8. A compound according to claim 1 wherein R.sub.20 is ##STR34##

9. A compound according to claim 1 wherein R.sub.20 is ##STR35##

10. A compound according to claim 1 wherein R.sub.20 is ##STR36##

11. A compound according to claim 10 wherein L is --(CH.sub.2).sub.n --, n being 3, 4, or 5, wherein Q is ##STR37## wherein R.sub.8 is hydrogen, methyl, or ethyl, and wherein ##STR38## is n-pentyl, 1,1-dimethylpentyl or, 1,1-difluoropentyl.

12. A compound according to claim 11 wherein X is --C.dbd.C--.

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

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

15. A compound according to claim 14 wherein R.sub.60 is ##STR39##

16. A compound according to claim 14 wherein R.sub.60 is ##STR40## wherein R.sub.10 and R.sub.11 are as defined in claim 1.

17. (5Z)-9-Deoxy-6,9.alpha.-epoxy-methano-.DELTA..sup.5 -PGF.sub.1, p-phenylphenacyl ester, a compound according to claim 16.
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