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Details
Inventors: Kelly, Robert C.;
Assignee: The Upjohn Company (Kalamazoo, MI)
Primary Examiner: Chan; Nicky
Assistant Examiner:
Attorney, Agent or Firm: Nielsen; Morris L.

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. Processess for preparing them and the appropriate intermediates are disclosed.

DETAILED DESCRIPTION I claim: 1.
A 5Z compound of the formula ##STR115## 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 ##STR116## 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 carbom atoms, inclusive, or (c) a pharmacologically acceptable cation; wherein R.
sub.
4 is ##STR117## 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 ##STR118## 3.
A compound according to claim 1 wherein R.
sub.
20 is ##STR119## 4.
A compound according to claim 1 wherein R.
sub.
20 is ##STR120## 5.
A compound according to claim 1 wherein R.
sub.
20 is ##STR121## 6.
A compound according to claim 5 wherein L is --(CH.
sub.
2).
sub.
n --, n being 3, 4, or 5, wherein Q is ##STR122## 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.
(5Z)-9-Deoxy-6,9.
alpha.
-epoxy-methano-.
DELTA.
.
sup.
5 -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 ##STR123## 9.
A compound according to claim 1 wherein R.
sub.
20 is ##STR124## 10.
A compound according to claim 1 wherein R



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