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Home Molecular Biology Various-15-deoxy-16-hydroxy-16-ethynyl-and-16-ethynylsubstituted-prostaglandins

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 Various 15-deoxy-16-hydroxy-16-ethynyl and 16-ethynylsubstituted prostaglandins

Details
Inventors: Floyd, Jr., Middleton B.; Weiss, Martin J.; Grudzinskas, Charles V.; Chen, Sow-mei L.;
Assignee: American Cyanamid Company (Stamford, CT)
Primary Examiner: Gerstl; Robert
Assistant Examiner:
Attorney, Agent or Firm: Johnson; Norton S.

15-Deoxy-16-hydroxy-16-ethynyl and 16-ethynylsubstituted prostanoic acids and congeners thereof, useful as bronchodilators, hypotensive agents and as agents for the control of excessive gastric secretion.

DETAILED DESCRIPTION We claim: 1.
An optically active compound of the formula: ##STR24## wherein R.
sub.
1 is selected from the group consisting of hydrogen and C.
sub.
1 to C.
sub.
6 alkyl; R.
sub.
2 is selected from the group C.
sub.
3 to C.
sub.
7 alkyl; R.
sub.
3 is selected from the group consisting of hydrogen and hydroxy; X is selected from the group consisting of a divalent moiety of the formula: ##STR25## wherein R.
sub.
5 is selected from the group consisting of ethynyl, 1-propynyl and trimethylsilylethynyl; Z is selected from the group consisting of --(CH.
sub.
2).
sub.
6 --, --(CH.
sub.
2).
sub.
4 SCH.
sub.
2 -- and --(CH.
sub.
2)--O--CH.
sub.
2 --; the racemic mixture thereof; the mirror image thereof; and, when R.
sub.
1 is hydrogen, the pharmacologically acceptable salts thereof.
2.
A compound according to claim 1, wherein Z is --(CH.
sub.
2).
sub.
6 --.
3.
A compound according to claim 1, wherein Z is selected from the group consisting of --(CH.
sub.
2).
sub.
4 OCH.
sub.
2 -- and --(CH.
sub.
2).
sub.
4 --S--CH.
sub.
2.
4.
A compound according to claim 2, wherein R.
sub.
3 is hydroxyl.
5.
A compound according to claim 2, wherein R.
sub.
3 is hydrogen.
6.
A compound according to claim 3, wherein R.
sub.
3 is hydroxyl.
7.
A compound according to claim 3, wherein R.
sub.
3 is hydrogen.
8.
The compound according to claim 4, wherein R.
sub.
1 is methyl or ethyl.
9.
The compound according to claim 5, wherein R.
sub.
1 is methyl or ethyl.
10.
The compound according to claim 6, wherein R.
sub.
1 is methyl or ethyl.
11.
The compound according to claim 4, dl-11.
alpha.
,16-dihydroxy-9-oxo-16-ethynyl-20-ethyl-13-trans-prostenoic acid.
12.
The compound according to claim 4, dl-methyl-11.
alpha.
,16-dihydroxy-9-oxo-16-ethynyl-13-trans-prostenoate.
13.
The compound according to claim 6, dl-11.
alpha.
,16-dihydroxy-9-oxo-3-oxa-16-ethynyl-13-trans-prostenoic acid.
14.
The compound according to claim 4, dl-11.
alpha.
,16-dihydroxy-9-oxo-16-(1-propynyl)-13-trans-prostenoic acid.
15.
The compound according to claim 6, dl-11.
alpha.
,16-dihydroxy-9-oxo-3-oxa-16-(1-propynyl)-13-trans-prostenoic acid



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