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Generated: February 21, 2018

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Title: 2-Decarboxy-2-aminomethyl-9-deoxy-5,9.alpha.-epoxy-4,5 -cis-17,18-tetradehydro-PGF.sub.1 compounds
Abstract:The present invention relates to novel 2-decarboxy-2-aminomethyl-9-deoxy-5,9.alpha.-epoxy-4,5-cis-17,18-tetra dehydro-PGF.sub.1 compounds, which are useful for inducing a variety of prostacyclin-like pharmacological effects. Accordingly, these compounds are useful pharmacological agents for the same purposes for which prostacyclin is employed.
Inventor(s): Johnson; Roy A. (Kalamazoo, MI)
Assignee: The Upjohn Company (Kalamazoo, MI)
Filing Date:Sep 07, 1979
Application Number:06/073,458
Claims:1. A compound of the formula ##STR2## wherein W.sub.1 is .alpha.--OH:.beta.--H, .alpha.--H:.beta.--OH, oxo, methylene, .alpha.--H:.beta.--H, .alpha.--CH.sub.2 OH:.beta.--H;

wherein L is

(1) --(CH.sub.2).sub.d --C(R.sub.2).sub.2, or

(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,

wherein R.sub.9 is hydrogen, methyl, or ethyl, and wherein R.sub.18 is hydrogen, alkyl of one to 4 carbon atoms, inclusive, aralkyl or 7 to 12 carbon atoms, inclusive, phenyl, or phenyl substituted with alkyl of one to 4 carbon atoms, inclusive;

wherein Q is oxo, .alpha.--H:.beta.--H, .alpha.--OH:.beta.--R.sub.8 or .alpha.--R.sub.8 :.beta.--OH

wherein R.sub.8 is hydrogen or alkyl of one to 4 carbon atoms, inclusive; 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 W.sub.1 is .alpha.--H:.beta.--OH.

3. A compound according to claim 1, wherein W.sub.1 is oxo.

4. A compound according to claim 1, wherein W.sub.1 is methylene.

5. A compound according to claim 1, wherein W.sub.1 is .alpha.--H:.beta.--H.

6. A compound according to claim 5, wherein L is --(CH.sub.2).sub.n --, n being 2, 3, or 4, wherein Q is oxo or .alpha.--OH:.beta.--R.sub.8 and wherein R.sub.8 is hydrogen, methyl, or ethyl.

7. A compound according to claim 1, wherein W.sub.1 is .alpha.--CH.sub.2 OH:.beta.--H.

8. A compound according to claim 1, wherein W.sub.1 is .alpha.--OH:.beta.--H.

9. A compound according to claim 8, wherein L is --(CH.sub.2).sub.n --, n being 2, 3, or 4, wherein Q is oxo or .alpha.--OH:.beta.--R.sub.8 and wherein R.sub.8 is hydrogen, methyl, or ethyl.

10. A compound according to claim 9, wherein X is --C.tbd.C--.

11. A compound according to claim 9, wherein X is --CH.sub.2 CH.sub.2 --.

12. A compound according to claim 9, wherein X is trans--CH.dbd.CH--.
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