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Generated: June 23, 2018

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Details for Patent: 4,234,492

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Title: 2-Decarboxy-2-aminomethyl-9-deo xy-6,9.alpha.-epoxymethano-5,6-didehydro-PGF.sub.1 compounds
Abstract:The present invention relates to novel 2-decarboxy-2-aminomethyl-9-deoxy-6,9.alpha.-epoxymethano-5,6-didehydro-PG F.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): Kelly; Robert C. (Kalamzoo, MI)
Assignee: The Upjohn Company (Kalamazoo, MI)
Filing Date:Aug 16, 1979
Application Number:06/067,493
Claims:1. A 5E compound of the formula ##STR3## 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,

(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 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,

wherein R.sub.9 is hydrogen, methyl, or ethyl;

wherein R.sub.18 is hydrogen, alkyl of one to 4 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, or phenyl substituted with 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 5Z compound of the formula ##STR4## 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,

(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 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 R.sub.9 is hydrogen, methyl, or ethyl;

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

3. 2-Decarboxy-2-aminomethyl-(5Z)-9-deo xy-6,9.alpha.-epoxymethano-.DELTA..sup.5 -17,18-cis-didehydro-PGF.sub.1, a compound according to claim 2.

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

5. A compound according to claim 1 or 2, wherein W.sub.1 is oxo.

6. A compound according to claim 1 or 2, wherein W.sub.1 is methylene.

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

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

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

10. A compound according to claim 9, wherein L is --(CH.sub.2).sub.n --, n being 3, 4, or 5, wherein Q is oxo or .alpha.-OH:.beta.-R.sub.8 and wherein R.sub.8 is hydrogen, methyl, or ethyl.

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

12. A compound according to claim 10, wherein X is --CH.sub.2 CH.sub.2 --.

13. A compound according to claim 10, wherein X is trans-CH.dbd.CH--.

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