Claims
- 1. The parabiphenyl esters of .omega.-pentanorprostaglandins having at the C.sub.15 position one hydrogen or lower alkyl group and one substituent of the structure:
- Ar -- (CH.sub.2).sub.n -- or -- (CH.sub.2).sub.m -- OR.sup.2
- wherein
- n is an integer from 0 to 5, with the proviso that when n is zero, said prostaglandin is a 13,14-dihydroprostaglandin;
- m is an integer from 1 to 4;
- R.sup.2 is lower alkyl,
- and Ar is .alpha.- or .beta.-furyl; .alpha.- or .beta.-thienyl; .alpha.- or .beta.-naphthyl; phenyl; 3,4-dimethoxy phenyl; 3,4-methylenedioxyphenyl; 3,4,5-trimethoxyphenyl or monosubstituted phenyl wherein said substituent is chloro, trifluoromethyl, phenyl, lower alkyl or lower alkoxy.
- 2. A compound of the structure: ##SPC10##
- wherein
- A is:
- Ar--(CH.sub.2).sub.n -- or -- (CH.sub.2).sub.m --OR.sup.2
- wherein
- n is an integer from 0 to 5,
- m is an integer from 2 to 3,
- R.sup.2 is lower alkyl,
- Ar is .alpha.- or .beta.-furyl; .alpha.- or .beta.-thienyl; .alpha.- or .beta.-naphthyl; phenyl; 3,4-dimethoxy phenyl; 3,4-methylenedioxyphenyl; 3,4,5-trimethoxyphenyl or monosubstituted phenyl wherein said substituent is chloro, trifluoromethyl, phenyl, lower alkyl or lower alkoxy,
- R.sub.1 is parabiphenyl;
- R is hydrogen or lower alkyl;
- W and L are each a single bond or cis double bond;
- Z is a single bond or trans double bond; with the proviso that when n is zero, Z is a single bond;
- M is keto, ##STR16## N is hydrogen or .alpha.-hydroxyl; and wherein
- L, m and N are so selected as to complete the structure of a prostaglandin of the A, E or F series.
- 3. The compounds of claim 1 wherein said C.sub.15 substituent is Ar -- (CH.sub.2).sub.n --.
- 4. The compounds of claim 1 wherein said C.sub.15 substituent is: (CH.sub.2).sub.m --OR.sup.2.
- 5. The compounds of claim 3 wherein said prostaglandin is of the E series.
- 6. The compounds of claim 3 wherein said prostaglandin is of the F series.
- 7. The compounds of claim 3 wherein said prostaglandin is of the A series.
- 8. The compounds of claim 4 wherein said prostaglandin is of the E series.
- 9. The compounds of claim 4 wherein said prostaglandin is of the F series.
- 10. The compounds of claim 4 wherein said prostaglandin is of the A series.
- 11. The compound of claim 5 wherein Ar is phenyl, n is 1 and said prostaglandin is PGE.sub.2.
- 12. The compound of claim 5 wherein Ar is phenyl, n is 1 and said prostaglandin is 13,14 dihydro PGE.sub.2.
- 13. The compound of claim 5 wherein Ar is phenyl, n is 1 and said prostaglandin is PGE.sub.1.
- 14. The compound of claim 5 wherein Ar is phenyl, n is 1 of said prostaglandin is PGE.sub.0.
- 15. The compound of claim 5 wherein Ar is phenyl, n is 2 and said prostaglandin is PGE.sub.2.
- 16. The compound of claim 6 wherein Ar is phenyl, n is 2 and said prostaglandin is PGF.sub.2.sub..alpha..
- 17. The compound of claim 5 wherein Ar is phenyl, n is 2 and said prostaglandin is PGE.sub.2.
- 18. The compound of claim 5 wherein Ar is .beta.-naphthyl, n is 1 and said prostaglandin is PGE.sub.2.
- 19. The compound of claim 5 wherein Ar is o-tolyl, n is 1 and said prostaglandin is PGE.sub.2.
- 20. The compound of claim 5 wherein Ar is p-tolyl, n is 1 and said prostaglandin is PGE.sub.2.
- 21. The compound of claim 5 wherein Ar is p-methoxyphenyl, n is 1 and said prostaglandin is PGE.sub.2.
- 22. The compound of claim 5 wherein Ar is .alpha.-thienyl, n is 1 and said prostaglandin is PGE.sub.2.
- 23. The compound of claim 5 wherein Ar is .beta.-thienyl, n is 1 and said prostaglandin is PGE.sub.2.
- 24. The compound of claim 6 wherein Ar is .alpha.-thienyl, n is 2 and said prostaglandin is PGF.sub.2.sub..alpha..
- 25. The compound of claim 6 wherein Ar is .alpha.-furyl, n is 2 and said prostaglandin is PGF.sub.2.sub..alpha..
- 26. The compound of claim 5 wherein Ar is phenyl, n is 0 and said prostaglandin is 13,14 dihydro PGE.sub.2.
- 27. The compound of claim 5 wherein Ar is phenyl, n is 1 and said prostaglandin is 15 methyl 13,14 dihydro PGE.sub.2.
- 28. The compound of claim 8 wherein m is 3, R.sup.2 is methyl and said prostaglandin is PGE.sub.2.
- 29. The compound of claim 9 wherein m is 3, R.sup.2 is methyl and said prostaglandin is PGF.sub.2.sub..alpha..
- 30. The compound of claim 8 wherein m is 4, R.sup.2 is methyl and said prostaglandin is PGE.sub.2.
- 31. The compound of claim 9 wherein m is 4, R.sup.2 is methyl and said prostaglandin is PGF.sub.2.sub..alpha..
- 32. The compound of claim 9 wherein m is 1, R is n-propyl and said prostaglandin is PGF.sub.2.sub..alpha..
- 33. The compound of claim 5 wherein n is 1, Ar is phenyl and said prostaglandin is 15 epi 13,14 dihydro PGE.sub.2.
- 34. The compound of claim 6 wherein n is 1, Ar is phenyl and said prostaglandin is PGF.sub.2.sub..alpha..
- 35. The compound of claim 6 wherein n is 1, Ar is phenyl and said prostaglandin is 13,14 dihydro PGF.sub.2.sub..beta..
- 36. The compound of claim 5 wherein n is 1, Ar is p-biphenyl and said prostaglandin is PGE.sub.2.
- 37. The compound of claim 5 wherein n is 1, Ar is .beta.-naphthyl and said prostaglandin is 15 epi-.omega.-tetranor PGE.sub.2.
CROSS REFERENCE TO RELATED APPLICATIONS
This application is a continuation-in-part of our earlier filed applications, Ser. No. 304,815 filed Nov. 7, 1972, and now abandoned, and Ser. No. 428,672, filed Dec. 27, 1973 and now abandoned.
Foreign Referenced Citations (1)
Number |
Date |
Country |
2,155,546 |
May 1972 |
DT |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
304815 |
Nov 1972 |
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