TREA

2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro PGF.sub.1 compounds

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Information

  • Patent Grant
  • 4204079
  • Patent Number
    4,204,079
  • Date Filed
    Wednesday, July 12, 1978
    47 years ago
  • Date Issued
    Tuesday, May 20, 1980
    45 years ago
Information
Abstract
This invention comprises certain analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol. Also provided in this invention, are novel chemical processes useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.
Description
Claims
  • 1. A prostaglandin analog of the formula ##STR1## wherein Y is trans -CH=CH-; wherein M.sub.1 is ##STR2## wherein R.sub.5 is hydrogen or methyl; wherein L.sub.1 is ##STR3## or a mixture of ##STR4## wherein R.sub.3 and R.sub.4 are hydrogen, methyl, or fluoro, the same or different, with the proviso that one of R.sub.3 and R.sub.4 is methyl only when the other is hydrogen or methyl;
  • wherein g is one, 2, or 3; and
  • wherein m is one to 5, inclusive.
  • 2. A compound according to claim 1 wherein m is one or 2.
  • 3. A compound according to claim 1, wherein m is 4 or 5.
  • 4. A compound according to claim 1, wherein m is 3.
  • 5. A compound according to claim 4, wherein g is one.
  • 6. A compound according to claim 5, wherein at least one of R.sub.3 and R.sub.4 is fluoro.
  • 7. A compound according to claim 6, wherein R.sub.3 and R.sub.4 are both fluoro.
  • 8. A compound according to claim 7, wherein R.sub.5 is hydrogen.
  • 9. 2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-16,16-difluoro-PGF.sub.1.alpha., a compound according to claim 8.
  • 10. 2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-16,16-difluoro-15-epi-PGF.sub.1.alpha., a compound according to claim 8.
  • 11. A compound according to claim 5, wherein at least one of R.sub.3 and R.sub.4 is methyl.
  • 12. A compound according to claim 11, wherein R.sub.3 and R.sub.4 are both methyl.
  • 13. A compound according to claim 12, wherein R.sub.5 is hydrogen.
  • 14. 2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-16,16-dimethyl-PGF.sub.1.alpha., a compound according to claim 13.
  • 15. 2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-16,16-dimethyl-15-epi-PGF.sub.1.alpha., a compound according to claim 13.
  • 16. A compound according to claim 5, wherein R.sub.3 and R.sub.4 are both hydrogen.
  • 17. A compound according to claim 16, wherein R.sub.5 is methyl.
  • 18. 2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-15-methyl-PGF.sub.1.alpha., a compound according to claim 17.
  • 19. 2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-15-epi-15-methyl-PGF.sub.1.alpha., a compound according to claim 17.
  • 20. A compound according to claim 16, wherein R.sub.5 is hydrogen.
  • 21. 2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-PGF.sub.1.alpha., a compound according to claim 20.
  • 22. 2-Decarboxy-2-hydroxymethyl-cis-4,5-didehydro-15-epi-PGF.sub.1.alpha., a compound according to claim 20.
Parent Case Info

The present application is a continuation application of Ser. No. 778,649, filed Mar. 17, 1977; which is a divisional application of Ser. No. 647,363, filed Jan. 8, 1976, now U.S. Pat. No. 4,028,419.

US Referenced Citations (7)
Number Name Date Kind
3878239 Hayashi et al. Apr 1975
3914282 Pike Oct 1975
3932463 Schaub et al. Jan 1976
3933889 Magerlein Jan 1976
3959346 Schneidner May 1976
3962293 Magerlein Jun 1976
3962312 Hayashi et al. Jun 1976
Non-Patent Literature Citations (2)
Entry
Burger, "Medicinal Chemistry," pp. 81-82 (1960).
Derwent Farmdec CPI No. 22,600 (British Patent 1,040,545-1-9-66).
Divisions (1)
Number Date Country
Parent 647363 Jan 1976
Continuations (1)
Number Date Country
Parent 778649 Mar 1977