2-Decarboxy-2-hydroxy-methyl-16-fluoro-PGE1 compounds

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.

I claim:  .[.1. A prostaglandin analog of the formula ##STR86## wherein M 1  is ##STR87## wherein R 5  is hydrogen or methyl; wherein L 1  is ##STR88## or a mixture of ##STR89## wherein R 3  and R 4  are hydrogen, methyl or fluoro, being the same or different, with the proviso that one of R 3  and R 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; with the proviso that at least one of R 3 , R 4 , and R 5  is methyl or at least one of R 3  and 
     
        R 4  is fluoro..]. .[.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 3  and R 4  is fluoro..]. .[.7. A compound according to claim 5, werein R 3  and R 4  are both fluoro..]. .[.8. A compound according to claim 7, wherein R 4  is hydrogen..]. .[.9. 2-Decarboxy-2-hydroxymethyl-16,16-difluoro-PGE 1 , a compound according to claim 8..]. .[.10. A compound according to claim 5 wherein at least one of R 3  and R 4  is methyl..]. .[.11. A compound according to claim 10, wherein R 3  and R 4  are both methyl..]. .[.12. A compound according to claim 11, wherein R 5  is hydrogen..]. .[.13. 2-Decarboxy-2-hydroxymethyl-16,16-dimethyl-PGE 1 , a compound according to claim 12..]. .[.14. A compound according to claim 5, wherein R 3  and R 4  are hydrogen and R 5  is methyl..].  .[.15. 2-Decarboxy-2-hydroxymethyl-15-methyl-PGE 1 , a compound according to claim 14..]. .Iadd. 16. A prostaglandin analog of the formula ##STR90## wherein M 1  is ##STR91## wherein R 5  is hydrogen or methyl; wherein g is one, 2, or 3; and 
     
     
       wherein m is one to 5, inclusive. .Iaddend..Iadd. 17. 2-Decarboxy-2-hydroxymethyl-16,16-difluoro-PGE 1 . .Iaddend.