2-Decarboxy-2-hydroxy-methyl-5-oxa-17-phenyl-18,19,20-trinor-PGF-analogs
AssigneeThe Upjohn Company
InventorNorman A. Nelson
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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.
Claims25
A prostaglandin analog of the formula ##STR160## wherein R.sub.8 is hydrogen or hydroxy;
- wherein Y is trans--CH.dbd.CH--;
- wherein M.sub.1 is ##STR161## wherein R.sub.5 is hydrogen or methyl:
- wherein L.sub.1 is ##STR162## or a mixture of ##STR163## wherein R.sub.3 and R.sub.4 are hydrogen, methyl or fluoro, being 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 Z.sub.2 is
- --CH.sub.2 --O--(CH.sub.2).sub.g --CH.sub.2 --;
- where g is one, 2, or 3;
- and
- wherein R.sub.7 is ##STR164## wherein Z.sub.3 is methylene, s is zero, one, 2, or 3 and T is chloro, fluoro, trifluoromethyl, alkyl of one to 3 carbon atoms, inclusive, or alkoxy of one to 3 carbon atoms, inclusive, the various T's being the same or different, with the provisio that not more than two T's are other than alkyl;
A compound according to claim 3, wherein at least one of R.sub.3 and
2-Decarboxy-2-hydroxymethyl-5-oxa-15-methyl-16,16-difluoro- 17-phenyl-18,19,20-trinor-11-deoxy-PGF.sub.1 .alpha., a compound according
2-Decarboxy-2-hydroxymethyl-5-oxa-16,16-difluoro-17phenyl-18, 19,20-trinor-11-deoxy-PGF.sub.1 .alpha., a compound according to claim 8.
A compound according to claim 3, wherein at least one of R.sub.3 and
2-Decarboxy-2-hydroxymethyl-5-oxa-15,16,16-trimethyl-17-phen yl-18,19,20-trinor-11-deoxy-PGF.sub.1 .alpha., a compound according to
2-Decarboxy-2-hydroxymethyl-5-oxa-16,16-dimethyl17-phenyl-18,1 9,20-trinor-11-deoxy-PGF.sub.1 .alpha., a compound according to claim 14.
A compound according to claim 3, wherein R.sub.3 and R.sub.4 are both
2-Decarboxy-2-hydroxymethyl-5-oxa-15-methyl-17-phenyl-18,19, 20-trinor-11-deoxy-PGF.sub.1 .alpha., a compound according to claim 17.
2-Decarboxy-2-hydroxymethyl-5-oxa-17-phenyl-18,19,20-trinor-11
A compound according to claim 21, wherein at least one of R.sub.3 and
2-Decarboxy-2-hydroxymethyl-5-oxo-15-methyl-16,16-difluoro-1 7-phenyl-18,19,20-trinor-PGF.sub.1 .alpha., a compound according to claim
2-Decarboxy-2-hydroxymethyl-5-oxa-16,16-difluoro17-phenyl-18,1
A compound according to claim 3, wherein at least one of R.sub.3 and
2-Decarboxy-2-hydroxymethyl-5-oxa-15,16,16-trimethyl-17-phen yl-18,19,20-trinor-PGF.sub.1 .alpha., a compound according to claim 30.
2-Decarboxy-2-hydroxymethyl-5-oxa-16,16-dimethyl17-p henyl-18,19,20-trinor-PGF.sub.1 .alpha., a compound according to claim 32.
A compound according to claim 21, wherein R.sub.3 and R.sub.4 are both
2-Decarboxy-2-hydroxymethyl-5-oxa-15-methyl-17-phenyl-18,19,
2-Decarboxy-2-hydroxymethyl-5-oxa-17-phenyl18,19,20-trinor-PGF
Dependencies are inferred from the claim text.