TREA

2-Decarboxy-2-hydroxymethyl-6-keto-PG compounds

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Information

  • Patent Grant
  • 4235822
  • Patent Number
    4,235,822
  • Date Filed
    Wednesday, October 17, 1979
    44 years ago
  • Date Issued
    Tuesday, November 25, 1980
    43 years ago
Information
Abstract
The present invention relates to novel 2-decarboxy-2-hydroxymethyl-6-keto-PG 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.
Description

BACKGROUND OF THE INVENTION
The present invention relates to novel2-decarboxy-2-hydroxymethyl-6-keto-PG 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.
The essential material constituting a disclosure of the preparation and use of the novel compounds of the present invention are incorporated here by reference from U.S. Pat. No. 4,158,667.
SUMMARY OF THE INVENTION
The present invention particularly provides:
A compound of the formula ##STR1## 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 wherein Y is a valence bond, --CH.sub.2 -- or --(CH.sub.2).sub.2,
wherein Q is keto, .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.5 and R.sub.6 are hydrogen, alkyl of one to 4 carbon atoms, inclusive, or fluoro, being the same or different, with the proviso that one of R.sub.5 and R.sub.6 is fluoro only when the other is hydrogen or fluoro and the further proviso that neither R.sub.5 nor R.sub.6 is fluoro when Z is oxa (--O--); wherein Z represents an oxa atom (--O--) or C.sub.j H.sub.2j, wherein C.sub.j H.sub.2j is a valence bond or alkylene of one to 9 carbon atoms, inclusive, with one to 6 carbon atoms, inclusive between CR.sub.5 R.sub.6 -- and the phenyl ring; wherein T is alkyl of one to 4 carbon atoms, inclusive, fluoro, chloro, trifluoromethyl, or --OR.sub.7 --, wherein R.sub.7 is alkyl of one to 4 carbon atoms, inclusive, and s is zero, one, 2, or 3, with the proviso that not more than two T's are other than alkyl and when s is 2 or 3 the T's are either the same or different; and
wherein X is
(1) trans--CH.dbd.CH--,
(2) cis--CH.dbd.CH--,
(3) --C.quadbond.C--, or
(4) --CH.sub.2 CH.sub.2 --;
including the lower alkanoates thereof.
With regard to the divalent substituents described in the claims, e.g., Q and W.sub.1, these divalent radicals are defined as .alpha.-R.sub.i :.beta.-R.sub.j, where R.sub.i represents a substituent of the divalent moiety of the alpha configuration with respect to the cyclopentane and R.sub.j represents a substituent of the divalent moiety of the beta configuration with respect to the cyclopentane ring. Accordingly, when Q is defined as .alpha.-OH:.beta.-R.sub.8, the hydroxy of the Q moiety is in the alpha configuration, i.e., as in prostacyclin, and the R.sub.8 substituent is in the beta configuration. Not all carbon atoms to which such divalent moieties are attached represent asymmetric centers. For example, when both valence bonds are to hydrogen (e.g., W.sub.1 or Q is .alpha.-H:.beta.-H), then no asymmetric center is present.





DESCRIPTION OF THE PREFERRED EMBODIMENTS
The present invention particularly relates to the following chemical compounds:
2-Decarboxy-2-hydroxymethyl-6-keto-11.beta.-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-11-deoxy-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-13,14-didehydro-15(S)-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-13,14-didehydro-(15R)-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1 ;
2-Decarboxy-2-hydroxymethyl-6-keto-13,14-dihydro-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6,15-diketo-13,14-dihydro-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha., 11,15-diacetate;
2-Decarboxy-2-hydroxymethyl-6,15-diketo-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-17-phenyl-18,19,20-trinor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-17-phenyl-18,19,20-trinor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-17-(m-trifluoromethylphenyl)-18,19,20-trinor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-17-(m-chlorophenyl)-18,19,20-trinor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-17-(p-fluorophenyl)-18,19,20-trinor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16,16-dimethyl-17-phenyl-18,19,20-trinor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16,16-difluoro-17-phenyl-18,19,20-trinor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16-(m-chlorophenoxy)-17,18,19,20-tetranor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16-(p-fluorophenoxy)-17,18,19,20-tetranor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16-methyl-16-phenoxy-18,19,20-trinor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16-(m-chlorophenoxy)-17,18,19,20-tetranor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16-(p-fluorophenoxy)-17,18,19,20-tetranor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16-methyl-16-phenoxy-18,19,20-trinor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-17-(m-chlorophenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-17-(m-fluorophenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16,16-difluoro-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16-methyl-16-phenoxy-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-17-(m-chlorophenyl)-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-17-(m-fluorophenyl)-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16,16-difluoro-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16-(p-fluorophenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16-methyl-16-phenoxy-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-17-(m-trifluoromethylphenyl)-18,19,20-trinor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-17-(m-chlorophenyl)-18,19,20-trinor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-17-(p-fluorophenyl)-18,19,20-trinor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16,16-dimethyl-17-phenyl-18,19,20-trinor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16,16-difluoro-17-phenyl-18,19,20-trinor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16-(m-chlorophenoxy)-17,18,19,20-tetranor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16-(p-fluorophenoxy)-17,18,19,20-tetranor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-16-methyl-16-phenoxy-18,19,20-trinor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-phenyl-18,19,20-trinor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-(m-trifluoromethylphenyl)-18,19,20-trinor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-(m-chlorophenyl)-18,19,20-trinor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-(p-fluorophenyl)-18,19,20-trinor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16,16-dimethyl-17-phenyl-18,19,20-trinor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16,16-difluoro-17-phenyl-18,19,20-trinor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-(m-chlorophenoxy)-17,18,19,20-tetranor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-(p-fluorophenoxy)-17,18,19,20-tetranor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-methyl-16-phenoxy-18,19,20-trinor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-(m-chlorophenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-(p-fluorophenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2,16,16-tetrafluoro-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-phenoxy-17,18,19,20-tetranor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-methyl-16-phenoxy-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-(m-chlorophenyl)-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-(p-fluorophenyl)-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2,16,16-tetrafluoro-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-phenoxy-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-(p-fluorophenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-methyl-16-phenoxy-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-phenyl-18,19,20-trinor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-(m-trifluoromethylphenyl)-18,19,20-trinor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-(m-chlorophenyl)-18,19,20-trinor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-(p-fluorophenyl)-18,19,20-trinor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16,16-dimethyl-17-phenyl-18,19,20-trinor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-phenyl-18,19,20-trinor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-phenoxy-17,18,19,20-tetranor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-(m-chlorophenoxy)-17,18,19,20-tetranor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-(p-fluorophenoxy)-17,18,19,20-tetranor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-methyl-16-phenoxy-18,19,20-trinor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-phenyl-18,19,20-trinor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-(m-trifluoromethylphenyl)-18,19,20-trinor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-(m-chlorophenyl)-18,19,20-trinor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16,16-dimethyl-17-phenyl-18,19,20-trinor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16,16-difluoro-17-phenyl-18,19,20-trinor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-(m-chlorophenoxy)-17,18,19,20-tetranor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-(p-fluorophenoxy)-17,18,19,20-tetranor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-methyl-16-phenoxy-18,19,20-trinor-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-(m-chlorophenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-(p-fluorophenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16,16-difluoro-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-phenoxy-17,18,19,20-tetranor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-methyl-16-phenoxy-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-(m-chlorophenyl)-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-(p-fluorophenyl)-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16,16-difluoro-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-phenoxy-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-(p-fluorophenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-methyl-16-phenoxy-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-phenyl-18,19,20-trinor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-(m-trifluoromethylphenyl)-18,19,20-trinor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-(m-chlorophenyl)-18,19,20-trinor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-(p-fluorophenyl)-18,19,20-trinor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16,16-dimethyl-17-phenyl-18,19,20-trinor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16,16-difluoro-17-phenyl-18,19,20-trinor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-phenoxy-17,18,19,20-tetranor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-(m-chlorophenoxy)-17,18,19,20-tetranor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-(p-fluorophenoxy)-17,18,19,20-tetranor-cis-13-PGF.sub.1.alpha. ;
2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-methyl-16-phenoxy-18,19,20-trinor-cis-13-PGF.sub.1.alpha. ; and
2-Decarboxy-2-hydroxymethyl-6-keto-17-phenyl-18,19,20-trinor-PGF.sub.1.alpha. ;
Claims
  • 1. A prostacyclin intermediate of formula ##STR2## 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 wherein Y is a valence bond, --CH.sub.2 -- or --(CH.sub.2).sub.2,
  • wherein Q is keto, .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.5 and R.sub.6 are hydrogen, alkyl of one to 4 carbon atoms, inclusive, or fluoro, being the same or different, with the proviso that one of R.sub.5 and R.sub.6 is fluoro only when the other is hydrogen or fluoro and the further proviso that neither R.sub.5 nor R.sub.6 is fluoro when Z is oxa (--O--); wherein Z represents an oxa atom (--O--) or C.sub.j H.sub.2j, wherein C.sub.j H.sub.2j is a valence bond or alkylene of one to 9 carbon atoms, inclusive, with one to 6 carbon atoms, inclusive between CR.sub.5 R.sub.6 - and the phenyl ring; wherein T is alkyl of one to 4 carbon atoms, inclusive, fluoro, chloro, trifluoromethyl, or --OR.sub.7 --, wherein R.sub.7 is alkyl of one to 4 carbon atoms, inclusive, and s is zero, one, 2, or 3, with the proviso that not more than two T's are other than alkyl and when s is 2 or 3 the T's are either the same or different; 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 compound according to claim 1, wherein W.sub.1 is .alpha.-H:.beta.-OH.
  • 3. 2-Decarboxy-2-hydroxymethyl-6-keto-11.beta.-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha., a compound according to claim 2.
  • 4. A compound according to claim 1, wherein W.sub.1 is oxo.
  • 5. A compound according to claim 1, wherein W.sub.1 is methylene.
  • 6. A compound according to claim 1, wherein W.sub.1 is .alpha.-H:.beta.-H.
  • 7. 2-Decarboxy-2-hydroxymethyl-6-keto-11-deoxy-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha., a compound according to claim 6.
  • 8. A compound according to claim 1, wherein W.sub.1 is .alpha.-CH.sub.2 OH:.beta.-H.
  • 9. A compound according to claim 1, wherein W.sub.1 is .alpha.-OH:.beta.-H, wherein L is --(CH.sub.2).sub.n, n being 3, 4, or 5, and wherein Q is oxo or .alpha.-OH:.beta.-R.sub.8.
  • 10. A compound according to claim 9, wherein X is --C.tbd.C--.
  • 11. 2-Decarboxy-2-hydroxymethyl-6-keto-13,14-didehydro-15(S)-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha., a compound according to claim 10.
  • 12. 2-Decarboxy-2-hydroxymethyl-6-keto-13,14-didehydro-(15R)-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha., a compound according to claim 10.
  • 13. A compound accordng to claim 9, wherein X is --CH.sub.2 CH.sub.2 --.
  • 14. 2-Decarboxy-2-hydroxymethyl-6-keto-13,14-dihydro-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha., a compound according to claim 13.
  • 15. 2-Decarboxy-2-hydroxymethyl-6,15-diketo-13,14-dihydro-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha., a compound according to claim 13.
  • 16. A compound according to claim 9, wherein X is trans--CH.dbd.CH--.
  • 17. 2-Decarboxy-2-hydroxymethyl-6-keto-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha., a compound according to claim 16.
  • 18. 2-Decarboxy-2-hydroxymethyl-6-keto-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha., 11,15-diacetate, a compound according to claim 16.
  • 19. 2-Decarboxy-2-hydroxymethyl-6,15-diketo-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha., a compound according to claim 16.
  • 20. 2-Decarboxy-2-hydroxymethyl-6-keto-17-phenyl-18,19,20-trinor-PGF.sub.1.alpha., a compound according to claim 16.
  • 21. 2-Decarboxy-2-hydroxymethyl-6-keto-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 13.
  • 22. 2-Decarboxy-2-hydroxymethyl-6-keto-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 10.
  • 23.2-Decarboxy-2-hydroxymethyl-6-keto-17-phenyl-18,19,20-trinor-cis-13-PGF.sub.1.alpha., a compound according to claim 9.
  • 24. 2-Decarboxy-2-hydroxymethyl-6-keto-17-(m-trifluoromethylphenyl)-18,19,20-trinor-PGF.sub.1.alpha., a compound according to claim 1.
  • 25. 2-Decarboxy-2-hydroxymethyl-6-keto-17-(m-chlorophenyl)-18,19,20-trinor-PGF.sub.1.alpha., a compound according to claim 1.
  • 26. 2-Decarboxy-2-hydroxymethyl-6-keto-17-(p-fluorophenyl)-18,19,20-trinor-PGF.sub.1.alpha., a compound according to claim 1.
  • 27. 2-Decarboxy-2-hydroxymethyl-6-keto-16,16-dimethyl-17-phenyl-18,19,20-trinor-PGF.sub.1.alpha., a compound according to claim 1.
  • 28. 2-Decarboxy-2-hydroxymethyl-6-keto-16,16-difluoro-17-phenyl-18,19,20-trinor-PGF.sub.1.alpha., a compound according to claim 1.
  • 29. 2-Decarboxy-2-hydroxymethyl-6-keto-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-PGF.sub.1.alpha., a compound according to claim 1.
  • 30. 2-Decarboxy-2-hydroxymethyl-6-keto-16-(m-chlorophenoxy)-17,18,19,20-tetranor-PGF.sub.1.alpha., a compound according to claim 1.
  • 31. 2-Decarboxy-2-hydroxymethyl-6-keto-16-(p-fluorophenoxy)-17,18,19,20-tetranor-PGF.sub.1.alpha., a compound according to claim 1.
  • 32. 2-Decarboxy-2-hydroxymethyl-6-keto-16-methyl-16-phenoxy-18,19,20-trinor-PGF.sub.1.alpha., a compound according to claim 1.
  • 33. 2-Decarboxy-2-hydroxymethyl-6-keto-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 34. 2-Decarboxy-2-hydroxymethyl-6-keto-17-(m-chlorophenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 35. 2-Decarboxy-2-hydroxymethyl-6-keto-17-(m-fluorophenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 36. 2-Decarboxy-2-hydroxymethyl-6-keto-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 37. 2-Decarboxy-2-hydroxymethyl-6-keto-16,16-difluoro-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 38. 2-Decarboxy-2-hydroxymethyl-6-keto-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 39. 2-Decarboxy-2-hydroxymethyl-6-keto-16-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 40. 2-Decarboxy-2-hydroxymethyl-6-keto-16-methyl-16-phenoxy-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha., compound according to claim 1.
  • 41. 2-Decarboxy-2-hydroxymethyl-6-keto-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha., compound according to claim 1.
  • 42. 2-Decarboxy-2-hydroxymethyl-6-keto-17-(m-chlorophenyl)-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 43. 2-Decarboxy-2-hydroxymethyl-6-keto-17-(m-fluorophenyl)-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 44. 2-Decarboxy-2-hydroxymethyl-6-keto-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 45. 2-Decarboxy-2-hydroxymethyl-6-keto-16,16-difluoro-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 46. 2-Decarboxy-2-hydroxymethyl-6-keto-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 47. 2-Decarboxy-2-hydroxymethyl-6-keto-16-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 48. 2-Decarboxy-2-hydroxymethyl-6-keto-16-(p-fluorophenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 49. 2-Decarboxy-2-hydroxymethyl-6-keto-16-methyl-16-phenoxy-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 50. 2-Decarboxy-2-hydroxymethyl-6-keto-17-(m-trifluoromethylphenyl)-18,19,20-trinor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 51. 2-Decarboxy-2-hydroxymethyl-6-keto-17-(m-chlorophenyl)-18,19,20-trinor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 52. 2-Decarboxy-2-hydroxymethyl-6-keto-17-(p-fluorophenyl)-18,19,20-trinor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 53. 2-Decarboxy-2-hydroxymethyl-6-keto-16,16-dimethyl-17-phenyl-18,19,20-trinor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 54. 2-Decarboxy-2-hydroxymethyl-6-keto-16,16-difluoro-17-phenyl-18,19,20-trinor-cis-13-PGF.sub.1.alpha. ; a compound according to claim 1.
  • 55. 2-Decarboxy-2-hydroxymethyl-6-keto-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 56. 2-Decarboxy-2-hydroxymethyl-6-keto-16-(m-chlorophenoxy)-17,18,19,20-tetranor-cis-13-PGF.sub.1.alpha. ; a compound according to claim 1.
  • 57. 2-Decarboxy-2-hydroxymethyl-6-keto-16-(p-fluorophenoxy)-17,18,19,20-tetranor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 58. 2-Decarboxy-2-hydroxymethyl-6-keto-16-methyl-16-phenoxy-18,19,20-trinor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 59. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-phenyl-18,19,20-trinor-PGF.sub.1.alpha., a compound according to claim 1.
  • 60. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-(m-trifluoromethylphenyl)-18,19,20-trinor-PGF.sub.1.alpha., a compound according to claim 1.
  • 61. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-(m-chlorophenyl)-18,19,20-trinor-PGF.sub.1.alpha., a compound according to claim 1.
  • 62. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-(p-fluorophenyl)-18,19,20-trinor-PGF.sub.1.alpha., a compound according to claim 1.
  • 63. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16,16-dimethyl-17-phenyl-18,19,20-trinor-PGF.sub.1.alpha., a compound according to claim 1.
  • 64. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16,16-difluoro-17-phenyl-18,19,20-trinor-PGF.sub.1.alpha., a compound according to claim 1.
  • 65. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha., a compound according to claim 1.
  • 66. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-PGF.sub.1.alpha., a compound according to claim 1.
  • 67. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-(m-chlorophenoxy)-17,18,19,20-tetranor-PGF.sub.1.alpha., a compound according to claim 1.
  • 68. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-(p-fluorophenoxy)-17,18,19,20-tetranor-PGF.sub.1.alpha., a compound according to claim 1.
  • 69. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-methyl-16-phenoxy-18,19,20-trinor-PGF.sub.1.alpha., a compound according to claim 1.
  • 70. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 71. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 72. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-(m-chlorophenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 73. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-(p-fluorophenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 74. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 75. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2,16,16-tetrafluoro-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 76. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-phenoxy-17,18,19,20-tetranor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 77. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 78. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 79. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-methyl-16-phenoxy-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 80. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 81. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 82. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-(m-chlorophenyl)-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 83. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-(p-fluorophenyl)-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 84. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 85. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2,16,16-tetrafluoro-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 86. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-phenoxy-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 87. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 88. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 89. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-(p-fluorophenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 90. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-methyl- 16-phenoxy-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 91. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-phenyl-18,19,20-trinor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 92. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-(m-trifluoromethylphenyl)-18,19,20-trinor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 93. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-(m-chlorophenyl)-18,19,20-trinor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 94. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-17-(p-fluorophenyl)-18,19,20-trinor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 95. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16,16-dimethyl-17-phenyl-18,19,20-trinor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 96. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-phenoxy-17,18,19,20-tetranor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 97. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 98. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-(m-chlorophenoxy)-17,18,19,20-tetranor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 99. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-(p-fluorophenoxy)-17,18,19,20-tetranor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 100. 2-Decarboxy-2-hydroxymethyl-6-keto-2,2-difluoro-16-methyl-16-phenoxy-18,19,20-trinor-cis-13- PGF.sub.1.alpha., a compound according to claim 1.
  • 101. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-phenyl-18,19,20-trinor-PGF.sub.1.alpha., a compound according to claim 1.
  • 102. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-(m-trifluoromethylphenyl)-18,19,20-trinor-PGF.sub.1.alpha., a compound according to claim 1.
  • 103. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-(m-chlorophenyl)-18,19,20-trinor-PGF.sub.1.alpha., a compound according to claim 1.
  • 104. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-(p-fluorophenyl)-18,19,20-trinor-PGF.sub.1.alpha., a compound according to claim 1.
  • 105. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16,16-dimethyl-17-phenyl-18,19,20-trinor-PGF.sub.1.alpha., a compound according to claim 1.
  • 106. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16,16-difluoro-17-phenyl-18,19,20-trinor-PGF.sub.1.alpha., a compound according to claim 1.
  • 107. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1.alpha., a compound according to claim 1.
  • 108. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-PGF.sub.1.alpha., a compound according to claim 1.
  • 109. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-(m-chlorophenoxy)-17,18,19,20-tetranor-PGF.sub.1.alpha., a compound according to claim 1.
  • 110. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-(p-fluorophenoxy)-17,18,19,20-tetranor-PGF.sub.1.alpha., a compound according to claim 1.
  • 111. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16- methyl-16-phenoxy-18,19,20-trinor-PGF.sub.1.alpha., a compound according to claim 1.
  • 112. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 113. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-(m-trifluoromethylphenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 114. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-(m-chlorophenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 115. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-(p-fluorophenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 116. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 117. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16,16-difluoro-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 118. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-phenoxy-17,18,19,20-tetranor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 119. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 120. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 121. b 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-methyl-16-phenoxy-18,,19,20-trinor-13,14-didehydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 122. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 123. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17- (m-trifluoromethylphenyl)-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 124. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-(m-chlorophenyl)-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 125. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-(p-fluorophenyl)-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 126. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 127. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16,16-difluoro-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 128. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16- phenoxy-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 129. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 130. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 131. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-(p-fluorophenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 132. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-methyl-16-phenoxy-18,19,20-trinor-13,14-dihydro-PGF.sub.1.alpha., a compound according to claim 1.
  • 133. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-phenyl-18,19,20-trinor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 134. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-(m-trifluoromethylphenyl)-18,19,20-trinor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 135. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-(m-chlorophenyl)-18,19,20-trinor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 136. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-17-(p-fluorophenyl)-18,19,20-trinor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 137. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16,16-dimethyl-17-phenyl-18,19,20-trinor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 138. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16,16-difluoro-17-phenyl-18,19,20-trinor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 139. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-phenoxy-17,18,19,20-tetranor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 140. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 141. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-(m-chlorophenoxy)-17,18,19,20-tetranor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 142. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-(p-fluorophenoxy)-17,18,19,20-tetranor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
  • 143. 2-Decarboxy-2-hydroxymethyl-6-keto-3-oxa-16-methyl-16-phenoxy-18,19,20-trinor-cis-13-PGF.sub.1.alpha., a compound according to claim 1.
CROSS REFERENCE TO RELATED APPLICATION

The present application is a divisional application of copending application Ser. No. 959,400, filed Nov. 9, 1978; which is a divisional application of Ser. No. 819,857, filed Jul. 28, 1977, now U.S. Pat. No. 4,158,667; which is a continuation-in-part of Ser. No. 725,548, filed Sept. 22, 1976, now abandoned; which is a continuation-in-part of Ser. No. 716,972, filed Aug. 23, 1976, now abandoned; which is a continuation-in-part of Ser. No. 655,110, filed Feb. 4, 1976, now abandoned.

Non-Patent Literature Citations (4)
Entry
Chem. Abst. 86:139492f, Skuballa, et al., Dec. 16, 1976, Ger. Offen. 2,523,676.
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Divisions (2)
Number Date Country
Parent 959400 Nov 1978
Parent 819857 Jul 1977
Continuation in Parts (3)
Number Date Country
Parent 725548 Sep 1976
Parent 716972 Aug 1976
Parent 655110 Feb 1976