3-Oxa phenyl-substituted PGE compounds

A compound of the formula:

• ##SPC65##
• wherein R.sub.1 is hydrogen, alkyl of one to 8 carbon atoms, inclusive, cycloalkyl of 3 to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, phenyl substituted with one, 2, or 3 chloro or alkyl of one to 4 carbon atoms, inclusive, or ethyl substituted in the .beta.-position with 3 chloro, 2 or 3 bromo, or 1, 2, or 3 iodo;
• wherein R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are hydrogen or alkyl of one to 4 carbon atoms, inclusive;
• wherein C.sub.p H.sub.2p is alkylene of one to 8 carbon atoms, inclusive, with one, 2, or 3 carbon atoms between --CH=CH-- and --O--;
• wherein C.sub.t H.sub.2t represents (1) a valence bond or (2) alkylene of one to 10 carbon atoms, inclusive, substituted with zero, one, or 2 fluoro, with one to 7 carbon atoms, inclusive, between --CR.sub.3 OH-- and the ring;
• wherein T is alkyl of one to 4 carbon atoms, inclusive, fluoro, chloro, trifluoromethyl, or --OR.sub.9, wherein R.sub.9 is hydrogen, alkyl of one to 4 carbon atoms, inclusive, or tetrahydropyranyl, and s is zero, one, 2, or 3, with the proviso that no more than two T are other than alkyl;
• and wherein .about. indicates attachment of the group to the ring in alpha or beta configuration;
• including the lower alkanoates thereof, and the pharmacologically acceptable salts thereof when R.sub.1 is hydrogen.

A compound of the formula:

• ##SPC66##
• wherein R.sub.1 is hydrogen, alkyl of one to 8 carbon atoms, inclusive, cycloalkyl of 3 to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, phenyl substituted with one, 2, or 3 chloro or alkyl or one to 4 carbon atoms, inclusive, or ethyl substituted in the .beta.-position with 3 chloro, 2 or 3 bromo, or 1, 2, or 3 iodo;
• wherein R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are hydrogen or alkyl of one to 4 carbon atoms, inclusive;
• wherein C.sub.p H.sub.2p is alkylene of one to 8 carbon atoms, inclusive, with one, 2, or 3 carbon atoms between --C.tbd.C-- and --O--;
• wherein C.sub.t H.sub.2t represents (1) a valence bond or (2) alkylene of one to 10 carbon atoms, inclusive, substituted with zero, one, or 2 fluoro, with one to 7 carbon atoms, inclusive, between --CR.sub.3 OH-- and the ring;
• wherein T is alkyl of one to 4 carbon atoms, inclusive, fluoro, chloro, trifluoromethyl, or --OR.sub.9, wherein R.sub.9 is hydrogen, alkyl of one to 4 carbon atoms, inclusive, or tetrahydropyranyl, and s is zero, one, 2, or 3, with the proviso that no more than two T are other than alkyl;
• and wherein .about. indicates attachment of the group to the ring in alpha or beta configuration;
• including the lower alkanoates thereof, and the pharmacologically acceptable salts thereof when R.sub.1 is hydrogen.

A compound of the formula:

• ##SPC67##
• wherein R.sub.1 is hydrogen, alkyl of one to 8 carbon atoms, inclusive, cycloalkyl or 3 to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, phenyl substituted with one, 2, or 3 chloro or alkyl of one to 4 carbon atoms, inclusive, or ethyl substituted in the .beta.-position with 3 chloro, 2 or 3 bromo, or 1, 2, or 3 iodo;
• wherein R.sub.2, R.sub.3, R.sub.4, R.sub.5, and R.sub.6 are hydrogen or alkyl of one to 4 carbon atoms, inclusive;
• wherein C.sub.n H.sub.2n is alkylene of one to 10 carbon atoms, inclusive, with one to 5 carbon atoms, inclusive, between --CHR.sub.2 -- and --O--;
• wherein C.sub.t H.sub.2t represents (1) a valence bond or (2) alkylene of one to 10 carbon atoms, inclusive, substituted with zero, one, or 2 fluoro, with one to 7 carbon atoms, inclusive, between --CR.sub.3 OH-- and the ring;
• wherein T is alkyl of one to 4 carbon atoms, inclusive, fluoro, chloro, trifluoromethyl, or --OR.sub.9, wherein R.sub.9 is hydrogen, alkyl of one to 4 carbon atoms, inclusive, or tetrahydropyranyl, and s is zero, one, 2, or 3, with the proviso that no more than two T are other than alkyl;
• and wherein .about. indicates attachment of the group to the ring in alpha or beta configuration;
• including the lower alkanoates thereof, and the pharmacologically acceptable salts thereof when R.sub.1 is hydrogen.