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Enlarged-hetero-ring prostacyclin analogs

  • US 4,490,548 A
  • Filed: 03/26/1979
  • Issued: 12/25/1984
  • Est. Priority Date: 04/19/1977
  • Status: Expired due to Term
First Claim
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1. A cyclic ether of the formula ##STR85## wherein L is (1) --(CH2)d -- wherein d is one to 5, inclusive, (2) --(CH2)t --CF2 -- wherein t is one, 2, or 3, (3) --CH═

  • CH--, (4) --CH2 --O--CH2 Y-- wherein Y is a valance bond or --(CH2)k -- wherein k is one or 2;

    wherein Q2 is ##STR86## wherein R3 is hydrogen or alkyl of one to 4 carbon atoms, inclusive, and wherein R4 is hydrogen;

    wherein ○

    R22 is ##STR87## wherein R5 and R6 are hydrogen, alkyl of one to 4 carbon atoms, inclusive, or fluoro, being the same or different, with the proviso that one of R5 and R6 is fluoro only when the other is hydrogen or fluoro and the further proviso that neither R5 nor R6 is fluoro when Z is oxa (--0--);

    wherein Z represents an oxa atom (--0--) or Cj H2j wherein Cj H2j is a valence bond or alkylene of one to 9 carbon atoms, inclusive, substituted with zero, one, or 2 fluoro, with one to 6 carbon atoms, inclusive between --CR5 R6 -- and the phenyl ring;

    wherein T is alkyl of one to 4 carbon atoms, inclusive, fluoro, chloro, trifluoromethyl, or --OR7 -- wherein R7 is alkyl of one to 4 carbon atoms, inclusive, and s is zero, one, 2, one 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;

    wherein R27 is (a) alkyl of one to 12 carbon atoms, inclusive, (b) cycloalkyl of 3 to 10 carbon atoms, inclusive, (c) aralkyl of 7 to 12 carbon atoms, inclusive, (d) phenyl, (e) phenyl substituted with one, 2, or 3 chloro or alkyl of one to 4 carbon atoms, inclusive;

    ##STR88## (1) hydrogen, or (m) a pharmacologically acceptable cation;

    wherein X is cis- or trans-CH═

    CH--, --C═

    C--, or --CH2 CH2 --;

    wherein ˜

    indicates attachment in alpha or beta configuration;

    including the lower alkanoates thereof.

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