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Trans-4,5,13,14-tetradehydro-PGI.sub.1 amides

  • US 4,167,625 A
  • Filed: 06/14/1978
  • Issued: 09/11/1979
  • Est. Priority Date: 08/03/1977
  • Status: Expired due to Term
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1. A prostacyclin analog of the formula ##STR1## wherein Y2 is --C.tbd.C--;

  • wherein Z2 is ##STR2## wherein Z1 is (1) --(CH2)g --CH2 --CH2 --, or(2) --(CH2)g --CH2 --CF2 --,wherein g is the integer zero, one, or 2;

    Wherein M1 is ##STR3## wherein R5 is hydrogen or alkyl with one to 4 carbon atoms, inclusive;

    Wherein L1 is ##STR4## or a mixture of ##STR5## wherein R3 and R4 are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R3 and R4 is fluoro only when the other is hydrogen or fluoro;

    wherein L4 is(a) amino of the formula --NR21 R22 ;

    wherein R21 and R22 are hydrogen;

    alkyl of one to 12 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, alkyl of one to 3 carbon atoms, inclusive;

    hydroxy, carboxy, alkoxycarbonyl of one to 4 carbon atoms, inclusive, or nitro;

    carboxyalkyl of one to 4 carbon atoms, inclusive;

    carbamoylalkyl of one to 4 carbon atoms, inclusive;

    cyanoalkyl of one to 4 carbon atoms, inclusive;

    acetylalkyl of one to 4 carbon atoms, inclusive;

    benzoylalkyl of one to 4 carbon atoms, inclusive, benzoylalkyl substituted by one, 2, or 3 chloro, alkyl of one to 3 carbon atoms, inclusive, hydroxy, alkoxy of one to 3 carbon atoms, inclusive, carboxy, alkoxycarbonyl of one to 4 carbon atoms, inclusive;

    or nitro;

    pyridyl;

    pyridyl substituted by one, 2, or 3 chloro, alkyl of one to 3 carbon atoms, inclusive, or alkoxy of one to 3 carbon atoms, inclusive;

    pyridylalkyl of one to 4 carbon atoms, inclusive;

    pyridylalkyl substituted by one, 2, or 3 chloro, alkyl of one to 3 carbon atoms, inclusive, hydroxy, or alkoxy of one to 3 carbon atoms, inclusive;

    hydroxyalkyl of one to 4 carbon atoms, inclusive;

    dihydroxyalkyl of one to 4 carbon atoms, and trihydroxyalkyl of one to 4 carbon atoms;

    with the further proviso that not more than one of R21 and R22 is other than hydrogen or alkyl;

    (b) cycloamino selected from the group consisting of ##STR6## wherein R21 and R22 are defined above;

    (c) carbonylamino of the formula --NR23 COR21, wherein R23 is hydrogen or alkyl of one to 4 carbon atoms and R21 is as defined above;

    (d) sulfonylamino of the formula --NR23 SO2 R21, wherein R21 and R23 are as defined above;

    or(e) hydrazino of the formula --NR23 R24, wherein R23 is as defined above and R24 is amino of the formula --NR21 R22, as defined above; and

    wherein R7 is(1) --(CH2)m --CH3, ##STR7## wherein m is the integer one to 5, inclusive, h is the integer zero to 3, inclusive;

    s is the integer 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, with the proviso that not more than two T'"'"'s are other than alkyl.

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