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Details for Patent: 4,215,222

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Details for Patent: 4,215,222

Title: 6-Keto prostaglandin derivatives
Abstract:Prostaglandin (PG.sub.1) derivatives having (1) a 6-keto feature, for example ##STR1## or (2) a 9-deoxy-6,9-epoxy feature together with a 5-halo or 6-hydroxy feature, for example ##STR2## said derivatives having pharmacological activity. Processes for preparing them and the appropriate intermediates are disclosed.
Inventor(s): Axen; Udo F. (Plainwell, MI)
Assignee: The Upjohn Company (Kalamazoo, MI)
Filing Date:Nov 09, 1978
Application Number:05/959,400
Claims:1. A compound of the formula

or a mixture comprising that compound and the enantiomer thereof

wherein R.sub.20 is ##STR12## 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 Y is a valence bond, --CH.sub.2 -- or --(CH.sub.2).sub.2 --,

wherein Q is ##STR13## wherein R.sub.8 is hydrogen or alkyl of one to 4 carbon atoms, inclusive, wherein R.sub.3 is (a) hydrogen, (b) alkyl of one to 12 carbon atoms, inclusive, (c) cycloalkyl of 3 to 10 carbon atoms, inclusive, (d) aralkyl of 7 to 12 carbon atoms, inclusive, (e) phenyl, (f) phenyl substituted with one, 2, or 3 chloro or alkyl of one to 4 carbon atoms, inclusive, ##STR14## wherein R.sub.10 is phenyl, p-bromophenyl, p-biphenylyl, p-nitrophenyl, p-benzamidophenyl, or 2-naphthyl, and wherein R.sub.11 is hydrogen or benzoyl, or (n) a pharmacologically acceptable cation,

wherein R.sub.4 is ##STR15## 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 R.sub.20 is ##STR16##

3. A compound according to claim 1 wherein R.sub.20 is ##STR17##

4. A compound according to claim 1 wherein R.sub.20 is ##STR18##

5. A compound according to claim 1 wherein R.sub.20 is ##STR19##

6. A compound according to claim 1 wherein R.sub.20 is ##STR20##

7. A compound according to claim 1 wherein R.sub.20 is ##STR21##

8. A compoun according to claim 1 wherein R.sub.20 is ##STR22## wherein L is -(CH.sub.2).sub.n, n being 3, 4, or 5, wherein Q is ##STR23## wherein R.sub.8 is limited to hydrogen, methyl, or ethyl, and wherein R.sub.4 is ##STR24##

9. A compound according to claim 8 wherein X is --C.tbd.C--.

10. A compound according to claim 8 wherein X is --CH.sub.2 CH.sub.2 --.

11. A compound according to claim 8 wherein X is trans--CH.dbd.CH--.

12. A compound according to claim 11 wherein R.sub.3 is ##STR25##

13. A compound according to claim 11 wherein R.sub.3 is ##STR26## wherein R.sub.10 and R.sub.11 are as defined in claim 1.

14. A compound according to claim 11 wherein R.sub.3 is hydrogen, alkyl of one to 12 carbon atoms, inclusive, or a pharmacologically acceptable cation.

15. A compound according to claim 14 wherein R.sub.3 is hydrogen, methyl, or a pharmacologically acceptable cation.

16. 6-Keto-17-phenyl-18,19,20-trinor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 15.

17. 6-Keto-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 15.

18. 6-Keto-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 10.

19. 6-Keto-16-phenoxy-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 10.

20. 6-Keto-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 9.

21. 6-Keto-16-phenoxy-17,18,19,20-tetranor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 9.

22. 6-Keto-17-phenyl-18,19,20-trinor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 9.

23. 6-Keto-16-phenoxy-17,18,19,20-tetranor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 9.

24. 6-Keto-17-(m-trifluoromethylphenyl)-18,19,20-trinor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

25. 6-Keto-17-(m-chlorophenyl)-18,19,20-trinor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

26. 6-Keto-17-(p-fluorophenyl)-18,19,20-trinor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

27. 6-Keto-16,16-dimethyl-17-phenyl-18,19,20-trinor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

28. 6-Keto-16,16-difluoro-17-phenyl-18,19,20-trinor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

29. 6-Keto-16-(m-trifluoromethylphenoxy)-17,18,19,20-tetranor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

30. 6-Keto-16-(m-chlorophenoxy)-17,18,19,20-tetranor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

31. 6-Keto-16-(p-fluorophenoxy)-17,18,19,20-tetranor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

32. 6-Keto-16-methyl-16-phenoxy-18,19,20-trinor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

33. 6-Keto-17-(m-trifluoromethylphenyl)- 18,19,20-trinor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

34. 6-Keto-17-(m-chlorophenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

35. 6-Keto-17-(p-fluorophenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

36. 6-Keto-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,1 4-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

37. 6-Keto-16-difluoro-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

38. 6-Keto-16-(m-trifluoromethylphenoxy)-17,18,19,20-tet ranor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim l.

39. 6-Keto-1 6-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

40. 6-Keto-16-methyl-16-phenoxy-18,19,20-trinor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

41. 6-Keto-17-(m-trifluoromethylphenyl)-18,19,20-trinor- 13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

42. 6-Keto-17-(m-chlorophenyl)-18,19,20-trinor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

43. 6-Keto-17-(p-fluorophenyl)-18,19,20-trinor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

44. 6-Keto-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

45. 6-Keto-16,16-difluoro-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

46. 6-Keto-16-(m-trifluoromethylphenoxy)-17,18,19,20-tet ranor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

47. 6-Keto-1 6-(m-chlorophenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

48. 6-Keto-16-(p-fluorophenoxy)-17,18,19,20-tet ranor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

49. 6-Keto-16-methyl-16-phenoxy-18,19,20-trinor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

50. 6-Keto-17-(m-trifluoromethylphenyl)-18,19,20-trinor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

51. 6-Keto-17-(m-chlorophenyl)-18,19,20-trinor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

52. 6-Keto-17-(p-fluorophenyl)-18,19,20-trinor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

53. 6-Keto-16,16-dimethyl-17-phenyl-18,19,20-trinor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

54. 6-Keto-16,16-difluoro-17-phenyl-18,19,20-trinor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

55. 6-Keto-16-(m-trifluoromethylphenoxy)-17,18,19,20-tet ranor-cis-13-PGF.sub.1 .alpha., methyl ester, a compond according to claim 1.

56. 6-Keto-16-(m-chlorophenoxy)-17,18,19,20-tetranor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

57. 6-Keto-16-(p-fluorophenoxy)-17,18,19,20-tetranor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

58. 6-Keto-16-methyl-16-phenoxy-18,19,20-trinor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

59. 6-Keto-2,2-difluoro-17-phenyl-18,19,20-trinor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

60. 6-Keto-2,2-difluoro-17-(m-trifluorom ethylphenyl)-18,19,20-trinor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

61. 6-Keto-2,2-difluoro-17-(m-chlorophenyl)-18,19,20-trinor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

62. 6-Keto-2,2-difluoro-17-(p-fluorophenyl)-18,19,20-trinor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

63. 6-Keto-2,2-difluoro-16,16-methyl-17-phenyl-18,19,20-trinor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

64. 6-Keto-2,2-difluoro-16,16-difluoro-17-phenyl-18,19,20-trinor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

65. 6-Keto-2,2-difluoro-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

66. 6-Keto-2,2-difluoro-16-(m-trifluoromethylph enoxy)-17,18,19,20-tetranor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

67. 6-Keto-2,2-difluoro-16-(m-chlorophenoxy)-17,18,19,20-tetranor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

68. 6-Keto-2,2-difluoro-16-(p-fluorophenoxy(-17,18,19,20-tetranor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

69. 6-Keto-2,2-difluoro-16-methyl-16-phenoxy-18,19,20-trinor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

70. 6-Keto-2,2-difluoro-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

71. 6-Keto-2,2-difluoro-17-(m-trifluoromethylphenyl)-18, 19,20-trinor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

72. 6-Keto-2,2-difluor o-17-(m-chlorophenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

73. 6-Keto-2,2-difluoro-17-(p-fluorophenyl)-18, 19,20-trinor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

74. 6-Keto-2,2-difluor o-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

75. 6-Keto-2,2,16,16-tetrafluoro-17-phenyl-18,19,20-trin or-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

76. 6-Ket o-2,2-difluoro-16-phenoxy-17,18,19,20-tetranor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

77. 6-Keto-2,2-difluoro-16-(m-trifluoromethylphenoxy)-17 ,18,19,20-tetranor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

78. 6-Keto-2,2-difluoro-16-(m-c hlorophenoxy)-17,18,19m20-tetranor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

79. 6-Keto-2,2-difluoro-16-methyl-16-phenoxy-18 ,19,20-trinor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

80. 6-Keto-2,2-difluoro-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

81. 6-Keto-2,2-difluoro-17-(m-trifluoromethylphenyl)-18, 19,20-trinor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

82. 6-Keto-2,2-difluor o-17-(m-chlorophenyl)-18,19,20-trinor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

83. 6-Keto-2,2-difluoro-17-(p-fluorophenyl)-18, 19,20-trinor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

84. 6-Keto-2,2-difluor o-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

85. 6-Keto-2,2,16,16-Tetrafluoro-17-phenyl-18,1 9,20-trinor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

86. 6-Keto-2,2-difluor o-16-phenoxy-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

87. 6-Keto-2,2-difluoro-16-(m-trifluorom ethylphenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

88. 6-Keto-2,2-difluoro-16-(m-chlorophen oxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

89. 6-Keto-2,2-difluoro-16-(p-f luorophenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

90. 6-Keto-2,2-difluoro-16-methyl-16-phe noxy-18,19,20-trinor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

91. 6-Keto-2,2-difluoro-17-phenyl-18,19,20-trinor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

92. 6-Keto-2,2-difluoro-17-(m-trifluoromethylph enyl)-18,19,20-trinor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

93. 6-Keto-2,2-difluor o-17-(m-chlorophenyl)-18,19,20-trinor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

94. 6-Keto-2,2-difluoro-17-(p-fluorophen yl)-18,19,20-trinor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

95. 6-Keto-2,2-difluor o-16,16-dimethyl-17-phenyl-18,19,20-trinor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

96. 6-Keto-2,2-difluoro-16,16-difluoro-1 7-phenyl-18,19,20-trinor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

97. 6-Keto-2,2-difluoro-16-phenoxy-17,18,19,20-tetranor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

98. 6-Keto-2,2-difluoro-16-(m-trifluoromethylphenoxy)-17 ,18,19,20-tetranor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

99. 6-Keto-2,2-difluor o-16-(m-chlorophenoxy)-17,18,19,20-tetranor-cis-13-PGF.sub.1 .alpha., methyl ester, a compund according to claim 1.

100. 6-Keto-2,2-difluoro-16-(p-fluorophenoxy)- 17,18,19,20-tetranor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

101. 6-Keto-2,2-difluo ro-16-methyl-16-phenoxy-18,19,20-trinor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

102. 6-Keto-3-oxa-17-phenyl-18,19,20-trinor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

103. 6-Keto-3-oxa-17-(m-trifluoromethylphenyl)-18,19,20,-trinor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

104. 6-Keto-3-oxa-17-(m-chlorophenyl)-18,19,20,-trinor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

105. 6-Keto-3-oxa-17-(p-fluorophenyl)-18,19,20-trinor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

106. 6-Keto-3-oxa-16,16-dimethyl-17-phenyl-18,19,20-trinor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

107. 6-Keto-3-oxa-16,16-difluoro-17-phenyl-18,19,20-trinor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

108. 6-Keto-3-oxa-16-phenoxy-17,18,19,20-tetranor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

109. 6-Keto-3-oxa-16-(m-trifluoromethylp henoxy)-17,18,19,20-tetranor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

110. 6-Keto-3-oxa-16-(m-chlorophenoxy)-17,18,19,20-tetranor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

111. 6-Keto-3-oxa-16-(p-fluorophenoxy)-17,18,19,20-tetranor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

112. 6-Keto-3-oxa-16-methyl-16-phenoxy-18,19,20-trinor-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

113. 6-Keto-3-oxa-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

114. 6-Keto-3-oxa-17-(m-trifluoromethylphenyl)-18,19,20- trinor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

115. 6-Keto-3-oxa-17-( m-chlorophenyl)-18,19,20-trinor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

116. 6-Keto-3-oxa-17-(p-fluorophenyl)-18 ,19,20-trinor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

117. 6-Keto-3-oxa-16,1 6-dimethyl-17-phenyl-18,19,20-trinor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

118. 6-Keto-3-oxa-16,16-difluoro-17-phenyl-18,1 9,20-trinor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

119. 6-Keto-3-oxa-16-phenoxy-17,18,19,20-tetranor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

120. 6-Keto-3-oxa-16-(m-trifluoromethylphenoxy)-17,18,19 ,20-tetranor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

121. 6-Keto-3-oxa-16-( m-chlorophenoxy)-17,18,19,20-tetranor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

122. 6-Keto-3-oxa-16-methyl-16-phenoxy-18,19,20 -trinor-13,14-didehydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

123. 6-Keto-3-oxa-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

124. 6-Keto-3-oxa-17-(m-trifluoromethylphenyl)-18,19,20- trinor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

125. 6-Keto- 3-oxa-17-(m-chlorophenyl)-18,19,20-trinor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

126. 6-Keto-3-oxa-17-(p-fluorophenyl)-18,19,20- trinor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

127. 6-Keto- 3-oxa-16,16-dimethyl-17-phenyl-18,19,20-trinor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

128. 6-Keto-3-oxa-16,16-difluoro-17-phenyl-18,19,20-trin or-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

129. 6-Keto-3-oxa-16-phenyl-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

130. 6-Keto-3-oxa-16-(m-trifluoromethylphenoxy)-17,18,19 ,20-tetranor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

131. 6-Keto-3-oxa-16-( m-chlorophenoxy)-17,18,19,20-tetranor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

132. 6-Keto-3-oxa-16-(p-fluorophenoxy)-17,18,19 ,20-tetranor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

133. 6-Keto-3-oxa-16-m ethyl-16-phenoxy-18,19,20-trinor-13,14-dihydro-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

134. 6-Keto-3-oxa-17-phenyl-18,19,20-trinor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

135. 6-Keto-3-oxa-17-(m-trifluoromethylphenyl)- 18,19,20-trinor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

136. 6-Keto-3-oxa-17-(m-chlorophenyl)-18,19,20-trinor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

137. 6-Keto-3-oxa-17-(p-fluorophenyl)-18,19,20-trinor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

138. 6-Keto-3-oxa-16,16-dimethyl-17-phenyl-18,19,20-trinor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

139. 6-Keto-3-oxa-16,16-difluoro-17-phenyl-18,19,20-trinor-cis-13PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

140. 6-Keto-3-oxa-16-phenoxy-17,18,19,20-tetranor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

141. 6-Keto-3-oxa-16-(m-trifluoromethylphenoxy) -17,18,19,20-tetranor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

142. 6-Keto-3-oxa-16-( m-chlorophenoxy)-17,18,19,20-tetranor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

143. 6-Keto-3-oxa-(p-fluorophenoxy)-17,18,19,20-tetranor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

144. 6-Keto-3-oxa-16-methyl-16-phenoxy-18,19,20-trinor-cis-13-PGF.sub.1 .alpha., methyl ester, a compound according to claim 1.

145. 6-Keto-17-phenyl-18,19,20-trinor-PGF.sub.1 .alpha., a compound according to claim 15.
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