PG-type, 1,9-lactones

Abstract

The present invention provides novel 1,9 lactones of prostaglandin-type free acids and a process for their preparation. These lactones are useful for the same pharmacological purposes as the corresponding prostaglandin-type free acids.

I claim: .[. 
     
       1.  A prostaglandin-type, 1,9-lactone of the formula ##STR280## wherein W 2  is ##STR281## wherein L 1  is ##STR282## or a mixture of ##STR283## wherein R 3  and R 4  are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R 3  and R 4  is fluoro, only when the other is hydrogen or fluoro; wherein M 1  is ##STR284## wherein R 5  is hydrogen or methyl; wherein R 7  is --(CH 2 ) m  --CH 3 , wherein m is one to 5, inclusive, cis--CH═CH--CH 2  --CH 3 , or ##STR285## wherein T is chloro, fluoro, trifluoromethyl, alkyl of one to 3 carbon atoms, inclusive, or alkoxy of one to 3 carbon atoms, inclusive, the various T's being the same or different, s is zero, one, 2, or 3, and Z 3  is oxa or methylene, with the provisio that not more than two T's are other than alkyl, and the further proviso that Z 3  is oxa only when R 3  and 4 4  are hydrogen or methyl, being the same or different;   wherein Y 1  is trans--CH═CH--, --CH 2  CH 2  --, cis--CH═CH--, or --C.tbd.C--; and   wherein Z 1  is   cis--CH═CH--CH.sub.2 --(CH.sub.2).sub.g --CH.sub.2 --, (1)       cis--CH═CH--CH.sub.2 --(CH.sub.2).sub.g --CF.sub.2 --, (2)       cis--CH.sub.2 --CH═CH--(CH.sub.2).sub.g --CH.sub.2 --, (3)       --(ch.sub.2).sub.3 --(ch.sub.2).sub.g --CH.sub.2 --,       (4)       --(ch.sub.2).sub.3 --(ch.sub.2).sub.g --CF.sub.2 --,       (5)       --ch.sub.2 --o--ch.sub.2 --(ch.sub.2).sub.g --CH.sub.2 --, (6) ##STR286## wherein g is one to 3, inclusive..]..[.       
     
     
       2.  A compound according to claim 1, wherein W 2  is ##STR287## .[. 
     
     
       3.  11-Deoxy-PGF 2 α, 1,9-lactone, a compound according to claim 2..]..[.4. A compound according to claim 1, wherein W 2  is ##STR288## 
     
     
         .[.5.  A compound according to claim 4, wherein Y 1  is --C.tbd.C--..]..[.6. 13,14-Didehydro-PGD 2 , 1,9-lactone, a compound according to claim 5..]..[.7. A compound according to claim 4, wherein Y 1  is cis--CH═CH--..]..[.8. cis-13-PGD 2 , 1,9-lactone..]..[.9. A compound according to claim 4, wherein Y 1  is --CH 2  CH 2  --..]..[.10. 13,14-Dihydro-PGD 2 , 1,9-lactone, a compound according to claim 9..]..[.11. A compound according to claim 4, wherein Y 1  is trans--CH═CH--..]..[.12. PGD 2 , 1,9-lactone, a compound according to claim 11..]..[.13. A compound according to claim 1, wherein W 2  is ##STR289## 
     
     
        .[.14.  A compound according to claim 13, wherein ˜ is α..]..[.15. A compound according to claim 14, wherein M 1  ##STR290## 
     
     
        .[.16.  15-epi-PGF 2 α, 1,9-lactone, a compound according to 15..]..[.17. A compound according to claim 14, wherein M 1  is ##STR291## 
     
     
        .[.18.  A compound according to claim 17, wherein Z 1  is --CH 2  --O--CH 2  --(CH 2 ) g  --CH 2  --..]..[.19. 5-oxa-PGF 1 α, 1,9-lactone, a compound according to claim 18..]. .[.20. A compound according to claim 17, wherein Z 1  is ##STR292## 
     
     
        .[.21.  3-oxa-3,7-inter-m-phenylene-4,5,6-trinor-PGF 1 α, 1,9-lactone, a compound according to claim 20..]..[.22. A compound according to claim 17, wherein Z 1  is ##STR293## 
     
     
         .[.23.  3,7-inter-m-phenylene-4,5,6-trinor-PGF 1 α, 1,9-lactone, a compound according to claim 22..]..[.24. A compound according to claim 17, wherein Z 1  is cis--CH 2  --CH═CH--(CH 2 ) g  --CH 2  --..]. .[.25. cis-4,5-Didehydro-PGF 1 α, 1,9-lactone, a compound according to claim 24..]. .[.26. A compound according to claim 17, wherein Z 1  is cis--CH═CH--CH 2  --(CH 2 ) g  --CF 2  --..]..[.27. 2,2,16,16-Tetrafluoro-PGF 2 α, 1,9-lactone, a compound according to claim 26..]..[.28. 2,2-Difluoro-16,16-dimethyl-PGF 2 α,1,9-lactone, a compound according to claim 26..]. .[.29. 2,2-Difluoro-15-methyl-PGF 2 α, 1,9-lactones, a compound according to claim 26..]..[.30. 2,2-Difluoro-PGF 2 α, 1,9-lactone, a compound according to claim 26..]..[.31. A compound according to claim 17, wherein Z 1  is --(CH 2 ) 3  --(CH 2 ) g  --CF 2  --..]..[.32. 2,2,16,16-Tetrafluoro-PGF 1 α, 1,9-lactone, a compound according 
     
     
        to claim 31..]..[.33.  2,2-Difluoro-16,16-dimethyl-PGF 1 α, 1,9-lactone, a compound according to claim 31..]..[.34. 2,2-Difluoro-15-methyl-PGF 1 α, 1,9-lactone, a compound according to claim 31..]..[.35. 2,2-Difluoro-PGF 1 α, 1,9-lactone, a compound according to claim 31..]..[.36. A compound according to claim 17, wherein Z 1  is --(CH 2 ) 3  --(CH 2 ) g  --CH 2  --..]..[.37. 16,16-Difluoro-PGF 1 α, 1,9-lactone, a compound according to claim 36..]..[.38. 16,16-Dimethyl-PGF 1 α, 1,9-lactone, a compound according to claim 36..]. .[.39. 15-Methyl-PGF 1 α, 1,9-lactone, a compound according to claim 36..]..[.40. PGF 1 α, 1,9-lactone, a compound according to claim 36..]..[.41. A compound according to claim 17, wherein Z 1  is cis--CH═CH--CH 2  --(CH 2 ) g  --CH 2  --..]..[.42. A compound according to claim 41, wherein g is 3..]. .[.43. A compound 
     
     
        according to claim 41, wherein g is 1..]. .[.44.  A compound according to claim 43, wherein Y 1  is --C.tbd.C--..]..[.45. 13,14-Didehydro-PGF 2 α, 1,9-lactone, a compound according to claim 44..]..[.46. A compound according to claim 43, wherein Y 1  is cis--CH═CH--..]..[.47. cis-13-PGF 2 α, 1,9-lactone, a compound according to claim 46..]..[.48. A compound according to claim 43, wherein Y 1  is --CH 2  CH 2  --..]..[.49. 13,14-dihydro PGF 2 α, 1,9-lactone, a compound according to claim 48..]..[.50. A compound according to claim 43, wherein Y 1  is trans--CH═CH--..]..[.51. A compound according to claim 50, wherein R 7  is cis--CH═CH--CH 2  --CH 3  --..]..[.52. PGF 3 α, 1,9-lactone, a compound according to claim 51..]..[.53. A compound according to claim 50, wherein 7 is ##STR294## 
     
     
        .[.54.  A compound according to claim 53, wherein s is zero or one and T is chloro, fluoro, or trifluoromethyl..]..[.55. A compound according to claim 54, wherein Z 3  is methylene..]..[.56. A compound according to claim 55, wherein R 5  is methyl..]..[.57. 15-Methyl-17-Phenyl-18,19,20-trinor-PGF 2 α, 1,9-lactone, a compound according to claim 56..]..[.58. A compound according to claim 55, wherein R 5  is hydrogen..]..[.59. A compound according to claim 58, wherein at least one of R 3  and R 4  are fluoro..]..[.60. 16,16-Difluoro-17-Phenyl-18,19,20-trinor-PGF 2 α, 1,9-lactone, a compound according to claim 59..]..[.61. A compound according to claim 58, wherein at least one of R 3  and R 4  is methyl..]. .[.62. 16,16-Dimethyl-17-phenyl-18,19,20-trinor-PGF 2 α, 1,9-lactone, a compound according to claim 61..]..[. 63. A compound according to claim 
     
     
        58, wherein R 3  and R 4  are both hydrogen..]..[.64. 17-Phenyl-18,19,20-trinor-PGF 2 α, 1,9-lactone, a compound according to claim 63..]..[.65. A compound according to claim 54, wherein Z 3  is oxa..]..[.66. A compound according to claim 65, wherein R 5  is methyl..]..[.67. 15-Methyl-16-Phenoxy-17,18,19,20-tetranor-PGF 2 α, 1,9-lactone, a compound according to claim 66..]..[.68. A compound according to claim 65, wherein R 5  is hydrogen..]..[.69. A compound according to claim 68, wherein at least one of R 3  and R 4  is methyl..]..[.70. 16-Methyl-16-Phenoxy-18,19,20-trinor-PGF 2 α, 1,9-lactone, a compound according to claim 69..]..[.71. A compound according to claim 68, wherein R 3  and R 4  are both hydrogen..]..[.72. 16-Phenoxy-17,18,19,20-tetranor-PGF 2 α, 1,9-lactone, a compound 
     
     
        according to claim 71..]..[.73.  A compound according to claim 50, wherein R 7 , is --(CH 2 ) m  --CH 3  --..]..[.74. A compound according to claim 73, wherein m is 30..]..[.75. A compound according to claim 74, wherein R 5  is methyl..]..[.76. A compound according to claim 75, wherein at least one of R 3  and R 4  is fluoro..]..[.77. 15-Methyl-16,16-difluoro-PGF 2 α, 1,9-lactone, a compound according to claim 76..]..[.78. A compound according to claim 75, wherein at least one of R 3  and R 4  is methyl..]..[.79. 15,16,16-Trimethyl-PGF 2 α, 1,9-lactone, a compound according to claim 78..]..[.80. A compound according to claim 75, wherein R 3  and R 4  are both hydrogen..]..[.81. 15-Methyl-PGF 2 α, 1,9-lactone, a compound according to claim 80..]. .[.82. A compound according to claim 74, wherein R 5  is hydrogen..]..[.83. A compound according to claim 82, wherein at least one of R 3  and R 4  is fluoro..]. .[.84. A compound according to claim 83, wherein R 3  and R 4  are both fluoro..]..[.85. 16,16-Difluoro-PGF 2 α, 1,9-lactone, a compound according to claim 84..]..[.86. A compound according to claim 82, wherein at least one of R 3  and R 4  is methyl..]..[.87. A compound according to claim 86, wherein R 3  and R 4  are both methyl..]..[.88. 16,16-Dimethyl-PGF 2 α, 1,9-lactone, a compound according to claim 87..]..[.89. A compound according to claim 82, wherein R 3  and R 4  are both hydrogen..]..[.90. PGF 2 α, 1,9-lactone, a compound according to 
     
     
        claim 89..]. .Iadd.91.  A prostaglandin-type, 1,9-lactone of the formula ##STR295## wherein W 2  is ##STR296## wherein L 1  is ##STR297## or a mixture of ##STR298## wherein R 3  and R 4  are hydrogen, methyl, or fluoro, being the same or different, with the proviso that one of R 3  and R 4  is fluoro, only when the other is hydrogen or fluoro; wherein M 1  is ##STR299## wherein R 5  is hydrogen or methyl; wherein R 7  is --(CH 2 ).sbsb.m--CH 3 , wherein m is one to 5, inclusive, cis--CH═CH--CH 2  --CH 3 , or ##STR300## wherein T is chloro, fluoro, trifluoromethyl, alkyl of one to 3 carbon atoms, inclusive, or alkoxy of one to 3 carbon atoms, inclusive, the various T's being the same or different, s is zero, one, 2, or 3, with the proviso that not more than two T's are other than alkyl;   wherein Y 1  is trans--CH═CH--, --CH 2  CH 2  --, cis--CH═CH--, or --C.tbd.C--; and   wherein Z 1  is    cis--CH═CH--CH.sub.2 --(CH.sub.2).sbsb.g--CH.sub.2 --,(1)        cis--CH═CH--CH.sub.2 --(CH.sub.2).sbsb.g--CF.sub.2 --,(2)        cis--CH.sub.2 --CH═CH--(CH.sub.2).sbsb.g--CH.sub.2 --,(3)        --ch.sub.2).sub.3 --(ch.sub.2).sbsb.g--CH.sub.2 --,       (4)        --(ch.sub.2).sub.3 --(ch.sub.2).sbsb.g--CF.sub.2 --,      (5)        --ch.sub.2 --o--ch.sub.2 --(ch.sub.2).sbsb.g--CH.sub.2 --,(6) ##STR301##       
     
     
        wherein g is one to 3 inclusive. .Iaddend. .Iadd.92.  A compound according to claim 91, wherein W 2  is ##STR302## 
     
     
       .Iaddend. .Iadd.93.  11-Deoxy-PGF 2  α, 1,9-lactone, a compound according to claim 92. .Iaddend..Iadd.94. A compound according to claim 91, wherein W 2  is ##STR303## 
     
     
       .Iaddend. .Iadd.95.  A compound according to claim 94, wherein Y 1  is --C.tbd.C--. .Iaddend..Iadd.96. 13,14-Didehydro-PGD 2 , 1,9-lactone, a compound according to claim 95. .Iaddend..Iadd.97. A compound according to claim 94, wherein Y 1  is cis--CH═CH--. .Iaddend..Iadd.98. cis-13-PGD 2 , 1,9-lactone, a compound according to claim 97. .Iaddend..Iadd.99. A compound according to claim 94, wherein Y 1  is --CH 2  CH 2  --. .Iaddend..Iadd.100. 13,14-Dihydro-PGD 2 , 1,9-lactone, a compound according to claim 99. .Iaddend..Iadd.101. A compound according to claim 94, wherein Y 1  is trans--CH═CH--. .Iaddend..Iadd.102. PGD 2  1,9-lactone, a compound according to claim 101. .Iaddend..Iadd.103. A compound according to claim 91, wherein W 2  is ##STR304## 
     
     
       .Iaddend. .Iadd.104.  A compound according to claim 103, wherein ˜ is α..Iaddend..Iadd.105. A compound according to claim 104, wherein M 1  is ##STR305## 
     
     
       .Iaddend. .Iadd.106.  15-epi-16-Methyl-PGF 2  α, 1,9-lactone, a compound according to claim 105. .Iaddend..Iadd.107. A compound according to claim 104, wherein M 1  is ##STR306## 
     
     
       .Iaddend. .Iadd.108.  A compound according to claim 107, wherein Z 1  is --CH 2  --O--CH 2  --(CH 2 ).sbsb.g--CH 2  --. .Iaddend..Iadd.109. 5-Oxa-PGF 1  α, 1,9-lactone, a compound according to claim 108. .Iaddend..Iadd.110. A compound according to claim 107, wherein Z 1  is ##STR307## 
     
     
       .Iaddend. .Iadd.111.  3-Oxa-3,7-inter-m-phenylene-4,5,6-trinor-PGF 1  α, 1,9-lactone, a compound according to claim 110. .Iaddend..Iadd.112. A compound according to claim 107, wherein Z 1  is ##STR308## 
     
     
       .Iaddend. .Iadd.113.  3,7-inter-m-phenylene-4,5,6-trinor-PGF 1  α, 1,9-lactone, a compound according to claim 112. .Iaddend..Iadd.114. A compound according to claim 107, wherein Z 1  is cis--CH 2  --CH═CH--(CH 2 ).sbsb.g--CH 2  --. .Iaddend..Iadd.115. cis-4,5-Didehydro-PGF 1  α, 1,9-lactone, a compound according to claim 114. .Iaddend..Iadd.116. A compound according to claim 107, wherein Z 1  is cis--CH═CH--CH 2  --(CH 2 ).sbsb.g--CF 2  --. .Iaddend..Iadd.117. 2,2,16,16-Tetrafluoro-PGF 2  α, 1,9-lactone, a compound according to claim 116. .Iaddend.. .Iadd.118. 2,2-Difluoro-16,16-dimethyl-PGF 2  α, 1,9-lactone, a compound according to claim 116. .Iaddend..Iadd.119. 2,2-Difluoro-15-methyl-PGF 2  α, 1,9-lactone, a compound according to claim 116. .Iaddend..Iadd.120. 2,2-Difluoro-PGF 2  α, 1,9-lactone, a compound according to claim 116. .Iaddend..Iadd.121. A compound according to claim 107, wherein Z 1  is --(CH 2 ) 3  --(CH 2 ).sbsb.g--CF 2  --. .Iaddend..Iadd.122. 2,2,16,16-Tetrafluoro-PGF 1  α, 1,9-lactone, a compound according 
     
     
        to claim 121. .Iaddend..Iadd.123.  2,2-Difluoro-16,16-dimethyl-PGF 1  α, 1,9-lactone, a compound according to claim 121. .Iaddend..Iadd.124. 2,2-Difluoro-15-methyl-PGF 1  α, 1,9-lactone, a compound according to claim 121. .Iaddend..Iadd.125. 2,2-Difluoro-PGF 1  α, 1,9-lactone, a compound according to claim 121. .Iaddend..Iadd.126. A compound according to claim 107, wherein Z 1  is --(CH 2 ) 3  --(CH 2 ).sbsb.g--CH 2  --. .Iaddend..Iadd.127. 16,16-Difuoro-PGF 1  α, 1,9-lactone, a compound according to claim 126. .Iaddend..Iadd.128. 16,16-Dimethyl-PGF 1  α, 1,9-lactone, a compound according to claim 126. .Iaddend..Iadd.129. 15-Methyl-PGF 1  α, 1,9-lactone, a compound according to claim 126. .Iaddend..Iadd.130. PGF 1  α, 1,9-lactone, a compound according to claim 126. .Iaddend..Iadd.131. A compound according to claim 107, wherein Z 1  is cis--CH═CH--CH 2  --(CH 2 ).sbsb.g--CH 2  --. .Iaddend..Iadd.132. A compound according to claim 131, wherein g is 3. .Iaddend..Iadd.133. A compound according to claim 131, wherein g is one. 
     
     
        .Iaddend..Iadd.134.  A compound according to claim 133 wherein Y 1  is --C.tbd.C--. .Iaddend..Iadd.135. 13,14-Didehydro-PGF 2  α, 1,9-lactone, a compound according to claim 134. .Iaddend..Iadd.136. A compound according to claim 133, wherein Y 1  is cis--CH═CH--. .Iaddend..Iadd.137. cis-13-PGF 2  α, 1,9-lactone, a compound according to claim 136. .Iaddend..Iadd.138. A compound according to claim 133, wherein Y 1  is --CH 2  CH 2  --. .Iaddend..Iadd.139. 13,14-Dihydro-PGF 2  α, 1,9-lactone, a compound according to claim 138. .Iaddend..Iadd.140. A compound according to claim 133, wherein Y 1  is trans--CH═CH--. .Iaddend..Iadd.141. A compound according to claim 140, wherein R 7  is cis--CH═CH--CH 2  --CH 3  --. .Iaddend..Iadd.142. PGF 3  α, 1,9-lactone, a compound according to claim 141. .Iaddend..Iadd.143. A compound according to claim 140, wherein R 7  is ##STR309## 
     
     
       .Iaddend. .Iadd.144.  A compound according to claim 143, wherein s is zero 
     
     
        or one and T is chloro, fluoro, or trifluoromethyl. .Iaddend..Iadd.145.  A compound according to claim 144, wherein R 5  is methyl. .Iaddend..Iadd.146. 15-Methyl-17-phenyl-18,19,20-trinor-PGF 2  α, 1,9-lactone, a compound according to claim 145. .Iaddend..Iadd.147. A compound according to claim 144, wherein R 5  is hydrogen. .Iaddend..Iadd.148. A compound according to claim 147, wherein at least one of R 3  and R 4  is fluoro. .Iaddend..Iadd.149. 16,16-Difluoro-17-phenyl-18,19,20-trinor-PGF 2  α, 1,9-lactone, a compound according to claim 148. .Iaddend..Iadd.150. A compound according to claim 147, wherein at least one of R 3  and R 4  is methyl. .Iaddend..Iadd.151. 16,16-Dimethyl-17-phenyl-18,19,20-trinor-PGF 2  α, 1,9-lactone, a compound according to claim 150. .Iaddend..Iadd.152. A compound according to claim 147, wherein R 3  and R 4  are both hydrogen. .Iaddend..Iadd.153. 17-Phenyl-18,19,20-trinor-PGF 2  α, 1,9-lactone, a compound according to claim 152. .Iaddend..Iadd.154. A compound according to claim 140, wherein R 7  is --(CH 2 ).sbsb.m--CH 3  --. .Iaddend..Iadd.155. A compound according to claim 154, wherein m is 3. .Iaddend..Iadd.156. A compound according to claim 155, wherein R 5  is 
     
     
        methyl. .Iaddend..Iadd.157.  A compound according to claim 156, wherein at least one of R 3  and R 4  is fluoro. .Iaddend..Iadd.158. 15-Methyl-16,16-difuoro-PGF 2  α, 1,9-lactone, a compound according to claim 157. .Iaddend..Iadd.159. A compound according to claim 156, wherein at least one of R 3  and R 4  is methyl. .Iaddend..Iadd.160. 15,16,16-Trimethyl-PGF 2  α, 1,9-lactone, a compound according to claim 159. .Iaddend..Iadd.161. A compound according to claim 156, wherein R 3  and R 4  are both hydrogen. .Iaddend..Iadd.162. 15-Methyl-PGF 2  α, 1,9-lactone, a compound according to claim 161. .Iaddend..Iadd.163. A compound according to claim 155, wherein R 5  is hydrogen. .Iaddend..Iadd.164. A compound according to claim 163, wherein at least one of R 3  and R 4  is fluoro. .Iaddend..Iadd.165. A compound according to claim 164, wherein R 3  and R 4  are both fluoro. .Iaddend..Iadd.166. 16,16-Difluoro-PGF 2  α, 1,9-lactone, a compound according to claim 165. 
     
     
        .Iaddend..Iadd.   .  A compound according to claim 163, wherein at least one of R 3  and R 4  is methyl. .Iaddend..Iadd.168. A compound according to claim 167, wherein R 3  and R 4  are both methyl. .Iaddend..Iadd.169. 16,16-Dimethyl-PGF 2  α, 1,9-lactone, a compound according to claim 168. .Iaddend..Iadd.170. A compound according to claim 163, wherein R 3  and R 4  are both hydrogen. .Iaddend..Iadd.171. PGF 2  α, 1,9-lactone, a compound according 
     
     
        to claim 170. .Iaddend..Iadd.172.  A prostaglandin-type, 1,9-lactone of the formula ##STR310## wherein W 2  is ##STR311## wherein L 1  is ##STR312## or a mixture of ##STR313## wherein R 3  and R 4  are hydrogen or methyl being the same or different; wherein M 1  is ##STR314## wherein R 5  is hydrogen or methyl wherein T is chloro, fluoro, alkyl of one to 3 carbon atoms, inclusive, or alkoxy of one to 3 carbon atoms, inclusive, the various T's being the same or different, s is zero, one, 2, or 3, with the proviso that not more than two T's are other than alkyl;   wherein Y 1  is trans--CH═CH--, --CH 2  CH 2  --, cis--CH═CH--, or --C.tbd.C--; and   wherein Z 1  is    cis--CH═CH--CH.sub.2 --(CH.sub.2).sbsb.g--CH.sub.2 --,(1)        cis--CH═CH--CH.sub.2 --(CH.sub.2).sbsb.g--CF.sub.2 --,(2)        cis--CH.sub.2 --CH═CH--(CH.sub.2).sbsb.g--CH.sub.2 --,(3)        --(ch.sub.2).sub.3 --(ch.sub.2).sbsb.g--CH.sub.2 --,      (4)        --(ch.sub.2).sub.3 --(ch.sub.2).sbsb.g--CF.sub.2 --,      (5)        --ch.sub.2 --o--ch.sub.2 --(ch.sub.2).sbsb.g--CH.sub.2 --,(6) ##STR315##       
     
     
        wherein g is one to 3, inclusive. .Iaddend..Iadd.173.  A compound according to claim 172, wherein W 2  is ##STR316## 
     
     
       .Iaddend. .Iadd.174.  A compound according to claim 172, wherein W 2  is ##STR317## 
     
     
       .Iaddend. .Iadd.175.  A compound according to claim 174, wherein Y 1  is --C.tbd.C--. .Iaddend..Iadd.176. A compound according to claim 174, wherein Y 1  is cis--CH═CH--. .Iaddend..Iadd.177. A compound according to claim 174, wherein Y 1  is --CH 2  CH 2  --..Iaddend..Iadd.178. A compound according to claim 174, wherein Y 1  is trans--CH═CH--. .Iaddend..Iadd.179. A compound according to claim 172, wherein W 2  is ##STR318## 
     
     
       .Iaddend. .Iadd.180.  A compound according to claim 179, wherein ˜ is α..Iaddend..Iadd.181. A compound according to claim 180, wherein M 1  is ##STR319## 
     
     
       .Iaddend. .Iadd.182.  A compound according to claim 180, wherein M 1  is ##STR320## 
     
     
       .Iaddend. .Iadd.183.  A compound according to claim 182, wherein Z 1  is --CH 2  --O--CH 2  --(CH 2 ).sbsb.g--CH 2  --. .Iaddend..Iadd.184. A compound according to claim 182, wherein Z 1  is ##STR321## 
     
     
       .Iaddend. .Iadd.185.  A compound according to claim 182, wherein Z 1  is ##STR322## 
     
     
       .Iaddend. .Iadd.186.  A compound according to claim 182, wherein Z 1  is cis--CH 2  --CH═CH--(CH 2 ).sbsb.g--CH 2  --. .Iaddend..Iadd.187. A compound according to claim 182, wherein Z 1  is cis--CH═CH--CH 2  --(CH 2 ).sbsb.g--CF 2  --. .Iaddend..Iadd.188. A compound according to claim 182, wherein Z 1  is --(CH 2 ) 3  --(CH 2 ).sbsb.g--CF 2  --. .Iaddend..Iadd.189. A compound according to claim 182, wherein Z 1  is --(CH 2 ) 3  --(CH 2 ).sbsb.g--CH 2  --. .Iaddend..Iadd.190. A compound according to claim 182, wherein Z 1  is cis--CH═CH--CH 2  --(CH 2 ).sbsb.g--CH 2  --. .Iaddend..Iadd.191. A compound according to claim 182, wherein g is 3. .Iaddend..Iadd.192. A compound according to claim 182, wherein g is one. .Iaddend..Iadd.193. A compound according to claim 192, wherein Y 1  is --C.tbd.C--. .Iaddend..Iadd.194. A compound according to claim 192, wherein Y 1  is cis--CH═CH--..Iaddend..Iadd.195. A compound according to claim 192, wherein Y 1  is trans--CH═CH--. .Iaddend..Iadd.196. A compound according to claim 192, wherein Y 1  is --CH 2  CH 2  --. .Iaddend..Iadd.197. A compound according to claim 196, wherein s is zero 
     
     
        or one and T is chloro, fluoro. .Iaddend..Iadd.198.  A compound according to claim 197, wherein R 5  is methyl. .Iaddend..Iadd.199. 15-Methyl-16-phenoxy-17,18,19,20-tetranor-PGF 2  α, 1,9-lactone, a compound according to claim 198. .Iaddend..Iadd.200. A compound according to claim 197, wherein R 5  is hydrogen. .Iaddend..Iadd.201. A compound according to claim 200, wherein at least one of R 3  and R 4  is methyl. .Iaddend..Iadd.202. 16-Methyl-16-pheoxy-18,19,20-trinor-PGF 2  α, 1,9-lactone, a compound according to claim 201. .Iaddend..Iadd.203. A compound according to claim 200, wherein R 3  and R 4  are both hydrogen. .Iaddend..Iadd.204. 16-Phenoxy-17,18,19,20-tetranor-PGF 2  α, 1,9-lactone, a compound according to claim 203. .Iaddend.