2-Decarboxy-2-hydroxymethyl-19,20-didehydro-PG1 compounds
CROSS REFERENCE TO RELATED APPLICATIONS 
     The present application is a division of Ser. No. 026,066, filed Apr. 2, 1979 pending issuance as a United States Patent. 
    
    
     BACKGROUND OF THE INVENTION 
     The present invention relates to novel prostaglandin analogs. Particularly, these compounds are analogs of the prostaglandins wherein the C-20-C-19 position is unsaturated. i.e., 19,20-didehydro-PG compounds. Most particularly, the present invention relates to novel 2-decarboxy-2-hydroxymethyl-19,20-didehydro-PG 1  compounds, a disclosure of the preparation and use of which is incorporated here by reference from U.S. Pat. No. 4,228,104. 
     Prior Art 
     Prostaglandin analogs exhibiting unsaturation in the C-17, C-18, or C-20 position are known in the art. See, for example, U.S. Pat. No. 3,919,285 German Offenlegungsschrift No. 2,635,985 (and its corresponding Derwent Farmdoc CPI No. 10302A), and U.S. Pat. No. 4,064,351 for examples of such compounds. See also the references cited in U.S. Ser. No. 026.066. 
    
    
     SUMMARY OF THE INVENTION 
     The present invention particularly provides: 
     A compound of the formula ##STR1## wherein D is (1) --(CH 2 ) 3  --(CH 2 ) g  --CH 2  --, 
     (2) --(CH 2 ) 3  --CH 2  --CF 2  --, 
     (3) --(CH 2 ) 3  --O--CH 2  --, 
     (4) --(CH 2 ) 2  --O--(CH 2 ) 2  --, 
     (5) --CH 2  --O--(CH 2 ) 3  --, ##STR2## wherein g is zero, one, two, or three; wherein Q is ##STR3## wherein R 5  is hydrogen or methyl, wherein R 2  is hydrogen, hydroxyl, or hydroxymethyl; 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 W is ##STR4## and wherein X is cis- or trans-CH═CH-- or --C.tbd.C--. 
     Specific embodiments of the present invention include 
     2-decarboxy-2-hydroxymethyl-19,20-didehydro-PGF 1 α, 
     2-decarboxy-2-hydroxymethyl-16,16-dimethyl-19,20-didehydro-PGF 1 α 
     2-decarboxy-2-hydroxymethyl-16,16-difluoro-19,20-didehydro-PGF 1 α 
     2-decarboxy-2-hydroxymethyl-11-deoxy-19,20-didehydro-PGF 1 α, 
     2-decarboxy-2-hydroxymethyl-11-deoxy-16,16-dimethyl-19,20-didehydro-PGF.sub.1α, 
     2-decarboxy-2-hydroxymethyl-11-deoxy-16,16-difluoro-19,20-didehydro-PGF.sub.1α, 
     2-decarboxy-2-hydroxymethyl-11-deoxy-11.sub.α -hydroxymethyl-19,20-didehydro-PGF 1 α, 
     2-decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-16,16-dimethyl-19,20-didehydro-PGF 1 α, 
     2-decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-16,16-difluoro-19,20-didehydro-PGF 1 α, 
     2-decarboxy-2-hydroxymethyl-19,20-didehydro-PGF 1 α, 
     2-decarboxy-2-hydroxymethyl-16,16-dimethyl-19,20-didehydro-PGF 1 β, 
     2-decarboxy-2-hydroxymethyl-16,16-difluoro-19,20-didehydro-PGF 1 β, 
     2-decarboxy-2-hydroxymethyl-11-deoxy-19,20-didehydro-PGF 1 β, 
     2-decarboxy-2-hydroxymethyl-11-deoxy-16,16-dimethyl-19,20-didehydro-PGF.sub.1β, 
     2-decarboxy-2-hydroxymethyl-16,16-difluoro-19,20-didehydro-PGF 1 β, 
     2-decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-19,20-didehydro-PGF 1 β, 
     2-decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-16,16-dimethyl-19,20-didehydro-PGF 1 β, 
     2-decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-16,16-difluoro-19,20-didehydro-PGF 1 β, 
     2-decarboxy-2-hydroxymethyl-19,20-didehydro-PGE 1 , 
     2-decarboxy-2-hydroxymethyl-16,16-dimethyl-19,20-didehydro-PGE 1 , 
     2-decarboxy-2-hydroxymethyl-16,16-difluoro-19,20-dihydro-PGE 1 , 
     2-decarboxy-2-hydroxymethyl-11-deoxy-19,20-didehydro-PGE 1 , 
     2-decarboxy-2-hydroxymethyl-11-deoxy-16,16-dimethyl-19,20-didehydro-PGE.sub.1, 
     2-decarboxy-2-hydroxymethyl-11-deoxy-16,16-difluoro-19,20-didehydro-PGE.sub.1, 
     2-decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-19,20-didehydro-PGE 1 , 
     2-decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-16,16-dimethyl-19,20-didehydro-PGE 1 , 
     2-decarboxy-2-hydroxymethyl-11-deoxy-11α-hydroxymethyl-16,16-difluoro-19,20-didehydro-PGE 1 , 
     2-decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-19,20-didehydro-PGE 1 , 
     2-decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-16,16-dimethyl-19,20-didehydro-PGE 1 , 
     2-decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-16,16-difluoro-19,20-didehydro-PGE 1 , 
     2-decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-19,20-didehydro-PGE 1 , 
     2-decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-16,16-dimethyl-19,20-didehydro-PGE 1 , 
     2-decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-16,16-difluoro-19,20-didehydro-PGE 1 , 
     2-decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-19,20-didehydro-PGE 1 , 
     2-decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-16,16-dimethyl-19,20-didehydro-PGE 1 , 
     2-decarboxy-2-hydroxymethyl-9-deoxo-9-methylene-11-deoxy-11α-hydroxymethyl-16,16-difluoro-19,20-didehydro-PGE 1 . 
     The compounds of the present invention are particularly useful for inducing prostaglandin-like biological effects, as is described in U.S. Ser. No. 026,066. Uses of compounds in accordance with the present invention include, therefore, anti-asthmatic indication.