USRE29469EExpiredUtility

Hydroxylated 15-deoxy derivatives of 9-hydroxyl-13-trans-prostenoic acid

13
Priority: Jun 19, 1974Filed: May 3, 1976Granted: Nov 8, 1977
Est. expiryJun 19, 1994(expired)· nominal 20-yr term from priority
C07C 405/00C07C 405/0016
13
PatentIndex Score
1
Cited by
1
References
41
Claims

Abstract

This disclosure describes certain 15-deoxy prostanoic acid derivatives having a hydroxy group further along in the beta-chain, useful as bronchodilators; hypotensive agents, anti-ulcer agents, or as intermediates.

Claims

exact text as granted — not AI-modified
We claim: 
     
       1. An optically active compound of the formula: ##STR57## or a racemic compound of that formula and the mirror image thereof wherein R 1  is selected from the group consisting of hydroxy, .[.lower alkoxy, tetrahydropyranyloxy, lower alkanoyloxy,.]. .Iadd.methoxy, ethoxy and .Iaddend.ω-hydroxy substituted .[.lower.]. alkoxy .[.and ω-tetrahydropyranyloxy substituted lower alkoxy.]. .Iadd.having from 2 to 4 carbon atoms; .Iaddend.R 2  is a moiety selected from the group consisting of those of the formulae: ##STR58## wherein R' is selected from the group consisting of .[.a straight chain alkyl group having from 2 to 10 carbon atoms and a straight chain alkyl group having from 2 to 6 carbon atoms and having one branched alkyl group of from 1 to 3 carbon atoms.]. .Iadd.n-propyl, n-butyl and n-pentyl.Iaddend., and R" is .Iadd.a moiety .Iaddend.selected from the group consisting of .[.a straight chain alkyl group having from 2 to 10 carbon atoms and substituted with an hydroxy group, a straight chain alkyl group having from 2 to 6 carbon atoms and having one branched alkyl group of from 1 to 3 carbon atoms and substituted with an hydroxy group, a straight chain alkenyl group having from 2 to 10 carbon atoms and substituted with an hydroxy group and a straight chain alkenyl group having from 2 to 6 carbon atoms and having one branched alkyl group of from 1 to 3 carbon atoms and substituted with an hydroxy group;.]. .Iadd.those of the formulae: .Iadd. ##STR59##.Iaddend. wherein m is an integer from 3 to 5, inclusive, p is an integer from 1 to 3, inclusive, q is zero, 1 or 2, and y is  .Iadd. ##STR60##.Iaddend. R 3  is selected from the group consisting of hydroxy .[.,.]. .Iadd.and .Iaddend.alkoxy having from 1 to .[.12.]. .Iadd.4 .Iaddend.carbon atoms .[.and tetrahydropyranyloxy.].; and Z is a divalent radical selected from the group consisting of those of the formulae: ##STR61## wherein n is an integer from .[.3.].  .Iadd.6 .Iaddend.to 8, inclusive .[., R 4  is an alkyl group having up to 3 carbon atoms, and R 5  is selected from the group consisting of an alkyl group having up to 3 carbon atoms, a fluorine atom and a phenyl group.].; and the pharmacologically acceptable cationic salts thereof when R 3  is hydroxy. 
     
     
       2. The optically active compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR62## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; l-9-oxo-11α,20-dihydroxy-13-trans-prostenoic acid. 
     
     
       3. The racemic compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR63## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; dl-9-oxo-11α,20-dihydroxy-13-trans-prostenoic acid. 
     
     
       4. The optically active compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR64## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; l-9-oxo-11α,16(S)-dihydroxy-13-trans-prostenoic acid. 
     
     
       5. The racemic compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR65## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; dl-9-oxo-11α,16.Iadd.(S).Iaddend.-dihydroxy-13-trans-prostenoic acid. 
     
     
       6. The mixture of the two racemic compounds according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR66## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; 9-oxo-11α,16-dihydroxy-13-trans-prostenoic acid. 
     
     
       7. The optically active compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR67## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; l-9-oxo-11α,16(R)-dihydroxy-13-trans-prostenoic acid. 
     
     
       8. The racemic compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR68## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; dl-9-oxo-11α,16.[.-epidihydroxy.]..Iadd.(R)-dihydroxy.Iaddend.-13-trans-prostenoic acid. 
     
     
       9. The optically active compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR69## R 3  is hydroxy, and Z is --(CH 2 ) 6  ; l-9-oxo-11α,16(S)-dihydroxy-20-methyl-13-trans-prostenoic acid. 
     
     
       10. The racemic compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR70## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; dl-9-oxo-11α,16.Iadd.(S).Iaddend.-dihydroxy-20-methyl-13-trans-prostenoic acid. 
     
     
       11. The mixture of the two racemic compounds according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR71## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; 9-oxo-11α,16-dihydroxy-20-methyl-13-trans-prostenoic acid. 
     
     
       12. The optically active compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR72## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; l-9-oxo-11α,16(R)-dihydroxy-20-methyl-13-trans-prostenoic acid. 
     
     
       13. The racemic compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR73## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; dl-9-oxo-11α,16.Iadd.(R).Iaddend.-.[.epi-.].dihydroxy-20-methyl-13-trans-prostenoic acid. 
     
     
       14. The optically active compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR74## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; l-9-oxo-11α,16(S)-dihydroxy-20-ethyl-13-trans-prostenoic acid. 
     
     
       15. The racemic compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR75## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; dl-9-oxo-11α,16.Iadd.(S).Iaddend.-dihydroxy-20-ethyl-13-trans-prostenoic acid. 
     
     
       16. The mixture of the two racemic compounds according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR76## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; 9-oxo-11α,16-dihydroxy-20-ethyl-13-trans-prostenoic acid. 
     
     
       17. The optically active compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR77## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; l-9-oxo-11α,16(R)-dihydroxy-20-ethyl-13-trans-prostenoic acid. 
     
     
       18. The racemic compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR78## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; dl-9-oxo-11α,16.[.-epidihydroxy.]..Iadd.(R)-dihydroxy.Iaddend.-20-ethyl-13-trans-prostenoic acid. 
     
     
       19. The optically active compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR79## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; l-9-oxo-11α,16(S)-dihydroxy-20-methyl-13-trans,17-trans-prostadienoic acid.  .[. 
     
     
       20.  The racemic compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR80## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; dl-9-oxo-11α,16(S)-dihydroxy-20-methyl-13-trans,17-trans-prostadienoic acid..]. 
     
     
       21. The mixture of the two racemic compounds according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR81## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; 9-oxo-11α,16-dihydroxy-20-methyl-13-trans,17-trans-prostadienoic acid.  .[. 
     
     
       22.  The optically active compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR82## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; l-9-oxo-11α,16(R)-dihydroxy-20-methyl-13-trans,17-trans-prostadienoic acid..]. .[. 
     
     
       23.  The racemic compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR83## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; dl-9-oxo-11α,16-epi-dihydroxy-20-methyl-13-trans,17-trans-prostadienoic acid..]. 
     
     
       24. The optically active compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR84## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; l-9-oxo-11α,17(S)-dihydroxy-13-trans-prostenoic acid.  .[. 
     
     
       25.  The racemic compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR85## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; dl-9-oxo-11α,17-dihydroxy-13-trans-prostenoic acid..]. .[. 
     
     
       26.  The optically active compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR86## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; l-9-oxo-11α,17(R)-dihydroxy-13-trans-prostenoic acid..].  .[. 
     
     
       27.  The racemic compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR87## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; dl-9-oxo-11α,17-epi-dihydroxy-13-trans-prostenoic acid..]. 
     
     
       28. The mixture of the two racemic compounds according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR88## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; 9-oxo-11α,17-dihydroxy-13-trans-prostenoic acid. 
     
     
       29. The optically active compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR89## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; l-9-oxo-11α-hydroxy-15(S)-hydroxymethyl-13-trans-prostenoic acid. .[. 
     
     
       30.  The racemic compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR90## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; dl-9-oxo-11α-hydroxy-15-hydroxymethyl-13-trans-prostenoic acid..]. 
     
     
       31. The mixture of the two racemic compounds according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR91## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; 9-oxo-11α-hydroxy-15-hydroxymethyl-13-trans-prostenoic acid. .[. 
     
     
       32.  The optically active compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR92## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; l-9-oxo-11α-hydroxy-15(R)-hydroxymethyl-13-trans-prostenoic acid..]. .[. 
     
     
       33.  The racemic compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR93## R 3  is hydroxy, and Z is --(CH 2 ) 6  --; dl-9-oxo-11α-hydroxy-15-epi-hydroxymethyl-13-trans-prostenoic acid..]. .Iadd. 
     
     
       34.  The optically active compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR94##.Iaddend. R 3  is hydroxy, and Z is --(CH 2 ) 4  --O--CH 2  --; l-9-oxo-11α,16(S)-dihydroxy-3-oxa-13-trans-prostenoic acid. .Iadd. 
     
     
       35.  The racemic compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR95##.Iaddend. R 3  is hydroxy, and Z is --(CH 2 ) 4  --O--CH 2  --; dl-9-oxo-11α,16(S)-dihydroxy-3-oxa-13-trans-prostenoic acid. .Iadd. 
     
     
       36.  The mixture of the two racemic compounds according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR96##.Iaddend. R 3  is hydroxy, and Z is --(CH 2 ) 4  --O--CH 2  --; 9-oxo-11α,16-dihydroxy-3-oxa-13-trans-prostenoic acid. .Iadd. 
     
     
       37.  The optically active compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR97##.Iaddend. R 3  is hydroxy, and Z is --(CH 2 ) 4  --O--CH 2  --; l-9-oxo-11α,16(R)-dihydroxy-3-oxa-13-trans-prostenoic acid. .Iadd. 
     
     
       38.  The racemic compound according to claim 1 wherein R 1  is hydroxy, R 2  is ##STR98##.Iaddend. R 3  is hydroxy, and Z is --(CH 2 ) 4  --O--CH 2  --; dl-9-oxo-11α,16(R)-dihydroxy-3-oxa-13-trans-prostenoic acid. .Iadd. 
     
     
       39.  The optically active compound according to claim 1 wherein R 1  is hydroxy, R 2  is .Iadd. ##STR99##.Iaddend. R 3  is ethoxy, and Z is --(CH 2 ) 6  --; l-ethyl 9-oxo-11α,16(S)-dihydroxy-20-methyl-13-trans,18-cis-prostadienoate. .Iadd. 
     
     
       40.  The mixture of the two racemic compounds according to claim 1 wherein R 1  is hydroxy, R 2  is  .Iadd. ##STR100##.Iaddend. R 3  is ethoxy, and Z is --(CH 2 ) 6  --; ethyl 9-oxo-11α,16-dihydroxy-20-methyl-13-trans,18-cis-prostadienoate. .Iadd. 
     
     
       41.  The optically active compound ethyl l-9-oxo-11α,16-dihydroxy-17-methyl-13-transprostenoate. .Iaddend. .Iadd.42. The racemic compound ethyl dl-9-oxo-11α,16-dihydroxy-17-methyl-13-transprostenoate. .Iaddend. .Iadd.43. The optically active compound l-9-oxo-11α,16-dihydroxy-17-methyl-13-trans-prostenoic acid. .Iaddend. .Iadd.44. The racemic compound dl-9-oxo-11α,16-dihydroxy-17-methyl-13-trans-prostenoic acid. .Iaddend. .Iadd.45. The optically active compound l-9-oxo-11α-hydroxy-16-hydroxy-17-methyl-19,20-dinor-13-trans-prostenoic acid. .Iaddend. .Iadd.46. The racemic compound dl-9-oxo-11α-hydroxy-16-hydroxy-17-methyl-19,20-dinor-13-trans-prostenoic acid. .Iaddend. .Iadd.47. The optically active compound l-9-oxo-11α-hydroxy-16-hydroxy-17-ethyl-20-nor-13-trans-prostenoic 
     
     
        acid. .Iaddend. .Iadd.48.  The racemic compound dl-9-oxo-11α-hydroxy-16-hydroxy-17-ethyl-20-nor-13-trans-prostenoic acid.

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