Kanojia, Ramesh M.; Wachter, Michael P.; Chen, Robert H. K.;

Oxepanes

Chemical compounds having a substituted oxepane ring and methods of preparing such compounds are described. The compounds are active as utero-evacuant agents.

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What is claimed is:

1. A compound selected from the group consisting of: ##STR439## wherein R.sub.1 is -XY wherein X is hydrogen or hydroxy provided that when X is hydrogen, Y is hydrogen; methyl; hydroxy; lower alkoxy; cycloalkoxy; phenoxy; substituted phenoxy; trialkylsilyloxy; -OCOR' wherein R' is lower alkyl, cycloalkyl, phenyl, and substituted phenyl; a sulfate, nitrate or phosphate radical; thiol; alkylthio; arylthio; halo; amino; alkylamino; dialkylamino; arylamino; and the quaternary ammonium and acid addition salts thereof; acylamino; --OCONHR wherein R is hydrogen or lower alkyl; and when X is hydroxy, Y is cyano; lower alkyl; lower alkenyl; lower alkynyl; propadienyl; benzyl; substituted benzyl; phenyl; substituted phenyl; provided that when d is unsaturated R.sub.1 is either X or Y; and R.sub.1 is oxo; oxo; thioxo; hydroxyimino; alkoxyimino; aryloxyimino; acyloxyimino; hydrazono; alkylhydrazono; arylhydrazono; arylsulfonylhydrazono; carbamoylhydrazono; ethylenedioxy; dialkoxy; methylenyl; alkyldenyl; alkylimino; or arylimino;

R.sub.4 is hydrogen; methyl or methylenyl;

R.sub.5 is hydrogen; hydroxy; hydroperoxy or --OCOR''' wherein R''' is lower alkyl;

R.sub.6 is methylenyl when g is unsaturated, and when g is saturated R.sub.6 is -CHXY wherein X is hydrogen or hydroxy, provided that when X is hydrogen, Y is hydrogen; methyl; hydroxy; lower alkoxy; cycloalkoxy; phenoxy; substituted phenoxy: trialkylsilyloxy; --OCOR' wherein R' is lower alkyl, cycloalkyl, phenyl or substituted phenyl; a sulfate, nitrate or phosphate radical; thiol; alkylthio; arylthio; halo; amino; alkylamino; dialkylamino; arylamino; and the quaternary ammonium and acid addition salts thereof; acylamino; --OCONHR wherein R is hydrogen or lower alkyl; and when X is hydroxy, Y is cyano; lower alkyl; lower alkenyl; lower alkynyl; propadienyl; benzyl; substituted benzyl; phenyl; substituted phenyl; and R.sub.6 is --CHZ wherein Z is oxo; thioxo; hydroxyimino; alkoxyimino; aryloxyimino; acyloxyimino; hydrazono; alkylhydrazono; arylhydrazono; arylsulfonylhydrazono; carbamoylhydrazono; ethylenedioxy; dialkoxy; methylenyl; alkylidenyl; alkylimino; or arylimino; or R.sub.6 is carboxy; --COOR' wherein R' is lower alkyl or cycloalkyl; phenyl or substituted phenyl; --COR" wherein R" is amino, alkylamino, dialkylamino, arylamino, halo, hydrazino, alkylhydrazino, dialkylhydrazino, arylhydrazino, arylsulfonylhydrazino; cyano; and ammonium, alkali metal and alkaline earth metal salts thereof where R.sub.6 is carboxy;

R.sub.7 is hydrogen; hydroxy; lower alkoxy; or --OCOR''' wherein R''' is lower alkyl;

and n is an integer from 0-5 provided that when b is unsaturated, C, d, & f are saturated.

2. A compound of claim 1 wherein n is 0.

3. A compound of claim 1 wherein n is 1.

4. A compound of claim 1 which compound is 2S,3R6S-6-ethenyl-2-methyl-2-(4,8-dimethyl-5-oxo-7-nonenyl)-3,6-oxidooxepa ne.

5. A compound of claim 1 which compound is 2S,3R,6S-6-ethyl-2-methyl-2-(4,8-dimethyl-5-oxononyl)-3,6-oxidooxepane.

6. A compound of claim 1 which compound is 2S,3R,6R-6-(2-oxoethyl)-2-methyl-2-(4,8-dimethyl-5-oxo-7-nonenyl)-3,6-oxid ooxepane.

7. A compound of claim 1 which compound is 2S,3R,6R-6-(2-hydroxyethyl)-2-methyl-2-(4,8-dimethyl-5-oxo-7-nonenyl)-3,6- oxidooxepane.

8. A compound of claim 1 which compound is 2S,3R,6R-2-methyl-6-carboxymethyl-2-(4,8-dimethyl-5-oxo-7-nonenyl)-3,6-oxi dooxepane.

9. A compound of claim 1 which compound is 2S,3R,6R-6-(2-hydroxyethyl)-2-methyl-2-(4,8-dimethyl-5-hydroxy-7-nonenyl)- 3,6-oxidooxepane.

10. A compound of claim 1 which compound is 2S,3R,6R-2-methyl-6-carboxymethyl-2-(4,8-dimethyl-5-hydroxy-7-nonenyl)-3,6 -oxidooxepane.

11. A compound of claim 1 which compound is 2S,3R,6R-2-methyl-6-carbmethoxymethyl-2-(4,8-dimethyl-5-hydroxy-7-nonenyl) -3,6-oxidooxepane.

12. A compound of claim 1 which compound is 2S,3R,6R-2-methyl-6-carboxymethyl-2-(4,8-dimethyl-5-ethynyl-5-hydroxy-7-no nenyl)-3,6-oxidooxepane.

13. A compound of claim 1 which compound is 2S,3R,6R-6-(2-oxoethyl)-2-methyl-2-(4,8-dimethyl-5-oxononyl)-3,6-oxidooxep ane.

14. A compound of claim 1 which compound is 2S,3R,6R-2-methyl-6-carboxymethyl-2-(4,8-dimethyl-5-oxononyl)-3,6-oxidooxe pane.

15. A compound of claim 1 which compound is 2S,3R,6R-2-methyl-6-carboxymethyl-2-(4,8-dimethyl-8-hydroxy-5-oxo-6-noneny l)-3,6-oxidooxepane.

16. A compound of claim 1 which compound is 2S,3R,6S-6-carboxy-2-methyl-2-(5-oxo-4,7,8-trimethyl-6E-nonenyl)-3,6-oxido oxepane.

17. A compound of claim 1 which compound is 2S,3R,6S-6-carboxy-2-methyl-2-(4,8-dimethyl-5-oxo-7-nonenyl)-3,6-oxidooxep ane.

18. A compound of claim 1 which compound is 2S,3R,6S-6-carboxy-2-methyl-2-(5-hydroxy-4,8-dimethyl-7-nonenyl)-3.6-oxido oxepane.

19. A compound of claim 1 which compound is 2S,3R,6R-2-methyl-6-carboxymethyl-2-(5-hydroxy-4,5,8-trimethyl-7-nonenyl)- 3,6-oxidooxepane.

20. A compound of claim 1 which compound is 2R,3R,6R-6-(2-hydroxyethyl)-2-methyl-2-(4,8-dimethyl-5-hydroxynonyl)-3,6-o xidooxepane.

21. A compound of claim 1 which compound is 2S,3R,6R-6-(2-oxoethyl)-2-methyl-2-(4,8-dimethyl-5-hydroxy-7-nonenyl)-3,6- oxidooxepane.

22. A compound of claim 1 which compound is 2S,3R,6R-6-(2-hydroxethyl)-2-methyl-2-(4,8-dimethyl-5-oxononyl)-3,6-oxidio oxepane.

23. A compound of claim 1 which compound is 2S,3R,6R-6-(2-oxoethyl)-2-methyl-2-(4,8-dimethyl-5-hydroxynonyl)-3,6-oxido oxepane.

24. A compound of claim 1 which compound is 2S,3R,6R-2-methyl-6-carboxymethyl-2-(4,8-dimethyl-5-hydroxynonyl)-3,6-oxid ooxepane.

25. A compound of claim 1 which compound is 2S,3R,6R-2-methyl-6-carboxymethyl-2-[5-oxo-4,7,8-trimethyl-6E-nonenyl]-3,6 -oxidooxepane.