Claims
- 1. An optically active compound of the formula ##STR78## or a mixture comprising that compound and the enantiomer thereof, wherein Q is ##STR79## wherein R.sub.3 is hydrogen or alkyl of one to 4 carbon atoms, inclusive; wherein R.sub.1 is hydrogen, alkyl of one to 12 carbon atoms, inclusive, cycloalkyl of 3 to 10 carbon atoms, inclusive, aralkyl of 7 to 12 carbon atoms, inclusive, phenyl, or phenyl substituted with one, 2, or 3 chloro or alkyl of one to 4 carbon atoms, inclusive; including the pharmacologically acceptable salts thereof when R.sub.1 is hydrogen; wherein R.sub.38 is ##STR80## wherein R.sub.39 and R.sub.40 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.39 and R.sub.40 is fluoro only when the other is hydrogen or fluoro and the further proviso that neither R.sub.39 nor R.sub.40 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.39 R.sub.40 -- and the phenyl ring; and wherein L is alkyl of one to 4 carbon atoms, inclusive, fluoro, chloro, trifluoromethyl, or --OR.sub.41 -- wherein R.sub.41 is alkyl of one to 4 carbon atoms, inclusive, and p is zero, one, 2 or 3, with the proviso that not more than two L's are other than alkyl and when p is 2 or 3 the L's are either the same or different.
- 2. A compound according to claim 1 wherein Z is oxa (--O--).
- 3. A compound according to claim 2 wherein Q is ##STR81##
- 4. A compound according to claim 2 wherein Q is ##STR82##
- 5. A compound according to claim 4 wherein R.sub.39 and R.sub.40 are hydrogen, methyl, or ethyl, being the same or different.
- 6. A compound according to claim 5 wherein both R.sub.39 and R.sub.40 are hydrogen.
- 7. A compound according to claim 6 wherein R.sub.3 is hydrogen.
- 8. A compound according to claim 7 wherein R.sub.1 is alkyl of one to 12 carbon atoms.
- 9. A compound according to claim 7 wherein R.sub.1 is hydrogen or a pharmacologically acceptable cation.
- 10. 4,5,6,17,18,19,20-Heptanor-3,7-inter-m-phenylene-16-phenoxy-PGA.sub.1, a compound according to claim 9.
- 11. 4,5,6,17,18,19,20-Heptanor-3,7-inter-m-phenylene-16-(m-tolyloxy)-PGA.sub.1, a compound according to claim 9.
- 12. 4,5,6,17,18,19,20-Heptanor-3,7-inter-m-phenylene-16-(p-tolyloxy)-PGA.sub.1, a compound according to claim 9.
- 13. 4,5,6,17,18,19,20-Heptanor-3,7-inter-m-phenylene-16-(m-chlorophenoxy)-PGA.sub.1, a compound according to claim 9.
- 14. 4,5,6,17,18,19,20-Heptanor-3,7-inter-m-phenylene-16-(p-chlorophenoxy)-PGA.sub.1, a compound according to claim 9.
- 15. 4,5,6,17,18,19,20-Heptanor-3,7-inter-m-phenylene-16-(m-fluorophenoxy)-PGA.sub.1, a compound according to claim 9.
- 16. 4,5,6,17,18,19,20-Heptanor-3,7-inter-m-phenylene-16-(p-fluorophenoxy)-PGA.sub.1, a compound according to claim 9.
- 17. 4,5,6,17,18,19,20-Heptanor-3,7-inter-m-phenylene-16-(m-trifluoromethylphenoxy)-PGA.sub.1, a compound according to claim 9.
- 18. 4,5,6,17,18,19,20-Heptanor-3,7-inter-m-phenylene-16-(p-trifluoromethylphenoxy)-PGA.sub.1, a compound according to claim 9.
- 19. 4,5,6,17,18,19,20-Heptanor-3,7-inter-m-phenylene-16-(m-anisyloxy)-PGA.sub.1, a compound according to claim 9.
- 20. 4,5,6,17,18,19,20-Heptanor-3,7-inter-m-phenylene-16-(p-anisyloxy)-PGA.sub.1, a compound according to claim 9.
- 21. A compound according to claim 6 wherein R.sub.3 is methyl.
- 22. A compound according to claim 5 wherein one or both of R.sub.39 and R.sub.40 are methyl.
- 23. A compound according to claim 22 wherein R.sub.3 is hydrogen.
- 24. A compound according to claim 23 wherein R.sub.1 is alkyl of one to 12 carbon atoms.
- 25. A compound according to claim 23 wherein R.sub.1 is hydrogen or a pharmacologically acceptable cation.
- 26. 4,5,6,18,19,20-Hexanor-3,7-inter-m-phenylene-16-methyl-16-phenoxy-PGA.sub.1, a compound according to claim 25.
- 27. A compound according to claim 1 wherein Z is C.sub.j H.sub.2j wherein C.sub.j H.sub.2j is as defined in claim 1.
- 28. A compound according to claim 27 wherein Q is ##STR83##
- 29. A compound according to claim 27 wherein Q is ##STR84##
- 30. A compound according to claim 29 wherein R.sub.39 and R.sub.40 are hydrogen, methyl, ethyl, or fluoro, being the same or different.
- 31. A compound according to claim 30 wherein R.sub.39 and R.sub.40 are both hydrogen.
- 32. A compound according to claim 31 wherein R.sub.3 is hydrogen.
- 33. A compound according to claim 32 wherein C.sub.j H.sub.2j is a valence bond.
- 34. 4,5,6,17,18,19,20-Heptanor-3,7-inter-m-phenylene-16-phenyl-PGA.sub.1, a compound according to claim 33.
- 35. A compound according to claim 32 wherein C.sub.j H.sub.2j is methylene.
- 36. 4,5,6,18,19,20-Hexanor-3,7-inter-m-phenylene-17-phenyl-PGA.sub.1, a compound according to claim 35.
- 37. 4,5,6,18,19,20-Hexanor-3,7-inter-m-phenylene-17-(m-tolyl)-PGA.sub.1, a compound according to claim 35.
- 38. 4,5,6,18,19,20-Hexanor-3,7-inter-m-phenylene-17-(p-tolyl)-PGA.sub.1, a compound according to claim 35.
- 39. 4,5,6,18,19,20-Hexanor-3,7-inter-m-phenylene-17-(m-chlorophenyl)-PGA.sub.1, a compound according to claim 35.
- 40. 4,5,6,18,19,20-Hexanor-3,7-inter-m-phenylene-17-(p-chlorophenyl)-PGA.sub.1, a compound according to claim 35.
- 41. 4,5,6,18,19,20-Hexanor-3,7-inter-m-phenylene-17-(m-fluorophenyl)-PGA.sub.1, a compound according to claim 35.
- 42. 4,5,6,18,19,20-Hexanor-3,7-inter-m-phenylene-17-(p-fluorophenyl)-PGA.sub.1, a compound according to claim 35.
- 43. 4,5,6,18,19,20-Hexanor-3,7-inter-m-phenylene-17-(m-trifluoromethylphenyl)-PGA.sub.1, a compound according to claim 35.
- 44. 4,5,6,18,19,20-Hexanor-3,7-inter-m-phenylene-17-(p-trifluoromethylphenyl)-PGA.sub.1, a compound according to claim 35.
- 45. 4,5,6,18,19,20-Hexanor-3,7-inter-m-phenylene-17-(m-anisyl)-PGA.sub.1, a compound according to claim 35.
- 46. 4,5,6,18,19,20-Hexanor-3,7-inter-m-phenylene-17-(p-anisyl)-PGA.sub.1, a compound according to claim 35.
- 47. A compound according to claim 32 wherein C.sub.j H.sub.2j is ethylene.
- 48. A compound according to claim 31 wherein R.sub.3 is methyl.
- 49. A compound according to claim 30 wherein one or both of R.sub.39 and R.sub.40 are methyl.
- 50. A compound according to claim 49 wherein R.sub.3 is hydrogen.
- 51. A compound according to claim 50 wherein C.sub.j H.sub.2j is a valence bond.
- 52. A compound according to claim 50 wherein C.sub.j H.sub.2j is methylene.
- 53. 4,5,6,18,19,20-Hexanor-3,7-inter-m-phenylene-16-methyl-17-phenyl-PGA.sub.1, a compound according to claim 52.
- 54. 4,5,6,18,19,20-Hexanor-3,7-inter-m-phenylene-16,16-dimethyl-17-phenyl-PGA.sub.1, a compound according to claim 52.
- 55. A compound according to claim 50 wherein C.sub.j H.sub.2j is ethylene.
- 56. A compound according to claim 30 wherein one or both of R.sub.39 and R.sub.40 are fluoro.
- 57. A compound according to claim 56 wherein R.sub.3 is hydrogen.
- 58. A compound according to claim 57 wherein C.sub.j H.sub.2j is a valence bond.
- 59. A compound according to claim 57 wherein C.sub.j H.sub.2j is methylene.
- 60. 4,5,6,18,19,20-Hexanor-3,7-inter-m-phenylene-16-fluoro-17-phenyl-PGA.sub.1, a compound according to claim 59.
- 61. 4,5,6,18,19,20-Hexanor-3,7-inter-m-phenylene-16,16-difluoro-17-phenyl-PGA.sub.1, a compound according to claim 59.
- 62. 4,5,6,19,20-Pentanor-3,7-inter-m-phenylene-18-phenyl-PGA.sub.1, a compound according to claim 57.
CROSS REFERENCE TO RELATED APPLICATIONS
This is a division of application Ser. No. 764,359, filed Jan., 31, 1977 now U.S. Pat. No. 4,118,577 which is in turn a continuation-in-part of application Ser. No. 677,874 filed Apr. 19, 1976 now abandoned which was a divisional of then co-pending application Ser. No. 604,158 filed Aug. 13, 1975 and since abandoned.
Non-Patent Literature Citations (1)
Entry |
Derwent Abstr. 48794y/28, BE850-204, 07/07/77. |
Divisions (2)
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Number |
Date |
Country |
Parent |
764359 |
Jan 1977 |
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Parent |
604158 |
Aug 1975 |
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Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
677874 |
Apr 1976 |
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