Claims
- 1. A compound of the formula ##STR117## wherein W.sub.2 is .alpha.-OH:.beta.-H, .alpha.-H:.beta.-OH, oxo, or .alpha.-H:.beta.-H; wherein D is
- (1) --(CH.sub.2).sub.d --, wherein d is one to 5, inclusive,
- (2) --(CH.sub.2).sub.d --CF.sub.2 --, wherein d is one to 5, inclusive,
- (3) --(CH.sub.2).sub.k --CH.dbd.CH--, wherein k is one or 2;
- wherein one of R.sub.4 and R.sub.5 is hydrogen, and the other is hydrogen, alkyl of one to 12 carbon atoms, inclusive, benzyl, or phenyl;
- wherein R.sub.11 is
- --C(R.sub.12)(R.sub.13)--C.sub.g H.sub.2g --CH.sub.3, (1)
- wherein C.sub.g H.sub.2g is alkylene of one to 9 carbon atoms, inclusive, with one to 5 carbon atoms, inclusive, in the chain between --CR.sub.12 R.sub.13 -- and terminal methyl, wherein R.sub.12 and R.sub.13 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.12 and R.sub.13 is fluoro only when the other is hydrogen or fluoro;
- --C(R.sub.12)(R.sub.13)--Z--(Ph), (2)
- wherein R.sub.12 and R.sub.13 are as defined above; 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, substituted with zero, one, or 2 fluoro, with one to 6 carbon atoms, inclusive between --CR.sub.12 R.sub.13 -- and (Ph), wherein (Ph) is phenyl or phenyl substituted by (T)s, wherein T is alkyl of one to 4 carbon atoms, inclusive, fluoro, chloro, trifluoromethyl, or --OR.sub.14, wherein R.sub.14 is alkyl of one to 4 carbon atoms, inclusive, and s is zero, one, 2, or 3, with the proviso that not more than two T s are other than alkyl and when s is 2 or 3 the T s are either the same or different; or
- cis--CH.sub.2 --CH.dbd.CH CH.sub.2 CH.sub.3 ; (3)
- ps wherein Q.sub.1 is .alpha.-OH:.beta.-R.sub.8 or .alpha.-R.sub.8 :.beta.-OH, wherein R.sub.8 is hydrogen or methyl;
- wherein X is trans--CH.dbd.CH--, cis-CH.dbd.CH--, --C.tbd.C--, or --CH.sub.2 CH.sub.2 --.
- 2. A compound according to claim 1, wherein X is --CH.sub.2 CH.sub.2 --.
- 3. A compound according to claim 2, wherein Q.sub.1 is .alpha.-OH:.beta.-R.sub.8, wherein R.sub.8 is hydrogen or methyl.
- 4. A compound according to claim 3, wherein R.sub.8 is hydrogen.
- 5. A compound according to claim 4, wherein W.sub.2 is .alpha.-OH:.beta.-H.
- 6. 2-Decarboxy-2-aminomethyl-(5E)-6a-carba-13,14-dihydro-PGI.sub.2, a compound according to claim 5.
- 7. 2-Decarboxy-2-aminomethyl-(5Z)-6a-carba-13,14-dihydro-PGI.sub.2, a compound according to claim 5.
- 8. A compound according to claim 3, wherein R.sub.8 is methyl.
- 9. A compound according to claim 8, wherein W.sub.2 is .alpha.-OH:.beta.-H.
- 10. 2-Decarboxy-2-aminomethyl-(5E)-6a-carba-13,14-dihydro-(15S)-15-methyl-PGI.sub.2, a compound according to claim 9.
- 11. 2-Decarboxy-2-aminomethyl-(5Z)-6a-carba-13,14-dihydro-(15S)-15-methyl-PGI.sub.2, a compound according to claim 9.
- 12. A compound according to claim 1, wherein X is trans--CH.dbd.CH--.
- 13. A compound according to claim 12, wherein Q.sub.1 is .alpha.-OH:.beta.-R.sub.8.
- 14. A compound according to claim 13, wherein R.sub.8 is hydrogen.
- 15. A compound according to claim 14, wherein W.sub.2 is .alpha.-H:.beta.-OH.
- 16. 2-Decarboxy-2-aminomethyl-(5E)-6a-carba-11.beta.-PGI.sub.2, a compound according to claim 15.
- 17. 2-Decarboxy-2-aminomethyl-(5Z)-6a-carba-11.beta.-PGI.sub.2, a compound according to claim 15.
- 18. A compound according to claim 14, wherein W.sub.2 is oxo.
- 19. 2-Decarboxy-2-aminomethyl-(5E)-6a-carba-11-dehydro-PGI.sub.2, a compound according to claim 18.
- 20. 2-Decarboxy-2-aminomethyl-(5Z)-6a-carba-11-dehydro-PGI.sub.2, a compound according to claim 18.
- 21. A compound according to claim 14, wherein W.sub.2 is .alpha.-H:.beta.-H.
- 22. 2-Decarboxy-2-aminomethyl-(5E)-6a-carba-11-deoxy-PGI.sub.2, a compound according to claim 21.
- 23. 2-Decarboxy-2-aminomethyl-(5Z)-6a-carba-11-deoxy-PGI.sub.2, a compound according to claim 21.
- 24. A compound according to claim 14, wherein W.sub.2 is .alpha.-OH:.beta.-H.
- 25. A compound according to claim 24, wherein D is --(CH.sub.2).sub.d --, wherein d is one to 5, inclusive.
- 26. A compound according to claim 25, wherein D is --(CH.sub.2).sub.3 --.
- 27. A compound according to claim 26, wherein R.sub.11 is n-pentyl.
- 28. 2-Decarboxy-2-aminomethyl-(5E)-6a-carba-PGI.sub.2, a compound according to claim 27.
- 29. 2-Decarboxy-2-aminomethyl-(5Z)-6a-carba-PGI.sub.2, a compound according to claim 27.
- 30. A compound according to claim 26, wherein R.sub.11 is --C(CH.sub.3).sub.2 --(CH.sub.3).sub.3 --CH.sub.3.
- 31. 2-Decarboxy-2-aminomethyl-(5E)-6a-carba-16,16-dimethyl-PGI.sub.2, a compound according to claim 30.
- 32. 2-Decarboxy-2-aminomethyl-(5Z)-6a-carba-16,16-dimethyl-PGI.sub.2, a compound according to claim 30.
- 33. A compound according to claim 26, wherein R.sub.11 is cis--CH.sub.2 --CH.dbd.CH--CH.sub.2 CH.sub.3.
- 34. 2-Decarboxy-2-aminomethyl-(5E)-6a-carba-PGI.sub.3, a compound according to claim 33.
- 35. 2-Decarboxy-2-aminomethyl-(5Z)-6a-carba-PGI.sub.3, a compound according to claim 33.
- 36. A compound according to claim 25, wherein D is --(CH.sub.2).sub.5 --.
- 37. A compound according to claim 36, wherein R.sub.11 is n-pentyl.
- 38. 2-Decarboxy-2-aminomethyl-(5E)-6a-carba-2a,2b-dihomo-PGI.sub.2, a compound according to claim 37.
- 39. 2-Decarboxy-2-aminomethyl-(5Z)-6a-carba-2a,2b-dihomo-PGI.sub.2, a compound according to claim 38.
- 40. A compound according to claim 36, wherein R.sub.11 is --C(CH.sub.3).sub.2 --(CH.sub.3).sub.3 --CH.sub.3.
- 41. 2-Decarboxy-2-aminomethyl-(5E)-6a-carba-2a,2b-dihomo-16,16-dimethyl-PGI.sub.2, a compound according to claim 40.
- 42. 2-Decarboxy-2-aminomethyl-(5Z)-6a-carba-2a,2b-dihomo-16,16-dimethyl-PGI.sub.2, a compound according to claim 40.
- 43. A compound according to claim 24, wherein D is --(CH.sub.2).sub.2 --CF.sub.2 --.
- 44. A compound according to claim 43, wherein R.sub.11 is n-pentyl.
- 45. 2-Decarboxy-2-aminomethyl-(5E)-6a-carba-2,2-difluoro-PGI.sub.2, a compound according to claim 44.
- 46. 2-Decarboxy-2-aminomethyl-(5Z)-6a-carba-2,2-difluoro-PGI.sub.2, a compound according to claim 44.
- 47. A compound according to claim 43, wherein R.sub.11 is --C(CH.sub.3).sub.2 --(CH.sub.3).sub.3 --CH.sub.3.
- 48. 2-Decarboxy-2-aminomethyl-(5E)-6a-carba-2,2-difluoro-16,16-dimethyl-PGI.sub.2, a compound according to claim 47.
- 49. 2-Decarboxy-2-aminomethyl-(5Z)-6a-carba-2,2-difluoro-16,16-dimethyl-PGI.sub.2, a compound according to claim 48.
- 50. A compound according to claim 13, wherein R.sub.8 is methyl.
- 51. A compound according to claim 50, wherein W.sub.2 is .alpha.-OH:.beta.-H.
- 52. A compound according to claim 51, wherein D is --(CH.sub.2).sub.d, wherein d is one to 5, inclusive.
- 53. A compound according to claim 52, wherein D is --(CH.sub.2).sub.3 --.
- 54. 2-Decarboxy-2-aminomethyl-(5E)-6a-carba-(15S)-15-methyl-PGI.sub.2, a compound according to claim 53.
- 55. 2-Decarboxy-2-aminomethyl-(5Z)-6a-carba-(15S)-15-methyl-PGI.sub.2, a compound according to claim 53.
- 56. A compound according to claim 52, wherein D is --(CH.sub.2).sub.5 --.
- 57. 2-Decarboxy-2-aminomethyl-(5E)-6a-carba-2a,2b-dihomo-(15S)-15-methyl-PGI.sub.2, a compound according to claim 56.
- 58. 2-Decarboxy-2-aminomethyl-(5Z)-6a-carba-2a,2b-dihomo-(15S)-15-methyl-PGI.sub.2, a compound according to claim 56.
- 59. A compound according to claim 51, wherein D is --(CH.sub.2).sub.2 --CF.sub.2 --.
- 60. 2-Decarboxy-2-aminomethyl-(5E)-6a-carba-2,2-difluoro-(15S)-15-methyl-PGI.sub.2, a compound according to claim 58.
- 61. 2-Decarboxy-2-aminomethyl-(5Z)-6a-carba-2,2-difluoro-(15S)-15-methyl-PGI.sub.2, a compound according to claim 58.
- 62. A compound according to claim 12, wherein Q.sub.1 is .alpha.-R.sub.8 :.beta.-OH.
- 63. A compound according to claim 61, wherein R.sub.8 is hydrogen.
- 64. 2-Decarboxy-2-aminomethyl-(5E)-6a-carba-15R-PGI.sub.2, a compound according to claim 62.
- 65. 2-Decarboxy-2-aminomethyl-(5Z)-6a-carba-15R-PGI.sub.2, a compound according to claim 62.
- 66. A compound according to claim 61, wherein R.sub.8 is methyl.
- 67. 2-Decarboxy-2-aminomethyl-(5E)-6a-carba-(15R)-15-methyl-PGI.sub.2, a compound according to claim 65.
- 68. 2-Decarboxy-2-aminomethyl-(5Z)-6a-carba-(15R)-15-methyl-PGI.sub.2, a compound according to claim 65.
DESCRIPTION 2-Decarboxy-2-aminomethyl-6a-carba-PGI.sub.2 compounds
The present application is a divisional application of U.S. Ser. No. 877,253, filed Feb. 13, 1978, now pending issuance as a United States patent.
US Referenced Citations (3)
Number |
Name |
Date |
Kind |
3776940 |
Just et al. |
Dec 1973 |
|
3862979 |
Gandolfi et al. |
Jan 1975 |
|
3935240 |
Mallion |
Jan 1976 |
|
Non-Patent Literature Citations (3)
Entry |
Bundy et al., "Tetrahedron Letters", No. 16, pp. 1371-1374 (1978). |
Kojima et al., "Tetrahedron Letters", No. 39, pp. 3743-3746 (1978). |
Nicolaou et al., "J.C.S., Chemical Communications", p. 1067 (1978). |
Divisions (1)
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Number |
Date |
Country |
Parent |
877253 |
Feb 1978 |
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