US4045449A
Expired / Lapsed
US
⏱️ 0.0 years remaining
PG-type 1,15-lactones
Assignee: Pharmacia and Upjohn Co
•
Filing: 1976-03-29
•
Granted: 1977-08-30
•
Expires: 1996-03-29
Abstract
Abstract The present invention provides novel 1,15 lactones of prostaglandin-type free acids and a process for their preparation. These lactones are useful for the same pharmacological purposes as the corresponding prostaglandin-type free acids.
Inventors
- 👤 Gordon L. Bundy
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 15:40
CPC Classifications
C; C07; C07C; C07C405/00; C07D; C07D309/00; C07D309/02; C07D309/08; C07D309/10; C07D309/12; C07D313/00; C07D321/00
Claims Analysis
Total Claims: 91
Claim 1
Independent Claim
276 words
A prostaglandin-type, 1,15-lactone of the formula ##STR285## wherein R 8 is hydrogen or hydroxy; wherein L 1 is ##STR286## or a mixture of ##STR287## and ##STR288## 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 M 1 is ##STR289## or ##STR290## wherein R 5 is hydrogen or methyl; wherein R 7 is --(CH 2 ) m --CH 3 ,wherein m is one to 5, inclusive, cis--CH═CH-CH 2 --CH 3 , or ##STR291## wherein T is chloro. fluoro, trifluoromethyl, alkyl of 1 to 3 carbon atoms, inclusive, or alkoxy of one to 3 carbon atoms, inclusive, the various T's being the same or different, s is 0, 1, 2, or 3, and Z 3 is oxa or methylene, with the proviso that not more than two T's are other than alkyl, and the further proviso that Z 3 is oxa only when R 3 and R 4 are hydrogen or methyl, being the same or different; wherein Y 1 is trans--CH═CH--, --CH 2 CH 2 --, cis--CH═CH--, or --C.tbd.C--; and wherein Z 1 is (1) cis--CH═CH--CH 2 --(CH 2 ) g --CH 2 --, (2) cis--CH═CH--CH 2 --(CH 2 ) g --CF 2 --, (3) cis--CH 2 --CH═CH--(CH 2 ) g --CH 2 --, (4) --(ch 2 ) 3 --(ch 2 ) g --CH 2 --, (5) --(CH 2 ) 3 --(CH 2 ) g --CF 2 --, (6) --CH 2 --O--CH 2 --(CH 2 ) g --CH 2 --, ##STR292## wherein g is one to 3, inclusive.
Claim 2
Dependent Claim
276 words
A prostaglandin-type, 1,15-lactone of the formula ##STR285## wherein R 8 is hydrogen or hydroxy; wherein L 1 is ##STR286## or a mixture of ##STR287## and ##STR288## 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 M 1 is ##STR289## or ##STR290## wherein R 5 is hydrogen or methyl; wherein R 7 is --(CH 2 ) m --CH 3 ,wherein m is one to 5, inclusive, cis--CH═CH-CH 2 --CH 3 , or ##STR291## wherein T is chloro. fluoro, trifluoromethyl, alkyl of 1 to 3 carbon atoms, inclusive, or alkoxy of one to 3 carbon atoms, inclusive, the various T's being the same or different, s is 0, 1, 2, or 3, and Z 3 is oxa or methylene, with the proviso that not more than two T's are other than alkyl, and the further proviso that Z 3 is oxa only when R 3 and R 4 are hydrogen or methyl, being the same or different; wherein Y 1 is trans--CH═CH--, --CH 2 CH 2 --, cis--CH═CH--, or --C.tbd.C--; and wherein Z 1 is (1) cis--CH═CH--CH 2 --(CH 2 ) g --CH 2 --, (2) cis--CH═CH--CH 2 --(CH 2 ) g --CF 2 --, (3) cis--CH 2 --CH═CH--(CH 2 ) g --CH 2 --, (4) --(ch 2 ) 3 --(ch 2 ) g --CH 2 --, (5) --(CH 2 ) 3 --(CH 2 ) g --CF 2 --, (6) --CH 2 --O--CH 2 --(CH 2 ) g --CH 2 --, ##STR292## wherein g is one to 3, inclusive.
Claim 3
Dependent Claim
11 words
A compound according to claim 1, wherein is ##STR293## or ##STR294##
Claim 4
Dependent Claim
9 words
PGA 2 1,15-lactone, a compound according to claim 2.
Claim 5
Dependent Claim
9 words
A compound according to claim 1, wherein is ##STR295##
Claim 6
Dependent Claim
9 words
PGB 2 1,15-lactone, a compound according to claim 4.
Claim 7
Dependent Claim
11 words
A compound according to claim 1, wherein is ##STR296## or ##STR297##
Claim 8
Dependent Claim
9 words
PGD 2 1,15-lactone, a compound according to claim 6.
Claim 9
Dependent Claim
11 words
A compound according to claim 1, wherein is ##STR298## or ##STR299##
Claim 10
Dependent Claim
11 words
A compound according to claim 8, wherein Y 1 is --C.tbd.C--.
Claim 11
Dependent Claim
9 words
13,14-Didehydro-PGE 2 1,15-lactone, a compound according to claim 9.
Claim 12
Dependent Claim
11 words
A compound according to claim 8, wherein Y 1 is cis--CH═CH--.
Claim 13
Dependent Claim
9 words
cis-13-PGE 2 1,15-lactone, a compound according to claim 11.
Claim 14
Dependent Claim
15 words
A compound according to claim 8, wherein Y 1 is --CH 2 CH 2 --.
Claim 15
Dependent Claim
9 words
13,14-Dihydro-PGE 2 1,15-lactone, a compound according to claim 13.
Claim 16
Dependent Claim
11 words
A compound according to claim 8, wherein Y 1 is trans--CH═CH--.
Claim 17
Dependent Claim
9 words
PGE 2 ,1,15-lactone, a compound according to claim 15.
Claim 18
Dependent Claim
11 words
A compound according to claim 1, wherein is ##STR300## or ##STR301##
Claim 19
Dependent Claim
20 words
A compound according to claim 17, wherein Z 1 is --CH 2 -- --CH 2 --(CH 2 ) g --.
Claim 20
Dependent Claim
9 words
5-oxa-PGF 1 α,1,15-lactone, a compound according to claim 18.
Claim 21
Dependent Claim
11 words
A compound according to claim 17, wherein Z 1 is ##STR302##
Claim 22
Dependent Claim
9 words
3-oxa-3,7-inter-m-phenylene-4,5,6-trinor-PGF 1 α,1,15-lactone, a compound according to claim 20.
Claim 23
Dependent Claim
11 words
A compound according to claim 17, wherein Z 1 is ##STR303##
Claim 24
Dependent Claim
9 words
3,7-inter-m-phenylene-4,5,6-trinor-PGF 1 α,1,15-lactone, a compound according to claim 22.
Claim 25
Dependent Claim
19 words
A compound according to claim 17, wherein Z 1 is cis-CH 2 -CH═CH-(CH 2 ) g -CH 2 -.
Claim 26
Dependent Claim
9 words
cis-4,5-Didehydro-PGF 1 α,1,15-lactone, a compound according to claim 24.
Claim 27
Dependent Claim
19 words
A compound according to claim 17, wherein Z 1 is cis--CH═CH--CH 2 --(CH 2 ) g --CF 2 --.
Claim 28
Dependent Claim
9 words
2,2,16,16-Tetrafluoro-PGF 2 α,1,15-lactone, a compound according to claim 26.
Claim 29
Dependent Claim
10 words
2,2-Difluoro-16,16-dimethyl-PGF 2 α, 1,15-lactone, a compound according to claim 26.
Claim 30
Dependent Claim
9 words
2,2-Difluoro-15-methyl-PGF 2 α,1,15-lactone, a compound according to claim 26.
Claim 31
Dependent Claim
9 words
2,2-Difluro-PGF 2 α,1,15-lactone, a compound according to claim 26.
Claim 32
Dependent Claim
21 words
A compound according to claim 17, wherein Z 1 is --(CH 2 ) 3 --(CH 2 ) g --CF 2 --.
Claim 33
Dependent Claim
9 words
2,2,16,16-Tetrafluoro-PGF 1 α,1,15-lactone, a compound according to claim 31.
Claim 34
Dependent Claim
10 words
2,2-Difluoro-16,16-dimethyl-PGF 1 α, 1,15-lactone, a compound according to claim 31.
Claim 35
Dependent Claim
9 words
2,2-DIfluoro-15-methyl-PGF 1 α,1,15-lactone, a compound according to claim 31.
Claim 36
Dependent Claim
9 words
2,2-Difluoro-PGF 1 α,1,15-lactone, a compound according to claim 31.
Claim 37
Dependent Claim
21 words
A compound according to claim 17, wherein Z 1 is --(CH 2 ) 3 --(CH 2 ) g --CH 2 --.
Claim 38
Dependent Claim
9 words
16,16-Difluoro-PGF 1 α,1,15-lactone, a compound according to claim 36.
Claim 39
Dependent Claim
9 words
16,16-Dimethyl-PGF 1 α,1,15-lactone, a compound according to claim 36.
Claim 40
Dependent Claim
9 words
15-Methyl-PGF 1 α,1,15-lactone, a compound according to claim 36.
Claim 41
Dependent Claim
9 words
PGF 1 α,1,15-lactone, a compound according to claim 36.
Claim 42
Dependent Claim
19 words
A compound according to claim 17, wherein Z 1 is cis--CH═CH--CH 2 --(CH 2 ) g --CH 2 --.
Claim 43
Dependent Claim
10 words
A compound according to claim 41, wherein g is 3.
Claim 44
Dependent Claim
10 words
A compound according to claim 41, wherein g is 1.
Claim 45
Dependent Claim
11 words
A compound according to claim 43, wherein Y 1 is --C.tbd.C--.
Claim 46
Dependent Claim
9 words
13,14-Didehydro-PGF 2 α,1,15-lactone, a compound according to claim 44.
Claim 47
Dependent Claim
11 words
A compound according to claim 43, wherein Y 1 is cis--CH═CH--.
Claim 48
Dependent Claim
9 words
cis-13-PGF 2 α,1,15-lactone, a compound according to claim 46.
Claim 49
Dependent Claim
15 words
A compound according to claim 43, wherein Y 1 is --CH 2 CH 2 --.
Claim 50
Dependent Claim
9 words
13,14-dihydro-PGF 2 α,1,15-lactone, a compound according to claim 48.
Claim 51
Dependent Claim
11 words
A compound according to claim 43, wherein Y 1 is trans--CH═CH--.
Claim 52
Dependent Claim
15 words
A compound according to claim 50, wherein R 7 is cis--CH═CH--CH 2 --CH 3 --.
Claim 53
Dependent Claim
9 words
PGF 3 α,1,15-lactone, a compound according to claim 51.
Claim 54
Dependent Claim
11 words
A compound according to claim 50, wherein R 7 is ##STR304##
Claim 55
Dependent Claim
19 words
A compound according to claim 53, wherein s is 0 or 1 and T is chloro, fluoro, or trifluoromethyl.
Claim 56
Dependent Claim
11 words
A compound according to claim 54, wherein Z 3 is methylene.
Claim 57
Dependent Claim
11 words
A compound according to claim 55, wherein R 5 is methyl.
Claim 58
Dependent Claim
9 words
15-Methyl-17-Phenyl-18,19,20-trinor-PGF 2 α,1,15-lactone, a compound according to claim 56.
Claim 59
Dependent Claim
10 words
A compound according to claim 55, wherein R5 is hydrogen.
Claim 60
Dependent Claim
18 words
A compound according to claim 58, wherein at least one of R 3 and R 4 are fluoro.
Claim 61
Dependent Claim
9 words
16,16-Difluoro-17-Phenyl-18,19,20-trinor-PFG 2 α,1,15-lactone, a compound according to claim 59.
Claim 62
Dependent Claim
18 words
A compound according to claim 58, wherein at least one of R 3 and R 4 is methyl.
Claim 63
Dependent Claim
9 words
16,16-Dimethyl-17-phenyl-18,19,20-trinor-PGF 2 α,1,15-lactone, a compound according to claim 61.
Claim 64
Dependent Claim
15 words
A compound according to claim 58, wherein R 3 and R 4 are both hydrogen.
Claim 65
Dependent Claim
9 words
17-Phenyl-18,19,20-trinor-PGF 2 α,1,15-lactone, a compound according to claim 63.
Claim 66
Dependent Claim
11 words
A compound according to claim 54, wherein Z 3 is oxa.
Claim 67
Dependent Claim
11 words
A compound according to claim 65, wherein R 5 is methyl.
Claim 68
Dependent Claim
9 words
15-Methyl-16-Phenoxy-17,18,19,20-tetranor-PGF 2 α,1,15-lactone, a compound according to claim 66.
Claim 69
Dependent Claim
11 words
A compound according to claim 65, wherein R 5 is hydrogen.
Claim 70
Dependent Claim
18 words
A compound according to claim 68, wherein at least one of R 3 and R 4 is methyl.
Claim 71
Dependent Claim
9 words
16-Methyl-16-Phenoxy-18,19,20-trinor-PGF 2 α,1,15-lactone, a compound according to claim 69.
Claim 72
Dependent Claim
15 words
A compound according to claim 68, wherein R 3 and R 4 are both hydrogen.
Claim 73
Dependent Claim
9 words
16-Phenoxy-17,18,19,20-tetranor-PGF 2 α,1,15-lactone, a compound according to claim 72.
Claim 74
Dependent Claim
18 words
A compound according to claim 50, wherein R 7 , is --(CH 2 ) m --CH 3 --.
Claim 75
Dependent Claim
10 words
A compound according to claim 73, wherein m is 3.
Claim 76
Dependent Claim
11 words
A compound according to claim 74, wherein R 5 is methyl.
Claim 77
Dependent Claim
18 words
A compound according to claim 75, wherein at least one of R 3 and R 4 is fluoro.
Claim 78
Dependent Claim
9 words
15-Methyl-16,16-difluoro-PGF 2 α,1,15-lactone, a compound according to claim 76.
Claim 79
Dependent Claim
17 words
A compound to claim 75, wherein at least one of R 3 and R 4 is methyl.
Claim 80
Dependent Claim
9 words
15,16,16-Trimethyl-PGF 2 α,1,15-lactone, a compound according to claim 78.
Claim 81
Dependent Claim
15 words
A compound according to claim 75, wherein R 3 and R 4 are both hydrogen.
Claim 82
Dependent Claim
9 words
15-Methyl-PGF 2 α,1,15-lactone, a compound according to claim 80.
Claim 83
Dependent Claim
11 words
A compound according to claim 74, wherein R 5 is hydrogen.
Claim 84
Dependent Claim
18 words
A compound according to claim 82, wherein at least one of R 3 and R 4 is fluoro.
Claim 85
Dependent Claim
15 words
A compound according to claim 83, wherein R 3 and R 4 are both fluoro.
Claim 86
Dependent Claim
9 words
16,16-Difluoro-PGF 2 α,1,15-lactone, a compound according to claim 84.
Claim 87
Dependent Claim
18 words
A compound according to claim 82, wherein at least one of R 3 and R 4 is methyl.
Claim 88
Dependent Claim
15 words
A compound according to claim 86, wherein R 3 and R 4 are both methyl.
Claim 89
Dependent Claim
9 words
16,16-Dimethyl-PGF 2 α,1,15-lactone, a compound according to claim 87.
Claim 90
Dependent Claim
15 words
A compound according to claim 82, wherein R 3 and R 4 are both hydrogen.
Claim 91
Dependent Claim
9 words
PGF 2 α,1,15-lactone, a compound according to claim 89.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-08-29 | 1981-02-28 | 1981-08-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-08-29 | 1985-02-28 | 1985-08-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-08-29 | 1989-02-28 | 1989-08-30 | $7700.00 | Window Closed / Lapsed |