US4119664A
Expired / Lapsed
US
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5-Oxa-13,14-didehydro-PGE1 compounds
Assignee: Pharmacia and Upjohn Co
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Filing: 1977-03-07
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Granted: 1978-10-10
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Expires: 1997-03-07
Abstract
Abstract This invention comprises certain analogs of the prostaglandins in which the double bond between C-13 and C-14 is replaced by a triple bond. Also provided in this invention, are novel chemical processes and novel chemical intermediates useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.
Inventors
- 👤 Herman W. Smith
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 15:34
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/77; C07D307/93; C07D307/935; A; A61; A61P; A61P43/00; C07C; C07C405/00; C07C405/0008; C07C405/0016; C07D263/00; C07D263/02; C07D263/04; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/40; C07F9/4003; C07F9/4006; C07F9/4056; C07F9/4059; C07F9/54; C07F9/5407
Claims Analysis
Total Claims: 54
Claim 1
Independent Claim
162 words
A prostaglandin analog of the formula: ##STR1## wherein D is ##STR2## wherein Y 1 is --C.tbd.C--; wherein g is 1, 2, or 3; Wherein m is 1 to 5, inclusive; Wherein M 1 is ##STR3## wherein R 5 and R 6 are hydrogen or methyl, with the proviso that one of R 5 and R 6 is methyl only when the other is hydrogen; Wherein L 1 is ##STR4## or a mixture of ##STR5## 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; and Wherein R 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, phenyl substituted with one, two, or three chloro or alkyl of one to 3 carbon atoms, inclusive, or a pharmacologically acceptable cation.
Claim 2
Dependent Claim
162 words
A prostaglandin analog of the formula: ##STR1## wherein D is ##STR2## wherein Y 1 is --C.tbd.C--; wherein g is 1, 2, or 3; Wherein m is 1 to 5, inclusive; Wherein M 1 is ##STR3## wherein R 5 and R 6 are hydrogen or methyl, with the proviso that one of R 5 and R 6 is methyl only when the other is hydrogen; Wherein L 1 is ##STR4## or a mixture of ##STR5## 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; and Wherein R 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, phenyl substituted with one, two, or three chloro or alkyl of one to 3 carbon atoms, inclusive, or a pharmacologically acceptable cation.
Claim 3
Dependent Claim
10 words
A compound according to claim 1, wherein D is ##STR6##
Claim 4
Dependent Claim
15 words
A compound according to claim 2, wherein M 1 is ##STR7## and g is 1.
Claim 5
Dependent Claim
22 words
A compound according to claim 3, wherein R 3 , R 4 , R 5 , and R 6 are all hydrogen.
Claim 6
Dependent Claim
15 words
A compound according to claim 2, wherein M 1 is ##STR8## and g is 1.
Claim 7
Dependent Claim
15 words
A compound according to claim 2, wherein R 3 and R 4 are both hydrogen.
Claim 8
Dependent Claim
11 words
A compound according to claim 6, wherein R 5 is methyl.
Claim 9
Dependent Claim
11 words
A compound according to claim 6, wherein R 6 is methyl.
Claim 10
Dependent Claim
11 words
5-Oxa-13,14-didehydro-8β,12α-PGE 1 , 15-methyl ether, a compound according to claim 8.
Claim 11
Dependent Claim
15 words
A compound according to claim 6, wherein R 5 and R 6 are both hydrogen.
Claim 12
Dependent Claim
9 words
5-Oxa-13,14-didehydro-8β,12α-PGE 1 , a compound according to claim 10.
Claim 13
Dependent Claim
18 words
A compound according to claim 2, wherein at least one of R 3 and R 4 is methyl.
Claim 14
Dependent Claim
15 words
A compound according to claim 12, wherein R 3 and R 4 are both methyl.
Claim 15
Dependent Claim
11 words
A compound according to claim 13, wherein R 5 is methyl.
Claim 16
Dependent Claim
9 words
5-Oxa-15,16,16-trimethyl-13,14-didehydro-8β,12α-PGE 1 , a compound according to claim 14.
Claim 17
Dependent Claim
11 words
A compound according to claim 13, wherein R 6 is methyl.
Claim 18
Dependent Claim
11 words
5-Oxa-16,16-dimethyl-13,14-didehydro-8β,12α-PGE 1 , 15-methyl ether, a compound according to claim 16.
Claim 19
Dependent Claim
15 words
A compound according to claim 13, wherein R 5 and R 6 are both hydrogen.
Claim 20
Dependent Claim
9 words
5-Oxa-16,16-dimethyl-13,14-didehydro-8β,12α-PGE 1 , a compound according to claim 18.
Claim 21
Dependent Claim
18 words
A compound according to claim 2, wherein at least one of R 3 and R 4 is fluoro.
Claim 22
Dependent Claim
15 words
A compound according to claim 20, wherein R 3 and R 4 are both fluoro.
Claim 23
Dependent Claim
11 words
A compound according to claim 21, wherein R 5 is methyl.
Claim 24
Dependent Claim
9 words
5-Oxa-15-methyl-16,16-difluoro-13,14-didehydro-8β,12.alpha.-PGE 1 , a compound according to claim 22.
Claim 25
Dependent Claim
11 words
A compound according to claim 22, wherein R 6 is methyl.
Claim 26
Dependent Claim
11 words
5-Oxa-16,16-difluoro-13,14-didehydro-8β,12α-PGE 1 , 15-methyl ether, a compound according to claim 24.
Claim 27
Dependent Claim
15 words
A compound according to claim 22, wherein R 5 and R 6 are both hydrogen.
Claim 28
Dependent Claim
9 words
5-Oxa-16,16-difluoro-13,14-didehydro-8β,12α-PGE 1 , a compound according to claim 26.
Claim 29
Dependent Claim
10 words
A compound according to claim 1, wherein D is ##STR9##
Claim 30
Dependent Claim
15 words
A compound according to claim 28, wherein M 1 is ##STR10## and g is 1.
Claim 31
Dependent Claim
22 words
A compound according to claim 29, wherein R 3 , R 4 , R 5 , and R 6 are all hydrogen.
Claim 32
Dependent Claim
15 words
A compound according to claim 28, wherein M 1 is ##STR11## and g is 1.
Claim 33
Dependent Claim
15 words
A compound according to claim 31, wherein R 3 and R 4 are both hydrogen.
Claim 34
Dependent Claim
11 words
A compound according to claim 32, wherein R 5 is methyl.
Claim 35
Dependent Claim
11 words
A compound according to claim 32, wherein R 6 is methyl.
Claim 36
Dependent Claim
11 words
5-Oxa-13,14-didehydro-PGE 1 , 15-methyl ether, a compound according to claim 34.
Claim 37
Dependent Claim
15 words
A compound according to claim 32, wherein R 5 and R 6 are both hydrogen.
Claim 38
Dependent Claim
9 words
5-Oxa-13,14-didehydro-PGE 1 , a compound according to claim 36.
Claim 39
Dependent Claim
18 words
A compound according to claim 31, wherein at least one of R 3 and R 4 is methyl.
Claim 40
Dependent Claim
15 words
A compound according to claim 38, wherein R 3 and R 4 are both methyl.
Claim 41
Dependent Claim
11 words
A compound according to claim 39, wherein R 5 is methyl.
Claim 42
Dependent Claim
9 words
5-Oxa-15,16,16-trimethyl-13,14-didehydro-PGE 1 , a compound according to claim 40.
Claim 43
Dependent Claim
11 words
A compound according to claim 39, wherein R 6 is methyl.
Claim 44
Dependent Claim
11 words
5-Oxa-16,16-dimethyl-13,14-didehydro-PGE 1 , 15-methyl ether, a compound according to claim 42.
Claim 45
Dependent Claim
15 words
A compound according to claim 39, wherein R 5 and R 6 are both hydrogen.
Claim 46
Dependent Claim
9 words
5-Oxa-16,16-dimethyl-13,14-didehydro-PGE 1 , a compound according to claim 44.
Claim 47
Dependent Claim
18 words
A compound according to claim 31, wherein at least one of R 3 and R 4 is fluoro.
Claim 48
Dependent Claim
15 words
A compound according to claim 46, wherein R 3 and R 4 are both fluoro.
Claim 49
Dependent Claim
11 words
A compound according to claim 47, wherein R 5 is methyl.
Claim 50
Dependent Claim
9 words
5-Oxa-15-methyl-16,16-difluoro-13,14-didehydro-PGE 1 , a compound according to claim 48.
Claim 51
Dependent Claim
11 words
A compound according to claim 47, wherein R 6 is methyl.
Claim 52
Dependent Claim
11 words
5-Oxa-16,16-difluoro-13,14-didehydro-PGE 1 , 15-methyl ether, a compound according to claim 50.
Claim 53
Dependent Claim
15 words
A compound according to claim 47, wherein R 5 and R 6 are both hydrogen.
Claim 54
Dependent Claim
9 words
5-Oxa-16,16-difluoro-13,14-didehydro-PGE 1 , a compound according to claim 52.
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) | 1981-10-09 | 1982-04-10 | 1982-10-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-10-09 | 1986-04-10 | 1986-10-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-10-09 | 1990-04-10 | 1990-10-10 | $7700.00 | Window Closed / Lapsed |