US4088663A
Expired / Lapsed
US
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Cis-4,5-didehydro-cis-13-PGF1 compounds
Assignee: Pharmacia and Upjohn Co
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Filing: 1977-03-03
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Granted: 1978-05-09
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Expires: 1997-03-03
Abstract
Abstract This invention comprises certain analogs of the prostaglandins in which the double bond between C-13 and C-14 is of the cis configuration. 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
- 👤 Ernest W. Yankee
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 05:44
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; C07C57/00; C07C57/30; C07C57/64; C07C57/72; C07D309/00; C07D309/02; C07D309/08; C07D309/10; C07D309/12; C07D311/00; C07D311/02; C07D311/94; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/40; C07F9/4003; C07F9/4006; C07F9/4056; C07F9/4059; C12; C12N; C12N9/00; C12N9/14; C12N9/16; C12N9/18
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
158 words
A compound of the formula ##STR1## wherein g is two, three, or 4; WHEREIN Y is cis-CH═CH-; wherein M 1 is ##STR2## 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 ##STR3## or a mixture of ##STR4## 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 is one to 5, inclusive; 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
158 words
A compound of the formula ##STR1## wherein g is two, three, or 4; WHEREIN Y is cis-CH═CH-; wherein M 1 is ##STR2## 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 ##STR3## or a mixture of ##STR4## 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 is one to 5, inclusive; 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 g is 4.
Claim 4
Dependent Claim
10 words
A compound according to claim 2, wherein m is 3.
Claim 5
Dependent Claim
18 words
A compound according to claim 3, wherein at least one of R 3 and R 4 is fluoro.
Claim 6
Dependent Claim
15 words
A compound according to claim 4, wherein R 3 and R 4 are both fluoro.
Claim 7
Dependent Claim
14 words
A compound according to claim 5, wherein R 5 and R 6 are hydrogen.
Claim 8
Dependent Claim
11 words
15-EPI-2A,2B-Dihomo-16,16-difluoro-cis-4,5-didehydro-cis-13-PGF 1 α, methyl ester, a compound according to claim 6.
Claim 9
Dependent Claim
18 words
A compound according to claim 3, wherein at least one of R 3 and R 4 is methyl.
Claim 10
Dependent Claim
15 words
A compound according to claim 8, wherein R 3 and R 4 are both methyl.
Claim 11
Dependent Claim
15 words
A compound according to claim 9, wherein R 5 and R 6 are both hydrogen.
Claim 12
Dependent Claim
11 words
15-epi-2a,2b-Dihomo-16,16-dimethyl-cis-4,5-didehydro-cis-13-PGF 1 α, methyl ester, a compound according to claim 10.
Claim 13
Dependent Claim
18 words
A compound according to claim 3, wherein R 3 , R 4 , and R 5 are hydrogen.
Claim 14
Dependent Claim
11 words
15-epi-2a,2b-Dihomo-cis-4,5-didehydro-cis-13-PGF 1 α, methyl ester, a compound according to claim 12.
Claim 15
Dependent Claim
10 words
A compound according to claim 1, wherein g is 2.
Claim 16
Dependent Claim
10 words
A compound according to claim 14, wherein m is 3.
Claim 17
Dependent Claim
18 words
A compound according to claim 15, wherein at least one of R 3 and R 4 is fluoro.
Claim 18
Dependent Claim
15 words
A compound according to claim 16, wherein both R 3 and R 4 are fluoro.
Claim 19
Dependent Claim
14 words
A compound according to claim 17, wherein R 5 and R 6 are hydrogen.
Claim 20
Dependent Claim
11 words
15-epi-16,16-Difluoro-cis-4,5-didehydro-cis-13-PGF 1 α, methyl ester, a compound according to claim 18.
Claim 21
Dependent Claim
18 words
A compound according to claim 15, wherein at least one of R 3 and R 4 is methyl.
Claim 22
Dependent Claim
15 words
A compound according to claim 20, wherein R 3 and R 4 are both methyl.
Claim 23
Dependent Claim
14 words
A compound according to claim 21, wherein R 5 and R 6 are hydrogen.
Claim 24
Dependent Claim
11 words
15-epi-16,16-Dimethyl-cis-4,5-didehydro-cis-13-PGF 1 α, methyl ester, a compound according to claim 22.
Claim 25
Dependent Claim
18 words
A compound according to claim 15, wherein R 3 , R 4 , and R 5 are hydrogen.
Claim 26
Dependent Claim
11 words
15-epi-cis-4,5-didehydro-cis-13-PGF 1 α, methyl ester, a compound according to claim 24.
References Cited (Backward Citations)
US3932479A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-05-08 | 1981-11-07 | 1982-05-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-05-08 | 1985-11-07 | 1986-05-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-05-08 | 1989-11-07 | 1990-05-09 | $7700.00 | Window Closed / Lapsed |