Patent US4190597A successfully refreshed from Google Patents.
US4190597A
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Various 15-deoxy-16-hydroxy-16-ethynyl and 16-ethynylsubstituted prostaglandins
Assignee: Wyeth Holdings LLC
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Filing: 1977-12-05
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Granted: 1980-02-26
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Expires: 1997-12-05
Abstract
Abstract 15-Deoxy-16-hydroxy-16-ethynyl and 16-ethynylsubstituted prostanoic acids and congeners thereof, useful as bronchodilators, hypotensive agents, and as agents for the control of excessive gastric secretion.
Inventors
- 👤 Middleton B. Floyd, Jr.
- 👤 Martin J. Weiss
- 👤 Charles V. Grudzinskas
- 👤 Sow-mei L. Chen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 21:58
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/02; C07D307/34; C07D307/38; C07D307/40; C07D307/42; C07C; C07C29/00; C07C29/09; C07C29/10; C07C29/36; C07C29/38; C07C29/42; C07C405/00; C07C405/0008; C07C405/0025; C07C405/0033; C07C45/00; C07C45/27; C07C45/29; C07C49/00; C07C49/20; C07C49/227; C07C49/587; C07C49/703; C07C49/743; C07C49/753; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/18; C07F7/1804; C07F7/22; C07F7/2208; C07B; C07B2200/00; C07B2200/09
Claims Analysis
Total Claims: 48
Claim 1
Independent Claim
113 words
An optically active compound of the formula: ##STR23## wherein R 1 is selected from the group consisting of hydrogen and C 1 to C 6 alkyl; R 2 is selected from the group consisting of C 3 to C 7 alkyl; X is selected from the group consisting of a divalent moiety of the formula: ##STR24## wherein R 5 is selected from the group consisting of ethynyl, 2-propynyl and trimethylsilylethynyl; Z is selected from the group consisting of --(CH 2 ) 6 --, --(CH 2 ) 4 SCH 2 -- and --(CH 2 ) 4 --O--CH 2 --; the racemic mixture thereof; and, when R 1 is hydrogen, the pharmacologically acceptable salts thereof.
Claim 2
Dependent Claim
113 words
An optically active compound of the formula: ##STR23## wherein R 1 is selected from the group consisting of hydrogen and C 1 to C 6 alkyl; R 2 is selected from the group consisting of C 3 to C 7 alkyl; X is selected from the group consisting of a divalent moiety of the formula: ##STR24## wherein R 5 is selected from the group consisting of ethynyl, 2-propynyl and trimethylsilylethynyl; Z is selected from the group consisting of --(CH 2 ) 6 --, --(CH 2 ) 4 SCH 2 -- and --(CH 2 ) 4 --O--CH 2 --; the racemic mixture thereof; and, when R 1 is hydrogen, the pharmacologically acceptable salts thereof.
Claim 3
Dependent Claim
14 words
A compound according to claim 1, wherein Z is --(CH 2 ) 6 --.
Claim 4
Dependent Claim
30 words
A compound according to claim 2, wherein Z is selected from the group consisting of --(CH 2 ) 4 OCH 2 -- and --(CH 2 ) 4 --S--CH 2 .
Claim 5
Dependent Claim
11 words
A compound according to claim 2, wherein R 3 is hydroxyl.
Claim 6
Dependent Claim
11 words
A compound according to claim 2, wherein R 3 is hydrogen.
Claim 7
Dependent Claim
11 words
A compound according to claim 3, wherein R 3 is hydroxyl.
Claim 8
Dependent Claim
11 words
A compound according to claim 3, wherein R 3 is hydrogen.
Claim 9
Dependent Claim
12 words
The optically active compound according to claim 4, nat. methyl-16-hydroxy-9-oxo-16-ethynyl-Δ 10 ,13-trans-prostadienoate.
Claim 10
Dependent Claim
13 words
The optically active compound according to claim 4, nat. 16-hydroxy-9-oxo-16-ethynyl-Δ 10 ,13-trans-prostadienoic acid.
Claim 11
Dependent Claim
12 words
The optically active compound according to claim 4, nat. methyl-16-hydroxy-9-oxo-16-ethynyl-Δ 10 ,13-trans-prostadienoate.
Claim 12
Dependent Claim
13 words
The optically active compound according to claim 4, nat. 16-hydroxy-9-oxo-16-ethynyl-20-ethyl-Δ 10 ,13-trans-prostadienoic acid.
Claim 13
Dependent Claim
12 words
The optically active compound according to claim 4, nat. methyl-16-hydroxy-9-oxo-16-(1-propynyl)-Δ 10 ,13-trans-prostadienoate.
Claim 14
Dependent Claim
13 words
The optically active compound according to claim 4, nat. 16-hydroxy-9-oxo-16-(1-propynyl)-Δ 10 ,13-trans-prostadienoic acid.
Claim 15
Dependent Claim
12 words
The optically active compound according to claim 4, nat. methyl-16-hydroxy-9-oxo-16-(1-propynyl)-20-ethyl-Δ 10 ,13-trans-prostadienoate.
Claim 16
Dependent Claim
13 words
The optically active compound according to claim 4, nat. 16-hydroxy-9-oxo-16-(1-propynyl)-20-ethyl-Δ 10 ,13-trans-prostadienoic acid.
Claim 17
Dependent Claim
12 words
The optically active compound according to claim 4, nat. methyl-16-hydroxy-9-oxo-16-trimethylsilylethynyl-Δ 10 ,13-trans-prostadienoate.
Claim 18
Dependent Claim
13 words
The optically active compound according to claim 4, nat. 16-hydroxy-9-oxo-16-trimethylsilylethynyl-Δ 10 ,13-trans-prostadienoic acid.
Claim 19
Dependent Claim
12 words
The optically active compound according to claim 4, nat. methyl-16-hydroxy-9-oxo-16-trimethylsilylethynyl)-20-ethyl-Δ 10 ,13-trans-prostadienoate.
Claim 20
Dependent Claim
13 words
The optically active compound according to claim 4, nat. 16-hydroxy-9-oxo-16-trimethylsilylethynyl-20-ethyl-Δ 10 ,13-trans-prostadienoic acid.
Claim 21
Dependent Claim
11 words
The racemic compound according to claim 4, dl-16-hydroxy-9-oxo-16-ethynyl-Δ 10 ,13-trans-prostadienoic acid.
Claim 22
Dependent Claim
10 words
The racemic compound according to claim 4, dl-hexyl-16-hydroxy-9-oxo-16-ethynyl-20-ethyl-Δ 10 ,13-trans-prostadienoate.
Claim 23
Dependent Claim
12 words
The optically active compound according to claim 4, nat. methyl-16-hydroxy-9-oxo-16-(1-propynyl)-Δ 10 ,13-trans-prostadienoate.
Claim 24
Dependent Claim
11 words
The racemic compound according to claim 4, dl-16-hydroxy-9-oxo-16-(1-propynyl)-20-ethyl-Δ 10 ,13-trans-prostadienoic acid.
Claim 25
Dependent Claim
11 words
The racemic compound according to claim 4, dl-16-hydroxy-9-oxo-16-trimethylsilylethynyl-Δ 10 ,13-trans-prostadienoic acid.
Claim 26
Dependent Claim
10 words
The racemic compound according to claim 4, dl-methyl-16-hydroxy-9-oxo-16-trimethylsilylethynyl-20-ethyl-Δ 1 0,13-trans-prostadienoate.
Claim 27
Dependent Claim
13 words
The optically active compound according to claim 4, nat. 16-hydroxy-9-oxo-16-trimethylsilylethynyl-20-ethyl-5,6-cis,Δ 10 ,13-trans-prostatrienoic acid.
Claim 28
Dependent Claim
11 words
The racemic compound according to claim 5, dl-16-hydroxy-9-oxo-16-ethynyl-Δ 10 ,13-trans-prostadienoic acid.
Claim 29
Dependent Claim
10 words
The racemic compound according to claim 5, dl-hexyl-16-hydroxy-9-oxo-16(propynyl)-Δ 10 ,13-trans-prostadienoate.
Claim 30
Dependent Claim
11 words
The racemic compound according to claim 5, dl-16-hydroxy-9-oxo-16-trimethylsilylethynyl-Δ 10 ,13-trans-prostadienoic acid.
Claim 31
Dependent Claim
10 words
The racemic compound according to claim 6, dl-methyl-16-hydroxy-9-oxo-16-ethynyl-3-thia-Δ 10 ,13-trans-prostadienoate.
Claim 32
Dependent Claim
11 words
The racemic compound according to claim 6, dl-16-hydroxy-9-oxo-16-ethynyl-20-ethyl-3-thia-Δ 10 ,13-trans-prostadienoic acid.
Claim 33
Dependent Claim
10 words
The racemic compound according to claim 6, dl-methyl-16-hydroxy-9-oxo-16-(1-propynyl)-3-thia-Δ 10 ,13-trans-prostadienoate.
Claim 34
Dependent Claim
11 words
The racemic compound according to claim 6, dl-16-hydroxy-9-oxo-16-(1-propynyl)-20-ethyl-3-thia-Δ 10 ,13-trans-prostadienoic acid.
Claim 35
Dependent Claim
10 words
The racemic compound according to claim 6, dl-hexyl-16-hydroxy-9-oxo-16-trimethylsilylethynyl-3-thia-Δ 10 ,13-trans-prostadienoate.
Claim 36
Dependent Claim
11 words
The racemic compound according to claim 6, dl-16-hydroxy-9-oxo-16-trimethylsilylethynyl-20-ethyl-3-thia-Δ 1 0,13-trans-prostadienoic acid.
Claim 37
Dependent Claim
11 words
The racemic compound according to claim 6, dl-16-hydroxy-9-oxo-16-ethynyl-3-oxa-Δ 10 ,13-trans-prostadienoic acid.
Claim 38
Dependent Claim
10 words
The racemic compound according to claim 6, dl-hexyl-16-hydroxy-9-oxo-16-ethynyl-20-ethyl-3-oxa-Δ 10 ,13-trans-prostadienoate.
Claim 39
Dependent Claim
11 words
The racemic compound according to claim 6, dl-16-hydroxy-9-oxo-16-(1-propynyl)-3-oxa-Δ 10 ,13-trans-prostadienoic acid.
Claim 40
Dependent Claim
10 words
The racemic compound according to claim 6, dl-hexyl-16-hydroxy-9-oxo-16-(1-propynyl)-20-ethyl-3-oxa-Δ 10 ,13-trans-prostadienoate.
Claim 41
Dependent Claim
11 words
The racemic compound according to claim 6, dl-16-hydroxy-9-oxo-16-trimethylsilylethynyl-3-oxa-Δ 10 ,13-trans-prostadienoic acid.
Claim 42
Dependent Claim
10 words
The racemic compound according to claim 6, dl-methyl-16-hydroxy-9-oxo-16-trimethylsilylethynyl-20-ethyl-3-oxa-Δ 10 ,13-trans-prostadienoate.
Claim 43
Dependent Claim
11 words
The racemic compound according to claim 7, dl-16-hydroxy-9-oxo-16-ethynyl-3-thia-Δ 10 ,13-trans-prostadienoic acid.
Claim 44
Dependent Claim
10 words
The racemic compound according to claim 6, dl-methyl-16-hydroxy-9-oxo-16-ethynyl-20-ethyl-3-oxa-Δ 10 ,13-trans-prostadienoate.
Claim 45
Dependent Claim
10 words
The racemic compound according to claim 7, dl-hexyl-16-hydroxy-9-oxo-16-(1-propynyl)-3-thia-Δ 10 ,13-trans-prostadienoate.
Claim 46
Dependent Claim
11 words
The racemic compound according to claim 7, dl-16-hydroxy-9-oxo-16-(1-propynyl)-20-ethyl-3-oxa-Δ 10 ,13-trans-prostadienoic acid.
Claim 47
Dependent Claim
10 words
The racemic compound according to claim 7, dl-methyl-16-hydroxy-9-oxo-16-triemthylsilylethynyl-3-thia-Δ 10 ,13-trans-prostadienoate.
Claim 48
Dependent Claim
11 words
The racemic compound according to claim 7, dl-16-hydroxy-9-oxo-16-trimethylsilylethynyl-20-ethyl-3-oxa-Δ 10 ,13-trans-prostadienoic acid.
References Cited (Backward Citations)
US3965193A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-02-25 | 1983-08-27 | 1984-02-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-02-25 | 1987-08-27 | 1988-02-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-02-25 | 1991-08-27 | 1992-02-26 | $7700.00 | Window Closed / Lapsed |