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US4056562A
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3,5-Bisoxygenated 2-(ω-halo-3-oxygenated-1-alkenyl)-cyclopentane-1-heptanoic acids and derivatives thereof
Assignee: GD Searle LLC
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Filing: 1976-07-19
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Granted: 1977-11-01
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Expires: 1996-07-19
Abstract
Abstract 3,5-Bisoxygenated 2-(ω-halo-3-oxygenated-1-alkenyl)-cyclopentane-1-heptanoic acids and derivatives thereof, conveniently obtained by processes utilizing 2-formyl-3-hydroxy-5-oxycyclopent-1-eneheptanoic acids as the starting materials, display valuable pharmacological properties, e.g. antifertility, bronchodilating, anti-secretory, smooth muscle stimulatory, and blood platelet aggregation-inhibiting.
Inventors
- 👤 Richard A. Mueller
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 12:08
CPC Classifications
C; C07; C07C; C07C405/00
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
100 words
A compound of the formula ##STR20## wherein R 1 is hydrogen or an alkyl radical containing 1-12 carbon atoms; R 2 is hydrogen, a tetrahydropyran-2-yl or trialkylsilyl radical, or alkanoyl radical containing 1-12 carbon atoms; X is a carbonyl radical; Y is a radical of the formula ##STR21## A being hydrogen or an alkanoyl radical containing 1-12 carbon atoms and B being hydrogen or an alkyl radical containing 1-12 carbon atoms; Z is a chloro, bromo, or iodo radical; Alk is an alkylene radical containing 3-8 carbon atoms; and the wavy lines represent the alternative α and β stereochemical configuration.
Claim 2
Dependent Claim
100 words
A compound of the formula ##STR20## wherein R 1 is hydrogen or an alkyl radical containing 1-12 carbon atoms; R 2 is hydrogen, a tetrahydropyran-2-yl or trialkylsilyl radical, or alkanoyl radical containing 1-12 carbon atoms; X is a carbonyl radical; Y is a radical of the formula ##STR21## A being hydrogen or an alkanoyl radical containing 1-12 carbon atoms and B being hydrogen or an alkyl radical containing 1-12 carbon atoms; Z is a chloro, bromo, or iodo radical; Alk is an alkylene radical containing 3-8 carbon atoms; and the wavy lines represent the alternative α and β stereochemical configuration.
Claim 3
Dependent Claim
103 words
A compound according to claim 1 of the formula ##STR22## wherein R 1 is hydrogen or an alkyl radical containing 1-6 carbon atoms; R 2 is hydrogen, a tetrahydropyran-2-yl or trialkylsilyl radical, or alkanoyl radical containing 1-6 carbon atoms; X is a carbonyl radical; Y is a radical of the formula ##STR23## A being hydrogen or an alkanoyl radical containing 1-6 carbon atoms and B being hydrogen or an alkyl radical containing 1-6 carbon atoms; Z is a chloro or bromo radical; Alk is an alkylene radical containing 4-5 carbon atoms; and the wavy line represents the alternative α and β stereo-chemical configurations.
Claim 4
Dependent Claim
10 words
As in claim 1, the compound which is 3α-acetoxy-2β-(7-chloro-3α-acetoxy-1-heptenyl)-5-oxocyclopentane-1α-heptanoic acid.
Claim 5
Dependent Claim
55 words
A compound according to claim 1 of the formula ##STR24## wherein X is a carbonyl radical; B is hydrogen or an alkyl radical containing 1-6 carbon atoms; Z is a chloro or bromo radical; Alk is an alkylene radical containing 4-5 carbon atoms; and the wavy line represents the alternative α and β stereochemical configurations.
Claim 6
Dependent Claim
10 words
As in claim 1, the compound which is 3α-hydroxy-2β-(7-chloro-3α-hydroxy-1-heptenyl)-5-oxocyclopentane-1α-heptanoic acid.
Claim 7
Dependent Claim
10 words
As in claim 1, the compound which is 3α-hydroxy-2β-(7-chloro-3β-hydroxy-1-heptenyl)-5-oxocyclopentane-1α-heptanoic acid.
Claim 8
Dependent Claim
10 words
As in claim 1, the compound which is 3α-hydroxy-2β-(7-chloro-3α-hydroxy-3β-methyl-1-heptenyl)-5-oxocyclopentane-1α-heptanoic acid.
Claim 9
Dependent Claim
10 words
As in claim 1, the compound which is 3α-hydroxy-2β-(7-chloro-3β-hydroxy-3α-methyl-1-heptenyl)-5-oxocyclopentane-1α-heptanoic acid.
Claim 10
Dependent Claim
10 words
As in claim 1, the compound which is 3α-hydroxy-2β-(7-chloro-5-methyl-3-hydroxy-1-heptenyl)-5-oxocyclopentane-1α-heptanoic acid.
Claim 11
Dependent Claim
10 words
As in claim 1, the compound which is 3α-hydroxy-2β-(8-bromo-3α-methyl-1-octenyl)-5-oxocyclopentane-1α-heptanoic acid.
Claim 12
Dependent Claim
10 words
As in claim 1, the compound which is 3α-hydroxy-2β-(8-bromo-3β-hydroxy-3α-methyl-1-octenyl)-5-oxocyclopentane-1α-heptanoic acid.
Claim 13
Dependent Claim
10 words
As in claim 1, the compound which is 3β-hydroxy-2β-(7-chloro-3α-hydroxy-1-heptenyl)-5-oxocyclopentane-1α-heptanoic acid.
References Cited (Backward Citations)
US3997588A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-10-31 | 1981-05-02 | 1981-11-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-10-31 | 1985-05-02 | 1985-11-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-10-31 | 1989-05-02 | 1989-11-01 | $7700.00 | Window Closed / Lapsed |