US4303670A
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US
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Bicyclic prostaglandins and process for their preparation
Assignee: Pfizer Italia SRL
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Filing: 1979-04-13
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Granted: 1981-12-01
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Expires: 1999-04-13
Abstract
Abstract Bicyclic prostaglandins and pharmaceutical and veterinary compositions containing them having numerous pharmaceutical or veterinary utilities, including, for example, hypotensive, vasodilatory, anti-aggregating, luteolytic, and cytoprotective activities. Processes for preparing the compounds and compositions are also disclosed.
Inventors
- 👤 Carmelo Gandolfi
- 👤 Carlo Passarotti
- 👤 Alessandro Andreoni
- 👤 Angelo Fumagalli
- 👤 Franco Faustini
- 👤 Roberto Ceserani
- 👤 Maria M. Usardi
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 16:14
CPC Classifications
C; C07; C07D; C07D307/00; C07D307/77; C07D307/93; C07D307/935; C07D307/937; A; A61; A61P; A61P43/00; C07C; C07C405/00
Claims Analysis
Total Claims: 39
Claim 1
Independent Claim
166 words
A compound of the formula ##STR53## wherein R c is H,C 1 -C 12 alkyl or C 2 -C 12 alkenyl; Z 1 is hydrogen or bromine; p is zero an integer of 1 to 7, Y is --CH 2 --CH 2 -- or ##STR54## one of R 2 and R 5 is hydrogen or C 1 -C 6 alkyl and the other is hydroxy; each of R 3 and R 4 , which are the same or different, may be hydrogen or C 1 -C 6 alkyl; each of n 1 and n 2 which are the same or different is zero or an integer of 1 to 6; m is zero or 1; R 6 is a C 3 -C 9 -cycloalkyl radical or a C 3 -C 9 -cycloalkenyl radical, unsubstituted or substituted by one or more substituents selected from the group consisting of C 1 -C 6 alkyl and C 1 -C 6 alkoxy, and the pharmaceutically or veterinarily acceptable salts thereof.
Claim 2
Dependent Claim
166 words
A compound of the formula ##STR53## wherein R c is H,C 1 -C 12 alkyl or C 2 -C 12 alkenyl; Z 1 is hydrogen or bromine; p is zero an integer of 1 to 7, Y is --CH 2 --CH 2 -- or ##STR54## one of R 2 and R 5 is hydrogen or C 1 -C 6 alkyl and the other is hydroxy; each of R 3 and R 4 , which are the same or different, may be hydrogen or C 1 -C 6 alkyl; each of n 1 and n 2 which are the same or different is zero or an integer of 1 to 6; m is zero or 1; R 6 is a C 3 -C 9 -cycloalkyl radical or a C 3 -C 9 -cycloalkenyl radical, unsubstituted or substituted by one or more substituents selected from the group consisting of C 1 -C 6 alkyl and C 1 -C 6 alkoxy, and the pharmaceutically or veterinarily acceptable salts thereof.
Claim 3
Dependent Claim
165 words
A compound of the formula ##STR55## wherein R c is H,C 1 -C 12 alkyl or C 2 -C 12 alkenyl; Z 1 is hydrogen or bromine; p is zero an integer of 1 to b 7, Y is --CH 2 --CH 2 -- one of R 2 and R 5 is hydrogen or C 1 -C 6 alkyl and the other is hydroxy; each of R 3 and R 4 , which are the same or different, may be hydrogen or C 1 -C 6 alkyl; each of n 1 and n 2 which are the same or different is zero or an integer of 1 to 6; m is zero or 1; R 6 is a C 3 -C 9 -cycloalkyl radical or a C 3 -C 9 -cycloalkenyl radical, unsubstituted or substituted by one or more substituents selected from the group consisting of C 1 -C 6 alkyl and C 1 -C 6 alkoxy, and the pharmaceutically or veterinarily acceptable salts thereof.
Claim 4
Dependent Claim
165 words
A compound of the formula ##STR55## wherein R c is H,C 1 -C 12 alkyl or C 2 -C 12 alkenyl; Z 1 is hydrogen or bromine; p is zero an integer of 1 to b 7, Y is --CH 2 --CH 2 -- one of R 2 and R 5 is hydrogen or C 1 -C 6 alkyl and the other is hydroxy; each of R 3 and R 4 , which are the same or different, may be hydrogen or C 1 -C 6 alkyl; each of n 1 and n 2 which are the same or different is zero or an integer of 1 to 6; m is zero or 1; R 6 is a C 3 -C 9 -cycloalkyl radical or a C 3 -C 9 -cycloalkenyl radical, unsubstituted or substituted by one or more substituents selected from the group consisting of C 1 -C 6 alkyl and C 1 -C 6 alkoxy, and the pharmaceutically or veterinarily acceptable salts thereof.
Claim 5
Dependent Claim
159 words
A compound of the formula ##STR56## wherein R c is H,C 1 -C 12 alkyl or C 2 -C 12 alkenyl; Z 1 is hydrogen or bromine; p is zero an integer of 1 to 7, Y is ##STR57## one of R 2 and R 5 is hydrogen or C 1 -C 6 alkyl and the other is hydroxy; each of R 3 and R 4 , which are the same or different, may be hydrogen or C 1 -C 6 alkyl; each of n 1 and n 2 which are the same or different is zero or an integer of 1 to 6; m is zero or 1; R 6 is C 3 -C 9 -cycloalkyl radical or a C 3 -C 9 -cycloalkenyl radical, unsubstituted or substituted by one or more substituents selected from the group consisting of C 1 -C 6 alkyl and C 1 -C 6 alkoxy, and the pharmaceutically or veterinarily acceptable salts thereof.
Claim 6
Dependent Claim
159 words
A compound of the formula ##STR56## wherein R c is H,C 1 -C 12 alkyl or C 2 -C 12 alkenyl; Z 1 is hydrogen or bromine; p is zero an integer of 1 to 7, Y is ##STR57## one of R 2 and R 5 is hydrogen or C 1 -C 6 alkyl and the other is hydroxy; each of R 3 and R 4 , which are the same or different, may be hydrogen or C 1 -C 6 alkyl; each of n 1 and n 2 which are the same or different is zero or an integer of 1 to 6; m is zero or 1; R 6 is C 3 -C 9 -cycloalkyl radical or a C 3 -C 9 -cycloalkenyl radical, unsubstituted or substituted by one or more substituents selected from the group consisting of C 1 -C 6 alkyl and C 1 -C 6 alkoxy, and the pharmaceutically or veterinarily acceptable salts thereof.
Claim 7
Dependent Claim
14 words
The compound of claim 1 wherein R is a free or salified carboxy group.
Claim 8
Dependent Claim
31 words
The compound of claim 1 wherein R is an esterified carboxy group of formula --COOR c wherein R c is C 1 -C 12 alkyl or C 2 -C 12 alkenyl.
Claim 9
Dependent Claim
14 words
The compound of claim 1 wherein p is an integer of 1 to 3.
Claim 10
Dependent Claim
17 words
The compound of claim 1 wherein n 1 is zero or an integer of 1 to 3.
Claim 11
Dependent Claim
15 words
The compound of claim 1 wherein n 2 is an integer of 1 to 3.
Claim 12
Dependent Claim
30 words
The compound of claim 1 wherein R 6 is a C 5 -C 7 cycloalkyl group optionally substituted by C 1 -C 6 alkyl or C 1 -C 6 alkoxy.
Claim 13
Dependent Claim
57 words
A compound selected from the group consisting of: 13t-6βH-6(9α)-oxide-11α,15S-dihydroxy-17-cyclopentyl-18,19,20-trinor-prost-13-enoic acid methyl ester, and the corresponding free acid and pharmaceutically or veterinarily acceptable salts thereof; 13t-6βH-6(9α)-oxide-11α,15S-dihydroxy-17-cyclohexyl-18,19,20-trinor-prost-13-enoic acid methyl ester and the corresponding free acid and pharmaceutically or veterinarily acceptable salts thereof; 13t-6βH-6,9α-oxide-11α,15S-dihydroxy-17-cyclohexyl-20,19,18-trinor-prost-13-enoic acid and the pharmaceutically or veterinarily acceptable salts thereof, as well as the corresponding methyl ester.
Claim 14
Dependent Claim
57 words
A compound selected from the group consisting of: 13t-6βH-6(9α)-oxide-11α,15S-dihydroxy-17-cyclopentyl-18,19,20-trinor-prost-13-enoic acid methyl ester, and the corresponding free acid and pharmaceutically or veterinarily acceptable salts thereof; 13t-6βH-6(9α)-oxide-11α,15S-dihydroxy-17-cyclohexyl-18,19,20-trinor-prost-13-enoic acid methyl ester and the corresponding free acid and pharmaceutically or veterinarily acceptable salts thereof; 13t-6βH-6,9α-oxide-11α,15S-dihydroxy-17-cyclohexyl-20,19,18-trinor-prost-13-enoic acid and the pharmaceutically or veterinarily acceptable salts thereof, as well as the corresponding methyl ester.
Claim 15
Dependent Claim
9 words
A 5-bromo derivative of the compound of claim 10.
Claim 16
Dependent Claim
10 words
A 15-R-hydroxy analog derivative of the compound of claim 10.
Claim 17
Dependent Claim
10 words
A 6αH analog derivative of the compound of claim 10.
Claim 18
Dependent Claim
19 words
A compound 13t-5-bromo-6βH-6(9α)-oxide-11α,15S-dihydroxy-17-cyclohexyl-18,19,20-trinor-prost-13-enoic acid methyl ester, and the corresponding free acid and the pharmaceutically or veterinarily acceptable salts thereof.
Claim 19
Dependent Claim
19 words
A compound 13t-5-bromo-6βH-6(9α)-oxide-11α,15S-dihydroxy-17-cyclohexyl-18,19,20-trinor-prost-13-enoic acid methyl ester, and the corresponding free acid and the pharmaceutically or veterinarily acceptable salts thereof.
Claim 20
Dependent Claim
41 words
A pharmaceutical or veterinary composition, suitable for use as a hypotensive agent, said composition comprising a therapeutically effective amount of a compound as claimed in one of claims 4, 2 or 3, and a pharmaceutically and/or veterinarily acceptable carrier and/or diluent.
Claim 21
Dependent Claim
42 words
A pharmaceutical or veterinary composition, suitable for use as a vasodilatory agent, said composition comprising a therapeutically effective amount of a compound as claimed in any one of claims 4, 2 or 3, and a pharmaceutically and/or veterinarily acceptabe carrier and/or diluent.
Claim 22
Dependent Claim
51 words
A pharmaceutical or veterinary composition, suitable for use as a platelet anti-aggregating agent, or agent for decreasing the adhesiveness of platelets, said composition comprising a therapeutically effective amount of a compound as claimed in any one of claims 4, 2 or 3, and a pharmaceutically and/or veterinarily acceptable carrier and/or diluent.
Claim 23
Dependent Claim
44 words
A pharmaceutical or veterinary composition, suitable for preventing or inhibiting thrombus formation in blood, said composition comprising a therapeutically effective amount of a compound as claimed in any one of claims 4, 2 or 3, and a pharmaceutically and/or veterinary acceptable carrier and/or diluent.
Claim 24
Dependent Claim
42 words
A pharmaceutical or veterinary composition suitable for use as a luteolytic agent, said composition comprising a therapeutically effective amount of a compound as claimed in any one of claims 4, 2 or 3, and a pharmaceutically and/or veterinarily acceptable carrier and/or diluent.
Claim 25
Dependent Claim
51 words
A pharmaceutical or veterinary composition, suitable for use as a cytoprotective agent active on the mucous membranes of the gastrointestinal tract, said composition comprising a therapeutically effective amount of a compound as claimed in any one of claims 4, 2 or 3, and a pharmaceutically and/or veterinarily acceptable carrier and/or diluent.
Claim 26
Dependent Claim
42 words
A pharmaceutical or veterinary composition, suitable for use as an anti-secretory agent, said composition comprising a therapeutically effective amount of a compound as claimed in any one of claims 4, 2 or 3, and a pharmaceutically and/or veterinarily acceptable carrier and/or diluent.
Claim 27
Dependent Claim
42 words
A pharmaceutical or veterinary composition, suitable for use as a bronchodilatory agent, said composition comprising a therapeutically effective amount of a compound as claimed in any one of claims 4, 2 or 3, and a pharmaceutically and/or veterinarily acceptable carrier and/or diluent.
Claim 28
Dependent Claim
42 words
A pharmaceutical or veterinary composition, suitable for use as an anti-asthmatic agent, said composition comprising a therapeutically effective amount of a compound as claimed in any one of claims 4, 2 or 3, and a pharmaceutically and/or veterinarily acceptable carrier and/or diluent.
Claim 29
Dependent Claim
42 words
A pharmaceutical or veterinary composition, suitable for use as an uterus stimulant, said composition comprising a therapeutically effective amount of a compound as claimed in any one of claims 4, 2 or 3, and a pharmaceutically and/or veterinarily acceptable carrier and/or diluent.
Claim 30
Independent Claim
39 words
A method of producing a hypotensive effect in a patient in need of such effect, said method comprising administering to said patient an effective amount of a compound as claimed in any one of claims 4, 2 or 3.
Claim 31
Independent Claim
39 words
A method of producing a vasodilatory effect in a patient in need of such effect, said method comprising administering to said patient an effective amount of a compound as claimed in any one of claims 4, 2 or 3.
Claim 32
Independent Claim
37 words
A method of inhibiting platelet aggregation, or of decreasing the adhesiveness of platelets, said method comprising contacting said platelets with an effective amount of a compound as claimed in any one of claims 4, 2 or 3.
Claim 33
Independent Claim
34 words
A method of preventing or inhibiting thrombus formation in blood, said method comprising contacting said blood with an effective amount of a compound as claimed in any one of claims 4, 2 or 3.
Claim 34
Independent Claim
39 words
A method of producing a luteolytic effect in a patient in need of such effect, said method comprising administering to said patient an effective amount of a compound as claimed in any one of claims 4, 2 or 3.
Claim 35
Independent Claim
47 words
A method of producing a cytoprotective effect on the mucous membranes of the gastrointestinal tract in a patient in need of such effect, said method comprising administering to said patient an effective amount of a compound as claimed in any one of claims 4, 2 or 3.
Claim 36
Independent Claim
39 words
A method of producing an anti-secretory effect in a patient in need of such effect, said method comprising administering to said patient an effective amount of a compound as claimed in any one of claims 4, 2 or 3.
Claim 37
Independent Claim
39 words
A method of producing a bronchodilatory effect in a patient in need of such effect, said method comprising administering to said patient an effective amount of a compound as claimed in any one of claims 4, 2 or 3.
Claim 38
Independent Claim
39 words
A method of producing an anti-asthmatic effect in a patient in need of such effect, said method comprising administering to said patient an effective amount of a compound as claimed in any one of claims 4, 2 or 3.
Claim 39
Independent Claim
42 words
A method of inducing labor or expelling a dead fetus in a patient in need of such treatment, said method comprising administering to said patient an effective amount of a compound as claimed in any one of claims 4, 2 or 3.
References Cited (Backward Citations)
US4125712A
Cited
GB2009148A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-11-30 | 1985-06-01 | 1985-12-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-11-30 | 1989-06-01 | 1989-12-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-11-30 | 1993-06-01 | 1993-12-01 | $7700.00 | Window Closed / Lapsed |