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US4977174A
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7-oxabicycloheptane imidazole prostaglandin analogs useful in the treatment of thrombotic and vasospastic disease
Assignee: ER Squibb and Sons LLC
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Filing: 1990-03-12
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Granted: 1990-12-11
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Expires: 2010-03-12
Abstract
Abstract 7-Oxabicycloheptane imidazole prostaglandin analogs are provided which are useful in treating thrombotic and vasospastic disease and have the structural formula ##STR1## wherein m is 0, 1, 2, 3 or 4; n is 1, 2 or 3; and p is 1, 2 or 3; Z is --CH═CH--, --CH 2 CH 2 -- or ##STR2## wherein Y is 1 or a single bond; R is CO 2 H, CO 2 lower alkyl, CO 2 alkali metal, CONHSO 2 R 2 (wherein R 2 is lower alkyl or aryl) or --CH 2 -5-tetrazolyl; A is CHOH, C═O, ##STR3## (wherein R 3 is H or lower alkyl), or a single bond; R 1 is lower alkyl, aryl, cycloalkyl or H, R 1 can be H only when A is a single bond.
Inventors
- 👤 Philip D. Stein
- 👤 Steven E. Hall
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 06:34
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/02; C07D493/08; A; A61; A61P; A61P11/00; A61P11/08; A61P13/00; A61P13/02; A61P15/00; A61P43/00; A61P7/00; A61P7/02; A61P9/00; A61P9/08; A61P9/10
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
156 words
A compound having the formula ##STR118## including all stereoisomers thereof, wherein m is 0, 1, 2, 3 or 4; n is 1, 2 or 3; p is 1, 2 or 3; Z is --CH═CH--, --CH 2 CH 2 --or ##STR119## wherein Y is O or a single bond; with the provisos that when Z is ##STR120## and m is 0, then Y is a single bone; and when Z is --CH═CH--or --CH 2 CH 2 --, m is 1, 2, 3 or 4; R is CO 2 H, CO 2 alkali metal, CO 2 lower alkyl, CONHSO 2 R 2 (wherein R 2 is lower alkyl or aryl) or --CH 2 -5-tetrazolyl; A is CHOH, C═O, ##STR121## (wherein R 3 is H or lower alkyl), or a single bond; R 1 is lower alkyl, phenyl, naphthyl C 3 to C 12 cycloalkyl or H, R 1 can be H only when A is a single bond.
Claim 2
Dependent Claim
156 words
A compound having the formula ##STR118## including all stereoisomers thereof, wherein m is 0, 1, 2, 3 or 4; n is 1, 2 or 3; p is 1, 2 or 3; Z is --CH═CH--, --CH 2 CH 2 --or ##STR119## wherein Y is O or a single bond; with the provisos that when Z is ##STR120## and m is 0, then Y is a single bone; and when Z is --CH═CH--or --CH 2 CH 2 --, m is 1, 2, 3 or 4; R is CO 2 H, CO 2 alkali metal, CO 2 lower alkyl, CONHSO 2 R 2 (wherein R 2 is lower alkyl or aryl) or --CH 2 -5-tetrazolyl; A is CHOH, C═O, ##STR121## (wherein R 3 is H or lower alkyl), or a single bond; R 1 is lower alkyl, phenyl, naphthyl C 3 to C 12 cycloalkyl or H, R 1 can be H only when A is a single bond.
Claim 3
Dependent Claim
11 words
The compound as defined in claim 1 having the formula ##STR122##
Claim 4
Dependent Claim
18 words
The compound as defined in claim 2 where m is 2, n is 1 and p is 1.
Claim 5
Dependent Claim
11 words
The compound as defined in claim 1 having the formula ##STR123##
Claim 6
Dependent Claim
18 words
The compound as defined in claim 4 wherein m is 2, n is 1 and p is 1.
Claim 7
Dependent Claim
11 words
The compound as defined in claim 1 having the formula ##STR124##
Claim 8
Dependent Claim
18 words
The compound as defined in claim 6 wherein n is 1, m is 2 and p is 1.
Claim 9
Dependent Claim
11 words
The compound as defined in claim 1 having the formula ##STR125##
Claim 10
Dependent Claim
18 words
The compound as defined in claim 8 wherein n is 1, m is 2 and p is 1.
Claim 11
Dependent Claim
21 words
The compound as defined in claim 1 wherein R is CO 2 H, CONHSO 2 R 2 or --CH 2 -5-tetrazolyl.
Claim 12
Dependent Claim
11 words
The compound as defined in claim 1 having the formula ##STR126##
Claim 13
Dependent Claim
11 words
The compound as defined in claim 1 having the formula ##STR127##
Claim 14
Dependent Claim
11 words
The compound as defined in claim 1 having the formula ##STR128##
Claim 15
Dependent Claim
13 words
The compound as defined in claim 13 wherein Y is a single bond.
Claim 16
Dependent Claim
19 words
The compound as defined in claim 1 having the name [1S-[1α, 2α(Z), 3α, 4α]]-6-[3-[[4-(4-cyclohexyl-1-hydroxybutyl)-1H-imidazol-1-yl]methyl]-7-oxabicyclo[2.2.1]hept-2-yl]-4-hexenoic acid or its methyl ester.
Claim 17
Dependent Claim
18 words
The compound as defined in claim 1 having the name [1S-[1α, 2α(Z),3α, 4α]]-6-[3-[[4-(3-cyclohexylpropyl)-1H-imidazol-1-yl]methyl]-7-oxabicyclo[2.2.1]hept-2-yl]-4-hexenoic acid or its methyl ester.
Claim 18
Dependent Claim
19 words
The compound as defined in claim 1 having the name [1S-]1α, 2α(Z), 3α, 4α]]-6-[3-[[4-(4-cyclohexyl-1-oxobutyl)-1H-imidazol-1-yl]methyl]-7-oxabicyclo[2.2.1]hept-2-yl]-4-hexenoic acid or its methyl ester.
Claim 19
Dependent Claim
19 words
The compound as defined in claim 1 having then name [1S-[1α, 2α(Z), 3α, 4α]]-6-[3-[(1H-imidazol-1-yl)methyl]-7-oxabicyclo[2.2.1]hept-2-yl]-4-hexenoic acid or its methyl ester.
Claim 20
Dependent Claim
19 words
The compound as defined in claim 1 having the name [1S-[1α, 2α(Z), 3α, 4α]]-6-[3-[[4-[[(4-cyclohexylbutyl)amino]carbonyl]-1H-imidazol-1-yl]-methyl]-7-oxabicyclo[2.2.1]hept-2-yl]-4-hexenoic acid, or its methyl ester.
Claim 21
Dependent Claim
19 words
The compound as defined in claim 1 having the name [1S-(1α, 2α, 3α, 4α)]-2-[[3-[[4-[[(cyclohexylbutyl)amino]carbonyl]-1H-imidazol-1-yl]methyl]-7-oxabicyclo[2.2.1]hept-2-yl]methyl]benzenepropanoic acid or its methyl ester.
Claim 22
Dependent Claim
19 words
The compound as defined in claim 1 having the name [1S-(1α, 2α, 3α, 4α)]-2-[[3-[[4-(4-cyclohexyl-1-oxobutyl)-1H-imidazol-1-yl]methyl]-7-oxabicyclo[2.2.1]hept-2-yl]methyl]benzenepropanoic acid or its methyl ester.
Claim 23
Dependent Claim
26 words
A composition for inhibiting platelet aggregation and bronchoconstriction comprising an effective amount of a compound as defined in claim 1, and a pharmaceutically acceptable carrier therefor.
Claim 24
Dependent Claim
24 words
A method of inhibiting platelet aggregation which comprises administering to a mammalian host an effective amount of a compound as defined in claim 1.
Claim 25
Dependent Claim
26 words
A method of inhibiting bronchoconstriction associated with asthma, with comprises administering to a mammalian host an effective amount of a compound as defined in claim 1.
Claim 26
Dependent Claim
30 words
A method for improving post-ischemic myocardial dysfunction, which comprises administering to a mammalian host in need of such treatment an effective amount of a compound as defined in claim 1.
Claim 27
Dependent Claim
30 words
A method for treating toxemia during pregnancy, which comprises administering to a mammalian host in need of such treatment an effective amount of a compound as defined in claim 1.
Claim 28
Dependent Claim
31 words
A method for preventing or reducing venous thrombosis, which comprises administering to a mammalian host in need of such treatment an effective amount of a compound as defined in claim 1.
Claim 29
Dependent Claim
34 words
A method for preventing or educing platelet loss during extracorporeal circulation, which comprises administering to a mammalian host in need of such treatment an effective amount of a compound as defined in claim 1.
Claim 30
Dependent Claim
38 words
A method for treating burn injuries and/or promoting wound healing, which comprises administering to a mammalian host in need of such treatment an effective amount of a compound as defined in claim 1 in systemic or topical form.
Claim 31
Dependent Claim
45 words
A method for reducing post-ischemic myocardial injury, which comprises administering to a mammalian host in need of such treatment an effective amount of a compound as defined in claim 1 and an effective amount of a thrombolytic agent within 6 hours of a myocardial infarction.
Claim 32
Dependent Claim
20 words
The method as defined in claim 23 wherein said thrombolytic is t-PA, streptokinase, urokinase, prourokinase or anisoylated plasminogenstreptokinase activator complex.
References Cited (Backward Citations)
US4500540A
Cited
US4418076A
Cited
US4416896A
Cited
GB2126218A
Cited
US4463015A
Cited
US4489089A
Cited
US4474804A
Cited
US4522949A
Cited
US4536513A
Cited
JPS62470A
Cited
US4663336A
Cited
US4663337A
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1993-12-10 | 1994-06-11 | 1994-12-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-12-10 | 1998-06-11 | 1998-12-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-12-10 | 2002-06-11 | 2002-12-11 | $7700.00 | Window Closed / Lapsed |