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US4555523A Expired / Lapsed US ⏱️ 0.0 years remaining

7-Oxabicycloheptane substituted thio prostaglandin analogs and their use in the treatment of thrombolytic disease

Assignee: ER Squibb and Sons LLC
•
Filing: 1984-06-04
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Granted: 1985-11-26
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Expires: 2004-06-04
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Abstract

Abstract 7-Oxabicycloheptane substituted thio prostaglandin analogs are provided having the structural formula ##STR1## wherein R is hydrogen, lower alkyl or alkali metal, R 1 is lower alkyl, arylalkyl, aryl, cycloalkyl or cycloalkylalkyl, X is O, S or NH, A is --CH═CH-- or --(CH 2 ) 2 , p is 0 to 4, n is 1 to 4, n' is 0 to 2, q is 1 to 4 and m is 0 to 8, and including all stereoisomers thereof. The compounds are cardiovascular agents useful, for example, in the treatment of thrombolytic disease; and are antiinflammatory agents useful, for example, in the treatment of rheumatoid arthritis.

Inventors

  • 👤 Steven E. Hall
  • 👤 Martin F. Haslanger

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 18:09
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/02; C07D493/08; A; A61; A61P; A61P29/00; A61P7/00; A61P7/02

Claims Analysis

Total Claims: 18
Claim 1
Independent Claim 202 words
A compound having the structural formula ##STR23## and including all stereoisomers thereof, wherein A is --CH═CH-- or --(CH 2 ) 2 --; p is 0 to 4; m is 0 to 8; n is 1 to 4; n' is 0, 1 or 2; q is 1 to 4; R is hydrogen, lower alkyl or alkali metal; X is S, O, or NH; and R 1 is lower alkyl, aryl, aralkyl, cycloalkyl or cycloalkylalkyl, wherein the term lower alkyl or alkyl by itself or as part of another group contains 1 to 12 carbons and is unsubstituted or substituted with halo, trifluoromethyl, alkoxy, haloaryl, cycloalkyl or alkylcycloalkyl; the term aryl by itself or as part of another group contains 6 to 10 carbons and is unsubstituted or substituted with lower alkyl, halogen or lower alkoxy; the term cycloalkyl by itself or as part of another group contains 3 to 12 carbons and is unsubstituted or substituted with 1 or 2 halogens, 1 or 2 lower alkyl groups and/or 1 or 2 lower alkoxy groups; and (CH 2 ) p , (CH 2 ) m , (CH 2 ) n and (CH 2 ) q can be substituted by one or more alkyl groups.
Claim 2
Dependent Claim 202 words
A compound having the structural formula ##STR23## and including all stereoisomers thereof, wherein A is --CH═CH-- or --(CH 2 ) 2 --; p is 0 to 4; m is 0 to 8; n is 1 to 4; n' is 0, 1 or 2; q is 1 to 4; R is hydrogen, lower alkyl or alkali metal; X is S, O, or NH; and R 1 is lower alkyl, aryl, aralkyl, cycloalkyl or cycloalkylalkyl, wherein the term lower alkyl or alkyl by itself or as part of another group contains 1 to 12 carbons and is unsubstituted or substituted with halo, trifluoromethyl, alkoxy, haloaryl, cycloalkyl or alkylcycloalkyl; the term aryl by itself or as part of another group contains 6 to 10 carbons and is unsubstituted or substituted with lower alkyl, halogen or lower alkoxy; the term cycloalkyl by itself or as part of another group contains 3 to 12 carbons and is unsubstituted or substituted with 1 or 2 halogens, 1 or 2 lower alkyl groups and/or 1 or 2 lower alkoxy groups; and (CH 2 ) p , (CH 2 ) m , (CH 2 ) n and (CH 2 ) q can be substituted by one or more alkyl groups.
Claim 3
Dependent Claim 11 words
The compound as defined in claim 1 wherein A is --CH═CH--.
Claim 4
Dependent Claim 11 words
The compound as defined in claim 1 wherein R is H.
Claim 5
Dependent Claim 11 words
The compound as defined in claim 1 wherein n' is 0.
Claim 6
Dependent Claim 11 words
The compound as defined in claim 1 wherein n' is 1.
Claim 7
Dependent Claim 11 words
The compound as defined in claim 1 wherein n' is 2.
Claim 8
Dependent Claim 43 words
The compound as defined in claim 1 wherein A is --CH═CH--, p is 1, m is 2 to 4, n is 1 or 2, n' is 0, q is 1 or 2; X is 0 and R 1 is lower alkyl or cycloalkyl.
Claim 9
Dependent Claim 39 words
The compound as defined in claim 1 wherein A is --CH═CH--, m is 3, n is 1, n' is 0, q is 2, X is 0, R is H or CH 3 , and R 1 is lower alkyl.
Claim 10
Dependent Claim 22 words
The compound as defined in claim 1 having the name [1β, 2α(Z),3α,4β]-7-[3-[[(2-phenoxyethyl)thio]methyl]-7-oxabicyclo[2.2.1]-hept-2-yl]-5-heptenoic acid or the methyl ester thereof including all stereoisomers thereof.
Claim 11
Dependent Claim 38 words
A method of inhibiting arachidonic acid-induced platelet aggregation and bronchoconstriction, which comprises administering to the circulatory system of a mammalian host an effective amount of a compound as defined in claim 1 or a pharmaceutically acceptable salt thereof.
Claim 12
Dependent Claim 26 words
The method as defined in claim 10 wherein said compound is administered in an amount within the range of from about 1 to about 100 mg/kg.
Claim 13
Dependent Claim 34 words
A composition for inhibiting arachidonic acid-induced platelet aggregation and bronchoconstriction comprising an effective amount of a compound as defined in claim 1 or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier therefor.
Claim 14
Dependent Claim 30 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 or a pharmaceutically acceptable salt thereof.
Claim 15
Dependent Claim 32 words
A method of inhibiting bronchoconstriction associated with asthma, which comprises administering to a mammalian host an effective amount of a compound as defined in claim 1 or a pharmaceutically acceptable salt thereof.
Claim 16
Dependent Claim 48 words
A method for inhibiting arachidonic acid-induced platelet aggregation and bronchoconstriction by inhibiting production of thromboxane A 2 by blocking the action of thromboxane synthetase, which comprises administering to a mammalian host an effective amount of a compound as defined in claim 1 or a pharmaceutically acceptable salt thereof.
Claim 17
Dependent Claim 38 words
A method for treating inflammation in a mammalian species in need of such treatment, which comprises administering to a mammalian host an effective amount of a compound as defined in claim 1 or a pharmaceutically acceptable salt thereof.
Claim 18
Dependent Claim 37 words
A method of relieving pain in a mammalian species which comprises administering to said mammalian species a composition containing an analgesically effective amount of a compound as defined in claim 1 or a pharmaceutically acceptable salt thereof.

References Cited (Backward Citations)

US4143054A Cited
US4187236A Cited
US4220594A Cited
US4254044A Cited
GB2039909A Cited
US4228180A Cited
EP0043292A2 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1988-11-25 1989-05-27 1989-11-26 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1992-11-25 1993-05-27 1993-11-26 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1996-11-25 1997-05-27 1997-11-26 $7700.00 Window Closed / Lapsed

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