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US4169152A Expired / Lapsed US ⏱️ 0.0 years remaining

Isohexide and tetrahydrofuran ethers and their carbamates in method of bringing about relaxation of skeletal musculature

Assignee: Zeneca Inc
•
Filing: 1977-10-31
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Granted: 1979-09-25
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Expires: 1997-10-31
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Abstract

Abstract Disclosed are isohexide and tetrahydrofuran ethers and their carbamates and pharmaceutical compositions thereof and related compounds that exhibit central nervous system depressant activity, particularly skeletal muscle relaxant activity.

Inventors

  • 👤 John W. LeMaistre
  • 👤 Taketoshi P. Mori

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-26 17:58
CPC Classifications
C; C07; C07D; C07D493/00; C07D493/02; C07D493/04; C07D307/00; C07D307/02; C07D307/04; C07D307/18; C07D307/20

Claims Analysis

Total Claims: 12
Claim 1
Independent Claim 178 words
A method of bringing about relaxation of skeletal musculature in a mammal comprising administering to a mammal therapeutically effective amount of a compound selected from the group consisting of those represented by the formulas: ##STR28## wherein each R 1 is a radical independently selected from the group consisting of hydrogen, aryl, aralkyl where the aralkyl radical contains from 9 to 12 carbon atoms, alkyl substituted aryl, haloalkyl substituted aryl, alkoxy substituted aryl, halogen substituted aryl, alkyl substituted aralkyl, haloalkyl substituted aralkyl, alkoxy substituted aralkyl, mono-halogen substituted aralkyl where the aralkyl radical contains from 7 to 12 carbon atoms, di- and tri-halogen substituted aralkyl where the aralkyl radical contains from 9 to 12 carbon atoms, and ##STR29## and each R 2 is independently selected from the group consisting of hydrogen, aryl, aralkyl, alkyl substituted aryl, haloalkyl substituted aryl, alkoxy substituted aryl, halogen substituted aryl, alkyl substituted aralkyl, haloalkyl substituted aralkyl, alkoxy substituted aralkyl, halogen substituted aralkyl, and ##STR30## with the proviso that at least one R 1 and R 2 in each formula is other than hydrogen or ##STR31##
Claim 2
Independent Claim 178 words
A method of bringing about relaxation of skeletal musculature in a mammal comprising administering to a mammal therapeutically effective amount of a compound selected from the group consisting of those represented by the formulas: ##STR28## wherein each R 1 is a radical independently selected from the group consisting of hydrogen, aryl, aralkyl where the aralkyl radical contains from 9 to 12 carbon atoms, alkyl substituted aryl, haloalkyl substituted aryl, alkoxy substituted aryl, halogen substituted aryl, alkyl substituted aralkyl, haloalkyl substituted aralkyl, alkoxy substituted aralkyl, mono-halogen substituted aralkyl where the aralkyl radical contains from 7 to 12 carbon atoms, di- and tri-halogen substituted aralkyl where the aralkyl radical contains from 9 to 12 carbon atoms, and ##STR29## and each R 2 is independently selected from the group consisting of hydrogen, aryl, aralkyl, alkyl substituted aryl, haloalkyl substituted aryl, alkoxy substituted aryl, halogen substituted aryl, alkyl substituted aralkyl, haloalkyl substituted aralkyl, alkoxy substituted aralkyl, halogen substituted aralkyl, and ##STR30## with the proviso that at least one R 1 and R 2 in each formula is other than hydrogen or ##STR31##
Claim 3
Independent Claim 206 words
A method of bringing about relaxation of skeletal musculature in a mammal comprising administering to a mammal a therapeutically effective amount of a compound selected from the group consisting of those represented by the formula: ##STR32## wherein each R 1 is a radical independently selected from the group consisting of hydrogen, phenyl, phenylalkyl (C 3 to C 6 ), alkyl (C 1 to C 6 ) substituted phenyl, haloalkyl (C 1 to C 6 ) substituted phenyl, alkoxy (C 1 to C 6 ) substituted phenyl, halogen substituted phenyl, alkyl (C 1 to C 6 ) substituted phenylalkyl (C 1 to C 6 ) where the substitution is on the phenyl ring, haloalkyl (C 1 to C 6 ) substituted phenyl alkyl (C 1 to C 6 ) where the substitution is on the phenyl ring, alkoxy (C 1 to C 6 ) substituted phenylalkyl (C 1 to C 6 ) where the substitution is on the phenyl ring, di- and tri-halogen substituted phenylalkyl (C 3 to C 6 ) where the substitution is on the phenyl ring, mono-halogen substituted benzyl where the substitution is on the phenyl ring, and ##STR33## with the proviso that at least one R 1 is other than hydrogen or ##STR34##
Claim 4
Independent Claim 206 words
A method of bringing about relaxation of skeletal musculature in a mammal comprising administering to a mammal a therapeutically effective amount of a compound selected from the group consisting of those represented by the formula: ##STR32## wherein each R 1 is a radical independently selected from the group consisting of hydrogen, phenyl, phenylalkyl (C 3 to C 6 ), alkyl (C 1 to C 6 ) substituted phenyl, haloalkyl (C 1 to C 6 ) substituted phenyl, alkoxy (C 1 to C 6 ) substituted phenyl, halogen substituted phenyl, alkyl (C 1 to C 6 ) substituted phenylalkyl (C 1 to C 6 ) where the substitution is on the phenyl ring, haloalkyl (C 1 to C 6 ) substituted phenyl alkyl (C 1 to C 6 ) where the substitution is on the phenyl ring, alkoxy (C 1 to C 6 ) substituted phenylalkyl (C 1 to C 6 ) where the substitution is on the phenyl ring, di- and tri-halogen substituted phenylalkyl (C 3 to C 6 ) where the substitution is on the phenyl ring, mono-halogen substituted benzyl where the substitution is on the phenyl ring, and ##STR33## with the proviso that at least one R 1 is other than hydrogen or ##STR34##
Claim 5
Independent Claim 111 words
A method of bringing about relaxation of skeletal musculature in a mammal comprising administering to a mammal a composition comprised of a therapeutically effective amount of a compound selected from the group consisting of those represented by the formulas: ##STR35## wherein each R 3 and R 4 is a radical independently selected from the group consisting of hydrogen, aryl, aralkyl, alkyl substituted aryl, haloalkyl substituted aryl, alkoxy substituted aryl, halogen substituted aryl, alkyl substituted aralkyl, haloalkyl substituted aralkyl, alkoxy substituted aralkyl, halogen substituted aralkyl, and ##STR36## with the proviso that at least one R 3 and R 4 in each formula is other than hydrogen or ##STR37## in a pharmaceutical carrier.
Claim 6
Independent Claim 111 words
A method of bringing about relaxation of skeletal musculature in a mammal comprising administering to a mammal a composition comprised of a therapeutically effective amount of a compound selected from the group consisting of those represented by the formulas: ##STR35## wherein each R 3 and R 4 is a radical independently selected from the group consisting of hydrogen, aryl, aralkyl, alkyl substituted aryl, haloalkyl substituted aryl, alkoxy substituted aryl, halogen substituted aryl, alkyl substituted aralkyl, haloalkyl substituted aralkyl, alkoxy substituted aralkyl, halogen substituted aralkyl, and ##STR36## with the proviso that at least one R 3 and R 4 in each formula is other than hydrogen or ##STR37## in a pharmaceutical carrier.
Claim 7
Dependent Claim 156 words
A method of claim 1 wherein each R 1 is a radical independently selected from the group consisting of hydrogen, phenyl, phenylpropyl, phenylbutyl, mono-alkyl (C 1 to C 4 ) substituted phenyl, mono-haloalkyl (C 1 to C 4 ) substituted phenyl, mono-alkoxy (C 1 to C 4 ) substituted phenyl, mono-halogen substituted phenyl, mono-alkyl (C 1 to C 4 ) substituted phenylalkyl (C 1 to C 4 ) where the substitution is on the phenyl ring, monohaloalkyl (C 1 to C 4 ) substituted phenylalkyl (C 1 to C 4 ) where the substitution is on the phenyl ring, mono-alkoxy (C 1 to C 4 ) substituted phenylalkyl (C 1 to C 4 ) where the substitution is on the phenyl ring, mono-halogen substituted phenylalkyl (C 1 to C 4 ) where the substitution is on the phenyl ring, and ##STR38## with the proviso that at least one R 1 is other than hydrogen or ##STR39##
Claim 8
Dependent Claim 109 words
A method of claim 1 wherein each R 1 is a radical independently selected from the group consisting of hydrogen, phenyl, phenylpropyl, mono-methyl substituted phenyl, mono-trifluoromethyl substituted phenyl, mono-methoxy substituted phenyl, mono-fluoro substituted phenyl, mono-chloro substituted phenyl, mono-methyl substituted benzyl where the substitution is on the phenyl ring, mono-trifluoromethyl substituted benzyl where the substitution is on the phenyl ring, mono-alkoxy substituted benzyl where the substitution is on the phenyl ring, mono-fluoro substituted benzyl where the substitution is on the phenyl ring, mono-chloro substituted benzyl where the substitution is on the phenyl ring, and ##STR40## with the proviso that at least one R 1 is other than hydrogen or ##STR41##
Claim 9
Independent Claim 192 words
A method of bringing about relaxation of skeletal musculature in a mammal comprising administering to a mammal a therapeutically effective amount of a compound selected from the group consisting of those represented by the formula: ##STR42## where each R 2 is a radical independently selected from the group consisting of hydrogen, phenyl, phenylalkyl (C 1 to C 6 ), alkyl (C 1 to C 6 ) substituted phenyl, haloalkyl (C 1 to C 6 ) substituted phenyl, alkoxy (C 1 to C 6 ) substituted phenyl, halogen substituted phenyl, alkyl (C 1 to C 6 ) substituted phenylalkyl (C 1 to C 6 ) where the substitution is on the phenyl ring, haloalkyl (C 1 to C 6 ) substituted phenylalkyl (C 1 to C 6 ) where the substitution is on the phenyl ring, alkoxy (C 1 to C 6 ) substituted phenylalkyl (C 1 to C 6 ) where the substitution is on the phenyl ring, halogen substituted phenylalkyl (C 1 to C 6 ) where the substitution is on the phenyl ring, and ##STR43## with the proviso that at least one R 2 is other than hydrogen or ##STR44##
Claim 10
Independent Claim 192 words
A method of bringing about relaxation of skeletal musculature in a mammal comprising administering to a mammal a therapeutically effective amount of a compound selected from the group consisting of those represented by the formula: ##STR42## where each R 2 is a radical independently selected from the group consisting of hydrogen, phenyl, phenylalkyl (C 1 to C 6 ), alkyl (C 1 to C 6 ) substituted phenyl, haloalkyl (C 1 to C 6 ) substituted phenyl, alkoxy (C 1 to C 6 ) substituted phenyl, halogen substituted phenyl, alkyl (C 1 to C 6 ) substituted phenylalkyl (C 1 to C 6 ) where the substitution is on the phenyl ring, haloalkyl (C 1 to C 6 ) substituted phenylalkyl (C 1 to C 6 ) where the substitution is on the phenyl ring, alkoxy (C 1 to C 6 ) substituted phenylalkyl (C 1 to C 6 ) where the substitution is on the phenyl ring, halogen substituted phenylalkyl (C 1 to C 6 ) where the substitution is on the phenyl ring, and ##STR43## with the proviso that at least one R 2 is other than hydrogen or ##STR44##
Claim 11
Dependent Claim 10 words
A method of claim 1 wherein the compound is 2-O-(o-chlorobenzyl)isosorbide.
Claim 12
Dependent Claim 10 words
A method of claim 1 wherein the compound is 5-O-(o-chlorobenzyl)isosorbide.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-09-24 1983-03-26 1983-09-25 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-09-24 1987-03-26 1987-09-25 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-09-24 1991-03-26 1991-09-25 $7700.00 Window Closed / Lapsed

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