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US4607053A Expired / Lapsed US ⏱️ 0.0 years remaining

Arylhydroxamates useful as antiallergy agents

Assignee: ER Squibb and Sons LLC
•
Filing: 1985-04-04
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Granted: 1986-08-19
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Expires: 2005-04-04
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Abstract

Abstract Arylhydroxamates are provided having the structure <IMAGE> wherein R1 is hydrogen, lower alkyl, aryl, lower alkenyl, cycloalkenyl, aralkyl, or <IMAGE> wherein n is 1 to 4 and X is hydroxy, alkoxy, amino, C1-C4-alkylamino or C1-C4-dialkylamino. R2 is hydrogen or lower alkyl; and R3 is C1-C20 alkyl or C3-C20 alkenyl, aryl, aryl-alkyl, cycloalkyl, aryl-alkenyl, lower alkoxy, lower alkenyloxy, aryl-alkoxy or cycloalkyloxy. These compound are useful as inhibitors of DELTA 5-lipoxygenase and as such are useful as antiallergy agents.

Inventors

  • 👤 Donald S. Karanewsky
  • 👤 Martin F. Haslanger

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 12:51
CPC Classifications
C; C07; C07C; C07C65/00; C07C65/21; C07C65/24; C07C235/00; C07C235/42; C07C63/00; C07C63/04; C07C65/26; C07C65/28

Claims Analysis

Total Claims: 34
Claim 1
Independent Claim 283 words
A compound having the structure ##STR72## wherein R 1 is lower alkyl, aryl, lower alkenyl aralkyl, or ##STR73## wherein n is 2 to 4 and X is hydroxy, alkoxy, amino, C 1 -C 4 -alkylamino or C 1 -C 4 -dialkylamino; R 2 is hydrogen or lower alkyl; and R 3 is C 1 -C 20 alkyl, C 3 -C 20 alkenyl, aryl, aryl-alkyl, cycloalkyl, aryl-alkenyl, lower alkoxy, lower alkenyloxy, aryl-alkoxy, aryloxy or cycloalkyloxy, including pharmaceutically acceptable monobasic and dibasic salts whereof, and wherein the term alkyl by itself or as part of another group is unsubstituted or substituted with a substituent which is a halo, trifluoromethyl, alkoxy, aryl, alkyl-aryl, haloaryl, cycloalkyl, alkylcycloalkyl, hydroxy, alkylamino, alkanoylamino, arylcarbonylamino, nitro, cyano, thiol or an alkylthio substituent, the term aryl by itself or as part of another group is unsubstituted or substituted with 1 or 2 halogens, 1 or 2 lower alkyl groups, 1 or 2 lower alkoxy groups, an aryl group, 1 or 2 hydroxyls, 1 or 2 alkylamino groups, 1 or 2 alkanoylamino groups, 1 or 2 arylcarbonylamino groups, 1 or 2 amino groups, 1 or 2 nitro groups, 1 or 2 cyano groups, 1 or 2 thiol groups and/or 1 or 2 alkythio groups; and the term cycloalkyl by itself or as Part of another group is unsubstituted or substituted with 1 or 2 halogens 1 or 2 lower alkyl groups, 1 or 2 alkoxy groups, an aryl group, 1 or 2 hydroxyls, 1 or 2 alkylamino groups, 1 or 2 alkanoylamino, 1 or 2 arylcarbonylamino groups, 1 or 2 amino groups, 1 or 2 nitro groups, 1 or 2 cyano groups, 1 or 2 thiol groups and/or 1 or 2 alkylthio groups.
Claim 2
Dependent Claim 283 words
A compound having the structure ##STR72## wherein R 1 is lower alkyl, aryl, lower alkenyl aralkyl, or ##STR73## wherein n is 2 to 4 and X is hydroxy, alkoxy, amino, C 1 -C 4 -alkylamino or C 1 -C 4 -dialkylamino; R 2 is hydrogen or lower alkyl; and R 3 is C 1 -C 20 alkyl, C 3 -C 20 alkenyl, aryl, aryl-alkyl, cycloalkyl, aryl-alkenyl, lower alkoxy, lower alkenyloxy, aryl-alkoxy, aryloxy or cycloalkyloxy, including pharmaceutically acceptable monobasic and dibasic salts whereof, and wherein the term alkyl by itself or as part of another group is unsubstituted or substituted with a substituent which is a halo, trifluoromethyl, alkoxy, aryl, alkyl-aryl, haloaryl, cycloalkyl, alkylcycloalkyl, hydroxy, alkylamino, alkanoylamino, arylcarbonylamino, nitro, cyano, thiol or an alkylthio substituent, the term aryl by itself or as part of another group is unsubstituted or substituted with 1 or 2 halogens, 1 or 2 lower alkyl groups, 1 or 2 lower alkoxy groups, an aryl group, 1 or 2 hydroxyls, 1 or 2 alkylamino groups, 1 or 2 alkanoylamino groups, 1 or 2 arylcarbonylamino groups, 1 or 2 amino groups, 1 or 2 nitro groups, 1 or 2 cyano groups, 1 or 2 thiol groups and/or 1 or 2 alkythio groups; and the term cycloalkyl by itself or as Part of another group is unsubstituted or substituted with 1 or 2 halogens 1 or 2 lower alkyl groups, 1 or 2 alkoxy groups, an aryl group, 1 or 2 hydroxyls, 1 or 2 alkylamino groups, 1 or 2 alkanoylamino, 1 or 2 arylcarbonylamino groups, 1 or 2 amino groups, 1 or 2 nitro groups, 1 or 2 cyano groups, 1 or 2 thiol groups and/or 1 or 2 alkylthio groups.
Claim 3
Dependent Claim 14 words
The compound as defined in claim 1 wherein R 1 is alkyl or ##STR74##
Claim 4
Dependent Claim 21 words
The compound as defined in claim 1 wherein R 1 is alkyl, R 2 is H and R 3 is alkyl.
Claim 5
Dependent Claim 26 words
The compound as defined in claim 1 wherein R 1 is phenyl, phenylalkyl, phenylalkenyl, C.sub. to C 20 alkyl or C 3 to C 20 alkenyl.
Claim 6
Dependent Claim 11 words
The compound as defined in claim 1 having the name 4-decyl-N-hydroxy-N-methylbenzamide.
Claim 7
Dependent Claim 12 words
The compound as defined in claim 1 having the name (Z)-4-[[4-(1-decenyl)benzoyl]hydroxyamino]butanoic acid.
Claim 8
Dependent Claim 16 words
The compound as defined in claim 1 having the name (Z)-4-[[4-(1-decenyl)benzoyl]hydroxyamino]butanoic acid including all stereoisomers thereof.
Claim 9
Dependent Claim 12 words
The compound as defined in claim 1 having the name 4-[(3-decylbenzoyl)hydroxyamino]butanoic acid.
Claim 10
Dependent Claim 16 words
The compound as defined in claim 1 having the name 4-[(2-decylbenzoyl)hydroxyamino]butanoic acid or its dilithium salt.
Claim 11
Dependent Claim 14 words
The compound as defined in claim 1 having the name 4-[(4-decylbenzoyl)hydroxyamino]butanoic acid, ethyl ester.
Claim 12
Dependent Claim 20 words
The compound as defined in claim I having the name, (Z)-4-[[4-(1-decenyl)benzoyl]methoxyamino]butanoic acid or its dicyclohexylamine salt(1:1) including all stereoisomers thereof.
Claim 13
Dependent Claim 11 words
The compound as defined in claim 1 having the name N-(4-amino-4-oxobutyl)-4-decyl-N-hydroxybenzamide.
Claim 14
Dependent Claim 12 words
The compound as defined in claim 1 having the name 4-[(4-decylbenzoyl)hydroxyamino]butanoic acid.
Claim 15
Dependent Claim 12 words
The compound as defined in claim 1 having the name 5-[(4-decylbenzoyl)hydroxyamino]pentanoic acid.
Claim 16
Dependent Claim 12 words
The compound as defined in claim 1 having the name (4-decyl-N-hydroxybenzamido)acetic acid.
Claim 17
Dependent Claim 12 words
The compound as defined in claim 1 having the name 4-[[3-(1-decenyl)benzoyl]hydroxyamino]butanoic acid.
Claim 18
Dependent Claim 15 words
The compound as defined in claim 1 having the name (Z)-4-(1-decenyl)-N-hydroxybenzamide, including all stereoisomers thereof.
Claim 19
Dependent Claim 11 words
The compound as defined in claim 1 having the name N-hydroxy-N-methyl-4-(4-phenylbutyl)benzamide.
Claim 20
Dependent Claim 11 words
The compound as defined in claim 1 having the name N-hydroxy-N-methyl[1,1'-biphenylyl]-4-carboxamide.
Claim 21
Dependent Claim 11 words
The compound as defined in claim 1 having the name N-hydroxy-N-methyl-4-(4-phenylbuten-1-yl)benzamide.
Claim 22
Dependent Claim 11 words
The compound as defined in claim 1 having the name N-hydroxy-4-(4-phenylbutyl)-N-(phenylmethyl)benzamide.
Claim 23
Dependent Claim 11 words
The compound as defined in claim 1 having the name N-hydroxy-N-phenyl-4-(4-phenylbutyl)benzamide.
Claim 24
Dependent Claim 11 words
The compound as defined in claim 1 having the name N-(1,1-dimethylethyl)-N-hydroxy[1,1'-biphenylyl]-4-carboxamide.
Claim 25
Dependent Claim 11 words
The compound as defined in claim 1 having the name N-cyclohexyl-N-hydroxy[1,1'-biphenylyl]-4-carboxamide.
Claim 26
Dependent Claim 11 words
The compound as defined in claim 1 having the name N-hydroxy-N-methyl-4-pentylbenzamide.
Claim 27
Dependent Claim 11 words
The compound as defined in claim 1 having the name 4-heptyl-N-hydroxy-N-methylbenzamide.
Claim 28
Dependent Claim 11 words
The compound as defined in claim 1 having the name 4-(cyclohexyloxy)-N-hydroxy-N-methylbenzamide.
Claim 29
Dependent Claim 11 words
The compound as defined in claim 1 having the name N-hydroxy-N-methyl-4-(3-phenylpropoxy)benzamide.
Claim 30
Dependent Claim 11 words
The compound as defined in claim 1 having the name N-(1,1-dimethylethyl)-N-hydroxy-4-(4-phenylbutyl)benzamide.
Claim 31
Dependent Claim 34 words
A composition for inhibiting allergic conditions in a mammalian species, comprising an effective amount of a compound as defined in claim 1 or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier thereof.
Claim 32
Dependent Claim 35 words
A method of inhibiting Δ 5 -lipoxygenase 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 33
Dependent Claim 26 words
The method as defined in claim 30 wherein said compound is administered in an amount within the range of from about 1 to about 100 mg/kg.
Claim 34
Dependent Claim 38 words
A method for treating asthma 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.

References Cited (Backward Citations)

US2279560A Cited
US2279973A Cited
CH220744A Cited
US3560519A Cited
US3900514A Cited
US3978208A Cited
US4528392A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1989-08-18 1990-02-17 1990-08-19 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1993-08-18 1994-02-17 1994-08-19 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1997-08-18 1998-02-17 1998-08-19 $7700.00 Window Closed / Lapsed

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