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US4716178A Expired / Lapsed US ⏱️ 0.0 years remaining

Substituted di-t-butylphenols

Assignee: Riker Laboratories Inc
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Filing: 1986-08-27
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Granted: 1987-12-29
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Expires: 2006-08-27
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Abstract

Abstract Novel compounds which are 2,6-di-t-butylphenols substituted on the 4 position by an anilino group, which anilino group is substituted by a group which includes carboxyl, tetrazolyl or N-methyltetrazolyl are useful as inhibitors of leukotriene synthesis and as antiallergic agents. Pharmaceutical compositions containing such compounds and pharmacological methods for use of such compounds are also disclosed.

Inventors

  • 👤 Robert A. Scherrer
  • 👤 Mark A. Rustad

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-06 16:25
CPC Classifications
C; C07; C07D; C07D257/00; C07D257/02; C07D257/04; A; A61; A61K; A61K31/00; A61K31/21; A61K31/215; C07C; C07C233/00; C07C233/01; C07C233/16

Claims Analysis

Total Claims: 10
Claim 1
Independent Claim 242 words
A compound of the formula ##STR3## wherein each R independently represents hydrogen, lower alkyl, lower alkoxy, halogen, amino, lower alkylamino, di(lower)alkylamino, hydroxy, lower acylamido, trifluoromethyl, benzoyloxy, carboxy, or a derivative of a compound wherein R is carboxy selected from a lower alkyl carboxylate ester, a (lower)alkylamino(lower)alkyl carboxylate ester, a pharmaceutically acceptable (lower)alkylamino(lower)alkyl ester acid-addition salt, and a pharmaceutically acceptable carboxylate salt; and n is 0, 1, 2 or 3, with the proviso that if n is 2 or 3, only one R substituent, at the most, is selected from carboxy, and further with the proviso that if n is 2 or 3, all R substituents combined contain no more than 6 carbon atoms; Z is a carbon-carbon bond, divalent alkyl of 1 to about 8 carbon atoms or divalent alkylene of 2 to about 8 carbon atoms, and when alkyl or alkylene, Z may optionally be substituted by methyl or phenyl and may contain an ether, thioether or phenylene linkage; A is selected from carboxyl, tetrazolyl, and N-methyl tetrazolyl, with the proviso that if Z is a carbon-carbon bond, A is carboxyl; or a derivative of the foregoing selected from a lower alkyl carboxylate ester, a (lower)alkylamino(lower)alkyl carboxylate ester, a pharmaceutically acceptable (lower)alkylamino(lower)alkyl carboxylate ester acid-addition salt and a pharmaceutically acceptable carboxylate salt of the carboxy moiety when A is carboxyl, and selected from a pharmaceutically acceptable alkali metal and an alkaline earth salt of the tetrazolyl moiety when A is tetrazolyl.
Claim 2
Dependent Claim 242 words
A compound of the formula ##STR3## wherein each R independently represents hydrogen, lower alkyl, lower alkoxy, halogen, amino, lower alkylamino, di(lower)alkylamino, hydroxy, lower acylamido, trifluoromethyl, benzoyloxy, carboxy, or a derivative of a compound wherein R is carboxy selected from a lower alkyl carboxylate ester, a (lower)alkylamino(lower)alkyl carboxylate ester, a pharmaceutically acceptable (lower)alkylamino(lower)alkyl ester acid-addition salt, and a pharmaceutically acceptable carboxylate salt; and n is 0, 1, 2 or 3, with the proviso that if n is 2 or 3, only one R substituent, at the most, is selected from carboxy, and further with the proviso that if n is 2 or 3, all R substituents combined contain no more than 6 carbon atoms; Z is a carbon-carbon bond, divalent alkyl of 1 to about 8 carbon atoms or divalent alkylene of 2 to about 8 carbon atoms, and when alkyl or alkylene, Z may optionally be substituted by methyl or phenyl and may contain an ether, thioether or phenylene linkage; A is selected from carboxyl, tetrazolyl, and N-methyl tetrazolyl, with the proviso that if Z is a carbon-carbon bond, A is carboxyl; or a derivative of the foregoing selected from a lower alkyl carboxylate ester, a (lower)alkylamino(lower)alkyl carboxylate ester, a pharmaceutically acceptable (lower)alkylamino(lower)alkyl carboxylate ester acid-addition salt and a pharmaceutically acceptable carboxylate salt of the carboxy moiety when A is carboxyl, and selected from a pharmaceutically acceptable alkali metal and an alkaline earth salt of the tetrazolyl moiety when A is tetrazolyl.
Claim 3
Dependent Claim 11 words
A compound according to claim 1, wherein each R is hydrogen.
Claim 4
Dependent Claim 20 words
A compound according to claim 1, selected from 5-(3,5-di-t-butyl-4-hydroxy-N-phenylanilino)-5-oxopentanoic acid, 4-(3,5-di-t-butyl-4-hydroxy-N-phenyl-anilino)-4-oxobutanoic acid, N-(3,5-di-t-butyl-4-hydroxyphenyl)-N-phenyl-2-carboxyphenylacetamide, N-(3-carboxyphenyl)-N-(3,5-di-t-butyl-4-hydroxyphenyl)succinamic acid, 4-[N-(3,5-di-t-butyl-4-hydroxyphenyl)-N-phenylcarbamoyl]-3-methylbutyric acid, and N-(3,5-di-t-butyl-4-hydroxyphenyl)-N-phenylmaleamic acid.
Claim 5
Dependent Claim 32 words
An antiallergic pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable vehicle, said compound being present in an amount effective for obtaining an antiallergic response in a mammal.
Claim 6
Dependent Claim 33 words
A method for inhibiting bronchoconstriction due to an allergic response in a mammal wherein a compound according to claim 1 is administered to said mammal in an amount effective for obtaining such inhibition.
Claim 7
Dependent Claim 13 words
A method according to claim 5, wherein said compound is administered by inhalation.
Claim 8
Dependent Claim 12 words
A method according to claim 5, wherein said compound is administered orally.
Claim 9
Dependent Claim 28 words
A method for inhibiting leukotriene synthesis in a mammal comprising administering to said mammal a compound according to claim 1 in an amount effective to inhibit said synthesis.
Claim 10
Dependent Claim 28 words
A method for inhibiting lipoxygenase activity in a mammal comprising administering to said mammal a compound according to claim 1 in an amount effective to inhibit said activity.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1990-12-28 1991-06-29 1991-12-29 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1994-12-28 1995-06-29 1995-12-29 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1998-12-28 1999-06-29 1999-12-29 $7700.00 Window Closed / Lapsed

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