AU2418692A - New 3,5-di-tert.butyl-4-hydroxyphenyl derivatives, methods of preparing them and drugs containing them - Google Patents

New 3,5-di-tert.butyl-4-hydroxyphenyl derivatives, methods of preparing them and drugs containing them

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Publication number
AU2418692A
AU2418692A AU24186/92A AU2418692A AU2418692A AU 2418692 A AU2418692 A AU 2418692A AU 24186/92 A AU24186/92 A AU 24186/92A AU 2418692 A AU2418692 A AU 2418692A AU 2418692 A AU2418692 A AU 2418692A
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AU
Australia
Prior art keywords
radical
aryl
chain
alkyl
tert
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
AU24186/92A
Inventor
Bruno Dreckmann-Behrendt
Alois Dresel
Reinhard Heck
Helmut Michel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Roche Diagnostics GmbH
Original Assignee
Boehringer Mannheim GmbH
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Boehringer Mannheim GmbH filed Critical Boehringer Mannheim GmbH
Publication of AU2418692A publication Critical patent/AU2418692A/en
Abandoned legal-status Critical Current

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    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
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    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
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    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
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    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
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    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
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    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Abstract

Compounds of the formula I <IMAGE> in which A represents a valency, or a straight or a branched alkyl chain having 1 to 5 C atoms, X represents an -NR-CO- (amide) or an -NR-CO-NR- (urea) group, in which R represents a hydrogen atom or a C1-C4-alkyl radical, and Y represents a straight-chain or branched, saturated or unsaturated hydrocarbon chain having 1 to 6 C atoms, which can be substituted by an aryl, hetaryl, aryloxy or arylthio radical, a C3-C6-cycloalkyl radical or an aryl radical, where the aryl or hetaryl radical concerned can each be substituted 1 to 3 times in all possible positions on the ring by CN, hydroxymethyl, methylenedioxy, halogen, trifluoromethyl, C1-C4-alkyl, amino, C1-C4-acylamino, di-(C1-C4)-alkylamino, hydroxyl, C1-C4-alkoxy, carboxyl, ethyl oxyacetate or nitro, with the proviso that Y only denotes unsubstituted phenyl if A has a meaning other than -CH2- or -CH2-CH2-, and their pharmacologically acceptable salts, a process for their preparation and pharmaceutical compositions which contain these compounds, for the treatment of metabolic disorders.
AU24186/92A 1991-08-13 1992-08-10 New 3,5-di-tert.butyl-4-hydroxyphenyl derivatives, methods of preparing them and drugs containing them Abandoned AU2418692A (en)

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DE4126662A DE4126662A1 (en) 1991-08-13 1991-08-13 NEW 3,5-DI-TERT.BUTYL-4-HYDROXYPHENYL DERIVATIVES, METHOD FOR THEIR PRODUCTION AND MEDICINAL PRODUCTS
DE4126662 1991-08-13

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US5643943A (en) * 1994-12-23 1997-07-01 Alcon Laboratories, Inc. Systemic administration of esters and amides of antioxidants which may be used as antioxidant prodrug therapy for oxidative and inflammatory pathogenesis
US5811453A (en) * 1994-12-23 1998-09-22 Alcon Laboratories, Inc. Viscoelastic compositions and methods of use
US5750564A (en) * 1995-09-12 1998-05-12 Hellberg; Mark Anti-oxidant esters of non-steroidal anti-inflammatory agents
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ES2164564B1 (en) * 1999-10-18 2003-02-16 Menarini Lab TRISUSTITUTED BENCHES UNITED TO AMIDAS, ESTERS AND CARBOXYL ACIDS AS NEW INHIBITORS OF CYCLLOXYGENASA II.
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US10751351B2 (en) 2016-02-26 2020-08-25 Debiopharm International S.A. Medicament for treatment of diabetic foot infections
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ZA926049B (en) 1994-02-14
IL102772A0 (en) 1993-01-31
EP0600949A1 (en) 1994-06-15
MX9204622A (en) 1993-04-01
DE4126662A1 (en) 1993-02-18
EP0600949B1 (en) 1996-01-10
ATE132849T1 (en) 1996-01-15
JPH06510030A (en) 1994-11-10
DE59205041D1 (en) 1996-02-22

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