HK148295A - Antihyperlipidemic and antiatherosclerotic compounds and compositions - Google Patents

Antihyperlipidemic and antiatherosclerotic compounds and compositions Download PDF

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Publication number
HK148295A
HK148295A HK148295A HK148295A HK148295A HK 148295 A HK148295 A HK 148295A HK 148295 A HK148295 A HK 148295A HK 148295 A HK148295 A HK 148295A HK 148295 A HK148295 A HK 148295A
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urea
tetrahydro
methylethyl
phenyl
bis
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HK148295A
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English (en)
French (fr)
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Kalidas Trivedi Bharat
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Warner-Lambert Company
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
    • C07D311/82—Xanthenes
    • C07D311/90—Xanthenes with hydrocarbon radicals, substituted by amino radicals, directly attached in position 9
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
    • C07D313/02—Seven-membered rings
    • C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
    • C07D313/08—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
    • C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
    • C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
    • C07C2603/18—Fluorenes; Hydrogenated fluorenes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Obesity (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Pyrane Compounds (AREA)

Claims (9)

  1. Verbindung der Formel worin bedeuten:
    R₁ und R₂   unabhängig voneinander Alkyl oder Alkoxy mit 1 bis 6 Kohlenstoffatomen;
    R₃   Wasserstoff, Alkyl mit 1 bis 7 Kohlenstoffatomen oder Phenylmethyl;
    X   Sauerstoff oder Schwefel;
    n   Null, 1 oder 2;
    A   eine Gruppierung ausgewählt aus der aus
    bestehenden Gruppe, worin
    n'   für 1 oder 2 steht; und
    Y   eine direkte Bindung, >CH₂, >O oder >S;
    Z   eine direkte Bindung >CH₂, -CH=CH-, -CH₂CH₂-, >O oder >S;
    R₄   Alkyl mit 1 bis 6 Kohlenstoffatomen, Hydroxy, Acetoxy, Alkoxy mit 1 bis 6 Kohlenstoffatomen, Phenoxy, Fluor, Chlor, Brom, Nitro, Trifluormethyl, Carboxy, -COO-Alkyl, worin die Alkylgruppe 1 bis 4 Kohlenstoffatome aufweist, Amino, Alkylamino mit 1 bis 6 Kohlenstoffatomen, Dialkylamino, worin die Alkylgruppen unabhängig voneinander 1 bis 6 Kohlenstoffatome aufweisen, und -NH-Acetyl
       darstellen; oder ein pharmazeutisch annehmbares Salz dieser Verbindungen.
  2. Verbindung wie in Anspruch 1 definiert, worin A eine der nachstehend aufgeführten Gruppierungen in unsubstituierter oder substituierter Form darstellt:    2,3-Dihydro-1H-inden-1-yl;    2,3-Dihydro-1H-inden-2-yl;    2,3-Dihydro-1-hydroxy-1-indenyl;    1,2,3,4-Tetrahydronaphth-1-yl;    1,2,3,4-Tetrahydronaphth-2-yl;    1,2,3,4-Tetrahydro-1-hydroxy-1-naphthyl;    6,7,8,9-Tetrahydro-5H-benzocycloheptan-8-yl;    6,7,8,9-Tetrahydro-5H-benzocycloheptan-9-yl;    9-Fluorenyl;    10,11-Dibenzo[a,d]cyclohepten-5-yl;    1,2,3,4-Tetrahydro-1,1,4,4-tetramethyl-naphthen-2-yl;    2,3-Dihydrobenzofuran-2-yl;    2,3-Dihydrobenzofuran-3-yl;    3,4-Dihydro-(2H)1-benzopyran-3-yl;    3,4-Dihydro-(2H)1-benzopyran-4-yl;    2,3,4,5-Tetrahydro-1-benzoxepin-4-yl;    2,3,4,5-Tetrahydro-1-benzoxepin-5-yl;    9-Xanthenyl;    2,3-Dihydrobenzo[b]thiophen-2-yl;    2,3-Dihydrobenzo[b]thiophen-3-yl;    2,3,4,5-Tetrahydro-1-benzothiepin-4-yl;    2,3,4,5-Tetrahydro-1-benzothiepin-5-yl;    9-Thioxanthenyl;    3,4-Dihydro-(2H)1-benzothiopyran-3-yl; und    3,4-Dihydro-(2H)1-benzothiopyran-4-yl.
  3. Verbindung, wie in den Ansprüchen 1 und 2 definiert, ausgewählt aus der aus N-[2,6-Bis(1-methylethyl)phenyl]-N'-(9H-fluoren-9-yl-methyl)harnstoff; N-[2,6-Bis(1-methylethyl)phenyl]-N'-[(2,3-dihydro-1H-inden-1-yl)methyl]harnstoff; N-[2,6-Bis(1-methylethyl)phenyl]-N'-(1,2,3,4-tetrahydro-2-naphthyl)harnstoff; N-[2,6-Bis(1-methylethyl)phenyl]-N'-[(1,2,3,4-tetrahydro-1-naphthyl)methyl]harnstoff; N-[2,6-Bis(1-methylethyl)phenyl]-N'-[(3,4-dihydro-1-naphthyl)methyl]harnstoff; N-[2,6-Bis(1-methylethyl)phenyl]-N'-[(2,3-dihydro-1-hydroxy-1H-inden-1-yl)methyl]harnstoff; N-[2,6-Bis(1-methylethyl)phenyl]-N'-[(1,2,3,4-tetrahydro-1-hydrory-1-naphthyl)methyl]harnstoff; N-(2,6-Dimethylphenyl)-N'-(1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-2-naphthyl)harnstoff; N-[2,6-Bis(1-methylethyl)phenyl]-N'-[(1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-2-naphthyl]harnstoff; N-[2,6-Bis(1-methylethyl)phenyl]-N'-[(1,2,3,4-tetrahydro-7-methoxy-2-naphthyl)methyl]harnstoff; N-[2,6-Bis(1-methylethyl)phenyl]-N'-(9H-xanthen-9-yl-methyl)-harnstoff; N-[2,6-Bis(1-methylethyl)phenyl]-N'-[(1,2,3,4-tetrahydro-1-benzoxepin-4-yl)harnstoff; N-[2,6-Bis(1-methylethyl)phenyl]-N'-(3,4-dihydro-2H-1-benzopyran-3-yl)harnstoff; und N'-[2,6-Bis(1-methylethyl)phenyl]-N-(3,4-dihydro-2H-1-benzopyran-3-yl)-N-(1-methylethyl)harnstoff besteheden Gruppe.
  4. Pharmazeutische Zubereitung zur Behandlung von Hypercholesterinämie oder Atherosklerose, enthaltend eine wirksame ACAT-hemmende Menge einer Verbindung, wie in den Ansprüchen 1 bis 3 definiert, in Kombination mit einem pharmazeutisch annehmbaren Trägerstoff.
  5. Verwendung einer Verbindung nach den Ansprüchen 1 bis 3 zur Herstellung von Arzneimitteln für die Behandlung von Hypercholesterinämie oder Atherosklerose.
  6. Verfahren zur Herstellung einer Verbindung der Formel worin bedeuten:
    R₁ und R₂   unabhängig voneinander Alkyl oder Alkoxy mit 1 bis 6 Kohlenstoffatomen;
    R₃   Wasserstoff, Alkyl mit 1 bis 7 Kohlenstoffatomen oder Phenylmethyl;
    X   Sauerstoff oder Schwefel;
    n   Null, 1 oder 2;
    A   eine Gruppierung ausgewählt aus der aus
    bestehenden Gruppe, worin
    n'   für 1 oder 2 steht; und
    Y   eine direkte Bindung, >CH₂, >O oder >S;
    Z   eine direkte Bindung >CH₂, -CH=CH-, -CH₂CH₂-, >O oder >S;
    R₄   Alkyl mit 1 bis 6 Kohlenstoffatomen, Hydroxy, Acetoxy, Alkoxy mit 1 bis 6 Kohlenstoffatomen, Phenoxy, Fluor, Chlor, Brom, Nitro, Trifluormethyl, Carboxy, -COO-Alkyl, worin die Alkylgruppe 1 bis 4 Kohlenstoffatome aufweist, Amino, Alkylamino mit 1 bis 6 Kohlenstoffatomen, Dialkylamino, worin die Alkylgruppen unabhängig voneinander 1 bis 6 Kohlenstoffatome aufweisen, und -NH-Acetyl
       darstellen; oder eines pharmazeutisch annehmbaren Salzes dieser Verbindung, dadurch gekennzeichnet, dass man eine Verbindung der Formel worin R₁, R₂ und X wie oben angegeben definiert sind, mit einem Amin der Formel         A-(CH₂)n-NHR₃ worin A und n wie oben angegeben definiert sind, umsetzt, danach das Reaktionsprodukt unter Anwendung herkömmlicher Methoden isoliert und, sofern erwünscht, das erhaltene Produkt in ein pharmazeutisch annehmbares Salz überführt.
  7. Verfahren nach Anspruch 6 zur Herstellung einer Verbindung, worin A eine der nachstehend aufgeführten Gruppierungen in unsubstituierter oder substituierter Form darstellt:    2,3-Dihydro-1H-inden-1-yl;    2,3-Dihydro-1H-inden-2-yl;    2,3-Dihydro-1-hydroxy-1-indenyl;    1,2,3,4-Tetrahydronaphth-1-yl;    1,2,3,4-Tetrahydronaphth-2-yl;    1,2,3,4-Tetrahydro-1-hydroxy-1-naphthyl;    6,7,8,9-Tetrahydro-5H-benzocycloheptan-8-yl;    6,7,8,9-Tetrahydro-5H-benzocycloheptan-9-yl;    9-Fluorenyl;    10,11-Dibenzo[a,d]cyclohepten-5-yl;    1,2,3,4-Tetrahydro-1,1,4,4-tetramethyl-naphthen-2-yl;    2,3-Dihydrobenzofuran-2-yl;    2,3-Dihydrobenzofuran-3-yl;    3,4-Dihydro-(2H)1-benzopyran-3-yl;    3,4-Dihydro-(2H)1-benzopyran-4-yl;    2,3,4,5-Tetrahydro-1-benzoxepin-4-yl;    2,3,4,5-Tetrahydro-1-benzoxepin-5-yl;    9-Xanthenyl;    2,3-Dihydrobenzo[b]thiophen-2-yl;    2,3-Dihydrobenzo[b]thiophen-3-yl;    2,3,4,5-Tetrahydro-1-benzothiepin-4-yl;    2,3,4,5-Tetrahydro-1-benzothiepin-5-yl;    9-Thioxanthenyl;    3,4-Dihydro-(2H)1-benzothiopyran-3-yl; und    3,4-Dihydro-(2H)1-benzothiopyran-4-yl.
  8. Verfahren nach Anspruch 6 oder 7 zur Herstellung einer aus der aus den nachstehend aufgeführten Verbindungen bestehenden Gruppe ausgewählten Verbindung: N-[2,6-Bis(1-methylethyl)phenyl]-N'-(9H-fluoren-9-yl-methyl)harnstoff; N-[2,6-Bis(1-methylethyl)phenyl]-N'-[(2,3-dihydro-1H-inden-1-yl)methyl]harnstoff; N-[2,6-Bis(1-methylethyl)phenyl]-N'-(1,2,3,4-tetrahydro-2-naphthyl)harnstoff; N-[2,6-Bis(1-methylethyl)phenyl]-N'-[(1,2,3,4-tetrahydro-1-naphthyl)methyl]harnstoff; N-[2,6-Bis(1-methylethyl)phenyl]-N'-[(3,4-dihydro-1-naphthyl)methyl]harnstoff; N-[2,6-Bis(1-methylethyl)phenyl]-N'-[(2,3-dihydro-1-hydroxy-1H-inden-1-yl)methyl]harnstoff; N-[2,6-Bis(1-methylethyl)phenyl]-N'-[(1,2,3,4-tetrahydro-1-hydroxy-1-naphthyl)methyl]harnstoff; N-(2,6-Dimethylphenyl)-N'-(1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-2-naphthyl)harnstoff; N-[2,6-Bis(1-methylethyl)phenyl]-N'-[(1,2,3,4-tetrahydro-1,1,4,4-tetramethyl-2-naphthyl]harnstoff; N-[2,6-Bis(1-methylethyl)phenyl]-N'-[(1,2,3,4-tetrahydro-7-methoxy-2-naphthyl)methyl]harnstoff; N-[2,6-Bis(1-methylethyl)phenyl]-N'-(9H-xanthen-9-yl-methyl)-harnstoff; N-[2,6-Bis(1-methylethyl)phenyl]-N'-[(1,2,3,4-tetrahydro-1-benzoxepin-4-yl)harnstoff; N-[2,6-Bis(1-methylethyl)phenyl]-N'-(3,4-dihydro-2H-1-benzopyran-3-yl)harnstoff; und N'-[2,6-Bis(1-methylethyl)phenyl]-N-(3,4-dihydro-2H-1-benzopryan-3-yl)-N-(1-methylethyl)harnstoff.
  9. Verfahren zur Herstellung einer pharmazeutischen Zubereitung, welche eine Kombination einer Verbindung nach den Ansprüchen 5 bis 7 mit einem pharmazeutisch annehmbaren Trägerstoff aufweist.
HK148295A 1988-03-30 1995-09-14 Antihyperlipidemic and antiatherosclerotic compounds and compositions HK148295A (en)

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US (1) US4868210A (de)
EP (1) EP0335375B1 (de)
JP (1) JPH0688957B2 (de)
AT (1) ATE90340T1 (de)
DE (1) DE68906940T2 (de)
ES (1) ES2055754T3 (de)
HK (1) HK148295A (de)

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Publication number Publication date
EP0335375B1 (de) 1993-06-09
JPH0688957B2 (ja) 1994-11-09
EP0335375A2 (de) 1989-10-04
EP0335375A3 (de) 1991-04-17
US4868210A (en) 1989-09-19
DE68906940D1 (de) 1993-07-15
JPH026457A (ja) 1990-01-10
DE68906940T2 (de) 1993-10-28
ES2055754T3 (es) 1994-09-01
ATE90340T1 (de) 1993-06-15

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