DE102010012233A1 - New substituted imidazole compounds, useful e.g. to treat cancer, pathological consequences of alcohol abuse, viral hepatitis, acute and chronic pancreatitis, toxic renal disease and hepatic insulin resistance in diabetes mellitus - Google Patents

New substituted imidazole compounds, useful e.g. to treat cancer, pathological consequences of alcohol abuse, viral hepatitis, acute and chronic pancreatitis, toxic renal disease and hepatic insulin resistance in diabetes mellitus Download PDF

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DE102010012233A1
DE102010012233A1 DE201010012233 DE102010012233A DE102010012233A1 DE 102010012233 A1 DE102010012233 A1 DE 102010012233A1 DE 201010012233 DE201010012233 DE 201010012233 DE 102010012233 A DE102010012233 A DE 102010012233A DE 102010012233 A1 DE102010012233 A1 DE 102010012233A1
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Dr. Diesinger Torsten
Dr. Haehner Thomas
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ACROVIS BIOSTRUCTURES GmbH
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/58—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen atoms

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Abstract

Substituted imidazole compounds (I) and their salts, are new. Substituted imidazole compounds of formula (I) and their salts, are new. R1 : H, halo, 1-6C-alkyl, 3-8C-cycloalkyl or aryl; R2 : H, halo, 1-6C-alkyl or 3-8C-cycloalkyl; R3 : H, halo, 1-6C-alkyl, 1-6C-alkyl-carbamoyl, aryl-carbamoyl or aryl-1-2C-alkyl-carbamoyl; n : 7-14; and m, p : 0-2. [Image] ACTIVITY : Cytostatic; Antialcoholic; Antiaddictive; Antiinflammatory; Hepatotropic; Virucide; Nephrotropic; Antidiabetic; Vasotropic; Antilipemic. MECHANISM OF ACTION : None given.

Description

Die Erfindung betrifft Imidazole sowie pharmazeutisch akzeptable Salze davon, ihre Herstellung sowie pharmazeutische Präparate enthaltend diese Imidazole oder pharmazeutisch akzeptable Salze davon.The invention relates to imidazoles and pharmaceutically acceptable salts thereof, their preparation and pharmaceutical preparations containing these imidazoles or pharmaceutically acceptable salts thereof.

Aus WO 2007/124734 A2 (Mueller-Enoch und Haehner) ist u. a. eine antineoplastische Wirkung und Cytotoxizität von 12-Imidazolyl-1-dodecanol bekannt, das auch die Bewegungsaktivität von HepG2-Zellen hemmt.Out WO 2007/124734 A2 (Mueller-Enoch and Haehner), inter alia, an antineoplastic action and cytotoxicity of 12-imidazolyl-1-dodecanol is known, which also inhibits the movement activity of HepG2 cells.

Aus WO 2005/105079 A2 (Bolton et al, Warner-Lambert) sind substituierte Imidazole bekannt, als potente Inhibitoren der Cholesterol-Biosynthese.Out WO 2005/105079 A2 (Bolton et al., Warner-Lambert), substituted imidazoles are known to be potent inhibitors of cholesterol biosynthesis.

Aus GB 2.016.452 A (lizuka et al, Ono Pharmaceutical) sind substituierte Imidazole bekannt, als Inhibitoren der Thromboxan-Synthetase.Out GB 2,016,452 A (Lizuka et al, Ono Pharmaceutical), substituted imidazoles are known as inhibitors of thromboxane synthetase.

Ping Lu et al, Archives of Biochemistry and Biophysics 1997, 1–7 , berichten über eine Reihenuntersuchung mit substituierten Imidazolen als Inhibitoren der Fettsäure-ώ-Hydroxylierung. Ping Lu et al, Archives of Biochemistry and Biophysics 1997, 1-7 , report on a screening with substituted imidazoles as inhibitors of fatty acid ώ-hydroxylation.

Davon ausgehend war es Aufgabe der vorliegenden Erfindung, in besonderer Weise substituierte Imidazole zur Verfügung zu stellen, mit denen sich ein therapeutischer Fortschritt erzielen lässt, insbesondere hinsichtlich Vorbeugung oder Behandlung von Krebserkrankungen, pathologischen Folgen des Alkoholmissbrauchs, viraler Hepatitis, Steato-Hepatitis, akuter und chronischer Pankreatitis, toxischer Nierenerkrankungen, hepatischer Insulinresistenz bei Diabetes mellitus, Leberschäden bei Morbus Wilson und Siderosen, Ischämie-Reperfusionsschäden, als Antidote gegen Umweltgifte und Medikamentenintoxikation, zur Verlängerung der Verweildauer von pharmazeutischen Medikamenten im Organismus, zur Bekämpfung toxischer Nebenwirkungen bei der Verabreichung von Chemotherapeutica, zur Vorbeugung oder Behandlung von Hyperlipidämien/Dyslipidämien, oder zur Vermeidung von Reperfusionsschäden bei transplantierten Organen, insbesondere vor und während der Lagerung, sowie kurz vor dem Implantieren in den Empfängerorganismus.On this basis, it was an object of the present invention to provide substituted imidazoles in a special way, with which a therapeutic progress can be achieved, in particular with regard to the prevention or treatment of cancers, pathological consequences of alcohol abuse, viral hepatitis, steato-hepatitis, acute and chronic pancreatitis, toxic kidney disease, hepatic insulin resistance in diabetes mellitus, liver damage in Wilson's disease and siderosis, ischemia-reperfusion injury, as an antidote to environmental toxins and drug intoxication, to prolong the residence time of pharmaceutical drugs in the organism, to combat toxic side effects when administering chemotherapeutic, for the prevention or treatment of hyperlipidemias / dyslipidemias, or for the prevention of reperfusion damage in transplanted organs, in particular before and during storage, as well as shortly before implantation in the recipient organism.

Dementsprechend betrifft die vorliegende Erfindung Imidazole der Formel (1)

Figure 00020001
worin n 7–14 und m 0, 1 oder 2 bedeutet, p 0, 1 oder 2 bedeutet, R1 H, Halogen, C1-C6-Alkyl, C3-C8-Cycloalkyl oder Aryl bedeutet, R2 H, Halogen, C1-C6-Alkyl oder C3-C8-Cycloalkyl bedeutet, und R3 H, Halogen, C1-C6-Alkyl, C1-C6-Alkyl-carbamoyl, Aryl-carbamoyl oder Aryl-C1-C2-alkyl-carbamoyl bedeutet, sowie pharmazeutisch akzeptable Salze davon.Accordingly, the present invention relates to imidazoles of the formula (1)
Figure 00020001
in which n is 7-14 and m is 0, 1 or 2, p is 0, 1 or 2, R 1 is H, halogen, C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl or aryl, R 2 is H , Halogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl, and R 3 is H, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-carbamoyl, aryl-carbamoyl or aryl C 1 -C 2 alkylcarbamoyl, as well as pharmaceutically acceptable salts thereof.

Halogen steht darin insbesondere für Chlor, Fluor oder Pseudohalogen, wie Cloromethyl, Fluoromethyl, Trifluoromethyl oder 1,1,1-Trifluoroethyl.Halogen is especially chlorine, fluorine or pseudohalogen, such as chloromethyl, fluoromethyl, trifluoromethyl or 1,1,1-trifluoroethyl.

C1-C6-Alkyl steht darin insbesondere für Methyl, Ethyl, n-Propyl, i-Propyl, n-Butyl, sec-Butyl oder tert-Butyl.C 1 -C 6 -alkyl is especially methyl, ethyl, n-propyl, i-propyl, n-butyl, sec-butyl or tert-butyl.

C3-C8-Cycloalkyl steht darin insbesondere für Cyclopropyl.C 3 -C 8 -cycloalkyl is in particular cyclopropyl.

Aryl steht darin insbesondere für Phenyl oder Halogen-substituiertes Phenyl, wie 4-Fluoro-phenyl oder 4-Chloro-phenyl.Aryl is in particular phenyl or halogen-substituted phenyl, such as 4-fluoro-phenyl or 4-chloro-phenyl.

C1-C6-Alkyl-carbamoyl steht darin insbesondere für Ethyl-carbamoyl, Aryl-carbamoyl für Phenyl-carbamoyl, und Aryl-C1-C2-alkyl-carbamoyl für Benzyl-carbamoyl oder Phenyl-ethyl-carbamoyl.In this formula, C 1 -C 6 -alkyl carbamoyl is in particular ethylcarbamoyl, arylcarbamoyl is phenylcarbamoyl, and arylC 1 -C 2 -alkylcarbamoyl is benzylcarbamoyl or phenylethylcarbamoyl.

Bevorzugt sind dabei solche Imidazole der Formel (1), worin n 9–12 bedeutet, m und p 0 bedeutet, R1 H, Halogen, C1-C3-Alkyl, Cyclopropyl, Phenyl oder Halogen-phenyl bedeutet, R2 H, Halogen, C1-C3-Alkyl oder Cyclopropyl bedeutet, und R3 H, Halogen, C1-C3-Alkyl, Phenyl-carbamoyl oder Benzyl-carbamoyl bedeutet.Preference is given here to those imidazoles of the formula (1) in which n is 9-12, m and p are 0, R 1 is H, halogen, C 1 -C 3 -alkyl, cyclopropyl, phenyl or halophenyl, R 2 H , Halogen, C 1 -C 3 -alkyl or cyclopropyl, and R 3 is H, halogen, C 1 -C 3 -alkyl, phenyl-carbamoyl or benzyl-carbamoyl.

Besonders bevorzugt sind dabei solche Imidazole der Formel (1), worin n 11 und m und p 0 bedeutet, R1 H, Halogen, C1-C3-Alkyl, Cyclopropyl, Phenyl oder Halogen-phenyl bedeutet, R2 H, Halogen, C1-C3-Alkyl oder Cyclopropyl bedeutet, und R3 H, Halogen, C1-C3-Alkyl, Phenyl-carbamoyl oder Benzyl-carbamoyl bedeutet. Particular preference is given here to those imidazoles of the formula (1) in which n is 11 and m and p are 0, R 1 is H, halogen, C 1 -C 3 -alkyl, cyclopropyl, phenyl or halophenyl, R 2 is H, halogen , C 1 -C 3 -alkyl or cyclopropyl, and R 3 is H, halogen, C 1 -C 3 -alkyl, phenyl-carbamoyl or benzyl-carbamoyl.

Ganz besonders bevorzugt sind dabei solche Imidazole der Formel (1), worin n 11 bedeutet, m und p 0 bedeutet, R1 H, Methyl, i-Propyl, Cyclopropyl, Phenyl oder 4-Fluoro-phenyl bedeutet, R2 H, Methyl, i-Propyl, oder Cyclopropyl bedeutet, und R3 H oder Benzyl-carbamoyl bedeutet.Very particular preference is given to those imidazoles of the formula (1) in which n is 11, m and p are 0, R 1 is H, methyl, isopropyl, cyclopropyl, phenyl or 4-fluorophenyl, R 2 is H, methyl , i-propyl, or cyclopropyl, and R 3 is H or benzyl-carbamoyl.

Bevorzugte Beispiele für erfindungsgemäße Imidazole der Formel (1) sind folgende:
n = 11, m = 0, p = 0, R1, R2 und R3 = H; nämlich:
2-Methyl-13-imidazolyl-n-tridecanol-(2).
n = 11, m = 0, p = 0, R1 = Methyl, R2 und R3 = H; nämlich:
2-Methyl-13-(2-methyl-imidazolyl)-n-tridecanol-(2).
n = 11, m = 0, p = 0, R1 = i-Propyl, und R2 und R3 = H; nämlich:
2-Methyl-13-(2-i-propyl-imidazolyl)-n-tridecanol-(2).
n = 11, m = 0, p = 0, R1 = Cyclopropyl, R2 und R3 = H; nämlich:
2-Methyl-13-(2-cyclopropyl-imidazolyl)-n-tridecanol-(2).
n = 11, m = 0, p = 0, R1 = 4-Fluoro-Phenyl, R2 und R3 = H; nämlich:
2-Methyl-13-(2-(4-fluoro-phenyl)-imidazolyl))-n-tridecanol-(2).
n = 11, m = 0, p = 0, R1 und R2 = H, R3 = Benzyl-carbamoyl; nämlich:
2-Methyl-13-(4-benzyl-carbamoyl-imidazolyl)-n-tridecanol-(2).Preferred examples of imidazoles of the formula (1) according to the invention are the following:
n = 11, m = 0, p = 0, R 1 , R 2 and R 3 = H; namely:
2-Methyl-13-imidazolyl-n-tridecanol (2).
n = 11, m = 0, p = 0, R 1 = methyl, R 2 and R 3 = H; namely:
2-Methyl-13- (2-methyl-imidazolyl) n-tridecanol (2).
n = 11, m = 0, p = 0, R 1 = i-propyl, and R 2 and R 3 = H; namely:
2-Methyl-13- (2-i-propyl-imidazolyl) n-tridecanol (2).
n = 11, m = 0, p = 0, R 1 = cyclopropyl, R 2 and R 3 = H; namely:
2-Methyl-13- (2-cyclopropyl-imidazolyl) n-tridecanol (2).
n = 11, m = 0, p = 0, R 1 = 4-fluoro-phenyl, R 2 and R 3 = H; namely:
2-Methyl-13- (2- (4-fluoro-phenyl) -imidazolyl)) - n-tridecanol (2).
n = 11, m = 0, p = 0, R 1 and R 2 = H, R 3 = benzylcarbamoyl; namely:
2-Methyl-13- (4-benzyl-carbamoyl-imidazolyl) n-tridecanol (2).

Die erfindungsgemäßen Imidazole können gegebenenfalls auch als Stereoisomere vorliegen.If appropriate, the imidazoles according to the invention can also be present as stereoisomers.

Die vorliegende Erfindung betrifft auch pharmazeutische Präparate enthaltend ein derartiges Imidazol, oder ein pharmazeutisch akzeptables Salze davon. Solche Präparate sind insbesondere geeignet zur Vorbeugung oder Behandlung von Krebserkrankungen, pathologischen Folgen des Alkoholmissbrauchs, viraler Hepatitis, Steato-Hepatitis, akuter und chronischer Pankreatitis, toxischer Nierenerkrankungen, hepatischer Insulinresistenz bei Diabetes mellitus, Leberschäden bei Morbus Wilson und Siderosen, Ischämie-Reperfusionsschäden, als Antidote gegen Umweltgifte und Medikamentenintoxikation, zur Verlängerung der Verweildauer von pharmazeutischen Medikamenten im Organismus, zur Bekämpfung toxischer Nebenwirkungen bei der Verabreichung von Chemotherapeutica, zur Vorbeugung oder Behandlung von Hyperlipidämien/Dyslipidämien, oder zur Vermeidung von Reperfusionsschäden bei transplantierten Organen, insbesondere vor und während der Lagerung, sowie kurz vor dem implantieren in den Empfängerorganismus.The present invention also relates to pharmaceutical preparations containing such an imidazole, or a pharmaceutically acceptable salt thereof. Such preparations are particularly useful for the prevention or treatment of cancers, pathological effects of alcohol abuse, viral hepatitis, steato-hepatitis, acute and chronic pancreatitis, toxic kidney disease, hepatic insulin resistance in diabetes mellitus, liver damage in Wilson's disease and siderosis, ischemia-reperfusion injury Antidotes against environmental toxins and drug intoxication, for prolonging the residence time of pharmaceutical drugs in the organism, for controlling toxic side effects when administering chemotherapeutics, for the prevention or treatment of hyperlipidemias / dyslipidemias, or for preventing reperfusion damage to transplanted organs, in particular before and during storage , as well as just before implanting in the recipient organism.

Die erfindungsgemäßen Imidazole können nach an sich bekannten Verfahren hergestellt werden, insbesondere nach Verfahren, wie sie in WO 2007/124734 A2 , WO 2005/105079 A2 und GB 2.016.452 A beschrieben sind. Sie können in geeigneter Weise mit weiteren pharmazeutischen Wirkstoffen zusammen verwendet werden.The imidazoles according to the invention can be prepared by processes known per se, in particular by processes as described in US Pat WO 2007/124734 A2 . WO 2005/105079 A2 and GB 2,016,452 A are described. They may be suitably used together with other pharmaceutical agents.

Die erfindungsgemäßen pharmazeutischen Präparate können nach an sich bekannten Verfahren hergestellt werden, insbesondere nach Verfahren, wie sie in WO 2007/124734 A2 , WO 2005/105079 A2 und GB 2.016.452 A beschrieben sind. Solche Präparate können in geeigneter Weise weitere pharmazeutische Wirkstoffe enthalten.The pharmaceutical preparations according to the invention can be prepared by processes known per se, in particular by processes as described in US Pat WO 2007/124734 A2 . WO 2005/105079 A2 and GB 2,016,452 A are described. Such preparations may suitably contain other pharmaceutically active substances.

Geeignete Testmodelle für erfindungsgemäße Imidazole und pharmazeutische Präparate sind u. a. in WO 2007/124734 A2 beschrieben.Suitable test models for imidazoles and pharmaceutical preparations according to the invention are, inter alia, in WO 2007/124734 A2 described.

ZITATE ENTHALTEN IN DER BESCHREIBUNG QUOTES INCLUDE IN THE DESCRIPTION

Diese Liste der vom Anmelder aufgeführten Dokumente wurde automatisiert erzeugt und ist ausschließlich zur besseren Information des Lesers aufgenommen. Die Liste ist nicht Bestandteil der deutschen Patent- bzw. Gebrauchsmusteranmeldung. Das DPMA übernimmt keinerlei Haftung für etwaige Fehler oder Auslassungen.This list of the documents listed by the applicant has been generated automatically and is included solely for the better information of the reader. The list is not part of the German patent or utility model application. The DPMA assumes no liability for any errors or omissions.

Zitierte PatentliteraturCited patent literature

  • WO 2007/124734 A2 [0002, 0019, 0020, 0021] WO 2007/124734 A2 [0002, 0019, 0020, 0021]
  • WO 2005/105079 A2 [0003, 0019, 0020] WO 2005/105079 A2 [0003, 0019, 0020]
  • GB 2016452 A [0004, 0019, 0020] GB 2016452 A [0004, 0019, 0020]

Zitierte Nicht-PatentliteraturCited non-patent literature

  • Ping Lu et al, Archives of Biochemistry and Biophysics 1997, 1–7 [0005] Ping Lu et al, Archives of Biochemistry and Biophysics 1997, 1-7 [0005]

Claims (12)

Imidazole der Formel (1)
Figure 00050001
worin n 7–14 und m 0, 1 oder 2 bedeutet, p 0, 1 oder 2 bedeutet, R1 H, Halogen, C1-C6-Alkyl, C3-C8-Cycloalkyl oder Aryl bedeutet, R2 H, Halogen, C1-C6-Alkyl oder C3-C8-Cycloalkyl bedeutet, und R3 H, Halogen, C1-C6-Alkyl, C1-C6-Alkyl-carbamoyl, Aryl-carbamoyl oder Aryl-C1-C2-alkyl-carbamoyl bedeutet, sowie pharmazeutisch akzeptable Salze davon.Imidazoles of the formula (1)
Figure 00050001
in which n is 7-14 and m is 0, 1 or 2, p is 0, 1 or 2, R 1 is H, halogen, C 1 -C 6 -alkyl, C 3 -C 8 -cycloalkyl or aryl, R 2 is H , Halogen, C 1 -C 6 -alkyl or C 3 -C 8 -cycloalkyl, and R 3 is H, halogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkyl-carbamoyl, aryl-carbamoyl or aryl C 1 -C 2 alkylcarbamoyl, as well as pharmaceutically acceptable salts thereof. Imidazole nach Anspruch 1, wobei n 9–12 bedeutet, m und p 0 bedeutet, R1 H, Halogen, C1-C3-Alkyl, Cyclopropyl, Phenyl oder Halogen-phenyl bedeutet, R2 H, Halogen, C1-C3-Alkyl oder Cyclopropyl bedeutet, und R3 H, Halogen, C1-C3-Alkyl, Phenyl-carbamoyl oder Benzyl-carbamoyl bedeutet, sowie pharmazeutisch akzeptable Salze davon.Imidazoles according to claim 1, wherein n is 9-12, m and p are 0, R 1 is H, halogen, C 1 -C 3 alkyl, cyclopropyl, phenyl or halophenyl, R 2 is H, halogen, C 1 - C 3 alkyl or cyclopropyl, and R 3 is H, halogen, C 1 -C 3 alkyl, phenyl carbamoyl or benzyl carbamoyl, as well as pharmaceutically acceptable salts thereof. Imidazole nach Anspruch 1, wobei n 11 bedeutet, m und p 0 bedeutet, R1 H, Halogen, C1-C3-Alkyl, Cyclopropyl, Phenyl oder Halogen-phenyl bedeutet, R2 H, Halogen, C1-C3-Alkyl oder Cyclopropyl bedeutet, und R3 H, Halogen, C1-C3-Alkyl, Phenyl-carbamoyl oder Benzyl-carbamoyl bedeutet, sowie pharmazeutisch akzeptable Salze davon.Imidazoles according to claim 1, wherein n is 11, m and p are 0, R 1 is H, halogen, C 1 -C 3 alkyl, cyclopropyl, phenyl or halophenyl, R 2 is H, halogen, C 1 -C 3 -Alkyl or cyclopropyl, and R 3 is H, halogen, C 1 -C 3 -alkyl, phenyl-carbamoyl or benzyl-carbamoyl, as well as pharmaceutically acceptable salts thereof. Imidazole nach Anspruch 1, wobei n 11 bedeutet, m und p 0 bedeutet, R1 H, Methyl, i-Propyl, Cyclopropyl, Phenyl oder 4-Fluoro-phenyl bedeutet, R2 H, Methyl, i-Propyl, oder Cyclopropyl bedeutet, und R3 H oder Benzyl-carbamoyl bedeutet, sowie pharmazeutisch akzeptable Salze davon.Imidazoles according to claim 1, wherein n is 11, m and p are 0, R 1 is H, methyl, i-propyl, cyclopropyl, phenyl or 4-fluorophenyl, R 2 is H, methyl, i-propyl, or cyclopropyl , and R 3 is H or benzylcarbamoyl, as well as pharmaceutically acceptable salts thereof. Imidazol nach Anspruch 1, wobei n 11 bedeutet, m und p 0 bedeutet, R1, R2 und R3 H bedeutet, nämlich 2-Methyl-13-imidazolyl-n-tridecanol-(2), sowie pharmazeutisch akzeptable Salze davon.An imidazole according to claim 1, wherein n is 11, m and p are 0, R 1 , R 2 and R 3 are H, namely 2-methyl-13-imidazolyl-n-tridecanol- (2), and pharmaceutically acceptable salts thereof. Imidazole nach Anspruch 1, wobei n 11 und m und p 0 bedeutet, R1 Methyl bedeutet, und R2 und R3 H bedeutet, nämlich 2-Methyl-13-(2-methyl-imidazolyl)-n-tridecanol-(2), sowie pharmazeutisch akzeptable Salze davon.Imidazoles according to claim 1, wherein n is 11 and m and p are 0, R 1 is methyl, and R 2 and R 3 are H, namely 2-methyl-13- (2-methyl-imidazolyl) -n-tridecanol- (2 ), as well as pharmaceutically acceptable salts thereof. Imidazole nach Anspruch 1, wobei n 11 und m und p 0 bedeutet, R1 i-Propyl bedeutet, und R2 und R3 H bedeutet, nämlich 2-Methyl-13-(2-i-propyl-imidazolyl)-n-tridecanol-(2), sowie pharmazeutisch akzeptable Salze davon.Imidazoles according to claim 1, wherein n is 11 and m and p is 0, R 1 is i-propyl, and R 2 and R 3 are H, namely 2-methyl-13- (2-i-propyl-imidazolyl) -n- tridecanol- (2), as well as pharmaceutically acceptable salts thereof. Imidazole nach Anspruch 1, wobei n 11 und m und p 0 bedeutet, R1 Cyclopropyl und R2 und R3 H bedeutet, nämlich 2-Methyl-13-(2-cyclopropyl-imidazolyl)-n-tridecanol-(2), sowie pharmazeutisch akzeptable Salze davon.Imidazoles according to claim 1, wherein n is 11 and m and p is 0, R 1 is cyclopropyl and R 2 and R 3 are H, namely 2-methyl-13- (2-cyclopropyl-imidazolyl) -n-tridecanol- (2), and pharmaceutically acceptable salts thereof. Imidazole nach Anspruch 1, wobei n 11 und m und p 0 bedeutet, R1 4-Fluoro-phenyl und R2 und R3 H bedeutet, nämlich 2-Methyl-13-(2-(4-fluoro-phenyl)-imidazolyl))-n-tridecanol-(2), sowie pharmazeutisch akzeptable Salze davon.Imidazoles according to claim 1, wherein n is 11 and m and p is 0, R 1 is 4-fluorophenyl and R 2 and R 3 are H, namely 2-methyl-13- (2- (4-fluoro-phenyl) -imidazolyl )) - n-tridecanol- (2), as well as pharmaceutically acceptable salts thereof. Imidazole nach Anspruch 1, wobei n 11 bedeutet, m und p 0 bedeutet, R1 und R2 H und R3 Benzyl-carbamoyl bedeutet, nämlich 2-Methyl-13-(4-benzyl-carbamoyl-imidazolyl)-n-tridecanol-(2), sowie pharmazeutisch akzeptable Salze davon.Imidazoles according to claim 1, wherein n is 11, m and p are 0, R 1 and R 2 are H and R 3 is benzylcarbamoyl, namely 2-methyl-13- (4-benzyl-carbamoyl-imidazolyl) -n-tridecanol - (2), as well as pharmaceutically acceptable salts thereof. Pharmazeutisches Präparat enthaltend ein Imidazol nach einem der Ansprüche 1–10, oder ein pharmazeutisch akzeptables Salze davon.A pharmaceutical preparation containing an imidazole according to any one of claims 1-10, or a pharmaceutically acceptable salt thereof. Pharmazeutisches Präparat enthaltend ein Imidazol nach einem der Ansprüche 1–10, oder ein pharmazeutisch akzeptables Salze davon, zur Vorbeugung oder Behandlung von Krebserkrankungen, pathologischen Folgen des Alkoholmissbrauchs, viraler Hepatitis, Steato-Hepatitis, akuter und chronischer Pankreatitis, toxischer Nierenerkrankungen, hepatischer Insulinresistenz bei Diabetes mellitus, Leberschäden bei Morbus Wilson und Siderosen, Ischämie-Reperfusionsschäden, als Antidote gegen Umweltgifte und Medikamentenintoxikation, zur Verlängerung der Verweildauer von pharmazeutischen Medikamenten im Organismus, zur Bekämpfung toxischer Nebenwirkungen bei der Verabreichung von Chemotherapeutica, zur Vorbeugung oder Behandlung von Hyperlipidämien/Dyslipidämien, oder zur Vermeidung von Reperfusionsschäden bei transplantierten Organen, insbesondere vor und während der Lagerung, sowie kurz vor dem Implantieren in den Empfängerorganismus.A pharmaceutical preparation containing an imidazole according to any one of claims 1-10, or a pharmaceutically acceptable salt thereof, for the prevention or treatment of cancers, pathological effects of alcohol abuse, viral hepatitis, steato-hepatitis, acute and chronic pancreatitis, toxic kidney disease, hepatic insulin resistance Diabetes mellitus, liver damage in morbus Wilson and siderosis, ischemia-reperfusion damage, as an antidote to environmental toxins and drug intoxication, for prolonging the retention of pharmaceutical drugs in the organism, for controlling toxic side effects when administering chemotherapeutics, for the prevention or treatment of hyperlipidemias / dyslipidemias, or for preventing reperfusion damage transplanted organs, especially before and during storage, as well as shortly before implantation in the recipient organism.
DE201010012233 2010-03-19 2010-03-19 New substituted imidazole compounds, useful e.g. to treat cancer, pathological consequences of alcohol abuse, viral hepatitis, acute and chronic pancreatitis, toxic renal disease and hepatic insulin resistance in diabetes mellitus Withdrawn DE102010012233A1 (en)

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Citations (3)

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GB2016452A (en) 1978-02-18 1979-09-26 Kissei Pharmaceutical Imidazole compounds
WO2005105079A2 (en) 2004-04-16 2005-11-10 Warner-Lambert Company Llc Novel imidazoles
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Publication number Priority date Publication date Assignee Title
GB2016452A (en) 1978-02-18 1979-09-26 Kissei Pharmaceutical Imidazole compounds
WO2005105079A2 (en) 2004-04-16 2005-11-10 Warner-Lambert Company Llc Novel imidazoles
WO2007124734A2 (en) 2006-04-28 2007-11-08 Dieter Mueller-Enoch Compounds a-r-x for the manufacture of pharmaceutical preparations

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