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HK1061679A1 - Phenylsulfonyl-1,3-dihydro-2h-indole-2-one derivatives, their preparation and their therapeutic use - Google Patents

Phenylsulfonyl-1,3-dihydro-2h-indole-2-one derivatives, their preparation and their therapeutic use Download PDF

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Publication number
HK1061679A1
HK1061679A1 HK04104546A HK04104546A HK1061679A1 HK 1061679 A1 HK1061679 A1 HK 1061679A1 HK 04104546 A HK04104546 A HK 04104546A HK 04104546 A HK04104546 A HK 04104546A HK 1061679 A1 HK1061679 A1 HK 1061679A1
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Hong Kong
Prior art keywords
dihydro
indol
chloro
compound
ethyl
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HK04104546A
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English (en)
French (fr)
Chinese (zh)
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HK1061679B (en
Inventor
亚伦迪麦塔
乔治盖西亚
理察洛克斯
布鲁诺萧恩提耶
克劳迪尼瑟拉戴尔-雷格
伯纳德东尼瑞
珍瓦格诺
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赛诺菲安万特
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Publication of HK1061679A1 publication Critical patent/HK1061679A1/xx
Publication of HK1061679B publication Critical patent/HK1061679B/xx

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Claims (8)

  1. Eine Verbindung der Formel: in der:
    - n 1 oder 2 bedeutet;
    - X eine Gruppe -CH2-; -O-; -NH-; -O-CH2-; -NH-CH2-; -NH-CH2-CH2 bedeutet;
    - R1 ein Halogenatom; (C1-C4)-Alkyl; (C1-C4)-Alkoxy darstellt;
    - R2 ein Wasserstoffatom; ein Halogenatom; (C1-C4)-Alkyl; (C1-C4)-Alkoxy; eine Trifluormethylgruppe darstellt;
    - R3 ein Halogenatom; (C1-C3)-Alkyl; (C1-C3)-Alkoxy; eine Trifluormethylgruppe; eine Trifluormethoxygruppe darstellt;
    - R4 ein Wasserstoffatom; ein Halogenatom; (C1-C3)-Alkyl-, (C1-C3)-Alkoxy bedeutet;
    - R5 eine Gruppe bedeutet, ausgewählt aus:
    - R6 (C1-C4)-Alkoxy bedeutet;
    - R7 (C1-C4)-Alkoxy bedeutet;
    sowie deren Salze mit anorganischen oder organischen Säuren, deren Solvate und/oder deren Hydrate.
  2. Verbindung nach Anspruch 1,worin:
    - n und X die in Anspruch 1 für die Verbindung der Formel (I) angegebenen Bedeutungen besitzen;
    - R1 ein Chloratom oder eine Methylgruppe darstellt;
    - R2 ein Wasserstoffatom bedeutet oder in der Position -6- des Indol-2-on-Rests steht und ein Chloratom, eine Methylgruppe, eine Methoxygruppe oder eine Trifluormethylgruppe bedeutet;
    - R3 ein Chloratom, ein Fluoratom, eine Methoxygruppe, eine Ethoxygruppe, eine Isopropoxygruppe, eine Trifluormethylgruppe oder eine Trifluormethoxygruppe darstellt;
    - R4 ein Wasserstoffatom oder eine Methoxygruppe bedeutet;
    - R5 2-Pyridinyl, 3-Pyridinyl, 4-Pyridinyl, 2-Pyrimidinyl, 2-Pyrazinyl, 3-Pyridazinyl, 1,3-Thiazol-2-yl bedeutet;
    - R6 in der -2-Stellung des Phenylrests steht und eine Methoxygruppe bedeutet;
    - R7 eine Methoxygruppe darstellt;
    sowie deren Salze mit anorganischen oder organischen Säuren, deren Solvate und/oder Hydrate.
  3. Eine Verbindung ausgewählt aus:
    - 5-Chlor-3-(2-ethoxyphenyl)-1-[(2,4-dimethoxyphenyl)-sulfonyl]-3-[2-oxo-2-[4-(4-pyridinyl)-1-piperazinyl]-ethyl]-1,3-dihydro-2H-indol-2-on;
    - 5-Chlor-3-(2-isopropoxyphenyl)-1-[(2,4-dimethoxyphenyl)-sulfonyl]-3-[2-oxo-2-[4-(4-pyridinyl)-1-piperazinyl]-ethyl]-1,3-dihydro-2H-indol-2-on;
    - 5-Chlor-1-[(2,4-dimethoxyphenyl)-sulfonyl]-3-(2-methoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl-4-(2-pyridinyl)-1-piperazincarboxylat;
    - 5-Chlor-1-[(2,4-dimethoxyphenyl)-sulfonyl]-3-(2-isopropoxyphenyl)-2-oxo-2,3-dihydro- 1H-indol-3-yl-4-(4-pyridinyl)-1-piperazincarboxylat;
    - N-[5-Chlor-1-[(2,4-dimethoxyphenyl)-sulfonyl]-3-(2-methoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-(4-pyridinyl)-homopiperazin-1-carboxamid;
    - N-[5-Chlor-1-[(2,4-dimethoxyphenyl)-sulfonyl]-3-(2-isopropoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-(3-pyridinyl)-piperazin-1-carboxamid;
    - N-[5-Chlor-1-[(2,4-dimethoxyphenyl)-sulfonyl]-3-(2-isopropoxyphenyl)-2-oxo-2, 3-dihydro-1H-indol-3-yl]-4-(4-pyridinyl)-piperazin-1-carboxamid;
    - 5-Chlor-1-[(2,4-dimethoxyphenyl)-sulfonyl]-3-(2-methoxyphenyl)-3-[[3-oxo-3-[4-(2-pyridinyl)-1-piperazinyl]-propyl]-amino]-1,3-dihydro-2H-indol-2-on;
    - 5,6-Dichlor-1-[(2,4-dimethoxyphenyl)-sulfonyl]-3-(2-methoxyphenyl)-3-[2-oxo-2-[4-(4-pyridinyl)-1-piperazinyl]-ethyl]-1,3-dihydro-2H-indol-2-on;
    - 5-Chlor-1-[(2,4-dimethoxyphenyl)-sulfonyl]-3-(2-methoxyphenyl)-6-methyl-3-[2-oxo-2-[4-(4-pyridinyl)-1-piperazinyl]-ethyl]-1,3-dihydro-2H-indol-2-on;
    - 5-Chlor-1-[(2,4-dimethoxyphenyl)-sulfonyl]-3-(2-methoxyphenyl)-6-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl-4-(4-pyridinyl)-1-piperazincarboxylat;
    - 5-Chlor-1-[(2,4-dimethoxyphenyl)-sulfonyl]-6-methoxy-3-(2-methoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl-4-(4-pyridinyl)-1-piperazincarboxylat;
    - N-[5-Chlor-3-(2-chlorphenyl)-1-[(2,4-dimethoxyphenyl)-sulfonyl]-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-(2-pyridinyl)-1-carboxamid;
    - N-[5-Chlor-1-[(2,4-dimethoxyphenyl)-sulfonyl]-3-(2-methoxyphenyl)-6-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-(4-pyridinyl)-piperazin-1-carboxamid;
    - N-[6-Chlor-3-(2-chlorphenyl)-1-[(2,4-dimethoxyphenyl)-sulfonyl]-5-methyl-2-oxo-2,3-dihydro-1H-indol-3-yl]-4-(4-pyridinyl)-piperazin-1-carboxamid;
    - 5-Chlor-1-[(2,4-dimethoxyphenyl)-sulfonyl]-3-(2-fluorphenyl)-3-[2-oxo-2-[4-(4-pyridinyl)-1-piperazinyl]-ethyl]-1,3-dihydro-2H-indol-2-on;
    - 5,6-Dichlor-1-[(2,4-dimethoxyphenyl)-sulfonyl]-3-(2-fluorphenyl)-3-[2-oxo-2-[4-(4-pyridinyl)-1-piperazinyl]-ethyl]-1,3-dihydro-2H-indol-2-on;
    - 5-Chlor-3-(2,3-dimethoxyphenyl)-1-[(2,4-dimethoxyphenyl)-sulfonyl]-3-[2-oxo-2-[4-(4-pyridinyl)-1-piperazinyl]-ethyl]-1,3-dihydro-2H-indol-2-on;
    - 5-Chlor-1-[(2,4-dimethoxyphenyl)-sulfonyl]-3-(2-ethoxyphenyl)-3-[2-oxo-2-[4-(3-pyridinyl)-1-piperazinyl]-ethyl]-1,3-dihydro-2H-indol-2-on;
    - 5-Chlor-1-[(2,4-dimethoxyphenyl)-sulfonyl]-3-(2-isopropoxyphenyl)-3-[2-oxo-2-[4-(3-pyridinyl)-1-piperazinyl]-ethyl]-1,3-dihydro-2H-indol-2-on;
    - 5-Chlor-1-[(2,4-dimethoxyphenyl)-sulfonyl]-3-(2-isopropoxyphenyl)-3-[2-oxo-2-[4-(4-pyridinyl)-1-homopiperazin]-ethyl]-1,3-dihydro-2H-indol-2-on;
    - 5-Chlor-1-[(2,4-dimethoxyphenyl)-sulfonyl]-3-(2-isopropoxyphenyl)-3-[2-oxo-2-[4-(1,3-thiazol-2-yl)-1-piperazinyl]-ethyl]-1,3-dihydro-2H-indol-2-on;
    - 5-Chlor-1-[(2,4-dimethoxyphenyl)-sulfonyl]-3-(2-ethoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl-4-(3-pyridinyl)-1-piperazincarboxylat;
    - 5-Chlor-1-[(2,4-dimethoxyphenyl)-sulfonyl]-3-(2-ethoxyphenyl)-2-oxo-2,3-dihydro-1H-indol-3-yl-4-(4-pyridinyl)-1-piperazincarboxylat;
    in Form der optisch reinen Isomeren oder in Form einer Mischung, sowie deren Salze mit anorganischen oder organischen Säuren, deren Solvate und/oder Hydrate.
  4. Verfahren zur Herstellung der Verbindungen der Formel (I) nach Anspruch 1, dadurch gekennzeichnet, daß man: eine Verbindung der Formel: in der R1, R2, R3, R4 und X die in Anspruch 1 für die Verbindung der Formel (I) angegebenen Bedeutungen besitzen, und:
    - Y eine Hydroxygruppe oder ein Chloratom darstellt, wenn X eine Gruppe der Formel -CH2-; -OCH2-; -NH-CH2-; -NH-CH2-CH2- bedeutet;
    - oder Y eine Phenoxygruppe bedeutet, wenn X eine Gruppe -O-; oder -NH- darstellt;
    - W ein Wasserstoffatom bedeutet, wenn X eine Gruppe -CH2-; oder -OCH2- darstellt;
    - oder W eine Gruppe der Formel bedeutet, in der R6 und R7 die in Anspruch 1 für die Verbindung der Formel (I) angegebenen Bedeutungen besitzen, wenn X eine Gruppe -O-; -NH-; -NH-CH2-; oder -NH-CH2-CH2- darstellt; mit einer Verbindung der Formel: in der n und R5 die in Anspruch 1 für die Verbindung der Formel (I) angegebenen Bedeutungen besitzen; umsetzt, so daß man
    - wenn W eine Gruppe bedeutet, die erwartete Verbindung der Formel (I) erhält;
    - oder wenn W ein Wasserstoffatom bedeutet, man die in dieser Weise erhaltene Verbindung der Formel:
    in Gegenwart einer Base mit einem Sulfonylhalogenid der Formel umsetzt: in der R6 und R7 die in Anspruch 1 für die Verbindung der Formel (I) angegebenen Bedeutungen besitzen und Hal ein Halogenatom darstellt.
  5. Verbindung der Formel: in der:
    - n 1 oder 2 bedeutet;
    - X eine Gruppe -CH2-; -O-CH2- darstellt;
    - R1 ein Halogenatom; (C1-C4)-Alkyl; (C1-C4)-Alkoxy bedeutet;
    - R2 ein Wasserstoffatom; ein Halogenatom; (C1-C4)-Alkyl; (C1-C4)-Alkoxy; eine Trifluormethylgruppe bedeutet;
    - R3 ein Halogenatom; (C1-C3)-Alkyl; (C1-C3)-Alkoxy; eine Trifluormethylgruppe; eine Trifluormethoxygruppe bedeutet;
    - R4 ein Wasserstoffatom; ein Halogenatom; (C1-C3)-Alkyl; (C1-C3)-Alkoxy darstellt;
    - R5 eine Gruppe bedeutet, ausgewählt aus:
    sowie deren Salze mit anorganischen oder organischen Säuren, in Form der optisch reinen Isomeren oder in Form einer Mischung.
  6. Arzneimittel, dadurch gekennzeichnet, daß es aus einer Verbindung nach einem der Ansprüche 1 bis 3 oder eines ihrer pharmazeutisch annehmbaren Salze mit anorganischen oder organischen Säuren, eines ihrer Solvate und/oder Hydrate gebildet ist.
  7. Pharmazeutische Zubereitung, dadurch gekennzeichnet, daß sie als Wirkstoff eine Verbindung nach einem der Ansprüche 1 bis 3 oder eines ihrer pharmazeutisch annehmbaren Salze mit anorganischen oder organischen Säuren, Solvate und/oder Hydrate sowie ein oder mehrere pharmazeutisch annehmbare Trägermaterialien enthält.
  8. Verwendung einer Verbindung nach einem der Ansprüche 1 bis 3, ihrer pharmazeutisch annehmbaren Salze mit anorganischen oder organischen Säuren, ihrer Solvate und/oder Hydrate für die Herstellung von Arzneimitteln zur Behandlung von kardiovaskulären Erkrankungen, Stress, Angst, der Depression, krampfartigen Besessenheitsstörungen, Panikanfällen, Erkrankungen des Nierensystems, Erkrankungen des Magensystems, Lungenkrebs mit kleinen Zellen, Fettsucht, Diabetes Typ II, Insulinresistenz, Hypertriglyceridämie, Atherosklerose, des Cushing-Syndroms, der Dysmenorrhoe und von vorzeitigen Wehen.
HK04104546.7A 2001-07-17 2002-07-15 Phenylsulfonyl-1,3-dihydro-2h-indole-2-one derivatives, their preparation and their therapeutic use HK1061679B (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0110359A FR2827604B1 (fr) 2001-07-17 2001-07-17 Nouveaux derives de 1-phenylsulfonyl-1,3-dihydro-2h-indol-2- one, un procede pour leur preparation et les compositions pharmaceutiques en contenant
FR01/10359 2001-07-17
PCT/FR2002/002500 WO2003008407A2 (fr) 2001-07-17 2002-07-15 Derives de 1-phenylsulfonyl-1,3-dihydro-2h-indol-2-one, leur preparation et leur application en therapeutique

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HK1061679A1 true HK1061679A1 (en) 2004-09-30
HK1061679B HK1061679B (en) 2005-07-22

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