Synthetic Studies on Condensed-Azole Derivatives. IV. Synthesis and Anti-asthmatic Activities of ω-Sulfamoylalkyloxyimidazo[1,2-b]pyridazines

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概要

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• A series of novel (imidazo[1,2-b]pyridazin-6-yl)oxyalkylsulfonamides was synthesized and evaluated for the ability to inhibit platelet activating factor (PAF)-induced bronchoconstriction in guinea pigs. The compounds bearing a gem-dialkyl or a cycloalkylidene group at the 2 position of the sulfamoylpropyloxy group in the side chain were found to have potent activity. Among them, 3-(imidazo[1,2-b]pyridazin-6-yl)oxy-2,2-dimethylpropanesulfonamide (6) showed excellent anti-asthmatic activity and the longest duration of action. The compounds bearing a methyl group at the 7 or 8 position of the imidazo[1,2-b]pyridazine ring were found to have enhanced activity. Among them, 3-(7-methylimidazo[1,2-b]pyridazin-6-yl)oxy-2,2-dimethylpropanesulfonamide (25) showed the most potent inhibitory effect, and its anti-asthmatic effect in an experimental model of allergic asthma was superior to that of theophylline. The structure-activity relationships in this series of compounds are discussed.

• 公益社団法人日本薬学会の論文
• 1996-01-15

著者

• MIYAKE Akio

  Pharmacology Research Laboratories I, Pharmaceutical Research Division, Takeda Chemical Industries,

• Miyake A

  Pharmaceutical Research Division Pharmaceutical Research Laboratories Iii Takeda Chemical Industries

• Miyake Akio

  Pharmaceutical Research Division Pharmaceutical Research Laboratories Ii Research Promotion Takeda C

• KUWAHARA Masaaki

  Pharmaceutical Research Division, Pharmaceutical Research Laboratories III, Takeda Chemical Industri

• KAWANO Yasuhiko

  Pharmaceutical Research Laboratories II, Takeda Chemical Industries, Ltd.,

• ASHIDA Yasuko

  Pharmaceutical Research Laboratories II, Takeda Chemical Industries, Ltd.,

• SHIMAZU Hiroshi

  Pharmaceutical Research Division, Pharmaceutical Research Laboratories III Takeda Chemical Industrie

• Ashida Y

  Pharmaceutical Research Division Takeda Chemical Industries Ltd.

• Kuwahara M

  Pharmaceutical Research Division Pharmaceutical Research Laboratories Iii Takeda Chemical Industries

• Kuwahara Masaaki

  Pharmaceutical Research Division Pharmaceutical Research Laboratories Ii Research Promotion Takeda C

• Shimazu Hiroshi

  Pharmaceutical Research Division Pharmaceutical Research Laboratories Iii Takeda Chemical Industries

• Kawano Y

  Otsuka Pharmaceutical Co. Ltd. Tokushima Jpn

• ASHIDA Yasuko

  Pharmaceutical Research Division, Takeda Chemical Industries, Ltd.

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