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AssigneeEisai Co., Ltd.
InventorsHitoshi Harada, Masanobu Shinoda, Richard Clark, Fumiyoshi Matsuura, Eita Emori, Shunji Kasai, Hideki Yoshitomi, Kazuto Yamazaki, Takashi Inoue, Sadakazu Miyashita, Taro Hihara
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The present invention provides a novel carboxylic acid derivative, a salt thereof or a hydrate of them which is useful as an insulin sensitizer, and a medicament comprising the derivative as the effective ingredient. More specifically, it provides a carboxylic acid compound represented by the formula (I), a salt thereof or a hydrate of them. In the formula, Ar represents a 6- to 14-membered aromatic ring group which may have at least one substituent; R1, R2, R3, R4, R5, R6, R7 and R8 are the same as or different from each other and each represents a hydrogen atom, a halogen atom, a hydroxyl group, a C1-6 alkyl group or a C1-6 alkoxy group; X represents an oxygen atom or a methylene group; Y represents a group represented by the formula (II) or (III): (wherein Z represents a group represented by the formula (IV): (wherein R9, R10, R11 and R12 are the same as or different from each other and each represents a hydrogen atom, a halogen atom, a hydroxyl group, a C1-6 alkyl group or a C1-6 alkoxy group)); m is 0 or 1; and n is 0 or 1.
A carboxylic acid compound represented by the formula (I), or a salt thereof:
Dependencies are inferred from the claim text.
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One oxygen atom: attached in position 2 or 6
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…
Drugs for disorders of the metabolism: antihyperlipidemics
For glucose homeostasis: for hyperglycaemia, e.g. antidiabetics
Term ended 17 Feb 2024 (estimated)
This application is the national phase under 35 U.S.C. § 371 of PCT International Application No. PCT/JP02/03003 which has an International filing date of Mar. 27, 2002, which designated the United States of America.
The present invention relates to a novel carboxylic acid compound useful for prevention or treatment of hyperglycemia and hyperlipemia, a salt thereof, an ester thereof or a hydrate of them, and to a medicament comprising the compound.
Diabetes mellitus refers to a durable hyperglycemic condition attributable to the absolute or relative shortage of intrinsic insulin (blood glucose-depressing hormone produced and secreted from Langerhans islet β cells in the pancreas), and in this disease, metabolic abnormalities caused by this condition appear as various morbid states.
Examples below will illustrate the present invention more in detail and more specifically. However, the invention should not be limited by these Examples.
To a solution of 2,4-dichlorophenoxy acetic acid (15.0 g) in tetrahydrofuran (300 mL) was added dropwise 1.0M borane-tetrahydrofuran complex/tetrahydrofuran solution (96 mL) under ice-cooling over 1.5 hours. The reaction solution was stirred at room temperature for 22 hours. After the reaction solution was concentrated, the residue was diluted with saturated aqueous ammonium chloride solution and ethyl acetate. The organic layer was washed with saturated ammonium chloride, saturated aqueous sodium hydrogencarbonate solution (×2) and saturated ammonium chloride, dried over anhydrous sodium sulfate and then concentrated, to give the title compound as a colorless oil (14 g).
1H-NMR(CDCl3)δ: 2.21 (d, J=6.4 Hz, 1H) 3.99 (dt, J=4.4, 6.4 Hz, 2H) 4.12 (t, J=4.4 Hz, 2H) 6.87 (d, J=8.8 Hz, 1H) 7.20 (dd, J=2.4, 8.8 Hz, 1H) 7.37 (d, J=2.4 Hz, 1H)