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Regulator of cannabinoid receptor

A technology of cannabinoid receptors and modulators, applied in antiviral agents, digestive system, metabolic diseases, etc.

Inactive Publication Date: 2006-08-09
TAKEDA PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since cannabinoid receptor agonists are not selective for the type of disease, cannabinoid receptor agonists can solve the problem of the time window of treatment

Method used

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Examples

Experimental program
Comparison scheme
Effect test

reference example 1

[0686] Hydroxy(4-isopropylphenyl)acetic acid

[0687] To a mixture of lithium chloride (17.0 g, 418 mmol), potassium hydroxide (44.9 g, 800 mmol) and ice (150 g) were added bromoform (17.5 mL, 200 mmol) and 4-isopropylbenzaldehyde ( 30.3 mL, 200 mmol) in 1,4-dioxane (150 mL), and the mixture was stirred at 5-10°C for 24 hours, and then at 35°C for 24 hours. The aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate. The extract was washed with water and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain a residue, which was crystallized from hexane-ethyl acetate to obtain 28.5 g (yield 73%) of the title compound. Melting point: 156-157°C.

[0688] 1 H-NMR (CDCl 3 )δ: 1.24 (6H, d, J = 7.0Hz), 2.91 (1H, septet, J = 7.0Hz), 5.21 (1H, s), 7.24 (2H, d, J = 8.8Hz), 7.36 (2H , d, J = 8.8 Hz), 2H unconfirmed.

reference example 2

[0690] 3-(4-Isopropylphenyl)-4,6,7-trimethyl-1-benzofuran-2(3H)-one

[0691] At room temperature, in the mixture of hydroxy (4-isopropylphenyl) acetic acid (11.8g, 60.8mmol) and 2,3,5-trimethylphenol (12.4g, 91.2mmol) synthesized in Reference Example 1 70% sulfuric acid (10 mL) was added, and the mixture was stirred at 115°C for 12 hr. The mixture was added to water and extracted with diisopropyl ether. The extract was washed with water and saturated sodium bicarbonate solution, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain a residue, which was purified by silica gel column chromatography (hexane:ethyl acetate=8:1) to obtain 10.9 g (yield 65%) of the title compound. Melting point: 107-108°C (hexane-ethyl acetate).

[0692] 1 H-NMR (CDCl 3)δ: 1.22 (6H, d, J = 6.6Hz), 1.93 (3H, s), 2.24 (3H, s), 2.29 (3H, s), 2.88 (1H, septet, J = 6.6Hz), 4.76 (1H, s), 6.76 (1H, s), 7.07 (2H, d, J = 8.1 Hz), 7.17 (2H, d, J = 8....

reference example 3

[0694] 3-(4-isopropylphenyl)-6,7-dimethyl-1-benzofuran-2(3H)-one

[0695] Using hydroxy(4-isopropylphenyl)acetic acid and 2,3-dimethylphenol synthesized in Reference Example 1, the title compound was synthesized in the same manner as in Reference Example 2. Yield 44%. Melting point: 58-60°C (methanol).

[0696] 1 H-NMR (CDCl 3 )δ: 1.22 (6H, d, J = 6.9Hz), 2.27 (3H, s), 2.32 (3H, s), 2.88 (1H, septet, J = 6.6Hz), 4.85 (1H, s), 6.91 (1H, d, J = 7.8 Hz), 6.95 (1H, d, J = 7.8 Hz), 7.13 (2H, d, J = 8.1 Hz), 7.19 (2H, d, J = 8.1 Hz).

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PUM

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Abstract

A cannabinoid receptor modulator which contains a compound represented by the formula (I0): (I0) (wherein X represents oxygen, etc.; R0 represents optionally substituted acylamino; ring A0 represents a benzene ring optionally having a substituent besides R0; and ring B represents optionally substituted five-membered heterocycle), a salt of the compound, or a prodrug of either.

Description

technical field [0001] The present invention relates to benzene ring-fused 5-membered heterocyclic compounds, especially benzofuran derivatives, as cannabinoid receptor modulators, and pharmaceutical compositions comprising these compounds. Background technique [0002] Cannabinoid receptors are G-protein coupled receptors with seven transmembrane domains. Among them, the CB1 receptor is mainly distributed in the central nervous system, and its existence is known from Devane W A et al. (Molecular Pharmacology, 34, 605-613 (1988)). The CB2 receptor, which has a predominantly cellular distribution in the immune system as well as peripheral tissues, was discovered by Munro S et al. (Nature, 365, 61-65 (1993)). CB1 receptor and CB2 receptor show 48% homology. 97-99% of the amino acid sequence of the CB1 receptor is maintained in rat, mouse and human. [0003] In the brain, CB1 receptors are found mainly in the hippocampus, striatum, substantia nigra, basal forebrain regions, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/79C07D307/80C07D405/10C07D333/54C07D405/06C07D407/04C07D405/04C07D417/04C07D409/04A61K31/343A61K31/4025A61K31/357A61K31/443A61K31/506A61K31/426A61K31/381A61K31/4178A61K31/453A61P3/04A61P11/06A61P25/00A61P25/08A61P27/06A61P43/00C07D307/86
CPCC07D307/83C07D307/86A61K31/381A61K31/506C07D405/04A61K31/357C07D307/79A61K31/453A61K31/4025A61K31/4178A61K31/426A61K31/443A61K31/343C07D333/54A61P1/00A61P1/04A61P1/08A61P11/00A61P11/06A61P17/00A61P17/06A61P19/02A61P25/00A61P25/08A61P25/16A61P25/22A61P25/24A61P25/28A61P25/30A61P25/34A61P27/00A61P27/06A61P31/12A61P31/22A61P3/04A61P37/00A61P43/00A61P9/10
Inventor 大川滋纪塚本彻哉清田义弘后藤美香山本昭三下条雅人瀬藤正记
Owner TAKEDA PHARMA CO LTD
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