Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Cannabinoid receptor modulator

a cannabinoid receptor and modulator technology, applied in the field of benzene ringfused 5membered heterocyclic compounds, can solve the problem of limiting the time-window for treatment, and achieve the effect of preventing, treating or diagnosing cerebrovascular diseases

Inactive Publication Date: 2009-01-22
TAKEDA PHARMA CO LTD
View PDF19 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

These compounds provide effective modulation of cannabinoid receptor function, potentially preventing, treating, or diagnosing cerebrovascular disorders and inflammatory diseases, offering brain-protective effects comparable to hypothermia therapy without the need for intensive care.

Problems solved by technology

For the treatment, a confirmation waiting time for a proper diagnosis by X-ray, CT or MRI image diagnosis is required, which limits time-window for treatment.
However, a cannabinoid receptor agonist can resolve the problem of time-window for treatment since it is not selective for a certain type of disease.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Cannabinoid receptor modulator
  • Cannabinoid receptor modulator
  • Cannabinoid receptor modulator

Examples

Experimental program
Comparison scheme
Effect test

reference example 1

Hydroxy(4-isopropylphenyl)acetic acid

[0598]To a mixture of lithium chloride (17.0 g, 418 mmol), potassium hydroxide (44.9 g, 800 mmol) and ice (150 g) was added a solution of bromoform (17.5 mL, 200 mmol) and 4-isopropyl benzaldehyde (30.3 mL, 200 mmol) in 1,4-dioxane (150 mL) at 0° C., and the mixture was stirred at 5-10° C. for 24 hours and then stirred at 35° C. for 24 hours. The aqueous layer was acidified with hydrochloric acid and was extracted with ethyl acetate. The extract was washed with water and then was 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.

[0599]1H-NMR (CDCl3) δ: 1.24 (6H, d, J=7.0 Hz), 2.91 (1H, septet, J=7.0 Hz), 5.21 (1H, s), 7.24 (2H, d, J=8.8 Hz), 7.36 (2H, d, J=8.8 Hz), 2H unidentified.

reference example 2

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

[0600]To a mixture of hydroxy(4-isopropylphenyl)acetic acid synthesized in Reference Example 1 (11.8 g, 60.8 mmol) and 2,3,5-trimethylphenol (12.4 g, 91.2 mmol) was added 70% sulfuric acid (10 mL) at room temperature, and the mixture was stirred at 115° C. for 12 hours. The mixture was added to water and was extracted with diisopropyl ether. The extract was washed with water and a saturated sodium hydrogen carbonate solution, and then was 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).

[0601]1H-NMR (CDCl3) δ: 1.22 (6H, d, J=6.6 Hz), 1.93 (3H, s), 2.24 (3H, s), 2.29 (3H, s), 2.88 (1H, septet, J=6.6 Hz), 4.76 (1H, s), 6.76 (1H, s), 7.07 (2H, d, J=8.1 Hz), 7.17 (2H, d, J=8.1 Hz).

reference example 3

3-(4-Isopropylphenyl)-6,7-dimethyl-1-benzofuran-2(3H)-one

[0602]Using hydroxy(4-isopropylphenyl)acetic acid synthesized in Reference Example 1 and 2,3-dimethylphenol, the title compound was synthesized in the same manner as in Reference Example 2. Yield 44%. Melting point: 58-60° C. (methanol).

[0603]1H-NMR (CDCl3) δ: 1.22 (6H, d, J=6.9 Hz), 2.27 (3H, s), 2.32 (3H, s), 2.88 (1H, septet, J=6.6 Hz), 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).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
cerebral temperatureaaaaaaaaaa
temperatureaaaaaaaaaa
temperatureaaaaaaaaaa
Login to View More

Abstract

A cannabinoid receptor modulator containing a compound represented by Formula (I0)wherein, X is an oxygen atom, etc., R0 is an optionally substituted acylamino group, ring A0 is a benzene ring which may further have a substituent in addition to R0, and ring B is an optionally substituted 5-membered heterocycle, or a salt thereof or a prodrug thereof.

Description

[0001]This is a divisional of U.S. application Ser. No. 10 / 561,483 filed Dec. 20, 2005, which is a National Stage application filed under §371 of PCT Application No. PCT / JP04 / 09355 filed Jun. 25, 2004. The entire disclosures of the prior applications are hereby incorporated by reference.TECHNICAL FIELD[0002]The present invention relates to a benzene ring-fused 5-membered heterocyclic compound, especially a benzofuran derivative as a cannabinoid receptor modulator, and a pharmaceutical composition containing the same.BACKGROUND ART[0003]Cannabinoid receptors belong to G-protein conjugated receptor having the seven transmembraneous domain. Among these, CB1 receptor is predominately distributed in the central nervous system, of which existence is known by Devane W A et al. (Molecular Pharmacology, 34, 605-613 (1988)). CB2 receptor, which has a predominant cell distribution in the immune system and in the peripheral tissues, has been discovered by Munro S et al. (Nature, 365, 61-65 (199...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/352C07D307/78C07D333/52A61P1/00A61P31/12A61P9/10A61P37/00A61P25/00A61K31/381A61K31/343A61K31/357A61K31/4025A61K31/4178A61K31/426A61K31/443A61K31/453A61K31/506A61P3/04A61P11/06A61P25/08A61P27/06A61P43/00C07D307/86C07D333/54
CPCA61K31/343A61K31/357A61K31/381A61K31/4025A61K31/4178A61K31/426C07D405/04A61K31/453A61K31/506C07D307/79C07D307/83C07D307/86C07D333/54A61K31/443A61P1/00A61P1/04A61P1/08A61P11/00A61P11/06A61P17/00A61P17/06A61P19/02A61P25/00A61P25/08A61P25/16A61P25/22A61P25/24A61P25/28A61P25/30A61P25/34A61P27/00A61P27/06A61P31/12A61P31/22A61P3/04A61P37/00A61P43/00A61P9/10
Inventor OHKAWA, SHIGENORITSUKAMOTO, TETSUYAKIYOTA, YOSHIHIROGOTO, MIKAYAMAMOTO, SHOUZOUSHIMOJOU, MASATOSETOU, MASAKI
Owner TAKEDA PHARMA CO LTD
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com