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

Cannabinoid Receptor Ligands and Uses Thereof

Inactive Publication Date: 2006-10-26
PFIZER INC
View PDF10 Cites 4 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0010] Current treatments for alcohol abuse or dependence generally suffer from non-compliance or potential h

Problems solved by technology

Older adrenergic weight-loss drugs (e.g., amphetamine, methamphetamine, and phenmetrazine), which strongly engage in dopamine pathways, are no longer recommended because of the risk of their abuse.
Fenfluramine and dexfenfluramine, both serotonergic agents used to regulate appetite, are no longer available for use.
Health risks associated with alcoholism include impaired motor control and decision making, cancer, liver disease, birth defects, heart disease, drug / drug interactions, pancreatitis and interpersonal problems.

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 Ligands and Uses Thereof
  • Cannabinoid Receptor Ligands and Uses Thereof
  • Cannabinoid Receptor Ligands and Uses Thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of 9-(4-Chlorophenyl)-8-(2,4-dichlorophenyl)-6-isopropoxy-9H-purine (IA-1)

[0265]

[0266] Sodium (7 mg, 0.3 mmol) was dissolved in isopropanol (1 ml) and to it was added 6-chloro-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purine I-(1A-1)d (30 mg, 0.07 mmol). After stirring at room temperature overnight, the reaction mixture was evaporated to dryness and extracted into ethyl acetate from saturated aqueous NaHCO3 solution. The organic layers were combined, dried (Na2SO4), filtered, and concentrated to dryness. The crude residue was purified on a TLC preparative plate using 4% methanol / methylene chloride as the solvent to yield title compound 1A-1. A solution of the material in methylene chloride was treated with excess 1 N HCl in diethyl ether, stirred, evaporated to dryness, and then triturated in diethyl ether to afford the hydrochloride salt of compound 1A-1 (8 mg, 26%): +ESI MS (M+1) 433.4; 1H NMR (400 MHz, CD3OD) δ 8.50 (s, 1H), 7.64 (d, J=8.3 Hz, 1H), 7.55 (d, J=1.7 ...

example 2

Preparation of 6-tert-Butoxy-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purine (2A-1)

[0268]

[0269] 6-Chloro-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purine I-(1A-1)d, potassium tert-butoxide (20 mg, 0.15 mmol) and tetrahydrofuran (1 ml) were combined and stirred overnight at ambient temperature. The reaction mixture was concentrated to dryness and the residue was extracted into ethyl acetate from saturated aqueous NaHCO3 solution. The organic layers were combined, dried (Na2SO4), filtered, and evaporated to dryness. The crude product was purified by chromatography on a preparative TLC plate using 4% methanol / methylene chloride as the solvent to give title compound 2A-1 as a yellow oil: +ESI MS (M+1) 447.5; 1H NMR (400 MHz, CD3OD) δ 8.48 (s, 1H), 7.64 (d, J=8.3 Hz, 1H), 7.55 (d, J=2.1 Hz, 1H), 7.49-7.44 (m, 3H), 7.34 (d, J=9.1 Hz, 2H), 1.77 (s, 9H).

example 3

Preparation of 6-(1-Benzhydrylazetidin-3-yloxy)-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purine (3A-1)

[0270]

[0271] To a tetrahydrofuran (1 ml) solution of 6-chloro-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-9H-purine I-(1A-1)d (30 mg, 0.073 mmol) and 1-benzhydrylazetidin-3-ol (53 mg, 0.22 mmol) was added potassium tert-butoxide (24 mg, 0.22 mmol). The combined reagents were stirred overnight at ambient temperature. The reaction mixture was concentrated to dryness and the residue was extracted into ethyl acetate from saturated NaHCO3 solution. The organic layers were combined, dried (Na2SO4), filtered, and evaporated to dryness. The crude product was purified by chromatography on a preparative TLC plate using 4% methanol / methylene chloride as the solvent to give title compound 3A-1 as a yellow oil. A solution of the material in methylene chloride was treated with excess 1 N HCl in diethyl ether, stirred, evaporated to dryness, and then triturated in diethyl ether to afford the hy...

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
Electrical conductanceaaaaaaaaaa
Electrical conductanceaaaaaaaaaa
Electrical conductanceaaaaaaaaaa
Login to View More

Abstract

Compounds of Formula (I) that act as cannabinoid receptor ligands and their uses in the treatment of diseases linked to the mediation of the cannabinoid receptors in animals are described herein.

Description

[0001] This application claims the benefit of U.S. Provisional Application No. 60 / 421,874 filed on Oct. 28, 2002 and incorporated herein by reference in its entirety.FIELD OF THE INVENTION [0002] The present invention relates to purine compounds and intermediates useful in the synthesis of the purine compounds. The purine compounds are useful as cannabinoid receptor ligands, in particular as CB-1 receptor antagonists. As a result, the present invention also relates to the use of the purine compounds in treating diseases, conditions and disorders modulated by cannabinoid receptor ligands including pharmaceutical compositions for such use. BACKGROUND [0003] Obesity is a major public health concern because of its increasing prevalence and associated health risks. Obesity and overweight are generally defined by body mass index (BMI), which is correlated with total body fat and estimates the relative risk of disease. BMI is calculated by weight in kilograms divided by height in meters sq...

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
IPC IPC(8): A61K31/52C07D473/12A61P3/04C07D239/48C07D473/00C07D473/30C07D473/34C07D473/40C07D519/00
CPCC07D239/48C07D473/00C07D473/40C07D473/34C07D473/30A61P1/00A61P1/14A61P1/16A61P11/00A61P15/00A61P15/10A61P17/02A61P19/02A61P25/00A61P25/06A61P25/08A61P25/14A61P25/16A61P25/18A61P25/20A61P25/22A61P25/24A61P25/28A61P25/30A61P25/32A61P25/34A61P25/36A61P3/00A61P31/00A61P35/00A61P3/04A61P3/06A61P39/02A61P43/00A61P5/24A61P7/02A61P9/00A61P9/10A61P3/10
Inventor GRIFFITH, DAVID A.
Owner PFIZER INC
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