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Phenyl derivatives and methods of use

a technology of phenyl derivatives and derivatives, applied in the field of new phenyl compounds, can solve the problems of causing a number of unwanted cns side effects, separating clinically undesirable psychotropic effects from therapeutically desirable effects on the peripheral nervous system, immune and endocrine system,

Inactive Publication Date: 2010-07-01
APOLOR CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, separation between the clinically undesirable psychotropic effects and the therapeutically desirable effects on the peripheral nervous systems, the cardiovascular system, and the immune and endocrine systems is problematic.
They also induce a number of unwanted CNS side effects.
Furthermore, the known cannabinoid receptor agonists are in general highly lipophilic and insoluble in water.

Method used

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  • Phenyl derivatives and methods of use
  • Phenyl derivatives and methods of use
  • Phenyl derivatives and methods of use

Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of 2-(3-(Benzyloxy)phenyl)-2-methylpropanenitrile (II)

[0338]

[0339]A solution of commercially available nitrile I (83.9 g, 0.38 mol) in DMSO (57 mL) and 50% NaOH solution (120 mL) were simultaneously added to DMSO (425 mL) previously saturated for one hour with bromomethane gas. Bromomethane was continuously bubbled through the reaction mixture during the addition and then for a further 1.5 hours with ice-cooling to maintain the temperature at 50° C. or less. The reaction mixture was added to a 600 mL H20-600 g ice mixture and then extracted with Et2O (3×800 mL), the ethereal layers were washed with water (1L) and brine (1L), dried and concentrated under reduced pressure to give a yellow oil. The yellow oil was cooled in a dry-ice acetone bath until it solidified and then left to stand at room temperature overnight to afford II as a light yellow crystalline solid (93.59 g, 98%). M+1=252.

example 2

Preparation of 2-(3-(benzyloxy)phenyl)-2-methylpropanal (III)

[0340]

[0341]Diisobutylaluminum hydride (300 mL, 0.3 mol of a 1.0 M solution in hexanes) was added dropwise to a cooled (15° C., ice-bath) solution of nitrile II (59.9 g, 0.24 mol) in anhydrous tetrahydrofuran (250 mL). The reaction temperature was maintained at 15-18° C. during the addition. The reaction was then allowed to warm to room temperature and stirred for an additional 2 hours. The reaction was hydrolyzed by addition of a cold solution of conc. H2SO4 (35.5 mL) in water (117.5 mL) with the temperature maintained at <30° C. The resultant mixture was stirred for a further 2 hours, then filtered, and the filtrate extracted with diethyl ether (2×250 mL), washed with water (300 mL), brine (300 mL), dried and concentrated under reduced pressure to give crude aldehyde III as a light-yellow oil (59.82 g, 98%) which was used without further purification. M+1=255.

example 3

Preparation of 2-(3-Benzyloxy-phenyl)-2-methyl-propan-1-ol (IV)

[0342]

[0343]Reduction of III was carried out under standard conditions using NaBH4 in tetrahydrofuran as described by Chaikin and Brown (J. Am. Chem. Soc. 1949, 71, 122) to generate IV quantitatively. M+1=257

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PUM

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Abstract

Novel phenyl compounds, pharmaceutical compositions containing these compounds, and methods for their pharmaceutical use are disclosed. In certain embodiments, the compounds are agonists and / or ligands of cannabinoid receptors and may be useful, inter alia, for treating and / or preventing pain, gastrointestinal disorders, genitourinary disorders, inflammation, glaucoma, auto-immune diseases, ischemic conditions, immune-related disorders, and neurodegenerative diseases, for providing cardioprotection against ischemic and reperfusion effects, for inducing apoptosis in malignant cells, and as an appetite stimulant.

Description

CROSS REFERENCE TO RELATED APPLICATION[0001]This application is a divisional of U.S. Application Ser. No. 11 / 242,318, filed Oct. 3, 2005, now allowed, which claims the benefit of U.S. Provisional Application Ser. No. 60 / 616,024, filed Oct. 5, 2004. The disclosures of these applications are incorporated herein by reference in their entireties.FIELD OF THE INVENTION[0002]The present invention generally relates to novel phenyl compounds and the use thereof. More particularly, the present invention relates to novel phenyl compounds and their use, inter alia, as agonists of cannabinoid receptors.BACKGROUND OF THE INVENTION[0003]Cannabis sativa preparations have long been known as therapeutic agents to treat various diseases (Mechoulam, R., “Cannabinoids as Therapeutic Agents” CRC Press, Boca Raton, Fla. 1-19, 1986). The native active constituent, delta 9-tetrahydrocannabinol (Δ9-THC), is prescribed today, under the generic name dronabinol, as an anti-emetic and for enhancement of appetit...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/5377C07C303/02C07C275/28C07D295/18C07D417/12C07D413/12C12N5/071A61K31/17A61K31/18A61K31/5375A61K31/485A61K31/445A61K31/192A61K31/195A61P1/14
CPCC07C275/24C07C275/32C07C311/04C07C311/08C07D207/28C07D207/34C07D213/82C07D213/89C07D231/14C07D241/24C07D261/18C07D285/06C07D295/096C07D295/185C07D307/24C07D307/68C07D333/38A61P1/02A61P1/04A61P1/08A61P1/12A61P1/14A61P11/00A61P11/06A61P13/00A61P13/10A61P13/12A61P15/00A61P17/06A61P19/02A61P19/10A61P21/00A61P21/04A61P25/00A61P25/04A61P25/14A61P25/16A61P25/28A61P27/06A61P29/00A61P37/02A61P37/06A61P37/08A61P43/00A61P9/06A61P9/10A61P9/12A61P3/10
Inventor DOLLE, ROLAND E.WORM, KARINZHOU, Q. JEAN
Owner APOLOR CORP
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