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Novel anthranilic acid derivatives

an anthranilic acid and derivative technology, applied in the field of new anthranilic acid derivatives, can solve the problems of reducing plaque stability, increasing cardiovascular risk, and hampered extensive use of niacin

Inactive Publication Date: 2006-12-14
F HOFFMANN LA ROCHE & CO AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Inflammation is a critical component of atherosclerosis, leading to recruitment of macrophages which both promote plaque development and decrease plaque stability thus increasing cardiovascular risk.
Extensive use of niacin has been hampered due to side effects, mainly intense cutaneous flushing.

Method used

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  • Novel anthranilic acid derivatives
  • Novel anthranilic acid derivatives
  • Novel anthranilic acid derivatives

Examples

Experimental program
Comparison scheme
Effect test

example 1

2-(4-Benzyloxy-benzoylamino)-benzoic acid

Step 1:

2-(4-Benzyloxy-benzoylamino)-benzoic acid methyl ester

[0353] To 2-amino-benzoic acid methyl ester (0.51 mL) and triethylamine (0.69 mL) in dichloromethane (31 mL) at −50° C. was slowly added a solution of 4-benzyloxy-benzoyl chloride [1486-50-6](1 g) in 31 mL of dichloromethane. The reaction mixture was then allowed to warm up to room temperature and stirred for an additional hour. After such time, the reaction mixture was washed with water. The aqueous phase was further extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (heptane-ethyl acetate: 0-50%) to yield 2-(4-benzyloxy-benzoylamino)-benzoic acid methyl ester (400 mg). MS (m / e): 362.5 (M+H+, 100%).

Step 2:

2-(4-Benzyloxy-benzoylamino)-benzoic acid

[0354] To 2-(4-benzyloxy-benzoylamino)-benzoic acid methyl ester (50 mg) in methanol (3 mL) was added lithium hydro...

example 2

2-[4-(4-Fluoro-phenoxy)-benzoylamino]-benzoic acid

[0355] To 2-(4-iodo-benzoylamino)-benzoic (acid methyl ester [75541-84-3](50 mg) in 1-methyl-2-pyrrolidinone (1 mL) was added 4-fluorophenol (29.4 mg), copper (I) chloride (6.6 mg), cesium carbonate (85 mg) and 8-hydroxy-chinolin (4.7 mg). The reaction mixture was stirred at 120° C. for 18 hours. After such time, the reaction mixture was allowed to cool down to room temperature, diluted with water, formic acid was added (0.3 mL) and the solution was purified by preparative HPLC to yield 2-[4-(4-fluoro-phenoxy)-benzoylamino]-benzoic acid (49.1 mg). MS (m / e): 332.1 (M−H−, 100%).

example 3

2-[4-(3,4-Dichloro-phenoxy)-benzoylamino]-benzoic acid

[0356] In analogy to example 2, 2-[4-(3,4-Dichloro-phenoxy)-benzoylamino]-benzoic acid was prepared from 2-(4-iodo-benzoylamino)-benzoic acid methyl ester [75541-84-3]and 3,4-dichlorophenol. MS (m / e): 400.0 (M−H−, 100%).

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Abstract

The invention is concerned with novel anthranilic acid derivatives of formula (I) wherein R1 to R14 and n are as defined in the description and in the claims, as well as physiologically acceptable salts and esters thereof. These compounds are HM74A agonists and can be used as medicaments.

Description

PRIORITY TO RELATED APPLICATIONS [0001] This application claims the benefit of European Application No. 05105176.1, filed Jun. 14, 2005, which is hereby incorporated by reference in its entirety. FIELD OF THE INVENTION [0002] The invention is directed to novel anthranilic acid derivatives of the formula (I) and pharmaceutically acceptable salts and pharmaceutically acceptable esters thereof. [0003] Further, the invention is directed to a process for the manufacture of the above compounds, pharmaceutical preparations which contain such compounds as well as the use of these compounds for the production of pharmaceutical preparations. [0004] All documents cited or relied upon below are expressly incorporated herein by reference. BACKGROUND [0005] Coronary heart disease (CHD) remains the leading cause of death in Western countries. In the United States 13.2 million or 4.85% of the population is affected, with 1.2 million new or recurrent attacks and around 500 thousand deaths per year...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/277A61K31/195C07C255/60C07C237/02
CPCC07C235/56C07C255/54C07C317/22C07D249/08C07D213/65C07D215/26C07D213/643A61P1/04A61P1/16A61P1/18A61P25/16A61P25/18A61P25/28A61P29/00A61P3/00A61P3/04A61P31/04A61P3/06A61P7/02A61P9/00A61P9/08A61P9/10A61P3/10C07C233/75
Inventor DEHMLOW, HENRIETTAGRETHER, UWEKRATOCHWIL, NICOLE A.NARQUIZIAN, ROBERTPANOUSIS, CONSTANTINOSPETERS, JENS-UWE
Owner F HOFFMANN LA ROCHE & CO AG
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