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Inhibitor used as antioxygen and 5-lipoxygenase, and anti-inflammatory non-steroid carboxylic ester and amide of non-steroid anti-inflammatory agent

A non-steroidal, carboxylic acid technology, applied in the direction of anti-toxic agents, anti-inflammatory agents, medical preparations of non-active ingredients, etc., can solve side effects and other problems, and achieve the effect of increasing lipophilicity

Inactive Publication Date: 2005-03-23
ALCON LAB INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are still some problems associated with NSAIA therapy, including how to deliver the drug to the proper site of action and their side effects ( Goodman and Gilman's The Pharmacological Basis of Therapeutics , pp. 638-669, Pergman Press, NY (1990))

Method used

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  • Inhibitor used as antioxygen and 5-lipoxygenase, and anti-inflammatory non-steroid carboxylic ester and amide of non-steroid anti-inflammatory agent
  • Inhibitor used as antioxygen and 5-lipoxygenase, and anti-inflammatory non-steroid carboxylic ester and amide of non-steroid anti-inflammatory agent
  • Inhibitor used as antioxygen and 5-lipoxygenase, and anti-inflammatory non-steroid carboxylic ester and amide of non-steroid anti-inflammatory agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0133] Synthesis of N-(2-(3,4-dihydroxyphenyl)-2-hydroxyethyl)-N-methyl 2-(6 -Methoxy-2-naphthyl)propionamide

[0134]Epinephrine (Aldrich, 3.18 grams [g], 17.3 mmol [mmol]), 1-hydroxybenzotriazole hydrate (Aldrich, 1.76 g, 12.9 mmol) and 1-(3-dimethylaminopropyl )-3-Ethylcarbodiimide HCl (Aldrich, 2.49 g, 12.9 mmol) was added to acetonitrile (200 milliliters [ml]). After stirring for 10 minutes, a solution of 6-methoxy-α-methyl-2-naphthaleneacetic acid (Aldrich, 2.0 g, 8.66 mmol) in 50 ml of acetonitrile was added dropwise. After stirring for 16 hours, the reaction mixture was concentrated in vacuo (reduced pressure) and the residue was partitioned between water (100ml) and dichloromethane (100ml). The layers were separated and the aqueous layer was extracted with dichloromethane (2 x 50ml) and ethyl acetate (50ml). The combined organic phases were treated with methanol until a clear solution formed. The solution was dried (magnesium sulfate) and concentrated in vacuo....

Embodiment 2

[0141] Synthesis of 2-(6-hydroxy-2,5,7,8-tetrafluoroethylene)propionate 2-(6-methoxy-2-naphthyl) Methyl-3,4-dihydro-2H-benzo[1,2-b]pyran-2-yl)methyl ester

[0142] Under nitrogen atmosphere, 6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzo[1,2-b]pyran-2-yl)methanol (2.00g, 8.46mmol), 6-Methoxy-α-methyl-2-naphthaleneacetic acid (2.14g, 9.31mmol), dimethylaminopyridine (Aldrich, 1.24g, 10.00mmol) and 1-(3-dimethylaminopropyl) - A solution of 3-ethylcarbodiimide hydrochloride (1.71 g, 8.89 mmol) in tetrahydrofuran (40 ml) was stirred at room temperature for 72 hours. The mixture was then diluted with ethyl acetate (200ml) and washed first with 0.5N hydrochloric acid (2x250ml) followed by water (2x250ml), then dried (sodium sulfate) and concentrated in vacuo. The residue was flash chromatographed (silica gel, 100-50:0-50, V:V, hexane:ethyl acetate) and the appropriate fractions were concentrated to give an oil. Recrystallization from ethyl acetate-hexane gave 2.21 g (58.3% yield) of...

Embodiment 3

[0149] Synthesis of N-[(6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzene And[1,2-b]pyran-2-yl)methyl)]-2-(6-methoxy-2-naphthyl)propionamide

[0150] First synthesize the intermediate (6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzo[1,2-b]pyran-2-yl)methanamine :

[0151] A 1M solution of lithium aluminum hydride in diethyl ether (Aldrich, 32.4 mL, 32.43 mmol) was slowly added dropwise to the stirred (2-cyano-6-hydroxy-2,5,7,8-tetramethyl -3,4-dihydro-2H-1-benzo[1,2-b]pyran in tetrahydrofuran (50ml) cold (4-6 ° C) solution. After 2 hours, under stirring, slowly add 10 % hydrated tetrahydrofuran (30 mL), 15% sodium hydroxide (10 mL) and water (20 mL), quenched the reaction mixture. The resulting suspension was filtered through celite, and the celite plate was washed with diethyl ether (400 mL). The organic layer was dried (Na 2 SO 4 ), and concentrated in vacuo to obtain a residue. To a solution of the residue in ether (100 mL) was then added 1M hydrogen chlo...

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Abstract

The compounds of the present invention are of the formula (I): A-X-(CH2)n-Y-(CH3)m-Z wherein the groups are defined in description. The compounds of the present invention also include pharmaceutically acceptable salts of the compounds of formula (I). Methods for treating inflammatory pathologies are disclosed. Particularly, the methods utilize pharmaceutical compositions containing certain compounds having an inti-inflammatory and anti-oxidant moiety covalently linked by an amide or ester bond. The compounds are useful in preventing and treating inflammatory disorders through several mechanisms.

Description

[0001] This application is an invention with the application number of 95197049.6 and the title of the invention "anti-inflammatory non-steroidal carboxylate and amide useful as antioxidant, 5-lipoxygenase inhibitor and non-steroidal anti-inflammatory drug" A divisional application of a patent application. This application is a continuation of the following two U.S. patent applications, the first of which was filed on December 23, 1994, with application number 08 / 362,718; the second of which was filed on June 7, 1995, with application number 08 / 472,445. technical field [0002] It is an object of the present invention to provide compounds having potent anti-inflammatory and antioxidant activities. The present invention further relates to compositions containing compounds of the present invention for pharmaceutical use. The present invention also relates to various methods of using the compounds and compositions of the present invention in pharmaceutical applications includi...

Claims

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Application Information

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IPC IPC(8): C07D317/60A61K31/165A61K31/34A61K31/343A61K31/35A61K31/352A61K31/353A61K31/355A61K31/357A61K31/40A61K31/403A61K31/4035A61P27/02A61P29/00C07C235/34C07C235/66C07D209/44C07D307/80C07D311/72C07D405/12
CPCC07C235/34A61K31/343A61K31/353C07D307/80A61K31/355A61K47/48061C07D311/72A61K47/545A61P27/00A61P27/02A61P29/00A61P39/06
Inventor M·赫尔伯格G·格拉夫D·A·加玛彻J·C·尼克森W·H·加纳
Owner ALCON LAB INC
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