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Naphthyloxy benzedrine derivatives and preparation method thereof

A technology of naphthoxyamphetamine and derivatives, which is applied in the field of compound preparation and achieves the effects of high bioavailability, high purity and fast absorption

Active Publication Date: 2013-07-24
HANGZHOU ADAMERCK PHARMLABS INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, no raw materials and preparations of dapoxetine acid salt and basic salt have been declared and listed on the market.

Method used

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  • Naphthyloxy benzedrine derivatives and preparation method thereof
  • Naphthyloxy benzedrine derivatives and preparation method thereof
  • Naphthyloxy benzedrine derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]

[0037] In a 100ml reaction bottle, add 305.42mg of naphthyloxyamphetamine, dissolve it with 50ml of anhydrous methanol, stir, add 98mg of sulfuric acid, after the reaction is completed, recover and concentrate to obtain 399mg of naphthyloxyamphetamine sulfate, and then add naphthyloxyamphetamine acid salt Mix in acetone, add 54mg of sodium methoxide to react for 2 hours, concentrate under reduced pressure, add an appropriate amount of ether, precipitate the solid, filter, wash with ether, and dry to obtain 422mg of white solid naphthyloxyamphetamine sodium bisulfate double salt, yield 92%.

Embodiment 2

[0039]

[0040] In a 100ml reaction bottle, add 305.42mg of naphthyloxyamphetamine, dissolve it with 50ml of absolute ethanol, stir, add 98mg of sulfuric acid, after the reaction is completed, recover and concentrate to obtain 399mg of naphthyloxyamphetamine sulfate, and then add naphthyloxyamphetamine acid salt Mix in DMF, add 84 mg of potassium ethylate to react for 2 hours, concentrate under reduced pressure, add appropriate amount of petroleum ether, precipitate solid, filter, wash with petroleum ether, and dry to obtain 386 mg of white solid naphthyloxyamphetamine potassium hydrogensulfate double salt, Yield 80%.

Embodiment 3

[0042]

[0043] In a 100ml reaction bottle, add 305.42mg of naphthyloxyamphetamine, dissolve with 50ml of anhydrous DMF, stir, add 98mg of sulfuric acid, after the reaction is completed, recover and concentrate to obtain 399mg of naphthyloxyamphetamine sulfate, and then add naphthyloxyamphetamine acid salt Mix in ethanol, add 92 mg of ammonium propionate to react for 3 hours, concentrate under reduced pressure, add an appropriate amount of n-hexane, precipitate the solid, filter, wash with n-hexane, and dry to obtain 319 mg of white solid naphthyloxyamphetamine ammonium bisulfate double salt , yield 65%.

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Abstract

The invention provides naphthyloxy benzedrine derivatives, which are prepared by subsequently reacting naphthyloxy benzedrine with acid and alkali metals or ammonium (including ammonia) compounds or amino acid or alkamine or directly reacting with acid salt; when the acid or acid salt is a sulfate radical, a naphthyloxy benzedrine sulfate complex salt is obtained; and when the acid or the acid salt is a phosphate radical, a naphthyloxy benzedrine phosphate complex salt is obtained. The method has the advantages of rational design, stable process and high production feasibility. The naphthyloxy benzedrine derivatives provided by the method have the remarkable advantages of high bioavailability, high purity, small side effect and the like. The naphthyloxy benzedrine derivatives can be prepared into a preparation, and has rapid absorption and quick response after oral administration by feeding the naphthyloxy benzedrine into blood, so that the curative effect of treating premature ejaculation and erectile dysfunction of men is better achieved. The naphthyloxy benzedrine derivatives have the structural formula shown in the description.

Description

technical field [0001] The invention belongs to compound preparation, and relates to a naphthyloxyamphetamine derivative and a preparation method. Background technique [0002] The clinical application of naphthyloxyamphetamine is its hydrochloride, and its chemical name is (S)-N,N-dimethyl-3-(naphthyl-1-oxyl)-1-amphetamine, also known as dapoxi Dapoxetine (trade name: Priligy), a drug for the treatment of premature ejaculation (PE) in men, has been approved for marketing in Finland and Norway, and is expected to be followed by five other EU countries, including Austria, Germany , Spain, Italy and Portugal. [0003] Dapoxetine is a new type of rapid selective serotonin reuptake inhibitor (SSRI) with a short half-life, which is widely used in the treatment of premature ejaculation and erectile dysfunction in men. [0004] After the drug is absorbed by the stomach, it takes about 20-30 minutes to take effect after oral administration; the action time lasts for dozens of days...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C217/16C07C213/00A61P15/10
Inventor 漆又毛
Owner HANGZHOU ADAMERCK PHARMLABS INC
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