# US 2014/0196523 A1 · 5,6,7,8-tetrahydro-6-[n,n-bis[(2-thienyl)ethyl]] amino-1-naphthol, and preparing method and use thereof

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- Number: US 2014/0196523 A1
- Document ID: US20140196523A1
- Status: Published application
- Kind: A1
- Application number: 14/238,936
- Filed: 2012-08-06
- Published: 2014-07-17
- Earliest claimed: 2011-08-17
- Assignees: Shandong Luye Pharmaceutical Co., Ltd.
- Inventors: Mina Yang; Yanyan Zhao; Fengmei Zhou; Quingguo Meng; Tao Wang
- Web page: https://patentgrep.com/patent/US20140196523A1

## CPC

- C07D 333/20: by nitrogen atoms (nitro, nitroso radicals C07D333/12)
- A61P 25/16: Anti-Parkinson drugs
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- G01N 30/02: Column chromatography
- G01N 2030/8877: {optical isomers}
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)

## Abstract

The present disclosure relates to 5,6,7,8-tetrahydro-6-[N,N-bis[(2-thienypethyl]]amino-1-naphthol, a method for preparing the same, and use of 5,6,7,8-tetrahydro-6-[N,N-bis[(2-thienypethyl]]amino-1-naphthol as a reference compound for determining an impurity in rotigotine or a preparation thereof.

## Claims

### Claim 1

A compound of formula (I):
wherein (*) represents a chiral center, and the compound of formula (I) is a R or S configuration or a racemic mixture.

### Claim 2 (depends on 1)

A method for preparing a compound of formula (I) of claim 1, comprising:
reacting a compound of formula (II) with a compound of formula (III),
wherein the compound of formula (II) is a R or S configuration or a racemic mixture, and R1 is methyl, trifluoromethyl, methylphenyl or nitrophenyl; and
purifying the compound of formula (I).

### Claim 3 (depends on 2)

The method of claim 2, wherein R1 is 4-methylphenyl or 4-nitrophenyl.

### Claim 4 (depends on 3)

The method of claim 3, wherein R1 is 4-methylphenyl.

### Claim 5 (depends on 1)

Use of a compound of formula (I) of claim 1 as a reference compound for determining an impurity in rotigotine or a preparation thereof.

### Claim 6 (depends on 1)

A method for determining the content of an impurity in rotigotine or a preparation thereof by high pressure liquid chromatography analysis, wherein the compound of claim 1 is used as a reference compound.

### Claim 7 (depends on 1, 6)

The method of claim 6, comprising:
preparing a reference solution of the compound of formula (I) in a pre-determined concentration;
preparing a test solution containing rotigotine or a preparation thereof;
obtaining HPLC chromatograms of the reference solution and the test solution by high pressure liquid chromatography analysis respectively;
comparing respective retention times in the HPLC chromatograms of the reference solution and the test solution to ascertain that the test solution contains the compound of formula (I) of claim 1; and
determining the content of the compound of claim 1 in rotigotine or the preparation thereof in weight percentage by an external standard method.

### Claim 8 (depends on 1)

A high-purity rotigotine, comprising rotigotine and a compound of claim 1 in an amount less than 0.5weight percent.