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Indacaterol intermediate salt and preparation method thereof

An intermediate, selected technology, applied in the field of salt of indacaterol intermediate and its preparation, can solve the problems of unsatisfactory yield and purity, and achieve the effect of low cost, easy realization and good reproducibility

Inactive Publication Date: 2017-08-08
SHANGHAI FANGNAN PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] Patent CN100363349 discloses the use of benzoic acid, maleic acid, succinic acid, fumaric acid, and tartaric acid to carry out salification treatment on the above-mentioned reaction solution, and the corresponding salt of the obtained formula (II) is separated and purified, but the achieved yield and purity is still not ideal

Method used

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  • Indacaterol intermediate salt and preparation method thereof
  • Indacaterol intermediate salt and preparation method thereof
  • Indacaterol intermediate salt and preparation method thereof

Examples

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Effect test

Embodiment 1

[0033] (R)-5-[2-[(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-(benzyloxy )-2 (1H) - preparation of quinolinone malate:

[0034] 8-Benzyloxy-5-(R)-oxiranyl-(1H)-quinolin-2-one (1.2 g) and 2-amino-(5,6-diethyl)-indan (1.1 g) was added to diethylene glycol dimethyl ether, heated to 110 ° C, and reacted at this temperature for 48 hours, the resulting suspension was cooled to 70 ° C, ethanol (70 ml) was added, followed by malic acid (0.6 g), the solution was cooled to 20-30° C., seed crystals were added, the resulting suspension was cooled to 0-5° C., the solid was separated by filtration, and vacuum-dried. The yield was 64%, and the HPLC purity was 98.4%.

Embodiment 2

[0036] (R)-5-[2-[(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-(benzyloxy )-2 (1H) - preparation of quinolinone oxalate:

[0037] 8-Benzyloxy-5-(R)-oxiranyl-(1H)-quinolin-2-one (1.2 g) and 2-amino-(5,6-diethyl)-indan (1.1 g) was added to n-butanol, heated to 120°C, and reacted at this temperature for 48 hours, the resulting suspension was cooled to 70°C, oxalic acid (0.5 g) was added, and the solution was cooled to 20-30°C , adding seed crystals, cooling the resulting suspension to 0-5° C., separating the solid by filtration, and drying in vacuo. The yield is 65%, and the HPLC purity is 98.6%.

Embodiment 3

[0039] (R)-5-[2-[(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]-8-(trityl Preparation of (oxy)-2(1H)-quinolinone malonate:

[0040] 8-trityloxy-5-(R)-oxiranyl-(1H)-quinolin-2-one (1.2 g) and 2-amino-(5,6-diethyl) - Indane (1.1 g) was added to diethylene glycol dimethyl ether, heated to 110 ° C, and reacted at this temperature for 48 hours, the resulting suspension was cooled to 70 ° C, and malonic acid (0.7 g) was added , the solution was cooled to 20-30° C., seed crystals were added, the resulting suspension was cooled to 0-5° C., the solid was separated by filtration, and vacuum-dried. The yield was 68%, and the HPLC purity was 99.0%. .

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Abstract

The invention relates to an indacaterol intermediate salt and a preparation method thereof, and the preparation method of the indacaterol intermediate salt has the advantages of simple operation, low cost, good reproducibility and easy realization, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a salt of an indacaterol intermediate and a preparation method thereof. Background technique [0002] Indacaterol (Indacaterol, trade name ), the structure is as shown in formula (VI): [0003] [0004] Indacaterol is a β-selective adrenoceptor agonist with potent bronchodilatory activity and is useful in the treatment of asthma and chronic obstructive pulmonary disease (COPD). Since 2009, it has been listed in more than 70 countries and regions around the world. In June 2012, it was approved to be launched in China by the State Food and Drug Administration. It is the first long-acting β2 receptor agonist approved for the treatment of COPD in China. [0005] Indacaterol is composed of (R)-5-[2-[(5,6-diethyl-2,3-dihydro-1H-inden-2-yl)amino]-1-hydroxyethyl]- 8-(Substituted oxy)-2(1H)-quinolinone [formula (II)] is obtained by deprotection. Therefore, formula (II) is the key intermediate for preparing indacaterol. And the m...

Claims

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Application Information

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IPC IPC(8): C07D215/26C07F7/18
CPCC07D215/26C07F7/1804C07F7/1892Y02P20/55
Inventor 张席妮熊志刚资春鹏周涛杨庆昆
Owner SHANGHAI FANGNAN PHARMA
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