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Method for preparing indole or indazole compound

A compound and alkyl technology, applied in the field of preparing pharmaceutical indole or indazole compounds, can solve the problems of difficulty in stable scale amplification and lower yield, and achieve the effect of reducing the generation of impurities

Pending Publication Date: 2022-02-25
LG CHEM LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Conventionally, since the intermediates produced during the synthesis of indole or indazole compounds are unstable, many impurities are generated, the yield is reduced, and it is difficult to be stably suitable for scale-up

Method used

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  • Method for preparing indole or indazole compound
  • Method for preparing indole or indazole compound
  • Method for preparing indole or indazole compound

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preparation example Construction

[0083] The preparation method of the present invention may comprise the following steps after forming the intermediate of the above formula 1: replacing the compound represented by the above formula 1 to prepare the compound represented by the following formula 4; reducing the compound represented by the formula 4 to prepare the compound represented by the formula 4 a compound represented by Formula 5; and reacting the compound represented by Formula 5 with a ketone or an aldehyde to prepare a compound represented by Formula 2 above.

[0084] [Formula 4]

[0085]

[0086] [Formula 5]

[0087]

[0088] In the above formula 4 and formula 5, n, m, X, A, R 1 , R 2 , R 3 and R 4 Same as defined above.

[0089] Hereinafter, embodiments of the present invention will be described in more detail so that those of ordinary skill in the art can easily practice the present invention. However, this invention may be embodied in different forms and should not be construed as limit...

Embodiment

[0091] Step a) Synthesis of 4-((7-nitro-2-phenyl-1H-indol-5-yl)methyl)thiomorpholine 1,1-dioxide

[0092] 5-(Hydroxymethyl)-7-nitro-2-phenyl-1H-indole (4.6 kg) and THF (46 L) were added to the reactor and stirred at room temperature, the reactor was cooled to a temperature of 0 °C , then add PBr 3 (2.8 kg) while maintaining the internal temperature of the reaction below 20°C. After the addition was complete, the temperature of the reactor was raised to 25°C, the mixture was stirred for 1 hour, and after analysis of the reaction mixture by sampling showed 5-(hydroxymethyl)-7-nitro-2-phenyl-1H - When the peak of indole is 1.0% or less, the reaction is terminated.

[0093] The completion of the reaction was confirmed, and the reaction mixture was cooled to 0° C., 1,1-diketothiomorpholine hydrochloride (4.4 kg) and N,N-diisopropylethylamine (DIPEA) (8.0 kg ), while maintaining the internal temperature of the reaction below 20°C. After the addition was complete, the temperatu...

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Abstract

The present invention relates to a novel method in which stable intermediates are introduced in the preparation of a pharmaceutically useful indole or indazole compound. This resolves problems caused by conventional unstable intermediates, thus reducing the occurrence of impurities, allows an indole or indazole compound to be prepared with superior yield, and can be stably used in scaled up production.

Description

technical field [0001] Cross References to Related Applications [0002] This application claims the benefit of Korean Patent Application No. 10-2019-0073018 filed with the Korean Intellectual Property Office on June 19, 2019, the disclosure of which is incorporated herein by reference in its entirety. technical field [0003] The present invention relates to a novel method for preparing pharmaceutically useful indole or indazole compounds by introducing stable intermediates. Background technique [0004] Typical diseases resulting from necrosis include ischemia (eg myocardial infarction, stroke, renal infarction), neurodegenerative and inflammatory diseases. Necrosis is uncontrolled, unexpected cell death under pathological conditions, and research is ongoing on the discovery and development of necrosis-inhibiting substances in order to treat ischemic, neurodegenerative, and inflammatory diseases, and to elucidate the biology and pathogenesis of necrosis. Physical reas...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12C07D209/08
CPCC07D405/12C07D209/08C07D407/12C07D417/14C07D209/30C07D231/56
Inventor 李相大朴隘利崔辅斘金奉赞
Owner LG CHEM LTD