Title:
NEW METHOD FOR SYNTHESIZING 1,6-(P-AMIDINOPHENYL)HEXYL DIETHER
Document Type and Number:
WIPO Patent Application WO/2019/161705
Kind Code:
A1
Abstract:
Disclosed is a new method for synthesizing 1,6-(p-amidinophenyl)hexyl diether, comprising the steps of: (1) preparing 1,6-(p-cyanophenyl)hexyl diether by reacting p-cyanophenol with 1,6-dibromohexane; (2) reacting the 1,6-(p-cyanophenyl)hexyl diether obtained in step (1) with hydroxylamine, or with hydroxylamine hydrochloride under a condition of the presence of a base, so as to prepare 1,6-(p-amidoximephenyl)hexyl diether; and (3) reducing the 1,6-(p-amidoximephenyl)hexyl diether obtained in step (2), to obtain the 1,6-(p-amidinophenyl)hexyl diether; or first reacting the 1,6-(p-amidoximephenyl)hexyl diether obtained in step (2) with an esterification reagent or etherification reagent to obtain an ester or ether, and then subjecting same to a reduction reaction, to obtain the 1,6-(p-amidinophenyl)hexyl diether. The new synthesis method of the present invention is more green and environmentally friendly than traditional processes, has a greatly improved yield, and is suitable for large-scale industrial production.
Inventors:
ZHENG QINGQUAN (CN)
Application Number:
PCT/CN2018/123346
Publication Date:
August 29, 2019
Filing Date:
December 25, 2018
Export Citation:
Assignee:
GUANGZHOU TROJAN PHARMATEC LTD (CN)
International Classes:
C07C259/18; C07C253/30; C07C255/54; C07C257/18
Domestic Patent References:
| WO2006011499A1 | 2006-02-02 |
Foreign References:
| CN105037206B | 2016-08-17 | |||
| EP2116236A1 | 2009-11-11 | |||
| CN104710329A | 2015-06-17 |
Other References:
JOSEPH VAMECQ ET AL.: "1, 2-Ethane bis-1-amino-4-benzamidine is active against several brain insult and seizure challenges through anti-NMDA mechanisms targeting the 3H-TCP binding site and antioxidant action", EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 3 April 2010 (2010-04-03), pages 3101 - 3110, XP028303005
DIMITRI STANICKI ET AL.: "Diamidines versus Monoamidines as Anti-Pneumocystis Agents: An in Vivo Study", PHARMACEUTICALS, 1 July 2013 (2013-07-01), pages 837 - 840, XP055631553
HOSCHA KOTTHAUS ET AL.: "NEW PRODRUGS OF THE ANTIPROTOZOAL DRUG PENTAMIDINE", CHEMMEDCHEM, 31 December 2011 (2011-12-31), pages 2233 - 2242, XP055631557
DIMITRI STANICKI ET AL.: "Diamidines versus Monoamidines as Anti-Pneumocystis Agents: An in Vivo Study", PHARMACEUTICALS, 1 July 2013 (2013-07-01), pages 837 - 840, XP055631553
HOSCHA KOTTHAUS ET AL.: "NEW PRODRUGS OF THE ANTIPROTOZOAL DRUG PENTAMIDINE", CHEMMEDCHEM, 31 December 2011 (2011-12-31), pages 2233 - 2242, XP055631557
Attorney, Agent or Firm:
SCIHEAD IP LAW FIRM (CN)
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