3CL protease inhibitor of non-peptide SARS coronavirus and use thereof

A coronavirus, protease technology, applied in antiviral agents, respiratory diseases, medical preparations containing active ingredients, etc., to achieve high accuracy and good reproducibility

Inactive Publication Date: 2007-05-23
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, so far there is no recommended drug for SARS

Method used

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  • 3CL protease inhibitor of non-peptide SARS coronavirus and use thereof
  • 3CL protease inhibitor of non-peptide SARS coronavirus and use thereof
  • 3CL protease inhibitor of non-peptide SARS coronavirus and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1. The synthesis of oxamide

[0029] [References: Liu Xiang, Liu Tinghui, Liu Baili. Journal of Shenyang Pharmaceutical University, 2001, 18(5), 327-328. ]

[0030] 1. Synthetic route:

[0031]

[0032] 2. Experimental steps:

[0033] Preparation of A, 1-isopropenyl-1,3-dihydro-2H-benzimidazol-2-one (2)

[0034] In a reaction flask equipped with a water separator, add 54g (0.5mol) of o-phenylenediamine and 220ml of xylene, and after heating and stirring to reflux, slowly add a mixture of 71.5g (0.55mol) of ethyl acetoacetate and 20ml of xylene , After dropping, stir and reflux, azeotropic dehydration until no water drops appear, continue to stir and reflux for 2h. After the reaction is complete, cool and precipitate crystals, filter and dry to obtain 56.2 g of white granular crystals (3) (64.6% yield), mp 121-122°C

[0035] B, the preparation of 1-(3-chloropropyl)-1,3-dihydro-2H-benzimidazol-2-one (3)

[0036] In the reaction flask, add (2) 5.042g (...

Embodiment 2

[0044] The synthesis of embodiment 2.1-benzhydryl-4-benzylpiperazine (pkumdl_cvs_1006)

[0045] According to the operating conditions of step E in Example 3, (4) was replaced by benzyl chloride to obtain 1-benzhydryl 4-benzylpiperazine, which was recrystallized from acetone to obtain colorless crystals with a yield of 81.2%.

[0046] 1 HNMR (CDCl 3 )δ: 2.46(s, 8H, hydrogen on the piperazine ring), 3.51(s, 2H, CH 2 Ph), 4.23 (s, 1H, ArCH), 7.14-7.42 (m, 15H, hydrogen on the benzene ring)

Embodiment 3

[0047] The synthesis of embodiment 3.1-benzhydryl-4-[(pyridin-3-yl) methyl] piperazine (pkumdl_cvs_1007)

[0048] According to the operating conditions of step E in Example 3, (4) is replaced by 3-chloromethylpyridine hydrochloride to obtain 1-benzhydryl-4-[(pyridin-3-yl)methyl]piperazine , recrystallized from acetone to obtain colorless crystals with a yield of 61.8%.

[0049] 1 HNMR (CDCl 3 )δ: 2.41 (s, 8H, hydrogen on the piperazine ring), 3.49 (s, 2H, CH 2 -), 4.27 (s, 1H, CH-), 7.12-7.42, 7.65-7.69, 8.43-8.45 (m, d, d, 14H, hydrogen on benzene ring and pyridine ring).

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Abstract

The invention relates to a restrainer non-peptide SARS corona-virus 3CL prolease, wherein said restrainer is cyclizine derivant functioning at volume occupation and dewatering function with 3CL prolease. The invention uses the enzyme active system of reverse-phase high-pressure liquid spectrum method and substrate pNA mark to test its effect on the activity of SARS corona-virus 3CL prolease. Said test can prove that it has restrain effect on 3CL prolease, and its cell test can restrain SARS coron-avirus of cell cultivation. The invention can treat and prevent SARS virus affection.

Description

technical field [0001] The present invention relates to a class of compounds for preventing and treating SARS coronavirus and other viral infections, in particular to a class of non-peptidic SARS coronavirus 3CL protease inhibitor benzhydryl piperazine derivatives. Background technique [0002] In the spring of 2003, SARS (Severe Acute Respiratory Syndrome) broke out in Hong Kong, Guangzhou, Beijing and other regions, causing great harm to people's physical and mental health. The SARS epidemic, which has no precedent for prevention or treatment, has aroused people's great attention. The research and development of drugs for SARS once became the focus of research by Chinese scientists. However, so far there is no recommended drug for SARS. [0003] Studies have shown that the variant coronavirus is the main culprit that causes SARS. The main protease or 3CL protease of coronavirus is a key protein in virus replication, and its main function is to hydrolyze two polyproteins...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/495A61P31/14A61P11/00
Inventor 来鲁华刘莹刘振明范可强黄常康魏平裴剑锋刘士勇陈浩
Owner PEKING UNIV
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