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Compound containing guanidyl group, and preparation method and application thereof

A compound and guanidine-based technology, applied in the field of preparation of the compound, method and intermediate, can solve the problems of limited curative effect and high cost

Pending Publication Date: 2021-08-06
HC SYNTHETIC PHARMA CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The monoclonal antibody palivizumab is available for immunoprophylaxis, but its use is limited to high-risk infants, eg, premature infants or those with congenital heart or lung disease, and is often cost prohibitive for general use
In addition, the nucleoside analog ribavirin has been approved as the only antiviral agent for the treatment of HRSV infection with limited efficacy

Method used

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  • Compound containing guanidyl group, and preparation method and application thereof
  • Compound containing guanidyl group, and preparation method and application thereof
  • Compound containing guanidyl group, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0122] Example 1: Ethyl (2S)-2-(chloro(phenoxy)phosphorylamino)propionate (chloride A1)

[0123]

[0124] Ethylalaninate hydrochloride (2.54g, 16.5mmol) was dissolved in anhydrous dichloromethane (30ml) and the mixture was cooled to 0°C with stirring under N2 (g). Phenyl dichlorophosphate (2.23 mL, 25 mmol) was added, followed by the dropwise addition of triethylamine over 10 min. The reaction mixture was then slowly warmed to RT and stirred for 12 h. Anhydrous acetic anhydride (150 mL) was added, and the mixture was stirred for 30 min. The solid formed was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was chromatographed on silica gel eluting with 0-50% EtOAc in hexanes to provide chloride Al (1.86 g, 39%).

[0125] 1 H NMR (300 MHz, CDC13) δ 7.39-7.27 (m, 5H), 4.27 (m, 3H), 1.52 (m, 3H), 1.32 (m, 3H).

[0126] 31 P NMR (121.4MHz, CDCl 3 )δ8.2,7.8.

Embodiment 2

[0127] Example 2: 9-ethylbutyl (2S)-2-(chloro(phenoxy)phosphorylamino)propionate (chloride B1)

[0128]

[0129] 2-Ethylbutylalanine chlorophosphoramidate B1 was prepared using the same procedure as chloride A1 except that 2-ethylbutylalanine was used instead of ethylalanine. The crude material was used in the next reaction. Treatment with methanol or ethanol forms a surrogate product with the desired LCMS signal.

Embodiment 3

[0130] Example 3: Isopropyl (2S)-2-(chloro(phenoxy)phosphorylamino)propionate (chloride C1)

[0131]

[0132] Isopropylalanine chlorophosphoramidate C1 was prepared using the same procedure as chloride A1 except that isopropylalanine was used instead of ethylalanine. The crude material was used in the next reaction. Treatment with methanol or ethanol forms a surrogate product with the desired LCMS signal.

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PUM

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Abstract

The invention provides a preparation containing a guanidino compound and used for treating pneumoviridae virus infection, a method, a compound of a formula I, and a method and an intermediate for synthesizing the compound of the formula I.

Description

technical field [0001] Provided herein are compounds, methods and pharmaceutical formulations for the treatment of Pneumovlrlnae virus infections, including, in particular, respiratory coronavirus infections, as well as methods and intermediates useful for the preparation of the compounds. Background technique [0002] Pneumovirinae viruses are negative-sense, single-stranded RNA viruses that are responsible for many prevalent human and animal diseases. The pneumovirinae subfamily of viruses is part of the Paramyxoviridae family and includes the human respiratory syncytial virus (HRSV). Almost all children experience HRSV infection by their second birthday. HRSV is a leading cause of lower respiratory tract infections in infants and children, with 0.5% to 2% of those infected requiring hospitalization. Older adults and adults with chronic heart disease, lung disease, or those who are immunosuppressed are also at high risk for developing severe HRSV disease. There is curre...

Claims

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Application Information

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IPC IPC(8): C07D487/04C07H13/12C07F9/6561C07H11/04C07H1/00C07H1/02C07H1/04A61K31/53A61K31/706A61K31/675A61K31/685A61P31/14
CPCC07D487/04C07H13/12C07F9/65616C07H11/04C07H1/00C07H1/02C07H1/04A61P31/14
Inventor 杨成陆华龙张起愿
Owner HC SYNTHETIC PHARMA CO LTD
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